Pesticidally active bi- or tricyclic heterocycles with sulfur containing substituents

Patent metadata

Field	Value
Publication number	US-11229208-B2
Application number	US-202017068334-A
Country	US
Kind code	B2
Filing date	Oct 12, 2020
Priority date	Jul 2, 2013
Publication date	Jan 25, 2022
Grant date	Jan 25, 2022

Abstract

Compounds of formula I

A-B  (I),
wherein A is a radical selected from the group consisting of formulae A 1 to A 8 :

wherein the arrow denotes the point of attachment to the radical B; and
B is a radical selected from the group consisting of formulae B 1 to B 11 :

wherein the arrow denotes the point of attachment to the radical A; and wherein the substituents are as defined in claim 1 , and the agrochemically acceptable salts and all stereoisomers and tautomeric forms of the compounds of formula I can be used as insecticides and can be prepared in a manner known per se.

First claim

What is claimed is:

1. A method, comprising:
applying 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 8 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, 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, or a composition comprising the compound of formula (I), to an insect, a locus of an insect, or a plant susceptible to attack by an insect.

2. The method of claim 1 , wherein the applying is of the composition comprising the compound of formula (I).

3. The method of claim 1 , wherein the applying is a pesticidally effective amount.

4. The method of claim 3 , wherein the pesticidally effective amount is an insecticidally effective amount.

5. The method of claim 4 , wherein the applying is to the insect.

6. The method of claim 4 , wherein the applying is to the locus of the insect.

7.

Assignees

• Syngenta Participations Ag

Inventors

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

Classifications

• C07D498/04

  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

• A61P33/00

  Antiparasitic agents · CPC title

• C07D487/04

  Ortho-condensed systems · CPC title

• C07D471/04

  Ortho-condensed systems · CPC title