DE4213026A1 - New 4-substd. 3-aryl-3-pyrroline-2-one derivs. - used as total or selective herbicides and fungicides - Google Patents

Abstract

4-(Hydroxy, hydrocarbyloxy or amino)-3-aryl-delta-3-pyrrolin-2-one derivs. of formula (I) are new. In (I), X, Y = H, halogen, alkyl, alkoxy, haloalkyl, haloalkoxy, aryl, aryloxy, benzyloxy or arylthio (the last 4 gps. being opt. substd.); Z = halogen, alkyl or alkoxy; R1, R2 = opt. halogen-substd. alkyl or alkoxyalkyl; R3 = alkyl, alkenyl, alkynyl, alkoxyalkyl, polyalkoxyalkyl or alkylthioalkyl (all opt. substd. by halogen); cycloalkyl (opt. interrupted by heteroatoms); arylalkyl, arylalkenyl or arylalkynyl (all opt. substd. by halogen, alkyl, haloalkyl, haloalkoxy, alkoxy and/or nitro); or aryl (opt. substd. by halogen, alkyl, alkoxy, phenoxy or phenylthio, the last two themselves opt. substd. by halogen, alkyl, alkoxy, haloalkyl and/or haloalkoxy), R4 = H; opt. halogen-substd. alkyl or cycloalkyl; or aryl or aralkyl (both opt. substd. by halogen, alkyl, alkoxy, haloalkyl or NO2); R5 = OH; alkoxy, alkenyloxy, alkynyloxy or polyalkoxy (all opt. substd. by halogen); cycloalkoxy (opt. substd. by halogen and/or alkyl); opt. substd. arylalkyloxy; or -NR6R7; R6, R7 = H, alkyl, alkenyl, alkoxyalkyl; alkylthioalkyl, polyalkoxyalkyl, cycloalkyl (opt. interrupted by heteroatoms), phenyl, phenylalkyl, phenoxyalkyl, heteroaryl or heteroarylalkyl (the last 5 gps. being opt. substd.); or NR6R7 = 3-9 membered heterocycle, opt. substd. and opt. interrupted by further heteroatoms; R7 may also = -CO-R8; R8 = H, opt. halogen-substd. alkyl, alkoxy, cycloalkyl, aryl, arylalkyl, benzyloxy or phenoxy (the last 4 gps. being opt. substd. by halogen, alkyl, alkoxy or haloalkyl; the following cpds. are excluded: 1,4-dihydro-4-hydroxy -1-(1,1,3,3-tetramethylbutyl) -3-(2,4,6-trimethylphenyl)-2H-pyrrol-2-one; 1-(1,1-dimethylethyl)-1,5 -dihydro-4-hydroxy-3 -(2,4,6-trimethylphenyl) -2H-pyrrol-2-one; 3(2,6-dichlorophenyl)-1,5-dihydro -4-hydroxy-1-(1,1,3,3-tetramethylbutyl) -2H-pyrrol-2-one; and 3-(2,6-dichlorophenyl) -1-(1,1-dimethylethyl) -1,5-dihydro-4-hydroxy-2H-pyrrol-2-one. USE - (I) are herbicides (claimed) useful as defoliants, desiccants, germination inhibitors and esp. weed killers. Depending on application rate, (I) are useful (i) as selective pref.- or post-emergence herbicides in perennial or annual culture plants, for combatting mono- or dicotyledorous weeds; or (ii) as total herbicides. Application rate is 1-10000 (pref. 10-5000) g/ha. (I) are also fungicides (not claimed), active against Pyricularia oryzae in rice.

Description

The invention relates to new 4-alkoxy or 4- (substit ized) amino-3-arylpyrrolinone derivatives, several processes and new intermediates for their manufacture and their use as herbicides and fungicides.

Of 3-acyl-pyrrolidine-2,4-diones are pharmaceutical Properties previously described (S. Suzuki et al., Chem. Pharm. Bull. 15 1120 (1967)). Furthermore, N-phenyl pyrrolidin-2,4-dione by R. Schmierer and H. Mildenber ger, Liebigs Ann. Chem. 1985 1095, synthesized. A biological activity of these compounds was not described.

In EP-A 02 62 399 a similarly structured verb is used dungen (3-aryl-pyrrolidin-2,4-dione) disclosed by de However, no herbicidal activity has become known is. In EP-A 03 77 893 3-aryl-pyrrolidine-2,4-dio ne and their acyl derivatives with herbicidal and insecticides the effect described.  

Furthermore, in EP-A 4 15 185 4-alkoxy- or 4- (Substituted) amino-3-arylpyrrolinone derivatives with her bicidal effect described. The in the above Registrations Connections mentioned are disclaimed by Definition of formula (I) and the scope of protection before lying registration excluded.

New 4-alkoxy or 4- (substituted) amino-3-aryl-Δ ³ -pyrrolin-2-one derivatives of the general formula (I) have now been found

in which
X and Y independently of one another represent hydrogen, halo, or a radical from the series alkyl, alkoxy, haloalkyl, haloalkoxy, each unsubstituted or substituted aryl, aryloxy, benzyloxy or arylthio,
Z represents halogen, alkyl or alkoxy,
n stands for a number 0, 1, 2 or 3,
R ¹ and R ² independently of one another represent alkyl or alkoxyalkyl optionally substituted by halogen,
R ³ for unsubstituted or in each case substituted by Ha logen alkyl, alkenyl, alkynyl, alk oxyalkyl, polyalkoxyalkyl or alkylthioalkyl, optionally cycloalkyl interrupted by heteroatoms, unsubstituted or substituted by halogen, alkyl, haloalkyl, haloalkoxy, alkoxy and / or nitro Arylalkyl, arylalkenyl, arylalkynyl or unsubstituted or substituted aryl, where halogen, alkyl, alkoxy, haloalkyl, haloalkoxy, in each case unsubstituted or substituted by halogen, alkyl, alkoxy, haloalkyl and / or haloalkoxy, phenoxy or phenylthio are suitable,
R ^{4 represents} hydrogen, optionally substituted by halogen alkyl or cycloalkyl or unsubstituted or substituted aryl or arylalkyl, halogen, alkyl, alkoxy and haloalkyl or nitro being suitable as substituents,
R ^{5 represents} hydroxyl, in each case unsubstituted or in each case substituted by halogen, alkoxy, alkenoxy, Al kinoxy or polyalkoxy, represents unsubstituted or substituted by halogen and / or alkyl cycloalkoxy or substituted or unsubstituted arylalkyloxy or

in which
R ⁶ and R ⁷ independently of one another are hydrogen, alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl, polyalkoxyalkyl, cycloalkyl, optionally interrupted by heteroatoms, each unsubstituted or substituted phenyl, phenylalkyl, phenoxyalkyl, hetaryl or hetarylalkyl or
R ⁶ and R ⁷ together with the nitrogen to which they are attached form a 3- to 9-membered, optionally substituted and, if appropriate, by further heteroatoms under a broken ring or
R ^{7 stands} for the group CO-R ⁸ , where R ^{8 stands} for hydrogen, alkyl, alkoxy, cycloalkyl optionally substituted by halogen, or unsubstituted or substituted aryl, arylalkyl, benzyloxy or phenoxy, where halogen, alkyl, Alkoxy and haloalkyl come into question,
except the connections
1,5-dihydro-4-hydroxy-1- (1,1,3,3-tetramethylbutyl) -3- (2,4,6-trimethylphenyl) -2H-pyrrol-2-one;
1- (1,1-dimethylethyl) -1,5-dihydro-4-hydroxy-3- (2,4,6-trimethylphenyl) -2H-pyrrol-2-one;
3- (2,6-dichlorophenyl) -1,5-dihydro-4-hydroxy-1- (1,1,3,3-tetramethylbutyl) -2H-pyrrol-2-one;
3- (2,6-dichlorophenyl) -1- (1,1-dimethylethyl) -1,5-dihydro-4-hydroxy-2H-pyrrol-2-one (cf. EP 3 77 893).

The aliphatic carbon chains, such as Are alkyl, haloalkyl, arylalkyl or phenoxyalkyl each straight or branched.

In substituted systems, such as substi Tuiert alkyl, alkenyl, cycloalkyl or aryl, can Substitution single or multiple, same or done differently. Aromatic systems are before moves from one to five times, especially easy to triple, substituted while cyclic systems before moves up to eight times, especially up to five times to be substituted.

Furthermore, it was found that the new 4-alkoxy or 4- (substituted) amino-3-aryl-Δ ³ -pyrrolin-2-one derivatives of the formula (I), with the exception of the compounds already mentioned, according to an im receives the following described procedure:

• A) The 4- (substituted) amino-3-aryl-Δ ³ -pyrrolin-2-one derivatives of the formula (Ia) according to the invention are obtained. in which
  R ¹ , R ² , R ³ , R ⁴ , R ⁶ , R ⁷ , X, Y, Z
  and n have the meanings given above and R ⁷ does not represent the group CO-R ⁸ ,
  if you either
  (A-α) 3-aryl-4-hydroxy-Δ ³ -pyrrolin-2-ones of the general formula (Ib) in which
  R ¹ , R ² , R ³ , R ⁴ , X, Y have the Z and n meanings given above,
  with amines of the formula (II) in which
  R ⁶ and R ^{7 have} the meanings given above and R ⁷ does not represent the group CO-R ⁸ ,
  if appropriate in the presence of a diluent and if appropriate in the presence of a dehydrating agent,
  or if you
  (A-β) compounds of the general formula (Ic) in which
  R ¹ , R ² , R ³ , R ⁴ , X, Y have the Z and n meanings given above and
  R ^{5 ′} represents unsubstituted or halogen-substituted alkoxy, alkenyloxy, alkynyloxy or polyalkoxy, unsubstituted or halogen and / or alkyl-substituted cycloalkoxy or substituted or unsubstituted arylalkoxy,
  with amines of the formula (II) in which
  R ⁶ and R ^{7 have} the meanings given above and R ⁷ does not represent the group CO-R ⁸ ,
  if appropriate in the presence of a diluent and if appropriate under elevated pressure.
• B) The 3-aryl Δ ³ -pyrrolin-2-one derivatives of the formula (Ia) according to the invention are also obtained in which
  R ¹ , R ² , R ³ , R ⁴ , X, Y, Z and the n meanings given above have and
  R ^{6 represents} hydrogen, alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl, polyalkoxyalkyl, if appropriate cycloalkyl interrupted by heteroatoms, in each case unsubstituted or substituted phenyl, phenylalkyl, phenoxyalkyl, hetaryl or hetarylalkyl and
  R ^{7 represents} the group -CO-R ⁸ , where
  R ^{8 represents} hydrogen, optionally substituted by halogen, alkyl, alkoxy, cycloalkyl or unsubstituted or substituted aryl, arylalkyl, benzyloxy or phenoxy, halogen, alkyl, alkoxy and haloalkyl being suitable as substitutes,
  if compounds of the formula (Id) in which
  R ¹ , R ² , R ³ , R ⁴ , X, Y, Z and n have the meanings given above and
  R ^{6 represents} hydrogen, alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl, polyalkoxyalkyl, cycloalkyl optionally interrupted by heteroatoms, in each case unsubstituted or substituted phenyl, phenylalkyl, phenoxyalkyl, hetaryl or hetarylalkyl,
  either
  (B-α) with acid halides of the general formula (III) in which
  R ^{7 represents} hydrogen, alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl, polyalkoxyalkyl, cycloal kyl optionally interrupted by heteroatoms, in each case unsubstituted or substituted phenyl, phenylalkyl, phenoxyalkyl, hetaryl or hetaryl alkyl and
  Hal represents halogen, especially chlorine and bromine,
  optionally in the presence of a diluent and optionally in the presence of an acid binder or
  (B-β) with carboxylic anhydrides of the general formula (IV) R ^{7 '} -CO-O-CO-R ^7' (IV) in which
  R ^{7 has} the meaning given above and is independently the same or different,
  if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder.

Finally, it was found that the new 4-alkoxy or 4- (substituted) amino-3-aryl-Δ ³ -pyrrolin-2-one derivatives of the general formula (I) have herbicidal and fungicidal properties.

Surprisingly, the 4-alkoxy- or 4- (substituted) amino-3-aryl-Δ ³ -pyrrolin-2-one derivatives according to the invention of the general formula (I) show very good herbicidal and fungicidal activity and, at the same time, excellent compatibility with important crops.

Compounds of the formula (I) in which
X and Y independently of one another for hydrogen, fluorine, chlorine, bromine, iodine or a radical of the series, C ₁ -C ₆ -alkyl, C ₁ -C ₆ -alkoxy, C ₁ -C ₆ -haloalkoxy, halogen-C ₁ - C ₄ alkyl, in each case unsubstituted or mono- to pentasubstituted, identically or differently substituted, phenyl, phenoxy, benzyloxy or phenylthio, the phenyl substituents selected being: fluorine, chlorine, bromine, iodine, C ₁ -C ₄ -alkyl, C ₁ -C ₄ alkoxy and halo-C ₁ -C ₄ alkyl,
Z represents fluorine, chlorine, bromine, iodine, C ₁ -C ₆ alkyl or C ₁ - C ₆ alkoxy,
n stands for a number 0, 1, 2 or 3,
R ¹ and R ² are each independently optionally substituted by fluorine and / or chlorine-substituted C ₁ - C ₆ alkyl or C ₁ -C ₄ -alkoxy-C ₁ -C ₄ -alkyl,
R ^{3 represents} unsubstituted or optionally substituted by halogen C ₁ -C ₁₂ alkyl, C ₃ -C ₈ alkenyl, C ₃ -C ₈ alkynyl, C ₁ -C ₁₀ alkoxy-C ₁ -C ₈ alkyl, C ₁ -C ₈ - polyalkoxy-C ₁ -C ₈ alkyl, C ₁ -C ₁₀ -alkylthio-C ₁ -C ₈ alkyl or stands for cycloalkyl with 3 to 8 ring atoms which is interrupted by oxygen, nitrogen and / or sulfur can be, or for each unsubstituted or in the phenyl part mono- to pentasubstituted, identically or differently substituted phenyl-C ₁ -C ₆ alkyl, phenyl-C ₁ -C ₆ -alkenyl, phenyl-C ₁ -C ₆ -alkynyl, phenyl or Naphthyl stands, the substituents selected in each case:
Fluorine, chlorine, bromine, iodine, C ₁ -C ₆ -alkyl, C ₁ -C ₆ -alkoxy, halogen-C ₁ -C ₆ -alkyl, halogen-C ₁ -C ₆ -alkoxy or in each case unsubstituted or single to five times , identical or different by fluorine, chlorine, bromine, iodine, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, halogen-C ₁ -C ₄ -alkyl and halogen-C ₁ -C ₄ -alkoxy substituted phenoxy or phenylthio,
R ⁴ for hydrogen, optionally substituted by halogen C ₁ -C ₆ alkyl, C ₃ -C ₈ cycloalkyl or for unsubstituted or by fluorine, chlorine, bromine, C ₁ - C ₆ alkyl, C ₁ -C ₆ - Haloalkyl, C ₁ -C ₆ -alkoxy or nitro-substituted phenyl phenyl-C ₁ -C ₅ -alkyl or naphthyl-C ₁ -C ₅ -alkyl,
R ^{5 stands} for hydroxy, in each case unsubstituted or substituted by fluorine, chlorine, bromine, iodine, C ₁ -C ₁₀ alkoxy, C ₁ -C ₅ alkenoxy, C ₁ -C ₅ alkynoxy, polyalkoxy, or furthermore cycloalkoxy with 3 to 7 ring atoms, the cycloalkyl radical being unsubstituted or mono- to pentasubstituted, identically or differently, by fluorine, chlorine, bromine and C ₁ -C ₄ -alkyl, or unsubstituted or by halogen, C ₁ -C ₆ - alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ alkoxy or nitro-substituted phenyl-C ₁ - C ₄ alkoxy or naphthyl-C ₁ -C ₄ alkoxy is,
or

in which
R ⁶ and R ⁷ independently of one another are hydrogen, C ₁ -C ₁₀ alkyl, C ₃ -C ₁₀ alkenyl, C ₁ -C ₈ alkoxy-C ₁ -C ₈ alkyl, C ₁ -C ₈ alkylthio -C ₁ -C ₈ alkyl, C ₁ -C ₈ polyalkoxy-C ₁ -C ₈ alkyl, cyc loalkyl having 3 to 8 ring atoms, which by one, two or three identical or different oxygen, nitrogen and sulfur atoms may be interrupted, depending on the case, unsubstituted or mono- to pentuplic, identical or differently substituted phenyl, phenyl-C ₁ -C ₆ -alkyl, phenoxy-C ₁ -C ₆ -alkyl, hetaryl or hetaryl-C ₁ -C ₆ - alkyl with 5 or 6 ring atoms each, 1 or 2 identical or different oxygen, nitrogen and sulfur atoms being contained in the ring, or
R ⁶ and R ⁷ together with the nitrogen to which they are attached form a 3- to 8-membered ring which can contain one or two double bonds and which contain one or two further, identical or different oxygen, sulfur or may contain nitrogen atoms, and the single fold to five, identical or different C ₁ - C ₄ alkyl and C ₁ -C ₄ alkylcarbonyl may be substi tuiert, or
R ^{7 represents} a group CO-R ⁸ , where
R ⁸ for hydrogen, optionally substituted by fluorine, chlorine, bromine, C ₁ -C ₁₀ alkyl, C ₁ -C ₁₀ alkoxy, C ₃ -C ₈ cycloalkyl or for unsubstituted or halogenated, C ₁ -C ₆ - alkyl, C ₁ -C ₆ haloalkyl, C ₁ - C ₆ alkoxy or nitro-substituted Phe nyl, phenyl-C ₁ -C ₆ -alkyl, naphthyl-C ₁ - C ₆ -alkyl, benzyloxy or phenoxy.

The group of compounds of the formula (I) in which
X for hydrogen, fluorine, chlorine, methyl, ethyl, n- or iso-propyl, methoxy, ethoxy, n- or i-prop oxy, halomethyl and halomethoxy with 1, 2 or 3 fluorine and / or chlorine atoms, haloethyl and Ha logenethoxy with 1 to 5, in particular 1 to 3, fluorine and / or chlorine atoms, each unsubstituted or monosubstituted to pentasubstituted, in particular monosubstituted to trisubstituted, identical or differently substituted phenyl, phenoxy, benzyloxy or phenylthio, the phenyl substituents selected being: fluorine , Chlorine, bromine, methyl, ethyl, n- or iso-propyl, methoxy, ethoxy, n- or iso-propoxy and trifluoromethyl,
Y represents hydrogen, fluorine, chlorine, methyl, ethyl, methoxy, ethoxy or trifluoromethyl,
Z represents fluorine, chlorine, methyl, ethyl, methoxy, ethoxy, halomethyl and halomethoxy with 1, 2 or 3 fluorine and / or chlorine atoms,
n represents 0, 1, 2 or 3,
R ¹ and R ² are each independently optionally substituted by fluorine and / or chlorine-substituted C ₁ - C ₅ alkyl or C ₁ -C ₃ alkoxy-C ₁ -C ₃ -alkyl,
R ³ for unsubstituted or optionally substituted by fluorine, chlorine and / or bromine methyl, ethyl, in each case straight-chain or branched and unsubstituted or optionally substituted by fluorine, chlorine and / or bromine, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, Decyl, C ₃ -C ₆ alkenyl, C ₃ -C ₆ alkynyl, C ₁ -C ₄ alkoxy-C ₁ -C ₄ alkyl, C ₁ -C ₄ alkylthio-C ₁ -C ₄ alkyl or represents cycloalkyl having 3 to 6 ring atoms, which can be interrupted by oxygen, nitrogen or sulfur, or represents unsubstituted or mono- to pentasubstituted, in particular monosubstituted to pentasubstituted, identical or differently substituted phenyl, benzyl, phenethyl, phenethenyl or phenethinyl, where the following are selected as substituents: fluorine, chlorine, methyl, ethyl, n- or iso-propyl, methoxy, ethoxy, trifluoromethyl, trifluoromethoxy or in each case unsubstituted or single to triple, identical or different, by fluorine, chlorine, methyl, methoxy, Tr ifluormethyl and trifluoromethoxy substituted phenoxy, phenyl thio,
R ⁴ for hydrogen, optionally substituted by fluorine and / or chlorine, substituted by C ₁ -C ₄ alkyl, C ₃ -C ₆ cycloalkyl or unsubstituted or by fluorine, chlorine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy or nitro substituted phenyl, phenyl-C ₁ -C ₂ alkyl or naphthyl-C ₁ -C ₂ alkyl,
R ⁵ for hydroxy, methoxy, ethoxy, n- or iso-propoxy, n-, iso-, sec-butoxy, C ₁ -C ₄ -alkenoxy, C ₁ -C ₄ -alkynoxy, polyalkoxy, halogen-C ₁ - C ₄ -alkoxy, where Halo is fluorine and / or chlorine, or cycloalkoxy with 3 to 6 ring atoms, the cycloalkyl radical being unsubstituted or monosubstituted to triple, identical or different, substituted by fluorine, chlorine, methyl and / or ethyl may be, or is unsubstituted or substituted by fluorine, chlorine, methyl, ethyl, trifluoromethyl, trifluoromethoxy or nitro phenyl-C ₁ -C ₄ -alkoxy or naphthyl-C ₁ -C ₄ -alkoxy or

in which
R ^{6 represents} hydrogen, methyl, ethyl, n- or isopropyl, allyl, n-, iso-, sec- or tert-butyl and
R ⁷ for hydrogen, methyl, ethyl, n-propyl, n-butyl, allyl, propargyl, methoxymethyl, meth oxyethyl, ethoxymethyl, ethoxyethyl, methyl thiomethyl, methylthioethyl, ethylthiomethyl, ethylthioethyl, cyclopropyl, cyclopentyl, cyclohexyl, in each case unsubstituted or simple phenyl, benzyl, phenethyl, pyridyl or pyrimidyl which is substituted by fluorine, chlorine, methyl, ethyl and trifluoromethyl, up to five times, in particular once to three times, or
R ⁶ and R ⁷ together with the nitrogen to which they are attached form a 5- or 6-membered ring which may contain one or two double bonds or which may contain a further nitrogen, oxygen or sulfur atom and which is simple can be substituted three times, identically or differently, by methyl, ethyl, methylcarbonyl or ethylcarbonyl, or
R ⁷ is a group CO-R ^8, wherein R ⁸ represents hydrogen, optionally fluorine- and / or chlorine C ₁ - C ₆ alkyl, C ₁ -C ₆ alkoxy, C ₃ -C ₇ cycloalkyl, or unsubstituted or substituted by fluorine, chlorine, C ₁ -C ₄ alkyl, C ₁ -C ₂ halo alkyl, C ₁ -C ₄ alkoxy or nitro substituted phenyl, phenyl C ₁ -C ₄ alkyl, naphthyl-C ₁ -C ₆ alkyl, benzyloxy or phenoxy.

The group of compounds in which
X for hydrogen, fluorine, chlorine, methyl, ethyl, n-propyl, i-propyl, methoxy, ethoxy, n-propoxy, iso-propoxy, trifluoromethyl or trifluoromethoxy, unsubstituted or mono- to trisubstituted, identically or differently substituted, phenyl, benzyloxy or phenoxy, the substituents selected from: fluorine, chlorine, methyl and trifluoromethyl,
Y represents hydrogen, fluorine or chlorine,
Z represents fluorine, chlorine, methyl, methoxy, trifluoromethyl or trifluoromethoxy,
n stands for 0, 1 and 2,
R ¹ optionally substituted by fluorine, methyl, ethyl, n- or i-propyl, n-, iso-, sec- or tert-butyl, n-, iso-, sec- or neo-pentyl or for methoxymethyl, ethoxymethyl, n- or iso-propoxy methyl,
R ^{2 represents} methyl, ethyl, n- or i-propyl,
R ^{3 is} unsubstituted, optionally substituted by fluorine, chlorine and / or bromine, methyl, ethyl, n-propyl, isopropyl, n-, iso-, sec- or tert-butyl, in each case straight-chain or branched pentyl, hexyl, heptyl, Octyl, allyl, propargyl, methoxymethyl, methoxyethyl, ethoxymethyl, ethoxy ethyl, cyclopropyl, cyclopentyl, cyclohexyl, or in each case unsubstituted or single to triple, identical or different by fluorine, chlorine, methyl, methoxy, trifluoromethyl, phenoxy and 4-trifluoromethyl phenoxy substituted phenyl, phenethyl, phenethenyl, phenethinyl or benzyl,
R ^{4 represents} hydrogen, methyl, ethyl, n- or isopropyl, n-, iso-, sec- or tert-butyl, unsubstituted or substituted by fluorine, chlorine, methyl, methoxy or trifluoromethyl, phenyl or benzyl,
R ⁵ for hydroxy, methoxy, ethoxy, n- or iso-propoxy, n-, iso- or sec-butoxy, trifluoroethoxy, for C ₃ - C ₆ cycloalkoxy or for unsubstituted or by fluorine, chlorine, methyl, trifluoromethyl, trifluorometh oxy or nitro substituted phenyl-C ₁ -C ₃ alkoxy or naphthyl-C ₁ -C ₃ alkoxy or

in which
R ^{6 represents} hydrogen, methyl, ethyl, n- or i-propyl, allyl, n-, iso-, sec- or tert-butyl and
R ^{7 represents} hydrogen, methyl, ethyl, n-propyl, allyl, n-butyl, unsubstituted or single to triple, identical or different phenyl substituted by fluorine, chlorine, methyl and trifluoromethyl or
R ⁶ and R ⁷ together with the nitrogen to which they are attached represent a heterocycle of the formula which is optionally monosubstituted to triple, identical or different by methyl, ethyl, methylcarbonyl or ethylcarbonyl:

or
R ^{7 represents} a group -CO-R ⁸ , where
R ⁸ for hydrogen, optionally substituted by fluorine, methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-butyl, C ₃ -C ₆ -cycloalkyl, methoxy, ethoxy, n- or i- Propoxy, n-, iso- or sec-butoxy, for unsubstituted or substituted by fluorine, chlorine, methyl, trifluoromethyl, methoxy or nitro, phenyl, phenyl-C ₁ -C ₃ -alkyl, naphthyl-C ₁ - C ₅ -alkyl , Benzyloxy or phenoxy.

Used according to the general manufacturing process (A-α) 3- (2-trifluoromethyl-phenyl) -1-tert-amyl-pyrroli din-2,4-dione and methylamine as starting materials, so the course of the method according to the invention by the the following reaction scheme can be reproduced:

If 3- (2-chloro-6-fluorophenyl) -4-methoxy-1- (1-methyl-1-phenyl) -ethyl-Δ ³ -pyrrolin-2-one is used according to the general preparation process (A-β) and isopropylamine as starting materials, the course of the process according to the invention is given again by the following reaction scheme:

According to process (B) (variant α), 3- (2-methoxyphenyl) -4-methylamino-1- (1,1,3,3-tetramethylbu tyl) -Δ ³ -pyrrolin-2-one and pivaloyl chloride are used as starting materials substance, the course of the process according to the invention can be represented by the following reaction scheme:

If 3- (2,6-dichlorophenyl) -1-tert-butyl-4-amino-Δ ³ -pyrrolin-2-one and acetic anhydride are used according to process B (variant β), the course of the process according to the invention can be determined by the following reaction scheme will be reproduced:

Formula (Ib) provides a general definition of the substituted 3-aryl-pyrrolidine-2,4-diones required as starting materials in process (A-α) for the preparation of compounds of the formula (Ia). In For mel (Ib) R ¹ , R ² , R ³ , R ⁴ , X, Y, Z and n are preferred or in particular for those meanings which have already been mentioned above in connection with the description of the compounds of the formula (I ) as preferred or as particularly preferred for R ¹ , R ² , R ³ , R ⁴ , X, Y, Z and n were specified.

The compounds of formula (Ib) are new and the subject of the invention except the compounds
1,5-dihydro-4-hydroxy-1- (1,1,3,3-tetramethylbutyl) -3- (2,4,6-trimethylphenyl) -2H-pyrrol-2-one;
1- (1,1-dimethylethyl) -1,5-dihydro-4-hydroxy-3- (2,4,6-trimethylphenyl) -2H-pyrrol-2-one;
3- (2,6-dichlorophenyl) -1,5-dihydro-4-hydroxy-1 - (1,1,3,3-tetramethylbutyl) -2H-pyrrol-2-one;
3- (2,6-dichlorophenyl) -1- (1,1-dimethylethyl) -1,5-dihydro-4-hydroxy-2H-pyrrol-2-one (cf. EP 3 77 893).

You will get if you get the N-acylamino acid ester Formula (V)

in which
R ¹ , R ² , R ³ , R ⁴ , X, Y, Z and n have the meanings given above, and
R ^{9 represents} alkyl, in particular methyl or ethyl,
intramolecularly condensed in the presence of a diluent and in the presence of a base.

To carry out the method according to the invention for the preparation of the compounds of formula (Ib) as Starting materials required N-acylamino acid esters from For mel (V) are partially known or can be im Principle known methods in a simple manner len.

For example, N-acylamino acid esters are obtained Formula (V) when acylamino acid esters of the formula (VI)

in which
R ^{9 represents} hydrogen or alkyl, in particular methyl or ethyl, and
R ¹ , R ² , R ³ and R ^{4 have} the meanings given above
with phenylacetic acid halides of the formula (VII)

in which
Hal represents halogen, in particular fluorine, chlorine or bromine, and
X, Y, Z and n have the meanings given above,
acylated in the usual way (cf. Chem. Rev. 52 (1953) 237-416 and Organikum, 9th edition 446 (1970) VEB German publisher of sciences)
or if one esterifies N-acylamino acids of the formula (V), in which R ^{9 represents} hydrogen, in a conventional manner (cf. Chem. Ind. (London) 1568 (1968)).

Compounds of the formula (V) in which R ^{9 is} hydrogen can also be prepared, for example, from phenylacetic acid halides of the formula (VII) and amino acids.

Compounds of the formula (VI) are known from the literature processes from α-halocarboxylic acids or esters and  Amines available (Advanced Organic Chemistry, J. March P. 377, Mc Graw-Hill Inc. (1977)).

The phenylacetic acid halides of the formula (VII) are known compounds of organic chemistry.

The following compounds of the formula (V) are mentioned by way of example:
N- (2-fluorophenylacetyl) -N-tert-butyl-amino-acetic acid, ethyl ester
N- (2-fluorophenylacetyl) -N- (1,1,3,3-tetramethyl) butyl aminoacetic acid ethyl ester
N- (2-fluorophenylacetyl) -N-tert-butylaminoacetic acid ethyl ester
N- (2-fluoropheny lacetyl) -N- (1,1,3,3-tetramethyl) butyl aminoacetic acid ethyl ester
N- (2-fluorophenylacetyl) -N-tert-amylaminoacetic acid ethyl ester
N- (2-fluorophenylacetyl) -N- (1-methyl-1-phenyl) ethyl aminoacetic acid ethyl ester
N- (2-fluorophenylacetyl) -N- (1-cyano-1-methyl) ethyl aminoacetic acid ethyl ester
N- (2-fluorophenylacetyl) -N- (1-ethynyl-1-methyl) ethyl aminoacetic acid ethyl ester
N- (2-Fluorophenylacetyl) -N- (1- (2-phenylethynyl) -1-methyl) ethylaminoacetate
N- (2-chlorophenylacetyl) -N-tert-butyl-aminoacetic acid ethyl ester
N- (2-chlorophenylacetyl) -N-tert-amylaminoacetic acid ethyl ester
N- (2-chlorophenylacetyl) -N- (1,1,3,3-tetramethyl) butyl aminoacetic acid ethyl ester
N- (2-chlorophenylacetyl) -N- (1-methyl-1-phenyl) ethyl aminoacetic acid ethyl ester
N- (2-chlorophenylacetyl) -N- (1-cyano-1-methyl) ethyl aminoacetic acid ethyl ester
N- (2-chlorophenylacetyl) -N- (1-ethynyl-1-methyl) ethylaminoacetate
N- (2-Chlorophenylacetyl-N- (1- (2-phenylethynyl) -1-methyl) ethylaminoacetate
N- (2,6-difluorophenylacethyl) -N-tert-butylaminoacetic acid, ethyl ester
N- (2,6-difluorophenylacetyl) -N- (1,1,3,3-tetramethyl) butyl ethyl aminoacetate
N- (2,6-difluorophenylacetyl) -N-tert-amylaminoacetic acid reethylester
N- (2,6-difluorophenylacetyl) -N- (1-methyl-1-phenyl) ethylaminoacetate
N- (2,6-difluorophenylacetyl) -N- (1-cyano-1-methyl) ethylaminoacetate
N- (2,6-difluorophenylacetyl) -N- (1-ethynyl-1-methyl) ethylaminoacetate
N- (2,6-difluorophenylacetyl) -N- (1- (2-phenylethynyl) -1-methyl) ethyl aminoacetic acid
N- (2,6-dichlorophenylacetyl) -N-tert-butyl-aminoacetic acid reethylester
N- (2,6-dichlorophenylacetyl) -N-tert-amylaminoacetic acid ethyl ester
N- (2,6-dichlorophenylacetyl) -N- (1,1,3,3-tetramethyl) butyl ethyl acetate
N- (2,6-dichlorophenylacetyl) -N- (1-methyl-1-phenyl) ethylaminoacetate
N- (2,6-dichlorophenylacetyl) -N- (1-cyano-1-methyl) ethyl aminoacetic acid ethyl ester
N- (2,6-dichlorophenylacetyl) -N- (1-ethynyl-1-methyl) ethylaminoacetate
N- (2,6-dichlorophenylacetyl-N- (1- (2-phenylethinyl) -1-methyl) ethyl aminoacetic acid, ethyl ester
N- (2-chloro-6-fluorophenylacetyl) -N-tert-butyl-aminoacetic acid, ethyl ester
N- (2-chloro-6-fluorophenylacetyl) -N- (1,1,3,3-tetramethyl) butylaminoacetic acid ethyl ester
N- (2-chloro-6-fluorophenylacetyl) -N-tert-amyl-aminoacetic acid, ethyl ester
N- (2-chloro-6-fluorophenylacetyl) -N- (1-methyl-1-phenyl) ethylaminoacetic acid ethyl ester
N- (2-chloro-6-fluorophenylacetyl) -N- (1-cyano-1-methyl) ethylaminoacetic acid ethyl ester
N- (2-chloro-6-fluorophenylacetyl) -N- (1-ethynyl-1-methyl) ethyl l-aminoacetic acid, ethyl ester
N- (2-Chloro-6-fluorophenylacetyl) -N- (1- (2-phenylethynyl) -1-methyl) ethylaminoacetic acid, ethyl ester
N- (2-trifluoromethylphenylacetyl) -N-tert-butylamino ethyl acetate
N- (2-Trifluoromethylphenylacetyl) -N-tert-amylaminoacetic acid, ethyl ester
N- (2-Trifluoromethylphenylacetyl) -N- (1,1,3,3-tetramethyl) butylaminoacetic acid ethyl ester
N- (2-trifluoromethylphenylacetyl) -N- (1-methyl-1-phenyl) ethylaminoacetic acid ethyl ester
N- (2-Trifluoromethylphenylacetyl) -N- (1-cyano-1-methyl) ethylaminoacetic acid ethyl ester
N- (2-Trifluoromethylphenylacetyl) -N- (1-ethynyl-1-methyl) ethylaminoacetic acid ethyl ester
N- (2-Trifluoromethylphenylacetyl-N- (1- (2-phenylethynyl) -1-methyl) ethylaminoacetic acid ethyl ester
N- (2-bromophenylacetyl) -N-tert-butyl-aminoacetic acid, ethyl ester
N- (2-bromophenylacetyl) -N- (1,1,3,3-tetramethyl) butyl aminoacetic acid ethyl ester
N- (2-bromophenylacetyl) -N-tert-amyl-aminoacetic acid ethyl ester
N- (2-bromophenylacetyl) -N- (1-methyl-1-phenyl) ethyl-amino-ethyl acetate
N- (2-bromophenylacetyl) -N- (1-cyano-1-methyl) ethyl-amino-ethyl acetate
N- (2-bromophenylacetyl) -N- (1-ethynyl-1-methyl) ethyl-aminoacetic acid ethyl ester
N- (2-Bromophenylacetyl) -N- (1- (2-phenylethynyl) -1-methyl) ethylaminoacetic acid, ethyl ester
N- (2-methylphenylacetyl) -N-tert-butylaminoacetic acid ethyl ester
N- (2-methylphenylacetyl) -N-tert-amylaminoacetic acid ethyl ester
N- (2-Methylphenylacetyl) -N- (1,1,3,3-tetramethyl) butyl aminoacetic acid ethyl ester
N- (2-methylphenylacetyl) -N- (1-methyl-1-phenyl) ethyl aminoacetic acid ethyl ester
N- (2-methylphenylacetyl) -N- (1-cyano-1-methyl) ethyl aminoacetic acid ethyl ester
N- (2-methylphenylacetyl) -N- (1-ethynyl-1-methyl) ethyl aminoacetic acid ethyl ester
N- (2-Methylphenylacetyl-N- (1- (2-phenylethynyl) -1-methyl) ethylaminoacetic acid, ethyl ester
N- (2-methoxyphenylacetyl) -N-tert-butylaminoacetic acid ethyl ester
N- (2-methoxyphenylacetyl) -N- (1,1,3,3-tetramethyl) butyl aminoacetic acid ethyl ester
N- (2-methoxyphenylacetyl) -N-tert-amylaminoacetic acid ethyl ester
N- (2-methoxyphenylacetyl) -N- (1-methyl-1-phenyl) ethyl aminoacetic acid ethyl ester
N- (2-methoxyphenylacetyl) -N- (1-cyano-1-methyl) ethyl aminoacetic acid ethyl ester
N- (2-methoxyphenyl acetyl) -N- (1-ethynyl-1-methyl) ethyl aminoacetic acid ethyl ester
N- (2-Methoxyphenylacetyl) -N- (1- (2-phenylethynyl) -1-methyl) ethylaminoacetate
N- (2-Benzyloxyphenylacetyl) -N-tert-butyl-aminoacetic acid reethylester
N- (2-Benzyloxyphe nylacetyl) -N-tert-amylaminoacetic acid ethyl ester
N- (2-Benzyloxyphenylacetyl) -N- (1,1,3,3-tetramethyl) butyl ethyl acetate
N- (2-Benzyloxyphenylacetyl) -N- (1-methyl-1-phenyl) ethyl aminoacetic acid ethyl ester
N- (2-Benzyloxyphenylacetyl) -N- (1-cyano-1-methyl) ethyl aminoacetic acid ethyl ester
N- (2-Benzyloxyphenylacetyl) -N- (1-ethynyl-1-methyl) ethyl aminoacetic acid ethyl ester
N- (2-Benzyloxyphenylacetyl-N- (1- (2-phenylethynyl) -1-methyl) ethylaminoacetic acid, ethyl ester.

For example, if one uses N- (2-fluorophenylacetyl) -N- tert-amylaminoacetic acid ethyl ester, so the course of the inventive method for producing the Compounds of formula (Ib) by the following reaction Scheme are reproduced:

The inventive method for producing the Ver bonds of formula (Ib) is characterized in that compounds of formula (V) in the presence of  Bases undergoes intramolecular condensation.

As a diluent in the invention Process for the preparation of the compounds of the formula (Ib) all customary inert organic solvents be set. Coal is preferably used substances such as toluene and xylene, furthermore ethers such as dibu tyl ether, tetrahydrofuran, dioxane, glycol dimethyl ether and diglycol dimethyl ether, also polar solvents tel, such as dimethyl sulfoxide, sulfolane, dimethylformamide and N-methyl-pyrrolidone.

Deprotonating agents which can be used to carry out the process according to the invention for the preparation of the compounds of the formula (Ib) are all customary proton acceptors. Alkali metal and alkaline earth metal oxides, hydroxides and carbonates, such as sodium hydroxide, potassium hydroxide, magnesium oxide, calcium oxide, sodium carbonate, potassium carbonate and calcium carbonate, which can also be used in the presence of phase transfer catalysts such as, for example, B. triethylbenzylammonium chloride, tetrabutylammonium bromide, Adogen 464 or TDA 1 (Adogen 464 = methyltrialkyl (C ₈ -C ₁₀ ) ammonium chloride TDA 1 = tris (methoxyethoxyethyl) amine) can be used. Furthermore, alkali metal and alkaline earth metal amides and hydrides, such as sodium amide, sodium hydride and calcium hydride, and also alkali metal alcoholates, such as sodium methylate, sodium ethyl and potassium tert-butoxide, can be used.

The reaction temperatures can be carried out of the inventive method for producing the Compounds of formula (Ib) within a larger one Range can be varied. Generally you work at temperatures between 0 ° C and 250 ° C, preferably between 50 ° C and 150 ° C.

The process according to the invention is generally described in Normal pressure carried out.

When carrying out the method according to the invention for the preparation of the compounds of formula (Ib) the reaction components of the formula (V) and the de protonating bases are generally approximately equimolar Quantities. However, it is also possible to use one or the other other component in a larger excess (up to 3 mol) to use.

The procedures (A- α) and (A-β) still required as starting materials Amines of the formula (II) are generally known compounds gene or can be prepared by known methods (see Houben-Weyl, Methods of Organic Chemistry, Vol. XI / 1, Georg-Thieme-Verlag, Stuttgart 1957).

As a diluent for performing the fiction According to method (A-α) preferably inert orga come nical solvents. This includes in particular aliphatic, alicyclic or aromatic otherwise halogenated hydrocarbons, such as such as gasoline, ligroin, benzene, toluene, xylene, chlorobene  zol, petroleum ether, pentane, hexane, heptane, cyclohexane, di chloromethane, chloroform, carbon tetrachloride, ether, such as diethyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl or diethyl ether, ketones such as acetone or butanone, nitriles such as acetonitrile or propionitrile, Amides such as dimethylformamide, dimethylacetamide, N-methyl formanilide, N-methylpyrrolidone or hexamethylphosphorus acid triamide or esters, such as ethyl acetate. The Amines of formula (IV) can be in liquid form in ent speaking excess also as a solvent be set.

The process (A-α) according to the invention is optionally in the presence of a dehydrating agent leads. Preferably used as a dehumidifier Medium alkali metal carbonates such. B. potassium carbonate; Molecular sieves or - in catalytic amounts - e.g. B. p- Toluenesulfonic acid. As a good practice the azeotropic distillation of the water during the reaction.

The reaction temperatures can be carried out the process (A-α) according to the invention in a larger one Range can be varied. Generally one works at Temperatures between 0 ° C and 250 ° C, preferably at Temperatures between 20 ° C and 200 ° C.

The process (A-α) according to the invention is customary carried out under normal pressure. However, it is also possible Lich to work under increased pressure.  

To carry out the method (A-α) is used per mole of compound of formula (Ib) in all generally 1 to 10 mol, preferably 1 to 2.5 mol Amine of formula (II) and optionally 1 to 5 moles dehydrating agent. The reaction procedure tion, processing and isolation of the reaction products takes place in analogy to generally known methods.

The compounds required as starting materials in the process (A-β) according to the invention for the preparation of compounds of the formula (Ia) are generally defined by the formula (Ic). In formula (Ic) R ^1, R ^2, R ^3, R ^4, R ^5, X, Y, Z and n are each preferably or in particular has those meanings which have already been mentioned above in connection with the description of the compounds of formula ( I) preferably or as in particular before given for R ¹ , R ² , R ³ , R ⁴ , R ⁵ , X, Y, Z and n were given.

The compounds of formula (Ic) are new and the subject the invention. You will get one if you connect gene of the formula (Ib)

in which
R ¹ , R ² , R ³ , R ⁴ , XY, Z and n have the meanings given above,
with alkylating agents of formula (VIII)

R¹⁰-X¹ (VIII)

in which
R ¹⁰ represents unsubstituted or in each case substituted by halogen, alkyl, alkenyl, alkynyl, polyalkoxyalkyl, unsubstituted or substituted by halogen and / or alkyl cycloalkyl or unsubstituted or substituted arylalkyl and
X ^{1 represents} halogen or another leaving group customary for alkylation reagents,
if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder. The compounds of formula (Ib) are compounds according to the invention and can be obtained by the process described above.

The continue as raw materials for the production of he compounds (Ic) according to the invention as starting materials required alkylating agents are represented by the formula (VIII) generally defined.

In formula (VIII), R ¹⁰ preferably represents C ₁ -C ₁₀ alkyl, C ₂ -C ₁₀ alkenyl, C ₂ -C ₁₀ alkynyl, halo-C ₁ -C ₁₀ alkyl, cycloalkyl having 3 to 7 ring atoms , where the cycloalkyl radical is unsubstituted or monosubstituted or substituted five times, identically or differently by fluorine, chlorine, bromine and C ₁ -C ₄ -alkyl, or for phenyl-C ₁ -C ₆ alkyl which is substituted by halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy or C ₁ -C ₄ haloalkyl may be substituted. R ¹⁰ particularly preferably represents methyl, ethyl, propyl or isopropyl, allyl, propynyl and benzyl substituted by fluorine, chlorine, methyl, methoxy or trifluoromethyl. In formula (VIII), X ¹ preferably represents chlorine, bromine or iodine, C ₁ -C ₄ -alkylsulfonyloxy, C ₁ -C ₄ -alkoxysulfonyloxy or p-toluenesulfonyloxy, such as methanesulfonyloxy, methoxysulfonyloxy or ethoxysulfonyloxy.

The alkylation reagents of formula (VIII) are be known compounds of organic chemistry.

To carry out the inventive method for Preparation of the compounds (Ic) according to the invention Inert organic solvents as diluents tel in question. Aliphatic, alicyclic or aromatic, optionally halogen hydrogenated hydrocarbons, such as gasoline, Benzene, toluene, xylene, pentane, hexane, heptane, cyclohe xan, petroleum ether, ligroin, methylene chloride, chloroform, Carbon tetrachloride, chlorobenzene or dichlorobenzene, Ethers, such as diethyl ether, diisopropyl ether, dioxane, Te trahydrofuran or ethylene glycol diethyl ether or di methyl ether, ketones such as acetone, butanone, methyl isopro pyl ketone or methyl isobutyl ketone, esters such as acetic acid  reethyl esters, acids such as acetic acid, nitriles such as Ace tonitrile or propionitrile, amides, such as dimethylformamide, Dimethylacetamide, N-methyl-pyrrolidone or hexamethyl phosphoric acid triamide. Is used as a reaction partner Compounds of formula (VIII) in liquid form it is also possible to use this in a corresponding excess to be used simultaneously as a diluent.

All commonly used acid binders are used possible inorganic and organic bases. Before alkali metal hydrides, hydroxides, amides, carbonates or bicarbonates, such as for example sodium hydride, sodium amide, sodium hydroxide, Sodium carbonate or sodium hydrogen carbonate, or also tertiary amines, such as triethylamine, N, N-Di methylaniline, pyridine, 4- (N, N-dimethylamino) pyridine, Diazabicyclooctane (DABCO), diazabicyclonones (DBN) or Diazabicycloundecene (DBU).

The reaction temperatures can be carried out can be varied over a wide range. In general NEN one works between -20 ° C and + 150 ° C, preferably between 0 ° C and + 100 ° C.

To carry out the inventive method for Preparation of the compound (Ic) according to the invention one per mole of compound of formula (Ib) in general 1 to 20 moles each, preferably 1 to 15 moles each, of alkylating agents of formula (VIII) and given if 1 to 3 moles, preferably 1 to 2 moles, of acid bin demittel one. The implementation of the reaction, workup and isolation of the reaction products of formula (Ib)  follows according to usual methods (see also the manufacturer examples).

Is used to produce the Ver Compounds of formula (Ic) for example 3- (2-chlorophene nyl) -1-tert-butyl-pyrrolidine-2,4-dione and p-toluenesul fonsäuremethylester as starting materials, the Ver course of the method according to the invention by the following Reaction scheme are reproduced:

As a diluent for performing the fiction According to method (A-β) preferably inert orga come nical solvents. This includes in particular aliphatic, alicyclic or aromatic otherwise halogenated hydrocarbons, such as such as gasoline, ligroin, benzene, toluene, xylene, chlorobene zol, petroleum ether, pentane, hexane, heptane, cyclohexane, di chloromethane, chloroform, carbon tetrachloride, ether, such as diethyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl or diethyl ether, nitriles such as aceto  nitrile or propionitrile, amides, such as dimethylformamide, Dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide or esters such as Es ethyl acetate. The amines of the formula (IV) in liquid ger form can also in a corresponding excess can be used as a solvent.

The reaction temperatures can be carried out of the method according to the invention (A-β) in a larger one Range can be varied. Generally one works at Temperatures between 0 ° C and 250 ° C, preferably at Temperatures between 20 ° C and 200 ° C.

The process (A-β) according to the invention is customary carried out under increased pressure. To carry out the Process (A-β) according to the invention is used per mole of Compound of the formula (Ic) generally 1 to 10 mol, preferably 1 to 2.5 mol of amine of the formula (II) and optionally 1 to 5 moles of dehydrating agent a. The implementation of the reaction, workup and The reaction products are isolated in analogy to generally known methods.

The compounds of the formula (Id) required as starting materials in the process (B) according to the invention for the preparation of the compounds of the formula (Ia) are generally defined by this formula. In formula (Id), R ^1, R ^2, R ^3, R ^4, R ^6, X, Y, Z and n are each preferably or in particular sondere for those meanings which have already above in connection with the description of the compounds of the invention of the formula (I) preferably or as in particular particularly preferred for R ¹ , R ² , R ³ , R ⁴ , R ⁶ , X, Y, Z and n have been specified.

The compounds of formula (Id) are new and the subject the invention. They are available according to process (A-α) and (A-β).

To carry out the method according to the invention (B-α) and (B-β) still required as starting materials Acid halides of formula (III) and the carboxylic acid Hydrides of the formula (IV) are generally known verbs organic chemistry.

The process (B-α) is characterized in that Compounds of formula (Id) with acid halides of Formula (III) is implemented. Can be used as a diluent the inventive method (B-α) when using the Acid halides are all inert to these compounds ten solvents are used. Preferably used are hydrocarbons such as gasoline, benzene, toluene, Xylene and tetralin, also halogenated hydrocarbons, such as methylene chloride, chloroform, carbon tetrachloride, Chlorobenzene and o-dichlorobenzene, also ketones, such as Acetone and methyl isopropyl ketone, further ether, such as Diethyl ether, tetrahydrofuran and dioxane, moreover Solvents such as dimethyl sulfoxide and sulfolane. If the Hydrolysis stability of the acid halide allows it the reaction is also carried out in the presence of water will.  

If the corresponding carboxylic acid halides are used thus comply with the implementation as an acid binder the inventive method (B-α) all the usual acid reactors into consideration. Are preferably usable tertiary amines such as triethylamine, pyridine, diazabicyclo octane (DABCO), diazabicycloundecene (DBU), diazabicyclo nonen (DBN), Hünig base and N, N-dimethyl-aniline, further Alkaline earth metal oxides, such as magnesium and calcium oxide, also alkali and alkaline earth metal carbonates, such as Na trium carbonate, potassium carbonate and calcium carbonate.

The reaction temperatures in the fiction method (B-α) also when using acid halides vary within a wide range will. Generally one works at temperatures between -20 ° C and + 250 ° C, preferably between 0 ° C and 150 ° C.

When carrying out the method according to the invention (B-α) become the starting materials of the formula (Id) and that Acid halide of the formula (III) in general in ange approaches equivalent amounts used. However, it is also possible the acid chloride in a larger excess (up to 5 moles). The processing takes place according to usual methods.

The process (B-β) is characterized in that Compounds of formula (Id) with carboxylic acid hydrides Implements formula (IV).

If one uses in the process according to the invention (B-β)  as a reaction component of formula (IV) Carbonsäureanhy dride, the diluents used can preferably be those diluents that are also used in the use of acid halides, preferably in Be come. In addition, an excess can carboxylic acid hydride used simultaneously as a diluent act.

The reaction temperatures in the fiction method (B-β) also when using Car bonic anhydrides within a wide range can be varied. Generally one works at Tempe temperatures between -20 ° C and + 250 ° C, preferably between 0 ° C and 150 ° C.

When carrying out the method according to the invention the starting materials of formula (Id) and the car bonic anhydride of the formula (IV) in general in ange approaches equivalent amounts used. However, it is also possible the carboxylic anhydride in a larger over shot (up to 5 moles). The processing he follows according to usual methods.

The general procedure is to use diluent tel and excess carboxylic acid anhydride and the resulting carboxylic acid by distillation or by washing with an organic solvent or removed with water.

The active compounds according to the invention can be used as defoliants, Desiccants, herbicides and especially as  Weed killers are used. Under Un herb in the broadest sense, all plants can be understood hen who grow up in places where they are undesirable. Whether the substances according to the invention as total or selek effective herbicides depend essentially on the turned amount.

The active compounds according to the invention can, for. B. at the following plants can be used:

Dicotyledon weeds of the genera

Sinapsis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Cheno podium, urtica, senecio, amaranthus, portulaca, xanthi um, convolvulus, ipomoea, polygonum, sesbania, ambrosia, Cirsium, Carduus, Sonchus, Solanum, Rorippa, Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, galeopsis, papaver, centaurea, trifolium, ranun culus, Taraxacum.

Dicotyledon cultures of the genera

Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, Lac tuca, cucumis, cucurbita.

Monocotyledonous weeds of the genera

Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagitta ria, Eleocharis, Scirpus, Paspalum, Ischaemum, Spheno clea, Dactyloctenium, Agrostis, Alopecurus, Apera.  

Monocot cultures of the genera

Oryza, Zea, Triticum, Hordeum, Avena, Secale, Sorghum, Panicum, Saccharum, Pineapple, asparagus, allium.

The use of the active compounds according to the invention is dependent by no means limited to these genres, but extends to other plants in the same way Zen.

The compounds are suitable depending on the Total weed control concentration e.g. B. on In industrial and track systems and on paths and squares and without tree cover. Likewise, the connections to Weed control in permanent crops, e.g. B. Forst, ornamental wooden, fruit, wine, citrus, nut, banana, coffee, Tea, gum, oil palm, cocoa, berry fruit and hops facilities, on ornamental and sports turf and pastures and for selective weed control in annual crops be used.

The compounds of formula (I) according to the invention are suitable to combat monocotyledons and dicotyledons Un herbs both pre- and post-emergence method.

The compounds also show activity against pyricula ria oryzae on rice.

The active ingredients can be in the usual formulations are transferred, such as solutions, emulsions, spray powder ver, suspensions, powders, dusts, pastes, sol  Liche powders, granules, suspension emulsion concentrates trate, active ingredient-impregnated natural and synthetic Fabrics as well as very fine encapsulation in polymeric fabrics.

These formulations are produced in a known manner provides, e.g. B. by mixing the active ingredients with Extenders, i.e. liquid solvents and / or solid carriers, optionally using of surface-active agents, i.e. emulsifiers and / or dispersants and / or foam generators Means.

In the case of the use of water as an extender z. B. also organic solvents as auxiliary solutions means are used. Com as liquid solvent Essentially possible: aromatics such as xylene, toluene ol, or alkylnaphthalenes, chlorinated aromatics and chlo aliphatic hydrocarbons such as chlorobenzo le, chlorethylene or methylene chloride, aliphatic Hydrocarbons such as cyclohexane or paraffins, e.g. B. Petroleum fractions, mineral and vegetable oils, alcohol get, such as butanol or glycol and their ether and Esters, ketones such as acetone, methyl ethyl ketone, methyl isobu tylketone or cyclohexanone, strongly polar solvents, such as dimethylformamide and dimethyl sulfoxide, and Water.

The following are suitable as solid carriers:
e.g. B. ammonium salts and natural rock powders such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders such as highly disperse silica, aluminum oxide and silicates; as solid carriers for granules are possible: z. B. broken and fractional natural rocks such as calcite, marble, pumice, sepiolite, Dolo with and synthetic granules from inorganic and organic flours as well as granules from organic mate rial such as sawdust, coconut shells, corn cobs and Ta bakstengelen; as emulsifying and / or foam-generating agents are possible: z. B. nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, poly oxyethylene fatty alcohol ethers, e.g. B. alkylaryl polyglycol ether, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates; Possible dispersants are: B. lignin sulfite and methyl cellulose.

Adhesives such as carboxy can be used in the formulations methyl cellulose, natural and synthetic powder, granular or latex-shaped polymers can be used, such as Gum arabic, polyvinyl alcohol, polyvinyl acetate, as well natural phospholipids such as cephalins and lecithins and synthetic phospholipids. Other additives can mineral and vegetable oils.

Dyes such as inorganic pigments, e.g. B. Iron oxide, titanium oxide, ferrocyan blue and organic color substances such as alizarin, azo and metal phthalocyanine color substances and trace nutrients such as salts of iron, manganese, Boron, copper, cobalt, molybdenum and zinc are used will.

The formulations generally contain between 0.1 and 95 percent by weight of 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 ones Weed herbicides find where possible with finished formulations or tank mixes are.

Known herbicides are suitable for the mixtures, for example anilides, such as. B. Diflufenican and Propa Nile; Arylcarboxylic acids, such as. B. dichloropicolinic acid, Di camba and picloram; Aryloxyalkanoic acids, such as. B. 2.4 D, 2.4 DB, 2.4 DP, fluroxypyr, MCPA, MCPP and triclopyr; Aryloxy-phenoxy-alkanoic acid esters, such as. B. Diclofop-me thyl, fenoxaprop-ethyl, fluazifop-butyl, haloxyfop-me thyl and quizalofop-ethyl: azinones such as e.g. B. Chloridazon and norflurazon; Carbamates, e.g. B. chlorpropham, Des medipham, phenmedipham and propham; Chloroacetanilides, such as B. alachlor, acetochlor, butachlor, metazachlor, Metolachlor, pretilachlor and propachlor; Dinitroanili no, such as B. Oryzalin, Pendimethalin and Trifluralin; Diphenyl ether, such as. B. Acifluorfen, Bifenox, Fluorogly cofen, fomesafen, halosafen, lactofen and oxyfluorfen; Ureas, such as B. chlorotoluron, diuron, fluometuron, Isoproturon, linuron and methabenzthiazuron; Hydroxyl amines such as B. Alloxydim, Clethodim, Cycloxydim, Seth oxydim and tralkoxydim; Imidazolinones, e.g. B. Imazeth apyr, imazamethabenz, imazapyr and imazaquin; Nitriles, such as B. bromoxynil, dichlobenil and ioxynil; Oxyacet amides such as B. Mefenacet; Sulfonylureas, such as. B. Amidosulfuron, bensulfuron-methyl, chlorimuron-ethyl,  Chlorsulfuron, Cinosulfuron, Metsulfuron-methyl, Nico sulfuron, primisulfuron, pyrazosulfuron-ethyl, thifene sulfuron-methyl, triasulfuron and tribenuron-methyl; Thiol carbamates, such as. B. butylates, cycloates, dialates, EPTC, Esprocarb, Molinate, Prosulfocarb, Thiobencarb and Triallates; Triazines, e.g. B. Atrazin, Cyanazin, Sima zin, Simetryne, Terbutryne and Terbutylazin; Triazinones, such as B. hexazinone, metamitron and metribuzin; other such as B. aminotriazole, benfuresate, bentazone, cinmethy lin, clomazone, clopyralid, difenzoquat, dithiopyr, Ethofumesate, fluorochloridone, glufosinate, glyphosate, Isoxaben, Pyridate, Quinchlorac, Quinmerac, Sulphosate and tridiphanes.

Also a mixture with other known active ingredients, such as fungicides, insecticides, acaricides, nematicides, Protection against bird feed, plant nutrients and Soil improvers are possible.

The active ingredients as such, in the form of their formu or the resulting from further dilution riding application forms, such as ready-made solutions gene, suspensions, emulsions, powders, pastes and granules late. The application is done in übli cher way, e.g. B. by pouring, spraying, spraying, litter en.

The active compounds according to the invention can be used both before and can also be applied after the plants have emerged.  They can also be worked into the soil before sowing will.

The amount of active ingredient used can be in a larger Be fluctuate richly. It essentially depends on the type of the desired effect. In general, the Application rates between 1.0 g and 10 kg of active ingredient per Hectares of soil, preferably between 10 g and 5 kg per hectare

The production and use of the invention Active ingredients are shown in the following examples.

Manufacturing examples Example (Ia-1) (Method (A-α))

7.48 g (0.03 mol) of 3- (2-fluorophenyl) -1-tert-butyl-pyrro Lidin-2,4-dione are in a mixture of 150 ml of xylene and 15 ml of glacial acetic acid dissolved. For this purpose, 18.8 ml (0.188 mol) of a 32% methylamine solution and 0.57 g (3 mmol) p-toluenesulfonic acid monohydrate and the Reaction to reflux and using heated by a water separator. After the reaction is complete, the solvent is reduced Distilled off pressure, the residue in 50 ml of dimethyl Formamide taken up and in 200 ml of 0.5 N sodium hydroxide solution stirred in. The precipitation that occurs is vacuumed and dried.

6.4 g (82% of theory) of 3- (2-fluorophenyl) -1-tert-butyl-4-methylamino-Δ ³ -pyrrolin-2-one with a melting point of 142 ° C. are obtained.

Analogous to the production example (Ia-1) and according to the general information on the method according to the invention the compounds listed in Table 1 are obtained of the general formula (Ia)

Table 1

Example (Ia-5) (Method (B-α))

2.48 g (0.01 mol) of 4-amino-3- (2-fluorophenyl) -1-tert-butyl-Δ ³ pyrrolin-2-one are added in portions to 25 ml of acetyl chloride at room temperature. The mixture is heated to reflux and the course of the reaction is followed by thin layer chromatography. After the reaction has ended, the solvent is distilled off under reduced pressure. The oil obtained is purified on a silica gel column (mobile phase: ethyl acetate / n-hexane 1:10).

1.1 g (38% of theory) of 4-acetylamino-3- (2-fluorophenyl) -1-tert-butyl- / Δ ³ -pyrrolin-2-one are obtained as a colorless oil.

Analogous to the production example (Ia-5) and according to the general information on the method according to the invention the compounds listed in Table 2 are obtained of the general formula (Ia)

Table 2

Preparation of the starting compounds (Ic) Example (Ic-1)

5.66 g (0.02 mol) of 3- (2-chloro-6-fluorophenyl) -1-tert-bu tyl-pyrrolidine-2,4-dione become a mixture of 100 ml of absolute acetonitrile 04955 00070 552 001000280000000200012000285910484400040 0002004213026 00004 04836l and 1.34 g (24 mmol) of solid KOH given and stirred for 5 minutes. 3.3 ml (22nd mmol) of toluenesulfonic acid methyl ester and the An Set heated to reflux. The reaction will end determined by thin layer chromatography. After cooling the precipitate which has precipitated becomes room temperature filtered. The filtrate is concentrated and over a Silica gel (mobile phase cyclohexane / ethyl acetate 1: 3) cleaned.

After recrystallization from methyl tert-butyl ether / n-hexane, 2.0 g (34% of theory) of 3- (2-chloro-6-fluorophenyl) -1-tert-butyl-4-methoxy are obtained -Δ ³ -pyrrolin-2-one with melting point 94-95 ° C.

Analogous to the production example (Ic-1) and according to the general information on the method according to the invention the compounds listed in Table 3 are obtained of the general formula (Ic).  

Preparation of the starting compounds (Ib) Example (Ib-1)

10.5 g (0.35 mol) of sodium hydride (80%) are converted into 200 ml of absolute toluene suspended. For this purpose, at Rück flow temperature 77 g (0.233 mol) of N- (2-chloro-6-fluorophe nyl-acetyl) -N-tert-butyl-aminoacetic acid ethyl ester in 230 ml of absolute toluene were added dropwise. The approach becomes Reflux heated and the end of the reaction thin determined by layer chromatography. Then will while cooling with ice, ethanol was added dropwise until the Hydrogen evolution has ended. The solvent is distilled off under reduced pressure and at Room temperature stirred in 400 ml of 2N hydrochloric acid. The precipitate is filtered off and at 70 ° C. dried in vacuo. The crude product obtained is made from Chloroform / hexane recrystallized.

39.0 g (60% of theory) of 3- (2-chloro-6-fluorine) are obtained phenyl) -1-tert-butyl-pyrrolidine-2,4-dione from the enamel point mp 237 ° C.  

Analogous to the preparation example (Ib-1) and according to the general information on the method according to the invention the compounds listed in Table 4 are obtained of the general formula (Ib)

Table 4

Preparation of the starting compounds (V) Example (V-13)

23.85 g (0.15 mol) of N-tert-butylglycine ethyl ester together with 21 ml triethylamine in 200 ml absolute Te trahydrofuran cooled to 0-10 ° C. To do this, go to intensive stirring 25.8 g of 2-fluoro-phenylacetic acid chloro rid, dissolved in 20 ml of absolute tetrahydrofuran, added drips and then the reaction batch to the back river boil heated. When the reaction has ended, the Mix in a mixture of 500 ml ice water and 100 ml 1N hydrochloric acid stirred in, extracted with dichloromethane, the organic phase dried and the solvent distilled off in vacuo.

38 g (85% of theory) of N- (2-fluorophenyl-ace) are obtained tyl) -N-tert-butylaminoacetic acid ethyl ester as an oil.

Analogous to the production example (V-1) and according to the general information on the method according to the invention the compounds listed in Table 5 are obtained of the general formula (V)  

Application example Example A

Pre-emergence test
Solvent: 5 parts by weight of acetone
Emulsifier: 1 part by weight of alkylaryl polyglycol ether.

For the preparation of a suitable active ingredient preparation mix 1 part by weight of active ingredient with the specified Native amount of solvent gives the specified amount of emul gator and dilute the concentrate with water to the desired concentration.

Seeds of the test plants are sown in normal soil and watered with the active ingredient preparation after 24 hours. The amount of water per unit area is expediently kept constant. The concentration of active substance in the preparation is irrelevant, the only decisive factor is the amount of active substance applied per unit area. After three weeks, the degree of damage to the plants is rated in% damage compared to the development of the untreated control. It means:
0% = no effect (like untreated control)
100% = total annihilation.

A clear superiority in effectiveness as well  as in crop selectivity compared to the stand the technology show in this test z. B. the connections according to the following production examples: (Ic-2) and (Ic-4).

Claims (14)

1. 4-alkoxy or 4- (substituted) amino-3-aryl-Δ ³ pyrrolin-2-one derivatives of the general formula (I) characterized in that
X and Y independently of one another represent hydrogen, halogen, or a radical from the series alkyl, alkoxy, haloalkyl, haloalkoxy, each unsubstituted or substituted aryl, aryloxy, benzyloxy or arylthio,
Z represents halogen, alkyl or alkoxy,
n stands for a number 0, 1, 2 or 3,
R ¹ and R ² independently of one another represent alkyl or alkoxyalkyl optionally substituted by halogen,
R ³ for unsubstituted or in each case substituted by Ha logen alkyl, alkenyl, alkynyl, alk oxyalkyl, polyalkoxyalkyl or alkylthioalkyl, optionally cycloalkyl interrupted by heteroatoms, unsubstituted or substituted by halogen, alkyl, haloalkyl, haloalkoxy, alkoxy and / or nitro Arylalkyl, arylalkenyl, arylalkynyl or unsubstituted or substituted aryl, where halogen, alkyl, alkoxy, haloalkyl, haloalkoxy, in each case unsubstituted or substituted by halogen, alkyl, alkoxy, haloalkyl and / or haloalkoxy, phenoxy or phenylthio are suitable,
R ^{4 represents} hydrogen, optionally substituted by halogen alkyl or cycloalkyl or unsubstituted or substituted aryl or arylalkyl, halogen, alkyl, alkoxy and haloalkyl or nitro being suitable as substituents,
R ^{5 represents} hydroxyl, in each case unsubstituted or in each case substituted by halogen, alkoxy, alkenoxy, Al kinoxy or polyalkoxy, represents unsubstituted or substituted by halogen and / or alkyl cycloalkoxy or substituted or unsubstituted arylalkyloxy or in which
R ⁶ and R ⁷ independently of one another are hydrogen, alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl, polyalkoxyalkyl, cycloalkyl, optionally interrupted by heteroatoms, each unsubstituted or substituted phenyl, phenylalkyl, phenoxyalkyl, hetaryl or hetarylalkyl or
R ⁶ and R ⁷ together with the nitrogen to which they are attached form a 3- to 9-membered, optionally substituted and, if appropriate, by further heteroatoms under a broken ring or
R ^{7 represents} the group CO-R ⁵ , where
R ^{8 represents} hydrogen, optionally substituted by halogen, alkyl, alkoxy, cycloalkyl or unsubstituted or substituted aryl, arylalkyl, benzyloxy or phenoxy, halogen, alkyl, alkoxy and haloalkyl being suitable as substitutes,
except the connections
1,5-dihydro-4-hydroxy-1- (1,1,3,3-tetramethylbutyl) -3- (2,4,6-trimethylphenyl) -2H-pyrrol-2-one;
1- (1,1-dimethylethyl) -1,5-dihydro-4-hydroxy-3- (2,4,6-trimethylphenyl) -2H-pyrrol-2-one;
3- (2,6-dichlorophenyl) -1,5-dihydro-4-hydroxy-1- (1,1,3,3-tetramethylbutyl) -2H-pyrrol-2-one;
3- (2,6-dichlorophenyl) -1- (1,1-dimethylethyl) -1,5-dihydro-4-hydroxy-2H-pyrrol-2-one. 2. 4-alkoxy or 4- (substituted) amine-3-aryl-Δ ³ pyrrolin-2-one derivatives of the general formula (I) according to claim 1, characterized in that
X and Y independently of one another for hydrogen, fluorine, chlorine, bromine, iodine or a radical of the series, C ₁ -C ₆ -alkyl, C ₁ -C ₆ -alkoxy, C ₁ - C ₆ -haloslkoxy, halogen-C ₁ - C ₄ -alkyl, each of which is unsubstituted or mono- to quintuple, identical or differently substituted phenyl, phenoxy, benzyloxy or phenylthio, the phenyl substituents selected being: fluorine, chlorine, bromine, iodine, C ₁ -C ₄ -alkyl, C ₁ -C ₄ alkoxy and halo-C ₁ -C ₄ alkyl,
Z represents fluorine, chlorine, bromine, iodine, C ₁ -C ₆ alkyl or C ₁ -C ₆ alkoxy,
n stands for a number 0, 1, 2 or 3,
R ¹ and R ² independently of one another represent C ₁ -C ₆ -alkyl or C ₁ -C ₄ -alkoxy-C ₁ -C ₄ -alkyl optionally substituted by fluorine and / or chlorine,
R ³ is unsubstituted or optionally halogen-substituted C ₁ -C ₁₂ alkyl, C ₃ - C ₈ alkenyl, C ₃ -C ₈ alkynyl, C ₁ -C ₁₀ -alkoxy-C ₁ - C ₈ alkyl, C ₁ -C ₈ polyalkoxy-C ₁ -C ₈ alkyl, C ₁ - C ₁₀ alkylthio-C ₁ -C ₈ alkyl or cycloalkyl having 3 to 8 ring atoms, which is caused by oxygen, nitrogen and / or Sulfur can be interrupted, or for each unsubstituted or in the phenyl part up to five times, identical or differently substituted phenyl-C ₁ -C ₆ -alkyl, phenyl-C ₁ -C ₆ -alkenyl, phenyl-C ₁ -C ₆ -alkynyl, phenyl or naphthyl, the substituents selected in each case:
Fluorine, chlorine, bromine, iodine, C ₁ -C ₆ alkyl, C ₁ -C ₆ alkoxy, halo C ₁ -C ₆ alkyl, halo C ₁ -C ₆ alkoxy
or in each case unsubstituted or single to five times, identical or different, by fluorine, chlorine, bromine, iodine, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alkoxy, halogen-C ₁ -C ₄ -alkyl and halogen-C ₁ -C ₄ alkoxy substituted phenoxy or phenylthio,
R ⁴ for hydrogen, optionally substituted by halogen C ₁ -C ₆ alkyl, C ₃ -C ₈ cycloalkyl or for unsubstituted or by fluorine, chlorine, bromine, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl , C ₁ -C ₆ alkoxy or nitro substituted phenyl phenyl-C ₁ -C ₅ alkyl or naphthyl-C ₁ -C ₅ alkyl,
R ^{5 is} hydroxyl, in each case unsubstituted or substituted by fluorine, chlorine, bromine, iodine, C ₁ -C ₁₀ alkoxy, C ₁ -C ₅ alkenoxy, C ₁ -C ₅ alkynoxy, polyalkoxy, or furthermore cycloalkoxy with 3 to 7 ring atoms, the cycloalkyl radical being unsubstituted or mono- to quintuple, identical or different, substituted by fluorine, chlorine, bromine and C ₁ -C ₄ -alkyl, or unsubstituted or by halogen, C ₁ -C ₆ -Alkyl, C ₁ -C ₆ -haloalkyl, C ₁ -C ₆ -alkoxy or nitro-substituted phenyl-C ₁ -C ₄ -alkoxy or naphthyl-C ₁ -C ₄ -alkoxy,
or in which
R ⁶ and R ⁷ independently of one another are hydrogen, C ₁ -C ₁₀ alkyl, C ₃ -C ₁₀ alkenyl, C ₁ -C ₈ alkoxy-C ₁ -C ₈ alkyl, C ₁ -C ₈ alkylthio -C ₁ -C ₈ alkyl, C ₁ -C ₈ polyalkoxy-C ₁ -C ₈ alkyl, cycloalkyl having 3 to 8 ring atoms, which by one, two or three identical or different oxygen, nitrogen and Sulfur atoms can be interrupted, each because unsubstituted or mono- to quintuple, identically or differently substituted phenyl, phenyl-C ₁ -C ₆ -alkyl, phenoxy-C ₁ -C ₆ -alkyl, hetaryl or hetaryl-C ₁ -C ₆ alkyl with 5 or 6 ring atoms each, 1 or 2 identical or different oxygen, nitrogen and sulfur atoms being contained in the ring, or
R ⁶ and R ⁷ together with the nitrogen to which they are attached form a 3- to 8-membered ring which may contain one or two double bonds, one or two further, identical or different oxygen, sulfur or nitrogen atoms may contain, and the single fold to five, identical or different C ₁ - C ₄ alkyl and C ₁ -C ₄ alkylcarbonyl may be substi tuiert, or
R ^{7 represents} a group CO-R ⁸ , where
R ⁸ for hydrogen, optionally substituted by fluorine, chlorine, bromine, C ₁ -C ₁₀ alkyl, C ₁ -C ₁₀ alkoxy, C ₃ -C ₈ cycloalkyl or for unsubstituted or halogenated, C ₁ -C ₆ - alkyl, C ₁ -C ₆ haloalkyl, C ₁ - C ₆ alkoxy or nitro-substituted Phe nyl, phenyl-C ₁ -C ₆ -alkyl, naphthyl-C ₁ - C ₆ -alkyl, benzyloxy or phenoxy. 3. 4-alkoxy or 4- (substituted) amino-3-aryl-Δ ³ pyrrolin-2-one derivatives of the general formula (I) according to claim 1, characterized in that
X for hydrogen, fluorine, chlorine, methyl, ethyl, n- or iso-propyl, methoxy, ethoxy, n- or i-propoxy, halomethyl and halomethoxy with 1, 2 or 3 fluorine and / or chlorine atoms, haloethyl and haloethoxy with 1 to 5, in particular 1 to 3, fluorine and / or chlorine atoms, each unsubstituted or monosubstituted to pentasubstituted, in particular monosubstituted to trisubstituted, the same or differently substituted phenyl, phenoxy, benzyloxy or phenylthio, the phenyl substituents selected being: Chlorine, bromine, methyl, ethyl, n- or iso-propyl, methoxy, ethoxy, n- or iso-propoxy and trifluoromethyl,
Y represents hydrogen, fluorine, chlorine, methyl, ethyl, methoxy, ethoxy or trifluoromethyl,
Z represents fluorine, chlorine, methyl, ethyl, methoxy, ethoxy, halomethyl and halomethoxy with 1, 2 or 3 fluorine and / or chlorine atoms,
n represents 0, 1, 2 or 3,
R ¹ and R ² independently of one another represent C ₁ -C ₅ -alkyl or C ₁ -C ₃ -alkoxy-C ₁ -C ₃ -alkyl optionally substituted by fluorine and / or chlorine,
R ³ for unsubstituted or optionally substituted by fluorine, chlorine and / or bromine methyl, ethyl, in each case straight-chain or branched and unsubstituted or, if appropriate, substituted by fluorine, chlorine and / or bromine, propyl, butyl, pentyl, hexyl, heptyl, Octyl, nonyl, decyl, C ₃ -C ₆ alkenyl, C ₃ -C ₆ alkynyl, C ₁ -C ₄ alkoxy-C ₁ -C ₄ alkyl, C ₁ - C ₄ alkylthio-C ₁ -C ₄ -alkyl stands for cycloalkyl with 3 to 6 ring atoms, which can be interrupted by oxygen, nitrogen or sulfur, or for unsubstituted or single to five times, in particular one to three times, equally or differently substituted phenyl, Benzyl, phen ethyl, phenethenyl or phenethinyl, the substituents selected in each case: fluorine, chlorine, methyl, ethyl, n- or isopropyl, methoxy, ethoxy, trifluoromethyl, tri 079 fluoromethoxy or in each case unsubstituted or single to triple, identical or different, by fluorine, chlorine, me thyl, methoxy, trifluoromethyl and trifluoromethoxy substituted phenoxy, phenylthio,
R ⁴ for hydrogen, optionally substituted by fluorine and / or chlorine-substituted C ₁ -C ₄ alkyl, C ₃ -C ₆ cycloalkyl or unsubstituted or by fluorine, chlorine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy or nitro sub substituted phenyl, phenyl-C ₁ -C ₂ -alkyl or naphthyl-C ₁ -C ₂ -alkyl,
R ⁵ for hydroxy, methoxy, ethoxy, n- or iso-propoxy n-, iso-, sec-butoxy, C ₁ -C ₄ -alkenoxy, C ₁ -C ₄ -alkinoxy, polyalkoxy, halogen-C ₁ -C ₄ alkoxy, where halogen is fluorine and / or chlorine, or cycloalkoxy with 3 to 6 ring atoms, where the cycloalkyl radical can be unsubstituted or monosubstituted to triple, identical or different by fluorine, chlorine, methyl and / or ethyl, or represents phenyl-C ₁ -C ₄ -alkoxy or naphthyl-C ₁ -C ₄ -alkoxy which is unsubstituted or substituted by fluorine, chlorine, methyl, ethyl, trifluoromethyl, trifluoromethoxy or nitro or in which
R ^{6 represents} hydrogen, methyl, ethyl, n- or isopropyl, allyl, n-, iso-, sec- or tert-butyl and
R ⁷ for hydrogen, methyl, ethyl, n-propyl, n-butyl, allyl, propargyl, methoxymethyl, meth oxyethyl, ethoxymethyl, ethoxyethyl, methyl thiomethyl, methylthioethyl, ethylthiomethyl, ethylthioethyl, cyclopropyl, cyclopentyl, cyclohexyl, in each case unsubstituted or simple phenyl, benzyl, phenethyl, pyridyl or pyrimidyl which is substituted by fluorine, chlorine, methyl, ethyl and trifluoromethyl, up to five times, in particular once to three times, or
R ⁶ and R ⁷ together with the nitrogen to which they are attached form a 5- or 6-membered ring which may contain one or two double bonds or which may contain a further nitrogen, oxygen or sulfur atom and which is simple can be substituted three times, identically or differently, by methyl, ethyl, methylcarbonyl or ethylcarbonyl, or
R ^{7 represents} a group CO-R ⁸ , where
R ⁸ represents hydrogen, optionally fluorine- and / or chlorine C ₁ - C ₆ alkyl, C ₁ -C ₆ alkoxy, C ₃ -C ₇ -cycloalkyl or unsubstituted or substituted by fluorine, chlorine, C ₁ -C ₄ Alkyl, C ₁ -C ₂ halo alkyl, C ₁ -C ₄ alkoxy or nitro substituted phenyl, phenyl-C ₁ -C ₄ alkyl, naphthyl-C ₁ -C ₆ alkyl, benzyloxy or phenoxy. 4. 4-alkoxy or 4- (substituted) amino-3-aryl-Δ ³ pyrrolin-2-one derivatives of the general formula (I) according to claim 1, characterized in that
X is hydrogen, fluorine, chlorine, methyl, ethyl, n-propyl, i-propyl, methoxy, ethoxy, n-propoxy, isopropoxy, trifluoromethyl or trifluoromethoxy, unsubstituted or mono- to trisubstituted, identically or differently, substituted phenyl , Benzyloxy or phenoxy, the following being selected as substituents: fluorine, chlorine, methyl and trifluoromethyl,
Y represents hydrogen, fluorine or chlorine,
Z represents fluorine, chlorine, methyl, methoxy, trifluoromethyl or trifluoromethoxy,
n stands for 0, 1 and 2,
R ¹ optionally substituted by fluorine, methyl, ethyl, n- or i-propyl, n-, iso-, sec- or tert-butyl, n-, iso-, sec- or neo-pentyl or for methoxymethyl, ethoxymethyl, n- or iso-propoxymethyl,
R ^{2 represents} methyl, ethyl, n- or i-propyl,
R ^{3 is} unsubstituted methyl, ethyl, n-propyl, isopropyl, n-, iso-, sec- or tert-butyl, optionally substituted by fluorine, chlorine and / or bromine, in each case straight-chain or branched pentyl, hexyl, heptyl, Octyl, allyl, propargyl, methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, cyclopropyl, cyclopentyl, cyclohexyl, or in each case unsubstituted or single to triple, identical or different by fluorine, chlorine, methyl, methoxy, trifluoromethyl, phenoxy and 4-trifluor methyl-phenoxy-substituted phenyl, phenyl, phenethenyl, phenethinyl or benzyl,
R ^{4 represents} hydrogen, methyl, ethyl, n- or isopropyl, n-, iso-, sec- or tert-butyl, unsubstituted or substituted by fluorine, chlorine, methyl, methoxy or trifluoromethyl,
R ⁵ for hydroxy, methoxy, ethoxy, n- or iso-propoxy, n-, iso- or sec-butoxy, trifluoroethoxy, for C ₃ -C ₆ -cycloalkoxy or for unsubstituted or by fluorine, chlorine, methyl, trifluoromethyl , Trifluoromethoxy or nitro substituted phenyl-C ₁ -C ₃ alkoxy or naphthyl-C ₁ -C ₃ alkoxy or in which
R ^{6 represents} hydrogen, methyl, ethyl, n- or i-propyl, allyl, n-, iso-, sec- or tert-butyl and
R ^{7 represents} hydrogen, methyl, ethyl, n-propyl, allyl, n-butyl, unsubstituted or single to triple, identical or different phenyl substituted by fluorine, chlorine, methyl and trifluoromethyl or
R ⁶ and R ⁷ together with the nitrogen to which they are attached represent a heterocycle of the formula which is optionally monosubstituted to triple, identical or different by methyl, ethyl, methylcarbonyl or ethylcarbonyl: or
R ^{7 represents} a group -CO-R ⁸ , where
R ⁸ for hydrogen, optionally substituted by fluorine, methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-butyl, C ₃ -C ₆ -cycloalkyl, methoxy, ethoxy, n- or i- Propoxy, n-, iso- or sec-butoxy, for unsubstituted or substituted by fluorine, chlorine, methyl, trifluoromethyl, methoxy or nitro, phenyl, phenyl-C ₁ -C ₃ -alkyl, naphthyl-C ₁ - C ₃ -alkyl , Benzyloxy or phenoxy. 5. Process for the preparation of 4-alkoxy or 4- (substituted) amino- _3- aryl-Δ ³ -pyrrolin-2-one derivatives of the general formula (I) in which
X and Y independently of one another represent hydrogen, halogen, or a radical from the series alkyl, alkoxy, haloalkyl, haloalkoxy, each unsubstituted or substituted aryl, aryloxy, benzyloxy or arylthio,
Z represents halogen, alkyl or alkoxy,
n stands for a number 0, 1, 2 or 3,
R ¹ and R ² independently of one another represent alkyl or alkoxyalkyl optionally substituted by halogen,
R ³ for unsubstituted or halogen-substituted alkyl, alkenyl, alkynyl, alkoxyalkyl, polyalkoxyalkyl or alkylthioalkyl, cycloalkyl optionally interrupted by hetero atoms, unsubstituted or substituted by halogen, alkyl, haloalkyl, haloalkoxy, alkoxy and / or nitro arylalkyl, Arylalkenyl, arylalkynyl or unsubstituted or substituted aryl, where halogen, alkyl, alkoxy, haloalkyl, haloalkalkoxy, in each case unsubstituted or substituted by halogen, alkyl, alkoxy, haloalkyl and / or haloalkoxy or phenylthio are suitable as substituents,
R ^{4 represents} hydrogen, optionally substituted by halogen-substituted alkyl or cycloalkyl or unsubstituted or substituted aryl or arylalkyl, halogen, alkyl, alkoxy and haloalkyl or nitro being suitable as substituents,
R ^{5 stands} for hydroxy, in each case unsubstituted or in each case substituted by halogen, alkoxy, alkenoxy, alkynoxy or polyalkoxy, for unsubstituted or substituted by halogen and / or alkyl cycloalkoxy or for substituted or unsubstituted arylalkyloxy or in which
R ⁶ and R ⁷ independently of one another are hydrogen, alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl, polyalkoxyalkyl, cycloalkyl, optionally interrupted by heteroatoms, each unsubstituted or substituted phenyl, phenylalkyl, phenoxyalkyl, hetaryl or hetarylalkyl or
R ⁶ and R ⁷ together with the nitrogen to which they are attached form a 3- to 9-membered, optionally substituted and, if appropriate, by further heteroatoms under a broken ring or
R ^{7 represents} the group CO-R ⁸ , where
R ^{8 represents} hydrogen, optionally substituted by halogen, alkyl, alkoxy, cycloalkyl or unsubstituted or substituted aryl, arylalkyl, benzyloxy or phenoxy, halogen, alkyl, alkoxy and haloalkyl being suitable as substitutes,
except the connections
1,5-Dihydro-4-hydroxy-1- (1,1,3,3-tetramethylbutyl) -3- (2,4,6-trimethylphenyl) -2H-pyrrol-2-one:
1- (1,1-dimethylethyl) -1,5-dihydro-4-hydroxy-3- (2,4,6-trimethylphenyl) -2H-pyrrol-2-one;
3- (2,6-dichlorophenyl) -1,5-dihydro-4-hydroxy-1- (1,1,3,3-tetramethylbutyl) -2H-pyrrol-2-one;
3- (2,6-dichlorophenyl) 1- (1,1-dimethylethyl) -1,5-dihydro-4-hydroxy-2H-pyrrol-2-one,
characterized in that one

• A) the 4- (substituted) amino-3-aryl-Δ ³ -pyrrolin-2-one derivatives according to the invention of the formula (Ia)

in which
R ¹ , R ² , R ³ , R ⁴ , R ⁶ , R ⁷ , X, Y, Z
and n have the meanings given above and R ⁷ does not represent the group CO-R ⁸ ,
get if you either
(A-α) 3-aryl-4-hydroxy-Δ ³ -pyrrolin-2-ones of the general formula (Ib) in which
R ¹ , R ² , R ³ , R ⁴ , X, Y have the Z and n meanings given above,
with amines of the formula (II) in which
R ⁶ and R ^{7 have} the meanings given above and R ⁷ does not represent the group CO-R ⁸ ,
if appropriate in the presence of a diluent and if appropriate in the presence of a dehydrating agent,
or if you
(A-β) compounds of the general formula (Ic) in which
R ¹ , R ² , R ³ , R ⁴ , X, Y have the Z and n meanings given above and
R ⁵ represents unsubstituted or halogen-substituted alkoxy, alkenyloxy, alkynyloxy or polyalkoxy, unsubstituted or halogen and / or alkyl-substituted cycloalkoxy or substituted or unsubstituted arylalkoxy,
with amines of the formula (II) in which
R ⁶ and R ^{7 have} the meanings given above and R ⁷ does not represent the group CO-R ⁸ ,
if appropriate in the presence of a diluent and if appropriate under elevated pressure,

• B) or the 3-aryl-Δ ³ pyrrolin-2-one derivatives of the formula (Ia) according to the invention in which

R ¹ , R ² , R ³ , R ⁴ , X, Y, Z and the n meanings given above have and
R ^{6 represents} hydrogen, alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl, polyalkoxyalkyl, if appropriate cycloalkyl interrupted by heteroatoms, in each case unsubstituted or substituted phenyl, phenylalkyl, phenoxyalkyl, hetaryl or hetarylalkyl and
R ^{7 represents} the group -CO-R ⁸ , where
R ^{8 represents} hydrogen, optionally substituted by halogen, alkyl, alkoxy, cycloalkyl or unsubstituted or substituted aryl, arylalkyl, benzyloxy or phenoxy, halogen, alkyl, alkoxy and haloalkyl being possible substitutes,
obtained if compounds of the formula (Id) in which
R ¹ , R ² , R ³ , R ⁴ , X, Y, Z and n have the meanings given above and
R ^{6 represents} hydrogen, alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl, polyalkoxyalkyl, cycloalkyl optionally interrupted by heteroatoms, in each case unsubstituted or substituted phenyl, phenylalkyl, phenoxyalkyl, hetaryl or hetarylalkyl,
either
(B-α) with acid halides of the general formula (III) in which
R ^{7 represents} hydrogen, alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl, polyalkoxyalkyl, cycloal kyl optionally interrupted by heteroatoms, in each case unsubstituted or substituted phenyl, phenylalkyl, phenoxyalkyl, hetaryl or hetaryl alkyl and
Hal represents halogen, especially chlorine and bromine,
if appropriate in the presence of a diluent and if appropriate in the value of an acid binder
or
(B-β) with carboxylic anhydrides of the general formula (IV) R ^{7 '} -CO-O-CO-R ^7' (IV) in which
R ^{7 'has} the meaning given above and is independently the same or different,
if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder. 6. Herbicidal agents, characterized by a content of at least one 4-alkoxy or 4- (substituted ten) -amino-3-aryl-Δ ³ -pyrroline-2 derivative of the formula (I) according to Claims 1 to 5. 7. A method of combating undesirable plants, characterized in that 4-alkoxy or 4- (substituted) -amino-3-aryl-Δ ³ -pyrrolin-2-one derivatives of the formula (I) according to the Claims 1 to 5 can act on unwanted plants and / or their living space. 8. Use of 4-alkoxy or 4- (substituted) - amino-3-aryl-Δ ³ -pyrrolin-2-one derivatives of the formula (I) according to Claims 1 to 5 for combating undesired plants. 9. A process for the preparation of herbicidal compositions, characterized in that 4-alkoxy or 4- (substituted) amino-3-aryl-Δ ³ -pyrrolin-2-one derivatives of the formula (I) according to Claims 1 to 5 mixed with extenders and / or surface-active substances. 10. 3-aryl-4-hydroxy-Δ ³ -pyrrolin-2-one derivative of the general formula (Ib) characterized in that
X and Y independently of one another represent hydrogen, halogen, or a radical from the series alkyl, alkoxy, haloalkyl, haloalkoxy, each unsubstituted or substituted aryl, aryloxy, benzyloxy or arylthio,
Z represents halogen, alkyl or alkoxy,
n stands for a number 0, 1, 2 or 3,
R ¹ and R ² independently of one another represent alkyl or alkoxyalkyl optionally substituted by halogen,
R ³ for unsubstituted or halogen-substituted alkyl, alkenyl, alkynyl, alkoxyalkyl, polyalkoxyalkyl or alkylthioalkyl, cycloalkyl optionally interrupted by hetero atoms, unsubstituted or substituted by halogen, alkyl, haloalkyl, haloalkoxy, alkoxy and / or nitro arylalkyl, Arylalkenyl, arylalkynyl or unsubstituted or substituted aryl, where halogen, alkyl, alkoxy, haloalkyl, haloalkoxy, in each case unsubstituted or phenoxy or phenylthio substituted by halogen, alkyl, alkoxy, haloalkyl and / or haloalkoxy are suitable,
R ^{4 represents} hydrogen, optionally substituted by halogen-substituted alkyl or cycloalkyl or unsubstituted or substituted aryl or arylalkyl, halogen, alkyl, alkoxy and haloalkyl or nitro being suitable as substituents,
except the connections
1,5-dihydro-4-hydroxy-1- (1,1,3,3-tetramethylbutyl) -3- (2,4,6-trimethylphenyl) -2H-pyrrol-2-one;
1- (1,1-dimethylethyl) -1,5-dihydro-4-hydroxy-3- (2,4,6-trimethylphenyl) -2H-pyrrol-2-one;
3- (2,6-dichlorophenyl) -1,5-dihydro-4-hydroxy-1- (1,1,3,3-tetramethylbutyl) -2H-pyrrol-2-one;
3- (2,6-dichlorophenyl) 1- (1,1-dimethylethyl) -1,5-dihydro-4-hydroxy-2H-pyrrol-2-one. 11. Compounds of the general formula (Ic) characterized in that
X and Y independently of one another represent hydrogen, halogen, or a radical from the series alkyl, alkoxy, haloalkyl, haloalkoxy, each unsubstituted or substituted aryl, aryloxy, benzyloxy or arylthio,
Z represents halogen, alkyl or alkoxy,
n stands for a number 0, 1, 2 or 3,
R ¹ and R ² independently of one another represent alkyl or alkoxyalkyl optionally substituted by halogen,
R ³ for unsubstituted or halogen-substituted alkyl, alkenyl, alkynyl, alkoxyalkyl, polyalkoxyalkyl or alkylthioalkyl, cycloalkyl optionally interrupted by hetero atoms, unsubstituted or substituted by halogen, alkyl, haloalkyl, haloalkoxy, alkoxy and / or nitro arylalkyl, Arylalkenyl, arylalkynyl or unsubstituted or substituted aryl, where halogen, alkyl, alkoxy, haloalkyl, haloalkalkoxy, in each case unsubstituted or substituted by halogen, alkyl, alkoxy, haloalkyl and / or haloalkoxy or phenylthio are suitable as substituents,
R ^{4 represents} hydrogen, optionally substituted by halogen alkyl or cycloalkyl or unsubstituted or substituted aryl or arylalkyl, halogen, alkyl, alkoxy and haloalkyl or nitro being suitable as substituents, and
R ⁵ represents unsubstituted or halogen-substituted alkoxy, alkenyl oxy, alkynyloxy or polyalkoxy, unsubstituted or halogen and / or alkyl-substituted cycloalkoxy or substituted or unsubstituted arylalkoxy. 12. Compounds of the formula (Id) characterized in that
X and Y independently of one another represent hydrogen, halogen, or a radical from the series alkyl, alkoxy, haloalkyl, haloalkoxy, each unsubstituted or substituted aryl, aryloxy, benzyloxy or arylthio,
Z represents halogen, alkyl or alkoxy,
n stands for a number 0, 1, 2 or 3,
R ¹ and R ² independently of one another represent alkyl or alkoxyalkyl optionally substituted by halogen,
R ³ represents unsubstituted or halogen-substituted alkyl, alkenyl, alkynyl, alkoxyalkyl, polyalkoxyalkyl or alkylthioalkyl, cycloalkyl optionally interrupted by hetero atoms, unsubstituted or substituted by halogen, alkyl, haloalkyl, haloalkoxy, alkoxy and / or nitro arylalkyl, Arylalkenyl, arylalkynyl or unsubstituted or substituted aryl, where halogen, alkyl, alkoxy, haloalkyl, haloalkoxy, in each case unsubstituted or substituted by halogen, alkyl, alkoxy, haloalkyl and / or haloalkoxy or phenylthio are suitable as substituents,
R ^{4 represents} hydrogen, optionally substituted by halogen-substituted alkyl or cycloalkyl or unsubstituted or substituted aryl or arylalkyl, halogen, alkyl, alkoxy and haloalkyl or nitro being suitable as substituents and
R ^{6 represents} hydrogen, alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl, polyalkoxyalkyl, optionally cycloalkyl interrupted by heteroatoms, in each case unsubstituted or substituted phenyl, phenylalkyl, phenoxyalkyl, hetaryl or hetarylalkyl.