KR20020058023A - Pesticidal Aminoheterocyclylamide Compounds - Google Patents

Abstract

The present invention relates to compounds of formula (I) and any enantiomers thereof.

<Formula I>

In the formula,

R ₁ is hydrogen, halogen, C ₁ -C ₆ -alkyl, C ₁ -C ₆ -alkoxy, C ₁ -C ₆ -haloalkyl, or unsubstituted phenyl or C ₁ -C ₆ -alkyl, C ₁ -C ₆ -Phenyl mono- or substituted-substituted by a substituent selected from the group consisting of haloalkyl, C ₁ -C ₆ -alkoxy, aryloxy, halogen, cyano and nitro, wherein the number of substituents is greater than 1 They may be the same or different from each other;

R ₂ is hydrogen, C ₁ -C ₆ -alkyl, (C ₁ -C ₆ -alkylene) phenyl, pyridyl, COOR ₆ , CONR ₇ R ₈ , COR ₆ , allyl or CH ₂ -OR ₆ ;

X ₁ is N or C (CN);

X ₂ is N, C (CN), C (COOR ₆ ), C (COR ₆ ), C (SOR ₆ ), C (CONR ₇ R ₈ ) or C (N0 ₂ );

X ₃ is O or S;

Q is CH or N;

R ₃ and R ₄ are independently of each other hydrogen, C ₁ -C ₆ -alkyl, or together with the C atom to which they are attached form a C ₃ -C ₇ -cycloalkyl ring;

R ₅ is C ₁ -C ₆ -alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkynyl, C ₁ -C ₆ -haloalkyl, C ₁ -C ₆ -alkoxy, aryloxy, halogen , Cyano, hydroxy, amino, nitro and mono- or substituted-substituted phenyl, wherein the phenyl substituent is C ₁ -C ₆ -alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkynyl, C ₁ -C ₆ -haloalkyl, C ₁ -C ₆ -alkoxy, aryloxy, halogen, cyano, hydroxy, amino and nitro, the number of substituents being 1 If greater, the substituents may be the same or different from each other, and when m is greater than 1, the substituents R ₅ may be identical or different from each other;

R ₆ is C ₁ -C ₆ -alkyl, phenyl or benzyl;

R ₇ and R ₈ are independently of each other hydrogen or C ₁ -C ₆ -alkyl;

m is 1, 2 or 3;

n is 0 or 1;

The active ingredient has advantageous pesticidal properties. The components are particularly suitable for controlling pests of livestock and farm animals.

Description

Insecticidal Aminoheterocyclylamide Compounds

The present invention relates to novel substituted aminoheterocyclylamides of formula (I), their preparations and their use in pest control, and pesticides containing at least one compound of formula (I).

In the formula,

R ₁ is hydrogen, halogen, C ₁ -C ₆ -alkyl, C ₁ -C ₆ -alkoxy, C ₁ -C ₆ -haloalkyl, or unsubstituted phenyl or C ₁ -C ₆ -alkyl, C ₁ -C ₆ -Phenyl mono- or substituted-substituted by a substituent selected from the group consisting of haloalkyl, C ₁ -C ₆ -alkoxy, aryloxy, halogen, cyano and nitro, wherein the number of substituents is greater than 1 They may be the same or different from each other;

R ₂ is hydrogen, C ₁ -C ₆ -alkyl, (C ₁ -C ₆ -alkylene) phenyl, pyridyl, COOR ₆ , CONR ₇ R ₈ , COR ₆ , allyl or CH ₂ -OR ₆ ;

X ₁ is N or C (CN);

X ₂ is N, C (CN), C (COOR ₆ ), C (COR ₆ ), C (SOR ₆ ), C (CONR ₇ R ₈ ) or C (N0 ₂ );

X ₃ is O or S;

Q is CH or N;

R ₃ and R ₄ are independently of each other hydrogen, C ₁ -C ₆ -alkyl, or together with the C atom to which they are attached form a C ₃ -C ₇ -cycloalkyl ring;

R ₅ is C ₁ -C ₆ -alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkynyl, C ₁ -C ₆ -haloalkyl, C ₁ -C ₆ -alkoxy, aryloxy, halogen , Cyano, hydroxy, amino, nitro and mono- or substituted-substituted phenyl, wherein the phenyl substituent is C ₁ -C ₆ -alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkynyl, C ₁ -C ₆ -haloalkyl, C ₁ -C ₆ -alkoxy, aryloxy, halogen, cyano, hydroxy, amino and nitro, the number of substituents being 1 If greater, the substituents may be the same or different from each other, and when m is greater than 1, the substituents R ₅ may be identical or different from each other;

R ₆ is C ₁ -C ₆ -alkyl, phenyl or benzyl;

R ₇ and R ₈ are independently of each other hydrogen or C ₁ -C ₆ -alkyl;

m is 1, 2 or 3;

n is 0 or 1;

Substituted aminoheterocyclylamides with pesticidal activity are described, for example, in DE 197 27 162. However, the active ingredients specifically disclosed in this patent may not always meet the requirements regarding efficacy and activity spectrum. Therefore, there is a need for active ingredients with improved pesticidal properties. Finally, it has been found that the aminoheterocyclylamides of formula I have excellent pesticidal properties, in particular against parasites in the body.

Alkyl groups defined in substituent definitions may be straight or branched chains, for example methyl, ethyl, n-propyl, isopropyl, n-butyl, sec.-butyl, isobutyl, tert.-butyl, pentyl and hexyl, But not their branched chain isomers.

In general, halogen represents fluorine, chlorine, bromine or iodine. The same applies to halogen in combination with other meanings such as halogenalkyl or halogenphenyl.

Preferably, the halogenalkyl group has a chain length of 1 to 6 carbon atoms. As the halogen alkyl, for example, fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, 2,2,2-trifluoroethyl, 2-fluoroethyl, 2- Chloroethyl, pentafluoroethyl, 1,1-difluoro-2,2,2-trichloroethyl, 2,2,3,3-tetrafluoroethyl and 2,2,2-trichloroethyl; Preferred are trichloromethyl, difluorochloromethyl, difluoromethyl, trifluoromethyl and dichlorofluoromethyl.

Preferably, the alkoxy group has a chain length of 1 to 6 carbon atoms. Alkoxy includes, for example, methoxy, ethoxy, propoxy, isopropoxy, n-butoxy, isobutoxy, sec.-butoxy and tert.-butoxy, as well as pentyloxy and hexyloxy isomers; Preferred are methoxy and ethoxy.

R ₁ is halogen, C ₁ -C ₆ -alkyl, C ₁ -C ₆ -alkoxy, C ₁ -C ₆ -haloalkyl, or unsubstituted phenyl or C ₁ -C ₆ -alkyl, C ₁ -C ₆ -halo Phenyl mono- or missubstituted by a substituent selected from the group consisting of alkyl, C ₁ -C ₆ -alkoxy, aryloxy, halogen, cyano and nitro, wherein when the number of substituents is greater than 1, the substituents May be the same or different;

R ₂ is hydrogen, C ₁ -C ₆ -alkyl, (C ₁ -C ₆ -alkylene) phenyl or pyridyl;

X ₁ is N or C (CN);

X ₂ is N or C (CN);

X ₃ is O or S;

Q is CH or N;

R ₃ and R ₄ are independently of each other hydrogen, C ₁ -C ₆ -alkyl, or together with the C atom to which they are attached form a C ₃ -C ₇ -cycloalkyl ring;

R ₅ is a substituent selected from the group consisting of C ₁ -C ₆ -alkyl, C ₁ -C ₆ -haloalkyl, C ₁ -C ₆ -alkoxy, aryloxy, halogen, cyano, hydroxy, amino and nitro When the number of substituents is more than 1, the substituents may be the same or different from each other;

m is 1, 2 or 3;

Preferred are compounds of formula I, wherein n is 0 or 1.

It is particularly preferred that the compound of formula (I) comprises a substance of formula (Ia)

Wherein the substituents are defined as in formula (I).

Preferred embodiments of compounds of Formula (I) and Formula (Ia) are:

(1) a compound of formula I wherein X ₃ is O;

(2) R ₁ is halogen or C ₁ -C ₆ -haloalkyl; Preferably fluorine, chlorine or C ₁ -C ₄ -haloalkyl; More preferably chlorine or C ₁ -C ₂ -haloalkyl; Most preferably chlorine or trifluoromethyl;

(3) R ₂ is hydrogen or C ₁ -C ₆ -alkyl; Preferably hydrogen or C ₁ -C ₂ -alkyl; Most preferably hydrogen is a compound of formula (I);

(4) R ₃ and R ₄ are independently of each other hydrogen or C ₁ -C ₂ -alkyl, or together with the C atom to which they are attached form a C ₃ -C ₆ -cycloalkyl ring; Preferably hydrogen or together with the C atom to which they are attached form a C ₃ -C ₅ -cycloalkyl ring; Most preferably a compound of formula (I) which is hydrogen or forms together with the C atom to which they are attached a cyclopropyl ring;

(5) a compound of formula I wherein m is 1 or 2, preferably 2;

(6) a compound of Formula I wherein n is 0;

(7) R ₁ is halogen or C ₁ -C ₆ -haloalkyl; R ₂ is hydrogen or C ₁ -C ₆ -alkyl; R ₃ and R ₄ are independently of each other hydrogen, C ₁ -C ₂ -alkyl or together with the C atom to which they are attached form a C ₃ -C ₆ -cycloalkyl ring; m is 1 or 2; a compound of formula (I) wherein n is O;

(8) R ₁ is fluorine, chlorine or C ₁ -C ₄ -haloalkyl; R ₂ is hydrogen or C ₁ -C ₂ -alkyl; R ₃ and R ₄ are hydrogen or together with the C atom to which they are attached form a C ₃ -C ₅ -cycloalkyl ring; m is 2; a compound of formula (I) wherein n is 0; And

(9) R ₁ is chlorine or C ₁ -C ₂ -haloalkyl; R ₂ is hydrogen; R ₃ and R ₄ are hydrogen or together with the C atom to which they are attached form a cyclopropyl ring; m is 2; n is 0.

A further object of the present invention is to prepare compounds of the formula (II), which can be prepared analogously to known or corresponding known compounds, for example in the presence of a basic catalyst, similarly to known or corresponding known compounds. Reacting with a compound of formula III

If necessary, a compound of formula (I) or an enantiomer thereof obtainable according to the above method or by another method can be converted to another compound of formula (I) or an enantiomer thereof, and thus obtained of enantiomers. Mixtures are processes for the preparation of compounds of formula (I) and any enantiomers thereof, which separate to isolate the desired enantiomers.

Wherein R ₁ , R ₂ , X ₁ and X ₂ are defined as given for Formula I)

Wherein X ₃ , R ₃ , R ₄ , R ₅ , m, n and Q are defined as given for Formula I and Z is a leaving group

Suitable leaving groups are halogen, C ₁ -C ₆ -alkoxy or hydroxy, preferably chlorine.

Suitable bases for promoting the reaction are, for example, trialkylamines, basic heterocycles or phosphines. Triethylamine, diisopropylethylamine, pyridine, 4- (N, N-dimethylamino) pyridine, quinuclidin, 1,5-diazabicyclo [5.4.0] undec-5-ene (DBU) and Triphenylphosphine may be mentioned by way of example. Diisopropylethylamine is preferred.

The reactants can be reacted together by themselves or can be reacted, for example in a molten state, without the addition of a solvent or diluent. However, it is generally advantageous to add inert solvents or diluents, or mixtures thereof. Examples of such solvents or diluents which may be mentioned are aromatic, aliphatic and cycloaliphatic hydrocarbons and halogen-hydrocarbons such as benzene, toluene, xylene, mesitylene, tetralin, chlorobenzene, dichlorobenzene, bromobenzene, petroleum Ether, hexane, cyclohexane, dichloromethane, trichloromethane, tetrachloromethane, dichloroethane, trichloroethene or tetrachloroethene; Ethers such as diethyl ether, dipropyl ether, diisopropyl ether, dibutyl ether, tert.-butylmethyl ether, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol dimethyl ether, dimethoxydiethyl Ether, tetrahydrofuran or dioxane; Ketones such as acetone, methyl ethyl ketone or methyl isobutyl ketone; Amides such as N, N-dimethyl formamide, N, N-diethyl formamide, N, N-dimethyl acetamide, N-methyl-pyrrolidone or hexamethyl phosphate triamide; Nitriles such as acetonitrile or propionitrile; And sulfoxides such as dimethyl sulfoxide. When reacting in the presence of a base, a base such as triethylamine, pyridine, N-methylmorpholine or N, N-diethylamine can be used in excess as a solvent or diluent. Preference is given to halogen hydrocarbons, in particular dichloromethane.

The reaction is advantageously carried out at a temperature of about -20 ° C to about +150 ° C, preferably about -10 ° C to about +80 ° C, most preferably about 0 ° C to +40 ° C.

In a preferred embodiment, the compound of formula (II) is reacted with a compound of formula (III) in a halogen hydrocarbon, preferably dichloromethane, at 0 ° C. to 120 ° C., preferably at 20 ° C.

Compounds of formula (I) are asymmetric carbons, e.g., pure isomers such as enantiomers and / or diastereomers, or mixtures of isomers such as enantiomeric mixtures, for example racemates, diastereomeric mixtures or racemic mixtures. Depending on the number, absolute and relative arrangement of the atoms, they may exist as one form of a possible isomer or as a mixture thereof. The present invention relates to both the pure isomers and all possible isomeric mixtures, and will be understood by themselves above and below, although the stereochemical details are not specifically mentioned in each case.

Depending on the choice of starting materials and methods, the diastereomeric mixtures and racemic mixtures of the formula (I) obtained according to the invention or another method are known, for example based on the physico-chemical differences of the constituents, It can be separated into pure diastereomers or racemates by fractional crystallization, distillation and / or chromatography.

Mixtures of enantiomers such as racemates which can thus be obtained are carried out on known methods, for example on chiral sorbents such as recrystallization from optically active solvents and high performance liquid chromatography on acetyl cellulose (HPLC). By chromatography with an appropriate microorganism, by cleavage with a particular immobilization enzyme, for example through the formation of an inclusion compound using chiral crown ethers with only one enantiomer conjugated. have.

According to the invention, in addition to the isolation of the corresponding isomeric mixtures, generally known diastereoselective or enantioselective synthesis methods are also pure, for example by carrying out the process of the invention using the corresponding appropriate stereochemical extracts. It can be applied to obtain diastereomers or enantiomers.

It is advantageous to isolate or synthesize in each case biologically more active isomers, such as isomer mixtures such as enantiomers or enantiomeric mixtures, provided that each component exhibits biologically different efficacy.

In the process of the invention, it is preferred that the starting materials and intermediates used are derived from compounds of formula (I) which are described as particularly useful at the time of initiation.

The present invention specifically relates to the production method described in the Examples.

The starting materials and intermediates which are novel and used according to the invention for the preparation of the compounds of the formula (I), their use and their preparation methods likewise form the object of the invention.

The compounds of formula (I) according to the invention are notable for their broad spectrum of activity and are very useful active ingredients for controlling pests, including the control of in- and in vitro-parasites parasitic in animals, while warm-blooded animals, fish And plants have good resistance to this compound.

In the present invention, in vitro parasites mean particularly insects, mites and mites. This includes insects of the following order: Lepidoptera (Lepidoptera),Coleoptera (Coleoptera),Cicada (Homoptera),Stinkwood (Heteroptera),Fly (Diptera),Locust (Thysanoptera),Locust (Orthoptera),Eye (Anoplura), Flea (Siphonaptera), Shrub (Mallophaga), Moth (Thysanura), Termite (Isoptera), Trimmed beetle (Psocoptera) And Logging (Hymenoptera). However, in vitro parasites that may be mentioned are particularly pests that plague humans or animals and carry pathogens, such as flies, such as house flies. (Musca domestica), Musca Betustima (Musca vetustissima), Musca Outumnalis (Musca autumnalis), Princess HouseflyFannia canicularis), Sarcopaga Canary (Sarcophaga carnaria), Gold Fly (Lucilia cuprina), Cowhide Fly (Hypoderma bovis), Hippoderma Lineatum (Hypoderma lineatum), Chrysomia chloropiga (Chrysomyia chloropyga), Horsefly (Dermatobia hominis), Cocliomia Hominiborax (Cochliomyia hominivorax), Gasterophyllus instininalis (Gasterophilus intestinalis), Oestrus Orbis (Oestrus ovis), Chimpanzee (Stomoxys calcitrans), Haematovia iritans (Haematobia irritans), And small insects (mosquitoes (Nematocera)), For example mosquitoes (Culicidae), Matiaceae (Simuliidae), Moth fly family (Psychodidae) And also blood-sucking in vitro parasites such as fleas such as cat fleas (Ctenocephalides felis) And Dog flea (Ctenocephalides canis) (Cat and dog fleas), tropical rat fleas (Xenopsylla cheopis), Man fleaPulex irritans), Dermatophilus penetrance (Dermatophilus penetrans), Second-rate (lice), Such as Damalia Orbis (Damalina ovis), Pediculus Humanis (Pediculus humanis), Biting flies and horse flies (backTabanidae) ,, Haematopota species (Haematopota spp.), Such as Haematopota fluvialis (Haematopota pluvialis), Tabanidea species (Tabanidea spp.), Such as Tabanus nigrovitatus (Tabanus nigrovittatus), Species in ChrysovsinaChrysopsinae spp.), Chrysoffs Caequiens(Chrysops caecutiens), Somatic flies, such as the somatic fly (GlossiniaSpecies, biting insects, especially cockroaches such as German wheels (Blatella germanica), Oriental WheelsBlatta orientalis), American wheel (Periplaneta americana), Mites, such as Dermanisus Galinae (Dermanyssus gallinae), Borer nematodes (Sarcoptes scabiei), Psorotropes Orbis (Psoroptes ovis) And Psorregates species (Psorergates spp.), And finally ticks. The latter is mite (AcarinaBelongs to). Known representative ticks are, for example, buphilus (Boophilus), Ambly Sponge (Amblyomma), Anocentor (Anocentor), Skin mitesDermacentor), Haemapisalis (Haemaphysalis), Hyaloma (Hyalomma), Exodes (Ixodes), Lipisentor (Rhipicentor), Margalophus (Margaropus), Lipicephalus (Rhipicephalus), Long princess tickArgas), Autobius (Otobius) And princess ticksOrnithodoros) Etc., preferably farm animals, such as cattle, pigs, sheep and goats, poultry such as chickens, turkeys and geese, fur animals such as mink, fox, chinchillas, rabbits and the like, as well as domestic animals For example cats and dogs, and also those that invade humans.

In addition, compounds of formula (I) include hygiene pests, in particular Diptera of the family Sarcophagidae , Anophilidae and Culicidae ; Orthoptera , Dictyoptera (e.g., Blattidae ) and Hymenoptera (e.g., Formicidae ).

In addition, the compounds of formula (I) have sustained efficacy against parasitic mites and insects of plants. In the case of leaf Mites mites neck (spider mite), tetra Nikki di (Tetranychidae) (tetrahydro you kusu species (Tetranychus spp.) And wave say kusu species (Panonychus spp.)) Is effective against eggs, larvae and adults of .

The compounds fluke (sucking insect) of Hemiptera (Homoptera), in particular aphids and (Aphididae), myeolgugwa (Delphacidae), maemichung and (Cicadellidae), Wood Science (Psyllidae), a CD (Loccidae), pod beolregwa (Diaspididae) and Pests of the family Eriophydidae (eg, rust mite of citrus fruit); The Hemiptera (Hemiptera), norinjae Amok (Heteroptera) and thrips (Thysanoptera), and Lepidoptera (Lepidoptera), Coleoptera (Coleoptera), Diptera (Diptera) and grasshopper plants consume high activity against the insects of the neck (Orthoptera) Have

The compounds are similarly suitable as soil insecticides against pests in the soil.

Thus, the compounds of formula (I) are effective against all developmental stages of insect repellent and uptake on crops such as cereals, cotton, rice, corn, soybeans, potatoes, vegetables, fruits, tobacco, hops, citrus fruits, avocados and other crops.

In addition, the compounds of formula (I) are root-knot nematode and (Meloidogyne), ssiseu root nematodes and (Heterodera), root rot nematode and (Pratylenchus), stem nematodes and (Ditylenchus), any pole Ruth (Radopholus), Rhizopus glycidyl crispus (Rizoglyphus It is effective against plant nematodes such as species.

In particular, the compounds are characterized in that the parasitic nematodes in the body can cause serious diseases of mammals and poultry such as sheep, pigs, goats, cattle, horses, monkeys, dogs, cats, guinea-pigs and exotic algae. Effective against parasites. In the instruction a typical nematode himon kusu (Haemonchus), oriental shaped nematode (Trichostrongylus), agarose Termini that wichung (Ostertagia), hookworm (Nematodirus), Cooper-shaped nematode (Cooperia), roundworm (Ascaris), buno testosterone num (Bunostonum) , Oesophagostonum , Charbertia , Trichuris , Strongylus ,

All nematode (Trichonema), soepye charge (Dictyocaulus), Moses nematode (Capillaria), cecum charge (Heterakis), Toxoplasma collar (Toxocara), Asker Lydia (Ascaridia), oxy we switch (Oxyuris), anthelmintic (Ancylostoma), taste or Uncinaria , Toxascaris and Parascaris . A particular advantage of the compounds of formula (I) is that they are potent against these parasites that are resistant to the active ingredient based on benzimidazole.

Hookworm (Nematodirus), Cooper-shaped nematode (Cooperia) and Oe couch dwelling num (Oesophagostonum) specific pest species while invasive to the Minister of the host animal, himon Syracuse (Haemonchus) and the Austrian hotel that wichung (Ostertagia) other servants Pests are parasitic in the stomach , and pests of the species Dictyocaulus are parasitic in the lung tissue. Parasites of onchocerciasis (Filariidae) and bristles nematode (Setariidae) group can be found in the body tissues and organs such as heart, blood vessels, lymph vessels and subcutaneous tissue. Of particular interest is the parasite Dirofilaria immitis in dogs. Compounds of formula (I) are very effective against these parasites.

In addition, the compounds of formula (I) are particularly suitable for the control of human pathogenic parasites. Among them, typical pests appearing in the digestive tract include Ancylostoma , Necator , Ascaris , Strongyloides , Trichinella , Capillaria , and Beetle. Trichuris ), and pests of the Enterobius species. In addition, the compounds of the present invention is blood, tissue and bouquet from onchocerciasis (Filariidae) group shown in the various organs LES Liao (Wuchereria), Phrygia (Brugia), onko Sergio car (Onchocerca) and Loa (Loa) of parasites of the species, and It is particularly effective against parasites of Dracunculus , Strongyloides and Trichinella species that infect the gastrointestinal tract.

Good pesticidal activity of the compounds of formula (I) corresponds to a mortality of at least 50-60% against the pests mentioned. In particular, the compounds of formula (I) are noteworthy for their very long term efficacy.

The activity against animal pests of the compounds according to the invention and compositions containing them can be substantially broad and can be adapted to the general environment by the addition of other insecticides and / or acaricides. Said additives can be for example representatives of the following classes of active ingredients: organophosphorus compounds, nitrophenols and derivatives thereof, formamidine, urea, carbamate, pyrethroid, chlorinated hydrocarbons, neoniconinoids and bacillus Bacillus thuringiensis preparations.

The compounds of the formula (I) are preferably used in unmodified form or preferably in combination with auxiliaries commonly used in the field of formulation, and are therefore, for example, emulsifiable thickeners, direct sprayable or dilutable solutions, dilute emulsions. It can be processed by known methods to obtain microencapsulating agents in wettable powders, soluble powders, powders, granules or polymeric materials. Taking into account the properties of the composition, application methods such as spraying, atomizing, dusting, scattering or pouring are selected according to the intended purpose and general environment.

Preparations containing the active ingredient of formula (I), i.e. reagents, preparations or compositions, or combinations of these active ingredients with other agrochemically active ingredients and optionally solid or liquid auxiliaries, may be prepared by methods known per se, for example active ingredients. It may be prepared by a method of directly mixing and / or grinding with a diluent composition such as a solvent, a solid carrier and optionally a surfactant compound (surfactant).

The solvent is an aromatic hydrocarbon, preferably an alkylbenzene fraction of 8 to 12 carbon atoms, for example xylene mixtures or alkylated naphthalenes, aliphatic or cycloaliphatic hydrocarbons, for example cyclohexane, paraffin or tetrahydronaphthalene, alcohols, for example Ethanol, propanol or butanol, glycols and ethers and esters thereof, such as propylene glycol, dipropylene glycol ether, ethylene glycol or ethylene glycol mono-methyl or -ethyl ether, ketones such as cyclohexanone, isophorone or Diacetanol alcohols, strong polar solvents such as N-methyl-2-pyrrolidone, dimethyl sulfoxide or dimethylformamide, or water, vegetable oils such as rape oil, castor oil, coconut oil Or soybean oil, and, if appropriate, silicone oil.

For example, solid carriers used for powders and dispersible powders generally include natural fillers such as calcite, talc, kaolin, montmorillonite or attapulgite. In addition, highly dispersed silicic acid or highly dispersed absorbent polymers may be added to improve physical properties. Suitable granulated adsorptive carriers are in porous form, such as pumice, masonry, pulverulite or bentonite, and suitable non-adsorbent carriers are materials such as calcite or sand. In addition, various inorganic or organic pregranulated materials, for example dolomite or ground plant residues, may be used.

Depending on the type of active ingredient of formula (I) to be formulated or the combination of these active ingredients with other insecticides or acaricides, suitable surface active compounds include, but are not limited to, nonionic, cationic and / or good emulsifying, dispersing and wetting properties. Anionic surfactants. Surfactants are also understood as surfactant mixtures.

Suitable anionic surfactants can be both so-called water soluble soaps and water soluble synthetic surfactant compounds.

Suitable soaps include alkali metal salts, alkaline earth metal salts, unsubstituted or substituted ammonium salts of high fatty acids (C ₁₀ -C ₂₂ ), for example sodium or potassium salts of oleic or stearic acid, or for example from coconut or resin oils. Sodium or potassium salts of natural fatty acid mixtures. In addition, fatty acid methyltaurine salts may be used as surfactants.

However, so-called synthetic surfactants, in particular fatty sulfonates, fatty sulfates, sulfonated benzimidazole derivatives or alkylarylsulfonates are more often used.

Fatty sulfonates or sulfates are usually in the form of alkali metal salts, alkaline earth metal salts, unsubstituted ammonium salts or substituted ammonium salts and comprise alkyl radicals having 8 to 22 carbon atoms and are alkyl residues of acyl radicals, for example lignin Sodium or calcium salts of sulfonic acid or dodecyl sulfate, or sodium or calcium salts of fatty alcohol sulfate mixtures obtained from natural fatty acids. These compounds also include the sulfuric acid esters of fatty alcohol / ethylene oxide addition products and salts of sulfonic acids. The sulfonated benzimidazole derivative preferably contains two sulfonic acid groups and one fatty acid radical having 8 to 22 carbon atoms. Examples of alkylarylsulfonates are the sodium, calcium or triethanolamine salts of dodecylbenzenesulfonic acid, dibutylnaphthalenesulfonic acid, or naphthalenesulfonic acid / formaldehyde condensation products. Also suitable are salts of the corresponding phosphate salts, such as p-nonylphenol and the addition product of 4 to 14 moles of ethylene oxide or phospholipid.

Preferred nonionic surfactants are aliphatic alcohols, cycloaliphatic alcohols, polyglycol ether derivatives of saturated fatty acids or unsaturated fatty acids and alkylphenols, wherein the derivatives comprise from 3 to 30 glycol ether groups and 8 to (aliphatic) hydrocarbon moieties. There are from 20 to 20 carbon atoms and there are from 6 to 18 carbon atoms in the alkyl moiety of the alkylphenol. Other suitable nonionic surfactants include water soluble addition products of polyethylene oxide and polypropylene glycol, ethylenediamine polypropylene glycol and alkylpolypropylene glycols, wherein there are 1 to 10 carbon atoms in the alkyl chain. Comprises 20 to 250 ethylene glycol ether groups and 10 to 100 propylene glycol ether groups. These compounds usually contain 1 to 5 ethylene glycol units per one propylene glycol unit.

Examples of nonionic surfactants are nonylphenolpolyethoxyethanol, castor oil polyglycol ether, polypropylene / polyethylene oxide adducts, tributylphenoxypolyethoxyethanol, polyethylene glycol and octylphenoxypolyethoxyethanol. Also suitable are fatty acid esters of polyoxyethylene sorbitan such as polyoxyethylene sorbitan trioleate.

Preferred cationic surfactants are quaternary ammonium salts comprising one or more C ₈ -C ₂₂ alkyl radicals as N-substituents and halogenated lower alkyl, benzyl or lower hydroxyalkyl radicals (as the case may be) as other substituents. . This salt is preferably present as halide, methylsulfate or ethylsulfate, preferably stearyl trimethylammonium chloride and benzyl-di (2-chloroethyl) -ethylammonium bromide.

Surfactants conventional in formulation technology are described by way of example in the following publications.

"Mc Cutcheon's Detergents and Emulsifiers Annual", McPublishing Corp., Glen Rock, NJ, USA, 1988 ",

H. Stache, "Tensid-Taschenbuch" (Surfactants Handbook), 2 ^nd edition, C. Hanser Publishing Munich, Vienna 1981.

M. and J. Ash. "Encyclopedia of Surfactants", Vol. I-III, Chemical Publishing Co., New York, 1980-1981.

Preferred application forms for use on warm-blooded animals in the control of enteric parasites include solutions, emulsions, suspensions (drenches), food additives, powders, tablets (including effervescent tablets), bolli (boli), capsules, microcapsules and pour-on formulations, whereby the physiological compatibility of the formulation excipients should be considered.

Binders for tablets and boli are chemically modified polymeric natural materials that are soluble in water or alcohols such as starch, cellulose or protein derivatives (e.g. methyl cellulose, carboxymethyl cellulose, ethyl hydroxyethyl Cellulose, proteins such as zein, gelatin and the like), as well as synthetic polymers such as polyvinyl alcohol, polyvinyl pyrrolidone and the like. In addition, tablets contain fillers (eg, starch, microcrystalline cellulose, sugars, lactose, etc.), glidants, and disintegrants.

If an anthelminthic is present in the form of a food thickener, the carrier used is, for example, a performance feed, feed grain or protein concentrate. Such feed concentrates or compositions, together with the active ingredient, also contain additives, vitamins, antibiotics, chemotherapeutic agents or other pesticides, mainly bacteriostats, fungistats, anticoccidiostats, or hormonal preparations. , Substances having an assimilation action, or promoting growth, affecting the meat quality of slaughter animals, or in another way may contain substances beneficial to the organism. When the composition or the active ingredient of formula (I) contained therein is added directly to the feed or beverage container, the formulated feed or drink preferably contains the active ingredient at a concentration of about 0.0005 to 0.02% by weight (5 to 200 ppm). Do.

The composition according to the invention is administered topically, orally, parenterally or subcutaneously to the animal to be treated, wherein the composition is a solution, an emulsion, a suspension, (drenches for use), powders, tablets, bowls, capsules. Present in the form of formulations and pour-on formulations.

The compounds of formula (I) according to the invention can be used alone or in combination with other pesticides. The compounds of the present invention may increase the activity, for example by combining with pesticides having the same activity range, or by combining with substances with different activity ranges, for example. It may also be desirable to add so-called insect repellents. If the range of activity is to be extended to parasites in the body (such as parasitic agents), the compounds of formula (I) are suitably combined with substances which exhibit parasitic resistance to parasites in the body. Of course, the compounds of formula (I) can also be used in combination with antimicrobial compositions. Since the compounds of formula (I) are biocidal agents, ie they are particularly effective against the adult stage of the target parasite, it may be very advantageous to add the pesticide to the larval stage of the parasite. In this way, the majority of parasites with very large economic losses will be controlled. This action will also contribute substantially to avoiding the formation of resistance. In addition, various combinations can lead to a synergistic effect, i.e. a reduction in the total amount of active ingredient, which is desirable from an economic point of view. A preferred group of blending partners and particularly preferred blending partners is named below and accordingly the blend may contain one or more of these partners together with the compound of formula (I).

Suitable partners in the mixtures include pesticides known to those skilled in the art for a long time, such as insecticides and acaricides which have a variety of active mechanisms, such as chitin synthesis inhibitors, growth regulators, named below; Active ingredients that act as larval hormones; Active ingredient which acts as an insecticide; Wide range of insecticides, wide range of acaricides and nematicides; And well-known insect repellent and insect- and / or mite-repelling substances, such insect repellents or desorbers.

Non-limiting examples of suitable insecticides and acaricides are as follows:

(I) aldicarbs; (II) azineforce-methyl; (III) benpuracarb; (IV) bifenthrin; (V) buprofezin; (VI) carbofuran; (VII) dibutylaminothio; (VII) cartab; (IX) chlorfluazuron; (X) chlorpyrifoss; (XI) cyfluthrin; (XII) lambda-sihalothrin; (XIII) alpha = cifermethrin; (XIV) zeta-cifermethrin; (XV) deltamethrin; (XVI) diflubenzuron; (XVII) endosulfan; (XVIII) thiophencarb; (XIX) phenythrothione; (XX) phenobucarb; (XXI) penvalerate; (XXII) formothione; (XXIII) methiocarb; (XXIV) heptenophos; (XXV) imidacloprid; (XXVI) isoprocarb; (XXVII) metamidose; (XXVIII) metomil; (XXIX) mevinforce; (XXX) parathion; (XXXI) parathion-methyl; (XXXII) posalon; (XXXIII) pyricarb; (XXXIV) propoxur; (XXXV) teflubenzuron; (XXXVI) terbufoss; (XXXVII) triamate; (XXXVIII) abamectin; (XXXIX) phenobucarb; (XL) tebufenozide; (XLI) fipronil; (XLII) beta-cifluthrin; (XLIII) silaflofen; (XLIV) fenpyroximate; (XLV) pyridaben; (LI) avermectin B ₁ ; (XLVI) penazaquin; (XLVII) pyriproxyfen; (XLVIII) pyrimidifene; (XLIX) nitenpyram; (L) NI-25, acetamiprid; (LII) avermectin B ₁ ; (LIII) insect-active extracts from plants; (LIV) agents containing insect-active nematodes; (LV) preparations obtained from Bacillus subtilis ; (LVI) agents containing insect-active fungi; (LVII) agents containing insect-active viruses; (LIX) AC 303 630; (LX) acepart; (LXI) acrinatrin; (LXII) alaniccarb; (LXIII) alphamethrin; (LXIV) amitraz; (LXV) AZ 60541; (LXVI) azineforce A; (LXVII) azineforce M; (LXVIII) azocyclotin; (LXIX) bendiocarb; (LXX) bensultab; (LXXI) betafluflurin; (LXXII) BPMC; (LXXIII) brofenprox; (LXXIV) bromophos A; (LXXV) bufencarb; (LXXVI) butocarcinine; (LXXVII) butylpyridaben; (LXXVIII) cardusaphas; (LXXIX) carbaryl; (LXXX) carbophenothione; (LXXXI) clotocarb; (LXXXII) cloethoxyforce; (LXXXIII) chlormefoss; (LXXXIV) cis-resmethrin; (LXXXV) clocitrin; (LXXXVI) clofentezin; (LXXXVII) cyanoforce; (LXXXVIII) cycloprotrin; (LXXXIX) cyhexatin; (XC) demethone M; (XCI) demethone S; (XCII) demethone-S methyl; (XCIII) diclopentione; (XCIV) Diclifoss; (XCV) diethion; (XCVI) dimethatoart; (XCVII) dimethyl bean force; (XCVIII) dioxathione; (XCIX) edifeneforce; (C) emamectin; (CI) espenvalerie; (CII) ethion; (CIII) etofenprox; (CIV) etoproforce; (CV) etrimforce; (CVI) phenamifoss; (CVII) fenbutatinoxide; (CVIII) phenothiocarb; (CIX) phenpropatrine; (CX) fenpyrad; (CXI) pention; (CXII) fluazinam; (CXIII) flucycloxon; (CXIV) flucitrinat; (CXV) flufenoxuron; (CXVI) flufenprox; (CXVII) phonophos; (CXVIII) phosphiazat; (CXIX) pufenfenrox; (CXX) HCH; (CXXI) hexaflumuron; (CXXII) hexiazox; (CXXIII) Ifprobenfoss; (CXXIV) isopenfoss; (CXXV) isoxation; (CXXVI) ivermectin; (CXXVII) lambda sihalothrin; (CXXVIII) malathion; (CXXIX) mecarbam; (CXXX) mesulfenforce; (CXXXI) metaldehyde; (CXXXII) metolcarb; (CXXXIII) milbemectin; (CXXXIV) moxidecin; (CXXXV) nal red; (CXXXVI) NC 184; (CXXXVII) ometoart; (CXXXVIII) oxamil; (CXXXIX) oxydemethone M; (CXL) Oxidedefoss; (CXLI) permethrin; (CXLII) pentoart; (CXLIII) forrat; (CXLIV) phosmet; (CXLV) bombardment; (CXLVI) pyrimifos M; (CXLVII) pyrimifos A; (CXLVIII) promecarb; (CXLIX) propaphos; (CL) prothioforce; (CLI) protoart; (CLII) pyraclophos; (CLIII) pyrada-pention; (CLIV) pyresmethrin; (CLV) pyrethium; (CLVI) RH 5992; (CLVII) salityone; (CLVIII) Cebu Force; (CLIX) sulfotep; (CLX) sulfpropos; (CLXI) tebufenpyrad; (CLXII) tebupyrimphos; (CLXIII) tefluthrin; (CLXIV) temefoss; (CLXV) terbam; (CLXVI) tetrachlorbinforce; (CLXVII) thiaphenox; (CLXVIII) thiodicarb; (CLXIX) thiophanox; (CLXX) thionazine; (CLXXI) thuringiensin; (CLXXII) tralomethrin; (CLXXIII) triartene; (CLXXIV) triazofoss; (CLXXV) triazurone; (CLXXVI) trichlorphone; (CLXXVII) triflumuron; (CLXXVIII) trimetacarb; (CLXXIX) bhammithion; (CLXXX) xylylcarb; (CLXXXI) YI 5301/5302; (CLXXXII) zetamethrin; (CLXXXIII) DPX-MP062; (CLXXXIV) RH-2485; (CLXXXV) D 2341; (CLXXXVI) XMC (3,5, -xylylmethylcarbamat); (CLXXXVII) loufenuron; (CLXXXVIII) fluazuron; (CLXXXIX) metoprene; (CXC) hydroprene; (CXCI) phenoxycarb; (CXCII) chlorfenapyr; Or (CXCIII) spinosad.

Non-limiting examples of suitable antiparasitic agents are described below, some of which also exhibit insecticidal and acaricidal activity in addition to parasitic activity, and some are already on the list.

(A1) prajikuantel = 2-cyclohexylcarbonyl-4-oxo-1,2,3,6,7,11 b-hexahydro-4H-pyrazino [2,1-α] isoquinoline

(A2) Chloxanthel = 3,5-diiodo-N- [5-chloro-2-methyl-4- (α-cyano-4-chlorbenzyl) phenyl] salicyamide

(A3) triclabendazole = 5-chloro-6- (2,3-dichlorphenoxy) -2-methylthio-1H-benzimidazole

(A4) levamisol = L-(-)-2,3,5,6-tetrahydro-6-phenylimidazo [2,1b] thiazole

(A5) mebendazole = (5-benzoyl-1H-benzimidazol-2-yl) carbamic acid methyl ester

(A6) Ompalotin = macrocyclic fermentation product of the Omphalotus olearius fungus described in WO 97/20857

(A7) Abamectin = Avemectin B1

(A8) ivermectin = 22,23-dihydroavermectin B1

(A9) moxidecin = 5-0-demethyl-28-deoxy-25- (1,3-dimethyl-1-butenyl) -6,28-epoxy-23- (methoxyimino) -milbemycin B

(A10) Doramectin = 25-cyclohexyl-5-O-demethyl-25-de (1-methylpropyl) -avermectin A1a

(A11) Milvemectin = mixture of Milbemic Acid A3 and Milbemycin A4

(A12) Milbemycinoxime = 5-oxime of Milvemectin

Non-limiting examples of suitable insect repellents and desorbents include (R1) DEET (N, N-diethyl-m-toluamide), (R2) KBR 3023 N-butyl-2-oxycarbonyl- (2-hydroxy) -Piperidine or (R3) cymiazole = N, -2,3-dihydro-3-methyl-1,3-thiazole-2-ylidene-2,4-xylidene.

The partners in the mixtures are best known to the expert in this field. Most of them are listed in several revisions of the Pesticide Manual, The British Crop Protection Council, London, and the rest are several revisions of The Merck Index, Merck & Co., Inc., Rahway, New Jersy, USA. Or in the patent literature. Thus, the following list is limited to some cases that may be presented by way of example.

(I) 2-methyl-2- (methylthio) propionaldehyde- O -methylcarbamoyloxime (Aldicarb) (Pesticide Manual, 11 Ed. (1997), The British Crop Protection Council, London, page 26) ;

(II) S- (3,4-Dihydro-4-oxobenzo [ d ]-[1,2,3] -triazin-3-ylmethyl) O, O -dimethyl-phosphorodithioate (azine Phosph-methyl) (The Pesticide Manual, 11th Ed. (1997), The British Crop Protection Council, London, page 67);

(III) ethyl-N- [2,3-dihydro-2,2-dimethylbenzofuran-7-yloxycarbonyl- (methyl) aminothio] -N-isopropyl-β-alanineate (benfura Carb) (The Pesticide Manual, 11th Ed. (1997), The British Crop Protection Council, London, page 96);

(IV) 2-methylbiphenyl-3-ylmethyl- ( Z )-(1 RS ) -cis-3- (2-chloro-3,3,3-trifluoroprop-1-enyl) -2, 2-dimethylcyclopropanecarboxylate (bifenthrin) (The Pesticide Manual, 11th Ed. (1997), The British Crop Protection Council, London, page 118);

(V) 2-tert-butylimino-3-isopropyl-5-phenyl-1,3,5-thiadiazin-4-one (buprofezin) (The Pesticide Manual, 11th Ed. (1997), The British Crop Protection Council, London, page 157);

(VI) 2,3-dihydro-2,2-dimethylbenzofuran-7-yl-methylcarbamate (carbofuran) (The Pesticide Manual, 11th Ed. (1997), The British Crop Protection Council, London, page 186);

(VII) 2,3-dihydro-2,2-dimethylbenzofuran-7-yl- (dibutylaminothio) methylcarbamate (carbosulphan) (The Pesticide Manual, 11th Ed. (1997), The British Crop Protection Council, London, page 188);

(VIII) S, S- (2-dimethylaminotrimethylene) -bis (thiocarbamate) (cartab) (The Pesticide Manual, 11th Ed. (1997), The British Crop Protection Council, London, page 193);

(IX) 1- [3,5-Dichloro-4- (3-chloro-5-trifluoromethyl-2-pyridyloxy) phenyl] -3- (2,6-difluorobenzoyl) -urea ( Chlorfluazuron) (The Pesticide Manual, 11 th Ed. (1997), The British Crop Protection Council, London, page 213);

(X) O, O -diethyl- O- 3,5,6-trichloro-2-pyridyl-phosphorothioate (chlorpyriphos) (The Pesticide Manual, 11th Ed. (1997), The British Crop Protection Council, London, page 235);

(XI) ( RS ) -α-cyano-4-fluoro-3-phenoxybenzyl- (1 RS , 3 RS ; 1 RS , 3 RS ) -3- (2,2-dichlorovinyl) -2 , 2-di-methylcyclopropanecarboxylate (cifluthrin) (The Pesticide Manual, 11th Ed. (1997), The British Crop Protection Council, London, page 293);

(XII) (S) -α-cyano-3-phenoxybenzyl- ( Z )-(1 R , 3 R ) -3- (2-chloro-3,3,3-trifluoropropenyl)- 2,2-dimethylcyclopropanecarboxylate and ( R ) -α-cyano-3-phenoxybenzyl- ( Z )-(1 R , 3 R ) -3- (2-chloro-3,3,3 A mixture of -trifluoropropenyl) -2,2-dimethylcyclopropanecarboxylate (lambda hahalthrin) (Pesticide Manual, 11th Ed. (1997), The British Crop Protection Council, London, page 300);

(XIII) ( S ) -α-cyano-3-phenoxybenzyl- (1 R , 3 R ) -3- (2,2-dichlorovinyl) -2,2-dimethylcyclopropanecarboxylate and ( R racemate composed of) -a-cyano-3-phenoxybenzyl- (1 S , 3 S ) -3- (2,2-dichlorovinyl) -2,2-dimethylcyclopropanecarboxylate (alpha- Cipermethrin) (Pesticide Manual, 11th Ed. (1997), The British Crop Protection Council, London, page 308);

(XIV) ( S ) -α-cyano-3-phenoxybenzyl (1 RS , 3 RS , 1 RS , 3 RS ) -3- (2,2-dichlorovinyl) -2,2-dimethylcyclopropanecar Stereoisomeric mixtures of carboxylates (zeta-cifermethrin) (The Pesticide Manual, 11th Ed. (1997), The British Crop Protection Council, London, page 314);

(XV) ( S ) -α-cyano-3-phenoxybenzyl- (1 R , 3 R) -3- (2,2-dibromovinyl) -2,2-dimethylcyclopropanecarboxylate ( Deltamethrin) (The Pesticide Manual, 11th Ed. (1997), The British Crop Protection Council, London, page 344);

(XVI) (4-chlorophenyl) -3- (2,6-difluorobenzoyl) urea (diflubenzuron) (The Pesticide Manual, 11 th Ed. (1997), The British Crop Protection Council, London, page 395 );

(XVII) (1,4,5,6,7,7-hexachloro-8,9-10-trinorborn-5-ene-2,3-ylenebismethylene) -sulfite (endosulfan) (The Pesticide Manual, 11th Ed. (1997), The British Crop Protection Council, London, page 459;

(XVIII) α-ethylthio-o-tolyl-methylcarbamate (ethiophencarb) (The Pesticide Manual, 11th Ed. (1997), The British Crop Protection Council, London, page 479);

(XIX) O, O -Dimethyl- O -4-nitro- m -tolyl-phosphothioate (phenythiion) (The Pesticide Manual, 11th Ed. (1997), The British Crop Protection Council, London, page 514 );

(XX) 2- sec -butylphenyl-methylcarbamate (phenobucarb) (The Pesticide Manual, 11th Ed. (1997), The British Crop Protection Council, London, page 516);

(XXI) ( RS ) -α-cyano-3-phenoxybenzyl- ( RS ) -2- (4-chlorophenyl) -3-methylbutyrate (fenvallate) (The Pesticide Manual, 11th Ed. (1997) ), The British Crop Protection Council, London, page 539);

(XXII) S- [formyl (methyl) carbamoylmethyl] -O, O -dimethyl-phosphorodithioate (formomones) (The Pesticide Manual, 11th Ed. (1997), The British Crop Protection Council , London, page 625;

(XXIII) 4-methylthio-3,5-xylyl-methylcarbamate (methiocarb) (The Pesticide Manual, 11th Ed. (1997), The British Crop Protection Council, London, page 813);

(XXIV) 7-chlorobicyclo [3.2.0] hepta-2,6-diene-6-yl-dimethylphosphate (heptenoforce) (The Pesticide Manual, 11th Ed. (1997), The British Crop Protection Council, London, page 670;

(XXV) 1- (6-chloro-3-pyridylmethyl) -N -nitroimidazolidin-2-ylideneamine (imidacloprid) (The Pesticide Manual, 11th Ed. (1997), The British Crop Protection Council , London, page 706;

(XXVI) 2-isopropylphenyl-methylcarbamate (isoprocarb) (The Pesticide Manual, 11th Ed. (1997), The British Crop Protection Council, London, page 729);

(XXVII) O, S -dimethyl-phosphoramidothioate (methamidophos) (The Pesticide Manual, 11th Ed. (1997), The British Crop Protection Council, London, page 808);

(XXVIII) S -methyl- N- (methylcarbamoyloxy) thioacetimidate (methomyl) (The Pesticide Manual, 11th Ed. (1997), The British Crop Protection Council, London, page 815);

(XXIX) methyl-3- (dimethoxyphosphinoyloxy) but-2-enoate (melvinforce) (The Pesticide Manual, 11th Ed. (1997), The British Crop Protection Council, London, page 844);

(XXX) O, O -diethyl- 0-4 -nitrophenyl-phosphothioate (parathion) (The Pesticide Manual, 11th Ed. (1997), The British Crop Protection Council, London, page 926);

(XXXI) O, O -Dimethyl- O -4-nitrophenyl-phosphothioate (parathion-methyl) (The Pesticide Manual, 11th Ed. (1997), The British Crop Protection Council, London, page 928);

(XXXII) S -6-Chloro-2,3-dihydro-2-oxo-1,3-benzoxazol-3-ylmethyl- O, O -diethyl-phosphodithioate (phosphalone) (The Pesticide Manual, 11th Ed. (1997), The British Crop Protection Council, London, page 963);

(XXXIII) 2-dimethylamino-5,6-dimethylpyrimidin-4-yl-dimethylcarbamate (pyricarb) (The Pesticide Manual, 11th Ed. (1997), The British Crop Protection Council, London, page 985);

(XXXIV) 2-isopropoxyphenyl-methylcarbamate (propoxy) (The Pesticide Manual, 11th Ed. (1997), The British Crop Protection Council, London, page 1036);

(XXXV) 1- (3,5-dichloro-2,4-difluorophenyl) -3- (2,6-difluorobenzoyl) urea (teflubenzuron) (The Pesticide Manual, 11th Ed. 1997), The British Crop Protection Council, London, page 1158;

(XXXVI) S -tert-Butylthiomethyl- O, O -dimethyl-phosphorodithioate (terbufos) (The Pesticide Manual, 11th Ed. (1997), The British Crop Protection Council, London, page 1165) ;

(XXXVII) ethyl- (3-tert-butyl-1-dimethylcarbamoyl-1 H -1,2,4-triazol-5-yl-thio) -acetate (triamate) (The Pesticide Manual, 11th Ed. (1997), The British Crop Protection Council, London, page 1224;

(XXXVIII) Avermectin (The Pesticide Manual, 11th Ed. (1997), The British Crop Protection Council, London, page 3);

(XXXIX) 2-sec-butylphenyl-methylcarbamate (phenobucarb) (The Pesticide Manual, 11th Ed. (1997), The British Crop Protection Council, London, page 516);

(XL) N -tert-butyl- N- (4-ethylbenzoyl) -3,5-dimethylbenzohydrazide (tebufenozide) (The Pesticide Manual, 11th Ed. (1997), The British Crop Protection Council, London, page 1147);

(XLI) (±) -5-amino-1- (2,6-dichloro-α, α, α-trifluoro-p-tolyl) -4-trifluoromethyl-sulfinylpyrazole-3-carboni Tril (fipronil) (The Pesticide Manual, 11th Ed. (1997), The British Crop Protection Council, London, page 545);

(XLII) ( RS ) -α-cyano-4-fluoro-3-phenoxybenzyl (1 RS , 3 RS ; 1 RS , 3 RS ) -3- (2,2-dichlorovinyl) -2,2 -Dimethylcyclopropanecarboxylate (beta-cifluthrin) (The Pesticide Manual, 11th Ed. (1997), The British Crop Protection Council, London, page 295);

(XLIII) (4-ethoxyphenyl)-[3- (4-fluoro-3-phenoxyphenyl) propyl] (dimethyl) silane (silafluorene) (The Pesticide Manual, 11th Ed. (1997), The British Crop Protection Council, London, page 1105);

(XLIV) tert-Butyl ( E ) -α- (1,3-dimethyl-5-phenoxypyrazol-4-yl-methyleneamino-oxy) -p-toluate (penpyroximate) (The Pesticide Manual, 11th Ed. (1997), The British Crop Protection Council, London, page 530;

(XLV) 2-tert-butyl-5- (4-tert-butylbenzylthio) -4-chloropyridazine-3 ( 2H ) -one (pyridaben) (The Pesticide Manual, 11th Ed. (1997), The British Crop Protection Council, London, page 1161);

(XLVI) 4-[[4- (1,1-dimethylphenyl) phenyl] ethoxy] -quinazolin (phenazquin) (The Pesticide Manual, 11th Ed. (1997), The British Crop Protection Council, London, page 507);

(XLVII) 4-phenoxyphenyl- ( RS ) -2- (pyridyloxy) propyl-ether (pyriproxyfen) (The Pesticide Manual, 11th Ed. (1997), The British Crop Protection Council, London, page 1073 );

(XLVIII) 5-chloro- N- {2- [4- (2-ethoxyethyl) -2,3-dimethylphenoxy] ethyl} -6-ethylpyrimidin-4-amine (pyrimidipene) Pesticide Manual, 11th Ed. (1997), The British Crop Protection Council, London, page 1070);

(XLIX) (E) - N - (6- chloro-3-pyridylmethyl) - N - ethyl - N - methyl-2-nitro-vinylidene-diamine (niten piram) (The Pesticide Manual, 11th Ed (1997). , The British Crop Protection Council, London, page 880;

(L) ( E ) -N ¹ -[(6-chloro-3-pyridyl) methyl] -N ² -cyano- N ¹ -methylacetamidine (NI-25, acetamiprid) (The Pesticide Manual , 11th Ed. (1997), The British Crop Protection Council, London, page 9);

(LI) Avermectin B ₁ (The Pesticide Manual, 11th Ed. (1997), The British Crop Protection Council, London, page 3);

(LII) insect-active extracts from plants, in particular (2 R , 6 aS , 12 aS ) -1,2,6,6a, 12,12a-hexhydro-2-isopropenyl-8,9-dimethoxy The Pesticide Manual, 11th Ed. (1997), The British Crop Protection Council, London, page 1097 -Chromeno [3,4-b] furo [2,3-h] chromen-6-one (rotenone) ); And extracts from Azadirachta indica, in particular Azadirachtin (The Pesticide Manual, 11th Ed. (1997), The British Crop Protection Council, London, page 59); And

(LIII) insect-active nematodes, preferably Heterorhabditis bacterophora and Heterorhabditis megidis (The British Crop Protection Council, London, page 671), Stenemema Peltier Preparations containing Steinemema feltiae (The British Crop Protection Council, London, page 1115) and Steinemema scapterisci (The British Crop Protection Council, London, page 1166);

(LIV) Bacillus subtilis (The Pesticide Manual, 11th Ed. (1997), The British Crop Protection Council, London, page 72), except for compounds isolated from GC91 or NCTC11821; Or agents obtainable from strains of Bacillus thuringiensis (The Pesticide Manual, 11th Ed. (1997), The British Crop Protection Council, London, page 73);

(LV) insect-active fungi, preferably Verticillium lecanii (The Pesticide Manual, 11th Ed. (1997), The British Crop Protection Council, London, page 1266; Beauveria brogniartii ) (The Pesticide Manual, 11th Ed. (1997), The British Crop Protection Council, London, page 85); and Beauveria bassiana (The Pesticide Manual, 11th Ed. (1997), The Preparations containing the British Crop Protection Council, London, page 83);

(LVI) insect-active virus, preferably Neodipridon Sertifer NPV (The Pesticide Manual, 11th Ed. (1997), The British Crop Protection Council, London, page 1342); Mamestra brassicae NPV (The Pesticide Manual, 11 th Ed. (1997), The British Crop Protection Council, London, page 759; and Cydia pomonella granulosis virus) (The Pesticide Manual, 11 th Ed. (1997), The British Crop Protection Council, London, page 291);

(CLXXXI) 7-chloro-2,3,4a, 5-tetrahydro-2- [methoxycarbonyl (4-trifluoromethoxyphenyl) -carbamoyl] indole [1,2 e ] oxazoline-4 a -carboxylate (DPX-MP062, indoxicarb) (The Pesticide Manual, 11th Ed. (1997), The British Crop Protection Council, London, page 453);

(CLXXXII) N -tert-butyl- N ' -(3,5-dimethylbenzoyl) -3-methoxy-2-methylbenzohydrazide (RH 2485, methoxyphenozide) (The Pesticide Manual, 11th Ed. (1997), The British Crop Protection Council, London, page 1094; And

(CLXXXIII) ( N ′ -[4-methoxy-biphenyl-3-yl] -hydrazinecarboxylic acid isopropyl ester (D 2341) (Brighton Crop Protection Conference, 1996, 487-493);

(R2) Abstract (212th ACS National Meeting Orlando, FL, August 25-29 (1996), AGRO-020. Publisher: American Chemical Society, Washington, D. C. CONEN: 63BFAF).

In summary, the other essential aspect of the present invention is characterized in that it comprises a compound of formula (I), containing at least one additional active ingredient having the same or the same range of activity and at least one physiologically acceptable carrier, A combination formulation for controlling parasitic parasites in warm-blooded animals. The present invention is not limited to a blend of the two.

In general, the insect repellent composition according to the invention comprises from 0.1 to 99% by weight, in particular from 0.1 to 95% by weight, and from 0 to 25% by weight of surfactant, in particular from 0.1 to 25% by weight of the active ingredient It contains 99.9 to 1% by weight, in particular 99.8 to 5% by weight of a solid or liquid mixture.

The pour-on or spot-on method consists of applying the compound of formula (I) to a specific location on the skin or fur, or advantageously, on the neck or spine of the animal. This is for example a cotton swab or spray application of a pour-on or spot-on formulation in a relatively narrow area of the skin and, due to the scattering properties of the formulation components and the help of animal behavior, the active substance can be applied from a relatively small area of the skin to Mostly distributed over automatically.

Pour-on or spot-on formulations suitably contain a carrier which promotes rapid dispersion on the skin surface of the host animal or in the shell and is generally regarded as a spreading oil. Suitable carriers include, for example, oily solutions; Alcoholic and isopropanolic solutions such as 2-octyldodecanol or oleyl alcohol; Esters of monocarboxylic acids of saturated fatty alcohols of chain length C ₁₂ -C ₁₈ , for example isopropyl myristate, isopropyl palmitate, lauric oxalate, oleic oleyl ester, oleic decyl ester, hexyl laurate , Solutions of oleyl oleate, decyl oleate, capric acid esters; Esters of dicarboxylic acids, such as dibutyl phthalate, diisopropyl isophthalate, adipic acid diisopropyl ester, solutions of di-n-butyl adipate or ester solutions of aliphatic acids, for example glycols . It may be advantageous to add dispersants such as those known in the pharmaceutical or cosmetic industry. Examples are 2-pyrrolidone, 2- (N-alkyl) pyrrolidone, acetone, polyethylene glycols, and ethers and esters thereof, propylene glycol or synthetic triglycerides.

Oily solutions include, for example, vegetable oils such as olive oil, peanut oil, sesame oil, sol oil, linseed oil or castor oil. In addition, vegetable oils may be present in epoxidized form. Paraffin and silicone oils can also be used.

Pour-on or spot-on formulations generally comprise 1 to 20% by weight of the compound of formula (I), 0.1 to 50% by weight of dispersant and 45 to 98.9% by weight of solvent.

The pour-on or spot-on method is particularly advantageous for use on livestock such as cattle, horses, sheep or pigs, which are difficult or time consuming to treat orally or by injection. The method is of course very popular with animal managers because of its simplicity, which can of course also be used for individual livestock or all other animals, including pets, and can often be performed without a professional veterinarian.

It is desirable to formulate a commercial product as a thickening agent, but the end user will generally use a dilute formulation.

In addition, such compositions may contain further additives such as stabilizers, antifoams, viscosity modifiers, binders or tackifiers, as well as other active ingredients, to achieve certain effects.

Insect repellent compositions of this type for use by end users likewise form a composition of the present invention.

In each method according to the invention for pest control or in each pest control composition according to the invention, the active ingredient of the formula (I) can be used in all steric configuration or mixtures thereof.

In addition, the present invention is characterized in that the active ingredient of formula (I) or an active ingredient preparation prepared therefrom is administered to an animal as an additive to a feed or beverage, or is administered orally, injected or parenterally in solid or liquid form. Methods of prophylactic protection of warm blooded animals against parasites, particularly livestock, domestic animals and pets. The invention also includes a compound of formula (I) according to the invention for the use of one of the above methods.

The following examples are provided for illustrative purposes only without limitation of the present invention, and the active ingredient terms refer to the materials listed in Table 1 below.

In particular, preferred formulations consist of:

(% = Weight percentage)

Formulation example

1.Emulsion Thickener a) b) c)

Active ingredient 25% 40% 50%

Ca dodecylbenzene sulfonate 5% 8% 6%

Castor Oil Polyethylene Glycol Ether

(36 mol ethylene oxide) 5%-

Tributylphenolpolyethylene glycol ether

(30 mol ethylene oxide) -12% 4%

Cyclohexanone-15% 20%

Xylene Mixture 65% 25% 20%

From these thickeners, emulsions of any desired concentration could be prepared by dilution with water.

2. Emulsion Concentrate a) b) c)

Active ingredient 10% 8% 60%

Octylphenol polyethylene glycol ether

(4-5 mole ethylene oxide) 3% 3% 2%

Ca dodecylbenzene sulfonate 3% 4% 4%

Castor Oil Polyethylene Glycol Ether

(35 mol ethylene oxide) 4% 5% 4%

Cyclohexanone 30% 40% 15%

Xylene Mixture 50% 40% 15%

From these thickeners, emulsions of any desired concentration could be prepared by dilution with water.

3. Suspension Thickener

40% active ingredient

Ethylene Glycol 10%

Nonylphenol Polyethylene Glycol Ether

(15 mol ethylene oxide) 6%

Na lignin sulfonate 10%

Carboxymethyl Cellulose 1%

37% formaldehyde aqueous solution 0.2%

0.8% silicone oil in the form of an aqueous emulsion

32% of water

The finely ground active ingredient was mixed directly with the mixture. In this process, a suspending thickener is obtained, which can be prepared by diluting a suspension of any desired thickener with water.

4. Powder mixtures dispersible in water a) b) c)

Active ingredient 25% 50% 75%

Na riginine sulfonate 5% 5%

Oleic acid 3% -5%

Na diisobutylnaphthalene sulfonate -6% 10%

Octylphenol polyethylene glycol ether

(7-8 mol ethylene oxide) -2%-

High Dispersed Silicate 5% 10% 10%

Kaolin 62% 27%-

The active ingredient was mixed thoroughly with the mixture and ground well in a suitable mill. Dilution with water gave a wettable powder that could form a suspension of any desired thickener.

5. Powder a) b)

Active ingredient 2% 5%

High Dispersion Silicate 1% 5%

Talc 97%-

Kaolin-90%

Mixing directly with the active ingredient and grinding the mixture gave a ready-to-use powder.

6. Granules a) b)

Active ingredient 5% 10%

Kaolin 94%

High Dispersion Silicate 1%-

Aterpulzite -90%

The active ingredient was dissolved in methylene chloride, sprayed onto a carrier, and then the solvent was concentrated by evaporation in vacuo. Granules of this kind could be mixed with the feed.

7. Granules

10% active ingredient

Na lignin sulfonate 2%

Carboxymethyl Cellulose 1%

Kaolin 87%

The active ingredient is mixed with the mixture, triturated and wetted with water. The mixture was extruded and then air dried.

8. Granule

Active ingredient 3%

Polyethylene glycol (mw 200) 3%

Kaolin 94%

(mw = molecular weight)

The finely ground active ingredient was mixed evenly in a mixer with kaolin wetted with polyethylene glycol. In this way, powder-free coated granules were obtained.

9. Tablet or Boli

I. Active ingredient 33.00%

Methylcellulose 0.80%

High Dispersion Silicate0.80%

Corn starch 8.40%

II crystalline lactose22.50%

Corn Starch 17.00%

Microcrystalline Cellulose 16.50%

Magnesium Stearate1.00%

I. Methyl cellulose was stirred in water. The material was swollen in water and the silicic acid was stirred and the mixture was suspended homogeneously. The active ingredient and corn starch were mixed. Aqueous suspension was added to the mixture and kneaded with a kneader. The resulting mass was passed through 12 M sieves to granulate and dry.

II. All four excipients were mixed thoroughly.

III. The premixes obtained according to I and II were mixed and compressed into tablets or boli.

10. Injectables

A. Planetary Vehicle (Delayed Release)

1.0.1-1.0 g of active ingredient

Add up to 100 ml of peanut oil

2.0.1-1.0 g of active ingredient

Add up to 100 ml of sesame oil

Preparation: The active ingredient was dissolved in oil, stirred with gentle heating if necessary, then cooled and then sterile filtered through a suitable membrane filter of pore size 0.22 mm, cooled to the desired volume.

B water-miscible solvent (release of standard rate)

0.1 to 1.0 g of active ingredient

40 g of 4-hydroxymethyl-1,3-dioxolane (glycerol formal)

Add up to 100 ml of 1,2-propanediol

0.1 to 1.0 g of active ingredient

Glycerol Dimethyl Ketal 40 g

Add up to 100 ml of 1,2-propanediol

Preparation: The active ingredient was dissolved in the solvent with stirring, brought to the desired volume and sterilized through a suitable membrane filter with a pore size of 0.22 mm.

C. aqueous solubilization (fast release)

1.0.1-1.0 g of active ingredient

Polyethoxylated Castor Oil

(40 ethylene oxide units) 10 g

20 g of 1,2-propanediol

1 g of benzyl alcohol

Add up to 100 ml of Aqua ad inject.

2.0.1-1.0 g of active ingredient

Polyethoxylated sorbitan monooleate

8 g (in 20 ethylene oxide units)

20 g of 4-hydroxymethyl-1,3-dioxolane (glycerol formal)

Benzyl Alcohol1 g

Add up to 100 ml of hydrogenated injection solution

Preparation: The active ingredient was dissolved in solvent and surfactant and made up to the desired volume with water. Filtration was carried out through an appropriate membrane filter with a pore size of 0.22 mm.

11.Pour-On

A.

5 g of active ingredient

10 g of isopropyl myristate

Add up to 100 ml of isopropanol

B

2 g of active ingredient

5 g of hexyl laurate

15 g of medium length chain triglycerides

Add up to 100 ml of ethanol

C.

2 g of active ingredient

5 g of oleyl oleate

40 g of N-methyl-pyrrolidone

Add up to 100 ml of isopropanol

In addition, the aqueous system may preferably be used for oral and / or intraruminal administration.

In addition, the composition may further comprise additives such as stabilizers that are additives, such as properly epoxidized vegetable oils (epoxylated coconut oil, rapeseed oil, or soybean oil) to achieve certain effects; Antifoams, typically silicone oils; antiseptic; Viscosity modifiers; Binders; And tackifiers, as well as fertilizers or other chemical agents.

In addition, additional biologically active substances or additives, as well as mineral salts or vitamins, which are neutral to the compound of formula I and which do not have a deleterious effect on the host animal to be treated, can be added to the described compositions.

The following examples are provided to illustrate the present invention. The following examples do not limit the invention. The letter 'h' represents time.

Production Example

Example 1 [N- (5-cyano-4-trifluoromethylthiazol-2-yl)]-1- [3,5-dichloropyrid-2-yl] -cyclopropyl-1-carbon amides

278 mg of 1- [3,5-dichloropyrid-2-yl] -cyclopropyl-1-carboxylic acid are dissolved in 3.3 ml of oxalyl chloride under nitrogen atmosphere at room temperature, 1 drop of dimethylformamide is added, and the mixture is Was boiled under reflux for 2 hours. After evaporation to concentration in vacuo, the residue was dissolved in 5 ml of anhydrous dichloromethane, then 193 mg of 2-amino-5-cyano-4-trifluoromethylthiazole was added, followed by 0.46 ml of diisopropylethylamine And 23.6 mg of 4-dimethylaminopyridine were added. The mixture was stirred at room temperature in a nitrogen atmosphere for 20 hours, then washed with a small amount of water, 25 ml of saturated sodium bicarbonate solution, and finally 25 ml of saturated sodium chloride solution. The organic phase was dried over magnesium sulfate, filtered and concentrated by evaporation, the residue was purified on an HPLC column and the title compound having a melting point of 195-197 ° C. was obtained.

The materials named in Tables 1 to 3 below could be prepared similarly to the methods described above. The value of the melting point is given in degrees Celsius.

Biological Examples:

1. Mongolian gerbilus rats with subcutaneous injection Mongolian gerbils ) ( Merriones Uguikulatus ( Meriones unguiculatus ))in Tricot Strong Illu Colubbriformis ( Trichostronqylus colubriformis ) And Himoncus Contortus ( Haemonchus contortus In vivo testing for

Approximately 2000 tees each to 6-8 week old Mongolian gerbilus rats . Miss Bridget kolru Fort (T. colubriformis) and HI. The third larva of H. contortus was invaded by artificial feeding. After 6 days of invasion, gerbilous rats were lightly anesthetized with N ₂ O and dissolved in a mixture of 2 parts of DMSO and 1 part of polyethylene glycol 400 at doses of 100, 32 and 10 mg to 0.1 mg / kg into the neck area. Treatment was by subcutaneous injection. Day 9 (3 days after treatment), most H that still survives . Contortus is the fourth larvae, and most tees. When Colubriformis was an immature adult, gerbilous mice were sacrificed to count parasites. Efficacy was calculated as the reduction rate for the number of parasites in each gerbilus rat compared to the geometric mean number of parasites found in eight invasive and untreated gerbilus rats.

In this test, a significant reduction in nematode invasion was achieved using the compound of formula (I). Similar results were obtained overall upon oral administration of the active ingredient.

2. Spodoptera Litoralis ( Spodoptera littoralis Gastrointestinal Toxicity Activities of Insecticides on

Five potted cottons were sprayed with acetone / aqueous test solution containing 1, 3, 12.5 or 50 ppm of the test subject compound, respectively.

After the spray deposits were dried, the cotton was metastasized to about 30 larvae of Spodoptera litoralis (L ₁ group). Two cottons were used per test compound and test species. Testing at about 24 ° C. and relative humidity of 60%. Assessments and intermediate assessments of dying animals, larvae and feeding impairments were performed after 24, 48 and 72 hours.

Compounds of formula (I) achieved complete lethality at only 3 ppm active ingredient concentration after 24 hours.

3. Activity against phytotoxic mites

OP-sensitive Tetranicus Urticae ( Tetranychus urticae )

Tea first leaves of legumes (Pace come loose vulgaris (Phaseolus vulgaris)),. The leaves of mass-cultivate pieces invaded with T. urticae were covered 16 hours prior to testing. After removing the leaf fragments, the plants infiltrated with all phase mites were sprayed with a test solution containing 0.2, 0.4 or 1.6 ppm of the test compound to the drip point. The temperature of the greenhouse was about 25 ° C. After 7 days, the percentages of mobile (adult and larval) ticks and eggs were measured microscopically.

Compounds of formula (I) achieved complete mortality at an active ingredient concentration of 0.4 ppm.

4. Lucilia Sericata ( Lucilia sericata ) L _One Activity against larvae

1 ml of the water suspension of the active substance to be tested was mixed with 3 ml of the specific larval growth medium at about 50 ° C. to obtain a homogenate having a content of 250 or 125 ppm of the active ingredient. Rusilriah (Lucilia) was used larvae (L ₁₎ of about 30 in each test tube sample. After 4 days, lethality was measured. The compound of formula (I) achieved 100% activity at 250 ppm.

5. Bupilus Microplus ( Boophilus microplus Acaricide activity against (Biarra strain)

A piece of adhesive tape is attached horizontally to a PVC sheet, bupil loose Micro Plus (Boophilus microplus) a back surface of 10 female ticks had sufficient probe (non-Ara system), side-by-side, could be attached to a single line. An injection needle was used to inject 1 μl of liquid into each tick. The liquid is a mixture of polyethylene glycol and acetone (1: 1) and the active ingredient is dissolved to be selected from a specific amount of 1, 0.1 or 0.01 μg per tick. Control animals were injected with no active ingredient. After treatment, animals were placed under normal conditions in an insect kennel at about 28 ° C. and 80% relative humidity until spawning, and control animals hatched larvae from eggs. The activity of the test substance was measured by IR ₉₀ , i.e., 9 of 10 female ticks (= 90%) were evaluated by the dose of the active ingredient when sterile eggs were laid after 30 days.

The compound of formula I had an IR ₉₀ of 0.1 μg.

6. test of the probe in which the female bupil loose Micro Plus (BIARRA) in vitro potency:

4x10 female female ticks of OP-resistant BIARRA strains were attached to long sticky strips and covered for 1 hour with cotton-wool balls immersed in emulsions or suspensions of test compounds at concentrations of 500, 125, 31 and 8 ppm, respectively. . Lethality, spawning and hatched larvae were measured after 28 days.

The activity of the test compound is expressed by the number of females exhibiting the following phenomena.

-Courier before laying eggs

-Survive for some time without laying eggs

Lay eggs without the formation of embryos

-Lays eggs that form embryos, but larvae do not hatch,

Lays embryonated eggs and hatches larvae within 26 to 27 days

In this test, the compound of formula (I) had a sudden mortality rate of at least 80% for female ticks.

7. Apis Krasivora ( Aphis craccivora ) Contact action

Peas seeds invading all developing stages of aphids were sprayed with an active ingredient solution prepared from an emulsion thickener, a solution containing 50, 25 or 12.5 ppm of active ingredient as desired. After 3 days, dead or fallen aphids were determined to be at least 80%. Formulations are classified as effective even at these levels of activity.

Compounds of formula (I) achieved complete mortality (= 100%) at concentrations of 12.5 ppm.

8. Aedes Aegifti ( Aedes aeaypti Insecticidal activity against

A 0.1% acetone solution of the active ingredient was pipetted to the surface of 150 ml of water in the container in an amount sufficient to achieve a selected concentration of 10, 3.3 or 1.6 ppm. After evaporation of acetone, the vessel was covered with about 30-40 aedes larvae on day 3 of development. After 1, 2 and 5 days, lethality was tested.

In this test, the compound of formula I completely killed all the larvae after only one day at a concentration of 1.6 ppm.

9. In vivo efficacy of adult cat flea ( Ctenocephalides felis ) after oral treatment

The test substance was orally administered to the home cats in gelatin capsules before and after feeding and the dose was varied from 0.5 to 20 mg / kg. After 1, 3, 7 and 10 days of treatment, each cat was exposed to 100 fleas (about 50 males and about 50 females), depending on the results of previous flea metastasis. The efficacy (% reduction in flea counts) was based on the number of surviving fleas found after combing for 10 minutes after 1 day of each new flea metastasis, and the% efficacy was calculated from the average number of live fleas in the control group. Subtracted by the number of surviving fleas, divided by the arithmetic mean of the number of surviving fleas of the control animals, and then multiplied by 100.

The dead fleas found in the cat kennel and collected by combing were placed in an incubator at 28 ° C. and 70% relative humidity and survival / lethality tested after 24 hours. The test compound is considered as a flea killer if most of the dying fleas are lethal and the test compound exhibits "knock-down" activity when the majority are alive.

In this test, the compound of formula I killed at least 80% of the fleas.

10. Spot-on of home cat after treatment Cat flea ( Ctenocephalides felis In vivo efficacy on adult

Test substance was administered to house cats as a spot-on treatment and the dose varied from 0.5 to 10 mg / kg. After 1, 3, 7 and 10 days of treatment, each cat was exposed to 100 fleas (about 50 males and about 50 females), depending on previous flea metastasis results.

Efficacy (% reduction in flea counts) was based on the number of surviving fleas found after combing for 10 minutes after 1 day of each new flea metastasis, and the% efficacy was calculated from the average number of live fleas in the control group. Subtracted by the number of surviving fleas, divided by the arithmetic mean of the number of surviving fleas of the control animals, and then multiplied by 100.

The dead fleas found in the cat kennel and collected by combing were placed in an incubator at 28 ° C. and 70% relative humidity and survival / lethality tested after 24 hours. The test compound is considered as a flea killer if most of the dying fleas are lethal and the test compound exhibits "knock-down" activity when the majority are alive.

In this test, the compound of formula I killed at least 90% of the fleas after 35 days.

11. Amblitham Hebraium ( Amblyomma hebraeum In vitro efficacy on larvae

About 5 fasted larvae were placed in polystyrene test tubes containing 2 ml of test compound in solution, suspension or emulsion.

After soaking for 10 minutes, the mixture was shaken for 2x10 seconds with a vortex mixer and the test tube was tightly sealed with a cotton-wool bundle and spun. As soon as the cotton-wool balls were soaked with liquid water, they were squeezed halfway into still rotating tubes, so that most of the liquids were squeezed out of the cotton-wool balls and flowed onto the petri dish.

Subsequently, the test tubes were placed under sunlight in a room temperature room until the measurement. After 14 days, the test tubes were immersed in a beaker with boiling water. If the tick starts to move in response to heat, the test substance is inert at the test concentration, and if the tick is considered dead, the test substance is considered active at the test concentration. All materials were tested at concentrations of 0.1 to 100 ppm.

In this test, the compound of formula (I) killed at least 80% of ticks.

12. Dermanisus Galinae ( Dermanyssus gallinae For)

2-3 ml of solution containing 10 ppm of active ingredient and about 200 mites of different developmental stages ( Dermanis gallinae ) were placed in a top open glass container. The vessel was then closed with a cotton-wool bundle, shaken for 10 minutes until the mite was completely wet, and then simply flipped over so that the remaining test solution could be absorbed by cotton-wool. After 3 days, the mortality of the mites was measured by counting the individuals that were killed and expressed as a percentage.

Compounds of formula (I) showed good activity against Dermanisus galina .

13. housefly ( Musca domestica For)

The sugar cubes were treated with a solution of the test substance in such a way that the concentration of the test substance in the sugar was allowed to dry overnight and then 250 ppm. The sugar cubes treated in the above manner were placed on an aluminum dish with wet cotton-wool, 10 adult fly flies, OP-resistant lines, covered with a beaker and incubated at 25 ° C. Lethality was measured after 24 hours.

In this test, the compound of formula I showed good activity against housefly.

Claims (7)

A compound of formula (I) <Formula I> In the formula, R ₁ is hydrogen, halogen, C ₁ -C ₆ -alkyl, C ₁ -C ₆ -alkoxy, C ₁ -C ₆ -haloalkyl, or unsubstituted phenyl or C ₁ -C ₆ -alkyl, C ₁ -C ₆ -Phenyl mono- or substituted-substituted by a substituent selected from the group consisting of haloalkyl, C ₁ -C ₆ -alkoxy, aryloxy, halogen, cyano and nitro, wherein the number of substituents is greater than 1 They may be the same or different from each other; R ₂ is hydrogen, C ₁ -C ₆ -alkyl, (C ₁ -C ₆ -alkylene) phenyl, pyridyl, COOR ₆ , CONR ₇ R ₈ , COR ₆ , allyl or CH ₂ -OR ₆ ; X ₁ is N or C (CN); X ₂ is N, C (CN), C (COOR ₆ ), C (COR ₆ ), C (SOR ₆ ), C (CONR ₇ R ₈ ) or C (N0 ₂ ); X ₃ is O or S; Q is CH or N; R ₃ and R ₄ are independently of each other hydrogen, C ₁ -C ₆ -alkyl, or together with the C atom to which they are attached form a C ₃ -C ₇ -cycloalkyl ring; R ₅ is C ₁ -C ₆ -alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkynyl, C ₁ -C ₆ -haloalkyl, C ₁ -C ₆ -alkoxy, aryloxy, halogen , Cyano, hydroxy, amino, nitro and mono- or substituted-substituted phenyl, wherein the phenyl substituent is C ₁ -C ₆ -alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkynyl, C ₁ -C ₆ -haloalkyl, C ₁ -C ₆ -alkoxy, aryloxy, halogen, cyano, hydroxy, amino and nitro, the number of substituents being 1 If greater, the substituents may be the same or different from each other, and when m is greater than 1, the substituents R ₅ may be identical or different from each other; R ₆ is C ₁ -C ₆ -alkyl, phenyl or benzyl; R ₇ and R ₈ are independently of each other hydrogen or C ₁ -C ₆ -alkyl; m is 1, 2 or 3; n is 0 or 1; Reacting a compound of formula (II), which may optionally be prepared in analogy with a known or corresponding known compound, in the presence of a basic catalyst, to a compound of formula (III) , If necessary, a compound of formula (I) or an enantiomer thereof obtainable according to the above method or by another method can be converted into another compound of formula (I) or an enantiomer thereof, and thus The process for preparing the compound of formula I according to claim 1, wherein the mixture separates to isolate the desired enantiomers. <Formula II> Wherein R ₁ , R ₂ , X ₁ and X ₂ are defined as given for Formula I) <Formula III> Wherein X ₃ , R ₃ , R ₄ , R ₅ , m, n and Q are defined as given for Formula I and Z is a leaving group A composition for controlling pests comprising a carrier and / or a dispersant and at least one compound of the formula (I) according to claim 1 as an active ingredient. Use of a compound of formula (I) as defined in claim 1 in pest control. A method of controlling pests by using at least one compound of the formula (I) according to claim 1 to an insect pest or an effective pesticide site. Use of a compound of formula (I) according to claim 1 in the control of parasites parasitic in warm blooded animals. Use of a compound of formula (I) according to claim 1 in the manufacture of a pharmaceutical composition for controlling parasites.