IP Library Granted Patent US 12,285,011
Granted Patent B2
US 12,285,011 · App. 17/309,641 · Granted Apr 29, 2025

Insecticidal formulation for vector and pest control with increased contact efficacy

Inventors: Arnoldus Vermeer (Monheim, DE); Peter Hertlein (Leichlingen, DE); Sebastian Horstmann (Leverkusen, DE); Volker Gutsmann (Langenfeld, DE); Alexander Arlt (Cologne, DE); Robert Velten (Langenfeld, DE)
Assignee: DISCOVERY PURCHASER CORPORATION
A01N25/10A01N37/18A01N43/56A01N43/76A01P7/04
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Quick Facts
Patent No.
US 12,285,011
App. No.
17/309,641
Granted
Apr 29, 2025
Kind
B2
Abstract

The present invention relates to insecticidal formulations for vector and pest control with increased contact efficacy, more particularly to insecticidal active ingredient—matrix particles and insecticidal compositions comprising such insecticidal active ingredient—matrix particles, as well as to methods and uses of such insecticidal formulations.

Claims (39)

1. Insecticidal active ingredient-matrix material particles with a particle size d50 of 0.1 to 75 microns, comprising

a) at least one insecticidal active ingredient selected from the group consisting of isoxazolines, meta-diamides, arylpyrazolheteroarylamides and arylpyrazolarylamides, wherein the at least one insecticidal active ingredient has a melting point of equal or above 110° C. and a water solubility of equal or below 0.1%, and wherein the at least one insecticidal active ingredient is distributed in

b) a matrix material wherein the matrix material is a wax, or a combination of waxes, wherein the matrix material has a softening point that is at least 30° C. under the melting point of the at least one insecticidal active ingredient,

wherein the insecticidal active ingredient-matrix material particle does not exhibit a melting peak of the active ingredient when measured in a second heating cycle after heating to a temperature of at least 20° C. above the melting point of the at least one insecticidal ingredient at a steady heating rate using Differential Scanning calorimetry.

2. The insecticidal active ingredient-matrix material particles of claim 1 , wherein in the first heating cycle of a Differential Scanning calorimetry the at least one insecticidal active ingredient and the matrix material are heated to a temperature of at least 20° C. above the melting point of the at least one insecticidal active ingredient at a steady heating rate.

3. The insecticidal active ingredient-matrix material particles of claim 2 , wherein the maximal heating temperature of the first heating cycle is retained for a period of at least 10 minutes.

4. The insecticidal active ingredient-matrix material particles of claim 2 , wherein the at least one insecticidal active ingredient and the matrix material are cooled down to a temperature of between 0° C. to 40° C. between the first and second heating cycle at a steady cooling rate.

5. The insecticidal active ingredient-matrix material particles according to claim 1 , wherein the weight ratio between the at least one insecticidal active ingredient and the matrix material is from 1:99 to 1:1.

6. The insecticidal active ingredient-matrix material particles according to claim 1 , wherein the at least one insecticidal active ingredient selected from the group consisting of 2-chloro-N-cyclopropyl-5-{1-[2,6-dichloro-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)phenyl]-1H-pyrazol-4-yl}-N-methylnicotinamide, 3-[benzoyl(methyl)amino]-N-[2-bromo-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-6-(trifluoromethyl)phenyl]-2-fluorobenzamide and 4-[(5S)-5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-N-[(4R)-2-ethyl-3-oxo-1,2-oxazolidin-4-yl]-2-methylbenzamide.

7. An insecticidal composition, wherein the insecticidal composition comprises

a) the insecticidal active ingredient-matrix material particles of claim 1 ,

b) one or more surfactant(s),

c) optionally further adjuvants selected from the group of anti-freeze agents, anti-foam agents, preservatives, anti-oxidants, thickeners and colorants, and

d) a liquid phase.

8. The insecticidal composition of claim 7 , wherein the insecticidal composition comprises

a) from 1 to 70% by weight of insecticidal active ingredient-matrix material particles according to claim 1 ,

b) from 1 to 25% of one or more surfactant(s),

c) from 0 to 25% by weight of adjuvants selected from the group of anti-freeze agents, anti-foam agents, preservatives, anti-oxidants, thickeners and colorants, and

d) a liquid phase, which adds up to 100% per weight of the total insecticidal composition.

9. The insecticidal composition according to claim 7 , wherein the insecticidal composition is in the form of a suspension concentrate (SC) or a spray solution thereof.

10. The insecticidal active ingredient-matrix material particles of claim 1 , wherein the at least one insecticidal active ingredient comprises an amorphous state.

11. The insecticidal active ingredient-matrix material particles of claim 1 , wherein the matrix material particles inhibit the growth of the at least one active ingredient in a crystalline state.

12. A method for controlling pests, comprising applying insecticidal active ingredient-matrix material particles of claim 1 .

13. A method to identify a useful matrix material for preparing the insecticidal active ingredient-matrix material particles of claim 1 with Differential Scanning calorimetry, comprising:

a) heating at least one insecticidal active ingredient selected from the group consisting of isoxazolines, meta-diamides, arylpyrazolheteroarylamides and arylpyrazolarylamides and a matrix material to be tested are heated to a temperature of at least 20° C. above the melting point of the at least one insecticidal active ingredient at a steady heating rate in a first heating cycle of the Differential Scanning calorimetry,

b) retaining the maximal heating temperature of the first heating cycle for a period of at least 10 minutes,

c) cooling the temperature is down to a temperature of between 0° C. to 40° C.,

d) in a second heating cycle step, raising the temperature to a temperature of at least 20° C. above the melting point of the at least one insecticidal active ingredient at a steady heating rate, and

e) identifying a useful matrix material in the case that the insecticidal active ingredient matrix material combination does not exhibit a melting peak when measured in the second heating cycle of the Differential Scanning calorimetry,

wherein the matrix material is a wax, or a combination of waxes.

14. A method for increasing the contact efficacy of an insecticidal active ingredient selected from the group consisting of isoxazolines, meta-diamides, arylpyrazolheteroarylamides and arylpyrazolarylamides with an insecticidal composition according to claim 9 , in comparison to a conventional suspension concentrate formulation with the same insecticidal active ingredient.

15. A method for controlling pests, comprising applying an insecticidal composition according to claim 7 .

16. A method to identify a useful matrix material for preparing the insecticidal composition of claim 7 with Differential Scanning calorimetry, comprising:

a) heating at least one insecticidal active ingredient selected from the group consisting of isoxazolines, meta-diamides, arylpyrazolheteroarylamides and arylpyrazolarylamides and a matrix material to be tested are heated to a temperature of at least 20° C. above the melting point of the at least one insecticidal active ingredient at a steady heating rate in a first heating cycle of the Differential Scanning calorimetry,

b) retaining the maximal heating temperature of the first heating cycle for a period of at least 10 minutes,

c) cooling the temperature is down to a temperature of between 0° C. to 40° C.,

d) in a second heating cycle step, raising the temperature to a temperature of at least 20° C. above the melting point of the at least one insecticidal active ingredient at a steady heating rate, and

e) identifying a useful matrix material in the case that the insecticidal active ingredient matrix material combination does not exhibit a melting peak when measured in the second heating cycle of the Differential Scanning calorimetry,

wherein the matrix material is a wax, or a combination of waxes.

Assignments (5)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 20, 2023
From: BAYER AKTIENGESELLSCHAFT
To: DISCOVERY PURCHASER CORPORATION
Reel/Frame 062442/0538 →
ABL PATENT SECURITY AGREEMENT Recorded Oct 4, 2022
From: DISCOVERY PURCHASER CORPORATION
To: BARCLAYS BANK PLC, AS ADMINISTRATIVE AGENT
Reel/Frame 061603/0988 →
FIRST LIEN PATENT SECURITY AGREEMENT Recorded Oct 4, 2022
From: DISCOVERY PURCHASER CORPORATION
To: BANK OF MONTREAL, AS COLLATERAL AGENT
Reel/Frame 061604/0001 →
SECOND LIEN PATENT SECURITY AGREEMENT Recorded Oct 4, 2022
From: DISCOVERY PURCHASER CORPORATION
To: BANK OF MONTREAL, AS COLLATERAL AGENT
Reel/Frame 061604/0013 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 2, 2021
From: VERMEER, ARNOLDUS; HERTLEIN, PETER; HORSTMANN, SEBASTIN; GUTSMANN, VOLKER; ARLT, ALEXANDER; VELTEN, ROBERT
To: BAYER AKTIENGESELLSCHAFT
Reel/Frame 058268/0719 →