IP Library Granted Patent US 12,490,741
Granted Patent B2
US 12,490,741 · App. 18/986,968 · Granted Dec 9, 2025

Molecules having pesticidal utility, and intermediates, compositions, and processes, related thereto

Inventors: Ronald J. Heemstra (Fishers, IN); Ronald Ross, Jr. (Mt. Dora, FL); Kyle A. Dekorver (Grandville, MI); Kaitlyn Gray (Indianapolis, IN); Daniel I. Knueppel (Zionsville, IN); Peter Vednor (Novi, MI); Timothy P. Martin (Noblesville, IN); Joseph D Eckelbarger (Carmel, IN); John F. Daeuble, Sr. (Carmel, IN); Ricky Hunter (Westfield, IN); David A. Demeter (Fishers, IN); Tony K. Trullinger (Westfield, IN); Erich W. Baum (South Hamilton, MA); Zoltan L. Benko (Indianapolis, IN); Nakyen Choy (Carmel, IN); Gary D. Crouse (Noblesville, IN); Fangzheng Li (Carmel, IN); Jeffrey Nissen (Indianapolis, IN); Monica B. Olson (Indianapolis, IN); Michelle Riener (Waltham, MA); Thomas C. Sparks (Greenfield, IN); Frank J. Wessels (Indianapolis, IN); Maurice C. Yap (Zionsville, IN)
Assignee: CORTEVA AGRISCIENCE LLC
A01N53/00A01N37/22A01N37/34A01N41/10A01N43/40A01N43/60A01N43/653A01N43/707A01N43/82A01N43/90C07C233/63C07C233/65C07C237/22C07C237/42C07C255/29C07C255/46C07C255/57C07C255/60C07C259/10C07C271/28C07C271/66C07C311/08C07C311/46C07C317/14C07C317/28C07C317/40C07C317/50C07C323/41C07C323/42C07C323/59C07C331/12C07C381/10C07D205/04C07D207/10C07D207/273C07D207/452C07D209/49C07D213/56C07D213/75C07D213/81C07D213/84C07D213/89C07D215/227C07D215/38C07D231/12C07D231/56C07D233/36C07D233/80C07D235/30C07D241/20C07D249/08C07D253/07C07D261/12C07D263/26C07D277/30C07D277/36C07D285/06C07D295/32C07D305/08C07D307/33C07D307/52C07D309/14C07D331/04C07D333/36C07D333/48C07D333/60C07D487/04C07C2601/02C07C2601/04C07C2601/08C07C2601/14
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 12,490,741
App. No.
18/986,968
Granted
Dec 9, 2025
Kind
B2
Abstract

This disclosure relates to the field of molecules having pesticidal utility against pests in Phyla Arthropoda, Mollusca, and Nematoda, processes to produce such molecules, intermediates used in such processes, pesticidal compositions containing such molecules, and processes of using such pesticidal compositions against such pests. These pesticidal compositions may be used, for example, as acaricides, insecticides, miticides, molluscicides, and nematicides. This document discloses molecules having the following formula (“Formula One”).

Claims (176)

1 . A molecule selected from one of the molecules listed in the following Table.

No.

Structure

F63

F64

F65

F75

F180

F187

F203

F211

F241

F242

F247

F252

F281

F297

F306

F309

F310

F311

F312

F316

F319

F330

F331

F342

F351

F352

F353

F354

F357

F383

F385

F386

F389

F390

F391

F392

F395

F396

F397

F398

F399

F400

F533

F541

F542

F543

F546

F547

F548

F549

F552

F553

F558

F559

F560

F561

F562

F563

F564

F565

F566

F572

F580

F584

F585

F586

F587

F588

F589

F590

F591

PF6

PF39

2 . A molecule according to claim 1 , wherein the carboxamido, and the phenyl, which are bonded to the cyclopropane, are in the R,R configuration.

3 . A composition comprising a molecule according to claim 1 , further comprises a carrier and/or an active ingredient.

4 . A composition according to claim 3 , the composition further comprises an active ingredient selected from acaricides, algicides, antifeedants, avicides, bactericides, bird repellents, chemosterilants, fungicides, herbicide safeners, herbicides, insect attractants, insect repellents, insecticides, mammal repellents, mating disrupters, molluscicides, nematicides, plant activators, plant growth regulators, rodenticides, synergists, and virucides, an active ingredient selected from AIGA, AI-1, AI-2, or AIGA-2, or further comprising Lotilaner, a structure selected from Table A, or a biopesticide.

TABLE A

Structure of M#—active ingredients

M#

Structure

M1

M2

M3

M4

M5

M6

5 . A composition according to claim 3 , the composition further comprises an active ingredient from Acetylcholinesterase (AChE) inhibitors; GABA-gated chloride channel antagonists; Sodium channel modulators; Nicotinic acetylcholine receptor (nAChR) agonists; Nicotinic acetylcholine receptor (nAChR) allosteric activators; Chloride channel activators; Juvenile hormone mimics; Miscellaneous nonspecific (multi-site) inhibitors; Modulators of Chordotonal Organs; Mite growth inhibitors; Microbial disruptors of insect midgut membranes; Inhibitors of mitochondrial ATP synthase; Uncouplers of oxidative phosphorylation via disruption of the proton gradient; Nicotinic acetylcholine receptor (nAChR) channel blockers; Inhibitors of chitin biosynthesis, type 0; Inhibitors of chitin biosynthesis, type 1; Moulting disruptor, Dipteran; Ecdysone receptor agonists; Octopamine receptor agonists; Mitochondrial complex III electron transport inhibitors; Mitochondrial complex I electron transport inhibitors; Voltage-dependent sodium channel blockers; Inhibitors of acetyl CoA carboxylase; Mitochondrial complex IV electron transport inhibitors; Mitochondrial complex II electron transport inhibitors; Ryanodine receptor modulators; or Group UN.

6 . A composition according to claim 3 , further comprises an active ingredient selected from group consisting of emamectin, eprinomectin, moxidectin and milbemycin oxime.

7 . A composition according to claim 5 , wherein the weight ratio of the molecule to the active ingredient is 100:1 to 1:100, 50:1 to 1:50, 20:1 to 1:20, 10:1 to 1:10, 5:1 to 1:5, 3:1 to 1:3, 2:1 to 1:2, or 1:1; and/or wherein the weight ratio of the molecule to the active ingredient is X:Y; wherein X is the parts by weight of the molecule and Y is the parts by weight of the active ingredient; further wherein the numerical range of the parts by weight for X is 0<X≤100 and the parts by weight for Y is 0<Y≤100; and further wherein X and Y are selected from Table C, optionally wherein a range of weight ratios of the molecule to the active ingredient is X 1 :Y 1 to X 2 :Y 2 ; further wherein X 1 >Y 1 and X 2 <Y 2 ; or wherein X 1 >Y 1 and X 2 >Y 2 ; or wherein X 1 <Y 1 and X 2 <Y 2 .

TABLE C

active

100

X, Y

X, Y

ingredient (Y)

50

X, Y

X, Y

X, Y

Parts by weight

20

X, Y

X, Y

X, Y

15

X, Y

X, Y

10

X, Y

X, Y

5

X, Y

X, Y

X, Y

3

X, Y

X, Y

X, Y

X, Y

2

X, Y

X, Y

X, Y

1

X, Y

X, Y

X, Y

X, Y

X, Y

1

2

3

5

10

molecule (X) Parts by weight

active

100

X, Y

ingredient (Y)

50

X, Y

X, Y

Parts by weight

20

X, Y

X, Y

15

X, Y

X, Y

X, Y

10

5

X, Y

3

X, Y

X, Y

X, Y

2

X, Y

X, Y

1

X, Y

X, Y

X, Y

X, Y

15

20

50

100

molecule (X) Parts by weight.

8 . A process to control a pest, wherein the process comprises applying to a locus, a pesticidally effective amount of a molecule or a composition according to claim 3 .

9 . A process according to claim 7 , wherein the pest is selected from the group consisting of ants, aphids, bed bugs, beetles, bristletails, caterpillars, cockroaches, crickets, earwigs, fleas, flies, grasshoppers, grubs, leafhoppers, lice, locusts, maggots, mites, nematodes, planthoppers, psyllids, sawflies, scales, silverfish, slugs, snails, spiders, springtails, stink bugs, symphylans, termites, thrips, ticks, wasps, whiteflies, and wireworms.

10 . A process according claim 7 , wherein the pest is a sap-feeding pest or a chewing pest; or wherein the pest is selected from the group consisting of aphids, leafhoppers, moths, scales, thrips, psyllids, mealybugs, stinkbugs, and whiteflies; or from the group consisting of caterpillars, beetles, grasshoppers, and locusts; or wherein the pest is selected from the group consisting of Orders Anoplura and Hemiptera; or from the group consisting of Coleoptera and Lepidoptera; or wherein the pest is selected from the group consisting of Aulacaspis spp., Aphrophora spp., Aphis spp., Bemisia spp., Coccus spp., Euschistus spp., Lygus spp., Macrosiphum spp., Nezara spp., and Rhopalosiphum spp; or from the group consisting of Anthonomus spp., Cerotoma spp., Chaetocnema spp., Colaspis spp., Cyclocephala spp., Diabrotica spp., Hypera spp., Phyllophaga spp., Phyllotreta spp., Sphenophorus spp., and Sitophilus spp.

Continuity (13)
Continuation 18802256 · Aug 13, 2024
Continuation 18166601 · Feb 9, 2023
Continuation 16794955 · Feb 19, 2020
Continuation 16203690 · Nov 29, 2018
Continuation 15679415 · Aug 17, 2017
Division 15092650 · Apr 7, 2016
Provisional Application 62148809 · Apr 17, 2015
Provisional Application 62148814 · Apr 17, 2015
Provisional Application 62148837 · Apr 17, 2015
Provisional Application 62148830 · Apr 17, 2015
Provisional Application 62148818 · Apr 17, 2015
Provisional Application 62148824 · Apr 17, 2015
Related Publication 20250134105A1 · May 1, 2025
References Cited (85)
US 7754717B2 · DiMauro et al. · 2010 [cited by applicant]
US 8067599B2 · Honold et al. · 2011 [cited by applicant]
US 8247597B2 · Fair et al. · 2012 [cited by applicant]
US 8492404B2 · Martin · 2013 [cited by examiner]
US 8756068B2 · Kikuiri et al. · 2014 [cited by applicant]
US 9215870B2 · Lo et al. · 2015 [cited by applicant]
US 9781935B2 · Heemstra · 2017 [cited by examiner]
US 9795139B2 · Eckelbarger et al. · 2017 [cited by applicant]
US 9795140B2 · Martin et al. · 2017 [cited by applicant]
US 10219516B2 · Heemstra · 2019 [cited by examiner]
US 10239817B2 · Choy et al. · 2019 [cited by applicant]
US 10258045B2 · Heemstra et al. · 2019 [cited by applicant]
US 10993440B2 · Heemstra et al. · 2021 [cited by applicant]
US 11632957B2 · Heemstra et al. · 2023 [cited by applicant]
US 20020068838A1 · Demassey et al. · 2002 [cited by applicant]
US 20030225302A1 · Demassey et al. · 2003 [cited by applicant]
US 20070072862A1 · DiMauro et al. · 2007 [cited by applicant]
US 20090306189A1 · Raemaekers et al. · 2009 [cited by applicant]
US 20090326065A1 · Matsumoto et al. · 2009 [cited by applicant]
US 20100234373A1 · DiMauro et al. · 2010 [cited by applicant]
US 20140171308A1 · Lo et al. · 2014 [cited by applicant]
US 20160302417A1 · Eckelbarger et al. · 2016 [cited by applicant]
US 20170339961A1 · Heemstra et al. · 2017 [cited by applicant]
US 20180000087A1 · Eckelbarger et al. · 2018 [cited by applicant]
US 20180007911A1 · Martin et al. · 2018 [cited by applicant]
US 20180098541A1 · Heemstra et al. · 2018 [cited by applicant]
US 20180099919A1 · Choy et al. · 2018 [cited by applicant]
US 20190090488A1 · Heemstra et al. · 2019 [cited by applicant]
US 20190150452A1 · Heemstra et al. · 2019 [cited by applicant]
US 20190166847A1 · Heemstra et al. · 2019 [cited by applicant]
US 20210015098A1 · Martin et al. · 2021 [cited by applicant]
US 20230180761A1 · Heemstra et al. · 2023 [cited by applicant]
EP 0604019B1 · 1996 [cited by applicant]
EP 0816330B1 · 2000 [cited by applicant]
EP 2319830A1 · 2011 [cited by applicant]
EP 3283459B1 · 2019 [cited by applicant]
EP 3578543A1 · 2019 [cited by applicant]
JP H1171336A · 1999 [cited by applicant]
WO 9008126A1 · 1990 [cited by applicant]
WO 9310100A1 · 1993 [cited by applicant]
WO 2005019240A2 · 2005 [cited by applicant]
WO 2008107091A1 · 2008 [cited by applicant]
WO 2010127928A1 · 2010 [cited by applicant]
WO 2010144959A1 · 2010 [cited by applicant]
WO 2011002951A1 · 2011 [cited by applicant]
WO 2014120355A1 · 2014 [cited by applicant]
WO 2016168056A1 · 2016 [cited by applicant]
WO 2016168058A1 · 2016 [cited by applicant]
WO 2016168059A1 · 2016 [cited by applicant]
WO 2017165256A1 · 2017 [cited by applicant]
WO 2018071320A1 · 2018 [cited by applicant]
WO 2018071327A1 · 2018 [cited by applicant]
WO 2018224455A1 · 2018 [cited by applicant]
WO 2019121143A1 · 2019 [cited by applicant]
WO 2019185413A1 · 2019 [cited by applicant]
WO 2019194982A1 · 2019 [cited by applicant]
Bastin R.J., et al., “Salt Selection and Optimisation Procedures for Pharmaceutical New Chemical Entities,” Organic Process Research &amp; Development, 2000, vol. 4, No. 5, pp. 427-435. [cited by applicant]
Chemical Encyclopedic Dictionary, Editor-in-chief IL Knunyants, Moskov, Soviet Encyclopedia, 1983, vol. 792, pp. 559-560. [cited by applicant]
Extended European Search Report for European Application No. 19174918.3, mailed Oct. 31, 2019, 07 Pages. [cited by applicant]
Extended European Search Report for European Application No. 19174959.7, mailed Oct. 31, 2019, 07 Pages. [cited by applicant]
Extended European Search Report for European Application No. 19175296.3, mailed Oct. 31, 2019, 09 Pages. [cited by applicant]
Gall D.L., et al., “Stereochemical Features of Glutathione-Dependent Enzymes in the [cited by applicant]
Govorushko S.M., “Mammals and Birds as Agricultural Pests: Global Situation,” Agricultural Biology, 2014, vol. 6, pp. 15-25. [cited by applicant]
International Preliminary Report on Patentability for International Application No. PCT/US2016/026409, mailed Oct. 26, 2017, 07 Pages. [cited by applicant]
International Preliminary Report on Patentability for International Application No. PCT/US2016/026413, mailed Oct. 26, 2017, 7 Pages. [cited by applicant]
International Preliminary Report on Patentability for International Application No. PCT/US2016/026417, mailed Oct. 26, 2017, 08 Pages. [cited by applicant]
International Search Report and Written Opinion for International Application No. PCT/US2016/026409, mailed Jun. 23, 2016, 09 Pages. [cited by applicant]
International Search Report and Written Opinion for International Application No. PCT/US2016/026413, mailed Jun. 17, 2016, 8 Pages. [cited by applicant]
International Search Report and Written Opinion for International Application No. PCT/US2016/026417, mailed Jun. 17, 2016, 10 Pages. [cited by applicant]
International Search Report and Written Opinion for International Application No. PCT/US2017/055699, mailed Jan. 3, 2018, 8 Pages. [cited by applicant]
International Search Report and Written Opinion for International Application No. PCT/US2017/055738, mailed Jan. 4, 2018, 10 Pages. [cited by applicant]
Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1975, pp. 2577-2579, vol. 11, ISSN 0004274310. [cited by applicant]
Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1979, vol. 10, pp. 2381-2383, ISSN 0004274312. [cited by applicant]
Kovalenko V.N., et al., “The Resolution of Trans-2,2-Dichloro-3-Methylcyclopropanecarboxylic Acid via Crystallization of its Salts With (+)- and (-)-α-Phenylethylamine, and the Transformation of the Resulting Enantiomer… [cited by applicant]
Kryshtal G.V., et al., “Recoverable Phase-Transfer Catalysts with Fluorinated Anions: Generation and Reactions of Dichlorocarbene and CCI3 Anion in the Heterogeneous System KOH(s)/CHCI3/nBu4NPF6,” European Journal of Or… [cited by applicant]
Russian Journal of Organic Chemistry, 2013, vol. 4911, pp. 1580-1593, ISSN 0004274313. [cited by applicant]
Shchekina E.G., “Helminthiasis: a Modern View of the Problem,” Provisional, 2007, No. 12, 8 pages, found on the Internet: https://provisor.com.ua/archive/2007/N12/gelmintoza.php, entire document. [cited by applicant]
Sheshenev A.E., et al., “Generation and Stereoselective Transformations of 3-Phenylcyclopropene,” Tetrahedron, Elsevier Science Publishers, Amsterdam, NL, Sep. 30, 2009, vol. 65, No. 48, pp. 10036-10046, DOI:10.1016/j.t… [cited by applicant]
Sheshenev A.E., et al., “Stereo-and Regiocontrol in Ene-dimerisation and Trimerisation of 1-Trimethylsilyl-3-Phenylcyclopropene,” Tetrahedron, Elsevier Science Publishers, Amsterdam, NL, Dec. 19, 2009, vol. 65, No. 51, … [cited by applicant]
Shvetsov S.V., et al., “Modern Computational Methods of Evaluation of Herbicidal and Pesticidal Activity of Organic Compounds,” Bashkir Chemical Journal, 2013, vol. 20(2), pp. 134-136. [cited by applicant]
Tetrahedron Letters, 2002, vol. 43, pp. 2699-2703, ISSN 0004562943. [cited by applicant]
Tyukavkina N.A., et al., Bioorganic Chemistry, 3rd edition, revised and updated, M.: Drofa, Moscow, 2004, vol. 539, pp. 47-85. [cited by applicant]
University of Groningen, Sel. Org. React. Database(SORD)1993, 1993, pp. 13-35, ISSN 0004274307. [cited by applicant]
Yasukochi H., et al., “Practical, General, and Systematic Method for Optical Resolution of Gem-Dihalo—and Monohalocyclopropanecarboxylic Acids Utilizing Chiral 1, 1′-Binaphtholmonemethyl Ethers: Application to the Synth… [cited by applicant]
Zhurnal Organicheskoi Khimii, 1983, vol. 192, pp. 263-265, ISSN 0004562946. [cited by applicant]