IP Library › Granted Patent US 10,219,516

Granted Patent B2

US 10,219,516 · App. 15/679,415 · Granted Mar 5, 2019

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

Inventors: Ronald J. Heemstra (Fishers, IN); Ronald Ross, Jr. (Zionsville, IN); Kyle A. DeKorver (Lafayette, IN); Kaitlyn Gray (Indianapolis, IN); Daniel I. Knueppel (Zionsville, IN); Peter Vednor (Carmel, IN); 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 (Greenwood, IN); 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 (Watertown, MA); Thomas C. Sparks (Greenfield, IN); Frank J. Wessels (Indianapolis, IN); Maurice C. Yap (Zionsville, IN)

Assignee: Dow AgroSciences LLC

A01N53/00 C07C233/63 C07C233/65 C07C237/22 C07C237/42 C07C255/29 C07C255/46 C07C255/57 C07C255/60 C07C259/10 C07C271/28 C07C271/66 C07C311/08 C07C311/46 C07C317/14 C07C317/28 C07C317/40 C07C317/50 C07C323/41 C07C323/42 C07C323/59 C07C331/12 C07C381/10 C07D205/04 C07D207/273 C07D207/452 C07D209/49 C07D213/56 C07D213/84 C07D213/89 C07D215/227 C07D215/38 C07D231/56 C07D233/36 C07D233/80 C07D235/30 C07D241/20 C07D253/07 C07D261/12 C07D263/26 C07D277/30 C07D277/36 C07D307/33 C07D307/52 C07D333/48 C07D333/60 C07D487/04 C07C2601/02 C07C2601/04 C07C2601/08 C07C2601/14

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Quick Facts

Patent No.: US 10,219,516
App. No.: 15/679,415
Granted: Mar 5, 2019
Kind: B2

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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 (138)

1. A process to control a pest, said process comprising, applying to a locus, a pesticidally effective amount of a molecule having the following formula

wherein:

(A) R 1 is selected from the group consisting of H, F, Cl, Br, CN, NH 2 , NO 2 , (C 1 -C 6 )alkyl, (C 3 -C 6 )cycloalkyl, (C 2 -C 6 )alkenyl, (C 3 -C 6 )cycloalkenyl, (C 2 -C 6 )alkynyl, (C 1 -C 6 )alkoxy, (C 1 -C 6 )haloalkyl, (C 3 -C 6 )halocycloalkyl, (C 2 -C 6 )haloalkenyl, (C 3 -C 6 )halocycloalkenyl, (C 1 -C 6 )haloalkoxy, S(C 1 -C 6 )alkyl, S(O)(C 1 -C 6 )alkyl, S(O) 2 (C 1 -C 6 )alkyl, S(C 1 -C 6 )haloalkyl, S(O)(C 1 -C 6 )haloalkyl, S(O) 2 (C 1 -C 6 )haloalkyl, (C 1 -C 6 )alkyl-S(O) 2 NH 2 , and (C 1 -C 6 )haloalkyl-S(O) 2 NH 2 ;

(B) R 2 is selected from the group consisting of H, F, Cl, Br, CN, NH 2 , NO 2 , (C 1 -C 6 )alkyl, (C 3 -C 6 )cycloalkyl, (C 2 -C 6 )alkenyl, (C 3 -C 6 )cycloalkenyl, (C 2 -C 6 )alkynyl, (C 1 -C 6 )alkoxy, (C 1 -C 6 )haloalkyl, (C 3 -C 6 )halocycloalkyl, (C 2 -C 6 )haloalkenyl, (C 3 -C 6 )halocycloalkenyl, (C 1 -C 6 )haloalkoxy, S(C 1 -C 6 )alkyl, S(O)(C 1 -C 6 )alkyl, S(O) 2 (C 1 -C 6 )alkyl, S(C 1 -C 6 )haloalkyl, S(O)(C 1 -C 6 )haloalkyl, S(O) 2 (C 1 -C 6 )haloalkyl, (C 1 -C 6 )alkyl-S(O) 2 NH 2 , and (C 1 -C 6 )haloalkyl-S(O) 2 NH 2 ;

(C) R 3 is selected from the group consisting of H, F, Cl, Br, CN, NH 2 , NO 2 , (C 1 -C 6 )alkyl, (C 3 -C 6 )cycloalkyl, (C 2 -C 6 )alkenyl, (C 3 -C 6 )cycloalkenyl, (C 2 -C 6 )alkynyl, (C 1 -C 6 )alkoxy, (C 1 -C 6 )haloalkyl, (C 3 -C 6 )halocycloalkyl, (C 2 -C 6 )haloalkenyl, (C 3 -C 6 )halocycloalkenyl, (C 1 -C 6 )haloalkoxy, S(C 1 -C 6 )alkyl, S(O)(C 1 -C 6 )alkyl, S(O) 2 (C 1 -C 6 )alkyl, S(C 1 -C 6 )haloalkyl, S(O)(C 1 -C 6 )haloalkyl, S(O) 2 (C 1 -C 6 )haloalkyl, (C 1 -C 6 )alkyl-S(O) 2 NH 2 , and (C 1 -C 6 )haloalkyl-S(O) 2 NH 2 ;

(D) R 4 is selected from the group consisting of H, F, Cl, Br, CN, NH 2 , NO 2 , (C 1 -C 6 )alkyl, (C 3 -C 6 )cycloalkyl, (C 2 -C 6 )alkenyl, (C 3 -C 6 )cycloalkenyl, (C 2 -C 6 )alkynyl, (C 1 -C 6 )alkoxy, (C 1 -C 6 )haloalkyl, (C 3 -C 6 )halocycloalkyl, (C 2 -C 6 )haloalkenyl, (C 3 -C 6 )halocycloalkenyl, (C 1 -C 6 )haloalkoxy, S(C 1 -C 6 )alkyl, S(O)(C 1 -C 6 )alkyl, S(O) 2 (C 1 -C 6 )alkyl, S(C 1 -C 6 )haloalkyl, S(O)(C 1 -C 6 )haloalkyl, S(O) 2 (C 1 -C 6 )haloalkyl, (C 1 -C 6 )alkyl-S(O) 2 NH 2 , and (C 1 -C 6 )haloalkyl-S(O) 2 NH 2 ;

(E) R 5 is selected from the group consisting of H, F, Cl, Br, CN, NH 2 , NO 2 , (C 1 -C 6 )alkyl, (C 3 -C 6 )cycloalkyl, (C 2 -C 6 )alkenyl, (C 3 -C 6 )cycloalkenyl, (C 2 -C 6 )alkynyl, (C 1 -C 6 )alkoxy, (C 1 -C 6 )haloalkyl, (C 3 -C 6 )halocycloalkyl, (C 2 -C 6 )haloalkenyl, (C 3 -C 6 )halocycloalkenyl, (C 1 -C 6 )haloalkoxy, S(C 1 -C 6 )alkyl, S(O)(C 1 -C 6 )alkyl, S(O) 2 (C 1 -C 6 )alkyl, S(C 1 -C 6 )haloalkyl, S(O)(C 1 -C 6 )haloalkyl, S(O) 2 (C 1 -C 6 )haloalkyl, (C 1 -C 6 )alkyl-S(O) 2 NH 2 , and (C 1 -C 6 )haloalkyl-S(O) 2 NH 2 ;

(F) R 6 is selected from the group consisting of H and (C 1 -C 6 )alkyl;

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

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

(I) R 9 is selected from the group consisting of H and (C 1 -C 6 )alkyl;

(J) Q 1 is selected from the group consisting of O and S;

(K) Q 2 is selected from the group consisting of O and S;

(L) R 10 is selected from the group consisting of H, (C 1 -C 6 )alkyl, (C 2 -C 6 )alkenyl, (C 1 -C 6 )haloalkyl, (C 1 -C 6 )alkyl(C 1 -C 6 )alkoxy, C(═O)(C 1 -C 6 )alkyl, and (C 1 -C 6 )alkoxy, C(═O)(C 1 -C 6 )alkyl;

(M) R 11 is selected from the group consisting of H, F, Cl, Br, I, CN, NH 2 , NO 2 , (C 1 -C 6 )alkyl, (C 3 -C 6 )cycloalkyl, (C 2 -C 6 )alkenyl, (C 3 -C 6 )cycloalkenyl, (C 2 -C 6 )alkynyl, (C 1 -C 6 )alkoxy, (C 1 -C 6 )haloalkyl, (C 3 -C 6 )halocycloalkyl, (C 2 -C 6 )haloalkenyl, (C 3 -C 6 )halocycloalkenyl, (C 1 -C 6 )haloalkoxy, S(C 1 -C 6 )alkyl, S(O)(C 1 -C 6 )alkyl, S(O) 2 (C 1 -C 6 )alkyl, S(C 1 -C 6 )haloalkyl, S(O)(C 1 -C 6 )haloalkyl, S(O) 2 (C 1 -C 6 )haloalkyl, (C 1 -C 6 )alkyl-S(O) 2 NH 2 , and (C 1 -C 6 )haloalkyl-S(O) 2 NH 2 ;

(N) R 12 is selected from the group consisting of H, F, Cl, Br, I, CN, NH 2 , NO 2 , (C 1 -C 6 )alkyl, (C 3 -C 6 )cycloalkyl, (C 2 -C 6 )alkenyl, (C 3 -C 6 )cycloalkenyl, (C 2 -C 6 )alkynyl, (C 1 -C 6 )alkoxy, (C 1 -C 6 )haloalkyl, (C 3 -C 6 )halocycloalkyl, (C 2 -C 6 )haloalkenyl, (C 3 -C 6 )halocycloalkenyl, (C 1 -C 6 )haloalkoxy, S(C 1 -C 6 )alkyl, S(O)(C 1 -C 6 )alkyl, S(O) 2 (C 1 -C 6 )alkyl, S(C 1 -C 6 )haloalkyl, S(O)(C 1 -C 6 )haloalkyl, S(O) 2 (C 1 -C 6 )haloalkyl, (C 1 -C 6 )alkyl-S(O) 2 NH 2 , and (C 1 -C 6 )haloalkyl-S(O) 2 NH 2 ;

(O) X 1 is selected from the group consisting of

(1) N,

(2) NO, and

(3) CR 13 ,

wherein R 13 is selected from the group consisting of H, F, Cl, Br, I, CN, NH 2 , NO 2 , CHO, (C 1 -C 6 )alkyl, (C 3 -C 6 )cycloalkyl, (C 2 -C 6 )alkenyl, (C 3 -C 6 )cycloalkenyl, (C 2 -C 6 )alkynyl, (C 1 -C 6 )alkoxy, (C 1 -C 6 )haloalkyl, (C 3 -C 6 )halocycloalkyl, (C 2 -C 6 )haloalkenyl, (C 3 -C 6 )halocycloalkenyl, (C 1 -C 6 )haloalkoxy, S(C 1 -C 6 )alkyl, S(O)(C 1 -C 6 )alkyl, S(O) 2 (C 1 -C 6 )alkyl, S(C 1 -C 6 )haloalkyl, S(O)(C 1 -C 6 )haloalkyl, S(O) 2 (C 1 -C 6 )haloalkyl, (C 1 -C 6 )alkyl-S(O) 2 NH 2 , (C 1 -C 6 )haloalkyl-S(O) 2 NH 2 , and triazolyl;

(P) X 2 is selected from the group consisting of

(1) N,

(2) NO, and

(3) CR 14 ,

wherein R 14 is selected from the group consisting of H, F, Cl, Br, I, CN, NH 2 , NO 2 , (C 1 -C 6 )alkyl, (C 3 -C 6 )cycloalkyl, (C 2 -C 6 )alkenyl, (C 3 -C 6 )cycloalkenyl, (C 2 -C 6 )alkynyl, (C 1 -C 6 )alkoxy, (C 1 -C 6 )haloalkyl, (C 3 -C 6 )halocycloalkyl, (C 2 -C 6 )haloalkenyl, (C 3 -C 6 )halocycloalkenyl, (C 1 -C 6 )haloalkoxy, S(C 1 -C 6 )alkyl, S(O)(C 1 -C 6 )alkyl, S(O) 2 (C 1 -C 6 )alkyl, S(C 1 -C 6 )haloalkyl, S(O)(C 1 -C 6 )haloalkyl, S(O) 2 (C 1 -C 6 )haloalkyl, (C 1 -C 6 )alkyl-S(O) 2 NH 2 , and (C 1 -C 6 )haloalkyl-S(O) 2 NH 2 ;

(Q) X 3 is selected from the group consisting of N(R 15 )(substituted or unsubstituted phenyl), N(R 15 )(substituted or unsubstituted heterocyclyl), and substituted or unsubstituted heterocyclyl,

(a) wherein said R 15 is selected from the group consisting of H, (C 1 -C 6 )alkyl, (C 2 -C 6 )alkenyl, (C 2 -C 6 )alkynyl, (C 1 -C 6 )haloalkyl, (C 1 -C 6 )alkyl(C 1 -C 6 )alkoxy, C(═O)(C 1 -C 6 )alkyl, and (C 1 -C 6 )alkoxyC(═O)(C 1 -C 6 )alkyl,

(b) wherein said substituted phenyl and substituted heterocyclyl has one or more substituents selected from the group consisting of F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO 2 , OH, (C 1 -C 6 )alkoxy, (C 1 -C 6 )alkyl, (C 1 -C 6 )alkylphenyl, (C 1 -C 6 )alkyl-S(O) 2 NH 2 , (C 1 -C 6 )haloalkoxy, (C 1 -C 6 )haloalkyl, (C 1 -C 6 )haloalkyl-S(O) 2 NH 2 , (C 2 -C 6 )alkenyl, (C 2 -C 6 )alkynyl, (C 2 -C 6 )haloalkenyl, (C 3 -C 6 )cycloalkenyl, (C 3 -C 6 )cycloalkyl, (C 3 -C 6 )halocycloalkenyl, (C 3 -C 6 )halocycloalkyl, (C 1 -C 6 )alkyl((C 1 -C 6 )alkyl)(═NO(C 1 -C 6 )alkyl), C(═NO(C 1 -C 6 )alkyl)(C 1 -C 6 )alkyl, C(O)(C 1 -C 6 )alkyl, C(O)NH(C 1 -C 6 )alkyl, C(O)NHphenyl, C(O)O(C 1 -C 6 )alkyl, CH(═NO(C 1 -C 6 )alkyl), imidazolyl, N((C 1 -C 6 )alkyl)(C(O)(C 1 -C 6 )alkyl), N((C 1 -C 6 )alkyl)(C(O)(C 1 -C 6 )alkyl-O(C 1 -C 6 )alkyl), N((C 1 -C 6 )alkyl)(C(O)(C 1 -C 6 )haloalkyl), N((C 1 -C 6 )alkyl)(C(O)O(C 1 -C 6 )alkyl), N((C 1 -C 6 )alkyl) 2 , N(C(O)O(C 1 -C 6 )alkyl) 2 , N═CH-phenyl, NH((C 1 -C 6 )alkylC(O)(C 1 -C 6 )alkyl), NH(C(O)(C 1 -C 6 )alkyl), NH(C(O)(C 2 -C 6 )alkenyl), NH(C(O)(C 3 -C 6 )cycloalkyl), NH(C 1 -C 6 )alkyl, NH(C 1 -C 6 )alkenyl, NH(C 1 -C 6 )alkynyl, NH(C 1 -C 6 )alkylphenyl, NH(S(O) 2 (C 1 -C 6 )alkyl), NH 2 , NHC(O)(C 1 -C 6 )alkylphenyl, NHC(O)(C 1 -C 6 )haloalkyl, NH—C(O)O(C 1 -C 6 )alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(═NCN)((C 1 -C 6 )alkyl), S(C 1 -C 6 )alkyl, S(C 1 -C 6 )haloalkyl, S(O)(═NCN)((C 1 -C 6 )alkyl), S(O)(C 1 -C 6 )alkyl, S(O)(C 1 -C 6 )haloalkyl, S(O) 2 (C 1 -C 6 )alkyl, S(O) 2 (C 1 -C 6 )haloalkyl, SCN, thiazolyl, thienyl, and triazolyl,

wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C 1 -C 6 )alkyl, NH(C 3 -C 6 )cycloalkylCH 2 O(C 1 -C 6 )alkyl, NH(C 3 -C 6 )cycloalkylCH 2 O(C 1 -C 6 )haloalkyl, NHCH 2 (C 3 -C 6 )cycloalkyl, NH 2 , NO 2 , oxo, (C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy, and C(O)O—(C 1 -C 6 )alkyl; and

N-oxides, agriculturally acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, resolved stereoisomers, and tautomers, of the molecules of Formula One.

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

3. A process according to claim 1 , wherein said molecule

wherein:

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

(B) R 2 is selected from the group consisting of H, F, Cl, and Br;

(D) R 4 is selected from the group consisting of H, F, Cl, and Br;

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

(F) R 6 is selected from the group consisting of H and (C 1 -C 6 )alkyl;

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

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

(I) R 9 is selected from the group consisting of H and (C 1 -C 6 )alkyl;

(J) Q 1 is O;

(K) Q 2 is O;

(L) R 10 is selected from the group consisting of H and (C 1 -C 6 )alkyl;

(M) R 11 is selected from the group consisting of H, F, Cl, Br, and I;

(N) R 12 is selected from the group consisting of H, F, Cl, Br, and I;

(O) X 1 is CR 13 ,

wherein R 13 is (C 1 -C 6 )alkyl;

(P) X 2 is CR 14 ,

wherein R 14 is H;

(Q) X 3 is selected from the group consisting of N(R 15 )(substituted or unsubstituted phenyl), N(R 15 )(substituted or unsubstituted heterocyclyl), and substituted or unsubstituted heterocyclyl,

4. A process according to claim 1 , wherein said molecule wherein:

(A) R 1 is selected from the group consisting of H, F, Cl, Br, CN, NO 2 , (C 1 -C 6 )haloalkoxy, and (C 1 -C 6 )haloalkyl;

(B) R 2 is selected from the group consisting of H, F, Cl, Br, CN, NO 2 , (C 1 -C 6 )haloalkoxy, and (C 1 -C 6 )haloalkyl;

(C) R 3 is selected from the group consisting of H, F, Cl, Br, CN, NO 2 , (C 1 -C 6 )haloalkoxy, and (C 1 -C 6 )haloalkyl;

(D) R 4 is selected from the group consisting of H, F, Cl, Br, CN, NO 2 , (C 1 -C 6 )haloalkoxy, and (C 1 -C 6 )haloalkyl;

(E) R 5 is selected from the group consisting of H, F, Cl, Br, CN, NO 2 , (C 1 -C 6 )haloalkoxy, and (C 1 -C 6 )haloalkyl;

(F) R 6 is H;

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

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

(I) R 9 is H;

(J) Q 1 is selected from the group consisting of O and S;

(K) Q 2 is selected from the group consisting of O and S;

(L) R 10 is selected from the group consisting of H and (C 1 -C 6 )alkyl;

(M) R 11 is selected from the group consisting of H, F, Cl, Br, CN, NO 2 , (C 1 -C 6 )alkyl, (C 1 -C 6 )haloalkyl, and (C 1 -C 6 )alkoxy;

(N) R 12 is selected from the group consisting of H, F, Cl, Br, CN, NO 2 , (C 1 -C 6 )alkyl, (C 1 -C 6 )haloalkyl, and (C 1 -C 6 )alkoxy;

(O) X 1 is CR 13 ,

wherein R 13 is selected from the group consisting of H, F, Cl, Br, CN, NO 2 , (C 1 -C 6 )alkyl, (C 1 -C 6 )haloalkyl, and (C 1 -C 6 )alkoxy;

(P) X 2 is CR 14 ,

wherein R 14 is selected from the group consisting H, F, Cl, Br, CN, NO 2 , (C 1 -C 6 )alkyl, (C 1 -C 6 )haloalkyl, and (C 1 -C 6 )alkoxy;

(Q) X 3 is selected from the group consisting of N(R 15 )(substituted or unsubstituted phenyl), N(R 15 )(substituted or unsubstituted heterocyclyl), and substituted or unsubstituted heterocyclyl,

wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, CN, OH, NH(C 1 -C 6 )alkyl, NH(C 3 -C 6 )cycloalkylCH 2 O(C 1 -C 6 )alkyl, NH(C 3 -C 6 )cycloalkylCH 2 O(C 1 -C 6 )haloalkyl, NHCH 2 (C 3 -C 6 )cycloalkyl, NH 2 , NO 2 , oxo, (C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy, and C(O)O—(C 1 -C 6 )alkyl.

5. A process according to claim 1 , wherein said molecule R 1 , R 2 , R 3 , R 4 , and R 5 are each independently selected from the group consisting of H, F, Cl, Br, OCF 3 , and CF 3 .

6. A process according to claim 1 , wherein said molecule R 7 and R 8 are Cl.

7. A process according to claim 1 , wherein said molecule R 7 and R 8 are not the same.

8. A process according to claim 1 , wherein said molecule R 12 is selected from the group consisting of H, F, Cl, Br, CH 3 , and CF 3 .

9. A process according to claim 1 , wherein said molecule X 1 is CR 13 , wherein R 13 is selected from the group consisting of F, Cl, CH 3 , and OCH 3 .

10. A process according to claim 1 , wherein said molecule X 2 is CR 14 , wherein R 14 is selected from the group consisting of H, F, and C 1 .

11. A process according to claim 1 , wherein said molecule

R 1 is selected from the group consisting of H, F, Cl, Br, OCF 3 , and CF 3 ;

R 2 is selected from the group consisting of H, F, Cl, Br, OCF 3 , and CF 3 ;

R 3 is selected from the group consisting of H, F, Cl, Br, OCF 3 , and CF 3 ;

R 4 is selected from the group consisting of H, F, Cl, Br, OCF 3 , and CF 3 ;

R 5 is selected from the group consisting of H, F, Cl, Br, OCF 3 , and CF 3 ;

R 7 is Cl;

R 8 is Cl;

Q 1 is O;

Q 2 is O;

R 10 is H;

R 11 is H;

R 12 is selected from the group consisting of H, F, Cl, Br, CH 3 , and CF 3 ;

X 1 is CR 13 , wherein R 13 is selected from the group consisting of F, Cl, CH 3 , and OCH 3 ;

X 2 is CR 14 , wherein R 14 is selected from the group consisting of H, F, and Cl; and

X 3 is selected from the group consisting of N(R 15 )(substituted or unsubstituted phenyl), N(R 15 )(substituted or unsubstituted heterocyclyl), and substituted or unsubstituted heterocyclyl,

(b) wherein said substituted phenyl and substituted heterocyclyl has one or more substituents selected from the group consisting of F, Cl, Br, H, CN, NO, NO 2 , OH, (C 1 -C 6 )alkoxy, (C 1 -C 6 )alkyl, (C 1 -C 6 )alkylphenyl, (C 1 -C 6 )alkyl-S(O) 2 NH 2 , (C 1 -C 6 )haloalkoxy, (C 1 -C 6 )haloalkyl, (C 1 -C 6 )haloalkyl-S(O) 2 NH 2 , (C 2 -C 6 )alkenyl, (C 2 -C 6 )alkynyl, (C 2 -C 6 )haloalkenyl, (C 3 -C 6 )cycloalkenyl, (C 3 -C 6 )cycloalkyl, (C 3 -C 6 )halocycloalkenyl, (C 3 -C 6 )halocycloalkyl, (C 1 -C 6 )alkyl((C 1 -C 6 )alkyl)(═NO(C 1 -C 6 )alkyl), C(═NO(C 1 -C 6 )alkyl)(C 1 -C 6 )alkyl, C(O)(C 1 -C 6 )alkyl, C(O)NH(C 1 -C 6 )alkyl, C(O)NHphenyl, C(O)O(C 1 -C 6 )alkyl, CH(═NO(C 1 -C 6 )alkyl), N((C 1 -C 6 )alkyl)(C(O)(C 1 -C 6 )alkyl), N((C 1 -C 6 )alkyl)(C(O)(C 1 -C 6 )alkyl-O(C 1 -C 6 )alkyl), N((C 1 -C 6 )alkyl)(C(O)(C 1 -C 6 )haloalkyl), N((C 1 -C 6 )alkyl)(C(O)O(C 1 -C 6 )alkyl), N((C 1 -C 6 )alkyl) 2 , N(C(O)O(C 1 -C 6 )alkyl) 2 , N═CH-phenyl, NH((C 1 -C 6 )alkylC(O)(C 1 -C 6 )alkyl), NH(C(O)(C 1 -C 6 )alkyl), NH(C(O)(C 2 -C 6 )alkenyl), NH(C(O)(C 3 -C 6 )cycloalkyl), NH(C 1 -C 6 )alkyl, NH(C 1 -C 6 )alkenyl, NH(C 1 -C 6 )alkynyl, NH(C 1 -C 6 )alkylphenyl, NH(S(O) 2 (C 1 -C 6 )alkyl), NH 2 , NHC(O)(C 1 -C 6 )alkylphenyl, NHC(O)(C 1 -C 6 )haloalkyl, NH—C(O)O(C 1 -C 6 )alkyl, S(═NCN)((C 1 -C 6 )alkyl), S(C 1 -C 6 )alkyl, S(C 1 -C 6 )haloalkyl, S(O)(═NCN)((C 1 -C 6 )alkyl), S(O)(C 1 -C 6 )alkyl, S(O)(C 1 -C 6 )haloalkyl, S(O) 2 (C 1 -C 6 )alkyl, S(O) 2 (C 1 -C 6 )haloalkyl, SCN,

wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, and halocycloalkyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C 1 -C 6 )alkyl, NH(C 3 -C 6 )cycloalkylCH 2 O(C 1 -C 6 )alkyl, NH(C 3 -C 6 )cycloalkylCH 2 O(C 1 -C 6 )haloalkyl, NHCH 2 (C 3 -C 6 )cycloalkyl, NH 2 , NO 2 , oxo, (C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy, and C(O)O—(C 1 -C 6 )alkyl.

12. A process according to claim 1 , wherein said molecule is selected from one of the following molecules

No.

Structure

F14

F18

F19

F22

F24

F25

F28

F31

F35

F37

F38

F39

F44

F51

F52

F53

F55

F77

F80

F87

F129

F279

F412

F414

F423

F533

F579

PF5

PF35

PF38

Assignments (2)

CHANGE OF NAME Recorded Nov 8, 2021

From: DOW AGROSCIENCES LLC

To: CORTEVA AGRISCIENCE LLC

Reel/Frame 058044/0184 →

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 8, 2017

From: HEEMSTRA, RONALD J.; ROSS, RONALD, JR.; DEKORVER, KYLE A.; GRAY, KAITLYN; KNUEPPEL, DANIEL I.; VEDNER, PETER; MARTIN, TIMOTHY P.; ECKELBARGER, JOSEPH D.; DAEUBLE, JOHN F.; HUNTER, RICKY; DEMETER, DAVID A.; TRULLINGER, TONY K; BAUM, ERICH W.; BENKO, ZOLTAN L.; CHOY, NAKYEN; CROUSE, GARY D.; LI, FANGZHENG; NISSEN, JEFFERY; OLSON, MONICA B.; RIENER, MICHELLE; SPARKS, THOMAS C.; WESSELS, FRANK J.; YAP, MAURICE C.

To: DOW AGROSCIENCES LLC

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Continuity (8)

Division 15092650 · Apr 7, 2016

Provisional Application 62148830 · Apr 17, 2015

Provisional Application 62148837 · Apr 17, 2015

Provisional Application 62148809 · Apr 17, 2015

Provisional Application 62148814 · Apr 17, 2015

Provisional Application 62148818 · Apr 17, 2015

Provisional Application 62148824 · Apr 17, 2015

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Cited By (2)

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