# US 12,213,484 B2 · Highly loaded formulations with insecticides of the ketoenol class for use in drip and drench applications

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- Number: US 12,213,484 B2
- Document ID: US12213484B2
- Status: Granted
- Kind: B2
- Application number: 17/046,743
- Filed: 2019-04-12
- Published: 2021-06-03
- Granted: 2025-02-04
- Earliest claimed: 2018-04-13
- Assignees: Bayer Aktiengesellschaft
- Applicants: Bayer Aktiengesellschaft
- Inventors: Gorka Peris; Pierre Philippe Haas; Stefan Herrmann
- Web page: https://patentgrep.com/patent/US12213484B2

## CPC

- A01N 43/12: condensed with a carbocyclic ring
- A01N 43/90: having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
- A01N 25/04: Dispersions, {emulsions, suspoemulsions, suspension concentrates} or gels (foams A01N25/16)
- A01N 43/80: five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
- A01N 47/06: containing —O—CO—O— groups; Thio analogues thereof
- 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

The present invention relates to solvent-free aqueous suspension concentrates having high active ingredient concentration, good biological efficacy and good rheological stability, and to processes for production thereof. The formulations of the invention are suitable for the field of plant protection.

## Claims

### Claim 1

A composition comprising:
a. at least one ketoenol insecticide
b. at least one dispersant,
c. at least one pH buffer,
d. xanthan as rheology modifier,
e. at least one antifreeze,
f. at least one biocide,
g. at least one defoamer, and
h. optionally further active ingredients and adjuvants, and
i. water,
wherein a) is a tetramic acid derivative of formula (I)
wherein,
W and Y are independently hydrogen, C1-C4-alkyl, chlorine, bromine, iodine or fluorine,
X is C1-C4-alkyl, C1-C4-alkoxy, chlorine, bromine or iodine,
A. B and the carbon atom to which they are bonded are C3-C6-cycloalkyl substituted by an optionally C1-C4-alkyl- or C1-C4-alkoxy-C1-C2-alkyl-substituted alkylenedioxy group that forms a 5-membered or 6-membered ketal together with the carbon atom to which it is bonded,
G is hydrogen (a) or is one of the groups
wherein,
E is a metal ion or an ammonium ion,
M is oxygen or sulfur,
R1 is straight-chain or branched C1-C6-alkyl,
R2 is straight-chain or branched C1-C6-alkyl,
and wherein components a through g are present as follows
a) 200-400 g/L
b) 40-90 g/L,
c) 0.9-2.0 g/L,
d) 3-5 g/L,
e) 100-150 g/L,
f) 0.05-1.5 g/L,
g) 0.05-1.5 g/L.

### Claim 2 (depends on 1)

The composition according to claim 1, wherein component a) is a compound of formula (I)
wherein
W is CH3,
X is CH3,
Y is CH3, Cl or Br, and
A and B together form

### Claim 3 (depends on 1)

The composition of claim 1, wherein component a) is a compound of formula (I-2)

### Claim 4 (depends on 1)

The composition of claim 1, wherein component b) is a nonionic dispersant based on one or more tristyrylphenol polyethylene glycol ethers.

### Claim 5 (depends on 1)

The composition of claim 1, wherein component c) is citrate- or phosphate-based pH buffer.

### Claim 6 (depends on 1)

The composition of claim 1, wherein component e) is an antifreeze selected from the group consisting of ureas, diols and polyols.

### Claim 7 (depends on 1)

The composition of claim 1, wherein component f) is a biocide selected from the group of the isothiazolinones.

### Claim 8 (depends on 1)

The composition of claim 1, wherein component g) is a silicone-based defoamer.

### Claim 9 (depends on 1)

The composition of claim 1, comprising
a. a compound of formula (I)
wherein the compound of formula (I) has the following definitions:
W is methyl,
X is chlorine or methyl,
Y is chlorine, bromine or methyl,
A, B and the carbon atom to which they are attached represent saturated C6-cycloalkyl which is substituted by an alkylenedioxy group which, together with the carbon atom to which it is attached, forms a 5-membered or 6-membered ketal,
G is hydrogen (a) or is one of the groups
in which
M is oxygen,
E is metal ion or an ammonium ion,
R1 is straight-chain or branched C1-C4-alkyl,
R2 is straight-chain or branched C1-C4-alky-,
b. at least one nonionic dispersant selected from the group consisting of tristyrylphenol alkoxylates and fatty acid polyglycol ether esters,
c. at least one pH buffer selected from the group consisting of citrate- and phosphate-based pH buffers,
d. at least one rheology modifier selected from the group consisting of organic thickeners based on xanthan,
e. at least one antifreeze selected from the group consisting of ureas, diols and polyols,
f. at least one biocide from the group of isothiazolinones,
g. at least one defoamer from the group of the silicone- or silane-based defoamers,
h. optionally further active ingredients and adjuvants.

### Claim 10 (depends on 1)

The composition of claim 1, comprising
a. a compound of formula (I-2):
b. at least one nonionic dispersant selected from the group consisting of tristyrylphenol alkoxylates,
c. at least one pH buffer selected from the group consisting of citrate- and phosphate-based pH buffers,
d. xanthan as rheology modifier,
e. at least one antifreeze selected from the group consisting of ethylene glycol, propylene glycol and glycerol,
f. benzisothiazolinone as biocide,
g. at least one defoamer from the group of the silicone-based defoamers,
h. optionally further active ingredients and adjuvants.

### Claim 11 (depends on 1)

A product comprising a content of a composition of claim 1.

### Claim 12 (depends on 11)

The product of claim 11 for controlling insects.