Pyridine Compounds for Controlling Invertebrate Pests II

Abstract

The present invention relates to novel pyridine compounds of the formulae I and II, to their salts, to their tautomers, to their N-oxides, and to the salts of these N-oxides or tautomers. The compounds are useful for combating or controlling invertebrate pests, in particular arthropod pests. The invention also relates to a method for controlling in-vertebrate pests by using these compounds. The invention further relates to plant propagation material and to agricultural compositions comprising said compounds. wherein A is a radical of the formulae A1, A2, A3, A4, A5 or A6 wherein # denotes the binding site to the remainder of formulae I or II; Z is O, S or N—R N ; X 1 is S, O or NR 1a ; X 2 is OR 2a , NR 2b R 2c , S(O) m R 2d ; X 3 is a lone pair or oxygen; R 1 , R 2 and R 3 are, inter alia, hydrogen, and R A1 , R A2 R A3 R A4 , R A5 , R A6 and R N , are as defined in claim 1.

1 - 25 . (canceled) 
     
     
         26 . 3-pyridyl compound of formulae (I) or (II) 
       
         
           
           
               
               
           
         
         wherein 
         A is a radical of the formulae A1, A2, A3, A4, A5 or A6 
       
       
         
           
           
               
               
           
         
         
           where # denotes the binding site to the remainder of formulae (I) and (II) 
           Z is O, S or N—R N ; 
           R A1 , R A2 , R A3 , R A4 , R A5 , R A6  independently of each other are selected from the group consisting of hydrogen, halogen, CN, NO 2 , C 1 -C 10 -alkyl, C 2 -C 10 -alkenyl and C 2 -C 10 -alkynyl, wherein the last three mentioned radicals may be unsubstituted, may be partially or fully halogenated or may carry 1, 2 or 3 identical or different substituents R x ,
 or from the group consisting of OR a , C(Y)R b , C(Y)OR c , S(O) m R d , NR e R f , C 3 -C 10 -cycloalkyl, C 5 -C 10 -cycloalkenyl, heterocyclyl, phenyl, hetaryl, C 3 -C 10 -cycloalkyl-C 1 -C s -alkyl, C 5 -C 10 -cycloalkenyl-C 1 -C 5 -alkyl, heterocyclyl-C 1 -C 5 -alkyl, hetaryl-C 1 -C 5 -alkyl, phenyl-C 1 -C 5 -alkyl and phenoxy-C 1 -C 5 -alkyl wherein the cyclic moieties of the eleven last mentioned radicals may be unsubstituted or may carry 1, 2, 3, 4 or 5 identical or different substituents R y ; and 
 
           R N  is selected from the group consisting of hydrogen, CN, NO 2 , C 1 -C 10 -alkyl, C 2 -C 10 -alkenyl and C 2 -C 10 -alkynyl, wherein the three last mentioned radicals may be unsubstituted, may be partially or fully halogenated or may carry 1, 2 or 3 identical or different substituents R x , or from the group consisting of OR a , C(Y)R b , C(Y)OR c , S(O) m R d , NR e R f , C(Y)NR g R h , S(O) m NR e R f , C(Y)NR i NR e R f , C 1 -C 5 -alkylen-OR a , C 1 -C 5 -alkylen-CN, C 1 -C 5 -alkylen-C(Y)R b , C 1 -C 5 -alkylen-C(Y)OR c , C 1 -C 5 -alkylen-NR e R f , C 1 -C 5 -alkylen-C(Y)NR g R h , C 1 -C 5 -alkylen-S(O) m R d , C 1 -C 5 -alkylen-S(O) m N e R f , C 1 -C 5 -alkylen-NR i NR e R f , C 3 -C 10 -cycloalkyl, C 5 -C 10 -cycloalkenyl, heterocyclyl, phenyl, hetaryl, C 3 -C 10 -cycloalkyl-C 1 -C 5 -alkyl, C 5 -C 10 -cycloalkenyl-C 1 -C 5 -alkyl, heterocyclyl-C 1 -C 5 -alkyl, hetaryl-C 1 -C 5 -alkyl, phenyl-C 1 -C 5 -alkyl and phenoxy-C 1 -C 5 -alkyl wherein the cyclic moieties of the eleven last mentioned radicals may be unsubstituted or may carry 1, 2, 3, 4 or 5 identical or different substituents R y ; 
           and where 
           m is O, 1 or 2 
           Y is O or S; 
         
         X 1  is S, O or NR 1a , where R 1a  is selected from the group consisting of hydrogen, C 1 -C 10 -alkyl, C 1 -C 4 -haloalkyl, C 3 -C 10 -cycloalkyl, C 3 -C 10 -cycloalkylmethyl, C 3 -C 10 -halocycloalkyl, C 2 -C 10 -alkenyl, C 2 -C 10 -haloalkenyl, C 2 -C 10 -alkynyl, C 1 -C 10 -alkoxy-C 1 -C 4 -alkyl, OR a , phenyl, hetaryl, phenyl-C 1 -C 4 -alkyl and hetaryl-C 1 -C 4 -alkyl, wherein the aromatic ring in the four last mentioned radicals may be unsubstituted or may carry 1, 2, 3, 4 or 5 substituents which, independently of each other, are selected from the group consisting of halogen, cyano, nitro, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy and C 1 -C 4 -haloalkoxy; 
         X 2  is OR 2a , NR 2b R 2c , S(O) m R 2d , where
 R 2a  is selected from the group consisting of C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halocycloalkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -haloalkenyl, C 2 -C 4 -alkynyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, phenyl, hetaryl, phenyl-C 1 -C 4 -alkyl and hetaryl-C 1 -C 4 -alkyl, wherein the aromatic ring in the four last mentioned radicals may be unsubstituted or may carry 1, 2, 3, 4 or 5 substituents which, independently of each other, are selected from the group consisting of halogen, cyano, nitro, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy and C 1 -C 4 -haloalkoxy; 
 R 2b , R 2c  are independently of each other selected from the group consisting of hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halocycloalkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -haloalkenyl, C 2 -C 4 -alkynyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkylcarbonyl, C 1 -C 4 -haloalkylcarbonyl, C 1 -C 4 -alkylsulfonyl, C 1 -C 4 -haloalkylsulfonyl, phenyl, phenylcarbonyl, phenylsulfonyl, hetaryl, hetarylcarbonyl, hetarylsulfonyl, phenyl-C 1 -C 4 -alkyl and hetaryl-C 1 -C 4 -alkyl, wherein the aromatic ring in the eight last mentioned radicals may be unsubstituted or may carry 1, 2, 3, 4 or 5 substituents which, independently of each other, are selected from the group consisting of halogen, cyano, nitro, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy and C 1 -C 4 -haloalkoxy; or 
 R 2b  and R 2c  together with the nitrogen atom to which they are bound form a 5- or 6-membered, saturated or unsaturated heterocycle, which may carry a further heteroatom being selected from the group consisting of O, S and N as a ring member atom and wherein the heterocycle may be unsubstituted or may carry 1, 2, 3, 4 or 5 substituents which, independently of each other, are selected from the group consisting of halogen, cyano, nitro, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy and C 1 -C 4 -haloalkoxyl; 
 R 2d  is selected from the group consisting of C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halocycloalkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -haloalkenyl, C 2 -C 4 -alkynyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, phenyl, hetaryl, phenyl-C 1 -C 4 -alkyl and hetaryl-C 1 -C 4 -alkyl, wherein the aromatic ring in the four last mentioned radicals may be unsubstituted or may carry 1, 2, 3, 4 or 5 substituents which, independently of each other, are selected from the group consisting of halogen, cyano, nitro, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy and C 1 -C 4 -haloalkoxy; 
 
         X 3  is a lone pair or oxygen; 
         R 1  is hydrogen, CN, C 1 -C 10 -alkyl, C 1 -C 10 -haloalkyl, C 2 -C 10 -alkenyl, C 2 -C 10 -haloalkenyl, C 2 -C 10 -alkynyl, C 3 -C 10 -haloalkynyl, OR a , C(Y)R b , C(Y)OR c , S(O) 2 R d , NR e R f , C(Y)NR g R b , S(O) m NR e R f , C(Y)NR i NR e R f , C 1 -C 5 -alkylen-OR a , C 1 -C 5 -alkylen-CN, C 1 -C 5 -alkylen-C(Y)R b , C 1 -C 5 -alkylen-C(Y)OR c , C 1 -C 5 -alkylen-NR e R f , C 1 -C 5 -alkylen-C(Y)NR g R h , C 1 -C 5 -alkylen-S(O) 2 R d , C 1 -C 5 -alkylen-S(O) m NR e R d , C 1 -C 5 -alkylen-C(Y)NR i NR e R f , phenyl, hetaryl, C 3 -C 10 -cycloalkyl, heterocyclyl, phenyl-C 1 -C 5 -alkyl, hetaryl-C 1 -C 5 -alkyl, heterocyclyl-C 1 -C 5 -alkyl, C 3 -C 10 -cycloalkyl-C 1 -C 5 -alkyl and phenoxy-C 1 -C 5 -alkyl, wherein the rings of the nine last mentioned radicals may be unsubstituted or may carry 1, 2, 3, 4 or 5 identical or different substituents selected from the radicals R y ; 
         R 2  is hydrogen, halogen, methyl, halomethyl, methoxy, halomethoxy, methylthio, halomethylthio, methylsulfinyl, halomethylsulfinyl, methylsulfonyl or halomethylsulfonyl; 
         R 3  is hydrogen, halogen, C 1 -C 4 -alkyl, 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 -alkylsulfinyl, C 1 -C 4 -haloalkylsulfinyl, C 1 -C 4 -alkylsulfonyl, C 1 -C 4 -haloalkylsulfonyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halocycloalkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -haloalkenyl, C 2 -C 4 -alkynyl or C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl; 
         R a , R b , R c  are independently of each other selected from the group consisting of hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkylmethyl, C 3 -C 6 -halocycloalkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -haloalkenyl, C 2 -C 4 -alkynyl,C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, phenyl, hetaryl, heterocyclyl, phenyl-C 1 -C 4 -alkyl, hetaryl-C 1 -C 4 -alkyl and heterocyclyl-C 1 -C 4 -alkyl, wherein the ring in the six last mentioned radicals may be unsubstituted or may carry 1, 2, 3, 4 or 5 substituents which, independently of each other, are selected from the group consisting of halogen, cyano, nitro, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy and C 1 -C 4 -haloalkoxy; 
         R d  is selected from C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkylmethyl, C 3 -C 6 -halocycloalkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -haloalkenyl, C 2 -C 4 -alkynyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, phenyl, hetaryl, heterocyclyl, phenyl-C 1 -C 4 -alkyl, hetaryl-C 1 -C 4 -alkyl and heterocyclyl-C 1 -C 4 -alkyl wherein the ring in the six last mentioned radicals may be unsubstituted or may carry 1, 2, 3, 4 or 5 substituents which are independently of each other selected from halogen, cyano, nitro, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy and C 1 -C 4 -haloalkoxy; 
         R e , R f  are independently of each other selected from hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkylmethyl, C 3 -C 6 -halocycloalkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -haloalkenyl, C 2 -C 4 -alkynyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkylcarbonyl, C 1 -C 4 -haloalkylcarbonyl, C 1 -C 4 -alkylsulfonyl, C 1 -C 4 -haloalkylsulfonyl, phenyl, phenylcarbonyl, phenylsulfonyl, hetaryl, hetarylcarbonyl, hetarylsulfonyl, heterocyclyl, heterocyclylcarbonyl, heterocyclylsulfonyl, phenyl-C 1 -C 4 -alkyl, hetaryl-C 1 -C 4 -alkyl and heterocyclyl-C 1 -C 4 -alkyl wherein the ring in the twelve last mentioned radicals may be unsubstituted or may carry 1, 2, 3, 4 or 5 substituents which, independently of each other, are selected from the group consiting of halogen, cyano, nitro, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy and C 1 -C 4 -haloalkoxy; or 
         R e  and R f  together with the nitrogen atom to which they are bound form a 5- or 6-membered, saturated or unsaturated heterocycle, which may carry a further heteroatom being selected from the group consisting of O, S and N as a ring member atom and wherein the heterocycle may be unsubstituted or may carry 1, 2, 3, 4 or 5 substituents which are independently of each other selected from the group consisting of halogen, cyano, nitro, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy and C 1 -C 4 -haloalkoxy; 
         R g , R h  are independently of each other selected from hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halocycloalkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -haloalkenyl, C 2 -C 4 -alkynyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, phenyl, hetaryl, heterocyclyl, phenyl-C 1 -C 4 -alkyl, hetaryl-C 1 -C 4 -alkyl and heterocyclyl-C 1 -C 4 -alkyl wherein the ring in the six last mentioned radicals may be unsubstituted or may carry 1, 2, 3, 4 or 5 substituents which are independently of each other selected from the group consisting halogen, cyano, nitro, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy and C 1 -C 4 -haloalkoxy; 
         R i  is selected from the group consisting hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkylmethyl, C 3 -C 6 -halocycloalkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -haloalkenyl, C 2 -C 4 -alkynyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, phenyl and phenyl-C 1 -C 4 -alkyl wherein the phenyl ring in the two last mentioned radicals may be unsubstituted or may carry 1, 2, 3, 4 or 5 substituents which are independently of each other selected from the group consisting of halogen, cyano, nitro, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy and C 1 -C 4 -haloalkoxy; 
         R x  are independently of each other selected from the group consisting cyano, nitro, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -haloalkylthio, C 1 -C 4 -alkylsulfinyl, C 1 -C 4 -haloalkylsulfinyl, C 1 -C 4 -alkylsulfonyl, C 1 -C 4 -haloalkylsulfonyl, C 1 -C 10 -alkylcarbonyl, C 3 -C 6 -cycloalkyl, 5- to 7-membered heterocyclyl, phenyl, C 3 -C 6 -cycloalkoxy, 3- to 6-membered heterocyclyloxy and phenoxy, wherein the last 6 mentioned radicals may be unsubstituted or may carry 1, 2, 3, 4 or 5 radicals selected from the group consisting of halogen, cyano, nitro, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy and C 1 -C 4 -haloalkoxy; 
         R y  is selected from the group consisting halogen, cyano, nitro, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, S(O) m R d , S(O) m NR e R f , C 1 -C 4 -alkylcarbonyl, C 1 -C 4 -haloalkylcarbonyl, C 1 -C 4 -alkoxycarbonyl, C 1 -C 4 -haloalkoxycarbonyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halocycloalkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -haloalkenyl, C 2 -C 4 -alkynyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl, 5- to 7-membered heterocyclyl, hetaryl, phenyl, C 3 -C 6 -cycloalkoxy, 3- to 6-membered heterocyclyloxy, hetaryloxy and phenoxy, wherein the last 8 mentioned radicals may be unsubstituted or may carry 1, 2, 3, 4 or 5 radicals selected from the group consisting of halogen, cyano, nitro, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy and C 1 -C 4 -haloalkoxy; 
         or a salt, an N-oxide, a tautomer thereof, or the salt of the N-oxide or the tautomer. 
       
     
     
         27 . The compound as claimed in  claim 26 , which is a compound of the formula I. 
     
     
         28 . The compound as claimed in  claim 27 , wherein X 1  in formula I is oxygen. 
     
     
         29 . The compound as claimed in  claim 26 , wherein R 1  is hydrogen, C 1 -C 10 -alkyl, C 1 -C 10 -haloalkyl, C 1 -C 4 -alkylene-CN, heterocyclyl-C 1 -C 5 -alkyl, hetaryl-C 1 -C 5 -alkyl, C 1 -C 5 -alkylen-OR a  or C 3 -C 10 -cycloalkyl-C 1 -C 5 -alkyl. 
     
     
         30 . The compound as claimed in  claim 29 , wherein R 1  is hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 3 -alkylen-O—C 1 -C 3 -alkyl or C 1 -C 4 -alkylene-CN. 
     
     
         31 . The compound as claimed in  claim 26 , wherein both radicals R 2  and R 3  are hydrogen. 
     
     
         32 . The compound as claimed in  claim 26 , wherein Z is NR N . 
     
     
         33 . The compound as claimed in  claim 32 , where R N  is selected from the group consisting of hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkylene-CN, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl, heterocyclyl-C 1 -C 4 -alkyl, where the cycloalkyl or heterocyclyl moieties in the last three mentioned radicals are unsubstituted or carry 1 or 2 radicals selected from the group consisting of halogen, CN, C 1 -C 2 -alkyl and C 1 -C 2 -haloalkyl;
 phenyl and phenyl-C 1 -C 4 -alkyl, where the phenyl moiety in the last two mentioned radicals is unsubstituted or carries 1 or 2 radicals selected from the group consisting of halogen, CN, C 1 -C 2 -alkyl, C 1 -C 2 -haloalkyl, C 1 -C 2 -alkoxy and C 1 -C 2 -haloalkoxy.   
     
     
         34 . The compound as claimed in  claim 26 , wherein Z is O. 
     
     
         35 . The compound as claimed in  claim 26 , wherein Z is S. 
     
     
         36 . The compound as claimed in  claim 26 , wherein A is a radical A1, A2 or A3. 
     
     
         37 . The compound as claimed in  claim 26 , wherein R A1 , R A2  and R A3 , independently of each other, are selected from the group consisting of hydrogen, halogen, CN, NO 2 , C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 3 -C 6 -cycloalkyl and C 3 -C 6 -halocycloalkyl. 
     
     
         38 . The compound as claimed in  claim 26 , wherein A is a radical A4, A5 or A6. 
     
     
         39 . The compound as claimed in  claim 39 , wherein R A4 , R 5A  and R A6 , independently of each other, are selected from the group consisting of hydrogen, halogen, CN, NO 2 , C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 3 -C 6 -cycloalkyl and C 3 -C 6 -halocycloalkyl. 
     
     
         40 . A method for controlling invertebrate pests which method comprises treating the pests, their food supply, their habitat or their breeding ground or a plant, seed, soil, area, material or environment in which the pests are growing or may grow, or the materials, plants, seeds, soils, surfaces or spaces to be protected from pest attack or infestation with a pesticidally effective amount of a compound of formula (I) or (II): 
       
         
           
           
               
               
           
         
         wherein 
         A is a radical of the formulae A1, A2, A3, A4, A5 or A6 
       
       
         
           
           
               
               
           
         
         
           where # denotes the binding site to the remainder of formulae (I) and (II) Z is O, S or N—R N ; 
           R A1 , R A2 , R A3 , R A4 , R A5 , R A6  independently of each other are selected from the group consisting of hydrogen, halogen, CN, NO 2 , C 1 -C 10 -alkyl, C 2 -C 10 -alkenyl and C 2 -C 10 -alkynyl, wherein the last three mentioned radicals may be unsubstituted, may be partially or fully halogenated or may carry 1, 2 or 3 identical or different substituents R x ,
 or from the group consisting of OR a , C(Y)R b , C(Y)OR c , S(O) m R d , NR e R f , C 3 -C 10 -cycloalkyl, C 5 -C 10 -cycloalkenyl, heterocyclyl, phenyl, hetaryl, C 3 -C 10 -cycloalkyl-C 1 -C s -alkyl, C 5 -C 10 -cycloalkenyl-C 1 -C 5 -alkyl, heterocyclyl-C 1 -C 5 -alkyl, hetaryl-C 1 -C 5 -alkyl, phenyl-C 1 -C 5 -alkyl and phenoxy-C 1 -C 5 -alkyl wherein the cyclic moieties of the eleven last mentioned radicals may be unsubstituted or may carry 1, 2, 3, 4 or 5 identical or different substituents R y ; and 
 
           R N  is selected from the group consisting of hydrogen, CN, NO 2 , C 1 -C 10 -alkyl, C 2 -C 10 -alkenyl and C 2 -C 10 -alkynyl, wherein the three last mentioned radicals may be unsubstituted, may be partially or fully halogenated or may carry 1, 2 or 3 identical or different substituents R x , or from the group consisting of OR a , C(Y)R b , C(Y)OR c , S(O) m R d , NR e R f , C(Y)NR g R h , S(O) m NR e R f , C(Y)NR i NR e R f , C 1 -C 5 -alkylen-OR a , C 1 -C 5 -alkylen-CN, C 1 -C 5 -alkylen-C(Y)R b , C 1 -C 5 -alkylen-C(Y)OR c , C 1 -C 5 -alkylen-NR e R f , C 1 -C 5 -alkylen-C(Y)NR g R h , C 1 -C 5 -alkylen-S(O) m R d , C 1 -C 5 -alkylen-S(O) m N e R f , C 1 -C 5 -alkylen-NR i NR e R f , C 3 -C 10 -cycloalkyl, C 5 -C 10 -cycloalkenyl, heterocyclyl, phenyl, hetaryl, C 3 -C 10 -cycloalkyl-C 1 -C 5 -alkyl, C 5 -C 10 -cycloalkenyl-C 1 -C 5 -alkyl, heterocyclyl-C 1 -C 5 -alkyl, hetaryl-C 1 -C 5 -alkyl, phenyl-C 1 -C 5 -alkyl and phenoxy-C 1 -C 5 -alkyl wherein the cyclic moieties of the eleven last mentioned radicals may be unsubstituted or may carry 1, 2, 3, 4 or 5 identical or different substituents R y ; 
           and where 
           m is O, 1 or 2 
           Y is O or S; 
         
         X 1  is S, O or NR 1a , where R 1a  is selected from the group consisting of hydrogen, C 1 -C 10 -alkyl, C 1 -C 4 -haloalkyl, C 3 -C 10 -cycloalkyl, C 3 -C 10 -cycloalkylmethyl, C 3 -C 10 -halocycloalkyl, C 2 -C 10 -alkenyl, C 2 -C 10 -haloalkenyl, C 2 -C 10 -alkynyl, C 1 -C 10 -alkoxy-C 1 -C 4 -alkyl, OR a , phenyl, hetaryl, phenyl-C 1 -C 4 -alkyl and hetaryl-C 1 -C 4 -alkyl, wherein the aromatic ring in the four last mentioned radicals may be unsubstituted or may carry 1, 2, 3, 4 or 5 substituents which, independently of each other, are selected from the group consisting of halogen, cyano, nitro, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy and C 1 -C 4 -haloalkoxy; 
         X 2  is OR 2a , NR 2b R 2c , S(O) m R 2d , where
 R 2a  is selected from the group consisting of C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halocycloalkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -haloalkenyl, C 2 -C 4 -alkynyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, phenyl, hetaryl, phenyl-C 1 -C 4 -alkyl and hetaryl-C 1 -C 4 -alkyl, wherein the aromatic ring in the four last mentioned radicals may be unsubstituted or may carry 1, 2, 3, 4 or 5 substituents which, independently of each other, are selected from the group consisting of halogen, cyano, nitro, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy and C 1 -C 4 -haloalkoxy; 
 R 2b , R 2c  are independently of each other selected from the group consisting of hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halocycloalkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -haloalkenyl, C 2 -C 4 -alkynyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkylcarbonyl, C 1 -C 4 -haloalkylcarbonyl, C 1 -C 4 -alkylsulfonyl, C 1 -C 4 -haloalkylsulfonyl, phenyl, phenylcarbonyl, phenylsulfonyl, hetaryl, hetarylcarbonyl, hetarylsulfonyl, phenyl-C 1 -C 4 -alkyl and hetaryl-C 1 -C 4 -alkyl, wherein the aromatic ring in the eight last mentioned radicals may be unsubstituted or may carry 1, 2, 3, 4 or 5 substituents which, independently of each other, are selected from the group consisting of halogen, cyano, nitro, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy and C 1 -C 4 -haloalkoxy; or 
 R 2b  and R 2c  together with the nitrogen atom to which they are bound form a 5- or 6-membered, saturated or unsaturated heterocycle, which may carry a further heteroatom being selected from the group consisting of O, S and N as a ring member atom and wherein the heterocycle may be unsubstituted or may carry 1, 2, 3, 4 or 5 substituents which, independently of each other, are selected from the group consisting of halogen, cyano, nitro, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy and C 1 -C 4 -haloalkoxyl; 
 R 2d  is selected from the group consisting of C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halocycloalkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -haloalkenyl, C 2 -C 4 -alkynyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, phenyl, hetaryl, phenyl-C 1 -C 4 -alkyl and hetaryl-C 1 -C 4 -alkyl, wherein the aromatic ring in the four last mentioned radicals may be unsubstituted or may carry 1, 2, 3, 4 or 5 substituents which, independently of each other, are selected from the group consisting of halogen, cyano, nitro, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy and C 1 -C 4 -haloalkoxy; 
 
         X 3  is a lone pair or oxygen; 
         R 1  is hydrogen, CN, C 1 -C 10 -alkyl, C 1 -C 10 -haloalkyl, C 2 -C 10 -alkenyl, C 2 -C 10 -haloalkenyl, C 2 -C 10 -alkynyl, C 3 -C 10 -haloalkynyl, OR a , C(Y)R b , C(Y)OR c , S(O) 2 R d , NR e R f , C(Y)NR g R b , S(O) m NR e R f , C(Y)NR i NR e R f , C 1 -C 5 -alkylen-OR a , C 1 -C 5 -alkylen-CN, C 1 -C 5 -alkylen-C(Y)R b , C 1 -C 5 -alkylen-C(Y)OR c , C 1 -C 5 -alkylen-NR e R f , C 1 -C 5 -alkylen-C(Y)NR g R h , C 1 -C 5 -alkylen-S(O) 2 R d , C 1 -C 5 -alkylen-S(O) m NR e R d , C 1 -C 5 -alkylen-C(Y)NR i NR e R f , phenyl, hetaryl, C 3 -C 10 -cycloalkyl, heterocyclyl, phenyl-C 1 -C 5 -alkyl, hetaryl-C 1 -C 5 -alkyl, heterocyclyl-C 1 -C 5 -alkyl, C 3 -C 10 -cycloalkyl-C 1 -C 5 -alkyl and phenoxy-C 1 -C 5 -alkyl, wherein the rings of the nine last mentioned radicals may be unsubstituted or may carry 1, 2, 3, 4 or 5 identical or different substituents selected from the radicals R y ; 
         R 2  is hydrogen, halogen, methyl, halomethyl, methoxy, halomethoxy, methylthio, halomethylthio, methylsulfinyl, halomethylsulfinyl, methylsulfonyl or halomethylsulfonyl; 
         R 3  is hydrogen, halogen, C 1 -C 4 -alkyl, 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 -alkylsulfinyl, C 1 -C 4 -haloalkylsulfinyl, C 1 -C 4 -alkylsulfonyl, C 1 -C 4 -haloalkylsulfonyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halocycloalkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -haloalkenyl, C 2 -C 4 -alkynyl or C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl; 
         R a , R b , R c  are independently of each other selected from the group consisting of hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkylmethyl, C 3 -C 6 -halocycloalkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -haloalkenyl, C 2 -C 4 -alkynyl,C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, phenyl, hetaryl, heterocyclyl, phenyl-C 1 -C 4 -alkyl, hetaryl-C 1 -C 4 -alkyl and heterocyclyl-C 1 -C 4 -alkyl, wherein the ring in the six last mentioned radicals may be unsubstituted or may carry 1, 2, 3, 4 or 5 substituents which, independently of each other, are selected from the group consisting of halogen, cyano, nitro, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy and C 1 -C 4 -haloalkoxy; 
         R d  is selected from C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkylmethyl, C 3 -C 6 -halocycloalkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -haloalkenyl, C 2 -C 4 -alkynyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, phenyl, hetaryl, heterocyclyl, phenyl-C 1 -C 4 -alkyl, hetaryl-C 1 -C 4 -alkyl and heterocyclyl-C 1 -C 4 -alkyl wherein the ring in the six last mentioned radicals may be unsubstituted or may carry 1, 2, 3, 4 or 5 substituents which are independently of each other selected from halogen, cyano, nitro, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy and C 1 -C 4 -haloalkoxy; 
         R e , R f  are independently of each other selected from hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkylmethyl, C 3 -C 6 -halocycloalkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -haloalkenyl, C 2 -C 4 -alkynyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkylcarbonyl, C 1 -C 4 -haloalkylcarbonyl, C 1 -C 4 -alkylsulfonyl, C 1 -C 4 -haloalkylsulfonyl, phenyl, phenylcarbonyl, phenylsulfonyl, hetaryl, hetarylcarbonyl, hetarylsulfonyl, heterocyclyl, heterocyclylcarbonyl, heterocyclylsulfonyl, phenyl-C 1 -C 4 -alkyl, hetaryl-C 1 -C 4 -alkyl and heterocyclyl-C 1 -C 4 -alkyl wherein the ring in the twelve last mentioned radicals may be unsubstituted or may carry 1, 2, 3, 4 or 5 substituents which, independently of each other, are selected from the group consiting of halogen, cyano, nitro, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy and C 1 -C 4 -haloalkoxy; or 
         R e  and R f  together with the nitrogen atom to which they are bound form a 5- or 6-membered, saturated or unsaturated heterocycle, which may carry a further heteroatom being selected from the group consisting of O, S and N as a ring member atom and wherein the heterocycle may be unsubstituted or may carry 1, 2, 3, 4 or 5 substituents which are independently of each other selected from the group consisting of halogen, cyano, nitro, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy and C 1 -C 4 -haloalkoxy; 
         R g , R h  are independently of each other selected from hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halocycloalkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -haloalkenyl, C 2 -C 4 -alkynyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, phenyl, hetaryl, heterocyclyl, phenyl-C 1 -C 4 -alkyl, hetaryl-C 1 -C 4 -alkyl and heterocyclyl-C 1 -C 4 -alkyl wherein the ring in the six last mentioned radicals may be unsubstituted or may carry 1, 2, 3, 4 or 5 substituents which are independently of each other selected from the group consisting halogen, cyano, nitro, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy and C 1 -C 4 -haloalkoxy; 
         R i  is selected from the group consisting hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkylmethyl, C 3 -C 6 -halocycloalkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -haloalkenyl, C 2 -C 4 -alkynyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, phenyl and phenyl-C 1 -C 4 -alkyl wherein the phenyl ring in the two last mentioned radicals may be unsubstituted or may carry 1, 2, 3, 4 or 5 substituents which are independently of each other selected from the group consisting of halogen, cyano, nitro, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy and C 1 -C 4 -haloalkoxy; 
         R x  are independently of each other selected from the group consisting cyano, nitro, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -haloalkylthio, C 1 -C 4 -alkylsulfinyl, C 1 -C 4 -haloalkylsulfinyl, C 1 -C 4 -alkylsulfonyl, C 1 -C 4 -haloalkylsulfonyl, C 1 -C 10 -alkylcarbonyl, C 3 -C 6 -cycloalkyl, 5- to 7-membered heterocyclyl, phenyl, C 3 -C 6 -cycloalkoxy, 3- to 6-membered heterocyclyloxy and phenoxy, wherein the last 6 mentioned radicals may be unsubstituted or may carry 1, 2, 3, 4 or 5 radicals selected from the group consisting of halogen, cyano, nitro, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy and C 1 -C 4 -haloalkoxy; 
         R y  is selected from the group consisting halogen, cyano, nitro, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, S(O) m R d , S(O) m NR e R f , C 1 -C 4 -alkylcarbonyl, C 1 -C 4 -haloalkylcarbonyl, C 1 -C 4 -alkoxycarbonyl, C 1 -C 4 -haloalkoxycarbonyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halocycloalkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -haloalkenyl, C 2 -C 4 -alkynyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl, 5- to 7-membered heterocyclyl, hetaryl, phenyl, C 3 -C 6 -cycloalkoxy, 3- to 6-membered heterocyclyloxy, hetaryloxy and phenoxy, wherein the last 8 mentioned radicals may be unsubstituted or may carry 1, 2, 3, 4 or 5 radicals selected from the group consisting of halogen, cyano, nitro, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy and C 1 -C 4 -haloalkoxy; 
         or a salt, an N-oxide, a tautomer thereof, or the salt of the N-oxide or the tautomer. 
       
     
     
         41 . The method as claimed in  claim 40 , wherein the invertebrate pests are arthropod pests and/or nematodes. 
     
     
         42 . The method as claimed in  claim 41 , wherein the invertebrate pests are insects. 
     
     
         43 . The method as claimed in  claim 42 , wherein the invertebrate pests are insects of the order Homoptera. 
     
     
         44 . The method as claimed in  claim 40 , which is a compound of the formula I. 
     
     
         45 . The method as claimed in  claim 41 , wherein X 1  in formula I is oxygen. 
     
     
         46 . The method as claimed in  claim 40 , wherein R 1  is hydrogen, C 1 -C 10 -alkyl, C 1 -C 10 -haloalkyl, C 1 -C 4 -alkylene-CN, heterocyclyl-C 1 -C 5 -alkyl, hetaryl-C 1 -C 5 -alkyl, C 1 -C 5 -alkylen-OR a  or C 3 -C 10 -cycloalkyl-C 1 -C 5 -alkyl. 
     
     
         47 . The method as claimed in  claim 46 , wherein R 1  is hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 3 -alkylen-O—C 1 -C 3 -alkyl or C 1 -C 4 -alkylene-CN. 
     
     
         48 . The method as claimed in  claim 40 , wherein both radicals R 2  and R 3  are hydrogen. 
     
     
         49 . The method as claimed in  claim 40 , wherein Z is NR N . 
     
     
         50 . The method as claimed in  claim 49 , where R N  is selected from the group consisting of hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkylene-CN, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl, heterocyclyl-C 1 -C 4 -alkyl, where the cycloalkyl or heterocyclyl moieties in the last three mentioned radicals are unsubstituted or carry 1 or 2 radicals selected from the group consisting of halogen, CN, C 1 -C 2 -alkyl and C 1 -C 2 -haloalkyl;
 phenyl and phenyl-C 1 -C 4 -alkyl, where the phenyl moiety in the last two mentioned radicals is unsubstituted or carries 1 or 2 radicals selected from the group consisting of halogen, CN, C 1 -C 2 -alkyl, C 1 -C 2 -haloalkyl, C 1 -C 2 -alkoxy and C 1 -C 2 -haloalkoxy.   
     
     
         51 . The method as claimed in  claim 40 , wherein Z is O. 
     
     
         52 . The method as claimed in  claim 40 , wherein Z is S. 
     
     
         53 . The method as claimed in  claim 40 , wherein A is a radical A1, A2 or A3. 
     
     
         54 . The method as claimed in  claim 40 , wherein R A1 , R A2  and R A3 , independently of each other, are selected from the group consisting of hydrogen, halogen, CN, NO 2 , C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 3 -C 6 -cycloalkyl and C 3 -C 6 -halocycloalkyl. 
     
     
         55 . The method as claimed in  claim 40 , wherein A is a radical A4, A5 or A6. 
     
     
         56 . The method as claimed in  claim 55 , wherein R A4 , R A5  and R A6 , independently of each other, are selected from the group consisting of hydrogen, halogen, CN, NO 2 , C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 3 -C 6 -cycloalkyl and C 3 -C 6 -halocycloalkyl.