# US 9,751,862 B2 · Pesticidally active substituted pyridyl carboxamides

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- Number: US 9,751,862 B2
- Document ID: US9751862B2
- Status: Granted
- Kind: B2
- Application number: 15/124,369
- Filed: 2015-03-18
- Published: 2017-04-20
- Granted: 2017-09-05
- Earliest claimed: 2014-03-20
- Assignees: Syngenta Participations AG
- Applicants: Syngenta Participations AG
- Inventors: Andre Jeanguenat; Andrew Edmunds; Roger Graham Hall
- Web page: https://patentgrep.com/patent/US9751862B2

## CPC

- C07D 401/14: containing three or more hetero rings
- A01N 43/56: 1,2-Diazoles; Hydrogenated 1,2-diazoles
- A01N 43/58: 1,2-Diazines; Hydrogenated 1,2-diazines
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A01N: PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF (preservation of food or foodstuff A23); BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES (preparations for medical, dental or toiletry purposes which kill or prevent the growth or proliferation of unwanted organisms A61K); PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS

## Abstract

Compounds of formula (I) wherein m is 0 or 1; Z is methine or nitrogen; X is oxygen or sulfur, R1 is C1-C6-alkyl, halo-C1-C6-alkyl, C3-C6-cycloalkyl or C2-C6-alkynyl; R2 is C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, halo-C3-C6-cycloalkyl, fluoro, chloro or bromo; R3 is C1-C3-alkyl; R4 is hydrogen, C1-C6-alkyl, fluoro, chloro, bromo or cyano; Y is CN, COOR9 or CONHR6; n is 0, 1 or 2; R5 is hydrogen, fluoro, chloro or bromo; R6 is C1-C4-alkyl; R9 is C1-C4-alkyl; R10 and R11 are, independently from each other, hydrogen, C1-C3-alkyl or C1-C3-alkoxy; or R10 and R11 taken together form with the carbon atom to which they are bonded a C3-C6-carbocyclic ring; or R10 and R11 taken together form a ketone or a ═NOR12 group; and R12 is hydrogen or C1-C4-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

### Claim 1

A compound of formula I
wherein
m is 0 or 1;
Z is methine or nitrogen;
X is oxygen or sulfur,
R1 is C1-C6-alkyl, halo-C1-C6-alkyl, C3-C6-cycloalkyl or C2-C6-alkynyl;
R2 is C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, halo-C3-C6-cycloalkyl, fluoro, chloro or bromo;
R3 is C1-C3-alkyl;
R4 is hydrogen, C1-C6-alkyl, fluoro, chloro, bromo or cyano;
Y is CN, COOR9 or NO2;
n is 0, 1 or 2;
R5 is hydrogen, fluoro, chloro or bromo;
R9 is C1-C4-alkyl;
R10 and R11 are, independently from each other, hydrogen, C1-C3-alkyl or C1-C3-alkoxy;
or R10 and R11 taken together form with the carbon atom to which they are bonded a C3-C6-carbocyclic ring;
or R10 and R11 taken together form a ketone or a ═NOR12 group; and
R12 is hydrogen or C1-C4-alkyl; and agrochemically acceptable salts of those compounds.

### Claim 2 (depends on 1)

A compound of formula I according to claim 1, wherein
m is 0;
n is 0;
R1 is C1-C4alkyl;
R2 is C1-C4alkyl;
R3 is C1-C4alkyl;
R5 is hydrogen;
X is oxygen;
Y is CN or COO—C1-C4alkyl;
Z is methine;
R10 is hydrogen or C1-C4alkyl;
R11 is hydrogen or C1-C4alkyl;
or R10 and R11 taken together form with the carbon atom to which they are bonded a C3-C6-carbocyclic ring;
or R10 and R11 taken together form a ═NOR12 group; wherein
R12 is hydrogen or C1-C4alkyl.

### Claim 3 (depends on 1)

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

### Claim 4 (depends on 3)

A compound of formula I according to claim 3, wherein
m is 0;
n is 0;
R1 is C1-C4alkyl;
R2 is C1-C4alkyl;
R3 is C1-C4alkyl;
R5 is hydrogen;
X is oxygen;
Z is methine;
R10 is hydrogen or C1-C4alkyl;
R11 is hydrogen or C1-C4alkyl;
or R10 and R11 taken together form with the carbon atom to which they are bonded a C3-C6-carbocyclic ring;
or R10 and R11 taken together form a ═NOR12 group; wherein
R12 is hydrogen or C1-C4alkyl.

### Claim 5 (depends on 1)

A compound of formula I according to claim 1, wherein Y is COOR9.

### Claim 6 (depends on 5)

A compound of formula I according to claim 5, wherein
m is 0;
n is 0;
R1 is C1-C4alkyl;
R2 is C1-C4alkyl;
R3 is C1-C4alkyl;
R5 is hydrogen;
R9 is C1-C4alkyl;
X is oxygen;
Z is methine;
R10 is hydrogen or C1-C4alkyl;
R11 is hydrogen or C1-C4alkyl;
or R10 and R11 taken together form with the carbon atom to which they are bonded a C3-C6-carbocyclic ring; in particular a cyclopropyl ring;
or R10 and R11 taken together form a ═NOR12 group; wherein
R12 is hydrogen or C1-C4alkyl.

### Claim 7 (depends on 1)

A compound of formula I according to claim 1, wherein Y is NO2.

### Claim 8 (depends on 7)

A compound of formula I according to claim 7, wherein
m is 0;
n is 0;
R1 is C1-C4alkyl;
R2 is C1-C4alkyl;
R3 is C1-C4alkyl;
R5 is hydrogen;
X is oxygen;
Z is methine;
R10 is hydrogen or C1-C4alkyl;
R11 is hydrogen or C1-C4alkyl;
or R10 and R11 taken together form with the carbon atom to which they are bonded a C3-C6-carbocyclic ring;
or R10 and R11 taken together form a ═NOR12 group; wherein
R12 is hydrogen or C1-C4alkyl.

### Claim 9 (depends on 1)

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.

### Claim 10 (depends on 9)

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.

### Claim 11 (depends on 1)

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.

### Claim 12 (depends on 1)

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