DE10205862A1 - DELTA 1 Pyrrolines - Google Patents

Abstract

New DELTA · 1 · pyrrolines of the formula (I) DOLLAR F1 in which DOLLAR AR · 1 ·, R · 2 ·, R · 3 ·, R · 4 ·, R · 5 · and m have the meanings given in the description , DOLLAR A several processes for the preparation of these substances and their use for controlling pests.

Description

The present invention relates to new Δ ¹ -pyrrolines, several processes for their preparation and their use as pesticides.

It is already known that numerous Δ ¹ -pyrrolines have insecticidal properties (cf. WO 00/21958, WO 99/59968, WO 99/59967 and WO 98/22438). The effectiveness of these substances is good, but leaves something to be desired in some cases.

New Δ ¹ pyrrolines of the formula (I)


found in which
R ^{1 represents} alkyl or optionally substituted aryl,
R ^{2 represents} halogen, cyano, nitro, amino, alkyl or alkoxy,
R ^{3 represents} hydrogen, halogen, alkyl or alkoxy,
R ^{4 stands} for the grouping -XYZE, with the proviso that Y does not stand for a direct bond if X does not stand for a direct bond,
R ^{5 represents} halogen, in each case optionally substituted alkyl, alkoxy or alkylthio,
m represents 0, 1, 2, 3 or 4, where the radicals R ^{5 can be the} same or different if m represents 2, 3 or 4,
X for a direct bond, oxygen, -S (O) _w -, -NR ⁶ -, carbonyl, carbonyloxy, oxycarbonyl, oxysulfonyl (OSO ₂ ), alkylene, haloalkylene, alkenylene, haloalkenylene, alkynylene, alkyleneoxy, oxyalkylene, oxyalkyleneoxy, - S (O) _{w is} alkylene, cyclopropylene or oxiranylene,
Y stands for a direct bond or for optionally substituted phenylene, naphthylene, tetrahydronaphthylene or heterocyclylene,
Z represents a direct bond or - (CH ₂ ) _n -,
E for hydrogen, halogen, hydroxy, cyano, formyl, nitro, trialkylsilyl, pentafluorothio, -S (O) _w R ⁷ , -OSO ₂ R ⁷ , -NR ⁸ R ⁹ , -COR ⁷ , -CO ₂ R ⁷ , - OC (O) R ⁷ , -CONR ¹⁰ R ¹¹ , N (R ¹² ) COR ¹³ , -C (R ¹⁴ ) = N-OR ¹⁵ , -SO ₂ NR ¹⁶ R ¹⁷ , -N (R ¹⁸ ) CO ₂ R ¹⁹ , -N (R ¹⁸ ) C (O) NR ¹⁹ R ²⁰ ; or represents in each case optionally substituted alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, cycloalkyl, cycloalkylalkyl, cycloalkyloxy, aryl, arylalkyl, aryloxy, aryloxyalkyl, saturated or unsaturated heterocyclyl or heterocyclylalkyl,
R ^{6 represents} in each case optionally substituted alkyl, cycloalkyl, cycloalkylalkyl, aryl or arylalkyl,
R ^{7 represents} in each case optionally substituted alkyl, cycloalkyl, aryl or arylalkyl,
R ⁸ and R ⁹ independently of one another represent hydrogen, -SO ₂ R ⁷ , each optionally substituted alkyl, alkenyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl or saturated or unsaturated heterocyclyl or heterocyclylalkyl,
R ⁸ and R ⁹ also together represent optionally substituted alkenylene or alkylene, where the alkylene chain can in each case be interrupted by -O-, -S- or -NR ²¹ -,
R ¹⁰ and R ¹¹ independently of one another represent hydrogen, -SO ₂ R ⁷ , each optionally substituted alkyl, alkenyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl or saturated or unsaturated heterocyclyl or heterocyclylalkyl,
R ¹⁰ and R ¹¹ also together represent optionally substituted alkylene, where the alkylene chain can be interrupted by -O-, -S- or -NR ²¹ -,
R ¹² and R ¹³ independently of one another represent hydrogen, in each case optionally substituted alkyl, cycloalkyl, cycloalkylalkyl, aryl or arylalkyl,
R ¹² and R ¹³ also together represent optionally substituted alkylene or alkenylene,
R ¹⁴ and R ¹⁵ independently of one another represent hydrogen, each optionally substituted alkyl or alkenyl,
R ¹⁶ and R ¹⁷ independently of one another represent hydrogen, each optionally substituted alkyl or cycloalkyl,
R ¹⁶ and R ¹⁷ also together represent optionally substituted alkylene, alkoxyalkylene or alkylthioalkylene,
R ^{18 represents} hydrogen or alkyl,
R ¹⁹ and R ²⁰ independently of one another represent hydrogen, in each case optionally substituted alkyl, alkenyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, saturated or unsaturated heterocyclyl or heterocyclylalkyl,
R ¹⁸ and R ¹⁹ also together represent optionally substituted alkylene, or
R ¹⁹ and R ²⁰ together with the nitrogen atom to which they are attached also represent a saturated or unsaturated heterocycle which can optionally contain a further hetero atom group from the series -O-, -S- or -NR ²² - and which optionally can be substituted
R ^{21 is} hydrogen, -SO ₂ R ⁷ , -COR ⁷ or -CO ₂ R ⁷ ; represents in each case optionally substituted alkyl, alkenyl, cycloalkyl, aryl, or saturated or unsaturated heterocyclyl,
R ^{22 represents} hydrogen, alkyl or alkenyl,
w represents 0, 1 or 2,
n stands for 1, 2, 3 or 4.

The compounds of formula (I) may optionally, depending on the type and number of substituents as geometric and / or optical isomers or Regioisomers or their isomer mixtures in different compositions available. Both the pure isomers and the isomer mixtures are claimed according to the invention.

• A) Aroylpyrrolidinone der Formel (II)
  
  
  in welcher
  R¹, R², R³, R⁴, R⁵ und m die oben angegebenen Bedeutungen haben,
  mit einer Säure gegebenenfalls in Gegenwart eines Verdünnungsmittels umsetzt, oder
• B) Verbindungen der Formel (III)
  
  
  in welcher
  R¹, R², R³, R⁴, R⁵ und m die oben angegebenen Bedeutungen haben,
  mit einer Säure gegebenenfalls in Gegenwart eines Verdünnungsmittels umsetzt.

It was also found that Δ ¹ -pyrrolines of the formula (I) can be prepared by

• A) Aroylpyrrolidinones of the formula (II)
  
  
  in which
  R ¹ , R ² , R ³ , R ⁴ , R ⁵ and m have the meanings given above,
  with an acid, if appropriate in the presence of a diluent, or
• B) Compounds of the formula (III)
  
  
  in which
  R ¹ , R ² , R ³ , R ⁴ , R ⁵ and m have the meanings given above,
  with an acid, if appropriate in the presence of a diluent.

• A) Δ¹-Pyrroline der Formel (I-b)
  
  
  in welcher
  R⁴² für Chlor, Brom, Iod, -OSO₂CF₃ oder -OSO₂(CF₂)₃CF₃ steht,
  R¹, R², R³, R⁵ und m die oben angegebenen Bedeutungen haben, mit cyclischen Verbindungen der Formel (IV)
  
  Δ¹-Y¹-E (IV)
  
  in welcher
  Y¹ und E die oben angegebenen Bedeutungen haben und
  A¹ für Chlor, Brom, Iod, -OSO₂CF₃ oder -OSO₂(CF₂)₃CF₃ steht,
  in Gegenwart eines Katalysators, in Gegenwart eines Diboronsäureesters und gegebenenfalls in Gegenwart eines Säurebindemittels und gegebenenfalls in Gegenwart eines Verdünnungsmittels in einer Tandem-Reaktion umsetzt, oder
• B) Δ¹-Pyrroline der Formel (V)
  
  
  in welcher
  A² für -B(OH)₂, (4,4,5,5-Tetramethyl-1,3,2-dioxaborolan)-2-yl, (5,5-Dimethyl-1,3,2-dioxaborinan)-2-yl, (4,4,6-Trimethyl-1,3,2-dioxaborinan)-2-yl oder 1,3,2-Benzodioxaborol-2-yl steht,
  R¹, R², R³, R⁵ und m die oben angegebenen Bedeutungen haben,
  mit cyclischen Verbindungen der Formel (IV)
  
  A¹-Y¹-E (IV)
  
  in welcher
  Y¹, E und A¹ die oben angegebenen Bedeutungen haben,
  in Gegenwart eines Katalysators, gegebenenfalls in Gegenwart eines Säurebindemittels und gegebenenfalls in Gegenwart eines Verdünnungsmittels umsetzt, oder
• C) Δ¹-Pyrroline der Formel (I-b)
  
  
  in welcher
  R¹, R², R³, R⁵, m und R⁴² die oben angegebenen Bedeutungen haben,
  mit Boronsäure-Derivaten der Formel (VI)
  
  A²-Y¹-E (VI)
  
  in welcher
  Y¹, E und A² die oben angegebenen Bedeutungen haben und
  in Gegenwart eines Katalysators, gegebenenfalls in Gegenwart eines Säurebindemittels und gegebenenfalls in Gegenwart eines Verdünnungsmittels umsetzt, oder
• D) Δ¹-Pyrroline der Formel (I-c)
  
  
  in welcher
  R⁴³ für Brom oder Iod steht,
  R¹, R², R³, R⁵ und m die oben angegebenen Bedeutungen haben,
  mit metallorganischen Verbindungen der Formel (VII)
  
  M-Y¹-E (VII)
  
  in welcher
  M für ZnCl, Sn(Me)₃ oder Sn(n-Bu)₃ steht,
  Y¹ und E die oben angegebenen Bedeutungen haben,
  in Gegenwart eines Katalysators, gegebenenfalls in Gegenwart eines Säurebindemittels und gegebenenfalls in Gegenwart eines Verdünnungsmittels umsetzt.

Δ ¹ -pyrrolines of the formula (Ia)


in which
R ^{41 stands} for the grouping -Y ¹ -E,
Y ^{1 represents} in each case optionally substituted phenylene or heterocyclylene,
R ¹ , R ² , R ³ , R ⁵ , m and E have the meanings given above,
can also be made by

• A) Δ ¹ -pyrrolines of the formula (Ib)
  
  
  in which
  R ^{42 represents} chlorine, bromine, iodine, -OSO ₂ CF ₃ or -OSO ₂ (CF ₂ ) ₃ CF ₃ ,
  R ¹ , R ² , R ³ , R ⁵ and m have the meanings given above, with cyclic compounds of the formula (IV)
  
  Δ ¹ -Y ¹ -E (IV)
  
  in which
  Y ¹ and E have the meanings given above and
  A ^{1 represents} chlorine, bromine, iodine, -OSO ₂ CF ₃ or -OSO ₂ (CF ₂ ) ₃ CF ₃ ,
  in a tandem reaction in the presence of a catalyst, in the presence of a diboronic acid ester and optionally in the presence of an acid binder and optionally in the presence of a diluent, or
• B) Δ ¹ -pyrrolines of the formula (V)
  
  
  in which
  A ² for -B (OH) ₂ , (4,4,5,5-tetramethyl-1,3,2-dioxaborolane) -2-yl, (5,5-dimethyl-1,3,2-dioxaborinane) - 2-yl, (4,4,6-trimethyl-1,3,2-dioxaborinan) -2-yl or 1,3,2-benzodioxaborol-2-yl,
  R ¹ , R ² , R ³ , R ⁵ and m have the meanings given above,
  with cyclic compounds of the formula (IV)
  
  A ¹ -Y ¹ -E (IV)
  
  in which
  Y ¹ , E and A ^{1 have} the meanings given above,
  in the presence of a catalyst, if appropriate in the presence of an acid binder and if appropriate in the presence of a diluent, or
• C) Δ ¹ -pyrrolines of the formula (Ib)
  
  
  in which
  R ¹ , R ² , R ³ , R ⁵ , m and R ^{42 have} the meanings given above,
  with boronic acid derivatives of the formula (VI)
  
  A ² -Y ¹ -E (VI)
  
  in which
  Y ¹ , E and A ^{2 have} the meanings given above and
  in the presence of a catalyst, if appropriate in the presence of an acid binder and if appropriate in the presence of a diluent, or
• D) Δ ¹ -pyrrolines of the formula (Ic)
  
  
  in which
  R ^{43 represents} bromine or iodine,
  R ¹ , R ² , R ³ , R ⁵ and m have the meanings given above,
  with organometallic compounds of the formula (VII)
  
  MY ¹ -E (VII)
  
  in which
  M represents ZnCl, Sn (Me) ₃ or Sn (n-Bu) ₃ ,
  Y ¹ and E have the meanings given above,
  in the presence of a catalyst, optionally in the presence of an acid binder and optionally in the presence of a diluent.

Finally, it was found that the compounds of the formula (I) have very good insecticidal properties and are useful both in crop protection as well as in material protection to combat unwanted pests, such as Insects, let use.

The Δ ¹ -pyrrolines according to the invention are generally defined by the formula (I).

Preferred are Δ ¹ -pyrrolines of the formula (I), in which
R ^{1 represents} C ₁ -C ₈ -alkyl or aryl which is optionally mono- or polysubstituted by identical or different substituents, the substituents being selected from the group consisting of halogen, cyano, nitro, alkyl, alkoxy, alkylthio, haloalkyl, haloalkoxy and haloalkylthio,
R ^{2 represents} halogen, cyano, nitro, amino, C ₁ -C ₄ alkyl or C ₁ -C ₄ alkoxy,
R ^{3 represents} hydrogen, halogen, C ₁ -C ₆ alkyl or C ₁ -C ₆ alkoxy,
R ^{4 stands} for the grouping -XYZE, with the proviso that Y does not stand for a direct bond if X does not stand for a direct bond,
R ^{5 represents} halogen, alkyl, alkoxy, alkylthio, haloalkyl, haloalkoxy or haloalkylthio,
m represents 0, 1, 2, 3 or 4, where the radicals R ^{5 can be the} same or different if m represents 2, 3 or 4,
X for a direct bond, oxygen, -S (O) _w -, -NR ⁶ -, carbonyl, carbonyloxy, oxycarbonyl, oxysulfonyl (OSO ₂ ), alkylene, haloalkylene, alkenylene, haloalkenylene, alkynylene, alkyleneoxy, oxyalkylene, oxyalkyleneoxy, - S (O) _{w is} alkylene, cyclopropylene or oxiranylene,
Y for a direct bond or for in each case optionally up to four times, identical or different, substituted by radicals from the list W ^1, phenylene, naphthylene, tetrahydronaphthylene or 5- to 10-membered, saturated or unsaturated heterocyclylene with one or more heteroatoms from the nitrogen series , Oxygen and sulfur stands,
Z represents a direct bond or - (CH ₂ ) _n -,
E for hydrogen, halogen, hydroxy, cyano, formyl, nitro, trialkylsilyl, pentafluorothio, -S (O) _w R ⁷ , -OSO ₂ R ⁷ , -NR ⁸ R ⁹ , -COR ⁷ , -CO ₂ R ⁷ , - OC (O) R ⁷ , -CONR ¹⁰ R ¹¹ , -N (R ¹² ) COR ¹³ , -C (R ¹⁴ ) = N-OR ¹⁵ , -SO ₂ NR ¹⁶ R ¹⁷ , -N (R ¹⁸ ) CO ₂ R ¹⁹ , -N (R ¹⁸ ) C (O) NR ¹⁹ R ²⁰ ; for alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy optionally substituted once or several times, identically or differently, by halogen, cyano, alkoxy and / or -NR ⁸ R ⁹ ; or for cycloalkyl, cycloalkylalkyl, cycloalkyloxy, aryl, arylalkyl, aryloxy, aryloxyalkyl optionally substituted once or several times, identically or differently, by halogen, cyano, nitro, alkyl, haloalkyl, alkenyl, haloalkenyl, alkoxy, haloalkoxy, alkylthio and / or haloalkylthio. saturated or unsaturated 5- to 10-membered heterocyclyl or heterocyclylalkyl with one or more heteroatoms from the series consisting of nitrogen, oxygen and sulfur,
W ¹ for halogen, cyano, formyl, nitro, trialkylsilyl, alkyl, haloalkyl, alkoxy, haloalkoxy, alkenyl, haloalkenyl, alkenyloxy, haloalkenyloxy, alkylcarbonyl, alkoxycarbonyl, -S (O) _w R ⁷ , -C (R ¹⁴ ) = N -OR ¹⁵ , -SO ₂ NR ¹⁶ R ¹⁷ , - (CH ₂ ) _p NR ¹⁶ R ¹⁷ , - (CH ₂ ) _p N (R ¹⁶ ) COR ¹⁷ , - (CH ₂ ) _p N (R ¹⁶ ) SO ₂ R ¹⁷ , -OSO ₂ R ¹⁶ , -OSO ₂ NR ¹⁶ R ¹⁷ .
R ^{6 stands} for alkyl, haloalkyl, or for cycloalkyl, cycloalkylalkyl, aryl or arylalkyl which is optionally mono- or polysubstituted, identically or differently, by halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio and / or haloalkylthio,
R ⁷ for optionally mono- or polysubstituted, identically or differently, by halogen and / or -NR ⁸ R ⁹ alkyl, for in each case optionally mono- or polysubstituted, identically or differently by halogen, cyano, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio and / or haloalkylthio substituted cycloalkyl, aryl or arylalkyl,
R ⁸ and R ⁹ independently of one another for hydrogen, -SO ₂ R ⁷ , for each optionally mono- or polysubstituted, identically or differently, by halogen, alkylcarbonyl, alkylcarbonyloxy, alkylamino, dialkylamino, alkoxy, haloalkoxy, alkylthio and / or haloalkylthio substituted alkyl or alkenyl ; for cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, saturated or unsaturated, 5- to 10-membered heterocyclyl or heterocyclylalkyl, each optionally mono- or polysubstituted, identically or differently, by halogen, cyano, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio and / or haloalkylthio with one or more heteroatoms from the series nitrogen, oxygen and sulfur,
R ⁸ and R ⁹ furthermore together for optionally mono- or polysubstituted, identically or differently by halogen, cyano, alkoxy, haloalkoxy, alkylthio and / or haloalkylthio or for optionally mono- or polysubstituted, identically or differently by halogen, cyano, alkyl, haloalkyl , Alkoxy, haloalkoxy, alkylthio and / or haloalkylthio substituted alkylene, where the alkylene chain can be interrupted by -O-, -S- or -NR ²¹ -,
R ¹⁰ and R ¹¹ independently of one another for hydrogen, -SO ₂ R ⁷ , for each optionally optionally mono- or polysubstituted, identically or differently, by halogen, alkylamino, dialkylamino, alkoxy and / or alkylthio substituted alkyl or alkenyl; for cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, saturated or unsaturated, 5- to 10-membered heterocyclyl or heterocyclylalkyl, each optionally mono- or polysubstituted, identically or differently, by halogen, cyano, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio and / or haloalkylthio with one or more heteroatoms from the series nitrogen, oxygen and sulfur,
R ¹⁰ and R ¹¹ also together represent optionally substituted one or more times, identically or differently, by halogen, cyano, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio and / or haloalkylthio, the alkylene chain being represented by -O-, -S- or -NR ²¹ - may be interrupted
R ¹² and R ¹³ independently of one another for hydrogen, for alkyl which is optionally mono- or polysubstituted identically or differently by halogen, cyano, alkoxy and / or alkylthio, for in each case optionally mono- or polysubstituted, identically or differently by halogen, cyano, alkyl, haloalkyl , Alkoxy, haloalkoxy, alkylthio and / or haloalkylthio substituted cycloalkyl, cycloalkylalkyl, aryl or arylalkyl,
R ¹² and R ¹³ furthermore each stand for alkylene or alkenylene which is optionally mono- or polysubstituted, identically or differently, by halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio and / or haloalkylthio,
R ¹⁴ and R ¹⁵ independently of one another represent hydrogen, alkyl, alkenyl, haloalkyl or haloalkenyl,
R ¹⁶ and R ¹⁷ independently of one another represent hydrogen, alkyl, haloalkyl or cycloalkyl which is optionally mono- or polysubstituted identically or differently by halogen or alkyl,
R ¹⁶ and R ¹⁷ furthermore each stand for alkylene, alkoxyalkylene or alkylthioalkylene which may be mono- or polysubstituted identically or differently by halogen or alkyl,
R ^{18 represents} hydrogen or alkyl,
R ¹⁹ and R ²⁰ independently of one another for hydrogen, each in each case mono- or polysubstituted, identically or differently, by halogen, alkylcarbonyl, alkylcarbonyloxy, alkylamino, dialkylamino, alkoxy, alkylthio, alkoxyalkoxy, haloalkoxy, haloalkylthio and / or haloalkoxyalkoxy-substituted alkyl or alkenyl;
for cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, saturated or unsaturated, 5- to 10-membered heterocyclyl, each optionally mono- or polysubstituted, identically or differently, by halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylcarbonyl and / or alkoxycarbonyl or heterocyclylalkyl,
R ¹⁸ and R ¹⁹ also together represent alkylene which is mono- or polysubstituted by alkyl, or
R ¹⁹ and R ²⁰ together with the nitrogen atom to which they are attached also represent a saturated or unsaturated 5- to 10-membered heterocycle which may optionally be a further heteroatom group from the series -O-, -S- or -NR ²² - Can contain and which can optionally be substituted one or more times, identically or differently by halogen, alkyl, alkoxy, alkylthio, haloalkyl, haloalkoxy and / or haloalkylthio, and
R ^{21 is} hydrogen, -SO ₂ R ⁷ , -COR ⁷ or -CO ₂ R ⁷ ; for alkyl or alkenyl which is optionally mono- or polysubstituted, identically or differently, by halogen, cyano, alkylamino, dialkylamino, alkoxy, haloalkoxy, alkylthio and / or haloalkylthio; for cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, saturated or unsaturated, 5- to 10-membered heterocyclyl or heterocyclylalkyl, each optionally mono- or polysubstituted, identically or differently, by halogen, cyano, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio and / or haloalkylthio with one or more heteroatoms from the series nitrogen, oxygen and sulfur,
R ^{22 represents} hydrogen, alkyl or alkenyl,
w represents 0, 1 or 2,
n represents 1, 2, 3 or 4,
p stands for 0, 1 or 2.

Δ ¹ -Pyrrolines of the formula (I), in which
R ^{1 stands} for C ₁ -C ₄ alkyl or for optionally single to tetrasubstituted, identical or differently substituted aryl (in particular phenyl), where the substituents from the series fluorine, chlorine, bromine, iodine, cyano, nitro, C ₁ -C ₄ alkyl, C ₁ - C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ -haloalkoxy and C ₁ -C ₄ -haloalkylthio having in each case 1 to 9 fluorine , Chlorine and / or bromine atoms are selected,
R ^{2 represents} fluorine, chlorine, bromine, cyano, nitro, amino, C ₁ -C ₄ alkyl or C ₁ -C ₄ alkoxy,
R ^{3 represents} hydrogen, fluorine, chlorine, bromine, C ₁ -C ₄ alkyl or C ₁ -C ₄ alkoxy,
R ^{4 stands} for the grouping -XYZE with the proviso that Y does not stand for a direct bond if X does not stand for a direct bond,
R ⁵ for fluorine, chlorine, bromine, C ₁ -C ₆ alkyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ alkylthio, C ₁ -C ₆ - haloalkyl, C ₁ -C ₆ haloalkoxy or C ₁ -C ₆ haloalkylthio each having 1 to 13 fluorine, chlorine and / or bromine atoms,
m represents 0, 1, 2 or 3, where the radicals R ^{5 can be} identical or different if m represents 2 or 3,
X for a direct bond, oxygen, -S (O) _w -, -NR ⁶ -, carbonyl, carbonyloxy, oxycarbonyl, oxysulfonyl (OSO ₂ ), C ₁ -C ₆ alkylene, C ₁ -C ₆ haloalkylene, C ₂ -C ₆ alkenylene, C ₂ -C ₆ haloalkenylene, C ₂ -C ₆ alkynylene, C ₁ -C ₆ alkyleneoxy, C ₁ -C ₆ oxyalkylene, oxy-C ₁ -C ₆ alkyleneoxy or - S (O) _{w is} -C ₁ -C ₆ -alkylene,
Y for a direct bond or for in each case optionally up to four times, identically or differently, 1,4-phenylene, 1,3-phenylene, 1,2-phenylene, 2,6-naphthylene substituted by radicals from the list W ¹ , 7-naphthylene, 1,4-naphthylene, 2,6- (1,2,3,4-tetrahydro) naphthylene, 2,7- (1,2,3,4-tetrahydro) naphthylene, 1,4- ( 1,2,3,4-tetrahydro) naphthylene, 5,8- (1,2,3,4-tetrahydro) naphthylene; or for in each case optionally up to four times, identically or differently, 5- or 6-membered, saturated or unsaturated heterocyclylene substituted by radicals from the list W ¹ with 1 to 3 heteroatoms which contains 0 to 3 nitrogen atoms, 0 to 2 non-adjacent oxygen atoms and / or contains 0 to 2 non-adjacent sulfur atoms (in particular furylene, thienylene, pyrrolylene, oxazolylene, thiazolylene, pyridinylene, pyrimidinylene or pyridazinylene or pyrazinylene),
Z represents a direct bond or - (CH ₂ ) _n -,
E for hydrogen, fluorine, chlorine, bromine, hydroxy, cyano, formyl, nitro, tri- (C ₁ - C ₆ alkyl) silyl, pentafluorothio, -S (O) _w R ⁷ , -OSO ₂ R ⁷ , -NR ⁸ R ⁹ , -COR ⁷ , -CO ₂ R ⁷ , -OC (O) R ⁷ , -CONR ¹⁰ R ¹¹ , -N (R ¹² ) COR ¹³ , -C (R ¹⁴ ) = N-OR ¹⁵ , - SO ₂ NR ¹⁶ R ¹⁷ -N (R ¹⁸ ) CO ₂ R ¹⁹ , -N (R ¹⁸ ) C (O) NR ¹⁹ R ²⁰ ; in each case optionally monosubstituted or polysubstituted by identical or different halogen, cyano, C ₁ -C ₁₀ - alkoxy and / or -NR ⁸ R ⁹ substituted C ₁ -C ₂₀ alkyl, C ₂ -C ₂₀ alkenyl, C ₂ - C ₁₀ alkynyl, C ₁ -C ₂₀ alkoxy, C ₂ -C ₂₀ alkenyloxy; or for in each case optionally up to four times, identically or differently, by halogen, cyano, nitro, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ haloalkenyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ haloalkoxy, C ₁ -C ₆ alkylthio and / or C ₁ - C ₆ haloalkylthio substituted C ₃ -C ₁₂ cycloalkyl, C ₃ -C ₇ cycloalkyl C ₁ -C ₄ alkyl, C ₃ -C ₁₂ cycloalkyloxy, aryl, arylC ₁ -C ₄ alkyl, aryloxy, aryloxyC ₁ -C ₄ alkyl, saturated or unsaturated 5- to 10-membered heterocyclyl or heterocyclyl-C ₁ -C ₄ -alkyl having 1 to 4 heteroatoms which contain 0 to 4 nitrogen atoms, 0 to 2 non-adjacent oxygen atoms and / or 0 to 2 non-adjacent sulfur atoms (in particular tetrazolyl, furyl, furfuryl, benzofuryl, tetrahydrofuryl, Thienyl, thenyl, benzothienyl, thiolanyl, pyrrolyl, indolyl, pyrrolinyl, pyrrolidino, pyrrolidinyl, oxazolyl, benzoxazolyl, isoxazolyl, imidazolyl, pyrazolyl, thiazolyl, benzothiazolyl, thiazolidinyl, pyridine yl, pyrimidinyl, pyridazyl, pyrazinyl, piperidinyl, piperidino, morpholinyl, thiomorpholinyl, morpholino, thiomorpholino, triazinyl, triazolyl, quinolinyl or isoquinolinyl),
W ¹ for fluorine, chlorine, bromine, cyano, formyl, nitro, tri- (C ₁ -C ₆ alkyl) silyl, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ - Alkoxy, C ₁ -C ₆ haloalkoxy, C ₂ -C ₆ alkenyl, C ₂ -C ₆ haloalkenyl, C ₂ -C ₆ alkenyloxy, C ₂ -C ₆ haloalkenyloxy, C ₁ -C ₆ alkylcarbonyl, C ₁ -C ₆ alkoxycarbonyl, -S (O) _w R ⁷ , -C (R ¹⁴ ) = N-OR ¹⁵ , -SO ₂ NR ¹⁶ R ¹⁷ , - (CH ₂ ) _p NR ¹⁶ R ¹⁷ , - ( CH ₂ ) _p N (R ¹⁶ ) COR ¹⁷ , - (CH ₂ ) _p N (R ¹⁶ ) SO ₂ R ¹⁷ , -SO ₂ R ¹⁶ , -OSO ₂ NR ¹⁶ R ¹⁷ ,
R ⁶ for C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, or for each optionally optionally up to four times, identically or differently by halogen, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ haloalkoxy, C ₁ -C ₆ alkylthio and / or C ₁ -C ₆ haloalkylthio substituted C ₃ -C ₇ cycloalkyl, C ₃ -C ₆ cycloalkyl- C ₁ -C ₄ alkyl, aryl or aryl-C ₁ -C ₄ alkyl,
R ⁷ for C ₁ -C ₂₀ -alkyl which is optionally mono- or polysubstituted, identically or differently, by halogen and / or -NR ⁸ R ⁹ , in each case optionally up to eight times, identically or differently by halogen, cyano, C ₁ -C ₆ Alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ haloalkoxy, C ₁ -C ₆ alkylthio and / or C ₁ -C ₆ haloalkylthio substituted C ₃ -C ₆ Cycloalkyl, aryl or aryl-C ₁ -C ₄ -alkyl,
R ⁸ and R ⁹ independently of one another for hydrogen, -SO ₂ R ⁷ , for each optionally optionally one or more times, identically or differently by halogen, C ₁ -C ₆ -alkylcarbonyl, C ₁ -C ₆ -alkylcarbonyloxy, C ₁ -C ₆ -Alkylamino, di- (C ₁ -C ₆ -alkyl) amino, C ₁ -C ₆ -alkoxy, C ₁ -C ₆ -haloalkoxy, C ₁ -C ₆ -alkylthio and / or C ₁ -C ₆ -haloalkylthio substituted C ₁ -C ₂₀ alkyl or C ₂ -C ₂₀ alkenyl; for each optionally one to four times, identical or different, by halogen, cyano, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ haloalkoxy, C ₁ - C ₆ alkylthio and / or C ₁ -C ₆ haloalkylthio substituted C ₃ -C ₁₂ cycloalkyl, C ₃ -C ₇ cycloalkyl-C ₁ -C ₄ alkyl, aryl, aryl-C ₁ -C ₄ alkyl , saturated or unsaturated, 5- to 10-membered heterocyclyl or heterocyclyl-C ₁ -C ₄ alkyl having 1 to 4 heteroatoms which contain 0 to 4 nitrogen atoms, 0 to 2 non-adjacent oxygen atoms and / or 0 to 2 non-adjacent sulfur atoms (in particular tetrazolyl, furyl, furfuryl, benzofuryl, tetrahydrofuryl, thienyl, thenyl, benzothienyl, thiolanyl, pyrrolyl, indolyl, pyrrolinyl, pyrrolidinyl, oxazolyl, benzoxazolyl, isoxazolyl, imidazolyl, pyrazolyl, thiazolylyl, pyriazoleyl, pyriazole Pyrazinyl, piperidinyl, morpholinyl, thiomorpholinyl, triazinyl, triazolyl, quinolinyl or isoquinoliny l) stand,
R ⁸ and R ⁹ furthermore together for optionally single or multiple, identical or different, by halogen, cyano, C ₁ -C ₆ alkoxy, C ₁ -C ₆ haloalkoxy, C ₁ -C ₆ alkylthio and / or C ₁ - C ₆ -haloalkylthio substituted C ₂ -C ₁₂ alkenylene or for one or more, optionally in the alkylene part, the same or different by halogen, cyano, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ -Alkoxy, C ₁ -C ₆ -haloalkoxy, C ₁ -C ₆ -alkylthio and / or C ₁ -C ₆ - haloalkylthio-substituted C ₃ -C ₁₂ -alkylene, the alkylene chain being -O-, -S- or - NR ²¹ - may be interrupted,
R ¹⁰ and R ¹¹ independently of one another represent hydrogen, -SO ₂ R ^7, in each case optionally substituted once to thirteen times by identical or different halogen, C ₁ -C ₆ - alkylamino, di- (C ₁ -C ₆ alkyl) amino, C ₁ -C ₆ alkoxy, C ₁ -C ₆ haloalkoxy, C ₁ -C ₆ alkylthio and / or C ₁ -C ₆ haloalkylthio substituted C ₁ -C ₆ alkyl or C ₂ -C ₆ alkenyl; for each optionally one to four times, identical or different, by halogen, cyano, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ haloalkoxy, C ₁ - C ₆ alkylthio and / or C ₁ -C ₆ haloalkylthio substituted C ₃ -C ₇ cycloalkyl, C ₃ -C ₇ cycloalkyl-C ₁ -C ₄ alkyl, aryl, aryl-C ₁ -C ₄ alkyl , saturated or unsaturated, 5- to 10-membered heterocyclyl or heterocyclyl-C ₁ -C ₄ alkyl having 1 to 4 heteroatoms which contain 0 to 4 nitrogen atoms, 0 to 2 non-adjacent oxygen atoms and / or 0 to 2 non-adjacent sulfur atoms (in particular tetrazolyl, furyl, furfuryl, benzofuryl, tetrahydrofuryl, thienyl, thenyl, benzothienyl, thiolanyl, pyrrolyl, indolyl, pyrrolinyl, pyrrolidinyl, oxazolyl, benzoxazolyl, isoxazolyl, imidazolyl, pyrazolyl, thiazolylyl, pyriazoleyl, pyriazole Pyrazinyl, piperidinyl, morpholinyl, thiomorpholinyl, triazinyl, triazolyl, quinolinyl or isoquinolinyl ) stand,
R ¹⁰ and R ¹¹ also together for optionally in the alkylene part single to quadruple, identical or different by halogen, cyano, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ alkoxy, C ₁ - C ₆ -C haloalkoxy, C ₁ -C ₆ alkylthio and / or C ₁ -C ₆ haloalkylthio substituted C ₃ -C ₆ alkylene, - (CH ₂ ) ₂ -O- (CH ₂ ) ₂ -, - (CH ₂ ) ₂ -S- (CH ₂ ) ₂ - or - (CH ₂ ) ₂ -N (R ²¹ ) - (CH ₂ ) ₂ -,
R ¹² and R ¹³ independently of one another for hydrogen, for optionally single to thirteen times, identical or different, substituted by halogen, cyano, C ₁ -C ₆ alkoxy, C ₁ -C ₆ alkylthio, C ₁ -C ₆ alkyl, for each optionally one to eight times, identical or different, by halogen, cyano, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ haloalkoxy, C ₁ -C ₆ alkylthio and / or C ₁ -C ₆ haloalkylthio-substituted C ₃ -C ₇ cycloalkyl, C ₃ -C ₇ - cycloalkyl-C ₁ -C ₄ alkyl, aryl or aryl-C ₁ -C ₄ are alkyl,
R ¹² and R ¹³ furthermore together, in each case optionally for one to eight times, identically or differently by halogen, C ₁ -C ₆ -alkyl, C ₁ -C ₆ -haloalkyl, C ₁ -C ₆ -alkoxy, C ₁ -C ₆ - Halogenalkoxy, C ₁ -C ₆ alkylthio and / or C ₁ -C ₆ haloalkylthio substituted C ₃ -C ₁₀ alkylene or C ₃ -C ₁₀ alkenylene,
R ¹⁴ and R ¹⁵ independently of one another represent hydrogen, C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl, C ₁ -C ₆ haloalkyl or C ₂ -C ₆ haloalkenyl,
R ¹⁶ and R ¹⁷ independently of one another for hydrogen, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl or for optionally up to eight times, identically or differently, by fluorine, chlorine, bromine and / or C ₁ -C ₆ - Alkyl substituted C ₃ -C ₇ cycloalkyl,
R ¹⁶ and R ¹⁷ furthermore together substituted in each case optionally substituted once to nine times in an identical or different manner by fluorine, chlorine, bromine and / or C ₁ -C ₆ alkyl, C ₃ -C ₆ alkylene, C ₁ -C ₃ alkoxy Are C ₁ -C ₃ alkylene or C ₁ -C ₃ alkylthio- C ₁ -C ₃ alkylene,
R ^{18 represents} hydrogen or C ₁ -C ₆ alkyl,
R ¹⁹ and R ²⁰ independently of one another represent hydrogen, represent in each case optionally monosubstituted or polysubstituted by identical or different fluorine, chlorine, bromine, C ₁ - C ₆ alkylcarbonyl, C ₁ -C ₆ alkylcarbonyloxy, C ₁ -C ₆ alkylamino , Di- (C ₁ -C ₆ alkyl) amino, C ₁ -C ₁₀ alkoxy, C ₁ -C ₁₀ alkylthio, C ₁ -C ₁₀ alkoxy-C ₁ -C ₁₀ alkoxy, C ₁ -C ₁₀ -haloalkoxy, C ₁ -C ₁₀ -haloalkylthio and / or C ₁ -C ₁₀ -haloalkoxy-C ₁ -C ₁₀ -alkoxy substituted C ₁ -C ₂₀ -alkyl or C ₂ -C ₂₀ -alkenyl;
for each optionally one to four times, identical or different, by fluorine, chlorine, bromine, C ₁ -C ₆ alkyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ alkylthio, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ haloalkoxy, C ₁ -C ₆ haloalkylthio, C ₁ -C ₆ alkylcarbonyl and / or C ₁ -C ₆ alkoxycarbonyl substituted C ₃ -C ₁₂ cycloalkyl, C ₃ -C ₇ cycloalkyl-C ₁ -C ₄ alkyl, aryl, aryl-C ₁ -C ₄ alkyl, saturated or unsaturated, 5- to 10-membered heterocyclyl or heterocyclyl-C ₁ -C ₄ alkyl having 1 to 4 heteroatoms, which are 0 to 4 Contain nitrogen atoms, 0 to 2 non-adjacent oxygen atoms and / or 0 to 2 non-adjacent sulfur atoms (especially tetrazolyl, furyl, furfuryl, benzofuryl, tetrahydrofuryl, thienyl, thenyl, benzothienyl, thiolanyl, pyrrolyl, indolyl, pyrrolinyl, pyrrolidinyl, oxazolyl, oxazolyl, oxazolyl, oxazolyl, Isoxazolyl, imidazolyl, pyrazolyl, thiazolyl, benzothiazolyl, thiazolidinyl, pyridinyl, pyrimidinyl, pyridazyl, pyrazinyl, piperidinyl, morpholinyl, thiomorphol inyl, triazinyl, triazolyl, quinolinyl or isoquinolinyl),
R ¹⁸ and R ¹⁹ furthermore together represent optionally mono- to tetrasubstituted by C ₁ - C ₄ alkyl-substituted C ₂ -C ₄ alkylene, or
R ¹⁹ and R ²⁰ together with the nitrogen atom to which they are attached also represent a saturated or unsaturated 5- to 10-membered heterocycle which, if appropriate, is a further heteroatom group from the series -O-, -S- or -NR ²² - Can contain and optionally, up to four times, identically or differently, by fluorine, chlorine, bromine, C ₁ -C ₆ alkyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ alkylthio, C ₁ -C ₆ - Haloalkyl, C ₁ -C ₆ haloalkoxy and / or C ₁ -C ₆ haloalkylthio may be substituted, and
R ^{21 is} hydrogen, -SO ₂ R ⁷ , -COR ⁷ or -CO ₂ R ⁷ ; in each case optionally monosubstituted or polysubstituted by identical or different halogen, cyano, C ₁ - C ₆ alkylamino, di- (C ₁ -C ₆ alkyl) amino, C ₁ -C ₆ alkoxy, C ₁ -C ₆ - Haloalkoxy, C ₁ -C ₆ alkylthio and / or C ₁ -C ₆ haloalkylthio substituted C ₁ -C ₂₀ alkyl or C ₂ -C ₂₀ alkenyl; for in each case optionally up to fourfold, identically or differently, by halogen, cyano, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ haloalkoxy, C ₁ - C ₆ alkylthio and / or C ₁ -C ₆ haloalkylthio substituted C ₃ -C ₁₂ cycloalkyl, C ₃ -C ₇ cycloalkyl-C ₁ -C ₄ alkyl, aryl, aryl-C ₁ -C ₄ alkyl , saturated or unsaturated, 5- to 10-membered heterocyclyl or heterocyclyl-C ₁ -C ₄ alkyl having 1 to 4 heteroatoms which contain 0 to 4 nitrogen atoms, 0 to 2 non-adjacent oxygen atoms and / or 0 to 2 non-adjacent sulfur atoms (in particular tetrazolyl, furyl, furfuryl, benzofuryl, tetrahydrofuryl, thienyl, thenyl, benzothienyl, thiolanyl, pyrrolyl, indolyl, pyrrolinyl, pyrrolidinyl, oxazolyl, benzoxazolyl, isoxazolyl, imidazolyl, pyrazolyl, thiazolylyl, pyriazoleyl, pyriazole Pyrazinyl, piperidinyl, morpholinyl, thiomorpholinyl, triazinyl, triazolyl, quinolinyl or isoquinoli nyl) stands,
R ^{22 represents} hydrogen, C ₁ -C ₆ alkyl or C ₂ -C ₆ alkenyl,
w represents 0, 1 or 2,
n represents 1, 2 or 3,
p stands for 0, 1 or 2.

Δ ¹ -pyrrolines of the formula (I), in which
R ^{1 stands} for methyl, ethyl, n- or i-propyl, or for aryl which is optionally mono- or disubstituted, identically or differently, the substituents from the series fluorine, chlorine, bromine, iodine, cyano, nitro, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ -haloalkoxy and C ₁ -C ₄ -haloalkylthio having in each case 1 to 9 fluorine , Chlorine and / or bromine atoms are selected,
R ^{2 represents} fluorine, chlorine, bromine, cyano, nitro, amino, C ₁ -C ₄ alkyl or C ₁ -C ₄ alkoxy,
R ^{3 represents} hydrogen, fluorine, chlorine, bromine, cyano, nitro, amino, C ₁ -C ₄ alkyl or C ₁ -C ₄ alkoxy,
R ^{4 stands} for the grouping -XYZE with the proviso that Y does not stand for a direct bond if X does not stand for a direct bond,
R ^{5 is} fluorine, chlorine, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio; C ₁ -C ₄ haloalkyl, C ₁ -C ₄ haloalkoxy, C ₁ -C ₄ haloalkylthio each having 1 to 9 fluorine, chlorine and / or bromine atoms,
m represents 0, 1 or 2, where the radicals R ^{5 can be} identical or different if m represents 2,
X for a direct bond, oxygen, -S (O) _w -, -NR ⁶ -, carbonyl, carbonyloxy, oxycarbonyl, oxysulfonyl (OSO ₂ ), C ₁ -C ₄ alkylene, C ₁ -C ₄ haloalkylene with 1 up to 8 fluorine, chlorine and / or bromine atoms, C ₂ -C ₄ alkenylene, C ₂ -C ₄ haloalkenylene with 1 to 6 fluorine, chlorine and / or bromine atoms, C ₂ -C ₄ alkynylene, C ₁ -C ₄ alkyleneoxy, oxy-C ₁ -C ₄ alkylene, oxy-C ₁ -C ₄ alkyleneoxy or -S (O) _w -C ₁ -C ₄ alkylene,
Y for a direct bond or for in each case optionally single to triple, identical or different, substituted by radicals from the list W ^1, 1,4-phenylene, 1,3-phenylene, 1,2-phenylene, 2,6-naphthylene, 2, 7-naphthylene, 1,4-naphthylene, 2,6- (1,2,3,4-tetrahydro) naphthylene, 2,7- (1,2,3,4-tetrahydro) naphthylene, 1,4- (1st , 2,3,4-tetrahydro) naphthylene, 5,8- (1,2,3,4-tetrahydro) naphthylene, 2,4-furylene, 2,4-thienylene, 2,4-pyrrolylene, 2,5- Oxazolylene, 2,5-thiazolylene, 2,5-pyridinylene, 2,6-pyridinylene, 2,5-pyrimidinylene or 3,6-pyridazinylene or 2,5-pyrazinylene,
Z represents a direct bond or - (CH ₂ ) _n -,
E for hydrogen, fluorine, chlorine, bromine, hydroxy, cyano, formyl, nitro, trimethylsilyl, dimethyl-tert-butylsilyl, -S (O) _w R ⁷ , -OSO ₂ R ⁷ , -NR ⁸ R ⁹ , -COR ⁷ , -CO ₂ R ⁷ , -OC (O) R ⁷ , -CONR ¹⁰ R ¹¹ , -N (R ¹² ) COR ¹³ , -SO ₂ NR ¹⁶ R ¹⁷ , -N (R ¹⁸ ) CO ₂ R ¹⁹ , - N (R ¹⁸ ) C (O) NR ¹⁹ R ²⁰ ; in each case optionally monosubstituted or polysubstituted by identical or different fluorine, chlorine, bromine, cyano, C ₁ - C ₆ alkoxy and / or -NR ⁸ R ⁹ substituted C ₁ -C ₁₆ alkyl, C ₂ -C ₁₆ alkenyl , C ₂ -C ₆ alkynyl, C ₁ -C ₁₆ alkoxy, C ₂ -C ₁₆ alkenyloxy; or for each optionally single to triple, identical or different, by fluorine, chlorine, bromine, cyano, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ - Haloalkyl, C ₁ -C ₄ haloalkoxy, C ₁ -C ₄ haloalkylthio each having 1 to 9 fluorine, chlorine and / or bromine atoms, C ₂ -C ₆ alkenyl and / or C ₂ -C ₆ haloalkenyl 1 to 8 fluorine, chlorine and / or bromine atoms substituted C ₃ -C ₁₀ cycloalkyl, C ₃ -C ₆ cycloalkyl-C ₁ -C ₄ alkyl, C ₃ -C ₁₀ cycloalkyloxy, phenyl, phenoxy, benzyl , Phenylethyl, benzyloxy, tetrazolyl, furyl, furfuryl, benzofuryl, tetrahydrofuryl, thienyl, thenyl, benzothienyl, thiolanyl, pyrrolyl, indolyl, pyrrolinyl, pyrrolidino, pyrrolidinyl, oxazolyl, benzoxazolyl, isoxazolyl, pyridolyloliazolyl, pyridylylolyloliazolyl, imidazylyloliazolyl, imidazylyliazolyl, imidazylyloliazolyl, imidazylyliazolyl, imidazylolidol , Pyrimidinyl, pyridazyl, pyrazinyl, piperidinyl, piperidino, morpholinyl, thiomorpholinyl, morpholino, thiomorpholino, triazinyl, triazolyl, quinolinyl or isoquinolinyl,
W ¹ for fluorine, chlorine, bromine, cyano, formyl, trimethylsilyl, dimethyl-tert-butylsilyl, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₂ -C ₄ alkenyl, C ₂ -C ₄ alkenyloxy; for C ₁ -C ₄ haloalkyl, C ₁ -C ₄ haloalkoxy each having 1 to 9 fluorine, chlorine and / or bromine atoms, C ₂ -C ₄ haloalkenyl, C ₂ -C ₄ haloalkenyloxy each having 1 to 8 fluorine, chlorine and / or bromine atoms; for C ₁ -C ₄ alkylcarbonyl, C ₁ -C ₄ alkoxycarbonyl, -S (O) _w R ⁷ , -SO ₂ NR ¹⁶ R ¹⁷ , - (CH ₂ ) _p NR ¹⁶ R ¹⁷ , - (CH ₂ ) _p N (R ¹⁶ ) COR ¹⁷ , - (CH ₂ ) _p N (R ¹⁶ ) SO ₂ R ¹⁷ , -OSO ₂ R ¹⁶ , -OSO ₂ NR ¹⁶ R ¹⁷ ,
R ⁶ for methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, trifluoromethyl, trifluoroethyl, or for each optionally one to four times, identical or different by fluorine, chlorine , bromine, C ₁ -C ₄ alkyl, C ₁ - C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ -haloalkoxy and / or C ₁ -C ₄ Haloalkylthio, each with 1 to 9 fluorine, chlorine and / or bromine atoms, substituted cyclopropyl, cyclopropylmethyl, cyclopentyl, cyclopentylmethyl, cyclohexyl, cyclohexylmethyl, phenyl, benzyl or phenylethyl,
R ⁷ for C ₁ -C ₁₀ alkyl optionally substituted once or several times, identically or differently by fluorine, chlorine, bromine and / or -NR ⁸ R ⁹ , for in each case optionally up to four times, identically or differently by fluorine, chlorine and / or bromine, cyano, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ -haloalkoxy and / or C ₁ - C ₄ haloalkylthio, each with 1 to 9 fluorine, chlorine and / or bromine atoms, substituted cyclopropyl, cyclopentyl, cyclohexyl, phenyl or benzyl,
R ⁸ and R ⁹ independently of one another for hydrogen, -SO ₂ R ⁷ , for each optionally one or more times, identically or differently by fluorine, chlorine and / or bromine, C ₁ -C ₄ -alkylcarbonyl, C ₁ -C ₄ -alkylcarbonyloxy , C ₁ -C ₄ alkylamino, di- (C ₁ -C ₄ alkyl) amino, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ haloalkoxy and / or C ₁ -C ₄ haloalkylthio each with 1 to 9 fluorine, chlorine and / or bromine atoms substituted C ₁ -C ₁₆ alkyl or C ₂ -C ₁₆ alkenyl; for each optionally single to triple, identical or different by fluorine, chlorine and / or bromine, cyano, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ -Halogenalkyl, C ₁ -C ₄ -haloalkoxy and / or C ₁ -C ₄ -haloalkylthio each with 1 to 9 fluorine, chlorine and / or bromine atoms substituted C ₃ -C ₁₀ cycloalkyl, C ₃ -C ₆ cycloalkyl -C ₁ -C ₄ alkyl, phenyl, benzyl, phenylethyl, tetrazolyl, furyl, furfuryl, benzofuryl, tetrahydrofuryl, thienyl, thenyl, benzothienyl, thiolanyl, pyrrolyl, indolyl, pyrrolinyl, pyrrolidinyl, oxazolyl, benzoxazolyl, isoxazolyl, imidazazolyl, imidazolylyl, imidazolyl , Thiazolyl, benzothiazolyl, thiazolidinyl, pyridinyl, pyrimidinyl, pyridazyl, pyrazinyl, piperidinyl, morpholinyl, thiomorpholinyl, triazinyl, triazolyl, quinolinyl or isoquinolinyl.
R ⁸ and R ⁹ furthermore together for optionally single or multiple, identical or different by fluorine, chlorine and / or bromine, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ haloalkoxy and / or C ₁ -C ₄ haloalkylthio, each with 1 to 9 fluorine, chlorine and / or bromine atoms, substituted C ₂ -C ₁₀ alkenylene or for one or more, optionally in the alkylene part, identical or different by fluorine, chlorine, cyano, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ - C ₄ alkylthio, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ haloalkoxy and / or C ₁ -C ₄ haloalkylthio with each 1 to 9 fluorine, chlorine and / or bromine atoms substituted C ₃ -C ₁₀ alkylene, where the alkylene chain can be interrupted by -O-, -S- or -NR ²¹ -,
R ¹⁰ and R ¹¹ independently of one another for hydrogen, -SO ₂ R ⁷ , each in each case optionally up to nine times, identically or differently by fluorine, chlorine and / or bromine, C ₁ -C ₄ -alkylamino, di- (C ₁ -C _4- alkyl) amino, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ haloalkoxy and / or C ₁ -C ₄ haloalkylthio, each with 1 to 9 fluorine, chlorine and / or bromine atoms substituted C ₁ -C ₆ alkyl or C ₂ -C ₆ alkenyl; for each optionally single to triple, identical or different by fluorine, chlorine and / or bromine, cyano, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ Haloalkyl, C ₁ -C ₄ haloalkoxy and / or C ₁ -C ₄ haloalkylthio each with 1 to 9 fluorine, chlorine and / or bromine atoms substituted C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ cycloalkyl -C ₁ - C ₄ alkyl, phenyl, benzyl, phenylethyl, tetrazolyl, furyl, furfuryl, benzofuryl, tetrahydrofuryl, thienyl, thenyl, benzothienyl, thiolanyl, pyrrolyl, indolyl, pyrrolinyl, pyrrolidinyl, oxazolyl, benzoxazolyl, isoxazylyl, imazazylolyl, imaz , Thiazolyl, benzothiazolyl, thiazolidinyl, pyridinyl, pyrimidinyl, pyridazyl, pyrazinyl, piperidinyl, morpholinyl, thiomorpholinyl, triazinyl, triazolyl, quinolinyl or isoquinolinyl,
R ¹⁰ and R ¹¹ furthermore together for each, optionally in the alkylene part, one to four times, identically or differently, by fluorine, chlorine, cyano, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ haloalkoxy and / or C ₁ -C ₄ haloalkylthio each with 1 to 9 fluorine, chlorine and / or bromine atoms substituted C ₄ -C ₅ alkylene, - ( CH ₂ ) ₂ -O- (CH ₂ ) ₂ -, - (CH ₂ ) ₂ -S- (CH ₂ ) ₂ -, - (CH ₂ ) ₂ -N (R ²¹ ) - (CH ₂ ) ₂ - .
R ¹² and R ¹³ independently of one another for hydrogen, for optionally _{1 to} 9 times, identically or differently, substituted by fluorine, chlorine, bromine, C ₁ -C ₄ alkoxy and / or C ₁ -C ₄ alkylthio, substituted C ₁ -C ₆ - Alkyl, each optionally up to four times, the same or different by fluorine, chlorine, bromine, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ haloalkyl , C ₁ -C ₄ haloalkoxy and / or C ₁ -C ₄ haloalkylthio each with 1 to 9 fluorine, chlorine and / or bromine atoms substituted C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ cycloalkyl-C ₁ -C ₄ alkyl, phenyl, benzyl or phenylethyl,
R ¹² and R ¹³ furthermore together for each optionally one to four times, identical or different by fluorine, chlorine, bromine, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ haloalkoxy and / or C ₁ -C ₄ haloalkylthio each with 1 to 9 fluorine, chlorine and / or bromine atoms substituted C ₃ -C ₈ alkylene or C ₃ -C _8- alkenylene, R ¹⁶ and R ¹⁷ independently of one another are hydrogen, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -haloalkyl having 1 to 9 fluorine, chlorine and / or bromine atoms or optionally up to four times, the same or different fluorine, chlorine, bromine and / or C ₁ -C ₄ alkyl substituted C ₃ -C ₆ cycloalkyl,
R ¹⁶ and R ¹⁷ also together for - (CH ₂ ) ₃ -, - (CH ₂ ) ₄ -, - (CH ₂ ) ₅ -, - (CH ₂ ) ₂ -O- (CH ₂ ) ₂ - or - ( CH ₂ ) ₂ -S- (CH ₂ ) ₂ - stand,
R ^{18 represents} hydrogen or C ₁ -C ₄ alkyl,
R ¹⁹ and R ²⁰ independently of one another represent hydrogen, represent in each case optionally monosubstituted or polysubstituted by identical or different fluorine, chlorine, bromine, C ₁ - C ₄ -alkylcarbonyl, C ₁ -C ₄ alkylcarbonyloxy, C ₁ -C ₄ alkylamino , Di- (C ₁ -C ₄ alkyl) amino, C ₁ -C ₁₀ alkoxy, C ₁ -C ₁₀ alkylthio, C ₁ -C ₁₀ alkoxy-C ₁ -C ₆ alkoxy, C ₁ -C ₁₀ -haloalkoxy, C ₁ -C ₁₀ -haloalkylthio and / or C ₁ -C ₁₀ -haloalkoxy-C ₁ -C ₆ -alkoxy, each with 1 to 21 fluorine, chlorine and / or bromine atoms, substituted C ₁ -C ₁₆ - Alkyl or C ₂ -C ₁₆ alkenyl;
for each optionally single to triple, identical or different by fluorine, chlorine, bromine, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ haloalkoxy, C ₁ -C ₄ haloalkylthio each having 1 to 9 fluorine, chlorine and / or bromine atoms, C ₁ -C ₄ alkylcarbonyl and / or C ₁ -C ₄ alkoxycarbonyl substituted C ₃ - C ₁₀ -cycloalkyl, C ₃ -C ₆ -cycloalkyl-C ₁ -C ₄ -alkyl, phenyl, benzyl, phenylethyl, tetrazolyl, furyl, furfuryl, benzofuryl, tetrahydrofuryl, thienyl, thenyl, benzothienyl, thiolanyl, pyrrolyl, indolyl, pyrrolinyl , Pyrrolidinyl, oxazolyl, benzoxazolyl, isoxazolyl, imidazolyl, pyrazolyl, thiazolyl, benzothiazolyl, thiazolidinyl, pyridinyl, pyrimidinyl, pyridazyl, pyrazinyl, piperidinyl, morpholinyl, thiomorpholinyl, triazinyl, triazolyl, quinolinyl, quinolinyl
R ¹⁸ and R ¹⁹ together also represent C ₂ -C ₃ alkylene which is optionally monosubstituted to trisubstituted by C ₁ -C ₄ alkyl, or
R ¹⁹ and R ²⁰ together with the nitrogen atom to which they are attached also represent a saturated or unsaturated 5- to 7-membered heterocycle which may optionally be a further heteroatom group from the series -O-, -S- or -NR ²² - May contain (in particular from the series Piperidino, Morpholino, Thiomorpholino, Piperazino, Pyrrolidino, Oxazolidino, Thiazolidino, 4H-1-Oxazinyl, 4H-1-Thiazinyl) and the optionally single to fourfold, identical or different by fluorine, chlorine, C ₁ -C ₄ alkyl, C ₁ -C ₄ - alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ -haloalkoxy and / or C ₁ -C ₄ -haloalkylthio having in each case 1 to 9 fluorine, chlorine and / or bromine atoms can be substituted, and
R ^{21 is} hydrogen, -SO ₂ R ⁷ , -COR ⁷ or -CO ₂ R ⁷ ; each optionally one or more times, identically or differently, by fluorine, chlorine, bromine, cyano, methylamino, ethylamino, di- (C ₁ -C ₆ -alkyl) amino, C ₁ -C ₄ -alkoxy, C ₁ - C ₄ -haloalkoxy C ₁ -C ₁₆ substituted with 1 to 9 fluorine, chlorine and / or bromine atoms, C ₁ -C ₄ -alkylthio and / or C ₁ -C ₄ -haloalkylthio with 1 to 9 fluorine, chlorine and / or bromine atoms Alkyl or C ₂ -C ₁₆ alkenyl; for each optionally single to triple, identical or different, by fluorine, chlorine, bromine, cyano, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ - C ₄ haloalkyl , C ₁ -C ₄ haloalkoxy and / or C ₁ -C ₄ haloalkylthio each with 1 to 9 fluorine, chlorine and / or bromine atoms substituted C ₃ -C ₁₀ cycloalkyl, C ₃ -C ₆ cycloalkyl-C ₁ -C ₄ alkyl, phenyl, benzyl, phenylethyl, tetrazolyl, furyl, furfuryl, benzofuryl, tetrahydrofuryl, thienyl, thenyl, benzothienyl, thiolanyl, pyrrolyl, indolyl, pyrrolinyl, pyrrolidinyl, oxazolyl, benzoxazolyl, isoxazolyl, pyrazoleyl , Benzothiazolyl, thiazolidinyl, pyridinyl, pyrimidinyl, pyridazyl, pyrazinyl, piperidinyl, morpholinyl, thiomorpholinyl, triazinyl, triazolyl, quinolinyl or isoquinolinyl,
R ^{22 represents} hydrogen, C ₁ -C ₄ alkyl or C ₂ -C ₄ alkenyl,
w represents 0, 1 or 2,
n represents 1 or 2,
p stands for 0 or 1.

In particular, Δ ¹ -pyrrolines of the formula (I), in which
R ^{1 represents} methyl, ethyl, or optionally monosubstituted aryl, where the substituents from the series fluorine, methyl, ethyl, n-, i-propyl, n-, i-, s-, t-butyl, methoxy, ethoxy , n-, i-propoxy, n-, i-, s-, t-butoxy, methylthio, ethylthio, n-, i-propylthio, n-, i-, s-, t-butylthio, trifluoromethyl, and trifluoromethoxy are,
R ^{2 represents} fluorine, chlorine, bromine, cyano or methyl,
R ^{3 represents} hydrogen or fluorine,
R ^{4 stands} for the grouping -XYZE with the proviso that Y does not stand for a direct bond if X does not stand for a direct bond,
R ⁵ for fluorine, chlorine, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, trifluoromethyl, trifluoroethyl, methoxy, ethoxy, n-propoxy, i-propoxy , n-butoxy, i-butoxy, s-butoxy, t-butoxy, trifluoromethoxy, trifluoroethoxy, methylthio, ethylthio, n-propylthio, i-propylthio, n-butylthio, i-butylthio, s-butylthio, t-butylthio, trifluoromethylthio or trifluoroethylthio,
m represents 0 or 1,
X for a direct bond, oxygen, sulfur, -SO ₂ -, -NR ⁶ -, -CO-, -C (O) -O-, -OC (O) -, -CH ₂ -, - (CH ₂ ) ₂ -, -C = C- (E or Z), -C ~ C-, -CH ₂ O-, - (CH ₂ ) ₂ O-, -OCH ₂ -, -O (CH ₂ ) ₂ -, - O-CH ₂ -O-, -SCH ₂ -, -S (CH ₂ ) ₂ -, -CH ₂ S- or - (CH ₂ ) ₂ S-,
Y for a direct bond or for in each case optionally single or double, identical or different, 1,4-phenylene, 1,3-phenylene, 2,6-naphthylene, 2,7-naphthylene, 2, substituted by radicals from the list W ¹ , 4-furylene, 2,4-thienylene, 2,5-pyridinylene, 2,5-pyrimidinylene, 3,6-pyridazinylene or 2,5-pyrazinylene,
Z is a direct bond, methylene or ethylene,
E for hydrogen, fluorine, chlorine, bromine, hydroxy, cyano, formyl, -S (O) _w R ⁷ , -OSO ₂ R ⁷ , -NR ⁸ R ⁹ , -COR ⁷ , -CO ₂ R ⁷ , -OC ( O) R ⁷ , -CONR ¹⁰ R ¹¹ , -N (R ¹² ) COR ¹³ , -SO ₂ NR ¹⁶ R ¹⁷ , -N (R ¹⁸ ) CO ₂ R ¹⁹ , -N (R ¹⁸ ) C (O) NR ¹⁹ R ²⁰ ; for C ₁ -C ₁₆ -alkyl, C ₂ -C ₁₆ -alkenyl substituted in each case optionally once or several times, identically or differently, by fluorine, chlorine, bromine, cyano, C ₁ -C ₆ -alkoxy and / or -NR ⁸ R ⁹ , C ₁ -C ₁₆ alkoxy, C ₂ -C ₁₆ alkenyloxy; or for each optionally single to triple, identical or different by fluorine, chlorine, bromine, cyano, methyl, ethyl, n-propyl, i-propyl, -CF ₃ , -CHF ₂ , -CClF ₂ , -CF ₂ CHFCl, - CF ₂ CH ₂ F, -CF ₂ CCl ₃ , -CH ₂ CF ₃ , -CF ₂ CHFCF ₃ , -CH ₂ CF ₂ H, -CH ₂ CF ₂ CF ₃ , -CF ₂ CF ₂ H, -CF ₂ CHFCF ₃ , vinyl, allyl, 1-propenyl, butenyl, -CF = CHF, -CF = CH ₂ , -CF = CCl ₂ , -CH = CF ₂ , -CF ₂ CF = CF ₂ , -CH = CFH, -CH ₂ CF = CF ₂ , -CF = CF ₂ , -CF ₂ CH = CF ₂ , methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy, t-butoxy, trifluoromethoxy, Difluoromethoxy, chlorodifluoromethoxy, trifluoroethoxy, methylthio, ethylthio, n-propylthio, i-propylthio, n-butylthio, i-butylthio, s-butylthio, t-butylthio, trifluoromethylthio, difluoromethylthio, chlordififluoromethyl, cyclodifluoromethyl Cyclopentyloxy, cyclohexyloxy, cyclopropylmethyl, cyclopentylmethyl, cyclohexylmethyl, phenyl, phenoxy, benzyl, phenylethyl, benzyloxy, tetrazolyl , Furyl, furfuryl, benzofuryl, tetrahydrofuryl, thienyl, thenyl, benzothienyl, thiolanyl, pyrrolyl, indolyl, pyrrolinyl, pyrrolidino, pyrrolidinyl, oxazolyl, benzoxazolyl, isoxazolyl, imidazolyl, pyrazolyl, thiazolyl, pyridylylzylinylazylyl, , Piperidinyl, piperidino, morpholinyl, thiomorpholinyl, morpholino, thiomorpholino, triazinyl, triazolyl, quinolinyl or isoquinolinyl,
W ¹ for fluorine, chlorine, bromine, cyano, formyl, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, methoxy, ethoxy, n-propoxy, i -Propoxy, n-butoxy, i-butoxy, s-butoxy, t-butoxy, vinyl, allyl, trifluoromethyl, trifluoroethyl, trifluoromethoxy, trifluoroethoxy, -OCF ₂ CF ₂ H, -CH = CF ₂ , -CH = CCl ₂ , -OCF = CF ₂ , -COMe, -COEt, -CO ₂ Me, -CO ₂ Et, -CO ₂ (t-Bu), -SMe, -SOMe, -SO ₂ Me, -SCF ₃ , -SOCF ₃ , -SO ₂ CF ₃ , -SCHF ₂ , -SOCHF ₂ , -SO ₂ CHF ₂ , -SO ₂ NMe ₂ , -NMe ₂ , -NEt ₂ , -N (n-Pr) ₂ , -N (Me) COMe, -N (Me) COEt, -N (Me) COPr, -N (Me) CO (t-Bu), 2-pyrrolidon-5-yl, 2-piperidon-6-yl, -N (Me) SO ₂ Me , -N (Me) SO ₂ Et, -N (Me) SO ₂ CF ₃ , -N (Et) SO ₂ CF ₃ , -N (Me) SO ₂ (CF ₂ ) ₃ CF ₃ or -OSO ₂ NMe ₂ stands,
R ⁶ for methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, trifluoromethyl, trifluoroethyl, cyclopropyl, cyclopropylmethyl, cyclopentyl, cyclopentylmethyl, cyclohexyl, cyclohexylmethyl, phenyl, benzyl or phenylethyl,
R ^{7 is} methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, pentyl, hexyl, -CF ₃ , -CHF ₂ , -CCl ₃ , -CCl ₂ F is dimethylaminomethyl, dimethylaminoethyl, diethylaminomethyl, diethylaminoethyl, cyclopropyl, cyclopentyl, cyclohexyl, phenyl or benzyl,
R ⁸ and R ⁹ independently of one another for hydrogen, -SO ₂ R ⁷ , for each optionally one or more times, identically or differently by fluorine, chlorine and / or bromine, C ₁ -C ₄ -alkylcarbonyl, C ₁ -C ₄ -alkylcarbonyloxy , C ₁ -C ₄ alkylamino, di (C ₁ -C ₄ alkyl) amino, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy with 1 to 9 fluorine, chlorine and / or bromine atoms C ₁ -C ₄ alkylthio and / or C ₁ -C ₄ haloalkylthio with 1 to 9 fluorine, chlorine and / or bromine atoms substituted C ₁ -C ₁₆ alkyl, C ₂ -C ₁₆ alkenyl; for in each case optionally single to triple, identical or different by fluorine, chlorine and / or bromine, cyano, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl with 1 to 9 fluorine, chlorine and / or bromine atoms, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy with 1 to 9 fluorine, chlorine and / or bromine atoms, C ₁ -C ₄ alkylthio and / or C ₁ -C ₄ haloalkylthio with 1 to 9 Fluorine, chlorine and / or bromine atoms substituted C ₃ -C ₈ cycloalkyl, cyclopropylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclopropylethyl, cyclopentylethyl, cyclohexylethyl, phenyl, benzyl, phenylethyl, tetrazolyl, furyl, furfuryl, benzofuryl, tetrahylrofuryl, thien Benzothienyl, thiolanyl, pyrrolyl, indolyl, pyrrolinyl, pyrrolidinyl, oxazolyl, benzoxazolyl, isoxazolyl, imidazolyl, pyrazolyl, thiazolyl, benzothiazolyl, thiazolidinyl, pyridinyl, pyrimidinyl, pyridazyl, pyrazinyl, piperidinyl, morphololinyl, morphololinyl, morphololinyl, morphololinyl, morphololinyl, morphololinyl, morphololinyl, morphololinyl .
R ⁸ and R ⁹ also together for optionally single or multiple, identical or different by fluorine, chlorine and / or bromine, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy with 1 to 9 fluorine, chlorine and / or bromine atoms, C ₁ -C ₄ alkylthio and / or C ₁ -C ₄ haloalkylthio with 1 to 9 fluorine, chlorine and / or bromine atoms substituted C ₂ -C ₈ alkenylene or for one or more, optionally in the alkylene part , identical or different by fluorine, chlorine, cyano, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, C ₁ -C ₄ haloalkyl with 1 to 9 Fluorine, chlorine and / or bromine atoms, methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy, t-butoxy, C ₁ -C ₄ haloalkoxy with 1 to 9 fluorine -, Chlorine and / or bromine atoms, methylthio, ethylthio, n-propylthio, i-propylthio, n-butylthio, i-butylthio, s-butylthio, t-butylthio and / or C ₁ -C ₄ -haloalkylthio with 1 to 9 Fluorine, chlorine and / or bromine atoms substituted C ₃ -C ₈ alkylene, the A alkylene chain can each be interrupted by -O-, -S- or -NR ¹⁴ -,
R ¹⁰ and R ¹¹ independently of one another for hydrogen, -SO ₂ CF ₃ , methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, pentyl, hexyl, -CF ₃ , -CH ₂ CF ₃ , - (CF ₂ ) ₃ CF ₃ , cyclopropyl, cyclopentyl, cyclohexyl, methoxymethyl, methoxyethyl, or for each optionally single to triple, identical or different by fluorine, chlorine, bromine, methyl, trifluoromethyl, methoxy , Trifluoromethoxy substituted phenyl or benzyl,
R ¹⁰ and R ¹¹ also together for - (CH ₂ ) ₄ -, - (CH ₂ ) ₅ -, - (CH ₂ ) ₆ -, -CH ₂ -CH (CH ₃ ) -CH ₂ -CH (CH ₃ ) -CH ₂ -, - (CH ₂ ) ₂ -O- (CH ₂ ) ₂ -, - (CH ₂ ) ₂ -S- (CH ₂ ) ₂ - or - (CH ₂ ) ₂ -N (R ²¹ ) - (CH ₂ ) ₂ - stand,
R ¹² and R ¹³ independently of one another are methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, n-hexyl, trifluoromethyl, trifluoroethyl, cyclopropyl, cyclopentyl, cyclohexyl or represent phenyl or benzyl which are each mono- to tetrasubstituted, identically or differently, by fluorine, chlorine, bromine, methyl, trifluoromethyl, methoxy, trifluoromethoxy,
R ¹² and R ¹³ furthermore together for in each case optionally up to four times, the same or different, substituted by fluorine, chlorine, bromine, methyl, ethyl, methoxy, ethoxy, methylthio, ethylthio, trifluoromethyl, trifluoromethoxy, trifluoromethylthio -, (CH ₂ ) ₃ -, - (CH ₂ ) ₄ -, - (CH ₂ ) ₅ -, - (CH ₂ ) ₆ - stand,
R ¹⁶ and R ¹⁷ independently of one another are hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, n-hexyl, trifluoromethyl, trifluoroethyl, cyclopropyl, cyclopentyl or Cyclohexyl,
R ¹⁶ and R ¹⁷ also together for - (CH ₂ ) ₃ -, - (CH ₂ ) ₄ -, - (CH ₂ ) ₅ -, - (CH ₂ ) ₂ -O- (CH ₂ ) ₂ - or - ( CH ₂ ) ₂ -S- (CH ₂ ) ₂ - stand,
R ^{18 represents} hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl or t-butyl,
R ¹⁹ and R ²⁰ independently of one another for hydrogen, each in each case optionally single or multiple, identical or different, by fluorine, chlorine, bromine, C ₁ -C ₄ -alkylcarbonyl, C ₁ -C ₄ -alkylcarbonyloxy, C ₁ -C ₄ - Alkylamino, di (C ₁ -C ₄ alkyl) amino, C ₁ -C ₁₀ alkoxy, C ₁ -C ₈ alkoxy-C ₁ -C ₆ alkoxy, C ₁ -C ₁₀ alkylthio, C ₁ - C ₁₀ haloalkoxy, C ₁ -C ₁₀ haloalkylthio each having 1 to 21 fluorine, chlorine and / or bromine atoms, C ₁ -C ₈ haloalkoxy-C ₁ -C ₆ alkoxy with 1 to 17 fluorine, chlorine - and / or bromine atoms substituted C ₁ -C ₁₀ alkyl or C ₂ -C ₁₀ alkenyl (especially methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl , the isomeric pentyls, the isomeric hexyls);
for each optionally single to triple, identical or different by fluorine, chlorine, bromine, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ haloalkoxy, C ₁ -C ₄ haloalkylthio each having 1 to 9 fluorine, chlorine and / or bromine atoms, C ₁ -C ₄ alkylcarbonyl and / or C ₁ -C ₄ alkoxycarbonyl substituted C ₃ - C ₈ -cycloalkyl, cyclopropylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclopropylethyl, cyclopentylethyl, cyclohexylethyl, phenyl, benzyl, phenylethyl, tetrazolyl, furyl, furfuryl, benzofuryl, tetrahydrofuryl, thienyl, thenyl, benzothienyl, pyrolylolololololylolololololololylolyrylolol , Benzoxazolyl, isoxazolyl, imidazolyl, pyrazolyl, thiazolyl, benzothiazolyl, thiazolidinyl, pyridinyl, pyrimidinyl, pyridazyl, pyrazinyl, piperidinyl, morpholinyl, thiomorpholinyl, triazinyl, triazolyl, quinolinyl or isoquinolinyl,
R ¹⁸ and R ¹⁹ also together represent in each case optionally single or double, identical or different, methylene or ethylene substituted by methyl, ethyl, n-propyl or i-propyl, or
R ¹⁹ and R ^20, together with the nitrogen atom to which they are attached, for a 5- to 6-membered heterocycle from the series piperidino, morpholino, thiomorpholino, piperazino, pyrrolidino, oxazolidino, thiazolidino, 4H-1-oxazinyl, 4H- 1-Thiazinyl are available, optionally up to four times, the same or different by fluorine, chlorine, bromine, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, methoxy , Ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy, t-butoxy, methylthio, ethylthio, n-propylthio, i-propylthio, n-butylthio, i-butylthio, s-butylthio , butylthio, C ₁ -C t- ₄ haloalkyl, C ₁ -C ₄ -haloalkoxy, C ₁ -C ₄ -haloalkylthio may be substituted with in each case 1 to 9 fluorine, chlorine and / or bromine atoms, the remainder being piperazino on the second nitrogen atom is substituted by R ²² , and
R ²¹ for hydrogen, -SO ₂ R ⁷ , for -COR ⁷ or -CO ₂ R ⁷ ; for each optionally one or more times, identically or differently, by fluorine, chlorine, bromine, cyano, methylamino, ethylamino, di- (C ₁ -C ₆ -alkyl) amino, C ₁ -C ₄ -alkoxy, C ₁ - C ₄ - Haloalkoxy with 1 to 9 fluorine, chlorine and / or bromine atoms, C ₁ -C ₄ alkylthio and / or C ₁ -C ₄ haloalkylthio with 1 to 9 fluorine, chlorine and / or bromine atoms substituted C ₁ -C ₁₆ alkyl, C ₂ -C ₁₆ alkenyl; for each optionally single to triple, identical or different, by fluorine, chlorine, bromine, cyano, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, C ₁ - C ₄ haloalkyl with 1 to 9 fluorine, chlorine and / or bromine atoms, methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy, t-butoxy, C ₁ -C ₄ -haloalkoxy with 1 to 9 fluorine, chlorine and / or bromine atoms, methylthio, ethylthio, n-propylthio, i-propylthio, n-butylthio, i-butylthio, s-butylthio, t-butylthio and / or C ₁ - C ₄ haloalkylthio with 1 to 9 fluorine, chlorine and / or bromine atoms substituted C ₃ -C ₈ cycloalkyl, cyclopropylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclopropylethyl, cyclopentylethyl, cyclohexylethyl, phenyl, benzyl, phenylethyl, tetrazolyl, furyl, furfuryl Benzofuryl, tetrahydrofuryl, thienyl, thenyl, benzothienyl, thiolanyl, pyrrolyl, indolyl, pyrrolinyl, pyrrolidinyl, oxazolyl, benzoxazolyl, isoxazolyl, imidazolyl, pyrazolyl, thiazolyl, benzothiazolyl, thiaz olidinyl, pyridinyl, pyrimidinyl, pyridazyl, pyrazinyl, piperidinyl, morpholinyl, thiomorpholinyl, triazinyl, triazolyl, quinolinyl or isoquinolinyl,
R ^{22 represents} hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, vinyl or allyl.

Also preferred are Δ ¹ -pyrrolines of the formula (I) in which R ^{1 represents} methyl.

Also preferred are Δ ¹ -pyrrolines of the formula (I) in which R ^{1 is} phenyl.

Also preferred are Δ ¹ -pyrrolines of the formula (I) in which R ² and R ^{3 represent} fluorine.

Also preferred are Δ ¹ -pyrrolines of the formula (I) in which R ^{2 represents} fluorine, chlorine, bromine, cyano or methyl and R ^{3 represents} hydrogen.

Also preferred are Δ ¹ -pyrrolines of the formula (I) in which R ^{4 represents} the grouping -YE, Y is 1,4-phenylene and E is the general, preferred, particularly preferred, very particularly preferred or in particular given above has particularly preferred meanings.

Δ ¹ -pyrrolines of the formula (Id) (group 1) are also preferred


in which
R ^{1a represents} C ₁ -C ₈ alkyl (preferably C ₁ -C ₄ alkyl),
R ^{2a represents} fluorine, chlorine, bromine, cyano, nitro, C ₁ -C ₄ alkyl or C ₁ -C ₄ alkoxy,
R ^{3a represents} hydrogen, fluorine, chlorine, bromine, C ₁ -C ₄ alkyl or C ₁ -C ₄ alkoxy,
R ^4a for hydrogen, fluorine, chlorine, bromine, iodine, C ₁ -C ₈ -alkyl, C ₁ -C ₈ -haloalkyl, -OSO ₂ CF ₃ or for optionally single or double, identical or different by halogen, C ₁ - C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ - C ₄ haloalkyl, C ₁ -C ₄ -haloalkoxy and C ₁ -C ₄ -haloalkylthio having in each case 1 to 9 fluorine -, Chlorine and / or bromine atoms substituted phenyl or for optionally simply by halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ - C ₄ alkylthio, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ haloalkoxy and C ₁ -C ₄ haloalkylthio each having 1 to 9 fluorine, chlorine and / or bromine atoms, C ₁ -C ₄ alkylamino or di (C ₁ -C ₄ alkyl) amino substituted Pyridyl or pyrimidinyl is.

Compounds of the formula (Id) in which
R ^{1a represents} methyl, ethyl, n-, i-propyl, n-, i-, s-, t-butyl,
R ^{2a represents} fluorine, chlorine, bromine, cyano or methyl,
R ^{3a represents} hydrogen or fluorine,
R ^{4a represents} hydrogen, fluorine, chlorine, bromine, iodine, -OSO ₂ CF ₃ or simply phenyl substituted in the 4-position by chlorine, methoxy, methylthio, trifluoromethyl, trifluoromethoxy, trifluoromethylthio.

Δ ¹ -pyrrolines of the formula (Ie) (group 2) are also preferred


in which
R ^1a for unsubstituted phenyl or for single or double, identical or different by fluorine, chlorine, bromine, iodine, cyano, nitro, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio , C ₁ -C ₄ haloalkyl, C ₁ -C ₄ haloalkoxy and C ₁ - C ₄ haloalkylthio, each with 1 to 9 fluorine, chlorine and / or bromine atoms, substituted phenyl,
R ^{2b represents} fluorine, chlorine, bromine, cyano, nitro, C ₁ -C ₄ alkyl or C ₁ -C ₄ alkoxy,
R ^{3b represents} hydrogen, fluorine, chlorine, bromine, C ₁ -C ₄ alkyl or C ₁ -C ₄ alkoxy,
R ^4b for hydrogen, fluorine, chlorine, bromine, C ₁ -C ₈ -alkyl, C ₁ -C ₈ -alkyl, C ₁ -haloalkyl, -OSO ₂ CF ₃ or for optionally single or double, identical or different by halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ - C ₄ haloalkyl, C ₁ -C ₄ -haloalkoxy and C ₁ -C ₄ -haloalkylthio having in each case 1 up to 9 fluorine, chlorine and / or bromine atoms substituted phenyl or for optionally simply by halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ - C ₄ alkylthio, C ₁ -C ₄ - Haloalkyl, C ₁ -C ₄ haloalkoxy and C ₁ -C ₄ haloalkylthio each having 1 to 9 fluorine, chlorine and / or bromine atoms, C ₁ -C ₄ alkylamino or di (C ₁ -C ₄ alkyl) ) amino substituted pyridyl or pyrimidinyl.

Compounds of the formula (Ie) in which
R ^{1b represents} unsubstituted phenyl or phenyl which is monosubstituted in the 4-position by fluorine, trifluoromethyl, trifluoromethoxy or trifluoromethylthio,
R ^{2b represents} fluorine, chlorine, bromine, cyano or methyl,
R ^{3b represents} hydrogen or fluorine,
R ^{4b represents} hydrogen, fluorine, chlorine, bromine, iodine, -OSO ₂ CF ₃ or simply phenyl substituted in the 4-position by chlorine, methoxy, methylthio, trifluoromethyl, trifluoromethoxy, trifluoromethylthio.

(R) -configured compounds of the formula (If) are very particularly preferred.


in which
R ¹ , R ² , R ³ , R ⁴ , R ⁵ and m have the meanings given above.

Compounds of the formula (I-f) are obtained by customary processes for Racemate resolution, such as by chromatography of the corresponding racemates a chiral stationary phase. It is possible to use both the racemic End products or racemic intermediates in this way in the two Decompose enantiomers.

Saturated hydrocarbon residues such as alkyl can, as far as possible, each straight chain or branched.

The general or preferred areas listed above Residual definitions or explanations can, however, also be used with one another, i.e. between the respective areas and preferred areas can be combined as desired. they seem for the end products as well as for the preliminary and intermediate products accordingly.

If tert-butyl-2- (4-chlorophenyl) -4- (2,6-difluorobenzoyl) -3-methyl-5-oxo-1-pyrrolidinecarboxylate is used as the starting material in the presence of sulfuric acid / glacial acetic acid, the course of the invention can Process (A) can be illustrated by the following formula scheme.

If tert-butyl-1- (4-chlorophenyl) -4- (2,6-difluorophenyl) -4-oxo-2-phenylbutylcarbamate and trifluoroacetic acid (TFA) are used, the course of process (B) according to the invention can be carried out by the following Formula scheme can be illustrated.

If 2- (4-chlorophenyl) -5- (2,6-difluorophenyl) -3-methyl-3,4-dihydro-2H-pyrrole and 1-bromo-4- (trifluoromethoxy) benzene, as well as 4,4, 4 ', 4', 5,5,5 ', 5'-octamethyl-2,2'-bi-1,3,2-dioxaborolane and a palladium catalyst, the course of process (C) according to the invention can be illustrated by the following formula are illustrated.

If 5- (2,6-difluorophenyl) -3-methyl-2- [4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl] -3.4 is used dihydro-2H-pyrrole and 1-bromo-4-trifluoromethoxybenzene as starting materials and a palladium catalyst, the course of process (D) according to the invention can be illustrated by the following formula.

If 2- (4-chlorophenyl) -5- (2,6-difluorophenyl) -3-methyl-3,4-dihydro-2H-pyrrole and 4- (trifluoromethoxy) phenylboronic acid are used as starting materials and a palladium catalyst, the course can be of the process (E) according to the invention are illustrated by the following formula.

If 2- (4-bromophenyl) -5- (2,6-difluorophenyl) -3-methyl-3,4-dihydro-2H-pyrrole and tributyl [4- (trifluoromethoxy) phenyl] stannane are used as starting materials and a palladium catalyst, the course of process (F) according to the invention can be illustrated by the following formula.

Explanation of the processes and intermediates Procedure (A)

Formula (II) provides a general definition of the aroylpyrrolidinones required as starting materials when carrying out process (A) according to the invention. In this formula, R ^1, R ^2, R ^3, R ^4, R ⁵ and m being preferred, particularly preferred, very particularly preferred or especially preferably has those meanings which have already been in connection with the description of the substances according to the invention of the formula (I) were mentioned as preferred, particularly preferred etc. for these radicals.

• a) Lactame der Formel (VIII)
  
  
  in welcher
  R¹, R⁴, R⁵ und m die oben angegebenen Bedeutungen haben,
  mit einer Verbindung der Formel (IX)
  
  
  in welcher
  R² und R³ die oben angegebenen Bedeutungen haben und
  G für Chlor, C₁-C₆-Alkoxycarbonyl oder -N(OCH₃)CH₃ steht,
  in Gegenwart einer Base [z. B. Lithium-bis(trimethylsilyl)amid] und in Gegenwart eines Verdünnungsmittels (z. B. Tetrahydrofuran) umsetzt (vgl. J. Org. Chem. 1998, 63, 1109; J. Org Chem. 1982, 47, 4165; Org. Prep. Proced. Int. 1995, 27, 510).

Aroylpyrrolidinones of formula (II) are new. They can be made by

• a) lactams of the formula (VIII)
  
  
  in which
  R ¹ , R ⁴ , R ⁵ and m have the meanings given above,
  with a compound of formula (IX)
  
  
  in which
  R ² and R ^{3 have} the meanings given above and
  G represents chlorine, C ₁ -C ₆ alkoxycarbonyl or -N (OCH ₃ ) CH ₃ ,
  in the presence of a base [e.g. B. lithium bis (trimethylsilyl) amide] and in the presence of a diluent (e.g. tetrahydrofuran) (cf. J. Org. Chem. 1998, 63, 1109; J. Org Chem. 1982, 47, 4165; Org Prep. Proced. Int. 1995, 27, 510).

Formula (VIII) provides a general definition of the lactams required as starting materials when carrying out process (a) according to the invention. In this formula, R ¹ , R ⁴ , R ⁵ and m are preferably, particularly preferably, very particularly preferably or particularly very particularly preferably for those meanings which are already in connection with the description of the compounds of the formula (I) according to the invention for these radicals preferred, particularly preferred, etc. were mentioned.

• a) Pyrrolidinone der Formel (X)
  
  
  in welcher
  R¹, R⁴, R⁵ und m die oben angegebenen Bedeutungen haben,
  mit Di-tert-butyldicarbonat in Anwesenheit einer Base (z. B. Dimethylaminopyridin) und gegebenenfalls in Gegenwart eines Verdünnungsmittels (z. B. Dimethylformamid) umsetzt. (vgl. Tetrahedron Letters, 1998, 39, 2705-2706).

Lactams of the formula (VIII) are new. They can be made by

• a) pyrrolidinones of the formula (X)
  
  
  in which
  R ¹ , R ⁴ , R ⁵ and m have the meanings given above,
  with di-tert-butyl dicarbonate in the presence of a base (e.g. dimethylaminopyridine) and optionally in the presence of a diluent (e.g. dimethylformamide). (see Tetrahedron Letters, 1998, 39, 2705-2706).

Formula (IX) provides a general definition of the compounds required as starting materials when carrying out process (a) according to the invention. In this formula, R ² and R ^{3 are} preferred, particularly preferred, very particularly preferred or in particular very particularly preferred for those meanings which are preferred, particularly preferred etc. in connection with the description of the compounds of the (I) according to the invention for these radicals, etc. were called. G preferably represents chlorine, methoxycarbonyl, ethoxycarbonyl, i-propoxycarbonyl, t-butoxycarbonyl or -N (OCH ₃ ) CH ₃ , particularly preferably chlorine.

Compounds of the formula (IX) are known and / or can be prepared according to known ones Establish processes (cf. J. Prakt. Chem. 2000, 342, 340).

Formula (X) provides a general definition of the pyrrolidinones required as starting materials when carrying out process (b) according to the invention. In this formula, R ¹ , R ⁴ , R ⁵ and m are preferably, particularly preferably, very particularly preferably or particularly very particularly preferably for those meanings which are already in connection with the description of the compounds of the formula (I) according to the invention for these radicals preferred, particularly preferred, etc. were mentioned.

• a) Aminosäuren der Formel (XI)
  
  
  in welcher
  R¹, R⁴, R⁵ und m die oben angegebenen Bedeutungen haben,
  gegebenenfalls in Gegenwart eines Verdünnungsmittels (z. B. Xylol) und gegebenenfalls in Gegenwart einer Base (z. B. wässrige Ammoniaklösung) umsetzt, oder
• b) Ketocarbonsäure-Derivate der Formel (XII)
  
  
  in welcher
  R¹, R⁴, R⁵ und m die oben angegebenen Bedeutungen haben,
  mit Ammoniak und Wasserstoff in Gegenwart eines Katalysators (z. B. Raney- Nickel) und gegebenenfalls in Gegenwart eines Verdünnungsmittels (z. B. Ethanol) unter Druck umsetzt (vgl. Eur. J. Med. Chem. 1993, 28, 129).

Pyrrolidinones of the formula (X) are new. They can be made by

• a) amino acids of the formula (XI)
  
  
  in which
  R ¹ , R ⁴ , R ⁵ and m have the meanings given above,
  if appropriate in the presence of a diluent (for example xylene) and if appropriate in the presence of a base (for example aqueous ammonia solution), or
• b) ketocarboxylic acid derivatives of the formula (XII)
  
  
  in which
  R ¹ , R ⁴ , R ⁵ and m have the meanings given above,
  with ammonia and hydrogen in the presence of a catalyst (e.g. Raney nickel) and optionally in the presence of a diluent (e.g. ethanol) under pressure (see Eur. J. Med. Chem. 1993, 28, 129) ,

Formula (XI) provides a general definition of the amino acids required as starting materials when carrying out process (c) according to the invention. In this formula, R ¹ , R ⁴ , R ⁵ and m are preferably, particularly preferably, very particularly preferably or particularly very particularly preferably for those meanings which are already in connection with the description of the compounds of the formula (I) according to the invention for these radicals preferred, particularly preferred, etc. were mentioned.

• a) Benzylamine der Formel (XIII)
  
  
  in welcher
  R⁴, R⁵ und m die oben angegebenen Bedeutungen haben,
  mit Benzophenon gegebenenfalls in Gegenwart eines Verdünnungsmittels (z. B. Toluol) in Gegenwart einer Säure (z. B. p-Toluolsulfonsäure) umsetzt und anschließend
  die resultierenden Verbindungen der Formel (XIV)
  
  
  in welcher
  R⁴, R⁵ und m die oben angegebenen Bedeutungen haben, mit einem α,β-ungesättigten Ester bzw. Nitrile der Formel (XV)
  
  
  in welcher
  R¹⁹ für C₁-C₄-Alkoxycarbonyl oder Cyano steht,
  R¹ die oben angegebenen Bedeutungen hat,
  in Gegenwart von Triethyldbenzylammoniumchlorid, in Gegenwart einer Base (z. B. Natriumhydroxid) und gegebenenfalls in Gegenwart eines Verdünnungsmittels (z. B. Toluol) umsetzt.

Amino acids of the formula (XI) are new. They can be made by

• a) Benzylamines of the formula (XIII)
  
  
  in which
  R ⁴ , R ⁵ and m have the meanings given above,
  with benzophenone, if appropriate in the presence of a diluent (for example toluene) in the presence of an acid (for example p-toluenesulfonic acid) and then
  the resulting compounds of formula (XIV)
  
  
  in which
  R ⁴ , R ⁵ and m have the meanings given above, with an α, β-unsaturated ester or nitrile of the formula (XV)
  
  
  in which
  R ^{19 represents} C ₁ -C ₄ alkoxycarbonyl or cyano,
  R ^{1 has} the meanings given above,
  in the presence of triethyldbenzylammonium chloride, in the presence of a base (e.g. sodium hydroxide) and optionally in the presence of a diluent (e.g. toluene).

Formula (XIII) provides a general definition of the benzylamines required as starting materials when carrying out process (e) according to the invention. In this formula, R ⁴ , R ⁵ and m are preferably, particularly preferably, very particularly preferably or particularly very particularly preferably for those meanings which are particularly preferred for these radicals already in connection with the description of the compounds of the formula (I) according to the invention preferred etc. were mentioned.

Benzylamines of the formula (XIII) are known and / or can be prepared according to known ones Establish process.

Formula (XV) provides a general definition of the α, β-unsaturated esters or nitriles required as starting materials when carrying out process (e) according to the invention. In this formula, R ¹ preferably, particularly preferably, very particularly preferably or in particular very particularly preferably represents those meanings which have already been mentioned as preferred, particularly preferred etc. for these radicals in connection with the description of the compounds of the formula (I) according to the invention , R ¹⁹ preferably represents methoxycarbonyl, ethoxycarbonyl, n-, i-propoxycarbonyl, n-, i-, s-, t-butoxycarbonyl or cyano, particularly preferably methoxycarbonyl, ethoxycarbonyl, i-propoxycarbonyl, t-butoxycarbonyl or cyano, very particularly preferred for methoxycarbonyl or cyano.

α, β-unsaturated esters or nitriles of the formula (XV) are known and / or leave produce themselves by known methods.

Formula (XII) provides a general definition of the ketocarboxylic acids required as starting materials when carrying out process (d) according to the invention. In this formula, R ¹ , R ⁴ , R ⁵ and m are preferably, particularly preferably, very particularly preferably or particularly very particularly preferably for those meanings which are already in connection with the description of the compounds of the formula (I) according to the invention for these radicals preferred, particularly preferred, etc. were mentioned.

Ketocarboxylic acids of the formula (XII) are known in some cases and / or can known methods can be prepared (see, for example, Eur. J. Med. Chem. 1993, 28, 129; J. Chin. Pharm. Sci. 1992, 1, 27).

Process (A) according to the invention is carried out in the presence of an acid. All acids can be used in carrying out the process according to the invention Protonic acids customary for such a reaction or strong ones organic acids (such as sulfonic acids) or halocarboxylic acids can be used. Hydrochloric acid, sulfuric acid, hydrofluoric acid, phosphoric acid, p-toluenesulfonic acid, methanesulfonic acid, trifluoroacetic acid or trichloroacetic acid. Hydrochloric acid, sulfuric acid p-toluenesulfonic acid are particularly preferably used or trifluoroacetic acid, very particularly preferably sulfuric acid. The one used Acid can optionally be used in a mixture with water.

If appropriate, the process according to the invention can be carried out in the presence of a Diluent are carried out. As a diluent come in the Carrying out the process according to the invention organic acids in question. Propionic acid, acetic acid or formic acid can preferably be used. Especially acetic acid is preferably used.

It is very particularly preferred to carry out the process according to the invention Process any mixture of sulfuric acid (as acid) and acetic acid (as Diluent) and optionally water. One is particularly suitable Mixture of concentrated sulfuric acid, water and acetic acid in the ratio from 1: 1: 2 (volume / volume / volume = v / v / v) or 1: 1: 3 (v / v / v). But it can other mixing ratios can also be set and used.

The reaction temperatures can be carried out when carrying out the inventive Process (A) can be varied over a wide range. Generally works one at temperatures between 20 ° C and 200 ° C, preferably at temperatures between 60 ° C and 150 ° C.

The course of the reaction is expediently checked by means of Thin layer chromatography. The response time depends on the type of used Compound of formula (II) between 0.5 h and 6 h.

When carrying out process (A) according to the invention, generally an excess of acid to 1 mol of aroylpyrrolidinone of the formula (II) (between 1 mole and 50 moles). However, other conditions of the Reaction components can be selected. The processing takes place according to usual Methods. In general, one proceeds in such a way that one Reaction mixture alkalized with sodium hydroxide, the product extracted, the organic Phase washes, dries and evaporates under reduced pressure. The raw product is then using conventional methods (e.g. chromatography or Recrystallization) freed of any residues that may still be present.

Procedure (B)

Formula (III) provides a general definition of the compounds required as starting materials when carrying out process (B) according to the invention. In this formula, R ^1, R ^2, R ^3, R ^4, R ⁵ and m being preferred, particularly preferred, very particularly preferred or especially preferably has those meanings which have already been in connection with the description of the substances according to the invention of the formula (I) were mentioned as preferred, particularly preferred etc. for these radicals.

• a) Lactame der Formel (VIII)
  
  
  in welcher
  R¹, R⁴, R⁵ und m die oben angegebenen Bedeutungen haben,
  mit einer Lithium-Verbindung der Formel (XVI)
  
  
  in welcher
  R² und R³ die oben angegebenen Bedeutungen haben
  gegebenenfalls in Gegenwart eines Verdünnungsmittels umsetzt.

Compounds of (III) are new. They can be made by

• a) lactams of the formula (VIII)
  
  
  in which
  R ¹ , R ⁴ , R ⁵ and m have the meanings given above,
  with a lithium compound of the formula (XVI)
  
  
  in which
  R ² and R ^{3 have} the meanings given above
  if appropriate in the presence of a diluent.

The starting materials when carrying out process (f) according to the invention required lactams of formula (VIII) are already in the explanation of the process (A).

Formula (XVI) provides a general definition of the lithium compounds required as starting materials when carrying out process (f) according to the invention. In this formula, R ² and R ^{3 are} preferred, particularly preferred, very particularly preferred or in particular very particularly preferred for those meanings which are preferred, particularly preferred etc. in connection with the description of the compounds of the (I) according to the invention for these radicals, etc. were called.

Lithium compounds of the formula (XVI) are known and / or can be reduced known processes from the corresponding 1,3-disubstituted phenyl derivatives produce.

Process (B) according to the invention is carried out in the presence of an acid. All acids can be used in carrying out the process according to the invention Protonic acids customary for such a reaction or strong ones organic acids (such as sulfonic acids) or halocarboxylic acids can be used. Hydrochloric acid, sulfuric acid, hydrofluoric acid, phosphoric acid, p-toluenesulfonic acid, methanesulfonic acid, trifluoroacetic acid or trichloroacetic acid. Trifluoroacetic acid is particularly preferably used. The acid used can optionally used in a mixture with water.

Suitable diluents for carrying out the process according to the invention Process (B) in each case all the usual inert, organic solvents in question. Halogenated aliphatic, alicyclic or aromatic hydrocarbons, such as petroleum ether, hexane, heptane, cyclohexane, Methylcyclohexane, benzene, toluene, xylene or decalin; Chlorobenzene, dichlorobenzene, Dichloromethane, chloroform, carbon tetrachloride, dichloroethane or trichloroethane; Ethers, such as diethyl ether, diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, Dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole. Dichloromethane is particularly preferably used.

The reaction temperatures can be carried out when carrying out the inventive Process (B) can be varied over a wide range. Generally works one at temperatures between -20 ° C and + 60 ° C, preferably at temperatures between -10 ° C and 40 ° C.

When carrying out process (B) according to the invention, generally an excess of acid to 1 mol of a compound of formula (III) (between 1 mole and 50 moles). However, other conditions of the Reaction components can be selected. The processing takes place according to usual Methods. In general, one proceeds in such a way that one Reaction mixture neutralized with sodium hydrogen carbonate, the product extracted, the organic phase washes, dries and concentrates under reduced pressure. The raw product is then carried out using customary methods (e.g. chromatography or Recrystallization) freed of any residues that may still be present.

Process (C)

In a first reaction step, a Δ ¹ -pyrroline of the formula (Ib) is coupled with a diboronic acid ester in the presence of a palladium catalyst, if appropriate in the presence of an acid binder and if appropriate in the presence of a solvent. Without isolating the intermediate product, a compound of the formula (IV) is coupled in the same reaction vessel in a second reaction step in the presence of a catalyst, if appropriate in the presence of an acid binder and if appropriate in the presence of a solvent (cf. e.g. Tetrahedron Lett. 1997, 38, 3841).

The process (C) according to the invention can be carried out in two variants. It can either be a compound of formula (I-b) or a compound of Formula (IV) are presented. Process (D) is the tandem reaction process (D) and (E) described below.

Formula (Ib) provides a general definition of the Δ ¹ -pyrrolines required as starting materials when carrying out process (C) according to the invention. In this formula, R ¹ , R ² , R ³ , R ⁵ and m are preferably, particularly preferably, very particularly preferably or particularly very particularly preferably those meanings which have already been associated with the description of the substances of the formula (I) according to the invention were mentioned as preferred, particularly preferred etc. for these radicals. R ⁴² preferably represents chlorine, bromine, iodine, -OSO ₂ CF ₃ or -SO ₂ (CF ₂ ) ₃ CF ₃ , particularly preferably chlorine, bromine, -OSO ₂ CF ₃ or -OSO ₂ (CF ₂ ) ₃ CF. ₃ , very particularly preferably for chlorine, bromine or -OSO ₂ CF ₃ .

Δ ¹ -pyrrolines of the formula (Ib) are the subject of this invention and can be prepared by one of processes (A) or (B).

Formula (IV) provides a general definition of the cyclic compounds required as starting materials when carrying out process (C) according to the invention. In this formula, E is preferably, particularly preferably, very particularly preferably or in particular very particularly preferably those meanings which have already been mentioned as preferred, particularly preferred etc. for these radicals in connection with the description of the substances of the formula (I) according to the invention , Y ¹ preferably represents in each case optionally up to four times, identical or different, phenylene substituted by radicals from the list W ¹ or 5- to 10-membered, saturated or unsaturated heterocyclylene with one or more heteroatoms from the series nitrogen, oxygen and sulfur. Y ¹ particularly preferably represents 1,4-phenylene, 1,3-phenylene, 1,2-phenylene which may be monosubstituted to tetrasubstituted, identically or differently, by radicals from the list W ¹ ; or represents in each case optionally mono- to tetrasubstituted by identical or different radicals from the list W ¹ is substituted 5- to 6-membered saturated or unsaturated heterocyclylene having 1 to 3 heteroatoms, containing 0 to 3 nitrogen atoms, 0 to 2 nonadjacent oxygen atoms and / or contains 0 to 2 non-adjacent sulfur atoms (especially furylene, thienylene, pyrrolylene, oxazolylene, thiazolylene, pyridinylene, pyrimidinylene, pyridazinylene or pyrazinylene). Y ¹ very particularly preferably represents 1,4-phenylene, 1,3-phenylene, 1,2-phenylene, 2,4-furylene, 2, which may be monosubstituted to trisubstituted identically or differently by radicals from the list W ¹ , 4-thienylene, 2,4-pyrrolylene, 2,5-oxazolylene, 2,5-thiazolylene, 2,5-pyridinylene, 2,6-pyridinylene, 2,5-pyrimidinylene, 3,6-pyridazinylene or 2,5- pyrazinylene. Y ¹ in particular very particularly preferably represents 1,4-phenylene, 1,3-phenylene, 1,3-phenylene, 2,4-furylene, 2,4-thienylene, 2 which may be substituted once or twice, identically or differently by radicals from the list W ' , 5-pyridinylene, 2,5-pyrimidinylene, 3,6-pyridazinylene or 2,5-pyrazinylene. W ¹ preferably, particularly preferably, very particularly preferably or in particular very particularly preferably represents those meanings which have already been mentioned as preferred, particularly preferred etc. in connection with the description of the compounds of the formula (I) according to the invention for these radicals. A ¹ preferably represents bromine, chlorine, iodine or -SO ₂ CF ₃ , particularly preferably bromine, chlorine or iodine, very particularly preferably bromine or chlorine.

The cyclic compounds of formula (IV) are known or can according to known methods can be prepared (see Aust. J. Chem. 1964, 17, 794; Chem. Ber. 1992, 125, 1169; Chem. Pharm. Bull. 1995, 43, 247; Eur. J. Med. Chem. 1989, 24, 249; J. Chem. Soc. C 1971, 1889; J. Chem. Soc. Perkin Trans. 1 1995, 2497; J. Med. Chem. 1991, 34, 315; J. Org. Chem. 1984, 49, 2240; J. Org. Chem. 1990, 55, 69; Org. Prep. Proced. Int. 1998, 30, 433; Synthesis 1999, 1163; Tetrahedron 1999, 40, 7975; Tetrahedron Lett. 1996, 37, 4447; Tetrahedron Lett. 2000, 41, 4335).

The diboronic acid esters used in carrying out the process according to the invention Process (C) 4,4,4 ', 4', 5,5,5 ', 5'-octamethyl-2,2'-bi-1,3,2-dioxaborolane, 5,5,5', 5 ' - Tetramethyl-2,2'-bi-1,3,2-dioxaborinane, 4,4,4 ', 4', 6,6'-hexamethyl-2,2'-bi-1,3,2-dioxaborinan or 2,2'-Bi-1,3,2-benzodioxaborol in question. It is preferred to use 4,4,4 ', 4', 5,5,5 ', 5'-octamethyl-2,2'-bi-1,3,2-dioxaborolane, 5.5.5', 5'-tetramethyl- 2,2'-bi-1,3,2-dioxaborinan or 4,4,4 ', 4', 6,6'-hexamethyl-2,2'-bi-1,3,2-dioxaborinan, particularly preferably 4,4,4 ', 4', 5,5,5 ' , 5'-octamethyl-2,2'-bi-1,3,2-dioxaborolane or 5,5,5 ', 5'-tetramethyl-2,2'-bi-1,3,2-dioxaborinan, very particularly preferred 4,4,4 ', 4', 5,5,5 ', 5'-octamethyl-2,2'-bi-1,3,2-dioxaborolane.

When carrying out process (C) according to the invention, 1 mol or a slight excess of a diborone ester and 1 mol or a slight excess of a cyclic compound of the formula (IV) are generally employed per mole of Δ ¹ -pyrroline of the formula (Ib), and 3% of a palladium catalyst. However, it is also possible to use the reaction components in other ratios. Optionally, the compound of formula (Ib) or the compound of formula (IV) can be submitted first. The processing takes place according to usual methods. In general, the procedure is such that the reaction mixture is diluted with water and extracted with ethyl acetate. The organic phase is washed, dried, filtered and concentrated. If appropriate, the residue is freed of any impurities which may still be present using customary methods, such as chromatography or recrystallization.

Procedure (D)

Formula (V) provides a general definition of the Δ ¹ -pyrrolines required as starting materials when carrying out process (D) according to the invention. In this formula, R ¹ , R ² , R ³ , R ⁵ and m are preferably, particularly preferably, very particularly preferably or particularly very particularly preferably those meanings which have already been associated with the description of the substances of the formula (I) according to the invention were mentioned as preferred, particularly preferred etc. for these radicals. A ² preferably represents -B (OH) ₂ , (4,4,5,5-tetramethyl-1,3,2-dioxaborolane) -2-yl, (5,5-dimethyl-1,3,2-dioxaborinane ) -2-yl, (4,4,6-trimethyl-1,3,2-dioxaborinan) -2-yl or 1,3,2-benzodioxaborol-2-yl, particularly preferred for - (OH) ₂ , ( 4,4,5,5-tetramethyl-1,3,2-dioxaborolane) -2-yl, (5,5-dimethyl-1,3,2-dioxaborinane) -2-yl or (4,4,6- Trimethyl-1,3,2-dioxaborinan) -2-yl, very particularly preferred for -B (OH) ₂ , (4,4,5,5-tetramethyl-1,3,2-dioxaborolan) -2-yl, (5,5-dimethyl-1,3,2-dioxaborinan) -2-yl.

• a) Verbindungen der Formel (I-b)
  
  
  in welcher
  R¹, R², R³, R⁵, m und R⁴² die oben angegebenen Bedeutungen haben,
  mit einem Diboronsäureester in Gegenwart eines Katalysators, gegebenenfalls in Gegenwart eines Säurebindemittels und gegebenenfalls in Gegenwart eines Verdünnungsmittels umsetzt (vgl. J. Org. Chem. 1995, 60, 7508; Tetrahedron Lett. 1997, 38, 3447).

D ¹ -pyrrolines of the formula (V) can be prepared by

• a) compounds of the formula (Ib)
  
  
  in which
  R ¹ , R ² , R ³ , R ⁵ , m and R ^{42 have} the meanings given above,
  with a diboronic acid ester in the presence of a catalyst, if appropriate in the presence of an acid binder and if appropriate in the presence of a diluent (cf. J. Org. Chem. 1995, 60, 7508; Tetrahedron Lett. 1997, 38, 3447).

Suitable diboronic acid esters for carrying out process (g) are in the Description of the process (C) according to the invention has already been mentioned.

The starting materials when carrying out process (D) according to the invention required cyclic compounds of formula (IV) have already been mentioned above in the Description of the method (C) described.

When carrying out process (D) according to the invention, 1 mol or a slight excess of a cyclic compound of the formula (IV) is generally employed per mol of Δ ¹ -pyrroline of the formula (V). However, it is also possible to use the reaction components in other ratios. The processing takes place according to usual methods. In general, the procedure is such that the reaction mixture is taken up in ethyl acetate and the organic phase is washed with water, dried over sodium sulfate, filtered and concentrated. If appropriate, the residue is freed of any impurities which may still be present using customary methods, such as chromatography or recrystallization.

Procedure (E)

The Δ ¹ -pyrrolines of the formula (Ib) required as starting materials when carrying out process (F) according to the invention have already been described in the description of process (C).

Formula (VI) provides a general definition of the boronic acid derivatives required as starting materials when carrying out process (E) according to the invention. In this formula, E is preferably, particularly preferably, very particularly preferably or in particular very particularly preferably those meanings which have already been mentioned as preferred, particularly preferred etc. for these radicals in connection with the description of the substances of the formula (I) according to the invention , Y ¹ preferably, particularly preferably, very particularly preferably or in particular very particularly preferably represents those meanings which have already been mentioned as preferred, particularly preferred etc. in connection with the description of the substances of the formula (IV) for these radicals. A ² preferably, particularly preferably, very particularly preferably or in particular very particularly preferably represents those meanings which have already been mentioned as preferred, particularly preferred etc. in connection with the description of the substances of the formula (V) for these radicals.

The compounds of formula (VI) are known or can be made according to known ones Produce processes (cf. J. Org. Chem. 1995, 60, 7508, Tetrahedron Lett. 1997, 38, 3447).

When carrying out process (E) according to the invention, the starting point is 1 mol Compound of formula (I-b) generally 1 mole or a slight excess a compound of formula (VI). However, it is also possible that Use reaction components in other ratios. The processing takes place after usual methods. In general, one proceeds in such a way that one Reaction mixture takes up in ethyl acetate and the organic phase with water washes, dries over sodium sulfate, filtered and concentrated. The backlog will optionally by customary methods, such as chromatography or recrystallization, freed of any impurities that may still be present.

Procedure (F)

Formula (Ic) provides a general definition of the Δ ¹ -pyrrolines required as starting materials when carrying out process (F) according to the invention. In this formula, R ¹ , R ² , R ³ , R ⁵ and m are preferably, particularly preferably, very particularly preferably or particularly very particularly preferably those meanings which have already been associated with the description of the substances of the formula (I) according to the invention were mentioned as preferred, particularly preferred etc. for these radicals. R ⁴³ preferably represents bromine or iodine.

Δ ¹ -pyrrolines of the formula (Ic) are the subject of this invention and can be prepared by one of processes (A) or (B).

Formula (VII) provides a general definition of the organometallic compounds required as starting materials when carrying out process (F) according to the invention. In this formula, E is preferably, particularly preferably, very particularly preferably or in particular very particularly preferably those meanings which have already been mentioned as preferred, particularly preferred etc. for these radicals in connection with the description of the substances of the formula (I) according to the invention , In this formula, Y ^{1 is} preferably, particularly preferably, very particularly preferably or particularly very particularly preferably those meanings which have already been mentioned as preferred, particularly preferred, etc. for these radicals in connection with the description of the substances of the formula (IV) according to the invention were. M preferably represents ZnCl, Sn (Me) ₃ or Sn (n-Bu) ₃ .

Organometallic compounds of the formula (VII) are known in some cases and / or can be prepared by known methods. It is Z. B. possible to prepare compounds of formula (VII) from the corresponding compounds of formula (IV), in which A ^{1 is} -OSO ₂ CF ₃ , in situ (cf. Tetrahedron Lett. 1995, 36, 9085).

When carrying out process (F) according to the invention, the starting point is 1 mol Compound of formula (I-c) generally 1 mole or a slight excess a compound of formula (VII). However, it is also possible that Use reaction components in other ratios. The processing takes place after usual methods. In general, one proceeds in such a way that one Reaction mixture takes up in ethyl acetate and the organic phase with water washes, dries over sodium sulfate, filtered and concentrated. The backlog will optionally by customary methods, such as chromatography or recrystallization, freed of any impurities that may still be present.

When carrying out processes (C), (D), (E) and (F) according to the invention, a palladium catalyst is used, which in turn can be used with or without the addition of further ligands. The catalyst used is preferably PdCl ₂ (dppf) [dppf = 1,1'-bis (diphenylphosphino) ferrocene], Pd (PPh ₃ ) ₄ , PdCl ₂ (PPh ₃ ) ₂ , PdCl ₂ (CH ₃ CN) ₂ , Pd ₂ (dba) ₃ [dba = dibenzylidene acetone] or Pd (Oac) ₂ , particularly preferably PdCl ₂ (dppf), Pd (PPh ₃ ) ₄ , PdCl ₂ (PPh ₃ ) ₂ , or Pd (Oac) ₂ , very particularly preferred PdCl ₂ (dppf) or PdCl ₂ (PPh ₃ ) ₂ .

Triarylphosphines, trialkylphosphines or arsines are suitable as ligands. Dppf, PPh ₃ , P (t-Bu) ₃ , Pcy ₃ or AsPh _{3 are} preferably used, particularly preferably dppf.

Suitable diluents for carrying out the inventive Process (C), (D) and (E) each have all the usual inert, organic solvents in Question. Halogenated aliphatic, alicyclic or aromatic hydrocarbons, such as petroleum ether, hexane, heptane, Cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin; Chlorobenzene, Dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane or trichloroethane; Ethers, such as diethyl ether, diisopropyl ether, methyl t-butyl ether, Methyl t-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole; Nitriles, such as acetonitrile, propionitrile, n- or i-butyronitrile or benzonitrile; Amides, such as N, N-dimethylformamide, N, N-dimethylacetamide, N- Methyl formanilide, N-methyl pyrrolidone or hexamethyl phosphoric acid triamide; ester such as methyl acetate or ethyl acetate; Sulfoxides, such as Dimethyl sulfoxide or sulfones such as sulfolane. Acetone is particularly preferably used, Dimethoxyethane, dioxane, tetrahydrofuran, dimethylformamide, dimethylacetamide, Dimethyl sulfoxide, ethanol, toluene or mixtures of these if appropriate Diluent with water.

Suitable diluents for carrying out the process according to the invention Process (F) in each case all the usual inert, organic solvents in question. Halogenated aliphatic, alicyclic or aromatic hydrocarbons, such as petroleum ether, hexane, heptane, cyclohexane, Methylcyclohexane, benzene, toluene, xylene or decalin; Chlorobenzene, dichlorobenzene, Dichloromethane, chloroform, carbon tetrachloride, dichloroethane or trichloroethane; Ethers, such as diethyl ether, diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, Dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole. Dioxane, tetrahydrofuran or toluene are particularly preferably used.

The acid binders used in carrying out the inventive Process (C), (D), (E) and (F) all all customary for such reactions inorganic and organic bases. Alkaline earth metal or alkali metal hydroxides, such as sodium hydroxide, calcium hydroxide, Potassium hydroxide, or ammonium hydroxide, alkali metal carbonates, such as Sodium carbonate, potassium carbonate, potassium hydrogen carbonate, sodium hydrogen carbonate, alkali or alkaline earth metal acetates such as sodium acetate, potassium acetate, calcium acetate, Alkali metal fluorides, and also tertiary amines, such as trimethylamine, triethylamine, Tributylamine, N, N-dimethylaniline, pyridine, N-methylpiperidine, N, N-dimethylaminopyridine, Diazabicyclooctane (DABCO), diazabicyclonones (DBN) or diazabicycloundecene (DBU). However, it is also possible to work without an additional acid binder, or to use the amine component in excess so that it is simultaneously acts as an acid binder. Barium hydroxide is particularly preferably used, Sodium hydroxide, potassium hydroxide, tripotassium phosphate, cesium carbonate, Potassium carbonate, sodium carbonate, potassium acetate, triethylamine, potassium tert-butanolate, Cesium fluoride or potassium fluoride.

The reaction temperatures can be carried out when the inventive Processes (C), (D) and (E) can each be varied within a relatively wide range. in the generally one works at temperatures between 0 ° C and 140 ° C, preferably between 20 ° C and 120 ° C, particularly preferably between 60 ° C and 100 ° C.

The reaction temperatures can be carried out when carrying out the inventive Process (F) can be varied over a wide range. In general one works at temperatures between 0 ° C and 140 ° C, preferably between 20 ° C and 120 ° C.

Chiral compounds of the formula (I-f)

To produce chiral compounds of the formula (If), for example, the Δ ¹ -pyrrolines of the formula (Ib) used as intermediates


in which
R ¹ , R ² , R ³ , R ⁵ , m and R ^{42 have} the meanings given above,
or the pyrrolidinones of the formula (X)


in which
R ¹ , R ⁴ , R ⁵ and m have the meanings given above,
be subjected to a resolution. For example, preparative chromatography, preferably high performance liquid chromatography (HPLC), is used. A chiral stationary silica gel phase is used. A silica gel modified with tris (3,5-dimethylphenylcarbamate) cellulose has proven to be particularly suitable for the separation of the compounds of the formula (Ib) into the two enantiomers. This separation material is commercially available. However, it is also possible to use other stationary phases. All customary inert, organic solvents and mixtures of these can be used as eluents. Halogenated aliphatic, alicyclic or aromatic hydrocarbons, such as petroleum ether, hexane, heptane, cyclohexane; Dichloromethane, chloroform; Alcohols, such as methanol, ethanol, propanol; Nitriles such as acetonitrile; Esters such as methyl acetate or ethyl acetate. It is particularly preferred to use aliphatic hydrocarbons, such as hexane or heptane, and alcohols, such as methanol or propanol, very particularly preferably n-heptane and isopropanol or mixtures of these. In general, temperatures between 10 ° C and 60 ° C, preferably between 10 ° C and 40 ° C, particularly preferably at room temperature. The (R) -configured enantiomers obtained in this way are then used as starting materials for processes (C) or (E).

With good plant tolerance and favorable toxicity to warm-blooded animals, the active substances are suitable for controlling animal pests, in particular insects, arachnids and nematodes, which occur in agriculture, in forests, in the protection of stored goods and materials, and in the hygiene sector. They can preferably be used as pesticides. They are effective against normally sensitive and resistant species as well as against all or individual stages of development. The pests mentioned above include:
From the order of the Isopoda z. B. Oniscus asellus, Armadillidium vulgare, Porcellio scaber.
From the order of the Diplopoda z. B. Blaniulus guttulatus.
From the order of the Chilopoda z. B. Geophilus carpophagus, Scutigera spp.
From the order of the Symphyla z. B. Scutigerella immaculata.
From the order of the Thysanura z. B. Lepisma saccharina.
From the order of the Collembola z. B. Onychiurus armatus.
From the order of the Orthoptera z. B. Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus spp., Schistocerca gregaria.
From the order of the Blattaria z. B. Blatta orientalis, Periplaneta americana, Leucophaea maderae, Blattella germanica.
From the order of the Dermaptera z. B. Auricular Forficula.
From the order of the Isoptera z. B. Reticulitermes spp.
From the order of the Phthiraptera z. B. Pediculus humanus corporis, Haematopinus spp., Linognathus spp., Trichodectes spp., Damalinia spp.
From the order of the Thysanoptera z. B. Hercinothrips femoralis, Thrips tabaci, Thrips palmi, Frankliniella accidentalis.
From the order of the Heteroptera z. B. Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus, Triatoma spp.
From the order of Homoptera z. B. Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Aphis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Phylloxera vastatrix, Pemphigus sppe, Phosiphodumumpp., Macrosiphumum padi, Empoasca spp., Euscelis bilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp., Psylla spp.
From the order of the Lepidoptera z. B. Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella xylostella, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp., Bucculatrix thurberiisppina, Fpp , Heliothis spp., Mamestra brassicae, Panolis flammea, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleria mellonella, Tineola bisselliella, Hofeamannellellaella, Hofeamannellaellaella, Tinea pellionella Capua reticulana, Choristoneura fumiferana, Clysia ambiguella, Homona magnanima, Tortrix viridana, Cnaphalocerus spp., Oulema oryzae.
From the order of the Coleoptera z. B. Anobium punctatum, Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus, Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedon cochleariae, Diabrotica spp., Psylliodes chrysocephppis, Orphusus spp. , Otiorrhynchus sulcatus, Cosmopolites sordidus, Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogoderma spp., Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinus spp., Giptusibbium psol. Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha, Amphimallon solstitialis, Costelytra zealandica, Lissorhoptrus oryzophilus.
From the order of the Hymenoptera z. B. Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp.
From the order of the Diptera z. B. Aedes spp., Anopheles spp., Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphora erythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp., Gastrophilus spp., Hyppobosca spp., Stomox ., Oestrus spp., Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae, Tipula paludosa, Hylemyia spp., Liriomyza spp.
From the order of the Siphonaptera z. B. Xenopsylla cheopis, Ceratophyllus spp.
From the class of the Arachnida z. B. Scorpio maurus, Latrodectus mactans, Acarus siro, Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalommodes spp., I ., Chorioptes spp., Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp., Hemitarsonemus spp., Brevipalpus spp.

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

The compounds of formula (I) according to the invention are particularly noteworthy through an excellent effect against caterpillars, beetle larvae, spider mites, Aphids and leaf flies.

The substances according to the invention also show a very good one Duration of action, such as B. against the caterpillars of the cotton capsule worm (Heliothis virescens) or the caterpillars of the army worm (Spodoptera frugiperda).

The compounds according to the invention can optionally be used in certain Concentrations or application rates also as herbicides and microbicides, for example as fungicides, antifungals and bactericides. she can optionally also be used as intermediates or precursors for the synthesis use other active ingredients.

According to the invention, all plants and parts of plants can be treated. Under Plants are understood here as all plants and plant populations desired and undesirable wild plants or crops (including naturally occurring crops). Crop plants can be plants that are caused by conventional breeding and optimization methods or by biotechnological and obtained genetic engineering methods or combinations of these methods can be, including the transgenic plants and including by Plant variety rights of protectable or non-protectable plant varieties. Under Plant parts should include all above-ground and underground parts and organs of plants, how sprout, leaf, flower and root are understood, examples being leaves, Needles, stems, stems, flowers, fruiting bodies, fruits and seeds as well as roots, Bulbs and rhizomes are listed. The plant parts also include Crops and vegetative and generative propagation material, for example Cuttings, bulbs, rhizomes, offshoots and seeds.

The treatment of the plants and plant parts according to the invention with the Active substances take place directly or by influencing their environment, habitat or Storage room according to the usual treatment methods, e.g. B. by diving, spraying, Evaporation, atomization, scattering, spreading and in the case of propagation material, especially in the case of seeds, further by single or multi-layer coating.

The active ingredients can be converted into the usual formulations, such as Solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, impregnated with active ingredients Natural and synthetic substances as well as very fine encapsulation in polymeric substances.

These formulations are prepared in a known manner, e.g. B. by mixing of the active ingredients with extenders, i.e. liquid solvents and / or solid Carriers, if appropriate using surface-active agents, that is Emulsifiers and / or dispersants and / or foaming agents.

In the case of the use of water as an extender, e.g. B. also organic Solvents are used as auxiliary solvents. As a liquid solvent essentially come into question: aromatics, such as xylene, toluene, or Alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as Chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, e.g. B. petroleum fractions, mineral and vegetable Oils, alcohols such as butanol or glycol and their ethers and esters, ketones such as Acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar Solvents such as dimethylformamide and dimethyl sulfoxide, and water.

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

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

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

The formulations generally contain between 0.1 and 95% by weight Active ingredient, preferably between 0.5 and 90%.

The active compounds according to the invention can be used as such or in their formulations also in a mixture with known fungicides, bactericides, acaricides, nematicides or insecticides can be used, e.g. B. the spectrum of activity broaden or prevent the development of resistance. In many cases you get it synergistic effects, d. H. the effectiveness of the mixture is greater than that Effectiveness of the individual components.

The following compounds, for example, are possible as mixing partners: fungicides aldimorph, ampropylfos, ampropylfos potassium, andoprim, anilazine, azaconazole, azoxystrobin,
Benalaxyl, benodanil, benomyl, benzamacril, benzamacrylic isobutyl, bialaphos, binapacrylic, biphenyl, bitertanol, blasticidin-S, bromuconazole, bupirimate, buthiobate,
Calcium polysulfide, carpropamide, capsimycin, captafol, captan, carbendazim, carboxin, carvone, quinomethionate (quinomethionate), chlobenthiazone, chlorfenazole, chloroneb, chloropicrin, chlorothalonil, chlozolinate, clozylacon, cufraneb, cymroconililanil
Debacarb, dichlorophene, diclobutrazole, diclofluanid, diclomezin, dicloran, diethofencarb, difenoconazole, dimethirimol, dimethomorph, diniconazole, diniconazol-M, dinocap, diphenylamine, dipyrithione, ditalimfos, dithorphoxin, dithorphononodine,
Ediphenphos, Epoxiconazole, Etaconazole, Ethirimol, Etridiazole,
Famoxadone, fenapanil, fenarimol, fenbuconazole, fenfuram, fenhexamid, fenitropan, fenpiclonil, fenpropidin, fenpropimorph, fentin acetate, fentin hydroxide, ferbam, ferimzon, fluazinam, flumetover, fluoromid, fluquinconazol, flurprimidololol, flurprimidolanilus, flurprimidololol, flurprimidololol, flurprimidololol, flurprimidololol, flurprimidololol, flurprimidololol, flurprimidololol, flurprimidololol, flurprimidololol, flurprimidololol, flurprimidololol, flurprimidolutolol Alminium, fosetyl sodium, fthalide, fuberidazole, furalaxyl, furametpyr, furcarbonil, furconazole, furconazole-cis, furmecyclox, guazatin,
Hexachlorobenzene, hexaconazole, hymexazole,
Imazalil, Imibenconazol, Iminoctadin, Iminoctadinealbesilat, Iminoctadinetriacetat, Iodocarb, Ipconazol, Iprobefos (IBP), Iprodione, Iprovalicarb, Irumamycin, Isoprothiolan, Isovaledione,
Kasugamycin, Kresoxim-methyl, copper preparations, such as: copper hydroxide, copper naphthenate, copper oxychloride, copper sulfate, copper oxide, oxine-copper and Bordeaux mixture,
Mancopper, Mancozeb, Maneb, Meferimzone, Mepanipyrim, Mepronil, Metalaxyl, Metconazol, Methasulfocarb, Methfuroxam, Metiram, Metomeclam, Metsulfovax, Mildiomycin, Myclobutanil, Myclozolin,
Nickel dimethyldithiocarbamate, nitrothal isopropyl, Nuarimol,
Ofurace, Oxadixyl, Oxamocarb, Oxolinicacid, Oxycarboxim, Oxyfenthiin,
Paclobutrazol, pefurazoate, penconazole, pencycuron, phosdiphen, picoxystrobin, PIMARICIN, piperalin, polyoxin, Polyoxorim, probenazole, prochloraz, procymidone, propamocarb, Propanosine sodium, propiconazole, propineb, pyraclostrobin, Pyrazohos, pyrifenox, pyrimethanil, pyroquilon, Pyroxyfur,
Quinconazole, quintozen (PCNB), quinoxyfen,
Sulfur and sulfur preparations, spiroxamines,
Tebuconazole, tecloftalam, tecnazene, Tetcyclacis, tetraconazole, thiabendazole, Thicyofen, Thifluzamide, thiophanate-methyl, thiram, Tioxymid, tolclofos-methyl, tolylfluanid, triadimefon, triadimenol, Triazbutil, triazoxide, Trichlamid, tricyclazole, tridemorph, trifloxystrobin, triflumizole, triforine, triticonazole,
Uniconazole, validamycin A, vinclozolin, viniconazole,
Zarilamid, Zineb, Ziram as well
Dagger G, OK-8705, OK-8801,
α- (1,1-dimethylethyl) -β- (2-phenoxyethyl) -1H-1,2,4-triazole-1-ethanol,
α- (2,4-dichlorophenyl) -β-fluoro-β-propyl-1H-1,2,4-triazole-1-ethanol,
α- (2,4-dichlorophenyl) -β-methoxy-α-methyl-1H-1,2,4-triazole-1-ethanol,
α- (5-methyl-1,3-dioxan-5-yl) -β - [[4- (trifluoromethyl) phenyl] methylene] -1H-1,2,4-triazol-1-ethanol,
(5RS, 6RS) -6-hydroxy-2,2,7,7-tetramethyl-5- (1H-1,2,4-triazol-1-yl) -3-octanone,
(E) -α- (methoxyimino) -N-methyl-2-phenoxy-phenylacetamide,
1- (2,4-dichlorophenyl) -2- (1H-1,2,4-triazol-1-yl) -ethanone-O- (phenylmethyl) oxime,
1- (2-methyl-1-naphthalenyl) -1H-pyrrole-2,5-dione,
1- (3,5-dichlorophenyl) -3- (2-propenyl) -2,5-pyrrolidinedione,
1 - [(diiodomethyl) sulphonyl] -4-methylbenzene,
1 - [[2- (2,4-dichlorophenyl) -1,3-dioxolan-2-yl] methyl] -1H-imidazole,
1 - [[2- (4-chlorophenyl) -3-phenyloxiranyl] methyl] -1H-1,2,4-triazole,
1- [1- [2 - [(2,4-dichlorophenyl) methoxy] phenyl] ethenyl] -1H-imidazole,
1-methyl-5-nonyl-2- (phenylmethyl) -3-pyrrolidinol,
2 ', 6'-dibromo-2-methyl-4'-trifluoromethoxy-4'-trifluoromethyl-1,3-thiazole-5-carboxanilide,
2,6-dichloro-5- (methylthio) -4-pyrimidinyl thiocyanate,
2,6-dichloro-N- (4-trifluoromethylbenzyl) -benzamide,
2,6-dichloro-N - [[4- (trifluoromethyl) phenyl] methyl] benzamide,
2- (2,3,3-triiodo-2-propenyl) -2H-tetrazole,
2 - [(1-methylethyl) sulphonyl] -5- (trichloromethyl) -1,3,4-thiadiazole,
2 - [[6-Deoxy-4-O- (4-O-methyl-β-D-glycopyranosyl) -α-D-glucopyranosyl] amino] -4- methoxy-1H-pyrrolo [2,3-d] pyrimidine-5-carbonitrile,
2-aminobutane,
2-bromo-2- (bromomethyl) -pentandinitril,
2-chloro-N- (2,3-dihydro-1,1,3-trimethyl-1H-inden-4-yl) -3-pyridine carboxamide,
2-chloro-N- (2,6-dimethylphenyl) -N- (isothiocyanatomethyl) -acetamide,
2-phenylphenol (OPP),
3,4-dichloro-1- [4- (difluoromethoxy) phenyl] -1H-pyrrole-2,5-dione,
3,5-dichloro-N- [cyano [(1-methyl-2-propynyl) -oxy] -methyl] -benzamide,
3- (1,1-dimethylpropyl-1-oxo-1H-indene-2-carbonitrile,
3- [2- (4-chlorophenyl) -5-ethoxy-3-isoxazolidinyl] -pyridine,
4-chloro-2-cyano-N, N-dimethyl-5- (4-methylphenyl) -1H-imidazol-1-sulfonamide,
4-methyl-tetrazolo [1,5-a] quinazolin-5 (4H) -one,
8-hydroxyquinoline sulfate,
9H-xanthene-9-carboxylic acid 2 - [(phenylamino) carbonyl] hydrazide,
bis (1-methylethyl) -3-methyl-4 - [(3-methylbenzoyl) oxy] -2,5-thiophene dicarboxylate,
cis-1- (4-chlorophenyl) -2- (1H-1,2,4-triazol-1-yl) cycloheptanol,
cis-4- [3- [4- (1,1-dimethylpropyl) -phenyl-2-methylpropyl] -2,6-dimethyl-morpholine,
Ethyl - [(4-chlorophenyl) azo] cyanoacetate,
potassium bicarbonate,
Methantetrathiol sodium salt,
Methyl-1- (2,3-dihydro-2,2-dimethyl-1H-inden-1-yl) -1H-imidazole-5-carboxylate,
Methyl-N- (2,6-dimethylphenyl) -N- (5-isoxazolylcarbonyl) -DL-alaninate,
Methyl N- (chloroacetyl) -N- (2,6-dimethylphenyl) -DL-alaninate,
N- (2,6-dimethylphenyl) -2-methoxy-N- (tetrahydro-2-oxo-3-furanyl) acetamide,
N- (2,6-dimethylphenyl) -2-methoxy-N- (tetrahydro-2-oxo-3-thienyl) acetamide,
N- (2-chloro-4-nitrophenyl) -4-methyl-3-nitro-benzenesulfonamide,
N- (4-Cyclohexylphenyl) -1,4,5,6-tetrahydro-2-pyrimidinamine,
N- (4-hexylphenyl) -1,4,5,6-tetrahydro-2-pyrimidinamine,
N- (5-chloro-2-methylphenyl) -2-methoxy-N- (2-oxo-3-oxazolidinyl) -acetamide,
N- (6-methoxy) -3-pyridinyl) -cyclopropanecarboxamide,
N- [2,2,2-trichloro-1 - [(chloroacetyl) -amino] -ethyl] -benzamide,
N- [3-chloro-4,5-bis- (2-propynyloxy) -phenyl] -N'-methoxy-methanimidamid,
N-formyl-N-hydroxy-DL-alanine-sodium salt,
O, O-diethyl [2- (dipropylamino) -2-oxoethyl] -ethylphosphoramidothioat,
O-methyl-S-phenyl-phenylpropylphosphoramidothioate,
S-Methyl-1,2,3-benzothiadiazole-7-carbothioate,
spiro [2H] -1-benzopyran-2,1 '(3'H) -isobenzofuran] -3'-one,
4- [3,4-dimethoxyphenyl) -3- (4-fluorophenyl) acryloyl] morpholine bactericidal bronopol, dichlorophene, nitrapyrin, nickel dimethyldithiocarbamate, kasugamycin, octhilinone, furan carboxylic acid, oxytetracycline, probenazole, streptomycin, tecloftalam and others, copper sulfate copper preparations. Insecticides / Acaricides / Nematicides Abamectin, Acephate, Acetamiprid, Acrinathrin, Alanycarb, Aldicarb, Aldoxycarb, Alpha-cypermethrin, Alphamethrin, Amitraz, Avermectin, AZ 60541, Azadirachtin, Azamethiphos, Azinphos M, Azinphos M,
Bacillus popilliae, Bacillus sphaericus, Bacillus subtilis, Bacillus thuringiensis, Baculoviruses, Beauveria bassiana, Beauveria tenella, Bendiocarb, Benfuracarb, Bensultap, Benzoximate, Betacyfluthrin, Bifenazate, Bifenthrin, Bioethanomifhrin, Bethenomifhrin, Bethenomifhrin, Bethanomifhrin , Butocarboxime, butylpyridaben,
Cadusafos, Carbaryl, Carbofuran, Carbophenothion, Carbosulfan, Cartap, Chloethocarb, Chlorethoxyfos, Chlorfenapyr, Chlorfenvinphos, Chlorfluazuron, Chlormephos, Chlorpyrifos, Chlorpyrifos M, Chlovaporthrin, Chromafenozide, Cis-Resmethrhrhrin, Clofethenethrin, Clofethenethrin, Clispethethrin, Cispocetine Thrin, Clispethethrin, Cispocetine Thrin, Clispethethrin, Clispethethrin, Cispocetine Thrin, Clispethethrin, Cispocetine Thrin, Clispethethrin, Clispethethrin, Cispocetine Thrin, Clispethethrin, Clispethethrin, Cispocetine Thrin, Clispethethrin, Clispethethrin, Cispocetine Thrin, Clispethethrin, Clispethethrin, Clispethethrin, Clispethethrin, Cispocetine Carbin , Cycloprothrin, cyfluthrin, cyhalothrin, cyhexatin, cypermethrin, cyromazine,
Deltamethrin, Demeton M, Demeton S, Demeton-S-methyl, Diafenthiuron, Diazinon, Dichlorvos, Dicofol, Diflubenzuron, Dimethoat, Dimethylvinphos, Diofenolan, Disulfoton, Docusat-sodium, Dofenapyn,
Eflusilanate, Emamectin, Empenthrin, Endosulfan, Entomopfthora spp., Esfenvalerate, Ethiofencarb, Ethion, Ethoprophos, Etofenprox, Etoxazole, Etrimfos,
Fenamiphos, Fenazaquin, Fenbutatin oxide, Fenitrothion, Fenothiocarb, Fenoxacrim, Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyrithrin, Fenpyroximate, Fenvalerate, Fipronil, Fluazuron, Flubrocythrinate, Flucycloxuron, Flytoxhrhrininate, Fumetoxinhrinate, Foncythrinate, Foncythrinate, Foncythrinate, Foncythrininate, Fonetoxin , Furathiocarb,
granulosis
Halofenozide, HCH, Heptenophos, Hexaflumuron, Hexythiazox, Hydroprene,
Imidacloprid, indoxacarb, isazofos, isofenphos, isoxathion, ivermectin,
nucleopolyhedroviruses
Lambda cyhalothrin, lufenuron
Malathion, Mecarbam, Metaldehyde, Methamidophos, Metharhician anisopliae, Metharhician flavoviride, Methidathione, Methiocarb, Methoprene, Methomyl, Methoxyfenozide, Metolcarb, Metoxadiazone, Mevinphos, Milbemectin, Milbemycin, Monocrotophos,
Naled, Nitenpyram, Nithiazine, Novaluron
Omethoate, oxamyl, oxydemethone M
Paecilomyces fumosoroseus, Parathion A, Parathion M, Permethrin, Phenthoat, Phorat, Phosalone, Phosmet, Phosphamidon, Phoxim, Pirimicarb, Pirimiphos A, Pirimiphos M, Profenofos, Promecarb, Propargite, Propoxur, Prothiofos, Prothrohrinos, Pothrohrinos, Pothrohrinos, Pothrohrinos , Pyridaben, pyridathione, pyrimidifen, pyriproxyfen,
Quinalphos, ribavirin,
Salithion, Sebufos, Silafluofen, Spinosad, Spirodiclofen, Sulfotep, Sulprofos,
Tau-fluvalinate, tebufenozide, tebufenpyrad, Tebupirimiphos, teflubenzuron, tefluthrin, temephos, Temivinphos, terbufos, tetrachlorvinphos, tetradifon, Thetacypermethrin, thiacloprid, thiamethoxam, Thiapronil, Thiatriphos, oxalate hydrogen thiocyclam, thiodicarb, thiofanox, thuringiensin, Tralocythrin, tralomethrin, triarathene, Triazamate, triazophos, triazuron, trichlophenidines, trichlorfon, triflumuron, trimethacarb,
Vamidothion, Vaniliprole, Verticillium lecanii
YI 5302, zeta-cypermethrin, zolaprofos
(1R-cis) - [5- (phenylmethyl) -3-furanyl] methyl-3 - [(dihydro-2-oxo-3 (2H) furanylidene) methyl] -2,2-dimethylcyclopropane carboxylate
(3-phenoxyphenyl) methyl-2,2,3,3-tetramethylcyclopropanecarboxylat
1 - [(2-Chloro-5-thiazolyl) methyl] tetrahydro-3,5-dimethyl-N-nitro-1,3,5-triazine-2 (1H) - imine
2- (2-chloro-6-fluorophenyl) -4- [4- (1,1-dimethylethyl) phenyl] -4,5-dihydro-oxazol
2- (Acetlyoxy) -3-dodecyl-1,4-naphthalenedione
2-chloro-N - [[[4- (1-phenylethoxy) phenyl] amino] carbonyl] -benzamide
2-chloro-N - [[[4- (2,2-dichloro-1,1-difluoroethoxy) phenyl] amino] carbonyl] -benzamide
3-methylphenyl propylcarbamate
4- [4- (4-ethoxyphenyl) -4-methylpentyl] -1-fluoro-2-phenoxy-benzene
4-Chloro-2- (1,1-dimethylethyl) -5 - [[2- (2,6-dimethyl-4-phenoxyphenoxy) ethyl] thio] - 3 (2H) pyridazinone
4-chloro-2- (2-chloro-2-methylpropyl) -5 - [(6-iodo-3-pyridinyl) methoxy] -3 (2H) - pyridazinone
4-chloro-5 - [(6-chloro-3-pyridinyl) methoxy] -2- (3,4-dichlorophenyl) -3 (2H) -pyridazinone
Bacillus thuringiensis strain EG-2348
Benzoic acid [2-benzoyl-1- (1,1-dimethylethyl) hydrazide
Butanoic acid 2,2-dimethyl-3- (2,4-dichlorophenyl) -2-oxo-1-oxaspiro [4.5] dec-3-en-4-yl ester
[3 - [(6-chloro-3-pyridinyl) methyl] -2-thiazolidinylidene] -cyanamide
Dihydro-2- (nitromethylene) -2H-1,3-thiazine-3 (4H) -carboxaldehyde
Ethyl [2 - [[1,6-dihydro-6-oxo-1- (phenylmethyl) -4-pyridazinyl] oxy] ethyl] carbamate
N- (3,4,4-trifluoro-1-oxo-3-butenyl) -glycine
N- (4-chlorophenyl) -3- [4- (difluoromethoxy) phenyl] -4,5-dihydro-4-phenyl-1H-pyrazole-1-carboxamide
N - [(2-chloro-5-thiazolyl) methyl] -N'-methyl-N "-nitro-guanidine
N-methyl-N '- (1-methyl-2-propenyl) -1,2-hydrazindicarbothioamid
N-methyl-N'-2-propenyl-1,2-hydrazindicarbothioamid
O, O-diethyl [2- (dipropylamino) -2-oxoethyl] -ethylphosphoramidothioat
N-cyanomethyl-4-trifluoromethyl-nicotinamide
3,5-dichloro-1- (3,3-dichloro-2-propenyloxy) -4- [3- (5-trifluoromethylpyridin-2-yloxy) propoxy] benzene

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

When used as insecticides, the active compounds according to the invention can also be used in their commercial formulations and in those formulations prepared application forms in a mixture with synergists. synergists are compounds that increase the effectiveness of the active ingredients without the added synergist itself must be active.

The active substance content of those prepared from the commercially available formulations Application forms can vary widely. The drug concentration of the Use forms can be from 0.0000001 to 95% by weight of active compound, preferably are between 0.0001 and 1% by weight.

The application takes place in a customary manner adapted to the application forms Wise.

When used against hygiene and storage pests, the Active ingredient through an excellent residual effect on wood and clay as well as through good stability to alkali on limed substrates.

As already mentioned above, according to the invention all plants and their parts can be treated. In a preferred embodiment, go wild occurring or by conventional organic breeding methods, such as crossing or Protoplast fusion obtained plant species and plant varieties and their parts treated. In a further preferred embodiment, transgenic plants and Plant varieties that may be in genetic engineering methods Combination with conventional methods were obtained (Genetic Modified Organisms) and treated their parts. The term "parts" or "parts of plants" or "Plant parts" was explained above.

Plants of the commercially available in each case are particularly preferred according to the invention or plant varieties in use. Among plant varieties is understood to mean plants with new properties ("traits") that are characterized by both conventional breeding, by mutagenesis or by recombinant DNA Techniques have been bred. These can be varieties, bio and genotypes.

Depending on the plant species or plant varieties, their location and Growth conditions (soils, climate, growing season, nutrition) can be determined by the Treatment according to the invention also results in superadditive (“synergistic”) effects. So are, for example, reduced application rates and / or extensions of the Spectrum of activity and / or an enhancement of the effect of the invention usable substances and agents, better plant growth, increased tolerance against high or low temperatures, increased tolerance to drought or against water or soil salt content, increased flowering performance, easier harvesting, Acceleration of ripeness, higher crop yields, higher quality and / or higher Nutritional value of the harvested products, higher shelf life and / or workability of the harvested products possible, which have the expected effects go out.

Among the preferred transgenic (genetic engineering received) plants or plant varieties include all plants by the genetic engineering modification received genetic material that this Gives plants special beneficial valuable properties ("traits"). Examples for such properties are better plant growth, increased tolerance against high or low temperatures, increased tolerance to drought or against water or soil salt content, increased flowering performance, easier harvesting, Acceleration of ripeness, higher crop yields, higher quality and / or higher Nutritional value of the harvested products, higher shelf life and / or workability of the harvested products. Further and particularly highlighted examples of such Properties are an increased defense against plants and animals microbial pests, such as insects, mites, phytopathogenic fungi, Bacteria and / or viruses and an increased tolerance of the plants to certain herbicidal active ingredients. The important ones are examples of transgenic plants Crops, such as cereals (wheat, rice), corn, soybeans, potatoes, cotton, Rapeseed and fruit plants (with the fruits apples, pears, citrus fruits and Grapes) mentioned, especially corn, soybeans, potatoes, cotton and rapeseed be highlighted. As properties ("traits") become special highlighted the increased defense of plants against insects by in the Plant-derived toxins, especially those caused by the genetic material from Bacillus thuringiensis (e.g. by the genes CryIA (a), CryIA (b), CryIA (c), CryIIA, CryIIIA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb and CryIF as well as their Combinations) are generated in the plants (hereinafter "Bt plants"). As Properties ("traits") are also particularly emphasized the increased defense of plants against fungi, bacteria and viruses by systemic acquirers Resistance (SAR), systemin, phytoalexins, elicitors and resistance genes and appropriately expressed proteins and toxins. As traits further emphasized the increased tolerance of plants certain herbicidal active ingredients, for example imidazolinones, Sulfonylureas, glyphosate or phosphinotricin (e.g. "PAT" gene). The each the desired properties ("traits") conferring genes can also in Combinations with each other occur in the transgenic plants. As examples of "Bt Plants "are maize, cotton, soy and potato under the trade names YIELD GARD® (e.g. maize, Cotton, soy), KnockOut® (e.g. maize), StarLink® (e.g. maize), Bollgard® (Cotton), Nucotn® (cotton) and NewLeaf® (potato). Examples of herbicide-tolerant plants are maize, cotton and Soybeans known as Roundup Ready® (Tolerance to glyphosates e.g. corn, cotton, soy), Liberty Link® (tolerance against phosphinotricin, e.g. Rape), IMI® (tolerance to imidazolinones) and STS® (Tolerance to sulfonylureas e.g. maize). As a herbicide resistant (conventionally grown to herbicide tolerance) plants are also the varieties sold under the name Clearfield® (e.g. maize). Of course, these statements also apply to future developed or future plant varieties with these or in the future developed genetic traits.

The plants listed can be particularly advantageous according to the invention with the Compounds of the general formula (I) or those according to the invention Active ingredient mixtures are treated. The above for the active ingredients or mixtures Preferred ranges given also apply to the treatment of these plants. Plant treatment with those in the present text should be particularly emphasized Specially listed compounds or mixtures.

The active compounds according to the invention act not only against pests from plants, hygiene and stored products, but also in the veterinary sector against animal parasites (ectoparasites) such as tick ticks, leather ticks, mites, running mites, flies (stinging and licking), parasitic fly larvae, lice, hair lice, Featherlings and fleas. These parasites include:
From the order of the Anoplurida z. B. Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp.
From the order of the Mallophagida and the subordinates Amblycerina and Ischnocerina z. B. Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp., Trichodectes spp., Felicola spp.
From the order Diptera and the subordinates Nematocerina and Brachycerina z. B. Aedes spp., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp., Chrysops spp., Hybomitra spp., Atylotus spp., Tabanus spp., Haematopota spp., Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fannia spp., Glossina spp., Calliphora spp., Lucilia spp., Chrysomyia spp ., Wohlfahrtia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp., Gasterophilus spp., Hippobosca spp., Lipoptena spp., Melophagus spp.
From the order of the Siphonapterida z. B. Pulex spp., Ctenocephalides spp., Xenopsylla spp., Ceratophyllus spp.
From the order of the Heteropterida z. B. Cimex spp., Triatoma spp., Rhodnius spp., Panstrongylus spp.
From the order of the Blattarida z. B. Blatta orientalis, Periplaneta americana, Blattela germanica, Supella spp.
From the subclass of Acaria (Acarida) and the orders of the Meta and Mesostigmata z. B. Argas spp., Ornithodorus spp., Otobius spp., Ixodes spp., Amblyomma spp., Boophilus spp., Dermacentor spp., Haemophysalis spp., Hyalomma spp., Rhipicephalus spp., Dermanyssus spp., Raillietia spp. Pneumonyssus spp., Sternostoma spp., Varroa spp.
From the order of the Actinedida (Prostigmata) and Acaridida (Astigmata) z. B. Acarapis spp., Cheyletiella spp., Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes spp. Pterolichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp., Laminosioptes spp.

The active compounds of the formula (I) according to the invention are also suitable for combating of arthropods, the farm animals, such as. B. cattle, sheep, goats, Horses, pigs, donkeys, camels, buffaloes, rabbits, chickens, turkeys, ducks, geese, Bees, other pets such as B. dogs, cats, house birds, aquarium fish as well as so-called experimental animals, such as. B. hamsters, guinea pigs, rats and Infest mice. By fighting these arthropods, deaths and Reductions in performance (for meat, milk, wool, skins, eggs, honey, etc.) can be reduced, so that by using the active compounds according to the invention more economical and easier animal husbandry is possible.

The active compounds according to the invention are used in the veterinary sector in in a known manner by enteral administration in the form of, for example, tablets, Capsules, watering, drenching, granules, pastes, boluses, the feed-through process, suppositories, by parenteral administration, such as by injections (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.), implants, through nasal Application, by dermal application in the form of, for example, diving or Bathing (dipping), spraying (spray), pouring (pour-on and spot-on), des Washing, powdering and with the help of shaped articles containing active ingredients, such as Collars, ear tags, tail tags, limb straps, holsters, Marking devices etc.

When used for cattle, poultry, pets etc., you can use the active ingredients in Formula (I) as formulations (for example powders, emulsions, flowable Agents), which contain the active ingredients in an amount of 1 to 80 wt .-%, directly or after 100 to 10,000-fold dilution or use it as a chemical bath use.

It was also found that the compounds of the invention have a high Show insecticidal activity against insects that destroy technical materials.

The following insects may be mentioned by way of example and preferably, but without limitation:
Beetle like
Hylotrupes bajulus, Chlorophorus pilosis, Anobium punctatum, Xestobium rufovillosum, Ptilinus pecticornis, Dendrobium pertinex, Ernobius mollis, Priobium carpini, Lyctus brunneus, Lyctus africanus, Lyctus planicollis, Lyctus linearesces, Lyctus pubis linearis, speculum Tryptodendron spec. Apate monachus, Bostrychus capucins, Heterobostrychus brunneus, Sinoxylon spec. Dinoderus minutus.
Skin wing like
Sirex juvencus, Urocerus gigas, Urocerus gigas taignus, Urocerus augur.
Termites like
Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicola, Reticulitermes flavipes, Reticulitermes santonensis, Reticulitermes lucifugus, Mastotermes darwiniensis, Zootermopsis nevadensis, Coptotermes formosanus.
Bristle tails such as Lepisma saccharina.

In the present context, technical materials include non-living ones Understand materials, such as preferably plastics, adhesives, glues, papers and cardboard, leather, wood, wood processing products and paints.

The one to be protected against insect attack is very particularly preferably Material around wood and wood processing products.

Wood and wood processing products that can be protected by the agent according to the invention or mixtures containing it are to be understood as examples:
Lumber, wooden beams, railway sleepers, bridge parts, jetties, wooden vehicles, boxes, pallets, containers, telephone poles, wooden cladding, wooden windows and doors, plywood, chipboard, carpentry or wooden products that are generally used in house construction or joinery.

The active ingredients can be used as such, in the form of concentrates or in general usual formulations such as powders, granules, solutions, suspensions, Emulsions or pastes can be applied.

The formulations mentioned can be prepared in a manner known per se be, e.g. B. by mixing the active ingredients with at least one solution or Diluents, emulsifiers, dispersants and / or binders or fixatives, Water repellants, possibly desiccants and UV stabilizers and optionally dyes and pigments and other processing aids.

The insecticidal agents or used to protect wood and wood-based materials Concentrates contain the active ingredient according to the invention in a concentration of 0.0001 to 95% by weight, in particular 0.001 to 60% by weight.

The amount of the agents or concentrates used depends on the type and the Occurrence of insects and depending on the medium. The optimal amount to use can be determined by test series in the application. In general however, it is sufficient 0.0001 to 20% by weight, preferably 0.001 to 10% by weight, of the active ingredient, based on the material to be protected.

An organic chemical is used as the solvent and / or diluent Solvent or solvent mixture and / or an oily or oily heavy volatile organic chemical solvent or solvent mixture and / or a polar organic chemical solvent or solvent mixture and / or water and optionally an emulsifier and / or wetting agent.

The organic chemical solvents used are preferably oily or oily ones Solvents with an evaporation number above 35 and a flash point above 30 ° C, preferably above 45 ° C, used. As such volatile, Water-insoluble, oily and oily solvents become corresponding mineral oils or their aromatic fractions or mineral oil-containing solvent mixtures, preferably white spirit, petroleum and / or alkylbenzene used.

Mineral oils with a boiling range of 170 to 220 ° C are advantageous, White spirit with a boiling range of 170 to 220 ° C, spindle oil with a boiling range from 250 to 350 ° C, petroleum or aromatics with a boiling range from 160 to 280 ° C, Turpentine oil and the like.

In a preferred embodiment, liquid aliphatic Hydrocarbons with a boiling range of 180 to 210 ° C or high-boiling mixtures of aromatic and aliphatic hydrocarbons with a boiling range of 180 to 220 ° C and / or locker oil and / or monochloronaphthalene, preferably α-monochloronaphthalene used.

The organic non-volatile oily or oily solvents with a Evaporation number above 35 and a flash point above 30 ° C, preferably above 45 ° C, can be caused in part by easily or moderately volatile organic chemical solvents are replaced, provided that Solvent mixture also has an evaporation number above 35 and a flash point above 30 ° C, preferably above 45 ° C, and that the insecticide fungicide Mixture is soluble or emulsifiable in this solvent mixture.

According to a preferred embodiment, part of the organic chemical Solvent or solvent mixture or an aliphatic polar organic chemical solvent or solvent mixture replaced. Preferably come aliphatic containing hydroxyl and / or ester and / or ether groups organic chemical solvents such as glycol ether, ester or the like. to use.

As organic-chemical binders in the context of the present Invention known per se and / or used in the water-dilutable organochemical solvents soluble or dispersible or emulsifiable Synthetic resins and / or binding drying oils, in particular binders from or containing an acrylic resin, a vinyl resin, e.g. B. polyvinyl acetate, Polyester resin, polycondensation or polyaddition resin, polyurethane resin, Alkyd resin or modified alkyd resin, phenolic resin, hydrocarbon resin such as indene Coumarone resin, silicone resin, drying vegetable and / or drying oils and / or physically drying binders based on a natural and / or synthetic resin used.

The synthetic resin used as a binder can be in the form of an emulsion, dispersion or solution. Bitumen or bituminous substances up to 10 wt .-%, are used. In addition, in itself known dyes, pigments, water repellants, odor correctors and Inhibitors or anticorrosive agents and the like are used.

According to the invention, preference is given to at least one organic chemical binder an alkyd resin or modified alkyd resin and / or a drying vegetable Contain oil in the medium or in the concentrate. Are preferred according to the invention Alkyd resins with an oil content of more than 45% by weight, preferably 50 to 68% by weight.

The binder mentioned can be wholly or partly by a Fixing agent (mixture) or a plasticizer (mixture) can be replaced. These additions should volatilize the active ingredients and crystallize or precipitate prevent. They preferably replace 0.01 to 30% of the binder (based on 100% of the binder used).

The plasticizers come from the chemical classes of phthalic acid esters such as Dibutyl, dioctyl or benzyl butyl phthalate, phosphoric acid esters such as Tributyl phosphate, adipic acid esters such as di (2-ethylhexyl) adipate, stearates such as butyl stearate or amyl stearate, oleates such as butyl oleate, glycerol ether or higher molecular weight Glycol ether, glycerol ester and p-toluenesulfonic acid ester.

Fixing agents are chemically based on polyvinyl alkyl ethers such as. B. Polyvinyl methyl ether or ketones such as benzophenone, ethylene benzophenone.

Water is also particularly suitable as a solvent or diluent, optionally in a mixture with one or more of the above-mentioned organic chemical solvents or diluents, emulsifiers and dispersants.

A particularly effective wood protection is achieved through industrial impregnation processes, z. B. vacuum, double vacuum or printing process.

The ready-to-use agents can, if appropriate, still further insecticides and optionally contain one or more fungicides.

The additional mixing partners are preferably those in WO 94/29 268 Insecticides and fungicides mentioned in question. The ones mentioned in this document Connections are an integral part of this application.

Insecticides, such as chlorpyriphos, phoxime, silafluofin, alphamethrin, cyfluthrin, cypermethrin, deltamethrin, permethrin, imidacloprid, NI-25, flufenoxuron, hexaflumuron, transfluthrin, thiacloziduron, methoxyclopidon, trifluoride
as well as fungicides such as epoxyconazole, hexaconazole, azaconazole, propiconazole, tebuconazole, cyproconazole, metconazole, imazalil, dichlorofluoride, tolylfluanid, 3-iodo-2-propynylbutylcarbamate, N-octyl-isothiazolin-3-one and 4,5- -octyl-isothiazolin-3-one.

At the same time, the compounds according to the invention can protect against fouling objects, in particular hulls, sieves, nets, structures, Quayside and signal systems, which are connected with sea or brackish water come, be used.

Overgrowth by sessile oligochaetes, such as lime tube worms and by mussels and species of the Ledamorpha (barnacles) group, such as various Lepas and Scalpellum species, or by species from the group Balanomorpha (barnacles), such as Balanus or pollicipes species, increases the frictional resistance of ships and subsequently leads through increased energy consumption and moreover through frequent Dry dock stays for a significant increase in operating costs.

In addition to the growth by algae, for example Ectocarpus sp. and Ceramium sp., comes in particular the vegetation by sessile Entomostraken groups, which under the name Cirripedia (barnacles) special meaning too.

It has now surprisingly been found that the inventive Compounds alone or in combination with other active ingredients, an excellent Have antifouling effect.

By using compounds according to the invention alone or in combination with other active ingredients, can rely on the use of heavy metals such. B. in Bis (trialkyltin) sulfides, tri-n-butyltin laurate, tri-n-butyltin chloride, copper (I) oxide, Triethyltin chloride, tri-n-butyl (2-phenyl-4-chlorophenoxy) tin, tributyltin oxide, Molybdenum disulfide, antimony oxide, polymeric butyl titanate, Phenyl (bispyridine) bismuth chloride, tri-n-butyltin fluoride, manganese ethylene bisthiocarbamate, Zinc dimethyldithiocarbamate, zinc ethylene bisthiocarbamate, zinc and copper salts of 2-pyridinthiol-1- oxide, bisdimethyldithiocarbamoylzinkethylenististhiocarbamate, zinc oxide, copper (I) - ethylene bisdithiocarbamate, copper thiocyanate, copper naphthenate and Tributyltin halides or the concentration of these compounds be significantly reduced.

The ready-to-use antifouling paints can also be used if necessary Active ingredients, preferably algicides, fungicides, herbicides, molluscicides or others Contain antifouling ingredients.

Suitable combination partners for the antifouling agents according to the invention are preferably:
Algicides like
2-tert-butylamino-4-cyclopropylamino-6-methylthio-1,3,5-triazine, dichlorophene, diuron, endothal, fentin acetate, isoproturon, methabenzthiazuron, oxyfluorfen, quinoclamine and terbutryn;
Fungicides like
Benzo [b] thiophenecarboxylic acid cyclohexylamide-S, S-dioxide, dichlofluanid, fluorfolpet, 3-iodo-2-propynyl-butylcarbamate, tolylfluanid and azoles such as azaconazole, cyproconazole, epoxyconazole, hexaconazole, metconazole, propiconazole and ticon;
Molluscicides like
Fentin acetate, metaldehyde, methiocarb, niclosamide, thiodicarb and trimethacarb;
or conventional antifouling agents such as
4,5-dichloro-2-octyl-4-isothiazolin-3-one, diiodomethylparatrylsulfone, 2- (N, N-dimethylthiocarbamoylthio) -5-nitrothiazyl, potassium, copper, sodium and zinc salts of 2-pyridinthiol-1 -oxide, pyridine-triphenylborane, tetrabutyldistannoxane, 2,3,5,6-tetrachloro-4- (methylsulfonyl) pyridine, 2,4,5,6-tetrachloroisophthalonitrile, tetramethylthiuram disulfide and 2,4,6-trichlorophenylmaleimide.

The antifouling agents used contain the active ingredient according to the invention compounds according to the invention in a concentration of 0.001 to 50% by weight, in particular from 0.01 to 20% by weight.

The antifouling agents according to the invention also contain the usual ones Components such as B. in Ungerer, Chem. Ind. 1985, 37, 730-732 and Williams, Antifouling Marine Coatings, Noyes, Park Ridge, 1973.

Antifouling paints contain algicidal, fungicidal, molluscicides and insecticidal active substances according to the invention, in particular binders.

Examples of recognized binders are polyvinyl chloride in one Solvent system, chlorinated rubber in one solvent system, acrylic resins in one Solvent system especially in an aqueous system, Vinyl chloride / vinyl acetate copolymer systems in the form of aqueous dispersions or in the form of organic solvent systems, butadiene / styrene / acrylonitrile rubbers, drying oils, such as linseed oil, resin esters or modified hard resins in Combination with tar or bitumen, asphalt and epoxy compounds, low Amounts of chlorinated rubber, chlorinated polypropylene and vinyl resins.

Paints may also contain inorganic pigments, organic Pigments or dyes, which are preferably insoluble in sea water. Further Paints can contain materials, such as rosin, to be controlled To enable release of the active ingredients. The paintings can also Plasticizers, modifiers influencing the rheological properties, and contain other conventional ingredients. Also in self-polishing antifouling Systems can be the compounds of the invention or those mentioned above Mixtures can be incorporated.

The active ingredients are also suitable for controlling animal pests, in particular insects, arachnids and mites, which live in closed spaces, such as, for example, apartments, factory halls, offices, vehicle cabins and the like. occur. To combat these pests, they can be used alone or in combination with other active ingredients and auxiliaries in household insecticide products. They are effective against sensitive and resistant species and against all stages of development. These pests include:
From the order of the Scorpionidea z. B. Buthus occitanus.
From the order of Acarina z. B. Argas persicus, Argas reflexus, Bryobia spp., Dermanyssus gallinae, Glyciphagus domesticus, Ornithodorus moubat, Rhipicephalus sanguineus, Trombicula alfreddugesi, Neutrombicula autumnalis, Dermatophagoides pteronissimus, Dermatophagoides formae.
From the order of the Araneae z. B. Aviculariidae, Araneidae.
From the order of the Opiliones z. B. Pseudoscorpiones chelifer, Pseudoscorpiones cheiridium, Opiliones phalangium.
From the order of the Isopoda z. B. Oniscus asellus, Porcellio scaber.
From the order of the Diplopoda z. B. Blaniulus guttulatus, Polydesmus spp.
From the order of the Chilopoda z. B. Geophilus spp.
From the order of the Zygentoma z. B. Ctenolepisma spp., Lepisma saccharina, Lepismodes inquilinus.
From the order of the Blattaria z. B. Blatta orientalies, Blattella germanica, Blattella asahinai, Leucophaea maderae, Panchlora spp., Parcoblatta spp., Periplaneta australasiae, Periplaneta americana, Periplaneta brunnea, Periplaneta fuliginosa, Supella longipalpa.
From the order of the Saltatoria z. B. Acheta domesticus.
From the order of the Dermaptera z. B. Auricular Forficula.
From the order of the Isoptera z. B. Kalotermes spp., Reticulitermes spp.
From the order of Psocoptera z. B. Lepinatus spp., Liposcelis spp.
From the order of the Coleptera z. B. Anthrenus spp., Attagenus spp., Dermestes spp., Latheticus oryzae, Necrobia spp., Ptinus spp., Rhizopertha dominica, Sitophilus granarius, Sitophilus oryzae, Sitophilus zeamais, Stegobium paniceum.
From the order of the Diptera z. B. Aedes aegypti, Aedes albopictus, Aedes taeniorhynchus, Anopheles spp., Calliphora erythrocephala, Chrysozona pluvialis, Culex quinquefasciatus, Culex pipiens, Culex tarsalis, Drosophila spp., Fannia canicularis. , Stomoxys calcitrans, Tipula paludosa.
From the order of the Lepidoptera z. B. Achroia grisella, Galleria mellonella, Plodia interpunctella, Tinea cloacella, Tinea pellionella, Tineola bisselliella.
From the order of the Siphonaptera z. B. Ctenocephalides canis, Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis.
From the order of the Hymenoptera z. B. Camponotus herculeanus, Lasius fuliginosus, Lasius niger, Lasius umbratus, Monomorium pharaonis, Paravespula spp., Tetramorium caespitum.
From the order of the Anoplura z. B. Pediculus humanus capitis, Pediculus humanus corporis, Phthirus pubis.
From the order of the Heteroptera z. B. Cimex hemipterus, Cimex lectularius, Rhodinus prolixus, Triatoma infestans.

The application in the field of household insecticides is carried out alone or in Combination with other suitable active ingredients such as phosphoric acid esters, carbamates, Pyrethroids, growth regulators or active ingredients from other known Classes of insecticides.

The application takes place in aerosols, unpressurized sprays, e.g. B. Pump and Atomizer sprays, automatic fog machines, foggers, foams, gels, Vaporizer products with vaporizer platelets made of cellulose or plastic, liquid vaporizers, Gel and membrane evaporators, propeller-driven evaporators, energy-free or passive evaporation systems, moth papers, moth bags and Moth angels, as granules or dusts, in lures or bait stations.

The manufacture and use of the substances according to the invention are based on following examples.

Herstellunpsbeispiele example 1

18 g (40 mmol) tert-butyl-2- (4-chlorophenyl) -4- (2,6-difluorobenzoyl) -3-methyl-5-oxo 1-pyrrolidine carboxylate (II-1) are dissolved in 30 ml of glacial acetic acid and with a mixture of 30 ml of 50% sulfuric acid. Reflux for about 3 hours, cool and makes alkaline under ice cooling with 15% sodium hydroxide solution. Then extracted you get the product with dichloromethane and after evaporating the Solvent 8.6 g of crude product, which over silica gel in the system Cyclohexane / ethyl acetate (2: 1) is cleaned.

4.4 g (36% of theory) of 2- (4-chlorophenyl) -5- (2,6-difluorophenyl) -3-methyl-3,4-dihydro-2H-pyrrole are obtained with the logP ( pH 2.3) = 3.00. Example 2

1.0 g (3.72 mmol) 2- (4-chlorophenyl) -5- (2,6-difluorophenyl) -3-methyl-3,4-dihydro- 2H-pyrrole (Ex. 1) becomes a mixture of 1.01 g (4.90 mmol) 4- (trifluoromethoxy) phenylboronic acid, 3.48 g (13.1 mmol) tripotassium phosphate trihydrate, 14.68 mg (0.065 mmol) palladium (II) acetate and 48.8 mg of 2- (di-tert-butylphosphino) biphenyl added in 25 ml of tetrahydrofuran under argon. The mixture is heated with stirring Mixture for a total of 9 h at reflux, pour the reaction solution onto water and extracts the product with ethyl acetate. It is obtained after evaporation of the solvent 2.36 g of red oil, which by column chromatography in Cyclohexane / ethyl acetate (4: 1) is cleaned.

1.0 g (70.9% of theory) of 5- (2,6-difluorophenyl) -3-methyl-2- [4 '- (trifluoromethoxy) -1,1'-biphenyl-4- yl] -3,4-dihydro-2H-pyrrole, melting point 85-86 ° C. Example 3

Procedure (A)

12.3 g (24 mmol) tert-Butyl-2- (4-chlorophenyl) -4- (2,6-difluorobenzoyl) -5-oxo-3-phenyl-1-pyrrolidinecarboxylate (II-2) are concentrated in a solution of 20 ml Sulfuric acid, 20 ml water and 40 ml glacial acetic acid refluxed for 4 h. After cooling is made alkaline with sodium hydroxide solution and the product with dichloromethane extracted. The organic phase is washed over with water Magnesium sulfate dried and evaporated in vacuo. The remaining oil turns on Chromatograph silica gel with dichloromethane.

3.0 g (34.0% of theory) of 2- (4-chlorophenyl) -5- (2,6-difluorophenyl) -3- are obtained phenyl-3,4-dihydro-2H-pyrrole with the logP (pH 2.3) = 4.56.

Procedure (B)

4.1 g (8.4 mmol) tert-Butyl-1- (4-chlorophenyl) -4- (2,6-difluorophenyl) -4-oxo-2-phenylbutylcarbamate (III-1) are dissolved in 40 ml dichloromethane and at 0 ° C with 10 ml Trifluoroacetic acid added dropwise. After stirring for 16 h, neutralize with sodium bicarbonate solution and extracted with dichloromethane. The After drying over magnesium sulfate, the organic phase is evaporated in vacuo and the residue was chromatographed on silica gel with dichloromethane.

0.6 g (19.4% of theory) of oily 2- (4-chlorophenyl) -5- (2,6-difluorophenyl) -3-phenyl-3,4-dihydro-2H-pyrrole from logP are obtained (pH 2.3) = 4.16 / 4.56 (mixture of diastereomers). Example 4

To the reaction mixture of 0.587 g (3.26 mmol) 4- (isopropoxy) phenylboronic acid, 2.317 g (8.7 mmol) tripotassium phosphate trihydrate, 9.8 mg (0.043 mmol) Palladium (II) acetate and 32.5 mg (0.11 mol) of 2- (di-tert-butylphosphine) biphenyl in 25 ml Tetrahydrofuran is added 0.8 g (2.175 mol) of 2- (2,6-difluorophenyl) -4-phenyl-5- (4- chlorophenyl) -3,4-dihydro-2H-pyrrole and refluxed under argon for 16 h. After this After cooling, the mixture is poured onto water and the product is extracted Dichloromethane. After drying, the organic phase is concentrated Chromatograph the residue on silica gel with cyclohexane / ethyl acetate (4: 1).

0.39 g (38.4% of theory) of oily 5- (2,6-difluorophenyl) -2- (4'-isopropoxy-1,1'- biphenyl-4-yl) -3-phenyl-3,4-dihydro-2H-pyrrole with the log p (pH 2.3) = 5.55 and the logP (pH 7.5) = 5.77.

The following compounds of the formula (Ig) can be obtained analogously to that of Examples 1 to 4 and in accordance with the general regulations for the preparation of these substances:

Preparation of starting materials of the formula (II) Example II-1

To dissolve 10.4 g (33.57 mmol) of tert-butyl-2- (4-chlorophenyl) -3-methyl-5-oxo-1- pyrrolidine carboxylate (VIII-1) in 80 ml tetrahydrofuran and 5.8 ml Hexamethylphosphoric triamide is added dropwise with stirring at -50 ° C to 67.1 ml of a 1 molar solution of bis (trimethylsilyl) lithium amide. After 10 min -50 ° C 5.93 g (33.5 mmol) 2,6-difluorobenzoyl chloride, dissolved in 10 ml absolute Tetrahydrofuran, added dropwise. Allow to rise slowly to room temperature and diluted with water after stirring for 16 h. After acidification with diluted Hydrochloric acid, the product is extracted with dichloromethane. The organic phase will separated, dried over magnesium sulfate and concentrated.

15 g (about 100% of theory) of tert-butyl-2- (4-chlorophenyl) -4- (2,6-difluorobenzoyl) -3-methyl-5-oxo-1-pyrrolidinecarboxylate are obtained as an oily crude product with the logP (pH 2.3) = 4.44. Example II-2

A solution of 7.8 g (21 mmol) of tert-butyl-2- (4-chlorophenyl) -5-oxo-3-phenyl-1- pyrrolidine carboxylate (VIII-2) in 40 ml of absolute tetrahydrofuran and 4 ml Hexamethylphosphorsäuretriamid is under argon at -50 ° C with stirring with 42 ml a 1 molar solution of bis (trimethylsilyl) lithium amide was added. After 10 minutes 3.7 g (21 mmol) of 2,6-difluorobenzoyl chloride are added and the mixture slowly brought to room temperature. After stirring for 16 h, ice water is added the reaction mixture, acidifies with hydrochloric acid and extracts the product Ethyl acetate, the organic phase dries and concentrates.

12.4 g of crude tert-butyl-2- (4-chlorophenyl) -4- (2,6-difluorobenzoyl) -5-oxo-3-phenyl-1-pyrrolidinecarboxylate with a melting point of 54-56 ° C. and logP (pH 2.3) = 5.11 / 4.77 (mixture of diastereomers). Preparation of starting materials of the formula (III) Example III-1

To dissolve 1.8 g (15.4 mmol) 1,3-difluorobenzene in 35 ml absolute Tetrahydrofuran is added dropwise at -78 ° C with stirring 10.5 ml of a 1.6 molar n-butyllithium solution (in hexane). After stirring for 1 h at -78 ° C, 3.0 g (11 mmol) tert-Butyl-2- (4-chlorophenyl) -5-oxo-3-phenyl-1-pyrrolidinecarboxylate (VIII-2) in a little tetrahydrofuran, added dropwise. The mixture is left at -78 ° C. for 3 h and then for Stir for 16 h at room temperature. After the addition of saturated Ammonium chloride solution, the product is extracted with dichloromethane and washed the organic phase with water, which after drying over magnesium sulfate in the Vacuum is rotated.

4.3 g (80.4% of theory) of tert-butyl-1- (4-chlorophenyl) -4- (2,6-difluorophenyl) -4-oxo-2-phenylbutylcarbamate are obtained as a crude resin product with the logP (pH 2.3) = 4.63. Preparation of starting materials of the formula (VIII) Example VIII-1

To dissolve 15.0 g (71.54 mmol) of 5- (4-chlorophenyl) -4-methyl-2-pyrrolidinone (X-1) in 100 ml dichloromethane and 1 g 4-dimethylaminopyridine are added Stirring at 20 ° C 31.23 g (143.1 mmol) di- (tert-butyl) dicarbonate added and 2 h touched. After stirring, the reaction mixture is mixed with water for 16 h and the product extracted with dichloromethane. After drying and evaporating in the The crude product is vacuum on silica gel with cyclohexane / ethyl acetate (2: 1) chromatographed.

4.8 g (21.7% of theory) of oily tert-butyl-2- (4-chlorophenyl) -3-methyl-5-oxo-1-pyrrolidinecarboxylate with the logP (pH 2.3) = 3.25 / 3.31 (mixture of diastereomers). Example VIII-2

6.0 g (22.1 mmol) of 5- (4-chlorophenyl) -4-phenyl-2-pyrrolidinone (X-2) are dissolved in 50 ml Dimethylformamide dissolved and after adding 0.4 g (3.28 mmol) 4-Dimethylaminopyridine at 20 ° C with 10.6 g (48.6 mmol) of bis (tert-butyl) dicarbonate. To After stirring for 16 h, the reaction mixture is diluted with water and the product is sucked off failed product.

7.8 g (95% of theory) of tert-butyl-2- (4-chlorophenyl) -5-oxo-3-phenyl-1- are obtained pyrrolidine carboxylate with a melting point of 164 ° C.

The following compounds of the formula (VIII) can be obtained analogously to that of Examples VIII-1 and VIII-2 and in accordance with the general instructions for the preparation of these substances:




Preparation of starting materials of the formula (X) Example X-1

45.0 g (198.54 mmol) 4- (4-chlorophenyl) -3-methyl-4-oxobutanoic acid (see Eur. J. Med. 1993, 28, 129) are liquid in 680 ml of ethanol after adding 340 ml Ammonia and 5 g of Raney nickel at 150 ° C and 150 bar of hydrogen for 3 h. After cooling and filtering off the catalyst, the filtrate is concentrated with Water added and extracted with dichloromethane. Then the organic Phase dried over magnesium sulfate and concentrated in vacuo.

40 g of crude 5- (4-chlorophenyl) -4-methyl-2-pyrrolidinone are obtained with the logP (pH 2.3) = 1.85 / 1.92 (mixture of diastereomers). Example X-2

18 g (62.12 mmol) of 4-amino-4- (4-chlorophenyl) -3-phenylbutanoic acid (XI-1) are in 200 ml of xylene suspended and refluxed for 16 h. After cooling, the Solution filtered and the filtrate concentrated. The residue is on silica gel Chromatographed ethyl acetate.

12.3 g (yield 66.9% of theory) of 5- (4-chlorophenyl) -4-phenyl-2-pyrrolidinone are obtained from melting point 116 ° C and logP (pH 2.3) = 2.28 / 2.50 as Diastereomeric mixture.

The following compounds of the formula (X) can be obtained analogously to that of Examples X-1 and X-2 and in accordance with the general instructions for the preparation of these substances:




Preparation of starting materials of the formula (XI) Example XI-1

53.5 g (330 mmol) of methyl cinnamate and 91.74 g (300 mol) of N- (4-chlorobenzyl) - N (diphenylmethylene) amine as a toluene solution (see Example XIV-1), and 3.5 g of triethylbenzylammonium chloride (TEBA chloride) are mixed with 12 ml of 50% Sodium hydroxide solution was added and the mixture was stirred at 20 ° C. for 16 h. Then 122 ml of 30% is added Hydrochloric acid and 50 ml of water and this mixture is also stirred for 16 h. The white crystalline precipitate is filtered off and washed well with hot Washed ethyl acetate to remove free benzophenone.

41 g (47.2% of theory) of crude 4-amino-4- (4-chlorophenyl) -3-phenylbutanoic acid with the logP (pH 2.3) = 1.52 are obtained. Preparation of starting materials of the formula (XIV) Example XIV-1

54.7 g (300 mmol) of benzophenone and 42.5 g (300 mmol) of 4-chlorobenzylamine in 500 ml of toluene with the addition of 1 g of p-toluenesulfonic acid for 24 h Boiled water separator. The cooled reaction solution of the N- (4-chlorobenzyl) - N- (diphenylmethylene) amine is directly in the without further treatment subsequent reaction to produce the 4-amino-4- (4-chlorophenyl) -3- phenylbutanoic acid (XI-1) used.

The determination of those in the tables and manufacturing examples above specified logP values are carried out in accordance with EEC Directive 79/831 Annex V.A8 HPLC (High Performance Liquid Chromatography) on a phase reversal column (C 18). Temperature: 43 ° C.

The determination is made in the acidic range at pH 2.3 with 0.1% aqueous Phosphoric acid and acetonitrile as eluents; linear gradient from 10% acetonitrile to 90% acetonitrile. The values are marked in the tables with a).

The determination is made in the neutral range at pH 7.5 with 0.01 molar aqueous Phosphate buffer solution and acetonitrile as eluents; linear gradient of 10% Acetonitrile to 90% acetonitrile. The values are marked with b) in the tables.

The calibration is carried out with unbranched alkan-2-ones (with 3 to 16 Carbon atoms) whose logP values are known (determination of the logP values using the Retention times through linear interpolation between two successive Alkanones).

The lambda max values were determined using the UV spectra from 200 nm to 400 nm the maxima of the chromatographic signals determined.

applications Example A Heliothis armigera test

Solvent 7 parts by weight of dimethylformamide

Emulsifier: 2 parts by weight of alkylaryl polyglycol ether

To prepare a suitable preparation of active compound, mix 1 Part by weight of active ingredient with the stated amounts of solvent and emulsifier and dilute the concentrate with water containing emulsifier to the desired level Concentration.

Soybean shoots (Glycine max) are dipped into the active ingredient preparation desired concentration and treated with caterpillars of the cotton capsule worm (Heliothis armigera) occupied while the leaves are still moist.

After the desired time, the kill is determined in%. 100% means that all caterpillars have been killed; 0% means that no caterpillars are killed were.

In this test, e.g. B. the following compounds of the preparation examples have good activity: Table A plant-damaging insects Heliothis armigera test

Example B Phaedon larvae test

Solvent: 7 parts by weight of dimethylformamide

Emulsifier: 2 parts by weight of alkylaryl polyglycol ether

To prepare a suitable preparation of active compound, mix 1 Part by weight of active ingredient with the stated amounts of solvent and emulsifier and dilute the concentrate to the desired level with water containing emulsifier Concentration.

Cabbage leaves (Brassica oleracea) are dipped into the active ingredient preparation the desired concentration and treated with larvae of the horseradish leaf beetle (Phaedon cochleariae) occupied while the leaves are still moist.

After the desired time, the kill is determined in%. 100% means that all beetle larvae have been killed; 0% means that no beetle larvae were killed.

In this test, e.g. B. the following compounds of the preparation examples good activity: Table B plant-damaging insects Phaedon larva test

Table B plant-damaging insect Phaedon larva test

Example C Plutella Test

Solvent: 7 parts by weight of dimethylformamide

Emulsifier: 2 parts by weight of alkylaryl polyglycol ether

To prepare a suitable preparation of active compound, mix 1 Part by weight of active ingredient with the stated amounts of solvent and emulsifier and dilute the concentrate with water containing emulsifier to the desired level Concentration.

Cabbage leaves (Brassica oleracea) are dipped into the active ingredient preparation of the desired concentration and treated with caterpillars (Plutella xylostella) as long as the leaves are still moist.

After the desired time, the kill is determined in%. 100% means that all caterpillars have been killed; 0% means that no caterpillars are killed were.

In this test, e.g. B. the following compounds of the preparation examples good activity: Table C plant-damaging insects Plutella larva test

Example D Spodoptera exigua test

Solvent: 7 parts by weight of dimethylformamide

Emulsifier: 2 parts by weight of alkylaryl polyglycol ether

To prepare a suitable preparation of active compound, mix 1 Part by weight of active ingredient with the stated amounts of solvent and emulsifier and dilute the concentrate with water containing emulsifier to the desired level Concentration.

Cabbage leaves (Brassica oleracea) are dipped into the active ingredient preparation the desired concentration and treated with caterpillars of the army worm (Spodoptera exigua) occupied while the leaves are still moist.

After the desired time, the kill is determined in%. 100% means that all caterpillars have been killed; 0% means that no caterpillars are killed were.

In this test, e.g. B. the following compounds of the preparation examples have good activity: Table D plant-damaging insects Spodoptera exigua larval test

Example E Spodoptera frugiperda test

Solvent: 7 parts by weight of dimethylformamide

Emulsifier: 2 parts by weight of alkylaryl polyglycol ether

To prepare a suitable preparation of active compound, mix 1 Part by weight of active ingredient with the stated amounts of solvent and emulsifier and dilute the concentrate with water containing emulsifier to the desired level Concentration.

Cabbage leaves (Brassica oleracea) are dipped into the active ingredient preparation the desired concentration and treated with caterpillars of the army worm (Spodoptera frugiperda) occupied while the leaves are still moist.

After the desired time, the kill is determined in%. 100% means that all caterpillars have been killed; 0% means that no caterpillars are killed were.

In this test, e.g. B. the following compounds of the preparation examples good activity: Table E plant-damaging insects Spodoptera frugiperda test

Table E plant-damaging insect Spodoptera frugiperda test

Example F Tetranychus test (OP-resistant / immersion treatment)

Solvent: 7 parts by weight of dimethylformamide

Emulsifier: 2 parts by weight of alkylaryl polyglycol ether

To prepare a suitable preparation of active compound, mix 1 Part by weight of active ingredient with the stated amounts of solvent and emulsifier and dilute the concentrate with water containing emulsifier to the desired level Concentration.

Bean plants (Phaseolus vulgaris), strongly of all stages of the common Spider mite (Tetranychus urticae) are infested in an active ingredient preparation the desired concentration.

After the desired time, the effect is determined in%. 100% means that all spider mites have been killed; 0% means that no spider mites were killed.

In this test, e.g. B. the following compounds of the preparation examples have good activity: Table F mites Tetranychus test (OP-resistant / immersion treatment)

Table F plant-damaging mite tetranychus test (OP-resistant / immersion treatment)

Example G Diabrotica balteata test (larvae in the soil) Limit concentration test / soil insect treatment of transgenic plants

Solvent: 7 parts by weight of dimethylformamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To prepare a suitable preparation of active compound, mix 1 Part by weight of active ingredient with the specified amount of solvent gives the specified Amount of emulsifier and dilute the concentrate with water to the desired level Concentration.

The active ingredient preparation is poured onto the floor. The plays Concentration of the active ingredient in the preparation practically no role, is crucial only the amount of active substance per unit volume of soil, which is in ppm (mg / l) is given. The bottom is filled into 0.25 l pots and left at 20 ° C stand.

Immediately after the preparation, 5 pre-germinated maize kernels of the YIELD variety are added to each pot GUARD (trademark of Monsanto Comp., USA). After 2 days the appropriate test insects are placed in the treated soil. After another 7 The effectiveness of the active ingredient is measured by counting the accumulated days Corn plants determined (1 plant = 20% effect).

Example H Heliothis virescens test (treatment of transgenic plants)

Solvent: 7 parts by weight of dimethylformamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To prepare a suitable preparation of active compound, mix 1 Part by weight of active ingredient with the specified amount of solvent and the specified Amount of emulsifier and dilute the concentrate with water to the desired one Concentration.

Soybean shoots (Glycine max) of the Roundup Ready variety (trademark of Monsanto Comp. USA) are the desired by diving into the active ingredient preparation Treated with concentration and filled with the tobacco bud caterpillar Heliothis virescens, as long as the leaves are still damp.

After the desired time, the kill is determined in%. 100% means that all caterpillars have been killed; 0% means that no caterpillars are killed were.

Claims (25)

1. Δ ¹ -pyrrolines of the formula (I)


found in which
R ^{1 represents} alkyl or optionally substituted aryl,
R ^{2 represents} halogen, cyano, nitro, amino, alkyl or alkoxy,
R ^{3 represents} hydrogen, halogen, alkyl or alkoxy,
R ^{4 stands} for the grouping -XYZE, with the proviso that Y does not stand for a direct bond if X does not stand for a direct bond,
R ^{5 represents} halogen, in each case optionally substituted alkyl, alkoxy or alkylthio,
m represents 0, 1, 2, 3 or 4, where the radicals R ^{5 can be the} same or different if m represents 2, 3 or 4,
X for a direct bond, oxygen, -S (O) _w -, -NR ⁶ -, carbonyl, carbonyloxy, oxycarbonyl, oxysulfonyl (OSO ₂ ), alkylene, haloalkylene, alkenylene, haloalkenylene, alkynylene, alkyleneoxy, oxyalkylene, oxyalkyleneoxy, - S (O) _w -alkylene, cyclopropylene or oxiranylene,
Y stands for a direct bond or for optionally substituted phenylene, naphthylene, tetrahydronaphthylene or heterocyclylene,
Z represents a direct bond or - (CH ₂ ) _n -,
E for hydrogen; Halogen, hydroxy, cyano, formyl, nitro, trialkylsilyl, pentafluorothio, -S (O) _w R ⁷ , -OSO ₂ R ⁷ , -NR ⁸ R ⁹ , -COR ⁷ , -CO ₂ R ⁷ , -OC (O) R ⁷ , -CONR ¹⁰ R ¹¹ , -N (R ¹² ) COR ¹³ , -C (R ¹⁴ ) = N-OR ¹⁵ , -SO ₂ NR ¹⁶ R ¹⁷ , -N (R ¹⁸ ) CO ₂ R ¹⁹ , - N (R ¹⁸ ) C (O) NR ¹⁹ R ²⁰ ; or represents in each case optionally substituted alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, cycloalkyl, cycloalkylalkyl, cycloalkyloxy, aryl, arylalkyl, aryloxy, aryloxyalkyl, saturated or unsaturated heterocyclyl or heterocyclylalkyl,
R ^{6 represents} in each case optionally substituted alkyl, cycloalkyl, cycloalkylalkyl, aryl or arylalkyl,
R ^{7 represents} in each case optionally substituted alkyl, cycloalkyl, aryl or arylalkyl,
R ⁸ and R ⁹ independently of one another represent hydrogen, -SO ₂ R ⁷ , each optionally substituted alkyl, alkenyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl or saturated or unsaturated heterocyclyl or heterocyclylalkyl,
R ⁸ and R ⁹ also together represent optionally substituted alkenylene or alkylene, where the alkylene chain can in each case be interrupted by -O-, -S- or -NR ²¹ -,
R ¹⁰ and R ¹¹ independently of one another represent hydrogen, -SO ₂ R ⁷ , each optionally substituted alkyl, alkenyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl or saturated or unsaturated heterocyclyl or heterocyclylalkyl,
R ¹⁰ and R ¹¹ also together represent optionally substituted alkylene, where the alkylene chain can be interrupted by -O-, -S- or -NR ²¹ -,
R ¹² and R ¹³ independently of one another represent hydrogen, in each case optionally substituted alkyl, cycloalkyl, cycloalkylalkyl, aryl or arylalkyl,
R ¹² and R ¹³ also together represent optionally substituted alkylene or alkenylene,
R ¹⁴ and R ¹⁵ independently of one another represent hydrogen, each optionally substituted alkyl or alkenyl,
R ¹⁶ and R ¹⁷ independently of one another represent hydrogen, each optionally substituted alkyl or cycloalkyl,
R ¹⁶ and R ¹⁷ also together represent optionally substituted alkylene, alkoxyalkylene or alkylthioalkylene,
R ^{18 represents} hydrogen or alkyl,
R ¹⁹ and R ²⁰ independently of one another represent hydrogen, in each case optionally substituted alkyl, alkenyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, saturated or unsaturated heterocyclyl or heterocyclylalkyl,
R ¹⁸ and R ¹⁹ also together represent optionally substituted alkylene, or
R ¹⁹ and R ²⁰ together with the nitrogen atom to which they are attached also represent a saturated or unsaturated heterocycle which can optionally contain a further hetero atom group from the series -O-, -S- or -NR ²² - and which optionally can be substituted
R ^{21 is} hydrogen, -SO ₂ R ⁷ , -COR ⁷ or -CO ₂ R ⁷ ; represents in each case optionally substituted alkyl, alkenyl, cycloalkyl, aryl, or saturated or unsaturated heterocyclyl,
R ^{22 represents} hydrogen, alkyl or alkenyl,
w represents 0, 1 or 2,
n stands for 1, 2, 3 or 4. 2. Δ ¹ -pyrrolines of formula (I) according to claim 1, in which
R ^{1 represents} C ₁ -C ₈ -alkyl or aryl which is optionally mono- or polysubstituted by identical or different substituents, the substituents being selected from the group consisting of halogen, cyano, nitro, alkyl, alkoxy, alkylthio, haloalkyl, haloalkoxy and haloalkylthio,
R ^{2 represents} halogen, cyano, nitro, amino, C ₁ -C ₄ alkyl or C ₁ -C ₄ alkoxy,
R ^{3 represents} hydrogen, halogen, C ₁ -C ₆ alkyl or C ₁ -C ₆ alkoxy,
R ^{4 stands} for the grouping -XYZE, with the proviso that Y does not stand for a direct bond if X does not stand for a direct bond,
R ^{5 represents} halogen, alkyl, alkoxy, alkylthio, haloalkyl, haloalkoxy or haloalkylthio,
m represents 0, 1, 2, 3 or 4, where the radicals R ^{5 can be the} same or different if m represents 2, 3 or 4,
X for a direct bond, oxygen, -S (O) _w -, -NR ⁶ -, carbonyl, carbonyloxy, oxycarbonyl, oxysulfonyl (OSO ₂ ), alkylene, haloalkylene, alkenylene, haloalkenylene, alkynylene, alkyleneoxy, oxyalkylene, oxyalkyleneoxy, - S (O) _w -alkylene, cyclopropylene or oxiranylene,
Y for a direct bond or for in each case optionally up to four times, identical or different, substituted by radicals from the list W ^1, phenylene, naphthylene, tetrahydronaphthylene or 5- to 10-membered, saturated or unsaturated heterocyclylene with one or more heteroatoms from the nitrogen series , Oxygen and sulfur stands,
Z represents a direct bond or - (CH ₂ ) _n -,
E for hydrogen, halogen, hydroxy, cyano, formyl, nitro, trialkylsilyl, pentafluorothio, -S (O) _w R ⁷ , -OSO ₂ R ⁷ , -NR ⁸ R ⁹ , -COR ⁷ , -CO ₂ R ⁷ , - OC (O) R ⁷ , -CONR ¹⁰ R ¹¹ , -N (R ¹² ) COR ¹³ , -C (R ¹⁴ ) = N-OR ¹⁵ , -SO ₂ NR ¹⁶ R ¹⁷ , -N (R ¹⁸ ) CO ₂ R ¹⁹ , -N (R ¹⁸ ) C (O) NR ¹⁹ R ²⁰ ; for alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy optionally substituted once or several times, identically or differently, by halogen, cyano, alkoxy and / or -NR ⁸ R ⁹ ; or for cycloalkyl, cycloalkylalkyl, cycloalkyloxy, aryl, arylalkyl, aryloxy, aryloxyalkyl optionally substituted once or several times, identically or differently, by halogen, cyano, nitro, alkyl, haloalkyl, alkenyl, haloalkenyl, alkoxy, haloalkoxy, alkylthio and / or haloalkylthio. saturated or unsaturated 5- to 10-membered heterocyclyl or heterocyclylalkyl with one or more heteroatoms from the series consisting of nitrogen, oxygen and sulfur,
W ¹ for halogen, cyano, formyl, nitro, trialkylsilyl, alkyl, haloalkyl, alkoxy, haloalkoxy, alkenyl, haloalkenyl, alkenyloxy, haloalkenyloxy, alkylcarbonyl, alkoxycarbonyl, -S (O) _w R ⁷ , -C (R ¹⁴ ) = N - OR ¹⁵ , -SO ₂ NR ¹⁶ R ¹⁷ , - (CH ₂ ) _p NR ¹⁶ R ¹⁷ , - (CH ₂ ) _p N (R ¹⁶ ) COR ¹⁷ , - (CH ₂ ) _p N (R ¹⁶ ) SO ₂ R ¹⁷ , -OSO ₂ R ¹⁶ , -OSO ₂ NR ¹⁶ R ¹⁷ .
R ^{6 stands} for alkyl, haloalkyl, or for cycloalkyl, cycloalkylalkyl, aryl or arylalkyl which is optionally mono- or polysubstituted, identically or differently, by halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio and / or haloalkylthio,
R ⁷ for optionally mono- or polysubstituted, identically or differently, by halogen and / or -NR ⁸ R ⁹ alkyl, for in each case optionally mono- or polysubstituted, identically or differently by halogen, cyano, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio and / or haloalkylthio substituted cycloalkyl, aryl or arylalkyl,
R ⁸ and R ⁹ independently of one another for hydrogen, -SO ₂ R ⁷ , for each optionally mono- or polysubstituted, identically or differently, by halogen, alkylcarbonyl, alkylcarbonyloxy, alkylamino, dialkylamino, alkoxy, haloalkoxy, alkylthio and / or haloalkylthio substituted alkyl or alkenyl ; for cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, saturated or unsaturated, 5- to 10-membered heterocyclyl or heterocyclylalkyl, each optionally mono- or polysubstituted, identically or differently, by halogen, cyano, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio and / or haloalkylthio with one or more heteroatoms from the series nitrogen, oxygen and sulfur,
R ⁸ and R ⁹ furthermore together for optionally mono- or polysubstituted, identically or differently by halogen, cyano, alkoxy, haloalkoxy, alkylthio and / or haloalkylthio or for optionally mono- or polysubstituted, identically or differently by halogen, cyano, alkyl, haloalkyl , Alkoxy, haloalkoxy, alkylthio and / or haloalkylthio substituted alkylene, where the alkylene chain can be interrupted by -O-, -S- or -NR ²¹ -,
R ¹⁰ and R ¹¹ independently of one another for hydrogen, -SO ₂ R ⁷ , for each optionally optionally mono- or polysubstituted, identically or differently, by halogen, alkylamino, dialkylamino, alkoxy and / or alkylthio substituted alkyl or alkenyl; for cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, saturated or unsaturated, 5- to 10-membered heterocyclyl or heterocyclylalkyl, each optionally mono- or polysubstituted, identically or differently, by halogen, cyano, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio and / or haloalkylthio with one or more heteroatoms from the series nitrogen, oxygen and sulfur,
R ¹⁰ and R ¹¹ also together represent optionally substituted one or more times, identically or differently, by halogen, cyano, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio and / or haloalkylthio, the alkylene chain being represented by -O-, -S- or -NR ²¹ - may be interrupted
R ¹² and R ¹³ independently of one another for hydrogen, for alkyl which is optionally mono- or polysubstituted identically or differently by halogen, cyano, alkoxy and / or alkylthio, for in each case optionally mono- or polysubstituted, identically or differently by halogen, cyano, alkyl, haloalkyl , Alkoxy, haloalkoxy, alkylthio and / or haloalkylthio substituted cycloalkyl, cycloalkylalkyl, aryl or arylalkyl,
R ¹² and R ¹³ furthermore each stand for alkylene or alkenylene which is optionally mono- or polysubstituted, identically or differently, by halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio and / or haloalkylthio,
R ¹⁴ and R ¹⁵ independently of one another represent hydrogen, alkyl, alkenyl, haloalkyl or haloalkenyl,
R ¹⁶ and R ¹⁷ independently of one another represent hydrogen, alkyl, haloalkyl or cycloalkyl which is optionally mono- or polysubstituted identically or differently by halogen or alkyl,
R ¹⁶ and R ¹⁷ furthermore each stand for alkylene, alkoxyalkylene or alkylthioalkylene which may be mono- or polysubstituted identically or differently by halogen or alkyl,
R ^{18 represents} hydrogen or alkyl,
R ¹⁹ and R ²⁰ independently of one another for hydrogen, each in each case mono- or polysubstituted, identically or differently, by halogen, alkylcarbonyl, alkylcarbonyloxy, alkylamino, dialkylamino, alkoxy, alkylthio, alkoxyalkoxy, haloalkoxy, haloalkylthio and / or haloalkoxyalkoxy-substituted alkyl or alkenyl;
for cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, saturated or unsaturated, 5- to 10-membered heterocyclyl, each optionally mono- or polysubstituted, identically or differently, by halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylcarbonyl and / or alkoxycarbonyl or heterocyclylalkyl,
R ¹⁸ and R ¹⁹ also together represent alkylene which is mono- or polysubstituted by alkyl, or
R ¹⁹ and R ²⁰ together with the nitrogen atom to which they are attached also represent a saturated or unsaturated 5- to 10-membered heterocycle which may optionally be a further heteroatom group from the series -O-, -S- or -NR ²² - Can contain and which can optionally be substituted one or more times, identically or differently by halogen, alkyl, alkoxy, alkylthio, haloalkyl, haloalkoxy and / or haloalkylthio, and
R ^{21 is} hydrogen, -SO ₂ R ⁷ , -COR ⁷ or -CO ₂ R ⁷ ; for alkyl or alkenyl which is optionally mono- or polysubstituted, identically or differently, by halogen, cyano, alkylamino, dialkylamino, alkoxy, haloalkoxy, alkylthio and / or haloalkylthio; for cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, saturated or unsaturated, 5- to 10-membered heterocyclyl or heterocyclylalkyl, optionally substituted once or several times, identically or differently, by halogen, cyano, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio and / or haloalkylthio with one or more heteroatoms from the series nitrogen, oxygen and sulfur,
R ^{22 represents} hydrogen, alkyl or alkenyl,
w represents 0, 1 or 2,
n represents 1, 2, 3 or 4,
p stands for 0, 1 or 2. 3. Δ ¹ -pyrrolines of the formula (I) according to claim 1, in which
R ^{1 stands} for C ₁ -C ₄ alkyl or for optionally single to tetrasubstituted, identical or differently substituted aryl (in particular phenyl), where the substituents from the series fluorine, chlorine, bromine, iodine, cyano, nitro, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ haloalkoxy and C ₁ -C ₄ haloalkylthio each with 1 to 9 fluorine , Chlorine and / or bromine atoms are selected,
R ^{2 represents} fluorine, chlorine, bromine, cyano, nitro, amino, C ₁ -C ₄ alkyl or C ₁ - C ₄ alkoxy,
R ^{3 represents} hydrogen, fluorine, chlorine, bromine, C ₁ -C ₄ alkyl or C ₁ -C ₄ alkoxy,
R ^{4 stands} for the grouping -XYZE with the proviso that Y does not stand for a direct bond if X does not stand for a direct bond,
R ⁵ represents fluorine, chlorine, bromine, C ₁ -C ₆ alkyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ -alkylthio, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ -haloalkoxy or C ₁ -C ₆ haloalkylthio each having 1 to 13 fluorine, chlorine and / or bromine atoms,
m represents 0, 1, 2 or 3, where the radicals R ^{5 can be} identical or different if m represents 2 or 3,
X for a direct bond, oxygen, -S (O) _w -, -NR ⁶ -, carbonyl, carbonyloxy, oxycarbonyl, oxysulfonyl (OSO ₂ ), C ₁ -C ₆ alkylene, C ₁ - C ₆ haloalkylene, C ₂ -C ₆ alkenylene, C ₂ -C ₆ haloalkenylene, C ₂ - C ₆ alkynylene, C ₁ -C ₆ alkyleneoxy, C ₁ -C ₆ oxyalkylene, oxy-C ₁ -C ₆ alkyleneoxy or - S (O) _{w is} -C ₁ -C ₆ -alkylene,
Y for a direct bond or for in each case optionally up to four times, identically or differently, 1,4-phenylene, 1,3-phenylene, 1,2-phenylene, 2,6-naphthylene substituted by radicals from the list W ¹ , 7-naphthylene, 1,4-naphthylene, 2,6- (1,2,3,4-tetrahydro) naphthylene, 2,7- (1,2,3,4-tetrahydro) naphthylene, 1,4- (1st , 2,3,4-tetrahydro) naphthylene, 5,8- (1,2,3,4-tetrahydro) naphthylene; or for in each case optionally up to four times, identically or differently, 5- or 6-membered, saturated or unsaturated heterocyclylene substituted by radicals from the list W ¹ with 1 to 3 heteroatoms which contains 0 to 3 nitrogen atoms, 0 to 2 non-adjacent oxygen atoms and / or contains 0 to 2 non-adjacent sulfur atoms (in particular furylene, thienylene, pyrrolylene, oxazolylene, thiazolylene, pyridinylene, pyrimidinylene or pyridazinylene or pyrazinylene),
Z is a direct bond or - (CH ₂ ) _n -, x
E for hydrogen, fluorine, chlorine, bromine, hydroxy, cyano, formyl, nitro, tri- (C ₁ -C ₆ alkyl) silyl, pentafluorothio, -S (O) _w R ⁷ , -OSO ₂ R ⁷ , -NR ⁸ R ⁹ , -COR ⁷ , -CO ₂ R ⁷ , -OC (O) R ⁷ , -CONR ¹⁰ R ¹¹ , -N (R ¹² ) COR ¹³ , -C (R ¹⁴ ) = N-OR ¹⁵ , SO ₂ NR ¹⁶ R ¹⁷ , -N (R ¹⁸ ) CO ₂ R ¹⁹ , -N (R ¹⁸ ) C (O) NR ¹⁹ R ²⁰ ; in each case optionally monosubstituted or polysubstituted by identical or different halogen, cyano, C ₁ -C ₁₀ - alkoxy and / or -NR ⁸ R ⁹ substituted C ₁ -C ₂₀ alkyl, C ₂ -C ₂₀ alkenyl, C ₂ - C ₁₀ alkynyl, C ₁ -C ₂₀ alkoxy, C ₂ -C ₂₀ alkenyloxy; or for in each case optionally up to four times, identically or differently, by halogen, cyano, nitro, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ haloalkenyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ haloalkoxy, C ₁ - C ₆ alkylthio and / or C ₁ -C ₆ haloalkylthio substituted C ₃ -C ₁₂ cycloalkyl, C ₃ -C ₇ cycloalkyl- C ₁ -C ₄ alkyl, C ₃ -C ₁₂ cycloalkyloxy, aryl, aryl-C ₁ -C ₄ alkyl, aryloxy, aryloxy-C ₁ -C ₄ alkyl, saturated or unsaturated 5- to 10-membered heterocyclyl or heterocyclyl-C ₁ -C ₄ -alkyl having 1 to 4 heteroatoms which contain 0 to 4 nitrogen atoms, 0 to 2 non-adjacent oxygen atoms and / or 0 to 2 non-adjacent sulfur atoms (in particular tetrazolyl, furyl, furfuryl, benzofuryl, tetrahydrofuryl, Thienyl, thenyl, benzothienyl, thiolanyl, pyrrolyl, indolyl, pyrrolinyl, pyrrolidino, pyrrolidinyl, oxazolyl, benzoxazolyl, isoxazolyl, imidazolyl, pyrazolyl, thiazolyl, benzothiazolyl, thiazolidinyl, pyridine yl, pyrimidinyl, pyridazyl, pyrazinyl, piperidinyl, piperidino, morpholinyl, thiomorpholinyl, morpholino, thiomorpholino, triazinyl, triazolyl, quinolinyl or isoquinolinyl),
W ¹ for fluorine, chlorine, bromine, cyano, formyl, nitro, tri- (C ₁ -C ₆ alkyl) silyl, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ - Alkoxy, C ₁ -C ₆ haloalkoxy, C ₂ -C ₆ alkenyl, C ₂ -C ₆ haloalkenyl, C ₂ -C ₆ alkenyloxy, C ₂ -C ₆ haloalkenyloxy, C ₁ -C ₆ alkylcarbonyl, C ₁ -C ₆ alkoxycarbonyl, -S (O) _w R ⁷ , -C (R ¹⁴ ) = N-OR ¹⁵ , -SO ₂ NR ¹⁶ R ¹⁷ , - (CH ₂ ) _p NR ¹⁶ R ¹⁷ , - ( CH ₂ ) _p N (R ¹⁶ ) COR ¹⁷ , - (CH ₂ ) _p N (R ¹⁶ ) SO ₂ R ¹⁷ , -OSO ₂ R ¹⁶ , -OSO ₂ NR ¹⁶ R ¹⁷ ,
R ⁶ for C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, or for each optionally optionally up to four times, identically or differently by halogen, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ haloalkoxy, C ₁ - C ₆ alkylthio and / or C ₁ -C ₆ haloalkylthio substituted C ₃ -C ₇ cycloalkyl, C ₃ -C ₆ cycloalkyl-C ₁ -C ₄ alkyl, aryl or aryl-C ₁ -C ₄ alkyl,
R ⁷ for C ₁ -C ₂₀ alkyl optionally substituted _one or more times, identically or differently by halogen and / or -NR ⁸ R ⁹ , for each optionally optionally up to eight times, identically or differently, by halogen, cyano, C ₁ -C ₆ Alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ haloalkoxy, C ₁ -C ₆ alkylthio and / or C ₁ -C ₆ haloalkylthio substituted C ₃ -C ₆ Cycloalkyl, aryl or aryl-C ₁ -C ₄ -alkyl,
R ⁸ and R ⁹ independently of one another for hydrogen, -SO ₂ R ⁷ , for each in each case optionally singly or multiply, identically or differently by halogen, C ₁ -C ₆ -alkylcarbonyl, C ₁ -C ₆ -alkylcarbonyloxy, C ₁ -C ₆ -Alkylamino, di- (C ₁ -C ₆ -alkyl) amino, C ₁ -C ₆ -alkoxy, C ₁ -C ₆ -haloalkoxy, C ₁ - C ₆ -alkylthio and / or C ₁ -C ₆ -haloalkylthio substituted C ₁ -C ₂₀ alkyl or C ₂ -C ₂₀ alkenyl; for each optionally one to four times, identical or different, by halogen, cyano, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ haloalkoxy, C ₁ - C ₆ - alkylthio and / or C ₁ -C ₆ haloalkylthio substituted C ₃ -C ₁₂ cycloalkyl, C ₃ -C ₇ cycloalkyl-C ₁ -C ₄ alkyl, aryl, aryl-C ₁ -C ₄ alkyl , saturated or unsaturated, 5- to 10-membered heterocyclyl or heterocyclyl-C ₁ -C ₄ alkyl having 1 to 4 heteroatoms which contain 0 to 4 nitrogen atoms, 0 to 2 non-adjacent oxygen atoms and / or 0 to 2 non-adjacent sulfur atoms (in particular tetrazolyl, furyl, furfuryl, benzofuryl, tetrahydrofuryl, thienyl, thenyl, benzothienyl, thiolanyl, pyrrolyl, indolyl, pyrrolinyl, pyrrolidinyl, oxazolyl, benzoxazolyl, isoxazolyl, imidazolyl, pyrazolyl, thiazolylyl, pyriazoleyl, pyriazole Pyrazinyl, piperidinyl, morpholinyl, thiomorpholinyl, triazinyl, triazolyl, quinolinyl or isoquinoli stand),
R ⁸ and R ⁹ furthermore together represent optionally monosubstituted or polysubstituted by identical or different halogen, cyano, C ₁ -C ₆ alkoxy, C ₁ -C ₆ - haloalkoxy, C ₁ -C ₆ alkylthio and / or C ₁ - C ₆ -Halogenalkylthio substituted C ₂ -C ₁₂ alkenylene or for one or more, optionally in the alkylene part, the same or different by halogen, cyano, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ -Alkoxy, C ₁ -C ₆ -haloalkoxy, C ₁ -C ₆ -alkylthio and / or C ₁ -C ₆ -haloalkylthio substituted C ₃ -C ₁₂ -alkylene, the alkylene chain being -O-, -S- or - NR ²¹ - may be interrupted,
R ¹⁰ and R ¹¹ independently of one another for hydrogen, -SO ₂ R ⁷ , for each in each case optionally up to thirteen times, identically or differently by halogen, C ₁ -C ₆ -alkylamino, di- (C ₁ -C ₆ -alkyl) amino, C ₁ -C ₆ alkoxy, C ₁ -C ₆ haloalkoxy, C ₁ -C ₆ alkylthio and / or C ₁ -C ₆ haloalkylthio substituted C ₁ -C ₆ alkyl or C ₂ -C ₆ alkenyl; for in each case optionally up to four times, identically or differently, by halogen, cyano, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ haloalkoxy, C ₁ - C ₆ alkylthio and / or C ₁ -C ₆ haloalkylthio substituted C ₃ -C ₇ cycloalkyl, C ₃ -C ₇ cycloalkyl-C ₁ -C ₄ alkyl, aryl, aryl-C ₁ -C ₄ alkyl , saturated or unsaturated, 5- to 10-membered heterocyclyl or heterocyclyl-C ₁ -C ₄ alkyl having 1 to 4 heteroatoms which contain 0 to 4 nitrogen atoms, 0 to 2 non-adjacent oxygen atoms and / or 0 to 2 non-adjacent sulfur atoms (in particular tetrazolyl, furyl, furfuryl, benzofuryl, tetrahydrofuryl, thienyl, thenyl, benzothienyl, thiolanyl, pyrrolyl, indolyl, pyrrolinyl, pyrrolidinyl, oxazolyl, benzoxazolyl, isoxazolyl, imidazolyl, pyrazolyl, thiazolylyl, pyriazoleyl, pyriazole Pyrazinyl, piperidinyl, morpholinyl, thiomorpholinyl, triazinyl, triazolyl, quinolinyl or isoquinoliny l) stand,
R ¹⁰ and R ¹¹ also together, optionally in the alkylene part, one to four times, identically or differently by halogen, cyano, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ alkoxy, C ₁ - C ₆ -haloalkoxy, C ₁ -C ₆ -alkylthio and / or C ₁ -C ₆ -haloalkylthio-substituted C ₃ -C ₆ -alkylene, - (CH ₂ ) ₂ -O- (CH ₂ ) ₂ -, - (CH ₂ ) ₂ -S- (CH ₂ ) ₂ - or - (CH ₂ ) ₂ -N (R ²¹ ) - (CH ₂ ) ₂ -,
R ¹² and R ¹³ independently of one another for hydrogen, for optionally single to thirteen times, identical or different, substituted by halogen, cyano, C ₁ -C ₆ alkoxy, C ₁ -C ₆ alkylthio, C ₁ -C ₆ alkyl, for each optionally one to eight times, identical or different, by halogen, cyano, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ haloalkoxy, C ₁ -C ₆ Alkylthio and / or C ₁ -C ₆ -haloalkylthio substituted C ₃ -C ₇ -cycloalkyl, C ₃ -C ₇ -cycloalkyl-C ₁ -C ₄ -alkyl, aryl or aryl-C ₁ -C ₄ -alkyl,
R ¹² and R ¹³ also together, in each case optionally for one to eight times, the same or different, by halogen, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ - Halogenalkoxy, C ₁ -C ₆ alkylthio and / or C ₁ -C ₆ haloalkylthio substituted C ₃ -C ₁₀ alkylene or C ₃ -C ₁₀ alkenylene,
R ¹⁴ and R ¹⁵ independently of one another represent hydrogen, C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl, C ₁ -C ₆ haloalkyl or C ₂ -C ₆ haloalkenyl,
R ¹⁶ and R ¹⁷ independently of one another for hydrogen, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl or for optionally up to eight times, identically or differently, by fluorine, chlorine, bromine and / or C ₁ -C ₆ - Alkyl substituted C ₃ -C ₇ cycloalkyl,
R ¹⁶ and R ¹⁷ furthermore together substituted in each case optionally substituted once to nine times in an identical or different manner by fluorine, chlorine, bromine and / or C ₁ -C ₆ alkyl, C ₃ -C ₆ alkylene, C ₁ -C ₃ alkoxy Are C ₁ -C ₃ alkylene or C ₁ -C ₃ alkylthio-C ₁ -C ₃ alkylene,
R ^{18 represents} hydrogen or C ₁ -C ₆ alkyl,
R ¹⁹ and R ²⁰ independently of one another for hydrogen, each in each case optionally singly or multiply, identically or differently by fluorine, chlorine, bromine, C ₁ -C ₆ -alkylcarbonyl, C ₁ -C ₆ -alkylcarbonyloxy, C ₁ -C ₆ -alkylamino , Di- (C ₁ -C ₆ alkyl) amino, C ₁ -C ₁₀ alkoxy, C ₁ -C ₁₀ alkylthio, C ₁ -C ₁₀ alkoxy-C ₁ -C ₁₀ alkoxy, C ₁ -C ₁₀ haloalkoxy, C ₁ - C ₁₀ haloalkylthio and / or C ₁ -C ₁₀ haloalkoxy, C ₁ -C ₁₀ -alkoxy-substituted C ₁ -C ₂₀ alkyl or C ₂ -C ₂₀ alkenyl;
for in each case optionally up to four times, identically or differently, by fluorine, chlorine, bromine, C ₁ -C ₆ -alkyl, C ₁ -C ₆ -alkoxy, C ₁ -C ₆ -alkylthio, C ₁ - C ₆ -haloalkyl, C ₁ -C ₆ haloalkoxy, C ₁ -C ₆ haloalkylthio, C ₁ - C ₆ alkylcarbonyl and / or C ₁ -C ₆ alkoxycarbonyl substituted C ₃ - C ₁₂ cycloalkyl, C ₃ -C ₇ cycloalkyl-C ₁ -C ₄ alkyl, aryl, aryl-C ₁ -C ₄ alkyl, saturated or unsaturated, 5- to 10-membered heterocyclyl or heterocyclyl-C ₁ -C ₄ alkyl having 1 to 4 heteroatoms, which are 0 to 4 Contain nitrogen atoms, 0 to 2 non-adjacent oxygen atoms and / or 0 to 2 non-adjacent sulfur atoms (in particular tetrazolyl, furyl, furfuryl, benzofuryl, tetrahydrofuryl, thienyl, thenyl, benzothienyl, thiolanyl, pyrrolyl, indolyl, pyrrolinyl, pyrrolidinyl, oxazolyl, oxazolyl, oxazolyl, oxazolyl, Isoxazolyl, imidazolyl, pyrazolyl, thiazolyl, benzothiazolyl, thiazolidinyl, pyridinyl, pyrimidinyl, pyridazyl, pyrazinyl, piperidinyl, morpholinyl, thiomorph olinyl, triazinyl, triazolyl, quinolinyl or isoquinolinyl),
R ¹⁸ and R ¹⁹ also together represent C ₂ -C ₄ alkylene which is optionally monosubstituted to tetrasubstituted by C ₁ -C ₄ alkyl, or
R ¹⁹ and R ²⁰ together with the nitrogen atom to which they are attached also represent a saturated or unsaturated 5- to 10-membered heterocycle which may optionally be a further heteroatom group from the series -O-, -S- or -NR ²² - Can contain and optionally up to four times, identical or different, by fluorine, chlorine, bromine, C ₁ -C ₆ alkyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ alkylthio, C ₁ -C ₆ - Haloalkyl, C ₁ -C ₆ haloalkoxy and / or C ₁ -C ₆ haloalkylthio may be substituted, and
R ^{21 is} hydrogen, -SO ₂ R ⁷ , -COR ⁷ or -CO ₂ R ⁷ ; for each optionally one or more times, identically or differently, by halogen, cyano, C ₁ -C ₆ -alkylamino, di- (C ₁ -C ₆ -alkyl) amino, C ₁ -C ₆ -alkoxy, C ₁ - C ₆ - Haloalkoxy, C ₁ -C ₆ alkylthio and / or C ₁ -C ₆ haloalkylthio substituted C ₁ -C ₂₀ alkyl or C ₂ -C ₂₀ alkenyl; for each optionally one to four times, identical or different, by halogen, cyano, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ haloalkoxy, C ₁ - C ₆ alkylthio and / or C ₁ -C ₆ haloalkylthio substituted C ₃ -C ₁₂ cycloalkyl, C ₃ -C ₇ cycloalkyl-C ₁ -C ₄ alkyl, aryl, aryl C ₁ -C ₄ alkyl , saturated or unsaturated, 5- to 10-membered heterocyclyl or heterocyclyl-C ₁ -C ₄ alkyl having 1 to 4 heteroatoms which contain 0 to 4 nitrogen atoms, 0 to 2 non-adjacent oxygen atoms and / or 0 to 2 non-adjacent sulfur atoms (in particular tetrazolyl, furyl, furfuryl, benzofuryl, tetrahydrofuryl, thienyl, thenyl, benzothienyl, thiolanyl, pyrrolyl, indolyl, pyrrolinyl, pyrrolidinyl, oxazolyl, benzoxazolyl, isoxazolyl, imidazolyl, pyrazolyl, thiazolylyl, pyriazoleyl, pyriazole Pyrazinyl, piperidinyl, morpholinyl, thiomorpholinyl, triazinyl, triazolyl, quinolinyl or isoquinoline yl) stands,
R ^{22 represents} hydrogen, C ₁ -C ₆ alkyl or C ₂ -C ₆ alkenyl,
w represents 0, 1 or 2,
n represents 1, 2 or 3,
p stands for 0, 1 or 2. 4. Δ ¹ -pyrrolines of formula (I) according to claim 1, in which
R ^{1 stands} for methyl, ethyl, n- or i-propyl, or for aryl which is optionally mono- or disubstituted, identically or differently, the substituents from the series fluorine, chlorine, bromine, iodine, cyano, nitro, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ -haloalkoxy and C ₁ -C ₄ -haloalkylthio having in each case 1 to 9 fluorine , Chlorine and / or bromine atoms are selected,
R ^{2 represents} fluorine, chlorine, bromine, cyano, nitro, amino, C ₁ -C ₄ alkyl or C ₁ - C ₄ alkoxy,
R ^{3 represents} hydrogen, fluorine, chlorine, bromine, cyano, nitro, amino, C ₁ -C ₄ alkyl or C ₁ -C ₄ alkoxy,
R ^{4 stands} for the grouping -XYZE with the proviso that Y does not stand for a direct bond if X does not stand for a direct bond,
R ^{5 is} fluorine, chlorine, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio; C ₁ -C ₄ haloalkyl, C ₁ -C ₄ haloalkoxy, C ₁ -C ₄ haloalkylthio each having 1 to 9 fluorine, chlorine and / or bromine atoms,
m represents 0, 1 or 2, where the radicals R ^{5 can be} identical or different if m represents 2,
X for a direct bond, oxygen, -S (O) _w -, -NR ⁶ -, carbonyl, carbonyloxy, oxycarbonyl, oxysulfonyl (OSO ₂ ), C ₁ -C ₄ alkylene, C ₁ - C ₄ haloalkylene with 1 up to 8 fluorine, chlorine and / or bromine atoms, C ₂ -C ₄ alkenylene, C ₂ -C ₄ haloalkenylene with 1 to 6 fluorine, chlorine and / or bromine atoms, C ₂ -C ₄ alkynylene, C ₁ -C ₄ -alkyleneoxy, oxy-C ₁ - C ₄ -alkylene, oxy-C ₁ -C ₄ -alkyleneoxy or -S (O) _w -C ₁ -C ₄ alkylene,
Y for a direct bond or for in each case optionally single to triple, identical or different, substituted by radicals from the list W ^1, 1,4-phenylene, 1,3-phenylene, 1,2-phenylene, 2,6-naphthylene, 2, 7-naphthylene, 1,4-naphthylene, 2,6- (1,2,3,4-tetrahydro) naphthylene, 2,7- (1,2,3,4-tetrahydro) naphthylene, 1,4- (1st , 2,3,4-tetrahydro) naphthylene, 5,8- (1,2,3,4-tetrahydro) naphthylene, 2,4-furylene, 2,4-thienylene, 2,4-pyrrolylene, 2,5- Oxazolylene, 2,5-thiazolylene, 2,5-pyridinylene, 2,6-pyridinylene, 2,5-pyrimidinylene or 3,6-pyridazinylene or 2,5-pyrazinylene,
Z represents a direct bond or - (CH ₂ ) _n -,
E for hydrogen, fluorine, chlorine, bromine, hydroxy, cyano, formyl, nitro, trimethylsilyl, dimethyl-tert-butylsilyl, -S (O) _w R ⁷ , -OSO ₂ R ⁷ , -NR ⁸ R ⁹ , -COR ⁷ , - CO ₂ R ⁷ , -OC (O) R ⁷ , -CONR ¹⁰ R ¹¹ , -N (R ¹² ) COR ¹³ , -SO ₂ NR ¹⁶ R ¹¹ , -N (R ¹⁸ ) CO ₂ R ¹⁹ , -N ( R ¹⁸ ) C (O) NR ¹⁹ R ²⁰ ; for C ₁ -C ₁₆ -alkyl, C ₂ -C ₁₆ -alkenyl substituted in each case optionally once or several times, identically or differently, by fluorine, chlorine, bromine, cyano, C ₁ -C ₆ -alkoxy and / or -NR ⁸ R ⁹ , C ₂ -C ₆ alkynyl, C ₁ -C ₁₆ alkoxy, C ₂ -C ₁₆ alkenyloxy; or for each optionally single to triple, identical or different, by fluorine, chlorine, bromine, cyano, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ - Haloalkyl, C ₁ -C ₄ haloalkoxy, C ₁ -C ₄ haloalkylthio each having 1 to 9 fluorine, chlorine and / or bromine atoms, C ₂ -C ₆ alkenyl and / or C ₂ -C ₆ haloalkenyl with 1 to 8 fluorine, chlorine and / or bromine atoms substituted C ₃ -C ₁₀ cycloalkyl, C ₃ -C ₆ cycloalkyl-C ₁ -C ₄ alkyl, C ₃ -C ₁₀ cycloalkyloxy, phenyl, phenoxy, benzyl , Phenylethyl, benzyloxy, tetrazolyl, furyl, furfuryl, benzofuryl, tetrahydrofuryl, thienyl, thenyl, benzothienyl, thiolanyl, pyrrolyl, indolyl, pyrrolinyl, pyrrolidino, pyrrolidinyl, oxazolyl, benzoxazolyl, isoxazolyl, pyridolyloliazolyl, pyridylylolyloliazolyl, imidazylyloliazolyl, imidazylyliazolyl, imidazylyloliazolyl, imidazylyliazolyl, imidazylolidol , Pyrimidinyl, pyridazyl, pyrazinyl, piperidinyl, piperidino, morpholinyl, thiomorpholinyl, morpholino, thiomorpholino, triazinyl, triazolyl, quinolinyl or isoquinolinyl,
W ¹ for fluorine, chlorine, bromine, cyano, formyl, trimethylsilyl, dimethyl-tert-butylsilyl, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₂ -C ₄ alkenyl, C ₂ -C ₄ alkenyloxy; for C ₁ -C ₄ haloalkyl, C ₁ -C ₄ haloalkoxy each having 1 to 9 fluorine, chlorine and / or bromine atoms, C ₂ -C ₄ haloalkenyl, C ₂ - C ₄ haloalkenyloxy each having 1 to 8 fluorine, chlorine and / or bromine atoms; for C ₁ -C ₄ alkylcarbonyl, C ₁ -C ₄ alkoxycarbonyl, -S (O) _w R ⁷ , -SO ₂ NR ¹⁶ R ¹⁷ , - (CH ₂ ) _p NR ¹⁶ R ¹⁷ , - (CH ₂ ) _p N (R ¹⁶ ) COR ¹⁷ , - (CH ₂ ) _p N (R ¹⁶ ) SO ₂ R ¹⁷ , -OSO ₂ R ¹⁶ , -OSO ₂ NR ¹⁶ R ¹⁷ ,
R ⁶ for methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, trifluoromethyl, trifluoroethyl, or for each optionally one to four times, identical or different by fluorine, chlorine , bromine, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ -haloalkoxy and / or C ₁ -C ₄ Haloalkylthio, each with 1 to 9 fluorine, chlorine and / or bromine atoms, substituted cyclopropyl, cyclopropylmethyl, cyclopentyl, cyclopentylmethyl, cyclohexyl, cyclohexylmethyl, phenyl, benzyl or phenylethyl,
R ⁷ for C ₁ -C ₁₀ -alkyl, optionally substituted _one or more times, identically or differently by fluorine, chlorine, bromine and / or -NR ⁸ R ⁹ , for each optionally optionally up to four times, identically or differently, by fluorine, chlorine and / or bromine, cyano, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ -haloalkoxy and / or C ₁ - C ₄ haloalkylthio, each with 1 to 9 fluorine, chlorine and / or bromine atoms, substituted cyclopropyl, cyclopentyl, cyclohexyl, phenyl or benzyl,
R ⁸ and R ⁹ independently of one another for hydrogen, -SO ₂ R ⁷ , for each optionally one or more times, identically or differently by fluorine, chlorine and / or bromine, C ₁ -C ₄ -alkylcarbonyl, C ₁ -C ₄ -alkylcarbonyloxy , C ₁ -C ₄ alkylamino, di- (C ₁ -C ₄ alkyl) amino, C ₁ -C ₄ alkoxy, C ₁ - C ₄ alkylthio, C ₁ -C ₄ haloalkoxy and / or C ₁ -C ₄ haloalkylthio each with 1 to 9 fluorine, chlorine and / or bromine atoms substituted C ₁ -C ₁₆ alkyl or C ₂ -C ₁₆ alkenyl; for each optionally single to triple, identical or different, by fluorine, chlorine and / or bromine, cyano, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ - Haloalkyl, C ₁ -C ₄ haloalkoxy and / or C ₁ -C ₄ haloalkylthio, each with 1 to 9 fluorine, chlorine and / or bromine atoms, substituted C ₃ -C ₁₀ cycloalkyl, C ₃ -C ₆ cycloalkyl -C ₁ -C ₄ alkyl, phenyl, benzyl, phenylethyl, tetrazolyl, furyl, furfuryl, benzofuryl, tetrahydrofuryl, thienyl, thenyl, benzothienyl, thiolanyl, pyrrolyl, indolyl, pyrrolinyl, pyrrolidinyl, oxazolyl, benzoxazolyl, isoxazolyl, imidazazolyl, imidazolylyl, imidazolyl , Thiazolyl, benzothiazolyl, thiazolidinyl, pyridinyl, pyrimidinyl, pyridazyl, pyrazinyl, piperidinyl, morpholinyl, thiomorpholinyl, triazinyl, triazolyl, quinolinyl or isoquinolinyl.
R ⁸ and R ⁹ furthermore together for optionally single or multiple, identical or different by fluorine, chlorine and / or bromine, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ haloalkoxy and / or C ₁ -C ₄ haloalkylthio, each with 1 to 9 fluorine, chlorine and / or bromine atoms, substituted C ₂ -C ₁₀ alkenylene or for one or more, optionally in the alkylene part, identical or different by fluorine, chlorine, cyano, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ haloalkoxy and / or C ₁ -C ₄ haloalkylthio with each 1 to 9 fluorine, chlorine and / or bromine atoms substituted C ₃ -C ₁₀ alkylene, where the alkylene chain can be interrupted by -O-, -S- or -NR ²¹ -,
R ¹⁰ and R ¹¹ independently of one another for hydrogen, -SO ₂ R ⁷ , each in each case optionally up to nine times, identically or differently by fluorine, chlorine and / or bromine, C ₁ -C ₄ -alkylamino, di- (C ₁ -C _4- alkyl) amino, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ haloalkoxy and / or C ₁ -C ₄ haloalkylthio, each with 1 to 9 fluorine, chlorine and / or bromine atoms substituted C ₁ -C ₆ alkyl or C ₂ -C ₆ alkenyl; for each optionally single to triple, identical or different by fluorine, chlorine and / or bromine, cyano, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ Haloalkyl, C ₁ -C ₄ haloalkoxy and / or C ₁ -C ₄ haloalkylthio each with 1 to 9 fluorine, chlorine and / or bromine atoms substituted C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ cycloalkyl -C ₁ -C ₄ alkyl, phenyl, benzyl, phenylethyl, tetrazolyl, furyl, furfuryl, benzofuryl, tetrahydrofuryl, thienyl, thenyl, benzothienyl, thiolanyl, pyrrolyl, indolyl, pyrrolinyl, pyrrolidinyl, oxazolyl, benzoxazolyl, isoxazolyl, imidazazolyl, imidazolylyl, imidazolyl , Thiazolyl, benzothiazolyl, thiazolidinyl, pyridinyl, pyrimidinyl, pyridazyl, pyrazinyl, piperidinyl, morpholinyl, thiomorpholinyl, triazinyl, triazolyl, quinolinyl or isoquinolinyl,
R ¹⁰ and R ¹¹ furthermore together for each, optionally in the alkylene part, one to four times, identically or differently, by fluorine, chlorine, cyano, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ haloalkoxy and / or C ₁ -C ₄ haloalkylthio each with 1 to 9 fluorine, chlorine and / or bromine atoms substituted C ₄ - C ₅ alkylene, - ( CH ₂ ) ₂ -O- (CH ₂ ) ₂ -, - (CH ₂ ) ₂ -S- (CH ₂ ) ₂ -, - (CH ₂ ) ₂ -N (R ²¹ ) - (CH ₂ ) ₂ - .
R ¹² and R ¹³ independently of one another for hydrogen, for optionally _{1 to} 9 times, identically or differently, substituted by fluorine, chlorine, bromine, C ₁ -C ₄ alkoxy and / or C ₁ -C ₄ alkylthio, substituted C ₁ -C ₆ - Alkyl, each optionally up to four times, the same or different by fluorine, chlorine, bromine, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ haloalkyl , C ₁ -C ₄ haloalkoxy and / or C ₁ -C ₄ haloalkylthio each with 1 to 9 fluorine, chlorine and / or bromine atoms substituted C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ cycloalkyl-C ₁ - C ₄ alkyl, phenyl, benzyl or phenylethyl,
R ¹² and R ¹³ furthermore together represent in each case optionally mono- to tetrasubstituted by identical or different fluorine, chlorine, bromine, C ₁ -C ₄ - alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ haloalkoxy and / or C ₁ -C ₄ haloalkylthio each with 1 to 9 fluorine, chlorine and / or bromine atoms substituted C ₃ -C ₈ alkylene or C ₃ -C ₈ -alkenylene,
R ¹⁶ and R ¹⁷ independently of one another for hydrogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl with 1 to 9 fluorine, chlorine and / or bromine atoms or for optionally up to four times, identical or different, by fluorine , Chlorine, bromine and / or C ₁ -C ₄ alkyl-substituted C ₃ -C ₆ cycloalkyl,
R ¹⁶ and R ¹⁷ also together for - (CH ₂ ) ₃ -, - (CH ₂ ) ₄ -, - (CH ₂ ) ₅ -, - (CH ₂ ) ₂ -O- (CH ₂ ) ₂ - or - ( CH ₂ ) ₂ -S- (CH ₂ ) ₂ - stand,
R ^{18 represents} hydrogen or C ₁ -C ₄ alkyl,
R ¹⁹ and R ²⁰ independently of one another for hydrogen, each in each case optionally singly or multiply, identically or differently by fluorine, chlorine, bromine, C ₁ -C ₄ alkylcarbonyl, C ₁ -C ₄ alkylcarbonyloxy, C ₁ -C ₄ alkylamino , Di- (C ₁ -C ₄ alkyl) amino, C ₁ -C ₁₀ alkoxy, C ₁ -C ₁₀ alkylthio, C ₁ -C ₁₀ alkoxy-C ₁ -C ₆ alkoxy, C ₁ -C ₁₀ haloalkoxy, C ₁ - C ₁₀ haloalkylthio and / or C ₁ -C ₁₀ -haloalkoxy-C ₁ -C ₆ alkoxy each having 1 to 21 fluorine, chlorine and / or bromine-substituted C ₁ -C ₁₆ - Alkyl or C ₂ -C ₁₆ alkenyl;
for each optionally single to triple, identical or different, by fluorine, chlorine, bromine, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ haloalkoxy, C ₁ -C ₄ haloalkylthio each having 1 to 9 fluorine, chlorine and / or bromine atoms, C ₁ -C ₄ alkylcarbonyl and / or C ₁ -C ₄ alkoxycarbonyl substituted C ₃ - C ₁₀ -cycloalkyl, C ₃ -C ₆ -cycloalkyl-C ₁ -C ₄ -alkyl, phenyl, benzyl, phenylethyl, tetrazolyl, furyl, furfuryl, benzofuryl, tetrahydrofuryl, thienyl, thenyl, benzothienyl, thiolanyl, pyrrolyl, indolyl, pyrrolinyl , Pyrrolidinyl, oxazolyl, benzoxazolyl, isoxazolyl, imidazolyl, pyrazolyl, thiazolyl, benzothiazolyl, thiazolidinyl, pyridinyl, pyrimidinyl, pyridazyl, pyrazinyl, piperidinyl, morpholinyl, thiomorpholinyl, triazinyl, triazolyl, quinolinyl, quinolinyl
R ¹⁸ and R ¹⁹ also jointly represent C ₂ -C ₃ alkylene which is optionally monosubstituted to trisubstituted by C ₁ -C ₄ alkyl, or
R ¹⁹ and R ²⁰ together with the nitrogen atom to which they are attached also represent a saturated or unsaturated 5- to 7-membered heterocycle which may optionally be a further heteroatom group from the series -O-, -S- or -NR ²² - May contain (in particular from the series Piperidino, Morpholino, Thiomorpholino, Piperazino, Pyrrolidino, Oxazolidino, Thiazolidino, 4H-1-Oxazinyl, 4H-1-Thiazinyl) and the optionally single to fourfold, identical or different by fluorine, chlorine, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ - C ₄ alkylthio, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ haloalkoxy and / or C ₁ - C ₄ haloalkylthio with each 1 to 9 fluorine, chlorine and / or bromine atoms can be substituted, and
R ²¹ for hydrogen, -SO ₂ R ⁷ , for -COR ⁷ or -CO ₂ R ⁷ ; for each optionally one or more times, identically or differently, by fluorine, chlorine, bromine, cyano, methylamino, ethylamino, di- (C ₁ -C ₆ -alkyl) amino, C ₁ -C ₄ -alkoxy, C ₁ -C ₄ -Halogenalkoxy with 1 to 9 fluorine, chlorine and / or bromine atoms, C ₁ -C ₄ alkylthio and / or C ₁ -C ₄ -haloalkylthio with 1 to 9 fluorine, chlorine and / or bromine atoms substituted C ₁ - C ₁₆ alkyl or C ₂ -C ₁₆ alkenyl; for each optionally single to triple, identical or different, by fluorine, chlorine, bromine, cyano, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ haloalkyl , C ₁ -C ₄ haloalkoxy and / or C ₁ -C ₄ haloalkylthio each with 1 to 9 fluorine, chlorine and / or bromine atoms substituted C ₃ -C ₁₀ cycloalkyl, C ₃ -C ₆ cycloalkyl-C ₁ -C ₄ alkyl, phenyl, benzyl, phenylethyl, tetrazolyl, furyl, furfuryl, benzofuryl, tetrahydrofuryl, thienyl, thenyl, benzothienyl, thiolanyl, pyrrolyl, indolyl, pyrrolinyl, pyrrolidinyl, oxazolyl, benzoxazolyl, isoxazolyl, pyrazoleyl , Benzothiazolyl, thiazolidinyl, pyridinyl, pyrimidinyl, pyridazyl, pyrazinyl, piperidinyl, morpholinyl, thiomorpholinyl, triazinyl, triazolyl, quinolinyl or isoquinolinyl,
R ^{22 represents} hydrogen, C ₁ -C ₄ alkyl or C ₂ -C ₄ alkenyl,
w represents 0, 1 or 2,
n represents 1 or 2,
p stands for 0 or 1. 5. Δ ¹ -pyrrolines of the formula (I) according to claim 1, in
R ^{1 represents} methyl, ethyl, or optionally monosubstituted aryl, where the substituents from the series fluorine, methyl, ethyl, n-, i-propyl, n-, i-, s-, t-butyl, methoxy, ethoxy , n-, i-propoxy, n-, i-, s-, t-butoxy, methylthio, ethylthio, n-, i-propylthio, n-, i-, s-, t-butylthio, trifluoromethyl, and trifluoromethoxy are,
R ^{2 represents} fluorine, chlorine, bromine, cyano or methyl,
R ^{3 represents} hydrogen or fluorine,
R ^{4 stands} for the grouping -XYZE with the proviso that Y does not stand for a direct bond if X does not stand for a direct bond,
R ⁵ for fluorine, chlorine, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, trifluoromethyl, trifluoroethyl, methoxy, ethoxy, n-propoxy, i-propoxy , n-butoxy, i-butoxy, s-butoxy, t-butoxy, trifluoromethoxy, trifluoroethoxy, methylthio, ethylthio, n-propylthio, i-propylthio, n-butylthio, i-butylthio, s-butylthio, t-butylthio, trifluoromethylthio or trifluoroethylthio,
m represents 0 or 1,
X for a direct bond, oxygen, sulfur, -SO ₂ -, -NR ⁶ -, -CO-, -C (O) -O-, -OC (O) -, -CH ₂ -, - (CH ₂ ) ₂ -, -C = C- (E or Z), -C ~ C-, -CH ₂ O-, - (CH ₂ ) ₂ O-, -OCH ₂ -, -O (CH ₂ ) ₂ -, - O-CH ₂ -O-, -SCH ₂ -, -S (CH ₂ ) ₂ -, -CH ₂ S- or - (CH ₂ ) ₂ S-,
Y for a direct bond or for in each case optionally single or double, identical or different, substituted by radicals from the list W ^1, 1,4-phenylene, 1,3-phenylene, 2,6-naphthylene, 2,7-naphthylene, 2, 4-furylene, 2,4-thienylene, 2,5-pyridinylene, 2,5-pyrimidinylene, 3,6-pyridazinylene or 2,5-pyrazinylene,
Z is a direct bond, methylene or ethylene,
E for hydrogen, fluorine, chlorine, bromine, hydroxy, cyano, formyl, -S (O) _w R ⁷ , -OSO ₂ R ⁷ , -NR ⁸ R ⁹ , -COR ⁷ , -CO ₂ R ⁷ , -OC ( O) R ⁷ , -CONR ¹⁰ R ¹¹ , -N (R ¹² ) COR ¹³ , -SO ₂ NR ¹⁶ R ¹⁷ -N (R ¹⁵ ) CO ₂ R ¹⁹ , -N (R ¹⁸ ) C (O) NR ¹⁹ R ²⁰ ; in each case optionally monosubstituted or polysubstituted by identical or different fluorine, chlorine, bromine, cyano, C ₁ - C ₆ alkoxy and / or -NR ⁸ R ⁹ substituted C ₁ -C ₁₆ alkyl, C ₂ -C ₁₆ - alkenyl , C ₁ -C ₁₆ alkoxy, C ₂ -C ₁₆ alkenyloxy; or for each optionally single to triple, identical or different by fluorine, chlorine, bromine, cyano, methyl, ethyl, n-propyl, i-propyl, -CF ₃ , -CHF ₂ , -CClF ₂ , -CF ₂ CHFCl, - CF ₂ CH ₂ F, -CF ₂ CCl ₃ , -CH ₂ CF ₃ , -CF ₂ CHFCF ₃ , -CH ₂ CF ₂ H, -CH ₂ CF ₂ CF ₃ , -CF ₂ CF ₂ H, -CF ₂ CHFCF ₃ , vinyl, allyl, 1-propenyl, butenyl, -CF = CHF, -CF = CH ₂ , -CF = CCl ₂ , -CH = CF ₂ , -CF ₂ CF = CF ₂ , -CH = CFH, -CH ₂ CF = CF ₂ , -CF = CF ₂ , -CF ₂ CH = CF ₂ , methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy, t-butoxy, trifluoromethoxy, Difluoromethoxy, chlorodifluoromethoxy, trifluoroethoxy, methylthio, ethylthio, n-propylthio, i-propylthio, n-butylthio, i-butylthio, s-butylthio, t-butylthio, trifluoromethylthio, difluoromethylthio, chlordififluoromethyl, cyclodifluoromethyl Cyclopentyloxy, cyclohexyloxy, cyclopropylmethyl, cyclopentylmethyl, cyclohexylmethyl, phenyl, phenoxy, benzyl, phenylethyl, benzyloxy, tetrazole yl, furyl, furfuryl, benzofuryl, tetrahydrofuryl, thienyl, thenyl, benzothienyl, thiolanyl, pyrrolyl, indolyl, pyrrolinyl, pyrrolidino, pyrrolidinyl, oxazolyl, benzoxazolyl, isoxazolyl, imidazolyl, pyrazolyl, thiazolyl, pyriazoleyl Pyrazinyl, piperidinyl, piperidino, morpholinyl, thiomorpholinyl, morpholino, thiomorpholino, triazinyl, triazolyl, quinolinyl or isoquinolinyl,
W ¹ for fluorine, chlorine, bromine, cyano, formyl, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, methoxy, ethoxy, n-propoxy, i -Propoxy, n-butoxy, i-butoxy, s-butoxy, t-butoxy, vinyl, allyl, trifluoromethyl, trifluoroethyl, trifluoromethoxy, trifluoroethoxy, -OCF ₂ CF ₂ H, -CH = CF ₂ , -CH = CCl ₂ , -OCF = CF ₂ , -COMe, -COEt, -CO ₂ Me, -CO ₂ Et, -CO ₂ (t-Bu), -SMe, -SOMe, -SO ₂ Me, -SCF ₃ , -SOCF ₃ , -SO ₂ CF ₃ , -SCHF ₂ , -SOCHF ₂ , -SO ₂ CHF ₂ , -SO ₂ NMe ₂ , -NMe ₂ , -NEt ₂ , -N (n-Pr) ₂ , -N (Me) COMe, -N (Me) COEt, -N (Me) COPr, -N (Me) CO (t-Bu), 2-pyrrolidon-5-yl, 2-piperidon-6-yl, -N (Me) SO ₂ Me , -N (Me) SO ₂ Et, -N (Me) SO ₂ CF ₃ , -N (Et) SO ₂ CF ₃ , -N (Me) SO ₂ (CF ₂ ) ₃ CF ₃ or -OSO ₂ NMe ₂ stands,
R ⁶ for methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, trifluoromethyl, trifluoroethyl, cyclopropyl, cyclopropylmethyl, cyclopentyl, cyclopentylmethyl, cyclohexyl, cyclohexylmethyl, phenyl, benzyl or phenylethyl,
R ^{7 is} methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, pentyl, hexyl, -CF ₃ , -CHF ₂ , -CCl ₃ , -CCl ₂ F is dimethylaminomethyl, dimethylaminoethyl, diethylaminomethyl, diethylaminoethyl, cyclopropyl, cyclopentyl, cyclohexyl, phenyl or benzyl,
R ⁸ and R ⁹ independently of one another for hydrogen, -SO ₂ R ⁷ , for each optionally one or more times, identically or differently by fluorine, chlorine and / or bromine, C ₁ -C ₄ -alkylcarbonyl, C ₁ -C ₄ -alkylcarbonyloxy , C ₁ -C ₄ alkylamino, di (C ₁ -C ₄ alkyl) amino, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy with 1 to 9 fluorine, chlorine and / or bromine atoms C ₁ -C ₄ alkylthio and / or C ₁ -C ₄ haloalkylthio with 1 to 9 fluorine, chlorine and / or bromine atoms substituted C ₁ -C ₁₆ alkyl, C ₂ - C ₁₆ alkenyl; for each optionally single to triple, identical or different, by fluorine, chlorine and / or bromine, cyano, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -haloalkyl having 1 to 9 fluorine, chlorine and / or bromine atoms, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy with 1 to 9 fluorine, chlorine and / or bromine atoms, C ₁ -C ₄ alkylthio and / or C ₁ -C ₄ haloalkylthio with 1 to 9 Fluorine, chlorine and / or bromine atoms substituted C ₃ -C ₈ cycloalkyl, cyclopropylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclopropylethyl, cyclopentylethyl, cyclohexylethyl, phenyl, benzyl, phenylethyl, tetrazolyl, furyl, furfuryl, benzofuryl, tetrahylrofuryl, thien Benzothienyl, thiolanyl, pyrrolyl, indolyl, pyrrolinyl, pyrrolidinyl, oxazolyl, benzoxazolyl, isoxazolyl, imidazolyl, pyrazolyl, thiazolyl, benzothiazolyl, thiazolidinyl, pyridinyl, pyrimidinyl, pyridazyl, pyrazinyl, piperidinyl, morphololinyl, morphololinyl, morphololinyl, morphololinyl, morphololinyl, morphololinyl, morphololinyl, morphololinyl .
R ⁸ and R ⁹ also together for optionally single or multiple, identical or different by fluorine, chlorine and / or bromine, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy with 1 to 9 fluorine, chlorine and / or bromine atoms, C ₁ -C ₄ alkylthio and / or C ₁ -C ₄ haloalkylthio with 1 to 9 fluorine, chlorine and / or bromine atoms substituted C ₂ -C ₈ alkenylene or for single or multiple, optionally in the alkylene part , identical or different by fluorine, chlorine, cyano, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, C ₁ -C ₄ haloalkyl with 1 to 9 Fluorine, chlorine and / or bromine atoms, methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy, t-butoxy, C ₁ -C ₄ haloalkoxy with 1 to 9 fluorine -, Chlorine and / or bromine atoms, methylthio, ethylthio, n-propylthio, i-propylthio, n-butylthio, i-butylthio, s-butylthio, t-butylthio and / or C ₁ -C ₄ -haloalkylthio with 1 to 9 Fluorine, chlorine and / or bromine atoms substituted C ₃ -C ₈ alkylene, the Alkylene chain can be interrupted in each case by -O-, -S- or -NR ¹⁴ -,
R ¹⁰ and R ¹¹ independently of one another are hydrogen, -SO ₂ CF ₃ , methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, pentyl, hexyl, -CF ₃ , -CH ₂ CF ₃ , - (CF ₂ ) ₃ CF ₃ , cyclopropyl, cyclopentyl, cyclohexyl, methoxymethyl, methoxyethyl, or for each optionally single to triple, identical or different by fluorine, chlorine, bromine, methyl, trifluoromethyl, methoxy , Trifluoromethoxy substituted phenyl or benzyl,
R ¹⁰ and R ¹¹ also together for - (CH ₂ ) ₄ -, - (CH ₂ ) ₅ -, - (CH ₂ ) ₆ -, -CH ₂ -CH (CH ₃ ) -CH ₂ -CH (CH ₃ ) -CH ₂ -, - (CH ₂ ) ₂ -O- (CH ₂ ) ₂ -, - (CH ₂ ) ₂ -S- (CH ₂ ) ₂ - or - (CH ₂ ) ₂ -N (R ²¹ ) - (CH ₂ ) ₂ - stand,
R ¹² and R ¹³ independently of one another are methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, n-hexyl, trifluoromethyl, trifluoroethyl, cyclopropyl, cyclopentyl, cyclohexyl or represent phenyl or benzyl which are each mono- to tetrasubstituted, identically or differently, by fluorine, chlorine, bromine, methyl, trifluoromethyl, methoxy, trifluoromethoxy,
R ¹² and R ¹³ furthermore together for in each case optionally up to four times, the same or different, substituted by fluorine, chlorine, bromine, methyl, ethyl, methoxy, ethoxy, methylthio, ethylthio, trifluoromethyl, trifluoromethoxy, trifluoromethylthio -, (CH ₂ ) ₃ -, - (CH ₂ ) ₄ -, - (CH ₂ ) ₅ -, - (CH ₂ ) ₆ - stand,
R ¹⁶ and R ¹⁷ independently of one another are hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, n-hexyl, trifluoromethyl, trifluoroethyl, cyclopropyl, cyclopentyl or Cyclohexyl,
R ¹⁶ and R ¹⁷ also together for - (CH ₂ ) ₃ -, - (CH ₂ ) ₄ -, - (CH ₂ ) ₅ -, - (CH ₂ ) ₂ -O- (CH ₂ ) ₂ - or - ( CH ₂ ) ₂ -S- (CH ₂ ) ₂ - stand,
R ^{18 represents} hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl or t-butyl,
R ¹⁹ and R ²⁰ independently of one another for hydrogen, each in each case optionally single or multiple, identical or different, by fluorine, chlorine, bromine, C ₁ -C ₄ -alkylcarbonyl, C ₁ -C ₄ -alkylcarbonyloxy, C ₁ -C ₄ - Alkylamino, di (C ₁ -C ₄ alkyl) amino, C ₁ -C ₁₀ alkoxy, C ₁ -C ₈ alkoxy- C ₁ -C ₆ alkoxy, C ₁ -C ₁₀ alkylthio, C ₁ - C ₁₀ haloalkoxy, C ₁ -C ₁₀ haloalkylthio each having 1 to 21 fluorine, chlorine and / or bromine atoms, C ₁ -C ₈ haloalkoxy-C ₁ -C ₆ alkoxy with 1 to 17 fluorine, chlorine - and / or bromine atoms substituted C ₁ -C ₁₀ alkyl or C ₂ -C ₁₀ alkenyl (especially methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl , the isomeric pentyls, the isomeric hexyls);
for each optionally single to triple, identical or different, by fluorine, chlorine, bromine, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ haloalkoxy, C ₁ -C ₄ haloalkylthio each having 1 to 9 fluorine, chlorine and / or bromine atoms, C ₁ -C ₄ alkylcarbonyl and / or C ₁ -C ₄ alkoxycarbonyl substituted C ₃ - C ₈ -cycloalkyl, cyclopropylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclopropylethyl, cyclopentylethyl, cyclohexylethyl, phenyl, benzyl, phenylethyl, tetrazolyl, furyl, furfuryl, benzofuryl, tetrahydrofuryl, thienyl, thenyl, benzothienyl, pyrolylolololololylolololololololylolyrylolol , Benzoxazolyl, isoxazolyl, imidazolyl, pyrazolyl, thiazolyl, benzothiazolyl, thiazolidinyl, pyridinyl, pyrimidinyl, pyridazyl, pyrazinyl, piperidinyl, morpholinyl, thiomorpholinyl, triazinyl, triazolyl, quinolinyl or isoquinolinyl,
R ¹⁸ and R ¹⁹ also together represent in each case optionally single or double, identical or different, methylene or ethylene substituted by methyl, ethyl, n-propyl or i-propyl, or
R ¹⁹ and R ²⁰ also together with the nitrogen atom to which they are attached for a 5- to 6-membered heterocycle from the series piperidino, morpholino, thiomorpholino, piperazino, pyrrolidino, oxazolidino, thiazolidino, 4H-1-oxazinyl, 4H -1-thiazinyl, which is optionally one to four times, identical or different, by fluorine, chlorine, bromine, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, Methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy, t-butoxy, methylthio, ethylthio, n-propylthio, i-propylthio, n-butylthio, i-butylthio, s- Butylthio, t-butylthio, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ haloalkoxy, C ₁ - C ₄ haloalkylthio can each be substituted with 1 to 9 fluorine, chlorine and / or bromine atoms, the rest Piperazino on the second nitrogen atom is substituted by R ²² , and
R ²¹ for hydrogen, -SO ₂ R ⁷ , for -COR ⁷ or -CO ₂ R ⁷ ; for each optionally one or more times, identically or differently, by fluorine, chlorine, bromine, cyano, methylamino, ethylamino, di- (C ₁ -C ₆ -alkyl) amino, C ₁ -C ₄ -alkoxy, C ₁ -C ₄ -Halogenalkoxy with 1 to 9 fluorine, chlorine and / or bromine atoms, C ₁ -C ₄ alkylthio and / or C ₁ -C ₄ -haloalkylthio with 1 to 9 fluorine, chlorine and / or bromine atoms substituted C ₁ - C ₁₆ alkyl, C ₂ -C ₁₆ alkenyl; for each optionally single to triple, identical or different, by fluorine, chlorine, bromine, cyano, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, C ₁ - C ₄ haloalkyl with 1 to 9 fluorine, chlorine and / or bromine atoms, methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy, t-butoxy, C ₁ -C ₄ -haloalkoxy with 1 to 9 fluorine, chlorine and / or bromine atoms, methylthio, ethylthio, n-propylthio, i-propylthio, n-butylthio, i-butylthio, s-butylthio, t-butylthio and / or C ₁ - C ₄ - haloalkylthio with 1 to 9 fluorine, chlorine and / or bromine atoms substituted C ₃ -C ₈ cycloalkyl, cyclopropylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclopropylethyl, cyclopentylethyl, cyclohexylethyl, phenyl, benzyl, phenylethyl, tetrazolyl, furyl, furfuryl, Benzofuryl, tetrahydrofuryl, thienyl, thenyl, benzothienyl, thiolanyl, pyrrolyl, indolyl, pyrrolinyl, pyrrolidinyl, oxazolyl, benzoxazolyl, isoxazolyl, imidazolyl, pyrazolyl, thiazolyl, benzothiazolyl, thiazole idinyl, pyridinyl, pyrimidinyl, pyridazyl, pyrazinyl, piperidinyl, morpholinyl, thiomorpholinyl, triazinyl, triazolyl, quinolinyl or isoquinolinyl,
R ^{22 represents} hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, vinyl or allyl. 6. Δ ¹ -pyrrolines of formula (I) according to any one of claims 1 to 5, in which R ^{1 is} methyl. 7. Δ ¹ -pyrrolines of the formula (I) according to one of claims 1 to 5, in which R ^{1 is} phenyl. 8. Δ ¹ -pyrrolines of the formula (I) according to one of claims 1 to 7, in which R ² and R ^{3 are} fluorine. 9. Δ ¹ -pyrrolines of the formula (I) according to one of claims 1 to 7, in which R ^{2 represents} fluorine, chlorine, bromine, cyano or methyl and R ^{3 represents} hydrogen. 10. Δ ¹ -pyrrolines of the formula (I) according to any one of claims 1 to 9, in which R ^{4 represents} the grouping -YE, where Y is 1,4-phenylene and E is that specified in one of claims 1 to 5 Has meanings. 11. Δ ¹ -pyrrolines of the formula (Id)


in which
R ^{1a represents} C ₁ -C ₈ alkyl (preferably C ₂ -C ₄ alkyl),
R ^{2a represents} fluorine, chlorine, bromine, cyano, nitro, C ₁ -C ₄ alkyl or C ₁ -C ₄ alkoxy,
R ^{3a represents} hydrogen, fluorine, chlorine, bromine, C ₁ -C ₄ alkyl or C ₁ -C ₄ alkoxy,
R ^4a for hydrogen, fluorine, chlorine, bromine, iodine, C ₁ -C ₈ -alkyl, C ₁ -C ₈ -haloalkyl, -OSO ₂ CF ₃ or for optionally single or double, identical or different by halogen, C ₁ - C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ -haloalkoxy and C ₁ - C ₄ haloalkylthio having in each case 1 to 9 fluorine -, Chlorine and / or bromine atoms substituted phenyl or for optionally simply by halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ haloalkoxy and C ₁ -C ₄ haloalkylthio, each with 1 to 9 fluorine, chlorine and / or bromine atoms, C ₁ -C ₄ alkylamino or di (C ₁ -C ₄ alkyl) amino substituted Pyridyl or pyrimidinyl is. 12. Compounds of formula (Id) according to claim 11, in which
R ^{1a represents} methyl, ethyl, n-, i-propyl, n-, i-, s-, t-butyl,
R ^{2a represents} fluorine, chlorine, bromine, cyano or methyl,
R ^{3a represents} hydrogen or fluorine,
R ^{4a represents} hydrogen, fluorine, chlorine, bromine, iodine, -OSO ₂ CF ₃ or simply phenyl substituted in the 4-position by chlorine, methoxy, methylthio, trifluoromethyl, trifluoromethoxy, trifluoromethylthio. 13. Δ ¹ -pyrrolines of the formula (Ie)


in which
R ^1a for unsubstituted phenyl or for single or double, identical or different by fluorine, chlorine, bromine, iodine, cyano, nitro, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio , C ₁ -C ₄ haloalkyl, C ₁ -C ₄ - haloalkoxy and C ₁ -C ₄ -haloalkylthio having in each case 1 to 9 fluorine, chlorine and / or bromine-substituted phenyl,
R ^{2b represents} fluorine, chlorine, bromine, cyano, nitro, C ₁ -C ₄ alkyl or C ₁ -C ₄ alkoxy,
R ^{3b represents} hydrogen, fluorine, chlorine, bromine, C ₁ -C ₄ alkyl or C ₁ -C ₄ alkoxy,
R ^4b for hydrogen, fluorine, chlorine, bromine, iodine, C ₁ -C ₈ -alkyl, C ₁ -C ₈ -haloalkyl, -OSO ₂ CF ₃ or for optionally single or double, identical or different by halogen, C ₁ - C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ -haloalkoxy and C ₁ - C ₄ haloalkylthio having in each case 1 to 9 fluorine -, Chlorine and / or bromine atoms substituted phenyl or for optionally simply by halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ haloalkoxy and C ₁ -C ₄ haloalkylthio, each with 1 to 9 fluorine, chlorine and / or bromine atoms, C ₁ -C ₄ alkylamino or di (C ₁ -C ₄ alkyl) amino substituted Pyridyl or pyrimidinyl is. 14. Compounds of formula (Ie) according to claim 13, in which
R ^{1b represents} unsubstituted phenyl or phenyl which is monosubstituted in the 4-position by fluorine, trifluoromethyl, trifluoromethoxy or trifluoromethylthio,
R ^{2b represents} fluorine, chlorine, bromine, cyano or methyl,
R ^{3b represents} hydrogen or fluorine,
R ^{4b represents} hydrogen, fluorine, chlorine, bromine, iodine, -OSO ₂ CF ₃ or simply phenyl substituted in the 4-position by chlorine, methoxy, methylthio, trifluoromethyl, trifluoromethoxy, trifluoromethylthio. 15. (R) -configured compounds of the formula (If)


in which
R ¹ , R ² , R ³ , R ⁴ , R ⁵ and m have the meanings given in one of Claims 1 to 10. 16. A method for producing Δ ¹ -pyrroline of the formula (I) according to claim 1, characterized in that A) Aroylpyrrolidinones of the formula (II)


in which
R ¹ , R ² , R ³ , R ⁴ , R ⁵ and m have the meanings given in Claim 1,
with an acid, if appropriate in the presence of a diluent, or B) Compounds of the formula (III)


in which
R ¹ , R ² , R ³ , R ⁴ , R ⁵ and m have the meanings given in Claim 1,
with an acid, if appropriate in the presence of a diluent, or that Δ ¹ -pyrrolines of the formula (Ia)


in which
R ^{41 stands} for the grouping -Y ¹ -E,
Y ^{1 represents} in each case optionally substituted phenylene or heterocyclylene,
R ¹ , R ² , R ³ , R ⁵ , m and E have the meanings given in claim 1,
obtained by A) Δ ¹ -pyrrolines of the formula (Ib)


in which
R ^{42 represents} chlorine, bromine, iodine, -OSO ₂ CF ₃ or -OSO ₂ (CF ₂ ) ₃ CF ₃ ,
R ¹ , R ² , R ³ , R ⁵ and m have the meanings given in Claim 1,
with cyclic compounds of the formula (IV)

A ¹ -Y ¹ -E (IV)

in which
Y ^{1 has} the meanings given above,
E have the meanings given in claim 1 and
A ^{1 represents} chlorine, bromine, iodine, -OSO ₂ CF ₃ or -OSO ₂ (CF ₂ ) ₃ CF ₃ ,
in a tandem reaction in the presence of a catalyst, in the presence of a diboronic acid ester and optionally in the presence of an acid binder and optionally in the presence of a diluent, or B) Δ ¹ -pyrrolines of the formula (V)


in which
A ² for for -B (OH) ₂ , (4,4,5,5-tetramethyl-1,3,2-dioxaborolane) -2-yl, (5,5-dimethyl-1,3,2-dioxaborinane) -2-yl, (4,4,6-trimethyl-1,3,2-dioxaborinan) -2-yl or 1,3,2-benzodioxaborol-2-yl,
R ¹ , R ² , R ³ , R ⁵ and m have the meanings given above,
with cyclic compounds of the formula (IV)

A ¹ -Y ¹ -E (IV)

in which
Y ¹ and A ^{1 have} the meanings given above and
E has the meanings given in claim 1,
in the presence of a catalyst, if appropriate in the presence of an acid binder and if appropriate in the presence of a diluent, or C) Δ ¹ -pyrrolines of the formula (Ib)


in which
R ¹ , R ² , R ³ , R ⁵ and m have the meanings given in claim 1, and
R ^{42 has} the meanings given above,
with boronic acid derivatives of the formula (VI)

A ² -Y ¹ -E (VI)

in which
Y ¹ and A ^{2 have} the meanings given above and
E has the meanings given in claim 1,
in the presence of a catalyst, if appropriate in the presence of an acid binder and if appropriate in the presence of a diluent, or D) Δ ¹ -pyrrolines of the formula (Ic)


in which
R ^{43 represents} bromine or iodine,
R ¹ , R ² , R ³ , R ⁵ and m have the meanings given in Claim 1,
with organometallic compounds of the formula (VII)

MY ¹ -E (VII)

in which
M represents ZnCl, Sn (Me) ₃ or Sn (n-Bu) ₃ ,
Y ^{1 has} the meanings given above,
E has the meanings given in claim 1,
in the presence of a catalyst, optionally in the presence of an acid binder and optionally in the presence of a diluent. 17. pesticide, characterized by a content of at least one compound of formula (I) according to claim 1 in addition to extenders and / or surfactants. 18. Use of compounds of formula (I) according to claim 1 for Pest control. 19. Method of combating pests, characterized in that compounds of formula (I) according to claim 1 on pests and / or their living space. 20. Process for the preparation of pesticides, thereby characterized in that compounds of formula (I) according to claim 1 with Extenders and / or surfactants mixed. 21. Aroylpyrrolidinones of the formula (II)


in which
R ¹ , R ² , R ³ , R ⁴ , R ⁵ and m have the meanings given in Claim 1. 22. Compounds of the formula (III)


in which
R ¹ , R ² , R ³ , R ⁴ , R ⁵ and m have the meanings given in Claim 1. 23. Lactams of the formula (VIII)


in which
R ¹ , R ⁴ , R ⁵ and m have the meanings given in Claim 1. 24. Pyrrolidinones of the formula (X)


in which
R ¹ , R ⁴ , R ⁵ and m have the meanings given in Claim 1. 25. Amino acids of the formula (XI)


in which
R ¹ , R ⁴ , R ⁵ and m have the meanings given in Claim 1.