# US 11,439,148 B2 · Pyrimidine derivatives

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- Number: US 11,439,148 B2
- Document ID: US11439148B2
- Status: Granted
- Kind: B2
- Application number: 16/768,269
- Filed: 2018-11-26
- Published: 2020-11-26
- Granted: 2022-09-13
- Earliest claimed: 2017-12-01
- Assignees: Syngenta Participations AG
- Applicants: Syngenta Participations AG
- Inventors: Niall Rae Thomson; Gordon Alastair Bell; Philip Taylor; Julia Lynne Ramsay; Stephanie Lucas; Renaud Perrin; Stephen Christopher Smith
- Web page: https://patentgrep.com/patent/US11439148B2

## CPC

- A01N 43/54: 1,3-Diazines; Hydrogenated 1,3-diazines
- A01N 25/30: characterised by the surfactants
- A01N 41/10: Sulfones; Sulfoxides
- A01N 43/40: six-membered rings
- A01N 43/56: 1,2-Diazoles; Hydrogenated 1,2-diazoles
- A01N 43/653: 1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- A01N 43/72: having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- C07D 239/52: Two oxygen atoms
- 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

This invention relates to pyrimidine derivatives, to compositions comprising the pyrimidine derivatives, to methods of making and using these compositions, and to the use of the pyrimidine derivatives as adjuvants, particularly for agrochemical use. In particular, the present invention relates to compositions comprising the pyrimidine derivatives selected from emulsifiable concentrates (EC), emulsions in water (EW), suspensions of particles in water (SC), soluble liquids (SL), capsule suspensions (CS), suspensions of particles with an emulsion (SE), dispersion concentrates (DC), suspensions of particles in oil (OD), water dispersible granules (WG), soluble granules (SG) and wettable powders (WP).

## Claims

### Claim 1

A compound of formula (I), or a salt thereof,
wherein
R1 is selected from C4-C20-alkyl and C4-C20-alkenyl;
R2 is selected from H, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl and t-butyl;
X is either
n is from 2 to 30.

### Claim 2 (depends on 1)

A compound or salt according to claim 1, wherein
X is

### Claim 3 (depends on 1)

A compound or salt according to claim 1, wherein
X is

### Claim 4 (depends on 1)

A compound or salt of claim 1 of formula (I)
wherein
R1 is selected from C6-C18-alkyl and C6-C18-alkenyl;
X is
n is from 2 to 20;
R2 is methyl or H.

### Claim 5 (depends on 4)

A compound or salt according to claim 4 wherein R2 is methyl and R1 and n are as defined in the table
Compound
R1
n
1
Hexyl
2
2
Hexyl
10
3
Hexyl
20
4
Nonyl
7
5
Nonyl
10
6
Dodecyl
7
7
Dodecyl
10
8
Hexadecyl
10
9
Oleyl
2
10
Oleyl
10
11
Oleyl
20.

### Claim 6 (depends on 1)

A compound of claim 1 of formula (I)
wherein
R1 is selected from C6-C18-alkyl and C6-C18-alkenyl;
X is
n is from 2 to 8;
R2 is methyl or H.

### Claim 7 (depends on 6)

A compound of claim 6 wherein R2 is methyl, R1 is dodecyl and n is 3.

### Claim 8 (depends on 1)

A composition comprising a biologically active ingredient, particularly an agrochemical active ingredient, and a compound according to claim 1.

### Claim 9 (depends on 1)

A tank-mix formulation comprising a compound according to claim 1.

### Claim 10 (depends on 8)

A method of controlling pests comprising applying the agrochemical composition of claim 8 to said pests or to a locus of said pests.

### Claim 11 (depends on 8)

A method of making an agrochemical composition according to claim 8, comprising combining a biologically active ingredient and a compound of formula (I), or a salt thereof,
Wherein
R1 is selected from C4-C20-alkyl and C4-C20-alkenyl;
R2 is selected from H, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl and t-butyl;
X is either
n is from 2 to 30.

### Claim 12 (depends on 1)

A composition comprising a biologically active ingredient and a compound according to claim 1, wherein the compound acts as an adjuvant in the composition.

### Claim 13 (depends on 12)

The composition of claim 12 wherein the biologically active ingredient is an agrochemical active ingredient.