Pesticidally active bi- or tricyclic heterocycles with sulfur containing substituents

Patent metadata

Field	Value
Publication number	US-10939682-B2
Application number	US-201414898597-A
Country	US
Kind code	B2
Filing date	Jun 19, 2014
Priority date	Jul 2, 2013
Publication date	Mar 9, 2021
Grant date	Mar 9, 2021

Abstract

Pesticidally active bi- or tricyclic heterocycles with sulphur-containing substituents, stereoisomers and tautomeric forms thereof that can be used as insecticides and can be prepared in a manner known per se.

First claim

What is claimed is:

1. A compound of formula I,
A-B  (I),

wherein A is

wherein the arrow denotes the point of attachment to the radical B; and
B is

wherein the arrow denotes the point of attachment to the radical A;
wherein
L 1 is a direct bond;
V 0 is CR 5 ;
V 1 is nitrogen;
V 2 is CR 21 ,
G 1 is CR 31 ;
G 2 is CR 32 , wherein R 32 is H;
G 3 is —NR 35 ;
G 4 is nitrogen;
G 5 is nitrogen;
R 1 represents hydrogen, halogen, C 1 -C 6 alkyl or C 1 -C 6 haloalkyl;
R 3 is a C 1 -C 6 alkyl, C 2 -C 6 alkenyl or C 2 -C 6 alkynyl group which can be mono- or polysubstituted by substituents selected from the group consisting of C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 2 -C 6 alkenyloxy, C 2 -C 6 haloalkenyloxy, C 2 -C 6 alkynyloxy, C 2 -C 6 haloalkynyloxy, C 1 -C 6 alkylsulphanyl, C 1 -C 6 haloalkylsulphanyl, C 1 -C 6 alkylsulphinyl, C 1 -C 6 haloalkylsulphinyl, C 1 -C 6 alkylsulphonyl, C 1 -C 6 haloalkylsulphonyl, C 2 -C 6 alkylcarbonyl, C 2 -C 6 haloalkylcarbonyl, C 2 -C 6 alkoxycarbonyl, C 2 -C 6 haloalkoxycarbonyl, cyano, hydroxy, halogen, C 3 -C 6 cycloalkyl, said C 3 -C 6 cycloalkyl itself can be mono- or polysubstituted by substituents selected from halogen and C 1 -C 3 alkyl; and by a 5- or 6-membered heterocyclic group, which can be mono- or polysubstituted by substituents selected from the group consisting of C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkylsulphanyl, C 1 -C 6 haloalkylsulphanyl, C 1 -C 6 alkylsulphinyl, C 1 -C 6 haloalkylsulphinyl, C 1 -C 6 alkylsulphonyl, C 1 -C 6 haloalkylsulphonyl, C 2 -C 6 alkylcarbonyl, C 2 -C 6 haloalkylcarbonyl, C 2 -C 6 alkoxycarbonyl, C 2 -C 6 haloalkoxycarbonyl, C 1 -C 6 alkylamino, C 1 -C 6 haloalkylamino, C 2 -C 8 dialkylamino, C 2 -C 5 halodialkylamino, halogen, cyano and nitro;
or R 3 is C 3 -C 6 cycloalkyl, which can be mono- or polysubstituted by substituents selected from the group consisting of C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 2 -C 6 alkenyloxy, C 2 -C 6 haloalkenyloxy, C 2 -C 6 alkynyloxy, C 2 -C 6 haloalkynyloxy and halogen;
or R 3 is a 5- or 6-membered heterocyclic group, which can be mono- or polysubstituted by substituents selected from the group consisting of C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkylsulphanyl, C 1 -C 6 haloalkylsulphanyl, C 1 -C 6 alkylsulphinyl, C 1 -C 6 haloalkylsulphinyl, C 1 -C 6 alkylsulphonyl, C 1 -C 6 haloalkylsulphonyl, C 2 -C 6 alkylcarbonyl, C 2 -C 6 haloalkylcarbonyl, C 2 -C 6 alkoxycarbonyl, C 2 -C 6 haloalkoxycarbonyl, C 1 -C 6 alkylamino, C 1 -C 6 haloalkylamino, C 2 -C 8 dialkylamino, C 2 -C 8 halodialkylamino, halogen, cyano and nitro;
or R 3 is —CO 2 R 36 , —C(O)R 36 or hydrogen;
R 35 is hydrogen, C 1 -C 6 alkyl which can be mono- or polysubstituted by substituents selected from the group consisting of C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 2 -C 6 alkenyloxy, C 2 -C 6 haloalkenyloxy, C 2 -C 6 alkynyloxy, C 2 -C 6 haloalkynyloxy, C 1 -C 6 alkylsulphanyl, C 1 -C 6 haloalkylsulphanyl, C 1 -C 6 alkylsulphinyl, C 1 -C 6 haloalkylsulphinyl, C 1 -C 6 alkylsulphonyl, C 1 -C 6 haloalkylsulphonyl, C 2 -C 6 alkylcarbonyl, C 2 -C 6 alkoxycarbonyl, cyano, hydroxy, halogen and C 3 -C 6 cycloalkyl, said C 3 -C 6 cycloalkyl itself can be mono- or polysubstituted by substituents selected from halogen and C 1 -C 3 alkyl; or an N-oxide thereof;
R 4 , R 5 , and R 21 are the same or different and represents cyano, nitro, halogen, hydroxy, C 1 -C 6 alkenyloxy, C 1 -C 6 -haloalkoxy, C 3 -C 6 cycloalkyl, —C(O)R 36 or hydrogen; or
C 1 -C 6 alkyl which can be mono- or polysubstituted by substituents selected from the group consisting of cyano, halogen, hydroxy, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 2 -C 6 alkenyloxy, C 2 -C 6 haloalkenyloxy, C 2 -C 6 alkynyloxy, C 2 -C 6 haloalkynyloxy, C 1 -C 6 alkylsulphanyl, C 1 -C 6 haloalkylsulphanyl, C 1 -C 6 alkylsulphinyl, C 1 -C 6 haloalkylsulphinyl, C 1 -C 6 alkylsulphonyl, C 1 -C 6 haloalkylsulphonyl, C 2 -C 6 alkylcarbonyl, C 2 -C 6 haloalkylcarbonyl, C 2 -C 6 alkoxycarbonyl, C 2 -C 6 haloalkoxycarbonyl, cyano, hydroxy, halogen and C 3 -C 6 cycloalkyl, said cycloalkyl itself can be substituted by substituents selected from the group consisting of halogen and C 1 -C 3 alkyl; or represents
a phenyl group which can be mono or polysubstituted by substituents selected from the group consisting of C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkylsulphanyl, C 1 -C 6 haloalkylsulphanyl, C 1 -C 6 alkylsulphinyl, C 1 -C 6 haloalkylsulphinyl, C 1 -C 6 alkylsulphonyl, C 1 -C 6 haloalkylsulphonyl, C 2 -C 6 alkylcarbonyl, C 2 -C 6 haloalkylcarbonyl, C 2 -C 6 alkoxycarbonyl, C 2 -C 6 haloalkoxycarbonyl, C 1 -C 6 alkylamino, C 1 -C 6 haloalkylamino, C 2 -C 8 dialkylamino, C 2 -C 8 halodialkylamino, halogen, cyano, and nitro;
R 7 represents C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, or hydrogen;
R 31 represents C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, —OR 7 , —S(O) n R 36 , —NR 36 R 37 , —CO 2 R 36 , —C(O)R 36 , cyano, nitro, halogen or hydrogen;
R 36 and R 37 are the same or different and represents hydrogen, C 1 -C 6 alkyl which can be mono- or polysubstituted by substituents selected from C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 2 -C 6 alkenyloxy, C 2 -C 6 haloalkenyloxy, C 2 -C 6 alkynyloxy, C 2 -C 6 haloalkynyloxy, C 1 -C 6 alkylsulphanyl, C 1 -C 6 haloalkylsulphanyl, C 1 -C 6 alkylsulphinyl, C 1 -C 6 haloalkylsulphinyl, C 1 -C 6 alkylsulphonyl, C 1 -C 6 haloalkylsulphonyl, C 2 -C 6 alkylcarbonyl, C 2 -C 6 haloalkylcarbonyl, C 2 -C 6 alkoxycarbonyl, C 2 -C 6 haloalkoxycarbonyl, cyano, hydroxy, halogen and C 3 -C 6 cycloalkyl, wherein said C 3 -C 6 cycloalkyl can be mono-or polysubstituted by substituents selected from the group consisting of halogen and C 1 -C 3 alkyl; or
R 36 and R 37 are the same or different and represents

a phenyl group which can be mono- or polysubstituted by substituents selected from the group consisting of C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkylsulphanyl, C 1 -C 6 haloalkylsulphanyl, C 1 -C 6 alkylsulphinyl, C 1 -C 6 haloalkylsulphinyl, C 1 -C 6 alkylsulphonyl, C 1 -C 6 haloalkylsulphonyl, C 2 -C 6 alkylcarbonyl, C 2 -C 6 haloalkylcarbonyl, C 2 -C 6 alkoxycarbonyl, C 2 -C 6 haloalkoxycarbonyl, C 1 -C 6 alkylamino, C 1 -C 6 haloalkylamino, C 2 -C 8 dialkylamino, C 2 -C 8 halodialkylamino, halogen, cyano, and nitro;
each m independently represents 0, 1 or 2, and n represents 0, 1 or 2, with the proviso that:
in —S(O) n R 36 , R 36 is hydrogen when n is 0;

or an agrochemically acceptable salt, enantiomer, diastereomer, tautomer, or N-oxide thereof.

2. A composition, comprising a compound of formula I according to claim 1 and a suitable carrier or diluent therefor.

3. The compound of claim 1 , wherein R 1 is C 1 -C 6 haloalkyl and R 21 is a phenyl group which can be mono or polysubstituted by substituents selected from the group consisting of C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkylsulphanyl, C 1 -C 6 haloalkylsulphanyl, C 1 -C 6 alkylsulphinyl, C 1 -C 6 haloalkylsulphinyl, C 1 -C 6 alkylsulphonyl, C 1 -C 6 haloalkylsulphonyl, C 2 -C 6 alkylcarbonyl, C 2 -C 6 haloalkylcarbonyl, C 2 -C 6 alkoxycarbonyl, C 2 -C 6 haloalkoxycarbonyl, C 1 -C 6 alkylamino, C 1 -C 6 haloalkylamino, C 2 -C 8 dialkylamino, C 2 -C 8 halodialkylamino, halogen, cyano, and nitro.

4. The compound of claim 1 , wherein R 1 is C 1 -C 6 alkyl and R 21 is C 1 -C 6 alkyl which can be mono- or polysubsti

Assignees

• Syngenta Participations Ag

Inventors

• Edmunds Andrew
• Muehlebach Michel
• Stoller Andre
• Loiseleur Olivier
• Buchholz Anke
• Hueter Ottmar Franz
• Hall Roger Graham
• Emery Daniel
• Jung Pierre Joseph Marcel
• Lu Long
• Wu Yaming
• Bigot Aurelien
• Chen Ruifang

Classifications

• C07D498/04

  Ortho-condensed systems · CPC title

• C07D487/04

  Ortho-condensed systems · CPC title

• A01N43/90 Primary

  having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system · CPC title

• C07D471/12

  in which the condensed system contains three hetero rings · CPC title

• C07D471/04

  Ortho-condensed systems · CPC title