IP Library Granted Patent US 12,256,738
Granted Patent B2
US 12,256,738 · App. 18/166,601 · Granted Mar 25, 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
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Quick Facts
Patent No.
US 12,256,738
App. No.
18/166,601
Granted
Mar 25, 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 (12)

1. A process comprising

reacting 13-2 with a carbene source comprising a bromoform or a chloroform, in the presence of an inorganic base, and (−)-N-dodecyl-N-methylephedrinium bromide as a phase-transfer catalyst, at a temperature from about ambient temperature up to below the boiling point of the haloform, to form molecule 13-3 wherein

(A) R 1 is selected from the group consisting of H, F, or Cl;

(B) R 2 is selected from the group consisting of H, F, Cl, Br, (C 1 -C 6 )alkyl, and (C 1 -C 6 )haloalkyl;

(C) R 3 is selected from the group consisting of H, F, Cl, Br, (C 1 -C 6 )alkyl, (C 1 -C 6 )haloalkyl, and (C 1 -C 6 )haloalkoxy;

(D) R 4 is selected from the group consisting of H, F, Cl, Br, (C 1 -C 6 )alkyl, and (C 1 -C 6 )haloalkyl;

(E) R 5 is selected from the group consisting of H, F, and Cl;

(F) R 6 is H;

(G) R 7 is selected from the group consisting of Cl and Br;

(H) R 8 is selected from the group consisting of Cl and Br;

(I) R 9 is H;

and R a is a (C 1 -C 6 )alkyl.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 1, 2024
From: HEEMSTRA, RONALD J.; ROSS, RONALD, JR.; DEKORVER, KYLE A.; GRAY, KAITLYN; KNUEPPEL, DANIEL I.; VEDNOR, PETER; MARTIN, TIMOTHY P.; ECKELBARGER, JOSEPH D.; DAEUBLE, JOHN F., SR.; HUNTER, RICKY; DEMETER, DAVID A.; TRULLINGER, TONY K.; BAUM, ERICH W.; BENKO, ZOLTAN L.; CHOY, NAKYEN; CROUSE, GARY D.; LI, FANGZHENG; NISSEN, JEFFREY; OLSEN, MONICA B.; RIENER, MICHELLE; SPARKS, THOMAS C.; WESSELS, FRANK J.; YAP, MAURICE C.
To: DOW AGROSCIENCES LLC
Reel/Frame 068258/0074 →
CHANGE OF NAME Recorded Aug 1, 2024
From: DOW AGROSCIENCES LLC
To: CORTEVA AGRISCIENCE LLC
Reel/Frame 068274/0116 →
Continuity (11)
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 20230180761A1 · Jun 15, 2023
References Cited (93)
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 et al. · 2013 [cited by applicant]
US 8756068B2 · Kikuiri et al. · 2014 [cited by applicant]
US 9215870B2 · Lo et al. · 2015 [cited by applicant]
US 9781935B2 · Heemstra et al. · 2017 [cited by applicant]
US 9795139B2 · Eckelbarger et al. · 2017 [cited by applicant]
US 9795140B2 · Martin et al. · 2017 [cited by applicant]
US 10219516B2 · Heemstra et al. · 2019 [cited by applicant]
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]
By Kryshtal et al., Eur. J. Org. Chem., (2008), p. 1777-1782. [cited by examiner]
Extended European Search Report for European Application No. 19174918.3, mailed Oct. 31, 2019, 7 Pages. [cited by applicant]
Extended European Search Report for European Application No. 19174959.7, mailed Oct. 31, 2019, 7 Pages. [cited by applicant]
Extended European Search Report for European Application No. 19175296.3, mailed Oct. 31, 2019, 9 Pages. [cited by applicant]
International Preliminary Report on Patentability for International Application No. PCT/US2016/026409, 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, 8 Pages. [cited by applicant]
International Search Report and Written Opinion for International Application No. PCT/US2016/026409, mailed Jun. 23, 2016, 9 Pages. [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 Synt… [cited by applicant]
Bastin R.J., et al., “Salt Selection and Optimisation Procedures for Pharmaceutical New Chemical Entities,” Organic Process Research & 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 Sphingobium sp. Strain SYK-6 Beta-Aryl Etherase Pathway,” The Journal of Biological Chemistry, Mar. 21, 2014, vol. 289, No. 12, pp. 865… [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 Synt… [cited by applicant]
Zhurnal Organicheskoi Khimii, 1983, vol. 192, pp. 263-265, ISSN 0004562946. [cited by applicant]