DE4426757A1 - 2-imidazolidinone derivatives - Google Patents

Abstract

The invention concerns novel 2-imidazolidinone derivatives of formula (I) in which R<1>, R<2> and R<3> have the meanings given in the description. The invention further concerns a number of processes for preparing these derivatives and their use as fungicides.

Description

The present invention relates to new 2-imidazolidinone derivatives, several Process for their preparation and their use as fungicides.

Various 1,5-disubstituted 2-imidazolidinones are already in the literature (see US Pat. No. 5,128,358, J. Med. Chem. 1991, 291-298, WO 87-06 576, Chem. Abstr. 107, 154 281 g and Chem. Abstr 91 157 661 t). Some of these compounds have pharmacological properties known. However, there is no fungicidal activity of these compounds reported.

There have now been new 2-imidazolidinone derivatives of the formula

in which
R1 represents alkyl, haloalkyl, alkoxyalkyl, alkenyl, optionally substituted cycloalkyl, optionally substituted aryl, optionally substituted phenylalkyl, optionally substituted phenylalkenyl, optionally substituted phenoxyalkyl, optionally substituted phenylthioalkyl or for optionally substituted heterocyclyl,
R² is alkyl, haloalkyl, alkoxyalkyl, alkenyl, optionally substituted cycloalkyl, optionally substituted aryl, optionally substituted phenylalkyl, optionally substituted phenylalkenyl, optionally substituted phenoxyalkyl, optionally substituted phenylthioalkyl or for optionally substituted heterocyclyl and
R³ for the groupings

stands, where
R⁴ represents hydrogen, alkyl, haloalkyl, alkoxyalkyl, alkylcarbonyl, alkylsulfonyl, haloalkylcarbonyl, alkoxyalkylcarbonyl, optionally substituted cycloalkyl, optionally substituted arylcarbonyl or represents optionally substituted arylsulfonyl,
R⁵ represents hydrogen, alkyl, haloalkyl, alkoxyalkyl, optionally substituted cycloalkyl, optionally substituted aryl or for optionally substituted heterocyclyl,
R⁶ represents hydrogen, alkyl, haloalkyl, alkoxyalkyl, alkylcarbonyl, alkylsulfonyl, haloalkylcarbonyl, alkoxyalkylcarbonyl, optionally substituted cycloalkyl, optionally substituted arylcarbonyl or represents optionally substituted arylsulfonyl,
R⁷ represents hydrogen, alkyl, haloalkyl, alkoxyalkyl, optionally substituted cycloalkyl, optionally substituted aryl or for optionally substituted heterocyclyl and
R⁸ represents hydrogen, alkyl, haloalkyl, alkoxyalkyl, optionally substituted cycloalkyl, optionally substituted aryl or for optionally substituted heterocyclyl,
found.

It was also found that 2-imidazolidinone derivatives of the formula (I) get when one

• a) 2-imidazolidinones of the formula in which
  R¹ and R² have the meanings given above,
  either with isocyanates of the formula R⁵-NCO (IIIa) in which
  R⁵ has the meanings given above,
  or with isothiocyanates of the formula R⁷-NCS (IIIb) in which
  R⁷ has the meanings given above,
  in each case if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder, or
• b) 2-imidazolidinone derivatives of the formula or in which
  R⁵ and R⁷ have the meanings given above,
  with compounds of the formula R⁹-Y (IV) in which
  R⁹ represents alkyl, haloalkyl, alkoxyalkyl, alkylcarbonyl, alkylsulfonyl, haloalkylcarbonyl, alkoxyalkylcarbonyl, optionally substituted cycloalkyl, optionally substituted arylcarbonyl or for optionally substituted arylsulfonyl and
  Y represents a leaving group,
  if appropriate in the presence of a diluent and if appropriate in the presence of a reaction auxiliary, or
• c) 2-imidazolidinones of the formula in which
  R¹ and R² have the meanings given above,
  with sulfonyl derivatives of the formula R⁸-SO₂-Z (V) in which
  R⁸ has the meanings given above and
  Z represents a leaving group,

optionally in the presence of a diluent and optionally in In the presence of an acid binder.

Furthermore, it was found that the 2-imidazolidinone derivatives according to the invention of the formula (I) have very good fungicidal properties.

It is extremely surprising that the substances according to the invention have a much better fungicidal effectiveness than the constitutional most similar, previously known compounds with the same direction of action.

The compounds of the invention are general by the formula (I) Are defined.

R¹ is preferably C₁-C₈-alkyl, C₁-C₈-haloalkyl having 1 to 9 halogen atoms,
for C₁-C₄-alkoxy-C₁-C₅-alkyl, C₂-C₈-alkenyl,
for C₃-C₁₀ cycloalkyl, where these radicals can be substituted up to six times, identically or differently, by halogen, C₁-C₄-alkyl and / or C₁-C₄-haloalkyl having 1 to 9 identical or different halogen atoms,
for phenyl, naphthyl, phenyl-C₁-C₄-alkyl, phenyl-C₂-C₄-alkenyl, phenoxy-C₁-C₄-alkyl or phenylthio-C₁-C₄-alkyl, each of these radicals being substituted one to five times, in the same or different manner can by halogen, cyano, nitro, amino, hydroxy, formyl, carboxy carbamoyl, thiocarbamoyl, each straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl each having 1 to 6 carbon atoms, each straight-chain or branched alkenyl or alkenyloxy each having 2 to 6 carbon atoms, each straight-chain or branched haloalkyl, haloalkoxy, haloalkylthio, haloalkylsulfinyl or haloalkylsulfonyl each having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, each straight-chain or branched haloalkenyl or haloalkenyloxy each having 2 to 6 carbon atoms and 1 to 13 same or different NEN halogen atoms, each straight-chain or branched alk ylamino, dialkylamino, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkyl sulfonyloxy, hydroximinoalkyl or alkoximinoalkyl each having 1 to 6 carbon atoms in the individual alkyl parts, in each case optionally one or more times, identically or differently, by halogen and / or straight-chain or branched alkyl having 1 to 4 carbon atoms and / or straight-chain or branched haloalkyl with 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, substituted and in each case doubly linked alkylene or dioxyalkylene, each with 1 to 6 carbon atoms, cycloalkyl with 3 to 6 carbon atoms, heterocyclyl or heterocyclyl-methyl, each with 3 to 7 ring members, each of which is 1 to 3 identical or different heteroatoms - in particular nitrogen, oxygen and / or sulfur - and in each case in the phenyl part, in each case, once to three times, identically or differently, by halogen, cyano and / or straight-chain or branched alk yl with 1 to 4 carbon atoms and / or straight-chain or branched haloalkyl with 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms and / or straight-chain or branched alkoxy with 1 to 4 carbon atoms and / or straight-chain or branched haloalkoxy with 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms substituted phenyl, phen oxy, benzyl, benzyloxy, phenylethyl or phenylethyloxy.

R1 also preferably represents optionally benzanellated Heterocyclyl with 5 or 6 ring members, at least one of which is for Oxygen, sulfur or nitrogen and optionally one or two further ring members stand for nitrogen, two in each of these residues geminal hydrogen atoms can be replaced by oxygen and where each of the heterocyclic residues is simple to triple, similar or can be differently substituted by halogen, cyano, nitro, amino, Hydroxy, Formyl, Carboxy Carbamoyl, Thiocarbamoyl, respectively straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulfinyl or Alkylsulfonyl, each with 1 to 6 carbon atoms, each straight-chain or branched alkenyl or alkenyloxy each having 2 to 6 Carbon atoms, each straight-chain or branched haloalkyl, Haloalkoxy, haloalkylthio, haloalkylsulfinyl or halogen alkylsulfonyl each having 1 to 6 carbon atoms and 1 to 13 the same or different halogen atoms, each straight-chain or branched Haloalkenyl or haloalkenyloxy, each with 2 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, each straight-chain or branched alkylamino, dialkylamino, alkylcarbonyl, Alkylcarbonyloxy, alkoxycarbonyl, alkylsulfonyloxy, hydroximinoalkyl or alkoximinoalkyl, each with 1 to 6 carbon atoms in the individual NEN alkyl parts, each optionally one or more times, the same or different from halogen and / or straight-chain or branched alkyl with 1 to 4 carbon atoms and / or straight-chain or branched Haloalkyl with 1 to 4 carbon atoms and 1 to 9 identical or ver different halogen atoms, each doubly linked Alkylene or dioxyalkylene, each with 1 to 6 carbon atoms, cyclo alkyl with 3 to 6 carbon atoms, heterocyclyl or heterocyclyl methyl with 3 to 7 ring members each, of which 1 to 3 are the same or are different heteroatoms - especially nitrogen, oxygen and / or sulfur -, and in each case optionally in the phenyl part  up to three times, identical or different by halogen, cyano and / or straight-chain or branched alkyl having 1 to 4 carbon atoms and / or straight-chain or branched haloalkyl with 1 to 4 carbons atoms and 1 to 9 identical or different halogen atoms and / or straight-chain or branched alkoxy with 1 to 4 carbon atoms and / or straight-chain or branched haloalkoxy with 1 to 4 Carbon atoms and 1 to 9 identical or different halogen atom-substituted phenyl, phenoxy, benzyl, benzyloxy, phenylethyl or phenylethyloxy.

R² is preferably C₁-C₈-alkyl, C₁-C₅-haloalkyl with 1 to 9 halo genatoms,
for C₁-C₄-alkoxy-C₁-C₈-alkyl, C₂-C₈-alkenyl,
for C₃-C₁₀ cycloalkyl, where these radicals can be substituted up to six times, identically or differently, by halogen, C₁-C₄-alkyl and / or C₁-C₄-haloalkyl having 1 to 9 identical or different halogen atoms,
for phenyl, naphthyl, phenyl-C₁-C₄-alkyl, phenyl-C₂-C₄-alkenyl, phenoxy-C₁-C₄-alkyl or phenylthio-C₁-C₄-alkyl, each of these radicals being substituted one to five times, in the same or different manner can by halogen, cyano, nitro, amino, hydroxy, formyl, carboxy carbamoyl, thiocarbamoyl, each straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl each having 1 to 6 carbon atoms, each straight-chain or branched alkenyl or alkenyloxy each having 2 to 6 carbon atoms, each straight-chain or branched haloalkyl, haloalkoxy, haloalkylthio, haloalkylsulfinyl or haloalkylsulfonyl each having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, each straight-chain or branched haloalkenyl or haloalkenyloxy each having 2 to 6 carbon atoms and 1 to 13 same or different NEN halogen atoms, each straight-chain or branched alk ylamino, dialkylamino, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkyl sulfonyloxy, hydroximinoalkyl or alkoximinoalkyl each having 1 to 6 carbon atoms in the individual alkyl parts, in each case optionally one or more times, identically or differently, by halogen and / or straight-chain or branched alkyl having 1 to 4 carbon atoms and / or straight-chain or branched haloalkyl with 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms substituted, in each case doubly linked alkylene or dioxyalkylene, each with 1 to 6 carbon atoms, cycloalkyl with 3 to 6 carbon atoms, heterocyclyl or heterocyclyl-methyl with 3 to 7 rings each, 1 to 3 of which are the same or different heteroatoms - in particular nitrogen, oxygen and / or sulfur - and in each case optionally in the phenyl part simply to triple, identical or different by halogen, cyano and / or straight chain or branched s alkyl having 1 to 4 carbon atoms and / or straight-chain or branched haloalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms and / or straight-chain or branched alkoxy having 1 to 4 carbon atoms and / or straight-chain or branched haloalkoxy having 1 up to 4 carbon atoms and 1 to 9 identical or different halogen atoms substituted phenyl, phenoxy, benzyl, benzyloxy, phenylethyl or phenylethyloxy.

R² also preferably represents hetero, optionally benzanellated cyclyl with 5 or 6 ring links, at least one for Sauer substance, sulfur or nitrogen and optionally one or two further ring members stand for nitrogen, two in each of these residues geminal hydrogen atoms can be replaced by oxygen and where each of the heterocyclic residues is simple to triple, similar or can be differently substituted by halogen, cyano, nitro, amino, Hydroxy, formyl, carboxy carbamoyl, thiocarbamoyl, each straight chain or branched alkyl, alkoxy, alkylthio, alkylsulfinyl or Alkylsulfonyl, each with 1 to 6 carbon atoms, each straight-chain or branched alkenyl or alkenyloxy, each with 2 to 6 Koh lenstoffatomen, each straight-chain or branched haloalkyl, halo genalkoxy, haloalkylthio, haloalkylsulfinyl or haloalkyl sulfonyl each having 1 to 6 carbon atoms and 1 to 13 the same or different halogen atoms, each straight-chain or branched Haloalkenyl or haloalkenyloxy, each with 2 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, each  straight-chain or branched alkylamino, dialkylamino, alkylcarbonyl, Alkylcarbonyloxy, alkoxycarbonyl, alkylsulfonyloxy, hydroximinoalkyl or alkoximinoalkyl, each with 1 to 6 carbon atoms in the individual NEN alkyl parts, each optionally one or more times, the same or different from halogen and / or straight-chain or branched alkyl with 1 to 4 carbon atoms and / or straight-chain or branched Haloalkyl with 1 to 4 carbon atoms and 1 to 9 identical or ver different halogen atoms, each doubly linked Alkylene or dioxyalkylene, each with 1 to 6 carbon atoms, cyclo alkyl with 3 to 6 carbon atoms, heterocyclyl or heterocyclyl methyl with 3 to 7 ring members each, of which 1 to 3 are the same or are different heteroatoms - especially nitrogen, oxygen and / or sulfur -, and in each case optionally in the phenyl part up to three times, identical or different by halogen, cyano and / or straight-chain or branched alkyl having 1 to 4 carbon atoms and / or straight-chain or branched haloalkyl with 1 to 4 carbons atoms and 1 to 9 identical or different halogen atoms and / or straight-chain or branched alkoxy with 1 to 4 carbon atoms and / or straight-chain or branched haloalkoxy with 1 to 4 Carbon atoms and 1 to 9 identical or different halogen atom-substituted phenyl, phenoxy, benzyl, benzyloxy, phenylethyl or phenylethyloxy.

R³ also preferably represents groups

R⁴ is preferably hydrogen, C₁-C₆ alkyl; C₁-C₆ halogen alkyl having 1 to 9 identical or different halogen atoms; C₁-C₄ alkoxy-C₁-C₄ alkyl; C₁-C₆ alkyl carbonyl; C₁-C₆ alkyl sulfonyl; C₁-C₆ haloalkylcarbonyl having 1 to 9 identical or different halogen atoms; C₁-C₄ alkoxy-C₁-C₄ alkyl carbonyl; for C₃-C₇-cycloalkyl, where these radicals can be substituted up to six times, identically or differently, by halogen, C₁-C₄-alkyl and / or C₁-C₄-haloalkyl having 1 to 9 identical or different halogen atoms,
for phenylcarbonyl or phenylsulfonyl, where each of these radicals can be mono- to fivefold, identical or differently substituted by halogen, hydroxy, cyano, amino, nitro, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-alkylthio, C₁- C₄-haloalkyl having 1 to 9 identical or different halogen atoms, C₁-C₄-alkylcarbonyl and / or phenyl, which itself can be substituted once to three times, identically or differently, by halogen and / or C₁-C₄-alkyl.

R⁵ is preferably hydrogen; C₁-C₆ alkyl; C₁-C₆ halogen alkyl having 1 to 9 identical or different halogen atoms; C₁-C₄ alkoxy-C₁-C₄ alkyl;
for C₃-C₇-cycloalkyl, where these radicals can be substituted up to six times, identically or differently, by halogen, C₁-C₄-alkyl and / or C₁-C₄-haloalkyl having 1 to 9 identical or different halogen atoms,
for phenyl or naphthyl, where each of these radicals can be mono- to pentasubstituted, identical or differently substituted by halogen, cyano, nitro, amino, hydroxy, formyl, carboxy carbamoyl, thiocarbamoyl, in each case straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl each having 1 to 6 carbon atoms, each straight-chain or branched alkenyl or alkenyloxy each having 2 to 6 carbon atoms, each straight-chain or branched haloalkyl, haloalkoxy, haloalkylthio, haloalkylsulfinyl or haloalkylsulfonyl each having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, each straight-chain or branched haloalkenyl or haloalkenyloxy each having 2 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, each straight-chain or branched alkylamino, dialkylamino, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylsulfonyloxy, hydroximinoa Alkyl or alkoximinoalkyl each having 1 to 6 carbon atoms in the individual alkyl parts, each optionally one or more times, identically or differently, by halogen and / or straight-chain or branched alkyl having 1 to 4 carbon atoms and / or straight-chain or branched haloalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms substituted, each having a double bond, alkylene or dioxyalkylene each having 1 to 6 carbon atoms, cycloalkyl having 3 to 6 carbon atoms, heterocyclyl or heterocyclyl-methyl each having 3 to 7 ring members, of which 1 to 3 are the same or different heteroatoms are - in particular nitrogen, oxygen and / or sulfur - and in each case optionally in the phenyl part from one to three times, the same or different by halogen, cyano and / or straight-chain or branched alkyl having 1 to 4 carbon atoms and / or straight chain or branched haloalkyl with 1 to 4 Carbon atoms and 1 to 9 identical or different halogen atoms and / or straight-chain or branched alkoxy with 1 to 4 carbon atoms and / or straight-chain or branched haloalkoxy with 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms substituted phenyl, phenoxy, benzyl , Benzyloxy, phenylethyl or phenylethyloxy.

R⁵ also preferably represents optionally benzanellated Heterocyclyl with 5 or 6 ring members, at least one of which stands for oxygen, sulfur or nitrogen and optionally one or two further ring members represent nitrogen, each in of these residues two geminal hydrogen atoms by oxygen can be replaced and wherein each of the heterocyclic radicals be single to triple, identical or differently substituted can be replaced by halogen, cyano, nitro, amino, hydroxy, formyl, Carboxy carbamoyl, thiocarbamoyl, each straight chain or branched alkyl, alkoxy, alkylthio, alkylsulfinyl or Alkylsulfonyl each having 1 to 6 carbon atoms, each straight-chain or branched alkenyl or alkenyloxy with each 2 to 6 carbon atoms, each straight-chain or branched  Haloalkyl, haloalkoxy, haloalkylthio, halogen alkylsulfinyl or haloalkylsulfonyl, each with 1 to 6 carbons atoms and 1 to 13 identical or different halogen atoms, each straight-chain or branched haloalkenyl or Haloalkenyloxy each having 2 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, each straight chain or branched alkylamino, dialkylamino, alkylcarbonyl, Alkylcarbonyloxy, alkoxycarbonyl, alkylsulfonyloxy, hydrox iminoalkyl or alkoximinoalkyl each having 1 to 6 carbon atoms in the individual alkyl parts, each optionally simple or multiple, the same or different by halogen and / or straight-chain or branched alkyl having 1 to 4 carbon atoms and / or straight-chain or branched haloalkyl with 1 to 4 Carbon atoms and 1 to 9 identical or different Halogen atoms substituted, each double-linked alkylene or dioxyalkylene each having 1 to 6 carbon atoms, cyclo alkyl with 3 to 6 carbon atoms, heterocyclyl or Heterocyclyl-methyl with 3 to 7 ring members each, of which 1 to 3 identical or different heteroatoms are - ins special nitrogen; Oxygen and / or sulfur - and each optionally up to three times in the phenyl part, identical or ver distinguished by halogen, cyano and / or straight-chain or ver branched alkyl having 1 to 4 carbon atoms and / or straight chain or branched haloalkyl with 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms and / or straight-chain or branched alkoxy with 1 to 4 carbons Substance atoms and / or straight-chain or branched haloalkoxy with 1 to 4 carbon atoms and 1 to 9 identical or ver different halogen atoms substituted phenyl, phenoxy, benzyl, Benzyloxy, phenylethyl or phenylethyloxy.

R⁶ is preferably hydrogen, C₁-C₆ alkyl; C₁-C₆ halogen alkyl having 1 to 9 identical or different halogen atoms;
C₁-C₄ alkoxy-C₁-C₄ alkyl; C₁-C₆ alkyl carbonyl; C₁-C₆ alkyl sulfonyl; C₁-C₆ haloalkylcarbonyl having 1 to 9 identical or different halogen atoms; C₁-C₄ alkoxy-C₁-C₄ alkyl carbonyl; for C₃-C₇-cycloalkyl, where these radicals can be substituted up to six times, identically or differently, by halogen, C₁-C₄-alkyl and / or C₁-C₄-haloalkyl having 1 to 9 identical or different halogen atoms,
for phenylcarbonyl or phenylsulfonyl, where each of these radicals can be mono- to fivefold, identical or differently substituted by halogen, hydroxy, cyano, amino, nitro, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-alkylthio, C₁- C₄-haloalkyl having 1 to 9 identical or different halogen atoms, C₁-C₄-alkylcarbonyl and / or phenyl, which itself can be substituted once to three times, identically or differently, by halogen and / or C₁-C₄-alkyl.

R⁷ is preferably hydrogen; C₁-C₆ alkyl; C₁-C₆ halogen alkyl having 1 to 9 identical or different halogen atoms; C₁-C₄ alkoxy-C₁-C₄ alkyl;
for C₃-C₇-cycloalkyl, where these radicals can be substituted up to six times, identically or differently, by halogen, C₁-C₄-alkyl and / or C₁-C₄-haloalkyl having 1 to 9 identical or different halogen atoms,
for phenyl or naphthyl, where each of these radicals can be mono- to pentasubstituted, identical or differently substituted by halogen, cyano, nitro, amino, hydroxy, formyl, carboxy carbamoyl, thiocarbamoyl, in each case straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl each having 1 to 6 carbon atoms, each straight-chain or branched alkenyl or alkenyloxy each having 2 to 6 carbon atoms, each straight-chain or branched haloalkyl, haloalkoxy, haloalkylthio, haloalkylsulfinyl or haloalkylsulfonyl each having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, each straight-chain or branched haloalkenyl or haloalkenyloxy each having 2 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, each straight-chain or branched alkylamino, dialkylamino, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylsulfonyloxy, hydroximinoa Alkyl or alkoximinoalkyl each having 1 to 6 carbon atoms in the individual alkyl parts, each optionally one or more times, identically or differently, by halogen and / or straight-chain or branched alkyl having 1 to 4 carbon atoms and / or straight-chain or branched haloalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms substituted, each having a double bond, alkylene or dioxyalkylene each having 1 to 6 carbon atoms, cycloalkyl having 3 to 6 carbon atoms, heterocyclyl or heterocyclyl-methyl each having 3 to 7 ring members, of which 1 to 3 are the same or different heteroatoms are especially nitrogen; Oxygen and / or sulfur -, and in each case in the phenyl part in each case single to triple, identical or different by halogen, cyano and / or straight-chain or branched alkyl having 1 to 4 carbon atoms and / or straight-chain or branched haloalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms and / or straight-chain or branched alkoxy with 1 to 4 carbon atoms and / or straight-chain or branched haloalkoxy with 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms substituted phenyl, phenoxy, benzyl, Benzyloxy, phenylethyl or phenylethyloxy.

R⁷ also preferably represents optionally benzanellated Heterocyclyl with 5 or 6 ring members, at least one of which stands for oxygen, sulfur or nitrogen and optionally one or two further ring members represent nitrogen, each in of these residues two geminal hydrogen atoms by oxygen can be replaced and wherein each of the heterocyclic radicals be single to triple, identical or differently substituted can be replaced by halogen, cyano, nitro, amino, hydroxy, formyl, Carboxy carbamoyl, thiocarbamoyl, each straight chain or  branched alkyl, alkoxy, alkylthio, alkylsulfinyl or Alkylsulfonyl each having 1 to 6 carbon atoms, each straight-chain or branched alkenyl or alkenyloxy with each 2 to 6 carbon atoms, each straight-chain or branched Haloalkyl, haloalkoxy, haloalkylthio, halogen alkylsulfinyl or haloalkylsulfonyl, each with 1 to 6 carbons atoms and 1 to 13 identical or different halogen atoms, each straight-chain or branched haloalkenyl or Haloalkenyloxy each having 2 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, each straight chain or branched alkylamino, dialkylamino, alkylcarbonyl, Alkylcarbonyloxy, alkoxycarbonyl, alkylsulfonyloxy, hydrox iminoalkyl or alkoximinoalkyl each having 1 to 6 carbon atoms in the individual alkyl parts, each optionally simple or multiple, the same or different by halogen and / or straight-chain or branched alkyl having 1 to 4 carbon atoms and / or straight-chain or branched haloalkyl with 1 to 4 Carbon atoms and 1 to 9 identical or different Halogen atoms substituted, each double-linked alkylene or dioxyalkylene each having 1 to 6 carbon atoms, cyclo alkyl with 3 to 6 carbon atoms, heterocyclyl or Heterocyclyl-methyl with 3 to 7 ring members each, of which 1 to 3 identical or different heteroatoms are - ins special nitrogen, oxygen and / or sulfur, and each optionally up to three times in the phenyl part, identical or ver distinguished by halogen, cyano and / or straight-chain or ver branched alkyl having 1 to 4 carbon atoms and / or straight chain or branched haloalkyl with 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms and / or straight-chain or branched alkoxy with 1 to 4 carbons Substance atoms and / or straight-chain or branched haloalkoxy with 1 to 4 carbon atoms and 1 to 9 identical or ver different halogen atoms substituted phenyl, phenoxy, benzyl, Benzyloxy, phenylethyl or phenylethyloxy.  

R⁸ is preferably hydrogen; C₁-C₆ alkyl; C₁-C₆ halogen alkyl having 1 to 9 identical or different halogen atoms; C₁-C₄ alkoxy-C₁-C₄ alkyl;
for C₃-C₇-cycloalkyl, where these radicals can be substituted up to six times, identically or differently, by halogen, C₁-C₄-alkyl and / or C₁-C₄-haloalkyl having 1 to 9 identical or different halogen atoms,
for phenyl or naphthyl, where each of these radicals can be mono- to pentasubstituted, identical or differently substituted by halogen, cyano, nitro, amino, hydroxy, formyl, carboxy carbamoyl, thiocarbamoyl, in each case straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl each having 1 to 6 carbon atoms, each straight-chain or branched alkenyl or alkenyloxy each having 2 to 6 carbon atoms, each straight-chain or branched haloalkyl, haloalkoxy, haloalkylthio, haloalkylsulfinyl or haloalkylsulfonyl each having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, each straight-chain or branched haloalkenyl or haloalkenyloxy each having 2 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, each straight-chain or branched alkylamino, dialkylamino, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylsulfonyloxy, hydroximinoa Alkyl or alkoximinoalkyl each having 1 to 6 carbon atoms in the individual alkyl parts, each optionally one or more times, identically or differently, by halogen and / or straight-chain or branched alkyl having 1 to 4 carbon atoms and / or straight-chain or branched haloalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms substituted, each having a double bond, alkylene or dioxyalkylene each having 1 to 6 carbon atoms, cycloalkyl having 3 to 6 carbon atoms, heterocyclyl or heterocyclyl-methyl each having 3 to 7 ring members, of which 1 to 3 are the same or are different heteroatoms - especially nitrogen; Oxygen and / or sulfur -, and in each case in the phenyl part in each case single to triple, identical or different by halogen, cyano and / or straight-chain or branched alkyl having 1 to 4 carbon atoms and / or straight-chain or branched haloalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms and / or straight-chain or branched alkoxy having 1 to 4 carbon atoms and / or straight-chain or branched haloalkoxy having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms substituted phenyl, phenoxy, benzyl, benzyloxy , Phenylethyl or phenylethyloxy.

R⁸ also preferably represents optionally benzanellated Heterocyclyl with 5 or 6 ring members, at least one of which for oxygen; Sulfur or nitrogen is and optionally or two further ring members represent nitrogen, each in of these residues two geminal hydrogen atoms by oxygen can be replaced and wherein each of the heterocyclic radicals be single to triple, identical or differently substituted can be replaced by halogen, cyano, nitro, amino, hydroxy, formyl, Carboxy carbamoyl, thiocarbamoyl, each straight chain or branched alkyl, alkoxy, alkylthio, alkylsulfinyl or Alkylsulfonyl each having 1 to 6 carbon atoms, each straight-chain or branched alkenyl or alkenyloxy with each 2 to 6 carbon atoms, each straight-chain or branched Haloalkyl, haloalkoxy, haloalkylthio, halogen alkylsulfinyl or haloalkylsulfonyl, each with 1 to 6 carbons atoms and 1 to 13 identical or different halogen atoms, each straight-chain or branched haloalkenyl or Haloalkenyloxy each having 2 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, each straight chain or branched alkylamino, dialkylamino, alkylcarbonyl, Alkylcarbonyloxy, alkoxycarbonyl, alkylsulfonyloxy, hydrox iminoalkyl or alkoximinoalkyl each having 1 to 6 carbon atoms in the individual alkyl parts, each optionally simple or multiple, the same or different by halogen and / or  straight-chain or branched alkyl having 1 to 4 carbon atoms and / or straight-chain or branched haloalkyl with 1 to 4 Carbon atoms and 1 to 9 identical or different Halogen atoms substituted, each double-linked alkylene or dioxyalkylene each having 1 to 6 carbon atoms, cyclo alkyl with 3 to 6 carbon atoms, heterocyclyl or Heterocyclyl-methyl with 3 to 7 ring members each, of which 1 to 3 identical or different heteroatoms are - ins special nitrogen, oxygen and / or sulfur, and each optionally up to three times in the phenyl part, identical or ver distinguished by halogen, cyano and / or straight-chain or ver branched alkyl having 1 to 4 carbon atoms and / or straight chain or branched haloalkyl with 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms and / or straight-chain or branched alkoxy with 1 to 4 carbons Substance atoms and / or straight-chain or branched haloalkoxy with 1 to 4 carbon atoms and 1 to 9 identical or ver different halogen atoms substituted phenyl, phenoxy, benzyl, Benzyloxy, phenylethyl or phenylethyloxy.

R¹ particularly preferably represents C₁-C₆ alkyl; C _1-6 haloalkyl having 1 to 9 identical or different halogen atoms; C₁-C₂ alkoxy-C₁-C₄ alkyl; C₂-C₄ alkenyl;
for C₃-C₆-cycloalkyl, where each of these radicals can be substituted up to four times, in the same way or differently, by fluorine, chlorine, bromine, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, sec .-Butyl, tert.-butyl, chloromethyl, dichloromethyl and / or trifluoromethyl,
for phenyl, naphthyl, benzyl, styryl, phenoxymethyl or phenylthio methyl, where each of these radicals can be monosubstituted to triple, identical or differently substituted by fluorine, chlorine, bromine, cyano, nitro, amino, hydroxy, formyl, carboxy, carbamoyl, thiocarbamoyl , Methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethyl sulfinyl, methylsulfonyl or ethylsulfonyl, trifluoromethyl, difluoromethoxy, trifluoromethoxy, difluoromethylthio, trifluoromethylthio, trifluoromethylsulfinyl or trifluoromethylsulfonyl, methylamino, ethylamino, n- or i-propylamino, dimethylamyl, methylyloxy, methylyloxy, methylyloxy, methylyloxy, methylyloxy, methylyloxy, methylyloxy, methylyloxy, methylyloxyethyloxyethyl, acyl, methylyloxy, methylyloxy, ethyl, methylyloxyethyloxyethyl, acyl, methylyloxyethyl, methylyloxyethyloxyethyl, acyl, methylethyloxyethyl, methylethyl, acyl, methylethyl, acyl, methylethyl, acyl, methylethyl, acyl, methylethyl, acyl, methylethyl sulfonyloxy, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, ethoximinomethyl, methoximinoethyl or ethoximinoethyl; each ge optionally single to fourfold, identical or different by fluorine, chlorine, methyl, ethyl, n- or i-propyl substituted trimethylene (propane-1,3-diyl), methylenedioxy or ethylenedioxy, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, and each in the phenyl part, if appropriate, once to three times, identically or differently, by fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy , n- or i-propoxy, difluoromethoxy or trifluoromethoxy substituted phenyl, phenoxy, benzyl or benzyloxy.

R¹ also particularly preferably represents furyl, tetrahydrofuryl, benzofuryl, Tetrahydropyranyl, thienyl, benzothienyl, pyrrolyl, dihydropyrrolyl, tetra hydropyrrolyl, benzopyrrolyl, benzodihydropyrrolyl, oxazolyl, benz oxazolyl, isoxazolyl, thiazolyl, benzthiazolyl, isothiazolyl, imidazolyl, Benzimidazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyrimidinyl, Pyridazinyl, pyrazinyl, 1,2,3-triazinyl, 1,2,4-triazinyl or 1,3,5-triazinyl, where two geminal hydrogen atoms are replaced by one oxygen atom can be and wherein each of these heterocyclic residues simply to can be triple, identical or differently substituted by fluorine, Chlorine, bromine, cyano, nitro, amino, hydroxy, formyl, carboxy, carb amoyl, thiocarbamoyl, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, Methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethyl sulfonyl, trifluoromethyl, difluoromethoxy, trifluoromethoxy, difluoromethyl thio, trifluoromethylthio, trifluoromethylsulfinyl or trifluoromethylsulfonyl, Methylamino, ethylamino, n- or i-propylamino, dimethylamino, diethyl amino, acetyl, propionyl, acetyloxy, methoxycarbonyl, ethoxycarbonyl, Methylsulfonyloxy, ethylsulfonyloxy, hydroximinomethyl, hydroximino ethyl, methoximinomethyl, ethoximinomethyl, methoximinoethyl or Ethoximinoethyl; each up to fourfold, if necessary, the same or different by fluorine, chlorine, methyl, ethyl, n- or i-propyl substituted  trimethylene (propane-1,3-diyl), methylenedioxy or ethylenedioxy, Cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, as well as ge if necessary, in the phenyl part, up to three times, the same or different by fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoro methoxy or trifluoromethoxy substituted phenyl, phenoxy, benzyl or Benzyloxy.

R² particularly preferably represents C₁-C₆-alkyl; C _1-6 haloalkyl having 1 to 9 identical or different halogen atoms; C₁-C₂ alkoxy-C₁-C₄ alkyl; C₂-C₄ alkenyl;
for C₃-C₆-cycloalkyl, where each of these radicals can be substituted up to four times, in the same way or differently, by fluorine, chlorine, bromine, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, sec .-Butyl, tert.-butyl, chloromethyl, dichloromethyl and / or trifluoromethyl,
for phenyl, naphthyl, benzyl, styryl, phenoxymethyl or phenylthio methyl, where each of these radicals can be monosubstituted to triple, identical or differently substituted by fluorine, chlorine, bromine, cyano, nitro, amino, hydroxy, formyl, carboxy, carbamoyl, thiocarbamoyl , Methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethyl sulfinyl, methylsulfonyl or ethylsulfonyl, trifluoromethyl, difluoromethoxy, trifluoromethoxy, difluoromethylthio, trifluoromethylthio, trifluoromethylsulfinyl or trifluoromethylsulfonyl, methylamino, ethylamino, n- or i-propylamino, dimethylamyl, methylyloxy, methylyloxy, methylyloxy, methylyloxy, methylyloxy, methylyloxy, methylyloxy, methylyloxy, methylyloxyethyloxyethyl, acyl, methylyloxy, methylyloxy, ethyl, methylyloxyethyloxyethyl, acyl, methylyloxyethyl, methylyloxyethyloxyethyl, acyl, methylethyloxyethyl, methylethyl, acyl, methylethyl, acyl, methylethyl, acyl, methylethyl, acyl, methylethyl, acyl, methylethyl sulfonyloxy, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, ethoximinomethyl, methoximinoethyl or ethoximinoethyl; each optionally single to fourfold, identical or different by fluorine, chlorine, methyl, ethyl, n- or i-propyl-substituted trimethylene (propane-1,3-diyl), methylenedioxy or ethylenedioxy, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, and each in the phenyl part, if appropriate, once to three times, identically or differently, by fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy , n- or i-propoxy, difluoromethoxy or trifluoro methoxy substituted phenyl, phenoxy, benzyl or benzyloxy.

R² also particularly preferably represents furyl, tetrahydrofuryl, benzofuryl, Tetrahydropyranyl, thienyl, benzothienyl, pyrrolyl, dihydropyrrolyl, tetra hydropyrrolyl, benzopyrrolyl, benzodihydropyrrolyl, oxazolyl, benz oxazolyl, isoxazolyl, thiazolyl, benzthiazolyl, isothiazolyl, imidazolyl, Benzimidazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyrimidinyl, Pyridazinyl, pyrazinyl, 1,2,3-triazinyl, 1,2,4-triazinyl or 1,3,5-triazinyl, where two geminal hydrogen atoms are replaced by one oxygen atom can be and wherein each of these heterocyclic residues simply to can be triple, identical or differently substituted by fluorine, Chlorine, bromine, cyano, nitro, amino, hydroxy, formyl, carboxy, carb amoyl, thiocarbamoyl, methyl, ethyl, n- or i-propyl, n-, i-, s- or t- Butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethyl sulfonyl, trifluoromethyl, difluoromethoxy, trifluoromethoxy, difluoromethyl thio, trifluoromethylthio, trifluoromethylsulfinyl or trifluoromethylsulfonyl, Methylamino, ethylamino, n- or i-propylamino, dimethylamino, diethyl amino, acetyl, propionyl, acetyloxy, methoxycarbonyl, ethoxycarbonyl, Methylsulfonyloxy, ethylsulfonyloxy, hydroximinomethyl, hydroximino ethyl, methoximinomethyl, ethoximinomethyl, methoximinoethyl or Ethoximinoethyl; each up to fourfold, if necessary, the same or different by fluorine, chlorine, methyl, ethyl, n- or i-propyl substituted trimethylene (propane-1,3-diyl), methylenedioxy or ethylenedioxy, Cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, as well as ge if necessary, in the phenyl part, up to three times, the same or different by fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoro methoxy or trifluoromethoxy substituted phenyl, phenoxy, benzyl or Benzyloxy.

R³ also particularly preferably stands for the groups

R⁴ particularly preferably represents hydrogen; C₁-C₄ alkyl; C₁-C₄ halo genalkyl having 1 to 6 identical or different halogen atoms; C₁-C₂-alkoxy-C₁-C₂-alkyl, C₁-C₄-alkyl-carbonyl; C₁-C₄-alkylsulfonyl, C₁-C₄-haloalkyl-carbonyl having 1 to 6 identical or different halogen atoms; C₁-C₂-alkoxy-C₁-C₂-alkylcarbonyl;
for C₃-C₆-cycloalkyl, where each of these radicals can be substituted up to four times, in the same way or differently, by fluorine, chlorine, bromine, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, sec .-Butyl, tert.-butyl, chloromethyl, dichloromethyl and / or trifluoromethyl,
for phenylcarbonyl or phenylsulfonyl, where each of these radicals can be mono- to tetrasubstituted, identical or differently substituted by fluorine, chlorine, bromine, hydroxyl, cyano, nitro, amino, methyl, ethyl, n- or i-propyl, n-, i- , sec- or tert-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, trifluoromethyl, difluoromethoxy, trifluoromethoxy, acetyl, ethylcarbonyl and / or phenyl, which itself is simple or can be substituted twice, identically or differently by fluorine, chlorine, methyl and / or ethyl.

R⁵ particularly preferably represents hydrogen; C₁-C₄ alkyl; C₁-C₄ halo genalkyl having 1 to 6 identical or different halogen atoms; C₁-C₂-alkoxy-C₁-C₂-alkyl,
for C₃-C₆-cycloalkyl, where each of these radicals can be substituted up to four times, in the same way or differently, by fluorine, chlorine, bromine, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, sec .-Butyl, tert.-butyl, chloromethyl, dichloromethyl and / or trifluoromethyl,
for phenyl or naphthyl, where each of these radicals can be monosubstituted to trisubstituted, identical or different, by fluorine, chlorine, bromine, cyano, nitro, amino, hydroxyl, formyl, carboxy, carbamoyl, thio carbamoyl, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, trifluoromethyl, Difluoromethoxy, trifluoromethoxy, difluoromethylthio, trifluoromethylthio, trifluoromethylsulphinyl or trifluoromethylsulphonyl, methyl amino, ethylamino, n- or i-propylamino, dimethylamino, diethylamino, acetyl, propionyl, acetyloxy, methoxyoxyethyl, hydroxymethyloxyethylmethyloxyethylmethyloxyethylmethyloxyethylmethyloxyethyl methyloxymethyloxymethyloxyethyl methyloxymethyloxy methylethylmethyloxyethyl methyloxymethyloxy Ethoximinomethyl, methoximinoethyl or ethoximinoethyl; in each case optionally up to four times, identically or differently, trimethylene (propane-1,3-diyl) substituted by fluorine, chlorine, methyl, ethyl, n- or i-propyl, methylenedioxy or ethylenedioxy, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, and in each case, if appropriate, in the phenyl part simply to triple, identical or different, by fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, Ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy substituted phenyl, phenoxy, benzyl or benzyloxy.

R⁵ also particularly preferably represents furyl, tetrahydrofuryl, benzofuryl, Tetrahydropyranyl, thienyl; Benzothienyl, pyrrolyl, dihydropyrrolyl, tetra hydropyrrolyl, benzopyrrolyl, benzodihydropyrrolyl, oxazolyl, benz oxazolyl, isoxazolyl, thiazolyl, benzthiazolyl, isothiazolyl, imidazolyl, Benzimidazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyrimidinyl, Pyridazinyl, pyrazinyl, 1,2,3-triazinyl, 1,2,4-triazinyl or 1,3,5-triazinyl, where two geminal hydrogen atoms are replaced by one oxygen atom can be and wherein each of these heterocyclic residues simply to can be triple, identical or differently substituted by fluorine, Chlorine, bromine, cyano, nitro, amino, hydroxy, formyl, carboxy, carb amoyl, thiocarbamoyl, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, Methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethyl sulfonyl, trifluoromethyl, difluoromethoxy, trifluoromethoxy, difluoromethyl thio, trifluoromethylthio, trifluoromethylsulfinyl or trifluoromethylsulfonyl, Methylamino, ethylamino, n- or i-propylamino, dimethylamino, diethyl amino, acetyl, propionyl, acetyloxy, methoxycarbonyl, ethoxycarbonyl, Methylsulfonyloxy, ethylsulfonyloxy, hydroximinomethyl, hydroximino  ethyl, methoximinomethyl, ethoximinomethyl, methoximinoethyl or Ethoximinoethyl; each up to fourfold, if necessary, the same or different by fluorine, chlorine, methyl, ethyl, n- or i-propyl substituted trimethylene (propane-1,3-diyl), methylenedioxy or ethylenedioxy, Cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, as well as ge if necessary, in the phenyl part, up to three times, the same or different by fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoro methoxy or trifluoromethoxy substituted phenyl, phenoxy, benzyl or Benzyloxy.

R⁶ particularly preferably represents hydrogen; C₁-C₄ alkyl; C₁-C₄ halo genalkyl having 1 to 6 identical or different halogen atoms; C₁-C₂-alkoxy-C₁-C₂-alkyl, C₁-C₄-alkyl-carbonyl; C₁-C₄-alkylsulfonyl, C₁-C₄-haloalkyl-carbonyl having 1 to 6 identical or different halogen atoms; C₁-C₂-alkoxy-C₁-C₂-alkylcarbonyl;
for C₃-C₆-cycloalkyl, where each of these radicals can be substituted up to four times, in the same way or differently, by fluorine, chlorine, bromine, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, sec .-Butyl, tert.-butyl, chloromethyl, dichloromethyl and / or trifluoromethyl,
for phenylcarbonyl or phenylsulfonyl, where each of these radicals can be mono- to tetrasubstituted, identical or differently substituted by fluorine, chlorine, bromine, hydroxyl, cyano, nitro, amino, methyl, ethyl, n- or i-propyl, n-, i- , sec- or tert-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, trifluoromethyl, difluoromethoxy, trifluoromethoxy, acetyl, ethylcarbonyl and / or phenyl, which itself is simple or can be substituted twice, identically or differently by fluorine, chlorine, methyl and / or ethyl.

R⁷ particularly preferably represents hydrogen; C₁-C₄ alkyl; C₁-C₄ halo genalkyl having 1 to 6 identical or different halogen atoms; C₁-C₂-alkoxy-C₁-C₂-alkyl,
for C₃-C₆-cycloalkyl, where each of these radicals can be substituted up to four times, in the same way or differently, by fluorine, chlorine, bromine, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, sec .-Butyl, tert.-butyl, chloromethyl, dichloromethyl and / or trifluoromethyl,
for phenyl or naphthyl, where each of these radicals can be monosubstituted to trisubstituted, identical or different, by fluorine, chlorine, bromine, cyano, nitro, amino, hydroxyl, formyl, carboxy, carbamoyl, thio carbamoyl, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, trifluoromethyl, Difluoromethoxy, trifluoromethoxy, difluoromethylthio, trifluoromethylthio, trifluoromethylsulphinyl or trifluoromethylsulphonyl, methyl amino, ethylamino, n- or i-propylamino, dimethylamino, diethylamino, acetyl, propionyl, acetyloxy, methoxyoxyethyl, hydroxymethyloxyethylmethyloxyethylmethyloxyethylmethyloxyethylmethyloxyethyl methyloxymethyloxymethyloxyethyl methyloxymethyloxy methylethylmethyloxyethyl methyloxymethyloxy Ethoximinomethyl, methoximinoethyl or ethoximinoethyl; in each case optionally up to four times, identically or differently, trimethylene (propane-1,3-diyl) substituted by fluorine, chlorine, methyl, ethyl, n- or i-propyl, methylenedioxy or ethylenedioxy, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, and in each case, if appropriate, in the phenyl part simply to triple, identical or different, by fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, Ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy substituted phenyl, phenoxy, benzyl or benzyloxy.

R⁷ also particularly preferably represents furyl, tetrahydrofuryl, benzofuryl, Tetrahydropyranyl, thienyl, benzothienyl, pyrrolyl, dihydropyrrolyl, tetra hydropyrrolyl, benzopyrrolyl, benzodihydropyrrolyl, oxazolyl, benz oxazolyl, isoxazolyl, thiazolyl, benzthiazolyl, isothiazolyl, imidazolyl, Benzimidazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyrimidinyl, Pyridazinyl, pyrazinyl, 1,2,3-triazinyl, 1,2,4-triazinyl or 1,3,5-triazinyl, where two geminal hydrogen atoms are replaced by one oxygen atom can be and wherein each of these heterocyclic residues simply to can be triple, identical or differently substituted by fluorine, Chlorine, bromine, cyano, nitro, amino, hydroxy, formyl, carboxy, carb amoyl, thiocarbamoyl, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl,  Methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethyl sulfonyl, trifluoromethyl, difluoromethoxy, trifluoromethoxy, difluoromethyl thio, trifluoromethylthio, trifluoromethylsulfinyl or trifluoromethylsulfonyl, Methylamino, ethylamino, n- or i-propylamino, dimethylamino, diethyl amino, acetyl, propionyl, acetyloxy, methoxycarbonyl, ethoxycarbonyl, Methylsulfonyloxy, ethylsulfonyloxy, hydroximinomethyl, hydroximino ethyl, methoximinomethyl, ethoximinomethyl, methoximinoethyl or Ethoximinoethyl; each up to fourfold, if necessary, the same or different by fluorine, chlorine, methyl, ethyl, n- or i-propyl substituted trimethylene (propane-1,3-diyl), methylenedioxy or ethylenedioxy, Cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, as well as ge if necessary, in the phenyl part, up to three times, the same or different by fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoro methoxy or trifluoromethoxy substituted phenyl, phenoxy, benzyl or Benzyloxy.

R⁵ particularly preferably represents hydrogen; C₁-C₄ alkyl; C₁-C₄ halo genalkyl having 1 to 6 identical or different halogen atoms; C₁-C₂-alkoxy-C₁-C₂-alkyl,
for C₃-C₆-cycloalkyl, where each of these radicals can be substituted up to four times, in the same way or differently, by fluorine, chlorine, bromine, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, sec .-Butyl, tert.-butyl, chloromethyl, dichloromethyl and / or trifluoromethyl,
for phenyl or naphthyl, where each of these radicals can be monosubstituted to trisubstituted, identical or different, by fluorine, chlorine, bromine, cyano, nitro, amino, hydroxyl, formyl, carboxy, carbamoyl, thio carbamoyl, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, trifluoromethyl, Difluoromethoxy, trifluoromethoxy, difluoromethylthio, trifluoromethylthio, trifluoromethylsulphinyl or trifluoromethylsulphonyl, methyl amino, ethylamino, n- or i-propylamino, dimethylamino, diethylamino, acetyl, propionyl, acetyloxy, methoxyoxyethyl, hydroxymethyloxyethylmethyloxyethylmethyloxyethylmethyloxyethylmethyloxyethyl methyloxymethyloxymethyloxyethyl methyloxymethyloxy methylethylmethyloxyethyl methyloxymethyloxy Ethoximinomethyl, methoximinoethyl or ethoximinoethyl; in each case optionally up to four times, identically or differently, trimethylene (propane-1,3-diyl) substituted by fluorine, chlorine, methyl, ethyl, n- or i-propyl, methylenedioxy or ethylenedioxy, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, and in each case, if appropriate, in the phenyl part simply to triple, identical or different, by fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, Ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy substituted phenyl, phenoxy, benzyl or benzyloxy.

R⁸ also particularly preferably represents furyl, tetrahydrofuryl, benzofuryl, Tetrahydropyranyl, thienyl, benzothienyl, pyrrolyl, dihydropyrrolyl, tetra hydropyrrolyl, benzopyrrolyl, benzodihydropyrrolyl, oxazolyl, benz oxazolyl, isoxazolyl, thiazolyl, benzthiazolyl, isothiazolyl, imidazolyl, Benzimidazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyrimidinyl, Pyridazinyl, pyrazinyl, 1,2,3-triazinyl, 1,2,4-triazinyl or 1,3,5-triazinyl, where two geminal hydrogen atoms are replaced by one oxygen atom can be and wherein each of these heterocyclic residues simply to can be triple, identical or differently substituted by fluorine, Chlorine, bromine, cyano, nitro, amino, hydroxy, formyl, carboxy, carb amoyl, thiocarbamoyl, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, Methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethyl sulfonyl, trifluoromethyl, difluoromethoxy, trifluoromethoxy, difluoromethyl thio, trifluoromethylthio, trifluoromethylsulfinyl or trifluoromethylsulfonyl, Methylamino, ethylamino, n- or i-propylamino, dimethylamino, diethyl amino, acetyl, propionyl, acetyloxy, methoxycarbonyl, ethoxycarbonyl, Methylsulfonyloxy, ethylsulfonyloxy, hydroximinomethyl, hydroximino ethyl, methoximinomethyl, ethoximinomethyl, methoximinoethyl or Ethoximinoethyl; each up to fourfold, if necessary, the same or different by fluorine, chlorine, methyl, ethyl, n- or i-propyl substituted trimethylene (propane-1,3-diyl), methylenedioxy or ethylenedioxy, Cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, as well as ge  if necessary, in the phenyl part, up to three times, the same or different by fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoro methoxy or trifluoromethoxy substituted phenyl, phenoxy, benzyl or Benzyloxy.

R¹ very particularly preferably represents methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, sec-butyl, tert-butyl, n-pentyl, i-pentyl, n-hexyl, i- Hexyl;
for chloromethyl, bromomethyl, chloroethyl, bromethyl;
for methoxymethyl, methoxyethyl, methoxypropyl, ethoxymethyl, ethoxyethyl, ethoxypropyl;
for allyl, n-butenyl, i-butenyl;
for cyclopropyl, cyclopentyl or cyclohexyl which are each mono- to tetrasubstituted, identically or differently, by fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, chloromethyl, dichloromethyl and / or trifluoromethyl;
as well as for phenyl, benzyl, phenoxymethyl, phenylthiomethyl, pyrimidinyl or pyridinyl, where each of these radicals can be substituted once to three times, identically or differently, by fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n- , i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, trifluoromethyl, difluoromethoxy, trifluoromethoxy, difluoromethylthio, Trifluoromethylthio, trifluoromethylsulfinyl or trifluoromethylsulfonyl, methoxycarbonyl, ethoxycarbonyl, methoximinomethyl, ethoximinomethyl, methoximinoethyl or ethoximinoethyl; each optionally one to four times, the same or different fluorine, chlorine, methyl or ethyl substituted methylene dioxy or ethylenedioxy, and in each case optionally in the phenyl part one to four times, the same or different by fluorine, chlorine, bromine, cyano, methyl, ethyl, n - or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy substituted phenyl, phenoxy, benzyl or benzyloxy.

R² very particularly preferably represents methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, sec-butyl, tert-butyl, n-pentyl, i-pentyl, n-hexyl, i- Hexyl;
for chloromethyl, bromomethyl, chloroethyl, bromethyl;
for methoxymethyl, methoxyethyl, methoxypropyl, ethoxymethyl, ethoxyethyl, ethoxypropyl;
for allyl, n-butenyl, i-butenyl;
for cyclopropyl, cyclopentyl or cyclohexyl which are each mono- to tetrasubstituted, identically or differently, by fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, chloromethyl, dichloromethyl and / or trifluoromethyl;
as well as for phenyl, benzyl, phenoxymethyl, phenylthiomethyl, pyrimidinyl or pyridinyl, where each of these radicals can be substituted once to three times, identically or differently, by fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n- , i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, trifluoromethyl, difluoromethoxy, trifluoromethoxy, difluoromethylthio, Trifluoromethylthio, trifluoromethylsulfinyl or trifluoromethylsulfonyl, methoxycarbonyl, ethoxycarbonyl, methoximinomethyl, ethoximinomethyl, methoximinoethyl or ethoximinoethyl; each optionally one to four times, the same or different 49118 00070 552 001000280000000200012000285914900700040 0002004426757 00004 48999 substituted by fluorine, chlorine, methyl or ethyl methylene dioxy or ethylenedioxy, and in each case optionally in the phenyl part one to four times, the same or different by fluorine, chlorine, bromine, cyano , Methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy substituted phenyl, phenoxy, benzyl or Benzyloxy.

R³ also very particularly preferably stands for the groupings

R⁴ very particularly preferably represents hydrogen;
for methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, sec-butyl, tert-butyl
for chloromethyl, bromomethyl, chloroethyl, bromoethyl, chloropropyl, bromopropyl;
for methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl;
for acetyl, ethylcarbonyl, propylcarbonyl, butylcarbonyl;
for methylsulfonyl, ethylsulfonyl, propylsulfonyl, butylsulfonyl;
for acetyl, ethylcarbonyl, propylcarbonyl or butylcarbonyl which are monosubstituted to trisubstituted by fluorine, chlorine and / or bromine,
for methoxyacetyl, methoxyethylcarbonyl, ethoxyacetyl or ethoxyethyl carbonyl,
for cyclopropyl, cyclopentyl or cyclohexyl which are each mono- to tetrasubstituted, identically or differently, by fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, chloromethyl, dichloromethyl and / or trifluoromethyl;
and for phenylcarbonyl or phenylsulfonyl, where each of these two radicals can be substituted once to three times, identically or differently, by fluorine, chlorine, bromine, hydroxyl, cyano, nitro, amino, methyl, ethyl, n- or i-propyl, n-, i-, sec- or tert-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, trifluoromethyl, difluoromethoxy, trifluoromethoxy, acetyl, ethylcarbonyl and / or phenyl, the same can be substituted once or twice, identically or differently, by fluorine, chlorine, methyl and / or ethyl.

R⁵ very particularly preferably represents hydrogen;
for methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, sec-butyl, tert-butyl;
for chloromethyl, bromomethyl, chloroethyl, bromoethyl, chloropropyl, bromopropyl;
for methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl;
for cyclopropyl, cyclopentyl or cyclohexyl which are each mono- to tetrasubstituted, identically or differently, by fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, chloromethyl dichloromethyl and / or trifluoromethyl;
as well as for phenyl, pyridyl or pyrimidinyl, where each of these radicals can be substituted once to three times, identically or differently, by fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, trifluoromethyl, difluoromethoxy, trifluoromethoxy, difluoromethylthio, trifluoromethylfluoromethyllio , Methoxycarbonyl, ethoxycarbonyl, methoximinomethyl, ethoximinomethyl, methoximinoethyl or ethoximinoethyl; in each case optionally up to four times, identically or differently, fluorine, chlorine, methyl or ethyl-substituted methylenedioxy or ethylenedioxy, and in each case, if appropriate, in the phenyl part simply up to four times the same or differently by fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-Propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy substituted phenyl, phenoxy, benzyl or benzyloxy.

R⁶ very particularly preferably represents hydrogen;
for methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, sec-butyl, tert-butyl
for chloromethyl, bromomethyl, chloroethyl, bromoethyl, chloropropyl, bromopropyl;
for methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl;
for acetyl, ethylcarbonyl, propylcarbonyl, butylcarbonyl;
for methylsulfonyl, ethylsulfonyl, propylsulfonyl, butylsulfonyl;
for acetyl, ethylcarbonyl, propylcarbonyl or butylcarbonyl which are monosubstituted to trisubstituted by fluorine, chlorine and / or bromine,
for methoxyacetyl, methoxyethylcarbonyl, ethoxyacetyl or ethoxyethyl carbonyl,
for cyclopropyl, cyclopentyl or cyclohexyl which are each mono- to tetrasubstituted, identically or differently, by fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, chloromethyl, dichloromethyl and / or trifluoromethyl;
and for phenylcarbonyl or phenylsulfonyl, where each of these two radicals can be substituted once to three times, identically or differently, by fluorine, chlorine, bromine, hydroxyl, cyano, nitro, amino, methyl, ethyl, n- or i-propyl, n-, i-, sec- or tert-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, trifluoromethyl, difluoromethoxy, trifluoromethoxy, acetyl, ethylcarbonyl and / or phenyl, the same can be substituted once or twice, identically or differently, by fluorine, chlorine, methyl and / or ethyl.

R⁷ very particularly preferably represents hydrogen;
for methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, sec-butyl, tert-butyl;
for chloromethyl, bromomethyl, chloroethyl, bromoethyl, chloropropyl, bromopropyl;
for methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl;
for cyclopropyl, cyclopentyl or cyclohexyl which are each mono- to tetrasubstituted, identically or differently, by fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, chloromethyl dichloromethyl and / or trifluoromethyl;
as well as for phenyl, pyridyl or pyrimidinyl, where each of these radicals can be substituted once to three times, identically or differently, by fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, trifluoromethyl, difluoromethoxy, trifluoromethoxy, difluoromethylthio, trifluoromethylfluoromethyllio , Methoxycarbonyl, ethoxycarbonyl, methoximinomethyl, ethoximinomethyl, methoximinoethyl or ethoximinoethyl; in each case optionally up to four times, identically or differently, fluorine, chlorine, methyl or ethyl-substituted methylenedioxy or ethylenedioxy, and in each case, if appropriate, in the phenyl part simply up to four times the same or differently by fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-Propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy substituted phenyl, phenoxy, benzyl or benzyloxy.

R⁸ very particularly preferably represents hydrogen;
for methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, sec-butyl, tert-butyl;
for chloromethyl, bromomethyl, chloroethyl, bromoethyl, chloropropyl, bromopropyl;
for methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl;
for cyclopropyl, cyclopentyl or cyclohexyl which are each mono- to tetrasubstituted, identically or differently, by fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, chloromethyl dichloromethyl and / or trifluoromethyl;
as well as for phenyl, pyridyl or pyrimidinyl, where each of these radicals can be substituted once to three times, identically or differently, by fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, trifluoromethyl, difluoromethoxy, trifluoromethoxy, difluoromethylthio, trifluoromethylfluoromethyllio , Methoxycarbonyl, ethoxycarbonyl, methoximinomethyl, ethoximinomethyl, methoximinoethyl or ethoximinoethyl; in each case optionally up to four times, identically or differently, fluorine, chlorine, methyl or ethyl-substituted methylenedioxy or ethylenedioxy, and in each case, if appropriate, in the phenyl part simply up to four times the same or differently by fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-Propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy substituted phenyl, phenoxy, benzyl or benzyloxy.

A preferred group of compounds according to the invention are 2-imidazolidinone derivatives of the formula

in which
R¹⁰ represents phenyl which is monosubstituted to trisubstituted in the same way or differently, the phenyl substituents mentioned in connection with the description of R¹ being preferred, particularly preferred or very particularly preferred and
R², R⁴ and R⁵ have the abovementioned general, preferred, particularly preferred or very particularly preferred meanings.

Another group of preferred compounds according to the invention are 2-imidazolidinone derivatives of the formula

in which
R¹⁰ represents phenyl which is monosubstituted to trisubstituted in the same way or differently, the phenyl substituents mentioned in connection with the description of R¹ being preferred, particularly preferred or very particularly preferred and
R², R⁶ and R⁷ have the abovementioned general, preferred, particularly preferred or very particularly preferred meanings.

Another group of preferred compounds according to the invention are 2-imidazolidinone derivatives of the formula

R¹⁰ represents phenyl which is monosubstituted to trisubstituted in the same way or differently, the phenyl substituents mentioned in connection with the description of R¹ being preferred, particularly preferred or very particularly preferred and
R² and R⁸ have the abovementioned general, preferred, particularly preferred or very particularly preferred meanings.

Another group of preferred compounds according to the invention are 2-imidazolidinone derivatives of the formula

in which
R¹¹ represents phenyl, pyridinyl or pyrimidinyl which may be monosubstituted to trisubstituted in the same way or differently, the substituents mentioned in connection with the description of R² being preferred, particularly preferred or very particularly preferred for these radicals and
R¹, R⁴ and R⁵ have the abovementioned general, preferred, particularly preferred or very particularly preferred meanings.

Another group of preferred compounds according to the invention are 2-imidazolidinone derivatives of the formula

in which
R¹¹ represents phenyl, pyridinyl or pyrimidinyl which may be monosubstituted to trisubstituted in the same way or differently, the substituents mentioned in connection with the description of R² being preferred, particularly preferred or very particularly preferred for these radicals and
R¹, R⁶ and R⁷ have the abovementioned general, preferred, particularly preferred or very particularly preferred meanings.

Another group of preferred compounds according to the invention are 2-imidazolidinone derivatives of the formula

in which
R¹¹ represents phenyl, pyridinyl or pyrimidinyl which may be monosubstituted to trisubstituted in the same way or differently, the substituents mentioned in connection with the description of R² being preferred, particularly preferred or very particularly preferred for these radicals and
R¹ and R⁸ have the abovementioned general, preferred, particularly preferred or very particularly preferred meanings.

Those mentioned above in the definition of the compounds according to the invention Hydrocarbon residues, like alkyl - also in connection with other atoms, like haloalkyl - as far as possible, in each case straight-chain or branched.

The general or preferred ranges listed above Residual definitions apply both to the end products of the formula (I) and  correspondingly for the respective starting materials or Intermediates.

The remainder definitions can be among each other, also between the specified ones Areas of preferred connections, can be combined as desired.

Examples of the compounds according to the invention are in the following table 1 listed:

Table 1

For example, 1- (4-chlorophenyl) -5-phenyl-2-imidazolidinone and 4-chlorophenyl isocyanate as starting materials, so the course of the reaction Represent process (a) according to the invention using the following formula:

For example, if 1,5-bisphenyl-3 - [(4-trifluoromethyl-cyclohexyl) - aminocarbonyl] -2-imidazolidinone and methyl iodide as starting materials, so can the course of the reaction of the method (b) according to the invention by the following Represent formula scheme:

For example, if 5- (2,4-dichlorophenyl) -1- (4-trifluoromethylphenyl) -2- imidazolidinone and 4-bromobenzenesulfonic acid chloride as starting materials, so lets the course of the reaction of process (c) according to the invention is characterized by represent the following formula:

The to carry out the processes (a) and (c) according to the invention as Formula (II) provides general 2-imidazolidinones required as starting materials Are defined. In the formula (II), R¹ and R² are preferably and particularly  prefers those meanings already in connection with the Description of the compounds of formula (I) as preferred or special were preferably given for R¹ and R².

The 2-imidazolidinones of the formula (II) are known (cf., for example, CA 118 (11), 101 978k; CA 114 (11), 101 824z; CA 109 (15), 129 006e; CA 107 (17), 154 281g or CA 91 (19), 157 66 lt) or in ahalogy to known processes available by e.g. B. urea derivatives of the formula

in which
R¹ and R² have the meaning given above,
optionally cyclized in the presence of a diluent and in the presence of a base under reflux (see, for example, Zh. Org. Khim (Engl. Transl.) 15 1077 (1979) and the preparation examples),
or
Ethylene diamines of the formula

in which
R¹ and R² have the meaning given above,
cyclized in the presence of urea (see, for example, BJ Chem. Soc., Perkin Trans. 2, 1981, 317 and the preparation examples).

The urea derivatives of the formula (VI) are known (cf., for example, Zh. Org. Khim (Engl. Transl.) 15, 1077 (1979) or 11, 2407 (1975) or 12, 522 (1976)) or available in analogy to the processes described there (see also the Manufacturing examples).

The ethylenediamines of the formula (VII) are known (cf., for example, J. Org. Chem. 56 5192 (1991) or Synthesis 1992, 664 or Helv. Chim. Acta 53, 47 (1970) or Synthesis 1993, 1013 or J. Chem. Soc., Perkin Trans. 2, 1981, 317) or in Analogous to the processes described there (see also the manufacturer examples).

The to carry out process (a) according to the invention as a reaction com Isocyanates required components are generally defined by the formula (IIIa). In this formula (IIIa) has R⁵ preferably or particularly preferably those Meanings already related to the description of the Compounds of formula (I) as preferred or particularly preferred for R⁵ were specified.

The isocyanates of the formula (IIIa) are known or can be prepared according to known ones Establish process.

Which also for performing the method (a) according to the invention as Reaction components required isothiocyanates are represented by the formula (IIIb) generally defined. In this formula (IIIb), R⁷ preferably or particularly prefers those meanings already in connection with the Description of the compounds of formula (I) as preferred or special were preferred for R⁷.

The isothiocyanates of the formula (IIIb) are known or can be prepared according to known ones Create methods.  

Those used to carry out process (b) according to the invention as starting materials required 2-imidazolidinone derivatives are represented by the formulas (Ia) and (Ib) generally defined. In these formulas (Ia) and (Ib), R¹, R², R⁵ and R⁷ preferably or particularly preferably those meanings which have already been given above in connection with the description of the compounds of formula (I) as were preferred or particularly preferred for R¹, R², R⁵ and R⁷.

The 2-imidazolidinone derivatives of the formulas (Ia) and (Ib) are according to the invention Substances that can be produced by process (a) according to the invention.

When performing process (b) according to the invention as a reak Compounds required components are general by the formula (IV) Are defined. In the formula (IV), R⁹, with the exception of hydrogen, is preferred or particularly preferably those meanings which have already been mentioned above in Connection with the description of the compounds of formula (I) as be were preferred or particularly preferably specified for the rest R⁴. Y is ahead preferably for hydroxy, methoxy, acetoxy, chlorine, bromine, iodine, trimethyl ammonium, phenylsulfonyl, p-tolylsulfonyl or 4-chlorophenylsulfonyl.

The compounds of formula (IV) are known or can be made according to known ones Create methods.

The reaction in carrying out process (c) according to the invention Components required sulfonyl derivatives are general by the formula (V) Are defined. In the formula (V), R⁸ preferably or particularly preferred those meanings that are already related to the description of the Compounds of formula (I) as preferred or particularly preferred for R⁸ were specified. Z preferably represents chlorine or bromine.

The 2-imidazolidinone derivatives of the formula according to the invention

in which
R¹, R², R⁶ and R⁷ have the meanings given above,
can also be prepared by using 2-imidazolidinone derivatives of the formula

in which
R¹, R², R⁴ and R⁵ have the meanings given above,
with a sulfurizing agent such as P₄S₁₀ or Lawesson's reagent [2,4-bis (4-methoxyphenyl) -1,3,2,4-dithiaphosphetane-2,4-dithione], optionally in the presence of a diluent such as xylene or Toluene, implemented at temperatures between 80 ° C and 200 ° C.

Suitable diluents for carrying out the process according to the invention Process (a) inert organic solvents in question. Preferably usable are aliphatic, alicyclic or aromatic, optionally halogenated Hydrocarbons such as gasoline, benzene, toluene, xylene, chlorine benzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloro  form, carbon tetrachloride; Ethers, such as diethyl ether, diisopropyl ether, dioxane, Tetrahydrofuran or ethylene glycol dimethyl or diethyl ether, nitriles, such as Acetonitrile, propionitrile or benzonitrile; Amides, such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexa methylphosphoric triamide or sulfoxides such as dimethyl sulfoxide.

The acid binders used in carrying out the invention Process (a) all customary inorganic and organic bases into consideration. Alkaline earth metal or alkali metal hydrides are preferably usable, hydroxides, amides, alcoholates, acetates, carbonates or bicarbonates, such as for example sodium hydride, sodium amide, sodium methylate, sodium ethylate, Potassium tert. -butylate, sodium hydroxide, potassium hydroxide, sodium acetate, Potassium acetate, calcium acetate, ammonium acetate, sodium carbonate, potassium carbonate, Potassium hydrogen carbonate, sodium hydrogen carbonate, also ammonium hydroxide or ammonium carbonate, and also tertiary amines, such as trimethylamine, triethylamine, Tributylamine, N, N-dimethylaniline, pyridine, N-methylpiperidine, N, N-dimethyl aminopyridine, diazabicyclooctane (DABCO), diazabicyclonones (DBN) or Diazabicycloundecene (DBU).

The reaction temperatures can be carried out when carrying out the process according to the invention Process (a) can be varied over a wide range. Generally works one at temperatures between -30 ° C and + 100 ° C, preferably at temperature between -20 ° C and + 60 ° C.

Process (a) according to the invention is usually carried out under normal pressure guided. However, it is also possible to increase or decrease pressure work.

To carry out process (a) according to the invention, 2- Imidazolidinone of formula (II) generally 1.0 to 3.0 mol, preferably 1.0 up to 1.5 mol of isocyanate of the formula (IIIa) or of isothiocyanate of the formula (IIIb) and optionally 0.01 to 1.0 mol, preferably 0.1 to 0.5 mol Acid binder. Carrying out the reaction, working up and isolating the Reaction products are carried out in the usual way (see also the production examples).  

As a diluent for carrying out process (b) according to the invention inert organic solvents are suitable. Are preferably usable aliphatic, alicyclic or aromatic, optionally halogenated carbons Hydrogen such as gasoline, benzene, toluene, xylene, chlorobenzene, Dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform or Carbon tetrachloride; Ethers such as diethyl ether, diisopropyl ether, dioxane, Tetrahydrofuran or ethylene glycol dimethyl or diethyl ether; Ketones like Acetone or butanone or methyl isobutyl ketone; Nitriles such as acetonitrile, Propionitrile or benzonitrile; Amides such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethyl phosphoric acid triamide, esters such as methyl acetate or ethyl acetate, Carboxylic acids such as formic acid or acetic acid, alcohols such as methanol, Ethanol, n- or i-propanol, ethylene glycol, ethylene glycol monomethyl ether or Ethylene glycol monoethyl ether, sulfoxides such as dimethyl sulfoxide. Besides that is too Water can be used as a diluent.

Process (b) according to the invention is preferably carried out in the presence of a suitable reaction auxiliary. As such, preferably come strong mineral acids, such as sulfuric acid or chlorine hydrochloric acid, or strongly acidic ion exchanger in question.

The reaction temperatures can be carried out when carrying out the process according to the invention Process (b) can be varied over a wide range. Generally works one at temperatures between 0 ° C and 150 ° C, preferably at temperatures between 40 ° C and 100 ° C.

To carry out process (b) according to the invention, 2-imidazolidinone derivative is employed per mole of the formula (Ia) or (Ib) in general 1.0 to 5.0 mol, preferably 1.0 to 2.5 mol of compound of formula (IV) and optionally 1.0 to 5.0 mol, preferably 1.0 to 2.5 mol, of reaction auxiliary.

Implementation, processing and isolation of the Reaction products are carried out according to known processes (see Synthesis 1973, 703; Tetrahedron 46, 1791 [1990]).  

As a diluent for carrying out process (c) according to the invention inert organic solvents are suitable. Are preferably usable aliphatic, alicyclic or aromatic, optionally halogenated carbons Hydrogen such as gasoline, benzene, toluene, xylene, chlorobenzene, Dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform or Carbon tetrachloride; Ethers such as diethyl ether, diisopropyl ether, dioxane, Tetrahydrofuran or ethylene glycol dimethyl or diethyl ether, ketones such as Acetone or butanone or methyl isobutyl ketone; Nitriles such as acetonitrile, Propionitrile or benzonitrile or esters such as methyl acetate or Ethyl acetate.

Process (c) according to the invention is preferably carried out in the presence of a suitable acid binder carried out. As such, all the usual ones come inorganic or organic bases in question. Are preferably usable Alkaline earth metal or alkali metal hydroxides, such as sodium hydroxide, calcium hydroxide, potassium hydroxide or ammonium hydroxide, alkali metal carbonates such as sodium carbonate, potassium carbonate, potassium hydrogen carbonate, sodium hydro gene carbonate, alkali metal or alkaline earth metal acetates, such as sodium acetate, Potassium carbonate, calcium acetate and tertiary amines such as trimethylamine, Triethylamine, tributylamine, N, N-dimethylaniline, pyridine, N-methylpiperidine, N, N-dimethylaminopyridine, Diazabicyclooctane (DABCO), diazabicyclonones (DBN) or diazabicycloundecene (DBU).

The reaction temperatures can be carried out when carrying out the process according to the invention Process (c) can be varied over a wide range. Generally works one at temperatures between 0 and 150 ° C, preferably at temperatures between 20 and 120 ° C.

Process (c) according to the invention is usually carried out under normal pressure carried out. However, it is also possible to increase or decrease it Pressure to work.

To carry out process (c) according to the invention, 2-imidazolidinone is used per mole of formula (II) generally 1.0 to 2.0 moles, preferably 1.0 to 1.3 mol of sulfonyl derivative of the formula (V) and optionally 1.0 to 2.0  Mol, preferably 1.0 to 1.3 mol of acid binder. The reaction management, The reaction products are worked up and isolated in accordance with known methods Method.

The active compounds according to the invention have a strong microbicidal action and can be useful to combat unwanted microorganisms be used. The active ingredients are for use as pesticides, particularly suitable as fungicides.

Fungicides in crop protection are used to combat plas modiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes, Deuteromycetes.

Some pathogens of fungal diseases that fall under the generic names listed above may be mentioned as examples, but not by way of limitation:
Pythium species, such as, for example, Pythium ultimum;
Phytophthora species, such as, for example, Phytophthora infestans;
Pseudoperonospora species, such as, for example, Pseudoperonospora humuli or Pseudoperonospora cubensis;
Plasmopara species, such as, for example, Plasmopara viticola;
Peronospora species, such as, for example, Peronospora pisi or Peronospora brassicae;
Erysiphe species, such as, for example, Erysiphe graminis;
Sphaerotheca species, such as, for example, Sphaerotheca fuliginea;
Podosphaera species, such as, for example, Podosphaera leucotricha;
Venturia species, such as, for example, Venturia inaequalis;
Pyrenophora species, such as, for example, Pyrenophorateres or Pyrenophora graminea (conidial form: Drechslera, synonym: Helminthosporium);
Cochliobolus species, such as, for example, Cochliobolus sativus (conidial form: Drechslera, synonym: Helminthosporium);
Uromyces species, such as, for example, Uromyces appendiculatus;
Puccinia species, such as, for example, Puccinia recondita;
Tilletia species, such as, for example, Tilletia caries;
Ustilago species, such as, for example, Ustilago nuda or Ustilago avenae;
Pellicularia species, such as, for example, Pellicularia sasakii;
Pyricularia species, such as, for example, Pyricularia oryzae;
Fusarium species, such as, for example, Fusarium culmorum;
Botrytis species, such as, for example, Botrytis cinerea;
Septoria species, such as, for example, Septoria nodorum;
Leptosphaeria species, such as, for example, Leptosphaeria nodorum;
Cercospora species, such as, for example, Cercospora canescens;
Alternaria species, such as, for example, Alternaria brassicae;
Pseudocercosporella species, such as, for example, Pseudocercosporella herpotrichoi des.

The good plant tolerance of the active ingredients in the control of the plant Concentrations necessary for diseases allow treatment from above parts of plants, planting and seeds and the soil.

The active compounds according to the invention can be used with particularly good success Combating diseases in fruit and vegetable growing, such as against Podosphaera and Uncinula species and for combating cereals diseases such as those used against Erysiphe and Septoria species will.

The active ingredients can depend on their respective physical and / or chemical properties converted into customary formulations such as solutions, emulsions, suspensions, powders, foams, pastes, Granules, aerosols, very fine encapsulations in polymeric substances and in Envelopes for seeds, as well as ULV cold and warm mist formulations.

These formulations are prepared in a known manner, e.g. B. by Mixing the active ingredients with extenders, i.e. liquid solvents, under Pressurized liquefied gases and / or solid carriers, if necessary using surface-active agents, ie emulsifiers and / or Dispersing agents and / or foaming agents. In case of use of water as an extender can e.g. B. also organic solvents as auxiliary solvents are used. Essentially come as liquid solvents lichen in question: aromatics, such as xylene, toluene, alkylnaphthalenes, chlorinated Aromatics or chlorinated aliphatic hydrocarbons, such as chlorobenzenes,  Chlorethylene, or methylene chloride, aliphatic hydrocarbons, such as cyclo hexane or paraffins, e.g. B. petroleum fractions, alcohols, such as butanol or glycol as well as their ethers and esters, ketones, such as acetone, methyl ethyl ketone, Methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as Dimethylformamide or dimethyl sulfoxide, and water; with liquefied gaseous extenders or carriers are meant such liquids which are gaseous at normal temperature and pressure, e.g. B. Aerosol propellants, such as halogenated hydrocarbons as well as butane, propane, nitrogen and carbon dioxide; as solid carriers come into question: B. natural rock flours, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powder, such as highly disperse Silica, alumina and silicates; as solid carriers for granules come into question: z. B. broken and fractionated natural rocks such as calcite, Marble, pumice, sepiolite, dolomite and synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust, Coconut shells, corn cobs and tobacco stalks; as emulsifying and / or Foaming agents are possible: B. non-ionic and anionic Emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. B. alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and Protein hydrolyzates; as dispersants come into question: z. B. Lignin sulfite liquor and methyl cellulose.

In the formulations, adhesives such as carboxymethyl cellulose, natural and synthetic, powdery, granular or latex-shaped polymers are used, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids such as cephalins and lecithins and synthetic Phospholipids. Other additives can be mineral and vegetable oils.

Dyes such as inorganic pigments, e.g. B. iron oxide, titanium oxide, Ferrocyan blue and organic dyes such as alizarin, azo and Metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, Boron, copper, cobalt, molybdenum and zinc can be used.

The formulations generally contain between 0.1 and 95 Weight percent active ingredient; preferably between 0.5 and 90%.  

The active compounds according to the invention can be used as such or in their Formulations also in a mixture with known fungicides, bactericides, Acaricides, nematicides or insecticides can be used, e.g. B. that To broaden the spectrum of activity or to prevent the development of resistance. In synergistic effects occur in some cases; d. H. the effectiveness of Mixing is higher than the effectiveness of the individual components.

For the mixtures, for example:

Fungicides:
2-aminobutane; 2-anilino-4-methyl-6-cyclopropyl-pyrimidine; 2 ′, 6′-dibromo-2-methyl-4′-trifluoromethoxy-4′-trifluoromethyl-1,3-thiazole-5-carboxanide; 2,6-di chloro-N- (4-trifluoromethylbenzyl) benzamide; (E) -2-methoxyimino-N-methyl-2- (2-phenoxyphenyl) acetamide; 8-hydroxyquinoline sulfate; Methyl- (E) -2- {2- [6- (2-cyanophenoxy) pyrimidin-4-yloxy] phenyl} -3-methoxyacrylate; Methyl (E) methoximino [alpha- (o-tolyloxy) -o-tolyl] acetate; 2-phenylphenol (OPP), aldimorph, ampropylfos, anilazine, azaconazole,
Benalaxyl, Benodanil, Benomyl, Binapacryl, Biphenyl, Bitertanol, Blasticidin-S, Bromuconazole, Bupirimate, Buthiobate,
Calcium polysulfide, captafol, captan, carbendazim, carboxin, quinomethionate (quinomethionate), chloroneb, chloropicrin, chlorothalonil, chlozolinate, cufraneb, cymoxanil, cyproconazole, cyprofuram,
Dichlorophen, diclobutrazole, dichlofluanid, diclomezin, dicloran, diethofencarb, difenoconazole, dimethirimol, dimethomorph, diniconazole, dinocap, diphenylamine, dipyrithione, ditalimfos, dithianon, dodin, drazoxolone,
Edifenphos, epoxyconazole, ethirimol, etridiazole,
Fenarimol, Fenbuconazole, Fenfuram, Fenitropan, Fenpiclonil, Fenpropidin, Fen propimorph, Fentinacetat, Fentinhydroxyd, Ferbam, Ferimzone, Fluazinam, Fludioxonil, Fluoromide, Fluquinconazole, Flusilazole, Flusulfamide, Flutolanyl, Futuberolosil, Futuberfosil , Furmecyclox,
Guazatine,
Hexachlorobenzene, hexaconazole, hymexazole,
Imazalil, Imibenconazol, Iminoctadin, Iprobefos (IBP), Iprodione, Isoprothiolan,
Kasugamycin, copper preparations such as: copper hydroxide, copper naphthenate, copper oxychloride, copper sulfate, copper oxide, oxine-copper and Bordeaux mixture,
Mancopper, Mancozeb, Maneb, Mepanipyrim, Mepronil, Metalaxyl, Metconazol, Methasulfocarb, Methfuroxam, Metiram, Metsulfovax, Myclobutanil,
Nickel dimethyldithiocarbamate, nitrothal isopropyl, Nuarimol,
Ofurace, oxadixyl, oxamocarb, oxycarboxin,
Pefurazoate, penconazole, pencycuron, phosdiphen, pimaricin, piperalin, polyoxin, probenazole, prochloraz, procymidon, propamocarb, propiconazole, propineb, pyrazophos, pyrifenox, pyrimethanil, pyroquilon,
Quintozen (PCNB),
Sulfur and sulfur preparations,
Tebuconazole, tecloftalam, tecnazene, tetraconazole, thiabendazole, Thicyofen, thiophanate-methyl, thiram, Tolclophos-methyl, tolylfluanid, triadimefon, triadimenol, triazoxide, Trichlamid, tricyclazole, tridemorph, triflumizole, triforine, triticonazole,
Validamycin A, vinclozolin,
Zineb, ziram

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

Insecticides / acaricides / nematicides:
Abamectin, Abamectin, Acephat, Acrinathrin, Alanycarb, Aldicarb, Alphamethrin, Amitraz, Avermectin, AZ 60541, Azadirachtin, Azinphos A, Azinphos M, Azocyc lotin,
Bacillus thuringiensis, 4-bromo-2- (4-chlorophenyl) -1- (ethoxymethyl) -5- (trifluoromethyl) -1H-pyrrole-3-carbonitrile, bendiocarb, benfuracarb, bensultap, betacyluthrin, bifenthrin, BPMC, Brofenprox, Bromophos A, Bufencarb, Buprofezin, Butocarb oxin, Butylpyridaben,
Cadusafos, Carbaryl, Carbofuran, Carbophenothion, Carbosulfan, Cartap, Chloethocarb, Chlorethoxyfos, Chloretoxyfos, Chlorfenvinphos, Chlorfluazuron, Chlormephos, N - [(6-Chloro-3-pyridinyl) -methyl] -N'-cyano-N-methyl ethanimidamide Chlorpyrifos, chlorpyrifos M, cis-resmethrin, clocythrin, clofentezin, cyanophos, cycloprothrin, cyfluthrin, cyhalothrin, cyhexatin, cypermethrin, cyromazine,
Deltamethrin, Demeton M, Demeton S, Demeton-S-methyl, Diafenthiuron, Diazinon, Dichlofenthion, Dichlorvos, Dicliphos, Dicrotophos, Diethion, Diflubenzuron, Dimethoat, Dimethylvinphos, Dioxathion, Disulfoton,
Edifenphos, Emam ectin, Esfenvalerat, Ethiofencarb, Ethion, Ethofenprox, Ethoprophos, Etrimphos,
Fenamiphos, Fenazaquin, Fenbutatinoxid, Fenitrothion, Fenobucarb, Fenothiocarb, Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyroximat, Fenthion, Fenvalerate, Fipronil, Fluazinam, Fluazuron, Flucycloxuron, Flucythrinat, Flufenxurophone, Flufenoxurion, Fufonxxuron, Flufenoxuron, Flufenoxuron, Fufionxuron, Fufionxuron, Fufionxuron, Fufionxuron, Fufionxuron, Fufionxuron, Fufionxuron, Fufionxuron, Fufionxuron, Fufone
HCH, heptenophos, hexaflumuron, hexythiazox,
Imidacloprid, Iprobefos, Isazophos, Isofenphos, Isoprocarb, Isoxathion, Ivemectin, Lamda-cyhalothrin, Lufenuron,
Malathion, Mecarbam, Mervinphos, Mesulfenphos, Metaldehyde, Methacrifos, Methamidophos, Methidathion, Methiocarb, Methomyl, Metolcarb, Milbemectin, Monocrotophos, Moxidectin,
Naled, NC 184, Nitenpyram
Omethoate, Oxamyl, Oxydemethon M, Oxydeprofos,
Parathion A, Parathion M, Permethrin, Phenthoat, Phorat, Phosalon, Phosmet, Phosphamdon, Phoxim, Pirimicarb, Pirimiphos M, Primiphos A, Profenofos, Profenophos, Promecarb, Propaphos, Propoxur, Prothiofos, Prothiophos, Prothoos, Pyothophos, Pym Pyradaphenthion, Pyresmethrin, Pyrethrum, Pyridaben, Pyrimidifen, Pyriproxifen,
Quinalphos,
Salithion, Sebufos, Silafluofen, Sulfotep, Sulprofos,
Tebufenozide, Tebufenpyrad, Tebupirimphos, Teflubenzuron, Tefluthrin, Temephos, Terbam, Terbufos, Tetrachlorvinphos, Thiafenox, Thiodicarb, Thiofanox, Thiomethon, Thionazin, Thuringiensin, Tralomenhrononium, Triomenethriazonium, Tri
Vamidothione, XMC, xylylcarb, zetamethrin.

A mixture with other known active ingredients, such as herbicides or with Fertilizers and growth regulators are possible.  

The active substances can be used as such, in the form of their formulations or in the form thereof prepared application forms, such as ready-to-use solutions, suspensions, Spray powder, pastes, soluble powders, dusts and granules are used will. The application is done in the usual way, e.g. B. by pouring, Spraying, spraying, scattering, dusting, foaming, brushing, etc. It is also possible to use the active ingredients according to the ultra-low-volume method apply or the drug preparation or the drug itself in the Inject soil. The seeds of the plants can also be treated.

When treating parts of plants, the active substance concentrations can be in the application forms can be varied over a wide range. They are in the generally between 1 and 0.0001% by weight, preferably between 0.5 and 0.001% by weight.

In the seed treatment, amounts of active ingredient are generally from 0.001 to 50 g per kilogram of seed, preferably 0.01 to 10 g.

When treating the soil, active ingredient concentrations are from 0.00001 to 0.1% by weight, preferably from 0.0001 to 0.02% by weight at the site of action required.

The manufacture and use of the active compounds according to the invention are described in following examples.

Manufacturing examples example 1 (Method a)

1.9 g (0.0062 mol) of 1- (6-chloropyridin-3-yl) -5- (4-chlorophenyl) -2-imidazolidinone are dissolved in 30 ml of dimethylformamide, at 0 ° C with 0.22 g (0.0074 mol) of 80% Sodium hydride suspension added and 20 minutes at this temperature touched. 1.28 g (0.0062 mol) of 4-trifluoromethylphenyl isocyanate are added dropwise and stirred for 15 hours at room temperature. The reaction mixture is then added to 500 ml of water and extracted with ethyl acetate. The organic phase is washed with water, dried over magnesium sulfate and constricted. The residue is stirred with diethyl ether, suction filtered and dried.

2.0 g (85% of theory) of 1- (6-chloropyridin-3-yl) -5- (4-chlorophenyl) -3- are obtained. [(4-trifluoromethylphenyl -) - aminocarbonyl] -2-imidazolidinone, melting point 159 ° C.  

Manufacture of raw materials

A mixture of 6.8 g (0.020 mol) of N- [2-chloro-2- (4-chlorophenyl) ethyl] -N ′ - [3- (6- chlorpyridin-3-yl)] - urea and 1.5 g (0.037 mol) of powdered sodium hydroxide in 25 ml of methanol is heated under reflux for 3 hours. The reaction mixture is evaporated to dryness. The residue is first with a little diethyl ether and then mixed with water.

After suction and drying, 4.2 g (69% of theory) 1- (6- Chlorpyridin-3-yl) -5- (4-chlorophenyl) -2-imidazolidinone with a logP = 2.20 (neutral).

8.5 g (0.039 mol) of 2-chloro-2- (4-chlorophenyl) ethyl isocyanate and 5.0 g (0.039 mol) 2-Chloro-5-aminopyridine in 80 ml of diethyl ether for 15 hours Room temperature stirred. The precipitate is filtered off and dried.

7.6 g (57% of theory) of N- [2-chloro-2- (4-chlorophenyl) ethyl] -N ′ - [3- (6-chloropyridin-3-yl)] - urea are obtained melting point 150 ° C.

23.0 g (0.078 mol) of N-chloro-N- [2-chloro-2- (4-chlorophenyl) ethyl] ethyl carbamate are in a mixture of 16.26 g (0.078 mol) of phosphorus pentachloride and 14.37 g (0.094 mol) of phosphorus oxychloride were stirred at 70 ° C. for 3 hours. After that leads one saturates at 0 ° C until saturation, volatile components are removed in a water jet vacuum and distilled the residue.

13.0 g (77% of theory) of 2-chloro-2- (4-chlorophenyl) ethyl isocyanate are obtained from the boiling point 120 ° C / 2 mbar.

To 30.47 g (0.22 mol) of 4-chlorostyrene, dissolved in 180 ml of toluene, is a at 50 ° C. Solution of 34.8 g (0.22 mol) of N, N-dichloroethane in 100 ml of toluene Dropped in inert gas atmosphere. The mixture is stirred at 50 ° C for 15 hours. The solvent is removed and the residue is distilled.

46.7 g (71% of theory) of N-chloro-N- [2-chloro-2- (4-chlorophenyl) ethyl] are obtained. ethyl carbamate with a boiling point of 112 ° C / l mbar.

Example 2 (Method a)

Reaction of 0.9 g (0.0033 mol) of 1- (4-chlorophenyl) -5-phenyl-2-imidazolidinone with 0.58 g (0.0036 mol) of 4-chlorophenyl isocyanate as in Example 1.  

1.0 g (71% of theory) of 1- (4-chlorophenyl) -3 - [(4-chlorophenyl) - aminocarbonyl] -5-phenyl-2-imidazolidinone, melting point 181 ° C.

Manufacture of raw materials

A mixture of 2.0 g (0.0073 mol) of 2- (4-chloroanilino) -2-phenylethylamine and 0.88 g (0.0147 mol) of urea is heated to 150 ° C. for 2.5 hours. After this After cooling, the residue is taken up in water with dichloromethane extracted and chromatographed on silica gel (ethyl acetate: cyclohexane = 1: 1).

1.0 g (50% of theory) of 1- (4-chlorophenyl) -5-phenyl-2-imidazdidinone are obtained with a logP = 2.41 (neutral).

5.09 g (0.021 mol) of 4-chloroanilino-benzyl cyanide in 84 ml of methanolic Animonia solution dissolved, mixed with Raney nickel (approx. 1.5 g) and at one Hydrogen pressure of 2.5 bar stirred for 24 hours at room temperature. After that the catalyst is separated off and the filtrate is concentrated.

4.9 g (85% of theory) of 2- (4-chloroanilino) -2-phenylethylamine are obtained a logP = 1.43 (acidic).

To a solution of 10.78 g (0.05 mol) of N-benzylidene-4-chloroaniline in 100 ml A solution of 3.9 g (0.06 mol) is added dropwise to methanol and 20 ml of glacial acetic acid at 0 ° C. Potassium cyanide in 50 ml of water within 25 minutes and stirred for a further 30 Minutes at 0 ° C. The mixture is poured onto ice, the precipitated product suction filtered, washed with water and dried.

8.5 g (68% of theory) of 4-chloroanilino-benzyl cyanide are obtained with a a logP = 3.20 (acidic).

15.3 g (0.12 mol) of 4-chloroaniline and 12.72 g (0.12 mol) of benzaldehyde in 250 ml Toluene is refluxed for 6 hours on a water separator. It is then concentrated.

27.4 g (100% of theory) of N-benzylidene-4-chloroaniline are obtained in the form of a Oil.

In a corresponding manner and in accordance with the general information on the manufacture the following 2-imidazolidinone derivatives of the formula (I) are obtained:  

Table 2

Examples of use Example A Uncinula test (vine) / protective

Solvent: 4.7 parts by weight of acetone
Emulsifier: 0.3 part by weight of alkyl aryl polyglycol ether

To prepare a suitable preparation of active compound, 1 Ge is mixed most of the active ingredient with the specified amounts of solvent and emulsifier and dilute the concentrate with water to the desired concentration.

To test for protective effectiveness, young plants are sprayed with the Active ingredient preparation to dripping wet. After the spray coating has dried on the plants are dusted with conidia of the Uncinula necator fungus.

The plants are then at 23 to 24 ° C and at a relative Air humidity of approx. 75% set up in the greenhouse.

Evaluation is carried out 14 days after the inoculation.

In this test, for example, shows the connection according to Production Example 5 with an active ingredient concentration of 25 ppm an efficiency of 100.  

Example B Podosphaera test (apple) / protective

Solvent: 4.7 parts by weight of acetone
Emulsifier: 0.3 part by weight of alkyl aryl polyglycol ether

To prepare a suitable preparation of active compound, 1 Ge is mixed most of the active ingredient with the specified amounts of solvent and emulsifier and dilute the concentrate with water to the desired concentration.

To test for protective effectiveness, young plants are sprayed with the Active ingredient preparation to dripping wet. After the spray coating has dried on the plants are pollinated with conidia of the apple scab pathogen Podosphaera leucotricha inoculated.

The plants are then grown in a greenhouse at 23 ° C and a relative Humidity of approx. 70% set up.

Evaluation is carried out 10 days after the inoculation.

In this test, for example, the connections according to the Production Examples 3, 4 and 5 at an active ingredient concentration of 25 ppm an efficiency of 100.

Claims (7)

1. 2-imidazolidinone derivatives of the formula in which
R1 represents alkyl, haloalkyl, alkoxyalkyl, alkenyl, optionally substituted cycloalkyl, optionally substituted aryl, optionally substituted phenylalkyl, optionally substituted phenylalkenyl, optionally substituted phenoxyalkyl, optionally substituted phenylthioalkyl or for optionally substituted heterylcyllyl,
R² is alkyl, haloalkyl, alkoxyalkyl, alkenyl, optionally substituted cycloalkyl, optionally substituted aryl, optionally substituted phenylalkyl, optionally substituted phenyl alkenyl, optionally substituted phenoxyalkyl, optionally substituted phenylthioalkyl or for optionally substituted heterocyclyl and
R³ for the groupings stands, where
R⁴ for hydrogen; Alkyl, haloalkyl, alkoxyalkyl, alkyl carbonyl, alkylsulfonyl, haloalkylcarbonyl, alkoxyalkyl carbonyl, optionally substituted cycloalkyl, optionally substituted arylcarbonyl or represents optionally substituted arylsulfonyl,
R⁵ for hydrogen; Alkyl, haloalkyl, alkoxyalkyl, optionally substituted cycloalkyl, optionally substituted aryl or represents optionally substituted heterocyclic,
R⁶ for hydrogen; Alkyl, haloalkyl, alkoxyalkyl, alkyl carbonyl, alkylsulfonyl, haloalkylcarbonyl, alkoxyalkyl carbonyl, optionally substituted cycloalkyl, optionally substituted arylcarbonyl or represents optionally substituted arylsulfonyl,
R⁷ for hydrogen; Alkyl, haloalkyl, alkoxyalkyl, optionally substituted cycloalkyl, optionally substituted aryl or optionally substituted heterocyclic and
R⁸ for hydrogen; Alkyl, haloalkyl, alkoxyalkyl, optionally substituted cycloalkyl, optionally substituted aryl or optionally substituted heterocyclic. 2. imidazolidinone derivatives of the formula (I) according to claim 1, in which
R¹ is C₁-C₈-alkyl, C₁-C₈-haloalkyl having 1 to 9 halogen atoms, represents C₁-C₄-alkoxy-C₁-C₈-alkyl, C₂-C₈-alkenyl, or
represents C₃-C₁₀-cycloalkyl, where these radicals can be substituted up to six times, identically or differently by halogen, C₁-C₄-alkyl and / or C₁-C₄-haloalkyl having 1 to 9 identical or different halogen atoms, or
represents phenyl, naphthyl, phenyl-C₁-C₄-alkyl, phenyl-C₂-C₄-alkenyl, phenoxy-C₁-C₄-alkyl or phenylthio-C₁-C₄-alkyl, each of these radicals being substituted one to five times, in the same or different manner can be halogen, cyano, nitro, amino, hydroxyl, formyl, carboxy carbamoyl, thiocarbamoyl, each straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl each having 1 to 6 carbon atoms, each straight-chain or branched alkenyl or alkenyloxy each having 2 up to 6 carbon atoms, each straight-chain or branched haloalkyl, haloalkoxy, haloalkylthio, haloalkylsulfinyl or haloalkylsulfonyl each having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, each straight-chain or branched haloalkenyl or haloalkenyloxy each having 2 to 6 carbon atoms and 1 to 13 same or different halogen atoms, each straight-chain or branched Alkylamino, dialkylamino, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylsulfonyloxy, hydroximinoalkyl or alkoximinoalkyl, each with 1 to 6 carbon atoms in the individual alkyl parts, each optionally one or more times, identically or differently by halogen and / or straight-chain or branched alkyl having 1 to 4 Carbon atoms and / or straight-chain or branched haloalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms substituted, in each case doubly linked alkylene or dioxyalkylene, each having 1 to 6 carbon atoms, cycloalkyl having 3 to 6 carbon atoms, heterocyclic or heterocyclyl-methyl each with 3 to 7 ring members, each of which is 1 to 3 identical or different heteroatoms, and in each case optionally in the phenyl part one to three times, identical or different, by halogen, cyano and / or straight-chain or branched alkyl having 1 to 4 carbon atoms and / or straight ketti saturated or branched haloalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms and / or straight-chain or branched alkoxy having 1 to 4 carbon atoms and / or straight-chain or branched halogenoalkoxy having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms Phenyl, phenoxy, benzyl, benzyloxy, phenylethyl or phenylethyloxy, or
R¹ is optionally benzanellated heterocyclyl with 5 or 6 ring members, at least one of which is oxygen, sulfur or nitrogen and optionally one or two further ring members are nitrogen, in each of which two geminal hydrogen atoms can be replaced by oxygen and where each the heterocyclic radicals can be monosubstituted to trisubstituted, identical or different, by halogen, cyano, nitro, amino, hydroxyl, formyl, carboxy carbamoyl, thiocarbamoyl, in each case straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl each having 1 to 6 carbon atoms , each straight-chain or branched alkenyl or alkenyloxy each having 2 to 6 carbon atoms, each straight-chain or branched haloalkyl, haloalkoxy, haloalkylthio, haloalkyl sulfinyl or haloalkylsulfonyl each having 1 to 6 carbon atoms and 1 to 13 identical or different halogena toms, each straight-chain or branched haloalkenyl or haloalkenyloxy, each having 2 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, each straight-chain or branched alkylamino, dialkylamino, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylsulfonyloxy, hydroximino alkyl or alkoximinoalkyl each with 1 to 6 Carbon atoms in the individual alkyl parts, each optionally one or more times, identically or differently by halogen and / or straight-chain or branched alkyl having 1 to 4 carbon atoms and / or straight-chain or branched haloalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms Substituted, each doubly linked alkylene or dioxyalkylene, each with 1 to 6 carbon atoms, cycloalkyl with 3 to 6 carbon atoms, heterocyclyl or heterocyclyl-methyl, each with 3 to 7 ring members, each of which has 1 to 3 identical or different hetero are atoms, as well as in the phenyl moiety in each case single to triple, identical or different by halogen, cyano and / or straight-chain or branched alkyl having 1 to 4 carbon atoms and / or straight-chain or branched haloalkyl having 1 to 4 carbon atoms and 1 to 9 same or different halogen atoms and / or straight-chain or branched alkoxy with 1 to 4 carbon atoms and / or straight-chain or branched haloalkoxy with 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms substituted phenyl, phenoxy, benzyl, benzyloxy, phenylethyl or phenylethyloxy,
R² is C₁-C₈-alkyl, C₁-C₈-haloalkyl having 1 to 9 halogen atoms, represents C₁-C₄-alkoxy-C₁-C₈-alkyl or C₂-C₈-alkenyl, or is C₃-C₁₀-cycloalkyl, these being Residues can be up to six times, identical or differently substituted by halogen, C₁-C₄-alkyl and / or C₁-C₄-haloalkyl having 1 to 9 identical or different halogen atoms, or
represents phenyl, naphthyl, phenyl-C₁-C₄-alkyl, phenyl-C₂-C₄-alkenyl, phenoxy-C₁-C₄-alkyl or phenylthio-C₁-C₄-alkyl, each of these radicals being substituted one to five times, in the same or different manner can be halogen, cyano, nitro, amino, hydroxyl, formyl, carboxy carbamoyl, thiocarbamoyl, each straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl each having 1 to 6 carbon atoms, each straight-chain or branched alkenyl or alkenyloxy each 2 to 6 carbon atoms, each straight-chain or branched haloalkyl, haloalkoxy, haloalkylthio, haloalkylsulfinyl or haloalkylsulfonyl each having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, each straight-chain or branched haloalkenyl or haloalkenyloxy each having 2 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, each straight-chain or branched Alkylamino, dialkylamino, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylsulfonyloxy, hydroximinoalkyl or alkoximinoalkyl, each with 1 to 6 carbon atoms in the individual alkyl parts, each optionally one or more times, identically or differently by halogen and / or straight-chain or branched alkyl having 1 to 4 Carbon atoms and / or straight-chain or branched haloalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms substituted, in each case doubly linked alkylene or dioxyalkylene, each having 1 to 6 carbon atoms, cycloalkyl having 3 to 6 carbon atoms, heterocyclic or heterocyclyl-methyl each with 3 to 7 ring members, each of which is 1 to 3 identical or different heteroatoms, and in each case optionally in the phenyl part one to three times, identical or different, by halogen, cyano and / or straight-chain or branched alkyl having 1 to 4 carbon atoms and / or straight chain iges or branched haloalkyl with 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms and / or straight-chain or branched alkoxy with 1 to 4 carbon atoms and / or straight-chain or branched haloalkoxy with 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms Phenyl, phenoxy, benzyl, benzyloxy, phenylethyl or phenylethyloxy, or
R² stands for optionally benzanellated heterocyclyl with 5 or 6 rings, at least one of which stands for oxygen, sulfur or nitrogen and optionally one or two further ring members for nitrogen, it being possible for two geminal hydrogen atoms to be replaced by oxygen in each of these residues and each of the heterocyclic radicals can be monosubstituted to trisubstituted, identical or different, by halogen, cyano, nitro, amino, hydroxyl, formyl, carboxy carbamoyl, thiocarbamoyl, in each case straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl each having 1 to 6 Carbon atoms, each straight-chain or branched alkenyl or alkenyloxy each having 2 to 6 carbon atoms, each straight-chain or branched haloalkyl, halo genalkoxy, haloalkylthio, haloalkylsulfinyl or haloalkylsulfonyl each having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, each straight-chain or branched haloalkenyl or haloalkenyloxy each having 2 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, each straight-chain or branched alkylamino, dialkylamino, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylsulfonyloxy, hydroximinoalkyl or alkox iminoalkyl each with 1 to 6 Carbon atoms in the individual alkyl parts, in each case optionally one or more times, identically or differently, by halogen and / or straight-chain or branched alkyl having 1 to 4 carbon atoms and / or straight-chain or branched haloalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms substituted, each having a double bond alkylene or dioxy alkylene each having 1 to 6 carbon atoms, cycloalkyl having 3 to 6 carbon atoms, heterocyclyl or heterocyclyl-methyl each having 3 to 7 ring members, each of which has 1 to 3 identical or different hetero eroatoms are, as well as in the phenyl part, in each case, single to triple, identical or different by halogen, cyano and / or straight-chain or branched alkyl having 1 to 4 carbon atoms and / or straight-chain or branched haloalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different Halogen atoms and / or straight-chain or branched alkoxy with 1 to 4 carbon atoms and / or straight-chain or branched haloalkoxy with 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms substituted phenyl, phenoxy, benzyl, benzyloxy, phenylethyl or phenylethyloxy,
R³ for the groups stands in what
R⁴ for hydrogen; C₁-C₆ alkyl; C₁-C₆ haloalkyl having 1 to 9 identical or different halogen atoms; C₁-C₄ alkoxy-C₁-C₄ alkyl; C₁-C₆ alkyl carbonyl; C₁-C₆ alkyl sulfonyl; C₁-C₆ haloalkylcarbonyl having 1 to 9 identical or different halogen atoms; C₁-C₄-alkoxy-C₁-C₄-alkyl carbonyl, or
represents C₃-C₇-cycloalkyl, these radicals can be substituted up to six times, identically or differently by halogen, C₁-C₄-alkyl and / or C₁-C₄-haloalkyl having 1 to 9 identical or different halogen atoms, or
represents phenylcarbonyl or phenylsulfonyl, where each of these radicals can be mono- to fivefold, identical or differently substituted by halogen, hydroxy, cyano, amino, nitro, C₁-C₁-alkyl, C₁-C₄-alkoxy, C₁-C₄-alkylthio, C₁ -C₄-haloalkyl with 1 to 9 identical or different halogen atoms, C₁-C₄-alkylcarbonyl and / or phenyl, which itself can be monosubstituted to trisubstituted, identically or differently, by halogen and / or C₁-C₄-alkyl,
R⁵ for hydrogen; C₁-C₆ alkyl; C₁-C₆ haloalkyl having 1 to 9 identical or different halogen atoms; C₁-C₄-alkoxy-C₁-C₄-alkyl, or
represents C₃-C₇-cydoalkyl, these radicals can be substituted up to six times, in the same or different manner, by halogen, C₁-C₄-alkyl and / or C₁-C₄-haloalkyl having 1 to 9 identical or different halogen atoms, or
represents phenyl or naphthyl, where each of these radicals can be mono- to pentasubstituted, identical or differently substituted by halogen, cyano, nitro, amino, hydroxy, formyl, carboxy carbamoyl, thiocarbamoyl, in each case straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulfinyl or Alkylsulfonyl each having 1 to 6 carbon atoms, each straight-chain or branched alkenyl or alkenyloxy each having 2 to 6 carbon atoms, each straight-chain or branched haloalkyl, haloalkoxy, haloalkylthio, haloalkylsulfinyl or haloalkylsulfonyl each having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms , each straight-chain or branched haloalkenyl or haloalkenyloxy each having 2 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, each straight-chain or branched alkylamino, dialkyl amino, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylsulfonyloxy, hydroximi noalkyl or alkoximinoalkyl, each having 1 to 6 carbon atoms in the individual alkyl parts, in each case optionally one or more times, identically or differently, by halogen and / or straight-chain or branched alkyl having 1 to 4 carbon atoms and / or straight-chain or branched halogen alkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, each substituted by two bonds, alkylene or dioxyalkylene, each with 1 to 6 carbon atoms, cycloalkyl with 3 to 6 carbon atoms, heterocyclyl or heterocyclyl-methyl, each with 3 to 7 ring members, of which 1 to 3 are the same or different heteroatoms, and in each case optionally in the phenyl part one to three times, the same or different by halogen, cyano and / or straight-chain or branched alkyl having 1 to 4 carbon atoms and / or straight-chain or branched haloalkyl having 1 to 4 carbon atoms and 1 to 9 same or different Halogen atoms and / or straight-chain or branched alkoxy with 1 to 4 carbon atoms and / or straight-chain or branched haloalkoxy with 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms substituted phenyl, phenoxy, benzyl, benzyloxy, phenylethyl or phenylethyloxy, or
R⁵ represents optionally benzanellated heterocyclyl with 5 or 6 ring members, of which at least one is oxygen, sulfur or nitrogen and optionally one or two further ring members are nitrogen, in which two geminal hydrogen atoms can be replaced by oxygen and wherein each of the heterocyclic radicals can be monosubstituted to trisubstituted, identical or different, by halogen, cyano, nitro, amino, hydroxyl, formyl, carboxy carbamoyl, thiocarbamoyl, in each case straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl each having 1 to 6 Carbon atoms, each straight-chain or branched alkenyl or alkenyloxy each having 2 to 6 carbon atoms, each straight-chain or branched haloalkyl, haloalkoxy, haloalkylthio, halogen alkylsulfinyl or haloalkylsulfonyl each having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, each straight-chain or branched haloalkenyl or haloalkenyloxy each having 2 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, each straight-chain or branched alkylamino, dialkylamino, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylsulfonyloxy, hydroximinoalkyl or alkoximinoalkyl each having 1 to 6 carbon atoms the individual alkyl parts, each optionally mono- or polysubstituted, identically or differently, by halogen and / or straight-chain or branched alkyl having 1 to 4 carbon atoms and / or straight-chain or branched haloalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, in each case doubly linked alkylene or dioxyalkylene each having 1 to 6 carbon atoms, cycloalkyl having 3 to 6 carbon atoms, heterocyclyl or heterocyclyl-methyl each having 3 to 7 ring members, each of which has 1 to 3 identical or different heteroato me, and in each case optionally in the phenyl moiety single to triple, identical or different by halogen, cyano and / or straight-chain or branched alkyl having 1 to 4 carbon atoms and / or straight-chain or branched haloalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different different halogen atoms and / or straight-chain or branched alkoxy with 1 to 4 carbon atoms and / or straight-chain or branched haloalkoxy with 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms substituted phenyl, phenoxy, benzyl, benzyloxy, phenylethyl or phenylethyloxy,
R⁶ for hydrogen; C₁-C₆ alkyl; C₁-C₆ haloalkyl having 1 to 9 identical or different halogen atoms; C₁-C₄ alkoxy-C₁-C₄ alkyl; C₁-C₆ alkyl carbonyl; C₁-C₆ alkyl sulfonyl; C₁-C₆ haloalkylcarbonyl having 1 to 9 identical or different halogen atoms; C₁-C₄-alkoxy-C₁-C₄-alkyl-carbonyl, or
represents C₃-C₇-cycloalkyl, these radicals can be substituted up to six times, identically or differently by halogen, C₁-C₄-alkyl and / or C₁-C₄-haloalkyl having 1 to 9 identical or different halogen atoms, or
represents phenylcarbonyl or phenylsulfonyl, where each of these radicals can be mono- to fivefold, identical or differently substituted by halogen, hydroxy, cyano, amino, nitro, C₁-C₁-alkyl, C₁-C₄-alkoxy, C₁-C₄-alkylthio, C₁ -C₄-haloalkyl having 1 to 9 identical or different halogen atoms, C₁-C₄-alkylcarbonyl and / or phenyl, which can itself be substituted up to three times, identically or differently, by halogen and / or C₁-C₄-alkyl,
R⁷ for hydrogen; C₁-C₆ alkyl; C₁-C₆ haloalkyl having 1 to 9 identical or different halogen atoms; C₁-C₄-alkoxy-C₁-C₄-alkyl, or
represents C₃-C₇-cycloalkyl, where these radicals can be substituted up to six times, identically or differently by halogen, C₁-C₄-alkyl and / or C₁-C₄-haloalkyl having 1 to 9 identical or different halogen atoms, or
represents phenyl or naphthyl, where each of these radicals can be mono- to pentasubstituted, identical or differently substituted by halogen, cyano, nitro, amino, hydroxy, formyl, carboxy carbamoyl, thiocarbamoyl, in each case straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulfinyl or Alkylsulfonyl each having 1 to 6 carbon atoms, each straight-chain or branched alkenyl or alkenyloxy each having 2 to 6 carbon atoms, each straight-chain or branched haloalkyl, haloalkoxy, haloalkylthio, haloalkylsulfinyl or haloalkylsulfonyl each having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms , each straight-chain or branched haloalkenyl or haloalkenyloxy each having 2 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, each straight-chain or branched alkylamino, dialkylamino, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylsulfonyloxy, hydroximine oalkyl or alkoximinoalkyl each having 1 to 6 carbon atoms in the individual alkyl parts, each optionally one or more times, identically or differently, by halogen and / or straight-chain or branched alkyl having 1 to 4 carbon atoms and / or straight-chain or branched haloalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, each having a double bond, alkylene or dioxyalkylene each having 1 to 6 carbon atoms, cycloalkyl having 3 to 6 carbon atoms, heterocyclyl or heterocyclyl-methyl each having 3 to 7 ring members, of which 1 to 3 are the same or different Heteroatoms are, as well as optionally in the phenyl part, single to triple, identical or different by halogen, cyano and / or straight-chain or branched alkyl having 1 to 4 carbon atoms and / or straight-chain or branched haloalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different different Ha logen atoms and / or straight-chain or branched alkoxy having 1 to 4 carbon atoms and / or straight-chain or branched haloalkoxy having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms substituted phenyl, phenoxy, benzyl, benzyloxy, phenylethyl or phenylethyloxy, or
R⁷ represents optionally benzanellated heterocyclyl with 5 or 6 ring members, at least one of which is oxygen; Sulfur or nitrogen and optionally one or two further ring members are nitrogen, in which two geminal hydrogen atoms in each of these radicals can be replaced by oxygen and in which each of the heterocyclic radicals can be monosubstituted to triple, identical or differently substituted by halogen, cyano, nitro , Amino, hydroxy, formyl, carboxy carbamoyl, thiocarbamoyl, each straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl each having 1 to 6 carbon atoms, each straight-chain or branched alkenyl or alkenyloxy each having 2 to 6 carbon atoms, each straight-chain or branched Haloalkyl, haloalkoxy, haloalkylthio, haloalkylsulfinyl or haloalkylsulfonyl each having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, each straight-chain or branched haloalkenyl or haloalkenyloxy each having 2 to 6 carbon atoms and 1 bi s 13 identical or different halogen atoms, each straight-chain or branched alkylamino, dialkylamino, alkylcarbonyl, alkyl carbonyloxy, alkoxycarbonyl, alkylsulfonyloxy, hydroximinoalkyl or alkoximinoalkyl, each with 1 to 6 carbon atoms in the individual alkyl parts, in each case if appropriate one or more times, the same or differently substituted by halogen and / or straight-chain or branched alkyl having 1 to 4 carbon atoms and / or straight-chain or ver branched haloalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, each having a doubly linked alkylene or dioxy alkylene, each with 1 up to 6 carbon atoms, cycloalkyl with 3 to 6 carbon atoms, heterocyclyl or heterocyclyl-methyl each with 3 to 7 ring members, each of which is 1 to 3 identical or different heteroatoms, and in each case optionally in the phenyl part one to three times, identical or different by halogen, Cyano and / or straight-chain or branched alkyl having 1 to 4 carbon atoms and / or straight-chain or branched haloalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms and / or straight-chain or branched alkoxy having 1 to 4 carbon atoms and / or straight-chain or branched halogen alkoxy having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms substituted phenyl, phenoxy, benzyl, benzyloxy, phenylethyl or phenylethyl oxy, and
R⁸ for hydrogen; C₁-C₆ alkyl; C₁-C₆ haloalkyl having 1 to 9 identical or different halogen atoms; C₁-C₄-alkoxy-C₁-C₄-alkyl, or
represents C₃-C₇-cydoalkyl, these radicals can be substituted up to six times, in the same or different manner, by halogen, C₁-C₄-alkyl and / or C₁-C₄-haloalkyl having 1 to 9 identical or different halogen atoms, or
represents phenyl or naphthyl, where each of these radicals can be mono- to pentasubstituted, identical or differently substituted by halogen, cyano, nitro, amino, hydroxy, formyl, carboxy carbamoyl, thiocarbamoyl, in each case straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulfinyl or Alkylsulfonyl each having 1 to 6 carbon atoms, each straight-chain or branched alkenyl or alkenyloxy each having 2 to 6 carbon atoms, each straight-chain or branched haloalkyl, haloalkoxy, haloalkylthio, haloalkylsulfinyl or haloalkylsulfonyl each having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms , each straight-chain or branched haloalkenyl or haloalkenyloxy each having 2 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, each straight-chain or branched alkylamino, dialkylamino, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylsulfonyloxy, hydroximine oalkyl or alkoximinoalkyl each having 1 to 6 carbon atoms in the individual alkyl parts, each optionally one or more times, identically or differently, by halogen and / or straight-chain or branched alkyl having 1 to 4 carbon atoms and / or straight-chain or branched haloalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms substituted, each having a double bond, alkylene or dioxyalkylene each having 1 to 6 carbon atoms, cycloalkyl having 3 to 6 carbon atoms, heterocyclyl or heterocyclyl-methyl each having 3 to 7 ring members, of which 1 to 3 are the same or different Heteroatoms are, as well as optionally in the phenyl part, single to triple, identical or different by halogen, cyano and / or straight-chain or branched alkyl having 1 to 4 carbon atoms and / or straight-chain or branched haloalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different different Ha logen atoms and / or straight-chain or branched alkoxy having 1 to 4 carbon atoms and / or straight-chain or branched haloalkoxy having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms substituted phenyl, phenoxy, benzyl, benzyloxy, phenylethyl or phenylethyloxy, or
R⁸ represents optionally benzanellated heterocyclyl with 5 or 6 ring members, of which at least one is oxygen, sulfur or nitrogen and optionally one or two further ring members are nitrogen, in which two geminal hydrogen atoms can be replaced by oxygen and wherein each of the heterocyclic radicals can be monosubstituted to trisubstituted, identical or different, by halogen, cyano, nitro, amino, hydroxyl, formyl, carboxy carbamoyl, thiocarbamoyl, in each case straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl each having 1 to 6 Carbon atoms, each straight-chain or branched alkenyl or alkenyloxy each having 2 to 6 carbon atoms, each straight-chain or branched haloalkyl, haloalkoxy, haloalkylthio, halogen alkylsulfinyl or haloalkylsulfonyl each having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, each straight-chain or branched haloalkenyl or haloalkenyloxy each having 2 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, each straight-chain or branched alkylamino, dialkylamino, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylsulfonyloxy, hydroximinoalkyl or alkoximinoalkyl each having 1 to 6 carbon atoms the individual alkyl parts, each optionally mono- or polysubstituted, identically or differently, by halogen and / or straight-chain or branched alkyl having 1 to 4 carbon atoms and / or straight-chain or branched haloalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, in each case doubly linked alkylene or dioxyalkylene each having 1 to 6 carbon atoms, cycloalkyl having 3 to 6 carbon atoms, heterocyclyl or heterocyclyl-methyl each having 3 to 7 ring members, each of which has 1 to 3 identical or different heteroato me, and in each case in the phenyl part in each case one to three times, identically or differently, by halogen, cyano and / or straight-chain or branched alkyl having 1 to 4 carbon atoms and / or straight-chain or branched haloalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different different halogen atoms and / or straight-chain or branched alkoxy having 1 to 4 carbon atoms and / or straight-chain or branched haloalkoxy having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms substituted phenyl, phenoxy, benzyl, benzyloxy, phenylethyl or phenylethyloxy. 3. Process for the preparation of 2-imidazolidinone derivatives of the formula in which
R1 represents alkyl, haloalkyl, alkoxyalkyl, alkenyl, optionally substituted cycloalkyl, optionally substituted aryl, optionally substituted phenylalkyl, optionally substituted phenylalkenyl, optionally substituted phenoxyalkyl, optionally substituted phenylthioalkyl or for optionally substituted heterocyclyl,
R² represents alkyl, haloalkyl, alkoxyalkyl, alkenyl, optionally substituted cycloalkyl, optionally substituted aryl, optionally substituted phenylalkyl, optionally substituted phenylalkenyl, optionally substituted phenoxyalkyl, optionally substituted phenylthioalkyl or for optionally substituted heterocyclyl and
R³ for groupings stands, where
R⁴ represents hydrogen, alkyl, haloalkyl, alkoxyalkyl, alkylcarbonyl, alkylsulfonyl, haloalkylcarbonyl, alkoxyalkylcarbonyl, optionally substituted cycloalkyl, optionally substituted arylcarbonyl or for optionally substituted arylsulfonyl,
R⁵ represents hydrogen, alkyl, haloalkyl, alkoxyalkyl, optionally substituted cycloalkyl, optionally substituted aryl or for optionally substituted heterocyclyl,
R⁶ for hydrogen; Alkyl, haloalkyl, alkoxyalkyl, alkyl carbonyl, alkylsulfonyl, haloalkylcarbonyl, alkoxyalkyl carbonyl, optionally substituted cycloalkyl, optionally substituted arylcarbonyl or represents optionally substituted arylsulfonyl,
R⁷ represents hydrogen, alkyl, haloalkyl, alkoxyalkyl, optionally substituted cycloalkyl, optionally substituted aryl or for optionally substituted heterocyclyl and
R⁸ represents hydrogen, alkyl, haloalkyl, alkoxyalkyl, optionally substituted cycloalkyl, optionally substituted aryl or for optionally substituted heterocyclyl,
characterized in that one

• a) 2-imidazolidinones of the formula in which
  R¹ and R² have the meanings given above,
  either with isocyanates of the formula R⁵-NCO (IIIa) in which
  R⁵ has the meanings given above,
  or with isothiocyanates of the formula R⁷-NCS (IIIb) in which
  R⁷ has the meanings given above,
  in each case if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder, or
• b) 2-imidazolidinone derivatives of the formula or in which
  R⁵ and R⁷ have the meanings given above,
  with compounds of the formula R⁹-Y (IV) in which
  R⁹ represents alkyl, haloalkyl, alkoxyalkyl, alkylcarbonyl, alkyl sulfonyl, haloalkylcarbonyl, alkoxyalkylcarbonyl, optionally substituted cycloalkyl, optionally substituted arylcarbonyl or for optionally substituted arylsulfonyl and
  Y represents a leaving group,
  if appropriate in the presence of a diluent and if appropriate in the presence of a reaction auxiliary, or
• c) 2-Imidazolidione of the formula in which
  R¹ and R² have the meanings given above,
  with sulfonyl derivatives of the formula R⁸-SO₂-Z (V) in which
  R⁸ has the meanings given above and
  Z represents a leaving group,
  if appropriate in the presence of a diluent and, if appropriate, in the presence of an acid binder.

4. Fungicidal agents, characterized by a content of at least one 2-imidazolidinone derivative of the formula (I) according to Claim 1. 5. Use of 2-imidazolidinone derivatives of the formula (I) according to Claim 1 for combating fungi. 6. A method of combating fungi, characterized in that 2-imidazolidinone derivatives of the formula (I) according to Claim 1 on the fungi and / or their habitat.   7. A process for the preparation of fungicidal compositions, characterized in that that with 2-imidazolidinone derivatives of formula (I) according to claim 1 Extenders and / or surfactants mixed.