Patent Publication Number: US-2009221596-A1

Title: Substtituted aryl oximes

Description:
The present invention relates to new substituted aryl oximes, to processes for preparing them and to their use as pesticides. 
     Substituted aryl oximes have already been disclosed as pesticides (cf. WO2003/042147A1). 
     New substituted aryl oximes have now been found of the general formula (I) 
     
       
         
         
             
             
         
       
     
     in which
     A 1  is one of the moieties —CH 2 —CH═CCl 2 , —CH 2 —CH═CBr 2 , —CH 2 —CH═CClF, —CH 2 —CF═CCl 2 , —(CH 2 ) 2 —CH═CF 2 , —CH 2 —CH═CBrCl, —CH 2 —CH═CBrF, —CF═CH—CH═CH 2 , —CH 2 —CF═CF—CH═CH 2 , —CH 2 —CH═CClCF 3 , —(CH 2 ) 2 —C(halogen) 3 , —(CH 2 ) 2 —CH(halogen) 2 , —CH 2 —CH(halogen)-CH(halogen) 2 , —CH 2 —CH═CClCH 3  and in which   A 2 -X is a bridging element. Located between X and R 6 , optionally, is the bridging element   

     
       
         
         
             
             
         
       
         
         
           
             in which the radicals R 21  and R 22  independently of one another are hydrogen, nitro, hydroxyl, amino, cyano, cyanato, thiocyanato, formyl, halogen, in each case optionally cyano-, halogen- or C 1 -C 6 -alkoxy-substituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino, dialkylamino or alkylcarbonylamino having in each case 1 to 4 carbon atoms in the alkyl groups, are C 1 -C 4 -alkyl-carbonyl, C 1 -C 4 -alkoxy-carbonyl, C 1 -C 4 -alkoximinoformyl, C 1 -C 4 -alkoximino-acetyl, or are C 2 -C 4 -alkenyl or C 2 -C 4 -alkynyl. 
           
         
         A 2 -X is either a direct bond or a straight-chain or branched or cyclic alkanediyl or an alkenediyl having in each case up to 8 carbon atoms and which in each case, optionally in attachment to the carbon chain, contains an oxygen atom, sulphur atom or a moiety selected from SO, SO 2 , NH and N(C 1 -C 4 -alkyl). 
         A 2 -X is additionally
       —(C 1 -C 4 -alkyl)-(CO)—O—, (C 1 -C 4 -alkyl)-(CO)—(NH)—, —(C 1 -C 4 -alkyl)-(CO)-[N—(C 1 -C 4 -alkyl)]-, —(C 1 -C 4 -alkyl)-(CO)—S—, —(C 1 -C 4 -alkyl)-O—(CO)—, —(C 1 -C 4 -alkyl)-(NH)—(CO)—, —(C 1 -C 4 -alkyl)-[N—(C 1 -C 4 -alkyl)]-(CO)—, —(C 1 -C 4 -alkyl)-S—(CO)—, —(C 2 -C 8 -alkenyl)-(CO)—O—, —(C 2 -C 8 -alkenyl)-(CO)—(NH)—, —(C 2 -C 8 -alkenyl)-(CO)-[N—(C 1 -C 4 -alkyl)]-, —(C 2 -C 8 -alkenyl)-(CO)—S—, —(C 2 -C 8 -alkenyl)-O—(CO)—(C 2 -C 8 -alkenyl)-(NH)—(CO—)—, —(C 1 -C 4 -alkyl)-[N—(C 1 -C 4 -alkyl)]-(CO)—, —(C 2 -C 8 -alkenyl)-S—(CO)—, —(C 1 -C 4 -alkyl)-[N—(C 1 -C 4 -alkyl)]-(CO)—, —(C 2 -C 8 -alkenyl)-S—(CO)—, —(C 1 -C 4 -alkyl)-(SO 2 )—(NH)—, —(C 2 -C 8 -alkenyl)-(CO)—S—, —(C 2 -C 8 -alkenyl)-(SO 2 )—(NH)—, —(C 1 -C 4 -alkyl)-O—N═C(R 9 )—, —(C 1 -C 8 -alkenyl)-O—N═C(R 9 )—,   
     
         R 9  is C 1 -C 4 -alkyl or is aryl, 
         A 2 -X is further a carbocyclic, optionally mono- or polyunsaturated, 5-, 6- or 7-membered ring system or is an optionally mono- or polyunsaturated, 7-10-membered bicyclic ring system, which optionally may be interrupted one or more times by oxygen, sulphur, sulphonyl, sulphoxyl, carbonyl, NO, or by optionally alkyl-substituted nitrogen, and optionally may be substituted one or more times. The attachment of these ring systems to the oxime oxygen is always via carbon. The attachment to the radical R 6  may be via carbon or a heteroatom (nitrogen or sulphur). 
         R 1  is hydrogen, nitro, hydroxyl, amino, cyano, fluoro, chloro, bromo, iodo, or is in each case optionally cyano-, fluoro-, chloro-, methoxy-, ethoxy-, n- or isopropoxy-substituted C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyloxy, C 3 -C 6  alkenyl, C 3 -C 6  alkenyloxy, C 3 -C 6  alkynyl, C 3 -C 6  alkynyloxy, C 1 -C 6  alkylcarbonyloxy, C 1 -C 3  alkylsulphonyl, methyl, ethyl, n- or isopropyl, n-, iso-, s- or t-butyl, methoxy, ethoxy, n- or isopropoxy, n-, iso-, s- or t-butoxy, methylthio, ethylthio, n- or isopropylthio, n-, iso-, s- or t-butylthio, methylamino, ethylamino, n- or isopropylamino, n-, iso-, s- or t-butylamino, dimethylamino, diethylamino, dipropylamino, acetylamino, propionylamino, n- or isobutyroylamino, methoximinomethyl, ethoximinomethyl, methoximinoethyl or ethoximinoethyl, 
         R 2  is hydrogen, nitro, hydroxyl, amino, cyano, cyanato, thiocyanato, formyl, halogen, is in each case optionally cyano-, halogen- or C 1 -C 6 -alkoxy-substituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino, dialkylamino or alkylcarbonylamino having in each case 1 to 6 carbon atoms in the alkyl groups, is C 1 -C 6 -alkyl-carbonyl, C 1 -C 6 -alkoxy-carbonyl, C 1 -C 6 -alkoximinoformyl, C 1 -C 6 -alkoximino-acetyl, or is C 2 -C 6 -alkenyl or C 2 -C 6 -alkynyl, 
         R 3  is hydrogen, nitro, hydroxyl, amino, cyano, halogen, is in each case optionally cyano-, halogen- or C 1 -C 6 -alkoxy-substituted alkyl, alkoxy, alkylthio, alkylamino, dialkylamino or alkylcarbonylamino having in each case 1 to 6 carbon atoms in the alkyl groups, 
         R 4  is hydrogen, nitro, hydroxyl, amino, cyano, halogen, is in each case optionally cyano-, halogen- or C 1 -C 6 -alkoxy-substituted alkyl, alkoxy, alkylthio, alkylamino, dialkylamino or alkylcarbonylamino having in each case 1 to 6 carbon atoms in the alkyl groups, 
         R 5  is hydrogen, straight-chain or branched or cyclic halogenalkanyl or halogenalkenyl having in each case up to 8 carbon atoms, aryl, substituted aryl, 
         R 6  is an alkenyl moiety, an alkynyl moiety having in each case 2 to 6 carbon atoms or cyclo-alkenyl moiety having 4 to 6 carbon atoms, which is optionally substituted by at least one substituent from the group nitro, cyano, carboxyl, carbamoyl, hydroxyl, carbonyl (C═O), hydroximino (C═N—OH), C 1 -C 6 -alkoxy, C 1 -C 6 -alkoxy-carbonyl, C 1 -C 6 -alkylamino, di(C 1 -C 6 -alkyl)amino, C 1 -C 6 -alkylamino-carbonyl, C 1 -C 6 -alkoxy-carbonylamino, C 1 -C 6 -alkoxy-C 1 -C 6 -alkoxy, C 1 -C 6 -alkoxyimino, C 3 -C 6 -alkenyloxy, C 3 -C 6 -alkynyloxy, C 3 -C 6 -alkenyloxy-carbonyl, C 3 -C 6 -alkynyloxy-carbonyl, C 3 -C 6 -alkenyloxyimino, C 3 -C 6 -alkynyloxyimino, C 3 -C 6 -cycloalkyl, furyl, benzofuryl, thienyl, benzothienyl, isoxazolyl, benzisoxazolyl, pyrazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl. 
         R 6  is additionally a moiety -A 3 -Z, where
       A 3  is a single bond or is straight-chain or branched and optionally halogen- or C 3 -C 6 -cycloalkyl-substituted alkanediyl having 1 to 6 carbon atoms and   Z is optionally nitro-, hydroxyl-, mercapto-, amino-, formyl-, cyano-, carboxyl-, carbamoyl-, halogen-, C 1 -C 6 -alkyl-, C 1 -C 6 -hydroxyalkyl-, C 1 -C 6 -haloalkyl-, C 1 -C 6 -alkyl-carbonyl-, C 1 -C 6 -haloalkyl-carbonyl-, C 1 -C 6 -alkoxy-, C 1 -C 6 -hydroxyalkoxy-, C 1 -C 6 -haloalkoxy-, C 1 -C 6 -alkoxy-carbonyl-, C 1 -C 6 -haloalkoxy-carbonyl-, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl-, C 1 -C 6 -haloalkoxy-C 1 -C 6 -alkyl-, C 1 -C 2 -alkylenedioxy-, C 1 -C 2 -haloalkylenedioxy-, C 1 -C 6 -alkoxyimino-C 1 -C 6 -alkyl-, C 2 -C 6 -alkenyl-, C 2 -C 6 -alkenyl-carbonyl-, C 2 -C 6 -haloalkenyl-, C 2 -C 6 -haloalkenyl-carbonyl-, C 2 -C 6 -alkenyloxy-C 1 -C 6 -alkyl-, C 2 -C 6 -haloalkenyloxy-C 1 -C 6 -alkyl-, C 2 -C 6 -alkynyl-, C 2 -C 6 -haloalkynyl-, C 2 -C 6 -alkenyloxy-, C 2 -C 6 -alkenyloxy-carbonyl-, C 2 -C 6 -haloalkenyloxy-, C 2 -C 6 -haloalkenyloxy-carbonyl-, C 2 -C 6 -alkynyloxy-, C 2 -C 6 -alkynyloxy-carbonyl-, C 2 -C 6 -haloalkynyloxy-, C 2 -C 6 -haloalkynyloxy-carbonyl-, C 2 -C 6 -alkynyloxy-C 1 -C 6 -alkyl-, C 2 -C 6 -haloalkynyloxy-C 1 -C 6 -alkyl-, C 3 -C 8 -cycloalkyl-, C 3 -C 8 -cycloalkyl-carbonyl-, C 3 -C 8 -cycloalkyl-C 1 -C 6 -alkyl-, C 3 -C 8 -cycloalkyl-C 1 -C 6 -alkyl-carbonyl-, C 3 -C 8 -cycloalkyloxy-, C 3 -C 8 -cycloalkyloxy-carbonyl-, C 3 -C 8 -cycloalkyl-C 1 -C 6 -alkoxy-, C 3 -C 8 -cycloalkyl-C 1 -C 6 -alkoxy-carbonyl-, C 3 -C 8 -cycloalkyloxy-C 1 -C 6 -alkyl-, C 3 -C 8 -cycloalkyloxy-C 1 -C 6 -alkoxy-, C 3 -C 8 -cycloalkyl-C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl-, C 1 -C 6 -alkyl-carbonyl-C 1 -C 6 -alkyl-, C 1 -C 6 -alkoxy-carbonyl-C 1 -C 6 -alkyl-, C 1 -C 6 -alkylthio-, C 1 -C 6 -haloalkylthio-, C 1 -C 6 -alkylsulphinyl-, C 1 -C 6 -haloalkylsulphinyl-, C 1 -C 6 -alkylsulphonyl-, C 1 -C 6 -haloalkylsulphonyl-, C 2 -C 6 -alkenylthio-, C 2 -C 6 -haloalkenyl-thio-, C 2 -C 6 -alkynylthio-, C 3 -C 6 -cycloalkylthio-, C 3 -C 6 -cycloalkyl-C 1 -C 6 -alkylthio-, C 1 -C 6 -alkylamino-, C 1 -C 6 -alkylamino-carbonyl-, di(C 1 -C 6 -alkyl)amino-, di(C 1 -C 6 -alkyl)amino-carbonyl-, C 1 -C 6 -alkyl-carbonylamino-, C 1 -C 6 -haloalkyl-carbonylamino-, C 1 -C 6 -alkoxy-carbonylamino-, C 1 -C 6 -alkyl-aminocarbonylamino-substituted, or phenyl-, phenyloxy-, benzyl-, benzyloxy-, phenylamino- or benzylamino-substituted (where in each case the phenyl groups are optionally substituted by nitro, hydroxyl, mercapto, amino, cyano, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkyl-carbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylsulphinyl, C 1 -C 6 -alkylsulphonyl or C 1 -C 6 -alkoxy-carbonyl) aryl or monocyclic or bicyclic heteroaryl having up to 10 carbon atoms and at least one heteroatom from the group N (nitrogen, 1 to 5 N atoms), O (oxygen, 1 or 2 O atoms), sulphur (1 or 2 S atoms) and optionally, as a replacement or in addition, an SO or SO 2  moiety, and optionally in addition a carbonyl moiety (C═O) and/or a thiocarbonyl moiety (C═S) as part of the heterocycle.   
     
         R 6  is further one of the following moieties: 
       
    
     
       
         
         
             
             
         
       
         
         A 3  is a bond or is a C 1 -C 6  alkylene bridge which is optionally substituted one or more times by halogen or by C 3 -C 8  cycloalkyl. 
         M is oxygen or NOR 7 . 
         R 7  is hydrogen, C 1 -C 12 alkyl, C 3 -C 8 cycloalkyl, C 1 -C 6 alkylcarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 alkynyl, aryl, heterocyclyl or benzyl, with alkyl, cycloalkyl, alkenyl and alkynyl radicals being unsubstituted or being optionally substituted one to five times by a radical from the following group: halogen, —N 3 , CN, NO 2 , OH, SH, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 2 -C 6 alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 3 -C 6 -alkynyloxy, C 3 -C 6 haloalkynyloxy, C 3 -C 8 cycloalkyl-C 1 -C 6 alkoxy, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 haloalkylcarbonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylcarbonyl-C 1 -C 6 alkyl, C 1 -C 6 alkoxycarbonyl-C 1 -C 6 alkyl, C 1 -C 6 alkylthio, C 2 -C 6 alkylthio, C 3 -C 6 alkynylthio, C 3 -C 6 cycloalkyl-C 1 -C 6 alkylthio, C 3 -C 6 haloalkynyl, C 2 -C 6 haloalkenylthio, C 1 -C 6 haloalkylthio, C 1 -C 6 alkoxy-C 1 -C 6 alkyl, C 1 -C 6 haloalkoxy-C 1 -C 6 alkyl, C 2 -C 6 alkenyloxy-C 1 -C 6 alkyl, C 2 -C 6 haloalkenyloxy-C 1 -C 6 alkyl, C 3 -C 6 alkynyloxy-C 1 -C 6 alkyl, NH 2 , NHC 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 3 -C 6 alkynyl, C 3 -C 8 cycloalkyl, C 3 -C 8 cycloalkyl-C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 2 -C 6 alkenyloxy, C 2 -C 6 haloalkenyloxy, C 3 -C 6 alkynyloxy, C 3 -C 6 haloalkynyloxy, C 3 -C 8 cycloalkyl-C 1 -C 6 alkoxy, C 1 -C 6 alkylcarbonyl, C 1 -C 6 haloalkyl-carbonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylcarbonyl-C 1 -C 6 -alkyl, C 1 -C 6 alkoxycarbonyl-C 1 -C 6 alkyl, C 1 -C 6 alkylthio, C 2 -C 6 alkenylthio, C 3 -C 6 alkynylthio, C 3 -C 6 cycloalkyl-C 1 -C 6 alkylthio, C 3 -C 6 haloalkynyl, C 2 -C 6 haloalkenylthio, C 1 -C 6 haloalkylthio, C 1 -C 6 alkoxy-C 1 -C 6 alkyl, C 1 -C 6 haloalkoxy-C 1 -C 6 alkyl, C 2 -C 6 alkenyloxy-C 1 -C 6 alkyl, C 2 -C 6 haloalkenyloxy-C 1 -C 6 alkyl, C 3 -C 6 alkynyloxy-C 1 -C 6 alkyl, N(C 1 -C 6 alkyl) 2 , the two alkyl groups independently of one another being able to be C 1 -C 6 alkylcarbonylamino, C 1 -C 6 haloalkylcarbonylamino, C 1 -C 6 alkoxycarbonylamino and C 1 -C 6 alkylaminocarbonylamino. 
         W is *C(R 32 R 33 ) or *C(R 32 R 33 )C(R 34 R 35 ), where the asterisk “*”
       denotes the attachment to oxygen, and in which R 32  to R 35  each independently of one another are halogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy(C 1 -C 4 )alkyl or halo(C 1 -C 4 )alkyl.   
     
         n can adopt values from 0 to 3, 
         R 8  is independently at each occurrence hydrogen, halogen, halo(C 1 -C 4 )alkyl, C 3 -C 6 cycloalkyl, C 2 -C 5 alkenyl, C 2 -C 5 alkynyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkylthio, C 1 -C 4 haloalkylthio, C 1 -C 4 alkylsulphonyl, C 1 -C 4 haloalkylsulphonyl, nitro, cyano, aryl, alkylcarbonylamino, arylcarbonylamino and C 1 -C 4 alkoxycarbonylamino. 
         R 10  and R 11  are in each case independently of one another hydrogen, halogen, hydroxyl, (C 1 -C 4 ) alkyl, halo(C 1 -C 4 )alkyl or (C 1 -C 4 )alkoxy or together are carbonyl, are —O—CH 2 —CH 2 —O—, S—CH 2 —CH 2 —S, ketal, thioketal or forming an oxime in the form NOR 2 , where 
         R 12  is (C 1 -C 3 )alkyl, (C 1 -C 3 )alkoxy(C 1 -C 3 )alkyl, aryl-(C 1 -C 3 )alkyl, C 2 -C 4 alkenyl-(C 1 -C 3 )alkyl, halo(C 2 -C 4 )alkenyl-(C 1 -C 3 )alkyl, di(C 1 -C 3 )alkylphosphonate, formyl, (C 1 -C 3 )alkylcarbonyl, halo(C 1 -C 3 )alkylcarbonyl, (C 1 -C 3 )alkoxy(C 1 -C 3 )alkylcarbonyl, arylcarbonyl and (C 1 -C 3 )alkylsulphonyl. 
       
    
     Preferred substituents and preferred ranges of the radicals present in the formulae recited above and below are defined in the following text.
     A 1  is preferably one of the following moieties:
       —CH 2 —CH═CCl 2 , —CH 2 —CH═CBr 2 , —CH 2 —CH═CClF, —CH 2 —CH═CBrCl, —CH 2 —CH═CBrF.   
       A 1  is with particular preference one of the following moieties:
       —CH 2 —CH═CCl 2 , —CH 2 —CH═CBr 2 , —CH 2 —CH═CBrCl.   
       A 1  is with very particular preference the moiety —CH 2 —CH═CCl 2 .   A 2 -X is preferably a straight-chain or branched alkanediyl or alkenediyl having in each case up to 8 carbon atoms, which optionally within the carbon chain contains an oxygen atom, sulphur atom or a moiety selected from SO, SO 2 , NH, N(C 1 -C 4 -alkyl), and also is
       —(C 1 -C 4 -alkyl)-(CO)—O—, —(C 1 -C 4 -alkyl)-(CO)—(NH)—, —(C 1 -C 4 -alkyl)-(CO)-[N—(C 1 -C 4 -alkyl)]-, —(C 1 -C 4 -alkyl)-(CO)—S—, (C 2 -C 8 -alkenyl)-(CO)—O—, —(C 2 -C 8 -alkenyl)-(CO)—(NH)—, —(C 2 -C 8 -alkenyl)-(CO)-[N—(C 1 -C 4 -alkyl)]-, —(C 2 -C 8 -alkenyl)-(CO)—S, piperidyl or piperazinyl, —(C 1 -C 4 -alkyl)-O—N═C(R 9 )—, —(C 1 -C 6 -alkenyl)-O—N═C(R 9 )—, in which   
       R 9  preferably is methyl or is aryl.   A 2 -X is with particular preference a straight-chain or branched alkanediyl or alkenediyl having in each case up to 8 carbon atoms, which optionally within the carbon chain contains an oxygen atom, and also is
       —(C 1 -C 4 -alkyl)-(CO)—O—, —(C 1 -C 4 -alkyl)-(CO)—(NH)—, —(C 1 -C 4 -alkyl)-(CO)-[N—(C 1 -C 4 -alkyl)]-, —(C 1 -C 4 -alkyl)-(CO)—S—, (C 2 -C 8 -alkenyl)-(CO)—O—, —(C 2 -C 8 -alkenyl)-(CO)—(NH)—, —(C 2 -C 8 -alkenyl)-(CO)-[N—(C 1 -C 4 -alkyl)]-, —(C 2 -C 8 -alkenyl)-(CO)—S, piperidyl or piperazinyl, —(C 1 -C 4 -alkyl)-O—N═C(R 9 )—, —(C 1 -C 6 -alkenyl)-O—N═C(R 9 )—, in which   
       R 9  is with particular preference methyl.   A 2 -X is with very particular preference a straight-chain or branched alkanediyl having up to 8 carbon atoms, which optionally within the carbon chain contains an oxygen atom, and also is —(C 1 -C 4 -alkyl)-(CO)—O—, —(C 1 -C 4 -alkyl)-(CO)—(NH)— or piperidyl.   

     Within the above definition of the optional bridge 
     
       
         
         
             
             
         
       
     
     the following definitions of the radicals R 21  and R 22  are preferred or particularly preferred.
     R 21  and R 22  are independently of one another preferably hydrogen, nitro, hydroxyl, amino, cyano, cyanato, thiocyanato, formyl, halogen or methyl,   R 21  and R 22  are with particular preference hydrogen.   R 1  is preferably hydrogen, nitro, hydroxyl, cyano, fluoro, chloro, bromo, methyl, ethyl, n- or isopropyl, methoxy, ethoxy, n- or isopropoxy, methylthio, ethylthio, n- or isopropylthio, methylamino, ethylamino, n- or isopropylamino, dimethylamino or is the moiety —O-A 1 , where A 1  has one of the definitions indicated above.   R 1  is with particular preference hydrogen, nitro, hydroxyl, cyano, fluoro, chloro, bromo, methyl, ethyl, n- or isopropyl, methoxy, ethoxy, n- or isopropoxy, methylthio, ethylthio, n- or isopropylthio, methylamino, ethylamino, n- or isopropylamino or dimethylamino.   R 1  is with very particular preference hydrogen, methyl, ethyl, methoxy, ethoxy or fluoro, chloro, bromo.   R 2  is preferably hydrogen, nitro, cyano, cyanato, thiocyanato, formyl, halogen, is in each case optionally cyano-, halogen- or C 1 -C 5 -alkoxy-substituted alkyl, alkoxy, alkylthio, alkylamino, dialkylamino or alkylcarbonylamino having in each case 1 to 5 carbon atoms in the alkyl groups, is C 1 -C 5 -alkyl-carbonyl, C 1 -C 5 -alkoxy-carbonyl, C 1 -C 5 -alkoximinoformyl, C 1 -C 5 -alkoximino-acetyl, or is C 2 -C 5 -alkenyl or C 2 -C 5 -alkynyl.   R 2  is with particular preference hydrogen, nitro, cyano, cyanato, thiocyanato, formyl, fluoro, chloro, bromo, iodo, is in each case optionally cyano-, fluoro-, chloro-, methoxy-, ethoxy-, n- or isopropoxy-substituted methyl, ethyl, n- or isopropyl, n-, iso-, s- or t-butyl, methoxy, ethoxy, n- or isopropoxy, n-, iso-, s- or t-butoxy, methylthio, ethylthio, n- or isopropylthio, n-, iso-, s- or t-butylthio, methylamino, ethylamino, n- or isopropylamino, n-, iso-, s- or t-butylamino, dimethylamino, diethylamino, acetylamino, propionylamino, n- or isobutyroylamino, acetyl, propionyl, n- or isobutyroyl, methoxycarbonyl, ethoxycarbonyl, n- or isopropoxycarbonyl, methoximinoformyl, ethoximinoformyl, methoximinoacetyl or ethoximinoacetyl.   R 2  is with very particular preference hydrogen, cyano, fluoro, chloro, bromo or iodo.   R 2  is most preferably hydrogen, fluoro, chloro or bromo.   R 3  is preferably hydrogen, nitro, halogen, is in each case optionally cyano-, halogen- or C 1 -C 5 -alkoxy-substituted alkyl, alkoxy, alkylthio or alkylamino having in each case 1 to 5 carbon atoms in the alkyl groups.   

     R 3  is with particular preference hydrogen, nitro, fluoro, chloro, bromo, iodo, is in each case optionally cyano-, fluoro-, chloro-, methoxy-, ethoxy-, n- or isopropoxy-substituted methyl, ethyl, n- or isopropyl, n-, iso-, s- or t-butyl, methoxy, ethoxy, n- or isopropoxy, n-, iso-, s- or t-butoxy, methylthio, ethylthio, n- or isopropylthio, n-, iso-, s- or t-butylthio, methylamino, ethylamino, n- or isopropylamino, n-, iso-, s- or t-butylamino.
     R 3  is with very particular preference hydrogen, cyano, fluoro, chloro, bromo, methyl, ethyl, methoxy or ethoxy.   R 4  is preferably hydrogen, nitro, halogen, is in each case optionally cyano-, halogen- or C 1 -C 5 -alkoxy-substituted alkyl, alkoxy, alkylthio or alkylamino having in each case 1 to 5 carbon atoms in the alkyl groups.   R 4  is with particular preference hydrogen, nitro, fluoro, chloro, bromo, iodo, is in each case optionally cyano-, fluoro-, chloro-, methoxy-, ethoxy-, n- or isopropoxy-substituted methyl, ethyl, n- or isopropyl, n-, iso-, s- or t-butyl, methoxy, ethoxy, n- or isopropoxy, n-, iso-, s- or t-butoxy, methylthio, ethylthio, n- or isopropylthio, n-, iso-, s- or t-butylthio, methylamino, ethylamino, n- or isopropylamino, n-, iso-, s- or t-butylamino.   R 4  is with very particular preference hydrogen, cyano, fluoro, chloro or bromo.   R 5  is preferably an alkanyl moiety or alkynyl moiety having in each case 2 to 5 carbon atoms or cycloalkanyl moiety having 4 to 6 carbon atoms, which contain in each case at least one substituent from the group nitro, cyano, carboxyl, carbamoyl, hydroxyl, carbonyl (C═O), hydroximino (C═N—OH), C 1 -C 5 -alkoxy, C 1 -C 5 -alkoxy-carbonyl, C 1 -C 5 -alkylamino, di(C 1 -C 4 -alkyl)-amino, C 1 -C 5 -alkylamino-carbonyl, C 1 -C 5 -alkoxy-carbonylamino, C 1 -C 5 -alkoxy-C 1 -C 5 -alkoxy, C 1 -C 5 -alkoxyimino, C 3 -C 5 -alkenyloxy, C 3 -C 5 -alkynyloxy, C 3 -C 5 -alkenyloxy-carbonyl, C 3 -C 5 -alkynyloxy-carbonyl, C 3 -C 5 -alkenyloxyimino, C 3 -C 5 -alkynyloxyimino, C 3 -C 6 -cycloalkyl.   R 5  is with particular preference hydrogen, methyl, isopropyl, cyclopropyl or cyclohexyl.   R 5  is with very particular preference methyl.   R 6  is preferably an alkenyl moiety or alkynyl moiety having in each case 2 to 6 carbon atoms or cycloalkenyl moiety having 4 to 6 carbon atoms, which is optionally substituted by at least one substituent from the group nitro, cyano, carboxyl, carbamoyl, hydroxyl, carbonyl (C═O), hydroximino (C═N—OH), C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxy-carbonyl, C 1 -C 4 -alkylamino, di(C 1 -C 4 -alkyl)-amino, C 1 -C 4 -alkylamino-carbonyl, C 1 -C 4 -alkoxy-carbonylamino, C 1 -C 4 -alkoxy-C 1 -C 6 -alkoxy, C 1 -C 4 -alkoxyimino, C 3 -C 4 -alkenyloxy, C 3 -C 4 -alkynyloxy, C 3 -C 4 -alkenyloxy-carbonyl, C 3 -C 4 -alkynyloxy-carbonyl, C 3 -C 4 -alkenyloxyimino, C 3 -C 5 -alkynyloxyimino, C 3 -C 6 -cycloalkyl, furyl, benzofuryl, thienyl, benzothienyl, isoxazolyl, benzisoxazolyl, pyrazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl.   

     Preference or particular preference is also given to the above-stated alternatives in the definition of R 6  in which the radicals A 3 , Z, M, R 7 , W, n, R 8 , R 10  and R 11  have the following preferred or particularly preferred definitions.
     A 3  is preferably a single bond or is straight-chain or branched and optionally halogen- or C 3 -C 6 -cycloalkyl-substituted alkanediyl having 1 to 6 carbon atoms,   A 3  is with particular preference a single bond or is in each case optionally fluoro-, chloro-, bromo-, cyclopropyl-, cyclobutyl-, cyclopentyl- or cyclohexyl-substituted methylene, ethane-1,1-diyl (ethylidene), ethane-1,2-diyl (dimethylene), propane-1,1-diyl (propylidene), propane-1,2-diyl, propane-1,3-diyl (trimethylene), butane-1,1-diyl (butylidene) or butane-1,4-diyl (tetramethylene),   A 3  is with very particular preference a single bond or is methylene,   Z is preferably in each case optionally nitro-, hydroxyl-, amino-, formyl-, cyano-, carboxyl-, carbamoyl-, fluoro-, chloro-, bromo-, methyl-, ethyl-, n- or isopropyl-, n-, iso-, s- or t-butyl-, fluoromethyl-, chloromethyl-, difluoromethyl-, dichloromethyl-, trifluoromethyl-, trichloromethyl-, fluoroethyl-, chloroethyl-, difluoroethyl-, dichloroethyl-, chlorofluoroethyl-, trifluoroethyl-, trichloroethyl-, chlorodifluoroethyl-, fluoropropyl-, chloropropyl-, difluoropropyl-, dichloropropyl-, trifluoropropyl-, fluoroisopropyl-, difluoroisopropyl-, trifluoroisopropyl-, tetrafluoroisopropyl-, pentafluoroisopropyl-, methoxy-, ethoxy-, n- or isopropoxy-, fluoromethoxy-, difluoromethoxy-, trifluoromethoxy-, fluorodichloromethoxy-, chlorodifluoromethoxy-, fluoroethoxy-, chloroethoxy-, difluoroethoxy-, dichloroethoxy-, trifluoroethoxy-, fluoropropoxy, methoxycarbonyl-, ethoxycarbonyl-, fluoroethoxycarbonyl-, chloroethoxycarbonyl-, methoxymethyl-, ethoxymethyl-, n- or isopropoxymethyl-, methoxyethyl-, ethoxyethyl-, n- or isopropoxyethyl-, ethenyl-, propenyl-, butenyl-, fluoroethenyl-, chloroethenyl-, difluoroethenyl-, dichloroethenyl-, trifluoroethenyl-, trichloroethenyl-, propenyloxymethyl-, butenyloxymethyl-, propenyloxyethyl-, butenyloxyethyl-, ethynyl-, propynyl-, butynyl-, propenyloxy-, butenyloxy-, fluoropropenyloxy-, chloropropenyloxy-, fluorobutenyloxy-, chlorobutenyloxy-, propenyloxycarbonyl-, butenyloxycarbonyl-, propynyloxy-, butynyloxy-, propynyloxycarbonyl-, butynyloxycarbonyl-, propynyloxymethyl-, butynyloxymethyl-, propynyloxyethyl-, butynyloxyethyl-, cyclopropyl-, cyclobutyl-, cyclopentyl-, cyclopropylcarbonyl-, cyclobutylcarbonyl-, cyclopentylcarbonyl-, cyclopropylmethyl-, cyclobutylmethyl-, cyclopentylmethyl-, cyclohexylmethyl-, cyclopropylmethylcarbonyl-, cyclobutylmethylcarbonyl-, cyclopentylmethylcarbonyl-, cyclopropyloxy-, cyclobutyloxy-, cyclopentyloxy-, cyclohexyloxy-, cyclopropyloxycarbonyl-, cyclobutyloxycarbonyl-, cyclopentyloxycarbonyl-, cyclohexyloxycarbonyl-, cyclopropylmethoxy-, cyclobutylmethoxy-, cyclopentylmethoxy-, cyclohexylmethoxy-, cyclopropylmethoxycarbonyl-, cyclobutylmethoxycarbonyl-, cyclopentylmethoxycarbonyl-, cyclohexylmethoxycarbonyl-, cyclopropylmethoxymethyl-, cyclobutylmethoxymethyl-, cyclopentylmethoxymethyl-, cyclopropyloxymethoxy-, cyclobutyloxymethoxy-, cyclopentyloxymethoxy-, acetylmethyl-, propionylmethyl-, n- or isobutyroylmethyl-, acetylethyl-, propionylethyl-, methoxycarbonylmethyl-, ethoxycarbonylmethyl-, n- or isopropoxycarbonylmethyl-, methoxycarbonylethyl-, ethoxycarbonylethyl-, n- or isopropoxycarbonylethyl-, methylthio-, ethylthio-, n- or isopropylthio-, difluoromethylthio-, trifluoromethylthio-, chlorodifluoromethylthio-, methylsulphinyl-, ethylsulphinyl-, trifluoromethylsulphinyl-, methylsulphonyl-, ethyl-sulphonyl-, trifluoromethylsulphonyl-, propenylthio-, butenylthio-, fluoropropenylthio-, chloropropenylthio-, fluorobutenylthio-, chlorobutenylthio-, propynylthio-, butynylthio-, cyclopropylthio-, cyclobutylthio-, cyclopentylthio-, cyclohexylthio-, cyclopropylmethylthio-, cyclobutylmethylthio-, cyclopentylmethylthio-, methylamino-, ethylamino-, n- or isopropylamino-, methylaminocarbonyl-, ethylaminocarbonyl-, n- or isopropylaminocarbonyl-, dimethylamino-, diethylamino-, dimethylaminocarbonyl-, diethylaminocarbonyl-, acetylamino-, propionylamino-, n- or isobutyroylamino-, methoxycarbonylamino-, ethoxycarbonylamino-, n- or isopropoxycarbonylamino-, methylaminocarbonylamino-, ethylaminocarbonylamino-, n- or isopropylaminocarbonylamino-substituted, or phenyl-, phenyloxy-, benzyl-, benzyloxy-, phenylamino- or benzylamino- (where in each case the phenyl groups are optionally substituted by nitro, hydroxyl, mercapto, amino, cyano, methyl, ethyl, n- or isopropyl, n-, iso-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or isopropoxy, difluoromethoxy, trifluoromethoxy, fluoroethoxy, difluoroethoxy, trifluoroethoxy, propenyloxy, butenyloxy, propynyloxy, butynyloxy, propynylthio, butynylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl, ethylsulphonyl, methoxycarbonyl, ethoxycarbonyl, n- or isopropoxycarbonyl) monocyclic heteroaryl having up to 5 carbon atoms and at least one heteroatom from the group N (nitrogen, 1 to 4 N atoms), O (oxygen, 1 O atom), sulphur (1 S atom) and optionally, in replacement or in addition, an SO or SO 2  moiety, and optionally in addition a carbonyl moiety (C═O) and/or a thiocarbonyl moiety (C═S) as part of the heterocycle, mention being made in particular, as heteroaryl moieties, of pyrrolyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, furyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, but especially tetrazolyl.   M is preferably oxygen,   R 7  is preferably hydrogen; C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 4 alkylcarbonyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, aryl, heterocyclyl or benzyl, where alkyl, cycloalkyl, alkenyl and alkynyl radicals are unsubstituted or are optionally substituted one to five times by a radical from the following group: halogen, —N 3 , CN, NO 2 , OH, SH, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 2 -C 4 alkenyloxy, C 2 -C 4 haloalkenyloxy, C 3 -C 4 alkynyloxy, C 3 -C 4 haloalkynyloxy, C 3 -C 6 cycloalkyl-C 1 -C 4 alkoxy, C 1 -C 4 alkylcarbonyl, C 1 -C 4 haloalkylcarbonyl, C 1 -C 4 alkoxycarbonyl, C 1 -C 4 alkylcarbonyl-C 1 -C 4 alkyl, C 1 -C 4 alkoxycarbonyl-C 1 -C 4 alkyl, C 1 -C 4 alkylthio, C 2 -C 4 alkylthio, C 3 -C 4 alkynylthio, C 3 -C 4 cycloalkyl-C 1 -C 4 alkylthio, C 3 -C 4 haloalkynyl, C 2 -C 4 haloalkenylthio, C 1 -C 4 haloalkylthio, C 1 -C 4 alkoxy-C 1 -C 4 Alkyl, C 1 -C 4 haloalkoxy-C 1 -C 4 alkyl, C 2 -C 4 alkenyloxy-C 1 -C 4 alkyl, C 2 -C 4 haloalkenyloxy-C 1 -C 4 alkyl, C 3 -C 4 alkynyloxy-C 1 -C 4 alkyl, NH 2 , NHC 2 -C 4 alkenyl, C 2 -C 4 haloalkenyl, C 3 -C 6 alkynyl, C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkyl-C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 2 -C 4 alkenyloxy, C 2 -C 4 haloalkenyloxy, C 3 -C 4 alkynyloxy, C 3 -C 4 haloalkynyloxy, C 3 -C 6 cycloalkyl-C 1 -C 4 alkoxy, C 1 -C 4 alkylcarbonyl, C 1 -C 4 haloalkyl-carbonyl, C 1 -C 4 alkoxycarbonyl, C 1 -C 4 alkylcarbonyl-C 1 -C 4 alkyl, C 1 -C 4 alkoxycarbonyl-C 1 -C 4 alkyl, C 1 -C 4 alkylthio, C 2 -C 4 alkenylthio, C 3 -C 4 alkynylthio, C 3 -C 6 cycloalkyl-C 1 -C 4 alkylthio, C 3 -C 4 haloalkynyl, C 2 -C 4 haloalkenylthio, C 1 -C 4 haloalkylthio, C 1 -C 4 alkoxy-C 1 -C 6 alkyl, C 1 -C 4 haloalkoxy-C 1 -C 4 alkyl, C 2 -C 4 alkenyloxy-C 1 -C 4 alkyl, C 2 -C 4 haloalkenyloxy-C 1 -C 4 alkyl, C 3 -C 4 alkynyloxy-C 1 -C 4 alkyl, N(C 1 -C 4 alkyl) 2 , where the two alkyl groups each independently of one another may be C 1 -C 4 alkylcarbonylamino, C 1 -C 4 haloalkylcarbonylamino, C 1 -C 4 -alkoxycarbonylamino and C 1 -C 4 alkylaminocarbonylamino.   W is preferably *C(R 32 R 33 ) and *C(R 32 R 33 )C(R 34 R 35 ), where the asterisk “*”
       denotes the attachment to O and in which R 32  to R 35  independently and in each case are halogen, C 1 -C 3 alkyl, C 1 -C 3 alkoxy(C 1 -C 3 )alkyl or halo(C 1 -C 3 )alkyl,   
       W is with particular preference C(R 32 R 33 ), where R 32 R 33  is halogen or C 1 -C 4 alkyl.   W is with very particular preference C(R 32 R 33 ), where R 32 R 33  is halogen or methyl.   n preferably adopts values from 0 to 2.   n is with particular preference 0.   R 8  is preferably, independently at each occurrence hydrogen, halogen, halo(C 1 -C 4 )alkyl or nitro.   R 9  is with particular preference hydrogen.   R 10  and R 11  are preferably, taken together, ═O or hydrogen.   

     Depending on factors which include the nature of the substituents, the compounds of the formula (I) may optionally be in the form of stereoisomers, i.e. in the form of geometrical and/or in the form of optical isomers or isomer mixtures in different compositions. Not only the pure stereoisomers but also any desired mixtures of these isomers are provided by this invention, despite reference being generally made only to the compounds of the formula (I). 
     The invention also provides the saltlike derivatives formed from compounds of the formula (I) by reaction with basic or acidic compounds. 
     Preferred substituents and preferred ranges of the radicals present in the formulae recited above and below are defined in the text below. 
     The general definitions of radicals recited above, or the above-recited definitions of radicals that are recited in ranges of preference, apply not only to the end products of the formula (I) but also, correspondingly, to the starting products or intermediates required in each case for their preparation. These definitions of radicals can be combined arbitrarily with one another, hence including arbitrary combinations of the preferred ranges specified. 
     Preference is given in accordance with the invention to those compounds of the formula (I) in which there is a combination of the definitions recited above as being preferred. 
     Particular preference is given in accordance with the invention to those compounds of the formula (I) in which there is a combination of the definitions recited above as being particularly preferred. 
     Very particular preference is given in accordance with the invention to those compounds of the formula (I) in which there is a combination of the definitions recited above as being very particularly preferred. 
     Maximum preference is given in accordance with the invention to those compounds of the formula (I) in which there is a combination of the definitions recited above as being most preferred. 
     In the definitions of radicals recited above and below, hydrocarbon radicals, such as alkyl, both alone and in conjunction with heteroatoms as in alkoxy, are in each case, as far as possible, linear or branched. 
     The new substituted aryl oximes of the general formula (I) exhibit advantageous biological properties. They are notable in particular for strong arthropodicidal (insecticidal and acaricidal) and nematicidal activity and can be used in agriculture, in forestry, in the protection of stored and other materials, and in the hygiene sector. 
     The new substituted aryl oximes of the general formula (I) can be prepared in accordance with the following general reaction scheme. The synthesis of the starting compounds of the formula (II) is described in DE 103 20 782 A1. 
     
       
         
         
             
             
         
       
     
     The precursors of the general formula H 2 N—O-A 2 -X—R 6  are obtainable via the following reaction pathway: 
     
       
         
         
             
             
         
       
     
     In the event that the bridge 
     
       
         
         
             
             
         
       
     
     the general reaction scheme for the synthesis of compounds of the general formula (I) is as follows: 
     
       
         
         
             
             
         
       
     
     In the event that the bridge 
     
       
         
         
             
             
         
       
     
     the general reaction scheme for the synthesis of compounds of the general formula (I) is as follows: 
     
       
         
         
             
             
         
       
     
     Optionally it is possible for the substituents of the compounds of the formula, such as the substituent R 1  for example, to be modified in further reaction steps as well. By way of example, in the event that R 1  is halogen, especially fluoro, a nucleophilic substitution with suitable nucleophils, within the bounds of the substituent definition of R 1 , can be undertaken in the presence of basic reaction auxiliaries, which are specified below. 
     The starting materials of the general formula (II) are known and/or can be prepared by methods which are known per se (cf. Preparation Examples). 
     The reaction temperatures when the process of the invention is carried out can be varied within a relatively large range. Generally speaking, temperatures are employed of between 0° C. and 150° C., preferably between 10° C. and 120° C. 
     The process of the invention is generally carried out under atmospheric pressure. It is, however, also possible to carry out the process of the invention under elevated or reduced pressure—in general between 0.1 bar and 10 bar. 
     For the implementation of the process of the invention the starting materials are generally used in approximately equimolar amounts. It is, however, also possible to use one of the components in a relatively large excess. The reaction is generally carried out in a suitable diluent in the presence of a reaction auxiliary, and the reaction mixture is generally stirred at the required temperature for a number of hours. Working up is carried out in accordance with typical methods (cf. the Preparation Examples). 
     The compounds of the invention of the general formula (I) can be converted, by methods which are known in principle, into other compounds of the general formula (I). Some of these possible conversion reactions are outlined exemplarily below: 
     The compounds of the invention of the general formula (I) can form salts. Suitable salts of the compounds of the general formula (I) include typical non-toxic salts, i.e. salts with bases and salts (“adducts”) with acids. Preference is given to salts with inorganic bases, such as alkali metal salts, examples being sodium, potassium or caesium salts, alkaline earth metal salts, examples being calcium or magnesium salts, ammonium salts, salts with organic bases, especially with organic amines, examples being triethylammonium, dicyclohexylammonium, N,N′-dibenzylethylene-diammonium, pyridinium, picolinium or ethanolammonium salts, salts with inorganic acids, examples being hydrochlorides, hydrobromides, dihydrosulphates, trihydrosulphates, or phosphates, and salts with organic carboxylic acids or organic sulpho acids, examples being formates, acetates, trifluoroacetates, maleates, tartrates, methanesulphonates, benzenesulphonates or para-toluenesulphonates. 
     Salts are formed in accordance with the standard methods for salt preparation. For example the compounds of the invention are reacted with corresponding acids in order to form acid addition salts. Representative acid addition salts are salts which are formed, for example, through reaction with inorganic acids, such as sulphuric acid, hydrochloric acid, hydrobromic acid and phosphoric acid, for example, or with organic carboxylic acids such as acetic acid, trifluoroacetic acid, citric acid, succinic acid, lactic acid, formic acid, maleic acid, camphoric acid, phthalic acid, glycolic acid, glutaric acid, stearic acid, salicylic acid, sorbic acid, cinnamic acid, picric acid, benzoic acid or organic sulphonic acids such as methanesulphonic acid and para-toluenesulphonic acid. 
     The compounds of the formula (I) can, if appropriate, be present in different polymorphic forms or as a mixture of different polymorphic forms. Both the pure polymorphs and the polymorph mixtures are provided by the invention and can be used according to the invention. 
     The active compounds of the invention, in combination with good plant tolerance and favourable toxicity to warm-blooded animals and being tolerated well by the environment, are suitable for protecting plants and plant organs, for increasing the harvest yields, for improving the quality of the harvested material and for controlling animal pests, in particular insects, arachnids, helminths, nematodes and molluscs, which are encountered in agriculture, in horticulture, in animal husbandry, in forests, in gardens and leisure facilities, in the protection of stored products and of materials, and in the hygiene sector. They may be preferably employed as plant protection agents. They are active against normally sensitive and resistant species and against all or some stages of development. The abovementioned pests include: 
     From the order of the Anoplura (Phthiraptera), for example,  Damalinia  spp.,  Haematopinus  spp.,  Linognathus  spp.,  Pediculus  spp.,  Trichodectes  spp. 
     From the class of the Arachnida, for example,  Acarus siro, Aceria sheldoni, Aculops  spp.,  Aculus  spp.,  Amblyomma  spp.,  Argas  spp.,  Boophilus  spp.,  Brevipalpus  spp.,  Bryobia praetiosa, Chorioptes  spp.,  Dermanyssus gallinae, Eotetranychus  spp.,  Epitrimerus pyri, Eutetranychus  spp.,  Eriophyes  spp.,  Hemitarsonemus  spp.,  Hyalomma  spp.,  Ixodes  spp.,  Latrodectus mactans, Metatetranychus  spp.,  Oligonychus  spp.,  Ornithodoros  spp.,  Panonychus  spp.,  Phyllocoptruta oleivora, Polyphagotarsonemus latus, Psoroptes  spp.,  Rhipicephalus  spp.,  Rhizoglyphus  spp.,  Sarcoptes  spp.,  Scorpio maurus, Stenotarsonemus  spp.,  Tarsonemus  spp.,  Tetranychus  spp.,  Vasates lycopersici.    
     From the class of the Bivalva, for example,  Dreissena  spp. 
     From the order of the Chilopoda, for example,  Geophilus  spp.,  Scutigera  spp. 
     From the order of the Coleoptera, for example,  Acanthoscelides obtectus, Adoretus  spp.,  Agelastica alni, Agriotes  spp.,  Amphimallon solstitialis, Anobium punctatum, Anoplophora  spp.,  Anthonomus  spp.,  Anthrenus  spp.,  Apogonia  spp.,  Atomaria  spp.,  Attagenus  spp.,  Bruchidius obtectus, Bruchus  spp.,  Ceuthorhynchus  spp.,  Cleonus mendicus, Conoderus  spp.,  Cosmopolites  spp.,  Costelytra zealandica, Curculio  spp.,  Cryptorhynchus lapathi, Dermestes  spp.,  Diabrotica  spp.,  Epilachna  spp.,  Faustinus cubae, Gibbium psylloides, Heteronychus arator, Hylamorpha elegans, Hylotrupes bajulus, Hypera postica, Hypothenemus  spp.,  Lachnostema consanguinea, Leptinotarsa decemlineata, Lissorhoptrus oryzophilus, Lixus  spp.,  Lyctus  spp.,  Meligethes aeneus, Melolontha melolontha, Migdolus  spp.,  Monochamus  spp.,  Naupactus xanthographus, Niptus hololeucus, Oryctes rhinoceros, Oryzaephilus surinamensis, Otiorrhynchus sulcatus, Oxycetonia jucunda, Phaedon cochleariae, Phyllophaga  spp.,  Popillia japonica, Premnotrypes  spp.,  Psylliodes chrysocephala, Ptinus  spp.,  Rhizobius ventralis, Rhizopertha dominica, Sitophilus  spp.,  Sphenophorus  spp.,  Sternechus  spp.,  Symphyletes  spp.,  Tenebrio molitor, Tribolium  spp.,  Trogo - derma  spp.,  Tychius  spp.,  Xylotrechus  spp.,  Zabrus  spp. 
     From the order of the Collembola, for example,  Onychiurus armatus.    
     From the order of the Dermaptera, for example,  Forficula auricularia.    
     From the order of the Diplopoda, for example,  Blaniulus guttulatus.    
     From the order of the Diptera, for example,  Aedes  spp.,  Anopheles  spp.,  Bibio hortulanus, Calliphora erythrocephala, Ceratitis capitata, Chrysomyia  spp.,  Cochliomyia  spp.,  Cordylobia anthropophaga, Culex  spp.,  Cuterebra  spp.,  Dacus oleae, Dermatobia hominis, Drosophila  spp.,  Fannia  spp.,  Gastrophilus  spp.,  Hylemyia  spp.,  Hyppobosca  spp.,  Hypoderma  spp.,  Liriomyza  spp.,  Lucilia  spp.,  Musca  spp.,  Nezara  spp.,  Oestrus  spp.,  Oscinella frit, Pegomyia hyoscyami, Phorbia  spp.,  Stomoxys  spp.,  Tabanus  spp.,  Tannia  spp.,  Tipula paludosa, Wohlfahrtia  spp. 
     From the class of the Gastropoda, for example,  Arion  spp.,  Biomphalaria  spp.,  Bulinus  spp.,  Deroceras  spp.,  Galba  spp.,  Lymnaea  spp.,  Oncomelania  spp.,  Succinea  spp. 
     From the class of the helminths, for example,  Ancylostoma duodenale, Ancylostoma ceylanicum, Acylostoma braziliensis, Ancylostoma  spp.,  Ascaris lubricoides, Ascaris  spp.,  Brugia malayi, Brugia timori, Bunostomum  spp.,  Chabertia  spp.,  Clonorchis  spp.,  Cooperia  spp.,  Dicrocoelium  spp,  Dictyocaulus filaria, Diphyllobothrium latum, Dracunculus medinensis, Echinococcus granulosus, Echinococcus multilocularis, Enterobius vermicularis, Faciola  spp.,  Haemonchus  spp.,  Heterakis  spp.,  Hymenolepis nana, Hyostrongulus  spp.,  Loa Loa, Nematodirus  spp.,  Oesophagostomum  spp.,  Opisthorchis  spp.,  Onchocerca volvulus, Ostertagia  spp.,  Paragonimus  spp.,  Schistosomen  spp,  Strongyloides fuellebomi, Strongyloides stercoralis, Stronyloides  spp.,  Taenia saginata, Taenia solium, Trichinella spiralis, Trichinella nativa, Trichinella britovi, Trichinella nelsoni, Trichinella pseudopsiralis, Trichostrongulus  spp.,  Trichuris trichuria, Wuchereria bancrofti.    
     It is furthermore possible to control Protozoa, such as  Eimeria.    
     From the order of the Heteroptera, for example,  Anasa tristis, Antestiopsis  spp.,  Blissus  spp.,  Calocoris  spp.,  Campylomma livida, Cavelerius  spp.,  Cimex  spp.,  Creontiades dilutus, Dasynus piperis, Dichelops furcatus, Diconocoris hewetti, Dysdercus  spp.,  Euschistus  spp.,  Eurygaster  spp.,  Heliopeltis  spp.,  Horcias nobilellus, Leptocorisa  spp.,  Leptoglossus phyllopus, Lygus  spp.,  Macropes excavatus, Miridae, Nezara  spp.,  Oebalus  spp.,  Pentomidae, Piesma quadrata, Piezodorus  spp.,  Psallus seriatus, Pseudacysta persea, Rhodnius  spp.,  Sahlbergella singularis, Scotinophora  spp.,  Stephanitis nashi, Tibraca  spp.,  Triatoma  spp. 
     From the order of the Homoptera, for example,  Acyrthosipon  spp.,  Aeneolamia  spp.,  Agonoscena  spp.,  Aleurodes  spp.,  Aleurolobus barodensis, Aleurothrixus  spp.,  Amrasca  spp.,  Anuraphis cardui, Aonidiella  spp.,  Aphanostigma piri, Aphis  spp.,  Arboridia apicalis, Aspidiella  spp.,  Aspidiotus  spp.,  Atanus  spp.,  Aulacorthum solani, Bemisia  spp.,  Brachycaudus helichrysii, Brachycolus  spp.,  Brevicoryne brassicae, Calligypona marginata, Carneocephala fulgida, Ceratovacuna lanigera, Cercopidae, Ceroplastes  spp.,  Chaetosiphon fragaefolii, Chionaspis tegalensis, Chlorita onukii, Chromaphis juglandicola, Chrysomphalus ficus, Cicadulina mbila, Coccomytilus halli, Coccus  spp.,  Cryptomyzus ribis, Dalbulus  spp.,  Dialeurodes  spp.,  Diaphorina  spp.,  Diaspis  spp.,  Doralis  spp.,  Drosicha  spp.,  Dysaphis  spp.,  Dysmicoccus  spp.,  Empoasca  spp.,  Eriosoma  spp.,  Erythroneura  spp.,  Euscelis bilobatus, Geococcus coffeae, Homalodisca coagulata, Hyalopterus arundinis, Icerya  spp.,  Idiocerus  spp.,  Idioscopus  spp.,  Laodelphax striatellus, Lecanium  spp.,  Lepidosaphes  spp.,  Lipaphis erysimi, Macrosiphum  spp.,  Mahanarva fimbriolata, Melanaphis sacchari, Metcalfiella  spp.,  Metopolophium dirhodum, Monellia costalis, Monelliopsis pecanis, Myzus  spp.,  Nasonovia ribisnigri, Nephotettix  spp.,  Nilaparvata lugens, Oncometopia  spp.,  Orthezia praelonga, Parabemisia myricae, Paratrioza  spp.,  Parlatoria  spp.,  Pemphigus  spp.,  Peregrinus maidis, Phenacoccus  spp.,  Phloeomyzus passerinii, Phorodon humuli, Phylloxera  spp.,  Pinnaspis aspidistrae, Planococcus  spp.,  Protopulvinaria pyriformis, Pseudaulacaspis pentagona, Pseudococcus  spp.,  Psylla  spp.,  Pteromalus  spp.,  Pyrilla  spp.,  Quadraspidiotus  spp.,  Quesada gigas, Rastrococcus  spp.,  Rhopalosiphum  spp.,  Saissetia  spp.,  Scaphoides titanus, Schizaphis graminum, Selenaspidus articulatus, Sogata  spp.,  Sogatella furcifera, Sogatodes  spp.,  Stictocephala festina, Tenalaphara malayensis, Tinocallis caryaefoliae, Tomaspis  spp.,  Toxoptera  spp.,  Trialeurodes vaporariorum, Trioza  spp.,  Typhlocyba  spp.,  Unaspis  spp.,  Viteus vitifolii.    
     From the order of the Hymenoptera, for example,  Diprion  spp.,  Hoplocampa  spp.,  Lasius  spp.,  Monomorium pharaonis, Vespa  spp. 
     From the order of the Isopoda, for example,  Armadillidium vulgare, Oniscus asellus, Porcellio scaber.    
     From the order of the Isoptera, for example,  Reticulitermes  spp.,  Odontotermes  spp. 
     From the order of the Lepidoptera, for example,  Acronicta major, Aedia leucomelas, Agrotis  spp.,  Alabama argillacea, Anticarsia  spp.,  Barathra brassicae, Bucculatrix thurberiella, Bupalus piniarius, Cacoecia podana, Capua reticulana, Carpocapsa pomonella, Chematobia brumata, Chilo  spp.,  Choristoneura fumiferana, Clysia ambiguella, Cnaphalocerus  spp.,  Earias insulana, Ephestia kuehniella, Euproctis chrysorrhoea, Euxoa  spp.,  Feltia  spp.,  Galleria mellonella, Helicoverpa  spp.,  Heliothis  spp.,  Hofinannophila pseudospretella, Homona magnanima, Hyponomeuta padella, Laphygma  spp.,  Lithocolletis blancardella, Lithophane antennata, Loxagrotis albicosta, Lymantria  spp.,  Malacosoma neustria, Mamestra brassicae, Mocis repanda, Mythimna separata, Oria  spp.,  Oulema oryzae, Panolis flammea, Pectinophora gossypiella, Phyllocnistis citrella, Pieris  spp.,  Plutella xylostella, Prodenia  spp.,  Pseudaletia  spp.,  Pseudoplusia includens, Pyrausta nubilalis, Spodoptera  spp.,  Thermesia gemmatalis, Tinea pellionella, Tineola bisselliella, Tortrix viridana, Trichoplusia  spp. 
     From the order of the Orthoptera, for example,  Acheta domesticus, Blatta orientalis, Blattella germanica, Gryllotalpa  spp.,  Leucophaea maderae, Locusta  spp.,  Melanoplus  spp.,  Periplaneta americana, Schistocerca gregaria.    
     From the order of the Siphonaptera, for example,  Ceratophyllus  spp.,  Xenopsylla cheopis.    
     From the order of the Symphyla, for example,  Scutigerella immaculata.    
     From the order of the Thysanoptera, for example,  Baliothrips biformis, Enneothrips flavens, Frankliniella  spp.,  Heliothrips  spp.,  Hercinothrips femoralis, Kakothrips  spp.,  Rhipiphorothrips cruentatus, Scirtothrips  spp.,  Taeniothrips cardamoni, Thrips  spp. 
     From the order of the Thysanura, for example,  Lepisma saccharina.    
     The phytoparasitic nematodes include, for example,  Anguina  spp.,  Aphelenchoides  spp.,  Belonoaimus  spp.,  Bursaphelenchus  spp.,  Ditylenchus dipsaci, Globodera  spp.,  Heliocotylenchus  spp.,  Heterodera  spp.,  Longidorus  spp.,  Meloidogyne  spp.,  Pratylenchus  spp.,  Radopholus similis, Rotylenchus  spp.,  Trichodorus  spp.,  Tylenchorhynchus  spp.,  Tylenchulus  spp.,  Tylenchulus semipenetrans, Xiphinema  spp. 
     The compounds of the formula (I) according to the invention have in particular excellent activity against . . . . 
     If appropriate, the compounds according to the invention can, at certain concentrations or application rates, also be used as herbicides, safeners, growth regulators or agents to improve plant properties, or as microbicides, for example as fungicides, antimycotics, bactericides, viricides (including agents against viroids) or as agents against MLO (Mycoplasma-like organisms) and RLO (Rickettsia-like organisms). If appropriate, they can also be employed as intermediates or precursors for the synthesis of other active compounds. 
     All plants and plant parts can be treated in accordance with the invention. Plants are to be understood as meaning in the present context all plants and plant populations such as desired and undesired wild plants or crop plants (including naturally occurring crop plants). Crop plants can be plants which can be obtained by conventional plant breeding and optimization methods or by biotechnological and genetic engineering methods or by combinations of these methods, including the transgenic plants and including the plant cultivars protectable or not protectable by plant breeders&#39; rights. Plant parts are to be understood as meaning all parts and organs of plants above and below the ground, such as shoot, leaf, flower and root, examples which may be mentioned being leaves, needles, stalks, stems, flowers, fruit bodies, fruits, seeds, roots, tubers and rhizomes. The plant parts also include harvested material, and vegetative and generative propagation material, for example cuttings, tubers, rhizomes, offshoots and seeds. 
     Treatment according to the invention of the plants and plant parts with the active compounds is carried out directly or by allowing the compounds to act on the surroundings, habitat or storage space by the customary treatment methods, for example by immersion, spraying, evaporation, fogging, scattering, painting on, injection and, in the case of propagation material, in particular in the case of seeds, also by applying one or more coats. 
     The active compounds can be converted to the customary formulations, such as solutions, emulsions, wettable powders, water- and oil-based suspensions, powders, dusts, pastes, soluble powders, soluble granules, granules for broadcasting, suspension-emulsion concentrates, natural materials impregnated with active compound, synthetic materials impregnated with active compound, fertilizers and microencapsulations in polymeric substances. 
     These formulations are produced in a known manner, for example by mixing the active compounds with extenders, that is liquid solvents and/or solid carriers, optionally with the use of surfactants, that is emulsifiers and/or dispersants and/or foam-formers. The formulations are prepared either in suitable plants or else before or during the application. 
     Suitable for use as auxiliaries are substances which are suitable for imparting to the composition itself and/or to preparations derived therefrom (for example spray liquors, seed dressings) particular properties such as certain technical properties and/or also particular biological properties. Typical suitable auxiliaries are: extenders, solvents and carriers. 
     Suitable extenders are, for example, water, polar and nonpolar organic chemical liquids, for example from the classes of the aromatic and non-aromatic hydrocarbons (such as paraffins, alkylbenzenes, alkylnaphthalenes, chlorobenzenes), the alcohols and polyols (which, if appropriate, may also be substituted, etherified and/or esterified), the ketones (such as acetone, cyclohexanone), esters (including fats and oils) and (poly)ethers, the unsubstituted and substituted amines, amides, lactams (such as N-alkylpyrrolidones) and lactones, the sulphones and sulphoxides (such as dimethyl sulphoxide). 
     If the extender used is water, it is also possible to employ, for example, organic solvents as auxiliary solvents. Essentially, suitable liquid solvents are: aromatics such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, for example petroleum fractions, mineral and vegetable oils, alcohols such as butanol or glycol and also their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethyl sulphoxide, and also water. 
     Suitable solid carriers are: 
     for example, ammonium salts and ground natural minerals such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as finely divided silica, alumina and silicates; suitable solid carriers for granules are: for example, crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite, and also synthetic granules of inorganic and organic meals, and granules of organic material such as paper, sawdust, coconut shells, maize cobs and tobacco stalks; suitable emulsifiers and/or foam-formers are: for example, nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonates and also protein hydrolysates; suitable dispersants are nonionic and/or ionic substances, for example from the classes of the alcohol-POE- and/or -POP-ethers, acid and/or POP-POE esters, alkyl aryl and/or POP-POE ethers, fat- and/or POP-POE adducts, POE- and/or POP-polyol derivatives, POE- and/or POP-sorbitan- or -sugar adducts, alkyl or aryl sulphates, alkyl- or arylsulphonates and alkyl or arylphosphates or the corresponding PO-ether adducts. Furthermore, suitable oligo- or polymers, for example those derived from vinylic monomers, from acrylic acid, from EO and/or PO alone or in combination with, for example, (poly)alcohols or (poly)amines. It is also possible to employ lignin and its sulphonic acid derivatives, unmodified and modified celluloses, aromatic and/or aliphatic sulphonic acids and their adducts with formaldehyde. 
     Tackifiers such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, as well as natural phospholipids such as cephalins and lecithins, and synthetic phospholipids, can be used in the formulations. 
     It is possible to use colorants such as inorganic pigments, for example iron oxide, titanium oxide and Prussian Blue, and organic dyestuffs, such as alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs, and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc. 
     Other possible additives are perfumes, mineral or vegetable, optionally modified oils, waxes and nutrients (including trace nutrients), such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc. 
     Stabilizers, such as low-temperature stabilizers, preservatives, antioxidants, light stabilizers or other agents which improve chemical and/or physical stability may also be present. 
     The formulations generally comprise between 0.01 and 98% by weight of active compound, preferably between 0.5 and 90%. 
     The active compound according to the invention can be used in its commercially available formulations and in the use forms, prepared from these formulations, as a mixture with other active compounds, such as insecticides, attractants, sterilizing agents, bactericides, acaricides, nematicides, fungicides, growth-regulating substances, herbicides, safeners, fertilisers or semiochemicals. 
     Particularly favourable mixing components are, for example, the following compounds: 
     Fungicides: 
     2-phenylphenol; 8-hydroxyquinoline sulphate; acibenzolar-S-methyl; aldimorph; amidoflumet; ampropylfos; ampropylfos-potassium; andoprim; anilazine; azaconazole; azoxystrobin; benalaxyl; benodanil; benomyl; benthiavalicarb-isopropyl; benzamacril; benzamacril-isobutyl; bilanafos; binapacryl; biphenyl; bitertanol; blasticidin-S; bromuconazole; bupirimate; buthiobate; butylamine; calcium polysulphide; capsimycin; captafol; captan; carbendazim; carboxin; carpropamid; carvone; quinomethionat; chlobenthiazone; chlorfenazole; chloroneb; chlorothalonil; chlozolinate; clozylacon; cyazofamid; cyflufenamid; cymoxanil; cyproconazole; cyprodinil; cyprofuram; Dagger G; debacarb; dichlofluanid; dichlone; dichlorophen; diclocymet; diclomezine; dicloran; diethofencarb; difenoconazole; diflumetorim; dimethirimol; dimethomorph; dimoxystrobin; diniconazole; diniconazole-M; dinocap; diphenylamine; dipyrithione; ditalimfos; dithianon; dodine; drazoxolon; edifenphos; epoxiconazole; ethaboxam; ethirimol; etridiazole; famoxadone; fenamidone; fenapanil; fenarimol; fenbuconazole; fenfuram; fenhexamid; fenitropan; fenoxanil; fenpiclonil; fenpropidin; fenpropimorph; ferbam; fluazinam; flubenzimine; fludioxonil; flumetover; flumorph; fluoromide; fluoxastrobin; fluquinconazole; flurprimidol; flusilazole; flusulfamide; flutolanil; flutriafol; folpet; fosetyl-Al; fosetyl-sodium; fuberidazole; furalaxyl; furametpyr; furcarbanil; furmecyclox; guazatine; hexachlorobenzene; hexaconazole; hymexazole; imazalil; imibenconazole; iminoctadine triacetate; iminoctadine tris(albesilate); iodocarb; ipconazole; iprobenfos; iprodione; iprovalicarb; irumamycin; isoprothiolane; isovaledione; kasugamycin; kresoxim-methyl; mancozeb; maneb; meferimzone; mepanipyrim; mepronil; metalaxyl; metalaxyl-M; metconazole; methasulfocarb; methfuroxam; metiram; metominostrobin; metsulfovax; mildiomycin; myclobutanil; myclozolin; natamycin; nicobifen; nitrothal-isopropyl; noviflumuron; nuarimol; ofurace; orysastrobin; oxadixyl; oxolinic acid; oxpoconazole; oxycarboxin; oxyfenthiin; paclobutrazole; pefurazoate; penconazole; pencycuron; phosdiphen; phthalide; picoxystrobin; piperalin; polyoxins; polyoxorim; probenazole; prochloraz; procymi-done; propamocarb; propanosine-sodium; propiconazole; propineb; proquinazid; prothioconazole; pyraclostrobin; pyrazophos; pyrifenox; pyrimethanil; pyroquilon; pyroxyfur; pyrrolnitrine; quinconazole; quinoxyfen; quintozene; simeconazole; spiroxamine; sulfur; tebuconazole; tecloftalam; tecnazene; tetcyclacis; tetraconazole; thiabendazole; thicyofen; thifluzamide; thiophanate-methyl; thiram; tioxymid; tolclofos-methyl; tolylfluanid; triadimefon; triadimenol; triazbutil; triazoxide; tricyclamide; tricyclazole; tridemorph, trifloxystrobin; triflumizole; triforine; triticonazole; uniconazole; validamycin A; vinclozolin; zineb; ziram; zoxamide; (2S)—N-[2-[4-[[3-(4-chlorophenyl)-2-propynyl]oxy]-3-methoxyphenyl]ethyl]-3-methyl-2-[(methylsulphonyl)amino]butanamide; 1-(1-naphthalenyl)-1H-pyrrole-2,5-dione; 2,3,5,6-tetrachloro-4-(methylsulphonyl)pyridine; 2-amino-4-methyl-N-phenyl-5-thiazolecarboxamide; 2-chloro-N-(2,3-dihydro-1,1,3-trimethyl-1H-inden-4-yl)-3-pyridinecarboxamide; 3,4,5-trichloro-2,6-pyridinedi-carbonitrile; actinovate; cis-1-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)cycloheptanol; methyl 1-(2,3-dihydro-2,2-dimethyl-1H-inden-1-yl)-1H-imidazole-5-carboxylate; monopotassium carbonate; N-(6-methoxy-3-pyridinyl)cyclopropanecarboxamide; N-butyl-8-(1,1-dimethylethyl)-1-oxaspiro-[4.5]decan-3-amine; sodium tetrathiocarbonate; and also copper salts and preparations, such as Bordeaux mixture; copper hydroxide; copper naphthenate; copper oxychloride; copper sulphate; cufraneb; copper oxide; mancopper; oxine-copper. 
     Bactericides: 
     bronopol, dichlorophen, nitrapyrin, nickel dimethyldithiocarbamate, kasugamycin, octhilinone, furancarboxylic acid, oxytetracyclin, probenazole, streptomycin, tecloftalam, copper sulphate and other copper preparations. 
     Insecticides/Acaricides/Nematicides: 
     Acetylcholine esterase (AChE) inhibitors
     1.1 Carbamates,
       for example alanycarb, aldicarb, aldoxycarb, allyxycarb, aminocarb, bendiocarb, benfuracarb, bufencarb, butacarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, cloethocarb, dimetilan, ethiofencarb, fenobucarb, fenothiocarb, formetanate, furathiocarb, isoprocarb, metam-sodium, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, promecarb, propoxur, thiodicarb, thiofanox, trimethacarb, XMC, xylylcarb, triazamate   
       1.2 Organophosphates,
       for example acephate, azamethiphos, azinphos (-methyl, -ethyl), bromophos-ethyl, bromfenvinfos (-methyl), butathiofos, cadusafos, carbophenothion, chlorethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos (-methyl/-ethyl), coumaphos, cyanofenphos, cyanophos, chlorfenvinphos, demeton-S-methyl, demeton-S-methylsulphon, dialifos, diazinon, dichlofenthion, dichlorvos/DDVP, dicrotophos, dimethoate, dimethylvinphos, dioxabenzofos, disulfoton, EPN, ethion, ethoprophos, etrimfos, famphur, fenamiphos, fenitrothion, fensulfothion, fenthion, flupyrazofos, fonofos, formothion, fosmethilan, fosthiazate, heptenophos, iodofenphos, iprobenfos, isazofos, isofenphos, isopropyl O-salicylate, isoxathion, malathion, mecarbam, methacrifos, methamidophos, methidathion, mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl, parathion (-methyl/-ethyl), phenthoate, phorate, phosalone, phosmet, phosphamidon, phosphocarb, phoxim, pirimiphos (-methyl/-ethyl), profenofos, propaphos, propetamphos, prothiofos, prothoate, pyraclofos, pyridaphenthion, pyridathion, quinalphos, sebufos, sulfotep, sulprofos, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, triclorfon, vamidothion   
       

     Sodium Channel Modulators/Voltage-Dependent Sodium Channel Blockers 
     
         
         2.1 Pyrethroids,
       for example acrinathrin, allethrin (d-cis-trans, d-trans), beta-cyfluthrin, bifenthrin, bioallethrin, bioallethrin-S cyclopentyl isomer, bioethanomethrin, biopermethrin, bioresmethrin, chlovaportn, cis-cypermethrin, cis-resmethrin, cis-permethrin, clocythrin, cycloprothrin, cyfluthrin, cyhalothrin, cypermethrin (alpha-, beta-, theta-, zeta-), cyphenothrin, deltamethrin, empenthrin (1R isomer), esfenvalerate, etofenprox, fenfluthrin, fenpropathrin, fenpyrithrin, fenvalerate, flubrocythrinate, flucythrinate, flufenprox, flumethrin, fluvalinate, fubfenprox, gamma-cyhalothrin, imiprothrin, kadethrin, lambda-cyhalothrin, metofluthrin, permethrin (cis-, trans-), phenothrin (1R trans-isomer), prallethrin, profluthrin, protrifenbute, pyresmethrin, resmethrin, RU 15525, silafluofen, taufluvalinate, tefluthrin, terallethrin, tetramethrin (1R isomer), tralomethrin, transfluthrin, ZXI 8901, pyrethrins (pyrethrum)   
     
       
    
     DDT
     2.2 Oxadiazines,
       for example indoxacarb   
       

     Acetylcholine Receptor Agonists/Antagonists 
     
         
         3.1 Chloronicotinyls,
       for example acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, nithiazine, thiacloprid, thiamethoxam   
     
         3.2 Nicotines, Bensultap, Cartap 
       
    
     Acetylcholine Receptor Modulators 
     
         
         4.1 Spinosyns,
       for example spinosad   
     
       
    
     GABA-Controlled Chloride Channel Antagonists 
     
         
         5.1 Organochlorines,
       for example camphechlor, chlordane, endosulfan, gamma-HCH, HCH, heptachlor, lindane, methoxychlor   
     
         5.2 Fiproles,
       for example acetoprole, ethiprole, fipronil, pyrafluprole, pyriprole, vaniliprole   
     
       
    
     Chloride Channel Activators 
     
         
         6.1 Mectins,
       for example avermectin, emamectin, emamectin-benzoate, ivermectin, milbemycin   
     
       
    
     Juvenile Hormone Mimetics, 
     
         
         
           
             for example diofenolan, epofenonane, fenoxycarb, hydroprene, kinoprene, methoprene, pyriproxifen, triprene 
           
         
       
    
     Ecdysone Agonists/Disruptors 
     
         
         8.1 Diacylhydrazines,
       for example chromafenozide, halofenozide, methoxyfenozide, tebufenozide   
     
       
    
     Chitin Biosynthesis Inhibitors 
     
         
         9.1 Benzoylureas,
       for example bistrifluoron, chlofluazuron, diflubenzuron, fluazuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, penfluoron, teflubenzuron, triflumuron   
     
         9.2 Buprofezin 
         9.3 Cyromazine 
       
    
     Oxidative Phosphorylation Inhibitors, ATP Disruptors 
     
         
         10.1 Diafenthiuron 
         10.2 Organotin Compounds,
       for example azocyclotin, cyhexatin, fenbutatin-oxide   
     
       
    
     Oxidative Phosphorylation Decouplers Acting by Interrupting the H-Proton Gradient 
     
         
         11.1 Pyrroles,
       for example chlorfenapyr   
     
         11.2 Dinitrophenols,
       for example binapacyrl, dinobuton, dinocap, DNOC   
     
       
    
     Site-I Electron Transport Inhibitors 
     
         
         12.1 METIs,
       for example fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad, tolfenpyrad   
     
         12.2 Hydramethylnon 
         12.3 Dicofol 
       
    
     Site-II Electron Transport Inhibitors 
     
         
         
           
             Rotenone
 
Site-III electron transport inhibitors
 
             Acequinocyl, fluacrypyrim 
           
         
       
    
     Microbial Disruptors of the Insect Gut Membrane 
     
         
         
           
               Bacillus thuringiensis  strains 
           
         
       
    
     Fat Synthesis Inhibitors 
     
         
         
           
             Tetronic Acids, 
             for example spirodiclofen, spiromesifen 
             Tetramic Acids, 
             for example spirotetramat (CAS Reg. No.: 203313-25-1) and 3-(2,5-dimethylphenyl)-8-methoxy-2-oxo-1-azaspiro[4.5]dec-3-en-4-yl ethyl carbonate (aka: carbonic acid, 3-(2,5-dimethylphenyl)-8-methoxy-2-oxo-1-azaspiro[4.5]dec-3-en-4-yl ethyl ester, CAS Reg. No.: 382608-10-8) 
             Carboxamides, 
             for example flonicamid 
             Octopaminergic Agonists, 
             for example amitraz 
           
         
       
    
     Inhibitors of Magnesium-Stimulated ATPase, 
     
         
         
           
             Propargite 
             activators of the ryanodine-sensitive calcium channel, for example 
             Benzoic Acid Dicarboxamides, 
             for example flubendiamides 
             Nereistoxin Analogues 
             for example thiocyclam hydrogen oxalate, thiosultap-sodium 
           
         
       
    
     Biologicals, Hormones or Pheromones 
     
         
         
           
               azadirachtin, Bacillus  spec.,  Beauveria  spec.,  codlemone, Metarrhizium  spec.,  Paecilomyces  spec.,  thuringiensin, Verticillium  spec.
 
Active Compounds with Unknown or Unspecific Mechanisms of Action
 
           
         
         23.1 Fumigants,
       for example aluminium phosphide, methyl bromide, sulfuryl fluoride   
     
         23.2. Antifeedants,
       for example cryolite, flonicamid, pymetrozine   
     
         23.3 Mite Growth Inhibitors,
       for example clofentezine, etoxazole, hexythiazox   
     
         23.4 Amidoflumet, benclothiaz, benzoximate, bifenazate, bromopropylate, buprofezin, chinomethionat, chlordimeform, chlorobenzilate, chloropicrin, clothiazoben, cycloprene, cyflumetofen, dicyclanil, fenoxacrim, fentrifanil, flubenzimine, flufenerim, flutenzin, gossyplure, hydramethylnone, japonilure, metoxadiazone, petroleum, piperonyl butoxide, potassium oleate, pyridalyl, sulfluramid, tetradifon, tetrasul, triarathene, verbutin 
       
    
     A mixture with other known active compounds, such as herbicides, fertilizers, growth regulators, safeners, semiochemicals, or else with agents for improving the plant properties, is also possible. 
     When used as insecticides, the active compounds according to the invention can furthermore be present in their commercially available formulations and in the use forms, prepared from these formulations, as a mixture with synergistic agents. Synergistic agents are compounds which increase the action of the active compounds, without it being necessary for the synergistic agent added to be active itself. 
     When used as insecticides, the active compounds according to the invention can furthermore be present in their commercially available formulations and in the use forms, prepared from these formulations, as a mixture with inhibitors which reduce degradation of the active compound after use in the environment of the plant, on the surface of parts of plants or in plant tissues. 
     The active compound content of the use forms prepared from the commercially available formulations can vary within wide limits. The active compound concentration of the use forms can be from 0.00000001 to 95% by weight of active compound, preferably between 0.00001 and 1% by weight. 
     The compounds are employed in a customary manner appropriate for the use forms. 
     As already mentioned above, it is possible to treat all plants and their parts according to the invention. In a preferred embodiment, wild plant species and plant cultivars, or those obtained by conventional biological breeding methods, such as crossing or protoplast fusion, and parts thereof, are treated. In a further preferred embodiment, transgenic plants and plant cultivars obtained by genetic engineering methods, if appropriate in combination with conventional methods (Genetically Modified Organisms), and parts thereof are treated. The terms “parts”, “parts of plants” and “plant parts” have been explained above. 
     Particularly preferably, plants of the plant cultivars which are in each case commercially available or in use are treated according to the invention. Plant cultivars are to be understood as meaning plants having novel properties (“traits”) which have been obtained by conventional breeding, by mutagenesis or by recombinant DNA techniques. These can be cultivars, bio- or genotypes. 
     Depending on the plant species or plant cultivars, their location and growth conditions (soils, climate, vegetation period, diet), the treatment according to the invention may also result in superadditive (“synergistic”) effects. Thus, for example, reduced application rates and/or a widening of the activity spectrum and/or an increase in the activity of the substances and compositions which can be used according to the invention, better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering performance, easier harvesting, accelerated maturation, higher harvest yields, higher quality and/or a higher nutritional value of the harvested products, better storage stability and/or processability of the harvested products are possible, which exceed the effects which were actually to be expected. 
     The transgenic plants or plant cultivars (obtained by genetic engineering) which are preferably to be treated according to the invention include all plants which, by virtue of the genetic modification, received genetic material which imparted particularly advantageous, useful traits to these plants. Examples of such traits are better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering performance, easier harvesting, accelerated maturation, higher harvest yields, higher quality and/or a higher nutritional value of the harvested products, better storage stability and/or processability of the harvested products. Further and particularly emphasized examples of such traits are a better defence of the plants against animal and microbial pests, such as against insects, mites, phytopathogenic fungi, bacteria and/or viruses, and also increased tolerance of the plants to certain herbicidally active compounds. Examples of transgenic plants which may be mentioned are the important crop plants, such as cereals (wheat, rice), maize, soya beans, potatoes, sugar beet, tomatoes, peas and other vegetable varieties, cotton, tobacco, oilseed rape and also fruit plants (with the fruits apples, pears, citrus fruits and grapes), and particular emphasis is given to maize, soya beans, potatoes, cotton, tobacco and oilseed rape. Traits that are emphasized are in particular increased defence of the plants against insects, arachnids, nematodes and worms by virtue of toxins formed in the plants, in particular those formed in the plants by the genetic material from  Bacillus thuringiensis  (for example by the genes CryIA(a), CryIA(b), CryIA(c), CryIIA, CryIIIA, CryIIIB2, Cry9c, Cry2Ab, Cry3Bb and CryIF and also combinations thereof) (referred to hereinbelow as “Bt plants”). Traits that are also particularly emphasized are the increased defence of the plants against fungi, bacteria and viruses by systemic acquired resistance (SAR), systemin, phytoalexins, elicitors and resistance genes and correspondingly expressed proteins and toxins. Traits that are furthermore particularly emphasized are the increased tolerance of the plants to certain herbicidally active compounds, for example imidazolinones, sulphonylureas, glyphosate or phosphinotricin (for example the “PAT” gene). The genes which impart the desired traits in question can also be present in combination with one another in the transgenic plants. Examples of “Bt plants” which may be mentioned are maize varieties, cotton varieties, soya bean varieties and potato varieties which are sold under the trade names YIELD GARD® (for example maize, cotton, soya beans), KnockOut® (for example maize), StarLink® (for example maize), Bollgard® (cotton), Nucotn® (cotton) and NewLeaf® (potato). Examples of herbicide-tolerant plants which may be mentioned are maize varieties, cotton varieties and soya bean varieties which are sold under the trade names Roundup Ready® (tolerance to glyphosate, for example maize, cotton, soya bean), Liberty Link® (tolerance to phosphinotricin, for example oilseed rape), IMI® (tolerance to imidazolinones) and STS® (tolerance to sulphonylureas, for example maize). Herbicide-resistant plants (plants bred in a conventional manner for herbicide tolerance) which may be mentioned include the varieties sold under the name Clearfield® (for example maize). Of course, these statements also apply to plant cultivars having these genetic traits or genetic traits still to be developed, which plants will be developed and/or marketed in the future. 
     The plants listed can be treated according to the invention in a particularly advantageous manner with the compounds of the general formula I and/or the active compound mixtures according to the invention. The preferred ranges stated above for the active compounds or mixtures also apply to the treatment of these plants. Particular emphasis is given to the treatment of plants with the compounds or mixtures specifically mentioned in the present text. 
     The active compounds according to the invention act not only against plant, hygiene and stored product pests, but also in the veterinary medicine sector against animal parasites (ecto- and endoparasites), such as hard ticks, soft ticks, mange mites, leaf mites, flies (biting and licking), parasitic fly larvae, lice, hair lice, feather lice and fleas. These parasites include: 
     From the order of the Anoplurida, for example,  Haematopinus  spp.,  Linognathus  spp.,  Pediculus  spp.,  Phtirus  spp.,  Solenopotes  spp. 
     From the order of the Mallophagida and the suborders Amblycerina and Ischnocerina, for example,  Trimenopon  spp.,  Menopon  spp.,  Trinoton  spp.,  Bovicola  spp.,  Werneckiella  spp.,  Lepikentron  spp.,  Damalina  spp.,  Trichodectes  spp.,  Felicola  spp. 
     From the order of the Diptera and the suborders Nematocerina and Brachycerina, for example,  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, for example,  Pulex  spp.,  Ctenocephalides  spp.,  Xenopsylla  spp.,  Ceratophyllus  spp. 
     From the order of the Heteropterida, for example,  Cimex  spp.,  Triatoma  spp.,  Rhodnius  spp.,  Panstrongylus  spp. 
     From the order of the Blattarida, for example,  Blatta orientalis, Periplaneta americana, Blattela germanica, Supella  spp. 
     From the subclass of the Acari (Acarina) and the orders of the Meta- and Mesostigmata, for example,  Argas  spp.,  Ornithodorus  spp.,  Otobius  spp.,  Ixodes  spp.,  Amblyomma  spp.,  Boophilus  spp.,  Dennacentor  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), for example,  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 controlling arthropods which infest agricultural productive livestock, such as, for example, cattle, sheep, goats, horses, pigs, donkeys, camels, buffalo, rabbits, chickens, turkeys, ducks, geese and bees, other pets, such as, for example, dogs, cats, caged birds and aquarium fish, and also so-called test animals, such as, for example, hamsters, guinea pigs, rats and mice. By controlling these arthropods, cases of death and reduction in productivity (for meat, milk, wool, hides, eggs, honey etc.) should be diminished, so that more economic and easier animal husbandry is possible by use of the active compounds according to the invention. 
     The active compounds according to the invention are used in the veterinary sector and in animal husbandry in a known manner by enteral administration in the form of, for example, tablets, capsules, potions, drenches, granules, pastes, boluses, the feed-through process and suppositories, by parenteral administration, such as, for example, by injection (intramuscular, subcutaneous, intravenous, intraperitoneal and the like), implants by nasal administration, by dermal use in the form, for example, of dipping or bathing, spraying, pouring on and spotting on, washing and powdering, and also with the aid of moulded articles containing the active compound, such as collars, ear marks, tail marks, limb bands, halters, marking devices and the like. 
     When used for cattle, poultry, pets and the like, the active compounds of the formula (I) can be used as formulations (for example powders, emulsions, free-flowing compositions), which comprise the active compounds in an amount of 1 to 80% by weight, directly or after 100 to 10 000-fold dilution, or they can be used as a chemical bath. 
     It has furthermore been found that the compounds according to the invention also have a strong insecticidal action against insects which destroy industrial materials. 
     The following insects may be mentioned as examples and as preferred—but without any limitation: 
     Beetles, such as  Hylotrupes bajulus, Chlorophorus pilosis, Anobium punctatum, Xestobium rufovillosum, Ptilinus pecticornis, Dendrobium pertinex, Emobius mollis, Priobium carpini, Lyctus brunneus, Lyctus africanus, Lyctus planicollis, Lyctus linearis, Lyctus pubescens, Trogoxylon aequale, Minthes rugicollis, Xyleborus  spec.  Tryptodendron  spec.  Apate monachus, Bostrychus capucins, Heterobostrychus brunneus, Sinoxylon  spec.  Dinoderus minutus;    
     Hymenopterons, such as  Sirex juvencus, Urocerus gigas, Urocerus gigas taignus, Urocerus augur;    
     Termites, such as  Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicola, Reticulitermes flavipes, Reticulitermes santonensis, Reticulitermes lucifugus, Mastotermes darwiniensis, Zootermopsis nevadensis, Coptotermes formosanus;    
     Bristletails, such as  Lepisma saccharina.    
     Industrial materials in the present connection are to be understood as meaning non-living materials, such as, preferably, plastics, adhesives, sizes, papers and cardboards, leather, wood and processed wood products and coating compositions. 
     The ready-to-use compositions may, if appropriate, comprise further insecticides and, if appropriate, one or more fungicides. 
     With respect to possible additional additives, reference may be made to the insecticides and fungicides mentioned above. 
     The compounds according to the invention can likewise be employed for protecting objects which come into contact with saltwater or brackish water, such as hulls, screens, nets, buildings, moorings and signalling systems, against fouling. 
     Furthermore, the compounds according to the invention, alone or in combination with other active compounds, may be employed as antifouling agents. 
     In domestic, hygiene and stored-product protection, the active compounds are also suitable for controlling animal pests, in particular insects, arachnids and mites, which are found in enclosed spaces such as, for example, dwellings, factory halls, offices, vehicle cabins and the like. They can be employed alone or in combination with other active compounds and auxiliaries in domestic insecticide products for controlling these pests. They are active against sensitive and resistant species and against all developmental stages. These pests include: 
     From the order of the Scorpionidea, for example,  Buthus occitanus.    
     From the order of the Acarina, for example,  Argas persicus, Argas reflexus, Bryobia  ssp.,  Dermanyssus gallinae, Glyciphagus domesticus, Ornithodorus moubat, Rhipicephalus sanguineus, Trombicula alfreddugesi, Neutrombicula autumnalis, Dermatophagoides pteronissimus, Dermatophagoides forinae.    
     From the order of the Araneae, for example,  Aviculariidae, Araneidae.    
     From the order of the Opiliones, for example,  Pseudoscorpiones chelifer, Pseudoscorpiones cheiridium, Opiliones phalangium.    
     From the order of the Isopoda, for example,  Oniscus asellus, Porcellio scaber.    
     From the order of the Diplopoda, for example,  Blaniulus guttulatus, Polydesmus  spp. 
     From the order of the Chilopoda, for example,  Geophilus  spp. 
     From the order of the Zygentoma, for example,  Ctenolepisma  spp.,  Lepisma saccharina, Lepismodes inquilinus.    
     From the order of the Blattaria, for example,  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, for example,  Acheta domesticus.    
     From the order of the Dermaptera, for example,  Forficula auricularia.    
     From the order of the Isoptera, for example,  Kalotermes  spp.,  Reticulitermes  spp. 
     From the order of the Psocoptera, for example,  Lepinatus  spp.,  Liposcelis  spp. 
     From the order of the Coleoptera, for example,  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, for example,  Aedes aegypti, Aedes albopictus, Aedes taeniorhynchus, Anopheles  spp.,  Calliphora erythrocephala, Chrysozona pluvialis, Culex quinquefasciatus, Culex pipiens, Culex tarsalis, Drosophila  spp.,  Fannia canicularis, Musca domestica, Phlebotomus  spp.,  Sarcophaga carnaria, Simulium  spp.,  Stomoxys calcitrans, Tipula paludosa.    
     From the order of the Lepidoptera, for example,  Achroia grisella, Galleria mellonella, Plodia interpunctella, Tinea cloacella, Tinea pellionella, Tineola bisselliella.    
     From the order of the Siphonaptera, for example,  Ctenocephalides canis, Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis.    
     From the order of the Hymenoptera, for example,  Camponotus herculeanus, Lasius fuliginosus, Lasius niger, Lasius umbratus, Monomorium pharaonis, Paravespula  spp.,  Tetramorium caespitum.    
     From the order of the Anoplura, for example,  Pediculus humanus capitis, Pediculus humanus corporis, Pemphigus  spp.,  Phylloera vastatrix, Phthirus pubis.    
     From the order of the Heteroptera, for example,  Cimex hemipterus, Cimex lectularius, Rhodinus prolixus, Triatoma infestans.    
     In the field of household insecticides, they are used alone or in combination with other suitable active compounds, such as phosphoric esters, carbamates, pyrethroids, neonicotinoides, growth regulators or active compounds from other known classes of insecticides. 
     They are used in aerosols, pressure-free spray products, for example pump and atomizer sprays, automatic fogging systems, foggers, foams, gels, evaporator products with evaporator tablets made of cellulose or polymer, liquid evaporators, gel and membrane evaporators, propeller-driven evaporators, energy-free, or passive, evaporation systems, moth papers, moth bags and moth gels, as granules or dusts, in baits for spreading or in bait stations. 
    
    
     PREPARATION EXAMPLES 
     Examples of Preparation of Precursors for the Synthesis of the Compounds of the General Formula (II) 
     (1): 1-(3-Chloro-2,5-dihydroxyphenyl)ethanone 
     
       
         
         
             
             
         
       
     
     Over the course of 2 h 57 g of N-chlorosuccinimide are added in portions and under nitrogen to a solution of 50 g of 2,5-dihydroxypentylacetone in 800 ml of DMF. 
     The reaction solution undergoes brown discoloration and is stirred at RT overnight. 
     The reaction mixture is poured into 1.5 l of water and is extracted a number of times with a 1:1 hexane/ethyl acetate mixture. The combined organic phases are washed twice with water, dried over Na 2 SO 4  and filtered and the filtrate is evaporated to dryness. The crude product is recrystallized from hexane/ethyl acetate. This gives 20.5 g of clean 1-(3-chloro-2,5-dihydroxyphenyl)ethanone and 28.5 g of mildly impure product. 
     M+(ES+)=(187, 100) 
       1 H-NMR (CD 3 CN): 2.60 (s, 3H, CH 3 ); 6.98 (bs, 1H, OH); 7.18 (d, J=0.3 Hz, 1H, aryl); 7.25 (d, J=0.3 Hz, 1H, aryl); 12.22 (s, 1H, OH) 
     (2): 1-(3-Chloro-2-hydroxy-5-triisopropylsilanyloxyphenyl)ethanone 
     
       
         
         
             
             
         
       
     
     First 5 g of 1-(3-chloro-2,5-dihydroxyphenyl)ethanone in 300 ml of dichloromethane are admixed with 4 g of triethylamine and 5.2 g of triisopropylsilyl chloride and the reaction mixture is stirred at RT for 3 h. It is washed with water, dried over Na 2 SO 4  and filtered and the filtrate is evaporated to dryness. This gives 8.28 g (in 73% pure form according to LC-MS) of 1-(3-chloro-2-hydroxy-5-triisopropylsilanyloxyphenyl)ethanone as a dark oil. 
     M+(ES+)=(343, 100) 
       1 H-NMR (CD 3 CN): 1.11 (d, J=7.2 Hz; 9H, CH 3 , iPr); 1.26-1.33 (m, 3H, CH, iPr); 2.60 (s, 3H, CH 3 ); 7.23 (d, J=2.9 Hz, 1H, aryl); 7.29 (d, J=2.9 Hz, 1H, aryl); 12.33 (s, 1H, OH). 
     In the same way as for (2) the following compounds were prepared: 
     
       
         
         
             
             
         
       
     
     (3): (3-Chloro-2-hydroxy-5-(triisopropylsilyloxy)phenyl)-2-methylpropan-1-one 
     Reaction of 33 g of 1-(3-chloro-2,5-dihydroxyphenyl)-2-methylpropan-1-one and 31.3 g of chlorotriisopropylsilane gave 56 g of product (93% pure according to LC-MS) of a brown oil. 
     M+(ES+)=(371, 100) 
       1 H-NMR (DMSO-D 6 ): 1.08 (d, J=7.3 Hz, 18H, Si-iPr 3 ) 1.14 (d, J=6.8 Hz, 6H, iPr); 1.25 (m, 3H, Si-iPr 3 ); 3.63 (m, 1H, iPr); 7.23 (d, J=2.9 Hz, 1H, aryl); 7.27 (d, J=2.9 Hz, aryl); 12.0 (s, 1H, OH) 
     (4): 3-Chloro-2-hydroxy-5-(triisopropylsilyloxy)phenyl cyclopropyl ketone 
     Reaction of 85 g of 3-chloro-2,5-dihydroxyphenyl cyclopropyl ketone and 81 g of chlorotriisopropylsilane followed by brief column filtration (5:1 cyclohexane/ethyl acetate) gave 85 g of a brown oil product. 
     M+(ES+)=(369, 100) 
       1 H-NMR (DMSO-D 6 ): 1.08 (d, J=7.3 Hz, 18H, -iPr); 1.09 (m, 4H, -cPr); 1.26 (m, 3H, -iPr); 2.17 (m, 1H, -cPr); 7.24 (d, J=2.9 Hz, 1H, aryl); 7.27 (d, J=2.9 Hz, aryl); 11.85 (s, 1H, OH) 
     (5): 3-Chloro-2-hydroxy-5-(triisopropylsilyloxy)phenyl cyclohexyl ketone 
     Reaction of 33 g of (3-chloro-2,5-dihydroxyphenyl)cyclohexyl ketone and 31.3 g of chlorotriisopropylsilane gave 56 g of a brown oil crude product, which was used without purification in the next step. 
     M+(ES+)=(411, 100) 
       1 H-NMR (DMSO-D 6 ): 1.08 (d, J=7.3 Hz, 18H, -iPr); 1.24 (m, 3H, -iPr); 1.33 (m, 2H, -cHex); 2.58-2.83 (bm, 8H, chex); 2.72 (m, 1H, -cHex); 7.25 (m, 2H, aryl); 12.0 (s, 1H, OH) 
     (6): 1-(3-Chloro-5-hydroxy-2-methoxyphenyl)ethanone 
     
       
         
         
             
             
         
       
     
     First 15 g of 1-(3-chloro-2-hydroxy-5-triisopropylsilanyloxyphenyl)ethanone are stirred into 250 ml of DMF together with 24 g of potassium carbonate and 24.8 g of dimethyl sulphate at RT for approximately 5 h. The reaction mixture is filtered and the residue is washed with dichloromethane. The combined organic phases are poured into water, stirred for 30 minutes thereafter and extracted three times with dichloromethane, the extracts being dried over Na 2 SO 4  and filtered and the filtrate being evaporated to dryness. 
     The crude product is taken off in 250 ml of ethanol, 1N NaOH is added, and the mixture is stirred under reflux for a number of hours until a TLC check indicates complete conversion. The batch is concentrated to dryness, the residue is admixed with water, brought to a pH&lt;7 with HCl and extracted a number of times with EE, the extracts are dried over Na 2 SO 4  and filtered and the filtrate is evaporated to dryness on a rotary evaporator. The crude product is purified by flash chromatography over silica gel (gradient: 4:1 hexane/ethyl acetate to 100% ethyl acetate). This gives two product fractions: 4.6 g (100% purity according to LC-MS) and 1.3 g (95% purity according to LC-MS). 
     M+(ES+)=(201, 100) 
       1 H-NMR: 2.67 (s, 3H, CH 3 ); 3.85 (s, 3H, OCH 3 ); 6.21 (s, 1H, OH); 7.11 (d, J=6.2 Hz, 1H, aryl); 7.12 (d, J=6.2 Hz, 1H, aryl) 
     In the same way as for (6) the following compounds were prepared: 
     
       
         
         
             
             
         
       
     
     (7): (3-Chloro-5-hydroxy-2-methoxyphenyl)-2-methylpropan-1-one 
     Reaction of 56.2 g of (3-chloro-2-hydroxy-5-(triisopropylsilyloxy)phenyl)-2-methylpropan-1-one and 28.6 ml of dimethyl sulphate gave a brown oil, which was stirred under reflux with 150 ml of 2N sodium hydroxide solution and 300 ml of ethanol for a number of hours and, following aqueous workup, was chromatographed over silica gel (5:1 cyclohexane/ethyl acetate). This gave 21.6 g of an orange-coloured oil (GC purity 71%). 
     M+(ES+)=(229, 100) 
       1 H-NMR (DMSO-D 6 ): 1.07 (d, J=6.9 Hz, 6H, -iPr); 3.26 (m, 1H, -iPr); 3.68 (s, 3H, —OMe); 6.75 (d, J=2.9 Hz, 1H, aryl); 6.98 (d, J=2.9 Hz, aryl); 9.88 (s, 1H, OH) 
     (8): 3-Chloro-5-hydroxy-2-methoxyphenyl cyclopropyl ketone 
     Reaction of 85 g of 3-chloro-2-hydroxy-5-(triisopropylsilyloxy)phenyl cyclopropyl ketone and 58 g of dimethyl sulphate gave a brown oil, which was refluxed with 290 ml of 2N NaOH and 500 ml of ethanol for a number of hours and, following aqueous workup, was chromatographed on silica gel (5:1 cyclohexane/ethyl acetate). This gave 15.3 g of an orange-coloured oil. 
     M+(ES+)=(227, 100) 
       1 H-NMR (DMSO-D 6 ): 1.07 (d, J=6.2 Hz, 4H, -cPr); 2.61 (m, 1H, -cPr); 3.72 (s, 3H, —OMe); 6.84 (d, J=3 Hz, aryl); 7.02 (d, J=3 Hz, aryl); 9.92 (s, 1H, OH) 
     (9): 3-Chloro-5-hydroxy-2-methoxyphenyl cyclohexyl ketone 
     Reaction of 83 g of 3-chloro-2-hydroxy-5-(triisopropylsilyloxy)phenyl cyclohexyl ketone and 51 g of dimethyl sulphate gave a brown oil, which was refluxed with 200 ml of 2N NaOH and 400 ml of ethanol for a number of hours and, following aqueous workup, was chromatographed on silica gel (5:1 cyclohexane/ethyl acetate). This gave 12 g of an orange-red oil. 
     M+(ES+)=(269, 100) 
       1 H-NMR (DMSO-D 6 ): 1.11-1.33 (bm, 4H, -cHex); 1.54-1.82 (bm, 6H, -cHex); 2.99 (m, 1H, -cHex); 3.68 (s, 3H, —OMe); 6.72 (d, J=2.9 Hz, aryl); 6.96 (d, J=2.9 Hz, aryl); 9.92 (s, 1H, OH) 
     Examples of Preparation of Compounds of the General Formula (II) 
     (10): 1-[3-Chloro-5-(3,3-dichloroallyloxy)-2-hydroxyphenyl]ethanone 
     
       
         
         
             
             
         
       
     
     First 8.6 g of potassium carbonate in 200 ml of absolute dimethylformamide are admixed under nitrogen with 5 g of 1-(3-chloro-2,5-dihydroxyphenyl)ethanone. Subsequently 4.7 g of dichloropropenyl bromide are added dropwise with vigorous stirring, as a solution in 10 ml of DMF, and the batch is stirred at RT for a further 5 h. It is then poured into approximately 200 ml of water, extracted a number of times with ethyl acetate; the organic phase is washed with water, dried over Na 2 SO 4  and filtered and the filtrate is evaporated to dryness. This gives 7.5 g (97% purity according to LC-MS) of 1-[3-chloro-5-(3,3-dichloroallyloxy)-2-hydroxyphenyl]ethanone as a viscose oil. 
     M+(ES+)=(309, 100) 
       1 H-NMR (CDCl 3 ): 2.65 (s, 3H, CH 3 ); 3.85 (s, 3H, OCH 3 ); 4.62 (d, J=6.3 Hz, 2H, CH 2 ); 6.12 (t, 1H, J=6.3 Hz, 1H, CH); 7.05 (d, J=3.2 Hz, 1H, CH aryl); 7.1 (d, J=3.2 Hz, 1H, CH aryl) 
     In analogy to the instructions for 1-[3-chloro-5-(3,3-dichloroallyloxy)-2-hydroxyphenyl]-ethanone (10) the following compounds were prepared: 
     
       
         
           
               
               
               
             
               
                   
               
               
                 Identification 
                 Structure 
                 Physical data 
               
               
                   
               
             
            
               
                 (11): [3-Chloro-5-(3,3-dichloro- allyloxy)-2-methoxyphenyl]- cyclohexylmethanone 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 M + (ES+) = (379, 100)  1 H-NMR(CD 3 CN): 1.30-1.39 (m, 4H, cHex); 1.64-1.92 (m, 6H, cHex); 3.03-3.06 (m, 1H, cHex); 3.76 (s, 3H, OCH 3 ); 4.66 (d, J = 6.4 Hz, 2H, CH 2 ); 6.23 (t, J = 6.4 Hz, 1H, CH); 6.85 (d, J = 3.0 Hz, 1H, aryl); 7.12 (d, J = 3.0 Hz, 1H, aryl) 
               
               
                   
               
               
                 (12): 1-[3-Chloro-5-(3,3-dichloro- allyloxy)-2-methoxyphenyl]-2- methylpropan-1-one 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 M + (ES+) = (337, 100)  1 H-NMR(CDCl 3 ): 1.16 (d, J = 6.9 Hz, 6H, CH 3 ); 3.33-3.38 (m, 1H, iPr); 3.80 (s, 3H, OCH 3 ); 4.62 (d, J = 6.3 Hz, 2H, CH 2 ); 6.13 (t, J = 6.3 Hz, 1H, CH); 6.81 (d, J = 3.0 Hz, 1H, aryl); 7.03 (d, J = 3.0 Hz, 1H, aryl) 
               
               
                   
               
               
                 (13): [3-Chloro-5-(3,3-dichloro- allyloxy)-2-methoxyphenyl]- cyclopropylmethanone 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 M + (ES+): (335, 100)  1 H-NMR(CD 3 CN): 1.06-1.11 (m, 2H, CH 2 , cPr); 1.12-1.17 (m, 2H, CH 2 , cPr); 2.62-2.68 (m, 1H CH, cPr); 4.68 (d, J = 6.4 Hz, 2H, CH 2 ); 6.26 (t, J = 6.4 Hz, 1H, CH); 7.00 (d, J = 3.1 Hz, 1H, aryl), 7.18 (d, J = 3.1 Hz, 1H, aryl) 
               
               
                   
               
            
           
         
       
     
     Examples of Preparation of Compounds of the General Formula (III) 
     (14): 1-[3-Chloro-5-(3,3-dichloroallyloxy)-2-methoxyphenyl]-2-methylpropan-1-one oxime 
     
       
         
         
             
             
         
       
     
     First 1 g of 1-[3-chloro-5-(3,3-dichloroallyloxy)-2-methoxyphenyl]-2-methylpropan-1-one are stirred together with 1.44 g of hydroxylammonium chloride and 1.7 g of sodium acetate in 10 ml of ethanol under reflux for approximately 3 hours. The reaction mixture is evaporated to dryness, the residue is extracted a number of times with ethyl acetate, the combined organic phases are dried over sodium sulphate and filtered and the filtrate is evaporated to dryness. This gives 1.06 g of 1-[3-chloro-5-(3,3-dichloroallyloxy)-2-methoxyphenyl]-2-methylpropan-1-one oxime as an E/Z isomer mixture. 
     M+(ES+)=(352, 100) 
       1 H-NMR (CD 3 CN): 1.03 (m, 12 Hz, 4×CH 3 , iPr); 2.67-2.74 (m, 1H, CH, iPr); 3.28-3.41 (m, 1H, CH, iPr); 3.71 (s, 3H, OCH 3 ); 3.72 (s, 3H, OCH 3 ); 4.64 (d, J=6.4 Hz, 2H, CH 2 C H CCl 2 ); 4.65 (d, J=6.4 Hz, 2H, C H   2 CHCCl 2 ); 6.25 (t, J=6.4 Hz, 2H, 2×CH 2 C H CCl 2 ); 6.54 (d, J=3.0 Hz, aryl); 6.63 (d, J=3.0 Hz, aryl); 7.00 (d, J=3.0 Hz, aryl); 7.03 (d, J=3.0 Hz, aryl). 
     In analogy to the instructions for 1-[3-chloro-5-(3,3-dichloroallyloxy)-2-methoxyphenyl]-2-methylpropan-1-one oxime (14) the following compounds were prepared: 
     
       
         
           
               
               
               
             
               
                   
               
               
                 Identification 
                 Structure 
                 Physical data 
               
               
                   
               
             
            
               
                 (15): [3-Chloro-5-(3,3- dichloroallyloxy)-2- methoxyphenyl]cyclo- hexylmethanone oxime 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 M + (ES+) = (392, 100)  1 H-NMR(CD 3 CN, E/Z isomers): 1.22-1.43 (m, H, cHex); 1.64-1.82 (m, H, cHex); 3.73 (s, 3H, OCH 3 ); 3.73 (s, 3H, OCH 3 ); 4.62-4.65 (m, 4H, 2x CH 2 CHCCl 2 ); 6.15 (t, 1H, CH 2 CHCCl 2 ); 6.22 (t, J = 6.4 1H, CH 2 CHCCl 2 ); 6.51 (d, J = 3 Hz, 1H, aryl); 6.60 (d, J = 3 Hz, 1H, aryl); 6.98 (d, J = 3 Hz, 1H, aryl); 7.00 (d, J = 3 Hz, 1H, aryl); 
               
               
                   
               
               
                 (16): [3-Chloro-5-(3,3- dichloroallyloxy)-2- methoxyphenyl]- cyclopropylmethanone oxime 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 M + (ES+) = (350, 90)  1 H-NMR(CD 3 CN), E/Z isomers): 0.38-0.40 (m, 2H, CH 2 , iPr); 0.59-0.61 (m, 2H, CH 2 , iPr); 0.72-0.75 (m, 2H, CH 2 , iPr); 0.80-0.83 (m, 2H, CH 2 , iPr); 1.72-1.93, (m, 1H, CH); 2.43-2.46 (m, 1H, CH, iPr); 3.74 (s, 6H, 2x OCH 3 ); 4.63 (d, J = 6.4 Hz, 4H, 2x CH 2 CHCCl 2 ); 6.24 (t, J = 6.4 Hz, 1H, CH 2 CHCCl 2 ); 6.25 (t, J = 6.4 Hz, 1H, CH 2 CHCCl 2 ); 6.53 (d, J = 3.0 Hz, aryl); 6.57 (d, J = 3.0 Hz, aryl); 7.00 (d, J = 3.0 Hz, aryl); 7.02 (d, J = 3.0 Hz, aryl). 
               
               
                   
               
            
           
         
       
     
     (17): 1-[3-Chloro-5-(3,3-dichloroallyloxy)-2-methoxyphenyl]ethanone oxime 
     
       
         
         
             
             
         
       
     
     First 1 g of 2-methoxy-3-chloro-5-dichloropropenoxybenzylacetone in 4.3 ml of ethanol is admixed with 2.2 g of aqueous hydroxylamine solution (50% strength) and heated at 70° C. for 2 hours. The mixture is cooled to RT, the suspension formed is filtered, the solid is dissolved in dichloromethane, the solution is dried over sodium sulphate and filtered and the filtrate is evaporated to dryness. This gives 824 mg of 1-[3-chloro-5-(3,3-dichloroallyloxy)-2-methoxyphenyl]ethanone oxime as E/Z isomers in a ratio of 20:1. 
     M+(ES+)=(324, 100) 
       1 H-NMR (CD 3 CN): 3.70 (s, 3H, OCH 3 ); 4.64 (d, J=6.4 Hz, 2H, C H   2 CHCCl 2 ); 6.26 (t, J=6.4 Hz, 1H, CH 2 C H CCl 2 ); 6.79 (d, J=3.0 Hz, 1H, aryl); 7.03 (d, J=3.0 Hz, 1H, aryl); 9.05 (s, 1H, OH). 
     The filtrate is evaporated to dryness, the residue is extracted twice with approximately 50 ml of dichloromethane, the extracts are dried over sodium sulphate and filtered and the filtrate is evaporated to dryness. This gives 209 mg of 1-[3-chloro-5-(3,3-dichloroallyloxy)-2-methoxyphenyl]ethanone oxime as E/Z isomers in a ratio of 1:1. 
     M+(ES+)=(324, 100) 
     (18): 1-[3-Chloro-5-(3,3-dichloroallyloxy)-2-methoxyphenyl]ethanone O-(2-hydroxyethyl)-oxime 
     
       
         
         
             
             
         
       
     
     First 400 mg of 1-[3-chloro-5-(3,3-dichloroallyloxy)-2-hydroxyphenyl]ethanone are stirred together with 510 mg of potassium carbonate and 700 mg of 2-chloroethanol at 100° C. under nitrogen for 90 minutes. A further 345 mg of 2-chloroethanol are added and the mixture is stirred at 100° C. for a further 4 h. 
     The reaction mixture is admixed with approximately 10 ml of water and extracted 2× with approximately 50 ml of dichloromethane, the combined organic phases are dried over Na 2 SO 4  and filtered and the filtrate is evaporated to dryness. This gives 560 mg of 1-[3-chloro-5-(3,3-dichloro-allyloxy)-2-methoxyphenyl]ethanone O-(2-hydroxyethyl)oxime. 
     M+(ES+)=(368, 25) 
     In the same way as for (18) the following compound is synthesized: 
     
       
         
           
               
               
               
             
               
                   
               
               
                 Identification 
                 Structure 
                 Physical data 
               
               
                   
               
             
            
               
                 (19): (1E)-1-{3-Chloro-5-[(3,3- dichloroprop-2-en-1-yl)oxy]-2- methoxyphenyl}ethanone O-(4-hydroxybutyl)oxime 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 (M + 396, 18) 
               
               
                   
               
            
           
         
       
     
     Examples of Preparation of Compounds of the General Formula (I) 
     (20): 1-[3-Chloro-5-(3,3-dichloroallyloxy)-2-methoxyphenyl]ethanone O-[2-(3-chloro-5-tri-fluoromethylpyridin-2-yloxy)ethyl]oxime 
     
       
         
         
             
             
         
       
     
     First 250 mg of 1-[3-chloro-5-(3,3-dichloroallyloxy)-2-methoxyphenyl]ethanone O-(2-hydroxyethyl)oxime, 133 mg of 2-hydroxy-5-trifluoromethylpyridine and 355 mg of triphenylphosphine are introduced together as an initial charge in 15 ml of absolute tetrahydrofuran. 236 mg of DEAD are added dropwise as a solution in 1 ml of tetrahydrofuran. The reaction mixture is stirred at RT overnight. It is evaporated to dryness and the crude product is purified via HPLC. This gives 6 mg of 1-[3-chloro-5-(3,3-dichloroallyloxy)-2-methoxyphenyl]ethanone O-[2-(3-chloro-5-trifluoromethylpyridin-2-yloxy)ethyl]oxime. 
     M+(ES+)=(547, 80) 
       1 H-NMR (CDCl 3 ): 2.20 (s, 3H, CH 3 ); 3.74 (s, 3H, OCH 3 ); 4.56 (dd, J=4.6; J=5.1; 2H, CH 2 ); 4.61 (d, J=6.3 Hz, C H   2 CHCCl 2 ); 4.75 (dd, J=4.6; J=5.1; 2H, CH 2 ); 6.12 (t, J=6.3 Hz, 1H, CH 2 C H CCl 2 ); 6.77 (d, J=3.1 Hz, 1H, aryl); 6.94 (d, J=3.1 Hz, 1H, aryl); 7.85 (d, J=2.1 Hz; 1H, pyridyl); 8.31 (d, J=1.2 Hz, 1H, pyridyl). 
     In analogy to the instructions for 1-[3-chloro-5-(3,3-dichloroallyloxy)-2-methoxyphenyl]-ethanone O-[2-(3-chloro-5-trifluoromethylpyridin-2-yloxy)ethyl]oxime (20) the following compounds of the general formula I were synthesized: 
     
       
         
         
             
             
         
       
     
     
       
         
           
               
             
               
                 TABLE 1 
               
             
            
               
                   
               
               
                 for X = O 
               
            
           
           
               
               
               
               
               
               
               
               
               
               
            
               
                 Name 
                 A 1   
                 R 1   
                 R 2   
                 R 3   
                 R 4   
                 R 5   
                 A 2   
                 R 6   
                 Physical data 
               
               
                   
               
               
                 (21): 
                 CH 2 CHCCl 2   
                 OCH 3   
                 Cl 
                 H 
                 H 
                 CH 3   
                 (CH 2 ) 2   
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 (M + 513, 10) 
               
               
                   
               
               
                 (22): 
                 CH 2 CHCCl 2   
                 OCH 3   
                 Cl 
                 H 
                 H 
                 CH 3   
                 (CH 2 ) 4   
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 (M + 541, 89) 
               
               
                   
               
               
                 (23): 
                 CH 2 CHCCl 2   
                 OCH 3   
                 Cl 
                 H 
                 H 
                 CH 3   
                 (CH 2 ) 4   
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 (M + 575, 63) 
               
               
                   
               
               
                 (24): 
                 CH 2 CHCCl 2   
                 OCH 3   
                 Cl 
                 H 
                 H 
                 CH 3   
                 (CH 2 ) 4   
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 (M + 608, 32);  1 H-NMR: 1.96- 2.06 (m, 4H, (CH2)2), 2.22 (s, 3H, CH3); 3.75 (s, 3H, OCH3); 4.09-4.14 (m, 2H); 4.21-4.29 (m, 2H); 4.61 (d, J = 6.3 Hz, 2H, OCH2CHCCl2); 6.12 (t, J = 6.3, 1H, OCH2CHCCl2); 6.77 (d, J = 3.1 Hz, 1H, aryl), 6.93 (d, J = 3.1 Hz, 1H, aryl); 7.57 (s, 2H, aryl) 
               
               
                   
               
            
           
         
       
     
     Variant for the preparation of the compound (27): 
     The synthesis of the amino ether side chains is described in DE 10301519 A1. 
     (25): 3-{[5-(Trifluoromethyl)pyridin-2-yl]oxy}propan-1-ol 
     
       
         
         
             
             
         
       
     
     A suspension of 4 g of sodium hydride in 100 ml of DMF is admixed with 12.6 g of 1,3-propanediol. After the evolution of gas has ended the mixture is stirred at room temperature for approximately 10 minutes. Subsequently 10 g of 2-chloro-5-trifluoromethylpyridine are added as a solution in 10 ml of DMF and the reaction mixture is stirred at room temperature overnight. It is poured into water and extracted three times with dichloromethane. The combined organic phases are dried over sodium sulphate and filtered and the filtrate is evaporated to dryness. The crude product is taken up in toluene, washed with water, dried over sodium sulphate and filtered and the filtrate is evaporated to dryness. 
     The oily residue is stirred together with pentane and placed in a deep-freeze for crystallization. The precipitated solid is filtered off on a frit, washed with pentane and dried under reduced pressure. This gives 5.2 g of 3-{[5-(trifluoromethyl)pyridin-2-yl]oxy}propan-1-ol. 
     M+(ES+)=(222, 100) 
       1 H-NMR (CDCl 3 ): 2.02 (dt, 2H, CH 2 ); 3.75 (t, J=6 Hz, 2H, CH 2 ); 4.55 (t, J=6 Hz, 2H, CH 2 ); 6.82 (d, J=8.8 Hz, 1H, CH, pyridyl); 7.78 (dd, J=8.8 Hz, J=2.5 Hz, 1H, CH, pyridyl); 8.42 (s, 1H, CH, pyridyl). 
     (26): 1-(3-{[5-(Trifluoromethyl)pyridin-2-yl]oxy}propoxy)pyrrolidine-2,5-dione 
     
       
         
         
             
             
         
       
     
     Under nitrogen 2.5 g of 3-{[5-(trifluoromethyl)pyridin-2-yl]oxy}propan-1-ol together with 1.3 g of N-hydroxyphthalimide and 2.96 g of triphenylphosphine are stirred in 200 ml of absolute tetrahydrofuran. At 0° C. 1.97 g of diethyl azodicarboxylate are added dropwise and the reaction mixture is stirred at room temperature overnight. It is evaporated to dryness and the residue is recrystallized from 4:1 hexane/EE. The solid obtained is redissolved in hot isopropanol and placed in a refrigerator for crystallization. This gives 3.25 g of 1-(3-{[5(trifluoromethyl)pyridin-2-yl]oxy}propoxy)pyrrolidine-2,5-dione as a colourless solid. 
     M+(ES+)=(319, 100) 
       1 H-NMR (CDCl 3 ): 2.10 (dt, 2H, CH2); 3.13 (s, 4H, CH2); 4.16 (t, J=6.3 Hz, 2H, CH2); 4.51 (t, J=6.4 Hz, 2H, CH2); 6.99 (d, J=8.7 Hz, 1H, CH, pyridyl); 8.01 (dd, J=8.8 Hz, J=6.5 Hz, 1H, CH pyridyl); 8.54 (s, 1H, CH, pyridyl) 
     (27): 2-[3-(Aminooxy)propoxy]-5-(trifluoromethyl)pyridine 
     
       
         
         
             
             
         
       
     
     First 2 g of 1-(3-{[5-(trifluoromethyl)pyridin-2-yl]oxy}propoxy)pyrrolidine-2,5-dione are introduced as an initial charge in 60 ml of dichloromethane and 3 ml of methanol. Subsequently 378 mg of hydrazine hydrate are added. The mixture is stirred under reflux for approximately 4 h. 
     After the batch has cooled it is extracted with 5N ammonia solution. The organic phase is separated off, dried over sodium sulphate and filtered and the filtrate is evaporated to dryness. This gives 0.77 g of 2-[3-(aminooxy)propoxy]-5-(trifluoromethyl)pyridine. 
       1 H-NMR (CD 3 CN): 2.02 (dt, 2H, CH 2 ); 3.72 (t, J=6.3 Hz, 2H, CH 2 ); 4.40 (t, J=6.6 Hz, 2H, CH 2 ); 6.88 (d, J=8.8 Hz, 1H, CH, pyridyl); 7.22 (bs, 2H, NH 2 ); 7.90 (dd, J=8.8 Hz, J=2.6 Hz, 1H, CH, pyridyl); 8.49 (s, 1H, CH, pyridyl). 
     (28): 1-[3-Chloro-5-(3,3-dichloroallyloxy)-2-methoxyphenyl]ethanone O-[1-(6-chloropyridin-3-yl)-ethyl]oxime 
     
       
         
         
             
             
         
       
     
     First 112 mg of O-[1-(6-chloropyridin-3-yl)ethyl]hydroxylamine are added under nitrogen to a solution of 1-[3-chloro-5-(3,3-dichloroallyloxy)-2-hydroxyphenyl]ethanone in 5 ml of absolute pyridine. The reaction mixture is stirred at 25° C. overnight. It is evaporated to dryness and the residue is chromatographed over silica gel using 4:1 cyclohexane:ethyl acetate. This gives 81 mg of 1-[3-chloro-5-(3,3-dichloroallyloxy)-2-methoxyphenyl]ethanone O-[1-(6-chloropyridin-3-yl)ethyl]oxime. 
     M+(ES+)=(M+463, 75) 
       1 H-NMR (CD 3 CN): 1.58 (d, J=6.7 Hz, 3H, CH 3 ); 2.22 (s, 3H, CH 3 ); 3.58 (s, 3H, OCH 3 ); 4.61 (d, J=6.4 Hz, 2H, OCH 2 CHCCl 2 ); 5.36 (g, J=6.7 Hz, 1H, CH); 6.22 (t, J=6.4 Hz, OCH 2 CHCCl 2 ); 6.68 (d, J=3.1 Hz, 1H, CH, aryl); 7.01 (d, J=3.1 Hz, 1H, CH, aryl); 7.38 (d, J=8.3 Hz, 1H, pyridyl); 7.75 (dd, J=8.3 and 2.4 Hz, 1H, pyridyl); 8.37 (d, J=2.4 Hz, 1H, pyridyl). 
     In analogy to the instructions for (35): 1-[3-chloro-5-(3,3-dichloroallyloxy)-2-methoxyphenyl]ethanone O-[1-(6-chloro-pyridin-3-yl)ethyl]oxime the following compounds of the general formula I were synthesized: 
     
       
         
         
             
             
         
       
     
     
       
         
           
               
             
               
                 TABLE 2a 
               
             
            
               
                   
               
               
                 for X = direct bond 
               
            
           
           
               
               
               
               
               
               
               
               
               
               
            
               
                 Name 
                 A 1   
                 R 1   
                 R 2   
                 R 3   
                 R 4   
                 R 5   
                 R 6   
                 A 2   
                 Physical data 
               
               
                   
               
               
                 (29): 
                 CH 2 CHCCl 2   
                 OCH 3   
                 Cl 
                 H 
                 H 
                 CH 3   
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 CH 2   
                 (M + 498, 100) 
               
               
                   
               
               
                 (30): 
                 CH 2 CHCCl 2   
                 OCH 3   
                 Cl 
                 H 
                 H 
                 CH 3   
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 CH 2   
                 (M + 524, 100) 
               
               
                   
               
               
                 (31): 
                 CH 2 CHCCl 2   
                 OCH 3   
                 Cl 
                 H 
                 H 
                 cyclo- propyl 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 CH 2   
                 (M + 550, 100) 
               
               
                   
               
               
                 (32): 
                 CH 2 CHCCl 2   
                 OCH 3   
                 Cl 
                 H 
                 H 
                 CH 3   
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 CH 2   
                 (M + 483, 68) 
               
               
                   
               
               
                 (33): 
                 CH 2 CHCCl 2   
                 OCH 3   
                 Cl 
                 H 
                 H 
                 CH 3   
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 CH 2   
                 (M + 449, 84) 
               
               
                   
               
               
                 (34): 
                 CH 2 CHCCl 2   
                 OCH 3   
                 Cl 
                 H 
                 H 
                 CH 3   
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 (CH 2 ) 2   
                 (M + 547, 100) 
               
               
                   
               
               
                 (35): 
                 CH 2 CHCCl 2   
                 OCH 3   
                 Cl 
                 H 
                 H 
                 CH 3   
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 CH(CH 3 ) 
                 (M + 463, 75);  1 H-NMR: 1.58 (d, J = 6.7 Hz, 3H, CH 3 ); 2.22 (s, 3H, CH 3 ); 3.58 (s, 3H, OCH 3 ); 4.61 (d, J = 6.4 Hz, 2H, OCH 2 CHCCl 2 ); 5.36 (g, J = 6.7 Hz, 1H, CH); 6.22 (t, J = 6.4 Hz, OCH 2 CHCCl 2 ); 6.68 (d, J = 3.1 Hz, 1H, CH, aryl); 7.01 (d, J = 3.1 Hz, 1H, CH, aryl); 7.38 (d, J = 8.3 Hz, 1H, pyridyl); 7.75 (dd, J = 8.3 and 2.4 Hz, 1H, pyridyl); 8.37 (d, J = 2.4 Hz, 1H, pyridyl). 
               
               
                   
               
               
                 (36): 
                 CH 2 CHCCl 2   
                 OCH 3   
                 Cl 
                 H 
                 H 
                 CH 3   
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 (CH 2 ) 2   
                 (M + 485, 100) 
               
               
                   
               
               
                 (37): 
                 CH 2 CHCCl 2   
                 OCH 3   
                 Cl 
                 H 
                 H 
                 CH 3   
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 (CH 2 ) 2   
                 (M + 513, 100) 
               
               
                   
               
               
                 (38): 
                 CH 2 CHCCl 2   
                 OCH 3   
                 Cl 
                 H 
                 H 
                 CH 3   
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 (CH 2 ) 2   
                 (M + 525, 100) 
               
               
                   
               
               
                 (39): 
                 CH 2 CHCCl 2   
                 OCH 3   
                 Cl 
                 H 
                 H 
                 CH 3   
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 (CH 2 ) 2   
                 (M + 473, 95) 
               
               
                   
               
               
                 (40): 
                 CH 2 CHCCl 2   
                 OCH 3   
                 Cl 
                 H 
                 H 
                 CH 3   
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 (CH 2 ) 2   
                 (M + 525, 98) 
               
               
                   
               
               
                 (41): 
                 CH 2 CHCCl 2   
                 OCH 3   
                 Cl 
                 H 
                 H 
                 CH 3   
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 (CH 2 ) 2   
                 (M + 543, 100) 
               
               
                   
               
               
                 (42): 
                 CH 2 CHCCl 2   
                 OCH 3   
                 Cl 
                 H 
                 H 
                 CH 3   
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 (CH 2 ) 2   
                 (M + 460, 95) 
               
               
                   
               
               
                 (43): 
                 CH 2 CHCCl 2   
                 OCH 3   
                 Cl 
                 H 
                 H 
                 CH 3   
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 (CH 2 ) 2   
                 (M + 511, 100) 
               
               
                   
               
               
                 (44): 
                 CH 2 CHCCl 2   
                 OCH 3   
                 Cl 
                 H 
                 H 
                 CH 3   
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 (CH 2 ) 2   
                 (M + 489, 95) 
               
               
                   
               
               
                 (45): 
                 CH 2 CHCCl 2   
                 OCH 3   
                 Cl 
                 H 
                 H 
                 CH 3   
                 Ph 
                 CHCH 3   
                 (M + 430, 100) 
               
               
                   
               
               
                 (46): 
                 CH 2 CHCCl 2   
                 OCH 3   
                 Cl 
                 H 
                 H 
                 CH 3   
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 CH 2   
                 (M + 430, 100) 
               
               
                   
               
               
                 (47): 
                 CH 2 CHCCl 2   
                 OCH 3   
                 Cl 
                 H 
                 H 
                 CH 3   
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 CHCH 3   
                 (M + 471, 100) 
               
               
                   
               
               
                 (48): 
                 CH 2 CHCCl 2   
                 OCH 3   
                 Cl 
                 H 
                 H 
                 CH 3   
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 CH 2   
                 (M + 567, 100) 
               
               
                   
               
               
                 Ph = phenyl, 
               
               
                 Me = methyl 
               
            
           
         
       
     
     In analogy to the instructions for (35): 1-[3-chloro-5-(3,3-dichloroallyloxy)-2-methoxyphenyl]ethanone O-[1-(6-chloropyridin-3-yl)ethyl]oxime the following compound of the general formula I was synthesized: 
     
       
         
         
             
             
         
       
     
     
       
         
           
               
             
               
                 TABLE 2b 
               
             
            
               
                   
               
               
                 for X = O bond 
               
            
           
           
               
               
               
               
               
               
               
               
               
               
            
               
                 Name 
                 A1 
                 R1 
                 R2 
                 R3 
                 R4 
                 R5 
                 R6 
                 A2 
                 Physical data 
               
               
                   
               
               
                 (49): 
                 CH 2 CHCCl 2   
                 OCH 3   
                 Cl 
                 H 
                 H 
                 CH 3   
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 (M + 552, 100) 
               
               
                   
               
            
           
         
       
     
     (50): N-{4-[2-({[(1E)-{3-Chloro-5-[(3,3-dichloroprop-2-en-1-yl)oxy]-2-methoxyphenyl}(cyclopropyl)methylene]amino}oxy)ethyl]phenyl}-2-methylpropanamide 
     
       
         
         
             
             
         
       
     
     First 132 mg of N-{4-[2-(aminooxy)ethyl]phenyl}-2-methylpropanamide are added under nitrogen to a solution of 100 mg of [3-chloro-5-(3,3-dichloroallyloxy)-2-methoxyphenyl]cyclopropylmethanone in 5 ml of absolute pyridine and 5 ml of toluene. The reaction mixture is stirred under reflux overnight with a water separator. The reaction mixture is evaporated to dryness. Subsequently a further 5 ml of pyridine and toluene are added. The mixture is again stirred under reflux overnight with a water separator. 
     The reaction mixture is evaporated to dryness and the residue is purified by flash chromatography (4:1 cyclohexane:ethyl acetate). This gives 44.5 mg of N-{4-[2-({[(1E)-{3-chloro-5-[(3,3-dichloro-prop-2-en-1-yl)oxy]-2-methoxyphenyl}(cyclopropyl)methylene]amino}oxy)ethyl]phenyl}-2-methylpropanamide as an E/Z isomer mixture. 
     M+(ES+)=(539, 100) 
       1 H-NMR (CD 3 CN): 0.41-0.43 (m, 2H, CH 2 , cPr); 0.64-0.69 (m, 2H, CH 2 , cPr); 0.77-0.84 (m, 4H, CH 2 , cPr); 1.71-1.80 (m, 1H, CH, cPr); 2.31-2.38 (m, 1H, CH); 2.50-2.52 (m, 1H, CH); 2.80 (t, J=6.6 Hz, 2H, CH 2 ); 2.95 (t, J=6.7 Hz, 2H, CH 2 ); 3.62 (s, 3H, OCH 3 ); 3.76 (s, 3H, OCH 3 ); 4.11 (t, J=6.6 Hz, 2H, CH 2 ); 4.28 (t, J=6.7 Hz, 2H, CH 2 ); 4.59 (d, J=6.5 Hz, 2H, OC H 2   CHCCl 2 ); 4.64 (d, J=6.4 Hz, 2H, OC H 2   CHCCl 2 ); 
     6.22-6.25 (m, 2×1H, OCH 2 C H CCl); 6.44 (d, J=3.0 Hz, 1H, aryl); 6.58 (d, J=3.0 Hz, 1H, aryl); 6.99-7.04 (m, H, aryl); 7.21 (d, J=8.5 Hz, 1H, aryl); 7.40 (d, J=8.5 Hz, 1H, aryl); 7.49 (d, J=8.5 Hz, 1H, aryl); 8.1-8.2 (bd, 2H, NH). 
     In analogy to the instructions for (50): N-{4-[2-({[(1E)-{3-chloro-5-[(3,3-dichloroprop-2-en-1-yl)oxy]-2-methoxyphenyl}(cyclopropyl)methylene]amino}oxy)ethyl]phenyl}-2-methylpropanamide the following compounds of the general formula I were synthesized: 
     
       
         
         
             
             
         
       
     
     
       
         
           
               
             
               
                 TABLE 3a 
               
             
            
               
                   
               
               
                 for X = direct bond 
               
            
           
           
               
               
               
               
               
               
               
               
               
               
            
               
                 Name 
                 A 1   
                 R 1   
                 R 2   
                 R 3   
                 R 4   
                 R 5   
                 R 6   
                 A 2   
                 Physical data 
               
               
                   
               
               
                 (51): 
                 CH 2 CHCCl 2   
                 OCH 3   
                 Cl 
                 H 
                 H 
                 IPr 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 (M + 616, 100) 
               
               
                   
               
               
                 (52): 
                 CH 2 CHCCl 2   
                 OCH 3   
                 Cl 
                 H 
                 H 
                 CH 3   
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 (CH 2 ) 2   
                 (M + 539, 100) 
               
               
                   
               
               
                 (53): 
                 CH 2 CHCCl 2   
                 OCH 3   
                 Cl 
                 H 
                 H 
                 cPr 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 (CH 2 ) 2   
                 (M + 551, 70) 
               
               
                   
               
               
                 (54): 
                 CH 2 CHCCl 2   
                 OCH 3   
                 Cl 
                 H 
                 H 
                 cPr 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 (CH 2 ) 2   
                 (M + 569, 100) 
               
               
                   
               
               
                 (55): 
                 CH 2 CHCCl 2   
                 OCH 3   
                 Cl 
                 H 
                 H 
                 cPr 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 (CH 2 ) 3   
                 (M + 486, 100) 
               
               
                   
               
               
                 (56): 
                 CH 2 CHCCl 2   
                 OCH 3   
                 Cl 
                 H 
                 H 
                 cPr 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 (CH 2 ) 2   
                 (M + 581, 100) 
               
               
                   
               
               
                 (57): 
                 CH 2 CHCCl 2   
                 OCH 3   
                 Cl 
                 H 
                 H 
                 CH 3   
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 (M + 586, 100) 
               
               
                   
               
               
                 (58): 
                 CH 2 CHCCl 2   
                 OCH 3   
                 Cl 
                 H 
                 H 
                 cHexyl 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 (CH 2 ) 2   
                 (M + 593, 100) 
               
               
                   
               
               
                 (59): 
                 CH 2 CHCCl 2   
                 OCH 3   
                 Cl 
                 H 
                 H 
                 IPr 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 (M + 616, 100) 
               
               
                   
               
               
                 (60): 
                 CH 2 CHCCl 2   
                 OCH 3   
                 Cl 
                 H 
                 H 
                 CH(CH 3 ) 2   
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 CH 2   
                 (M + 552, 100) 
               
               
                   
               
               
                 (61): 
                 CH 2 CHCCl 2   
                 OCH 3   
                 Cl 
                 H 
                 H 
                 CH(CH 3 ) 2   
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 CH 2   
                 (M + 512, 60) 
               
               
                   
               
            
           
         
       
     
     In analogy to the instructions for (50): N-{4-[2-({[(1E)-{3-chloro-5-[(3,3-dichloroprop-2-en-1-yl)oxy]-2-methoxyphenyl}(cyclopropyl)methylene]amino}oxy)ethyl]phenyl}-2-methylpropanamide the following compound of the general formula I was synthesized: 
     
       
         
         
             
             
         
       
     
     
       
         
           
               
             
               
                 TABLE 3b 
               
             
            
               
                   
               
               
                 for X = O bond 
               
            
           
           
               
               
               
               
               
               
               
               
               
               
            
               
                 Name 
                 A 1   
                 R 1   
                 R 2   
                 R 3   
                 R 4   
                 R 5   
                 R 6   
                 A 2   
                 Physical data 
               
               
                   
               
               
                 (62): 
                 CH 2 CHCCl 2   
                 OCH 3   
                 Cl 
                 H 
                 H 
                 CH 3   
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 (M + 609, 90) 
               
               
                   
               
            
           
         
       
     
     (63): 4-{1-[3-Chloro-5-(3,3-dichloroallyloxy)-2-methoxyphenyl]ethylideneaminooxy}butyric acid 
     
       
         
         
             
             
         
       
     
     First 1.2 g of 1-[3-chloro-5-(3,3-dichloroallyloxy)-2-hydroxyphenyl]ethanone are stirred together with 664 mg of 4-aminooxybutyroyl hydrochloride at RT for 3 days in the presence of molecular sieve in 60 ml of absolute methanol. The reaction mixture is filtered, the filtrate is evaporated to dryness, the residue is diluted with ethyl acetate, washed with water, dried over sodium sulphate and filtered and the filtrate is concentrated to dryness. 
     The residue is taken up in methanol, 2 ml of water and 1 g of potassium carbonate are added and the reaction mixture is stirred at RT overnight. It is evaporated to dryness and the residue is taken up in 1:1 water/EE and extracted once with ethyl acetate. The aqueous phase is acidified using 1N HCl and extracted a number of times with ethyl acetate. The combined organic phases are dried over sodium sulphate and filtered and the filtrate is evaporated to dryness. This gives 354 mg of 4-{1-[3-chloro-5-(3,3-dichloroallyloxy)-2-methoxyphenyl]ethylideneaminooxy}butyric acid. 
     M+(ES+)=(408, 98) 
       1 H-NMR (CD 3 CN): 2.08-2.26 (m, 2H, CH 2  and water); 2.16 (s, 3H, CH 3 ); 2.40 (t, J=7.3 Hz, 2H, CH 2 ); 3.72 (s, 3H, CH 3 ); 4.16 (t, J=6.3 Hz, 2H, CH 2 ); 4.65 (d, J=6.4 Hz, 2H, OC H 2   CHCCl 2 ); 6.26 (t, J=6.4 Hz, 1H, OCH 2 CHCCl 2 ); 6.81 (d, J=3.1 Hz, CH, aryl); 7.04 (d, (d, J=3.1 Hz, CH, aryl) 
     (64): 4-{1-[3-Chloro-5-(3,3-dichloroallyloxy)-2-methoxyphenyl]ethylideneaminooxy}-N-phenylbutyramide 
     
       
         
         
             
             
         
       
     
     First 50 mg of 4-{1-[3-chloro-5-(3,3-dichloroallyloxy)-2-methoxyphenyl]ethylideneaminooxy}-butyric acid are introduced as an initial charge in 2 ml of dichloromethane and 13 mg of aniline, 7.5 mg of DMAP and 37 mg of triethylamine are added. Subsequently 28 mg of N-(3-dimethylaminopropyl)-N-ethylcarbodiimide hydrochloride, in solution in 1 ml of dichloromethane, are added dropwise and the reaction mixture is stirred at RT overnight. It is washed with 1N HCl, the organic phase is dried over sodium sulphate and filtered and the filtrate is evaporated to dryness. The crude product is purified by flash chromatography (eluent: 98:2 dichloromethane/methanol). This gives 18 mg of 4-{1-[3-chloro-5-(3,3-dichloroallyloxy)-2-methoxyphenyl]ethylideneaminooxy}-N-phenylbutyramide. 
     (M+485, 100) 
       1 H-NMR (CD 3 CN): 2.04 (t, J=7.2 Hz, CH 2 ); 2.15 (s, 33.71H, CH 3 ); 2.44 (t, J=7.3 Hz, 2H, CH 2 ); 3.71 (s, 3H, OCH 3 ); 4.21 (t, J=6.3 Hz, 2H, CH 2 ); 4.64 (d, J=6.4 Hz, 2H, OCH 2 CHCCl 2 ); 6.25 (t, J=6.4 Hz, 1H, OC H   2 CHCCl 2 ); 6.82 (d, J=3.1 Hz, 1H, aryl); 7.04 (d, J=3.1 Hz, 1H, aryl); 7.04-7.08 (m, 1H, aniline); 7.29 (dd, 2H, J=5.8 and 6.6 Hz, aniline); 7.55 (d, 2H; J=7.6 Hz); 8.3 (bs, 1H, NH). 
     In the same way as for (64) (65) was synthesized: 
     
       
         
           
               
               
               
               
               
               
               
               
               
               
             
               
                   
               
               
                 Name 
                 A 1   
                 R 1   
                 R 2   
                 R 3   
                 R 4   
                 R 5   
                 R 6   
                 A 2   
                 Physical data 
               
               
                   
               
             
            
               
                 (65): 
                 CH 2 CHCCl 2   
                 OCH 3   
                 Cl 
                 H 
                 H 
                 CH 3   
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 (CH 2 ) 3 CO 
                 (M + 543, 100) 
               
               
                   
               
            
           
         
       
     
     (66): Ethyl (2E)-3-{4-[(4-{[((1E)-1-{3-chloro-5-[(3,3-dichloroprop-2-en-1-yl)oxy]-2-methoxyphenyl}ethylidene)amino]oxy}butanoyl)amino]phenyl}acrylate 
     
       
         
         
             
             
         
       
     
     First 50 mg of 4-{1-[3-chloro-5-(3,3-dichloroallyloxy)-2-methoxyphenyl]ethylideneaminooxy}-butyric acid are introduced as an initial charge in 2 ml of dichloromethane and 17 mg of oxalyl chloride and one drop of DMF are added. After evolution of gas has ended, 25 mg of ethyl (2E)-3-(4-aminophenyl)acrylate are added dropwise as a solution in 1 ml of dichloromethane together with 37 mg of triethylamine. The mixture is stirred at room temperature overnight. 
     The reaction mixture is washed with 1N HCl, the organic phase is dried over sodium sulphate and filtered and the filtrate is evaporated to dryness. The crude product is purified by flash chromatography (eluent: 98:2 dichloromethane/methanol). This gives 11 mg of ethyl (2E)-3-{4-[(4-{[((1E)-1-{3-chloro-5-[(3,3-dichloroprop-2-en-1-yl)oxy]-2-methoxyphenyl}ethylidene)amino]oxy}-butanoyl)amino]phenyl}acrylate. 
       1 H-NMR: 1.33 (t, J=7.1 Hz, 3H, CH 3  ethyl); 2.16 (t, J=6.5 Hz, 2H, CH 2 ); 2.22 (s, 3H, CH 3 ); 2.54 (t, J=6.9 Hz, 2H, CH 2 ); 3.76 (s, 3H, OCH 3 ); 4.27-4.30 (m, 4H, 2×CH 2 ); 4.59 (d, J=6.3 Hz, 2H, OC H   2 CHCCl 2 ); 6.10 (t, J=6.3 Hz, 1H, OCH 2 C H CCl 2 ); 6.35 (d, J=16 Hz, 1H, CH═CH); 6.75 (d, J=3.0 Hz, 1H, aryl); 6.95 (d, J=3.0 Hz, 1H, aryl); 7.44-7.51 (m, 4H, aryl); 7.62 (d, J=16 Hz, 1H, CH); 7.76 (bs, 1H, NH). 
     In analogy to the instructions for (66): ethyl (2E)-3-{4-[(4-{[((1E)-1-{3-chloro-5-[(3,3-dichloroprop-2-en-1-yl)oxy]-2-methoxyphenyl}ethylidene)amino]oxy}butanoyl)amino]-phenyl}acrylate the following compounds of the general formula I were synthesized: 
     
       
         
         
             
             
         
       
     
     
       
         
           
               
             
               
                 TABLE 4 
               
             
            
               
                   
               
               
                 for X = NH 
               
            
           
           
               
               
               
               
               
               
               
               
               
               
            
               
                 Name 
                 A 1   
                 R 1   
                 R 2   
                 R 3   
                 R 4   
                 R 5   
                 R 6   
                 A 2   
                 Physical data 
               
               
                   
               
               
                 (67): 
                 CH 2 CHCCl 2   
                 OCH 3   
                 Cl 
                 H 
                 H 
                 CH 3   
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 (CH 2 ) 3 CO 
                 (M + 623, 100) 
               
               
                 (68): 
                 CH 2 CHCCl 2   
                 OCH 3   
                 Cl 
                 H 
                 H 
                 CH 3   
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 (CH 2 ) 3 CO 
                 (M + 581, 100) 
               
               
                   
               
            
           
         
       
     
     (69): 2,2-Dimethyl-2,3-dihydro-1-benzofuran-7-yl 4-{[((1E)-1-{3-chloro-5-[(3,3-dichloroprop-2-en-1-yl)oxy]-2-methoxyphenyl}ethylidene)amino]oxy}butyrate 
     
       
         
         
             
             
         
       
     
     First 50 mg of 4-{1-[3-chloro-5-(3,3-dichloroallyloxy)-2-methoxyphenyl]ethylideneaminooxy}-butyric acid are introduced as an initial charge in 2 ml of dichloromethane and admixed in succession with 22 mg of 2,2-dimethyl-2,3-dihydro-1-benzofuran-7-ol, 7.5 mg of 4-dimethylaminopyridine and 40 mg of triethylamine. Subsequently 28 mg of 1,3-dicyclohexylcarbodiimide are added dropwise as a solution in 1 ml of dichloromethane and the mixture is stirred at RT overnight. It is subsequently stirred under reflux for 1 h. 
     The reaction mixture is washed with 1N HCl, the organic phase is dried over sodium sulphate and filtered and the filtrate is evaporated to dryness. Purification by means of HPLC gives 27 mg of 2,2-dimethyl-2,3-dihydro-1-benzofuran-7-yl 4-{[((1E)-1-{3-chloro-5-[(3,3-dichloroprop-2-en-1-yl)oxy]-2-methoxyphenyl}ethylidene)amino]oxy}butanoate as an E/Z isomer mixture. 
     M+(ES+)=(556, 100) 
       1 H-NMR (CD 3 CN): 2.06-2.12 (m, 4H, 2×CH 2 ); 2.14 (s, 12H, 4×CH 3 ); 2.15 (s, 3H, CH 3 ); 2.18 (s, 3H, CH 3 ); 4.15 (t, J=6.3 Hz, 2H, CH 2 ); 4.25 (t, J=6.3 Hz, 2H, CH 2 ); 4.64-4.66 (m, 4H, 2×OC H CHCCl 2 ); 6.23-6.26 (m, 2H, 2×OCH 2 C H CCl 2 ); 6.81-6.84 (m, 6H, aryl); 7.04-7.05 (m, 4H, aryl). 
     (70): 2-Hydroxy-5-methoxyphenyl cyclopropyl ketone (A) 
     2,5-Dimethoxyphenyl cyclopropyl ketone (B) 
     
       
         
         
             
             
         
       
     
     Under inert gas 48.2 g of AlCl 3  are introduced as an initial charge in 350 ml of 1,2-dichloroethane and this initial charge is admixed with 50 g of 1,4-dimethoxybenzene. Subsequently 37.8 g of cyclopropylcarbonyl chloride are slowly added dropwise and the mixture is stirred under reflux for a number of hours. After the mixture has cooled it is discharged into ice-water, a little concentrated HCl is added and the aqueous phase is extracted twice with dichloromethane. The combined organic phases are dried and concentrated. This gives 50 g of a 2:1 mixture of 2-hydroxy-5-methoxyphenyl)cyclopropyl ketone (A) and 2,5-dimethoxyphenyl cyclopropyl ketone (B) as a yellow solid which is used in the next step. 
     M+(ES+)=(193, 100) for A; (207, 100) for B 
       1 H-NMR (DMSO-D6) for A: 1.11 (m, 4H, -cPr); 3.04 (m, 1H, -cPr); 3.78 (s, 3H, —OMe); 6.92 (d, J=9 Hz, 1H, aryl); 7.17 (dd, J=2.1 Hz, 9 Hz, 1H, aryl); 7.53 (d, J=3.1 Hz, 1H, aryl); 11.58 (s, 1H, OH) 
       1 H-NMR (DMSO-D6) for B: 1.00 (m, 4H, -cPr); 2.71 (m, 1H, -cPr); 3.73 (s, 3H, —OMe); 3.83 (s, 3H, —OMe); 6.97 (m, 1H, aryl); 7.12 (m, 2H, aryl); 11.20 (s, 1H, OH) 
     (71) 3-Chloro-2-hydroxy-5-methoxyphenyl cyclopropyl ketone-(2,5-dimethoxyphenyl cyclo-propyl ketone 
     
       
         
         
             
             
         
       
     
     A solution of 68 g of an approximately 2:1 mixture of 1-(2-hydroxy-5-methoxyphenyl)cyclopropyl ketone and 2,5-dimethoxyphenyl cyclopropyl ketone in DMF is admixed under inert gas with 57.2 g of N-chlorosuccinimide in portions over the course of 1 h. The reaction solution undergoes brown discoloration and is stirred at RT overnight. The reaction mixture is poured into 600 ml of water, producing 53 g of 3-chloro-2-hydroxy-5-methoxyphenyl cyclopropyl ketone as a beige solid. The supernatant aqueous solution is extracted a number of times with dichloromethane, the combined organic phases are washed a number of times with water, dried over Na 2 SO 4  and filtered, and the filtrate is evaporated to dryness. This gives 35 g of 2,5-dimethoxyphenyl cyclopropyl ketone as a reddish oil. Both compounds are used without purification in the next step. 
     M+(ES+)=(227, 100) 
       1 H-NMR (DMSO-D 6 ): 1.17 (m, 4H, -cPr); 3.07 (m, 1H, -cPr); 3.81 (s, 3H, —OMe); 7.42 (d, J=3 Hz, 1H, aryl); 7.66 (d, J=3 Hz, 1H, aryl); 12.25 (s, 1H, OH). 
     (72): 3-Chloro-2,5-dihydroxyphenyl cyclopropyl ketone 
     
       
         
         
             
             
         
       
     
     Under inert gas 53 g of 3-chloro-2-hydroxy-5-methoxyphenyl cyclopropyl ketone are introduced as an initial charge in 400 ml of dichloromethane and at 0° C. a solution of 44.2 ml of BBr 3  in 100 ml of dichloromethane is added dropwise. Subsequently the mixture is stirred at room temperature for 1 h and poured carefully into ice-water. After phase separation the aqueous phase is extracted once with dichloromethane and the combined organic phases are dried and concentrated. 
     M+(ES+)=(213, 100) 
       1 H-NMR (DMSO-D 6 ): 1.16 (m, 4H, -cPr); 3.13 (m, 1H, -cPr); 7.16 (d, J=2.8 Hz, 1H, aryl); 7.24 (d, J=2.8 Hz, aryl); 9.5 (s, 1H, OH); 11.8 (s, 1H, OH) 
     (73): 2,5-Dihydroxyphenyl cyclopropyl ketone 
     (74): 3-Chloro-2,5-dihydroxyphenyl cyclopropyl ketone 
     
       
         
         
             
             
         
       
     
     (73): Under inert gas 35 g of 2,5-dimethoxyphenyl cyclopropyl ketone are introduced as an initial charge in 300 ml of dichloromethane and cooled to 0° C. Subsequently a solution of 32 ml of BBr 3  in 100 ml of dichloromethane is slowly added dropwise. Thereafter the mixture is stirred at room temperature for 1 h and poured carefully into ice-water. After phase separation the aqueous phase is extracted once with dichloromethane and the combined organic phases are dried and concentrated. This gives 34 g of 2,5-dihydroxyphenyl cyclopropyl ketone in the form of a reddish oil which is used without further purification in the next step. 
     M+(ES+)=(195, 100) 
     (74): Over a period of 33.1 g of N-chlorosuccinimide are added under nitrogen and in portions to a solution of 34 g of 2,5-dihydroxyphenyl cyclopropyl ketone in 400 ml of DMF. The reaction solution undergoes brown discoloration and is stirred at RT overnight. The reaction mixture is poured into 0.5 l of water and extracted a number of times with dichloromethane. The combined organic phases are washed a number of times with water, dried over Na 2 SO 4  and filtered and the filtrate is evaporated to dryness. This gives 39 g of product (75% purity according to LC-MS) as a solid which is used without purification in the next step. 
     (75): (2-Hydroxy-5-methoxyphenyl)-2-methylpropan-1-one 
     
       
         
         
             
             
         
       
     
     At room temperature 48.2 g of AlCl 3  and 50 g of 1,4-dimethoxybenzene are introduced as an initial charge in 350 ml of 1,2-dichloroethane and this initial charge is admixed slowly dropwise with 37.9 ml of isobutyryl chloride. The reaction mixture is subsequently stirred under reflux for 16 h. It is worked up by cooling it, pouring it cautiously with stirring onto 500 ml of ice and stirring the subsequent mixture for 10 minutes. The phases are then separated and the aqueous phase is extracted 2× with dichloromethane. Combined organic phases are dried over sodium sulphate and evaporated to dryness. This gives 77 g of mildly impure product (92% purity according to LC-MS) as an orange coloured oil which is used without purification in the next step. 
     M+(ES+)=(195, 100) 
       1 H-NMR (DMSO-D 6 ): 1.13 (d, J=6.8 Hz, 6H, iPr); 3.74 (m, 1H, iPr); 3.75 (s, 3H, OMe); 6.90 (d, J=9 Hz, 1H, aryl); 7.14 (dd, J=3.1 Hz, 9 Hz, aryl); 7.30 (d, J=3.1 Hz, 1H, aryl); 11.4 (s, 1H, OH) 
     (76): (3-Chloro-2-hydroxy-5-methoxyphenyl)-2-methylpropan-1-one 
     
       
         
         
             
             
         
       
     
     Over the course of 1 h 53.6 g of N-chlorosuccinimide are added under nitrogen and in portions to a solution of 60 g of (2-hydroxy-5-methoxyphenyl)-2-methylpropan-1-one in 600 ml of DMF. The reaction solution undergoes brown discoloration and is stirred at RT overnight. The reaction mixture is poured into 1.2 l of water and extracted a number of times with dichloromethane. The combined organic phases are washed a number of times with water, dried over Na 2 SO 4  and filtered and the filtrate is evaporated to dryness. This gives 70 g of product (75% purity according to LC-MS) as a solid which is used without purification in the next step. 
     M+(ES+)=(229, 100) 
       1 H-NMR (DMSO-D 6 ): 1.15 (d, J=6.8 Hz, 6H, iPr); 3.79 (m, 1H, iPr); 3.79 (s, 3H, OMe); 7.40 (s, 2H, aryl); 12.0 (s, 1H, OH) 
     (77): (3-Chloro-2,5-dihydroxyphenyl)-2-methylpropan-1-one 
     
       
         
         
             
             
         
       
     
     Under inert gas 36 g of (3-chloro-2-hydroxy-5-methoxyphenyl)-2-methylpropan-1-one are introduced as an initial charge in 360 ml of dichloromethane, and this initial charge is cooled to 0° C. and admixed dropwise over the course of 10 minutes with a solution of 30 ml of BBr 3  in 180 ml of dichloromethane. After 2 h of subsequent stirring at the given temperature the reaction mixture is poured onto 0.7 l of ice, stirred for 30 minutes thereafter and neutralized by addition of 350 ml of saturated NaHCO 3  solution. Following phase separation the aqueous phase is extracted 3× with 150 ml of dichloromethane and the combined organic phases are dried and evaporated to dryness. This gives 33 g of product (75% purity according to LC-MS) as an oil which is used without purification in the next step. 
     M+(ES+)=(215, 100) 
       1 H-NMR (DMSO-D 6 ): 1.14 (d, J=6.8 Hz, 6H, iPr); 3.62 (m, 1H, iPr); 7.16 (d, J=2.8 Hz, 1H, aryl); 7.26 (d, J=2.8 Hz, aryl); 9.5 (s, 1H, OH); 11.9 (s, 1H, OH) 
     (78): 2,5-Dimethoxyphenyl cyclohexyl ketone+2-hydroxy-5-methoxyphenyl cyclohexyl ketone 
     
       
         
         
             
             
         
       
     
     At room temperature 48.2 g of AlCl 3  and 50 g of 1,4-dimethoxybenzene are introduced as an initial charge in 350 ml of 1,2-dichloroethane and this initial charge is admixed slowly dropwise with 53 g of cyclohexylcarbonyl chloride. The reaction mixture is subsequently stirred under reflux for 16 h. For workup it is cooled and poured cautiously with stirring onto 500 ml of ice, followed by stirring for 10 minutes. Subsequently the phases are separated and the aqueous phase is extracted 2× with dichloromethane. Combined organic phases are dried over sodium sulphate and evaporated to dryness. The crude product obtained was 93 g of mildly impure product (96% purity according to LC-MS) as a mixture of 2,5-dimethoxyphenyl cyclohexyl ketone (B, 83%) and 2-hydroxy-5-methoxyphenyl cyclohexyl ketone (A, 14%) as an orange-coloured oil which is used without purification in the next step. 
     M+(ES+)=(235, 100) for B; (221, 100) for A 
       1 H-NMR (DMSO-D 6 ) (B only): 1.18 (m, 1H, -cHex); 1.37 (bm, 4H, -cHex); 1.65 (m, 1H, -cHex); 1.73 (m, 2H, -cHex); 1.83 (m, 2H, -cHex); 3.46 (m, 1H, -cHex); 3.76 (s, 6H, —OMe); 6.91 (d, J=9 Hz, 1H, aryl); 7.16 (dd, J=3.1 Hz, 9 Hz, 1H, aryl); 7.29 (d, J=3.1 Hz, 1H, aryl); 9.08 (s, 1H, OH); 11.39 (s, 1H, OH) 
     (79): 2,5-Dihydroxyphenyl cyclohexyl ketone 
     
       
         
         
             
             
         
       
     
     Under inert gas 84.3 g of 2,5-dihydroxyphenyl cyclohexyl ketone are introduced as an initial charge in 550 ml of dichloromethane, and this initial charge is cooled to 0° C. and admixed dropwise over a period of 30 minutes with a solution of 68 ml of BBr 3  in 200 ml of dichloromethane. After 2 h of subsequent stirring at the given temperature the reaction mixture is poured onto 0.7 l of ice, followed by subsequent stirring for 30 minutes and neutralization by addition of 400 ml of saturated NaHCO 3  solution. Following phase separation the aqueous phase is extracted a number of times with dichloromethane and the combined organic phases are dried and evaporated to dryness. This gives 37.7 g of 2,5-dihydroxyphenyl cyclohexyl ketone (99% purity according to LC-MS) as an oil which is used without purification in the next step. 
     M+(ES+)=(221, 100) 
       1 H-NMR (DMSO-D 6 ): 1.19 (m, 1H, -cHex); 1.35 (bm, 4H, -cHex); 1.67 (m, 1H, -cHex); 1.78 (bm, 4H, -cHex); 3.34 (m, 1H, -cHex); 6.81 (d, J=8.8 Hz, 1H, Aryl); 6.97 (dd, J=2.9 Hz, 8.8 Hz, 1H, aryl); 7.20 (d, J=2.9 Hz, 1H, aryl); 9.08 (s, 1H, OH); 11.37 (s, 1H, OH) 
     (80): 3-Chloro-2,5-dihydroxyphenyl cyclohexyl ketone 
     
       
         
         
             
             
         
       
     
     Over the course of 1 h 29 g of N-chlorosuccinimide are added under nitrogen and in portions to a solution of 36.7 g of 2,5-dihydroxyphenyl cyclohexyl ketone in 170 ml of DMF. The reaction solution undergoes brown discoloration and is stirred at RT overnight. The reaction mixture is poured into 0.6 l of water and extracted a number of times with dichloromethane. The combined organic phases are washed a number of times with water, dried over Na 2 SO 4  and filtered and the filtrate is evaporated to dryness. This gives 70 g of 3-chloro-2,5-dihydroxyphenyl cyclohexyl ketone (50% purity according to LC-MS) as a solid which is used without purification in the next step. 
     M+(ES+)=(255, 100) 
       1 H-NMR (DMSO-D 6 ): 1.10-1.39 (bm, 5H, -cHex); 1.57-1.88 (m, 5H, -cHex); 3.35 (m, 1H, -cHex); 7.16 (d, J=2.8 Hz, 1H, aryl); 7.28 (m, J=2.8 Hz, 1H, aryl); 9.50 (s, 1H, OH); 11.96 (s, 1H, OH) 
     BIOLOGICAL EXAMPLES 
     Example No. A 
       
     
       
         
           
               
             
               
                   
               
               
                   Spodoptera frugiperda  test (spray treatment) 
               
               
                   
               
             
            
               
                   
               
            
           
           
               
               
               
            
               
                   
                 Solvent: 
                  78 parts by weight of acetone 
               
               
                   
                   
                 1.5 parts by weight of dimethylformamide 
               
               
                   
                 Emulsifier: 
                 0.5 part by weight of alkylaryl polyglycol ether 
               
               
                   
                   
               
            
           
         
       
     
     An appropriate preparation of active compound is produced by mixing 1 part by weight of active compound with the stated amounts of solvent and emulsifier and diluting the concentrate to the desired concentration using emulsifier-containing water. 
     Maize leaf discs ( Zea mays ) are sprayed with a preparation of active compound at the desired concentration and after they have dried off they are populated with caterpillars of the army worm ( Spodoptera frugiperda ). 
     After the desired time the activity is measured in %. Here 100% means that all of the caterpillars have been killed; 0% means that no caterpillar has been killed. 
     In this test effective activity is exhibited by, for example, the following compounds of the Preparation Examples: see table 
     
       
         
           
               
               
               
               
             
               
                 TABLE A 
               
               
                   
               
               
                 Example 
                 Structure 
                 g a. i./ha 
                 % 7 d 
               
               
                   
               
             
            
               
                   
               
            
           
           
               
               
               
               
            
               
                 24 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 500 
                 100 
               
               
                   
               
               
                 21 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 500 
                 100 
               
               
                   
               
               
                 22 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 500 
                 100 
               
               
                   
               
               
                 23 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 500 
                 100 
               
               
                   
               
               
                 20 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 500 
                 100 
               
               
                   
               
               
                 49 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 500 
                 100 
               
               
                   
               
               
                 29 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 500 
                 100 
               
               
                   
               
               
                 40 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 500 
                 100 
               
               
                   
               
               
                 41 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 500 
                 100 
               
               
                   
               
               
                 42 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 500 
                 100 
               
               
                   
               
               
                 39 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 500 
                 100 
               
               
                   
               
               
                 30 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 500 
                 100 
               
               
                   
               
               
                 45 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 500 
                 83 
               
               
                   
               
            
           
         
       
     
     Example No. B 
       
     
       
         
           
               
             
               
                   
               
               
                 Phaedon test (spray treatment) 
               
               
                   
               
             
            
               
                   
               
            
           
           
               
               
               
            
               
                   
                 Solvent: 
                  78 parts by weight of acetone 
               
               
                   
                   
                 1.5 parts by weight of dimethylformamide 
               
               
                   
                 Emulsifier: 
                 0.5 part by weight of alkylaryl polyglycol ether 
               
               
                   
                   
               
            
           
         
       
     
     An appropriate preparation of active compound is produced by mixing 1 part by weight of active compound with the stated amounts of solvent and emulsifier and diluting the concentrate to the desired concentration using emulsifier-containing water. 
     Chinese cabbage leaves ( Brassica pekinensis ) are sprayed with a preparation of active compound at the desired concentration and after they have dried off they are populated with larvae of the mustard beetle ( Phaedon cochleariae ). 
     After the desired time the activity is measured in %. Here 100% means that all of the beetle larvae have been killed; 0% means that no beetle larvae have been killed. 
     In this test effective activity is exhibited by, for example, the following compounds of the Preparation Examples: see table 
     
       
         
           
               
               
               
               
             
               
                 TABLE B 
               
               
                   
               
               
                 Example 
                 Structure 
                 g a. i./ha 
                 % 7 d 
               
               
                   
               
             
            
               
                 14 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 500 
                 100 
               
               
                   
               
            
           
         
       
     
     Example No. C 
       
     
       
         
           
               
             
               
                   
               
               
                   Aedes Aegypti  test 
               
               
                   
               
             
            
               
                   
               
            
           
           
               
               
               
            
               
                   
                 Solvent: 
                 1000 parts by weight of dimethyl sulphoxide 
               
               
                   
                   
               
            
           
         
       
     
     An appropriate preparation of active compound is produced by mixing the active compound with the stated amounts of solvent and diluting the concentrate to the desired concentration with water. 
     The  Aedsae aegypti  larvae (third larval stage, L3) are treated with a preparation of active compound at the desired concentration. 
     After the desired time the activity is measured in %. Here 100%, means that all of the  Aedsae aegypti  have been killed; 0% means that no  Aedsae aegypti  have been killed, and -1 denotes that no evaluation was possible. 
     In this test effective activity is exhibited by, for example, the following compound of the Preparation Examples: see table 
     
       
         
           
               
               
               
               
             
               
                 TABLE C 
               
               
                   
               
               
                 Example 
                 Structure 
                 g a. i./ha 
                 % 2 d 
               
               
                   
               
             
            
               
                 14 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 20 
                 80