Pesticidally active 1,2,4-triazole derivatives with sulphur containing substituents

1. A compound of formula I

wherein

G 1 is nitrogen or CR 2 ;

G 2 is nitrogen or CR 3 ;

G 3 is nitrogen or CR 4 ;

G 4 is nitrogen or CR 5 ;

G 5 is nitrogen or CR 6 , with the proviso that not more than 2 nitrogens as G may follow consecutively;

R 2 , R 3 , R 4 , R 5 or R 6 are, independently from each other, hydrogen, halogen, C 1 -C 4 haloalkyl, C 1 -C 4 haloalkyl substituted by one or two hydroxy, C 1 -C 4 haloalkyl substituted by one or two methoxy, C 1 -C 4 haloalkyl substituted by one or two cyano; or

R 2 , R 3 , R 4 , R 5 or R 6 are, independently from each other, C 1 -C 4 haloalkylsulfanyl, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 haloalkylsulfonyl, C 1 -C 4 haloalkoxy, SF 5 , phenylcarbonylthio, cyano, mercapto, C 1 -C 4 alkoxycarbonyl, C 1 -C 4 alkylcarbonyl or —C(O)C 1 -C 4 haloalkyl; or

R 2 , R 3 , R 4 , R 5 or R 6 are, independently from each other, 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;

or two adjacent R i, wherein R i is selected from R 2 , R 3 , R 4 , R 5 and R 6 , taken together may form a fragment —OCH 2 O— or —OCF 2 O—,

R 8 is hydrogen, C 1 -C 4 alkyl or C 1 -C 4 haloalkyl;

R 7 is a radical selected from the group consisting of formula Q1 and Q2

wherein the arrow denotes the point of attachment to the triazole ring;

and wherein A represents CH or N;

Q is phenyl which can be mono- or polysubstituted by substituents selected from the group consisting of halogen, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 haloalkoxy, C 1 -C 4 alkoxy, C 1 -C 4 haloalkylsulfanyl, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 haloalkylsulfonyl and —C(O)C 1 -C 4 haloalkyl; or

Q is a five- to ten-membered monocyclic or fused bicyclic ring system linked via a carbon atom to the ring which contains the group A, said ring system can be aromatic, partially saturated or fully saturated and contains 1 to 4 hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur, it not being possible for each ring system to contain more than 2 oxygen atoms and more than 2 sulfur atoms, said five-to ten-membered ring system can be mono- to polysubstituted by substituents independently selected from the group consisting of halogen, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 haloalkoxy, C 1 -C 4 alkoxy, C 1 -C 4 alkylsulfanyl, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, —C(O)C 1 -C 4 alkyl, C 1 -C 4 haloalkylsulfanyl, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 haloalkylsulfonyl and —C(O)C 1 -C 4 haloalkyl; or

Q is a five- to six-membered, aromatic, partially saturated or fully saturated ring system linked via a nitrogen atom to the ring which contains the group A, said ring system can be mono- or polysubstituted by substituents selected from the group consisting of halogen, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 haloalkoxy, C 1 -C 4 alkoxy, C 1 -C 4 alkylsulfanyl, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, —C(O)C 1 -C 4 alkyl, C 1 -C 4 haloalkylsulfanyl, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 haloalkylsulfonyl and —C(O)C 1 -C 4 haloalkyl; and said ring system contains 1, 2 or 3 heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur, where said ring system may not contain more than one oxygen atom and not more than one sulfur atom; or

Q is C 3 -C 6 cycloalkyl, or C 3 -C 6 cycloalkyl mono- or polysubstituted by substituents selected from the group consisting of halogen, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 3 -C 6 cycloalkyl and phenyl, wherein said phenyl can be mono- or polysubstituted by substituents selected from the group consisting of halogen, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 haloalkoxy, C 1 -C 4 alkoxy, C 1 -C 4 haloalkylsulfanyl, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 haloalkylsulfonyl and —C(O)C 1 -C 4 haloalkyl; or

Q is C 2 -C 6 alkenyl, or C 2 -C 6 alkenyl mono- or polysubstituted by substituents selected from the group consisting of halogen, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 3 -C 6 cycloalkyl and phenyl, wherein said phenyl can be mono- or polysubstituted by substituents selected from the group consisting of halogen, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 haloalkoxy, C 1 -C 4 alkoxy, C 1 -C 4 haloalkylsulfanyl, C 1 -C 4 halo-alkylsulfinyl, C 1 -C 4 haloalkylsulfonyl and —C(O)C 1 -C 4 haloalkyl; or

Q is C 2 -C 6 alkynyl, or C 2 -C 6 alkynyl mono- or polysubstituted by substituents selected from the group consisting of halogen, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 3 -C 6 cycloalkyl, tri(C 1 -C 4 alkyl)silyl and phenyl, wherein said phenyl can be mono- or polysubstituted by substituents selected from the group consisting of halogen, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 haloalkoxy, C 1 -C 4 alkoxy, C 1 -C 4 haloalkylsulfanyl, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 haloalkylsulfonyl and —C(O)C 1 -C 4 haloalkyl; or

Q is C 1 -C 6 haloalkylsulfanyl, C 1 -C 6 haloalkylsulfinyl, C 1 -C 6 haloalkylsulfonyl, C 1 -C 6 haloalkoxy, —C(O)C 1 -C 4 haloalkyl, C 1 -C 6 alkylsulfanyl, C 1 -C 6 alkylsulfinyl, or C 1 -C 6 alkylsulfonyl;

X is S, SO or SO 2 ; and

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

R 1 is C 3 -C 6 cycloalkyl mono- or polysubstituted by substituents selected from the group consisting of halogen, cyano and C 1 -C 4 alkyl; or

R 1 is C 3 -C 6 cycloalkyl-C 1 -C 4 alkyl mono- or polysubstituted by substituents selected from the group consisting of halogen, cyano and C 1 -C 4 alkyl; or

R 1 is C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl or C 2 -C 6 alkynyl;

and agrochemically acceptable salts, stereoisomers, enantiomers, tautomers and N -oxides of the compounds of formula I.

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

Q is selected from the group consisting of the following heterocyclic groups:

pyrrolyl; pyrazolyl; isoxazolyl; furanyl; thienyl; imidazolyl; oxazolyl; thiazolyl;

isothiazolyl; triazolyl; oxadiazolyl; thiadiazolyl; tetrazolyl; furyl; pyridyl;

pyrimidyl; pyrazinyl; pyridazinyl; triazinyl, pyranyl; quinazolinyl;

isoquinolinyl; indolizinyl; isobenzofuranylnaphthyridinyl; quinoxalinyl;

cinnolinyl; phthalazinyl; benzothiazolyl; benzoxazolyl; benzotriazolyl;

indazolyl; indolyl; (1H-pyrrol-1-yl)-; (1H-pyrrol-2-yl)-; (1H-pyrrol-3-yl)-; (1H-pyrazol -1-yl)-; (1H-pyrazol-3-yl)-; (3H-pyrazol-3-yl)-; (1H-pyrazol-4-yl)-; (3-isoxazolyl)-; (5-isoxazolyl)-; (2-furanyl)-; (3-furanyl)-; (2-thienyl)-; (3-thienyl)-; (1H-imidazol-2-yl)-; (1H-imidazol-4-yl)-; (1H-imidazol-5-yl)-; (2-oxazol-2-yl)-; (oxazol-4-yl)-; (oxazol-5-yl)-; (thiazol-2-yl)-; (thiazol-4-yl)-; (thiazol-5-yl)-; (isothiazol-3-yl)-; (isothiazol-5-yl)-; (1H-1,2,3-triazol-1-yl)-; (1H-1,2,4-triazol-3-yl)-; (4H-1,2,4-triazol-4-yl)-; (1H-1,2,4-triazol-1-yl)-; (1,2,3-oxadiazol-2-yl)-; (1,2,4-oxadiazol-3-yl)-; (1,2,4-oxadiazol-4-yl)-; (1,2,4-oxadiazol-5-yl)-; (1,2,3-thiadiazol-2-yl)-; (1,2,4-thiadiazol-3-yl)-; (1,2,4-thiadiazol-4-yl)-; (1,3,4-thiadiazol-5-yl)-; (1H-tetrazol-1-yl)-; (1H-tetrazol-5-yl)-; (2H-tetrazol-5-yl)-; (2-pyridyl)-; (3-pyridyl)-; (4-pyridyl)-; (2-pyrimidinyl)-; (4-pyrimidinyl)-; (5-pyrimidinyl)-; (2-pyrazinyl)-; (3-pyridazinyl)-; (4-pyridazinyl)-; (1,3,5-triazin-2-yl)-; (1,2,4-triazin-5-yl)-; (1,2,4-triazin-6-yl)-; (1,2,4-triazin-3-yl)-; (furazan-3-yl)-; (2-quinolinyl)-; (3-quinolinyl)-; (4-quinolinyl)-; (5-quinolinyl)-; (6-quinolinyl)-; (3-isoquinolnyl)-; (4-isoquinolnyl)-; (2-quinozolinyl)-; (2-quinoxalinyl)-; (5-quinoxalinyl)-; (pyrido[2,3-b]pyrazin-7-yl)-; (benzoxazol-5-yl)-; (benzothiazol-5-yl)-; (benzo[b]thien-2-yl) and (benzo[1,2,5]oxadiazol-5-yl)-; indolinyl and tetrahydroquinolynyl.

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

Q is selected from the group consisting of J-0 to J-51:

wherein each group J-0 to J-48 is mono-, di- or trisubstituted with Rx, wherein each Rx is, independently selected from hydrogen, halogen, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 haloalkoxy, C 1 -C 4 alkoxy, C 1 -C 4 alkylsulfanyl, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, —C(O)C 1 -C 4 alkyl, C 1 C 4 haloalkylsulfanyl, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 haloalkylsulfonyl and —C(O)C 1 -C 4 haloalkyl.

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

wherein

A, Q, G 1 , G 2 , G 3 , G 4 , and G 5 are as defined under formula I in claim 1 ;

X 1 is S, SO or SO 2 ;

R 11 is methyl, ethyl, n-propyl, i-propyl or cyclopropylmethyl; and

R 8 is as defined under formula I in claim 1 .

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

wherein

A, G 1 , G 2 , G 3 , G 4 , and G 5 are as defined under formula I in claim 1 ;

X 2 is S, SO or SO 2;

R 12 is methyl, ethyl, n-propyl, i-propyl or cyclopropylmethyl;

R 8 is as defined above under formula I in claim 1 ; and

Qa 1 is selected from the group consisting of

wherein each group J-0 to J-48 is mono-, di- or trisubstituted with Rx, wherein each Rx is, independently selected from hydrogen, halogen, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 haloalkoxy, C 1 -C 4 alkoxy, C 1 -C 4 alkylsulfanyl, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, —C(O)C 1 -C 4 alkyl, C 1 -C 4 haloalkylsulfanyl, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 haloalkylsulfonyl and —C(O)C 1 -C 4 haloalkyl.

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

wherein

A is N or CH;

R 10 is pyridyl or pyrimidyl mono- or polysubstituted by C 1 -C 4 haloalkyl;

X 3 is S or SO 2 ;

Qa 2 is selected from the group consisting of

wherein each group J-0 to J-48 is mono-, di- or trisubstituted with Rx, wherein each Rx is, independently selected from hydrogen, halogen, cyano, C 1 -C 4 haloalkyl and C 1 -C 4 alkoxy;

R 13 is C 1 -C 4 alkyl; and

R 8 is C 1 -C 4 alkyl.

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

wherein

R 10 ′ is pyridyl or pyrimidyl monosubstituted by C 1 -C 4 haloalkyl; and

Qa 4 is selected from the group consisting of

wherein each Rx is independently selected from hydrogen, halogen, cyano, C 1 -C 4 haloalkyl and C 1 -C 4 alkoxy.

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

wherein

R 5 is C 1 -C 4 haloalkyl; and

Qa 5 is selected from the group consisting of

wherein each Rx is, independently selected from hydrogen, halogen, cyano, C 1 -C 4 haloalkyl and C 1 -C 4 alkoxy.

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

wherein

R 6 is C 1 -C 4 haloalkyl; and

Qa 6 is selected from the group consisting of

wherein each Rx is, independently selected from hydrogen, halogen and cyano.

10. A compound of formula I according to claim 1 , represented by the compounds of formula I-1p

wherein

A, Q, G l , G 2 , G 3 , G 4 , and G 5 are as defined under formula I in claim 1 ;

X 1 is S, SO or SO 2 ;

R 11 is methyl, ethyl, n-propyl, i-propyl or cyclopropylmethyl; and

R 8 is as defined under formula I in claim 1 .

11. A compound of formula I according to claim 1 represented by the compounds of formula I-2p

wherein

A, Q, G l , G 2 , G 3 , G 4 , and G 5 are as defined under formula I in claim 1 ;

X 2 is S, SO or SO 2;

R 12 is methyl, ethyl, n-propyl, i-propyl or cyclopropylmethyl;

R 8 is as defined above under formula I in claim 1 ; and

Q is selected from the group consisting of

wherein each group J-0 to J-43 is mono-, di- or trisubstituted with Rx, wherein each Rx is, independently selected from hydrogen, halogen, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 haloalkoxy, C 1 -C 4 alkoxy, C 1 -C 4 alkylsulfanyl, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, —C(O)C 1 -C 4 alkyl, C 1 -C 4 haloalkylsulfanyl, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 haloalkylsulfonyl and —C(O)C 1 -C 4 haloalkyl.

12. 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.

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 .

15. A compound of formula (Iab)

wherein

G 1 is nitrogen or CR 2 ;

G 2 is nitrogen or CR 3 ;

G 3 is nitrogen or CR 4 ;

G 4 is nitrogen or CR 5 ;

G 5 is nitrogen or CR 6 , with the proviso that not more than 2 nitrogens as G may follow consecutively;

R 2 , R 3 , R 4 , R 5 or R 6 are, independently from each other, hydrogen, halogen, C 1 -C 4 haloalkyl, C 1 -C 4 haloalkyl substituted by one or two hydroxy, C 1 -C 4 haloalkyl substituted by one or two methoxy, C 1 -C 4 haloalkyl substituted by one or two cyano; or

R 2 , R 3 , R 4 , R 5 or R 6 are, independently from each other, C 1 -C 4 haloalkylsulfanyl, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 haloalkylsulfonyl, C 1 -C 4 haloalkoxy, SF 5 ,

phenylcarbonylthio, cyano, mercapto, C 1 -C 4 alkoxycarbonyl, C 1 -C 4 alkylcarbonyl or —C(O)C 1 -C 4 haloalkyl; or

R 2 , R 3 , R 4 , R 5 or R 6 are, independently from each other, 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;

or two adjacent R i , wherein R i is selected from R 2 , R 3 , R 4 , R 5 and R 6 , taken together may form a fragment —OCH 2 O— or —OCF 2 O—,

R 8 is hydrogen, C 1 -C 4 alkyl or C 1 -C 4 haloalkyl;

A represents CH or N;

X is S, SO or SO 2 ; and

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

R 1 is C 3 -C 6 cycloalkyl mono- or polysubstituted by substituents selected from the group consisting of halogen, cyano and C 1 -C 4 alkyl; or

R 1 is C 3 -C 6 cycloalkyl-C 1 -C 4 alkyl mono- or polysubstituted by substituents selected from the group consisting of halogen, cyano and C 1 -C 4 alkyl; or

R 1 is C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl or C 2 -C 6 alkynyl.

16. A compounds of formula XVII-Int

wherein

G 1 is nitrogen or CR 2 ;

G 2 is nitrogen or CR 3 ;

G 3 is nitrogen or CR 4 ;

G 4 is nitrogen or CR 5 ;

G 5 is nitrogen or CR 6 , with the proviso that not more than 2 nitrogens as G may follow consecutively;

R 2 , R 3 , R 4 , R 5 or R 6 are, independently from each other, hydrogen, halogen, C 1 -C 4 haloalkyl, C 1 -C 4 haloalkyl substituted by one or two hydroxy, C 1 -C 4 haloalkyl substituted by one or two methoxy, C 1 -C 4 haloalkyl substituted by one or two cyano; or

R 2 , R 3 , R 4 , R 5 or R 6 are, independently from each other, C 1 -C 4 haloalkylsulfanyl, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 haloalkylsulfonyl, C 1 -C 4 haloalkoxy, SF 5 ,

phenylcarbonylthio, cyano, mercapto, C 1 -C 4 alkoxycarbonyl, C 1 -C 4 alkylcarbonyl or—C(O)C 1 -C 4 haloalkyl; or

R 2 , R 3 , R 4 , R 5 or R 6 are, independently from each other, 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;

or two adjacent R i , wherein R i is selected from R 2 , R 3 , R 4 , R 5 and R 6 , taken together may form a fragment —OCH 2 O— or —OCF 2 O—,

R 8 is hydrogen, C 1 -C 4 alkyl or C 1 -C 4 haloalkyl;

A represents CH or N;

X is S, SO or SO 2; and

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

R 1 is C 3 -C 6 cycloalkyl mono- or polysubstituted by substituents selected from the group consisting of halogen, cyano and C 1 -C 4 alkyl; or

R 1 is C 3 -C 6 cycloalkyl-C 1 -C 4 alkyl mono- or polysubstituted by substituents selected from the group consisting of halogen, cyano and C 1 -C 4 alkyl; or

R 1 is C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl or C 2 -C 6 alkynyl;

Yb 3 is —B(OH) 2 , —B(OR b2 ) 2 , in which R b2 is a C 1 -C 6 alkyl or Yb 3 is

(a 4,4,5,5-tetramethyl-1,3,2-dioxaborolane group).