Delta 1-pyrrolines used as pesticides

Abstract

Novel Δ 1 -pyrrolines of the formula (I) in which R 1 , R 2 , R 3 , A, R 4 and m have the meanings given in the description, a number of processes for preparing these substances and their use for controlling pests, and also novel intermediates and their preparation.

1 . Δ 1 -Pyrrolines of the formula (I)  
     
       
         
         
             
             
         
       
       in which  
       R 1  represents halogen or methyl,  
       R 2  represents hydrogen or halogen,  
       R 3  represents —N(R 6 )—C(═Y)—X—R 7 ,  
       and  
       a) 
 A represents arylene or 5-membered heteroarylene having 1 to 3 heteroatoms, containing 0 to 3 nitrogen atoms, 0 to 1 oxygen atom and/or 0 to 1 sulphur atom, or 6-membered heteroarylene having 3 nitrogen atoms or 6-membered heteroarylene having 1 nitrogen atom and 1 to 2 further heteroatoms, of which 0 to 2 may be oxygen atoms and/or 0 to 2 may be sulphur atoms, each arylene or heteroarylene being optionally substituted from one to four times by identical or different substituents R 5 , and  
 Y represents O (oxygen) or S (sulphur), and  
 X represents O (oxygen), S (sulphur) or NR 8 ,  
 
       or  
       b) 
 A represents pyridinylene, pyrimidinylene, pyrazinylene or pyridazinylene each optionally substituted once or twice by identical or different substituents R 5 , and  
 Y represents O (oxygen) or S (sulphur), and  
 X represents S (sulphur) or NR 8 ,  
 
       or  
       c) 
 A represents pyridinylene, pyrimidinylene, pyrazinylene or pyridazinylene each optionally substituted once or twice by identical or different substituents R 5 , and  
 Y represents S (sulphur), and  
 X represents O (oxygen),  
 
       or  
       d) 
 A represents pyridinylene, pyrimidinylene, pyrazinylene or pyridazinylene each optionally substituted once or twice by identical or different substituents R 5 , and  
 Y represents O (oxygen), and  
 X represents O (oxygen),  
 
       and  
       R 4  and R 5  independently of one another represent halogen, alkyl, alkoxy, alkylthio, haloalkyl, haloalkoxy or haloalkylthio,  
       m represents 0, 1, 2, 3 or 4,  
       R 6  represents hydrogen or alkyl,  
       R 7  and R 8  independently of one another represent hydrogen or represent alkyl or alkenyl each optionally substituted one or more times by identical or different substituents selected from the group consisting of halogen, alkylcarbonyl, alkylcarbonyloxy, alkylamino, dialkylamino, alkoxy, alkylthio, alkoxyalkoxy, haloalkoxy, haloalkylthio and halogenalkoxyalkoxy; 
 or represent cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, saturated or unsaturated 5- to 10-membered heterocyclyl or heterocyclylalkyl each of which is optionally substituted one or more times by identical or different substitutents selected from the group consisting of halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylcarbonyl and alkoxycarbonyl,  
 
       R 6  and R 7  further together represent alkylene optionally substituted one or more times by alkyl, or  
       R 7  and R 8  further, together with the nitrogen atom to which they are attached, represent a saturated or unsaturated 5- to 10-membered heterocycle which may optionally contain a further heteroatom group from the series —O—, —S— and —NR 9 — and which may optionally be substituted one or more times by identical or different substituents selected from the group consisting of halogen, alkyl, alkoxy, alkylthio, haloalkyl, haloalkoxy and haloalkylthio, and  
       R 9  represents hydrogen, alkyl or alkenyl.  
     
   
   
       2 . Δ 1 -Pyrrolines of the formula (I) according to  claim 1 , in which 
 R 1  represents fluorine, chlorine, bromine or methyl,    R 2  represents hydrogen, fluorine, chlorine or bromine,    R 3  represents —N(R 6 )—C(═Y)—X—R 7 ,    and    a) 
 A represents arylene (especially phenylene) or 5-membered heteroarylene having 1 to 3 heteroatoms, containing 0 to 3 nitrogen atoms, 0 to 1 oxygen atom and/or 0 to 1 sulphur atom (in particular from the series pyrrolylene, furylene, thienylene, pyrazylene, imidazylene, triazylene, thiazylene or oxazylene), or 6-membered heteroarylene having 3 nitrogen atoms (especially triazinylene) or 6-membered heteroarylene having 1 nitrogen atom and 1 to 2 further heteroatoms, of which 0 to 2 may be oxygen atoms and/or 0 to 2 may be sulphur atoms (in particular from the series oxazinylene or thiazinylene), each being optionally substituted from one to three times by identical or different substituents R 5 , and  
 Y represents O (oxygen) or S (sulphur) and  
 X represents O (oxygen), S (sulphur) or NR 8 ,  
   or    b) 
 A represents pyridinylene, pyrimidinylene, pyrazinylene or pyridazinylene each optionally substituted once or twice by identical or different substituents R 5 , and  
 Y represents O (oxygen) or S (sulphur), and  
 X represents S (sulphur) or NR 8 ,  
   or    c) 
 A represents pyridinylene, pyrimidinylene, pyrazinylene or pyridazinylene each optionally substituted once or twice by identical or different substituents R 5 , and  
 Y represents S (sulphur), and  
 X represents O (oxygen),  
   or    d) 
 A represents pyridinylene, pyrimidinylene, pyrazinylene or pyridazinylene each optionally substituted once or twice by identical or different substituents R 5 , and  
 Y represents O (oxygen), and  
 X represents O (oxygen),  
   and    R 4  and R 5  independently of one another 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,    m represents 0, 1, 2 or 3,    R 6  represents hydrogen or C 1 -C 6 -alkyl,    R 7  and R 8  independently of one another represent hydrogen or represent C 1 -C 20 -alkyl or C 2 -C 20 -alkenyl each optionally substituted one or more times by identical or different substituents selected from the group consisting of 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 C 1 -C 10 -haloalkoxy-C 1 -C 10 -alkoxy; 
 or represent 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, containing 0 to 4 nitrogen atoms, 0 to 2 non-adjacent oxygen atoms and/or 0 to 2 non-adjacent sulphur atoms (especially 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 or isoquinolinyl) each optionally substituted from one to four times by identical or different substituents selected from the group consisting of 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 C 1 -C 6 -alkoxycarbonyl,  
   R 6  and R 7  further together represent C 2 -C 4 -alkylene optionally substituted from one to four times by C 1 -C 4 -alkyl, or    R 7  and R 8  further represent, together with the nitrogen atom to which they are attached, a saturated or unsaturated 5- to 10-membered heterocycle which may optionally contain a further heteroatom group from the series —O—, —S— or —NR 9 — and which may optionally be substituted from one to four times by identical or different substituents selected from the group consisting of 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, and    R 9  represents hydrogen, C 1 -C 6 -alkyl or C 2 -C 6 -alkenyl.    
   
   
       3 . Δ 1 -Pyrrolines of the formula (I) according to  claim 1 , in which 
 R 1  represents fluorine, chlorine or methyl,    R 2  represents hydrogen, fluorine or chlorine,    R 3  represents —N(R 6 )—C(═Y)—X—R 7 ,    and    a) 
 A represents phenylene, pyrrolylene, furylene, thienylene, pyrazylene, imidazylene, triazylene, thiazylene or oxazylene each optionally substituted once or twice by identical or different substituents R 5 , and  
 Y represents O (oxygen) or S (sulphur), and  
 X represents O (oxygen), S (sulphur) or NR 8 ,  
   or    b) 
 A represents pyridinylene, pyrimidinylene, pyrazinylene or pyridazinylene each optionally substituted once or twice by identical or different substituents R 5 , and  
 Y represents O (oxygen) or S (sulphur), and  
 X represents S (sulphur) or NR 8 ,  
   or    c) 
 A represents pyridinylene, pyrimidinylene, pyrazinylene or pyridazinylene each optionally substituted once or twice by identical or different substituents R 5 , and  
 Y represents S (sulphur), and  
 X represents O (oxygen),  
   or    d) 
 A represents pyridinylene, pyrimidinylene, pyrazinylene or pyridazinylene each optionally substituted once or twice by identical or different substituents R 5 , and  
 Y represents O (oxygen), and  
 X represents O (oxygen),  
   and    R 4  and R 5  independently of one another represent 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 or C 1 -C 4 -haloalkylthio having in each case 1 to 9 fluorine, chlorine and/or bromine atoms,    m represents 0, 1 or 2,    R 6  represents hydrogen or C 1 -C 4 -alkyl,    R 7  and R 8  independently of one another represent hydrogen or represent C 1 -C 16 -alkyl or C 2 -C 16 -alkenyl each optionally substituted one or more times by identical or different substituents selected from the group consisting of 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 C 1 -C 10 -haloalkoxy-C 1 -C 6 -alkoxy having in each case 1 to 21 fluorine, chlorine and/or bromine atoms; 
 or represent 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 or isoquinolinyl each optionally substituted from one to three times by identical or different substituents selected from the group consisting of 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 having in each case 1 to 9 fluorine, chlorine and/or bromine atoms, C 1 -C 4 -alkylcarbonyl and C 1 -C 4 -alkoxycarbonyl,  
   R 6  and R 7  further together represent C 2 -C 3 -alkylene optionally substituted from one to three times by C 1 -C 4 -alkyl, or    R 7  and R 8  further represent, together with the nitrogen atom to which they are attached, a saturated or unsaturated 5- to 7-membered heterocycle which may optionally contain a further heteroatom group from the series —O—, —S— or —NR 9 — (in particular from the series piperidino, morpholino, thiomorpholino, piperazino, pyrrolidino, oxazolidino, thiazolidino, 4H-1-oxazinyl, 4H-1-thiazinyl) and which may optionally be substituted from one to four times by identical or different substituents selected from the group consisting of 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, and    R 9  represents hydrogen, C 1 -C 4 -alkyl or C 2 -C 4 -alkenyl.    
   
   
       4 . Δ 1 -Pyrrolines of the formula (I) according to  claim 1 , in which 
 R 1  represents fluorine or chlorine,    R 2  represents hydrogen or fluorine,    R 3  represents —N(R 6 )—C(═Y)—X—R 7 ,    and    a) 
 A represents 1,2-phenylene, 1,4-phenylene, 2,5-pyrrolylene, 2,5-furylene, 2,4-furylene, 2,5-thienylene, 2,4-thienylene, 2,5-thiazylene, 2,4-thiazylene, 2,5-oxazylene or 2,4-oxazylene each optionally substituted once by R 5 , and  
 Y represents O (oxygen) or S (sulphur), and  
 X represents O (oxygen), S (sulphur) or NR 8 ,  
   or    b) 
 A represents 2,5-pyridinylene, 2,5-pyrimidinylene, 2,5-pyrazinylene or 3,6-pyridazinylene each optionally substituted once by R 5 , and  
 Y represents O (oxygen) or S (sulphur), and  
 X represents S (sulphur) or NR 8 ,  
   or    c) 
 A represents 2,5-pyridinylene, 2,5-pyrimidinylene, 2,5-pyrazinylene or 3,6-pyridazinylene each optionally substituted once by R 5 , and  
 Y represents S (sulphur), and  
 X represents O (oxygen),  
   or    d) 
 A represents 2,5-pyridinylene, 2,5-pyrimidinylene, 2,5-pyrazinylene or 3,6-pyridazinylene each optionally substituted once by R 5 , and  
 Y represents O (oxygen), and  
 X represents O (oxygen),  
   and    R 4  and R 5  independently of one another represent fluorine, chlorine, 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, trifluoromethyl, trifluoroethyl, trifluoromethoxy, trifluoroethoxy, trifluoromethylthio or trifluoroethylthio,    m represents 0 or 1,    R 6  represents hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl or t-butyl,    R 7  and R 8  independently of one another represent hydrogen or represent 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) each optionally substituted one or more times by identical or different substituents selected from the group consisting of 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 having in each case 1 to 21 fluorine, chlorine and/or bromine atoms, C 1 -C 8 -haloalkoxy-C 1 -C 6 -alkoxy having 1 to 17 fluorine, chlorine and/or bromine atoms; 
 or represent 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, thiazolidinyl, pyridinyl, pyrimidinyl, pyridazyl, pyrazinyl, piperidinyl, morpholinyl, thiomorpholinyl, triazinyl, triazolyl, quinolinyl or isoquinolinyl each optionally substituted from one to three times by identical or different substituents selected from the group consisting of 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 having in each case 1 to 9 fluorine, chlorine and/or bromine atoms, C 1 -C 4 -alkylcarbonyl and C 1 -C 4 -alkoxycarbonyl,  
   R 6  and R 7  further together represent methylene or ethylene each optionally substituted once or twice by identical or different methyl, ethyl, n-propyl or i-propyl substituents, or    R 7  and R 8  further represent, together with the nitrogen atom to which they are attached, a 5- to 6-membered heterocycle from the series piperidino, morpholino, thiomorpholino, piperazino, pyrrolidino, oxazolidino, thiazolidino, 4H-1-oxazinyl, 4H-1-thiazinyl which may optionally be substituted from one to four times by identical or different substituents selected from the group consisting of 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 having in each case 1 to 9 fluorine, chlorine and/or bromine atoms, the piperazino radical being substituted on the second nitrogen atom by R 9 , and    R 9  represents hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, vinyl or allyl.    
   
   
       5 . Δ 1 -Pyrrolines of the formulae (I-1) and (I-2)  
     
       
         
         
             
             
         
       
       in each of which  
       a) 
 Y represents O (oxygen) or S (sulphur), and  
 X represents O (oxygen), S (sulphur) or NR 8 ,  
 
       and R 1 , R 2 , R 4 , R 5 , m, R 6 , R 7 , R 8  have the meanings given in  claim 1 .  
     
   
   
       6 . Δ 1 -Pyrrolines of the formulae (I-3) to (I-8)  
     
       
         
         
             
             
         
       
       in each of which  
       p represents 0, 1 or 2,  
       b) 
 Y represents O (oxygen) or S (sulphur), and  
 X represents S (sulphur) or NR 8 ,  
 
       or  
       c) 
 Y represents S (sulphur), and  
 X represents O (oxygen),  
 
       or  
       d) 
 Y represents O (oxygen), and  
 X represents O (oxygen),  
 
       and R 1 , R 2 , R 4 , R 5 , m, R 6 , R 7  and R 8  have the meanings given in  claim 1 .  
     
   
   
       7 . Δ 1 -Pyrrolines of the formula (I) according to  claim 1 , in which A represents phenylene, preferably 1,4-phenylene.  
   
   
       8 . Δ 1 -Pyrrolines of the formula (I) according to  claim 1 , in which A represents pyridinylene, pyrimidinylene, pyrazinylene or pyridazinylene, preferably 2,5-pyridinylene, 2,5-pyrimidinylene, 2,5-pyrazinylene or 3,6-pyridazinylene.  
   
   
       9 . Δ 1 -Pyrrolines of the formula (I) according to  claim 1 , in which Y represents O (oxygen).  
   
   
       10 . Δ 1 -Pyrrolines of the formula (I) according to  claim 1 , in which X represents O (oxygen) or NR 8 , preferably represents O (oxygen).  
   
   
       11 . Δ 1 -Pyrrolines of the formula (I) according to  claim 1 , in which Y and X each represent O (oxygen).  
   
   
       12 . Δ 1 -Pyrrolines of the formula (I) according to  claim 1 , in which Y represents O (oxygen) and X represents NR 8 .  
   
   
       13 . Δ 1 -Pyrrolines of the formula (I) according to  claim 1 , in which A represents phenylene, preferably 1,4-phenylene, Y represents O (oxygen) or S (sulphur), preferably O (oxygen), and X represents O (oxygen), S (sulphur) or NR 8 , preferably O (oxygen) or NR 8 , with particular preference O (oxygen).  
   
   
       14 . Δ 1 -Pyrrolines of the formula (I) according to  claim 1 , in which R 1  and R 2  each represent fluorine.  
   
   
       15 . Δ 1 -Pyrrolines of the formula (I) according to  claim 1 , in which R 1  represents methyl and R 2  represents hydrogen.  
   
   
       16 . Δ 1 -Pyrrolines of the formula (I) according to  claim 1 , in which R 1  represents chlorine and R 2  represents hydrogen.  
   
   
       17 . Δ 1 -Pyrrolines of the formula (I) according to  claim 1 , in which R 1  represents chlorine and R 2  represents fluorine.  
   
   
       18 . Δ 1 -Pyrrolines of the formula (I) according to  claim 1 , in which R 6  represents hydrogen.  
   
   
       19 . Δ 1 -Pyrrolines of the formula (I-a) with (R) configuration in position 5 of the pyrroline ring.  
     
       
         
         
             
             
         
       
       in which  
       R 1 , R 2 , A, R 3 , R 4  and m have the meanings given in  claim 1 .  
     
   
   
       20 . Process for preparing compounds of the formula (I) according to  claim 1 , characterized by 
 A) reacting Δ 1 -pyrrolines of the formula (II)                        in which    R 1 , R 2 , R 4  and m have the meanings given in  claim 1  and    Z 1  represents chlorine, bromine, iodine, —OSO 2 CF 3  or —OSO 2 (CF 2 ) 3 CF 3 ,    in a tandem reaction with (hetero)cycles of the formula (III)                          in which    A, R 6  and R 7  have the meanings given in  claim 1 ,    Y 1  represents O (oxygen),    X 1  represents O (oxygen) or NR 8 ,    E represents chlorine, bromine, iodine, —OSO 2 CF 3  or —OSO 2 (CF 2 ) 3 CF 3 ,    in the presence of a catalyst, in the presence of a diboronic ester and, where appropriate, in the presence of an acid binder and, where appropriate, in the presence of a diluent,      or    B) reacting Δ 1 -pyrrolines of the formula (IV)                        in which    R 1 , R 2 , R 4  and m have the meanings given in  claim 1 ,    Z 2  represents —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 or 1,3,2-benzodioxaborol-2-yl,    with (hetero)cycles of the formula (III)                          in which    A, R 6  and R 7  have the meanings given in  claim 1 ,    E, Y 1  and X 1  have the above given meanings,    in the presence of a catalyst, where appropriate in the presence of an acid binder and, where appropriate, in the presence of a diluent,      or    C) reacting Δ 1 -pyrrolines of the formula (II)                        in which    R 1 , R 2 , R 4  and m Z 1  have the meanings given in  claim 1 ,    Z 1  have the meanings given above,    with boronic acid derivatives of the formula (V)                          in which    A, R 6  and R 7  have the meanings given in  claim 1 ,    Z 2 , Y 1  and X 1  have the meanings given above,    in the presence of a catalyst, where appropriate in the presence of an acid binder and, where appropriate, in the presence of a diluent,      or    D) reacting Δ 1 -pyrrolines of the formula (II-a)                        in which    R 1 , R 2 , R 4  and m have the meanings given in  claim 1 ,    Z 3  represents bromine or iodine    with organometallic compounds of the formula (VI)                          in which    A, R 6  and R 7  have the meanings given in  claim 1 ,    Y 1  and X 1  have the meanings given above,    M represents ZnCl, Sn(Me) 3  or Sn(n-Bu) 3 ,    in the presence of a catalyst, where appropriate in the presence of an acid binder and, where appropriate, in the presence of a diluent,      or    E) reacting Δ 1 -pyrrolines of the formula (VII)                        in which    R 1 , R 2 , A, R 4  and m have the meanings given in  claim 1       either with an iso(thio)cyanate of the formula (VIII)      R 7 —N═C═Y  (VIII)  in which    Y and R 7  have the meanings given in  claim 1     or with a (thio)carbonate of the formula (IX)                          in which    Y and R 7  have the meanings given in  claim 1 ,    X 2  represents O (oxygen) or S (sulphur),    in each case where appropriate in the presence of a diluent and, where appropriate, in the presence of an acid binder.      
   
   
       21 . Pesticides, characterized in that they comprise at least one compound of the formula (I) according to  claim 1  in addition to extenders and/or surface-active substances.  
   
   
       22 . Use of compounds of the formula (I) according to  claim 1  for controlling pests.  
   
   
       23 . Method of controlling pests, characterized in that compounds of the formula (I) according to  claim 1  are caused to act on pests and/or their habitat.  
   
   
       24 . Process for producing pesticides, characterized in that compounds of the formula (I) according to  claim 1  are mixed with extenders and/or surface-active substances.