IP Library › Granted Patent US 12,356,976
Granted Patent B2
US 12,356,976 · App. 18/202,681 · Granted Jul 15, 2025

Selective detection of bed bugs

Inventors: Mark W. Beach (Midland, MI); Andrey N. Soukhojak (Midland, MI); Neil A. Spomer (Carmel, IN); Shane L. Mangold (Midland, MI); Ravi B. Shankar (Midland, MI); Sukrit Mukhopadhyay (Midland, MI); Jeremy Chris P. Reyes (Lake Jackson, TX); Bruce A. Jacobs (Fishers, IN); William L. Winniford (Lake Jackson, TX); Ronda L. Hamm (Carmel, IN); Phillip J. Howard (Greenville, SC); Andrew J. Pasztor, Jr. (Midland, MI); Mary D. Evenson (Zionsville, IN); Thomas G. Patterson (Westfield, IN); Natalie C. Giampietro (Carmel, IN)
Assignee: Ecolab USA Inc.
A01M1/026A01M1/023A01M2200/011
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Quick Facts
Patent No.
US 12,356,976
App. No.
18/202,681
Granted
Jul 15, 2025
Kind
B2
Abstract

A chemical agent useful for controlling pests is disclosed. The agent can be a thiol, such as a cyclic thiol according to Formula I. The agent can be used to react with a targeted biochemical analyte secreted by pests, such as bed bugs, to provide an adduct. The agent can be useful in a pest control device, system, or method for detecting pests, which can involve use of a controller and a sensor cell coated with composition containing the agent. The disclosure also describes the adduct obtained from the agent and the analyte, as well as a composition containing the agent or adduct.

Claims (55)

1. A composition comprising a gel medium and a cyclic thiol of the formula I

or a tautomer thereof, wherein

X is S or O;

Z 1 and Z 2 are each independently O or S;

R 1 is selected from the group consisting of hydrogen, C 4 -C 10 alkyl, C 2 -C 12 alkenyl, C 6 -C 10 aryl, 5- to 7-membered heteroaryl, —OR 5 , —SR 5 , —(OC 1 -C 4 alkylene) x R 5 , —(SC 1 -C 4 alkylene) y R 5 —(OC 1 -C 4 alkylene) x (SC 1 -C 4 alkylene) y R 5 , —(SC 1 -C 4 alkylene) y (OC 1 -C 4 alkylene) x R 5 , C 1 -C 3 alkylene(OC 1 -C 4 alkylene) x R 5 , C 1 -C 3 alkylene(SC 1 -C 4 alkylene) y R 5 , C 1 -C 3 alkylene(OC 1 -C 4 alkylene) x (SC 1 -C 4 alkylene) y R 5 , and C 1 -C 3 alkylene(SC 1 -C 4 alkylene) y (OC 1 -C 4 alkylene) x R 5 ;

R 2 is selected from the group consisting of hydrogen, C 4 -C 10 alkyl, C 2 -C 12 alkenyl, C 6 -C 10 aryl, 5- to 7-membered heteroaryl, —OR 5 , —SR 5 , —(OC 1 -C 4 alkylene) x R 5 , —(SC 1 -C 4 alkylene) y R 5 —(OC 1 -C 4 alkylene) x (SC 1 -C 4 alkylene) y R 5 , —(SC 1 -C 4 alkylene) y (OC 1 -C 4 alkylene) x R 5 , C 1 -C 3 alkylene(OC 1 -C 4 alkylene) x R 5 , C 1 -C 3 alkylene(SC 1 -C 4 alkylene) y R 5 , C 1 -C 3 alkylene(OC 1 -C 4 alkylene) x (SC 1 -C 4 alkylene) y R 5 , and C 1 -C 3 alkylene(SC 1 -C 4 alkylene) y (OC 1 -C 4 alkylene) x R 5 ;

R 3 , R 3′ , R 4 , and R 4′ are each independently selected from the group consisting of hydrogen, C 1 -C 8 alkyl, C 2 -C 8 alkenyl, and C 6 -C 10 aryl;

R 5 is selected from the group consisting of hydrogen, C 1 -C 8 alkyl, C 2 -C 8 alkenyl, C 6 -C 10 aryl, and a polymeric bulking group;

a is 0 or 1; and

x and y are each independently an integer from 1 to 10.

2. The composition of claim 1 , wherein X is S.

3. The composition of claim 1 , wherein Z 1 is O.

4. The composition of claim 1 , wherein Z 1 and Z 2 are each O.

5. The composition of claim 1 , wherein R 1 and R 2 are each C 4 -C 10 alkyl and are the same.

6. The composition of claim 1 , wherein R 1 and R 2 are each octyl.

7. The composition of claim 1 , having the formula

wherein R 1 is selected from the group consisting of hydrogen, C 4 -C 10 alkyl, C 2 -C 12 alkenyl, C 6 -C 10 aryl, 5- to 7-membered heteroaryl, —OR 5 , —SR 5 , —(OC 1 -C 4 alkylene) x R 3 , —(SC 1 -C 4 alkylene) y R 5 —(OC 1 -C 4 alkylene) x (SC 1 -C 4 alkylene) y R 5 , —(SC 1 -C 4 alkylene) y (OC 1 -C 4 alkylene) x R 5 , C 1 -C 3 alkylene(OC 1 -C 3 alkylene) x R 5 , C 1 -C 3 alkylene(SC 1 -C 4 alkylene) y R 5 , C 1 -C 3 alkylene(OC 1 -C 4 alkylene) x (SC 1 -C 4 alkylene) y R 5 , and C 1 -C 3 alkylene(SC 1 -C 4 alkylene) y (OC 1 -C 4 alkylene) x R 5 ; and

R 2 is selected from the group consisting of hydrogen, C 4 -C 10 alkyl, C 2 -C 12 alkenyl, C 6 -C 10 aryl, 5- to 7-membered heteroaryl, —OR 5 , —SR 5 , —(OC 1 -C 4 alkylene) x R 5 , —(SC 1 -C 4 alkylene) y R 5 —(OC 1 -C 4 alkylene) x (SC 1 -C 4 alkylene) y R 5 , —(SC 1 -C 4 alkylene) y OC 1 -C 4 alkylene) x R 5 , C 1 -C 3 alkylene(OC 1 -C 4 alkylene) x R 5 , C 1 -C 3 alkylene(SC 1 -C 4 alkylene) y R 5 , C 1 -C 3 alkylene(OC 1 -C 4 alkylene) x (SC 1 -C 4 alkylene) y R 5 , and C 1 -C 3 alkylene(SC 1 -C 4 alkylene) y (OC 1 -C 4 alkylene) x R 5 .

8. The composition of claim 1 having the formula

wherein R 1 and R 2 are each octyl.

9. The composition of claim 1 , wherein the cyclic thiol forms a cyclic adduct with an unsaturated aldehyde an unsaturated aldehyde.

10. The composition of claim 9 , wherein the unsaturated aldehyde was secreted by a pest.

11. The composition of claim 1 , wherein the gel medium comprises one or more polymers and a solvent.

12. The composition of claim 1 , wherein the gel medium comprises one or more polymers selected from polymethylphenylsiloxiane (PMPS), polydimethylsiloxane (PDMS), fluoroalcohol polycarbosilane, fluoroalcohol polysiloxane, bisphenol-containing polymer (BSP3), and poly-2-dimethylamin-ethyl-methacrylate (PDMAEMC).

13. The composition of claim 1 , wherein the gel medium immobilizes the cyclic thiol.

14. A cyclic adduct of the formula II

or a tautomer thereof, wherein

X is S or O;

Z 1 and Z 2 are each independently O or S;

R 1 is selected from the group consisting of hydrogen, C 1 -C 12 alkyl, C 2 -C 12 alkenyl, C 6 -C 10 aryl, 5- to 7-membered heteroaryl, —OR 5 , —SR 5 , —(OC 1 -C 4 alkylene) x R 5 , —(SC 1 -C 4 alkylene) y R 5 —(OC 1 -C 4 alkylene) x (SC 1 -C 4 alkylene) y R 5 , —(SC 1 -C 4 alkylene) y (OC 1 -C 4 alkylene) x R 5 , C 1 -C 3 alkylene(OC 1 -C 4 alkylene) x R 5 , C 1 -C 3 alkylene(SC 1 -C 4 alkylene) y R 5 , C 1 -C 3 alkylene(OC 1 -C 4 alkylene) x (SC 1 -C 4 alkylene) y R 5 , and C 1 -C 3 alkylene(SC 1 -C 4 alkylene) y (OC 1 -C 4 alkylene) x R 5 ;

R 2 is selected from the group consisting of hydrogen, C 1 -C 12 alkyl, C 2 -C 12 alkenyl, C 6 -C 10 aryl, 5- to 7-membered heteroaryl, —OR 5 , —SR 5 , —(OC 1 -C 4 alkylene) x R 5 , —(SC 1 -C 4 alkylene) y R 5 —(OC 1 -C 4 alkylene) x (SC 1 -C 4 alkylene) y R 5 , —(SC 1 -C 4 alkylene) y (OC 1 -C 4 alkylene) x R 5 , C 1 -C 3 alkylene(OC 1 -C 4 alkylene) x R 5 , C 1 -C 3 alkylene(SC 1 -C 4 alkylene) y R 5 , C 1 -C 3 alkylene(OC 1 -C 4 alkylene) x (SC 1 -C 4 alkylene) y R 5 , and C 1 -C 3 alkylene(SC 1 -C 4 alkylene) y (OC 1 -C 4 alkylene) x R 5 ;

R 3 , R 3′ , R 4 , and R 4′ are each independently selected from the group consisting of hydrogen, C 1 -C 8 alkyl, C 2 -C 8 alkenyl, and C 6 -C 10 aryl;

R 5 is selected from the group consisting of hydrogen, C 1 -C 8 alkyl, C 2 -C 8 alkenyl, C 6 -C 10 aryl, and a polymeric bulking group;

R 6 is C 1 -C 12 alkyl or oxo substituted C 1 -C 12 alkyl;

a is 0 or 1; and

x and y are each independently an integer from 1 to 10.

15. The cyclic adduct of claim 14 , wherein R 6 is selected from the group consisting of propyl, pentyl, 1-oxopropyl, and 1-oxopentyl.

16. The cyclic adduct of claim 14 , wherein R 6 is pentyl.

17. The cyclic adduct of claim 14 having formula

wherein R 1 is selected from the group consisting of hydrogen, C 1 -C 12 alkyl, C 2 -C 12 alkenyl, C 6 -C 10 aryl, 5- to 7-membered heteroaryl, —OR 5 , —SR 5 , —(OC 1 -C 4 alkylene) x R 5 , —(SC 1 -C 4 alkylene) y R 5 —(OC 1 -C 4 alkylene) x (SC 1 -C 4 alkylene) y R 5 , —(SC 1 -C 4 alkylene) y (OC 1 -C 4 alkylene) x R 5 , C 1 -C 3 alkylene(OC 1 -C 4 alkylene) x R 5 , C 1 -C 3 alkylene(SC 1 -C 4 alkylene) y R 5 , C 1 -C 3 alkylene(OC 1 -C 4 alkylene) x (SC 1 -C 4 alkylene) y R 5 , and C 1 -C 3 alkylene(SC 1 -C 4 alkylene) y (OC 1 -C 4 alkylene) x R 5 ;

R 2 is selected from the group consisting of hydrogen, C 1 -C 12 alkyl, C 2 -C 12 alkenyl, C 6 -C 10 aryl, 5- to 7-membered heteroaryl, —OR 5 , —SR 5 , —(OC 1 -C 4 alkylene) x R 5 , —(SC 1 -C 4 alkylene) y R 5 —(OC 1 -C 4 alkylene) x (SC 1 -C 4 alkylene) y R 5 , —(SC 1 -C 4 alkylene) y (OC 1 -C 4 alkylene) x R 5 , C 1 -C 3 alkylene(OC 1 -C 4 alkylene) x R 5 , C 1 -C 3 alkylene(SC 1 -C 4 alkylene) y R 5 , C 1 -C 3 alkylene(OC 1 -C 4 alkylene) x (SC 1 -C 4 alkylene) y R 5 , and C 1 -C 3 alkylene(SC 1 -C 4 alkylene) y (OC 1 -C 4 alkylene) x R 5 ; and

R 6 is C 1 -C 12 alkyl or oxo substituted C 1 -C 12 alkyl.

18. The cyclic adduct of claim 14 having formula

wherein R 1 and R 2 are each octyl, and R 6 is pentyl.

19. A cyclic adduct of a cyclic thiol with a biochemical analyte secreted from a pest, wherein the cyclic thiol has the structure of Formula I:

or a tautomer thereof, wherein

X is S or O;

Z 1 and Z 2 are each independently O or S;

R is selected from the group consisting of hydrogen C 4 -C 10 alkyl C 2 -C 12 alkenyl, C 6 -C 10 aryl, 5- to 7-membered heteroaryl, —OR 5 , —SR 5 , —(OC 1 -C 4 alkylene) x R 5 , —(SC 1 -C 4 alkylene) y R 5 —(OC 1 -C 4 alkylene) x (SC 1 -C 4 alkylene) y R 5 , —(SC 1 -C 4 alkylene) y (OC 1 -C 4 alkylene) x R 5 , C 1 -C 3 alkylene(OC 1 -C 4 alkylene) x R 5 , C 1 -C 3 alkylene(SC 1 -C 4 alkylene) x R 5 , C 1 -C 3 alkylene(OC 1 -C 4 alkylene) x (SC 1 -C 4 alkylene) y R 5 , and C 1 -C 3 alkylene SC 1 -C 4 alkylene) y (OC 1 -C 4 alkylene) x R 5 ;

R 2 is selected from the group consisting of hydrogen, C 4 -C 10 alkyl C 2 -C 12 alkenyl C 6 -C 10 aryl, 5- to 7-membered heteroaryl, —OR 5 , —SR 5 , —(OC 1 -C 4 alkylene) x R 5 , —(SC 1 -C 4 alkylene) x R 5 —(OC 1 -C4 alkylene) x (SC 1 -C 4 alkylene) y R 5 , —(SC 1 -C 4 alkylene) y (OC 1 -C 4 alkylene) x R 5 , C 1 -C 3 alkylene(OC 1 -C 4 alkylene) x R 5 , C 1 -C 3 alkylene(SC 1 -C 4 alkylene) y R 5 , C 1 -C 3 alkylene(OC 1 -C 4 alkylene) x (SC 1 -C 4 alkylene) y R 5 , and C 1 -C 3 alkylene(SC 1 -C 4 alkylene) y (OC 1 -C 4 alkylene) x R 5 ;

R 3 , R 3′ , R 4 , and R 4′ are each independently selected from the group consisting of hydrogen, C 1 -C 8 alkyl, C 2 -C 8 alkenyl, and C 6 -C 10 aryl;

R 5 is selected from the group consisting of hydrogen, C 1 -C 8 alkyl, C 2 -C 8 alkenyl C 6 -C 10 aryl, and a polymeric bulking group;

a is 0 or 1; and

x and y are each independently an integer from 1 to 10.

20. A composition comprising a gel medium and the cyclic adduct of claim 14 .

Assignments (3)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 17, 2024
From: CORTEVA AGRISCIENCE LLC
To: ECOLAB USA INC.
Reel/Frame 066339/0593 →
CHANGE OF NAME Recorded Oct 23, 2023
From: DOW AGROSCIENCES LLC
To: CORTEVA AGRISCIENCE LLC
Reel/Frame 065316/0211 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 20, 2023
From: BEACH, MARK W.; SOUKHOJAK, ANDREY N.; SPOMER, NEIL A.; MANGOLD, SHANE L.; SHANKAR, RAVI B.; MUKHOPADHYAY, SUKRIT; REVES, JEREMY CHRIS P.; JACOBS, BRUCE A.; WINNIFORD, WILLIAM L.; HAMM, RONDA L.; HOWARD, PHILLIP J.; PASZTOR, ANDREW J., JR.; EVENSON, MARY D.; PATTERSON, THOMAS G.; GIAMPIETRO, NATALIE C.
To: DOW AGROSCIENCES LLC
Reel/Frame 065302/0238 →
Continuity (6)
Continuation 17226222 · Apr 9, 2021
Continuation 16295785 · Mar 7, 2019
Continuation 15985093 · May 21, 2018
Provisional Application 62577437 · Oct 26, 2017
Provisional Application 62509501 · May 22, 2017
Related Publication 20230337651A1 · Oct 26, 2023
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