# US 10,246,417 B2 · Picolinamides as fungicides

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- Number: US 10,246,417 B2
- Document ID: US10246417B2
- Status: Granted
- Kind: B2
- Application number: 15/862,769
- Filed: 2018-01-05
- Published: 2018-07-05
- Granted: 2019-04-02
- Earliest claimed: 2017-01-05
- Assignees: Dow AgroSciences LLC
- Applicants: Dow AgroSciences LLC
- Inventors: Brian A. Loy; Jared W. Rigoli; Brannon Sam; Kevin G. Meyer; Chenglin Yao
- Web page: https://patentgrep.com/patent/US10246417B2

## CPC

- C07D 213/81: Amides; Imides
- A01N 43/40: six-membered rings
- A01N 43/90: having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
- A01N 47/06: containing —O—CO—O— groups; Thio analogues thereof
- A01N 47/12: containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring
- A61P 31/10: Antimycotics
- C07C 229/08: the nitrogen atom of the amino group being further bound to hydrogen atoms
- C07C 271/22: to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
- C07D 213/83: Thioacids; Thioesters; Thioamides; Thioimides
- C07D 213/89: with hetero atoms directly attached to the ring nitrogen atom
- C07D 317/54: Radicals substituted by oxygen atoms
- C07D 498/04: Ortho-condensed systems
- C07B 2200/07: Optical isomers
- C07C 2601/02: with a three-membered ring
- C07C 2601/04: with a four-membered ring
- C07C 2601/08: the ring being saturated
- C07C 2601/14: The ring being saturated
- 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
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07B: GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR (preparation of carboxylic acid esters by telomerisation C07C67/47; telomerisation C08F)

## Abstract

This disclosure relates to picolinamides of Formula I and their use as fungicides.

## Claims

### Claim 1

A composition for the control of a fungal pathogen including mixtures of at least one of the compounds of Formula I
wherein:
Q is
X is hydrogen or C(O)R5;
Y is hydrogen or C(O)R5;
Z is N or N+→O− and W is O or S;
R1 is hydrogen or alkyl, substituted with 0, 1 or multiple R8;
R2 is methyl;
R3 and R3′ are independently chosen from C2-C6 alkyl, C3-C6 cycloalkyl, aryl or heteroaryl, each optionally substituted with 0, 1 or multiple R8; Alternatively, R3 and R3′ may be taken together to form a 3-6 membered saturated or partially saturated carbocycle or heterocycle, optionally substituted with 0, 1 or multiple R8;
R4 is chosen from aryl or heteroaryl, each optionally substituted with 0, 1 or multiple R8;
R5 is chosen from alkoxy or benzyloxy, each optionally substituted with 0, 1, or multiple R8;
R6 is chosen from hydrogen, alkoxy, or halo, each optionally substituted with 0, 1, or multiple R8;
R7 is chosen from hydrogen, —C(O)R9, or —CH2OC(O)R9;
R8 is chosen from hydrogen, alkyl, aryl, acyl, halo, alkenyl, alkynyl, alkoxy, cyano, or heterocyclyl, each optionally substituted with 0, 1, or multiple R10;
R9 is chosen from alkyl, alkoxy, or aryl, each optionally substituted with 0, 1, or multiple R8;
R10 is chosen from hydrogen, alkyl, aryl, acyl, halo, alkenyl, alkoxy, or heterocyclyl;
R11 is chosen from hydrogen or alkyl, each substituted with 0, 1 or multiple R8; and
a phytologically acceptable carrier material.

### Claim 2 (depends on 1)

The composition according to claim 1, wherein O is
wherein X is hydrogen.

### Claim 3 (depends on 2)

The composition according to claim 2 wherein Z is N.

### Claim 4 (depends on 3)

The composition according to claim 3 wherein W is O.

### Claim 5 (depends on 4)

The composition according to claim 4, wherein R6 is alkoxy.

### Claim 6 (depends on 5)

The composition according to claim 5, wherein R7 is hydrogen.

### Claim 7 (depends on 6)

The composition according to claim 6, wherein R1 and R11 are independently chosen from hydrogen or alkyl, R3 and R3′ are independently chosen from C1-C6 alkyl or taken together to form a 3-6 membered saturated carbocycle, each optionally substituted with 0, 1 or multiple R8, and R4 is aryl, optionally substituted with 0, 1 or multiple R8.

### Claim 8 (depends on 5)

The composition according to claim 5, wherein R7 is chosen from —C(O)R9 or —CH2OC(O)R9.

### Claim 9 (depends on 8)

The composition according to claim 8, wherein R9 is alkyl, optionally substituted with 0, 1 or multiple R8.

### Claim 10 (depends on 9)

The composition according to claim 9, wherein R1 and Rn are independently chosen from hydrogen or alkyl, R3 and R3′ are independently chosen from C1-C6 alkyl or taken together to form a 3-6 membered saturated carbocycle, each optionally substituted with 0, 1 or multiple R8, and R4 is aryl, optionally substituted with 0, 1 or multiple R8.

### Claim 11 (depends on 1)

The composition according to claim 1 wherein the fungal pathogen is one of Leaf Blotch of Wheat (Zymoseptoria tritici), Wheat Brown Rust (Puccinia triticina), Stripe Rust (Puccinia stritformis), Scab of Apple (Venturia inaequalis), Blister Smut of Maize (Ustilago maydis), Powdery Mildew of Grapevine (Uncinula necator), Barley scald (Rhynchosporium secalis), Blast of Rice (Pyricularia oryzae), Rust of Soybean (Phakopsora pachyrhizi), Glume Blotch of Wheat (Parastagonospora nodorum), Powdery Mildew of Wheat (Blumeria graminis f. sp. tritici), Powdery Mildew of Barley (Blumeria graminis f. sp. hordes), Powdery Mildew of Cucurbits (Erysiphe cichoracearum), Anthracnose of Cucurbits (Colletotrichum lagenarium), Leaf Spot of Beet (Cercospora beticola), Early Blight of Tomato (Alternaria solani), and Net Blotch of Barley (Pyrenophora teres).

### Claim 12 (depends on 7)

The composition according to claim 7 wherein the fungal pathogen is one of Leaf Blotch of Wheat (Zymoseptoria tritici), Wheat Brown Rust (Puccinia triticina), Scab of Apple (Venturia inaequalis), Barley scald (Rhynchosporium secalis), Blast of Rice (Pyricularia oryzae), Rust of Soybean (Phakopsora pachyrhizi), Glume Blotch of Wheat (Parastagonospora nodorum), Anthracnose of Cucurbits (Colletotrichum lagenarium), Leaf Spot of Beet (Cercospora beticola), and Early Blight of Tomato (Alternaria solani).

### Claim 13 (depends on 8)

The composition according to claim 8 wherein the fungal pathogen is one of Leaf Blotch of Wheat (Zymoseptoria tritici), Wheat Brown Rust (Puccinia triticina), Scab of Apple (Venturia inaequalis), Barley scald (Rhynchosporium secalis), Blast of Rice (Pyricularia oryzae), Rust of Soybean (Phakopsora pachyrhizi), Glume Blotch of Wheat (Parastagonospora nodorum), Anthracnose of Cucurbits (Colletotrichum lagenarium), Leaf Spot of Beet (Cercospora beticola), and Early Blight of Tomato (Alternaria solani).

### Claim 14 (depends on 10)

The composition according to claim 10 wherein the fungal pathogen is one of Leaf Blotch of Wheat (Zymoseptoria tritici), Wheat Brown Rust (Puccinia triticina), Scab of Apple (Venturia inaequalis), Barley scald (Rhynchosporium secalis), Blast of Rice (Pyricularia oryzae), Rust of Soybean (Phakopsora pachyrhizi), Glume Blotch of Wheat (Parastagonospora nodorum), Anthracnose of Cucurbits (Colletotrichum lagenarium), Leaf Spot of Beet (Cercospora beticola), and Early Blight of Tomato (Alternaria solani).

### Claim 15 (depends on 7)

A method for the control and prevention of fungal attack on a plant, the method including the step of:
applying a fungicidally effective amount of at least one of the compositions of claim 7 to at least one of the plant, an area adjacent to the plant, soil adapted to support growth of the plant, a root of the plant, and foliage of the plant.

### Claim 16 (depends on 10)

A method for the control and prevention of fungal attack on a plant, the method including the step of:
applying a fungicidally effective amount of at least one of the compositions of claim 10 to at least one of the plant, an area adjacent to the plant, soil adapted to support growth of the plant, a root of the plant, and foliage of the plant.

### Claim 17 (depends on 11)

A method for the control and prevention of fungal attack on a plant, the method including the step of:
applying a fungicidally effective amount of at least one of the compositions of claim 11 to at least one of the plant, an area adjacent to the plant, soil adapted to support growth of the plant, a root of the plant, and foliage of the plant.

### Claim 18 (depends on 14)

A method for the control and prevention of fungal attack on a plant, the method including the step of:
applying a fungicidally effective amount of at least one of the compositions of claim 14 to at least one of the plant, an area adjacent to the plant, soil adapted to support growth of the plant, a root of the plant, and foliage of the plant.