Pesticidally active bicyclic heterocycles with sulphur containing substituents
View Patent ↗Compounds of the formula (I), and the agrochemically acceptable salts and N-oxides of those compounds, including all stereoisomers and tautomeric forms, and wherein the substituents are as defined in claim 1 , are useful for controlling animal pests and can be prepared in a manner known per se.
1. A compound of the formula I
wherein
X is S═N—R 10 or S(O)═N—R 10 , wherein R 10 is hydrogen, nitro, cyano, C(O)R 26 , C(O)OR 27 , CONR 28 R 29 , SO 2 R 30 , CONH 2 , C(S)NH 2 ; or R 10 is C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl or C 1 -C 6 alkoxy-C 1 -C 6 alkyl;
R is hydrogen, halogen, C 1 -C 4 haloalkyl, OR 31 or S(O) n R 32 ;
X 1 is O, S or N—R 3 , wherein R 3 is C 1 -C 4 alkyl, C 1 -C 4 haloalkyl or C 1 -C 6 alkoxy-C 1 -C 6 alkyl, or X 1 is N-(4-methoxy-benzyl) or N-(propargyl);
X 2 is N, CH, C-halogen, C—CN, C—O—C 1 -C 4 alkyl, C—S—C 1 -C 4 alkyl, C—SO 2 —C 1 -C 4 alkyl, C—S-phenyl, C—SO 2 -phenyl or C—SO 2 —C 1 -C 4 halolakyl;
R 1 is C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl or C 2 -C 6 alkynyl;
R 2 is halogen, C 1 -C 4 haloalkyl, OR 31 , S(O) n R 32 , or SF 5 ;
R 4 is hydrogen or halogen;
R 26 is hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl or C 1 -C 6 alkoxy-C 1 -C 6 alkyl:
R 27 , R 28 , R 29 , R 30 independently of one another are C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl or C 1 -C 6 alkoxy-C 1 -C 6 alkyl;
R 31 and R 32 independently of one another are C 1 -C 4 alkyl or C 1 -C 4 haloalkyl;
n is 0, 1 or 2; and
agrochemically acceptable salts, stereoisomers, enantiomers, tautomers and N-oxides of those compounds.
2. A compound of formula I according to claim 1 , wherein the compound of formula I is represented by the compounds of formula I-1
wherein
X 3 is S═N—R 10 or S(O)═N—R 10 and R 10 is hydrogen, cyano or C(O)CF 3 ;
R 5 is hydrogen, halogen or C 1 -C 4 haloalkyl; R 6 is methyl, ethyl, n-propyl or i-propyl; and R 7 is halogen or C 1 -C 4 haloalkyl; and agrochemically acceptable salts, stereoisomers, enantiomers, tautomers and N-oxides of those compounds.
3. A compound of formula I according to claim 1 , wherein the compound of formula I is represented by the compounds of formula I-1a
wherein
X 3a is S(O)═N—R 10 and R 10 is C 1 -C 6 alkyl, C(O)R 26 , C(O)OR 27 , CONR 28 R 29 , SO 2 R 30 , CONH 2 or C(S)NH 2 ;
in which R 26 is hydrogen, C 1 -C 6 alkyl or C 1 -C 6 haloalkyl, and R 27 , R 28 , R 29 , R 30 independently of one another are C 1 -C 6 alkyl;
R 5a is hydrogen, halogen or C 1 -C 4 haloalkyl; R 6a is methyl, ethyl, n-propyl or i-propyl; and R 7a is halogen or C 1 -C 4 haloalkyl; and agrochemically acceptable salts, stereoisomers, enantiomers, tautomers and N-oxides of those compounds.
4. An insecticidal, acaricidal, nematicidal or molluscicidal composition, comprising an insecticidally, acaricidally, nematicidally or molluscicidally effective amount of a compound of formula I according to claim 1 and a suitable carrier or diluent therefor.