Pesticidally active polycyclic derivatives with 5-membered sulfur containing heterocyclic ring systems

Patent metadata

Field	Value
Publication number	US-10736320-B2
Application number	US-201615762994-A
Country	US
Kind code	B2
Filing date	Sep 19, 2016
Priority date	Sep 25, 2015
Publication date	Aug 11, 2020
Grant date	Aug 11, 2020

Abstract

Pesticidally active polycyclic derivatives with 5-membered sulfur containing heterocyclic ring systems of formula (I), wherein the substituents are as defined in claim 1 , and the agrochemically acceptable salts 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.

First claim

The invention claimed is:

1. A compound of formula I

wherein
A 1 is methine and A 2 is methine or N;
R 2 is C 1 -C 4 alkyl, C 3 -C 4 cycloalkyl, or C 1 -C 4 alkyl-C 3 -C 4 -cycloalkyl;
n is 0, 1 or 2;
R 1 is selected from a group consisting of J 0 to J 30

wherein the arrow represents the point of attachment to formula I, and each of the groups J 0 to J 30 can be mono- di- or trisubstituted by a group Rx, wherein Rx is 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(O)C 1 -C 4 haloalkyl, C 1 -C 4 haloalkylsulfanyl, C 1 -C 4 haloalkylsulfinyl and C 1 -C 4 haloalkylsulfonyl, and
wherein R 001 represents hydrogen or C 1 -C 4 alkyl;
R 3 and R 4 , independently from each other, are hydrogen, halogen, C 1 -C 4 haloalkoxy, C 1 -C 4 haloalkyl, amino, hydroxy or cyano; or
R 3 and R 4 , independently from each other, are 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
R 3 and R 4 , independently from each other, are a five- to ten-membered monocyclic or fused bicyclic ring system linked via a carbon atom to the ring which contains the group A 2 , 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, with the proviso that each ring system cannot contain more than 2 oxygen atoms or 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
R 3 and R 4 , independently from each other, are a five- to six-membered, aromatic, partially saturated or fully saturated ring system containing 1, 2 or 3 heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur with the proviso that said ring system cannot contain more than one oxygen atom or more than one sulfur atom and linked via a nitrogen atom to the ring which contains the group A 2 , 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; or
R 3 and R 4 , independently from each other, are 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 halo-alkylsulfinyl, C 1 -C 4 haloalkylsulfonyl and —C(O)C 1 -C 4 haloalkyl; or
R 3 and R 4 , independently from each other, are 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 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
R 3 and R 4 , independently from each other, are 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 halo-alkylsulfanyl, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 haloalkyl sulfonyl and —C(O)C 1 -C 4 haloalkyl; or
R 3 and R 4 , independently from each other, are C 1 -C 6 alkyl, or C 1 -C 6 alkyl 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 halo-alkylsulfanyl, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 haloalkylsulfonyl and —C(O)C 1 -C 4 haloalkyl; and
agrochemically acceptable salts, stereoisomers, enantiomers, tautomers of the compounds of formula I.

2. The compound of formula I according to claim 1 , wherein
R 3 and R 4 , independently from each other, are hydrogen, C 1 -C 4 haloalkyl, halogen or selected from a group consisting of Z-0 to Z-50:

wherein each group Z-0 to Z-50 is mono- di- or trisubstituted with Rx; wherein
each Rx is, independently selected from the group consisting of 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; and R 002 represents hydrogen or C 1 -C 4 haloalkyl.

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

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

5. The compound of formula I according to claim 1 , wherein
R 1 is pyridine which is monosubstituted by C 1 -C 4 haloalkyl;
R 2 is C 1 -C 4 alkyl;
R 3 is hydrogen, C 1 -C 4 haloalkyl, C 1 -C 6 cycloalkyl or pyrimidinyl;
R 4 is hydrogen, C 1 -C 4 haloalkyl, C 1 -C 6 cycloalkyl or pyrimidinyl;
n is 2.

6. The compound of formula I according to claim 1 , wherein R x is selected from cyano, C 1 -C

Assignees

• Syngenta Participations Ag

Inventors

• Edmunds Andrew
• Muehlebach Michel
• Jung Pierre Joseph Marcel
• Emery Daniel
• Buchholz Anke
• Chen Ruifang
• Lu Long
• Wu Yaming

Classifications

• C07D417/04 Primary

  directly linked by a ring-member-to-ring-member bond · CPC title

• C07D417/14

  containing three or more hetero rings · CPC title

• A01N43/78

  1,3-Thiazoles; Hydrogenated 1,3-thiazoles · CPC title

• A01N43/82 Primary

  five-membered rings with three ring hetero atoms · CPC title