IP Library Granted Patent US 9,751,862
Granted Patent B2
US 9,751,862 · App. 15/124,369 · Granted Sep 5, 2017

Pesticidally active substituted pyridyl carboxamides

View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 9,751,862
App. No.
15/124,369
Granted
Sep 5, 2017
Kind
B2
Abstract

Compounds of formula (I) wherein m is 0 or 1; Z is methine or nitrogen; X is oxygen or sulfur, R 1 is C 1 -C 6 -alkyl, halo-C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl or C 2 -C 6 -alkynyl; R 2 is C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -cycloalkyl, halo-C 3 -C 6 -cycloalkyl, fluoro, chloro or bromo; R 3 is C 1 -C 3 -alkyl; R 4 is hydrogen, C 1 -C 6 -alkyl, fluoro, chloro, bromo or cyano; Y is CN, COOR 9 or CONHR 6 ; n is 0, 1 or 2; R 5 is hydrogen, fluoro, chloro or bromo; R 6 is C 1 -C 4 -alkyl; R 9 is C 1 -C 4 -alkyl; R 10 and R 11 are, independently from each other, hydrogen, C 1 -C 3 -alkyl or C 1 -C 3 -alkoxy; or R 10 and R 11 taken together form with the carbon atom to which they are bonded a C 3 -C 6 -carbocyclic ring; or R 10 and R 11 taken together form a ketone or a ═NOR 12 group; and R 12 is hydrogen or C 1 -C 4 -alkyl; and agrochemically acceptable salts and enantiomers of those compounds can be used as insecticides an can be prepared in a manner known per se.

Claims (82)

1. A compound of formula I

wherein

m is 0 or 1;

Z is methine or nitrogen;

X is oxygen or sulfur,

R 1 is C 1 -C 6 -alkyl, halo-C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl or C 2 -C 6 -alkynyl;

R 2 is C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -cycloalkyl, halo-C 3 -C 6 -cycloalkyl, fluoro, chloro or bromo;

R 3 is C 1 -C 3 -alkyl;

R 4 is hydrogen, C 1 -C 6 -alkyl, fluoro, chloro, bromo or cyano;

Y is CN, COOR 9 or NO 2 ;

n is 0, 1 or 2;

R 5 is hydrogen, fluoro, chloro or bromo;

R 9 is C 1 -C 4 -alkyl;

R 10 and R 11 are, independently from each other, hydrogen, C 1 -C 3 -alkyl or C 1 -C 3 -alkoxy;

or R 10 and R 11 taken together form with the carbon atom to which they are bonded a C 3 -C 6 -carbocyclic ring;

or R 10 and R 11 taken together form a ketone or a ═NOR 12 group; and

R 12 is hydrogen or C 1 -C 4 -alkyl; and agrochemically acceptable salts of those compounds.

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

m is 0;

n is 0;

R 1 is C 1 -C 4 alkyl;

R 2 is C 1 -C 4 alkyl;

R 3 is C 1 -C 4 alkyl;

R 5 is hydrogen;

X is oxygen;

Y is CN or COO—C 1 -C 4 alkyl;

Z is methine;

R 10 is hydrogen or C 1 -C 4 alkyl;

R 11 is hydrogen or C 1 -C 4 alkyl;

or R 10 and R 11 taken together form with the carbon atom to which they are bonded a C 3 -C 6 -carbocyclic ring;

or R 10 and R 11 taken together form a ═NOR 12 group; wherein

R 12 is hydrogen or C 1 -C 4 alkyl.

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

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

m is 0;

n is 0;

R 1 is C 1 -C 4 alkyl;

R 2 is C 1 -C 4 alkyl;

R 3 is C 1 -C 4 alkyl;

R 5 is hydrogen;

X is oxygen;

Z is methine;

R 10 is hydrogen or C 1 -C 4 alkyl;

R 11 is hydrogen or C 1 -C 4 alkyl;

or R 10 and R 11 taken together form with the carbon atom to which they are bonded a C 3 -C 6 -carbocyclic ring;

or R 10 and R 11 taken together form a ═NOR 12 group; wherein

R 12 is hydrogen or C 1 -C 4 alkyl.

5. A compound of formula I according to claim 1 , wherein Y is COOR 9 .

6. A compound of formula I according to claim 5 , wherein

m is 0;

n is 0;

R 1 is C 1 -C 4 alkyl;

R 2 is C 1 -C 4 alkyl;

R 3 is C 1 -C 4 alkyl;

R 5 is hydrogen;

R 9 is C 1 -C 4 alkyl;

X is oxygen;

Z is methine;

R 10 is hydrogen or C 1 -C 4 alkyl;

R 11 is hydrogen or C 1 -C 4 alkyl;

or R 10 and R 11 taken together form with the carbon atom to which they are bonded a C 3 -C 6 -carbocyclic ring; in particular a cyclopropyl ring;

or R 10 and R 11 taken together form a ═NOR 12 group; wherein

R 12 is hydrogen or C 1 -C 4 alkyl.

7. A compound of formula I according to claim 1 , wherein Y is NO 2 .

8. A compound of formula I according to claim 7 , wherein

m is 0;

n is 0;

R 1 is C 1 -C 4 alkyl;

R 2 is C 1 -C 4 alkyl;

R 3 is C 1 -C 4 alkyl;

R 5 is hydrogen;

X is oxygen;

Z is methine;

R 10 is hydrogen or C 1 -C 4 alkyl;

R 11 is hydrogen or C 1 -C 4 alkyl;

or R 10 and R 11 taken together form with the carbon atom to which they are bonded a C 3 -C 6 -carbocyclic ring;

or R 10 and R 11 taken together form a ═NOR 12 group; wherein

R 12 is hydrogen or C 1 -C 4 alkyl.

9. An insecticidal, acaricidal, nematicidal or molluscicidal composition, comprising an insecticidally, acaricidally, nematicidally or molluscicidally effective amount of a compound of formula I according to claim 1 and a suitable carrier or diluent therefor.

10. 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 9 .

11. A method of combating and controlling pests which comprises applying an insecticidally, acaricidally, nematicidally or molluscicidally effective amount of a compound of formula I according to claim 1 or a composition comprising a compound of formula I, to a pest, a locus of pest, or to a plant susceptible to attack by a pest, with the exception of a method for treatment of the human or animal body by surgery or therapy and diagnostic methods practiced on the human or animal body.

12. A plant propagation material comprising the compound of formula I according to claim 1 .

Assignments (2)
MERGER AND CHANGE OF NAME Recorded Mar 14, 2025
From: SYNGENTA PARTICIPATIONS AG; SYNGENTA PARTICIPATIONS AG
To: SYNGENTA CROP PROTECTION AG
Reel/Frame 070517/0697 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 8, 2016
From: JEANGUENAT, ANDRE; EDMUNDS, ANDREW; HALL, ROGER GRAHAM
To: SYNGENTA PARTICIPATIONS AG
Reel/Frame 039670/0824 →