Pesticidally active heterocyclic derivatives with sulfur containing substituents

1 . A compound of formula (I)

wherein

G 1 and G 2 are, independently from each other, CH or N;

R 2 is C 1 -C 6 haloalkyl, C 1 -C 4 haloalkylsulfanyl, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 haloalkylsulfonyl, C 1 -C 6 haloalkoxy or C 1 -C 4 haloalkylsulfonyloxy;

Q is a radical of formula Qa

wherein the arrow denotes the point of attachment to the nitrogen atom of the bicyclic ring;

and wherein,

X is S, SO, or SO 2 ;

R 1 is C 1 -C 4 alkyl or C 3 -C 6 cycloalkyl-C 1 -C 4 alkyl;

R 3 , and R 4 , are, independently from each other, hydrogen, halogen, C 1 -C 4 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkyl monosubstituted by cyano, C 1 -C 6 cyanoalkyl, C 1 -C 6 cyanoalkoxy, C 3 -C 6 cyanocycloalkylC 1 -C 4 alkoxy, cyano, C 1 -C 4 alkoxy, C 1 -C 6 haloalkoxy, —N(R 7 ) 2 , or —N(R 7 )C(═O)R 8 ; and

R 7 and R 8 are, independently from each other, hydrogen, C 1 -C 4 alkyl, C 1 -C 6 haloalkyl, or C 3 -C 6 cycloalkyl;

or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide of a compound of formula I.

2 . A compound of formula I according to claim 1 , represented by the compounds of formula (I-1)

wherein R 2 , G 1 , G 2 , X, R 1 , R 3 , R 4 , R 7 and R 8 are as defined under formula I in claim 1 , or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide thereof.

3 . A compound according to claim 1 , wherein either G 1 is N and G 2 is CH, or G 1 is CH and G 2 is N.

4 . A compound according to claim 1 , wherein either both G 1 and G 2 are N, or both G 1 and G 2 are CH.

5 . A compound of formula I according to claim 1 , represented by the compounds of formula (I-3)

wherein Q is a radical of formula Qa

wherein the arrow denotes the point of attachment to the nitrogen atom of the bicyclic ring; and

R 2 , X, R 1 , R 3 , R 4 , R 7 and R 8 are as defined under formula I in claim 1 , or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide thereof.

6 . A compound of formula I according to claim 1 , represented by the compounds of formula (I-4)

wherein Q is a radical of formula Qa

wherein the arrow denotes the point of attachment to the nitrogen atom of the bicyclic ring; and

R 2 , X, R 1 , R 3 , R 4 , R 7 and R 8 are as defined under formula I in claim 1 , or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide thereof.

7 . A compound of formula I according to claim 1 , represented by the compounds of formula (I-5)

wherein Q is a radical of formula Qa

wherein the arrow denotes the point of attachment to the nitrogen atom of the bicyclic ring; and

R 2 , X, R 1 , R 3 , R 4 , R 7 and R 8 are as defined under formula I in claim 1 , or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide thereof.

8 . A compound of formula I according to claim 1 , represented by the compounds of formula (I-6)

wherein Q is a radical of formula Qa

wherein the arrow denotes the point of attachment to the nitrogen atom of the bicyclic ring; and

R 2 , X, R 1 , R 3 , R 4 , R 7 and R 8 are as defined under formula I in claim 1 , or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide thereof.

9 . A compound according to claim 1 , wherein:

X is S or SO 2 ; and

R 1 is C 1 -C 4 alkyl or cyclopropyl-C 1 -C 4 alkyl.

10 . A compound according to claim 1 , wherein:

R 2 is C 1 -C 2 haloalkyl, C 1 -C 2 haloalkylsulfanyl, C 1 -C 2 haloalkylsulfinyl, C 1 -C 2 haloalkylsulfonyl, C 1 -C 2 haloalkoxy or C 1 -C 2 haloalkylsulfonyloxy.

11 . A compound according to claim 10 , wherein R 2 is —CF 3 , —OCHF 2 , —OCF 3 or —SO 2 CF 3 .

12 . A compound according to claim 1 , wherein:

Q is Qa; and

R 4 is hydrogen and R 3 is hydrogen, bromo, methyl, trifluoromethyl, 1,1-difluoroethyl, cyclopropyl, 1-cyanocyclopropyl, 1-cyano-1-methyl-ethyl, 1-cyano-1-methyl-ethoxy, methoxy, isopropoxy, difluoromethoxy, 2,2,2-trifluoroethoxy, 2,2-difluoroethoxy, or —NHC(O)CH 3 ; or

R 3 is hydrogen and R 4 is bromo, methyl, trifluoromethyl, 1,1-difluoroethyl, cyclopropyl, 1-cyanocyclopropyl, 1-cyano-1-methyl-ethyl, 1-cyano-1-methyl-ethoxy, methoxy, isopropoxy, difluoromethoxy, 2,2,2-trifluoroethoxy, 2,2-difluoroethoxy, or —NHC(O)CH 3 .

13 . A compound of formula I according to claim 1 , selected from the group consisting of:

6-[3-ethylsulfonyl-7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-3-(trifluoromethyl)-7H-pyrrolo[3,4-b]pyridin-5-one (compound P2);

1-[3-ethylsulfonyl-2-[5-oxo-3-(trifluoromethyl)-7H-pyrrolo[3,4-b]pyridin-6-yl]imidazo[1,2-a]pyridin-7-yl]cyclopropanecarbonitrile (compound P3);

6-[3-ethylsulfonyl-6-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-3-(trifluoromethyl)-7H-pyrrolo[3,4-b]pyridin-5-one (compound P4);

1-[3-ethylsulfonyl-2-[1-oxo-6-(trifluoromethoxy)isoindolin-2-yl]imidazo[1,2-a]pyridin-7-yl]cyclopropanecarbonitrile (compound P5);

2-[3-ethylsulfonyl-6-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-6-(trifluoromethoxy)isoindolin-1-one (compound P6);

2-[3-ethylsulfonyl-7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-6-(trifluoromethoxy)isoindolin-1-one (compound P7);

6-(3-ethylsulfonyl-6-methoxy-imidazo[1,2-a]pyridin-2-yl)-3-(trifluoromethyl)-7H-pyrrolo[3,4-b]pyridin-5-one (compound P8);

6-(3-ethylsulfonyl-6-isopropoxy-imidazo[1,2-a]pyridin-2-yl)-3-(trifluoromethyl)-7H-pyrrolo[3,4-b]pyridin-5-one (compound P9);

6-[6-(difluoromethoxy)-3-ethylsulfonyl-imidazo[1,2-a]pyridin-2-yl]-3-(trifluoromethyl)-7H-pyrrolo[3,4-b]pyridin-5-one (compound P10);

6-[3-ethylsulfonyl-6-(2,2,2-trifluoroethoxy)imidazo[1,2-a]pyridin-2-yl]-3-(trifluoromethyl)-7H-pyrrolo[3,4-b]pyridin-5-one (compound P11);

6-[3-ethylsulfonyl-7-(2,2,2-trifluoroethoxy)imidazo[1,2-a]pyridin-2-yl]-3-(trifluoromethyl)-7H-pyrrolo[3,4-b]pyridin-5-one (compound P12);

6-(3-ethylsulfonyl-7-methoxy-imidazo[1,2-a]pyridin-2-yl)-3-(trifluoromethyl)-7H-pyrrolo[3,4-b]pyridin-5-one (compound P13);

1-[3-ethylsulfonyl-2-[1-oxo-6-(trifluoromethoxy)isoindolin-2-yl]imidazo[1,2-a]pyridin-6-yl]cyclopropanecarbonitrile (compound P14);

1-[3-ethylsulfonyl-2-[5-oxo-3-(trifluoromethyl)-7H-pyrrolo[3,4-b]pyridin-6-yl]imidazo[1,2-a]pyridin-6-yl]cyclopropanecarbonitrile (compound P15);

1-[3-ethylsulfonyl-2-[1-oxo-6-(trifluoromethyl)isoindolin-2-yl]imidazo[1,2-a]pyridin-6-yl]cyclopropanecarbonitrile (compound P16);

2-[6-(1,1-difluoroethyl)-3-ethylsulfonyl-imidazo[1,2-a]pyridin-2-yl]-6-(trifluoromethoxy)isoindolin-1-one (compound P17);

6-[6-(1,1-difluoroethyl)-3-ethylsulfonyl-imidazo[1,2-a]pyridin-2-yl]-3-(trifluoromethyl)-7H-pyrrolo[3,4-b]pyridin-5-one (compound P18);

6-[6-(2,2-difluoroethoxy)-3-ethylsulfonyl-imidazo[1,2-a]pyridin-2-yl]-3-(trifluoromethyl)-7H-pyrrolo[3,4-b]pyridin-5-one (compound P19);

2-[3-ethylsulfonyl-2-[5-oxo-3-(trifluoromethyl)-7H-pyrrolo[3,4-b]pyridin-6-yl]imidazo[1,2-a]pyridin-6-yl]oxy-2-methyl-propanenitrile (compound P20);

6-(6-bromo-3-ethylsulfonyl-imidazo[1,2-a]pyridin-2-yl)-3-(trifluoromethyl)-7H-pyrrolo[3,4-b]pyridin-5-one (compound P21);

6-(7-bromo-3-ethylsulfonyl-imidazo[1,2-a]pyridin-2-yl)-3-(trifluoromethyl)-7H-pyrrolo[3,4-b]pyridin-5-one (compound P22);

6-(3-ethylsulfonyl-7-methyl-imidazo[1,2-a]pyridin-2-yl)-3-(trifluoromethyl)-7H-pyrrolo[3,4-b]pyridin-5-one (compound P23);

6-(7-cyclopropyl-3-ethylsulfonyl-imidazo[1,2-a]pyridin-2-yl)-3-(trifluoromethyl)-7H-pyrrolo[3,4-b]pyridin-5-one (compound P24);

6-[7-(1,1-difluoroethyl)-3-ethylsulfonyl-imidazo[1,2-a]pyridin-2-yl]-3-(trifluoromethyl)-7H-pyrrolo[3,4-b]pyridin-5-one (compound P25);

2-[3-ethylsulfonyl-2-[1-oxo-6-(trifluoromethoxy)isoindolin-2-yl]imidazo[1,2-a]pyridin-6-yl]oxy-2-methyl-propanenitrile (compound P26);

6-(6-cyclopropyl-3-ethylsulfonyl-imidazo[1,2-a]pyridin-2-yl)-3-(trifluoromethyl)-7H-pyrrolo[3,4-b]pyridin-5-one (compound P27);

2-[3-ethylsulfonyl-7-(2,2,2-trifluoroethoxy)imidazo[1,2-a]pyridin-2-yl]-6-(trifluoromethoxy)isoindolin-1-one (compound P28);

2-(6-bromo-3-ethylsulfonyl-imidazo[1,2-a]pyridin-2-yl)-6-(trifluoromethoxy)isoindolin-1-one (compound P29);

2-(6-bromo-3-ethylsulfonyl-imidazo[1,2-a]pyridin-2-yl)-6-(trifluoromethylsulfonyl)isoindolin-1-one (compound P30);

1-[[3-ethylsulfonyl-2-[5-oxo-3-(trifluoromethyl)-7H-pyrrolo[3,4-b]pyridin-6-yl]imidazo[1,2-a]pyridin-6-yl]oxymethyl]cyclopropanecarbonitrile (compound P31);

2-[3-ethylsulfonyl-6-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-6-(trifluoromethylsulfonyl)isoindolin-1-one (compound P32);

2-[3-ethylsulfonyl-7-(2,2,2-trifluoroethoxy)imidazo[1,2-a]pyridin-2-yl]-6-(trifluoromethylsulfonyl)isoindolin-1-one (compound P33);

6-(difluoromethoxy)-2-[3-ethylsulfonyl-6-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]isoindolin-1-one (compound P34);

2-[3-ethylsulfonyl-2-[5-oxo-3-(trifluoromethyl)-7H-pyrrolo[3,4-b]pyridin-6-yl]imidazo[1,2-a]pyridin-6-yl]-2-methyl-propanenitrile (compound P35);

N-[3-ethylsulfonyl-2-[5-oxo-3-(trifluoromethyl)-7H-pyrrolo[3,4-b]pyridin-6-yl]imidazo[1,2-a]pyridin-6-yl]acetamide (compound P36);

2-[3-ethylsulfonyl-7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-6-(trifluoromethylsulfonyl)isoindolin-1-one (compound P37); and

6-[7-(2,2-difluoroethoxy)-3-ethylsulfonyl-imidazo[1,2-a]pyridin-2-yl]-3-(trifluoromethyl)-7H-pyrrolo[3,4-b]pyridin-5-one (compound P38).

14 . A composition comprising an insecticidally, acaricidally, nematicidally or molluscicidally effective amount of a compound of formula (I), or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide thereof, as defined in claim 1 and, optionally, an auxiliary or diluent.

15 . A method of combating and controlling insects, acarines, nematodes or molluscs which comprises applying to a pest, to a locus of a pest, or to a plant susceptible to attack by a pest an insecticidally, acaricidally, nematicidally or molluscicidally effective amount of a compound of formula (I), or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide thereof, as defined in claim 1 .

16 . A method for the protection of plant propagation material from the attack by insects, acarines, nematodes or molluscs, which comprises treating the propagation material or the site, where the propagation material is planted, with a composition according to claim 14 .

17 . A method of combating and controlling insects, acarines, nematodes or molluscs which comprises applying to a pest, to a locus of a pest, or to a plant susceptible to attack by a pest in insecticidally, acaricidally, nematicidally or molluscicidally effective amount of a compound of formula (I), or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide thereof, as defined in claim 1 , or a composition thereof.

18 . The compound according to claim 3 , wherein G 1 is N and G 2 is CH.

19 . The compound according to claim 9 , wherein:

X is S02; and

R 1 is ethyl or cyclopropylmethyl.

20 . The compound according to claim 10 , wherein R 2 is —CF 3 , —CF 2 CF 3 , —SCF 3 , —SOCF 3 , —SO 2 CF 3 , —OCHF 2 , —OCF 3 or —OSO 2 CF 3 .

21 . The compound according to claim 12 , wherein:

R 4 is hydrogen and R 3 is bromo, trifluoromethyl, 1,1-difluoroethyl, cyclopropyl, 1-cyanocyclopropyl, 1-cyano-1-methyl-ethyl, 1-cyano-1-methyl-ethoxy, methoxy, isopropoxy, difluoromethoxy, 2,2,2-trifluoroethoxy, 2,2-difluoroethoxy, or —NHC(O)CH 3 ; or

R 3 is hydrogen and R 4 bromo, methyl, trifluoromethyl, 1,1-difluoroethyl, cyclopropyl, 1-cyanocyclopropyl, methoxy, or 2,2,2-trifluoroethoxy.