Pesticidally active tetracyclic derivatives with sulfur containing substituents
Compounds of formula I, wherein the substituents are as defined in claim 1 , and the agrochemically acceptable salts, stereoisomers, enantiomers, tautomers and N-oxides of those compounds, can be used as insecticides and can be prepared in a manner known per se.
1. A compound of formula I,
wherein
A is CH or N;
X is S, SO or SO 2 ;
R 1 is C 1 -C 4 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl, C 1 -C 4 haloalkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkyl-C 1 -C 4 alkyl; or is C 3 -C 6 cycloalkyl mono- or polysubstituted by substituents selected from the group consisting of halogen, cyano, C 1 -C 4 haloalkyl and C 1 -C 4 alkyl; or is C 3 -C 6 cycloalkyl-C 1 -C 4 alkyl mono- or polysubstituted by substituents selected from the group consisting of halogen, cyano, C 1 -C 4 haloalkyl and C 1 -C 4 alkyl;
R 2 is hydrogen, halogen, C 1 -C 4 haloalkylsulfanyl, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 haloalkylsulfonyl, O(C 1 -C 4 haloalkyl), —SF 5 , C(O)C 1 -C 4 haloalkyl, cyano, C 1 -C 6 haloalkyl or is C 1 -C 6 haloalkyl substituted by one or two substituents selected from the group consisting of hydroxyl, methoxy and cyano; or is C 3 -C 6 cycloalkyl which can be mono- or polysubstituted by substituents selected from the group consisting of halogen, cyano, C 1 -C 4 haloalkyl and C 1 -C 4 alkyl;
G 1 is N or CR 4 ;
G 2 is N or CR 5 , with the proviso that when G 1 is N, G 2 is CR 5 ;
R 6 is hydrogen, halogen or C 1 -C 4 alkyl;
R 4 and R 5 , independently from each other, are hydrogen, halogen, cyano, nitro, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, or are C 3 -C 6 cycloalkyl which can be mono- or polysubstituted by R 8 ; or are C 3 -C 6 cycloalkyl-C 1 -C 4 alkyl which can be mono- or polysubstituted by R 9 ; or
R 4 and R 5 , independently from each other, are C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl, C 2 -C 6 haloalkynyl, C 1 -C 6 haloalkoxy, C 1 -C 6 alkoxy, C 1 -C 6 alkylsulfanyl, C 1 -C 4 alkylsulfonyl, C 1 -C 6 alkylsulfinyl C 1 -C 6 haloalkylsulfanyl, C 1 -C 4 haloalkylsulfonyl, C 1 -C 6 haloalkylsulfinyl or hydroxyl;
R 8 and R 9 , independently from each other, are halogen, nitro, cyano, C 1 -C 4 haloalkoxy, C 1 -C 4 alkoxy C 1 -C 4 alkyl or C 1 -C 4 haloalkyl; and
L 1 , L 2 , L 3 and L 4 form together with the two carbon atoms to which L 1 and L 4 are attached, an aromatic, partially saturated carbocyclic or heterocyclic ring system;
wherein
L 1 is nitrogen, S(O)n, oxygen, N—R 10a or C(R 10a ) m ;
L 2 is nitrogen, S(O)n, oxygen, N—R 10b , or C(R 10b ) m ;
L 3 is nitrogen, S(O)n, oxygen, N—R 10c , or C(R 10c ) m ;
L 4 is nitrogen, S(O)n, oxygen, a direct bond, N—R 10d or C(R 10d ) m ; with the provisos that no more than 2 substituents selected from L 1 , L 2 , L 3 and L 4 can be oxygen or sulfur;
and if two L groups are oxygen, they are not adjacent to each other; and no more than three L groups can be nitrogen;
n is 0 to 2;
m is 1 or 2;
R 10a , R 10b , R 10c , and R 10d , independently from each other, are hydrogen, halogen, nitro, cyano, amino, hydroxyl, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 6 cycloalkyl, C 1 -C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 2 -C 6 haloalkynyl, C 3 -C 6 halocycloalkyl, C 1 -C 6 alkoxy, C 1 -C 4 alkoxy C 1 -C 4 alkyl, C 1 -C 6 haloalkoxy, C 1 -C 6 alkylthio, C 1 -C 6 alkylsulfinyl, C 1 -C 6 alkylsulfonyl, C 1 -C 6 haloalkylthio, C 1 -C 6 haloalkylsulfinyl, C 1 -C 6 haloalkylsulfonyl, C 2 -C 6 alkylcarbonyl, C 2 -C 6 alkoxycarbonyl, C 2 -C 6 haloalkylcarbonyl, C 2 -C 6 haloalkoxycarbonyl, (C 1 -C 6 alkyl)NH, (C 1 -C 6 alkyl) 2 N, (C 1 -C 6 cycloalkyl)NH, (C 1 -C 6 cycloalkyl) 2 N, C 1 -C 6 alkylcarbonylamino, C 1 -C 6 cycloalkylcarbonylamino or —SF 5 ;
additionally one of R 10a , R 10b , R 10c and R 10d can be oxo; or
R 10a , R 10b , R 10c , and R 10d , independently from each other, are C 3 -C 6 cycloalkyl mono- or polysubstituted by substituents selected from the group consisting of C 1 -C 4 haloalkyl, C 1 -C 4 alkyl and cyano; or
R 10a , R 10b , R 10c , and R 10d , independently from each other, are phenyl which can be mono- or polysubstituted by substituents selected from the group consisting of halogen, C 1 -C 4 haloalkyl, C 1 -C 4 alkyl, C 1 -C 4 alkoxy and cyano; or an agrochemically acceptable salt, a stereoisomer, an enantiomer, a tautomer and an N-oxide of those compounds.
2. A compound of formula I according to claim 1 represented by the compounds of formula I-1
wherein the substituents X, A, R 1 , R 2 , R 6 , L 1 , L 2 , L 3 and L 4 are as defined under formula I in claim 1 .
3. A compound of formula I-1 according to claim 2 , wherein
A is C—H or N;
R 1 is C 1 -C 4 alkyl, 03-C 6 cycloalkyl-C 1 -C 4 alkyl or C 3 -C 6 cycloalkyl;
R 2 is halogen, C 1 -C 4 haloalkylsulfanyl, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 haloalkylsulfonyl, C 1 -C 4 haloalkoxy, C 1 -C 4 haloalkyl, cyano or is C 3 -C 6 cycloalkyl which can be mono- or polysubstituted by substituents selected from the group consisting of halogen, cyano and C 1 -C 4 alkyl;
X, R 6 , L 1 , L 2 , L 3 and L 4 are as defined under formula I in claim 1 ; and
R 10a , R 10b , R 10c , and R 10d , independently from each other, are hydrogen, halogen, nitro, cyano, hydroxyl, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkyl-C 1 -C 4 cycloalkyl, C 1 -C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 2 -C 6 haloalkynyl, C 3 -C 6 halocycloalkyl, C 3 -C 6 cyclohaloalkyl-C 1 -C 4 cycloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 haloalkylthio, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 haloalkylsulfonyl, C 2 -C 4 alkylcarbonyl, C 2 -C 6 alkoxycarbonyl, —SF 5 ; additionally one of R 10a , R 10b , R 10c and R 10d can be oxo.
4. A compound of formula I according to claim 1 represented by the compounds of formula I-2
wherein the substituents X, A, R 1 , R 2 , R 6 , L 1 , L 2 , L 3 and L 4 are as defined under formula I in claim 1 .
5. A compound of formula I-2 according to claim 4 , wherein
A is C—H or N;
R 1 is C 1 -C 4 alkyl, C 3 -C 6 cycloalkyl-C 1 -C 4 alkyl or C 3 -C 6 cycloalkyl;
R 2 is halogen, C 1 -C 4 haloalkylsulfanyl, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 haloalkylsulfonyl, C 1 -C 4 haloalkoxy, C 1 -C 4 haloalkyl, cyano or is C 3 -C 6 cycloalkyl which can be mono- or polysubstituted by substituents selected from the group consisting of halogen, cyano and C 1 -C 4 alkyl;
X, R 6 , L 1 , L 2 , L 3 and L 4 are as defined under formula I in claim 1 ; and
R 10a , R 10b , R 10c , and R 10d , independently from each other, are hydrogen, halogen, nitro, cyano, hydroxyl, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkyl-C 1 -C 4 cycloalkyl, C 1 -C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 2 -C 6 haloalkynyl, C 3 -C 6 halocycloalkyl, C 3 -C 6 cyclohaloalkyl-C 1 -C 4 cycloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 haloalkylthio, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 haloalkylsulfonyl, C 2 -C 4 alkylcarbonyl, C 2 -C 6 alkoxycarbonyl, —SF 5 ; additionally one of R 10a , R 10b , R 10c and R 10d can be oxo.
6. A compound of formula I according to claim 1 represented by the compounds of formula I-3;
wherein the substituents X, A, R 1 , R 2 , L 1 , L 2 , L 3 and L 4 are as defined under formula I in claim 1 .
7. A compound of formula I-3 according to claim 6 , wherein
A is C—H or N;
R 1 is C 1 -C 4 alkyl, C 3 -C 6 cycloalkyl-C 1 -C 4 alkyl or C 3 -C 6 cycloalkyl;
R 2 is halogen, C 1 -C 4 haloalkylsulfanyl, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 haloalkylsulfonyl, C 1 -C 4 haloalkoxy, C 1 -C 4 haloalkyl, cyano or is C 3 -C 6 cycloalkyl which can be mono- or polysubstituted by substituents selected from the group consisting of halogen, cyano and C 1 -C 4 alkyl;
X, R 6 , L 1 , L 2 , L 3 and L 4 are as defined under formula I in claim 1 ; and
R 10a , R 10b , R 10c , and R 10d , independently from each other, are hydrogen, halogen, nitro, cyano, hydroxyl, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkyl-C 1 -C 4 cycloalkyl, C 1 -C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 2 -C 6 haloalkynyl, C 3 -C 6 halocycloalkyl, C 3 -C 6 cyclohaloalkyl-C 1 -C 4 cycloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 haloalkylthio, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 haloalkylsulfonyl, C 2 -C 4 alkylcarbonyl, C 2 -C 6 alkoxycarbonyl, —SF 5 ; additionally one of R 10a , R 10b , R 10c and R 10d can be oxo.
8. A compound of formula I-1a
wherein J is selected from the group J 1 -J 27
and A, R 1 , R 2 , X, R 10a , R 10b , R 10c , R 10d , are as defined in claim 3 , and X 2 is oxygen or S(O)n 1 , wherein n 1 is 0, 1, or 2, and R 10e is hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, 03-C 6 cycloalkyl or C 3 -C 6 halocycloalkyl.
9. A compound formula I-2a
wherein J is selected from the group J 1 -J 27
and A, R 1 , R 2 , X, R 10a , R 10b , R 10c , R 10d , are as defined in claim 5 , and X 2 is oxygen or S(O)n 1 , wherein n 1 is 0, 1, or 2, and R 10e is hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkyl or C 3 -C 6 halocycloalkyl.
10. A compound of formula I-3a
wherein J is selected from the group consisting of
and A, R 1 , R 2 , X, R 10a , R 10b , R 10c , R 10d , are as defined in claim 7 , and X 2 is oxygen or S(O)n 1 , wherein n 1 is 0, 1, or 2, and R 10e is hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkyl or C 3 -C 6 halocycloalkyl.
11. A compound of formula I according to claim 1 , wherein
A is CH or N;
X is SO 2 ;
R 1 is C 1 -C 4 alkyl;
R 2 is C 1 -C 4 haloalkyl or C 1 -C 4 haloalkylsufanyl;
G 1 is N or CR 4 ; wherein R 4 is hydrogen;
G 2 is CR 5 , wherein R 5 is hydrogen;
R 6 is hydrogen;
L 1 , L 2 , L 3 and L 4 form together with the two carbon atoms to which L 1 and L 4 are attached, a phenyl group or form an imidiazolyl group which can be mono- or di-substituted by substituents selected from the group consisting of C 1 -C 4 alkyl and C 1 -C 4 haloalkyl.
12. A pesticidal composition, which comprises at least one compound of formula I according to claim 1 or a tautomer thereof, in each case in free form or in agrochemically utilizable salt form, as active ingredient and at least one auxiliary.
13. A method for controlling pests, which comprises applying a composition according to claim 12 to the pests or their environment with the exception of a method for treatment of the human or animal body by surgery or therapy and diagnostic methods practised on the human or animal body.
14. A method for the protection of plant propagation material from the attack by pests, which comprises treating the propagation material or the site, where the propagation material is planted, with a composition according to claim 12 .