Heteroarylpiperidine and - piperazine derivatives as fungicides

Abstract

Heteroarylpiperidine and -piperazine derivatives of the formula (I) in which the symbols are each as defined in the description, and agrochemically active salts thereof, and use thereof for controlling phytopathogenic harmful fungi, and also processes for preparing compounds of the formula (I).

1 - 8 . (canceled) 
     
     
         9 . A compound of formula (XXXI), or a salt, a metal complex or a N-oxide thereof 
       
         
           
           
               
               
           
         
         W is a leaving group, 
         R 12  is —C(═Y 2 )Y 3 —R 1  or —C(═O)O—(C 1 -C 2 -alkyl), 
         and/or
 a compound of formula (XXXIV), or a salt, a metal complex or a N-oxide thereof 
 
       
       
         
           
           
               
               
           
         
         R 12  is —C(═Y 2 )Y 3 —R 1  or —C(═O)O—(C 1 -C 2 -alkyl), 
         W VI  is chlorine, bromine, iodine, toluenesulphonyloxy or methanesulphonyloxy and/or
 a compound of formula (XXXV), or a salt, a metal complex or a N-oxide thereof 
 
       
       
         
           
           
               
               
           
         
         E is A-L 1 (Y 1 )- or acetyl, C 1 -C 4 -alkoxycarbonyl, benzyl or benzyloxycarbonyl, 
         R 12  is —C(═O)OH, 
         wherein 
         A is phenyl which is bonded to L 1  and may contain up to five further substituents, 
         where the substituents are each independently selected from Z A-1 , 
         or 
         A is an optionally benzofused, unsubstituted or substituted 5- or 6-membered heteroaryl which is bonded to L 1  and may contain up to four further substituents, where the substituents on carbon are each independently selected from Z A-2  and the substituents on nitrogen are each independently selected from Z A-3 , 
         Z A-1  are the same or different and are each independently hydrogen, halogen, hydroxyl, thioxy, nitro, cyano, —C(═O)H, —C(═O)OH, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, cycloalkenyl, halocycloalkyl, halocycloalkenyl, hydroxyalkyl, cyanoalkyl, formylalkyl, alkoxyalkyl, haloalkoxyalkyl, cycloalkoxyalkyl, alkynyloxyalkyl, alkylthioalkyl, alkylsulphinylalkyl, alkylaminoalkyl, haloalkylaminoalkyl, cycloalkylaminoalkyl, dialkylaminoalkyl, alkylcarbonylalkyl, alkylsulphonylalkyl, alkylcycloalkyl, alkylcycloalkenyl, alkoxy, alkylcycloalkylalkyl, halocycloalkoxy, alkylthio, haloalkylthio, cycloalkylthio, alkynylthio, alkenyloxy, alkynyloxy, haloalkoxy, haloalkenyloxy, haloalkynyloxy, cycloalkoxy, alkoxyalkoxy, cycloalkylalkoxy, alkylcarbonyloxy, haloalkylcarbonyloxy, cycloalkylcarbonyloxy, cycloalkylamino, alkylcarbonylamino, cycloalkylcarbonylamino, alkoxycarbonylamino, alkylsulphonylamino, haloalkylsulphonylamino, phenylsulphonylamino, cycloalkylalkyl, halocycloalkylalkyl, cycloalkylcycloalkyl, alkoxyalkoxyalkyl, alkylaminocarbonyloxy, alkylcarbonylalkoxy, cycloalkylaminocarbonyl, cycloalkylalkoxycarbonyl, alkylsulphinyl, haloalkylsulphinyl, alkylsulphonyl, haloalkylsulphonyl, cycloalkylsulphonyl, alkylcarbonyl, haloalkylcarbonyl, cycloalkylcarbonyl, alkoxycarbonyl, cycloalkoxycarbonyl, trialkylsilyl, —SF 5 , phenyl, —C(═O)NR 3 R 4  or —NR 3 R 4 , 
         Z A-2  and R G1  are the same of different and are each independently hydrogen, halogen, hydroxyl, thioxy, nitro, cyano —C(═O)H, —C(═O)OH, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, halocycloalkyl, hydroxyalkyl, formylalkyl, alkoxyalkyl, alkylcarbonylalkyl, alkylcycloalkyl, alkoxy, alkylcycloalkyalkyl, alkylthio, haloalkylthio, alkynylthio, alkenyloxy, alkynyloxyl, haloalkoxy, alkoxyalkoxy, alkylcarbonyloxy, haloalkylcarbonyloxy, cycloalkylcarbonylamino, alkylsulphonylamino, haloalkylsulphonylamino, phenylsulphonylamino, cycloalkylalkyl, halocycloalkylalkyl, cycloalkylcycloalkyl, alkoxycarbonyloxy, alkylcarbonylthio, alkylsulphinyl, haloalkylsulphinyl, alkylsulphonyl, haloalkylsulphonyl, alkylcarbonyl, haloalkylcarbonyl, alkoxycarbonyl, alkylaminocarbonyloxy, —C(═O)NR 3 R 4  or —NR 3 R 4 . 
         Z A-3  and R G2  are the same or different and are each independently hydrogen, —C(═O)H, —(═O)NR 3 R 4 , alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, halocycloalkyl, alkylcycloalkyl, cycloalkylalkyl, alkoxyalkyl, alkylsulphonyl, haloalkylsulphonyl, cycloalkylsulphonyl, phenylsulphonyl, alkylcarbonyl, haloalkylcarbonyl, alkoxycarbonyl, haloalkoxycarbonyl, cycloalkoxycarbonyl, phenyl or benzyl, 
         R 3 , R 4  and R 7  are the same or different and are each independently hydrogen, alkyl, alkenyl, alkynyl, haloalkyl, cycloalkyl, benzyl or phenyl, 
         L 1  is NR L12  or C(R L11 ) 2 , 
         R L11  is the same or different and is independently hydrogen, halogen, hydroxyl, cyano, —C(═O)H, —(═O)OH, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxyalkyl, alkylthioalkyl, alkylaminoalkyl, dialkylaminoalkyl, alkoxy, alkylthio, haloalkylthio, haloalkoxy, alkylcarbonyloxy, alkylcarbonylamino, alkylcarbonylthio, alkylsulphonyl, haloalkylsulphonyl, alkylcarbonyl, haloalkylcarbonyl, alkoxycarbonyl, trialkylsilyloxy, —NR 3 R 4  or —C(═O)NR 3 R 4 , 
         or the two R L11  radicals, together with the carbon atom to which they are bonded, form a cyclopropyl ring, or 
         the two R 11  radicals are ═CH 2 , ═COR 3 , ═NOR 3  or ═CHN(R 3 ) 2 , 
         R L12  is hydrogen —C(═O)H, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, halocycloalkyl, alkylcycloalkyl, cycloalkylalkyl, cycloalkylaminocarbonyl, haloalkylaminocarbonyl, alkylsulphonyl, haloalkylsulphonyl, cycloalkylsulphonyl, alkylcarbonyl, haloalkylcarbonyl, alkoxycarbonyl, haloalkoxycarbonyl, cycloalkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, phenyl or benzyl, 
         Y 1  is sulphur or oxygen, 
         X is carbon or nitrogen, 
         R X2  and R 8  are the same or different and are each independently is hydrogen, alkyl, alkenyl, haloalkyl, alkoxy, halogen, cyano or hydroxyl, 
         R 2  is oxo, alkyl, alkenyl, haloalkyl, alkoxy, halogen, cyano or hydroxyl, 
         p is 0, 1 or 2, 
         G is 5-membered heteroaryl which is substituted by X or Q 1  and may be unsubstituted or substituted, where the substituents on carbon are each independently selected from R G1  and the substituents on nitrogen are each independently selected from R G2 , 
         Q 1  is saturated or partly or fully unsaturated 5-membered heterocyclyl which is substituted by G and —C(═Y 2 )—Y 3 —R 1  and may be unsubstituted or substituted, where the substituents are each independently selected form R Q1 , 
         R Q1  is bonded to carbon of the 5-membered heterocyclyl or Q 1 , 
         hydrogen, oxo, halogen, cyano, hydroxyl, nitro, —CHO, —C(═O)OH, —C(═O)NH 2 , —C(═O)NR 3 R 4 , alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, halocycloalkyl, alkylcycloalkyl, cycloalkylalkyl, cycloalkylcycloalkyl, halocycloalkylalkyl, alkylcycloalkylalkyl, cycloalkenyl, halocycloalkenyl, alkoxyalkyl, haloalkoxyalkyl, cycloalkoxyalkyl, alkoxyalkoxyalkyl, alkylthioalkyl, formylalkyl, alkylcarbonylalkyl, alkylsulphinylalkyl, alkylsulphonylalkyl, alkylaminoalkyl, dialkylaminoalkyl, haloalkylaminoalkyl, cycloalkylaminoalkyl, alkylcarbonyl, haloalkylcarbonyl, cycloalkylcarbonyl, alkoxycarbonyl, cycloalkoxycarbonyl, cycloalkylalkoxycarbonyl, cycloalkylaminocarbonyl, hydroxyalkyl, alkoxy, haloalkoxy, cycloalkoxy, halocycloalkoxy, cycloalkylalkoxy, alkenyloxy, haloalkenyloxy, alkynyloxy, haloalkynyloxy, alkoxyalkoxy, alkylcarbonyloxy, haloalkylcarbonyloxy, cycloalkylcarbonyloxy, alkylcarbonylalkoxy, alkylthio, haloalkylthio, cycloalkylthio, alkylsulphinyl, haloalkylsulphinyl, alkylsulphonyl, haloalkylsulphonyl, cycloalkylsulphonyl, trialkylsilyl, alkylsulphonylamino, haloalkylsulphonylamino, phenyl or 5- or 6-membered heteroaryl radical, where the phenyl or the 5- or 6-membered heteroaryl radical may bear up to two further substituents which are each independently selected from: alkenyl, alkenylamino, alkenyloxy, alkenylthio, alkynyl, alkynylamino, alkynyloxy, alkynylthio, alkoxy, alkoxyalkenyl, alkoxyalkynyl, alkoxyalkoxy, alkoxyalkoxyalkyl, alkoxyalkoxycarbonyl, alkoxyalkyl, alkoxyalkylaminocarbonyl, alkoxyalkylcarbonyl, alkoxyamino, alkoxycarbonyl, alkoxycarbonylalkoxy, alkoxycarbonylalkyl, alkoxycarbonylamino, alkoxyhaloalkoxy, alkoxyhaloalkyl, alkyl, alkylamino, alkylaminoalkyl, alkylaminocarbonyl, alkylaminocarbonylalkylamino, alkylaminocarbonylamino, alkylaminosulphonyl, alkylaminothiocarbonyl, alkylaminothiocarbonylamino, alkylcarbonyl, alkylcarbonylalkoxy, alkylcarbonylamino, alkylcarbonyloxy, alkylcarbonylthio, alkylcycloalkyl, alkylcycloalkylalkyl, alkylsulphinyl, alkylsulphinylalkyl, alkylsulphonyl, alkylsulphonylalkyl, alkylsulphonylamino, alkylsulphonylaminocarbonyl, alkylthio, alkylthioalkyl, alkylthiocarbonyl, alkylthiocarbonyloxy, amino, aminocarbonyl, C(═N—OR 7 )R 3 , C(═O)NHCN, C(═O)OH, cyano, cyanoalkoxy, cyanoalkyl, cycloalkenyl, cycloalkenyloxyalkyl, cycloalkoxy, cycloalkoxyalkyl, cycloalkoxycarbonyl, cycloalkyl, cycloalkylalkoxy, cycloalkylalkoxycarbonyl, cycloalkylalkyl, cycloalkylalkylamino, cycloalkylalkylaminoalkyl, cycloalkylamino, cycloalkylaminoalkyl, cycloalkylaminocarbonyl, cycloalkylcarbonyl, cycloalkylcarbonyloxy, cycloalkylcycloalkyl, cycloalkylsulphonyl, cycloalkylthio, dialkoxyalkyl, dialkylamino, dialkylaminoalkyl, dialkylaminocarbonyl, dialkylaminocarbonylamino, dialkylaminosulphonyl, dialkylaminothiocarbonyl, dialkylaminothiocarbonylamino, halogen, haloalkenyl, haloalkenyloxy, haloalkynyl, haloalkynyloxy, haloalkoxy, haloalkoxyalkoxy, haloalkoxyalkyl, haloalkoxyamino, haloalkoxycarbonyl, haloalkoxycarbonylamino, haloalkoxyhaloalkoxy, haloalkoxyhaloalkyl, haloalkyl, haloalkylamino, haloalkylaminoalkyl, haloalkylcarbonyl, haloalkylcarbonylamino, haloalkylcarbonyloxy, haloalkylsulphinyl;, haloalkylsulphonyl, haloalkylsulphonylamino, haloalkylsulphonylaminocarbonyl, haloalkylthio, halocycloalkenyl, halocycloalkenyloxyalkyl, halocycloalkoxy, halocycloalkoxyalkyl, halocycloalkyl, halocycloalkylalkyl, halocycloalkylcarbonyloxy, halodialkylamino, halodialkylaminoalkyl, hydroxy, hydroxyalkyl, NHCHO, NHCN, nitro, phenylsulphonylamino, SH, SF 5 , SO 2 NHCN, thioxy, trialkylsilyl, hydrogen; or 
         R Q1  is bonded to nitrogen of the 5-membered heterocyclyl of Q 1 ; 
         hydrogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, halocycloalkyl, alkylcycloalkyl, cycloalkylalkyl, phenyl, benzyl, alkylsulphonyl, phenylsulphonyl, —C(═O)H, alkoxycarbonyl, benzyloxycarbonyl, alkylcarbonylalkyl or alkylcarbonyl, 
         Y 2  is oxygen or sulphur, 
         Y 3  is oxygen, sulphur or —(NR Y3 )—, 
         R Y3  is hydrogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, cycloalkylalkyl, halocycloalkyl, benzyl, phenyl, NR 3 R 4 , alkylcarbonyl, alkyloxycarbonyl, alkylaminocarbonyl, trialkylsilyl, benzyloxycarbonyl, alkoxy, haloalkoxy, phenoxy or benzyloxy, 
         R 1  is substituted C 1 -C 5 -alkyl, 
         where the substituents are each independently selected from -Q 2  and/or Z 1a , 
         or 
         R 1  is unsubstituted or substituted C 6 -C 10 -alkyl, 
         where the substituents are each independently selected from -Q 2  and/or Z 1b  when Y 3 =O, S, —NH—, 
         or 
         R 1  is substituted C 6 -C 10 -alkyl, 
         where the substituents are each independently selected from -Q 2  and/or Z 1b  when Y 3 =—(NR Y3 )—and R Y3 ≠H. 
         or 
         R 1  is unsubstituted C 6 -C 10 -alkyl when Y 2 =S and Y 3 =—(NR Y3 )— and R Y3 ≠H, 
         or 
         R 1  is unsubstituted C 8 -C 11 -alkyl, 
         when Y 3 =—(NR Y3 )— and R Y3 ≠H and Y 2 ≠s, 
         or 
         R 1  is unsubstituted or substituted C 2 -C 6 -alkenyl or C 2 -C 6 -alkynyl, 
         where the substituents are each independently selected from -Q 2  and/or Z 1c    
         or 
         R 1  is substituted C 3 -C 7 -cycloalkyl, 
         where the substituents are each independently selected from -Q 2 , Z 1d , oxo and/or thioxo, 
         or 
         R 1  is substituted C 3 -C 7 -cycloalkyl-C 1 -C 3 -alkyl, 
         where the substituents are each independently selected from -Q 2 , Z 1d , oxo and/or thioxo, 
         or 
         R 1  is unsubstituted C 3 -C 7 -cycloalkyl-C 1 -C 3 -alkyl when Y 3  is NR Y3 , 
         or 
         R 1  is unsubstituted or substituted C 5 -C 10 -cycloalkenyl or C 5 -C 10 cycloalkenyl-C 1 -C 4 where the substituents are each independently selected from -Q 2 , Z 1e , oxo and/or thioxo, 
         or 
         R 1  is unsubstituted or substituted phenyl, benzyl or naphthalenyl, 
         where the substituents are each independently selected from -L 2 Q 2  and/or Z 1f , 
         or 
         R 1  represents saturated or partly or fully unsaturated, unsubstituted or substituted, bi- or tricyclic 8- to 11-membered carbocyclic or heterocyclic ring systems 
         where the substituents are each independently selected from Z 1g , oxo and/or thioxo, 
         or 
         R 1  is an unsubstituted or substituted optionally 5- or 6-membered heteroaryl radical, 
         where the substituents on carbon are each independently selected from -L 2 Q 2  and/or Z 1h , and the substituents on nitrogen are each independently selected from Z 1i , 
         or 
         R 1  is a benzofused unsubstituted or substituted 5- or 6-membered heteroaryl radical, 
         where the substituents on carbon are each independently selected from Z 1j , and the substituents on nitrogen are each independently selected from Z 1k , 
         or 
         R 1  is unsubstituted or substituted 5-, 6- or 7-membered, nonaromatic (saturated or partly unsaturated) heterocyclyl systems, 
         where the substituents on carbon are each independently selected from Z 1l , oxo and/or thioxo, and the substituents on nitrogen are each independently selected from Z 1m , 
         or 
         R 1  forms with R Y3 , when Y 3  is —(NR Y3 )—, together with the nitrogen atom through which they are bonded, a 5 to 15-membered, unsubstituted or substituted, saturated or partly saturated or unsaturated mono-, bi- or tricyclic ring system which may contain up to two further heteroatoms selected from N, O and S, where no two oxygen atoms are adjacent and where possible substituents on carbon are each independently selected from R 10 , oxo and/or thioxo, and where possible substituents on nitrogen are each independently selected from R 11 , 
         or 
         R 1  is unsubstituted C 1 -C 5 -alkyl, unsubstituted C 3 -C 7 cycloalkyl or unsubstituted C 3 -C 7 -cycloalkyl C 1 -C 6 -alkyl when Y 3  is sulphur and/or Y 2  is sulphur, 
         Q 2  is a phenyl ring which bears up to two substituents each independently selected from Z 1f , 
         or 
         Q 2  is a 5- or 6-membered heteroaryl radical which may contain up to two substituents, where the substituents are each independently; 
         substituents on carbon: hydrogen, halogen, cyano, hydroxyl, formyl, SH, nitro, NR 6 R 7 alkyl, alkenyl, alkenyloxy, alkynyl, alkynyloxy, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, halocycloalkyl, alkylcycloalkyl, cycloalkylalkyl, cycloalkylcycloalkyl, alkylcycloalkylalkyl, alkoxyalkyl, alkylcarbonyl, alkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, hydroxylakyl, alkoxy, haloalkoxy, alkylcarbonyloxy, alkylcarbonylthio, alkylthio, haloalkylthio, alkylsulphinyl, haloalkylsulphinyl, alkylsulphonyl, haloalkylsulphonyl, trialkylsilyl or phenyl, 
         substituents on nitrogen: hydrogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, halocycloalkyl, alkylcycloalkyl, cycloalkylalkyl, phenyl, benzyl, alkylsulphonyl, phenylsulphonyl, C(═O)H, alkoxycarbonyl, benzyloxycarbonyl, 
         alkylaminocarbonyl, alkylcarbonylalkyl or alkylcarbonyl, 
         R 6  and R 9  are the same or different and are each independently hydrogen, alkyl, alkenyl, alkynyl, haloalkyl, cycloalkyl, benzyl, phenyl, alkylsulphonyl, phenylsulphonyl, alkoxycarbonyl, haloalkoxycarbonyl, benzyloxycarbonyl, alkylaminocarbonyl, alkylcarbonylalkyl alkylcarbonyl haloalkylcarbonyl or trialkylsilyl, 
         L 2  is a direct bond, —O—, —C(═O), —S(O) m , —CHR 8  or —NR 9 -, —(C═O)O—, —(C═O)NR 3 —, —O(C═O)— or —NR 3 (C═O)—, 
         m is 0, 1 or 2, 
         Z 1a  is cyano, halogen, nitro, formyl, NR 6 R 7 , haloalkyl, cycloalkylcycloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, trialkylsilyl, phenyl, hydroxyl, SH, oxo, alkoxy, alkoxyalkoxy, haloalkoxy, alkenyloxy, alkynyloxy, cycloalkyloxy, cycloalkylalkyloxy, halocycloalkyloxy, halocycloalkylalkyloxy, alkoxycarbonyl, alkylcarbonyloxy, alkylcarbonyl, alkylthio or haloalkylthio, phenoxy, 
         Z 1b , Z 1c , Z 1b , Z 1e , Z 1g  are the same or different and are each independently is cyano, halogen, nitro, NR 6 R 7 , alkyl, haloalkyl, cycloalkyl, cycloalkylcycloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, trialkylsilyl, phenyl, hydroxyl, SH, oxo, alkoxy, alkoxylalkoxy, haloalkoxy, alkenyloxy, alkynyloxy, cycloalkyloxy, cycloalkylalkyloxy, halocycloalkyloxy, halocycloalkylalkyloxy, alkoxycarbonyl, alkylcarbonyloxy, alkylcarbonyl, alkylthio or haloalkylthio, or phenoxy, 
         Z 1f  is hydrogen, alkenyl, alkenylamino, alkenyloxy, alkenylthio, alkynyl, alkynylamino, alkynyloxy, alkynylthio, alkoxy, alkoxyalkenyl, alkoxyalkynyl, alkoxyalkoxy, alkoxyalkoxyalkyl, alkoxyalkoxycarbonyl, alkoxyalkyl, alkoxylalkylaminocarbonyl, alkoxyalkylcarbonyl, alkoxyamino, alkoxycarbonyl, alkoxycarbonylalkoxy, alkoxycarbonylalkyl, alkoxycarbonylamino, alkoxyhaloalkoxy, alkoxyhaloalkyl, alkyl, alkylamino, alkylaminoalkyl, alkylaminocarbonyl, alkylaminocarbonylalkylamino, alkylaminocarbonylamino, alkylaminosulphonyl, alkylaminothiocarbonyl, alkylaminothiocarbonylamino, alkylcarbonyl, alkylcarbonylalkoxy, alkylcarbonylamino, alkylcarbonyloxy, alkylcarbonylthio, alkylcycloalkyl, alkylcycloalkylalkyl, alkylsulphinyl, alkylsulphinylalkyl, alkylsulphonyl, alkylsulphonylalkyl, alkylsulphonylamino, alkylsulphonylaminocarbonyl, alkylthio, alkylthioalkyl, alkylthiocarbonyl, alkylthiocarbonyloxy, amino, aminocarbonyl, C(═N—OR 7 )R 8 , C(═O)H, C(═O)NHCN, C(═O)OH, cyano, cyanoalkoxy, cyanoalkyl, cycloalkenyl, cycloalkenyloxyalkyl, cycloalkoxy, cycloalkoxyalkyl, cycloalkoxycarbonyl, cycloalkyl, cycloalkylalkoxy, cycloalkylalkoxycarbonyl, cycloalkylalkyl, cycloalkylalkylamino, cycloalkylalkylaminoalkyl, cycloalkylamino, cycloalkylaminoalkyl, cycloalkylaminocarbonyl, cycloalkylcarbonyl, cycloalkylcarbonyloxy, cycloalkylcycloalkyl, cycloalkylsulphonyl, cycloalkylthio, dialkoxyalkyl, dialkylamino, dialkylaminoalkyl, dialkylaminocarbonyl, dialkylaminocarbonylamino, dialkylaminosulphonyl, dialkylaminothiocarbonyl, dialkylaminothiocarbonylamino, halogen, haloalkenyl, haloalkenyloxy, haloalkynyl, haloalkynyloxy, haloalkoxy, haloalkoxyalkoxy, haloalkoxyalkyl, haloalkoxyamino, haloalkoxycarbonyl, haloalkoxycarbonylamino, haloalkoxyhaloalkoxy, haloalkoxyhaloalkyl, haloalkyl, haloalkylamino, haloalkylaminoalkyl, haloalkylcarbonyl, haloalkylcarbonylamino, haloalkylcarbonyloxy, haloalkylsulphinyl, haloalkylsulphonyl, haloalkylsulphonylamino, haloalkylsulphonylaminocarbonyl, haloalkylthio, halocycloalkenyl, halocycloalkenyloxyalkyl, halocycloalkoxy, halocycloalkoxyalkyl, halocycloalkyl, halocycloalkylalkyl, halocycloalkylcarbonyloxy, halodialkylamino, halodialkylaminoalkyl, hydroxy, hydroxyalkyl, NHCHO, NHCN, nitro, phenylsulphonylamino, SH, SF 5 , SO 2 NHCN, thioxy, or trialkylsilyl, 
         Z 1h , Z 1j  and Z 1l  are the same or different and are each independently hydrogen, oxo, halogen, cyano, hydroxyl, nitro, —CHO, —C(═O)Oh, —C(═O)NH 2 , —C(═O)NR 3 R 4 , —NR 3 R 4 , alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, halocycloalkyl, alkylcycloalkyl, cycloalkylalkyl, cycloalkylcycloalkyl, halocycloalkylalkyl, alkylcycloalkylalkyl, cycloalkenyl, halocycloalkenyl, alkoxyalkyl, haloalkoxyalkyl, cycloalkoxyalkyl, alkoxyalkoxyalkyl, alkylthioalkyl, formylalkyl, alkylcarbonylalkyl, alkylsulphinylalkyl, alkylsulphonylalkyl, alkylaminoalkyl, dialkylaminoalkyl, haloalkylaminoalkyl, cycloalkylaminoalkyl, alkylcarbonyl, haloalkylcarbonyl, cycloalkylcarbonyl, alkoxycarbonyl, cycloalkoxycarbonyl, cycloalkylalkoxycarbonyl, cycloalkylaminocarbonyl, hydroxyalkyl, alkoxy, haloalkoxy, cycloalkoxy, halocycloalkoxy, cycloalkylalkoxy, alkenyloxy, haloalkenyloxy, alkynyloxy, haloalkynyloxy, alkoxyalkoxy, alkylcarbonyloxy, haloalkylcarbonyloxy, cycloalkylcarbonyloxy, alkylcarbonylalkoxy, alkylthio, haloalkylthio, cycloalkylthio, alkylsulphinyl, haloalkylsulphinyl, alkylsulphonyl, haloalkylsulphonyl, cycloalkylsulphonyl, trialkylsilyl, alkylsulphonylamino, haloalkylsulphonylamino, 
         Z 1i , Z 1k  and Z 1m  are the same or different and are each independently hydrogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, halocycloalkyl, alkylcycloalkyl, cycloalkylalkyl, phenyl, benzyl, alkylsulphonyl, —C(═O)H, alkoxycarbonyl, benzyloxycarbonyl or alkylcarbonyl, 
         R 10  is hydrogen, cyano, halogen, NR 6 R 7 , alkyl, haloalkyl, cycloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, trialkylsilyl, phenyl, hydroxyl, oxo, alkoxy, haloalkoxy, alkenyloxy, alkynyloxy, alkylthio or haloalkylthio, and 
         R 11  is hydrogen, alkyl, haloalkyl, cycloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, trialkylsilyl, benzyl, phenyl, alkylsulphonyl, phenylsulphonyl, C(═O)H, alkoxycarbonyl, haloalkoxycarbonyl, benzyloxycarbonyl, alkylaminocarbonyl, alkylcarbonylalkyl, alkylcarbonyl or haloalkylcarbonyl. 
       
     
     
         10 - 15 . (canceled) 
     
     
         16 . The compound according to  claim 9 ,
 wherein   A is pyrazol-1-yl which is bonded to L 1  and may contain up to two substituents, where the substituents are each independently methyl, ethyl, chlorine, bromine, fluorine, difluoromethyl or trifluoromethyl, or   A is phenyl which is bonded to L 1  and may contain up to two substituents, where the substituents are each independently methyl, ethyl, iodine, chlorine, bromine, fluorine, methoxy, ethoxy, difluoromethyl or trifluoromethyl.   
     
     
         17 . The compound of according to  claim 9 ,
 wherein   L 1  is CHR L1 , and   R L11  is hydrogen, methyl, ethyl or cyclopropyl.   
     
     
         18 . The compound of according to  claim 9 ,
 wherein   Y 1  is oxygen,   X is carbon, and   R X2  is hydrogen or fluorine.   
     
     
         19 . The compound of according to  claim 9 ,
 wherein   G is G 1 , G 2 , or G 3      
       
         
           
           
               
               
           
         
         where the bond identified by “v” is bonded directly to X and where the bond identified by “w” is bonded directly to Q 1 . 
       
     
     
         20 . The compound of according to  claim 9 ,
 wherein   Q is   
       
         
           
           
               
               
           
         
         where the bond identified by “x” is bonded directly to G, and where the bond identified by “y” is bonded directly to —C(═Y 2 )—Y 3 —R 1 , 
         R Q1  is hydrogen, fluorine, cyano, methyl, trifluoromethyl, difluoromethyl or methoxymethyl, or 
         R Q1  is a phenyl ring which is bonded to the carbon atom of Q 1  and which bears up to two substituents each independently selected from the group consisting of hydrogen, fluorine, chlorine, nitro, trifluoromethyl, C(═O)H, methyl, ethyl, methoxy, ethoxy, prop-2-yn-1-yloxy, but-2-yn-1-yloxy, pent-2-yn-1-yloxy, but-3-yn-1-yloxy, but-3-en-1-yloxy, 3-chloroprop-2-yn-1-yloxy, cyanomethoxy, and allyloxy. 
       
     
     
         21 . The compound according to  claim 9 ,
 wherein   Y 2  is oxygen,   Y 3  is oxygen and —(NR Y3 )—, and   R Y3  is hydrogen, methyl or cyclopropyl.   
     
     
         22 . The compound according to  claim 9 ,
 wherein   R 1  is, when Y 3 =S, cyclopropyl, cyclopentyl or cyclohexyl,   or   R 1  is substituted cyclopropyl or cyclohexyl, where the substituents are each independently selected from fluorine, chlorine, bromine, cyano, methyl, ethyl or phenyl,   or   R 1  is cyclopentenyl or cyclohexenyl,   or   R 1  is unsubstituted or substituted phenyl or benzyl, where the substituents are each independently selected from fluorine, chlorine, bromine, cyano, methyl, ethyl or methoxy.