Pesticidally active pyridyl- and pyrimidyl- substituted pyrazole derivatives

1. A compound of formula I

wherein

X 1 is nitrogen or CR 1 ;

G 1 is nitrogen or CR 2 ;

G 2 is nitrogen or CR 3 ;

or G 1 -G 2 together is —S—, —O—, —NH—, or N—CH 3 ;

A 1 is oxygen, S(O)n 1 , S(O)(═NR 4 ), C═O, NR 5 , CR 6 R 7 , —CR 8 CR 9 — or a direct bond;

A 2 is oxygen, S(O)n 2 , NR 10 , C═O or CR 11 R 12 ;

A 3 is oxygen, NR 13 , CR 14 R 15 or —CR 16 CR 17 —;

or A 2 -A 3 together represents a group —CR 18 ═CR 19 —;

with the provisos that;

a) not more than 1 substituent A can be oxygen or sulfur;

b) not more than 2 substituents A can be nitrogen;

c) 2 substituents A as nitrogen can be adjacent to each other or separated by a sulfur or carbon substituent;

R 1 is hydrogen or halogen;

R 2 and R 3 , independently from each other, are hydrogen, halogen, C 1 -C 3 alkyl or C 1 -C 3 haloalkyl;

R 4 , R 5 , R 10 and R 13 , independently from each other, are hydrogen, cyano, C 1 -C 2 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 2 haloalkyl, C(O)C 1 -C 3 alkyl, (CO)OC 1 -C 3 alkyl, SO 2 NHC 1 -C 3 alkyl, SO 2 N(C 1 -C 3 alkyl), SO 2 C 1 -C 3 alkyl, SO 2 -phenyl, wherein the said phenyl can be mono- or polysubstituted on the phenyl ring by substituents selected from the group consisting of C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, halogen, cyano and nitro;

R 6 , R 7 , R 8 , R 9 , R 11 , R 12 , R 14 , R 15 , R 16 and R 17 , independently from each other, are hydrogen, halogen, nitro, cyano, hydroxy, CHO, 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 4 alkoxy, C 1 -C 4 alkoxy-C 1 -C 4 alkoxy-C 1 -C 4 alkyl, C 1 -C 4 haloalkoxy, C 1 -C 4 alkylthio, C 1 -C 4 haloalkylthio, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 haloalkylsulfonyl, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 alkylsulfonyl-C 1 -C 4 alkyl, C 1 -C 4 alkylsulfoximino-C 1 -C 4 alkyl, C 1 -C 4 alkylamino, C 2 -C 4 dialkylamino, C 3 -C 6 cycloalkylamino, C 1 -C 6 alkyl-C 3 -C 6 cycloalkylamino, C 2 -C 4 alkylcarbonyl, C 2 -C 6 alkoxycarbonyl, C 2 -C 6 alkylaminocarbonyl, C 3 -C 6 dialkylaminocarbonyl, C 2 -C 6 alkoxycarbonyloxy, C 2 -C 6 alkylaminocarbonyloxy, C 3 -C 6 dialkylaminocarbonyloxy, C 1 -C 4 alkoxyimino-C 1 -C 4 alkyl, —CONHSO 2 —C 1 -C 6 -alkyl, —CONHSO 2 N(C 1 -C 6 -alkyl) 2 , or are a three- to ten-membered, monocyclic or fused bicyclic ring system which may be aromatic, partially saturated or fully saturated, said three- to ten-membered, monocyclic or fused bicyclic ring system can be substituted by one to three substituents independently selected from the group consisting of C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 3 -C 6 cycloalkyl, C 1 -C 4 haloalkyl, C 2 -C 4 haloalkenyl, C 2 -C 4 haloalkynyl, C 3 -C 6 halocycloalkyl, halogen, cyano, nitro, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 alkylsulfoximino, C 1 -C 4 alkylamino, C 2 -C 6 dialkylamino, C 3 -C 6 cycloalkylamino, C 1 -C 4 alkyl-C 3 -C 6 cycloalkylamino, C 2 -C 4 alkylcarbonyl, C 2 -C 6 alkoxycarbonyl, C 2 -C 6 alkylaminocarbonyl, and C 2 -C 8 dialkylaminocarbonyl;

R 18 and R 19 , independently from each other, are hydrogen, halogen, nitro, cyano, hydroxy, CHO, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 alkoxy, 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 4 alkylsulfonyl, C 1 -C 4 alkylsulfonyl-C 1 -C 4 alkyl, C 2 -C 4 alkylcarbonyl, C 2 -C 6 alkoxycarbonyl, C 2 -C 6 alkylaminocarbonyl, C 3 -C 6 dialkylaminocarbonyl, C 2 -C 6 alkoxycarbonyloxy, C 2 -C 6 alkylaminocarbonyloxy, C 3 -C 6 dialkylaminocarbonyloxy, C 1 -C 4 alkoxyimino-C 1 -C 4 alkyl, —CONHSO 2 —C 1 -C 6 -alkyl, —CONHSO 2 N(C 1 -C 6 -alkyl) 2 , or are a three- to ten-membered, monocyclic or fused bicyclic ring system which may be aromatic, partially saturated or fully saturated, said three- to ten-membered, monocyclic or fused bicyclic ring system can be substituted by one to three substituents independently selected from the group consisting of C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 3 -C 6 cycloalkyl, C 1 -C 4 haloalkyl, C 2 -C 4 haloalkenyl, C 2 -C 4 haloalkynyl, C 3 -C 6 halocycloalkyl, halogen, cyano, nitro, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 alkylsulfoximino, C 1 -C 4 alkylamino, C 2 -C 6 dialkylamino, C 3 -C 6 cycloalkylamino, C 1 -C 4 alkyl-C 3 -C 6 cycloalkylamino, C 2 -C 4 alkylcarbonyl, C 2 -C 6 alkoxycarbonyl, C 2 -C 6 alkylaminocarbonyl, and C 2 -C 8 dialkylaminocarbonyl;

Z 1 is oxygen, NOR 20 , NR 21 , N—NR 22 R 23 , or N—N(R 24 )SO 2 (R 25 ),

R 20 , R 21 , R 22 and R 25 independently from each other, are hydrogen, 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 alkyl-C 3 -C 6 cycloalkylamino, C 2 -C 4 alkylcarbonyl, C 2 -C 6 alkoxycarbonyl, C 2 -C 6 alkylaminocarbonyl, C 3 -C 6 dialkylaminocarbonyl, —CONHSO 2 —C 1 -C 6 -alkyl, —CONHSO 2 N(C 1 -C 6 -alkyl) 2 or are a five- to ten-membered monocyclic or fused bicyclic ring system which may be aromatic, saturated or partially saturated and may contain 1 to 4 heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur, where the ring system is attached directly or via a C 1 -C 4 alkylene, C 2 -C 4 alkenyl-C 1 -C 4 alkylene, C 2 -C 4 alkynyl-C 1 -C 4 alkylene, —NH—C 1 -C 4 alkylene, —N(C 1 -C 4 alkyl)C 1 -C 4 alkylene,

SO—C 1 -C 4 alkylene, SO—C 1 -C 4 alkylene, —SO 2 —C 1 -C 4 alkylene or O— C 1 -C 4 alkylene group to the heteroatom substituent, and where each ring system may not contain more than two oxygen atoms and not more than two sulfur atoms and the ring system for its part may be mono-, di- or trisubstituted by C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl, C 2 -C 6 haloalkynyl, C 1 -C 6 alkoxy, hydroxyl, C 1 -C 6 haloalkoxy, C 3 -C 6 alkenyloxy, C 3 -C 6 alkynyloxy, mercapto, C 1 -C 6 alkylthio, C 1 -C 6 haloalkylthio, C 3 -C 6 alkenylthio, C 3 -C 6 haloalkenylthio, C 3 -C 6 alkynylthio, C 2 -C 5 alkoxyalkylthio, C 3 -C 5 acetylalkylthio, C 3 -C 6 alkoxycarbonylalkylthio, C 2 -C 4 cyanoalkylthio, C 1 -C 6 alkylsulfinyl, C 1 -C 6 haloalkylsulfinyl, C 1 -C 6 alkylsulfonyl, C 1 -C 6 haloalkylsulfonyl, aminosulfonyl, C 1 -C 2 alkylaminosulfonyl, di(C 1 -C 2 alkyl)aminosulfonyl, di(C 1 -C 4 alkyl)amino, halogen, cyano, nitro, phenyl and benzylthio, said phenyl and benzylthio can be mono- or polysubstituted on the phenyl ring by substituents selected from the group consisting of C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, halogen, cyano and nitro, and where the substituents on the nitrogen in the heterocyclic ring are different from halogen;

R 23 and R 24 are hydrogen or C 1 -C 3 alkyl;

Q is a ring system Q 1

wherein R 26 is hydrogen, C 1 -C 4 alkyl, halogen, C 1 -C 4 haloalkyl, cyano, C 1 -C 4 alkoxy, hydroxyl, amino, C 1 -C 4 alkylamino, di-(C 1 -C 4 alkyl)amino, C 1 -C 4 alkylthio or nitro;

or R 26 is a three- to four- membered ring system which can be partially saturated or fully saturated and can contain one heteroatom selected form the group consisting of nitrogen, oxygen and sulfur; said three- to four- membered ring system can be mono- to polysubstituted by substituents independently selected from the group consisting of halogen, methyl and trifluoromethyl;

m 1 is 0 or 1; and

n 1 and n 2 , independently from each other, are 0, 1 or 2; and agrochemically acceptable salts/enantiomers/tautomers/N-oxides of those compounds.

2. A compound of formula I according to claim 1 , wherein

X 1 is CH or C—F;

A 1 is oxygen, S(O)n 1 , C═O, NR 5 , CR 6 R 7 , —CR 8 CR 9 — or a direct bond;

A 2 is CR 11 R 12 ; and

A 3 is CR 14 R 15 or —CR 16 CR 17 —; and

R 26 is hydrogen, C 1 -C 4 alkyl, halogen, C 1 -C 4 haloalkyl, cyano, C 1 -C 4 alkoxy, hydroxyl, amino, C 1 -C 4 alkylamino, di-(C 1 -C 4 alkyl)amino, C 1 -C 4 alkylthio or nitro.

3. A compound of formula I according to claim 1 , wherein

X 1 is CH or C—F;

G 1 is CR 2 ;

G 2 is CR 3 ; or

G 1 -G 2 together is —S—, —O—;

A 1 is oxygen, S(O)n 1 , C═O, NR 5 , CR 6 R 7 , —CR 8 CR 9 — or a direct bond;

A 2 is CR 11 R 12 ;

A 3 is CR 14 R 15 or —CR 16 CR 17 —; and

R 26 is hydrogen, C 1 -C 4 alkyl, halogen, C 1 -C 4 haloalkyl, cyano, C 1 -C 4 alkoxy, hydroxyl, amino, C 1 -C 4 alkylamino, di-(C 1 -C 4 alkyl)amino, C 1 -C 4 alkylthio or nitro.

4. A compound of formula I according to claim 1 , wherein

X 1 is CH;

G 1 is CH;

G 2 is CH; or

G 1 -G 2 together is —S—;

A 1 is oxygen, S(O)n 1 , C═O, NR 5 , CR 6 R 7 , —CR 8 CR 9 — or a direct bond;

A 2 is CR 11 R 12 ;

A 3 is CR 14 R 15 or —CR 16 CR 17 —; and

R 26 is hydrogen, C 1 -C 4 alkyl, halogen, C 1 -C 4 haloalkyl, cyano, C 1 -C 4 alkoxy, hydroxyl, amino, C 1 -C 4 alkylamino, di-(C 1 -C 4 alkyl)amino, C 1 -C 4 alkylthio or nitro.

5. A compound of formula I according to claim 1 , wherein

X 1 is CH;

G 1 is CH;

G 2 is CH; or

G 1 -G 2 together is —S—;

A 1 is oxygen, S(O)n 1 , C═O, NR 5 , CR 6 R 7 , —CR 8 CR 9 — or a direct bond;

A 2 is CR 11 R 12 ;

A 3 is CR 14 R 15 or —CR 16 CR 17 —;

R 26 is hydrogen, C 1 -C 4 alkyl, halogen, C 1 -C 4 haloalkyl, cyano, C 1 -C 4 alkoxy, hydroxyl, amino, C 1 -C 4 alkylamino, di-(C 1 -C 4 alkyl)amino, C 1 -C 4 alkylthio or nitro; and

Z 1 is NOR 20 , N—NR 22 R 23 , or N—N(R 24 )SO 2 (R 25 ).

6. A compound of formula I according to claim 1 , wherein

X 1 is CH;

G 1 is CH;

G 2 is CH; or

G 1 -G 2 together is —S—;

A 1 is oxygen, S(O)n 1 , C═O, NR 5 , CR 6 R 7 , —CR 8 CR 9 — or a direct bond;

A 2 is CH 2 ;

A 3 is CH 2 or —CH 2 CH 2 —;

R 26 is hydrogen, C 1 -C 4 alkyl, halogen, C 1 -C 4 haloalkyl, cyano, C 1 -C 4 alkoxy, hydroxyl, amino, C 1 -C 4 alkylamino, di-(C 1 -C 4 alkyl)amino, C 1 -C 4 alkylthio or nitro; and

Z 1 is NOR 20 , N—NR 22 R 23 , or N—N(R 24 )SO 2 (R 25 ).

7. A compound of formula I according to claim 1 , wherein

X 1 is CH;

G 1 is CH;

G 2 is CH;

A 1 is oxygen, S(O)n 1 , C═O, NR 5 , CH 2 , —CH 2 CH 2 — or a direct bond;

A 2 is CH 2 ;

A 3 is CH 2 or —CH 2 CH 2 —;

R 26 is hydrogen, C 1 -C 4 alkyl, halogen, C 1 -C 4 haloalkyl, cyano, C 1 -C 4 alkoxy, hydroxyl, amino, C 1 -C 4 alkylamino, di-(C 1 -C 4 alkyl)amino, C 1 -C 4 alkylthio or nitro; and

Z 1 is NOR 20 , N—NR 22 R 23 , or N—N(R 24 )SO 2 (R 25 ).

8. A compound of formula I according to claim 1 , wherein

X 1 is CH;

G 1 is CH;

G 2 is CH; or

G 1 -G 2 together is —S—;

A 1 is oxygen, S(O)n 1 , C═O, NR 5 , CH 2 , —CH 2 CH 2 — or a direct bond;

A 2 is CH 2 ;

A 3 is CH 2 ,

R 26 is hydrogen, C 1 -C 4 alkyl, halogen, C 1 -C 4 haloalkyl, cyano, C 1 -C 4 alkoxy, hydroxyl, amino, C 1 -C 4 alkylamino, di-(C 1 -C 4 alkyl)amino, C 1 -C 4 alkylthio or nitro; and

Z 1 is NOR 20 .

9. A compound of formula I according to claim 1 , wherein

X 1 is CH;

G 1 is CH;

G 2 is CH;

A 1 is oxygen, S(O)n 1 , NR 5 , CH 2 or a direct bond;

A 2 is CH 2 ;

A 3 is CH 2 ;

R 26 is hydrogen, C 1 -C 4 alkyl, halogen, C 1 -C 4 haloalkyl, cyano, C 1 -C 4 alkoxy, hydroxyl, amino, C 1 -C 4 alkylamino, di-(C 1 -C 4 alkyl)amino, C 1 -C 4 alkylthio or nitro; and

Z 1 is NOR 20 , N—NR 22 R 23 , or N—N(R 24 )SO 2 (R 25 ).

10. A pesticidal composition, which comprises at least one compound of formula I according to claim 1 or, where appropriate, a tautomer thereof, in each case in free form or in agrochemically utilizable salt form, as active ingredient and at least one auxiliary.

11. A method for controlling pests, which comprises applying a composition according to claim 5 to the pests or their environment with the exception of a method for treatment of a human or animal body by surgery or therapy and diagnostic methods practised on the human or animal body.

12. A method for the protection of plant propagation material from attack by pests, which comprises treating the propagation material or a site, where the propagation material is planted, with a composition according to claim 10 .

13. Plant propagation material treated in accordance with the method described in claim 12 .