KR100364018B1 - Alkoxy-alkyl-substituted 1H-3-aryl-pyrrolidine-2,4-dione used as herbicide and insecticide - Google Patents

Abstract

The present invention relates to novel 1H-3-aryl-pyrrolidine-2,4-dione derivatives of the following general formula (I), methods for their preparation, and intermediates thereof.

In the above formula,

A, B, G, X, Y and Z have the meanings mentioned in the specification.

Compounds of general formula (I) are used as insecticides and herbicides.

Description

Alkoxy-alkyl substituted 1H-3-aryl-pyrrolidine-2,4-dione used as herbicide and pesticide

The present invention relates to novel 1H-3-aryl-pyrrolidine-2,4-dione derivatives, many methods for their preparation, and their use as pesticides, in particular pesticides and acaricides.

The pharmaceutical properties of 3-acyl-pyrrolidine-2,4-dione have already been described (S. Suzuki et al. Chem. Pharm. Bull. 15 1120 (1967)). In addition, N-phenylpyrrolidine-2, 4-dione is Al. R. Schmierer and H. It was synthesized by H. Mildenberger (Liebigs Ann. Chem. 1985 1095). The biological activity of these compounds is not yet known.

EP-A 0 262 399 and GB-A 2 266 888 describe compounds of similar structure (3-aryl-pyrrolidine-2,4-dione), but do not describe their herbicidal, pesticidal or acaricide activity. Did. Unsubstituted bicyclic 3-aryl-pyrrolidine-2,4-dione derivatives (EP-A 355 599 and EP 415 211) and substituted monocyclic 3-aryl-pyrrolidine-2,4-dione Derivatives (EP-A 377 893 and EP 442 077) are known as compounds having herbicidal, insecticidal or acaricide activity.

Polycyclic 3-aryl-pyrrolidine-2,4-dione derivatives (EP 442 073) and 1H-3-aryl-pyrrolidine-dione derivatives (EP 456 063 and EP 521 334) are also known.

According to the invention a novel substituted 1H-3-aryl-pyrrolidine-2,4-dione derivative of the general formula (I)

Where

A represents hydrogen, or in each case optionally represents halogeno-substituted alkyl, alkenyl, alkoxy alkyl, polyalkoxyalkyl or alkylthioalkyl, or cycloalkyl optionally interrupted and optionally substituted by at least one hetero atom Or in each case optionally represents halogen-, alkyl-, halogenoalkyl-, alkoxy- or nitro-substituted aryl, arylalkyl or hetaryl,

B represents alkyl or alkoxyalkyl, or

A and B together with the C atom to which they are attached represent an unsubstituted or substituted ring which is optionally interrupted and saturated or unsaturated by at least one heteroatom,

X represents alkyl or alkoxy,

Y represents hydrogen, alkyl or alkoxy,

Z represents hydrogen, alkyl or alkoxy,

G is hydrogen (a) or a group

E represents one equivalent of a metal ion or an ammonium ion,

L represents oxygen or sulfur,

M represents oxygen or sulfur,

R ¹ is in each case optionally halogen- or alkyl-substituted cyclo, which may be interrupted by halogeno-substituted alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl or polyalkoxyalkyl, or at least one hetero atom Alkyl, or in each case optionally substituted phenyl, phenylalkyl, hydroxy, phenoxyalkyl or hydroxyaryloxyalkyl,

R ² in each case optionally represents halogeno-substituted alkyl, alkenyl, alkoxyalkyl or polyalkoxyalkyl, or in each case optionally represents cycloalkyl, phenyl or benzyl,

R ³ , R ⁴ and R ⁵ independently of each other represent in each case optionally halogeno-substituted alkyl, alkoxy, alkylamino, dialkylamino, alkylthio, alkenylthio or cycloalkylthio, or in each case optionally Substituted phenyl, phenoxy or phenylthio,

R ⁶ and R ⁷ independently of one another represent hydrogen or in each case optionally represent halogeno-substituted alkyl, cycloalkyl, alkenyl, alkoxy or alkoxyalkyl, optionally substituted phenyl, or optionally substituted Benzyl or a ring optionally interrupted by oxygen or sulfur with the N atom to which they are attached,

Provided that at least one of substituents X and Z represents alkoxy when X represents alkyl.

Considering the various meanings (a), (b), (c), (d), (e), (f) and (g) of the group G, the following main structures (Ia) to (Ig) are obtained:

Where

A, B, E, L, M, X, Y, Z, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ and R ⁷ have the meanings mentioned above.

By one or more chiral centers, the compounds of the general formulas (Ia) to (Ig) are generally obtained in the form of stereoisomeric mixtures which can be separated by conventional means, if appropriate. They can be used in the form of their diastereomeric mixtures and also in the form of pure diastereomers or enantiomers. For convenience, the compounds of general formulas (Ia) to (Ig) are intended to mean always mixtures containing pure compounds and different proportions of isomers, enantiomers and stereoisomeric compounds.

According to the invention also novel substituted 1H-3-aryl-pyrrolidine-2,4-dione derivatives of general formula (I)

(A) Intramolecular condensation reaction of N-acylamino acid ester of the following general formula (II) in the presence of a diluent and in the presence of a base to give 1H-3-aryl-pyrrolidine-2,4 of the following general formula (Ia) Preparing diones and / or enols thereof;

(B) the compound of the following general formula (Ia),

a) reacting with an acid halide of the general formula (III), optionally in the presence of a diluent and optionally in the presence of an acid-binding agent,

B) reacting with a carboxylic anhydride of formula (IV), optionally in the presence of a diluent, and optionally in the presence of an acid-binding agent, to obtain a compound of formula (Ib)

(C) The compound of formula (Ia) is reacted with a chloroformic acid ester or chloroformic acid thioester of formula (V), optionally in the presence of a diluent, and optionally in the presence of an acid-binding agent obtaining the compound of -a)

(D) the compound of the following general formula (Ia),

a) reacting with a chloromonothioformic ester or chlorodithioformic ester of the general formula (VI), optionally in the presence of a diluent and optionally in the presence of an acid-binding agent,

B) optionally reacting with carbon disulfide in the presence of a diluent and optionally in the presence of a base, followed by reaction with an alkyl halide of the general formula (VII) to give a compound of the general formula (Ic-b)

(E) reacting a compound of formula (Ia) with sulfonyl chloride of formula (VIII), optionally in the presence of a diluent, and optionally in the presence of an acid-binding agent, To obtain,

(F) 1H-3-aryl-pyrrolidine-2,4-dione of Formula (Ia) and / or an enol thereof, in the presence of a diluent, and optionally in the presence of an acid-binding agent Reacting with the phosphorus compound of (IX) to give 3-aryl-pyrrolidine-2,4-dione of the general formula (Ie), or (G) the compound of the general formula (Ia), optionally in the presence of a diluent It was found that it was obtained by one of the methods of reacting with a metal hydroxide, a metal alkoxide or an amine of the following general formulas (X) and (XI) to give a compound of the following general formula (If).

Where

A, B, L, X, Y, Z, R ¹ , R ² , R ³ , R ⁴ and R ⁵ have the meanings mentioned above,

R ⁸ represents alkyl, in particular C ₁ -C ₆ -alkyl,

Hal in formulas (III) and (IX) represents halogen, in particular chlorine or bromine,

M represents oxygen or sulfur,

Hal in formula (VII) represents chlorine, bromine or iodine,

E represents one equivalent of a metal ion or an ammonium ion,

Me represents monovalent or divalent metal ions such as lithium, sodium, potassium, magnesium or calcium,

t represents a number of 1 or 2,

R ⁹ , R ¹⁰ and R ¹¹ independently of one another represent hydrogen and / or alkyl, in particular C ₁ -C ₆ -alkyl.

In addition, (H) a compound of the following general formula (Ig) is a compound of the following general formula (Ia), α) isocyanate or iso isobarate of the following general formula (XII) optionally in the presence of a diluent and optionally in the presence of a catalyst React with thiocyanate,

β) it was found to be obtained by reacting with carbamoyl chloride or thiocarbamoyl chloride of the general formula (XIII), optionally in the presence of a diluent, and optionally in the presence of an acid-binding agent.

Where

A, B, L, X, Y, Z, R ⁶ and R ⁷ have the meanings mentioned above.

It has also been found in accordance with the present invention that the novel 1H-3-aryl-pyrrolidine-2,4-dione derivatives of general formula (I) exhibit excellent pesticidal, acaricide and herbicidal activity.

The following description shows the ranges for the preferred substituents and / or radicals set forth above and in the following formulas.

A preferably represents hydrogen or in each case is optionally mono- or poly-halogeno-substituted C ₁ -C ₁₂ -alkyl, C ₃ -C ₈ -alkenyl, C ₁ -C ₁₀ -alkoxy-C _1- C ₈ -alkyl, C ₁ -C ₈ -polyalkoxy-C ₁ -C ₈ -alkyl or C ₁ -C ₁₀ -alkylthio-C ₁ -C ₆ -alkyl, or blocked by oxygen and / or sulfur Which may be from 3 to 8 ring atoms and optionally halogen-, C ₁ -C ₄ -alkyl- or C ₁ -C ₄ -alkoxy-substituted cycloalkyl, in each case optionally mono- to poly-halogen- , C ₁ -C ₆ - alkyl -, C ₁ -C ₆ - halogenoalkyl -, C ₁ -C ₆ - alkoxy - and / or - a nitro-substituted phenyl, naphthyl, pyridyl, imidazolyl, indole Reel, thiazolyl, furanyl, thienyl, phenyl-C ₁ -C ₆ -alkyl or naphthyl-C ₁ -C ₆ -alkyl,

B preferably represents C ₁ -C ₁₂ -alkyl or C ₁ -C ₈ -alkoxy-C ₁ -C ₆ -alkyl,

A, B and the carbon atoms to which they are attached are preferably C ₁ -C ₆ -alkyl, C ₃ -C ₈ -cycloalkyl, C ₁ -C ₄ -halogenoalkyl, C ₁ -C ₆ -alkoxy, C ₁ Or represent saturated or unsaturated C ₃ -C ₁₀ -spirocyclic radicals optionally mono- or polysubstituted by -C ₆ -alkylthio, halogen or phenyl and optionally blocked by oxygen or sulfur, or

A, B and the carbon atoms to which they are attached are preferably substituted by alkylenediyl groups optionally interrupted by one or two oxygen and / or sulfur atoms or substituted by alkylenedioxy or alkylenedithio groups ₃ -C ₆ -spirocyclic radical, wherein the alkylenediyl, alkylenedioxy or alkylenedithio group together with the carbon atom to which they are attached form an additional 5- to 8-membered spirocyclic ring or ,

A, B and the carbon atom to which they are attached is preferably two with the substituent C ₁ -C ₄ - saturation which can optionally substituted by alkoxy or halogen, and blocked by the oxygen or sulfur -alkyl, C ₁ -C ₄ Or C ₃ -C ₈ -spirocyclic radical representing an unsaturated 5- or 8-membered ring.

A particularly preferably represents hydrogen or in each case is optionally mono to hexa-fluoro- or chloro-substituted C ₁ -C ₁₀ -alkyl, C ₂ -C ₆ -alkenyl, C ₁ -C _8- Alkoxy-C ₁ -C ₆ -alkyl, C ₁ -C ₆ -polyalkoxy-C ₁ -C ₆ -alkyl or C ₁ -C ₈ -alkylthio-C ₁ -C ₆ -alkyl, or 1 or 2 oxygen And / or optionally fluoro-, chloro-, C ₁ -C ₃ -alkyl- or C ₁ -C ₃ -alkoxy-substituted cycloalkyl having 3 to 7 atoms, which can be interrupted by sulfur atoms or , in each case optionally mono- or di-fluoro-, chloro-, bromo -, -C ₁ -C ₄ - alkyl -, -C ₁ -C ₄ - halogenoalkyl -, -C ₁ -C ₄ - Alkoxy or -nitro-substituted phenyl, pyridyl, thienyl, furanyl, imidazolyl, indolyl or phenyl-C ₁ -C ₄ -alkyl,

B particularly preferably represents C ₁ -C ₁₀ -alkyl or C ₁ -C ₆ -alkoxy-C ₁ -C ₄ -alkyl,

A, B and the carbon atoms to which they are attached are particularly preferably C ₁ -C ₆ -alkyl, C ₃ -C ₈ -cycloalkyl, C ₁ -C ₃ -halogenoalkyl, C ₁ -C ₆ -alkoxy, C Saturated or unsaturated C ₃ -C ₉ -spirocyclic radicals, optionally substituted one or more times by _1- C ₆ -thioalkyl, fluorine, chlorine or petyl and optionally blocked by oxygen or sulfur, or

A, B and the carbon atoms to which they are attached are particularly preferably C ₃ substituted by alkylenediyl groups optionally interrupted by one or two oxygen or sulfur atoms or substituted by alkylenedioxy or alkylenedithio groups -C ₆ -spirocyclic radical, wherein the alkylenediyl, alkylenedioxy or alkylenedithio group together with the carbon atom to which they are attached form an additional 5- to 7-membered spirocyclic ring,

A, B and the carbon atoms to which they are attached are particularly preferably two substituents together optionally substituted by C ₁ -C ₃ -alkyl, C ₁ -C ₃ -alkoxy, fluorine, chlorine or bromine and by oxygen or sulfur C ₃ -C ₆ -spirocyclic radicals which represent saturated or unsaturated 5- to 7-membered rings which may be blocked.

A very particularly preferably represents hydrogen or in each case is optionally mono- to tri-fluoro- and / or -chloro-substituted C ₁ -C ₈ -alkyl, C ₂ -C ₄ -alkenyl, C _1- C ₆ -alkoxy-C ₁ -C ₄ -alkyl, C ₁ -C ₄ -polyalkoxy-C ₁ -C ₄ -alkyl or C ₁ -C ₆ -alkylthio-C ₁ -C ₄ -alkyl, or Represents optionally fluoro-, chloro-, methyl-, ethyl-, methoxy- or ethoxy-substituted cycloalkyl having 3 to 6 ring atoms which may be interrupted by 1 to 2 oxygen and / or sulfur atoms Or in each case optionally mono- or di-fluoro-, -chloro-, -bromo-, -methyl-, -ethyl-, -propyl, -isopropyl-, -methoxy-, -ethoxy-, -Trifluoromethyl- and / or -nitro-substituted phenyl, furanyl, thienyl, imidazolyl, indolyl, pyridyl or benzyl,

B very particularly preferably represents C ₁ -C ₈ -alkyl or C ₁ -C ₄ -alkoxy-C ₁ -C ₂ -alkyl,

A, B and the carbon atoms to which they are attached are very particularly preferably methyl, ethyl, propyl, isopropyl, butyl, isobutyl, Sec-butyl, t-butyl, cyclohexyl, trifluoromethyl, methoxy, ethoxy Is optionally substituted one or more times by propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, t-butoxy, methylthio, ethylthio, fluorine, chlorine or phenyl and by oxygen or sulfur Represent an optionally blocked saturated or unsaturated C ₃ -C ₈ -spirocyclic radical, or

A, B and the carbon atoms to which they are attached are very particularly preferably C ₃ -C ₆ -spirocyclic radicals substituted by alkylenediyl groups optionally substituted by oxygen or sulfur atoms or substituted by alkylenedioxy groups Wherein the alkylenediyl or alkylenedioxy group together with the carbon atom to which they are attached form additional 5- to 7-membered spirocyclic radicals, or

A, B and the carbon atoms to which they are attached are very particularly preferably C ₃ -C ₆ -spirosides which represent saturated or unsaturated 5- or 6-membered rings in which two substituents together may be interrupted by oxygen or sulfur Represents a click radical.

X preferably represents C ₁ -C ₆ -alkyl or C ₁ -C ₆ -alkoxy.

X particularly preferably represents C ₁ -C ₅ alkyl or C ₁ -C ₄ -alkoxy.

X very preferably represents methyl, ethyl, propyl, isopropyl, methoxy, ethoxy, propoxy or isopropoxy.

Y preferably represents hydrogen, C ₁ -C ₆ -alkyl or C ₁ -C ₆ -alkoxy.

Y particularly preferably represents hydrogen, C ₁ -C ₅ -alkyl or C ₁ -C ₄ -alkoxy.

Y very preferably represents hydrogen, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, t-butyl, methoxy, ethoxy, propoxy or isopropoxy.

Z preferably represents hydrogen, C ₁ -C ₆ -alkyl or C ₁ -C ₆ -alkoxy.

Z particularly preferably represents hydrogen, C ₁ -C ₄ -alkyl or C ₁ -C ₄ -alkoxy.

Z very preferably represents hydrogen, methyl, ethyl, propyl, isopropyl, methoxy, ethoxy, propoxy or isopropoxy.

In this regard, when X represents alkyl, at least one of the substituents Y and Z represents alkoxy.

G is preferably hydrogen (a) or a group

From here,

E represents one equivalent of a metal ion or an ammonium ion,

L represents oxygen or sulfur,

M represents oxygen or sulfur,

R ¹ is preferably in each case optionally mono- or poly-halogeno-substituted C ₁ -C ₂₀ -alkyl, C ₂ -C ₂₀ -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 ₂ -C ₈ -alkyl or to be interrupted by at least one oxygen and / or sulfur atom Optionally represent 3 to 8 optionally halogen- or C ₁ -C ₆ -alkyl-substituted cycloalkyl, or

Optionally mono-to penta-halogenoalkyl -, - nitro -, -C ₁ -C ₆ - alkyl -, -C ₁ -C ₆ - alkoxy -, -C ₁ -C ₆ - halogenoalkyl -, -C ₁ - C ₆ -halogenoalkoxy-, -C ₁ -C ₆ -halogenoalkylthio or -C ₁ -C ₆ -alkylsulfonyl-substituted phenyl,

Optionally mono-to penta-halogenoalkyl -, -C ₁ -C ₆ - alkyl -, -C ₁ -C ₆ - alkoxy -, -C ₁ -C ₆ - halogenoalkyl -, or -C ₁ -C ₆ - haloalkyl Genoaloxy-substituted phenyl-C ₁ -C ₆ -alkyl, or

Optionally represents mono- to tri-halogeno- or -C ₁ -C ₆ -alkyl-substituted pyridyl, thienyl, furanyl, pyrazolyl, pyrimidyl or thiazolyl,

Optionally mono- to tri-halogeno- or -C ₁ -C ₆ -alkyl-substituted phenoxy-C ₁ -C ₆ -alkyl, or

Optionally mono- or di-halogeno-, -amino- or -C ₁ -C ₆ -alkyl-substituted pyridinyloxy-C ₁ -C ₆ -alkyl, pyrimidinyloxy-C ₁ -C ₆ -alkyl or thiazolyl oxy -C ₁ -C ₆ - represents alkyl,

R ² is preferably in each case optionally mono- or poly-halogeno-substituted C ₁ -C ₂₀ -alkyl, C ₃ -C ₂₀ -alkenyl, C ₁ -C ₈ -alkoxy-C ₂ -C ₈ -Alkyl or C ₁ -C ₈ -polyalkoxy-C ₂ -C ₈ -alkyl, or

Optionally represents mono- or poly-halogeno-, -C ₁ -C ₄ -alkyl- and / or -C ₁ -C ₄ -alkoxy-substituted C ₃ -C ₈ -cycloalkyl, or

Optionally mono-or tri-halogeno-, - nitro -, -C ₁ -C ₆ - alkyl -, -C ₁ -C ₆ - alkoxy -, or -C ₁ -C ₆ - halogenoalkyl-substituted phenyl or benzyl ,

R ³ , R ⁴ and R ⁵ are preferably independently of each other at each occurrence optionally mono- or poly-halogeno-substituted C ₁ -C ₈ -alkyl, C ₁ -C ₈ -alkoxy, C ₁ -C ₈ -Alkylamino, di- (C ₁ -C ₈ ) -alkoxyamino, C ₁ -C ₈ -alkylthio, C ₃ -C ₆ -alkenylthio or C ₃ -C ₇ -cycloalkylthio, or Halogen, nitro, cyano, C ₁ -C ₄ -alkoxy, C ₁ -C ₄ -halogenoalkoxy, C ₁ -C ₄ -alkylthio, C ₁ -C ₄ -halogenoalkylthio, C _1- Phenyl, phenoxy or phenylthio optionally mono- or poly-substituted by C ₄ -alkyl or C ₁ -C ₄ -halogenoalkyl,

R ⁶ and R ⁷ preferably represent hydrogen independently of one another, or in each case optionally mono- or poly-halogeno-substituted C ₁ -C ₃ -alkyl, C ₃ -C ₈ -cycloalkyl, C ₁ -C ₈ -alkoxy, C ₃ -C ₈ -alkenyl or C ₁ -C ₈ -alkoxy-C ₁ -C ₈ -alkyl, or optionally mono- to tri-halogeno-, -C ₁ -C ₈ - halogenoalkyl -, -C ₁ -C ₈ - alkyl -, or -C ₁ -C ₈ - alkoxy - represents an optionally substituted phenyl or optionally mono- to tri-halogeno -, -C ₁ -C ₈ - alkyl, -, -C ₁ -C ₈ -halogenoalkyl- or -C ₁ -C ₈ -alkoxy-substituted benzyl or together represent C ₃ -C ₆ -alkylene radicals which are optionally interrupted by oxygen or sulfur .

G is particularly preferably hydrogen (a) or a group

From here,

E represents one equivalent of a metal ion or an ammonium ion,

L represents oxygen or sulfur,

M represents oxygen or sulfur,

R ¹ is particularly preferably in each case optionally mono- to hexa-fluoro- or -chloro-substituted C ₁ -C ₁₆ -alkyl, C ₂ -C ₁₆ -alkenyl, C ₁ -C ₆ -alkoxy- C ₁ -C ₆ -alkyl, C ₁ -C ₆ -alkylthio-C ₁ -C ₆ -alkyl, C ₁ -C ₆ -polyalkoxy-C ₂ -C ₆ -alkyl or 1 or 2 oxygen and / or Optionally represents fluoro-, chloro- or C ₁ -C ₅ -alkyl-substituted cycloalkyl having 3 to 7 ring atoms which may be interrupted by a sulfur atom, or

Optionally mono-to tri-fluoro--chloro -, - bromo -, - nitro -, -C ₁ -C ₄ - alkyl -, -C ₁ -C ₄ - alkoxy -, -C ₁ -C ₃ - halogenoalkyl -, -C ₁ -C _{3-halogeno-alkoxy} -, -C ₁ -C ₄ - alkylthio -, or -C ₁ -C ₄ - alkylsulfonyl-or represent a substituted phenyl,

Optionally mono-to tri-fluoro-, - chloro -, - bromo -, -C ₁ -C ₄ - alkyl -, -C ₁ -C ₄ - alkoxy -, -C ₁ -C ₃ - halogenoalkyl - Or -C ₁ -C ₃ -halogenoalkoxy-substituted phenyl-C ₁ -C ₄ -alkyl, or

Optionally represents mono- or di-fluoro-, -chloro-, -bromo- or C ₁ -C ₄ -alkyl-substituted pyridyl, thienyl, furanyl, pyrazolyl, pyrimidyl or thiazolyl,

Optionally mono- or di-fluoro -, - chloro -, - bromo - or -C ₁ -C ₄ - alkyl - substituted phenoxy during -C ₁ -C ₅ - or represent alkyl,

Optionally mono- or di-fluoro -, - chloro -, - bromo -, - amino - or -C ₁ -C ₄ - alkyl-substituted pyrimidinyl oxy -C ₁ -C ₅ - alkyl, pyridyloxy -C ₁ -C ₅ -alkyl or thiazolyloxy-C ₁ -C ₅ -alkyl,

R ² is particularly preferably in each case halogen mono- to hexa-fluoro- or -chloro-substituted C ₁ -C ₁₆ -alkyl, C ₃ -C ₁₆ -alkenyl, C ₁ -C _6- Alkoxy-C ₂ -C ₆ -alkyl or C ₁ -C ₆ -polyalkoxy-C ₂ -C ₆ -alkyl, or

Optionally mono- to hexa-fluoro-, -chloro-, -C ₁ -C ₃ -alkyl- or -C ₁ -C ₃ -alkoxy-substituted C ₃ -C ₇ -cycloalkyl, or

Optionally mono- or di-fluoro -, - chloro -, - bromo -, - nitro -, -C ₁ -C ₄ - alkyl -, -C ₁ -C ₃ - alkoxy - or -C ₁ -C ₃ - Halogenoalkyl-substituted phenyl or benzyl,

R ³ , R ⁴ and R ⁵ are particularly preferably independently of one another in each case optionally mono- to hexa-fluoro- or -chloro-substituted C ₁ -C ₆ -alkyl, C ₁ -C ₆ -alkoxy, C ₁ -C ₆ -alkylamino, di- (C ₁ -C ₆ ) -alkylamino, C ₁ -C ₆ -alkylthio, C ₃ -C ₄ -alkenylthio or C ₃ -C ₆ -cycloalkylthio Or fluorine, chlorine, bromine, nitro, cyano, C ₁ -C ₃ -alkoxy, C ₁ -C ₃ -halogenoalkoxy, C ₁ -C ₃ -alkylthio, C ₁ -C ₃ -halo, respectively Phenyl, phenoxy or phenylthio optionally monosubstituted or disubstituted by genoalkylthio, C ₁ -C ₃ -alkyl or C ₁ -C ₃ -halogenoalkyl,

R ⁶ and R ⁷ particularly preferably independently represent hydrogen, or in each case optionally mono- to hexa-fluoro- or -chloro-substituted C ₁ -C ₆ -alkyl, C ₃ -C _6- Cycloalkyl, C ₁ -C ₆ -alkoxy, C ₃ -C ₆ -alkenyl or C ₁ -C ₆ -alkoxy-C ₂ -C ₆ -alkyl, or represent fluorine, chlorine, bromine, C ₁ -C ₅ Phenyl optionally mono- or di-substituted by halogenoalkyl, C ₁ -C ₅ -alkyl or C ₁ -C ₅ -alkoxy, or fluorine, chlorine, bromine, C ₁ -C ₅ -alkyl, C _1- Benzyl optionally monosubstituted or disubstituted by C ₅ -halogenoalkyl or C ₁ -C ₅ -alkoxy, or together represent C ₃ -C ₆ -alkylene radicals which are optionally interrupted by oxygen or sulfur.

G is very particularly preferably hydrogen (a) or a group

From here,

E represents 1 equivalent of a metal ion or an ammonium ion,

L represents oxygen or sulfur,

M represents oxygen or sulfur,

R ¹ is very particularly preferably in each case optionally mono- to tri-fluoro- or -chloro-substituted C ₁ -C ₁₄ -alkyl, C ₂ -C ₁₄ -alkenyl, C ₁ -C ₄ -alkoxy -C ₁ -C ₆ - alkyl, C ₁ -C ₄ - alkylthio -C ₁ -C ₆ - alkyl or C ₁ -C ₄ - alkoxy poly -C ₂ -C ₄ - alkyl, or one or two oxygen and And / or optionally fluoro-, chloro-, methyl-, ethyl-, propyl-, iso-propyl-, butyl-, isobutyl- or t-butyl- of 3 to 6 ring atoms which may be interrupted by sulfur atoms; Substituted cycloalkyl, or

Optionally mono- or di-fluoro-, -chloro-, -bromo-, -methyl-, -ethyl-, -propyl-, -isopropyl-, -methoxy-, -ethoxy-, -trifluoro Methyl-, -trifluoromethoxy-, -methylthio-, -ethylthio-, -methylsulfonyl-, -ethylsulfonyl- or -nitro-substituted phenyl,

Optionally mono- or di-fluoro-, -chloro-, -bromo-, -methyl-, -ethyl-, -propyl-, -isopropyl-, -methoxy-, -ethoxy-, -trifluoro methyl-or-trifluoromethoxy-substituted phenyl, -C ₁ -C ₃ - alkyl, or represent,

Optionally represents moro- or di-fluoro-, -chloro-, -bromo-, -methyl- or -ethyl-substituted thienyl, furanyl or pyridyl, or

Optionally represents mono- or di-fluoro-, -chloro-, -methyl- or -ethyl-substituted phenoxy-C ₁ -C ₄ -alkyl, or

In each case optionally mono- or di-fluoro -, - chloro -, - amino-, -methyl- or -ethyl-substituted pyrimidinyl oxy -C ₁ -C ₄ - alkyl, pyridyloxy -C ₁ - C ₄ -alkyl or thiazolyloxy-C ₁ -C ₄ -alkyl,

R ² is very particularly preferably in each case optionally mono- to tri-fluoro-, -chloro-substituted C ₁ -C ₁₄ -alkyl, C ₃ -C ₁₄ -alkenyl, C ₁ -C ₄ -alkoxy -C ₂ -C ₆ -alkyl or C ₁ -C ₄ -polyalkoxy-C ₂ -C ₆ -alkyl, or

Optionally represents mono- to tri-fluoro-, -chloro-, -methyl-, -ethyl-, -propyl-, -isopropyl- or -methoxy-substituted C ₃ -C ₆ -cycloalkyl,

In each case optionally mono- or di-fluoro-, -chloro-, -nitro-, -methyl-, -ethyl-, -propyl-, -isopropyl-, -methoxy-, -ethoxy- or -tri Fluoromethyl- substituted phenyl or benzyl,

R ³ , R ⁴ and R ⁵ are very particularly preferably independently of each other in each case optionally mono- to tri-fluoro- or -chloro-substituted C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alkoxy , C ₁ -C ₄ -alkylamino, di- (C ₁ -C ₄ ) -alkylamino or C ₁ -C ₄ -alkylthio, or represent fluorine, chlorine, bromine, nitro, cyano, C _1- C ₂ -alkoxy, C ₁ -C ₂ -fluoroalkoxy, C ₁ -C ₂ -alkylthio, C ₁ -C ₂ -fluoroalkylthio, C ₁ -C ₂ -alkyl or C ₁ -C ₂ -fluor Phenyl, phenoxy or phenylthio optionally mono- or di-substituted by roalkyl,

R ⁶ and R ⁷ very particularly preferably represent hydrogen independently of one another, or in each case optionally mono- to tri-fluoro- or -chloro-substituted C ₁ -C ₄ -alkyl, C ₃ -C ₆ -Cycloalkyl, C ₁ -C ₄ -alkoxy, C ₃ -C ₄ -alkenyl or C ₁ -C ₄ -alkoxy-C ₂ -C ₄ -alkyl or represent fluorine, chlorine, bromine, C ₁ -C ₄ - halogenoalkyl, C ₁ -C ₄ - alkyl or C ₁ -C ₄ - represents a day or disubstituted by alkoxy, or phenyl, optionally, fluorine, chlorine, bromine, C ₁ -C ₄ - alkyl, C ₁ - Benzyl optionally mono- or disubstituted by C ₄ -halogenoalkyl or C ₁ -C ₄ -alkoxy, or together represent C ₃ -C ₆ -alkylene radicals which are optionally interrupted by oxygen or sulfur.

In the above definition, saturated or unsaturated alkyl radicals (also when bonded with hetero atoms such as for example alkoxy or alkylthio) can be as straight or branched as possible.

Optionally polysubstituted radicals may be substituted by the same or different substituents selected from those specified for these radicals.

The definitions and / or descriptions of the general or preferred radicals mentioned above may combine them freely with one another, ie also combinations between the respective ranges and the preferred ranges are also possible. These apply correspondingly to the final product and the precursors and intermediates.

According to the invention, preferred compounds of general formula (I) are compounds which combine the abovementioned definitions as being preferred.

According to the invention, particularly preferred compounds of general formula (I) are compounds which combine the definitions mentioned above as particularly preferred.

According to the invention, very particularly preferred compounds of formula (I) are compounds which combine the definitions mentioned above as very particularly preferred.

Preferred groups of compounds also include compounds of the general formula (Ih) below.

Where

X and Z represent alkyl,

Y represents alkoxy,

A, B and G have the above-mentioned meanings.

Preference is furthermore given to compounds of the general formula (Ih) in which X and Y represent alkyl, Z represents alkoxy and A, B and G have the meanings mentioned above.

Preference is furthermore given to compounds of the formula (Ih) in which X represents alkyl, Y represents hydrogen, Z represents alkoxy and A, B and G have the meanings mentioned above.

Further groups of preferred compounds include compounds of the formula (Ih) in which X represents alkyl, Y represents alkoxy, Z represents hydrogen and A, B and G have the meanings mentioned above.

Another group of preferred compounds includes compounds of the general formula (Ih) in which X represents alkoxy, Y represents alkyl, Z represents hydrogen and A, B and G have the meanings mentioned above.

In addition to the compounds mentioned in the preparation examples, compounds of the general formula (Ia) may be mentioned specifically:

In addition to the compounds mentioned in the preparation examples, compounds of the general formula (Ib) may be mentioned specifically:

In addition to the compounds mentioned in the preparation examples, compounds of the general formula (Ic) may be mentioned specifically:

In addition to the compounds mentioned in the preparation examples, compounds of the general formula (Id) may be mentioned specifically:

In addition to the compounds mentioned in the preparation examples, compounds of the general formula (Ie) may be mentioned specifically:

Table 5

In addition to the compounds mentioned in the preparation examples, compounds of the general formula (If-a) may be mentioned specifically:

Table 6a

In addition to the compounds mentioned in the preparation examples, compounds of the following formula (If-b) may be mentioned individually:

Table 6a

In addition to the compounds mentioned in the preparation examples, compounds of the general formula (Ig-a) may be mentioned specifically:

Table 7a

In addition to the compounds mentioned in the preparation examples, compounds of the general formula (Ig-b) may be mentioned specifically:

Table 7b

Reaction of the process according to the invention when ethyl N- (2-methyl-4-methoxyphenylacetyl) -1-amino-4-ethyl-cyclohexanecarboxylate is used as starting compound according to process (A) The process can be represented by the following scheme:

When 3- (2-methyl-6-methoxyphenyl) -5,5-dimethyl-pyrrolidine-2,4-dione and pivaloyl chloride are used as starting compounds according to the method (B _α ), The reaction process of the process according to the invention can be represented by the following scheme.

According to method (B _β ) 3- (2,4-dimethyl-6-methoxyphenyl) -5-isopropyl-5-methyl-pyrrolidine-2,4-dione and acetic anhydride are used as starting compounds In the case, the reaction process of the process according to the invention can be represented by the following scheme:

According to process (C) 3- (2-methoxy-4-methyl-phenyl) -5,5-diethyl-pyrrolidine-2,4-dione and ethoxyethyl chloroformate are used as starting compounds In the case, the reaction process of the process according to the invention can be represented by the following scheme:

According to method (D _α ) 3- (2,6-dimethyl-4-methoxyphenyl) -5,5-pentamethylene-pyrrolidine-2,4-dione and methyl chloromonothioformate as starting materials When used, the reaction process of the process according to the invention can be represented by the following scheme:

3- (2-Methyl-4-ethoxyphenyl) -5,5-ethylmercaptoethyl-pyrrolidine-2,4-dione, carbon disulfide and methyl iodide according to method (D _β ) are starting components When used as, the reaction process of the process according to the invention can be represented by the following scheme:

According to process (E) 3- (2-methyl-4-isopropoxy-phenyl) -5,5- (2-methyl) -pentamethylene-pyrrolidine-2,4-dione and methanesulfonyl chloride When used as starting material, the reaction process of the process according to the invention can be represented by the following scheme:

3- (2-methoxy-4-methylphenyl) -5-isobutyl-5-methyl-pyrrolidine-2,4-dione and methanethio-phosphonyl chloride 2,2,2- according to method (F) When trifluoroethyl ester is used as starting product, the reaction process of the process according to the invention can be represented by the following scheme:

When 3- (2-methyl-4-methoxyphenyl) -5-cyclopropyl-5-methyl-pyrrolidine-2,4-dione and NaOH are used as starting components according to method (G), The reaction process of the process according to the invention can be represented by the following scheme:

When 3- (2-methyl-4-ethoxyphenyl) -5,5-hexamethylene-pyrrolidine-2,4-dione and ethyl isocyanate are used as starting materials according to the method (H _α ), The reaction process of the process according to the invention can be represented by the following scheme:

When 3- (2-methoxy-4-methylphenyl) -5-methyl-pyrrolidine-2,4-dione and dimethylcarbamoyl chloride are used as starting materials according to the method (H _β ), The reaction process of the method according to the present invention can be represented by the following scheme:

The compounds of the following general formula (II) which are required as starting materials for process (A) according to the invention are novel.

Where

A, B, X, Y, X and R ⁸ have the meanings mentioned above.

Acyl-amino acid esters of formula (II) are for example acylated with amino acid derivatives of formula (XIV) with phenylacetyl halides of formula (XV) (see Chem. Reviews 52, 237-416). (1953); Bhattacharya, Indian J. Chem. 6, 341-5, 1968), obtained by esterifying acylamino acids of the general formula (IIa): Chem. Ind. (London) 1568 (1968); .

Where

R ^{12 ′} represents hydrogen (XIVa) or alkyl (XIVb),

A, B, X, Y and Z have the meanings mentioned above,

Hal represents chlorine or bromine,

R ¹² represents hydrogen.

When substituents A and B form a ring, the resulting general (XIVa) substituted cyclic aminocarboxylic acids can generally be obtained by Bucherer-Bergs reaction or Strecker synthesis, in which case they are multi-isomeric forms Is obtained. Thus, under the conditions of the Bucherer-Bergs reaction, isomers in which the radicals R and the carboxyl groups are in the horizontal position (referred to as β for convenience) are mainly formed, while in the conditions of Strecker synthesis, isomers in which the amino groups and the radicals R are in the horizontal position. (Hereinafter referred to as α) is mainly formed (L. Munday, J. Chem. Soc. 4372 (1961); JT Eward, C. Jitrangeri, Can. J. Chem. 53, 3339 (1975)).

In addition, the starting material of the general formula (II) used in the above method (A) was reacted with the aminonitrile of the following general formula (XVI) with the phenylacetyl halide of the following general formula (XV) to the compound of the general formula (XVII) Can be obtained, and the compound can be prepared by subsequently alcoholic decomposition in the presence of sulfuric acid.

Where

A, B, X, Y, Z and R ⁸ have the aforementioned meanings,

Hal represents chlorine or bromine.

Compounds of general formula (XVII) are likewise also novel.

In addition to the intermediates mentioned in the preparation examples, compounds of the following general formula (II) may be mentioned by way of example, but are not limited to:

N- (2-methyl-4-methoxyphenylacetyl) -alanine methyl ester,

N- (2-methyl-4-methoxyphenylacetyl) -leucine methyl ester,

N- (2-methyl-4-methoxyphenylacetyl) -isoleucine methyl ester,

N- (2-methyl-4-methoxyphenylacetyl) -valine methyl ester,

Methyl N- (2-methyl-4-methoxyphenylacetyl) -aminoisobutyrate,

Methyl N- (2-methyl-4-methoxyphenylacetyl) -2-ethyl-2-aminobutyrate,

Methyl N- (2-methyl-4-methoxyphenylacetyl) -2-methyl-2-aminovalerate,

Methyl N- (2-methyl-4-methoxyphenylacetyl) -2,3-dimethyl-2-aminovalerate,

Methyl N- (2-methyl-4-methoxyphenylacetyl) -1-amino-cyclopentanecarboxylate,

Methyl N- (2-methyl-4-methoxyphenylacetyl) -1-amino-cyclohexanecarboxylate,

Methyl N- (2-methyl-4-methoxyphenylacetyl) -1-amino-cycloheptancarboxylate,

Methyl N- (2-methyl-4-methoxyphenylacetyl) -1-amino-cyclooctanecarboxylate,

N- (2,6-dimethyl-4-methoxyphenylacetyl) -alanine methyl ester,

N- (2,6-dimethyl-4-methoxyphenylacetyl) -leucine methyl ester,

N- (2,6-dimethyl-4-methoxyphenylacetyl) -isoleucine methyl ester,

N- (2,6-dimethyl-4-methoxyphenylacetyl) -valine methyl ester,

Methyl N- (2,6-dimethyl-4-methoxyphenylacetyl) -aminoisobutyrate,

Methyl N- (2,6-dimethyl-4-methoxyphenylacetyl) -2-ethyl-2-aminobutyrate,

Methyl N- (2,6-dimethyl-4-methoxyphenylacetyl) -2-methyl-2-aminovalerate,

Methyl N- (2,6-dimethyl-4-methoxyphenylacetyl) -2,3-dimethyl-2-aminovalerate,

Methyl N- (2,6-dimethyl-4-methoxyphenylacetyl) -1-amino-cyclopentanecarboxylate,

Methyl N- (2,6-dimethyl-4-methoxyphenylacetyl) -1-amino-cyclohexanecarboxylate,

Methyl N- (2,6-dimethyl-4-methoxyphenylacetyl) -1-amino-cycloheptancarboxylate,

Methyl N- (2,6-dimethyl-4-methoxyphenylacetyl) -1-amino-cyclooctanecarboxylate,

N- (2,4-dimethyl-6-methoxyphenylacetyl) -alanine methyl ester,

N- (2,4-dimethyl-6-methoxyphenylacetyl) -leucine methyl ester,

N- (2,4-methyl-6-methoxyphenylacetyl) -isoleucine methyl ester,

N- (2,4-methyl-6-methoxyphenylacetyl) -valine methyl ester,

Methyl N- (2,4-dimethyl-6-methoxyphenylacetyl) -aminoisobutyrate,

Methyl N- (2,4-dimethyl-6-methoxyphenylacetyl) -2-ethyl-2-aminobutyrate,

Methyl N- (2,4-dimethyl-6-methoxyphenylacetyl) -2-methyl-2-aminovalerate,

Methyl N- (2,4-dimethyl-6-methoxyphenylacetyl) -2,3-dimethyl-2-aminovalerate,

Methyl N- (2,4-dimethyl-6-methoxyphenylacetyl) -1-amino-cyclopentanecarboxylate,

Methyl N- (2,4-dimethyl-6-methoxyphenylacetyl) -1-amino-cyclohexanecarboxylate,

Methyl N- (2,4-dimethyl-6-methoxyphenylacetyl) -1-amino-cycloheptancarboxylate,

Methyl N- (2,4-dimethyl-6-methoxyphenylacetyl) -1-amino-cyclooctanecarboxylate,

Methyl N- (2-methyl-4-methoxyphenylacetyl) -1-amino-2-methyl-cyclohexanecarboxylate,

Methyl N- (2-methyl-4-methoxyphenylacetyl) -1-amino-3-methyl-cyclohexanecarboxylate,

Methyl N- (2-methyl-4-methoxyphenylacetyl) -1-amino-4-methyl-cyclohexanecarboxylate,

Methyl N- (2-methyl-4-methoxyphenylacetyl) -1-amino-3,4-dimethyl-cyclohexanecarboxylate,

Methyl N- (2-methyl-4-methoxyphenylacetyl) -1-amino-4-ethyl-cyclohexanecarboxylate,

Methyl N- (2-methyl-4-methoxyphenylacetyl) -1-amino-4-isopropyl-cyclohexanecarboxylate,

Methyl N- (2-methyl-4-methoxyphenylacetyl) -1-amino-4-t-butyl-cyclohexanecarboxylate,

Methyl N- (2-methyl-4-methoxyphenylacetyl) -1-amino-4-methoxy-cyclohexanecarboxylate,

Methyl N- (2,4-dimethyl-6-methoxyphenylacetyl) -1-amino-2-methyl-cyclohexanecarboxylate,

Methyl N- (2,4-dimethyl-6-methoxyphenylacetyl) -1-amino-3-methyl-cyclohexanecarboxylate,

Methyl N- (2,4-dimethyl-6-methoxyphenylacetyl) -1-amino-4-methyl-cyclohexanecarboxylate,

Methyl N- (2,4-dimethyl-6-methoxyphenylacetyl) -1-amino-3,4-dimethyl-cyclohexanecarboxylate,

Methyl N- (2,4-dimethyl-6-methoxyphenylacetyl) -1-amino-4-ethyl-cyclohexanecarboxylate,

Methyl N- (2,4-dimethyl-6-methoxyphenylacetyl) -1-amino-4-isopropyl-cyclohexanecarboxylate,

Methyl N- (2,4-dimethyl-6-methoxyphenylacetyl) -1-amino-4-t-butyl-cyclohexanecarboxylate,

Methyl N- (2,4-dimethyl-6-methoxyphenylacetyl) -1-amino-4-methoxy-cyclohexanecarboxylate,

Methyl N- (2,6-dimethyl-4-methoxyphenylacetyl) -1-amino-2-methyl-cyclohexanecarboxylate,

Methyl N- (2,6-dimethyl-4-methoxyphenylacetyl) -1-amino-3-methyl-cyclohexanecarboxylate,

Methyl N- (2,6-dimethyl-4-methoxyphenylacetyl) -1-amino-4-methyl-cyclohexanecarboxylate,

Methyl N- (2,6-dimethyl-4-methoxyphenylacetyl) -1-amino-3,4-dimethyl-cyclohexanecarboxylate,

Methyl N- (2,6-dimethyl-4-methoxyphenylacetyl) -1-amino-4-ethyl-cyclohexanecarboxylate,

Methyl N- (2,6-dimethyl-4-methoxyphenylacetyl) -1-amino-4-isopropyl-cyclohexanecarboxylate,

Methyl N- (2,6-dimethyl-4-methoxyphenylacetyl) -1-amino-4-t-butyl-cyclohexanecarboxylate,

Methyl N- (4-chloro-2-methoxyphenylacetyl) -1-amino-4-methoxy-cyclohexanecarboxylate.

In addition to the intermediates mentioned in the preparation examples, compounds of the general formula (IIa) may be mentioned by way of example but are not limited to:

N- (2-methyl-4-methoxyphenylacetyl) -alanine,

N- (2-methyl-4-methoxyphenylacetyl) -leucine,

N- (2-methyl-4-methoxyphenylacetyl) -isoleucine,

N- (2-methyl-4-methoxyphenylacetyl) -valine,

N- (2-methyl-4-methoxyphenylacetyl) -aminoisobutyric acid,

N- (2-methyl-4-methoxyphenylacetyl) -2-ethyl-2-aminobutyric acid,

N- (2-methyl-4-methoxyphenylacetyl) -2-methyl-2-aminovaleric acid,

N- (2-methyl-4-methoxyphenylacetyl) -2,3-dimethyl-2-aminovaleric acid,

N- (2-methyl-4-methoxyphenylacetyl) -1-amino-cyclopentanecarboxylic acid,

N- (2-methyl-4-methoxyphenylacetyl) -1-amino-cyclohexanecarboxylic acid,

N- (2-methyl-4-methoxyphenylacetyl) -1-amino-cycloheptancarboxylic acid,

N- (2-methyl-4-methoxyphenylacetyl) -1-amino-cyclooctanecarboxylic acid,

N- (methyl-2-methoxyphenylacetyl) -alanine,

N- (2,6-dimethyl-4-methoxyphenylacetyl) -alanine,

N- (2,6-dimethyl-4-methoxyphenylacetyl) -leucine,

N- (2,6-dimethyl-4-methoxyphenylacetyl) -isoleucine,

N- (2,6-dimethyl-4-methoxyphenylacetyl) -valine,

N- (2,6-dimethyl-4-methoxyphenylacetyl) -aminoisobutyric acid,

N- (2,6-dimethyl-4-methoxyphenylacetyl) -2-ethyl-2-aminobutyric acid,

N- (2,6-dimethyl-4-methoxyphenylacetyl) -2-methyl-2-aminovaleric acid,

N- (2,6-dimethyl-4-methoxyphenylacetyl) -2,3-dimethyl-2-aminovaleric acid,

N- (2,6-dimethyl-4-methoxyphenylacetyl) -1-amino-cyclopentanecarboxylic acid,

N- (2,6-dimethyl-4-methoxyphenylacetyl) -1-amino-cyclohexanecarboxylic acid,

N- (2,6-dimethyl-4-methoxyphenylacetyl) -1-amino-cycloheptancarboxylic acid,

N- (2,6-dimethyl-4-methoxyphenylacetyl) -1-amino-cyclooctanecarboxylic acid,

N- (2,4-dimethyl-6-methoxyphenylacetyl) -alanine,

N- (2,4-dimethyl-6-methoxyphenylacetyl) -leucine,

N- (2,4-dimethyl-6-methoxyphenylacetyl) -isoleucine,

N- (2,4-dimethyl-6-methoxyphenylacetyl) -valine,

N- (2,4-dimethyl-6-methoxyphenylacetyl) -aminoisobutyric acid,

N- (2,4-dimethyl-6-methoxyphenylacetyl) -2-ethyl-2-aminobutyric acid,

N- (2,4-dimethyl-6-methoxyphenylacetyl) -2-methyl-2-aminovaleric acid,

N- (2,4-dimethyl-6-methoxyphenylacetyl) -2,3-dimethyl-2-aminovaleric acid,

N- (2,4-dimethyl-6-methoxyphenylacetyl) -1-amino-cyclopentanecarboxylic acid,

N- (2,4-dimethyl-6-methoxyphenylacetyl) -1-amino-cyclohexanecarboxylic acid,

N- (2,4-dimethyl-6-methoxyphenylacetyl) -1-amino-cycloheptancarboxylic acid,

N- (2,4-dimethyl-6-methoxyphenylacetyl) -1-amino-cyclooctanecarboxylic acid,

N- (2-methyl-4-methoxyphenylacetyl) -1-amino-2-methyl-cyclohexanecarboxylic acid,

N- (2-methyl-4-methoxyphenylacetyl) -1-amino-3-methyl-cyclohexanecarboxylic acid,

N- (2-methyl-4-methoxyphenylacetyl) -1-amino-4-methyl-cyclohexanecarboxylic acid,

N- (2-methyl-4-methoxyphenylacetyl) -1-amino-3,4-dimethyl-cyclohexanecarboxylic acid,

N- (2-methyl-4-methoxyphenylacetyl) -1-amino-4-ethyl-cyclohexanecarboxylic acid,

N- (2-methyl-4-methoxyphenylacetyl) -1-amino-4-isopropyl-cyclohexanecarboxylic acid,

N- (2-methyl-4-methoxyphenylacetyl) -1-amino-4-t-butyl-cyclohexanecarboxylic acid,

N- (2-methyl-4-methoxyphenylacetyl) -1-amino-4-methoxy-cyclohexanecarboxylic acid,

N- (2,6-dimethyl-4-methoxyphenylacetyl) -1-amino-2-methyl-cyclohexanecarboxylic acid,

N- (2,6-dimethyl-4-methoxyphenylacetyl) -1-amino-3-methyl-cyclohexanecarboxylic acid,

N- (2,6-dimethyl-4-methoxyphenylacetyl) -1-amino-4-methyl-cyclohexanecarboxylic acid,

N- (2,6-dimethyl-4-methoxyphenylacetyl) -1-amino-3,4-dimethyl-cyclohexanecarboxylic acid,

N- (2,6-dimethyl-4-methoxyphenylacetyl) -1-amino-4-ethyl-cyclohexanecarboxylic acid,

N- (2,6-dimethyl-4-methoxyphenylacetyl) -1-amino-4-isopropyl-cyclohexanecarboxylic acid,

N- (2,6-dimethyl-4-methoxyphenylacetyl) -1-amino-4-t-butyl-cyclohexanecarboxylic acid,

N- (2,6-dimethyl-4-methoxyphenylacetyl) -1-amino-4-methoxy-cyclohexanecarboxylic acid,

N- (2,4-dimethyl-6-methoxyphenylacetyl) -1-amino-2-methyl-cyclohexanecarboxylic acid,

N- (2,4-dimethyl-6-methoxyphenylacetyl) -1-amino-3-methyl-cyclohexanecarboxylic acid,

N- (2,4-dimethyl-6-methoxyphenylacetyl) -1-amino-4-methyl-cyclohexanecarboxylic acid,

N- (2,4-dimethyl-6-methoxyphenylacetyl) -1-amino-3,4-dimethyl-cyclohexanecarboxylic acid,

N- (2,4-dimethyl-6-methoxyphenylacetyl) -1-amino-4-ethyl-cyclohexanecarboxylic acid,

N- (2,4-dimethyl-6-methoxyphenylacetyl) -1-amino-4-isopropyl-cyclohexanecarboxylic acid,

N- (2,4-dimethyl-6-methoxyphenylacetyl) -1-amino-4-t-butyl-cyclohexanecarboxylic acid,

N- (2,4-dimethyl-6-methoxyphenylacetyl) -1-amino-4-methoxy-cyclohexanecarboxylic acid.

Compounds of formula (IIa) can be obtained, for example, from phenylacetyl halides of formula (XV) and amino acids of formula (XIVa) according to the Schotten-Baumann method (see Organikum, 9th Edition, 446 ( 1970) VEB Deutscher Verlag der Wissenschaften, Berlin).

Phenylacetyl halides of formula (XV) are new in some cases.

Where

X, Y and Z have the meanings mentioned above,

Hal represents bromine or chlorine.

This compound can be prepared simply by known methods from the corresponding known phenyl acetic acid.

Compounds which are further needed as starting materials for carrying out the processes (B), (C), (D), (E), (F), (G) and (H) according to the invention, ie of general formula (III) Acid halides, carboxylic anhydrides of general formula (IV), chloroformic acid esters or chloroformic acid thioesters of general formula (V), chloromonothioformic acid esters of general formula (VI) or chlorodithioformic acid esters, general formula (VII) Alkyl halides, sulfonyl chlorides of formula (VIII), phosphorus compounds of formula (IX), metal compounds of formulas (X) and (XI) or amines and isocyanates of formula (XIII), isothiocyanates Or carbamoyl chloride is generally a known compound of organic and / or inorganic chemistry.

Method (A) is characterized in that A, B, X, Y, Z and R ⁸ intramolecular condensation of the compound of formula (II), in which the above-mentioned meanings are present in the presence of a base.

Diluents which can be used in process (A) according to the invention are all inert organic solvents. Preferably used may include hydrocarbons such as toluene and xylene, and also ethers such as dibutyl ether, tetrahydrofuran, dioxane, glycol dimethyl ether, diglycol dimethyl ether, and also dimethyl sulfoxide, sulfolane, dimethylform Polar solvents such as amides and N-methyl-pyrrolidone and alcohols such as methanol, ethanol, propanol, isopropanol, butanol, isobutanol and t-butanol.

Bases (deprotonating agents) that can be used to carry out process (A) according to the invention are all conventional proton acceptors. Preferred for use are oxides, hydroxides and carbonates of alkali and alkaline earth metals such as sodium hydroxide, potassium hydroxide, magnesium oxide, calcium oxide, sodium carbonate, potassium carbonate and calcium carbonate, which are also for example triethylbenzylammonium chloride , Tetrabutylammonium bromide, adogen 464 (= methyltrialkyl (C ₈ -C ₁₀ ) -ammonium chloride) or TDA 1 (= tris- (methoxyethoxyethyl) amine) can be used in the presence of have.

Alkali metals such as sodium or potassium may also be used. In addition, 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 ethylate and potassium t-butylate can be used.

In carrying out process (A) according to the invention, the reaction temperature can vary within a relatively wide range. In general, the reaction is carried out at temperatures of 0 ° C to 250 ° C, preferably 50 ° C to 150 ° C.

Method (A) is generally carried out at atmospheric pressure.

In carrying out process (A) according to the invention, about 2 moles of deprotonation base are used per mole of reaction component of formula (II). However, it is also possible to use one component or another component in a large- excess (up to 3 moles).

Process (B _α ) is characterized by reacting a compound of formula (Ia) with a carboxylic acid halide of formula (III).

Diluents usable in the process (Bα) according to the invention are all solvents which are inert to the acid halide. Preferred that can be used are hydrocarbons such as benzine, benzene, toluene, xylene and tetralin, and also halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, chlorobenzene and o-dichlorobenzene, and also acetone and methyl isopropyl Ketones such as ketones, and further ethers such as diethyl ether, tetrahydrofuran and dioxane, carboxylic acid esters such as ethyl acetate, and also strong polar solvents such as dimethyl sulfoxide and sulfolane. If stable to hydrolysis of the acid halide, the reaction can also be carried out in the presence of water.

Suitable acid-binding agents for the reaction according to the process (B _α ) of the invention are all customary acid acceptors. Preferably used may be tertiary amines such as triethylamine, pyridine, diazabicyclooctane (DABCO), diazabicycloundecene (DBU), diazabicyclononene (DBN), Hunich Base and N, N-dimethylaniline, and also alkaline earth metal oxides such as magnesium oxide and calcium oxide, and also alkali metal carbonates and alkaline earth metal carbonates such as sodium carbonate, potassium carbonate and calcium carbonate, and also sodium hydroxide and potassium hydroxide It is the same alkali metal hydroxide.

In the case of carrying out the process (B _α ) according to the invention, the reaction temperature can be varied within a relatively wide range. In general, the reaction is carried out at a temperature of -20 ° C to + 150 ° C, preferably 0 ° C to 100 ° C.

When carrying out the process (B _α ) of the present invention, the starting material of general formula (Ia) and the carboxylic acid halide of general formula (III) are generally used in approximately equivalent amounts. However, it is possible to use carboxylic acid halides in a relatively large amount (up to 5 moles). Post-treatment is carried out by conventional methods.

Process (B _β ) is characterized by reacting a compound of formula (Ia) with a carboxylic anhydride of formula (IV).

When carboxylic anhydrides are used as reactants of the general formula (IV) in the process (B _β ) according to the invention, the diluents which can be used are mentioned as being preferred when using acid halides. In addition, excess carboxylic anhydride also simultaneously acts as a diluent.

In the process (B _β ) according to the invention the reaction temperature can vary within a relatively wide range. In general, the reaction is carried out at a temperature of -20 ° C to + 150 ° C, preferably 0 ° C to 100 ° C.

In carrying out the process according to the invention, the starting materials of the general formula (Ia) and the carboxylic anhydrides of the general formula (IV) are generally used in approximately equivalent amounts. However, it is possible to use carboxylic anhydride in a relatively large excess (5 mol or less). Post-treatment is carried out by conventional methods.

Generally, the diluent and excess carboxylic anhydride and also the carboxylic acid formed are removed by distillation or by washing with organic solvents or water.

Process (C) is characterized by reacting a compound of general formula (Ia) with a chloroformic acid ester or chloroformic acid thioester of general formula (V).

In the case of using the corresponding chloroformic ester or chloroformic thioester, the diluents which can be used in the process (C) according to the invention are all conventional acid acceptors. Preferably used may be higher amines, for example triethylamine, pyridine, DABCO, DBU, DBN, Hunich Base and N, N-dimethylaniline, and also alkaline earth metal oxides such as magnesium oxide and calcium oxide, and also alkali metal carbonates and alkaline earth metal carbonates such as sodium carbonate, potassium carbonate and calcium carbonate, and also sodium hydroxide and potassium hydroxide It is the same alkali metal hydroxide.

In the case of using chloroformic esters or chloroformic thioesters, the diluents usable in the process (C) according to the invention are all solvents which are inert to these components. Preferred which can be used are hydrocarbons such as benzine, benzene, toluene, xylene and tetralin, and also halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, chlorobenzene and o-dichlorobenzene, and also acetone and methylisopropyl Ketones such as ketones, and further ethers such as diethyl ether, tetrahydrofuran and dioxane, carboxylic acid esters such as ethyl acetate, and also strong polar solvents such as dimethyl sulfoxide and sulfolane.

When chloroformic esters and / or chloroformic acid thioesters are used as the carboxylic acid derivatives of the general formula (V), the reaction temperature according to the process (C) of the present invention can be varied within a relatively wide range. When the reaction is carried out in the presence of a diluent and an acid-binder, the reaction temperature is from -20 deg. C to +100 deg.

Process (C) of the invention is generally carried out under atmospheric pressure.

When carrying out process (C) according to the invention, the starting materials of the general formula (Ia) and the corresponding chloroformic esters and / or chloroformic thioesters of the general formula (V) are generally used in approximately equivalent amounts. . However, it is possible to use one component or another component in a relatively large amount (up to 2 moles). The post treatment is then carried out by conventional methods. Generally, the remaining reaction mixture is concentrated by removing the precipitated salts and removing the diluent.

In the preparation method (D _α ), about 1 mole of chloromonothioformic acid ester or chlorodithioformic acid thioester of general formula (VI) per mol of the starting compound of general formula (Ia) is 0 to 120 ° C., preferably 20 To 60 ° C.

Suitable diluents which may optionally be added are all inert polar organic solvents such as ethers, amides, sulfones, sulfoxides and halogenoalkanes.

Preference is given to using dimethyl sulfoxide, tetrahydrofuran, dimethylformamide or methylene chloride.

In a preferred embodiment, for example, a strong deprotonating agent such as sodium hydride or potassium t-butylate is added to synthesize the enolate salt of formula (Ia), with no further addition of the acid-binder necessary. .

Where acid-binding agents are used, customary inorganic or organic bases are suitable, examples of which may be mentioned sodium hydroxide, sodium carbonate, potassium carbonate, pyridine and triethylamine.

The reaction can be carried out at atmospheric or elevated pressure, preferably at atmospheric pressure. Post-treatment is carried out by conventional methods.

In the production method (D _β ), an equimolar amount or excess carbon disulfide per mole of starting compound of the general formula (Ia) is added. In this case the reaction is preferably carried out at 0 to 50 ° C, in particular at 20 to 30 ° C.

In the method (D _α ) of the present invention, bases that can be used are all conventional proton acceptors. Preferably used may be alkali metal hydrides, alkali metal alcoholates, alkali metal or alkaline earth metal carbonates or bicarbonates, or nitrogen bases. Examples that may be mentioned are sodium hydride, sodium methanolate, sodium hydroxide, calcium hydroxide, potassium carbonate, sodium bicarbonate, triethylamine, dibenzylamine, diisopropylamine, pyridine, quinoline, diazabicyclooctane (DABCO), dias Zabicycloundecene (DBU) and diazabicyclononene (DBN).

Diluents that can be used in this method are all conventional solvents. Preferably used may include aromatic hydrocarbons such as benzene or toluene, alcohols such as methanol, ethanol, isopropanol or ethylene glycol, ethers such as nitrile such as acetonitrile, tetrahydrofuran or dioxane, dimethylformamide or dimethyl sulfoxide Or other polar solvents such as sulfolane.

Often, for convenience, the corresponding salts are prepared from compounds of general formula (la) by first adding a deprotonating agent (such as potassium t-butylate or sodium hydride). After the formation of the intermediate compound is complete, for example, after stirring for several hours at room temperature, compound (Ia) is reacted with carbon disulfide.

Further reactions of the general formula (VII) with alkyl halides are preferably carried out at temperatures of 0 to 70 ° C, and especially 20 to 50 ° C. In this case at least equimolar amounts of alkyl halides are used.

The reaction can be carried out at atmospheric or elevated pressure, preferably at atmospheric pressure.

In addition, the post-treatment is carried out by conventional methods.

In the preparation method (E), about 1 mol of sulfonyl chloride of the general formula (VIII) per 1 mol of the starting compound of the general formula (Ia) is reacted at -20 to 150 캜, preferably 20 to 70 캜.

Suitable diluents which may optionally be added are all inert polar organic solvents, for example halogenated hydrocarbons such as ethers, amides, nitriles, sulfones and sulfoxides or methylene chlorides.

Preference is given to using dimethyl sulfoxide, tetrahydrofuran, dimethylformamide, dimethyl sulfide or methylene chloride.

In a preferred embodiment, for example, a strong deprotonating agent such as sodium hydride or potassium t-butylate is added to synthesize the enolate salt of formula (Ia), with no further addition of the acid-binder necessary. .

Where acid-binding agents are used, customary inorganic or organic bases are suitable, examples of which may be mentioned sodium hydroxide, sodium carbonate, potassium carbonate, pyridine and triethylamine.

The reaction can be carried out at atmospheric or elevated pressure, preferably at atmospheric pressure. Post-treatment is carried out by conventional methods.

In the preparation method (F), in order to obtain a compound of the general formula (Ie), 1 to 2, preferably 1 to 1.3 moles of the phosphorus compound of the general formula (IX) per mol of the starting compound of the general formula (Ia) The reaction is carried out at -40 to 150 캜, preferably at -10 to 110 캜.

Suitable diluents which may optionally be added are all inert polar organic solvents, for example ethers, amides, nitriles, alcohols, sulfides, sulfons, sulfoxides and the like.

Preference is given to using acetonitrile, dimethyl sulfoxide, tetrahydrofuran, dimethylformamide or methylene chloride.

Suitable acid-binding agents which may optionally be added are conventional inorganic or organic bases such as hydroxides, carbonates or amines. Sodium hydroxide, sodium carbonate, potassium carbonate, pyridine and triethylamine may be mentioned by way of example.

The reaction can be carried out at atmospheric or elevated pressure, preferably at atmospheric pressure. Post-treatment is carried out by conventional methods. The final product obtained is preferably purified by crystallization, chromatography purification or so-called partial distillation, ie by removing volatiles in vacuo.

Process (G) is characterized by reacting a compound of formula (Ia) with a metal compound (X) or an amine (XI).

Diluents which can be used in the process according to the invention are preferably ethers such as tetrahydrofuran, dioxane or diethyl ether, in addition to alcohols such as methanol, ethanol or isopropanol, and water. Process (G) according to the invention is generally carried out under atmospheric pressure. The reaction temperature is generally -20 to 100 ° C, preferably 0 to 50 ° C.

In the production method (H _α ), about 1 water of isocyanate of general formula (XII) is reacted at 0 to 100 ° C., preferably 20 to 50 ° C. per mole of starting compound of general formula (Ia).

Suitable diluents which are optionally added are all inert organic solvents such as ethers, amides, nitriles, sulfones and sulfoxides.

Optionally, a catalyst can be added to promote the reaction. Very advantageously usable catalysts are organotin compounds such as, for example, dibutyltin dilaurate. This method is preferably carried out at atmospheric pressure.

In the preparation method (H _β ), about 1 mole of carbamoyl chloride of the general formula (XIII) per 1 mol of the starting compound of the general formula (Ia) is reacted at 0 to 150 ° C., preferably 20 to 70 ° C.

Suitable diluents which are optionally added are all inert polar organic solvents such as ethers, amides, sullons, sulfoxides or halogenated hydrocarbons.

Dimethyl sulfoxide, tetrahydrofuran, dimethylformamide or methylene chloride are preferably used.

In a preferred embodiment, for example, a strong deprotonating agent such as sodium hydride or potassium t-butylate is added to synthesize the enolate salt of formula (Ia), with no further addition of the acid-binder necessary. .

When acid-binding agents are used, customary inorganic or organic bases are suitable, examples of which may be mentioned sodium hydroxide, sodium carbonate, potassium carbonate, triethylamine and pyridine.

The reaction can be carried out at atmospheric or elevated pressure, preferably at atmospheric pressure. Post-treatment is carried out by conventional methods.

The active compounds of the present invention are suitable for controlling animal pests, preferably arthropods and nematodes, particularly insects and spider subclasses, appearing in the fields of agriculture, forestry, storage and materials, and hygiene. They are active against normally sensitive and resistant species and all or part of the growing season. The pests mentioned above include the following:

Isopoda neck, for example Oniscus asellus, Armadillidium vulgare and Porcellio scaber.

From the order of Diloplopoda, for example Blaniulus guttulatus.

From the neck of Chilopoda, for example, Geophilus carp-ophagus and Scutigera spec.

From the order of the symphyla, for example Scutigerella immaculata.

From the order of Thysanura, for example, Lepisma saccharina.

The neck of Collembola, for example Onychiur-us armatus.

From the order of Orthoptera, for example, Blata orientalis, Periplaneta americana, Leucophaea maderae, Blatella germanica, Ah Keta domestikus, Gryllotalpa spp., Locusta migratoria migratorioides, Melano-oplus differentialis and Shh Stostocerca gregaria.

From the order of the dermaptera, for example Porficula auricularia.

Termite Isoptera, for example Reticulitermes spp.

Anoplura, for example, Phylloxera vastatrix, Pemphigus spp., Pediculus huma-nus corporis, Haematopinus subspecies spp.) and Linognathus spp.

Allophaga, for example Trichodectes spp. And Damalinea spp.

Thysanoptera, for example Hercinothrips femoralis and Tripps tabaci.

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

The cicada (Homoptera), for example Aleurodes bra-ssicae, Bemisia tabaci, Trialuro-rodes vaporariorum, Apis gossipi Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Apis fabae, Doralis pomi, Eriosoma lan-igerum ), Hyopteroptera arundinis, Macrosiphum avenae, Myzus spp., Phorodon humuli, Rhopalosiphum padi , Empoasca spp., Eucelis bilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae ), Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp. And Psylla spp. ).

The order of the Lepidoptera, for example Pectinophoragossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella Phonometa padella, Plutella maculi-pennis, Malacosoma neustria, Euprotis chrysorrhoea, Lymantria spp. ), Buculatrix thurberiella, Phyloknistis citrella, Agrotis spp., Euxoa spp., Feltia spp., Earias insulana, Heliothis spp., Spodoptesa exigua, Mamestra brassicae, Panolis flammea, Prolo Prodenia litura, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo subspecies ( Chilo spp.), Pyrausta nubilalis, Ephestia kuehniel-la, Galeria mellonella, Tineola bissellie-lla, Tynea Tinea pellionella, Hofmann-ophila pseudospretella, Cacoacia podana, Capua reticulana, Coristoneura pumiferana fumiferana), Clysia ambiguella, Homona magnanima, and Tortrix viridana.

The order of the Coleoptera, for example, Anobium puncta-tum, Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides of Tectus obtectus, Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedon cochleariae, Diabrotica subspecies Diabrotica spp., Psylliodes chrysocephala, Epilachna varivestis, Atomaria spp., Oryzaephilus surinamensis, Antoninomu Anthomomus spp., Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus, Cethrorinkus assimilus thorrhynch-us assimilis, Hypera postica, Dermestes spp., Trogoderma spp., Anthrenus spp., Athenus subspecies ( Attagenus spp.), L-yctus spp., Melligethes aeneus, Ptinus spp., Niptus hololeucus, Givium psylloy Gibbium psylloides, Tribolium spp., Tenebrio molitor, Agriotes spp., Conoderus spp., Melonta mellonta Melolontha melolontha, Amphimallon solstitialis and Costelitra zeallandica.

Hymenopera, for example Diprion spp., Hoplocampa spp., Lasius spp., Mono-morium pharaonis and Vespa Subspecies (Vespa spp.).

Diptera, for example Aedes spp., Anopheles spp., Culex spp., Drosophila melanogaster, Musca subspecies ( musca spp., Fannia spp., Califora erythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp. , Gast-rophilus spp., Hippobosca spp., Stomoxys spp., Oestrus spp., Hypoderma spp. ), Tabanus spp., Tannia spp., Bibio hortul-anus, Oscinella frit, Porbia spp., Pegomia Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae, and Tipula paluosa ( Tipula paludosa).

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

Arachnida, for example Scorpio maurus and Latrodectus mactans.

From the order of Acarina, for example, Acarus siro, Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriopies Eriophyes ribis, Phyllocoptruta oleivora, Bophylus spp., Ripicephalus spp., Amblyomma spp., Hyaloma subspecies (Hyalom subspecies) -ma spp.), Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp., Tarsonemus subspecies ( Ta-rsonemus spp.), Bryobia praetiosa, Pano-nychus spp and Tetranychus spp.

The active compounds according to the invention exhibit potent pesticidal and acaricide activity.

They can be successfully used in particular for phytopathogenic insects, such as, for example, mustard beetle larvae (Phaedon cocleariae), cactus larvae (Nepotetics sinctifs) or Chinese cabbage moth (flutella maculenis). have.

The compounds according to the invention also exhibit fungicidal activity against, for example, Venturia inaequalis.

The active compounds according to the invention can also be used as deciduous, drying, broadleaf plant killing agents and in particular weed-removing agents. The term "weeds" broadly means all plants that grow in unwanted places. Whether the compounds according to the invention act as total or selective herbicides depends essentially on the concentration used.

The active compounds according to the invention can be used, for example, in connection with the following plants:

Dicotyledonous weeds in the following genus : Sinapis, Lepidium, Gallium, Stellaria, Matricaria, Anthemis, Galinsoga, Ke Nopodium, Urtica, Senesio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum, Rorippa, Rotala ), Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galcopsis, Papaver, Centaurea, Trifolium, Ranunculus and Taraxacum.

Dicotyledonous crops of the following genus : Gossypium, Glycine, Beta, Doucus, Phaseolus, Pisum, Solanum, Linum ), Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, Lactuca, Cucumis ) And Cucurbita.

Monocots in the genus : Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festus, Festuca, Eleusin, Brachiaria, Lolium, Bromus, Avena, Cyperus, Sorghum, Agropyron, Sino Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum, Ischacmum ), Sphenoclea, Dactyloctenium, Agrostis, Alopecurus and Apera.

Monocot crops of the following genus : Oryza, Zea, Triticum, Hordeum, Avena, Secale, Sorghum, Panicum Panicum), Saccharum, Ananas, Asparagus and Allium.

However, the use of the active compounds according to the invention is not limited at all in the above, but extends to other plants in the same way.

The compounds of the invention are suitable for the overall control of weeds, depending on concentration, for example, on industrial areas and railroads, and on walkways and plazas with or without trees. Similarly, the compounds of the present invention grow on plantations, ornamental water, orchards, vineyards, citrus fields, nut orchards, banana plantations, coffee plantations, tea plantations, rubber plantations, palm plantations, cocoa plantations, soft fruit plantations and hop fields. It can be used to control weeds in perennial crops and to selectively control annual weeds.

The active compounds according to the invention are suitable for the selective control of monocotyledonous weeds by both pre- and post-emergence methods in dicotyledonous crops. They can be very successfully used to control forage harmful plants, for example in cotton or beets.

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

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

When water is used as the extender, for example an organic solvent can also be used as an auxiliary solvent. Liquid solvents are mainly aromatic compounds such as xylene, toluene or alkylnaphthalene, chlorinated aromatic or chlorinated aliphatic hydrocarbons such as chlorobenzene, chloroethylene or methylene chloride, cyclohexane or paraffins, for example mineral oil fractions, mineral oils and vegetable oils. Alcohols such as aliphatic hydrocarbons, butanol or glycol and ethers and esters thereof, as well as strong polar solvents such as ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, dimethylformamide and dimethyl sulfoxide, are suitable Do.

Solid carriers are suitable, for example, ground natural minerals such as kaolin, clay, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals such as highly dispersed silica, alumina and silicates. Solid carriers for granulation include, for example, pulverized and classified natural rocks such as calcite, marble, pumice, calcite and dolomite, and synthetic granules of inorganic and organic powders, and organic such as sawdust, coconut husk, corncobs and tobacco stems. Granules of material are suitable. Emulsifiers and / or foam-forming agents include, for example, nonionic and anionic emulsifiers, for example polyoxyethylene fatty alcohol ethers such as polyoxyethylene fatty acid esters, alkylaryl polyglycol ethers, alkylsulfonates, alkyl sulfates, aryls Sulfonates and albumen hydrolysis products are suitable. Suitable dispersants are, for example, lignin-sulfite waste liquors and methylcellulose.

Adhesives, for example, natural and synthetic polymers in the form of powders, granules or emulsions, such as carboxymethylcellulose, gum arabic, polyvinyl alcohol and polyvinyl acetate, and natural phospholipids such as cephalin and lecithin, and synthetic phospholipids may be used in the formulation. Can be. As other additives, mineral oil and vegetable oil may be used.

Inorganic pigments such as iron oxide, titanium oxide and prussian blue, and colorants such as alizarin dyes, azo dyes and organic dyes such as metal phthalocyanine dyes and micronutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc You can also use

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

The active compounds according to the invention are prepared from commercially available formulations and mixtures of these with other active compounds such as insecticides, attractants, fungicides, acaricides, nematicides, fungicides, growth-modulating compounds or herbicides. May exist in the form of use. Pesticides include, for example, phosphates, carbamates, carboxylic acid esters, chlorinated hydrocarbons, phenylurea and substances produced by microorganisms and the like.

Examples of particularly advantageous components for the mixture are as follows:

Fungicides:

2-aminobutane; 2-anilino-4-methyl-6-cyclopropyl-pyrimidine; 2 ', 6'-dibromo-2-methyl-4'-trifluoromethoxy-4'-trifluoro-methyl-1,3-thiazole-5-carboxanilide; 2,6-dichloro-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, Ampropyl Force, Anilazine, Azaconazole, Benalacyl, Benodanil, Benomil, Binapacryl, Biphenyl, Vitertanol, Blastisidin-S, Bromuconazole, burimate, butiobate, calcium polysulfide, captapol, captan, carbendazim, carboxycin, quinomethionate, chloroneb, chloropicrine, chlorothalonil, clozolinate, cupraneb, Cymoxanyl, cyproconazole, cyprofuram, dichlorophene, diclobutrazole, diclofloanide, diclomezin, dichloran, dietofencarb, difenokazole, dimethymolol, dimethomorph , Diconazole, dinocap, diphenylamine, dipyrithione, ditalimfoss, dithianon, dodine, drazoxolone, edifene force, epoxyconazole, etirimole, ethriazole, phenarimol, fenbuco Nazol, fenfuram, phenytropane, fenpiclonyl, fenpropidine, fenpropormoff, fentin a Tate, Phenyl Hydroxide, Ferbam, Perimzone, Fluazinam, Fludioxonyl, Fluoride, Fluquinconazole, Flusilazole, Flusulfamid, Plutoranyl, Flutriafol, Polpet, Pocetyl -Aluminum, phthalide, fuberidazole, furlaxyl, purmecyclox, guazintin, hexachlorobenzene, hexaconazole, hymexazole, imazaryl, imbenconazole, iminooctadine, ifprobenfos (IBP ), Iprodione, isoprothiolane, kasugamycin, copper preparations such as copper hydroxide, copper naphthenate, copper oxychloride, copper sulfate, copper oxide, auxin-copper and Bordeaux mixtures, mancopers, manco Zeb, Manev, Mepanipyrim, Mepronyl, Metallaccil, Metconazole, Metasulfocarb, Metfuroxam, Methiram, Metsulfobox, Michaelrobutanyl, Nickel Dimethyldithiocarbamate, Nitrotal Isopropyl, noir mall, opuras, oxa Yarn, oxamocarb, oxycarboxycin, pepurazoate, fenconazole, penicuron, phosphodiphene, phthalide, fimaricin, piperaline, polycarbamate, polyoxin, probenazole, prochloraz, pro Simidone, propamocarb, propiconazole, propineb, pyrazophos, pyriphenox, pyrimethanyl, pyroquilon, quintogen (PCNB), sulfur and sulfur preparations, tebuconazole, teclophthalam, Tecnazen, tetraconazole, thibendazole, thiathiophene, thiophanate-methyl, thiram, tollclofos-methyl, tolylufluoride, triadimefon, triadimenol, triazoxide, trichlamide, Tricyclazole, tridemorph, triflumizol, tripolin, triticazole, validamycin A, vinclozoline, geneb, zelam.

Fungicides:

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

Insecticide / Acaricide / Acaricide:

Abamectin, AC 303 630, Acetate, Acrinatrin, Alanicab, Aldicarb, Alphametzin, Amitraz, Avermectin, AZ 60541, Azadirachtin, Ajinfoss A, Ajinfoss M, Azo Cyclotin, Bacillus thuringiensis, Bendiocarb, Benfuracarb, Bensultope, Betacyfluthrin, Bifenthrin, BPMC, Brofenprox, Bromophos A, Bufencarb, Bupropezin, Butocaxin, Butylpyridaben, kadusafos, carbaryl, carbofuran, carbophenothione, carbosulphan, catam, CGA 157 419, CGA 184 699, cloetocarb, chlorethoxyphosphate, chlorfenbinfos, chlorfluazuron, chlor Mephos, chlorpyrifos, chlorpyrifos M, cis-resmethrin, clocitrin, clofenthezin, cyanophosph, cycloprothrin, cyfluthrin, cyhalothrin, cyhexatin, cypermethrin, Cyromazine, deltamethrin, Demetone-M, Demetone-S, Demetone-S-methyl, Di Pentiuron, diazinon, diclopention, dichlorboth, diclifoss, dicrotophos, diethione, diflubenzuron, dimethatoate, dimethylbinfoss, dioxation, disulfotone, ediffenfoss, emma Mectin, Espenvalate, Ethiophenecarb, Ethion, Etofenprox, Etoprophos, Etrifoam, Phenamifoss, Penazaquine, Penbutatin, Phenytrothion, Phenobucarb, Phenothiocarb , Phenoxycarb, phenpropartin, fenpyrad, fenpyroximate, pention, fenvalrate, fipronil, fluazinam, flucycloxanthone, flucitalinate, flufenoxuron, flufenprox , Fluvalinate, phonophos, formitol, phosphthiazate, fufenfenx, furathiocarb, HCH, heptenophos, hexaflumuron, hexiax, imidacloprid, isprobenfos, isazofoss , Isopenfoss, isoprocarb, isoxation, ibe Tin, lambda-cyhalothrin, lufenuron, malathion, mecarbam, mebinfos, mesulfenfos, metaldehyde, metacryphos, metamidophos, methidathione, methiocarb, methamyl, methol Carb, Milvemectin, Monoclotophos, Moxidecin, Naled, NC 184, NI 25, Nitenpyram, Ometoate, Oxamyl, Oxidemetone M, Oxidepropos, Parathion A, Parathion M, Permethrin, Pento 8, forate, posalon, posmet, phosphamdone, bombard, pyrimicab, pyrimifos M, pyrimifos A, propenophos, promecarb, propaphos, propoxur, prothiophos, Protoate, pymetrozine, pyraclophos, pyridapention, pyresmethrin, pyrethrum, pyridabene, pyrimidipene, pyripropoxyphene, quinalforce, RH 5992, salityon, cebufoss, silafluorophene , Sulfofep, sulfprophos, tebufenozide, tebufenpyrad, tebupyrimifos, te Rubenzuron, Tefluthrin, Temefos, Terbam, Terbufos, Tetrachlorbinfos, Thiaphenox, Thiodicarb, Thiopanox, Thiomethone, Tionazine, Turingiencin, Tralomethrin, Triara Ten, triazofoss, triazuron, trichlorphone, triflumuron, trimetacarb, tamidothion, XMC, xylylcarb, YI 5301/5302, zetamethrin.

Herbicides:

Anilides such as, for example, diflufenican and propanyl; Arylcarboxylic acids such as, for example, dichloropicolinic acid, dicamba and picloram; Aryloxyalkanoic acids such as, for example, 2,4-D, 2,4-DB, 2,4-DP, fluoxypyr, MCPA, MCPP, and triclopyr; Aryloxy-phenoxy-alkanoic acid esters such as, for example, diclofomethyl, phenoxaprop-ethyl, fluazifop-butyl, halooxyphosph-methyl, and quinacofop-ethyl; Azinones such as, for example, chloridazone and norflurazon; Carbamate, such as chlorprofam, desmedapem, penmedipam and profam; Chloroacetanilides such as, for example, alachlor, acetochlor, butachlor, metazachlor, metolachlor, pretilachlor and propachlor; Dinitroanilines such as, for example, oryzaline, pendimethalin, and trituralin; Diphenyl ethers such as, for example, asifluorophene, biphenox, fluoroglycopene, pomesaphene, halosafé, lactofen and oxyfluorfen; Ureas such as, for example, chlorotoluron, diuron, fluoromethuron, isoproturon, linuron and metabenzthiazuron; Hydroxylamines such as, for example, alkoxydim, cletodim, cyclooxydim, cetoxydim, and trakoxydim; Imidazolinones such as for example imazetapyr, imazamethabenz, imazapyr and imazaquin; Nitriles such as, for example, bromoxynil, diclobenyl and oxynyl; Oxyacetamides such as, for example, mefenacet; For example amidosulfuron, bensulfuron-methyl, chlorimuron-ethyl, chlorsulfone, cynosulfuron, metsulfuron-methyl, nicosulfuron, prebisulfuron, pyrazosulfuron-ethyl, thifensulfuron-methyl Sulfonylureas such as triasulfuron and tribenuron-methyl; Thiol carbamates such as, for example, butyrate, cycloate, di-acrylate, EPTC, esprocarb, molinate, prosulfocarb, thiobencarb and tri-acrylate; Triazines such as, for example, atrazine, cyanazine, simazine, cymetrin, terbutryn and terbutylazine; Triazinones such as, for example, hexazinone, metamitrone, and metrizine; For example aminotriazole, benfuresate, bentazone, synmethylin, clomazone, clopyralide, dipfencuart, dithiopyr, etofumesate, fluorochloridone, glufosinate, glyphosate And others such as isoxaben, pyridate, quinclolac, quinmerak, sulfosate and tridiphane.

The active compounds according to the invention can also be present in admixture with synergists in their commercially available formulations and in the use forms prepared from these formulations. Synergists are compounds that increase the action of the active compound without the need for the synergist added itself to be activated.

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

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

In the cervix used for hygienic pests and stored pests, the active compounds according to the invention show excellent residual activity against wood and clay and excellent stability against alkalis on the lime surface.

In addition to being active against plant pests, sanitary pests and stockpile pests, the active compounds according to the invention can be used in the field of veterinary extermination, such as scaly mites, argasid mites, scab mites and thrombus. It is also active against bichlid mites, flies (acupuncture and inhalation flies), parasitic fly larvae, teeth, hair teeth, avian teeth and fleas. For example, they show excellent activity against ticks, such as, for example, Bifilus microfluus.

The active compounds according to the invention can also be used for agricultural productivity animals such as, for example, cattle, sheep, goats, horses, pigs, donkeys, camels, buffaloes, rabbits, chickens, turkeys, ducks, geese and bees, dogs, cats, ornamentals It is suitable for controlling arthropods that are prevalent in pets such as crude and freshwater fish, and also in experimental animals such as, for example, hamsters, guinea pigs, rats and mice. By controlling these arthropods, deaths and yield reductions (e.g. meat, milk, wool, leather, eggs and honey, etc.) are reduced, thus enabling more economical and simple animal breeding using the active compounds of the present invention. Become.

The active compounds according to the invention are prepared by methods known in the art of veterinary administration, for example by intestinal administration in the form of tablets, capsules, homemades, potions, granules, pastes, antagonists, and the like. By suppository or by parenteral administration, for example by means of injection (intramuscular, subcutaneous, intravenous and intraperitoneal, etc.), by form of insertion, by intranasal administration, for example, In the form of immersion or immersion, spraying, pouring and dropping, washing and misting, and in the form of shaped articles containing the active compound, for example, necklaces, ear tags, tail marks, leg bands, tethers or markings. It can be applied by transdermal administration.

The preparation and use of the material according to the invention is explained with reference to the following examples.

Example (Ia-1):

13.96 g (0.124 mol) of potassium t-butylate is introduced into 45 ml of dry THF and 20.4 g (0.0564 mol) of methyl N- (2,6-dimethyl-4 in 120 ml of anhydrous toluene at reflux temperature -Methoxyphenyl) acetyl-4-methyl-1-amino-cyclohexanecarboxylate is added dropwise. The mixture is heated at reflux for 1.5 h, then cooled, 180 ml of water are added, the aqueous phase is separated off, extraction is carried out with 70 ml of water, the aqueous phases combined and about 20 ml of concentrated hydrochloric acid After acidification at 10-20 [deg.] C., the precipitate is suction filtered and dried. After stirring with methyl t-butyl (MTB) ether / n-hexane, 16.8 g (94% of theory) of the above-described compound having a melting point of 169 ° C. are obtained.

Similar to Example (Ia-1), the compounds shown in the following table are obtained:

Example (Ib-1):

4.73 g (15 mmol) of 3- (2,6-dimethyl-4-methoxyphenyl) -5,5- (3-methyl) -pentamethylene-pyrrolidine-2,4-dione in 70 ml of anhydrous It is introduced into methylene chloride and 2.1 ml of triethylamine are added, followed by dropwise addition of 1.58 ml of isobutyryl chloride in 5 ml of anhydrous methylene chloride at 0-10 ° C. Stirring is continued at room temperature while checking by thin film-chromatography. After completion of the reaction, the organic phase is washed twice with 100 mL of 0.5 N sodium hydroxide solution, dried over magnesium sulfate and then concentrated by evaporation in vacuo. Recrystallization with MTB ether / n-hexane afforded 2.6 g (45% of theory) of the compound given above with a melting point of 218 ° C.

Similar to Example (Ib-1), the compounds shown in Table 9 are obtained:

Example (Ic-1):

4.73 g (15 mmol) of 3- (2,6-dimethyl-4-methoxyphenyl) -5,5- (3-methyl) -pentamethylene-pyrrolidine-2,4-dione in 70 ml of anhydrous It is introduced into methylene chloride and 2.1 ml of triethylamine are added, followed by dropwise addition of 1.5 ml of ethyl chloroformate in 5 ml of anhydrous methylene chloride at 0-10 占 폚. Stirring is continued at room temperature while checking by thin film-chromatography. After completion of the reaction, the organic pairs are washed twice with 100 ml of 0.5 N sodium hydroxide solution, dried over magnesium sulfate and then concentrated by increasing in vacuo. Recrystallization with MTB ether / n-hexane affords 3.9 g (67% of theory) of the compound given above with a melting point of 202 ° C.

Similar to Example (Ic-1), the compounds described in Table 10 are obtained:

Example (II-1)

15 g (0.0773 mole) of 2,6-dimethyl-4-methoxyphenylacetic acid are heated with 11.3 mL of thionyl chloride at 80 ° C. until gas evolution ceases. Excess thionyl chloride is removed in vacuo at 50 ° C. and the residue is dissolved in 100 ml of anhydrous tetrahydrofuran. This solution is added dropwise to a suspension of 27.1 mL of triethylamine and 16.1 g of methyl cis-1-amino-4-methylcyclohexanecarboxylate at 0-10 ° C. in 200 mL of anhydrous tetrahydrofuran. The mixture is then stirred at rt for 1 h, the precipitate is suction filtered, washed with tetrahydrofuran and the filtrate is concentrated in vacuo. The residue is dissolved in methylene chloride, washed with 0.5 N HCl, dried over magnesium sulfate and concentrated by evaporation. Recrystallization with MTB ether / n-hexane yields 20.4 g (73% of theory) of the compound shown above with a melting point of 108 ° C.

Example (II-2)

47.7 g (0.158 mol) of N- (2,6-dimethyl-4-methoxy-phenylacetyl) -4-amino-pyran-4-carbonitrile suspended in 320 ml of anhydrous methylene chloride at 30 to 40 ° C Add dropwise to 77.4 g (0.79 moles) of concentrated sulfuric acid. The mixture is stirred at 40 ° C. for 2 hours, 109 mL of anhydrous methanol is added dropwise, and the mixture is heated at a bath temperature of 40 to 70 ° C. for 6 hours. The reaction mixture is poured into 0.8 kg of ice and extracted with methylene chloride, then the combined organic phases are washed with sodium bicarbonate solution, dried over magnesium sulfate and the solvent is evaporated in vacuo. After recrystallization with MTB ether / n-hexane, 37.7 g (71% of theory) of the above-described compound having a melting point of 168 ° C. are obtained.

The substances of the general formula (II) described in Table 11 below are similarly obtained:

Example (XVII-1)

38.6 g (0.2 mol) of 2,6-dimethyl-4-methoxyphenylacetic acid are heated at 50 to 60 ° C with 29.3 ml of thionyl chloride until gas evolution ceases. Excess thionyl chloride was distilled in vacuo and the residue was dissolved in 100 mL of anhydrous tetrahydrofuran, then the solution was 28 mL (0.2 mol) of tree in 400 mL of anhydrous tetrahydrofuran at 0-10 ° C. To the solution of ethylyne and 25.2 g (0.2 mol) of 4-amino-pyran-4-carbonitrile is added dropwise, and then the mixture is stirred at room temperature for 1 hour. The reaction mixture is poured into a mixture of 900 ml of water and 100 ml of 2N hydrochloric acid, the precipitate is suction filtered off, dried and recrystallized with MTB ether / n-hexane. 47 g (79% of theory) of the above-described compound having a melting point of 156 ° C. are obtained.

The compound of formula (XVII) described in Table 12 below is obtained similarly to Example (XVII-1).

Example of use

Example A

Miss Juice Test

Solvent: Dimethylformamide 7 parts by weight

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

1 part by weight of the active compound is mixed with the specified amount of solvent and the specified amount of emulsifier, and the concentrate is distilled with water to a desired concentration to prepare a suitable formulation of the active compound.

Cabbage leaves (Brasica oleracea) heavily infected with peach aphid (Myzus persicae) were treated by immersing in the active compound preparation at the desired concentration.

After a certain period of time, the percentage of relief is determined. 100% means that all peach aphids have been killed; 0% means that none of the peach aphids have been killed.

In this test, for example, a compound according to Preparation Examples Ia-1, Ia-2, Ia-6 and Ic-1 has a rescue rate of at least about 80% after 6 days at an exemplary active compound concentration of 0.1% Indicated.

Example B

Germination test

Solvent: 3 parts by weight of acetone

Emulsion: 1 part by weight of alkylaryl polyglycol ether

1 part by weight of the active compound was mixed with the solvent of the specified amount, the emulsifier of the specified amount was added, and the concentrate was diluted with water to the desired concentration to prepare a suitable formulation of the active compound.

Seeds of the test plants were sown in standard soil and after 24 hours the active compound formulations were irrigated. It is important to keep the amount of water per unit area constant. The concentration of active compound in the formulation is not important, only the application rate of active compound per unit area is important. Three weeks later, the degree of damage of the plants was compared to the development of the untreated control and the damage was assessed in%. The figures have the following meanings:

0% has no effect (as in untreated controls),

100% indicates complete death.

Example C

Tetranicus test (OP tolerance / spray treatment)

Solvent: 3 parts by weight of dimethylformamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

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

Soybean plants (Phaseolus vulgaris) heavily infected with greenhouse red spider mites (Tetranychus urticae) at all stages of growth were sprayed with active compound formulations of the desired concentration.

After a certain period of time, the% action was determined. 100% means that all spider mites have been killed; 0% means that no spider mite has been killed.

In this test, for example, the compound according to Preparation Example Ia-6 exhibited a rescue rate of at least about 98% after 7 days at an exemplary active compound concentration of 0.01%.

Claims (13)

1H-3-aryl-pyrrolidine-2,4-dione derivative of formula (I). Where A represents hydrogen or in each case optionally represents halogeno-substituted alkyl, alkenyl, alkoxyalkyl, polyalkoxyalkyl or alkylthioalkyl, or cycloalkyl optionally interrupted and optionally substituted by at least one hetero atom Or in each case optionally represents halogen-, alkyl-, halogenoalkyl-, alkoxy- or nitro-substituted aryl, arylalkyl or hetaryl, B represents alkyl or alkoxyalkyl, or A and B together with the C atom to which they are attached represent an unsubstituted or substituted ring which is optionally interrupted and saturated or unsaturated by at least one heteroatom, X represents alkyl or alkoxy, Y represents hydrogen, alkyl or alkoxy, Z represents hydrogen, alkyl or alkoxy, G is hydrogen (a) or a group Indicates E represents a metal ion equivalent or ammonium ion, L represents oxygen or sulfur, M represents oxygen or sulfur, R ¹ at each occurrence optionally represents a halogeno-substituted alkyl, alkenyl, alkoxyalkyl, altylthioalkyl or polyalkoxyalkyl, or an optionally halogen- or alkyl-substituted cycloalkyl which may be interrupted by at least one hetero winza Or in each case optionally substituted phenyl, phenylalkyl, hetaryl, phenoxyalkyl or hetaryloxyalkyl, R ² in each case optionally represents halogeno-substituted alkyl, alkenyl, alkoxyalkyl or polyalkoxyalkyl, or in each case optionally represents cycloalkyl, phenyl or benzyl, R ³ , R ⁴ and R ⁵ independently of each other represent in each case optionally halogeno-substituted alkyl, alkoxy, alkylalkyl, dialkylamino, alkylthio, alkenylthio or cycloalkylthio, or in each case optionally Substituted phenyl, phenoxy or phenylthio, R ⁶ R ⁷ independently of one another represents hydrogen, in each case optionally represents halogeno-substituted alkyl, cycloalkyl, alkenyl, alkoxy or alkoxyalkyl, optionally substituted phenyl, or optionally substituted benzyl Or a ring optionally interrupted by oxygen or sulfur together with the N atom to which they are attached, Provided that at least one of substituents X and Z represents alkoxy when X represents alkyl. A compound according to claim 1 having the following structures (Ia) to (Ig) according to the meanings (a), (b), (c), (d), (e), (f) and (g) of group G. 1H-3-aryl-pyrrolidine-2,4-dione derivative of general formula (I). Where A, B, E, L, M, X, Y, Z, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ and R ⁷ have the meanings mentioned in claim 1. (A) Intramolecular condensation reaction of N-acylamino acid ester of general formula (II) in the presence of a diluent and in the presence of a base to give 1H-3-aryl-pyrrolidine-2,4-dione of general formula (Ia) And / or to prepare an enol thereof, (B) a compound of the general formula (Ia), α) reacting with an acid halide of formula (III), optionally in the presence of a diluent, and optionally in the presence of an acid-bond, β) reacting with a carboxylic anhydride of formula (IV) optionally in the presence of a diluent and optionally in the presence of an acid-binder to yield a compound of formula (Ib), (C) Reacting a compound of formula (Ia) with a chloroformic acid ester or chloroformic acid thioester of formula (V), optionally in the presence of a diluent, and optionally in the presence of an acid-binder, to yield a compound of formula (Ic-a) To obtain a compound of (D) a compound of the general formula (Ia), α) reacting with a chloromonothioformic ester or chlorodithioformic ester of general formula (VI), optionally in the presence of a diluent, and optionally in the presence of an acid-binding agent, β) optionally reacted with carbon disulfide in the presence of a diluent and optionally in the presence of a base, followed by reaction with an alkyl halide of formula (VII) to obtain a compound of formula (Ic-b), (E) reacting a compound of formula (Ia) with sulfonyl chloride of formula (VIII), optionally in the presence of a diluent, and optionally in the presence of an acid-binder, to obtain a compound of formula (Id), (F) 1H-3-aryl-pyrrolidine-2,4-diol of Formula (Ia) and / or an enol thereof, in general in the presence of a diluent, and optionally in the presence of an acid-binding agent React with a phosphorus compound of to give 3-aryl-pyrrolidine-2,4-dione of formula (Ie), or (G) reacting a compound of formula (Ia) with a metal hydroxide, metal alkoxide or amine of formulas (X) and (XI), optionally in the presence of a diluent, to obtain a compound of formula (I-f), or (H) a compound of the general formula (Ia), α) is reacted with an isocyanate or isothiocyanate of the general formula (XII), optionally in the presence of a diluent and optionally in the presence of a catalyst, β) reacting with carbamoyl chloride or thiocarbamoyl chloride of the general formula (XIII) to obtain a compound of formula (Ig), optionally in the presence of a diluent, and optionally in the presence of an acid-binding agent, A process for preparing the 1H-3-aryl-pyrrolidine-2,4-dione derivative of formula (I) according to claim 1. Where A, B, L, X, Y, Z, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ and R ⁷ have the meanings mentioned in claim 1, R ⁸ represents alkyl, Hal in general formula (III) represents halogen, Hal in formula (VII) represents chlorine, bromine or iodine, Hal in general formula (IX) represents halogen, M represents oxygen or sulfur, E represents a metal ion equivalent or ammonium ion, Me represents a monovalent or divalent metal ion, t represents the number of 1 or 2, R ⁹ , R ¹⁰ and R ¹¹ independently of one another represent hydrogen and / or alkyl. The method of claim 1, A represents hydrogen or in each case is optionally mono- or poly-halogeno-substituted C ₁ -C ₁₂ -alkyl, C ₂ -C ₈ -alkenyl, C ₁ -C ₁₀ -alkoxy-C ₁ -C _May be blocked by ₈ -alkyl, C ₁ -C ₈ -polyalkoxy-C ₁ -C ₈ -alkyl or C ₁ -C ₁₀ -alkylthio-C ₁ -C ₆ -alkyl, or by oxygen and / or sulfur; 3 to 8 ring atoms and optionally halogen-, C ₁ -C ₄ alkyl- or C ₁ -C ₄ -alkoxy-substituted cycloalkyl, in each case optionally mono- to poly-halogen-, C _1- C ₆ - alkyl -, C ₁ -C ₆ - halogenoalkyl -, C ₁ -C ₆ - alkoxy - and / or - a nitro-substituted phenyl, naphthyl, pyridyl, imidazolyl, indolyl, thiazolyl , Furanyl, thienyl, phenyl-C ₁ -C ₆ -alkyl or naphthyl-C ₁ -C ₆ -alkyl, B represents C ₁ -C ₁₂ -alkyl or C ₁ -C ₈ -alkoxy-C ₁ -C ₆ -alkyl, or A, B and the carbon atoms to which they are attached are C ₁ -C ₆ -alkyl, C ₃ -C ₈ -cycloalkyl, C ₁ -C ₄ -halogenoalkyl, C ₁ -C ₆ -alkoxy, C ₁ -C ₆ -Represent saturated or unsaturated C ₃ -C ₁₀ -spirocyclic radicals optionally mono- or polysubstituted by alkylthio, halogen or phenyl and optionally blocked by oxygen or sulfur, or A, B and the carbon atoms to which they are attached are C ₃ -C substituted by alkylenediyl groups optionally interrupted by one or two oxygen and / or sulfur atoms or substituted by alkylenedioxy or alkylenedithio groups ₆ -spirocyclic radical, wherein the alkylenylyl, alkylenedioxy or alkylenedithio group together with the carbon atom to which they are attached form an additional 5- to 8-membered spirocyclic ring, A, B and the carbon atom to which they are two of the substituents are with C ₁ -C ₄ bond-alkoxy or by halogen, optionally substituted saturated or unsaturated, which may be interrupted by oxygen or sulfur -alkyl, C ₁ -C ₄ C ₃ -C ₈ -spirocyclic radicals representing 5- to 8-membered rings, X represents C ₁ -C ₆ -alkyl or C ₁ -C ₆ -alkoxy, Y represents hydrogen, C ₁ -C ₆ -alkyl or C ₁ -C ₆ -alkoxy, Z represents hydrogen, C ₁ -C ₆ -alkyl or C ₁ -C ₆ -alkoxy, G is hydrogen (a) or a group Indicates From here, E represents a metal ion equivalent or ammonium ion, L represents oxygen or sulfur, M represents oxygen or sulfur, R ¹ is in each case optionally mono- or poly-halogeno-substituted C ₁ -C ₂₀ -alkyl, C ₂ -C ₂₀ -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 ₂ -C ₈ -alkyl or rings which may be interrupted by at least one oxygen and / or sulfur atom Or optionally halogen- or C ₁ -C ₆ -alkyl-substituted cycloalkyl having 3 to 8 atoms, Optionally mono-to penta-halogenoalkyl -, - nitro -, -C ₁ -C ₆ - alkyl -, -C ₁ -C ₆ - alkoxy -, -C ₁ -C ₆ - halogenoalkyl -, -C ₁ - C ₆ -halogenoalkoxy-, -C ₁ -C ₆ -alkylthio- or -C ₁ -C ₆ -alkylsulfonyl-substituted phenyl, Optionally mono-to penta-halogenoalkyl -, -C ₁ -C ₆ - alkyl -, -C ₁ -C ₆ - alkoxy -, -C ₁ -C ₆ - halogenoalkyl -, or -C ₁ -C ₆ - haloalkyl halogeno-alkoxy-substituted phenyl -C ₁ -C ₆ - or represent alkyl, Optionally represents mono- to tri-halogeno- or -C ₁ -C ₆ -alkyl-substituted pyridyl, thienyl, furanyl, pyrazolyl, pyrimidyl or thiazolyl, Optionally mono- to tri-halogeno- or -C ₁ -C ₆ -alkyl-substituted phenoxy-C ₁ -C ₆ -alkyl, or Optionally mono- or di-halogeno-, -amino- or -C ₁ -C ₆ -alkyl-substituted pyridinyloxy-C ₁ -C ₆ -alkyl, pyrimidinyloxy-C ₁ -C ₆ -alkyl or thiazolyl oxy -C ₁ -C ₆ - represents an alkyl, R ² in each case is optionally mono- or poly-halogeno-substituted C ₁ -C ₂₀ -alkyl, C ₃ -C ₂₀ -alkenyl, C ₁ -C ₈ -alkoxy-C ₂ -C ₈ -alkyl or C ₁ -C ₈ -polyalkoxy-C ₂ -C ₈ -alkyl, or Optionally mono- or poly-halogeno-, -C ₁ -C ₄ -alkyl- and / or -C ₁ -C ₄ -alkoxy-substituted C ₃ -C ₈ -cycloalkyl, or Optionally mono-or tri-halogeno-, - _- nitro, -C ₁ -C ₆ - alkyl -, -C ₁ -C ₆ - alkoxy -, or -C ₁ -C ₆ - halogenoalkyl-substituted phenyl or Benzyl, R ³ , R ⁴ and R ⁵ independently of one another in each occurrence are optionally mono- or poly-halogeno-substituted C ₁ -C ₈ -alkyl, C ₁ -C ₈ -alkoxy, C ₁ -C ₈ -alkylamino , Di- (C ₁ -C ₈ ) -alkylamino, C ₁ -C ₈ -alkylthio, C ₃ -C ₆ -alkenylthio or C ₃ -C ₇ -cycloalkylthio, or in each case halogen , Nitro, cyano, C ₁ -C ₄ -alkoxy, C ₁ -C ₄ -halogenoalkoxy, C ₁ -C ₄ -alkylthio, C ₁ -C ₄ -halogenoalkylthio, C ₁ -C _4- Phenyl, phenoxy or phenylthio optionally mono- or poly-substituted by alkyl or C ₁ -C ₄ -halogenoalkyl, R ⁶ and R ⁷ independently represent hydrogen or, in each case, optionally mono- or poly-halogeno-substituted C ₁ -C ₈ -alkyl, C ₃ -C ₈ -cycloalkyl, C ₁ -C ₈ -Alkoxy, C ₃ -C ₈ -alkenyl or C ₁ -C ₈ -alkoxy-C ₂ -C ₈ -alkyl, or optionally mono- to tri-halogeno-, -C ₁ -C ₈ -halogeno alkyl-, -C ₁ -C ₈ - alkyl -, or -C ₁ -C ₈ - alkoxy - represents an optionally substituted phenyl or optionally mono- to tri-halogeno -, -C ₁ -C ₈ - alkyl -, - C ₁ -C ₈ - halogenoalkyl - and / or -C ₁ -C ₈ - alkoxy - represents the a-substituted benzyl, or they are combined by an oxygen or sulfur atom together with the N random block C ₃ -C ₆ - An alkylene ring, Provided that when X represents alkyl, 1H-3-aryl-pyrrolidine-2,4-dione of formula (I) wherein at least one of substituents Y and Z represents alkoxy. The method of claim 1, A represents hydrogen or in each occurrence is optionally mono to hexa-fluoro- or chloro-substituted C ₁ -C ₁₀ -alkyl, C ₂ -C ₆ -alkenyl, C ₁ -C ₈ -alkoxy-C ₁ -C ₆ -alkyl, C ₁ -C ₆ -polyalkoxy-C ₁ -C ₆ -alkyl or C ₁ -C ₈ -alkylthio-C ₁ -C ₆ -alkyl, or 1 or 2 oxygen and / or Optionally represents fluoro-, chloro-, C ₁ -C ₃ -alkyl- or C ₁ -C ₃ -alkoxy-substituted cycloalkyl having 3 to 7 ring atoms which may be interrupted by a sulfur atom, or in each case to optionally mono- or di-fluoro-, chloro-, bromo -, -C ₁ -C ₄ - alkyl -, -C ₁ -C ₄ - halogenoalkyl -, -C ₁ -C ₄ - alkoxy, or - Nitro-substituted phenyl, pyridyl, thienyl, furanyl, imidazolyl, indolyl or phenyl-C ₁ -C ₄ -alkyl, B represents C ₁ -C ₁₀ -alkyl or C ₁ -C ₆ -alkoxy-C ₁ -C ₄ -alkyl, or A, B and the carbon atoms to which they are attached are C ₁ -C ₆ -alkyl, C ₃ -C ₈ -cycloalkyl, C ₁ -C ₃ -halogenoalkyl, C ₁ -C ₆ -alkoxy, C ₁ -C ₅ -Represent saturated or unsaturated C ₃ -C ₉ -spirocyclic radicals optionally substituted one or more times by thioalkyl, fluorine, chlorine or panyl and optionally blocked by oxygen or sulfur, or A, B and the carbon atoms to which they are attached are C ₃ -C ₆ -substituted by alkylenediyl groups optionally interrupted by one or two oxygen or sulfur atoms or substituted by alkylenedioxy or alkylenedithiothio groups. Spirocyclic radicals, wherein alkylenediyl, alkylenedioxy or alkylenedithio groups together with the carbon atoms to which they are attached form an additional 5- to 7-membered spirocyclic ring, A, B and the carbon atom to which they are attached are two substituents together are C ₁ -C ₃ - alkyl, C ₁ -C ₃ - alkoxy, which is optionally substituted by fluorine, chlorine or bromine which may be interrupted by oxygen or sulfur C ₃ -C ₆ -spirocyclic radicals representing saturated or unsaturated 5- to 7-membered rings, X represents C ₁ -C ₅ -alkyl or C ₁ -C ₄ -alkoxy, Y represents hydrogen, C ₁ -C ₅ -alkyl or C ₁ -C ₄ -alkoxy, Z represents hydrogen, C ₁ -C ₄ -alkyl or C ₁ -C ₄ -alkoxy, G is hydrogen (a) or a group Indicates From here, E represents a metal ion equivalent or ammonium ion, L represents oxygen or sulfur, M represents oxygen or sulfur, R ¹ is in each case optionally mono- to hexa-fluoro- or -chloro-substituted C ₁ -C ₁₆ -alkyl, C ₂ -C ₁₆ -alkenyl, C ₁ -C ₆ -alkoxy-C ₁ -C _{To 6} -alkyl, C ₁ -C ₆ -alkylthio-C ₁ -C ₆ -alkyl, C ₁ -C ₆ -polyalkoxy-C ₂ -C ₆ -alkyl, or to 1 or 2 oxygen and / or sulfur atoms Optionally represents fluoro-, chloro- or C ₁ -C ₅ -alkyl-substituted cycloalkyl having 3 to 7 ring atoms which can be interrupted, or Optionally mono-to tri-fluoro--chloro -, - bromo -, - nitro -, -C ₁ -C ₄ - alkyl -, -C ₁ -C ₄ - alkoxy -, -C ₁ -C ₃ - Halogenoalkyl-, —C ₁ -C ₃ -halogenoalkoxy-, —C ₁ -C ₄ -alkylthio- and / or —C ₁ -C ₄ -alkylsulfonyl-substituted phenyl, Optionally mono-to tri-fluoro-, - chloro -, - bromo -, -C ₁ -C ₄ - alkyl -, -C ₁ -C ₄ - alkoxy -, -C ₁ -C ₃ - halogenoalkyl - Or -C ₁ -C ₃ -halogenoalkoxy-substituted phenyl-C ₁ -C ₄ -alkyl, or Optionally represents mono- or di-fluoro-, -chloro-, -bromo- or C ₁ -C ₄ -alkyl-substituted pyridyl, thienyl, furanyl, pyrazolyl, pyrimidyl or thiazolyl, Optionally mono- or di-fluoro -, - chloro -, - bromo - or -C ₁ -C ₄ - alkyl - substituted phenoxy during -C ₁ -C ₅ - or represent alkyl, Optionally mono- or di-fluoro -, - chloro -, - bromo -, - amino - or -C ₁ -C ₄ - alkyl-substituted pyrimidinyl oxy -C ₁ -C ₅ - alkyl, pyridyloxy -C ₁ -C ₅ -alkyl or thiazolyloxy-C ₁ -C ₅ -alkyl, R ² in each case is mono- to hexa-fluoro- and / or -chloro-substituted C ₁ -C ₁₆ -alkyl, C ₃ -C ₁₆ -alkenyl, C ₁ -C _6- Alkoxy-C ₁ -C ₆ -alkyl or C ₁ -C ₆ -polyalkoxy-C ₂ -C ₆ -alkyl, or Optionally mono- to hexa-fluoro-, -chloro-, -C ₁ -C ₃ -alkyl- or -C ₁ -C ₃ -alkoxy-substituted C ₃ -C ₇ -cycloalkyl, or Optionally mono- or di-fluoro -, - chloro -, - bromo -, - nitro -, -C ₁ -C ₄ - alkyl -, -C ₁ -C ₃ - alkoxy - or -C ₁ -C ₃ - Halogenoalkyl-substituted phenyl or benzyl, R ³ , R ⁴ and R ⁵ independently of one another in each occurrence are optionally mono- to hexa-fluoro- or -chloro-substituted C ₁ -C ₆ -alkyl, C ₁ -C ₆ -alkoxy, C ₁ -C ₆ -alkylamino, di- (C ₁ -C ₆ ) -alkylamino, C ₁ -C ₆ -alkylthio, C ₃ -C ₄ -alkenylthio or C ₃ -C ₆ -cycloalkylthio, or Fluorine, chlorine, bromine, nitro, cyano, C ₁ -C ₃ -alkoxy, C ₁ -C ₃ -halogenoalkoxy, C ₁ -C ₃ -alkylthio, C ₁ -C ₃ -halogenoalkylthio, C ₁ -C ₃ - alkyl or C ₁ -C ₃ - haloalkyl optionally substituted by a halogeno or alkyl-disubstituted phenyl, represents a phenoxy or phenylthio, R ⁶ and R ⁷ independently represent hydrogen or, in each case, optionally mono- to hexa-fluoro- or -chloro-substituted C ₁ -C ₆ -alkyl, C ₁ -C ₆ -cycloalkyl, C1 -C6-alkoxy, C3-C6-alkenyl or C1-C6-alkoxy-C2-C6-alkyl, or represent fluorine, chlorine, bromine, C ₁ -C ₅ -halogenoalkyl, C ₁ -C ₅ -alkyl Or phenyl optionally monosubstituted or disubstituted by C ₁ -C ₅ -alkoxy, fluorine, chlorine, bromine, C ₁ -C ₅ -alkyl, C ₁ -C ₅ -halogenoalkyl or C ₁ -C ₅ -Represents a benzyl optionally monosubstituted or disubstituted by alkoxy, or a C ₃ -C ₆ -alkylene ring optionally interrupted by oxygen or sulfur together with the N atom to which they are attached, Provided that when X represents alkyl, at least one of substituents Y and Z represents 1H-3-aryl-pyrrolidine-2,4-dione of formula (I), which represents alkoxy, The method of claim 1, A represents hydrogen or in each occurrence is optionally mono- to tri-fluoro- or-chloro-substituted C ₁ -C ₈ -alkyl, C ₂ -C ₄ -alkenyl, C ₁ -C ₆ -alkoxy- C ₁ -C ₄ -alkyl, C ₁ -C ₄ -polyalkoxy-C ₁ -C ₄ -alkyl or C ₁ -C ₆ -alkylthio-C ₁ -C ₄ -alkyl, or 1 or 2 oxygen and / Or optionally fluoro-, chloro-, methyl-, ethyl-, methoxy- or ethoxy-substituted cycloalkyl having 3 to 6 ring atoms which may be interrupted by a sulfur atom, or in each case optionally mono Or di-fluoro-, -chloro-, -bromo-, -methyl-, -ethyl-, -propyl, -isopropyl-, -methoxy-, -ethoxy-, -trifluoromethyl- and / Or -nitro-substituted phenyl, furanyl, thienyl, imidazolyl, indolyl, pyridyl or benzyl, B represents C ₁ -C ₈ -alkyl or C ₁ -C ₄ -alkoxy-C ₁ -C ₂ -alkyl, A, B and the carbon atoms to which they are attached are methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, t-butyl, cyclohexyl, trifluoromethyl, methoxy, ethoxy, propoxy, iso Saturated, optionally substituted one or more times with propoxy, butoxy, isobutoxy, sec-butoxy, t-butoxy, methylthio, ethylthio, fluorine, chlorine or phenyl and optionally blocked by oxygen or sulfur or Represent unsaturated C ₃ -C ₈ -spirocyclic radicals, or A, B and the carbon atoms to which they are attached represent C ₅ -C ₆ -spirocyclic radicals substituted by alkylenediyl groups optionally substituted by oxygen or sulfur atoms or substituted by alkylenedioxy groups, wherein Alkylenediyl or alkylenedioxy groups together with the carbon atoms to which they are attached form additional 5- to 7-membered spirocyclic radicals, A, B and the carbon atoms to which they are attached represent C ₃ -C ₆ -spirocyclic radicals which represent a saturated or unsaturated 5- or 6-membered ring in which two substituents together may be interrupted by oxygen or sulfur, X represents a methyl, ethyl, propyl, isopropyl, methoxy, ethoxy, propoxy or isopropoxy group, Y represents hydrogen, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, t-butyl, methoxy, ethoxy, propoxy or isopropoxy, Z represents hydrogen, methyl, ethyl, propyl, isopropyl, methoxy, ethoxy, propoxy or isopropoxy, G is hydrogen (a) or a group Indicates, From here, E represents a metal ion equivalent or ammonium ion, L represents oxygen or sulfur, M represents oxygen or sulfur, R ¹ is in each case optionally mono- to tri-fluoro- or -chloro-substituted C ₁ -C ₁₄ -alkyl, C ₂ -C ₁₄ -alkenyl, C ₁ -C ₄ -alkoxy-C ₁ -C _{To 6} -alkyl, C ₁ -C ₄ -alkylthio-C ₁ -C ₆ -alkyl or C ₁ -C ₄ -polyalkoxy-C ₂ -C ₄ -alkyl, or to 1 or 2 oxygen and / or sulfur atoms Optionally substituted fluoro-, chloro-, methyl-, ethyl-, propyl-, iso-propyl-, butyl-, isobutyl or t-butyl-substituted cycloalkyl which may be interrupted by Or Optionally mono- or di-fluoro-, -chloro-, -bromo--, -methyl-, -ethyl-, -propyl-, -isopropyl-, -methoxy-, -ethoxy-, -trifluoro Chloromethyl, -trifluoromethoxy-, -methylthio-, -ethylthio-, -methylsulfonyl-, -ethylsilfonyl- or -nitro-substituted phenyl, Optionally mono- or di-fluoro-, -chloro-, -bromo-, -methyl-, -ethyl-, -propofyl-, -isopropyl-, -methoxy-, -ethoxy-, -trifluoro Romero butyl-or-trifluoromethoxy-substituted phenyl, -C ₁ -C ₃ - alkyl, or represent, Optionally represents mono- or di-fluoro-, -chloro-, -bromo-, -methyl- or -ethyl-molar thienyl, furanyl or pyridyl, or Optionally represents mono- or di-fluoro-, -chloro-, -methyl- or -ethyl-substituted phenoxy-C ₁ -C ₄ -alkyl, or A mouth in each case mono-fluoro-or di, - a glow -, - amino -, -methyl or -ethyl-substituted pyridyloxy -C ₁ -C ₄ - alkyl, pyrimidinyl oxy -C _1- C ₄ -alkyl or thiazolyloxy-C ₁ -C ₄ -alkyl, R ² is in each case optionally mono- to tri-fluoro-, -chloro-substituted C ₁ -C ₁₄ -alkyl, C ₃ -C ₁₄ -alkenyl, C ₁ -C ₄ -alkoxy-C ₁ -C ₆ -alkyl or C ₁ -C ₄ -polyalkoxy-C ₂ -C ₆ -alkyl, or Optionally represents mono- to tri-fluoro-, -chloro-, -methyl-, -ethyl-, -propyl-, -isopropyl- or -methoxy-substituted C ₃ -C ₆ -cycloalkyl, In each case optionally mono- or di-fluoro-, -chloro-, -nitro-, -methyl-, -ethyl-, -propyl-, -isopropyl-, -methoxy-, -ethoxy- or -tri Fluoro-methyl-substituted phenyl or benzyl, R ³ , R ⁴ and R ⁵ independently of one another in each occurrence are optionally mono- to tri-fluoro- or -chloro-substituted C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alkoxy, C ₁ -C ₄ -alkylamino, di- (C ₁ -C ₄ ) -alkylamino or C ₁ -C ₄ -alkylthio or represent fluorine, chlorine, bromine, nitro, cyano, C ₁ -C ₂ -alkoxy, C ₁ -C ₂ - fluoro-alkoxy, C ₁ -C ₂ - alkylthio, C ₁ -C ₂ - alkylthio, C ₁ -C ₂ fluoroalkyl -alkyl or C ₁ -C ₂ - alkyl optionally substituted by fluoro Mono- or di-substituted phenyl, phenoxy or phenylthio, R ⁶ and R ⁷ independently represent hydrogen or, in each case, optionally mono- to tri-fluoro- or -chloro-substituted C ₁ -C ₄ -alkyl, C ₃ -C ₆ -cycloalkyl, C ₁ -C ₄ -alkoxy, C ₃ -C ₄ -alkenyl or C ₁ -C ₄ -alkoxy-C ₂ -C ₄ -alkyl, or represent fluorine, chlorine, bromine, C ₁ -C ₄ -halogenoalkyl, Phenyl optionally substituted by C ₁ -C ₄ -alkyl and / or C ₁ -C ₄ -alkoxy, fluorine, chlorine, bromine, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -halo Benzyl optionally mono- or di-substituted by genoalkyl and / or C ₁ -C ₄ -alkoxy, or C ₃ -C ₆ -alkyrene ring optionally blocked by oxygen or sulfur with the N atom to which they are attached , Provided that when X represents alkyl, 1H-3-aryl-pyrrolidine-2,4-dione of formula (I) wherein at least one of substituents Y and Z represents alkoxy. Compound of general formula (II). Where A, B, X, Y and Z have the meanings mentioned in claim 1, R ⁸ represents alkyl. Amino acid derivatives of formula (XIV) are acylated with phenylacetyl halides of formula (XV), esterified acylamino acids of formula (IIa), or aminonitriles of formula (XVI) Reacting with phenylacetyl halide of) to give a compound of formula (XVII), which is then subjected to an alcoholic decomposition in the presence of sulfuric acid, acyl- of formula (II) according to claim 7 Method for preparing the amino acid ester. Where R ^{12 '} represents hydrogen (XIVa) or alkyl (XIVb), A, B, X, Y and Z have the meanings mentioned in claim 1, Hal represents chlorine or bromine, R ¹² represents hydrogen. Compound of formula (XVII). Where A, B, X, Y and Z have the meanings mentioned in claim 1. A process for preparing a compound of formula (XVII) according to claim 9 characterized by reacting an aminonitrile of formula (XVI) with a phenylacetyl halide of formula (XV). Where A, B, X, Y and Z have the meanings mentioned in claim 1, Hal represents chlorine or bromine. A pesticide or weed control composition comprising at least one 1H-3-aryl-pyrrolidine-2,4-dione derivative of formula (I) according to claim 1. 1H-3-aryl-pyrrolidine-2,4-dione derivatives of general formula (I) according to claim 1, characterized in that they act on pests and / or their habitats or weeds and / or their habitats How to get rid of weeds. A pesticide or weed control agent is prepared by mixing the 1H-3-amine-pyrrolidine-2,4-dione derivative of formula (I) according to claim 1 with a weight agent and / or a surfactant. How to.