# US 10,765,114 B2 · 4-amino-6-(pyridyl and 2-substitutedphenyl)-picolinates and 6-amino-2-(pyridyl and 2-substitutedphenyl)-pyrimidine-4-carboxylates and their use as herbicides

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- Number: US 10,765,114 B2
- Document ID: US10765114B2
- Status: Granted
- Kind: B2
- Application number: 14/209,675
- Filed: 2014-03-13
- Published: 2014-09-18
- Granted: 2020-09-08
- Earliest claimed: 2013-03-15
- Assignees: Dow AgroSciences LLC
- Applicants: Dow AgroSciences LLC
- Inventors: Joseph D. Eckelbarger; Jeffrey B. Epp; Lindsey G. Fischer; Natalie C. Giampietro; Jeremy Kister; Jeffrey Petkus; Joshua Roth; Norbert M. Satchivi; Paul R. Schmitzer; Thomas L. Siddall; Carla N. Yerkes
- Web page: https://patentgrep.com/patent/US10765114B2

## CPC

- A01N 43/54: 1,3-Diazines; Hydrogenated 1,3-diazines
- A01N 43/40: six-membered 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

## Abstract

4-amino-6-(pyridyl and 2-substitutedphenyl)-picolinic acids and their derivatives; 6-amino-2-(pyridyl and 2-substitutedphenyl)-pyrimidine-4-carboxylates and their derivatives; and methods of using the same as herbicides.

## Claims

### Claim 1

A compound of Formula (I):
wherein
X is CY, wherein Y is hydrogen or halogen;
R1 is OR1′, wherein R1′ is H, C1-C8 alkyl, or C7-C10 arylalkyl;
R2 is halogen, C1-C4 alkyl, C2-C4 alkenyl, or C1-C4 alkoxy;
R3 and R4 are independently hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 alkenyl, C3-C6 haloalkenyl, C3-C6 alkynyl, C3-C6 haloalkynyl, hydroxy, C1-C6 alkoxy, C1-C6 haloalkoxy, formyl, (C1-C3 alkyl)carbonyl, (C1-C3 haloalkyl)carbonyl, (C1-C6 alkoxy)carbonyl, (C1-C6 alkyl)carbamyl, (C1-C6 alkyl)sulfonyl, tri(C1-C6 alkyl)silyl, di(C1-C6 alkyl)phosphonyl, or R3 and R4 taken together with the nitrogen atom to which they are attached form a 5- or 6-membered saturated ring, or R3 and R4 taken together represent ═CR3′R4′, wherein R3′ and R4′ are independently hydrogen, C1-C6 alkyl, C3-C6 alkenyl, C3-C6 alkynyl, C1-C6 alkoxy or C1-C6 alkylamino, or, R3′ and R4′ taken together with the carbon atom to which they are attached form a 5- or 6-membered saturated ring;
Ar is:
X2 is F, Cl, Br, I, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 alkoxy, CN, or NO2;
W2 is hydrogen or F; and
Z3 is C1-C4 haloalkyl, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, or C1-C4 alkoxy;
or an N-oxide or agriculturally acceptable salt thereof.

### Claim 2 (depends on 1)

The compound according to claim 1, wherein W2 is hydrogen.

### Claim 3 (depends on 1)

The compound of claim 1, wherein R2 is Cl.

### Claim 4 (depends on 1)

The compound of claim 1, wherein Z3 is C1 haloalkyl, C1 alkyl, C2 alkenyl, C2 alkynyl, or C1 alkoxy.

### Claim 5 (depends on 1)

The compound of claim 1, wherein Y is F.

### Claim 6 (depends on 5)

The compound of claim 5, wherein Z3 is C1 haloalkyl, C1 alkyl, C2 alkenyl, C2 alkynyl, or C1 alkoxy.

### Claim 7 (depends on 6)

The compound of claim 6, wherein X2 is Cl.

### Claim 8 (depends on 1)

The compound of claim 1, wherein R3 and R4 are each hydrogen.

### Claim 9 (depends on 8)

The compound of claim 8, wherein X2 and R2 are each Cl.

### Claim 10 (depends on 8)

The compound of claim 8, wherein Z3 is C1 haloalkyl, C1 alkyl, C2 alkenyl, C2 alkynyl, or C1 alkoxy.

### Claim 11

A compound having the formula:
or an N-oxide or agriculturally acceptable salt thereof.

### Claim 12 (depends on 1)

A herbicidal composition comprising the compound of claim 1 and an agriculturally acceptable adjuvant or carrier.

### Claim 13 (depends on 12)

The composition of claim 12, further comprising at least one additional herbicidal compound.

### Claim 14 (depends on 12)

The composition of claim 12, further comprising a safener.