DD298384A5 - DERIVATIVES CARBOCYCLIC ANILIDES - Google Patents

Abstract

Described are novel cycloalkyl or Cycloalkenylcarbonsaeureanilide the general formula * in which X is optionally substituted alkyl-substituted cycloalkyl or optionally alkyl substituted cycloalkenyl, Hal is halogen and Y1, Y2 and Y3 are independently hydrogen, halogen, optionally halogen-substituted alkyl, optionally halogen-substituted alkoxy or optionally halogen-substituted alkylthio and Z represents the groups COOR2 or COR1, where R1 and R2 are identical or different and represents optionally halogen-substituted alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl, polyalkoxyalkyl and optionally substituted cycloalkyl, optionally substituted phenyl, optionally substituted phenylalkyl or substituted phenoxyalkyl, as well as a process for their preparation and their use for the control of pests.

Description

The present invention relates to novel cycloalkyl or Cycloalkenylcarbonsäureanilide, a process for their preparation and

their use for controlling pests, especially fungi.

It is known that certain carbamates possess good fungicidal properties (cf EP 293718). Furthermore, many carboxylic acid anilides with fungicidal activity, in particular with high activity against benzimidazole tolerante Plant pathogens, known (see EP 117024, EP 125901, EP 100615). There have been new cycloalkyl- or cycloalkenyl-carboxylic acid anilides of the general formula (I)

shark

in which

X is optionally alkyl-substituted cycloalkyl or optionally alkyl-substituted cycloalkenyl, Shark stands for halogen and

Y ', Y ² u. Y ³ independently of one another are hydrogen, halogen, optionally halogen-substituted alkyl, optionally halogen-substituted alkoxy or optionally halogen-substituted alkylthio, and

Z represents the groups COOR ² or COR *, where R 'and R ^{2 are the} same or different and are optionally halogen-substituted alkyl, alkenyl, alkoxyalkyi,

Alkylthioalkyl, polyalkoxyalkyl and optionally substituted cycloalkyl, optionally substituted phenyl, optionally substituted phenylalkyl or substituted phenoxyalkyl,

found.

The substituted cycloalkyl- or cycloalkenyl-carboxylic acid anilides of the formula (I) contain one or more Asymmetry centers and can thus be in the form of diastereomers or diastereomeric mixtures, which in

incurred in different proportions. Most of them are obtained as racemates.

Furthermore, it has been found that the novel substituted cycloalkyl or Cycloalkenylcarbonsäureanilide of formula (I)

NH-C-X

(D ₁ shark

in which

X is optionally alkyl-substituted cycloalkyl or optionally alkyl-substituted cycloalkenyl, Shark for halogen and Y ', Y ² u. Y ^{3 are} identical or different and represent hydrogen, halogen, optionally halogen-substituted alkyl,

optionally halogen-substituted alkoxy or optionally halogen-substituted alkylthio and

Z stands for the groups COOR ² or COR ¹ , where R ¹ and R ^{2 are the} same or different and represent optionally substituted halogen, alkyl, alkenyl, alkoxyalkyl,

Alkylthioalkyl, polyalkoxyalkyl and optionally substituted cycloalkyl, optionally substituted phenyl, optionally substituted phenylalkyl or substituted phenoxyalkyl,

obtained when aminophenols of the formula (II)

in which

Hal, Y ¹ , Y ² and Y ^{3 have} the meanings given above, in a first reaction step with carboxylic acid derivatives of

Formula (III)

O XC-HaI ¹ (III)

in which

X has the meaning given above and Hal ^{1 represents} halogen, preferably chlorine, or a leaving group commonly used in acylating reactions, preferably one

activating estarrest, stands,

if appropriate in the presence of an acid acceptor and if appropriate in the presence of a solvent or diluent, and in a second reaction step these intermediates of the formula (IV)

(IV)

in which

X, Y ¹ . Y ² . Y ³ and Hai have the abovementioned meaning, with carbonyl derivatives of the formula (V)

Z-HaI ² (V)

in which

Z has the abovementioned meaning and Hal ^{2 represents} halogen, preferably chlorine, or a leaving group commonly used in acylation reactions, preferably one

activating ester residue,

if appropriate in the presence of an acid radical acceptor and if appropriate in the presence of a solvent or diluent.

Finally, it has been found that the substituted cycloalkyl or cycloalkenylcarboxylic acid anilides of the formula (I) and (IVa) i.a. have a high fungicidal activity. The novel compounds can also be used with other known, highly effective compounds in synergistic mixtures.

In the context of the present invention, the substituents preferably have the following meanings: Halogen may, wherever not indicated otherwise, mean fluorine, chlorine, bromine and iodine, preferably fluorine, chlorine and bromine. Alkyl, alkoxy and alkylthio are a radical which has 1-8 each alkyl unit, preferably 1-6 and particularly preferably 1-4 carbon atoms, for. For example, methyl, ethyl, η- and iso-propyl, n-, sec-, iso- and tert-butyl, pentyl, n-hexyl or iso-hexyl, methoxy, ethoxy, n- and iso-propoxy, n- , see. ·, Iso- and tert-butoxy, pentoxy and hexoxy, methylthio, ethylthio, n- and iso-Propylthio, n-, see-, iso- and tert-butylthio, pentylthio and hexylthio.

Halogenoalkoxy or Halogonalkylthlo is generally a bonded via oxygen or sulfur, straight or branched hydrocarbon residue with 1-6 carbon atoms and 1-9 identical or different halogen atoms. Preference is given to radicals mi 4 carbon atoms and 1-5 identical or different halogen atoms. Very particular preference is given to radicals m ^; of the 2 carbon atoms and 1-3 same or different halogen atoms. Examples which may be mentioned are: trifluoromethoxy.trichloromethoxy, difluorochloromethoxy, dichlorofluoromethoxy, difluoroethoxy, trifluoroethoxy, tetrafluoroethoxy, pentafluoroethoxy, trifluoromethylthio, trichloromethylthio, difluorochloromethylthio, dichlorofluoromethylthio, difluoroethylthio, trifluoromethylthio, tetrafluoroethylthio.

Haloalkyl has the meaning of haloalkoxy, with the difference that the oxygen or sulfur atom is missing. Cycloalkyl is generally a cyclic hydrocarbon radical of 3-10 carbon atoms. Preferred are radicals having 3-7 carbon atoms. Examples include: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclodecanyl.

The cycloalkyl radicals may be monosubstituted to polysubstituted. Substituents which may be mentioned are alkyl having 1-4 carbon atoms, halogen, haloalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, alkoxy having 1 to 4 carbon atoms, hydroxy and alkylcarbonylox having 1 to 6 carbon atoms in the alkyl part. Cycloalkenyl is generally a cyclic hydrocarbon radical having 5-10 carbon atoms. Preference is given to radicals having 5-7 carbon atoms. Examples include: cyclopentenyl, cyclohexenyl and cycloheptenyl.

The cycloalkenyl radicals may be monosubstituted to polysubstituted. As substituents alkyl with 1-6 carbon atoms may be mentioned.

Alkyl here has the preferred and particularly preferred meaning, which has already been given above. Phenyl, phenyl and substituted Phonoxyalkyl are generally phenyl, phenylalkyl and phenoxyalkyl, in which Phenyiwasserstoffatome optionally replaced by one or more substituents Y '' - Υ ⁶ '. Y '' - Υ ⁵ 'here have the meaning of Y ¹ , Y ² and Y ³ and nitro and cyano.

Alkenyl is generally a straight-chain or branched hydrocarbon radical having 2 to 8 carbon atoms and one or more, preferably with one or two double bonds. Lower alkenyl having 2 to 6 carbon atoms and one double bond is preferred. Particularly preferred is an alkenyl group having 2 to 5 carbon atoms and a double bond.

The substituted cycloalkyl- or cycloalkenylcarboxylic acid anilides according to the invention are generally represented by the formula (I)

Are defined. Preference is given to compounds of the formula (I) in which

X is optionally one to four times, identically or differently by straight-chain or branched alkyl with

1-4 carbon atoms substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or cycloheptyl or represents cycloalkenyl with 5-7 ring members, wherein the cycloalkyl or cycloalkenyl one to six times, identically or differently substituted by straight-chain or branched alkyl having 1-4 carbon atoms know his,

Hai stands for fluorine, chlorine or bromine,

Y ¹ , Y ² u. Y ^{3 are} identical or different and represent hydrogen, fluorine, chlorine, bromine, straight-chain or branched alkyl having 1-4 carbon atoms, straight-chain or branched alkoxy or alkylthio each having 1-4 carbon atoms, haloalkyl, haloalkoxy or haloalkylthio each having 1 -4 carbon atoms in the straight-chain or branched alkyl part and with 1-5 identical or different halogen atoms,

Z stands for COOR ² or COR ¹ , where

R 'and R ^{2 are} identical or different and represent optionally C 1 -C ₈ -alkyl, C 1 -C ₈ -alkenyl, C 1 -C ₄ -alkoxy-C 1 -C ₄ -alkyl, CrAlkoxy-C ^ Cralkoxy-Cr Cralkyl, C, -C ₄ alkylthio-C, alkyl, or -C ₄ unsubstituted or monosubstituted to pentasubstituted by identical or different C | -C ₄ haloalkyl, halogen, C) -C ₄ -AlkVl ₁ C ₁ -C ₄ -AlkOXy, hydroxy, C ₁ -C ₆ -alkylcarbonyloxy substituted C ₃ -C ₇ -cycloalkyl or phenyl unsubstituted or in the phenyl moiety mono- to trisubstituted, identically or differently by Y ¹ VY "substituted phenyl -C ₄ alkyl or unsubstituted or in the phenyl moiety to five times, identically or differently by Y "-Y ⁵ 'substituted phenoxyalkyl, wherein Y''- Υ ⁶ ' the meaning of Y'-Y ³ , NO ₂ and cyano to have.

Particular preference is given to compounds of the formula (I) in which X is one or two times, identical or different, by straight-chain or branched alkyl with

1-4 carbon atoms substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or cycloheptyl, optionally represents mono- or di-pentane, identically or differently substituted by straight-chain or branched alkyl having 1-4 carbon atoms, substituted cyclopentenyl, cyclohexenyl, cycloheptenyl,

Y ¹ , Y ² u. Y ^{3 are the} same or different and are hydrogen, fluorine, chlorine, bromine, methyl or trifluoromethyl and Hai stands for fluorine, chlorine or bromine, Z stands for COOR ² or COR ¹ , where R ¹ and R ^{2 are the} same or different and are C ₁ -C ₄ -alkyl, C ₁ -C ₆ -alkenyl, C ₁ -C ₄ -alkoxy-C ₁ -C ₄ -alkyl,

C 1 -C 4 alkoxy-C 1 -C ₄ alkoxy-C 1 -C 4 -alkyl, C 1 -C ₄ -alkylthio-C ₁ -C ₂ -alkv 1, or unsubstituted or mono- to trisubstituted by identical or different fluorine, chlorine, bromine and C 1 -C 12 -alkyl , C 1 -C 2 -alkoxy, C ₁ -C 6 -alkylcarbonyloxy, substituted C ₃ -C 12 -cycloalkyl, or unsubstituted or mono- to trisubstituted by identical or different nitro, cyano, fluoro, chloro, bromo, methyl, trifluoromethyl, trifluoromethylthio, methoxy Trifluoromethoxy-substituted phenyl or unsubstituted or monosubstituted to trisubstituted by the same or different nitro, cyano, fluoro, chloro, bromo, methyl, trifluoromethyl, trifluoromethylthio, methoxy, trifluoromethoxy, phenyl-C ₁ -C ₂ -alkyl or unsubstituted or simple to three times, identically or differently by nitro, cyano, fluorine, chlorine, bromine, methyl, trifluoromethyl, trifluoromethylthio, methoxy, trifluoromethoxy substituted phenoxy-C, -C2-alkyl.

Very particular preference is given to compounds of the formula (I) in which X for methyl or ethyl substituted in the 1 - or 1,3-position cyclopentyl, cyclohexyl, cycloheptyl,

Cyclopentenyl, cyclohexenyl, cycloheptenyl, which are optionally additionally substituted by another alkyl radical having 1-3 carbon atoms,

Shark stands for fluorine, chlorine or bromine and Y ¹ , Y ² u. Y ^{3 are} identical or different and represent hydrogen, fluorine, chlorine, bromine or trifluoromethyl, Z stands for COOR ² or COR ¹ , where R ¹ and R ² are identical or different and represent C ₁ -C ₄ -alkyl, CHVAIkenyl, C, -C ₄ alkoxy-C _r C ₄ alkyl,

CHVakoxy-C ^ Cvalkoxy-Ct-C ^ alkyl or are mono- to trisubstituted by identical or different methoxy, fluorine, chlorine, bromine, methyl, C, -C ₄ alkylcarbonyloxy-substituted Cj ^ -cycloalkyl or mono- to trisubstituted , phenyl which is monosubstituted or disubstituted by phenyl which is nitro, cyano, fluoro, chloro, bromo, methyl, methoxy or phenylimethyl which is monosubstituted to trisubstituted identically or differently by nitro, cyano, fluoro, chloro, bromo, methyl, methoxy.

If, for example, 2,6-dichloro-4-amino-phenol, 1-methyl-chlorocarbonylcyclohexane and butyl chloroformate are used as starting materials, the course of the reaction can be represented by the following formula scheme:

Cl-C CH ₃ O

h Il

Cl

egg

ClCOOC ₄ H ₉ -n

OC ₄ H ₉ -n

The aminophenols required as starting materials for carrying out the process according to the invention are generally defined by the formula (II). In this formula (II), the radicals Hai and Y'-Y ³ have the properties already given in connection with the description of the compounds of the formula (I) according to the invention. The compounds are largely known and can be prepared by analogy processes (cf., Methods of Organic Chemistry, Houben-Weyl, Volume VI / 1c, Phenols, Part 1, Georg Thieme Verlag, Stuttgart, 1976, and "Reactions of Organic Synthesis", Cesare Ferri, p.81,89,91,97,118,120,122,124,126,128, Georg Thieme vertag, Stuttgart, 1978).

The 4-amino-2-chloro- or ^ -bromo-e-trifluoromethylphenols are known from Jp. Kokai Tokkyo Koho Jp 61/126055 and z. B. 4-amino-2,3,5,6-tetrafluorophenol from Zh. Org. Khim. 10 (9), 1923-1927 (1974). The compounds of the formula (HA)

Cl

HoN

(HA)

in which

Y ^{4 is} fluorine or chlorine are the subject of EP-A-293718 and z. B. prepared from corresponding hydroxybenzoic acids of the formula (VA)

HOOC

(VA)

by decarboxylation with subsequent nitration of the resulting phenols of the formula (VI A)

(Via)

to the nitro compounds of the formula (VIIA) F Cl

(VIIA)

which are then hydrogenated, z. B. with hydrogen and Raney nickel, to the corresponding amines of the formula (UA).

The compounds of formula (VIIA) are the subject of EP-A-293718 European application. In addition, the cycloalkanecarboxylic acid or Cycloalkenecarboxylic acid derivatives are generally defined by the formula (III) wherein X is cycloalkyl or cycloalkenyl. In

of this formula (III) have the radicals X and hai ¹ already in connection with the description of the invention

Compounds of formula (I) valued meanings. The compounds are known and can be prepared by analogy methods

(See Diversi et al., Synthesis 1971, 258; US 3674831; "Organic Synthesis Reactions", Cesare Ferri, S.460,461, 1978;

Georg Thieme Verlag, Stuttgart); Houben-Weyl, Methods of Organic Chemistry, Bd.EB TI. 1, S. 211,320,343,428ff., G. Thieme Verlag, Stuttgart, 1985). The carboxylic acid and carbonic acid derivatives additionally required for carrying out the process according to the invention Formula (V) in which Z and Hai ^{2 have} the abovementioned meaning are known and preparable by analogy

(See "Reactions of Organic Synthesis" Cesare Ferri, p.432ff "460ff., 1978, Georg Thieme Verlag, Stuttgart; Houben-Weyl," Methods of Organic Chemistry, Carbonic Acid Derivatives, Vol. E4, p.9ff. , Georg Thieme Verlag, Stuttgart, 1S83; Bd. E 5 TI. 1,

P. 193 ff., Georg Thieme Verlag, Stuttgart, 1985). The acylaminophenols used as intermediates in the process according to the invention are represented by the formula (IV)

Are defined.

Among the compounds of the formula (IV), the compounds of the formula (IVa)

(IVa)

in which

X 'is an optionally alkyl-substituted cycloalkenyl rust, preferably a Ci-Cj-alkyl-substituted

Cyclopentenyl, cyclohexenyl or Cycloheptenylrest, and Y ', Y ² , Y ³ and Hai have the abovementioned meaning, new

 The novel acylamino derivatives of the formula (IVa) are obtained by reacting aminophenols of the formula (II)

Y ¹ shark

Y ²

in which

Y ¹ , Y ¹ , Y ³ and Hal have the abovementioned meaning, with carboxylic acid derivatives of the formula (IIIa)

O Il X'-C-Hal ¹ (purple),

in which

X 'and HaP have the abovementioned meaning, if appropriate in the presence of a solvent and, if appropriate, in Reacting the presence of an acid acceptor. The remaining compounds of formula (IV) can be obtained according to or by known methods. If appropriate, the process according to the invention is carried out in the presence of acid acceptors. As acid acceptors

kö / inen all common acid binder find use. Alkali carbonates and alcoholates, such as

Sodium and potassium carbonate, sodium and potassium methylate or ethylate, furthermore aliphatic, aromatic and heterocyclic Amines, for example triethylamine, trimethylamine, dimethylaniline, diazabicyclo-tSAOl-undec-ene, dimethylbenzylamine

and pyridine.

For carrying out the process according to the invention, preference is given in the first reaction step to one mol of amino acid. Phenol of the general formula (II) 1-2 mol, in particular 1-1.4 mol, of the compounds of the general formula (III) or (IIIa) For the second reaction step of the process according to the invention is preferably used to 1 mole of acylaminophenol the Formula (IV) or (IVa) 1-2 mol, in particular 1-1.4 mol, of the compounds of general formula (V). Suitable diluents for carrying out the process according to the invention are virtually all inert organic Diluents in question. These include in particular all-phytic and aromatic, gegebonenfalls halogenated Hydrocarbons, such as pentane, hexane, heptane, cyclohexane, petroleum ether, gasoline, ligroin, toluene, xylene, methylene chloride, Ethylene chloride, chloroform, carbon tetrachloride, chlorobenzene and o-dichlorobenzene, ethers such as diethyl and dibutyl ether, Glycol dimethyl ether and oily glycol dimethyl ether, tetrahydrofuran and dioxane, ketones such as acetone, methylethyl, Methyl isopropyl and methyl isobutyl ketone, esters such as methyl acetate and ethyl acetate, nitriles such as. For example, acetonitrile and Proplonit.il, amides such. B. dimethylformamide, dimethylacetamide and N-methylpyrrolldone and dimethylsulfoxide, Tetramethylene sulfone and hexamethylphosphoric triamide. The ancestor according to the invention is generally carried out at temperatures between -5O ⁰ C and 12O ⁰ C. Prefers

The P range is between 0 ° C and 110 ° C. The reactions are generally carried out at atmospheric pressure.

The workup is carried out by customary methods, for example by extraction of the products with toluene or methylene chloride

from the water pre-diluted reaction mixture, washing the organic phase with water, drying and distilling or so-called " distillation ", ie, prolonged heating under reduced pressure to moderately elevated temperatures to remove the last volatiles or by chromatographic purification over silica gel or e.g. B. through

Crystallization. The compounds are characterized by refractive index, melting point, R _r value or boiling point. The active compounds according to the invention are for use for controlling ν. ·: Pests, especially as funigzides

suitable.

Fungicides in crop protection are used to combat Plasmodiophoromycetes, Oomycetes, Chytt idiomycetes, Zygomycetes, Ascomycetos, Basidiomycetes, Deuteromycetes. Bactericidal agents are used in crop protection for controlling Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae used.

By way of example, but not by way of limitation, some pathogens of fungal and bacterial diseases, which fall under the abovementioned generic terms, are named:

Xanthomonas species, such as Xanthomonas campestris pv. Oryzae; Pseudomonas species, such as Pseudomonas syringae pv. Lachrymans; Erwinia species, such as Erwinia amylovora; Pythium species such as Pythium ultimum; Phytophthora species, such as Phytophthora infestans; Pseudoperonospora species, such as Pseudoperonospora humuli or Pseudoperonospora cubense; Plasmopara species, such as Plasmopara viticola; Peronospora species such as Peronospora pisi or P. brassicae; Erysiphe species, such as Erysiphe graminis; Sphaerotheca species, such as Sphaerotheca fuliginea; Podosphaera species, such as Podosphaora leucotricha; Venturia species, such as Venturia inaec.ualis; Pyrenophora species, such as, for example, Pyrenophora teres or P.graminea (conidia form: Drechslera, Syn: Helminthosporium); Cochliobolus species, such as Cochliobolus sativus (conidia form: Drechslera, Syn: Helminthosporium); Uromyces species, such as Uromyces appendiculatus; Puccinia species, such as Puccinia recondita; Tillotia species such as Tilletla caries; Ustilago species such as Ustilago nuda or Ustilago avenae; Pellicularia species, such as, for example, Pellicularia sasakii; Pyricularia species, such as Pyricularia oryzae; Fusarium species such as Fusarium culmorum; Botrytis species, such as Botrytis cinerea; Septoria species such as Septoria nodorum; Leptosphaeria species, such as Leptosphaeria nodorum; Cercospora species, such as Cercospora canescens; Alternaria species, such as Alternaria brassicae; Pseudocercosporella species, such as Pseudocercosporella herpotrichoides.

The good plant tolerance of the active ingredients in the necessary concentrations for controlling plant diseases allows treatment of aboveground plant parts, of plant and seed, and the soil. In this case, the active compounds according to the invention can be used with particularly good success for controlling botrytis fungi on beans and for combating cereal diseases, such as, for example, against Pseudocercosporella. The active compounds are furthermore suitable for controlling animal pests, preferably arthropods and nematodes, in particular insects and arachnids, which occur in agriculture, in forests, in the protection of stored products and materials, and in the hygiene sector. They are effective against normally sensitive and resistant species as well as against all or individual developmental factors. The above-mentioned pests include:

From the order of Isopoda z. B. Oniscus asellus, Armadillidium vulgaris, Porcellio scaber. From the order of Diplopoda z. B. Blaniulus guttulatus. From the order of Chilopoda e.g. Geophilus carpophagus, Scutigera spec. From the order of Symphyla z. B. Scutlgerella immacul & ta. From the order of Thysanura z. B. Lepisma saccarina. From the order of Collembola z. B. Onychiurus armatus. From the order of Orthoptera z. B. BIaUa orientalis, Perip laneta americana, Leucophaea maderae, Blattella

germanica, Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus differential,

Schistocerca gregaria.

From the order of Dermaptera z. S. Forflcula auricularia

 From the order of Isoptera z. Reticulitermes spp.

From the order of Anoplura z. Phylloxera vastatrlx, Pemphigus spp., Pediculus humanus corporis, Haematopinus spp., Linognathus spp.

From the order of Mallophaga z. B. Trichodectes spp., Damalinea spp. From the order of Thysanoptera z. B. Hercinothrips femoralis, Thrips tabacl.

From the order of Heteroptera z. Eurygaster spp., Dysdercus intermedius, Plesma quadrata, Cimex loctularius, Rhodnius prolixus, Triatoma spp.

From the order of Homoptera z. Aleurodes brassicae, Bemlsia tabacl, Trialeurodes vaporariorum, Aohis. gossypii, Brevicoryne brassicae, Cryptomyzus ribs, Aphis fabae, Doralis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Macrosiphum avenae, Myzus spp., Phorodon humuli, Rhopalosiphum padi, Empoasca spp., Euscelis bilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp. Psylla spp.

From the order of Lepidoptera e.g. Pectinophora gossypiello, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella maculipennis, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria & pp Bucculatrix thurberiella, Phyllocnistis cltrella, Agrotis spp., Euxoa spp., Feltia spp., Earias insulana, Heliothis spp Spodoptera exigua, Mamestra brassicae, Panolis flammea, Prodenia litura, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleria mellonella, Tineola bisselliella, Tinea pellionella, Hofmannophila pseudospretella, Cacoecia podana, Capua reticulana, Choristoneura fumiferana, Clysia amblguella, Homona magnanima, Tortrix viridana. From the order of Coleoptera z. B. Anobium punctatum, Rhizopertha dominica, Acanthoscelides obtectus, Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedon cochleariae, Diabrotica spp., Psylliodes chrysocephala, Epilachna varivestis, Atomaria spp., Oryzaephilus surinamensis, Anthonomus spp., Sitophilus spp., Otiorrhynchus sulcatuu , Cosmopolites sordidus, Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogoderma spp., Anthrenus spp ,, Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp., Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha, Arnphimallon solstitialis, Coste! / Tra zealandica.

From the order of Hymenoptera z. B. Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp.

From the order of Diptera z. B. Aedes spp., Anopheles spp., Culex spp., Drosophila me'anogaster, Musca spp., Fannia spp., Calliphora erythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp., Gastrophyllus spp., Hyppobosca spp. , Stomoxys spp., Oestrus spp., Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortnlanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae, Tipula paludosa. From the order of Siphonaptera z. Xenopsylla cheopis, Ceratophyllus spp. From the order of Arachnida z. B. Scorpio maurus, Latrodectus mactans.

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

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

The active compounds can be converted into the customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, ultrafine encapsulations in polymeric substances and in seed coating compositions, as well as ULV formulations.

These formulations are prepared in a known manner, for. Example, by mixing the active compounds with extenders, that is liquid solvents, liquefied gases under pressure and / or solid carriers, optionally with the use of surfactants, emulsifiers and / or dispersants and / or foam-forming agents. In the case of using water as extender t. As well as organic solvents can be used as auxiliary solvent. Suitable liquid solvents are essentially: aromatics, such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, choroethylene or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for. As petroleum fractions, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water. By liquefied gaseous diluents or carriers are meant liquids which are gaseous at normal temperature and under normal pressure, eg. As aerosol propellants, such as halogenated hydrocarbons and butane, propane, nitrogen and carbon dioxide. Suitable solid carriers are: z. Example, natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic minerals, such as finely divided silica, alumina and silicates. As a solid carrier for granules are: z. As broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules jhe granules of inorganic and organic flours and granules of organic material such as sawdust, coconut shells, corn cobs and tobacco stalks. Suitable emulsifiers and / or foam-formers are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, eg. B. Alkylaryipolyglycol ether, alkyl sulfonates, alkyl sulfates, arylsulfonates and protein hydrolysates. Suitable dispersants are: for example, lignin sulfite bites and methyl cellulose.

Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex polymers may be used in the formulations, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, as well as natural phospholipids such as cephalins and lecithins, and synthetic phospholipids. Other additives may be mineral and vegetable oils.

Dyes such as inorganic pigments, eg., Iron oxide, titanium oxide, ferrocyan blue and organic dyes, such as Alizarin, A20 and metal phthalocyanine dyes and trace nutrients such as salts of Elsen, manganese, boron, copper, cobalt, Molybdenum and zinc have been used. The formulations generally contain between 0.1 and 95% by weight of active compound, preferably between 0.5 and 90%. The active compounds according to the invention can be present in the formulations in a mixture with other known active compounds,

such as fungicides, insecticides, acaricides and herbicides, as well as in mixtures with fertilizers and others

Growth regulators. The active compounds can be used as such, in the form of their formulations or the use forms prepared therefrom, such as

ready to use solutions, emulsifiable concentrates, emulsions, foams, suspensions, wettable powders, pastes, soluble

Powder, dusts and granules are applied. The application is done in the usual way, for. By pouring, Spraying, spraying, scattering, dusting, foaming, brushing, etc. It is also possible, after the active ingredients

the ultra-low-volume method or inject the active ingredient preparation or the active ingredient itself into the soil. It can also be the seed of the plants to be treated.

In the treatment of parts of plants, the drug concentrations in the use forms in a larger Range can be varied. They are generally between 1 and 0.0001 wt .-%, preferably between 0.5 and 0.001%. In the seed treatment, in general, amounts of active ingredient of 0.001 to 50g per kilogram of seed, preferably

0.01 to 10 g needed.

When treating the soil, active ingredient concentrations of 0.00001 to 0.1 wt .-%, preferably from 0.0001 to 0.02% on Site of action required. example 1

OCH ₃

4 g (13, OmMoI) 2,3-dichloro-4- (1-methyl-cyclohexyl-carbonyl) -amino-phenol are dissolved in 50 ml of tetrahydrofuran and treated with 2.5 ml (18.5 mmol) of triethylamine. 1.5 g (14,3mMol) methyl chloroformate are then added dropwise to the reaction mixture at 2O ⁰ C. The mixture is stirred for two hours at 20 ° C and then distilled off the solvent in a water jet vacuum. The remaining residue is then chromatographed on silica gel (mobile phase: pet / olether: acetone = 8: 2). Yield: 4.4 g (98% of theory). Mp .: 125 ° C

 Analogously, the following compounds of the formula (I)

(I) shark

manufactured.

Example No. XY ¹ Y ² Y ³ Hal Z Phys. Data (Mp.)

* ^ V "Cl HH Cl COOCH ₂ CH (CH ₃ ) ₂ 109 ⁰ C

\ ___ X 'Cl HH Cl C00C ₃ H ₇ n 122 ⁰ C

CH ₃

{yC Cl H H Cl COOCH₂CH (CH₃) C₂H₅ 67 ° C

CH ₃

CH ₃

Ος

Cl HH Cl CO-X> 63 ^° C

Cl H H CI CO ^ 91 ° C

CH ₃ OCOCH ₃

Cl HH Cl CCcA 107 ⁰ C

Cl

ro to co

Example no.

Hal Z

phys. data (mp.)

CH

Cl

H H

OCH

125 ^° C

CH

Cl

H H

CH

HO ⁰ C

10

Cl

H H

COCH

105 ⁰ C

11

or

Cl H

Cl COC ₄ H ₉ -t

136 ⁰ C

12

Cl

H H

Cl COCH (C ₂ H ₅ ) C ₄ H ₉ -Ii 45 ° C

13

Cl

H H

Cl C0CH ₂

71 ° C

Example No. »X

CX

ck *

_γ 2 _Y 3 _Hal

phys. data (mp.)

CH-

Cl H H Cl

102 ⁰ C.

Cl H H Cl

CH ₃ CH ₃

COCH ₂ - ^ '

CHr

Cl H H Cl

105 ⁰ C

V \ A

Cl

HH Cl COCH ₂ -C> -F 66 ° C

CH ₃

^CH

Cl HH Cl COCH ₂ -C _x

90 ⁰ C

CFr

Example No. X

_γ 2 _Y 3 _Hal

phys. data (mp.)

o < ⁽

, ^CH 3

Cl H H

CHr

Cl H H

Cl

Cl H H Cl

145 ⁰ C

Cl

CH ₃ Cl COCH ₂ - \ __ / ~ ^ H ₃ 104 ⁰ C

CH ₃ CH ₃

Cl Cl COC (CH 2) - T-TC 7-Cl 82 ° C

HH Cl COCH ₂

128 ⁰ C.

br

/ -V ^CH 3

\ Λ

Cl HH Cl COCH ₂ -CVOCH ₃ 122 ⁰ C Example No. X

Y ¹ Y ² Y ³ Hal Z

phys. data (mp.)

CH-

C < ^CH! CH-

Cl H H Cl COCH-

H ₃ 93 ° C

CH ₃ CH ₃

F F F Cl

35 ⁰ C

Q < ^CH:

Cl H H Cl COOCH-

CH-

CH-

CH-

Cl H H Cl COOCH-

CH-

H-

Cl HH Cl COOCH ₃

ISJ (O 00 CO

Example no.

Hal Z

phys. data (mp.)

CH

Cl H

Cl H H Cl COOCH

CX ¹

Cl

H H

Cl COOCH-

\ X

Cl H

Cl COCH

^C1H

Cl

^C1 f COCH ₂

⁷² ° ^C

/ Vx

\ X

Cl H

Cl COOCH ₂ CH ₂ OC ₂ H ₅

^CH

Cl H H

Cl COOCH ₂ CH ₂ OC ₂ H ₅ 52 ° C

Example no.

Hal Z

phys. data (mp.)

/ -V ^c " ³

S A

Cl H

Cl COOCH ₂ CH ₂ OCH ₃

Cl H

Cl COOCH ₂ CH ₂ OC ₃ H ₇ -I

Cl H

Cl C00CH ₂ CH ₂ 0C ₄ H ₉ -n

O < ^CH3

Cl

H Cl COOCH ₂ CH ₂ OCH (Ch ₃ ) C ₂ H ₅

O <

CH-

Cl H

Cl COOCH ₂ CH ₂ OC ₃ H ₇ -Ii

Cl

HH

Cl COOCH ₂ CH (CH ₃ ) OCh ₃

/ ^{-V CH3}

\ A

Cl

H H

Cl COOCH ₂ CH ₂ OCh ₂ CH ₂ OC ₂ H ₅ ng ⁰

1.5116

CH:

Cl

H H

Cl COOCH ₂ CH ₂ OC ₂ H ₅

Production Examples of Starting Compounds: Example AV.

18.5 g (0.085 mol) of 4-amino-2,6-dichlorophenol are dissolved in 150 ml of tetrahydrofuran and first with 8.6 g (0.085 mol) of triethylamine, then at ⁰ ° C. internal temperature with 15 g (0.094 mol) of 1-methylcyclohexanecarboxylic acid chloride added. The mixture is stirred overnight at 2O ⁰ C and then added to complete the reaction again 5g carboxylic acid chloride and 2.8 g of triethylamine to the reaction mixture. After 2 hours, it is poured onto ice and the extracted solid is recrystallized from toluene. The abovementioned compound having the melting point 14O ⁰ C is obtained; Yield: 22.3 g (= 87% of theory). Analogously, the compounds of the formula (IV) or (IVa) are obtained:

Example A2

3,5-Dichloro ^, 6-difluoro-4-hydroxybenzoic acid

In a stirred apparatus, 300 g of potassium hydroxide, 600 ml of water, 15 g of tetrabutylammonium chloride and 135 g of 3,5-dichloroethane are added.

Submitted 2,4,6-trifluorobenzotrifluoride and then heated for 5 hours at reflux. After the reaction has ended, the mixture is cooled and acidified by adding hydrochloric acid. The solid product is filtered off with suction and dried in vacuo. Yield: 93g with a melting point of 102-105 ⁰ C.

Example A3

3-chloro-2,5,6-trifluoro-4-hydroxy-benzoic acid

As in Example A1, from 400 g of NaOH, 1200 ml of water, 15 g of tetraethylammonium chloride and 276 g

3-Chlorotetrafluorobenzotrifluoride, refluxed for 6 hours. 238g of product obtained with a melting point of

Example A4

2,6-Dichloro-3,5-difluorophenol 50g SS-dichloro-.-DifluoroM-hydroxy-benzoic acid and 10 ml dimethylformamide are mixed and heated. At 105-13O ⁰ C carbon dioxide evolves and allowed to react at this temperature. Then, 200 ml of toluene and then 80 ml of water, the phases are separated, the organic phase is dried and then distilled. You get 34g of the

Product with a boiling point of 87-88 ⁰ C and a refractive index of n ": 1.5310. Example A5 Analogously to Example A3, 2-chloro-3,5,6-trifluorophenol, having a boiling point 68-70 ° C / 20 mbar. Example A6

2,6-dichloro-3,5-difluoro-4-nitrophenol

20 g of 2,6-dichloro-3,5-difluorophenol are placed in 70 ml of acetic acid and 8 g of 98% strength nitric acid are added dropwise. Subsequently

is stirred for 2 hours at room temperature, taken up in 150 ml of dichloromethane and washed twice with water. After distilling off the dichloromethane left 18g product. 94% by GC analysis.

Example A7

2-chloro-3,5,6-trifluoro-4-nitrophenol

By analogy with Example A5, 25 g of 2-chloro-3,5,6-trifluoro-4-nitrophenol are obtained by nitration from 28 g of 2-chloro-3,5,6-trifluorophenol

obtained with a purity of 93% and a melting point of 107-109 ° C.

Example A8

2,6-Dichloro-3,5-difluoro-4-amino-phenol 18g 2,6-dichloro-3,5-difluoro-4-nitrophenol are dissolved in 100 ml of methanol in the presence of 1.5 g of Raney nickel at 25-45 ° C hydrogenated with 30-50bar hydrogen until the end of hydrogen uptake. After filtration, the solution is concentrated under reduced pressure

Pressure released from the solvent. There remain 13 g of aminophenol (GC purity 98.4%); Mp 151 ⁰ C. Example A9

2-chloro-3,5,6-trifluoro-4-amino-phenol

From Example 25, 25 g of 2-chloro-3,5,6-trifluoro-4-nitro-phenol in 120 ml of methanol and 2 g of Raney nickel Hydrogenation 20g aminophenol (GC purity 97%). Analogously to Example A1, the following compounds of the formula (IVa) are obtained.

-20- 298 334

OY ¹ Kai

 Χ

NH

Expl X ¹

Y ¹ Y ² Y ³ Hal phy. dates

Alles

Cl H H Cl

A12

Cl H Cl H

A13

A14

CH-

Cl H H Cl

Cl H Cl H

CH ₃ CH ₃

A15 CH-

Cl H Cl H

A16 CHr

CH ₃ CH ₃

CHr

Cl H H Cl

CH.

example Bo-.rytis test (bean) / protective Solvent: 4.7 parts by weight of acetone Emulsifier: 0.3 part by weight of alkylaryl polyglycol ether To prepare a suitable preparation of active compound, 1 part by weight of active compound is mixed with the indicated Amounts solvent and emulsifier and dilute the concentrate with water to the desired concentration. To test for protective activity, young plants are sprayed with the preparation of the active ingredient until dripping wet. To As the spray coating dries, 2 small pieces of agar covered with Botrytis cinerea are placed on each leaf. The

Inoculated plants are placed in a darkened humid chamber at 2O ⁰ C. 3 days after inoculation, the size of the infestation spots on the leaves is evaluated.

An excellent effectiveness show in this test z. B. the compounds according to the following preparation examples: 1,2,3,4,

6,7,8,9,35 and 42.

Claims (10)

1. Cycloalkyl- or cycioalkenyl-carboxylic acid anilides of the general formula O NH-C-X shark in which X is optionally alkyl-substituted cycloalkyl or optionally Alkyl-substituted cycloalkenyl, Shark stands for halogen and Y \ Y ² uY ³ independently of one another represent hydrogen, halogen, optionally halogen-substituted alkyl, optionally halogen-substituted alkoxy or optionally halogen-substituted alkylthio, and Z stands for the groups COOR ² or COR ¹ , where R ¹ and R ^{2 are the} same or different and are optionally halogen-substituted alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl, polyalkoxyalkyl and optionally substituted cycloalkyl, optionally substituted phenyl, optionally substituted phenylalkyl or substituted phenoxyalkyl. 2. Compounds of formula (I) according to claim 1, wherein X is optionally one to four times, the same or different by straight-chain or branched alkyl having 1-4 carbon atoms substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or cycloheptyl or represents cycloalkenyl with -7 ring members, where the cycloalkyl radical or cycloalkenyl radical is one to six times, identically or differently, by straight-chain or branched alkyl having 1- 4 carbon atoms can be substituted, Hai stands for fluorine, chlorine or bromine, Y ¹ , Y ² u. Y ^{3 are the} same or different and are hydrogen, fluorine, chlorine, bromine, straight-chain or branched alkyl having 1-4 carbon atoms, straight-chain or branched alkoxy or alkylthio each having 1-4 carbon atoms, haloalkyl, haloalkoxy or haloalkylthio each having 1-4 Carbon atoms in the straight-chain or branched alkyl part and with 1-5 identical or different halogen atoms, Z stands for COOR ² or COR ¹ , where R ¹ and R ^{2 are the} same or different and for optionally mono- to trisubstituted by halogen-substituted C ₁ -C ₈ -AlkYl, C ₂ -Ca-AlkenyI, ^ - ^ - alkoxy-C ^ Gj-alkyl, ^ -CrAlkoxy-C ^ Gralkoxy-Ci-Cvalkyl, CH ^ j-alkylthio-Cr-C ^ alkyl or unsubstituted or monosubstituted to fivefold, identically or differently by CH ^ -haloalkyl, halogen, C ₁ -C ₄ -AlkYl, Ci-C ₄ -Aikoxy, hydroxy, C 1 -C 6 -alkylcarbonyloxy, substituted C 1 -C 6 -cycloalkyl or unsubstituted or in the phenyl moiety monosubstituted to five-fold, identically or differently, substituted by γΐ »_γ 5 -substituted phenyl-C 1-8 -alkyl or unsubstituted or in phenylthail, up to five times, are the same or different represented by Y ¹ '-Y ⁵ ' substituted phenoxyalkyl,
wherein Y ¹ '-Y ⁵ ' have the meaning of Y ¹ -Y ³ , NO ₂ and cyano. 3. Compounds of formula (I) according to claim 1, wherein X is one or two times, the same or different, by straight-chain or branched Cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or cycloheptyl substituted by alkyl having 1-4 carbon atoms, cyclopentenyl, cyclohexenyl, cycloheptenyl optionally substituted once or twice, identically or differently by straight-chain or branched alkyl having 1-4 carbon atoms, Y ¹ , Y ² u. Y ^{3 are the} same or different and are hydrogen, fluorine, chlorine, bromine, methyl or trifluoromethyl and Hai stands for fluorine, chlorine or bromine, Z is COOR ² or COR ¹ , wherein R ¹ and R ^{2 are the} same or different and for C ₁ -C ₆ -alkyl, Cz-Ce-alkenyl, C ₁ -C ₄ -alkoxy-C ₁ -C ₄ -alkyl, ₁ Ci-Ct-alkoxy-C ^ C ^ alkoxy - ^ - C ^ alkyl, C ₁ -C ₄ -alkylthio-C ₁ -C ₂ -alkyl or unsubstituted or mono- to trisubstituted by identical or different fluorine, chlorine, Bromine, C ₁ -C ₂ -alkyl, C ₁ -C ₂ -alkoxy, C ₁ -C ₂ -alkylcarbonyloxy-substituted C ₃ -C ₇ -cycloalkyl, or represent unsubstituted or mono- to trisubstituted by identical or different substituents by nitro, cyano, fluorine, Chloro, bromo, methyl, trifluoromethyl, trifluoromethylthio, methoxy, trifluoromethoxy substituted phenyl or unsubstituted or monosubstituted to trisubstituted by identical or different nitro, cyano, fluoro, chloro, bromo, methyl, trifluoromethyl, trifluoromethylthio, methoxy, trifluoromethoxy phenyl - ^ - alkyl or unsubstituted or monosubstituted to trisubstituted by identical or different nitro, cyano, fluoro, chloro, bromo, methyl, trifluoromethyl, trifluoromethylthio, methoxy, trifluoromethoxy-substituted phenoxy-C! -C 2 -alkyl. 4. Compounds of formula (I) according to claim 1, wherein X represents methyl or ethyl substituted cyclopentyl in the 1- or 1,3-position, Cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, which are optionally additionally substituted by another alkyl radical having 1-3 carbon atoms, Shark stands for fluorine, chlorine or bromine and Y \ Y ² u. Y ^{3 are} identical or different and represent hydrogen, fluorine, chlorine, bromine or trifluoromethyl, Z is COOR ² or COR ¹ , wherein R ¹ and R ^{2 are the} same or different and for C ₁ -C ₄ alkyl, C ₁ -C ₆ alkenyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkyl, _{Ci-C4-alkoxy-Ci-C4-alkoxy-Ci-C 4} -alkyl or füreinfach to trisubstituted by identical or different methoxy, fluorine, chlorine, bromine, methyl, C ₁ -C ₄ alkylcarbonyloxy substituted Cy Cj-cycloalkyl or are monosubstituted to trisubstituted by identical or different substituents by nitro, cyano, fluoro, chloro, bromo, methyl, methoxy-substituted phenyl or monosubstituted to trisubstituted by identical or different nitro, cyano, fluoro, chloro, bromo, methyl , Methoxy substituted phenylmethyl stand. 5. Process for the preparation of substituted cycloalkyl- or cycloalkenylcarboxylic acid anilides of the formula (I) NH-C-X (I) shark in which X is optionally alkyl-substituted cycloalkyl or optionally Al kyl-substituted cycloalkenyl, Shark for halogen and Y ¹ , Y ² u. Y ^{3 are the} same or different and are hydrogen, halogen, optionally halogen-substituted alkyl, optionally halogen-substituted alkoxy or optionally halogen-substituted alkylthio and Z stands for the groups COOR ² or COR ¹ , where R ¹ and R ^{2 are the} same or different and are optionally halogen-substituted alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl, polyalkoxyalkyl and optionally substituted cycloalkyl, optionally substituted phenyl, optionally substituted phenylalkyl or substituted phenoxyalkyl, characterized in that aminophenols of the formula (II)
Y ¹ shark H ₂ N- <V-OH (ID yj γ2 in which Hal, Y ¹ , Y ² and Y ^{3 have} the meanings given above, in a first reaction step with carboxylic acid derivatives of the formula (III) O
XC-HaI ¹ (III) in which X has the meaning given above and Hai ^{1 represents} halogen, or a leaving group commonly used in acylation reactions, if appropriate in the presence of an acid acceptor and if appropriate in the presence of a solvent or diluent, and then in a second reaction step these intermediates of the formula (IV) Il Yi Hai (IV), in which X, Y ¹ , Y ² , Y ³ and Hal have the abovementioned meaning, with carbonyl derivatives of the formula (V) Z-HaI ² (V) ₍ in which Z has the abovementioned meaning and Hal ^{2 is} halogen or a leaving group commonly used in acylation reactions, if appropriate in the presence of an acid acceptor and if appropriate in the presence of a solvent or diluent. 6. pest control agent, characterized by a content of at least one cycloalkyl or cycloalkenyl-carboxylic acid anilide of the formula (I) according to claims 1 to 5. 7. Use of cycloalkyl or Cycloalkenylcarbonsäureanilid of formula (I) according to claims 1 to 5 for controlling pests. 8. A method for controlling pests, characterized in that cycloalkyl- or cycloalkenyl-carboxylic acid anilide of the formula (I) according to claims 1 to 5 is allowed to act on pests and / or their habitat. 9. A process for the preparation of pesticides, characterized in that mixed cycloalkyl or cycloalkenyl-carboxylic acid anilide of the formula (I) according to claims 1 to 5 with extenders and / or surface-active agents. 10. Acylaminophenols of the formula (IVa) Y ¹ shark X 'NH-C> -0H Y ³ Y ² in which X 'is an optionally alkyl-substituted cycloalkenyl radical, preferably a C ₁ -C 2 alkyl-substituted cyclopentenyl, cyclohexenyl or cycloheptenyl radical, and Shark stands for halogen Y ¹ , Y ² , Y ³ independently of one another represent hydrogen, halogen, optionally halogen-substituted alkyl, optionally halogen-substituted alkoxy or optionally halogen-substituted alkylthio.