KR20070018821A - Pyrazolinols used as pesticides - Google Patents

Abstract

The present invention relates to the use of pyrazolinol of general formula (I) for the control of animal pests, novel pyrazolinol and methods for preparing these compounds:

Where

A, Q, R ¹ , R ² , R ³ , R ⁴ and R ⁵ are as defined in the specification.

Description

Pyrazolinols used as pesticides}

The present invention provides crop processing agents, in particular known and novel pyrazolinols and derivatives thereof for controlling animal pests, crop processing agents based on known and novel pyrazolinols and derivatives thereof, and novel trifluoromethylpyrazolol and derivatives thereof. And a method for producing the same.

A relatively large number of pyrazolinol derivatives are known from the literature. Chemistry of Heterocycl. Compounds (Translation of Khim. Geterots. Soedin.) 35 (1999), 87-92; Doklad. Akad. Nauk Respub. Uzbekistan 2000, 42-45-Chem. Cited in Abstracts 136: 69766; Eur. J. Pharmacol. 451 (2002), 141-147; Heteroatom Chemistry 14 (2003), 132-137; J. Chem. Res., Synopses 2001, 12-13, 133-147; J. Fluorine Chem. 92 (1998), 23-26; 99 (1999), 177-182; J. Med. Chem. 14 (1971), 997-998; Khim. Geterots. Soedin. 1986, 128-Chem. Cited in Abstracts 105: 172346; Khim. Geterots. Soedin. 1990, 1260-1270-Chem. Cited in Abstracts 114: 228877; Khim. Geterots. Soedin. 1993, 267-268-Chem. Cited in Abstracts 120: 54516; Russian J. Org. Chem. (Translation of Zhurnal Organi. Khim.) 35 (1999), 357-363; 36 (2000), 1144-1149; Spectroscopy Letters 32 (1999), 851-865; Synthesis 2002; 1079-1083; US 2002, 2353-2358; Synthetic Commun. 30 (2000), 1457-1465; Tetrahedron 55 (1999), 345-352; Tetrahedron Lett. 43 (2002), 8701-8705; Zhurnal Obshchei Khimii 57 (1987), 584-595-Chem. Cited in Abstracts 108: 150362; Zhurnal Organi. Khimii 31 (1995), 937-943-Chem. Abstracts 124: 260918.

However, these compounds have only been described as chemical scientific research products without commercialization.

It has been found according to the invention that pyrazolinol and derivatives thereof, some of which are known, are very active against animal pests:

Where

A represents optionally substituted alkyl,

Q represents oxygen or sulfur,

R ¹ represents hydrogen or in each case optionally substituted alkyl, alkylcarbonyl, alkenyl, alkenylcarbonyl, cycloalkyl, cycloalkylcarbonyl, aryl, arylcarbonyl, arylalkyl or arylalkylcarbonyl Indicate,

R ² represents hydrogen or in each case optionally substituted alkyl, alkylcarbonyl, alkoxycarbonyl, cycloalkyl, aryl, arylalkyl or heterocyclyl,

R ³ in each case represents optionally substituted alkyl, alkenyl, cycloalkyl, aryl, arylalkyl or heterocyclyl, or

R ² and R ³ together also represent alkanediyl (alkylene),

R ⁴ represents hydrogen, amino, or in each occurrence optionally substituted alkyl, alkylcarbonyl, alkylsulfonyl, alkylamino, alkylcarbonylamino, alkylsulfonylamino, alkenyl, alkenylcarbonyl or Alkynyl,

R ⁵ represents hydrogen or in each case optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heterocyclyl or heterocyclylalkyl.

Saturated or unsaturated hydrocarbon radicals, such as alkyl or alkenyl, including those bonded with heteroatoms such as, for example, alkoxy, are in each case as straight or branched as possible.

The optionally substituted radical may be monosubstituted or polysubstituted, in which case the substituents may be the same or different.

The compounds of formula (I) according to the invention have at least one asymmetrically substituted carbon atom and therefore may exist in different enantiomers (R- and S-configuration form) or diastereomeric forms. The present invention relates to the use of different possible respective enantiomers or stereoisomers of compounds of general formula (I) and to mixtures of these isomeric compounds.

Hereinafter, the preferred substituents or radical ranges mentioned in the general formulas above and after will be described:

A preferably represents hydroxyl-, cyano-, halogen-, C ₁ -C ₄ -alkoxy- or C ₁ -C ₄ -haloalkoxy-substituted C ₁ -C ₈ -alkyl.

A is particularly preferably in each case optionally hydroxyl-, cyano-, fluorine-, chlorine-, bromine-, methoxy-, ethoxy-, n- or isopropoxy-, monofluoromethoxy-, di Fluoromethoxy-, trifluoromethoxy-, monofluoroethoxy-, difluoroethoxy- or trifluoroethoxy-substituted methyl, ethyl, n- or isopropyl, n-, iso- or sec -Butyl, pentyl, hexyl, heptyl or octyl.

A very particularly preferably in each case optionally represents fluorine- and / or chlorine-substituted methyl, ethyl, n- or isopropyl, n-, iso- or sec-butyl, hexyl or octyl.

A is particularly preferably difluoromethyl, trifluoromethyl, fluorodichloromethyl, chlorodifluoromethyl, trichloromethyl, 1,1,2,2-tetrafluoroethyl, pentafluoroethyl, hepta Fluoro-n-propyl, heptafluoroisopropyl, nonafluorobutyl, perfluorohexyl or perfluorooctyl.

A is in particular difluoromethyl, trifluoromethyl, fluorodichloromethyl, chlorodifluoromethyl, trichloromethyl, 1,1,2,2-tetrafluoroethyl or pentafluoroethyl, especially trifluoro Methyl is indicated.

Q preferably represents oxygen.

Q also preferably represents sulfur.

R ¹ preferably represents hydrogen, or in each case optionally hydroxyl-, cyano-, halogen-, C ₁ -C ₄ -alkoxy- or C ₁ -C ₄ -haloalkoxy-substituted C ₁ -C C ₂ -C ₁₀ -alkenyl or (C ₂ -C ₁₀ -alkenyl) which represents ₁₀ -alkyl or (C ₁ -C ₁₀ -alkyl) carbonyl, or in each case optionally cyano- or halogen-substituted Carbonyl or in each case optionally cyano-, halogen-, C ₁ -C ₄ -alkyl- or C ₁ -C ₄ -haloalkyl-substituted C ₃ -C ₆ -cycloalkyl or (C _3- C ₆ -cycloalkyl) carbonyl, or in each case optionally nitro-, cyano-, halogen-, C ₁ -C ₄ -alkyl-, C ₁ -C ₄ -haloalkyl-, C ₁ -C ₄ -Alkoxy- or C ₁ -C ₄ -haloalkoxy-substituted C ₆ -C ₁₀ -aryl or (C ₆ -C ₁₀ -aryl) carbonyl, or in each case optionally nitro-, cyano-, halogen -, C ₁ -C ₄ - alkyl -, C ₁ -C ₄ - haloalkyl -, C ₁ -C ₄ - alkoxy - or C ₁ -C ₄ - haloalkyl alkoxyl - it represents a (alkyl C ₆ -C ₁₀ - - aryl -C ₁ -C ₄₎ carbonyl substituted (C ₆ -C ₁₀ - - aryl) -C ₁ -C ₄ alkyl.

R ¹ particularly preferably represents hydrogen or in each case optionally cyano-, fluorine-, chlorine-, bromine-, methoxy-, ethoxy-, n- or isopropoxy-, n-, iso- , sec- or t-butoxy-substituted methyl, ethyl, n- or isopropyl, n-, iso-, sec- or t-butyl, n-, iso-, sec-, t- or neopentyl, acetyl , Propionyl, n- or isobutyroyl, or in each case optionally cyano-, fluorine, chlorine- or bromine-substituted propenyl, butenyl, pentenyl, propenylcarbonyl, butenylcarbonyl Or pentenylcarbonyl, or in each case optionally cyano-, fluorine, chlorine, bromine-, methyl-, ethyl-, n- or isopropyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclo Hexyl, cyclopropylcarbonyl, cyclobutylcarbonyl, cyclopentylcarbonyl or cyclohexylcarbonyl, or in each case optionally Rho-, cyano-, fluorine-, chlorine-, bromine-, iodine-, methyl-, ethyl-, n- or isopropyl-, n-, iso-, sec- or t-butyl-, fluoromethyl- , Chloromethyl-, difluoromethyl-, dichloromethyl-, trifluoromethyl-, trichloromethyl-, methoxy-, ethoxy-, n- or isopropoxy-, n-, iso-, sec- Or t-butoxy-, fluoromethoxy-, difluoromethoxy-, trifluoromethoxy-, chlorodifluoromethoxy-, fluoroethoxy-, chloroethoxy-, difluoroethoxy-, dichloro Ethoxy-, fluorochloroethoxy- or trifluoroethoxy-substituted phenyl, naphthyl, phenylcarbonyl or naphthylcarbonyl, or in each case optionally nitro-, cyano-, fluorine-, Chlorine-, bromine-, iodine-, methyl-, ethyl-, n- or isopropyl-, n-, iso-, sec- or t-butyl-, fluoromethyl-, chloromethyl-, difluoromethyl- , Dichloromethyl-, tri Fluoromethyl-, trichloromethyl-, methoxy-, ethoxy-, n- or isopropoxy-, n-, iso-, sec- or t-butoxy-, fluoromethoxy-, difluoromethoxy -, Trifluoromethoxy-, chlorodifluoromethoxy-, fluoroethoxy-, chloroethoxy-, difluoroethoxy-, dichloroethoxy-, fluorochloroethoxy- or trifluoroethoxy -Substituted benzyl, phenylethyl, naphthylmethyl, phenylmethylcarbonyl, phenylethylcarbonyl or naphthylmethylcarbonyl.

R ¹ very particularly preferably represents hydrogen or in each case optionally cyano-, fluorine-, chlorine-, methoxy-, ethoxy-, n- or isopropoxy-substituted methyl, ethyl, n- Or propenyl, butenyl, propenylcarbo, or isopropyl, n-, iso- or sec-butyl, acetyl, propionyl, n- or isobutyroyl, or in each case optionally Nil or butenylcarbonyl, or in each case optionally represents fluorine-, chlorine- or methyl-substituted cyclopropyl, cyclopentyl, cyclohexyl, cyclopropylcarbonyl, cyclopentylcarbonyl or cyclohexylcarbonyl In each case optionally nitro-, cyano-, fluorine-, chlorine-, bromine-, iodine-, methyl-, ethyl-, n- or isopropyl-, n-, iso-, sec- or t-butyl- , Fluoromethyl-, chloromethyl-, difluoromethyl-, dichloromethyl-, trifluoro Tyl-, trichloromethyl-, methoxy-, ethoxy-, n- or isopropoxy-, fluoromethoxy-, difluoromethoxy-, trifluoromethoxy-, chlorodifluoromethoxy-, fluoro Ethoxy-, chloroethoxy-, difluoroethoxy-, dichloroethoxy-, fluorochloroethoxy- or trifluoroethoxy-substituted phenyl or phenylcarbonyl, or in each case optionally Cyano-, fluorine-, chlorine-, bromine-, iodine-, methyl-, ethyl-, n- or isopropyl-, n-, iso-, sec- or t-butyl-, fluoromethyl-, Chloromethyl-, difluoromethyl-, dichloromethyl-, trifluoromethyl-, trichloromethyl-, methoxy-, ethoxy-, n- or isopropoxy-, n-, iso-, sec- or t-butoxy-, fluoromethoxy-, difluoromethoxy-, trifluoro methoxy-, chlorodifluoromethoxy-, fluoroethoxy-, chloroethoxy-, difluoro Loethoxy-, dichloroethoxy-, fluorochloroethoxy- or trifluoroethoxy-substituted benzyl, phenylethyl, phenylmethylcarbonyl or phenylethylcarbonyl.

R ¹ particularly preferably represents hydrogen.

R ² preferably represents hydrogen or optionally cyano-, halogen- or C ₁ -C ₄ -alkoxy-substituted C ₁ -C ₁₀ -alkyl, (C ₁ -C ₁₀ -alkyl) carbonyl or ( C ₁ -C ₁₀ -alkoxy) carbonyl or optionally cyano-, halogen- or C ₁ -C ₄ -alkyl-substituted C ₃ -C ₆ -cycloalkyl, in each case optionally nitro- , Cyano-, halogen-, C ₁ -C ₄ -alkyl-, C ₁ -C ₄ -haloalkyl-, C ₁ -C ₄ -alkoxy- or C ₁ -C ₄ -haloalkoxy-substituted C _6- C ₁₀ -aryl or C ₆ -C ₁₀ -aryl-C ₁ -C ₄ -alkyl, or optionally nitro-, cyano-, halogen-, C ₁ -C ₄ -alkyl-, C ₁ -C _4- Haloalkyl-, C ₁ -C ₄ -alkoxy- or C ₁ -C ₄ -haloalkoxy-substituted heterocycle having up to 6 carbon atoms and at least one hetero atom selected from the group consisting of N, O and S Reel is shown.

R ² particularly preferably represents hydrogen or in each case optionally cyano-, fluorine-, chlorine-, bromine-, methoxy-, ethoxy-, n- or isopropoxy-, n-, iso- , sec- or t-butoxy-substituted methyl, ethyl, n- or isopropyl, n-, iso-, sec- or t-butyl, acetyl, propionyl, n- or isobutyroyl, methoxycarbo Neyl, ethoxycarbonyl, n- or isopropoxycarbonyl, or in each case optionally cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or isopropyl-substituted Cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, or in each case optionally nitro-, cyano-, fluorine-, chlorine-, bromine-, iodine-, methyl-, ethyl-, n- or isopropyl- , n-, iso-, sec- or t-butyl-, fluoromethyl-, chloromethyl-, difluoromethyl-, dichloromethyl-, trifluoromethyl-, trichloromethyl-, methoxy-, Ethoxy-, n- or isopropoxy-, n-, iso-, sec- or t-butoxy-, fluoromethoxy-, difluoromethoxy-, trifluoromethoxy-, chlorodifluoromethoxy- , Fluoroethoxy-, chloroethoxy-, difluoroethoxy-, dichloroethoxy-, fluorochloroethoxy- or trifluoroethoxy-substituted phenyl, naphthyl, benzyl or phenylethyl Or optionally nitro-, cyano-, fluorine-, chlorine-, bromine-, iodine-, methyl-, ethyl-, n- or isopropyl-, n-, iso-, sec- or t-butyl-, fluorine Chloromethyl-, chloromethyl-, difluoromethyl-, dichloromethyl-, trifluoromethyl-, trichloromethyl-, methoxy-, ethoxy-, n- or isopropoxy-, n-, iso- , sec- or t-butoxy-, fluoromethoxy-, difluoromethoxy-, trifluoromethoxy-, chlorodifluoromethoxy-, fluoroethoxy-, chloroethoxy-, difluoro Ethoxy-, dichloroethoxy-, fluorochloroethoxy- or trifluoroethoxy-substituted furyl, tetrahydrofuryl, thienyl, pyrrolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, iso Heterocyclyl selected from the group consisting of thiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyrazinyl, pyridazinyl and pyrimidinyl.

R ² very particularly preferably represents hydrogen or in each case is optionally cyano-, fluorine-, chlorine-, methoxy-, ethoxy-, n- or isopropoxy-substituted methyl, ethyl, n- Or isopropyl, acetyl, propionyl, methoxycarbonyl or ethoxycarbonyl, in each case optionally fluorine-, chlorine- or methyl-substituted cyclopropyl, cyclopentyl or cyclohexyl, in each case Optionally at nitro-, cyano-, fluorine-, chlorine-, bromine-, iodine-, methyl-, ethyl-, n- or isopropyl-, n-, iso-, sec- or t-butyl-, fluoro Methyl-, chloromethyl-, difluoromethyl-, dichloromethyl-, trifluoromethyl-, trichloromethyl-, methoxy-, ethoxy-, n- or isopropoxy-, fluoromethoxy-, Difluoromethoxy-, trifluoromethoxy-, chlorodifluoromethoxy-, fluoroethoxy-, chloroethoxy-, Fluoroethoxy-, dichloroethoxy-, fluorochloroethoxy- or trifluoroethoxy-substituted phenyl, benzyl or phenylethyl, or optionally cyano-, fluorine-, chlorine-, bromine-, Methyl-, ethyl-, n- or isopropyl-, fluoromethyl-, chloromethyl-, difluoromethyl-, dichloromethyl-, trifluoromethyl-, trichloromethyl-, methoxy-, ethoxy- , n- or isopropoxy-, fluoromethoxy-, difluoromethoxy-, trifluoromethoxy-, chlorodifluoromethoxy-, fluoroethoxy-, chloroethoxy-, difluoroethoxy- , Consisting of dichloroethoxy-, fluorochloroethoxy- or trifluoroethoxy-substituted furyl, thienyl, pyrrolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, pyridinyl and pyrimidinyl Heterocyclyl selected from the group.

R ² particularly preferably represents hydrogen or methyl.

R ³ preferably represents cyano-, halogen- or C ₁ -C ₄ -alkoxy-substituted C ₁ -C ₁₀ -alkyl, or optionally cyano-, halogen- or C ₁ -C ₄ -alkyl -Substituted C ₃ -C ₆ -cycloalkyl, or in each case optionally nitro-, cyano-, halogen-, C ₁ -C ₄ -alkyl-, C ₁ -C ₄ -haloalkyl-, C ₁ -C ₄ -alkoxy- or C ₁ -C ₄ -haloalkoxy-substituted C ₆ -C ₁₀ -aryl or C ₆ -C ₁₀ -aryl-C ₁ -C ₄ -alkyl, or optionally nitro-, cya No-, halogen-, C ₁ -C ₄ -alkyl-, C ₁ -C ₄ -haloalkyl-, C ₁ -C ₄ -alkoxy- or C ₁ -C ₄ -haloalkoxy-substituted and up to 6 carbons Heterocyclyl having an atom and at least one hetero atom selected from the group consisting of N, O and S.

R ³ is particularly preferably in each case optionally cyano-, fluorine-, chlorine-, bromine-, methoxy-, ethoxy-, n- or isopropoxy-, n-, iso-, sec- or t -Butoxy-substituted methyl, ethyl, n- or isopropyl, n-, iso-, sec- or t-butyl, or in each case optionally cyano-, fluorine-, chlorine-, bromine-, methyl -, Ethyl-, n- or isopropyl-substituted cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, or in each case optionally nitro-, cyano-, fluorine-, chlorine-, bromine-, iodine- , Methyl-, ethyl-, n- or isopropyl-, n-, iso-, sec- or t-butyl-, fluoromethyl-, chloromethyl-, difluoromethyl-, dichloromethyl-, trifluoro Methyl-, trichloromethyl-, methoxy-, ethoxy-, n- or isopropoxy-, n-, iso-, sec- or t-butoxy-, fluoromethoxy-, difluoromethoxy-, Trifluoromethoxy-, Chlorodifluoromethoxy-, fluoroethoxy-, chloroethoxy-, difluoroethoxy-, dichloroethoxy-, fluorochloroethoxy- or trifluoroethoxy-substituted phenyl, naphthyl, Benzyl or phenylethyl or optionally nitro-, cyano-, fluorine-, chlorine-, bromine-, iodine-, methyl-, ethyl-, n- or isopropyl-, n-, iso-, sec- or t-butyl-, fluoromethyl-, chloromethyl-, difluoromethyl-, dichloromethyl-, trifluoromethyl-, trichloromethyl-, methoxy-, ethoxy-, n- or isopropoxy- , n-, iso-, sec- or t-butoxy-, fluoromethoxy-, difluoromethoxy-, trifluoromethoxy-, chlorodifluoromethoxy-, fluoroethoxy-, chloroethoxy- , Difluoroethoxy-, dichloroethoxy-, fluorochloroethoxy- or trifluoroethoxy-substituted furyl, tetrahydrofuryl, thienyl, p Heterocyclyl selected from the group consisting of rollyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxdiazolyl, thiadiazolyl, pyridinyl, pyrazinyl, pyridazinyl and pyrimidinyl .

R ³ is very particularly preferably in each case optionally cyano-, fluorine-, chlorine-, methoxy-, ethoxy-, n- or isopropoxy-substituted methyl, ethyl, n- or isopropyl, iso Propyl or t-butyl, or in each case optionally fluorine-, chlorine- or methyl-substituted cyclopropyl, cyclopentyl or cyclohexyl, or in each case optionally nitro-, cyano-, fluorine-, chlorine -, Bromine-, iodine-, methyl-, ethyl-, n- or isopropyl-, n-, iso-, sec- or t-butyl-, fluoromethyl-, chloromethyl-, difluoromethyl-, Dichloromethyl-, trifluoromethyl-, trichloromethyl-, methoxy-, ethoxy-, n- or isopropoxy-, fluororomethoxy-, difluoromethoxy-, trifluoromethoxy-, chloro Difluoromethoxy-, fluoroethoxy-, chloroethoxy-, difluoroethoxy-, dichloroethoxy-, fluorochloro Ethoxy- or trifluoroethoxy-substituted phenyl, benzyl or phenylethyl, or optionally cyano-, fluorine-, chlorine-, bromine-, iodine-, methyl-, ethyl-, n- or isopropyl -, n-, iso, sec- or t-butyl-, fluoromethyl-, chloromethyl-, difluoromethyl-, dichloromethyl-, trifluoromethyl-, trichloromethyl-, methoxy-, e Oxy-, n- or isopropoxy-, n-, iso, sec- or t-butoxy-, fluoromethoxy-, difluoromethoxy-, trifluoromethoxy-, chlorodifluoromethoxy-, fluoro Loethoxy-, chloroethoxy-, difluoroethoxy-, dichloroethoxy-, fluorochloroethoxy- or trifluoroethoxy-substituted furyl, thienyl, pyrrolyl, pyrazolyl, oxazolyl , Heterocyclyl selected from the group consisting of isoxazolyl, thiazolyl, pyridinyl and pyrimidinyl.

R ³ is particularly preferably methyl, ethyl, isopropyl, isobutyl, t-butyl, trifluoromethyl, 1,1,2,2-tetrafluoroethyl, pentafluoroethyl, 1-chlorocyclopropyl, Phenyl, bromophenyl, nitrophenyl, methoxyphenyl, methylphenyl, naphthyl, 2-furyl, 3-furyl, 2-thienyl or 3-thienyl.

R ³ especially represents methyl, ethyl, isopropyl.

R ² and R ³ together also preferably represent C ₃ -C ₅ -alkanediyl (alkylene).

R ² and R ³ together also represent particularly preferably propane-1,3-diyl (trimethylene), butane-1,4-diyl (tetramethylene) or pentane-1,5-diyl (pentamethylene) .

R ² and R ³ together also very particularly preferably represent propane-1,3-diyl (trimethylene) or butane-1,4-diyl (tetramethylene).

R ⁴ preferably represents hydrogen, amino, or in each case optionally hydroxyl-, cyano-, halogen- or C ₁ -C ₄ -alkoxy-substituted C ₁ -C ₁₀ -alkyl, ( C ₁ -C ₁₀ -alkyl) carbonyl, C ₁ -C ₁₀ -alkylsulfonyl, C ₁ -C ₁₀ -alkylamino, (C ₁ -C ₁₀ -alkyl) carbonylamino or C ₁ -C ₁₀ -alkyl Represents sulfonylamino, or in each case optionally cyano- or halogen-substituted C ₂ -C ₁₀ -alkenyl, (C ₂ -C ₁₀ -alkenyl) carbonyl or C ₂ -C ₁₀ -alkynyl Indicates.

R ⁴ particularly preferably represents hydrogen, amino, or in each case optionally hydroxyl-, cyano-, fluorine-, chlorine-, bromine-, methoxy-, ethoxy-, n- or iso Propoxy-, n-, iso-, sec- or t-butoxy-substituted methyl, ethyl, n- or isopropyl, n-, iso-, sec- or t-butyl, acetyl, propionyl, n- Or isobutyroyl, methylsulfonyl, ethylsulfonyl, n- or isopropylsulfonyl, n-, iso-, sec- or t-butylsulfonyl, methylamino, ethylamino, n- or isopropylamino, n-, iso-, sec- or t-butylamino, acetylamino, propionylamino, n- or isobutyroylamino, methylsulfonylamino, ethylsulfonylamino, n- or isopropylsulfonylamino, n -Propenyl, butenyl, pente, which represent iso-, sec- or t-butylsulfonylamino, or in each case optionally cyano-, fluorine-, chlorine- or bromine-substituted Nil, propenylcarbonyl, butenylcarbonyl, pentenylcarbonyl, propynyl, butynyl or pentynyl.

R ⁴ very particularly preferably represents hydrogen, amino, or in each case optionally cyano-, fluorine-, chlorine-, bromine-, methoxy-, ethoxy-, n- or isopropoxy- Substituted methyl, ethyl, n- or isopropyl, n-, iso- or sec-butyl, acetyl, propionyl, n- or isobutyroyl, methylsulfonyl, ethylsulfonyl, n- or isopropylsulfonyl , Methylamino, ethylamino, n- or isopropylamino, acetylamino, propionylamino, methylsulfonylamino, ethylsulfonylamino, n- or isopropylsulfonylamino, or in each case optionally fluorine-, Chlorine- or bromine-substituted propenyl, butenyl, propenylcarbonyl, butenylcarbonyl, propynyl or butynyl.

R ⁴ particularly preferably represents hydrogen or methyl.

R ⁵ preferably represents hydrogen or optionally represents hydroxyl-, cyano-, halogen- or C ₁ -C ₄ -alkoxy-substituted C ₁ -C ₁₀ -alkyl, or in each case optionally cyano -Or halogen-substituted C ₂ -C ₁₀ -alkenyl or C ₂ -C ₁₀ -alkynyl or optionally cyano-, halogen- or C ₁ -C ₄ -alkyl-substituted C ₃ -C ₆ -Cycloalkyl or C ₃ -C ₆ -cycloalkyl-C ₁ -C ₄ -alkyl, or in each case optionally nitro-, cyano-, halogen-, C ₁ -C ₄ -alkyl-, C _1- C ₄ -haloalkyl-, C ₁ -C ₄ -alkoxy-, C ₁ -C ₄ -haloalkoxy-, C ₁ -C ₄ -alkylthio-, C ₁ -C ₄ -haloalkylthio-, phenyl-, Phenoxy- or piperazinyl- (optionally substituted by C ₁ -C ₄ -alkyl or optionally by halogen-, C ₁ -C ₄ -alkyl- or C ₁ -C ₄ -alkoxy-substituted phenyl) substitution C ₆ -C ₁₀ -aryl or C ₆ -C ₁₀ -aryl-C ₁ -C ₄ -alkyl, or in each case optionally Nitro-, cyano-, halogen-, C ₁ -C ₄ -alkyl-, C ₁ -C ₄ -haloalkyl-, C ₁ -C ₄ -alkoxy- or C ₁ -C ₄ -haloalkoxy-substituted and hetero Heterocyclyl or heterocyclyl-C ₁ -C ₄ -alkyl having up to 6 carbon atoms in the cyclyl group and at least one hetero atom selected from the group consisting of N, O and S.

R ⁵ particularly preferably represents hydrogen or in each case is optionally hydroxyl-, cyano-, fluorine-, chlorine-, methoxy-, ethoxy-, n- or isopropoxy-substituted methyl, ethyl , n- or isopropyl, n-, iso- or sec-butyl, or in each case optionally cyano-, fluorine, chlorine- or bromine-substituted propenyl, butenyl, pentenyl, propynyl, Butynyl or pentynyl, or in each case optionally cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or isopropyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclo Hexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, or in each case optionally nitro-, cyano-, fluorine-, chlorine-, bromine-, iodine-, methyl-, ethyl- , n- or isopropyl-, n-, iso-, sec- or t-butyl-, fluoromethyl-, chlorome -, Difluoromethyl-, dichloromethyl-, trifluoromethyl-, trichloromethyl-, methoxy-, ethoxy-, n- or isopropoxy-, n-, iso-, sec- or t- Butoxy-, fluoromethoxy-, difluoromethoxy-, trifluoromethoxy-, chlorodifluoromethoxy-, fluoroethoxy-, chloroethoxy-, difluoroethoxy-, dichloroethoxy- , Fluorochloroethoxy-, trifluoroethoxy-, methylthio-, ethylthio-, n- or isopropylthio-, n-, iso-, sec- or t-butylthio-, difluoromethyl Thio-, trifluoromethylthio-, phenyl-, phenoxy- or piperazinyl- (methyl, ethyl, n- or isopropyl, n-, iso-, sec- or t-butyl, or optionally fluorine -Chlorine-, bromine-, methyl-, ethyl-, n- or isopropyl-, n-, iso-, sec- or t-butyl-, methoxy-, ethoxy-, n- or isopropoxy- , n-, iso-, sec- or t-butoxy-substituted Optionally substituted with nil) substituted phenyl, naphthyl, benzyl, phenylethyl or naphthylmethyl, or in each case optionally nitro-, cyano-, fluorine-, chlorine-, bromine-, iodine-, methyl -, Ethyl-, n- or isopropyl-, n-, iso-, sec- or t-butyl-, fluoromethyl-, chloromethyl-, difluoromethyl-, dichloromethyl-, trifluoromethyl- , Trichloromethyl-, methoxy-, ethoxy-, n- or isopropoxy-, n-, iso-, sec- or t-butoxy-, fluoromethoxy-, difluoromethoxy-, trifluoro Methoxy-, chlorodifluoromethoxy-, fluoroethoxy-, chloroethoxy-, difluoroethoxy-, dichloroethoxy-, fluorochloroethoxy- or trifluoroethoxy-substituted furyl , Furylmethyl, tetrahydrofuryl, tetrahydrofurylmethyl, thienyl, thienylmethyl, pyrrolyl, pyrrolylmethyl, pyrazolyl, pyrazolylmethyl, jade Sazolyl, oxazolylmethyl, isoxazolyl, isoxazolylmethyl, thiazolyl, thiazolylmethyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyridinylmethyl, pyridinylethyl, pyrazinyl, pyri Heterocyclyl or heterocyclylalkyl selected from the group consisting of dazinyl, pyrimidinyl and pyrimidinylmethyl.

R ⁵ very particularly preferably represents hydrogen or in each case is optionally cyano-, fluorine-, chlorine-, methoxy-, ethoxy-, n- or isopropoxy-substituted methyl, ethyl, n- Or isopropyl, n-, iso- or sec-butyl, or in each case optionally represents fluorine-, chlorine- or bromine-substituted propenyl, butenyl, propynyl or butynyl, or optionally in each case Fluorine-, chlorine- or methyl-substituted cyclopropyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclopentylmethyl or cyclohexylmethyl, or in each case optionally , Bromine-, iodine-, methyl-, ethyl-, n- or isopropyl-, n-, iso-, sec- or t-butyl-, fluoromethyl-, chloromethyl-, difluoromethyl-, dichloro Methyl-, trifluoromethyl-, trichloromethyl-, methoxy-, ethoxy-, n- or isof Foxy-, fluoromethoxy-, difluoromethoxy-, trifluoromethoxy-, chlorodifluoromethoxy-, fluoroethoxy-, chloroethoxy-, difluoroethoxy-, dichloroethoxy-, Fluorochloroethoxy-, trifluoroethoxy-, methylthio-, ethylthio-, n- or isopropylthio-, difluoromethylthio-, trifluoromethylthio-, phenyl-, phenoxy- Or by piperazinyl- (methyl, ethyl, n- or isopropyl, or optionally fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or isopropyl-, methoxy-, ethoxy-, optionally substituted with n- or isopropoxy-substituted phenyl) substituted phenyl, benzyl or phenylethyl, or in each case optionally nitro-, cyano-, fluorine-, chlorine-, bromine-, iodine- , Methyl-, ethyl-, n- or isopropyl-, n-, iso-, sec- or t-butyl-, fluoromethyl-, chloromethyl-, difluoromethyl- , Dichloromethyl-, trifluoromethyl-, trichloromethyl-, methoxy-, ethoxy-, n- or isopropoxy-, n-, iso-, sec- or t-butoxy-, fluoromethoxy -, Difluoromethoxy-, trifluoromethoxy-, chlorodifluoromethoxy-, fluoroethoxy-, chloroethoxy-, difluoroethoxy-, dichloroethoxy-, fluorochloroethoxy- Or trifluoroethoxy-substituted furyl, furylmethyl, tetrahydrofuryl, tetrahydrofurylmethyl, thienyl, thienylmethyl, pyrrolyl, pyrrolylmethyl, pyrazolyl, pyrazolylmethyl, oxazolyl, oxazolylmethyl , Isoxazolyl, isoxazolylmethyl, thiazolyl, thiazolylmethyl, isothiazolyl, oxdiazolyl, thiadiazolyl, pyridinyl, pyridinylmethyl, pyridinylethyl, pyrimidinyl and pyrimidinylmethyl Heterocyclyl or heterocyclylalkyl selected from the group To burn.

Saturated or unsaturated hydrocarbon radicals, such as alkyl or alkenyl, including those bonded with heteroatoms such as, for example, alkoxy, are in each case as straight or branched as possible.

The optionally substituted radical may be monosubstituted or polysubstituted, in which case the substituents may be the same or different.

Halogen-substituted radicals such as halomethyl are mono- or polyhalogenated. In the case of polyhalogenation, the halogen atoms can be the same or different. Halogen atoms here represent fluorine, chlorine, bromine and iodine, in particular fluorine, chlorine and bromine.

The general or preferred radical definitions mentioned above apply to the compounds of the general formula (I) and correspondingly in each case the starting materials or intermediates necessary for preparation. These radical definitions can be combined with one another as desired, ie, combinations are possible between given preferred ranges.

In the present invention, preference is given to compounds of the formula (I) which comprise a combination of the meanings mentioned above as being preferred.

In the present invention, particular preference is given to compounds of the formula (I) which comprise a combination of the meanings mentioned above as being particularly preferred.

In the present invention, very particular preference is given to compounds of the formula (I) which comprise a combination of the meanings mentioned above as very particularly preferred.

Some known compounds of formula (I) used according to the invention are illustrated in Tables 1 and 2 below:

Table 1 :

Examples of Compounds of Formula (I)

Table 2 :

Another example of a compound of formula (I)

Some of the compounds of formula (I) used according to the invention are known (see literature mentioned in the introduction).

Some of the compounds of formula (I) used according to the invention are not known from the literature.

Thus, the compounds of the general formula (IA) below are claimed as novel compounds according to the invention.

Particular groups of compounds used according to the invention as novel compounds as claimed in the present application are represented by general formula (IA):

Where

A ^A represents haloalkyl,

Q ^A represents oxygen or sulfur,

R ^1A represents hydrogen or, in each case, optionally substituted alkyl, alkylcarbonyl, cycloalkyl, cycloalkylcarbonyl, aryl, arylcarbonyl, arylalkyl or arylalkylcarbonyl,

R ^2A represents hydrogen or, in each case, optionally substituted alkyl, alkylcarbonyl, alkoxycarbonyl, cycloalkyl, aryl, arylalkyl or heterocyclyl,

R ^3A in each occurrence represents optionally substituted alkyl, cycloalkyl, aryl, arylalkyl or heterocyclyl, or

R ^2A and R ^3A together also represent alkanediyl (alkylene),

R ^4A represents hydrogen, amino, or in each occurrence optionally substituted alkyl, alkylcarbonyl, alkylsulfonyl, alkylamino, alkylcarbonylamino, alkylsulfonylamino, alkenyl, alkenylcarbonyl or Alkynyl,

R ^5A represents in each case alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heterocyclyl or heterocyclylalkyl having at least two carbon atoms optionally substituted.

Hereinafter, the preferred ranges of the preferred substituents or radicals present in the general formula (IA) given above will be described:

A ^A preferably represents C ₁ -C ₈ -haloalkyl.

A ^A particularly preferably represents fluorine- and / or chlorine-substituted C ₁ -C ₅ -alkyl.

A ^A is very particularly preferably in each case optionally fluorine- and / or chlorine-substituted methyl, ethyl, n-propyl or isopropyl such as trifluoromethyl, difluoromethyl, pentafluoroethyl, hepta Fluoroisopropyl).

A ^A particularly preferably represents trifluoromethyl.

Q ^A preferably represents oxygen.

Q ^A also preferably represents sulfur.

R ^1A preferably represents hydrogen or in each case optionally cyano-, halogen- or C ₁ -C ₄ -alkoxy-substituted C ₁ -C ₁₀ -alkyl or (C ₁ -C ₁₀ -alkyl) carbo Or in each case optionally cyano-, halogen- or C ₁ -C ₄ -alkyl-substituted C ₃ -C ₆ -cycloalkyl or (C ₃ -C ₆ -cycloalkyl) carbonyl In each case optionally nitro-, cyano-, halogen-, C ₁ -C ₄ -alkyl-, C ₁ -C ₄ -haloalkyl-, C ₁ -C ₄ -alkoxy- or C ₁ -C ₄ -halo Alkoxy-substituted C ₆ -C ₁₀ -aryl or (C ₆ -C ₁₀ -aryl) carbonyl, or in each case optionally nitro-, cyano-, halogen-, C ₁ -C ₄ -alkyl-, C ₁ -C ₄ -haloalkyl-, C ₁ -C ₄ -alkoxy- or C ₁ -C ₄ -haloalkoxy-substituted (C ₆ -C ₁₀ -aryl) -C ₁ -C ₄ -alkyl or (C _6- C ₁₀ -aryl-C ₁ -C ₄ -alkyl) carbonyl.

R ^1A particularly preferably represents hydrogen, or in each case optionally cyano-, fluorine-, chlorine-, bromine-, methoxy-, ethoxy-, n- or isopropoxy-, n-, iso- , sec- or t-butoxy-substituted methyl, ethyl, n- or isopropyl, n-, iso-, sec- or t-butyl, n-, iso-, sec-, t- or neopentyl, acetyl , Propionyl, n- or isobutyroyl, or in each case optionally cyano-, fluorine-, chlorine- or bromine-substituted propenyl, butenyl, pentenyl, propenylcarbonyl, butenylcarbon Nyl or pentenylcarbonyl, or in each case optionally cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or isopropyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, Cyclohexyl, cyclopropylcarbonyl, cyclobutylcarbonyl, cyclopentylcarbonyl or cyclohexylcarbonyl, or in each case optionally Rho-, cyano-, fluorine-, chlorine-, bromine-, iodine-, methyl-, ethyl-, n- or isopropyl-, n-, iso-, sec- or t-butyl-, fluoromethyl- , Chloromethyl-, difluoromethyl-, dichloromethyl-, trifluoromethyl-, trichloromethyl-, methoxy-, ethoxy-, n- or isopropoxy-, n-, iso-, sec- Or t-butoxy-, fluoromethoxy-, difluoromethoxy-, trifluoromethoxy-, chlorodifluoromethoxy-, fluoroethoxy-, chloroethoxy-, difluoroethoxy-, dichloro Ethoxy-, fluorochloroethoxy- or trifluoroethoxy-substituted phenyl, naphthyl, phenylcarbonyl or naphthylcarbonyl, or in each case optionally nitro-, cyano-, fluorine-, Chlorine-, bromine-, iodine-, methyl-, ethyl-, n- or isopropyl-, n-, iso-, sec- or t-butyl-, fluoromethyl-, chloromethyl-, difluoromethyl- , Dichloromethyl-, tri Fluoromethyl-, trichloromethyl-, methoxy-, ethoxy-, n- or isopropoxy-, n-, iso-, sec- or t-butoxy-, fluoromethoxy-, difluoromethoxy -, Trifluoromethoxy-, chlorodifluoromethoxy-, fluoroethoxy-, chloroethoxy-, difluoroethoxy-, dichloroethoxy-, fluorochloroethoxy- or trifluoroethoxy -Substituted benzyl, phenylethyl, naphthylmethyl, phenylmethylcarbonyl, phenylethylcarbonyl or naphthylmethylcarbonyl.

R ^1A very particularly preferably represents hydrogen.

R ^2A preferably represents hydrogen or optionally cyano-, halogen- or C ₁ -C ₄ -alkoxy-substituted C ₁ -C ₁₀ -alkyl, (C ₁ -C ₁₀ -alkyl) carbonyl or ( C ₁ -C ₁₀ -alkoxy) carbonyl or optionally cyano-, halogen- or C ₁ -C ₄ -alkyl-substituted C ₃ -C ₆ -cycloalkyl, in each case optionally nitro- , Cyano-, halogen-, C ₁ -C ₄ -alkyl-, C ₁ -C ₄ -haloalkyl-, C ₁ -C ₄ -alkoxy- or C ₁ -C ₄ -haloalkoxy-substituted C _6- C ₁₀ -aryl or C ₆ -C ₁₀ -aryl-C ₁ -C ₄ -alkyl, or optionally nitro-, cyano-, halogen-, C ₁ -C ₄ -alkyl-, C ₁ -C _4- Haloalkyl-, C ₁ -C ₄ -alkoxy- or C ₁ -C ₄ -haloalkoxy-substituted heterocycle having up to 6 carbon atoms and at least one hetero atom selected from the group consisting of N, O and S Reel is shown.

R ^2A particularly preferably represents hydrogen or in each case optionally cyano-, fluorine-, chlorine-, bromine-, methoxy-, ethoxy-, n- or isopropoxy-, n-, iso- , sec- or t-butoxy-substituted methyl, ethyl, n- or isopropyl, n-, iso-, sec- or t-butyl, acetyl, propionyl, n- or isobutyroyl, methoxycarbo Neyl, ethoxycarbonyl, n- or isopropoxycarbonyl, or in each case optionally cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or isopropyl-substituted Cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, or in each case optionally nitro-, cyano-, fluorine-, chlorine-, bromine-, iodine-, methyl-, ethyl-, n- or isopropyl- , n-, iso-, sec- or t-butyl-, fluoromethyl-, chloromethyl-, difluoromethyl-, dichloromethyl-, trifluoromethyl-, trichloromethyl-, methoxy- , Ethoxy-, n- or isopropoxy-, n-, iso-, sec- or t-butoxy-, fluoromethoxy-, difluoromethoxy-, trifluoromethoxy-, chlorodifluoromethoxy -Fluoroethoxy-, chloroethoxy-, difluoroethoxy-, dichloroethoxy-, fluorochloroethoxy- or trifluoroethoxy-substituted phenyl, naphthyl, benzyl or phenylethyl Or optionally nitro-, cyano-, fluorine-, chlorine-, bromine-, iodine-, methyl-, ethyl-, n- or isopropyl-, n-, iso-, sec- or t-butyl-, Fluoromethyl-, chloromethyl-, difluoromethyl-, dichloromethyl-, trifluoromethyl-, trichloromethyl-, methoxy-, ethoxy-, n- or isopropoxy-, n-, iso -, sec- or t-butoxy-, fluoromethoxy-, difluoromethoxy-, trifluoromethoxy-, chlorodifluoromethoxy-, fluoroethoxy-, chloroethoxy-, difluoro Ethoxy-, dichloroethoxy-, fluorochloroethoxy- or trifluoroethoxy-substituted furyl, tetrahydrofuryl, thienyl, pyrrolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, iso Heterocyclyl selected from the group consisting of thiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyrazinyl, pyridazinyl and pyrimidinyl.

R ^2A very particularly preferably represents hydrogen, or in each case optionally cyano-, fluorine-, chlorine-, methoxy-, ethoxy-, n- or isopropoxy-substituted methyl, ethyl, n- Or isopropyl, methoxycarbonyl or ethoxycarbonyl, in each case optionally fluorine-, chlorine- or methyl-substituted cyclopropyl, cyclopentyl or cyclohexyl, or in each case optionally Nitro-, cyano-, fluorine-, chlorine-, bromine-, iodine-, methyl-, ethyl-, n- or isopropyl-, n-, iso-, sec- or t-butyl-, fluoromethyl- , Chloromethyl-, difluoromethyl-, dichloromethyl-, trifluoromethyl-, trichloromethyl-, methoxy-, ethoxy-, n- or isopropoxy-, fluoromethoxy-, difluorome Methoxy-, trifluoromethoxy-, chlorodifluoromethoxy-, fluoroethoxy-, chloroethoxy-, difluoro Ethoxy-, dichloroethoxy-, fluorochloroethoxy- or trifluoroethoxy-substituted phenyl, benzyl or phenylethyl, or optionally cyano-, fluorine-, chlorine-, bromine-, methyl- , Ethyl-, n- or isopropyl-, fluoromethyl-, chloromethyl-, difluoromethyl-, dichloromethyl-, trifluoromethyl-, trichloromethyl-, methoxy-, ethoxy-, n Or isopropoxy-, fluoromethoxy-, difluoromethoxy-, trifluoromethoxy-, chlorodifluoromethoxy-, fluoroethoxy-, chloroethoxy-, difluoroethoxy-, dichloro From the group consisting of ethoxy-, fluorochloroethoxy- or trifluoroethoxy-substituted furyl, thienyl, pyrrolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, pyridinyl and pyrimidinyl Represents selected heterocyclyl.

R ^2A particularly preferably represents hydrogen.

R ^3A preferably represents cyano-, halogen- or C ₁ -C ₄ -alkoxy-substituted alkyl having 1 to 10 carbon atoms, or optionally cyano-, halogen- or C ₁ -C _4- Alkyl-substituted cycloalkyl having 3 to 6 carbon atoms, or in each case having 6 or 10 carbon atoms in the aryl group and optionally 1 to 4 carbon atoms in the alkyl moiety and optionally in each case nitro-, cyano- , Halogen-, C ₁ -C ₄ -alkyl-, C ₁ -C ₄ -haloalkyl-, C ₁ -C ₄ -alkoxy- or C ₁ -C ₄ -haloalkoxy-substituted aryl or arylalkyl , Optionally nitro-, cyano-, halogen-, C ₁ -C ₄ -alkyl-, C ₁ -C ₄ -haloalkyl-, C ₁ -C ₄ -alkoxy- or C ₁ -C ₄ -haloalkoxy-substituted And heterocyclyl having up to 6 carbon atoms and at least one hetero atom selected from the group consisting of N, O and S.

R ^3A is particularly preferably in each case optionally cyano-, fluorine-, chlorine-, bromine-, methoxy-, ethoxy-, n- or isopropoxy-, n-, iso-, sec- or t -Butoxy-substituted methyl, ethyl, n- or isopropyl, n-, iso-, sec- or t-butyl, or in each case optionally cyano-, fluorine-, chlorine-, bromine-, methyl -, Ethyl-, n- or isopropyl-substituted cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, or in each case optionally nitro-, cyano-, fluorine-, chlorine-, bromine-, iodine- , Methyl-, ethyl-, n- or isopropyl-, n-, iso-, sec- or t-butyl-, fluoromethyl-, chloromethyl-, difluoromethyl-, dichloromethyl-, trifluoro Methyl-, trichloromethyl-, methoxy-, ethoxy-, n- or isopropoxy-, n-, iso-, sec- or t-butoxy-, fluoromethoxy-, difluoromethoxy-, Trifluoromethoxy-, Chlorodifluoromethoxy-, fluoroethoxy-, chloroethoxy-, difluoroethoxy-, dichloroethoxy-, fluorochloroethoxy- or trifluoroethoxy-substituted phenyl, naphthyl, Benzyl or phenylethyl or optionally nitro-, cyano-, fluorine-, chlorine-, bromine-, iodine-, methyl-, ethyl-, n- or isopropyl-, n-, iso-, sec- or t-butyl-, fluoromethyl-, chloromethyl-, difluoromethyl-, dichloromethyl-, trifluoromethyl-, trichloromethyl-, methoxy-, ethoxy-, n- or isopropoxy- , n-, iso-, sec- or t-butoxy-, fluoromethoxy-, difluoromethoxy-, trifluoromethoxy-, chlorodifluoromethoxy-, fluoroethoxy-, chloroethoxy- Difluoroethoxy-, dichloroethoxy-, fluorochloroethoxy- or trifluoroethoxy-substituted furyl, tetrahydrofuryl, thienyl, Heterocyclyl selected from the group consisting of rollyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxdiazolyl, thiadiazolyl, pyridinyl, pyrazinyl, pyridazinyl and pyrimidinyl .

R ^3A is very particularly preferably in each case optionally cyano-, fluorine-, chlorine-, methoxy-, ethoxy-, n- or isopropoxy-substituted methyl, ethyl, n- or isopropyl, iso Propyl or t-butyl, or in each case optionally fluorine-, chlorine- or methyl-substituted cyclopropyl, cyclopentyl or cyclohexyl, or in each case optionally nitro-, cyano-, fluorine-, chlorine -, Bromine-, iodine-, methyl-, ethyl-, n- or isopropyl-, n-, iso-, sec- or t-butyl-, fluoromethyl-, chloromethyl-, difluoromethyl-, Dichloromethyl-, trifluoromethyl-, trichloromethyl-, methoxy-, ethoxy-, n- or isopropoxy-, fluororomethoxy-, difluoromethoxy-, trifluoromethoxy-, chloro Difluoromethoxy-, fluoroethoxy-, chloroethoxy-, difluoroethoxy-, dichloroethoxy-, fluorocle Ethoxy- or trifluoroethoxy-substituted phenyl, benzyl or phenylethyl, or optionally cyano-, fluorine-, chlorine-, bromine-, iodine-, methyl-, ethyl-, n- or isopropyl -, n-, iso-, sec- or t-butyl-, fluoromethyl-, chloromethyl-, difluoromethyl-, dichloromethyl-, trifluoromethyl-, trichloromethyl-, methoxy-, Ethoxy-, n- or isopropoxy-, n-, iso-, sec- or t-butoxy-, fluoromethoxy-, difluoromethoxy-, trifluoromethoxy-, chlorodifluoromethoxy- , Fluoroethoxy-, chloroethoxy-, difluoroethoxy-, dichloroethoxy-, fluorochloroethoxy- or trifluoroethoxy-substituted furyl, thienyl, pyrrolyl, pyrazolyl, Heterocyclyl selected from the group consisting of oxazolyl, isoxazolyl, thiazolyl, pyridinyl and pyrimidinyl.

R ^3A is particularly preferably methyl, ethyl, isopropyl, isobutyl, t-butyl, trifluoromethyl, 1,1,2,2-tetrafluoroethyl, pentafluoroethyl, 1-chlorocyclopropyl, Phenyl, bromophenyl, nitrophenyl, methoxyphenyl, methylphenyl, naphthyl, 2-furyl, 3-furyl, 2-thienyl or 3-thienyl.

R ^3A represents especially methyl, ethyl, isopropyl.

R ^2A and R ^3A together also preferably represent C ₃ -C ₅ -alkanediyl (alkylene).

R ^2A and R ^3A together also represent particularly preferably propane-1,3-diyl (trimethylene), butane-1,4-diyl (tetramethylene) or pentane-1,5-diyl (pentamethylene) .

R ^2A and R ^3A together also very particularly preferably represent propane-1,3-diyl (trimethylene) or butane-1,4-diyl (tetramethylene).

R ^4A preferably represents hydrogen, amino, or in each case optionally cyano-, halogen- or C ₁ -C ₄ -alkoxy-substituted C ₁ -C ₁₀ -alkyl, (C ₁ -C ₁₀ -alkyl) carbonyl, C ₁ -C ₁₀ -alkylsulfonyl, C ₁ -C ₁₀ -alkylamino, (C ₁ -C ₁₀ -alkyl) carbonylamino or C ₁ -C ₁₀ -alkylsulfonylamino Or in each case optionally halogen-substituted C ₂ -C ₁₀ -alkenyl, (C ₂ -C ₁₀ -alkenyl) carbonyl or C ₂ -C ₁₀ -alkynyl.

R ^4A particularly preferably represents hydrogen, amino, or in each case optionally cyano-, fluorine-, chlorine-, bromine- methoxy-, ethoxy-, n- or isopropoxy-, n-, iso-, sec- or t-butoxy-substituted methyl, ethyl, n- or isopropyl, n-, iso-, sec- or t-butyl, acetyl, propionyl, n- or isobutyro 1, methylsulfonyl, ethylsulfonyl, n- or isopropylsulfonyl, n-, iso-, sec- or t-butylsulfonyl, methylamino, ethylamino, n- or isopropylamino, n-, iso sec- or t-butylamino, acetylamino, propionylamino, n- or isobutyroylamino, methylsulfonylamino, ethylsulfonylamino, n- or isopropylsulfonylamino, n-, iso- , sec- or t-butylsulfonylamino, or in each case optionally cyano-, fluorine-, chlorine- or bromine-substituted propenyl, butenyl, pentenyl, propenyl Carbonyl, butenylcarbonyl, pentenylcarbonyl, propynyl, butynyl or pentynyl.

R ^4A very particularly preferably represents hydrogen, amino, or in each case optionally cyano-, fluorine-, chlorine-, bromine-, methoxy-, ethoxy-, n- or isopropoxy- Substituted methyl, ethyl, n- or isopropyl, n-, iso- or sec-butyl, acetyl, propionyl, n- or isobutyroyl, methylsulfonyl, ethylsulfonyl, n- or isopropylsulfonyl , Methylamino, ethylamino, n- or isopropylamino, acetylamino, propionylamino, methylsulfonylamino, ethylsulfonylamino, n- or isopropylsulfonylamino, or in each case optionally fluorine-, Chlorine- or bromine-substituted propenyl, butenyl, propenylcarbonyl, butenylcarbonyl, propynyl or butynyl, especially hydrogen.

R ^4A particularly preferably represents hydrogen or methyl.

R ^5A preferably represents cyano-, halogen- or C ₁ -C ₄ -alkoxy-substituted C ₂ -C ₁₀ -alkyl, or in each case optionally halogen-substituted C ₂ -C ₁₀ -al alkenyl or C ₂ -C ₁₀ - alkynyl, or represent optionally cyano-, halogen- or C ₁ -C ₄ - alkyl-substituted C ₃ -C ₆ - cycloalkyl or C ₃ -C ₆ - cycloalkyl, - C ₁ -C ₄ -alkyl, or in each case optionally nitro-, cyano-, halogen-, C ₁ -C ₄ -alkyl-, C ₁ -C ₄ -haloalkyl-, C ₁ -C ₄ -Alkoxy-, C ₁ -C ₄ -haloalkoxy-, C ₁ -C ₄ -alkylthio-, C ₁ -C ₄ -haloalkylthio-, phenyl-, phenoxy- or piperazinyl- (C _1- Optionally substituted by C ₄ -alkyl or optionally by halogen-, C ₁ -C ₄ -alkyl- or C ₁ -C ₄ -alkoxy-substituted phenyl) C ₆ -C ₁₀ -aryl or C _6- C ₁₀ -aryl-C ₁ -C ₄ -alkyl, or in each case optionally nitro-, cyano-, halogen-, C ₁ -C ₄ -alkyl-, C ₁ -C ₄ -haloalkyl-, C ₁ -C ₄ -alkoxy- or C ₁ -C ₄ -haloalkoxy-substituted and at least one selected from the group consisting of up to 6 carbon atoms in the heterocyclyl group and consisting of N, O and S Heterocyclyl or heterocyclyl-C ₁ -C ₄ -alkyl having a hetero atom of

R ^5A is particularly preferably in each case optionally hydroxyl-, cyano-, fluorine-, chlorine-, methoxy-, ethoxy-, n- or isopropoxy-substituted ethyl, n- or isopropyl, n-, iso- or sec-butyl, or in each case optionally cyano-, fluorine-, chlorine- or bromine-substituted propenyl, butenyl, pentenyl, propynyl, butynyl or pentynyl Or in each case optionally cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or isopropyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclo Butylmethyl, cyclopentylmethyl or cyclohexylmethyl, or in each case optionally nitro-, cyano-, fluorine-, chlorine-, bromine-, iodine-, methyl-, ethyl-, n- or isopropyl-, n-, iso-, sec- or t-butyl-, fluoromethyl-, chloromethyl-, difluoromethyl-, dickle Roromethyl-, trifluoromethyl-, trichloromethyl-, methoxy-, ethoxy-, n- or isopropoxy-, n-, iso-, sec- or t-butoxy-, fluoromethoxy- , Difluoromethoxy-, trifluoromethoxy-, chlorodifluoromethoxy-, fluoroethoxy-, chloroethoxy-, difluoroethoxy-, dichloroethoxy-, fluorochloroethoxy-, Trifluoroethoxy-, methylthio-, ethylthio-, n- or isopropylthio-, n-, iso-, sec- or t-butylthio-, difluoromethylthio-, trifluoromethylthio -, By phenyl-, phenoxy- or piperazinyl- (methyl, ethyl, n- or isopropyl, n-, iso-, sec- or t-butyl, or optionally fluorine-, chlorine-, bromine-, Methyl-, ethyl-, n- or isopropyl-, n-, iso-, sec- or t-butyl-, methoxy-, ethoxy-, n- or isopropoxy-, n-, iso-, sec Or optionally substituted by t-butoxy-substituted phenyl C) substituted phenyl, naphthyl, benzyl, phenylethyl or naphthylmethyl, or in each case optionally nitro-, cyano-, fluorine-, chlorine-, bromine-, iodine-, methyl-, ethyl-, n- or isopropyl-, n-, iso-, sec- or t-butyl-, fluoromethyl-, chloromethyl-, difluoromethyl-, dichloromethyl-, trifluoromethyl-, trichloromethyl- , Methoxy-, ethoxy-, n- or isopropoxy-, n-, iso-, sec- or t-butoxy-, fluoromethoxy-, difluoromethoxy-, trifluoromethoxy-, chloro Difluoromethoxy-, fluoroethoxy-, chloroethoxy-, difluoroethoxy-, dichloroethoxy-, fluorochloroethoxy- or trifluoroethoxy-substituted furyl, furylmethyl, tetra Hydrofuryl, tetrahydrofurylmethyl, thienyl, thienylmethyl, pyrrolyl, pyrrolylmethyl, pyrazolyl, pyrazolylmethyl, oxazolyl, oxazolylmethyl, Soxazolyl, isoxazolylmethyl, thiazolyl, thiazolylmethyl, isothiazolyl, oxdiazolyl, thiadiazolyl, pyridinyl, pyridinylmethyl, pyridinylethyl, pyrazinyl, pyridazinyl, pyrimidinyl and pyri Heterocyclyl or heterocyclylalkyl selected from the group consisting of midinylmethyl.

R ^5A is very particularly preferably in each case optionally cyano-, fluorine-, chlorine-, methoxy-, ethoxy-, n- or isopropoxy-substituted ethyl, n- or isopropyl, n-, Iso- or sec-butyl, in each case optionally fluorine-, chlorine- or bromine-substituted propenyl, butenyl, propynyl or butynyl, or in each case optionally fluorine-, chlorine- or methyl -Substituted cyclopropyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclopentylmethyl or cyclohexylmethyl, or in each case optionally nitro-, cyano-, fluorine-, chlorine-, bromine-, iodine-, Methyl-, ethyl-, n- or isopropyl-, n-, iso-, sec- or t-butyl-, fluoromethyl-, chloromethyl-, difluoromethyl-, dichloromethyl-, trifluoromethyl -, Trichloromethyl-, methoxy-, ethoxy-, n- or isopropoxy-, fluoromethoxy-, Difluoromethoxy-, trifluoromethoxy-, chlorodifluoromethoxy-, fluoroethoxy-, chloroethoxy-, difluoroethoxy-, dichloroethoxy-, fluorochloroethoxy-, tri Fluoroethoxy-, methylthio-, ethylthio-, n- or isopropylthio-, difluoromethylthio-, trifluoromethylthio-, phenyl-, phenoxy- or piperazinyl- (methyl, With ethyl, n- or isopropyl, or optionally fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or isopropyl-, methoxy-, ethoxy-, n- or isopropoxy-substituted Optionally substituted with phenyl) substituted phenyl, benzyl or phenylethyl, or in each case optionally nitro-, cyano-, fluorine-, chlorine-, bromine-, iodine-, methyl-, ethyl-, n Or isopropyl-, n-, iso-, sec- or t-butyl-, fluoromethyl-, chloromethyl-, difluoromethyl-, dichloromethyl-, triple Oromethyl-, trichloromethyl-, methoxy-, ethoxy-, n- or isopropoxy-, n-, iso-, sec- or t-butoxy-, fluoromethoxy-, difluoromethoxy- , Trifluoromethoxy-, chlorodifluoromethoxy-, fluoroethoxy-, chloroethoxy-, difluoroethoxy-, dichloroethoxy-, fluorochloroethoxy-, trifluoroethoxy- Substituted furyl, furylmethyl, tetrahydrofuryl, tetrahydrofurylmethyl, thienyl, thienylmethyl, pyrrolyl, pyrrolylmethyl, pyrazolyl, pyrazolylmethyl, oxazolyl, oxazolylmethyl, isoxazolyl, isoxa Heterocyclyl selected from the group consisting of zolylmethyl, thiazolyl, thiazolylmethyl, isothiazolyl, oxdiazolyl, thiadiazolyl, pyridinyl, pyridinylmethyl, pyridinylethyl, pyrimidinyl and pyrimidinylmethyl or Heterocyclylalkyl.

Compounds of general formula (IB) are important:

Where

A ^A represents fluorine- and / or chlorine-substituted C ₁ -C ₈ -alkyl,

Q ^A represents oxygen or sulfur,

R ^3A represents methyl, ethyl, isopropyl, isobutyl, t-butyl, 1-chlorocyclopropyl, phenyl, 2-furyl, 3-furyl, 2-thienyl or 3-thienyl,

R ^5A in each case is optionally hydroxyl-, cyano-, fluorine-, chlorine-, methoxy-, ethoxy-, n- or isopropoxy-substituted ethyl, n- or isopropyl, n-, iso Or sec-butyl, or in each case optionally cyano-, fluorine-, chlorine- or bromine-substituted propenyl, butenyl, pentenyl, propynyl, butynyl or pentynyl, or in each case Optionally cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or isopropyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclo Pentylmethyl or cyclohexylmethyl, or in each case optionally nitro-, cyano-, fluorine-, chlorine-, bromine-, iodine-, methyl-, ethyl-, n- or isopropyl-, n-, iso -, sec- or t-butyl-, fluoromethyl-, chloromethyl-, difluoromethyl-, dichloromethyl-, tripleru Oromethyl-, trichloromethyl-, methoxy-, ethoxy-, n- or isopropoxy-, n-, iso-, sec- or t-butoxy-, fluoromethoxy-, difluoromethoxy- , Trifluoromethoxy-, chlorodifluoromethoxy-, fluoroethoxy-, chloroethoxy-, difluoroethoxy-, dichloroethoxy-, fluorochloroethoxy-, trifluoroethoxy- , Methylthio-, ethylthio-, n- or isopropylthio-, n-, iso-, sec- or t-butylthio-, difluoromethylthio-, trifluoromethylthio-, phenyl-, Phenoxy- or piperazinyl- (methyl, ethyl, n- or isopropyl, n-, iso-, sec- or t-butyl, or optionally fluorine-, chlorine-, bromine-, methyl-, ethyl- , n- or isopropyl-, n-, iso-, sec- or t-butyl-, methoxy-, ethoxy-, n- or isopropoxy-, n-, iso-, sec- or t-part Optionally substituted by oxy-substituted phenyl) substituted phenyl, Propyl, benzyl, phenylethyl or naphthylmethyl, or optionally in each case nitro-, cyano-, fluorine-, chlorine-, bromine-, iodine-, methyl-, ethyl-, n- or isopropyl-, n-, iso-, sec- or t-butyl-, fluoromethyl-, chloromethyl-, difluoromethyl-, dichloromethyl-, trifluoromethyl-, trichloromethyl-, methoxy-, ethoxy -, n- or isopropoxy-, n-, iso-, sec- or t-butoxy-, fluoromethoxy-, difluoromethoxy-, trifluoromethoxy-, chlorodifluoromethoxy-, fluoro Loethoxy-, chloroethoxy-, difluoroethoxy-, dichloroethoxy-, fluorochloroethoxy- or trifluoroethoxy-substituted furyl, furylmethyl, tetrahydrofuryl, tetrahydrofurylmethyl , Thienyl, thienylmethyl, pyrrolyl, pyrrolylmethyl, pyrazolyl, pyrazolylmethyl, oxazolyl, oxazolylmethyl, isoxazolyl, isoxazole Ylmethyl, thiazolyl, thiazolylmethyl, isothiazolyl, oxadizolyl, thiadiazolyl, pyridinyl, pyridinylmethyl, pyridinylethyl, pyrazinyl, pyridazinyl, pyrimidinyl, and pyrimidinylmethyl Heterocyclyl or heterocyclylalkyl selected from the group consisting of:

A ^A represents trifluoromethyl, trichloromethyl, difluoromethyl, pentafluoroethyl, heptafluoropropyl or heptafluoroisopropyl,

Q ^A represents oxygen or sulfur,

R ^3A represents methyl, ethyl, isopropyl, isobutyl, t-butyl, 1-chlorocyclopropyl, phenyl, 2-furyl, 3-furyl, 2-thienyl or 3-thienyl,

R ^5A represents cyclohexyl or in each case optionally nitro-, cyano-, fluorine-, chlorine-, bromine-, iodine-, methyl-, ethyl-, n- or isopropyl-, n-, iso- , sec- or t-butyl-, fluoromethyl-, chloromethyl-, difluoromethyl-, dichloromethyl-, trifluoromethyl-, trichloromethyl-, methoxy-, ethoxy-, n- or Isopropoxy-, fluoromethoxy-, difluoromethoxy-, trifluoromethoxy-, chlorodifluoromethoxy-, fluoroethoxy-, chloroethoxy-, difluoroethoxy-, dichloroethoxy -, Fluorochloroethoxy-, trifluoroethoxy-, methylthio-, ethylthio-, n- or isopropylthio-, difluoromethylthio-, trifluoromethylthio-, phenyl-, phenoxy By ci- or piperazinyl- (methyl, ethyl, n- or isopropyl, or optionally fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or isopropyl-, Especially substituted by methoxy-, ethoxy-, n- or isopropoxy-substituted phenyl) Particular preference is given to compounds of the formula (IB) which represent substituted phenyl, benzyl, phenylethyl or pyridinyl.

Saturated or unsaturated hydrocarbon radicals, such as alkyl or alkenyl, including those bonded with heteroatoms such as, for example, alkoxy, are in each case as straight or branched as possible.

The optionally substituted radical may be monosubstituted or polysubstituted, in which case the substituents may be the same or different.

Halogen-substituted radicals such as halomethyl are mono- or polyhalogenated. In the case of polyhalogenation, the halogen atoms can be the same or different. Halogen atoms here represent fluorine, chlorine, bromine and iodine, in particular fluorine, chlorine and bromine.

In the invention, ^preference is given to compounds of the formula (IA) in which Q ^A , R ^1A , R ^2A , R ^3A , R ^4A and R ^5A comprise a combination of the meanings mentioned above as being preferred.

In the present invention, particular preference is given to compounds of the formula (IA) in which Q ^A , R ^1A , R ^2A , R ^3A , R ^4A and R ^5A comprise a combination of the meanings mentioned above as being particularly preferred.

In the present invention, very particular preference is given to compounds of the formula (IA) in which Q ^A , R ^1A , R ^2A , R ^3A , R ^4A and R ^5A comprise a combination of the meanings mentioned above as very particularly preferred.

New trifluoromethylpyrazolinol and derivatives thereof of general formula (IA)-and similarly pyrazolol and derivatives thereof of general formula (I), some of which are also known

(a) the (thio) semicarbazide of formula (III), wherein the 1,3-dicarbonyl compound of formula (II) is optionally in the presence of one or more diluents and optionally in the presence of one or more reaction aids Or react with

(b) reacting the alkoxyalkenyl ketone of formula (IV) with (thio) semicabazide of formula (III), optionally in the presence of one or more diluents and optionally in the presence of one or more reaction aids Or

(c) an aminocarbonyl compound of general formula (VI) or a general formula (VII), wherein pyrazolin of general formula (V) is optionally in After reacting with iso (thio) cyanate of

If desired, a compound of formula (IA) obtained according to the method of (a), (b) or (c) above may be prepared by a conventional method. It was found to be obtained by conversion to:

Where

R ^2A , R ^3A , Q ^A , R ^4A and R ^5A are as defined above, provided that in general formula (VII) R ^5A is not H (hydrogen),

R represents alkyl,

X represents halogen,

Formula (IV) in addition to the cis- or Z-configuration of the above formula also includes the corresponding trans- or E-configuration.

Compounds of the general formula (IA) in which R ^1A represents H (hydrogen) are generally preferably in the presence and optionally a diluent such as tetrahydrofuran, in the presence of a reaction aid such as triethylamine or ethyldiisopropylamine, In the presence of 1,4-dioxane, methylisobutyl ketone, N, N-dimethylformamide or N, N-dimethylacetamide, R ^1A has the meaning excluding hydrogen and X ¹ is By reacting with a compound of formula X ¹ -R ^1A (VIII) representing halogen, R ^1A can be converted by conventional means to the corresponding compound of formula (IA) in which the meanings given further above are given. It is also possible to use diazomethane or trimethyloxonium tetrafluoroborate for methylation.

For example, when using 1,1,1-trifluorohexane-2,4-dione and 4-phenylthiosemicarbazide as starting materials, the reaction process of the method (a) according to the present invention is as follows. It can be represented by the same scheme:

For example, when 2-methoxy-5,5,5-trifluoro-2-penten-4-one and 4-ethyl semicarbazide are used as starting materials, the process (b) of the present invention The reaction process can be represented by the following scheme:

For example, when using 3-methyl-5-trifluoromethyl-4,5-dihydro-lH-pyrazole-5-ol and cyclohexyl isocyanate as starting materials, the process according to the invention (c) The reaction process can be represented by the following equation:

Formula (II) provides a general definition of 1,3-dicarbonyl compounds which are used as starting materials for carrying out process (a) according to the invention for the preparation of compounds of formula (IA). In this general formula (II), R ^2A and R ^3A are preferably, particularly preferably and very particularly preferred for these radicals with respect to the description of the compounds of the general formula (IA) according to the invention. Or very particularly preferred and the like.

Starting materials of formula (II) are known and / or may be prepared by known methods per se. See J. Fluorine Chem. 118 (2002), 135-148; J. Med. Chem. 40 (1997), 1347-1365; Synthesis 11 (1997), 1321-1324; Tetrahedron Lett. 43 (2002), 8701-8705.

Formula (IV) provides a general definition of alkoxyalkenyl ketones used as starting materials for carrying out process (b) according to the invention for preparing compounds of formula (IA). In this general formula (IV), R ^2A and R ^3A are preferably, particularly preferably and very particularly preferred for these radicals with respect to the description of the compounds of the general formula (IA) according to the invention. Or very particularly preferred and the like.

Starting materials of general formula (IV) are known and / or can be prepared by known methods per se. Chem. Ber. 115 (1982), 2766; 117 (1984), 3270; Chem. Lett. 1976, 499-502; J. Fluorine Chem. 99 (1999), 177-182; Synthesis 1986, 1013-1014; 1991, 483; Production Example].

Formula (III) provides a general definition of (thio) semicarbazide which is also used as starting material for carrying out the processes (a) and (b) according to the invention for the preparation of compounds of formula (IA). . In this general formula (III), Q ^A , R ^4A and R ^5A are preferably, particularly preferably and very particularly preferred for these radicals in connection with the description of the compounds of the general formula (IA) according to the invention. Or particularly preferred or very particularly preferred and the like.

Starting materials of formula (III) are known and / or can be prepared by known methods per se. Pharm. 335 (2002), 129-134; Bioorg. Med. Chem. Lett. 11 (2001), 1149-1152; Egypt. J. Chem. 41 (1998), 257-266; Org. Synth. Collect. Vol. 5 (1973), 168-170; Pharmazie 55 (2000), 500-502; 56 (2001), 121-124; Production Example].

Formula (V) provides a general definition of pyrazolinol used as starting material for carrying out process (c) according to the invention for preparing compounds of formula (IA). In this general formula (V), R ^2A and R ^3A are preferably, particularly preferably and very particularly preferred for these radicals with respect to the description of the compounds of the general formula (IA) according to the invention. Or very particularly preferred and the like.

Starting materials of general formula (V) are known and / or may be prepared by known methods per se. Chem. Het. Comp. 38 (2002), 668-676; J. Fluorine Chem. 94 (1999), 199-203; Russ. Chem. Bull. 51 (2002), 1280-1291; Production Example].

Formula (VI) provides a general definition of aminocarbonyl compounds which are also used as starting materials for carrying out process (c) according to the invention for preparing compounds of formula (IA). In this general formula (VI), Q ^A , R ^4A and R ^5A are preferably, particularly preferably and very particularly preferred for these radicals in connection with the description of the compounds of the general formula (IA) according to the invention. Or particularly preferred or very particularly preferred and the like.

Aminocarbonyl compounds of formula (VI) are known organic reagents for synthesis.

Formula (VII) provides a general definition of iso (thio) cyanate which is also used as starting material for carrying out process (c) according to the invention for preparing compounds of general formula (IA). In this formula (VII), Q ^A and R ^5A are preferably, particularly preferably and very particularly preferably preferred or particularly preferred for these radicals in connection with the description of the compounds of the general formula (IA) according to the invention. Or very particularly preferred and the like.

Iso (thio) cyanates of formula (VII) are known organic reagents for synthesis.

Processes (a), (b) and (c) according to the invention for preparing compounds of general formula (IA) are preferably carried out using one or more diluents. Suitable diluents for carrying out the processes (a), (b) and (c) according to the invention are especially inert organic solvents. These are especially optionally halogenated aliphatic, alicyclic or aromatic hydrocarbons such as benzine, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, carbon tetrachloride; Ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran, ethylene glycol dimethyl ether or ethylene glycol diethyl ether; Ketones such as acetone, butanone or methyl isopropyl; Nitriles such as acetonitrile, propionitrile or butyronitrile; Amides such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide; Esters such as methyl acetate or ethyl acetate; Sulfoxides such as dimethyl sulfoxide; Alcohols such as methanol, ethanol, n- or isopropanol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, mixtures of these and water or pure water.

Processes (a), (b) and (c) according to the invention for the preparation of compounds of general formula (I) are optionally carried out using one or more reaction aids. Suitable reaction aids for carrying out the process according to the invention are generally customary inorganic or organic base or acid acceptors. They are preferably alkali metal or alkaline earth metal acetates, amides, carbonates, bicarbonates, hydrides, hydroxides or alkoxides, for example sodium acetate, potassium acetate, calcium acetate, lithium amide, sodium amide, potassium amide, calcium amide , Sodium carbonate, potassium carbonate, cesium carbonate, calcium carbonate, sodium bicarbonate, potassium bicarbonate, calcium bicarbonate, lithium hydride, sodium hydride, potassium hydride, calcium hydride, lithium hydroxide, sodium hydroxide, potassium hydroxide, calcium hydroxide, sodium methoxide, ethoxide , n-propoxide or isopropoxide, n-butoxide, isobutoxide, sec-butoxide, t-butoxide, potassium methoxide, ethoxide, n-propoxide or isopropoxide, n -Butoxide, isobutoxide, sec-butoxide, t-butoxide; And also basic organic nitrogen compounds such as tri methylamine, triethylamine, tripropylamine, tributylamine, ethyldiisopropylamine, N, N-dimethylcyclohexylamine, dicyclohexylamine, ethyldicyclohexyl Amines, N, N-dimethylaniline, N, N-dimethylbenzylamine, pyridine, 2-methyl-, 3-methyl-, 4-methyl-, 2,4-dimethyl-, 2,6-dimethyl-, 3, 4-dimethyl- and 3,5-dimethylpyridine, 5-ethyl-2-methylpyridine, 4-dimethylaminopyridine, N-methylpiperidine, 1,4-diazabicyclo [2.2.2] octane (DABCO) , 1,5-diazabicyclo [4.3.0] non-5-ene (DBN) or 1,8-diazabicyclo- [5.4.0] undec-7-ene (DBU).

When carrying out the processes (a), (b) and (c) according to the invention, the reaction temperature can vary within a relatively wide range. Generally these processes are carried out at temperatures of 0 to 150 ° C, preferably 10 to 120 ° C.

Processes (a), (b) and (c) according to the invention are generally carried out under atmospheric pressure. However, it is also possible to carry out the process according to the invention at elevated or reduced pressure—generally from 0.1 to 10 bar.

When carrying out the processes (a), (b) and (c) according to the invention, the starting materials are generally used in approximately equimolar amounts. However, it is also possible to use one component in relative excess. The reaction is generally carried out in a suitable diluent in the presence of a reaction aid and the reaction mixture is generally stirred for several hours at the required temperature. Post-treatment is carried out in a conventional manner (see Preparation Examples).

Processes (a), (b) and (c) are equally suitable for novel compounds of general formula (IA) and some of the compounds of general formula (I) in which some are known. When preparing compounds of formula (I), the radicals R ^2A , R ^3A , R ^4A and R ^5A of the general formulas (II) to (VII) mean R ² , R ³ , R ⁴ and R ⁵ Corresponds to

The active compounds according to the invention protect plants and plant organs, increase the yield of harvesting products, improve the quality of harvesting materials, and meet in the field of protection and hygiene in agriculture, forestry, gardening, leisure facilities, storage products and materials. It is suitable for controlling animal pests, in particular insects, arachnids and nematodes, has good plant compatibility, exhibits acceptable levels of toxicity to warm-blooded animals and is environmentally friendly. These can preferably be used as plant protection agents. They are effective against moderately sensitive or resistant species and all or some stages of development. The pests mentioned above include:

The order of Isopoda , for example Oniscus asellus , Armadillidium vulgare and Porcellio scaber .

Millipedes (Diplopoda) tree, for example Blast niul loose obtain Tula tooth (Blaniulus guttulatus).

From the genus Chilopoda , for example Geophilus carpophagus and Scutigera spp .

From the order of Symphyla , for example Scutigerella immaculata.

Thysanura , for example Lepisma saccharina .

From Collembola , for example Onychiurus armatus.

Orthoptera , for example, Acheta domesticus, Gryllotalpa spp. , Locusta migratoria migratorioides , Melanofluus species ( Melanoplus spp.) And Schistocerca gregaria .

From the order of Blattaria , for example Blatta orientalis , Periplaneta americana , Leucophaea maderae and Blattella germanica .

Dermaptera , for example Forficula auricularia.

Termite Isoptera , for example Reticulitermes spp .

Phthiraptera , for example, Pediculus humanus corporis, Haematopinus spp ., Linognathus spp ., Trichodectes spp. .) And damalinia spp .

Thysanoptera , for example Hercinothrips femoralis , Thrips tabaci , Thrips palmi and Frankliniella accidentalis ).

From the order of Heteroptera , for example Eurygaster spp ., Dysdercus intermedius , Piesma quadrata , Cimex lectularius , Rodney Rhodnius prolixus and Triatoma spp .

Cicadas (Homoptera) tree, for example, waters right Death in Brassica (Aleurodes brassicae), bemi cyano other dedicate (Bemisia tabaci), the tree Valley right des bar Fora Rio room (Trialeurodes vaporariorum), Apis notice blood (Aphis gossypii), the breather Vico Rhine Brassica (Brevicoryne brassicae), the creep Tommy juice Leavis (Cryptomyzus ribis), Apis wave bar (Aphis fabae), Apis breech (Aphis pomi), Erie O Soma Raney gerum (Eriosoma lanigerum), hyaluronic rope Teruel's Arun Hyniopterus arundinis , Phylloxera vastatrix , Pemphigus spp. , Macrosiphum avenae , Myzus spp ., Phorodon humulli humuli , Rhopalosiphum padi , Empoasca spp ., Euscelis bilobatus , Nephotettix cincticeps , Lecanium corn i), the poinsettia Ole Ah between (Saissetia oleae), Lao del Parks Austria Tel Ruth (Laodelphax striatellus), Neela Parque Bata Lou Regensburg (Nilaparvata lugens), Oh sludge de Ella Augusta is T (Aonidiella aurantii), Oh Speedy Aspidiotus hederae , Pseudococcus spp . And Psylla spp .

Lepidoptera , for example Pectinophora gossypiella, Bupalus piniarius , Cheimatobia brumata , Lithocolletis blancardella , Hyponomeuta padella , Plutella x ylostella , Malacosoma neustria , Euproctis chrysorrhoea , Lymantria spp. ), part Kula matrix Tour Barry Ella (Bucculatrix thurberiella), Philo greatest seutiseu sheet mozzarella (Phyllocnistis citrella), Agrobacterium-Tees species (Agrotis spp.), six pediatric species (Euxoa spp.), Pell Tia species (Feltia spp.), Earias insulana , Heliothis spp ., Mamestra brassicae , Panolis flammea , 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 ambiguella , Homona magnanima , Tortrix viridana , Cnaphalocerus spp . And Oulema oryzae .

Coleoptera , for example, Anobium punctatum, Rhizopertha dominica , Bruchidius obtectus , Acanthoscelides obtectus , Hylotrupes bajulus , Agelastica alni , Leptinotarsa decemlineata , Phaedon cochleariae , Diabrotica spp ), peusil Rio des Creative sose Palacio (Psylliodes chrysocephala), epilra keuna Bari Betsy's (Epilachna varivestis), Ato Maria kinds (Atomaria spp.), duck chair Phil Ruth repairs namen system (Oryzaephilus surinamensis), St labor's servants (Anthonomus spp.), Citrus peel loose species (Sitophilus spp.), cut out ot kusu sulka tooth (Otiorrhynchus sulcatus), poly Cosmo test sorbitan di Douce (Cosmopolites sordidus), establish Torin Scotland know Millie's (Ceuthorrhynchus assimilis), Hebrews Blow Force Galactica (Hypera postica), no scalpel test species (Dermestes spp.), Tree logo Dumaguete species (Trogoderma spp.), No trail pandanus species (Anthrenus spp.), Oh ride Attagenus spp ., Lyctus spp ., Meligethes aeneus , Ptinus spp ., Niptus hololeucus , Gibiumuf Gibbium psylloides , Tribolium spp ., Tenebrio molitor , Agriotes spp ., Conoderus spp ., Melonta Melonta ( Melolontha melolontha ), Amphimallon solstitialis , Costelytra zealandica and Lissorhoptus oryzophilus .

Hymenopera species, for example Diprion spp ., Hoplocampa spp ., Lasius spp ., Monomorium pharaonis and Vespa species Vespa spp .

Diptera , for example Aedes spp ., Anopheles spp ., Culex spp ., Drosophila melanogaster , Musca species. Musca spp .), Fannia spp ., Calliphora erythrocephala , Lucilia spp ., Chrysomyia spp ., Cuterebra spp . ), Gastrophilus spp ., Hyppobosca spp ., Stomoxys spp ., Oestrus spp ., Hypoderma spp . , Tabanus spp. , Tannia spp ., Bibio hortulanus , Oscinella frit , Phorbia spp ., Pegomia hyosquiami ( Pegomyia hyoscyami ), Ceratitis capitata , Dacus oleae , Tifula paludosa ( Tipula paludosa ), Hylemyia spp . And Liriomyza spp .

From the order of Siphonaptera , for example Xenopsylla cheopis and Ceratophyllus spp .

Arachnida , for example, Scorpio maurus , Latrodectus mactans , Acarus siro , Argas spp ., Ornitodoros species ( 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. .), the other hemi Sone Hemitarsonemus (mousse species spp.) and breather bipal crispus species (Bre vipalpus spp .).

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

Compounds of general formula (I) according to the invention are particularly useful for ticks (such as Myzus persicae ), beetles and their corresponding larvae (such as paedone cocleari), butterfly caterpillars (such as spodope Spodoptera frugiperda ), leaf mites (such as Tetranychus urticae ), fleas (such as Ctenocephalides felis ), flies and their larvae (such as Lucilia cuprina) ( Lucilia cuprina )) and also nematodes (such as Meloidogyne incognita ).

In some cases, the compounds according to the invention can also be used at certain concentrations or in application rates and also as herbicides and microbicides, for example fungicides, antibacterials and fungicides. If desired, they can also be used as intermediates or precursors for synthesizing other active compounds.

According to the invention, all plants and plant parts can be treated. Plant is to be understood here as meaning all plants and plant populations, such as desired or unwanted wild plants or crops (including naturally occurring crops). Crops include plant varieties and transgenic plants that may or may not be protected by the authority of a plant breeder, by conventional breeding and optimization methods, by biotechnology and genetic engineering methods or by these methods. It may be a plant obtainable in combination. Plant part means all above-ground and underground parts and organs of the plant, such as, for example, shoots, leaves, flowers and roots, for example leaves, needles, stalks, stems, flowers, Fruits, fruits, seeds, roots, tubers and rhizomes may be mentioned. Plant parts also include harvested plants, and nutritional and reproductive materials such as seedlings, tubers, rhizomes, grounds and seeds.

Treatment of plants and plant parts with the active compounds according to the invention is also carried out according to conventional processing methods, for example by dipping, spraying, evaporating, misting, spraying, applying, injecting, in the case of propagating materials, in particular seed By applying one or more coatings directly or on their surroundings, environment or storage space.

Active compounds are usually used as solutions, emulsions, hydrating powders, suspensions, powders, powders, pastes, soluble powders, granules, suspension-emulsion concentrates, natural and synthetic materials impregnated with the active compounds, and microcapsules in polymeric materials. It can be converted into the formulation of.

These formulations are prepared by known methods, for example by mixing the active compounds with extenders, ie liquid solvents and / or solid carriers, optionally using surfactants, ie emulsifiers and / or dispersants and / or foam formers.

If the extender used is water, for example an organic solvent may be used as the auxiliary solvent. Suitable liquid solvents are mainly aromatic compounds such as xylene, toluene or alkylnaphthalene, chlorinated aromatic and chlorinated aliphatic hydrocarbons such as chlorobenzene, chloroethylene or methylene chloride, cyclohexane or paraffins, for example mineral oil fractions, mineral oils and vegetable oils. Strong aliphatic hydrocarbons such as aliphatic hydrocarbons, butanol or glycols and ethers and esters thereof, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, dimethylformamide and dimethyl sulfoxide and water.

Suitable solid carriers are, for example, ammonium salts and ground natural minerals such as kaolin, clay, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground powders such as highly dispersed silica, alumina and silicates. It is a synthetic material. Suitable granular carriers for granules are, for example, pulverized and classified natural rocks such as calcite, marble, pumice, calcite and dolomite, and synthetic granules of inorganic and organic flours, and sawdust, coconut husks, corncobs and tobacco stems. Granules of organic matter. Suitable emulsifiers and / or foam formers are for example nonionic and anionic emulsifiers, for example polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulfonates, alkyls Sulfates, arylsulfonates and protein hydrolysates. Suitable dispersants are, for example, lignosulphite waste liquors and methylcellulose.

Tackifiers such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latex, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, and also natural phospholipids such as cephalin and lecithin, and synthetic phospholipids Can be used for Other additives may be mineral and vegetable oils.

Colorants such as inorganic pigments such as iron oxide, titanium oxide and prussian blue, and organic colorants such as alizarin colorants, azo colorants and metal phthalocyanine colorants and salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc. Micronutrients may also be used.

The formulations generally contain 0.1 to 95% by weight, preferably 0.5 to 90% by weight of active compound.

The active compounds according to the present invention can be used in the commercially available formulations and in the use forms prepared from these formulations with other active compounds such as insecticides, attractants, disinfectants, fungicides, acaricides, nematicides, fungicides, growth regulators or herbicides. May be present as a mixture of. Pesticides include, for example, phosphate esters, carbamates, carboxylates, chlorinated hydrocarbons, phenylurea, materials produced by microorganisms, and the like.

Examples of particularly advantageous components in the mixtures are the following compounds:

Fungicides:

2-phenylphenol, 8-hydroxyquinoline sulfate,

Acibenzola-S-methyl, Aldimorph, Amidoflumet, Ampropyl force, Ampropyl force-potassium, Andoprim, Anilazin, Azaconazole, Azoxystrobin,

Benalacyl, Benodanil, Benomyl, Ventiavalicab-isopropyl, Benzamacryl, Benzamacryl-Isobutyl, Villanaphos, Vinapacryl, Biphenyl, Bittertanol, Blastisidin-S, Bromuco Nazol, buririmate, butiobate, butylamine,

Calcium-polysulfide, capsaicin, captapol, captan, carbendazim, carboxycin, capropamide, carbon, quinomethionate, clobenthiazone, chlorfenazole, chloroneb, chlorotalonyl, clozolinate , Clozilacon, cyazopamide, cyflufenamide, cymoxanyl, cyproconazole, cyprodinyl, cyprofuram,

Dagger G, devacarb, diclofluanide, diclones, dichlorophene, diclocemet, diclomezin, dichloran, dietofencarb, difenokazole, diflumethorim, dimethirimol, dimetho Morph, Dimoxistrobin, Diconazole, Diconazole-M, Dinocap, Diphenylamine, Dipyrithione, Ditalimfoss, Dithianon, Dodine, Dragoxolone,

Edifene Force, Epoxyconazole, Ethaboxam, Ethirimole, Etridazole,

Soxaxadon, phenamidone, phenananil, phenarimol, fenbuconazole, fenfuram, phenhexamide, phenytropan, phenoxanyl, fenpiclonyl, phenpropidine, phenpropimod, ferbam, Fluazinam, Flubenzimin, Fludioxonyl, Flumetober, Flumorph, Fluoromid, Fluoxastrobin, Fluquinconazole, Fluprimidol, Flusilazole, Flusulfamid, Flutolanil , Flutriafol, polpet, pocetyl-Al, pocetyl-sodium, fuberidazole, furalacyl, furametpyr, purcarbanyl, purmecyclolox,

Guazatin,

Hexachlorobenzene, hexaconazole, hymexazole,

Imazalil, imibenconazole, iminottadine triacetate, iminottadine tris (albesylate), iodocarb, ifconazole, iprobenfos, iprodione, iprovalicab, irumamycin, isoprothiolane, Isovaledion,

Kasugamycin, Cresoxime-Methyl,

Mancozeb, maneb, meperimzone, mepanipyrim, mepronil, metallaxyl, metallaxyl-M, metconazole, metasulfocarb, metfuroxam, metiram, metomistrobin, metsulfobox, Mildiomycin, Michael Robutanil, Michael Rozoline,

Natamycin, nicobifen, nitrotal-isopropyl, nobiflumuron, noarimol,

Opuras, orissastrobin, oxadixyl, oxolinic acid, oxpoconazole, oxycarboxycin, oxypentetiin,

Paclobutrazole, pepurazoate, fenconazole, pensicuron, phosphodiphene, phthalide, picoxistrobin, piperaline, polyoxine, polyoxorim, provenazole, prochloraz, procymidone, pro Pamocarb, propanosine-sodium, propiconazole, propineb, proquinazide, prothioconazole, pyraclostrobin, pyrazophos, pyriphenox, pyrimethanyl, pyroquilon, pyroxipur Pyrronitrin,

Quinconazole, quinoxifen, quintogen,

Cymeconazole, spiroxamine, sulfur,

Tebuconazole, Teclophthalam, Tecnazen, Tecyclcyclase, Tetraconazole, Thiabendazole, Tiothiophene, Tifluzamide, Thiophanate-methyl, Thiram, Thioxymide, Tollclofos-methyl , Tolylufluoride, triadimefon, triadimenol, triazbutyl, triazoxide, tricyclamide, tricyclazole, tridemorph, trixystrobin, triflumizol, tripolin, tri Ticonazole,

Uniconazole,

Validamycin A, vinclozoline,

Geneb, Zeram, Joksamid,

(2S) -N- [2- [4-[[3- (4-chlorophenyl) -2-propynyl] oxy] -3-methoxyphenyl] ethyl] -3-methyl-2-[(methylsul Phonyl) amino] butanamide,

1- (1-naphthalenyl) -1H-pyrrole-2,5-dione,

2,3,5,6-tetrachloro-4- (methylsulfonyl) pyridine,

2-amino-4-methyl-N-phenyl-5-thiazolecarboxamide,

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

3,4,5-trichloro-2,6-pyridine dicarbonitrile,

Actinate,

Cis-1- (4-chlorophenyl) -2- (1H-1,2,4-triazol-1-yl) cycloheptanol,

Methyl 1- (2,3-dihydro-2,2-dimethyl-1H-inden-1-yl) -1H-imidazole-5-carboxylate,

Potassium carbonate,

N- (6-methoxy-3-pyridinyl) cyclopropane carboxamide,

N-butyl-8- (1,1-dimethylethyl) -1-oxaspiro [4.5] decan-3-amine,

Sodium tetrathiocarbonate, and

Copper salts and preparations, such as Bordeaux mixtures, copper hydroxide, copper naphthenate, copper oxychloride, copper sulfate, cupraneb, copper oxide, mancopper, auxin-copper.

disinfectant:

Bronopol, dichlorophene, nitrapyrin, nickel dimethyldithiocarbamate, kasugamycin, octylinone, furancarboxylic acid, oxytetracycline, probenazole, streptomycin, teclophthalam, copper sulfate and other copper agents.

Pesticides / Acaricides / Nematicides:

Abamectin, ABG-9008, Acetate, Acequinosyl, Acetamiprid, Acetoprole, Acrinatrin, AKD-1022, AKD-3059, AKD-3088, Alanicab, Aldicarb, Aldoxicarb, Allerthrin , Alpha-cypermethrin (alphamethrin), amidoflumet, aminocarb, amitraz, avermectin, AZ 60541, azadirachtin, azametifoss, azinfos-methyl, azinfos-ethyl, azocyclo Teen,

Bacillus pophilia, Bacillus sp. Erytheus, Bacillus subtilis, Bacillus thuringiensis, Bacillus thuringiensis strain EG-2348, Bacillus thuringiensis strain GC-91, Bacillus thuringiensis strain NCTC-11821, Baculova Ireress, Buberia Bassiana, Buberian Tenella, Benclothiaz, Bendiocarb, Benpuracarb, Bensultap, Benzoximate, Beta-Cyfluthrin, Beta-Cypermethrin, Bifenazate, B Pentrin, Vinapacryl, Bioaletrin, Bioaletrin-S-cyclopentyl-isomer, Bioethanomethrin, Biopermethrin, Bioresmethrin, Bistrifluron, BPMC, Brofenprox, Bromophos-ethyl , Bromopropylate, bromfenbinfoss (-methyl), BTG-504, BTG-505, bufencarb, buprofezin, butathiofoss, butocarboxime, butoxycarboxime, butylpyridaben,

Kadusafos, campechlor, cabaril, cabofuran, cabofennotion, carbosulphan, katop, CGA-50439, quinomethionate, chlordan, chlordimeform, chloretocab, chlorethoxyphosph, chlorfenapyr , Chlorfenbin Force, Chlorfluazuron, Chlormephos, Chlorobenzylate, Chloropicrine, Chlorproxyfen, Chlorpyriphos-methyl, Chlorpyriphos (-ethyl), Clovafortrin, Chromafenozide, Cis-Sai Permethrin, cis-resmethrin, cis-permethrin, clocitrin, cloetocarb, clopentezin, clotianidine, clothiazobene, cordlemon, coomaphos, cyanophenfos, cyanophos, cycloprene, Cycloprotrin, cydia formonela, cyfluthrin, sihalothrin, cyhexatin, cypermethrin, cyphenotrin (1R-trans isomer), cyromargin,

DDT, deltamethrin, demethone-S-methyl, demethone-S-methylsulfone, diafenthiuron, dialilifos, diazinone, diclopention, dichlorbos, dicopol, dicrotofoss, dicycla Neil, Diflubenzuron, Dimefluthrin, Dimethoate, Dimethylbinfos, Dinobutone, Dinocap, Dinotefuran, Diophenolran, Disulfotone, Docusat-Sodium, Dofenapain, DOWCO-439,

Eflusilanate, emamectin, emamectin-benzoate, empentrin (1R-isomer), endosulfan, entomorphora species (spp.), EPN, espenvalelate, ethiophencarb, ethiprole, ethione , Etoprophos, etofenprox, ethoxazole, erythropose,

Pampur, Penamifoss, Penazaquine, Penbutatin Oxide, Penfluthrin, Phenythrothione, Phenobucarb, Phenothiocarb, Phenoxa Cream, Phenoxycarb, Penpropartlin, Penpyrad, Penpyri Trine, Phenpyroximate, Pensulfothion, Pention, Pentripanyl, Fenvalrate, Fipronil, Flornicamid, Fluacrypyrim, Fluazuron, Flubenzimin, Flubrositeinate, Flusai Clock-Suron, Flusiteinate, Flufenerim, Flufenoxuron, Flufenprox, Flumethrin, Flupyrazophos, Flutenzin (Flufenzin), Fluvalinate, Phonophos, Formate, Formimoti On, phosphmethyllan, phosphthiazate, fufenfenx (fluxyfen), furathiocarb,

Gamma-cyhalothrin, gamma-HCH, gosiflure, glandlure, granulosis virus,

Halfenprox, halofenozide, HCH, HCN-801, heptenophos, hexaflumuron, hexthiaxose, hydrammonone, hydroprene,

IKA-2002, imidacloprid, imiprotrin, indoxacarb, iodofenfos, iprobenfos, isosafos, isofenfos, isoprocarb, isoxation, ivermectin,

Japonilure,

Cadetrin,

Nuclea polyhedrosis virus,

Quinoprene,

Lambda cyhalothrin, lindane, lufenuron,

Malathion,

1. Acetylcholine esterase (AChE) inhibitors.

1.1 carbamate, for example

Alanicarb, Aldicarb, Aldoxicarb, Alixicarb, Aminocarb, Azametifoss, Bendiocarb, Benfuracarb, Buppencarb, Butacarb, Butokkasimsim, Butoxycarbsim, Cabaril, Cabofuran, Cabo Sulfan, cloetocarb, coomafoss, cyanofenfoss, cyanofoss, dimethyllan, ethiophencarb, phenobucarb, phenothiocarb, formmethate, furathiocarb, isoprocarb, metham-sodium, methiocarb , Metomil, metholcarb, oxamyl, pyrimikab, promecarb, propoxur, thiodicarb, thiophanox, trimetacarb, XMC, xylylcarb,

1.2 organic phosphates, for example

Acetate, Azametifoss, Ajinfoss (-methyl, -ethyl), Bromophos-ethyl, Brompfenbinfoss (-methyl), Butadithiofoss, Cardusafoss, Carbophenothione, Chloethoxyfoss, Chlor Penvinforce, Chlormephos, Chlorpyriphos (-methyl / -ethyl), Coomaphos, Cyanophenfoss, Cyanophos, Chlorfenbinfos, Demethone-S-methyl, Demethone-S-methylsulfone, Diali Phos, diazinon, diclofenvinthion, dichlorbos / DDVP, dicrotophos, dimethoate, dimethylbinfos, dioxabenzophos, disulfotone, EPN, ethion, etoprophos, etrimpos, Pampur, Penamifoss, Phenythrothione, Pensulfothion, Pention, Flupyrazophos, Phonophos, Formomolion, Phosmethyllan, Phosthiazate, Heptenophos, Iodofenfos, Iprobenfo Isazofos, isofenfoss, isopropyl O-salicylate, isoxation, malathion, mecarbam, methacryfoss , Metamidofos, metidathione, mevinfoss, monocrotophos, naled, ometoate, oxydemethone-methyl, parathion (-methyl / -ethyl), pentoate, forate, posalon, posmet, Phosphomidone, Phosphocarb, Depth of Heart, Pyrimifos (-methyl / -ethyl), Propenophos, Propaphos, Propetafoss, Prothiophos, Protoate, Pycloclofos, Pyridapention, Pyri Dation, Quinal Force, Cebu Force, Sulpotep, Sulprophos, Tebupyrimphos, Temephos, Terbufoss, Tetrachlorbinfos, Tiomethone, Triazophos, Trichlorpon, Bamidothione,

2. Sodium Channel Regulators / Voltage-Dependent Sodium Channel Blockers

2.1 pyrethroids, for example

Acrinatrin, alletrin (d-cis-trans, d-trans), beta-cyfluthrin, bifenthrin, bioaletrin, bioaletrin-S-cyclopentyl isomer, bioethanomethrin, biopermethrin , Bioresmethrin, clovapotrin, cis-cypermethrin, cis-resmethrin, cis-permethrin, clositerin, cycloprotrin, cyfluthrin, cyhalothrin, cypermethrin (alpha-, beta-, Theta-, zeta-), cyphenotrin, DDT, deltamethrin, empentrin (1R-isomer), esfenvaleric, etofenprox, fenflutrin, phenpropatrine, phenpytrin, pen Valerate, flubrocithinate, flucithinate, flufenprox, flumethrin, fluvalinate, fufenfenrox, gamma-cyhalothrin, imiprotrin, cardetrine, ramma-cyhalothrin , Metofluthrin, permethrin (cis-, trans-), phenothrin (1R-trans isomer), fr Lalettrin, profluthrin, protrifenbut, pyrethmetrin, resmetrin, RU 15525, silafluorene, tau-fluvalinate, tefluthrin, traletrine, tetramethrin (1R-isomer), Tralomethrin, transflutrin, ZXI 8901, pyrethrin (pyrethrum),

2.2 oxadiazines such as indoxacarb,

3. Acetylcholine Receptor Agonists / antagonists

3.1 chloronicotinyl, for example

Acetamiprid, clothianidine, dinotefuran, imidacloprid, nitenpyram, nithiazine, tiacloprid, thiamethoxam,

3.2 nicotine, bensultap, katap,

4. Acetylcholine Receptor Modulator

4.1 Spinosine, for example spinosad

5. GABA-Regulating Chloride Channel Antagonists

5.1 cyclodiene organic chlorine, for example

Campechlor, chlordan, endosulfan, gamma-HCH, HCH, heptachlor, lindane, methoxycyclo,

5.2 pipefall, for example

Acetoprole, etiprole, fipronil, vaniliprole,

6. Chloride Channel Activator

6.1 mectin, for example

Abamectin, avermectin, emamectin, emamectin-benzoate, ivermectin, milbectin, milbimecin,

7. Larva hormone mimetics, eg

Diphenols, epopenonane, phenoxycarb, hydroprene, quinoprene, metoprene, pyriproxyfen, triprene,

8. Ecdyson agonists / disruptors

8.1 diacylhydrazines, for example

Chromafenozide, halofenozide, methoxyfenozide, tebufenozide,

9. Chitin Biosynthesis Inhibitors

9.1 benzoylurea, for example

Bistrifluron, Clofluazuron, Diflubenzuron, Fluazuron, Flucycloloxone, Flufenoxlon, Hexaflumuron, Lufenuron, Novaluron, Nobifluuron, Fenfluron, Tflubenzuron , Triple lumuron,

9.2 Buprofezin

9.3 Cyclo Margin,

10. Oxidative phosphorylation inhibitors, ATP disruptors

10.1 diafenthiuron,

10.2 organic tin, for example azocyclotin, cyhexatin, fenbutatin-oxide,

11. oxidative phosphorylation inhibitors by blocking H-proton gradients,

11.1 pyrrole, for example chlorfenapyr,

11.2 dinitrophenols such as vinapacryl, dinobutone, dinocap, DNOC,

12. I-side electron transfer inhibitor

12.1 METIs, for example penazaquine, penpyroximate, pyrimidipene, pyridaben, tebufenpyrad, tolfenpyrad,

12.2 idamethylnon,

12.3 decopol,

13. II-Side Electron Transfer Inhibitor

13.1 rotenone,

14. III-Side Electron Transfer Inhibitor

Acequinosyl, Fluacrypyrim,

15. Insect Vesicle Microbial Disintegrant

Bacillus thuringiensis strains,

16. fat synthesis inhibitors,

Tetronic acid such as spirodiclofen, spiromesifen,

Tetramic acid, for example 3- (2,5-dimethylphenyl) -8-methoxy-2-oxo-1-azaspiro [4.5] de-3-sen-4-yl ethyl carbonate (aka carboxylic acid, 3 -(2,5-dimethylphenyl) -8-methoxy-2-oxo-1-azaspiro [4,5] de-3-sen-4-yl ethyl ester, CAS-Reg.-No .: 382608- 10-8) and carboxylic acid, cis-3- (2,5-dimethylphenyl) -8-methoxy-2-oxo-1-azaspiro [4,5] de-3-sen-4-yl ethyl ester , CAS-Reg.-No .: 203313-25-1),

17, carboxamides, for example flornicamid,

18. octopaminergic agonist, for example amitraz,

19, magnesium-promoting ATPase inhibitors such as propargite,

20. phthalamide, for example N ² - [1,1- dimethyl-2- (methylsulfonyl) ethyl] -3-iodo -N ¹ - [2- methyl-4- [1,2,2, 2-tetrafluoro-1- (trifluoromethyl) ethyl] phenyl] -1,2-benzenedicarboxamide (CAS-Reg.-No .: 272451-65-7),

21. Neracetoxin analogues such as thiocyclam hydrogen oxalate, thiosulfato-sodium,

22. Biological agents, hormones or pheromones, eg

Azadirachtin, Bacillus species, Burberry species, Codmon species, Metadium species, Paesilomyces species, Turingienxins, Verticillium species,

23. Active compounds of unknown or nonspecific mechanism of action,

23.1 fumigants such as aluminum phosphide, methyl bromide, sulryl fluoride,

23.2 Selective food intake inhibitors such as cryolite, floricamid, pymetrozine,

23.3 mite growth inhibitors, for example clofentezin, ethoxazole, hexiaxox,

23.4 Amidoflumet, benclothiaz, benzoxmate, bifenazate, bromopropylate, buprofezin, quinomethionate, chlordimeform, chlorobenzylate, chloropicrine, clothiazobene, cycloprene , Dicyclanyl, phenoxa cream, pentrifanil, flubenzimin, flufenerim, flutenzin, gosiflure, hydrammethylnon, japonilurere, methoxadione, petroleum, piperonyl butoxide , Potassium oleate, pyridalyl, sulfluramid, tetradipon, tetrasul, traarate, verbutin,

Compound 3-methyl phenyl propylcarbamate (chumaside Z),

Compound 3- (5-chloro-3-pyridinyl) -8- (2,2,2-trifluoroethyl) -8-azabicyclo [3.2.1] octane-3-carbonitrile (CAS Reg. 185982-80-3) and the corresponding 3-endo-isomer (CAS Reg. No. 185984-60-5) (WO-96 / 37494, WO-98 / 25923),

And formulations containing pesticidal active plant extracts, nematodes, fungi or viruses.

Mixtures with other known active ingredients such as herbicides, fertilizers, growth regulators, anti-mitogens and / or signaling substances are also possible.

When used as a pesticide in their commercially available formulations and in the use forms prepared from these formulations, the active compounds according to the invention can also be present as mixtures with synergists. Synergists are compounds which increase the activity of the active compound without the synergist added being themselves need to be active.

When used as a pesticide in commercially available formulations thereof and in the use forms prepared from these formulations, the active compounds according to the invention are also inhibitors which reduce degradation of the active compounds after application to plant habitats, surface of plant parts or plant tissue It may be present in the form of a mixture with.

The active compound content of the use forms prepared from commercially available formulations can vary within wide ranges. The active compound concentration of the use forms is 0.0000001 to 95% by weight, preferably 0.0001 to 1% by weight.

The compound is applied in a conventional manner suitable for the use form.

When used in hygienic pests and stored product pests, the active compounds exhibit excellent residual activity against wood and clay, as well as good stability against alkalis on lime substrates.

As mentioned above, all plants and their parts can be treated according to the invention. In a preferred embodiment, wild plant species and plant cultivars or plant cultivars obtained by conventional biological cultivation methods such as hybrid breeding or protoplast fusion and some of them are treated. In another preferred embodiment, genetically engineered transgenic plants and plant cultivars (genetically modified organisms) and portions thereof are treated with conventional methods, where appropriate. The terms "part" "part of the plant" or "plant part" have been described above.

Particularly preferably, plant cultivars, which are commercially available or in use in each case, are treated according to the invention. Plant cultivars should be understood as plants having new properties (“characteristics”) that can be obtained by conventional cultivation, mutagenesis or recombinant DNA techniques. These may be cultivar, varieties, biotypes or genotypes.

Depending on the plant type and / or plant species, their location and growth conditions (soil, climate, growth period, nutrients), an additive ("raising") effect may also be seen by treatment according to the present invention. Thus, for example, reduction in the amount of use of substances and preparations that can be used according to the invention and / or broadening the activity spectrum and / or increasing activity, improving plant growth, increasing hot or cold resistance, drought, or water or soil salinity Effects such as increased resistance to plants, increased flowering, ease of harvest, increased maturity, increased crop yields, improved quality and / or nutritional value of harvested products, and improved shelf life and / or throughput of harvested products May appear.

Preferred transgenic plants (ie, those obtained genetically) and / or plant cultivars treated according to the present invention contain genetic material that confers useful properties ("characteristics") that are particularly advantageous to these plants by genetic engineering modifications. Includes all plants. Examples of such properties include improved plant growth, increased high or low temperature resistance, drought, or increased resistance to water or soil salts, increased flowering, ease of harvest, increased maturity, increased crop yields, improved quality of harvested products, and / or Increased nutritional value, and increased shelf life and / or processability of harvested products. Further particular highlights of such properties include increased plant defense against animal and microbial pests such as insects, mites, phytopathogenic fungi, bacteria and / or viruses, and also increased plant resistance to certain herbicidally active substances. Examples of transgenic plants may include important crops such as cereals (wheat, rice), corn, soybeans, potatoes, cotton, tobacco, oilseed rape and also fruit trees (opening apples, pears, citrus fruits and grape fruits). Corn, soybeans, potatoes, cotton, tobacco and oilseed rape. The properties to be emphasized (“characteristics”) are particularly pronounced in plant-derived toxins, in particular genetic material obtained from Bacillus thuringiensis (eg genes CryIA (a), CryIA (b), CryIA (c), CryIIA, Toxins formed in plants (hereinafter referred to as "Bt plants") by CryIIIA, CryIIIB2, Cry9c, Cry2Ab, Cry3Bb and CryIF and combinations thereof increase the plant's defense against insects, arachnids, nematodes, slugs and snails. . Also of particular emphasis is the increased defense of plants against fungi, bacteria and viruses due to systemically acquired resistance (SAR), cystemine, phytoalexin, eliminator and resistance genes and correspondingly expressed proteins and toxins. . Other particularly emphasized properties ("characteristics") also include the ability of plants for certain herbicidal active substances, such as imidazolinone, sulfonylurea, glyphosate or phosphinothricin (eg "PAT" gene). Increased tolerability. In each case certain genes conferring the desired properties (“characteristics”) may also be present in transgenic plants in combination. Examples of "Bt plants" include YIELD GARD ^® (e.g. corn, cotton, soybean), KnockOut ^® (e.g. corn), StarLink ^® (e.g. corn), Bollgard ^® (e.g. cotton), Nucotn ^® (e.g. cotton) And corn varieties, cotton varieties, soybean varieties and potato varieties which are commercially available under the NewLeaf ^® (eg potato) brand name. Examples of herbicide-tolerant plants include Roundup Ready ^® (glyphosate tolerant, eg corn, cotton, soybean), Liberty Link ^® (phosphinothricin tolerant, e.g. oilseed rape), IMI ^® (imidazolinone tolerant) And corn varieties, cotton varieties and soybean varieties available under the trade name STS ^® (sulfonylurea tolerant such as corn). Examples of herbicide-tolerant plants (plants bred by conventional methods for herbicide tolerability) may also be mentioned varieties sold under the name Clearfield ^® (eg maize). Of course, the above description also applies to plant varieties which have the above-described genetic properties or which remain to be developed, with plants to be developed and / or marketed in the future.

The plants listed above can be treated particularly advantageously according to the invention with a compound of the general formula (I) or a mixture of active compounds according to the invention. The preferred ranges mentioned above for the active compounds or mixtures also apply to the treatment of these plants. Particular emphasis is given to the treatment of plants with the compounds or mixtures specifically mentioned in the present text.

The active compounds according to the invention are not only plant pests, sanitary pests and stored product pests, but also animal parasites (in vitro parasites) in the field of veterinary medicine, for example true mites, princess mites, scabies mites, tromculid mites. It is active against, fly (shoot and lick), parasitic fly larvae, teeth, hair, algae and fleas. These parasites include:

Anoplurida , for example Haematopinus spp ., Linognathus spp ., Pediculus spp ., Pthirus spp ., Sole Novotes spp .

Hairs (Mallophagida) neck and arm assembly Serena (Amblycerina) and yiseukeu furnace Serena (Ischnocerina) suborder, such as tree Agate phone species (Trimenopon spp.), Agate phone species (Menopon spp.), Trinoton spp (teurino tone species. ), Bovicola spp ., Werneckiella spp ., Lepikentron spp ., Damalina spp ., Trichodectes spp ., Felicola spp .

Diptera and Nematocerina and Brachycerina subfamily, for example Aedes spp ., Anopheles spp ., Culex spp ., simul Solarium species (Simulium spp.), Yushi water Solarium species (Eusimulium spp.), play bottoming mousse species (Phlebotomus spp.), Lucho Mia species (Lutzomyia spp.), Cooley Koh des species (Culicoides spp.), chestnut Thorpe Crysops spp ., Hybomitra spp ., Atylotus spp ., Tabanus spp ., Haematopota spp ., Filippomia spp . Philipomyia spp. ), Braula spp ., Musca spp ., Hydrotaea spp ., Stomoxys spp ., Haematobia spp . , Morelia species (Morellia spp.), plates Chania species (Fannia spp.), Gloucestershire Sinai species (Glossina spp.), Carly Fora species (Calliphora spp.), rusilriah species (Luci lia spp .), Chrysomyia spp ., Wolhlfahrtia spp. , Sarcophaga spp ., Oestrus spp ., Hypoderma spp . ), Gasterophilus spp ., Hyppobosca spp ., Lipoptena spp ., Melophagus spp .

Siphonapterida species, for example Pulex spp ., Ctenocephalides spp ., Xenopsylla spp ., Ceratophyllus spp .

From the order of Heteropterida , for example Cimex spp ., Triatoma spp ., Rhodnius spp ., Panstrongylus spp .

Blattarida neck, for example Blatta orientalis , Periplaneta americana , Blatta germanica , Supella spp .

Mites (Acaria (Acarida)) subclass and meta- and meso stigmasterol other - (. Ornithodorus spp) (Meta and Mesostigmata) tree, for example, are the gas species (. Argas spp), ornithine Todo loose species, auto Flavian species (Otobius spp.), Rhodes ikso species (Ixodes spp.), cancer Bulletin Mama species (Amblyo㎜a spp.), Ruth bupil species (Boophilus spp.), der Do centaur species (Dermancentor spp.), under the village killed lease species ( Haemaphysalis spp.), kind of hyaluronic romma (Hyalo㎜a spp.), Lippi Palouse three species (Rhipicephalus spp.), der Mani Seuss species Dermanyssus (spp.), Raillietia (Tia Riley species spp.), Seuss pneumoniae species ( Pneumonyssus spp .), Sternostoma spp ., Varroa spp .

Actinedida ( Prostigmata ) and Acaridida ( Astigmata ) necks, for example Acarapis spp ., Cheyletiella spp . ), Ornithocheyletia spp ., Myobia spp ., Psorergates spp ., Demodex spp ., Trombicula spp . , Listrophorus spp ., Acarus spp ., Tyrophagus spp ., Caloglyphus spp ., Hypodectes spp . , Pterolichus spp. , Psoroptes spp. , Chorioptes spp ., Otodectes spp ., Sarcoptes spp . dress species in Noto (Notoedres spp.), shown immense Cope test species (Knemidocoptes spp.), Citrus di test species (Cytodites spp.), La Shi-off test species (Laminosioptes spp.).

The active compounds of general formula (I) according to the invention can also be used for agricultural livestock, such as cattle, sheep, goats, horses, pigs, donkeys, camels, buffaloes, rabbits, chickens, turkeys, ducks, geese, bees, and other houses. Are suitable for controlling arthropods that invade, for example, dogs, cats, birds in bird cages and fish tanks, and so-called laboratory animals such as hamsters, guinea pigs, rats, and mice. By controlling these arthropods, death and yield reduction (in meat, milk, wool, leather, eggs, honey, etc.) are reduced, and thus more economical and convenient animal management is possible by using the active compounds according to the present invention.

The active compounds according to the invention are administered parenterally in the field of veterinary medicine, for example, by enteral administration in the form of tablets, capsules, beverages, potions, granules, pastes, pills, feeds, suppositories, eg For example by injection (intramuscular, subcutaneous, intravenous and intraperitoneal, etc.), by insertion, by intranasal administration, for example by dipping or dipping, spraying, swelling, spotting-on, washing and Applied in a known manner by application of the skin by means of spraying or in the form of shaped articles containing the active compound, eg in the form of necklaces, ear tags, tail marks, leg bands, bridles, indicators, etc. do.

When used in livestock, poultry, domestic animals, etc., the active compound is directly or 100 to 10,000 times diluted as a preparation containing the active compound in an amount of 1 to 80% by weight (e.g. powders, emulsions, flow agents). It may be used in the form of, or in the form of a drug bath.

It has also been found that the active compounds according to the invention exhibit potent insecticidal action against insects which destroy industrial materials.

The following insects may be mentioned as preferred examples, but are not limited to these:

Beetles , for example Hylotrupes bajulus , Chlorophorus pilosis , Anobium punctatum , Xestobium rufovillosum , Ptilinus pecticornis , Dendrobium pertinex , Ernobius mollis , Priobium carpini , Lyctus brunneus , Rick Lyctus africanus , Lyctus planicollis , Lyctus linearis , Lyctus pubescens , Trogoxylon aequale , Mintes lugi Minthes rugicollis , Xyleborus spec ., Tryptodendron spec ., Apate monachus , Bostrychus capucins ), Heterobostrychus brunnes , Synoxylon spec ., Dinoderus minutus .

The Marv Terrance (Hermapterans), for example, when Rex juben kusu (Sirex jubencus), right three loose exhaust gas (Urocerus gigas), right three loose exhaust gas tie the Taunus (Urocerus gigas taignus), right three loose brother rolls (Urocerus augur ).

Termites (Termites), for example, a knife Termez flaviviruses Collins (Kalotermes flavicollis), Cryptococcus Termez brevis (Cryptotermes brevis), heteroaryl Termez indicator coke (Heterotermes indicola), retinal Cooley Termez flaviviruses Fes (Reticulitermes flavipes) , Reticulitermes santonensis , Reticulitermes lucifugus , Mastotermes darwiniensis , Zootermopsis nevadensis , Coff Cottertotermes formosanus .

Bristletails , for example Lepisma saccharina .

Industrial materials in the context of the present invention are understood in the sense of non-living materials, preferably synthetic materials, adhesives, glues, paper, boards, leather, wood, woodwork and paint.

Materials to be protected from insect infestation are particularly preferably wood and woodworking articles.

Woods and woodworkings which may be protected by the composition according to the invention or mixtures comprising them are for example construction timbers, wooden beams, railway sleepers, bridge components, breakwaters, vehicles made of wood, Box, pallet, container, telephone pole, wooden sign, window and door made of wood, plywood, chipboard, joining, or wood products that are very commonly used in house building or building furniture.

The active compounds can be used on their own in the form of concentrates or generally customary preparations, for example powders, granules, solutions, suspensions, emulsions or pastes.

The abovementioned preparations can be prepared by themselves in a known manner, for example, the active compound can be prepared by, for example, at least one solvent or diluent, emulsifier, dispersant and / or binder or fixative, waterproofing agent, optionally drying agent and UV stabilizer, and It may optionally be prepared by mixing with colorants and pigments and other processing aids.

The pesticidal compositions or concentrates used to protect wood and woodworking products contain the active compounds according to the invention in concentrations of 0.0001 to 95% by weight, in particular 0.001 to 60% by weight.

The amount of composition or concentrate used depends on the species and the incidence and medium of the insect. The optimum rate of application can be determined by a series of tests in each case at the time of application. In general, however, it is sufficient to use from 0.0001 to 20% by weight, preferably from 0.001 to 10% by weight, based on the material to be protected.

The solvents and / or diluents used are organic chemical solvents or solvent mixtures and / or low volatility oily or oily organic chemical solvents or solvent mixtures and / or polar organic chemical solvents or solvent mixtures and / or water, and emulsifiers and / or if appropriate Or humectant.

Organic chemical solvents which are preferably used are oily or oily solvents having an evaporation number of at least 35 and a flash point of at least 30 ° C, preferably at least 45 ° C. The low volatility and water-insoluble oily and oily solvents used are suitable mineral oils or their aromatic fractions, or solvent mixtures containing mineral oils, preferably white spirit, petroleum and / or alkylbenzenes.

Advantageously used materials include mineral oils having a boiling range of 170 to 220 ° C, white oils having a boiling range of 170 to 220 ° C, spindle oils having a boiling range of 250 to 350 ° C, boiling of 160 to 280 ° C Petroleum and aromatic compounds having a range, turpentine oil and the like.

In a preferred embodiment, liquid aliphatic hydrocarbons having a boiling range of 180 to 210 ° C. or high-boiling mixtures of aromatic and aliphatic hydrocarbons having a boiling range of 180 to 220 ° C. and / or spindle oil and / or monochloronaphthalene, preferably Α-monochloronaphthalene is used.

Low volatility organic oily or oily solvents having an evaporation index of at least 35 and a flash point of at least 30 ° C., preferably at least 45 ° C., wherein the solvent mixture also has a flash point of at least 35 and a flash point of at least 30 ° C., preferably at least 45 ° C. If the pesticide / fungicide mixture can be dissolved or emulsified in the solvent mixture, it can be partially replaced by an intermediate or highly volatile organic chemical solvent.

In a preferred embodiment, a portion of the organic chemical solvent or solvent mixture is replaced with an aliphatic polar organic chemical solvent or solvent mixture. Aliphatic organic chemical solvents containing hydroxyl and / or ester and / or ether groups such as glycol ethers, esters and the like are preferably used.

The organic chemical binders used for the purposes of the present invention are known per se and can be diluted with water and / or synthetic resins and / or combined dry oils, in particular acrylates, which can be dissolved, dispersed or emulsified in the organic chemical solvents used. Resins, vinyl resins such as polyvinyl acetate, polyester resins, polycondensation or polyaddition resins, polyurethane resins, alkyd resins or modified alkyd resins, phenolic resins, hydrocarbon resins such as indene-coumarone A binder consisting of or comprising a physical dry binder based on a cumarone resin, a silicone resin, a dry vegetable oil and / or a dry oil and / or a natural and / or synthetic resin.

Synthetic resins used as binders can be used in the form of emulsions, dispersions or solutions. Bitumen or bituminous materials can also be used as binders in amounts of up to 10% by weight. In addition, colorants, pigments, waterproofing agents, odour-masking agents and inhibitors or anticorrosive agents known per se may be used.

According to the invention, the composition or concentrate preferably contains at least one alkyd resin or modified alkyd resin and / or dry vegetable oil as organic chemical binder. Alkyd resins which are preferably used according to the invention are those having an oil content of at least 45% by weight, preferably from 50 to 68% by weight.

All or part of the above mentioned binders may be replaced with fixatives (mixtures) or plasticizers (mixtures). These additives are used to prevent evaporation and also crystallization or precipitation of the active compounds. They preferably replace 0.01 to 30% of the binder (based on 100% binder used).

Plasticizers are phthalic acid esters such as dibutyl phthalate, dioctyl phthalate or benzyl butyl phthalate, phosphoric acid esters such as tributyl phosphate, adipic acid esters such as di- (2-ethylhexyl) adi Selected from the chemical groups of pates, stearates, for example butyl stearate or amyl stearate, oleate, for example butyl oleate, glycerol ether or high molecular weight glycol ethers, glycerol esters and p-toluenesulfonic acid esters do.

The fixative is chemically based on polyvinyl alkyl ethers such as polyvinyl methyl ether, or ketones such as benzophenone or ethylenebenzophenone.

The solvent or diluent is in particular also water, as the case may be, as a mixture with one or more of the aforementioned organic chemical solvents or diluents, emulsifiers and dispersants.

Wood is particularly effectively protected by industrial scale injection methods, for example vacuum, double vacuum or compression treatment.

In some cases, the ready-to-use composition may also contain other pesticides and also optionally one or more fungicides.

Suitable further components which can be mixed are preferably the insecticides and fungicides mentioned in WO 94/29 268. The compounds mentioned in this document are expressly incorporated herein by reference.

Very particularly preferred components that can be mixed are insecticides, for example chlorpyriphos, bombardment, silafluorine, alphamethrin, cyflutrin, cipermethrin, deltamethrin, permethrin, imidacloprid, NI-25, flu Phenoxalone, hexaflumuron, transflutrin, thiacloprid, methoxyphenozide, triflumuron, clotianidine, spinosad, tefluthrin, and fungicides such as epoxyconazole, Hexaconazole, azaconazole, propiconazole, tebuconazole, cyproconazole, metconazole, imazalyl, diclofluanide, tolylufluoride, 3-iodo-2-propynylbutylcarba Mate, N-octyl-isothiazolin-3-one and 4,5-dichloro-N-octylisothiazolin-3-one.

The active compounds according to the invention can be used to protect objects contaminated with brine or seawater at the same time, for example from ship hulls, screens, nets, structures, berths and signaling systems from contamination.

Species of fixed Oligochaetae , for example Serpulidae , and crustaceans and Ledamorpha family ( goose barnacle ), for example various Lepas and Contamination by the Scalpellum species, or species of the Balanomorpha family (acorn clam), for example Balanus or Pollicipes species, increases the frictional resistance of the vessel As a result, the energy consumption is high and the operating costs are significantly increased by frequently anchoring to dry docks.

Sticking crustaceans belonging to the genus Cirripedia ( cirriped crustacea ), in addition to contamination by algae, for example Ectocarpus sp . And Ceramium sp. Contamination by the Entomostraca group is particularly important.

Surprisingly, the active compounds according to the invention have been found to have excellent antifouling action, alone or in combination with other active compounds.

By using the active compounds according to the invention, for example, bis (trialkyltin) sulfide, tri-n-butyltin laurate, tri-n-butyltin chloride, copper oxide (I), triethyltin chloride, tri -n-butyl (2-phenyl-4-chlorophenoxy) tin, tributyltin oxide, molybdenum disulfide, antimony oxide, polymerized butyl titanate, phenyl (bispyridine) bismuth chloride, tri-n-butyltin fluoride, Manganese ethylenebisthiocarbamate, zinc dimethyldithiocarbamate, zinc ethylenebisthiocarbamate, zinc salt and copper salt of 2-pyridinethiol 1-oxide, bisdimethyldithiocarbamoylzinc ethylenebisthiocarbamate, zinc oxide Heavy metals in copper (I) ethylene-bisdithiocarbamate, copper thiocyanate, copper naphthenate and tributyltin halide, or The concentration of the compound can be significantly reduced.

If desired, the ready-to-use antifouling paint may further comprise other active compounds, preferably fungicides, fungicides, herbicides, arachnids or other antifouling active compounds.

Preferred suitable components for combination with the antifouling composition according to the invention are as follows:

Algalicides, for example 2-t-butylamino-4-cyclopropylamino-6-methylthio-1,3,5-triazine, dichlorophene, diuron, endortal, pentine acetate, isoproturon, meta Benzthiazurone, oxyfluorfen, quinoclammine and terbutryn;

Fungicides, for example benzo [b] thiophenecarboxylic acid cyclohexylamide S, S-dioxide, diclofloanide, fluoropolpet, 3-iodo-2-propynyl butylcarbamate, tolylufluoride and azoles For example azaconazole, cyproconazole, epoxyconazole, hexaconazole, metconazole, propiconazole and tebuconazole;

Acaricides such as fentin acetate, metaldehyde, methiocarb, niclosamide, thiodicarb and trimetacarb;

Fe chelating agent, or

Conventional antifouling active compounds such as 4,5-dichloro-2-octyl-4-isothiazolin-3-one, diiodomethylparatryl sulfone, 2- (N, N-dimethylthiocarbamoylthio) -5-nitrothiazyl, potassium, copper, sodium and zinc salts of 2-pyridinethiol 1-oxide, pyridinetriphenylborane, tetrabutyldistanoxane, 2,3,5,6-tetrachloro-4- (methyl Sulfonyl) pyridine, 2,4,5,6-tetrachloroisophthalonitrile, tetramethylthiuram disulfide and 2,4,6-trichlorophenylmaleimide.

The antifouling composition used contains the active compound according to the invention in a concentration of 0.001 to 50% by weight, in particular 0.01 to 20% by weight.

In addition, antifouling compositions according to the invention are described, for example, in Ungerer, Chem. Ind. 1985 , 37, 730-732 and Williams, Antifouling Marine Coatings, Noyes, Park Ridge, 1973 .

The antifouling composition according to the invention contains, in particular, a binder, in addition to algae, fungicides, vertebral animals and pesticidal active compounds.

Examples of certified binders include polyvinyl chloride in solvent systems, chlorinated rubbers in solvent systems, vinyl chloride / vinyl acetate copolymer systems in the form of acrylic resins, aqueous dispersions or organic solvent systems, particularly in aqueous systems, butadiene / Styrene / acrylonitrile rubbers, dry oils such as linseed oil, asphalt and epoxy compounds, modified cured resins or resin esters in combination with tar or bitumen, small amounts of chlorine rubber, chlorinated polypropylene and vinyl resins.

If desired, the paint also contains inorganic pigments, organic pigments or colorants which are preferably insoluble in saline. The paint may include a material such as rosin so that the active compound is released slowly. The paint may also include plasticizers, modifiers that affect flowability, and other conventional ingredients. The active compounds according to the invention can also be incorporated into auto-gloss antifouling systems.

The active compounds according to the invention are also suitable for controlling animal pests, in particular insects, arachnids and mites, which appear in confined spaces such as houses, factory halls, offices, vehicle cabins and the like. They may be used alone or in combination with other active compounds and auxiliaries in household pesticidal products for controlling such pests. They are active against sensitive and resistant species and all stages of development. These pests include:

Scorpion (Scorpionidea) tree, for example tooth portion oxide Kita Taunus (Buthus occitanus).

From the order of Acarina , for example, Argas persicus , Argas reflexus , Bryobia ssp ., Dermanyssus gallinae , Glishpa Cush also scalpel Tea Goose (Glyciphagus domestigus), ornithine Todo Ruth Motor baht (Ornithodorus moubat), Lippi three Palouse sangwi Neuss (Rhipicephalus sanguineus), Tromso non Temecula Alfred settled upon (Trombicula alfreddugesi), newoo Tromso non Temecula brother tumnal lease (Neutrombicula autumnalis ), Dermatophagoides pteronissimus , Dermatophagoides forinae .

Araneae , for example Aviculariidae , Araneidae

Opiliones , for example Pseudoscorpiones chelifer , Pseudoscorpiones cheiridium , Opiliones phalangium .

Isopoda , for example Oniscus asellus , Porcellio scaber .

Millipedes (Diplopoda) tree, for example Blast niul loose obtain Tula tooth (Blaniulus guttulatus), poly des mousse species (Polydesmus spp.).

The genus Chilopoda , for example Geophilus spp .

Zygentoma , for example Ctenolepisma spp. , Lepisma saccharina , Lepismodes inquilinus .

Neck of Blattaria , for example Blatta orientalis , Blattella germanica , Blattella asahinai , Leucophaea maderae , Panclo Panchlora spp. , Parcoblatta spp ., Periplaneta australasiae , Periplaneta americana , Periplaneta brunnea , Periplaneta brunnea Periplaneta fuliginosa , Supella longipalpa .

From the genus Saltatoria , for example Acheta domesticus.

Dermaptera , for example Forficula auricularia.

Termites ( Isoptera ), for example Kalotermes spp. , Reticulitermes spp .

Psocoptera species, for example Lepinatus spp. , Liposcelis spp .

Beetles (Coleoptera) Thursday, for example, in the eyes Trail Taunus species (Anthrenus spp.), Oh ridden pandanus species (Attagenus spp.), No scalpel test species (Dermestes spp.), Latte, tea Couscous Duck Party (Latheticus oryzae) , Necrobia spp. , Ptinus spp ., Rhizopertha dominica , Sitophilus granarius , Sitophilus oryzae , Sito Sitophilus zeamais , Stegobium paniceum .

Diptera , for example Aedes aegypti , Aedes albopictus , Aedes taeniorhynchus , Anopheles spp . , Calliphora erythrocephala , Chrysozona pluvialis , Culex quinquefasciatus , Culex pipiens , Culex pipiens , Culex tarsalis tarsalis , Drosophila spp. , Fannia canicularis , Musca domestica , Phlebotomus spp. , Sarcophaga canaria carnaria ), Simulium spp ., Stomoxys calcitrans , Tipula paludosa .

Lepidoptera , for example Achroia grisella , Galleria mellonella , Plodia interpunctella , Tinea cloacella , Tinnea pelionel Tinea pellionella , Tineola bisselliella .

Siphonaptera tree, for example Ctenocephalides canis, Ctenocephalides felis , Pulex irritans , Tunga penetrans , Xenofilasila Xenopsylla cheopis .

Bee (Hymenopera) tree, for example camphorsulfonic no tooth Herr cool LEA Taunus (Camponotus herculeanus), La siwooseu loosened furnace Versus (Lasius fuliginosus), La siwooseu nigeo (Lasius niger), La siwooseu Umbra tooth (Lasius umbratus), mono Morium pharaonis , Paravespula spp. , Tetramorium caespitum .

Anoplura , for example Pediculus humanus capitis, Pediculus humanus corporis , Pthirus pubis .

From the order of Heteroptera , for example Cimex hemipterus , Cimex lectularius , Rhodnius prolixus , Triatoma infestans .

In the field of household pesticides, they are used alone or in combination with other suitable active compounds, for example phosphate esters, carbamates, pyrethroids, growth regulators or other known pesticide groups.

They are aerosols, pressureless spray products, for example pumps and atomizer sprays, automatic spray systems, sprayers, foams, gels, cellulose or polymer evaporative tablets, liquid evaporators, gels and membrane evaporators As evaporation products, propellant-operated evaporators, energy-free evaporation systems or manual evaporation systems, moth papers, mos bags and moss gels, as granules or powders at the bait or attraction point for application Used.

Manufacturing Example

Example 1

[Method (b)]

0.50 g (2.38 mmol) 4-ethoxy-1,1,1-trifluoro-5-methyl-hex-3-en-2-one, 0.44 g (2.38 mmol) 4- (4-fluoro A mixture of phenyl) thiosemicarbazide and 10 ml of methanol was stirred at room temperature (about 20 ° C.) for 24 hours and then concentrated under reduced pressure. The residue was worked up by column chromatography (silica gel, cyclohexane / ethyl acetate, vol.: 5: 1).

0.71 g (85.5% of theory) of N- (2-fluorophenyl) -5-hydroxyl-3- (i-propyl) -5-trifluoromethyl-4,5-dihydro-1H-pyrazole -1-carbothioamide was obtained as an oil [log P (pH = 2.3): 3.86].

Example 2

[Method (c)]

0.50 g (2.0 mmol) of 3- (t-butyl) -5-trifluoromethyl-4,5-dihydro-1H-pyrazole-5-ol, 0.40 g (2.0 mmol) of 2 prepared at room temperature A mixture of -chlorophenyl isothiocyanate, 6 ml of 1,4-dioxane and 5 drops triethylamine was heated to reflux for 16 hours under reflux and then concentrated under reduced pressure. The residue was then triturated with petroleum ether and the resulting crystalline product was separated by suction filtration. 0.31 g (32% of theory) N- (2-chlorophenyl) -5-hydroxyl-3- (t-butyl) -5-trifluoromethyl-4,5-dihydro-1H-pyrazole- 1-carbothioamide was obtained.

It is also possible to prepare compounds of the general formula (IA) of Table 3 below, similarly to Examples 1 and 2 and according to the general preparation methods according to the invention.

Table 3 :

Examples of Compounds of Formula (IA)

The logP values given in the table above were measured according to EEC Directive 79/831 Annex V.A8 by HPLC (high performance liquid chromatography) using a reversed phase column (C 18). Temperature: 43 ° C.

(a) In the acidic range (pH 2.3), the measurement was carried out with a linear gradient of 0.1% aqueous phosphoric acid and acetonitrile from 10% acetonitrile to 90% acetonitrile in the mobile phase (the corresponding measurement results are indicated as a in Table 1). Became).

(b) In the neutral range (pH 7.5), measurements were carried out with a linear gradient of 0.01 mol phosphate aqueous buffer solution and acetonitrile from 10% acetonitrile to 90% acetonitrile in the mobile phase (the corresponding measurement results are shown in Table 1b). Was indicated).

Calibration was performed using unbranched alkan-2-ones (3-16 carbon atoms), where logP values are known (determining logP values by residence time using linear interpolation between two consecutive alkanones).

UV spectra of 200-400 nm were used to determine the lambda max value as the maximum of the chromatographic signal.

Preparation of Starting Material of Formula (III)

Example (III-1)

Step 1

14.5 g (101 mmol) of o-toluidine hydrochloride and 36 mL (207 mmol) of ethyldiisopropylamine are dissolved in 120 mL of dichloromethane, cooled to 0 ° C., and then 10.1 mL (106 mmol) of ethyl Chloroformate was added dropwise. The mixture was stirred at rt (about 20 ° C.) for 3 h and 100 ml of water were added. The organic phase was washed with water and saturated sodium chloride solution, dried over sodium sulfate and then filtered. The solvent was carefully distilled from the filtrate under reduced pressure. 18.2 g (100% of theory) of O-ethyl N- (2-methylphenyl) carbamate were obtained as a yellow oil and used in the next two steps without further purification.

Step 2

17.2 g (96 mmol) of O-ethyl N- (2-methylphenyl) -0-ethylcarbamate and 23.24 mL (480 mmol) of hydrazine hydrate were stirred at 120 ° C. for 16 hours. After cooling, the mixture was stored at -14 ° C for 16 hours. The resulting crystalline product was isolated by suction filtration, washed with diethyl ether and pentane and then dried under high vacuum. 9.5 g (60% of theory) of 4- (2-methylphenyl) semicarbazide were obtained as a colorless solid.

Example (III-2)

9.8 g (54 mmol) of 2- (2-chlorophenyl) ethyl isocyanate were first introduced into 60 mL of ethanol, cooled to 0 ° C., and then 8.25 mL (59.3 mmol) of 35% aqueous hydrazine monohydrate solution was slowly Added dropwise. Cooling was released and the reaction mixture was stirred for 16 hours (about 20 hours). The resulting solid was separated by suction filtration and discarded. The solvent was carefully distilled from the filtrate under reduced pressure, and the residue was dried under high vacuum. 10.7 g (93% of theory) of 4- [2- (2-chlorophenyl) ethyl] semicarbazide was crystallized to give a colorless oil which became a white solid.

Preparation of Starting Material of Formula (IV)

Example (IV-1)

Step 1

50 g (0.58 mol) of 3-methyl-2-butanone and 86 g (0.58 mol) of triethyl orthoformate were first introduced into 300 mL of ethanol, followed by addition of concentrated hydrochloric acid drop. The mixture was stirred at room temperature (about 20 ° C.) for 16 hours, poured into saturated sodium bicarbonate solution and extracted three times with 100 ml of methyl-t-butyl ether each time, and then the organic phase was dried over sodium sulfate. The solvent was distilled off under reduced pressure and the crude product obtained as a residue was used for the next step.

Yield: 68.7 g (64% of theory).

Step 2

10 g (62 mmol) of crude product obtained in step 1 was dissolved in 60 mL of chloroform with 10 mL of pyridine (124 mmol). This solution was added dropwise to 17.5 mL (124 mmol) anhydrous trifluoroacetic acid at 0 ° C. After completion of the dropwise addition, the mixture was stirred at room temperature (about 20 ° C.) for 17 hours, washed once with 0.1 M hydrochloric acid and then three times with water. The organic phase was dried over sodium sulfate and filtered. The solvent was carefully distilled from the filtrate under reduced pressure. 12 g (92% of theory) of 3-ethoxy-2-methyl-6,6,6-trifluoro-3-hexen-5-one were obtained as an amorphous residue.

Preparation of Starting Material of Formula (V)

Example (V-1)

0.31 g (6 mmol) of hydrazine monohydrate was first introduced into 15 mL of ethanol, followed by 1 g (5 mmol) of 1,1,1-trifluoro-5,5-dimethyl-2,4-hexanedione. Dropwise at room temperature (about 20 ° C.). The mixture was stirred at rt for 2 h and concentrated under reduced pressure. The residue was extracted again with water and ethyl acetate. The organic phase was dried over sodium sulfate and filtered. The solvent was carefully distilled from the filtrate under reduced pressure. 0.96 g (91.5% of theory) of 3-t-butyl-5-trifluoromethyl-4,5-dihydro-1H-pyrazole-5-ol were obtained as an amorphous residue.

Example (V-2)

1 g (6 mmol) of 1,1,1-trifluoro-2,4-hexanedione was first introduced into 30 mL of methyl-t-butyl ether, and 0.31 g (6 mmol) of hydrazine hydrate was added to room temperature ( Slowly at about 20 ° C). The mixture was stirred for 3.5 h and concentrated under reduced pressure. The residue was extracted again with water and ethyl acetate. The organic phase was dried over sodium sulfate and filtered. The solvent was carefully distilled from the filtrate under reduced pressure. 0.57 g (52% of theory) of 3-ethyl-5-trifluoromethyl-4,5-dihydro-1H-pyrazole-5-ol were obtained as an amorphous residue.

Example of use:

Example A

Meloidogine test

Solvent: Dimethylformamide 7 parts by weight

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

One part by weight of the active compound is mixed with the solvents and emulsifiers in the amounts mentioned above, and then the concentrate is diluted with water to the desired concentration to prepare a suitable formulation of the active compound.

The vessel was introduced with sand, active compound solution, meloidocyne incognita egg / larvae suspension and lettuce seed. Lettuce germinates and grows into plants. Worms on the roots

After a certain period of time, nematicidal functionality was determined in% by the formation of insects. 100% means that no insects were observed at all, and 0% means that the number of insects on the treated plants corresponds to that of the untreated control.

In this test, for example, the compounds of Preparation Examples 14, 19, 43, 100, 114, 115, 122, and 123 showed excellent activity.

Table A

Nematodes that damage plants

Meloidogine test

Example B

Miss juice test (spray processing)

Solvent: 78 parts by weight of acetone

         Dimethylformamide 1.5 parts by weight

Emulsifier: 0.5 parts by weight of alkylaryl polyglycol ether

A suitable formulation of the active compound is prepared by mixing 1 part by weight of the active compound with the solvents and emulsifiers in the amounts mentioned above and diluting the concentrate with water containing the emulsifier to the desired concentration.

The cabbage ( Brassica pekinensis ) heavily infected with peach hump aphid ( Miscus persicae ) was sprayed with the active compound preparation of the desired concentration.

After a certain period of time, the activity was determined in%. 100% means that all aphids have been killed; 0% means that the aphid has not been killed at all.

In this test, for example, the compounds of Preparation Examples 1, 12, 15, 20, 24, 27, 31, 33, 40, 42, 46 and 70 showed excellent activity.

TABLE B

Insects that damage plants

Miss juice test (spray processing)

Table B-Continue

Insects that damage plants

Miss juice test (spray processing)

Example C

Phaedon Test (Spray Treatment)

Solvent: 78 parts by weight of acetone

         Dimethylformamide 1.5 parts by weight

Emulsifier: 0.5 parts by weight of alkylaryl polyglycol ether

A suitable formulation of the active compound is prepared by mixing 1 part by weight of the active compound with the solvents and emulsifiers in the amounts mentioned above and diluting the concentrate with water containing the emulsifier to the desired concentration.

The cabbage (Brassica pekinensis) discs were sprayed with the active compound formulation of the desired concentration and, when dried, infected with mustard worms (Phaedon cocicleae) larvae.

After a certain period of time, the activity was determined in%. 100% means that all mustard larvae have been killed; 0% means that no mustard larvae have been killed.

In this test, for example, the compounds of Preparation Examples 1, 26, 27, 29, 30, 31, 32, 33, 34, 42, 44, 53, 55, 56, 63, 64, 73, 74 and 75 Excellent activity was shown.

Table C

Insects that damage plants

Phaedon Test (Spray Treatment)

Table C-continued

Insects that damage plants

Phaedon Test (Spray Treatment)

Table C-continued

Insects that damage plants

Phaedon Test (Spray Treatment)

Example D

Spodoptera prugiferda test (spray treatment)

Solvent: 78 parts by weight of acetone

         Dimethylformamide 1.5 parts by weight

Emulsifier: 0.5 parts by weight of alkylaryl polyglycol ether

A suitable formulation of the active compound is prepared by mixing 1 part by weight of the active compound with the solvents and emulsifiers in the amounts mentioned above and diluting the concentrate with water containing the emulsifier to the desired concentration.

Corn ( Zea mays ) leaf plots were sprayed with the active compound formulation of the desired concentration and, when dried, infected with scab moth (Spodoptera prugiferda) caterpillars.

After a certain period of time, the activity was determined in%. 100% means that all caterpillars have been killed; 0% means that the caterpillar has not been killed at all.

In this test, for example, the compounds of Preparation Examples 1, 20, 24, 26, 27, 29, 31, 32, 42, 44, 55, 63, 64, 73, 74, 75, and 83 show good activity. It was.

Table D

Insects that damage plants

Spodoptera prugiferda test (spray treatment)

Table D-continued

Insects that damage plants

Spodoptera prugiferda test (spray treatment)

Example E

Tetranicus test (OP-resistant / spray treated)

Solvent: 78 parts by weight of acetone

         Dimethylformamide 1.5 parts by weight

Emulsifier: 0.5 parts by weight of alkylaryl polyglycol ether

A suitable formulation of the active compound is prepared by mixing 1 part by weight of the active compound with the solvents and emulsifiers in the amounts mentioned above and diluting the concentrate with water containing the emulsifier to the desired concentration.

The soybeans (Paceolus vulgaris ) leaf beds severely infected with greenhouse spot mites of all stages (Tetranicus urticae) were sprayed with the active compound formulation of the desired concentration.

After a certain period of time, the activity was determined in%. 100% means that all the spots have been killed; 0% means that the mites have not been killed at all.

In this test, for example, the compounds of Preparation Examples 1, 22, 24, 27, 30, 34, 42, 44, 55, 56, 74, 75, 106, 118 and 126 showed good activity.

Table E

Insects that damage plants

Tetranicus test (OP-resistant / spray treated)

Table E-continued

Insects that damage plants

Tetranicus test (OP-resistant / spray treated)

Example F

Test / oral intake for cat fleas

Ktenosepalides Felice (Oral)

Test Animals: Xenocephalides Adults

Solvent: Dimethyl Sulfoxide (DMSO)

To prepare a suitable formulation, a suitable active compound solution was prepared from 10 mg of active compound and 0.5 ml of dimethyl sulfoxide. 10 μl of this formulation was added to the citrated bovine serum and stirred.

Twenty hungry adults (Ctenosepalides Felis, "Georgi" species) were placed in a chamber (Ø 5 cm) and the top and bottom were closed with gauze. A metal cylinder with a bottom covered with parafilm was introduced into the chamber. The cylinder contains a 2 ml blood / active compound preparation that fleas can take through the parafilm membrane. Blood was warmed to 37 ° C. and the temperature of the flea chamber space was adjusted to room temperature. Controls were mixed with equal volume of DMSO without compound addition. After 24 and 48 hours, mortality was determined in%.

Compounds that control at least 75% of fleas within 48 hours are considered effective.

In this test, for example, the compounds of Preparation Examples 29 and 34 showed good activity.

TABLE F

Animal parasites

Test / oral intake for cat fleas

Example G

Fly larva test

Lucilia Cuprina (48 hours)

Test Animal: Lucilia Cuprina

Solvent: Dimethyl Sulfoxide

10 mg of the active compound was dissolved in 0.5 ml of dimethyl sulfoxide. Suitable formulations are prepared by diluting the active compound solution with water to the desired specific concentration.

About 20 Lucilia cuprinas were placed in a test tube containing about 1 cm 3 of horse meat and 0.5 ml of the active compound formulation to be tested. After 48 hours, the activity of the active compound formulation was determined in%.

In this test, for example, the compound of Preparation Example 26 showed excellent activity.

Table G

Animal parasites

Fly larva test

Example H

Diabrotica balteata test (larvae larvae)

Critical Concentration Test / Soil Insect-Treatment of Transgenic Plants

Solvent: Dimethylformamide 7 parts by weight

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

A suitable formulation of the active compound is prepared by mixing 1 part by weight of the active compound with the solvent in the amounts mentioned above, adding the above mentioned amount of emulsifier and then diluting the concentrate with water to the desired concentration.

The active compound formulation is poured into the soil. At this time, the active compound concentration in the formulation is of no practical importance, only the weight of the active compound applied in soil (ppm (mg / L)) applied is the key. The soil was charged to a 0.25 L pot and left at 20 ° C.

Immediately after preparation, five germinated corn kernels of YIELD GUARD cultivar (registered trademark of Monsanto Comp., USA) were introduced into each pot. Two days later, appropriate test insects were introduced into the treated soil. After seven more days, the number of germinated corn plants was counted to determine the efficiency of the active compound (one plant = 20% active).

Example J

Heliothis virescens test (treatment of transgenic plants)

Solvent: Dimethylformamide 7 parts by weight

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

One part by weight of the active compound is mixed with the aforementioned amount of solvent and the aforementioned amount of emulsifier, and then the concentrate is diluted with water to the desired concentration to prepare a suitable formulation of the active compound.

Soybean sprigs ( Glycine max ) of the Roundup Ready variety (Monsanto Comp., USA) are immersed in an active compound formulation of the desired concentration and infected with tobacco shoot beetles Heliotis viresense while the leaves are moist. I was.

After a certain period of time, insect control rates were determined in%. 100% means that all caterpillars have been killed; 0% means that the caterpillar has not been killed at all.

Claims (8)

Use of pyrazolinol and its derivatives of general formula (I) to control animal pests:

Where A represents optionally substituted alkyl, Q represents oxygen or sulfur, R ¹ represents hydrogen or in each case optionally substituted alkyl, alkylcarbonyl, alkenyl, alkenylcarbonyl, cycloalkyl, cycloalkylcarbonyl, aryl, arylcarbonyl, arylalkyl or arylalkylcarbonyl Indicate, R ² represents hydrogen or in each case optionally substituted alkyl, alkylcarbonyl, alkoxycarbonyl, cycloalkyl, aryl, arylalkyl or heterocyclyl, R ³ in each case represents optionally substituted alkyl, alkenyl, cycloalkyl, aryl, arylalkyl or heterocyclyl, or R ² and R ³ together also represent alkanediyl (alkylene), R ⁴ represents hydrogen, amino, or in each occurrence optionally substituted alkyl, alkylcarbonyl, alkylsulfonyl, alkylamino, alkylcarbonylamino, alkylsulfonylamino, alkenyl, alkenylcarbonyl or Alkynyl, R ⁵ represents hydrogen or in each case optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heterocyclyl or heterocyclylalkyl. The method of claim 1, A optionally represents hydroxyl-, cyano-, halogen-, C ₁ -C ₄ -alkoxy- or C ₁ -C ₄ -haloalkoxy-substituted C ₁ -C ₈ -alkyl, Q represents oxygen or sulfur, R ¹ represents hydrogen or in each case optionally hydroxyl-, cyano-, halogen-, C ₁ -C ₄ -alkoxy- or C ₁ -C ₄ -haloalkoxy-substituted C ₁ -C ₁₀ -alkyl Or (C ₁ -C ₁₀ -alkyl) carbonyl, or in each case optionally cyano- or halogen-substituted C ₂ -C ₁₀ -alkenyl or (C ₂ -C ₁₀ -alkenyl) carbonyl Or in each case optionally cyano-, halogen-, C ₁ -C ₄ -alkyl- or C ₁ -C ₄ -haloalkyl-substituted C ₃ -C ₆ -cycloalkyl or (C ₃ -C _6- Cycloalkyl) carbonyl or optionally in each case nitro-, cyano-, halogen-, C ₁ -C ₄ -alkyl-, C ₁ -C ₄ -halo alkyl-, C ₁ -C ₄ -alkoxy- Or C ₁ -C ₄ -haloalkoxy-substituted C ₆ -C ₁₀ -aryl or (C ₆ -C ₁₀ -aryl) carbonyl, in each case optionally nitro-, cyano-, halogen-, C _1- C ₄ -alkyl-, C ₁ -C ₄ -haloalkyl-, C ₁ -C ₄ -alkoxy- or C ₁ -C ₄ -haloalkoxy-substituted (C _6- C ₁₀ -aryl) -C ₁ -C ₄ -alkyl or (C ₆ -C ₁₀ -aryl-C ₁ -C ₄ -alkyl) carbonyl, R ² represents hydrogen or optionally cyano-, halogen- or C ₁ -C ₄ -alkoxy-substituted C ₁ -C ₁₀ -alkyl, (C ₁ -C ₁₀ -alkyl) carbonyl or (C _1- C ₁₀ -alkoxy) carbonyl or optionally cyano-, halogen- or C ₁ -C ₄ -alkyl-substituted C ₃ -C ₆ -cycloalkyl, in each case optionally nitro-, cyano -, Halogen-, C ₁ -C ₄ -alkyl-, C ₁ -C ₄ -haloalkyl-, C ₁ -C ₄ -alkoxy- or C ₁ -C ₄ -haloalkoxy-substituted C ₆ -C _10- Aryl or C ₆ -C ₁₀ -aryl-C ₁ -C ₄ -alkyl, or optionally nitro-, cyano-, halogen-, C ₁ -C ₄ -alkyl-, C ₁ -C ₄ -haloalkyl- , C ₁ -C ₄ -alkoxy- or C ₁ -C ₄ -haloalkoxy-substituted and having at least 6 carbon atoms and heterocyclyl having at least one hetero atom selected from the group consisting of N, O and S , R ³ optionally represents cyano-, halogen- or C ₁ -C ₄ -alkoxy-substituted C ₁ -C ₁₀ -alkyl, or optionally cyano-, halogen- or C ₁ -C ₄ -alkyl-substituted C ₃ -C ₆ -cycloalkyl, or in each case optionally nitro-, cyano-, halogen-, C ₁ -C ₄ -alkyl-, C ₁ -C ₄ -haloalkyl-, C ₁ -C ₄ -alkoxy- or C ₁ -C ₄ -haloalkoxy-substituted C ₆ -C ₁₀ -aryl or C ₆ -C ₁₀ -aryl-C ₁ -C ₄ -alkyl, or optionally nitro-, cyano- , Halogen-, C ₁ -C ₄ -alkyl-, C ₁ -C ₄ -haloalkyl-, C ₁ -C ₄ -alkoxy- or C ₁ -C ₄ -haloalkoxy-substituted and up to 6 carbon atoms and Heterocyclyl having at least one hetero atom selected from the group consisting of N, O and S, or R ² and R ³ together also represent C ₃ -C ₅ -alkanediyl (alkylene), R ⁴ represents hydrogen, amino, or in each case optionally hydroxyl-, cyano-, halogen- or C ₁ -C ₄ -alkoxy-substituted C ₁ -C ₁₀ -alkyl, (C _1- C ₁₀ -alkyl) carbonyl, C ₁ -C ₁₀ -alkylsulfonyl, C ₁ -C ₁₀ -alkylamino, (C ₁ -C ₁₀ -alkyl) carbonylamino or C ₁ -C ₁₀ -alkylsulfonylamino Or in each case optionally cyano- or halogen-substituted C ₂ -C ₁₀ -alkenyl, (C ₂ -C ₁₀ -alkenyl) carbonyl or C ₂ -C ₁₀ -alkynyl, R ⁵ represents hydrogen or optionally represents hydroxyl-, cyano-, halogen- or C ₁ -C ₄ -alkoxy-substituted C ₁ -C ₁₀ -alkyl, in each case optionally cyano- or halogen -Substituted C ₂ -C ₁₀ -alkenyl or C ₂ -C ₁₀ -alkynyl or optionally cyano-, halogen- or C ₁ -C ₄ -alkyl-substituted C ₃ -C ₆ -cyclo Alkyl or C ₃ -C ₆ -cycloalkyl-C ₁ -C ₄ -alkyl, or in each case optionally nitro-, cyano-, halogen-, C ₁ -C ₄ -alkyl-, C ₁ -C ₄ -Haloalkyl-, C ₁ -C ₄ -alkoxy-, C ₁ -C ₄ -haloalkoxy-, C ₁ -C ₄ -alkylthio-, C ₁ -C ₄ -haloalkylthio-, phenyl-, phenoxy -Or piperazinyl- (optionally substituted by C ₁ -C ₄ -alkyl or optionally by halogen-, C ₁ -C ₄ -alkyl- or C ₁ -C ₄ -alkoxy-substituted phenyl) substituted C ₆ -C ₁₀ -aryl or C ₆ -C ₁₀ -aryl-C ₁ -C ₄ -alkyl, or in each case optionally nitro-, cya No-, halogen-, C ₁ -C ₄ -alkyl-, C ₁ -C ₄ -haloalkyl-, C ₁ -C ₄ -alkoxy- or C ₁ -C ₄ -haloalkoxy-substituted and in the heterocyclyl group Pyrazolinol of formula (I), which represents heterocyclyl or heterocyclyl-C ₁ -C ₄ -alkyl having up to 6 carbon atoms and at least one hetero atom selected from the group consisting of N, O and S And the use of derivatives thereof. A pesticide comprising at least one compound of the general formula (I) according to claim 1 together with an extender and / or a surfactant. A method for controlling pests, characterized in that the compounds of formula (I) according to claim 1 are acted on pests and / or their habitats. A process for preparing pesticides, characterized in that the compound of formula (I) according to claim 1 is mixed with an extender and / or a surfactant. Compound of formula (IA):

Where Q ^A represents oxygen or sulfur, R ^1A represents hydrogen or, in each case, optionally substituted alkyl, alkylcarbonyl, cycloalkyl, cycloalkylcarbonyl, aryl, arylcarbonyl, arylalkyl or arylalkylcarbonyl, R ^2A represents hydrogen or, in each case, optionally substituted alkyl, alkylcarbonyl, alkoxycarbonyl, cycloalkyl, aryl, arylalkyl or heterocyclyl, R ^3A in each occurrence represents optionally substituted alkyl, cycloalkyl, aryl, arylalkyl or heterocyclyl, or R ^2A and R ^3A together also represent alkanediyl (alkylene), R ^4A represents hydrogen, amino, or in each occurrence optionally substituted alkyl, alkylcarbonyl, alkylsulfonyl, alkylamino, alkylcarbonylamino, alkylsulfonylamino, alkenyl, alkenylcarbonyl or Alkynyl, R ^5A represents in each case alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heterocyclyl or heterocyclylalkyl having at least two carbon atoms optionally substituted. The method of claim 6, Q ^A represents oxygen or sulfur, R ^1A represents hydrogen or in each case optionally represents cyano-, halogen- or C ₁ -C ₄ -alkoxy-substituted C ₁ -C ₁₀ -alkyl or (C ₁ -C ₁₀ -alkyl) carbonyl Or in each case optionally cyano-, halogen- or C ₁ -C ₄ -alkyl-substituted C ₃ -C ₆ -cycloalkyl or (C ₃ -C ₆ -cycloalkyl) carbonyl, in each case Optionally nitro-, cyano-, halogen-, C ₁ -C ₄ -alkyl-, C ₁ -C ₄ -haloalkyl-, C ₁ -C ₄ -alkoxy- or C ₁ -C ₄ -haloalkoxy-substituted C ₆ -C ₁₀ -aryl or (C ₆ -C ₁₀ -aryl) carbonyl, or in each case optionally nitro-, cyano-, halogen-, C ₁ -C ₄ -alkyl-, C _1- C ₄ -haloalkyl-, C ₁ -C ₄ -alkoxy- or C ₁ -C ₄ -haloalkoxy-substituted (C ₆ -C ₁₀ -aryl) -C ₁ -C ₄ -alkyl or (C ₆ -C ₁₀ -aryl-C ₁ -C ₄ -alkyl) carbonyl, R ^2A represents hydrogen or optionally cyano-, halogen- or C ₁ -C ₄ -alkoxy-substituted C ₁ -C ₁₀ -alkyl, (C ₁ -C ₁₀ -alkyl) carbonyl or (C _1- C ₁₀ -alkoxy) carbonyl or optionally cyano-, halogen- or C ₁ -C ₄ -alkyl-substituted C ₃ -C ₆ -cycloalkyl, in each case optionally nitro-, cyano -, Halogen-, C ₁ -C ₄ -alkyl-, C ₁ -C ₄ -haloalkyl-, C ₁ -C ₄ -alkoxy- or C ₁ -C ₄ -haloalkoxy-substituted C ₆ -C _10- Aryl or C ₆ -C ₁₀ -aryl-C ₁ -C ₄ -alkyl, or optionally nitro-, cyano-, halogen-, C ₁ -C ₄ -alkyl-, C ₁ -C ₄ -haloalkyl- , C ₁ -C ₄ -alkoxy- or C ₁ -C ₄ -haloalkoxy-substituted and having at least 6 carbon atoms and heterocyclyl having at least one hetero atom selected from the group consisting of N, O and S , R ^3A optionally represents cyano-, halogen- or C ₁ -C ₄ -alkoxy-substituted alkyl having 1 to 10 carbon atoms, or optionally cyano-, halogen- or C ₁ -C ₄ -alkyl-substituted Cycloalkyl having 3 to 6 carbon atoms, or in each case having 6 or 10 carbon atoms in the aryl group and optionally 1 to 4 carbon atoms in the alkyl moiety, optionally in each case nitro-, cyano-, halogen-, C ₁ -C ₄ -alkyl-, C ₁ -C ₄ -haloalkyl-, C ₁ -C ₄ -alkoxy- or C ₁ -C ₄ -haloalkoxy-substituted aryl or arylalkyl, or optionally nitro- , Cyano-, halogen-, C ₁ -C ₄ -alkyl-, C ₁ -C ₄ -haloalkyl-, C ₁ -C ₄ -alkoxy- or C ₁ -C ₄ -haloalkoxy- substituted and up to 6 Heterocyclyl having a carbon atom of and at least one hetero atom selected from the group consisting of N, O and S, or R ^2A and R ^3A together also represent C ₃ -C ₅ -alkanediyl (alkylene), R ^4A represents hydrogen, amino, or in each case optionally cyano-, halogen- or C ₁ -C ₄ -alkoxy-substituted C ₁ -C ₁₀ -alkyl, (C ₁ -C ₁₀ -alkyl ) Carbonyl, C ₁ -C ₁₀ -alkylsulfonyl, C ₁ -C ₁₀ -alkylamino, (C ₁ -C ₁₀ -alkyl) carbonylamino or C ₁ -C ₁₀ -alkylsulfonylamino, or In each case optionally represents halogen-substituted C ₂ -C ₁₀ -alkenyl, (C ₂ -C ₁₀ -alkenyl) carbonyl or C ₂ -C ₁₀ -alkynyl, R ^5A optionally represents cyano-, halogen- or C ₁ -C ₄ -alkoxy-substituted C ₂ -C ₁₀ -alkyl, in each case optionally halogen-substituted C ₂ -C ₁₀ -alkenyl or C ₂ -C ₁₀ -alkynyl or optionally cyano-, halogen- or C ₁ -C ₄ -alkyl-substituted C ₃ -C ₆ -cycloalkyl or C ₃ -C ₆ -cycloalkyl-C _1- C ₄ -alkyl or optionally in each case nitro-, cyano-, halogen-, C ₁ -C ₄ -alkyl-, C ₁ -C ₄ -haloalkyl-, C ₁ -C ₄ -alkoxy-, C ₁ -C ₄ -haloalkoxy-, C ₁ -C ₄ -alkylthio-, C ₁ -C ₄ -haloalkylthio-, phenyl-, phenoxy- or piperazinyl- (C ₁ -C ₄ -alkyl Or optionally substituted with halogen-, C ₁ -C ₄ -alkyl- or C ₁ -C ₄ -alkoxy-substituted phenyl) substituted C ₆ -C ₁₀ -aryl or C ₆ -C _10- Aryl-C ₁ -C ₄ -alkyl, or in each case optionally nitro-, cyano-, halogen-, C ₁ -C ₄ -alkyl-, C ₁ -C ₄ -haloalkyl-, C ₁ -C ₄ -alkoxy- or C ₁ -C ₄ -haloalkoxy-substituted hetero having up to 6 carbon atoms in the heterocyclyl group and at least one hetero atom selected from the group consisting of N, O and S A compound of formula (IA) representing cyclyl or heterocyclyl-C ₁ -C ₄ -alkyl. (a) the (thio) semicarbazide of formula (III), wherein the 1,3-dicarbonyl compound of formula (II) is optionally in the presence of one or more diluents and optionally in the presence of one or more reaction aids Or react with (b) reacting an alkoxyalkenyl ketone of formula (IV) with (thio) semicarbazide of formula (III), optionally in the presence of one or more diluents and optionally in the presence of one or more reaction aids Or (c) an aminocarbonyl compound of general formula (VI) or a general formula (VII), wherein pyrazolin of general formula (V) is optionally in After reacting with iso (thio) cyanate of If desired, a compound of formula (IA) obtained according to the method of (a), (b) or (c) above may be prepared by a conventional method. A process for preparing a compound of formula (IA) according to claim 6 characterized by the conversion to:

Where R ^2A , R ^3A , Q ^A , R ^4A and R ^5A are as defined in claim 6 except that in formula (VII) R ^5A is not H (hydrogen), R represents alkyl, X represents halogen, Formula (IV) in addition to the cis- or Z-configurations also includes the corresponding trans- or E-configurations.