# US 9,750,253 B2 · Pesticidally active substituted pyridyl carboxamides

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- Number: US 9,750,253 B2
- Document ID: US9750253B2
- Status: Granted
- Kind: B2
- Application number: 14/782,382
- Filed: 2014-04-03
- Published: 2016-02-25
- Granted: 2017-09-05
- Earliest claimed: 2013-04-10
- Assignees: Syngenta Participations AG
- Applicants: Syngenta Participations AG
- Inventors: Roger Graham Hall; Andrew Edmunds; Andre Jeanguenat
- Web page: https://patentgrep.com/patent/US9750253B2

## CPC

- A01N 43/56: 1,2-Diazoles; Hydrogenated 1,2-diazoles
- A01N 43/58: 1,2-Diazines; Hydrogenated 1,2-diazines
- C07D 401/14: containing three or more hetero rings
- 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
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## 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-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; n is 0, 1, 2 or 3; R5 is hydrogen, fluoro, chloro or bromo; and agrochemically acceptable salts and enantiomers of those compounds can be used as insecticides and 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;
n is 0, 1, 2 or 3;
R5 is hydrogen, fluoro, chloro or bromo;
or an agrochemically acceptable salt thereof.

### Claim 2 (depends on 1)

A compound of formula I according to claim 1, wherein Z is methine.

### Claim 3 (depends on 1)

A compound of formula I according to claim 1, wherein Z is nitrogen.

### Claim 4 (depends on 1)

A compound of formula I according to claim 1, wherein
R1 is methyl, ethyl, isopropyl, cyclopropyl, CH2CF3, or prop-2-ynyl.

### Claim 5 (depends on 1)

A compound of formula I according to claim 1, wherein R2 is methyl, ethyl, isopropyl, cyclopropyl, CF3, CF2H or chloro.

### Claim 6 (depends on 1)

A compound of formula I according to claim 1, wherein R3 is methyl, ethyl or isopropyl.

### Claim 7 (depends on 1)

A compound of formula I according to claim 1, wherein
m is 0;
Z is methine;
X is oxygen;
R1 is methyl, ethyl, isopropyl, cyclopropyl, CH2CF3, or prop-2-ynyl;
R2 is methyl, ethyl, isopropyl, cyclopropyl, CF3, CF2H or chloro; and
R3 is methyl, ethyl or isopropyl.

### Claim 8 (depends on 1)

A compound of formula I according to claim 1, wherein
m is 0;
Z is nitrogen;
X is oxygen;
R1 is methyl, ethyl, isopropyl, cyclopropyl, CH2CF3, or prop-2-ynyl;
R2 is methyl, ethyl, isopropyl, cyclopropyl, CF3, CF2H or chloro; and
R3 is methyl, ethyl or isopropyl.

### Claim 9 (depends on 1)

A compound of formula I according to claim 1, wherein
m is 0;
Z is methine;
X is oxygen;
R1 is methyl, ethyl or prop-2-ynyl,
R2 is methyl, ethyl or isopropyl, and
R3 is methyl, ethyl or isopropyl.

### Claim 10 (depends on 1)

A compound of formula I according to claim 1, wherein
m is 1;
Z is CH;
X is oxygen;
R1 is methyl, ethyl, isopropyl, cyclopropyl, CH2CF3, or prop-2-ynyl;
R2 is methyl, ethyl, isopropyl, cyclopropyl, CF3, CF2H or chloro; and
R3 is methyl, ethyl or isopropyl.

### Claim 11 (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 12 (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 practised on the human or animal body.

### Claim 13 (depends on 11)

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 11.

### Claim 14 (depends on 1)

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