Pesticidally active heterocyclic derivatives with sulphur containing substituents
View Patent ↗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 represents CH or N;
Q is attached to the 3- or 4-position; and 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, —C(O)OH, —C(O)NH 2 , phenyl and 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 halo-alkylsulfinyl,
C 1 -C 4 haloalkylsulfonyl and —C(O)C 1 -C 4 haloalkyl;
X is S, SO or SO 2 ;
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 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;
R 2 is halogen, cyano, C 1 -C 6 haloalkyl or C 1 -C 6 haloalkyl substituted by one or two substituents selected from the group consisting of hydroxyl, methoxy and cyano; or
R 2 is C 1 -C 4 haloalkylsulfanyl, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 haloalkylsulfonyl, O(C 1 -C 4 haloalkyl), or —C(O)C 1 -C 4 haloalkyl; or
R 2 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 1 is O, S or NR 3 , wherein R 3 is hydrogen, C 1 -C 4 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 4 alkoxy-
C 1 -C 4 alkyl or C 3 -C 6 cycloalkyl; or an agrochemically acceptable salt, a stereoisomer, an enantiomer, a tautomer or an N-oxide of a compound of formula I.
2. The compound of claim 1 , represented by the compounds of formula I-1
wherein R 2 and Q are as defined under formula I in claim 1 ;
Xa 1 is S, SO or SO 2 ; and
Ra 1 is methyl, ethyl, n-propyl, i-propyl or cyclopropylmethyl.
3. The compound of claim 1 , represented by the compounds of formula I-2
wherein R 2 and Q are as defined under formula I in claim 1 ;
Xa 2 is S, SO or SO 2 ; and
Ra 2 is methyl, ethyl, n-propyl, i-propyl or cyclopropylmethyl.
4. The compound of claim 1 , represented by the compounds of formula I-3
wherein R 2 and Q are as defined under formula I in claim 1 ;
Xa 3 is S, SO or SO 2 ; and
Ra 3 is methyl, ethyl, n-propyl, i-propyl or cyclopropylmethyl.
5. The compound of claim 1 , represented by the compounds of formula Ia-1
wherein
A is CH or N;
X 2 is S or SO 2 ;
X 3 is N—(C 1 -C 4 alkyl);
R 4 is C 1 -C 4 alkyl;
R 5 is C 1 -C 4 haloalkyl or C 1 -C 4 haloalkylsulfanyl; and
Q a 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(O)OH and —C(O)NH 2 .
6. The compound of claim 1 , represented by the compounds of formula Ia-2
wherein
A is CH or N;
X 4 is N—(C 1 -C 4 alkyl);
R 6 is C 1 -C 4 haloalkyl or C 1 -C 4 haloalkylsulfanyl; and
Q b is C 3 -C 6 cycloalkyl, or C 3 -C 6 cycloalkyl monosubstituted by substituents selected from the group consisting of cyano, —C(O)OH and —C(O)NH 2 .
7. The compound of claim 1 , represented by the compounds of formula Ia-3
wherein
A is CH or N;
X 2p is S or SO 2 ;
X 3p is N—(C 1 -C 4 alkyl);
R 4p is C 1 -C 4 alkyl;
R 5p is C 1 -C 4 haloalkyl or C 1 -C 4 haloalkylsulfanyl; and
Q ap 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(O)OH, —C(O)NH 2 and phenyl.
8. The compound of claim 1 , represented by the compounds of formula Ia-4
wherein
A is CH or N;
X 4p is N—(C 1 -C 4 alkyl);
R 6p is C 1 -C 4 haloalkyl or C 1 -C 4 haloalkylsulfanyl; and
Q bp is C 3 -C 6 cycloalkyl, or C 3 -C 6 cycloalkyl monosubstituted by substituents selected from the group consisting of cyano, —C(O)OH and —C(O)NH 2 .
9. The compound of claim 1 , represented by a compound of formula VI-a
wherein
A, Q, X 1 and R 2 are as defined under formula I in claim 1 ; and
Xb 30 is halogen.
10. 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.
11. A method for controlling pests, which comprises applying a composition according to claim 10 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.
12. 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 B is planted, with a composition according to claim 10 .
13. Plant propagation material treated in accordance with the method described in claim 12 .
14. The compound of claim 1 , wherein R 2 is halogen, cyano, C 1 -C 6 haloalkyl or C 1 -C 6 haloalkyl substituted by one or two substituents selected from the group consisting of hydroxyl, methoxy and cyano; or
R 2 is C 1 -C 4 haloalkylsulfanyl, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 haloalkylsulfonyl, O(C 1 -C 4 haloalkyl), or —C(O)C 1 -C 4 haloalkyl; or
R 2 is cyclopentyl or cyclohexyl which can be mono- or polysubstituted by substituents selected from the group consisting of halogen, cyano and C 1 -C 4 alkyl.