JPH09501170A - Substituted 4-carbamoyl-pyrrolin-2-one and 4-carbamoyl-dihydrofuran-2-one derivatives and their use as pest control agents - Google Patents

Abstract

(57) Abstract: The present invention provides a compound of the formula (I) Wherein A, B, Z, G, X, R ¹ and R ² have the meanings described herein, the novel substituted 4-carbamoylpyrrolin-2-one and dihydrofuran-2-one Derivatives, several processes for their preparation and their use as pest control agents.

Description

Detailed Description of the Invention   Substituted 4-carbamoyl-pyrrolin-2-one derivative and 4-carbamoy Ru-dihydrofuran-2-one derivative and use thereof as pest control agent   The present invention provides novel 4-carbamoyl-pyrrolin-2-one derivatives and 4-carbamoyl Moyl-dihydrofuran-2-one derivatives, several processes for their production and their harmful effects It relates to its use as a pesticide, especially an insecticide.   3-Aryl-4-carbamoyl-pyrrolin-2-one and its herbicides and insecticides Or acaricidal effects have been disclosed (eg European patent applications) (See No. 442,077, No. 528,156 and No. 529,334).   However, the effects of these compounds are not satisfactory in all cases .   The present invention relates to a compound of the formula (I)     Wherein A is hydrogen, or in each case optionally halogen, alkoxy or halo. Represents alkyl or cycloalkyl optionally substituted with genoalkoxy Or an optionally substituted aryl or aralkyl in each case Represent     B represents hydrogen or alkyl, or     A and B are optionally containing heteroatoms together with adjacent carbon atoms. Represents a ring which may be replaced,     Z represents nitrogen or oxygen,     X is hydrogen, or in each case optionally halogen, alkyl, alkoxy, ar Quilthio, halogenoalkyl, halogenoalkoxy or halogenoalkylthio Alkyl, cycloalkyl, alkoxy or alkyl optionally substituted with Represents Thio,     R¹Represents alkyl, alkenyl or acyl,     R²Is an alkyl, alkene optionally substituted with halogen in each case. Represents a nyl, alkoxyalkyl or aryl, or optionally a heteroatom Represents a cycloalkyl which may be contained, or     R¹And R²Are optionally substituted together with the nitrogen atom to which these are bound And optionally represents a ring which may further contain a heteroatom,     G is hydrogen when Z represents nitrogen, or optionally halogen or al in each case. Alkyl, alkenyl, optionally substituted with cooxy or halogenoalkoxy Or ar, which represents cycloalkyl or is optionally substituted in each case Or aralkyl, or acyl, or     A and G are optionally substituted with the atoms to which they are attached And represents a ring which may further contain a heteroatom, New substituted 4-carbamoyl-pyrrolin-2-one derivatives of It relates to a vamoyl-dihydrofuran-2-one derivative.   Due to one or more chiral centers, the compounds of formula (I) are generally suitable Raba occurs as a mixture of stereoisomers that can be separated by conventional methods. These things are Astereomeric mixture states and pure diastereomers or enantiomers It can be used in both. On the other hand, for simplicity, the compound of formula (I) is Trendy compounds and isomers, enantiomers and stereoisomers of different properties It is intended to mean both mixtures containing.   The present invention also provides a compound of formula (I)     In the formula, A, B, X, Z, G, R¹And R²Has the above meaning, 4-carbamoyl-pyrrolin-2-one and 4-carbamoyl-dihydrofuran In the production of N-2-one, the formula (II)     Wherein A, B, X, Z and G have the meanings given above, Compound   a) Formula (III) optionally in the presence of a diluent and optionally in the presence of an acid binder.     Where R¹And R²Has the above meaning, and     Hal represents halogen, especially chlorine or bromine, With carbamoyl halide of   b) Phosgene in the first step optionally in the presence of a diluent and optionally in the presence of an acid binder. Or formula (IV)         R^Three-O-CO-Cl (IV)     Where R^ThreeRepresents an optionally halogen-substituted alkyl, Reacting with the formate ester and the compound thus obtained in the second step Formula (V) optionally in the presence of a diluent     Where R¹And R²Has the above meaning, 4-carbamoyl-pyrrolid of formula (I) characterized by reacting with an amine of And a method for producing 4-carbamoyl-dihydrofuran-2-one. I do.   Furthermore, novel 4-carbamoyl-pyrrolin-2-one derivatives of formula (I) and 4- Carbamoyl-dihydrofuran-2-one derivatives are characterized by remarkable insecticidal activity .   The new compounds are generally defined by formula (I).   A is preferably hydrogen, or in each case optionally halogen, C₁~ C_Four-Alkoki Si and / or C₁~ C_Four-C optionally substituted with halogenoalkoxy₁-C_Ten -Alkyl or C_Three~ C_Ten-Cycloalkyl, or optionally halogen in each case N, CN, nitro, C₁-C₈-Alkyl, C₁~ C₈-Alkoxy, C₁~ C₈-A Lucircio, C₁-C₈-Halogenoa Rukiru and / or C₁~ C₈-A group which may be substituted with halogenoalkoxy Nyl, naphthyl or phenyl-C₁~ C₆Represents alkyl.   B is preferably hydrogen or C₁~ C₈-Represents alkyl or A and B are Optionally together with the carbon atom to which they are attached, halogen, alkyl and / or Or optionally substituted with alkoxy, and optionally nitrogen, oxygen, sulfur or groups Represents a 3- to 8-membered ring which may include -O-CO-.   X is preferably hydrogen, or in each case optionally halogen, C₁~ C₆-Alkyl , C₁~ C₆-Alkoxy, C₁~ C₆-Alkylthio, C₁~ C₆-Halogeno Archi And / or C₁~ C₆-C optionally substituted with halogenoalkoxy₁~ C₆ -Alkyl, C₁~ C₆-Alkoxy, C₁~ C₆-Alkylthio or C_Three~ C₇− Represents cycloalkyl.   R¹Is preferably C₁~ C₆-Alkyl or C_Three~ C₆-Alkenyl or radical Or -SO₂Represents one of -OR, Here, R and R'are independently of each other, in each case optionally halogen, C₁~ C₆-Al Kill, C₁~ C₆-Alkoxy, C₁~ C₆-Halogenoalkyl and / or C₁~ C₆-C optionally substituted with halogenoalkoxy₁~ C_Ten-Alkyl, C_Three~ C_Ten-Cycloalkyl, phenyl, phenyl-C₁~ C_Four-Alkyl or Hetari And then R'may also represent hydrogen, or R and R ', together with the nitrogen atom to which they are attached, are optionally C₁~ Optionally substituted with C4 -alkyl and optionally up to 2 more nitrogens or acids It represents a 5- to 7-membered ring which may contain an elementary atom.   R²Is preferably in each case optionally substituted halogen.₁~ C₂₀− Alkyl, C_Three~ C₂₀-Alkenyl, C₁~ C₈-Alkoxy-C₁~ C₈-Archi Le, C₁~ C₈-Alkylthio-C₁~ C₈-Alkyl, phenyl or optionally 2 C which may contain oxygen and / or sulfur atoms in_Three~ C₈-Cycloalkyl Express or R¹And R²Preferably at any time together with the nitrogen atom to which they are attached, C₁ ~ C_FourOptionally substituted with alkyl, and optionally up to 2 oxygens and / or Represents a 3- to 7-membered ring which may contain sulfur.   Z preferably represents nitrogen or oxygen.   G is preferably hydrogen when Z represents nitrogen, or optionally halo in each case. Gen, C₁~ C₆-Alkoxy and / or C₁~ C₆-Substituted with halogenoalkoxy C that may be₁~ C₈-Alkyl, C_Three~ C₈-Alkenyl or C_Three~ C₈− Cycloalkyl, or optionally in each case halogen, CN, nitro, C₁~ C₆− Alkyl, C₁~ C₆-Alkoxy, C₁~ C₆-Alkylthio, C₁~ C₆-Halogen Noalkyl, C₁~ C₆-Halogenoalkylthio and / or C₁~ C₆-Halogeno Phenyl, naphthyl or phenyl-C optionally substituted with alkoxy₁~ C_Four-Alkyl or group Or -SO₂Represents one of -OR, Here, R and R'are independently of each other, in each case optionally halogen, C₁~ C₆-Alkyl, C₁~ C₆-Alkoxy, C₁~ C₆-Halogenoalkyl and / or Or C₁~ C₆-C optionally substituted with halogenoalkoxy₁~ C₈-Alkyl , C_Three~ C₇-Cycloalkyl, phenyl, phenyl-C₁~ C_Four-Alkyl or Represents Hetaryl, and R'can also represent hydrogen, or R and R ', together with the nitrogen atom that binds to them, are optionally C₁~ C_Four-A It may be substituted with rukyi and optionally up to two more nitrogen or oxygen atoms. Represents a 5 to 7 membered ring which may be included, or A and G together with the atom to which they are attached are optionally halogen and / or Is C₁~ C_FourOptionally substituted with alkyl, optionally containing oxygen or sulfur atoms It represents a 4- to 8-membered ring which may be optionally unsaturated.   A is particularly preferably hydrogen, or in each case optionally fluorine, chlorine, bromine, C₁ ~ C_Four-Alkoxy, triple orthomethoxy and / or pentafluoroethoxy C optionally substituted with Si₁~ C₈-Alkyl or C_Three~ C₈-Cycloalkyl Or each time, fluorine, chlorine, bromine, CN, nitro, C₁~ C_Four-Alkyl, C₁ ~ C_Four-Alkoxy, C₁~ C_Four-Alkylthio, C₁~ C_Four-Halogenoalkyl and And / or C₁~ C_Four-Phenyl, optionally substituted with halogenoalkoxy, Futyl or Phenyl-C₁~ C_FourRepresents alkyl.   B is particularly preferably hydrogen, or C₁~ C₆Represents alkyl, or A and B are particularly preferably optionally together with the carbon atom to which they are attached. Fluorine, chlorine, bromine, C₁~ C_Four-Alkyl and / or C₁~ C_Four Optionally substituted with alkoxy and optionally containing oxygen or sulfur atoms Represents a 3- to 7-membered ring which may be present.   X is particularly preferably hydrogen, or in each case optionally fluorine, chlorine, bromine, C₁ ~ C_Four-Alkyl, C₁~ C_Four-Alkoxy, C₁~ C_Four-Alkylthio, C₁~ C_Four -Halogenoalkyl and / or C₁~ C_Four-Substituted by halogenoalkoxy May be C₁~ C_Four-Alkyl or C_Three~ C₆-Represents cycloalkyl.   R¹Is particularly preferably C₁~ C_Four-Alkyl or C_Three~ C_Four-Arkeni Where R is optionally fluorine, chlorine, bromine, C in each case.₁~ C_Four-Alkyl, C₁~ C_Four-Alkoxy, C₁~ C_Four-Halogenoalkyl and / or C₁~ C_Four-Halogen C optionally substituted with noalkoxy₁~ C₈-Alkyl, C_Three~ C₈-Cycloa Represents rualkyl, phenyl, benzyl, pyryl, thienyl or pyridyl.   R²Is particularly preferably C optionally optionally substituted in each case with fluorine and / or chlorine.₁ ~ C₁₄-Alkyl, C_Three~ C₁₄-Alkenyl, C₁~ C_Four-Alkoxy-C₁~ C₆ -Alkyl, C₁~ C_Four-Alkylthio-C₁~ C₆-Alkyl, phenyl or optional C which may contain oxygen and / or sulfur atoms_Three~ C₇-Represents cycloalkyl Forget or R¹And R²Is particularly preferably together with the nitrogen atom to which they are attached. Hour C₁~ C_ThreeOptionally substituted with alkyl and optionally oxygen and / or sulfur Represents a 3- to 6-membered ring which may contain atoms.   Z particularly preferably represents nitrogen or oxygen.   G is particularly preferably hydrogen when Z represents nitrogen or, in each case, optionally fluorine. Fluorine, chlorine, bromine, C₁~ C_Four-Alkoxy and / or C₁~ C_Four-Halogenoal C optionally substituted by Coxy₁~ C₆-Alkyl, C_Three~ C₆Alkenyl or Is C_Three~ C₆-Cycloalkyl, or optionally in each case fluorine, chlorine, bromine, C N, nitro, C₁~ C_Four-Alkyl, C₁~ C_Four-Alkoxy, C₁~ C_Four-Alkyl Thio, C₁~ C_Four-Halogenoalkyl, C₁~ C_Four-Halogenoalkoxy and / or Is C₁~ C_Four-Phenyl, naphthyl optionally substituted with halogenoalkylthio , Benji Represents one of Here, R and R'independently of one another are in each case optionally fluorine, chlorine, bromine, C₁ -C_Four-Alkyl, C₁~ C_Four-Alkoxy, C₁-C_Four-Halogenoalkyl and / Or C₁~ C_Four-C optionally substituted with halogenoalkoxy₁~ C₈-Archi Le, C_Three~ C₈-Cycloalkyl, phenyl, benzyl, pyryl, thienyl or Represents pyridyl, and R'may also represent hydrogen, or R and R ', together with the nitrogen atom to which they are attached, are optionally C₁~ C_Four-A Optionally substituted with rukyi and optionally further containing oxygen and / or nitrogen atoms Represents a 5- to 7-membered ring which may be A and G, together with the atom to which they are attached, are C at any time₁~ C_Four-Alkyl Represents a 5- to 8-membered carbocycle which may be substituted with.   A is very particularly preferably hydrogen, or in each case the same or different 1 One or more methyl substituted with one or more fluorine or chlorine, Ethyl, propyl, i-propyl, n-butyl, s-butyl, i-butyl, t- Represents butyl, phenyl or benzyl.   B is very particularly preferably hydrogen, methyl, ethyl, propyl, i-propyl, represents n-butyl, s-butyl, i-butyl or t-butyl, or A and B together form a group-(CH₂)_Four-,-(CH₂)₂-,-(CH₂)₆−, -(CH₂)_Four-CH (CH_Three)-,-(CH₂)_Three-CH (CH_Three) -CH₂−, − (CH₂)₂-CH (CH_Three)-(CH₂)₂-,-(CH₂)₂-CH (C₂H_Five)- (CH₂)₂-,-(CH₂)₂-CH (C_ThreeH₇)-(CH₂)₂-,-(CH₂)₂− CH (C_FourH₉)-(CH₂)₂-, -CH₂O (CH₂)₂-, -CH₂S- (CH₂ )₂-,-(CH₂)₂-O- (CH₂)₂-Or-(CH₂)₂-S- (CH₂)₂ Represents one of the   X is very particularly preferably hydrogen, or in each case optionally fluorine, chlorine, bromine. , Methyl, ethyl, propyl, i-propyl, methoxy, ethoxy, trifluor Methyl and / or optionally substituted with trifluoromethoxy Tyl, propyl, i-propyl, n-butyl, s-butyl, i-butyl, t-bu Tyl, methoxy, ethoxy, cyclopropyl, cyclopentyl or cyclohex Represents sill.   R¹Is very particularly preferably methyl, ethyl, propyl, i-propyl, ali. Represents methyl, methylsulfonyl, ethylsulfonyl or propylsulfonyl.   R²Is very particularly preferably optionally substituted in each case with fluorine and / or chlorine C that may be₁~ C_Ten-Alkyl, C_Three~ C_Ten-Alkenyl, C_Three~ C₆− Shi Chloroalkyl, C₁~ C_Three-Alkoxy-C₁~ C_Four-A Represents rualkyl or phenyl, or R¹And R²Very particularly preferably together with the nitrogen atom to which they are attached. Optionally substituted with methyl and / or ethyl, and optionally oxygen atom Represents a 3- to 6-membered ring which may contain.   Z very particularly preferably represents nitrogen or oxygen.   G is very particularly preferably hydrogen if Z represents nitrogen, or in each case Methyl, ethyl, propyl optionally substituted with fluorine and / or chlorine , I-propyl, butyl, s-butyl, i-butyl or t-butyl, or optionally Sometimes fluorine, chlorine, nitro, C₁~ C_Four-Alkyl and / or C₁~ C_Four-Alkoki Phenyl optionally substituted with Si, Here, R and R ′ independently of one another are in each case optionally fluorine and / or chlorine. Optionally substituted C₁~ C₆-Alkyl, C_Three~ C₆-Alkenyl, phenyl Or benzyl, and R'may also represent hydrogen, or R and R'may together form a group-(CH₂ )_Three-,-(CH₂)_Four-,-(CH₂)_Five-, -CH₂-CH (CH_Three) (CH₂)₂ -, -CH₂O- (CH₂)₂-Or-CH₂S- (CH₂)₂− Represents one of the A and G very particularly preferably together with the radical-(CH₂)_Three−, Represents one of the   The definitions or explanations of the above general groups, or those shown in the preferable ranges are as follows. Freely combined within them, ie also between individual and preferred ranges. These are applied to the final products and precursors and intermediates in a corresponding manner .   According to the invention, a combination of the meanings indicated above as (preferably) preferred. Compounds of general formula (I) in which are present are preferred.   According to the invention, there are combinations of the meanings given above as being particularly suitable. Compounds of general formula (I) are particularly preferred.   According to the invention, the meaning of those meanings indicated above as being very particularly suitable is given. Very particular preference is given to compounds of the general formula (I) in which a combination is present.   The following compounds of formulas (Ia) and (Ib) may be mentioned individually:   3-Ethyl-5,5- (2, as starting compound for preparing the compound of formula (I) 3-Dimethyl) -pentamethylene-4-hydroxy-pyrrolin-2-one and salts When using dimethylcarbamoyl chloride, the reaction pathway can be represented by the following formula:   As a starting compound for preparing the compound of formula (I) With droxy-dihydrofuran-2-one and morpholinecarbamoyl chloride In this case, the reaction pathway can be represented by the formula:   The compounds of formula (II) required as starting compounds in the novel process are partially Or in literature such as Matsuo, Tanaka; Chem. Pharm. Bull.32， 3 724 (1984): Noland, Sundberg, J. et al. Org. Chem.28, 3150 (1963); Brandange , J. et al. Org. Chem.49, 927 (1984) by a known method.   The following pyrrolin-2-ones of formula (IIa) may be mentioned individually: The individual pyrrolin-2-ones of formula (IIa) may be mentioned:   Carbamoyl halides of formula (III) are well known in organic chemistry synthetic chemistry It is a drug.   The following compounds of formula (III) may be mentioned individually: dimethylcarbamoyl chloride, chloride Diethylcarbamoyl, dipropylcarbamoyl chloride, diisopropylcarbyl chloride Vamoyl, dibutylcarbamoyl chloride, ethylmethylcarbamoyl chloride, dichloride Allylcarbamoyl, pyrrolidinecarbamoyl chloride, piperidinecarbamoyl chloride And morpholine carbamoyl chloride.   The reaction of the compound of formula (II) with the carbamoyl halide of formula (III) is a diluent and It can occur in the presence of acid bonds.   All solvents that are inert towards compounds (II) and (III) are used as diluents. Can be used. Hydrocarbons such as benzine, benzene, and toluene are preferably used. , Xylene and tetralin, as well as halohydrocarbons such as methylene chloride , Chloroform, carbon tetrachloride, chlorobenzene and o-dichlorobenzene, lined up Ketones such as acetone and methyl isopropyl ketone, and also ethers For example, diethyl ether, tetrahydrofuran and dioxane, as well as Carboxylic acid esters such as ethyl acetate, and also strong polar solvents such as dimethyi. And sulfolane. Hydrolytic stability of acid halides The reaction can also be carried out in the presence of water if the properties are acceptable.   All customary acid acceptors are suitable as acid binders. The one that can be preferably used is the third one. Primary amines such as triethylamine, pyridine, diazabicyclooctane (DAB CO), diazabicycloundecene (DBU), dia Methyl-aniline as well as alkaline earth metal oxides such as oxide magnesia Nesium and calcium oxide, and also alkali metal carbonates and alkaline earth metals Genus carbonates such as sodium carbonate, potassium carbonate and calcium carbonate, and also Alkali metal hydroxides such as sodium hydroxide and potassium hydroxide.   The reaction temperature can be varied within wide limits. Generally, the temperature is between -20 and + 150 ° C, It is preferably between 0 and 100 ° C.   When carrying out this method, the starting compound of formula (II) and the halogenated carbamonium of formula (III) Ile is generally used in approximately equivalent amounts. However, also carbamoyl halide Can be used in a relatively large excess (up to 5 mol). The treatment is performed by a conventional method.   5,5- (2-methyl) -as a starting compound in the preparation of the compound of formula (I) Tetramethylene-pyrrolidine-2,4-dione and trichloromethyl chloroformate In addition, when morpholine is used next, the route of the novel method is represented by the following reaction formula. Can:   This method involves first adding a compound of formula (II), optionally in the presence of a diluent and an acid binder. Characterized by reacting with phosgene or a chloroformate of formula (IV) in the presence There is.   All customary acid acceptors are suitable as acid binders. The one that can be preferably used is the third one. Primary amines such as triethylamine, pyridine, DABCO, DBU, DBA, Zünig's base and N, N-dimethyl-aniline, and additionally alkaline earth metal acids Compounds such as magnesium oxide and calcium oxide, and also alkali metal carbonates Salts and alkaline earth metal carbonates such as sodium carbonate, potassium carbonate and calcium carbonate Cesium, and also alkali metal hydroxides such as sodium hydroxide and potassium hydroxide. Is lium.   Uses as diluent any solvent that is inert to compounds (IV) and (V) I can do it. Hydrocarbons such as benzine, benzene and toluene are preferably used. , Xylene and tetralin, and additionally halogenohydrocarbons such as methylene chloride , Chloroform, carbon tetrachloride, chlorobenzene and o-dichlorobenzene, lined up And ketones such as acetone and methyl isopropyl ketone, and further ether. Such as diethyl ether, tetrahydrofuran and dioxane, and in addition Carboxylic esters such as ethyl acetate, and also strong polar solvents such as dimethyl Sulfoxide and sulfolane.   The reaction temperature can be varied within a relatively wide range. Reaction in the presence of diluent and acid binder Reaction temperature is generally between −20 and + 100 ° C., preferably 0-50. It is between ° C.   The new method is generally carried out under standard pressure.   When carrying out the novel process, the starting compound of formula (II) and the appropriate chloroform of formula (IV) Acid esters are generally used in approximately equivalent amounts. However, also Certain or other components can be used in relatively large excess (up to 2 moles).   After the reaction has taken place, the amine of formula (V) is added to the reaction solvent. 8 transaminations It is carried out at a temperature between 0 and 200 ° C., preferably at the boiling point of the solvent used.   The novel compounds of formula (I) can be used for controlling pests. Pests With undesired animal pests, especially insects that damage plants or higher animals is there.   The novel active compounds are used in agriculture, forestry, protection of stored products and materials and in Animal pests encountered in the live field, preferably arthropods, especially kelp Suitable for insect control and well tolerated by plants, its preference for warm-blooded animals It has a new level of toxicity. They are normal sensitive and resistant species and all Active against certain growth stages. The above pests include the following: Included:   Of the Isopoda, such as Oniscus asellus , Vulgare (Armadillidium vulgare), and Porcellio scover (Por) cellio scabar).   Of the Diplopoda, for example, Blaniul us guttulatus).   Those of the Chilopoda order, for example Geopheus carpohugus (G eophilus carpohagus) and Schitigera spp.   Those of the order Symphyla, for example, Scutgerella imakiyurata (Scut igerella immaculata).   Thysanura, such as Lepisma sacchar ina).   Those of the Collembola, eg Onychi Armas urus armatus).   Orthoptera, such as Blatta ori entalis), American cockroach (Periplaneta americana), Leukohuae Madera D (Leucophaea maderae), Yellow cockroach (Blattella germanica), Cheetah domesticus (Acheta domesticus), kerula (Gryllotalpa spp.) Nosama Batsuta (Locusta migratoria migratorioides), Melanopurus jihue Lenti Alice (Melanoplus differentialis) and Cystselka Gregaria (S chistocerca gregaria).   From the order of the Earwig (Dermaptere), for example Horffikiula auriclaria (Forficula auricularia).   From the order of the Isoptera, for example Reticulitermes  spp.).   Those of the order Lice (Anoplura), eg Phylloxe ra vastatrix), Penfigus (Pemphigus spp.), and Human lice (Pediculu) s humanus corporis), the bedbug (Haematopinus spp.) and the beetle Lami (Linognathus spp.).   From the order of the Liceoptera (Mallophaga), for example the bedbug (Trichodectes spp) .) And Damalinea spp.   Those of the order Thysanoptera, for example Hercinot hrips femoralis) and thrips thrips (Thrips tabaci).   Hemiptera (Heteroptera), such as the green stink bug (Eurygaster spp.) , Dysdercus intermediu s), Piesma quadrata, Bedbug (Cimex lectul) arius), Rhodnius prolixus and Triatma (Tria) toma spp.).   From the order of the Homoptera, for example Aleurodes b. rassicae), cotton whitefly (Bemisia tabaci), Trialeurodes vaporrary Orum (Trialeurodes vaporariorum), cotton aphid (Aphis gossypii), Japanese radish aphid (Brevicoryne brassicae), Cryptomis Libis (Cry ptomyzus ribis), Aphis fabae, Doralis pomi (Dor) alis pomi), apple ringworm (Eriosoma lanigerum), peach aphid (Hyalopterus arundinis), Aphis gossypii (Macrosiphum avenae) , Aphid (Myzus spp.), Aphid (Phorodon humuli) , Yellow-billed aphid (Rhopalosiphum padi), Leafhopper (Empoasca spp) .), Euscelis bilobatus, Green leafhopper (N) ephotettix cincticeps), Cornus scales (Lecanium corni), ori -Scale scale insects (Saissetia oleae) and small-billed planthoppers (Laodelphax stri) atellus), brown planthopper (Nilaparvata lugens), red scale bug (A) onidiella aurantii), white scale bug (Aspidiotus hederae), push Pseudodococcus spp. And Psylla spp.   Lepidoptera, such as the cotton bollworm (Pectinophora gossyp) iella), Bupalus piniarius, Keimatvian Bull Mata (Cheimatobia brumata), Lithocolletis  blancardella), Hypnotomi Yuta Pa Della (Hyponomeuta padella), diamondback moth (Plutella maculipennis), plum bug (Malacosoma neustria), crocodile (Euproctis chrysorrhoea), ma Imaiga (Lyman-tria spp.), Bucculatr ix thurberiella), mandarin orange moth (Phyllocnistis citrella), and moth (Agr) otis spp.), Euxoa spp., Feltia spp., Airi Earias insulana, Heliothis spp., Spo Spodoptesa exigua, weevil (Mamestra brassicae) ), Panolis flammea, and Spodoptera litura (Prodenia Iitu) ra), Spodoptera spp., Trichoplusia ni (Trichoplusia) ni), Carpocapsa pomonella, and Pseudomonas (Pieris s) pp.), Nikameichiyu (Chilo spp.), Awanomeiga (Pyrausta nubilalis) , Blue-toothed cod moth (Ephestia kuehniella), Honey hemlock (Galleria mell) onella), Tineo1a bisselliella, Tenea Peri Onea (Tinea pellionella), Hofmanofura Pseudospletera (Hofma) nnophila pseudospretella), Cacoecia podana, cap Capua reticulana, Cristoneura Fumifuerana toneura fumiferana), Clysia ambiguella, Ciya Hamaki (Homona magnanima) and Tortrix viridana ).   Those of the order Coleoptera, for example, Anobium pu nctatum), diamondback moth (Rhizopertha dominica), common bean Weevil (Acanthoscelides obtectus), Hirotorupe Hylotrupes bajulus, Agelastica a lni), Leptinotarsa decemlineata, Hue Phaedon cochleariae, Diabrotica sp. p.), Psylliodes chrysocephala, rainbow trout Epilachna varivestis, Atomaria spp., No Short-tailed Beetle (Oryzaephilus surinamensis), Weevils (Anthonomus) spp.), weevil (Sitophilus spp.), Othiolinks sulcatus (Oti orrhychus sulcatus), Weevils (Cosmopolites sordidus) Ceuthorrhynchus assimillis, Hypera Postica ( Hypera postica), Beetle (Dermestes spp.), Trogoderma (Trogod erma spp.), Anthrenus spp., Attagenus spp. ), Flat beetle (Lyctus spp.), Meligethes Aeneus (Meligethes) aeneus), Pyrus beetle (Ptinus spp.), Niptus holoreucus (Niptus) hololeucus), Semall's beetle (Gibbium psylloides), Kokunusutomodo Ki (Tribolium spp.), Tenebrio molitor , Click beetle (Agriotes spp.), Conoderus (Conoderus spp.), Melolone Melolontha melolontha, Amfimaron Solschichiari (Amphimallon solstitialis) and Costelytra zearandika (Costelytra)  zealandica).   Hymenoptera, such as honeybee bees (Diprion spp.), Hoplo Kampo (Hoplocampa spp.), Lasius (Lasius spp.), Yellow ants (Monomo) rium pharaonis) and hornets (Vespa spp.).   Diptera species such as Aedes spp. And Anopheles eles spp.), Culex spp., Culex spp., Drosophila me lanogaster), house fly (Musca spp.), housefly (Fannia spp.), black Calliphoro erythrocephala and Lucilia s pp.), lobster fly (Chrysomya spp.), cutebra (Cuterebra spp.), cormorant Fruit fly (Gastrophilus spp.), Hitppobosca (Hyppobosca spp.) Stomoxys spp.), Sheep flies (Oestrus spp.), Bull flies (Hypoderma spp.) , Abu (Tabanus spp.), Tania (Tannia spp.), Fly (Bibio hortulanus) ), Oscinella frit, Black fly (Phorbia spp.), Red-legged fly (Pegomyia hyoscyami), Serratitis kyapitata (Ce ratitis capitata), fruit fly oleae (Dacus oleae) and crab paldo Sa (Tipula paludosa).   Those of the flea order (Siphonaptera), such as Xenopsylla che opis) and Nagano flea (Ceratopyllus spp.).   Those of Arachinida, such as Scorpio maurus ), Latrodectus mactans.   For use as insecticides, the new active compounds are found in and in their commercial preparations. Other active compounds, such as insecticides, in both the application forms prepared from these preparations , Attractants, sterilizers, acaricides, nematicides (nemat) icides), fungicides, growth regulator compounds or herbicides I can do it. Insecticides include, for example, phosphoric acid esters, carbamates, carboxylic acid esters, Contains chlorinated hydrocarbons, phenylurea, substances produced by microorganisms, etc. No.   The following compounds may be mentioned:   Acrinathrin, alphamethrin, beta-cyfluthrin, bifenthrin, Brofenprox, cis-resmethrin, clocitrin, cycloprothrin, Cyfluthrin, cyhalothrin, cypermethrin, deltamethrin, esfenba Relate, ethofenprox, fenpropatorin, fenvalerate, full Citrinate, fluvalinate, Lambuda-cyhalothrin, permethrin, pyret Smetrin, pyrethrum, silafluofen, tralomethrin, zeta-metry ,   Alanikalb, Bengiocarb, Benfracarb, Bufencarb, Butkar Voxime, Carbaryl, Cartap, Ethiophene Carb, Fenobu Carb, Fu Enoxycarb, isoprocarb, methiocarb, methomyl, metolcarb, o Xamil, pirimicarb, promecarb, propoxur, tarbam, thiodical Bu, thiophanox, trimetacarb, XMC, xylylcarb,   Acephate, azinophos A, azinophos M, bromophos A, kassaf Os, carbophenothion, chlorfenbinofos, chlormephos, chlor Pyrifos, Chlorpyrifos M, Cyanophos, Demeton M, Demeton-S- Methyl, demeton S, diazinon, dichlorvos, dicrifos, dichlorfe Nthion, dicrotophos, dimethoate, dimethylvinphos, dioxathio , Disulfon, edifenfos, ethion, etrimfoss, phenyto Rotion, Fention, Phonophos, Formothion, Heptenophos, Lee Provenfos, Isazophos, Isoxathion, Folate, Malathion, Me Carbam, Mevinfoss, Mesulfenfoss, Methacphos, Meta Midophos, Naredo, Omentoate, Oxydemeton M, Oxydeprophos , Parathion A, Parathion M, Fentate, Folate, Phosalon, F Osmet, Fosfamidon, Foxime, Pirimifos A, Pirimifos M , Propaphos, Prothiophos, Protoate, Pyraclofos, Piridafe Nthion, quinalfoss, salicion, cebufoss, sulfotep, sulpro Phoss, tetrachlorbinfoss, temefos, thiomethone, thionazine, avian Chlorfon, triazophos, bamidthione,   Buprofezin, Chlorfluazuron, Diflubenzuron, Flucycloquisulo , Flufenoxuron, hexaflumuron, pyriproxyfen, tebufeno Zido, teflubenzuron, triflumuron, imidacloprid, nitonpyram, N-[(6-chloro-3-pyridinyl) methyl] -N'-cyano-N-methyl- Ethaneimidamide (NI-25),   Adamectin, Amitrazine, Avermectin, Azadirachtin, Bensulta Bacillus thurungiensis, cyromazine, Diafenthiuron, Emamectin, Etofenprox, Fempirad, Phy Pronil, flufenprox, lufenuron, methaaldehyde, milbemecchi , Pymetrozine, tebufenpyrad, triazuron,   Aldicarb, Benfuracarb, Cabofran, Carboslefan, Chloret Xyphos, Chloetocarb, Disulfon, Etoflofos, Etrimfo Su, fenamiphos, fipronil, phonophos, fostiazate, furachi Ocarb, HCH, isazophos, isofenphos, methiocarb, monochrome Tofoss, nitenpyram, oxami Le, folate, foxime, prothiophos, pyraclofos, cebufos, Silafluofen, Tebupirimphos, Tefluthrin, Turbufos, Thiodica Lube, Chiafenox,   Azocyclotin, Butylpyridaben, Clofentedine, Cyhexatin, Dia Fenthiuron, diethion, esmectin, fenazaquin, fenbutatin Xide, phenothiocarb, fenpropatorin, fempirad, fenpyroki Simate, Fluazinam, Fluazuron, Flucycloquisulone, Flufenox Ron, fulvalinate, bubufenblox, hekinchiazox, ivemek Chin, methidathion, monocrotophos, moxidectin, nail, fosaro , Profenofos, pyraclophos, pyridaben, pyrimidifen, tebuhu Empirad, Turindiensine, Trialatin and 4-Bromo-2- (4-chloro) Rophenyl) -1- (ethoxymethyl) -5- (trifluoromethyl) -1H- Pyrrole-3-carbonitrile (AC 303630). Other known activities With compounds such as bird repellants, plant nutrients and soil conditioners Mixing is also possible.   The active compound as such, in the form of its preparations, or these preparations Forms of application prepared by further dilution from, for example, ready-to-use solutions, suspensions It can be used in the form of turbidity agents, emulsions, powders, coating agents and granules. These things are normal For example, application by liquid application, spraying, atomizing or granule application.   The novel active compounds can be applied both before and after germination of the plants.   They can also be treated in the soil before sowing.   The amount of active compound applied can be varied within a relatively wide range. It is a book Qualitatively depends on the properties of the desired effect. Generally, the amount used is 1 hectare of soil surface Active compound per unit between 0.01 and 10 kg, preferably between 0.05 and 5 kg .   For the preparation of insecticides, the novel active compounds are given their physical and / or physical properties. Ordinary compositions, depending on their chemical properties, such as solutions, emulsions, suspensions, powders, foams Drops, coatings, granules, aerosols, natural and synthetic substances impregnated with active compounds, Ultrafine capsules in polymeric materials and coating compositions for seeds and combustion devices Composition used for storage, such as fumigation cartridge, fumigation can, fumigation coil, etc. And ULV cold and hot mist compositions.   These compositions may be prepared in a known manner, for example by incorporating the active compound into extenders, i.e. liquid Solvent, liquefied gas and / or solid carrier under pressure and optionally surfactant, ie It is produced by mixing with an emulsifier and / or a dispersant and / or a foaming agent. Extension When water is used as the agent, for example, an organic solvent can be used as the auxiliary solvent. . As the liquid solvent, mainly aromatic hydrocarbons such as xylene, toluene or acetic acid are used. Examples of rukir naphthalene, chlorinated aromatic or chlorinated aliphatic hydrocarbons Examples are chlorobenzene, chloroethylene or methylene chloride, and aliphatic hydrocarbons. For example cyclohexane, or paraffins such as mineral oil fractions, alcohols such as butter Nols or glycols and their ethers and esters, ketones such as acetone Tons, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone Strong polar solvents such as dimethylformamide and dimethylsulfoxide and Water is suitable; liquefied gas extenders or carriers are gases at room temperature and pressure. Means a liquid that is, for example, a halogen Hydrocarbons and aerodynamics such as butane, propane, nitrogen and carbon dioxide Sol propellant bases; as solid carriers, ground natural minerals, such as kaolin, Clay, talc, chiyoke, quartz, attapulgite, montmorillonite, Or diatomaceous earth and ground synthetic minerals such as highly dispersible silicic acid, alumina and And silicates are suitable; as a solid carrier for granules, ground and fractionated Natural rocks such as calcite, marble, pumice, sepiolite and dolomite and inorganic and organic Grinding of synthetic granules and granules of organic substances such as sawdust, coconut, corn Cobs and tobacco stems are suitable; nonionic as emulsifier and / or foaming agent And anionic emulsifiers such as polyoxyethylene-fatty acid esters, polyoxy Ethylene aliphatic alcohol ethers such as alkylaryl polyglycol ether Tell, alkyl sulfonate, alkyl sulfonate, aryl sulfonate And albumin hydrolysis products are suitable; as dispersants, for example lignins. Rufite waste liquor and methylcellulose are suitable.   Adhesives such as carboxymethyl cellulose and powders, granules or latices Natural and synthetic polymers in the form of gums such as gum arabic, polyvinyl alcohol and poly Vinyl acetate and natural phospholipids such as cephalin and lecithin, and synthetic Phospholipids can be used in the composition. Other additives are mineral and vegetable oils. Can be.   Colorants such as inorganic pigments such as iron oxide, titanium oxide and Prussian blue Organic dyes such as alizarin dyes, azo dyes and metal phthalocyanine dyes, and Trace nutrients such as iron, manganese, boron, copper, cobalt, molybdenum and zinc Can be used.   The preparations generally comprise between 0.1 and 95% by weight of active compound, preferably between 0.5 and 95. %, Preferably between 0.5 and 90%.   Since these compounds have a favorable toxicity for warm-blooded animals, the active compounds are Domestic and agricultural animals as well as zoos, laboratories, Animal pests occurring in test and leisure animals, such as arthropods, preferably It is also suitable for controlling insects and arachnids (ectoparasites). In connection with this, this From all or individual developmental stages of pests and pest tolerance and communication. Active against species that are always sensitive.   Control of animal pests involves disease and its transmission, death and loss of productivity (eg meat). , In the production of milk, wool, leather and eggs) and therefore use active compounds To make animal care more economical and easier, or to some extent Is only possible with active compounds.   Pests include:   Those of the order Lice (Anoplura), such as the bedbug (Haematopinus spp.), White lice (Linognathus spp.), Bull lice (Solenopotes spp.), Lice (Pe) diculus spp.) and Pthirus spp.);   Those of the order of the Lice (Mallophaga), such as Trimenopon (Trimenopon spp.), Menopon spp., Eomenacanthus spp., Menaka Mint (Menacanthus spp.), Lice (Trichodectes spp.), Ferricola (F elicola spp.), Damarina (Damalinea spp.) and Boyicola spp. );   Diptera species, such as Chrysop spp., Abu (Ta banus spp.), housefly (Musca spp.), Haematobosca spp. , Haematobia spp., Stomoxys spp., Japanese housefly (Fannia spp.), Tset fly (Glossina spp.), Fruit fly (Lucilia spp.) , Blowfly (Calliphora spp.), Oak meromyia (Auchmeromyia spp.) Wolverine (Condylobia spp.), Cochliiomyia (Cochliiomyia spp.), Blue Fly (Chrysomyia spp.), Flesh fly (Sarcophaga spp.), Wallferty A (Wohlfartia spp.), Horsefly (Gasterophilus spp.), Esteromia (Oes teromyia spp.), Edemagena (Oedemagena spp.), Hypoderma spp. ), Estorus (Oestrus spp.), Reno Estorus (Rhinoestrus spp.), Melo Fagus (Melophagus spp.) And Hippobosca spp.   Of the flea order (Siphonaptera), such as the dog flea (Ctenocephalides spp.) Nichinomi (Echidnophaga spp.) And Ceratophyllus spp.   Those of the wall-eye (Metastigmata), such as ticks (Hyalomma spp.), Lipicepha Ruth (Rhipicephalus spp.), Bovine mite (Boophilus spp.),   Makabe Amblyomma spp., Haemophysalis spp., Derma Centr (Dermacentor spp.), Ixodes spp., Ixodes spp.  spp.), spider mites (Ornithodorus spp.) and spinous ear worms (Otobius spp.),   Those of the order Mesastigmata (Mesastigmata), such as chicken mites (Dermanyssus spp.), Ornithonissus spp., and lung wall larvae (Pneumonyssus s) pp.).   Those of the subgenus Prostigmata, such as cat lice (Cheyletiella spp.), Psorergates spp., Myobia spp., Demodex mites (Demodex spp.) And Neothrombicula spp .;   Those from Astigmata, such as mites (Acarus spp.) And Myocoptes (My ocoptes spp.), Psoroptes spp., Corioptes  spp.), fleas mites (Otodectes spp.), spider mites (Sarcoptes spp.), cats Mite (Notoedres spp.), Knemidocoptes (Knemidocoptes spp.), Neokune Midocoptes (Neoknemidocoptes spp.), Lytodites spp. And And Laminosioptes spp.   Producers and captive animals include mammals such as cows, horses, sheep, pigs, goats and camels. , Water buffalo, donkey, rabbit, deer and reindeer, fur animals such as mink, chin Chilas and raccoons, birds such as chickens, geese, turkeys and ducks , Freshwater and saltwater fish such as trout, carp and eel, reptiles and insects such as honeybee Chi and silkworm are included.   Research and laboratory animals include mice, rats, guinea pigs, and golden hamsters. , Dogs and cats are included.   Pets include dogs and cats.   Application of the active compounds can be carried out directly or in the form of suitable preparations, enterally, dermally. , By treatment of the environment or by moldings containing active compounds, eg strips, pres Use label, tape, color, ear tag, rim band or label device Do it.   Enteral applications of the active compounds are eg powders, suppositories, tablets, capsules, liniments, Orally in the form of beverages, granules, drenches, pills, drug-containing feed or drinking water. Sutra Skin applications are, for example, dipping, spraying, bathing, washing, pouring and spotting-on. , And powder application.   Suitable preparations include: solutions such as oral solutions, for oral administration after dilution Thickeners, cutaneous or body cavity solutions, injectable compositions and gels; milk for oral and dermal use Agents and suspensions, as well as semi-solid preparations; the active compound as an ointment base or oil-based. Water-in-water or water-in-water -oil) emulsion-based treated compositions; solid preparations such as powders, premixes or Thickeners, granules, pellets, tablets, pills and capsules; aerosols and activated Compound-containing molded body.   Solutions are prepared by dissolving the active compound in a suitable solvent and then adding additives such as solubilizers, acids, It is prepared by adding a base, buffer salts, antioxidants and protectants.   Solvents may include: physiologically acceptable solvents such as water, alcohol For example, ethanol, butanol, benzyl alcohol or glycerin, charcoal Hydrogen fluoride, propylene glycol, polyethylene glycol, N-methylpyrrolide And mixtures thereof.   If appropriate, it is also possible to use plants or plants which are physiologically acceptable for the active compound and which are suitable for injection. Can be dissolved in synthetic oil.   The solubilizers may include: Facilitates the dissolution of the active compound in the main solvent Substances which prevent the precipitation of solvents or active compounds. Examples are polyvinylpyrrolidone, po Reoxyethylated castor oil and polyoxyethylated sorbitan s There is a tell.   Protective agents include: benzyl alcohol, trichlorobutano , P-hydroxybenzoic acid ester and n-butanol.   Oral solutions are given directly. Concentrate is orally administered after initial dilution to the administration concentration I do.   Liquids used on the skin can be dropped, applied, rubbed in, sprayed on, Or atomize. These solutions are prepared as described above.   It is advantageous to add a sizing agent during the preparation.   Pastes include: Inorganic pastes such as bentonite, colloidal silica and And aluminum monostearate, as well as organic pastes such as cellulose derivatives, Rivinyl alcohol and its copolymers, acrylates and methacrylates.   Gel applied to skin or painted or introduced into body cavity I do. Gel is an ointment-like viscous solution prepared as described for injectable solutions. It is prepared by treating with an amount of paste that produces a transparent lump. The paste used is It is the one of the note.   The injectable composition is injected or sprayed onto a limited part of the skin, with activation The compound penetrates the skin and acts systemically.   Injectable compositions are prepared by dissolving the active compound in a suitable skin-tolerant solvent or solvent mixture. Prepare by suspending or emulsifying. If appropriate, auxiliary substances such as dyes, Add absorption enhancers, antioxidants, sunscreens or adhesives.   Solvents that may be mentioned are: water, alkanols, glycols, polyethylene. Examples of ren glycol, polypropylene glycol, glycerin, aromatic alcohol For example, benzyl alcohol, phenyl ethanol or Phenoxyethanol, esters such as ethyl acetate, butyl acetate or benzoic acid Benzyl, ethers such as alkylene glycol alkyl ethers such as dipro Pyrene glycol monomethyl ether or diethylene glycol monobutyl ether Ethers, ketones such as acetone or methyl ethyl ketone, aromatic and / or Aliphatic hydrocarbons, vegetable or synthetic oils, DMF, dimethylacetamide, N-methyl Lupyrrolidone or 2,2-dimethyl-4-oxy-methylene-1,3-dioxy Soran.   Colorants can be dissolved or suspended and can be used on animals. All permitted colorings.   Absorption enhancers include, for example, DMSO, bulking oils such as isopropyl myristate, and Dipropylene glycol largonate, silicone oil, fatty acid ester, triglyceride It is a ceria or fatty alcohol.   Antioxidants include sulfites or metabisulfites such as potassium metabisulfite. , Ascorbic acid, butylhydroxytoluene, butylhydroxyanisole or Or tocopherol.   The light-shielding agent is, for example, Novantisol acid.   The adhesive may be, for example, cellulose derivative, starch derivative, polyacrylate, or natural It is, of course, a polymer such as alginate or gelatin.   The emulsion may be used orally, dermally or as an injection.   Emulsions are either water-in-oil type or oil-in-water tie. It is one of the   These dissolve the active compound in a hydrophobic or hydrophilic phase, and A suitable emulsifier and, if appropriate, further auxiliaries such as colorants, absorption enhancers, Protectants, antioxidants, sunscreens and thickeners with other Prepare by homogenizing with the phase solvent.   The hydrophobic phase (oil) may include: paraffin oil, silicone oil, heaven. Natural vegetable oils such as sesame oil, almond oil and castor oil, synthetic triglycerides such as Capryl / capric acid biglyceride, triglyceride and chain length C_8-12Vegetable fat A mixture with acids or other specially selected natural fatty acids, saturated or unsaturated, or Partial glyceride mixture of fatty acids which may contain hydroxyl, or C₈/ C_{1 0} -Fatty acid mono- and diglycerides.   Fatty acid esters such as ethyl stearate, di-n-butyryl adipate, la Hexyl urate, Dipropylene glycol pelargonate, average branched chain length Fatty acids and chain length C₁₆~ C₁₈Ester of saturated fatty alcohol, myristic acid Sopropyl, isopropyl palmitate, chain length C₁₂~ C₁₈Saturated fatty alcohol Capryl / caprate, isopropyl stearate, oleic oleate Ile, decyl oleate, ethyl oleate, ethyl lactate, waxy fatty acid Stell, dibutyl phthalate, diisopropyl adipate, esters of the latter Mixture of etc.   Fatty alcohols such as isotridecyl alcohol, 2-octyldodecanol , Cetylstearyl alcohol or oleyl alcohol.   Fatty acids such as oleic acid and mixtures thereof.   The hydrophilic phases may include: water, alcohols such as propylene glycol. , Glycerin, sorbitol and mixtures thereof.   Emulsifying agents may include: nonionic surfactants such as polyoxye Chilled castor oil, polyoxyethylated monooleic Sorbitan acid salt, sorbitan monostearate, glycerin monostearate, Polyoxyethyl stearate and alkylphenol polyglycol ether An amphoteric surfactant such as di-Na-N-lauryl β-iminodipropionate or Or lecithin; anionic surfactants such as Na lauryl sulfate, fatty alcohols Sulfate ether and mono / dialkyl polyglycol ether or orthophosphoric acid Mono-ethanolamine salts of esters; cationic surfactants such as cetyl chloride Trimethylammonium.   Further auxiliary agents which may be mentioned are: thickeners and emulsion stabilizers such as carbohydrates. Xymethylcellulose, methylcellulose and other celluloses and starch derivatives Body, polyacrylate, alginate, gelatin, gum arabic, polyvinylpi Of loridone, polyvinyl alcohol, methyl vinyl ether and maleic anhydride Copolymer, polyethylene glycol, wax, colloidal silica or the above A quality mixture.   The suspension may be used orally or transdermally. This is an active compound if appropriate Further auxiliary agents such as wetting agents, coloring agents, absorption enhancers, protective agents, antioxidants, light-shielding agents It is prepared by adding an agent and suspending it in the excipient solution.   The excipients which may be mentioned are all homogeneous solvents and solvent mixtures.   Wetting agents (dispersants) which may be mentioned are the abovementioned surfactants.   Further auxiliaries which may be mentioned are those mentioned above. Semisolid preparations are oral or transdermal It can be administered by This is the same as the above suspensions and emulsions only in its high viscosity. different.   For the preparation of solid preparations, the active compound is admixed with auxiliaries if appropriate Are mixed with a suitable carrier material and converted to the desired shape.   Carrier substances which may be mentioned are all physiologically acceptable inert solid substances. Inorganic and organic materials can be used for this role. Inorganic substances include sodium chloride , Carbonates such as calcium carbonate or hydrogen carbonate, aluminum oxide, silicic acid, There is white clay, precipitated or colloidal silicon dioxide or phosphate.   Organic substances include, for example, sugar, cellulose, nutrients and feeds such as milk powder, animal There is meat, grain and coarse flour, or starch.   Auxiliary substances are the protective agents, antioxidants or colorants already mentioned above.   Further suitable auxiliary substances are lubricants and glidants such as magnesium stearate, Stearic acid, talc, bentonite, disintegration promoting substances such as starch or cross-linking Combined polyvinylpyrrolidone, binders such as starch, gelatin or straight chain Rivinylpyrrolidone and also dry binders such as microcrystalline cellulose.   The invention therefore also finds use as an ectoparasiticides. And a composition for controlling ectoparasites. It relates to the use of compounds of general formula (I) for the preparation.   The ready-to-use preparation should have a concentration of 10 ppm to 20% by weight, preferably 0.1 to 10% by weight. Containing the active compound in a degree.   Preparations diluted before use are 0.5-90% by weight, preferably 5-50% by weight Of the active compound.   Generally, about 1 to about 1 kg / day of body weight to achieve effective results. It has proven to be advantageous to administer an amount of 100 mg of the active compound.   All percentages are weight percentages unless otherwise stated.   The following preparation examples and the following biological examples are respectively new compounds of the general formula (I) It is for explaining the production of a product and its biological activity. Example 1   2.54 g (20 millilitres) of 5,5-dimethyl-pyrrolidine-2,4-dione First) introduced into 70 ml of anhydrous methylene chloride and triethylamine 2. 8 ml was added. 2.34 ml of morpholine carbamoyl chloride was added dropwise at 0-10 ° C. While monitoring the agitation of the mixture by thin layer chromatography. From room temperature to room temperature. The reaction solution was washed twice with 0.5N NaOH and the organic phase was dried. , And the solvent was evaporated in vacuo. Recrystallization of the residue from ethyl acetate / n-hexane did. Melting point 198 ° C   The compounds of Table 5 were similarly obtained: Preparation of starting compounds Example (II-1)   100.6 g (0.898 mol) of potassium t-butyrate was added to THF50 at room temperature. Ethyl 2-isovaleroyloxy-isobutyrate in 0 ml 49.5 g (0.229 mol. Solution). After stirring this at room temperature overnight, the mixture was mixed with 500 ml of water. And the whole was acidified with concentrated HCl. The organic phase is separated, and the aqueous phase is vinegar. It was extracted twice with ethyl acidate. The combined organic phases are MgSO 4._FourDried over, filtered, Then the solvent was removed. The crystalline residue thus obtained was mixed with petroleum ether. Purified by stirring. It was then washed with water and dried. Yield: 21.5 g, theoreticalΔ55%, pale yellow crystalline powder. Melting point: 188-189 ° C   Example   Ethyl 2-isovaleroyloxyisobutyrate   Isovaleroyl chloride (30.1 g, 0.25 mol) was added to 2-hydroxyisosol at 40 ° C. It was added dropwise to 33.0 g (0.25 mol) of ethyl butyrate. Gassing the mixture Stir until end of and then briefly heated to 100 ° C. The resulting crude product (yellow (Colored oil) is degassed in an oil pump vacuum, Then, it was reacted without further purification. Yield 53.3 g (99% of theory).   Example II-2   N- (2-cyclopropyl-alanine in 100 ml of anhydrous tetrahydrofuran Methyl ester) -malonic acid methyl ester amide 94 g (0.386 mol) Sodium ethoxide 2 in 200 ml of anhydrous tetrahydrofuran at 10-20 ° C It was added dropwise to 6.2 g (0.386 mol). 1 hour later, anhydrous methanol 5 37.8 g (0.386 mol) of concentrated sulfuric acid in 0 ml was added to the mixture at 0-10 ° C, and then This was stirred for 15 minutes. The mixture is suction filtered and the filtrate is concentrated and the residue CH residue₂Cl₂Taken up, this solution is washed twice with 40 ml of water, MgSO 4._Four Dried in and concentrated again. The residue was suspended in 380 ml of acetonitrile, 9 g of water are added and the mixture is mixed with CO₂Boiled under reflux until the generation of . 26.9 g (theoretical value) of the above compound having a melting point of 114 ° C.△46%) evaporates Obtained following recrystallization of the residue from ethyl acetate / n-hexane.   The compounds shown in Table 6 were produced in the same manner as in Examples II-1 and II-2. Example A Phaedon larva test Solvent: 3 parts by weight of dimethylformamide Emulsifier: 1 part by weight of alkylaryl polyglycol ether   To prepare a suitable preparation of active compound, 1 part by weight of active compound Mix with solvent and the above amount of emulsifier and dilute the concentrate with water to the desired concentration. I chose   Cabbage leaves (Brassica oleracea) in a preparation of active compound of the desired concentration. Treated by dipping, and mustard beetle (Phaedon cochlearia The larvae of e) were infected as long as the leaves were moist.   After a certain period of time, the degree of eradication in% was measured. 100% of all beetles It means the killing of worms; 0% means that no beetle larvae are killed.   In this test, for example, the compound according to Preparation Example 3 has a concentration of, for example, 0.1%. After 7 days, the degree of eradication was 100%. Example B Critical concentration test / Root-systemic action Test insect: Aphis fabae Solvent: 4 parts by weight of acetone Emulsifier: 1 part by weight of alkylaryl polyglycol ether   To prepare a suitable preparation of active compound, 1 part by weight of active compound Mix with solvent, add the above amount of emulsifier and dilute this concentrate with water to the desired concentration. did.   A preparation of this active compound was mixed thoroughly with soil. Of the active compound in the formulation The concentration is not really important, as it relates to the weight of active compound per unit volume of soil. Only determined and given in ppm (= mg / l). Pack the treated soil in Then, cabbage (Brassica oleracea) was planted in these plants. Live like this It is possible to take up sex compounds from the soil by the roots of plants and transfer them into the leaves. did it.   Only the leaves were infected 7 days later with the above test animals to show the root-systemic effect. Evaluation was performed by counting or estimating dead animals after a further 2 days. . The root-systemic effect of the active compounds is calculated by subtracting the number of kills. Everything 100% of all test animals die.   In this test, for example, the compounds according to Preparation Examples 1 and 2 are added to, for example, 20 pp. An active compound concentration of m produced 100% eradication. Example C Aphid (Myzus) test Solvent: dimethylformamide 7 parts by weight Emulsifier: 1 part by weight of alkylaryl polyglycol ether   To prepare a suitable preparation of active compound, 1 part by weight of active compound Mix with the above amount of solvent containing emulsifier and dilute this concentrate with water to obtain the desired concentration. I chose   Cabbage leaves (Brassi) severely infected with the aphid Myzus persicae. ca oleracea) with a preparation of active compound at the desired concentration Processed until   After a certain period of time, the degree of eradication was measured as a percentage. 100% is all aphids 0% means that the aphids did not die. To taste.   In this test, for example, the compounds according to Preparation Examples 2, 4 and 5 are, for example, 0.1%. At a concentration of 1% active compound a eradication of at least 95% was produced after 6 days. Example D Aphis test (systemic effect) Solvent: dimethylformamide 7 parts by weight Emulsifier: 1 part by weight of alkylaryl polyglycol ether   To prepare a suitable preparation of active compound, 1 part by weight of active compound Mix with solvent and the above amount of emulsifier and dilute the concentrate with water to the desired concentration. I chose   Bean plants seriously infected with Aphis fabae (Vic ia faba) infiltrate the soil with a preparation of the active compound without wetting the above-ground parts of each. Wet with 20 ml of the preparation of active compound at the desired concentration. Is the active compound the root? Was taken in and moved to the ground.   After a certain period of time, the degree of eradication in% was measured. 100% of all Affis Means death; 0% means that Affis does not die.   In this test, for example, the compound of Preparation Example 1 was used at a concentration of, for example, 0.1%. After 100 days, the degree of eradication was 100%. Example E Test with Lucilia cuprina-resistant larvae Emulsifier: 35 parts by weight of ethylene glycol monomethyl ether         Nonylphenol polyglycol ether 35 parts by weight   To prepare a suitable preparation of active compound, 3 parts by weight of active compound are prepared. Mix 7 parts by weight of the above mixture, and dilute the concentrate thus obtained with water Was set to the concentration of.   About 20 cm of Lucilia cuprina resistant larvae^ThreeHorse Of meat and 0.5 ml of a preparation of active compound was introduced into a test tube. 24:00 After a while, the degree of eradication was measured.   In this test, for example, the compounds according to Preparation Examples 3, 4 and 6 are for example 10 100% eradication occurred with an active compound concentration of 00 ppm.

────────────────────────────────────────────────── ─── Continuation of front page    (81) Designated countries EP (AT, BE, CH, DE, DK, ES, FR, GB, GR, IE, IT, LU, M C, NL, PT, SE), OA (BF, BJ, CF, CG , CI, CM, GA, GN, ML, MR, NE, SN, TD, TG), AU, BB, BG, BR, BY, CA, CN, CZ, FI, HU, JP, KR, KZ, LK, N O, NZ, PL, RO, RU, SK, UA, US (72) Inventor Erderen, Christoph             Federal Republic of Germany Day 42799 Reichlin             Gen Unterbiyucher Hof 15 (72) Inventors Hartwig, Jürgen             Federal Republic of Germany Day 42799 Reichlin             Gen Am Kloster 39 (72) Inventors Toulberg, Andreas             Federal Republic of Germany-40699 Elkler             To Naebeek 19 (72) Inventor Menke, Norbert             Federal Republic of Germany Day 51381 Rafel             Kusen Grundermiyure 2

Claims (1)

[Claims]   1. Formula (I)     Wherein A is hydrogen, or in each case optionally halogen, alkoxy or halo. Represents alkyl or cycloalkyl optionally substituted with genoalkoxy Or an optionally substituted aryl or aralkyl in each case Represent     B represents hydrogen or alkyl, or     A and B are optionally containing heteroatoms together with adjacent carbon atoms. Represents a ring which may be replaced,     Z represents nitrogen or oxygen,     X is hydrogen, or in each case optionally halogen, alkyl, alkoxy, ar Quilthio, halogenoalkyl, halogenoalkoxy or halogenoalkylthio Alkyl, cycloalkyl, alkoxy or alkyl optionally substituted with Represents Thio,     R¹Represents alkyl, alkenyl or acyl,     R²Is an alkyl, alkene optionally substituted with halogen in each case. Represents a nyl, alkoxyalkyl or aryl, or optionally a heteroatom Represents a cycloalkyl which may be contained, or     R¹And R²At any time together with the nitrogen atom to which these things bind Represents a ring which may be substituted and may optionally contain further heteroatoms. ,     G is hydrogen when Z represents nitrogen, or optionally halogen or a in each case. Alkoxy, alkeni optionally substituted with lucoxy or halogenoalkoxy Represents an alkyl or cycloalkyl, or is optionally substituted in each case Represents reel or aralkyl, or represents acyl, or     A and G are optionally substituted with the atoms to which they are attached And represents a ring which may further contain a heteroatom, Substituted 4-carbamoyl-pyrrolin-2-one derivatives and 4-carbamoy Ru-dihydrofuran-2-one derivative.   2. A is hydrogen, or halogen in each case, C₁~ C_Four-Alkoxy and / Or C₁~ C_Four-C optionally substituted with halogenoalkoxy₁~ C_Ten-A Rukiru or C_Three~ C_Ten-Cycloalkyl, or optionally halogen in each case, CN, nitro, C₁~ C₈-Alkyl, C₁~ C₈-Alkoxy, C₁~ C₈-Archi Lucio, C₁~ C₈-Halogenoalkyl and / or C₁~ C₈-Halogenoalkoki Phenyl, naphthyl or phenyl-C optionally substituted with Si₁~ C₆-Al Represents a kill, B is hydrogen or C₁~ C₈Represents alkyl, or A and B together with the carbon atom to which they are attached are optionally halogen, Optionally substituted with a kill and / or alkoxy, and optionally nitrogen, oxygen, sulfur. Represents a 3- to 8-membered ring which may contain yellow or a group -O-CO-, X is hydrogen, or halogen in each case, C₁~ C₆-Alkyl, C₁ ~ C₆-Alkoxy, C₁-C₆-Alkylthio, C₁~ C₆-Halogenoalkyl and And / or C₁~ C₆-C optionally substituted with halogenoalkoxy₁~ C₆-A Luquil, C₁~ C₆-Alkoxy, C₁~ C₆-Alkylthio or C_Three~ C₇-Shiku Represents lower alkyl, R¹Is C₁~ C₆-Alkyl or C_Three~ C₆-Alkenyl or radical Or -SO₂Represents one of -OR, Here, R and R'are independently of each other, in each case optionally halogen, C₁~ C₆-Al Kill, C₁~ C₆-Alkoxy, C₁~ C₆-Halogenoalkyl and / or C₁~ C₆-C optionally substituted with halogenoalkoxy₁~ C_Ten-Alkyl, C_Three~ C_Ten-Cycloalkyl, phenyl, phenyl-C₁~ C_Four-Alkyl or Hetari Represents R'may also represent hydrogen, or R and R ', together with the nitrogen atom to which they are attached, are optionally C₁~ C_Four-A It may be substituted with rukyi and optionally up to two more nitrogen or oxygen atoms. Represents a 5- to 7-membered ring which may be included, R²Is in each case optionally halogen-substituted C₁~ C₂₀-Alkyl, C_Three ~ C₂₀-Alkenyl, C₁~ C₈-Alkoxy-C₁~ C₈-Alkyl, C₁~ C₈ -Alkylthio-C₁~ C₈-Alkyl, phenyl or optionally up to 2 oxygens and And / or C optionally containing a sulfur atom_Three~ C₈Represents cycloalkyl, or Iha R¹And R²And C at any time together with the nitrogen atom to which these are bound₁~ C_Four-A It may be replaced by rutile and may contain up to 2 oxygens at any time. And / or a 3- to 7-membered ring which may contain sulfur, Z preferably represents nitrogen or oxygen, G is hydrogen when Z represents nitrogen, or optionally halogen in each case, C₁~ C₆-Alkoxy and / or C₁~ C₆-Substituted by halogenoalkoxy Good C₁~ C₈-Alkyl, C_Three~ C₈-Alkenyl or C_Three~ C₈-Cycloal Kill, or optionally halogen, CN, nitro, C in each case₁~ C₆-Alkyl, C₁~ C₆-Alkoxy, C₁-C₆-Alkylthio, C₁~ C₆-Halogenoalkyl , C₁~ C₆-Halogenoalkylthio and / or C₁~ C₆-Halogenoalkoxy Optionally substituted with phenyl, naphthyl or phenyl-C₁~ C_Four-Archi Or Or -SO₂Represents one of -OR, Here, R and R'are independently of each other, in each case optionally halogen, C₁~ C₆-Al Kill, C₁~ C₆-Alkoxy, C₁~ C₆-Halogenoalkyl and / or C₁~ C₆-C optionally substituted with halogenoalkoxy₁~ C₈-Alkyl, C_Three~ C₇ -Cycloalkyl, phenyl, phenyl-C₁~ C_Four-Alkyl or hetary Represents the R'can also represent hydrogen, or R and R ', together with the nitrogen atom that binds to them, are optionally C₁~ C_Four-A It may be substituted with rukyi and optionally up to two more nitrogen or oxygen atoms. Represents a 5 to 7 membered ring which may be included, or A and G together with the atoms to which they are attached are optionally halogen and / or Is C₁~ C_FourOptionally substituted with alkyl, optionally oxygen or Is a 4- to 8-membered ring which may contain a sulfur atom and may be optionally unsaturated. Express A compound of formula (I) according to claim 1.   3. A is hydrogen, or in each case, fluorine, chlorine, bromine, C₁~ C_Four-Al Substituted with cooxy, trifluoromethoxy and / or pentafluoroethoxy May be C₁~ C₈-Alkyl or C_Three~ C₈-Cycloalkyl, or each Fluorine, chlorine, bromine, CN, nitro, C at any time₁~ C_Four-Alkyl, C₁~ C_Four-Al Coxy, C₁~ C_Four-Alkylthio, C₁~ C_Four-Halogenoalkyl and / or C₁ ~ C_Four-Phenyl, naphthyl or optionally substituted with halogenoalkoxy Phenyl-C₁~ C_FourRepresents an alkyl, B is hydrogen, or C₁~ C₆Represents alkyl, or A and B, together with the carbon atom to which they are attached, are optionally fluorine, chlorine, Bromine, C₁~ C_Four-Alkyl and / or C₁~ C_Four-Substituted by alkoxy And a 3- to 7-membered ring optionally containing an oxygen or sulfur atom. , X is hydrogen, or in each case optionally fluorine, chlorine, bromine, C₁~ C_Four-Alkyl, C₁~ C_Four-Alkoxy, C₁~ C_Four-Alkylthio, C₁~ C_Four-Halogenoalkyl And / or C₁~ C_Four-C optionally substituted with halogenoalkoxy₁~ C_Four− Alkyl or C_Three~ C₆Represents -cycloalkyl, R¹Is C₁~ C_Four-Alkyl or C_Three~ C_Four-Alkenyl or radical Represents Where R is optionally fluorine, chlorine, bromine, C in each case.₁~ C_Four-Alkyl, C₁~ C_Four-Alkoxy, C₁~ C_Four-Halogenoalkyl and / or C₁~ C_Four-Halogen C optionally substituted with noalkoxy₁~ C₈-Alkyl, C_Three~ C₈-Cycloa Represents alkyl, phenyl, benzyl, pyryl, thienyl or pyridyl, R²Is optionally fluorine- and / or chlorine-substituted C in each case₁~ C₁₄-Alkyl , C_Three~ C₁₄-Alkenyl, C₁~ C_Four-Alkoxy-C₁~ C₆-Alkyl, C₁~ C_Four-Alkylthio-C₁~ C₆-Alkyl, phenyl or optionally oxygen and / or Is C which may contain a sulfur atom_Three~ C₇Represents cycloalkyl, or R¹And R²And C at any time together with the nitrogen atom to which these are bound₁~ C_Three-A Optionally substituted with rukyi and optionally containing oxygen and / or sulfur atoms Represents a 3- to 6-membered ring which may be Z represents nitrogen or oxygen, When G represents Z, hydrogen, or in each case optionally fluorine, chlorine, odor Elementary, C₁~ C_Four-Alkoxy and / or C₁~ C_Four-Substituted by halogenoalkoxy May be C₁~ C₆-Alkyl, C_Three~ C₆-Alkenyl or C_Three~ C₆− Shi Chloroalkyl, or optionally in each case fluorine, chlorine, bromine, CN, nitro, C₁ ~ C_Four-Alkyl, C₁~ C_Four-Alkoxy, C₁~ C_Four-Alkylthio, C₁~ C_Four -Halogenoalkyl, C₁~ C_Four-Halogenoalkoxy and / or C₁~ C_Four-C Phenyl, naphthyl, benzyl optionally substituted with logenoalkylthio, or Is phenylethyl or a group Represents one of Here, R and R'independently of one another are in each case optionally fluorine, chlorine, bromine, C₁ ~ C_Four-Alkyl, C₁~ C_Four-Alkoxy, C₁~ C_Four-Halogenoalkyl and / Or C₁~ C_Four-C optionally substituted with halogenoalkoxy₁~ C₈-Archi Le, C_Three~ C₈-Cycloalkyl, phenyl, benzyl, pyryl, thienyl or Represents pyridyl, R'may also represent hydrogen, or R and R ', optionally together with the nitrogen atom to which they are attached, C₁~ C_Four-A Optionally substituted with rukyi and optionally further containing oxygen and / or nitrogen atoms Represents a 5- to 7-membered ring which may be A and G, together with the atoms to which they are attached, are optionally C₁~ C_Four-Alkyl Represents a 5- to 8-membered saturated carbocycle which may be substituted with A compound of formula (I) according to claim 1.   4. A is hydrogen, or in each case the same or different or one or more Methyl, ethyl, propyl, i-propyl, substituted with the above fluorine or chlorine, n-butyl, s-butyl, i-butyl, t-butyl, phenyl or benzyl Represent B is hydrogen, methyl, ethyl, propyl, i-propyl, n-butyl, s-butyl Represents i-butyl or t-butyl, or A and B together form a group-(CH₂)_Four-,-(CH₂)_Five-,-(CH₂)₆−, -(CH₂)_Four-CH (CH_Three)-,-(CH₂)_ThreeCH (CH_Three) -CH₂-,-( CH₂)₂-CH (CH_Three)-(CH₂)₂-,-(CH₂)₂ -CH (C₂H_Five)-(CH₂)₂-,-(CH₂)₂-CH (C_ThreeH₇)-(CH₂)₂ -,-(CH₂)₂-CH (C_FourH₉)-(CH₂)₂-, -CH₂O (CH₂)₂−, -CH₂S- (CH₂)₂-,-(CH₂)₂-O- (CH₂)₂-Or-(CH₂)₂ -S- (CH₂)₂Represents one of the X is hydrogen, or in each case optionally fluorine, chlorine, bromine, methyl, ethyl, pro Pill, i-propyl, methoxy, ethoxy, trifluoromethyl and / or Methyl, ethyl, propyl, i-p which may be substituted with trifluoromethoxy Ropyl, n-butyl, s-butyl, i-butyl, t-butyl, methoxy, etoxy Represents cyclo, cyclopropyl, cyclopentyl or cyclohexyl, R¹Is methyl, ethyl, propyl, i-propyl, allyl, methylsulfonyl, Represents ethylsulfonyl or propylsulfonyl, R²C in each case optionally substituted with fluorine and / or chlorine₁~ C_Ten -Alkyl, C_Three~ C_Ten-Alkenyl, C_Three~ C₆-Cycloalkyl, C₁~ C_Three -Alkoxy-C₁~ C_FourRepresents alkyl or phenyl, or R¹And R²Are optionally methyl and / or with the nitrogen atom to which these are bound Alternatively, it may be substituted with ethyl and may optionally contain an oxygen atom. 3 ~ Represents a 6-membered ring, Z represents nitrogen or oxygen, When G represents Z, hydrogen, or in each case optionally fluorine and / or Is methyl, ethyl, propyl, i-propyl, buty which may be substituted with chlorine. Ru, s-butyl, i-butyl or t-butyl, or optionally fluorine, chlorine, nit B, C₁~ C_Four-Alkyl and / or C₁~ C_Four-Phenyl optionally substituted with alkoxy, or a group Where R and R'are independent of each other and in each case optionally fluorine and / or chlorine. Optionally substituted C₁~ C₆-Alkyl, C_Three~ C₆-Alkenyl, phenyl Or benzyl, R'may also represent hydrogen, or R and R'are taken together to form the group-(CH₂ )_Three-,-(CH₂)_Four-,-(CH₂)_Five-, -CH₂-CH (CH_Three) (CH₂)₂ -, -CH₂O- (CH₂)₂-Or-CH₂S- (CH₂)₂-Represents one of Or A and G together form a group-(CH₂)_Three-,-(CH₂)_Four−, Represents one of the A compound of formula (I) according to claim 1.   5. Formula (I)     In the formula, A, B, X, Z, G, R¹And R²Has the meaning described in claim 1. Do 4-carbamoyl-pyrrolin-2-one and 4-carbamoyl-dihydrofuran In the production of N-2-one, the formula (II)     Wherein A, B, X, Z and G have the meanings given above, Compound   a) Formula (III) optionally in the presence of a diluent and optionally in the presence of an acid binder.     Where R¹And R²Has the meaning defined in claim 1, and     Hal represents halogen, With carbamoyl halide of   b) Phosgene in the first step optionally in the presence of a diluent and optionally in the presence of an acid binder. Or formula (IV)         R^Three-O-CO-Cl (IV)     Where R^ThreeRepresents an optionally halogen-substituted alkyl, Reacting with the formate ester and the compound thus obtained in the second step Formula (V) optionally in the presence of a diluent     Where R¹And R²Has the meaning defined in claim 1, 4-carbamoyl-pyrrolid of the formula (I), characterized in that it is reacted with an amine of And a method for producing 4-carbamoyl-dihydrofuran-2-one.   6. The content of at least one compound of formula (I) according to claim 1 is characterized. A pest control agent.   7. The content of at least one compound of formula (I) according to claim 1 is characterized. An agent for arthropodicides.   8. Plant protection, household, hygiene, protection of stored products and pests in animals Use of a compound of formula (I) according to claim 1 for controlling.   9. Arthropods in plant protection, household, hygiene, protection of stored products and animals Use of a compound of formula (I) as defined in claim 1 in controlling.   10. A compound of formula (I) according to claim 1 with a filler and / or a surfactant A method for producing a pest control agent, which comprises mixing.