IP Library › Granted Patent US 9,661,854
Granted Patent B2
US 9,661,854 · App. 15/254,092 · Granted May 30, 2017

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

Inventors: Natalie C. Giampietro (Carmel, IN); Gary D. Crouse (Noblesville, IN); Thomas C. Sparks (Greenfield, IN); David A. Demeter (Fishers, IN)
Assignee: Dow AgroSciences LLC
A01N47/36C07D417/12C07D417/14
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Quick Facts
Patent No.
US 9,661,854
App. No.
15/254,092
Granted
May 30, 2017
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 (198)

1. A molecule of the following formula

wherein:

(A) Ar 1 is selected from the group consisting of furanyl, phenyl, pyridazinyl, A pyridyl, pyrimidinyl, and thienyl,

wherein each furanyl, phenyl, pyridazinyl, pyridyl, pyrimidinyl, and thienyl may be optionally substituted with one or more substituents independently selected from the group consisting of H, F, Cl, Br, I, CN, NO 2 , (C 1 -C 4 )alkyl, (C 1 -C 4 )haloalkyl, (C 3 -C 8 )cycloalkyl, (C 1 -C 4 )alkoxy, (C 1 -C 4 )haloalkoxy, (C 2 -C 6 )alkenyl, (C 2 -C 6 )alkynyl, S(O) n —(C 1 -C 4 )alkyl, S(O) n —(C 1 -C 4 )haloalkyl, OSO 2 —(C 1 -C 4 )alkyl, OSO 2 —(C 1 -C 4 )haloalkyl, C(O)—NR x R y , (C 1 -C 4 )alkyl-NR x R y , C(O)—(C 1 -C 4 )alkyl, C(O)O—(C 1 -C 4 )alkyl, C(O)—(C 1 -C 4 )haloalkyl, C(O)O—(C 1 -C 4 )haloalkyl, C(O)—(C 3 -C 8 )cycloalkyl, C(O)O—(C 3 -C 8 )cycloalkyl, C(O)—(C 2 -C 6 )alkenyl, C(O)O—(C 2 -C 6 )alkenyl, (C 1 -C 4 )alkyl-O—(C 1 -C 4 )alkyl, (C 1 -C 4 )alkyl-S(O) n —(C 1 -C 4 )alkyl, C(O)—(C 1 -C 4 )alkyl-C(O)O—(C 1 -C 4 )alkyl, phenyl, and phenoxy,

wherein each alkyl, haloalkyl, cycloalkyl, alkoxy, haloalkoxy, alkenyl, alkynyl, phenyl, and phenoxy substituent may be optionally substituted with one or more substituents independently selected from the group consisting of H, F, Cl, Br, I, CN, NO 2 , (C 1 -C 4 )alkyl, (C 1 -C 4 )haloalkyl, (C 3 -C 8 )cycloalkyl, (C 1 -C 4 )alkoxy, (C 1 -C 4 )haloalkoxy, (C 2 -C 6 )alkenyl, (C 2 -C 6 )alkynyl, S(O) n —(C 1 -C 4 )alkyl, S(O) n —(C 1 -C 4 )haloalkyl, OSO 2 —(C 1 -C 4 )alkyl, OSO 2 —(C 1 -C 4 )haloalkyl, C(O)—NR x R y , (C 1 -C 4 )alkyl-NR x R y , C(O)—(C 1 -C 4 )alkyl, C(O)O—(C 1 -C 4 )alkyl, C(O)—(C 1 -C 4 )haloalkyl, C(O)O—(C 1 -C 4 )haloalkyl, C(O)—(C 3 -C 8 )cycloalkyl, C(O)O—(C 3 -C 8 )cycloalkyl, C(O)—(C 2 -C 6 )alkenyl, C(O)O—(C 2 -C 6 )alkenyl, (C 1 -C 4 )alkyl-O—(C 1 -C 4 )alkyl, (C 1 -C 4 )alkyl-S(O) n —(C 1 -C 4 )alkyl, C(O)—(C 1 -C 4 )alkyl-C(O)O—(C 1 -C 4 )alkyl, phenyl, and phenoxy;

(B) Het is a 5- or 6-membered, saturated or unsaturated, heterocyclic ring, containing one or more heteroatoms independently selected from nitrogen, sulfur, or oxygen, and where Ar 1 and L 1 are not ortho to each other, but may be meta or para, such as, for a five-membered ring they are 1,3, and for a 6-membered ring they are either 1,3 or 1,4,

wherein each heterocyclic ring may be optionally substituted with one or more substituents independently selected from the group consisting of H, F, Cl, Br, I, CN, NO 2 , oxo, (C 1 -C 4 )alkyl, (C 1 -C 4 )haloalkyl, (C 3 -C 8 )cycloalkyl, (C 1 -C 4 )alkoxy, (C 1 -C 4 )haloalkoxy, (C 2 -C 6 )alkenyl, (C 2 -C 6 )alkynyl, S(O) n —(C 1 -C 4 )alkyl, S(O) n —(C 1 -C 4 )haloalkyl, OSO 2 —(C 1 -C 4 )alkyl, OSO 2 —(C 1 -C 4 )haloalkyl, C(O)—NR x R y , (C 1 -C 4 )alkyl-NR x R y , C(O)—(C 1 -C 4 )alkyl, C(O)O—(C 1 -C 4 )alkyl, C(O)—(C 1 -C 4 )haloalkyl, C(O)O—(C 1 -C 4 )haloalkyl, C(O)—(C 3 -C 8 )cycloalkyl, C(O)O—(C 3 -C 8 )cycloalkyl, C(O)—(C 2 -C 6 )alkenyl, C(O)O—(C 2 -C 6 )alkenyl, (C 1 -C 4 )alkyl-O—(C 1 -C 4 )alkyl, (C 1 -C 4 )alkyl-S(O) n —(C 1 -C 4 )alkyl, C(O)—(C 1 -C 4 )alkyl-C(O)O—(C 1 -C 4 )alkyl, phenyl, and phenoxy,

wherein each alkyl, haloalkyl, cycloalkyl, alkoxy, haloalkoxy, alkenyl, alkynyl, phenyl, and phenoxy substituent may be optionally substituted with one or more substituents independently selected from the group consisting of H, F, Cl, Br, I, CN, NO 2 , (C 1 -C 4 )alkyl, (C 1 -C 4 )haloalkyl, (C 3 -C 8 )cycloalkyl, (C 1 -C 4 )alkoxy, (C 1 -C 4 )haloalkoxy, (C 2 -C 6 )alkenyl, (C 2 -C 6 )alkynyl, S(O) n —(C 1 -C 4 )alkyl, S(O) n —(C 1 -C 4 )haloalkyl, OSO 2 —(C 1 -C 4 )alkyl, OSO 2 —(C 1 -C 4 )haloalkyl, C(O)—NR x R y , (C 1 -C 4 )alkyl-NR x R y , C(O)—(C 1 -C 4 )alkyl, C(O)O—(C 1 -C 4 )alkyl, C(O)—(C 1 -C 4 )haloalkyl, C(O)O—(C 1 -C 4 )haloalkyl, C(O)—(C 3 -C 8 )cycloalkyl, C(O)O—(C 3 -C 8 )cycloalkyl, C(O)—(C 2 -C 6 )alkenyl, C(O)O—(C 2 -C 6 )alkenyl, (C 1 -C 4 )alkyl-O—(C 1 -C 4 )alkyl, (C 1 -C 4 )alkyl-S(O) n —(C 1 -C 4 )alkyl, C(O)—(C 1 -C 4 )alkyl-C(O)O—(C 1 -C 4 )alkyl, phenyl, and phenoxy;

(C) L 1 is selected from the group consisting of (C 1 -C 4 )alkyl, (C 1 -C 4 )haloalkyl, (C 3 -C 8 )cycloalkyl, (C 2 -C 6 )alkenyl, and (C 2 -C 6 )alkynyl,

wherein each alkyl, haloalkyl, cycloalkyl, alkenyl, and alkynyl may be optionally substituted with one or more substituents independently selected from the group consisting of H, F, Cl, Br, I, CN, NO 2 , (C 1 -C 4 )alkyl, (C 1 -C 4 )haloalkyl, (C 3 -C 8 )cycloalkyl, (C 1 -C 4 )alkoxy, (C 1 -C 4 )haloalkoxy, (C 2 -C 6 )alkenyl, and (C 2 -C 6 )alkynyl;

(D) Ar 2 is selected from the group consisting of furanyl, phenyl, pyridazinyl, pyridyl, pyrimidinyl, and thienyl,

wherein each furanyl, phenyl, pyridazinyl, pyridyl, pyrimidinyl, and thienyl may be optionally substituted with one or more substituents independently selected from the group consisting of H, F, Cl, Br, I, CN, NO 2 , (C 1 -C 4 )alkyl, (C 1 -C 4 )haloalkyl, (C 3 -C 8 )cycloalkyl, (C 1 -C 4 )alkoxy, (C 1 -C 4 )haloalkoxy, (C 2 -C 6 )alkenyl, (C 2 -C 6 )alkynyl, S(O) n —(C 1 -C 4 )alkyl, S(O) n —(C 1 -C 4 )haloalkyl, OSO 2 —(C 1 -C 4 )alkyl, OSO 2 —(C 1 -C 4 )haloalkyl, C(O)—NR x R y , (C 1 -C 4 )alkyl-NR x R y , C(O)—(C 1 -C 4 )alkyl, C(O)O—(C 1 -C 4 )alkyl, C(O)—(C 1 -C 4 )haloalkyl, C(O)O—(C 1 -C 4 )haloalkyl, C(O)—(C 3 -C 8 )cycloalkyl, C(O)O—(C 3 -C 8 )cycloalkyl, C(O)—(C 2 -C 6 )alkenyl, C(O)O—(C 2 -C 6 )alkenyl, (C 1 -C 4 )alkyl-O—(C 1 -C 4 )alkyl, (C 1 -C 4 )alkyl-S(O) n —(C 1 -C 4 )alkyl, C(O)—(C 1 -C 4 )alkyl-C(O)O—(C 1 -C 4 )alkyl, phenyl, and phenoxy,

wherein each alkyl, haloalkyl, cycloalkyl, alkoxy, haloalkoxy, alkenyl, alkynyl, phenyl, and phenoxy substituent may be optionally substituted with one or more substituents independently selected from the group consisting of H, F, Cl, Br, I, CN, NO 2 , (C 1 -C 4 )alkyl, (C 1 -C 4 )haloalkyl, (C 3 -C 8 )cycloalkyl, (C 1 -C 4 )alkoxy, (C 1 -C 4 )haloalkoxy, (C 2 -C 6 )alkenyl, (C 2 -C 6 )alkynyl, S(O) n —(C 1 -C 4 )alkyl, S(O) n —(C 1 -C 4 )haloalkyl, OSO 2 —(C 1 -C 4 )alkyl, OSO 2 —(C 1 -C 4 )haloalkyl, C(O)—NR x R y , (C 1 -C 4 )alkyl-NR x R y , C(O)—(C 1 -C 4 )alkyl, C(O)O—(C 1 -C 4 )alkyl, C(O)—(C 1 -C 4 )haloalkyl, C(O)O—(C 1 -C 4 )haloalkyl, C(O)—(C 3 -C 8 )cycloalkyl, C(O)O—(C 3 -C 8 )cycloalkyl, C(O)—(C 2 -C 6 )alkenyl, C(O)O—(C 2 -C 6 )alkenyl, (C 1 -C 4 )alkyl-O—(C 1 -C 4 )alkyl, (C 1 -C 4 )alkyl-S(O) n —(C 1 -C 4 )alkyl, C(O)—(C 1 -C 4 )alkyl-C(O)O—(C 1 -C 4 )alkyl, phenyl, and phenoxy;

(E) R 15 is selected from the group consisting of H, (C 1 -C 4 )alkyl, (C 3 -C 8 )cycloalkyl, (C 2 -C 6 )alkenyl, (C 2 -C 6 )alkynyl, S(O) n —(C 1 -C 4 )alkyl, C(O)—NR x R y , C(O)-phenyl, (C 1 -C 4 )alkyl-NR x R y , C(O)O—(C 1 -C 4 )alkyl, C(O)—(C 3 -C 8 )cycloalkyl, C(O)O—(C 3 -C 8 )cycloalkyl, C(O)—(C 2 -C 6 )alkenyl, C(O)O—(C 2 -C 6 )alkenyl, (C 1 -C 4 )alkyl-O—(C 1 -C 4 )alkyl, (C 1 -C 4 )alkyl-OC(O)—(C 1 -C 4 )alkyl, (C 1 -C 4 )alkyl-S(O) n —(C 1 -C 4 )alkyl, and (C 1 -C 4 )alkyl-OC(O)O—(C 1 -C 4 )alkyl,

wherein each alkyl, cycloalkyl, alkenyl, alkynyl, and phenyl may be optionally substituted with one or more substituents independently selected from the group consisting of H, F, Cl, Br, I, CN, NO 2 , oxo, (C 1 -C 4 )alkyl, (C 1 -C 4 )haloalkyl, (C 3 -C 8 )cycloalkyl, (C 1 -C 4 )alkoxy, (C 1 -C 4 )haloalkoxy, (C 2 -C 6 )alkenyl, (C 2 -C 6 )alkynyl, S(O) n —(C 1 -C 4 )alkyl, S(O) n —(C 1 -C 4 )haloalkyl, OSO 2 —(C 1 -C 4 )alkyl, OSO 2 —(C 1 -C 4 )haloalkyl, C(O)—NR x R y , (C 1 -C 4 )alkyl-NR x R y , C(O)—(C 1 -C 4 )alkyl, C(O)O—(C 1 -C 4 )alkyl, C(O)—(C 1 -C 4 )haloalkyl, C(O)O—(C 1 -C 4 )haloalkyl, C(O)—(C 3 -C 8 )cycloalkyl, C(O)O—(C 3 -C 8 )cycloalkyl, C(O)—(C 2 -C 6 )alkenyl, C(O)O—(C 2 -C 6 )alkenyl, (C 1 -C 4 )alkyl-O—(C 1 -C 4 )alkyl, (C 1 -C 4 )alkyl-S(O) n —(C 1 -C 4 )alkyl, C(O)—(C 1 -C 4 )alkyl-C(O)O—(C 1 -C 4 )alkyl, phenyl, and phenoxy;

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

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

(H) R 16 is selected from the group consisting of (K), H, (C 1 -C 4 )alkyl, (C 3 -C 8 )cycloalkyl, (C 2 -C 6 )alkenyl, (C 2 -C 6 )alkynyl, C(O)—(C 1 -C 4 )alkyl, (C 1 -C 4 )alkyl-O—(C 1 -C 4 )alkyl, (C 1 -C 4 )alkyl-S(O) n —(C 1 -C 4 )alkyl, (C 1 -C 4 )alkylphenyl, (C 1 -C 4 )alkyl-O-phenyl, C(O)-(Het-1), Het-1, (C 1 -C 4 )alkyl-(Het-1), (C 1 -C 4 )alkyl-OC(O)—(C 1 -C 4 )alkyl, (C 1 -C 4 )alkyl-OC(O)—(C 1 -C 4 )alkyl, (C 1 -C 4 )alkyl-OC(O)O—(C 1 -C 4 )alkyl, (C 1 -C 4 )alkyl-OC(O)—NR x R y , (C 1 -C 4 )alkyl-C(O)—N(R x )(C 1 -C 4 )alkyl-(Het-1), (C 1 -C 4 )alkyl-C(O)-(Het-1), (C 1 -C 4 )alkyl-C(O)—N(R x )(C 1 -C 4 )alkyl(NR x R y )—C(O)OH, (C 1 -C 4 )alkyl-C(O)—N(R x )(C 1 -C 4 )alkyl-NR x R y , (C 1 -C 4 )alkyl-C(O)—N(R x )(C 1 -C 4 )alkyl-N(R x )—C(O)O—(C 1 -C 4 )alkyl, (C 1 -C 4 )alkyl-C(O)—N(R x )(C 1 -C 4 )alkyl(N(R x )—C(O)O—(C 1 -C 4 )alkyl)-C(O)OH, (C 1 -C 4 )alkyl-C(O)-(Het-1)-C(O)O—(C 1 -C 4 )alkyl, (C 1 -C 4 )alkyl-OC(O)O—(C 1 -C 4 )alkyl, (C 1 -C 4 )alkyl-OC(O)—(C 1 -C 4 )alkyl, (C 1 -C 4 )alkyl-OC(O)—(C 3 -C 8 )cycloalkyl, (C 1 -C 4 )alkyl-OC(O)-(Het-1), (C 1 -C 4 )alkyl-OC(O)—(C 1 -C 4 )alkyl-N(R x )—C(O)O—(C 1 -C 4 )alkyl, (C 1 -C 4 )alkyl-NR x R y , (C 1 -C 4 )alkyl-S(O) n -(Het-1), and (C 1 -C 4 )alkyl-O-(Het-1),

wherein each alkyl, cycloalkyl, alkenyl, alkynyl, phenyl, and (Het-1) may be optionally substituted with one or more substituents independently selected from the group consisting of H, F, Cl, Br, I, CN, NO 2 , NR x R y , (C 1 -C 4 )alkyl, (C 1 -C 4 )haloalkyl, (C 3 -C 8 )cycloalkyl, (C 1 -C 4 )alkoxy, (C 2 -C 6 )alkenyl, (C 2 -C 6 )alkynyl, S(O) n —(C 1 -C 4 )alkyl, S(O) n —(C 1 -C 4 )haloalkyl, OSO 2 —(C 1 -C 4 )alkyl, OSO 2 —(C 1 -C 4 )haloalkyl, C(O)H, C(O)OH, C(O)—NR x R y , (C 1 -C 4 )alkyl-NR x R y , C(O)—(C 1 -C 4 )alkyl, C(O)O—(C 1 -C 4 )alkyl, C(O)—(C 1 -C 4 )haloalkyl, C(O)O—(C 1 -C 4 )haloalkyl, C(O)—(C 3 -C 8 )cycloalkyl, C(O)O—(C 3 -C 8 )cycloalkyl, C(O)—(C 2 -C 6 )alkenyl, C(O)O—(C 2 -C 6 )alkenyl, (C 1 -C 4 )alkyl-O—(C 1 -C 4 )alkyl, (C 1 -C 4 )alkyl-S(O) n —(C 1 -C 4 )alkyl, C(O)—(C 1 -C 4 )alkyl-C(O)O—(C 1 -C 4 )alkyl), phenyl, phenoxy, Si((C 1 -C 4 )alkyl) 3 , S(O) n —NR x R y , and (Het-1);

(I) R 17 is selected from the group consisting of (K), H, (C 1 -C 4 )alkyl, (C 3 -C 8 )cycloalkyl, (C 2 -C 6 )alkenyl, (C 2 -C 6 )alkynyl, C(O)—(C 1 -C 4 )alkyl, (C 1 -C 4 )alkyl-O—(C 1 -C 4 )alkyl, (C 1 -C 4 )alkyl-S(O) n —(C 1 -C 4 )alkyl, (C 1 -C 4 )alkylphenyl, (C 1 -C 4 )alkyl-O-phenyl, C(O)-(Het-1), Het-1, (C 1 -C 4 )alkyl-(Het-1), (C 1 -C 4 )alkyl-OC(O)—(C 1 -C 4 )alkyl, (C 1 -C 4 )alkyl-OC(O)—(C 1 -C 4 )alkyl, (C 1 -C 4 )alkyl-OC(O)O—(C 1 -C 4 )alkyl, (C 1 -C 4 )alkyl-OC(O)—NR x R y , (C 1 -C 4 )alkyl-C(O)—N(R x )(C 1 -C 4 )alkyl-(Het-1), (C 1 -C 4 )alkyl-C(O)-(Het-1), (C 1 -C 4 )alkyl-C(O)—N(R x )(C 1 -C 4 )alkyl(NR x R y )—C(O)OH, (C 1 -C 4 )alkyl-C(O)—N(R x )(C 1 -C 4 )alkyl-NR x R y , (C 1 -C 4 )alkyl-C(O)—N(R x )(C 1 -C 4 )alkyl-N(R x )—C(O)O—(C 1 -C 4 )alkyl, (C 1 -C 4 )alkyl-C(O)—N(R x )(C 1 -C 4 )alkyl(N(R x )—C(O)O—(C 1 -C 4 )alkyl)-C(O)OH, (C 1 -C 4 )alkyl-C(O)-(Het-1)-C(O)O—(C 1 -C 4 )alkyl, (C 1 -C 4 )alkyl-OC(O)O—(C 1 -C 4 )alkyl, (C 1 -C 4 )alkyl-OC(O)—(C 1 -C 4 )alkyl, (C 1 -C 4 )alkyl-OC(O)—(C 3 -C 8 )cycloalkyl, (C 1 -C 4 )alkyl-OC(O)-(Het-1), (C 1 -C 4 )alkyl-OC(O)—(C 1 -C 4 )alkyl-N(R x )—C(O)O—(C 1 -C 4 )alkyl, (C 1 -C 4 )alkyl-NR x R y , (C 1 -C 4 )alkyl-S(O) n -(Het-1), and (C 1 -C 4 )alkyl-O-(Het-1),

wherein each alkyl, cycloalkyl, alkenyl, alkynyl, phenyl, and (Het-1) may be optionally substituted with one or more substituents independently selected from the group consisting of H, F, Cl, Br, I, CN, NO 2 , NR x R y , (C 1 -C 4 )alkyl, (C 1 -C 4 )haloalkyl, (C 3 -C 8 )cycloalkyl, (C 1 -C 4 )alkoxy, (C 2 -C 6 )alkenyl, (C 2 -C 6 )alkynyl, S(O) n —(C 1 -C 4 )alkyl, S(O) n —(C 1 -C 4 )haloalkyl, OSO 2 —(C 1 -C 4 )alkyl, OSO 2 —(C 1 -C 4 )haloalkyl, C(O)H, C(O)OH, C(O)—NR x R y , (C 1 -C 4 )alkyl-NR x R y , C(O)—(C 1 -C 4 )alkyl, C(O)O—(C 1 -C 4 )alkyl, C(O)—(C 1 -C 4 )haloalkyl, C(O)O—(C 1 -C 4 )haloalkyl, C(O)—(C 3 -C 8 )cycloalkyl, C(O)O—(C 3 -C 8 )cycloalkyl, C(O)—(C 2 -C 6 )alkenyl, C(O)O—(C 2 -C 6 )alkenyl, (C 1 -C 4 )alkyl-O—(C 1 -C 4 )alkyl, (C 1 -C 4 )alkyl-S(O) n —(C 1 -C 4 )alkyl, C(O)—(C 1 -C 4 )alkyl-C(O)O—(C 1 -C 4 )alkyl, phenyl, phenoxy, Si((C 1 -C 4 )alkyl) 3 , S(O) n —NR x R y , and (Het-1);

(J) L 2 is selected from the group consisting of (C 3 -C 8 )cycloalkyl, phenyl, (C 1 -C 4 )alkylphenyl, (C 1 -C 4 )alkyl-O-phenyl, (C 2 -C 6 )alkenyl-O-phenyl, (Het-1), (C 1 -C 4 )alkyl-(Het-1), and (C 1 -C 4 )alkyl-O-(Het-1),

wherein each alkyl, cycloalkyl, alkenyl, phenyl, and (Het-1) may be optionally substituted with one or more substituents independently selected from the group consisting of H, F, Cl, Br, I, CN, NO 2 , NR x R y , (C 1 -C 4 )alkyl, (C 1 -C 4 )haloalkyl, (C 3 -C 8 )cycloalkyl, (C 1 -C 4 )alkoxy, (C 1 -C 4 )haloalkoxy, (C 2 -C 6 )alkenyl, (C 2 -C 6 )alkynyl, S(O) n —(C 1 -C 4 )alkyl, S(O) n —(C 1 -C 4 )haloalkyl, OSO 2 —(C 1 -C 4 )alkyl, OSO 2 —(C 1 -C 4 )haloalkyl, C(O)H, C(O)—NR x R y , (C 1 -C 4 )alkyl-NR x R y , C(O)—(C 1 -C 4 )alkyl, C(O)O—(C 1 -C 4 )alkyl, C(O)—(C 1 -C 4 )haloalkyl, C(O)O—(C 1 -C 4 )haloalkyl, C(O)—(C 3 -C 8 )cycloalkyl, C(O)O—(C 1 -C 4 )cycloalkyl, C(O)—(C 2 -C 6 )alkenyl, C(O)O—(C 2 -C 6 )alkenyl, O—(C 1 -C 4 )alkyl, S—(C 1 -C 4 )alkyl, (C 1 -C 4 )alkyl-O—(C 1 -C 4 )alkyl, C(O)—(C 1 -C 4 )alkyl-C(O)O—(C 1 -C 4 )alkyl, phenyl, phenoxy, and (Het-1),

wherein each alkyl, cycloalkyl, alkenyl, phenyl, and (Het-1) substituent may be optionally substituted with one or more substituents independently selected from the group consisting of H, F, Cl, Br, I, CN, NO 2 , NR x R y , (C 1 -C 4 )alkyl, (C 1 -C 4 )haloalkyl, (C 3 -C 8 )cycloalkyl, (C 1 -C 4 )alkoxy, (C 1 -C 4 )haloalkoxy, (C 2 -C 6 )alkenyl, (C 2 -C 6 )alkynyl, S(O) n —(C 1 -C 4 )alkyl, S(O) n —(C 1 -C 4 )haloalkyl, OSO 2 —(C 1 -C 4 )alkyl, OSO 2 —(C 1 -C 4 )haloalkyl, C(O)H, C(O)—NR x R y , (C 1 -C 4 )alkyl-NR x R y , C(O)—(C 1 -C 4 )alkyl, C(O)O—(C 1 -C 4 )alkyl, C(O)—(C 1 -C 4 )haloalkyl, C(O)O—(C 1 -C 4 )haloalkyl, C(O)—(C 3 -C 8 )cycloalkyl, C(O)O—(C 1 -C 4 )cycloalkyl, C(O)—(C 2 -C 6 )alkenyl, C(O)O—(C 2 -C 6 )alkenyl, O—(C 1 -C 4 )alkyl, S—(C 1 -C 4 )alkyl, (C 1 -C 4 )alkyl-O—(C 1 -C 4 )alkyl, C(O)—(C 1 -C 4 )alkyl-C(O)O—(C 1 -C 4 )alkyl, phenyl, phenoxy, and (Het-1);

(K) R 16 and R 17 along with C x (Q 2 )(N x ), form a 4- to 7-membered saturated or unsaturated, hydrocarbyl cyclic group, which may further contain one or more heteroatoms selected from the group consisting of nitrogen, sulfur, and oxygen,

wherein said hydrocarbyl cyclic group may be optionally substituted with one or more substituents independently selected from the group consisting of oxo, R 18 , and R 19 ,

wherein R 18 and R 19 are each independently selected from the group consisting of H, F, Cl, Br, I, CN, NO 2 , oxo, thioxo, (C 1 -C 4 )alkyl, (C 1 -C 4 )haloalkyl, (C 3 -C 8 )cycloalkyl, (C 1 -C 4 )alkoxy, (C 1 -C 4 )haloalkoxy, (C 2 -C 6 )alkenyl, (C 2 -C 6 )alkynyl, S(O) n —(C 1 -C 4 )alkyl, S(O) n —(C 1 -C 4 )haloalkyl, OSO 2 —(C 1 -C 4 )alkyl, OSO 2 —(C 1 -C 4 )haloalkyl, C(O)H, C(O)—(C 1 -C 4 )alkyl, C(O)O—(C 1 -C 4 )alkyl, C(O)—(C 1 -C 4 )haloalkyl, C(O)O—(C 1 -C 4 )haloalkyl, C(O)—(C 3 -C 8 )cycloalkyl, C(O)O—(C 3 -C 8 )cycloalkyl, C(O)—(C 2 -C 6 )alkenyl, C(O)O—(C 2 -C 6 )alkenyl, (C 1 -C 4 )alkyl-O—(C 1 -C 4 )alkyl, (C 1 -C 4 )alkyl-S(O) n —(C 1 -C 4 )alkyl, C(O)—(C 1 -C 4 )alkyl-C(O)O—(C 1 -C 4 )alkyl, phenyl, and (Het-1);

(L) R x and R y are each independently selected from the group consisting of H, (C 1 -C 4 )alkyl, (C 1 -C 4 )haloalkyl, (C 3 -C 8 )cycloalkyl, (C 1 -C 4 )alkoxy, (C 1 -C 4 )haloalkoxy, (C 2 -C 6 )alkenyl, (C 2 -C 6 )alkynyl, S(O) n —(C 1 -C 4 )alkyl, S(O) n —(C 1 -C 4 )haloalkyl, OSO 2 —(C 1 -C 4 )alkyl, OSO 2 —(C 1 -C 4 )haloalkyl, C(O)H, C(O)—(C 1 -C 4 )alkyl, C(O)O—(C 1 -C 4 )alkyl, C(O)—(C 1 -C 4 )haloalkyl, C(O)O—(C 1 -C 4 )haloalkyl, C(O)—(C 3 -C 8 )cycloalkyl, C(O)O—(C 3 -C 8 )cycloalkyl, C(O)—(C 2 -C 6 )alkenyl, C(O)O—(C 2 -C 6 )alkenyl, (C 1 -C 4 )alkyl-O—(C 1 -C 4 )alkyl, (C 1 -C 4 )alkyl-S(O) n —(C 1 -C 4 )alkyl, C(O)—(C 1 -C 4 )alkyl-C(O)O—(C 1 -C 4 )alkyl, and phenyl,

wherein each alkyl, haloalkyl, cycloalkyl, alkoxy, haloalkoxy, alkenyl, alkynyl, and phenyl may be optionally substituted with one or more substituents independently selected from the group consisting of H, F, Cl, Br, I, CN, NO 2 , (C 1 -C 4 )alkyl, (C 1 -C 4 )haloalkyl, (C 3 -C 8 )cycloalkyl, (C 1 -C 4 )alkoxy, (C 1 -C 4 )haloalkoxy, (C 2 -C 6 )alkenyl, (C 2 -C 6 )alkynyl, S(O) n —(C 1 -C 4 )alkyl, S(O) n —(C 1 -C 4 )haloalkyl, OSO 2 —(C 1 -C 4 )alkyl, OSO 2 —(C 1 -C 4 )haloalkyl, C(O)H, C(O)—(C 1 -C 4 )alkyl, C(O)O—(C 1 -C 4 )alkyl, C(O)—(C 1 -C 4 )haloalkyl, C(O)O—(C 1 -C 4 )haloalkyl, C(O)—(C 3 -C 8 )cycloalkyl, C(O)O—(C 3 -C 8 )cycloalkyl, C(O)—(C 2 -C 6 )alkenyl, C(O)O—(C 2 -C 6 )alkenyl, (C 1 -C 4 )alkyl-O—(C 1 -C 4 )alkyl, (C 1 -C 4 )alkyl-S(O) n —(C 1 -C 4 )alkyl, C(O)—(C 1 -C 4 )alkyl-C(O)O—(C 1 -C 4 )alkyl, phenyl, and (Het-1);

(M) (Het-1) is a 5- or 6-membered, saturated or unsaturated, heterocyclic ring, containing one or more heteroatoms independently selected from nitrogen, sulfur, or oxygen,

wherein each heterocyclic ring may be optionally substituted with one or more substituents independently selected from the group consisting of H, F, Cl, Br, I, CN, NO 2 , oxo, (C 1 -C 4 )alkyl, (C 1 -C 4 )haloalkyl, (C 3 -C 8 )cycloalkyl, (C 1 -C 4 )alkoxy, (C 1 -C 4 )haloalkoxy, (C 2 -C 6 )alkenyl, (C 2 -C 6 )alkynyl, S(O) n —(C 1 -C 4 )alkyl, S(O) n —(C 1 -C 4 )haloalkyl, OSO 2 —(C 1 -C 4 )alkyl, OSO 2 —(C 1 -C 4 )haloalkyl, C(O)—NR x R y , (C 1 -C 4 )alkyl-NR x R y , C(O)—(C 1 -C 4 )alkyl, C(O)O—(C 1 -C 4 )alkyl, C(O)—(C 1 -C 4 )haloalkyl, C(O)O—(C 1 -C 4 )haloalkyl, C(O)—(C 3 -C 8 )cycloalkyl, C(O)O—(C 3 -C 8 )cycloalkyl, C(O)—(C 2 -C 6 )alkenyl, C(O)O—(C 2 -C 6 )alkenyl, (C 1 -C 4 )alkyl-O—(C 1 -C 4 )alkyl, (C 1 -C 4 )alkyl-S(O) n —(C 1 -C 4 )alkyl, C(O)—(C 1 -C 4 )alkyl-C(O)O—(C 1 -C 4 )alkyl, phenyl, and phenoxy,

wherein each alkyl, haloalkyl, cycloalkyl, alkoxy, haloalkoxy, alkenyl, alkynyl, phenyl, and phenoxy substituent may be optionally substituted with one or more substituents independently selected from the group consisting of H, F, Cl, Br, I, CN, NO 2 , (C 1 -C 4 )alkyl, (C 1 -C 4 )haloalkyl, (C 3 -C 8 )cycloalkyl, (C 1 -C 4 )alkoxy, (C 1 -C 4 )haloalkoxy, (C 2 -C 6 )alkenyl, (C 2 -C 6 )alkynyl, S(O) n —(C 1 -C 4 )alkyl, S(O) n —(C 1 -C 4 )haloalkyl, OSO 2 —(C 1 -C 4 )alkyl, OSO 2 —(C 1 -C 4 )haloalkyl, C(O)—NR x R y , (C 1 -C 4 )alkyl-NR x R y , C(O)—(C 1 -C 4 )alkyl, C(O)O—(C 1 -C 4 )alkyl, C(O)—(C 1 -C 4 )haloalkyl, C(O)O—(C 1 -C 4 )haloalkyl, C(O)—(C 3 -C 8 )cycloalkyl, C(O)O—(C 3 -C 8 )cycloalkyl, C(O)—(C 2 -C 6 )alkenyl, C(O)O—(C 2 -C 6 )alkenyl, (C 1 -C 4 )alkyl-O—(C 1 -C 4 )alkyl, (C 1 -C 4 )alkyl-S(O) n —(C 1 -C 4 )alkyl, C(O)—(C 1 -C 4 )alkyl-C(O)O—(C 1 -C 4 )alkyl, phenyl, and phenoxy;

(N) n are each independently 0, 1, or 2; and N-oxides, agriculturally acceptable acid addition salts, solvates, crystal polymorphs, isotopes, resolved stereoisomers, and tautomers, of the molecules of Formula One.

2. A molecule according to claim 1 , wherein Ar 1 is (1a)

wherein:

(1) X 1 is N or CR 1 , wherein R 1 is H;

(2) R 2 and R 4 are each independently H;

(3) R 3 is CF 3 or OCF 3 ; and

(4) R 5 is H or Cl.

3. A molecule according to claim 1 , wherein Het is (1b)

wherein R 6 is H.

4. A molecule according to claim 1 , wherein L 1 is (1c)

wherein R 7 and R 8 are each independently H.

5. A molecule according to claim 1 , wherein L 1 is (1d)

wherein R 7 , R 8 , R 9 , and R 10 are each independently H or CH 3 .

6. A molecule according to claim 1 , wherein L 1 is (1e)

wherein R 7 , R 8 , R 9 , and R 10 are each independently H.

7. A molecule according to claim 1 , wherein Ar 2 is (1f)

wherein:

(1) R 11 is H, F, CH 3 or OCH 3 ;

(2) R 12 is H, F, Cl, CF 3 , OCH 3 , or C(O)O—CH 3 ;

(3) X 2 is N or CR 13 , wherein R 13 is H, F, Cl, CF 3 , OCH 3 , or C(O)O—CH 3 ; and

(4) R 14 is H or F.

8. A molecule according to claim 1 , wherein R 15 is H.

9. A molecule according to claim 1 , wherein Q 1 is O.

10. A molecule according to claim 1 , wherein Q 2 is S.

11. A molecule according to claim 1 , wherein L 2 is (1g)

wherein:

(1) R 20 is F, Cl, CH 2 CH 2 CH 3 , CH(CH 3 ) 2 , CF 3 , cyclopropyl, OCH 3 , OCH 2 CH 3 , OCH(CH 3 ) 2 , OCH(CH 3 )CH 2 CH 3 , OC(CH 3 ) 3 , OCF 3 , OCH 2 CF 3 , CH 2 OCH 3 , or CH(CH 3 )OCH 3 ;

(2) R 21 is H;

(3) R 22 is H or F;

(4) R 23 is CH 3 and CF 3 ; and

(5) R 24 is H.

12. A molecule according to claim 1 , wherein L 2 is (1h)

wherein R 20 , R 21 , R 22 , R 23 , and R 24 are each independently H.

13. A molecule according to claim 1 , wherein R 16 and R 17 along with C(Q 2 )(N x ), is (1i)

wherein R 18 and R 19 are each independently H.

14. A molecule according to claim 1 , wherein R 16 and R 17 along with C(Q 2 )(N x ), is (1j)

wherein R 18 and R 19 are each independently H.

15. A molecule according to claim 1 , wherein

(A) Ar 1 is (1a)

wherein:

(1) X 1 is selected from the group consisting of N and CR 1 , and

(2) R 1 , R 2 , R 3 , R 4 , and R 5 are each independently selected from the group consisting of H, Cl, (C 1 -C 4 )haloalkyl, and (C 1 -C 4 )haloalkoxy;

(B) Het is (1b)

wherein, R 6 is H;

(C) L 1 is selected from the group consisting of

wherein, each R 7 , R 8 , R 9 , and R 10 are independently selected from the group consisting of H and (C 1 -C 4 )alkyl;

(D) Ar 2 is (1f)

wherein:

(1) X 2 is selected from the group consisting of N and CR 13 , and

(2) R 11 , R 12 , R 13 , and R 14 are each independently selected from the group consisting of H, F, Cl, (C 1 -C 4 )alkyl, (C 1 -C 4 )haloalkyl, (C 1 -C 4 )alkoxy, and C(O)O—(C 1 -C 4 )alkyl;

(E) R 15 is H;

(F) Q 1 is O;

(G) Q 2 is S;

(H) R 16 is (K);

(I) R 17 is (K);

(J) L 2 is selected from the group consisting of

wherein, R 20 , R 21 , R 22 , R 23 , and R 24 are each independently selected from the group consisting of H, F, Cl, (C 1 -C 4 )alkyl, (C 1 -C 4 )haloalkyl, (C 3 -C 8 )cycloalkyl, (C 1 -C 4 )alkoxy, (C 1 -C 4 )haloalkoxy, and (C 1 -C 4 )alkyl-O—(C 1 -C 4 )alkyl; and

(K) R 16 and R 17 along with C(Q 2 )(N x ), is selected from the group consisting of

wherein R 18 and R 19 are each H.

16. A molecule according to claim 1 , wherein

(A) Ar 1 is (1a)

wherein:

(1) X 1 is selected from the group consisting of N and CR 1 , and

(2) R 1 , R 2 , R 3 , R 4 , and R 5 are each independently selected from the group consisting of H, Cl, CF 3 , and OCF 3 ;

(B) Het is (1b)

wherein, R 6 is H;

(C) L 1 is selected from the group consisting of

wherein, each R 7 , R 8 , R 9 , and R 10 are independently selected from the group consisting of H and CH 3 ;

(D) Ar 2 is (1f)

wherein:

(1) X 2 is selected from the group consisting of N and CR 13 , and

(2) R 11 , R 12 , R 13 , and R 14 are each independently selected from the group consisting of H, F, Cl, CH 3 , CF 3 , OCH 3 , and C(O)O—CH 3 ;

(E) R 15 is H;

(F) Q 1 is O;

(G) Q 2 is S;

(H) R 16 is (K);

(I) R 17 is (K);

(J) L 2 is selected from the group consisting of

wherein, R 20 , R 21 , R 22 , R 23 , and R 24 are each independently selected from the group consisting of H, F, Cl, CH 3 , CH 2 CH 2 CH 3 , CH(CH 3 ) 2 , CF 3 , cyclopropyl, OCH 3 , OCH 2 CH 3 , OCH(CH 3 ) 2 , OC(CH 3 ) 3 , OCH(CH 3 )CH 2 CH 3 , OCF 3 , OCH 2 CF 3 , CH 2 OCH 3 , and CH(CH 3 )OCH 3 ; and

(K) R 16 and R 17 along with C(Q 2 )(N x ), is selected from the group consisting of

wherein R 18 and R 19 are each H.

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

No.

Structure

F1 

F2 

F3 

F4 

F5 

F6 

F7 

F8 

F9 

F10

F11

F12

F13

F14

F15

F16

F17

F18

F19

F20

F21

F22

F23

F24

F25

F26

F27

F28

F29

F30

F31

F32

F33

F34

F35

F36

F37

F38

F39

F40

F41

F42

F43

F44

F45

F46

F47

F48

F49

F50

F51

F52

F53

F54

F55

F56

F57

F58

F59

F60

F61

F62

F63

F64

F65

F66

F67

F68

F69

F70

F71

F72

F73

F74

F75

F76

F77

F78

18. A pesticidal composition comprising

(a) a molecule according to claim 1 and

(b) an active ingredient.

19. A process to control a pest said process comprising applying to a locus, a pesticidally effective amount of a molecule according to claim 1 .

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 Oct 28, 2016
From: GIAMPIETRO, NATALIE C.; CROUSE, GARY D.; SPARKS, THOMAS C.; DEMETER, DAVID A.
To: DOW AGROSCIENCES, LLC
Reel/Frame 040157/0499 →
Continuity (3)
Provisional Application 62214252 · Sep 4, 2015
Provisional Application 62214255 · Sep 4, 2015
Related Publication 20170064962A1 · Mar 9, 2017