IP Library › Granted Patent US 9,107,413

Granted Patent B2

US 9,107,413 · App. 14/224,477 · Granted Aug 18, 2015

Pesticidal compositions and processes related thereto

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Patent No.: US 9,107,413
App. No.: 14/224,477
Granted: Aug 18, 2015
Kind: B2

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Abstract

This document discloses molecules having the following formulas (“Formula One” & “Formula Two” and “Formula Three”) The Ar 1 , Het, Ar 2 , R1, R2, R3, R4, and R5 are further described herein.

Claims (276)

1. A process comprising applying a composition to a locus to control a pest, in an amount sufficient to control such pest said composition comprising a molecule according to Formulas One or Two

wherein:

(a) Ar 1 is

(1) furanyl, phenyl, pyridazinyl, pyridyl, pyrimidinyl, thienyl, or

(2) substituted furanyl, substituted phenyl, substituted pyridazinyl, substituted pyridyl, substituted pyrimidinyl, or substituted thienyl,

wherein said substituted furanyl, substituted phenyl, substituted pyridazinyl, substituted pyridyl, substituted pyrimidinyl, and substituted thienyl, have one or more substituents independently selected from H, F, Cl, Br, I, CN, NO 2 , C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl, C 3 -C 6 cycloalkoxy, C 3 -C 6 halocycloalkoxy, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, S(═O) n (C 1 -C 6 alkyl), S(═O) n (C 1 -C 6 haloalkyl), OSO 2 (C 1 -C 6 alkyl), OSO 2 (C 1 -C 6 haloalkyl), C(═O)NR x R y , (C 1 -C 6 alkyl)NR x R y , C(═O)(C 1 -C 6 alkyl), C(═O)O(C 1 -C 6 alkyl), C(═O)(C 1 -C 6 haloalkyl), C(═O)O(C 1 -C 6 haloalkyl), C(═O)(C 3 -C 6 cycloalkyl), C(═O)O(C 3 -C 6 cycloalkyl), C(═O)(C 2 -C 6 alkenyl), C(═O)O(C 2 -C 6 alkenyl), (C 1 -C 6 alkyl)O(C 1 -C 6 alkyl), (C 1 -C 6 alkyl)S(C 1 -C 6 alkyl), C(═O)(C 1 -C 6 alkyl)C(═O)O(C 1 -C 6 alkyl), phenyl, phenoxy, substituted phenyl, and substituted phenoxy,

wherein such substituted phenyl and substituted phenoxy have one or more substituents independently selected from H, F, Cl, Br, I, CN, NO 2 , C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl, C 3 -C 6 cycloalkoxy, C 3 -C 6 halocycloalkoxy, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, S(═O) n (C 1 -C 6 alkyl), S(═O) n (C 1 -C 6 haloalkyl), OSO 2 (C 1 -C 6 alkyl), OSO 2 (C 1 -C 6 haloalkyl), C(═O)NR x R y , (C 1 -C 6 alkyl)NR x R y , C(═O)(C 1 -C 6 alkyl), C(═O)O(C 1 -C 6 alkyl), C(═O)(C 1 -C 6 haloalkyl), C(═O)O(C 1 -C 6 haloalkyl), C(═O)(C 3 -C 6 cycloalkyl), C(═O)O(C 3 -C 6 cycloalkyl), C(═O)(C 2 -C 6 alkenyl), C(═O)O(C 2 -C 6 alkenyl), (C 1 -C 6 alkyl)O(C 1 -C 6 alkyl), (C 1 -C 6 alkyl)S(C 1 -C 6 alkyl), C(═O)(C 1 -C 6 alkyl)C(═O)O(C 1 -C 6 alkyl) phenyl, and phenoxy;

(b) Het is 1,2,4-triazolyl

(1) furanyl, phenyl, pyridazinyl, pyridyl, pyrimidinyl, thienyl, or

(2) substituted furanyl, substituted phenyl, substituted pyridazinyl, substituted pyridyl, substituted pyrimidinyl, or substituted thienyl, wherein said substituted furanyl, substituted phenyl, substituted pyridazinyl, substituted pyridyl, substituted pyrimidinyl, and substituted thienyl, have one or more substituents independently selected from H, F, Cl, Br, I, CN, NO 2 , C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl, C 3 -C 6 cycloalkoxy, C 3 -C 6 halocycloalkoxy, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, S(═O) n (C 1 -C 6 alkyl), S(═O) n (C 1 -C 6 haloalkyl), OSO 2 (C 1 -C 6 alkyl), OSO 2 (C 1 -C 6 haloalkyl), C(═O)NR x R y , (C 1 -C 6 alkyl)NR x R y , C(═O)(C 1 -C 6 alkyl), C(═O)O(C 1 -C 6 alkyl), C(═O)(C 1 -C 6 haloalkyl), C(═O)O(C 1 -C 6 haloalkyl), C(═O)(C 3 -C 6 cycloalkyl), C(═O)O(C 3 -C 6 cycloalkyl), C(═O)(C 2 -C 6 alkenyl), C(═O)O(C 2 -C 6 alkenyl), (C 1 -C 6 alkyl)O(C 1 -C 6 alkyl), (C 1 -C 6 alkyl)S(C 1 -C 6 alkyl), C(═O)(C 1 -C 6 alkyl)C(═O)O(C 1 -C 6 alkyl), phenyl, phenoxy, substituted phenyl and substituted phenoxy,

wherein such substituted phenyl and substituted phenoxy have one or more substituents independently selected from H, F, Cl, Br, I, CN, NO 2 , C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl, C 3 -C 6 cycloalkoxy, C 3 -C 6 halocycloalkoxy, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, S(═O) n (C 1 -C 6 alkyl), S(═O) n (C 1 -C 6 haloalkyl), OSO 2 (C 1 -C 6 alkyl), OSO 2 (C 1 -C 6 haloalkyl), C(═O)H, C(═O)NR x R y , (C 1 -C 6 alkyl)NR x R y , C(═O)(C 1 -C 6 alkyl), C(═O)O(C 1 -C 6 alkyl), C(═O)(C 1 -C 6 haloalkyl), C(═O)O(C 1 -C 6 haloalkyl), C(═O)(C 3 -C 6 cycloalkyl), C(═O)O(C 3 -C 6 cycloalkyl), C(═O)(C 1 -C 6 haloalkyl), C(═O)(C 2 -C 6 alkenyl), C(═O)O(C 2 -C 6 alkenyl), (C 1 -C 6 alkyl)O(C 1 -C 6 alkyl), (C 1 -C 6 alkyl)S(C 1 -C 6 alkyl), C(═O)(C 1 -C 6 alkyl)C(═O)O(C 1 -C 6 alkyl), phenyl, and phenoxy;

(d) R1 is selected from H, CN, F, Cl, Br, I, C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkoxy, C 1 -C 6 alkoxy, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, S(═O) n (C 1 -C 6 alkyl), OSO 2 (C 1 -C 6 alkyl), C(═O)NR x R y , (C 1 -C 6 alkyl)NR x R y , C(═O)(C 1 -C 6 alkyl), C(═O)O(C 1 -C 6 alkyl), C(═O)(C 3 -C 6 cycloalkyl), C(═O)O(C 3 -C 6 cycloalkyl), C(═O)(C 2 -C 6 alkenyl), C(═O)O(C 2 -C 6 alkenyl), (C 1 -C 6 alkyl)O(C 1 -C 6 alkyl), (C 1 -C 6 alkyl)S(C 1 -C 6 alkyl), C(═O)(C 1 -C 6 alkyl)C(═O)O(C 1 -C 6 alkyl), phenyl, or phenoxy,

wherein each alkyl, cycloalkyl, cycloalkoxy, alkoxy, alkenyl, alkynyl, phenyl, and phenoxy, are optionally substituted with one or more substituents independently selected from F, Cl, Br, I, CN, NO 2 , oxo, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl, C 3 -C 6 cycloalkoxy, C 3 -C 6 halocycloalkoxy, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, S(═O) n (C 1 -C 6 alkyl), S(═O) n (C 1 -C 6 haloalkyl), OSO 2 (C 1 -C 6 alkyl), OSO 2 (C 1 -C 6 haloalkyl), C(═O)NR x R y , (C 1 -C 6 alkyl)NR x R y , C(═O) (C 1 -C 6 alkyl), C(═O)O(C 1 -C 6 alkyl), C(═O)(C 1 -C 6 haloalkyl), C(═O)O(C 1 -C 6 haloalkyl), C(═O)(C 3 -C 6 cycloalkyl), C(═O)O(C 3 -C 6 cycloalkyl), C(═O)(C 2 -C 6 alkenyl), C(═O)O(C 2 -C 6 alkenyl), (C 1 -C 6 alkyl)O(C 1 -C 6 alkyl), (C 1 -C 6 alkyl)S(C 1 -C 6 alkyl), C(═O)(C 1 -C 6 alkyl)C(═O)O(C 1 -C 6 alkyl), phenyl, and phenoxy;

(e) R2 is H, C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C(═O)H, C(═O)(C 1 -C 6 alkyl), C(═O)O(C 1 -C 6 alkyl), C(═O)(C 3 -C 6 cycloalkyl), C(═O)O(C 3 -C 6 cycloalkyl), C(═O)(C 2 -C 6 alkenyl), C(═O)O(C 2 -C 6 alkenyl), (C 1 -C 6 alkyl)O(C 1 -C 6 alkyl), (C 1 -C 6 alkyl)S(C 1 -C 6 alkyl), C(═O)(C 1 -C 6 alkyl)C(═O)O(C 1 -C 6 alkyl), phenyl, C 1 -C 6 alkylphenyl, C 1 -C 6 alkyl-O-phenyl, C(═O)Het-1, Het-1, C 1 -C 6 alkylHet-1, or C 1 -C 6 alkyl-O-Het-1,

wherein each alkyl, cycloalkyl, alkenyl, alkynyl, phenyl, and Het-1 are optionally substituted with one or more substituents independently selected from F, Cl, Br, I, CN, NO 2 , NR x R y , C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl, C 3 -C 6 cycloalkoxy, C 3 -C 6 halocycloalkoxy, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 2 -C 6 alkenyl, C 3 -C 6 cycloalkenyl, C 2 -C 6 alkynyl, S(═O) n (C 1 -C 6 alkyl), S(═O) n (C 1 -C 6 haloalkyl), OSO 2 (C 1 -C 6 alkyl), OSO 2 (C 1 -C 6 haloalkyl), C(═O)H, C(═O)NR x R y , (C 1 -C 6 alkyl)NR x R y , C(═O)(C 1 -C 6 alkyl), C(═O)O(C 1 -C 6 alkyl), C(═O)(C 1 -C 6 haloalkyl), C(═O)O(C 1 -C 6 haloalkyl), C(═O)(C 3 -C 6 cycloalkyl), C(═O)O(C 3 -C 6 cycloalkyl), C(═O)(C 2 -C 6 alkenyl), C(═O)O(C 2 -C 6 alkenyl), (C 1 -C 6 alkyl)O(C 1 -C 6 alkyl), (C 1 -C 6 alkyl)S(C 1 -C 6 alkyl), C(═O)(C 1 -C 6 alkyl)C(═O)O(C 1 -C 6 alkyl), phenyl, phenoxy, and Het-1;

(f) R3 is C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C(═O)H, C(═O)(C 1 -C 6 alkyl), C(═O)O(C 1 -C 6 alkyl), C(═O)(C 3 -C 6 cycloalkyl), C(═O)O(C 3 -C 6 cycloalkyl), C(═O)(C 2 -C 6 alkenyl), C(═O)O(C 2 -C 6 alkenyl), (C 1 -C 6 alkyl)O(C 1 -C 6 alkyl), (C 1 -C 6 alkyl)S(C 1 -C 6 alkyl), C(═O)(C 1 -C 6 alkyl)C(═O)O(C 1 -C 6 alkyl), phenyl, C 1 -C 6 alkylphenyl, C 1 -C 6 alkyl-O-phenyl, C(═O)Het-1, Het-1, C 1 -C 6 alkylHet-1, C 1 -C 6 alkyl-O—C(═O)C 1 -C 6 alkyl-O—C 1 -C 6 alkyl, C 1 -C 6 alkyl-O—C(═O)C 1 -C 6 alkyl-O—C 1 -C 6 alkyl-O—C 1 -C 6 alkyl, C 1 -C 6 alkyl-O—C(═O)C 1 -C 6 alkyl-O—C 1 -C 6 haloalkyl, C 1 -C 6 alkyl-O—C(═O)C 1 -C 6 alkyl-N(R x )C(═O)—O-phenyl, C 1 -C 6 alkyl-O—C(═O)C 1 -C 6 alkyl-N(R x )C(═O)—O—C 1 -C 6 alkylphenyl, C 1 -C 6 alkylC(═O)N(R x )C 1 -C 6 alkyl, C 1 -C 6 alkylC(═O)N(R x )C 1 -C 6 alkylHet-1C(═O)—O—C 1 -C 6 alkyl, C 1 -C 6 alkylC(═O)N(R x )C 1 -C 6 alkylHet-1, C 1 -C 6 alkylC(═O)Het-1, C 1 -C 6 alkylC(═O)N(R x )C 1 -C 6 alkyl(N(R x )(R y ))(C(═O)OH), C 1 -C 6 alkylC(═O)N(R x )C 1 -C 6 alkylN(R x )(R y ), C 1 -C 6 alkylC(═O)N(R x )C 1 -C 6 alkylN(R x )C(═O)—O—C 1 -C 6 alkyl, C 1 -C 6 alkylC(═O)N(R x )C 1 -C 6 alkyl(N(R x )C(═O)—O—C 1 -C 6 alkyl)(C(═O)OH), C 1 -C 6 alkylC(═O)Het-1C(═O)—O—C 1 -C 6 alkyl, C 1 -C 6 alkyl-O—C(═O)—O—C 1 -C 6 alkyl, C 1 -C 6 alkyl-O—C(═O)C 1 -C 6 alkyl, C 1 -C 6 alkyl-O—C(═O)C 3 -C 6 cycloalkyl, C 1 -C 6 alkyl-O—C(═O)Het-1, C 1 -C 6 alkyl-O—C(═O)C 1 -C 6 alkyl-N(R x )C(═O)—O—C 1 -C 6 alkyl, C 1 -C 6 alkyl-NR x R y , or C 1 -C 6 alkyl-O-Het-1,

wherein each alkyl, cycloalkyl, alkenyl, alkynyl, phenyl, and Het-1 are optionally substituted with one or more substituents independently selected from F, Cl, Br, I, CN, NO 2 , NR x R y , C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl, C 3 -C 6 cycloalkoxy, C 3 -C 6 halocycloalkoxy, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 2 -C 6 alkenyl, C 3 -C 6 cycloalkenyl, C 2 -C 6 alkynyl, S(═O) n (C 1 -C 6 alkyl), S(═O) n (C 1 -C 6 haloalkyl), OSO 2 (C 1 -C 6 alkyl), OSO 2 (C 1 -C 6 haloalkyl), C(═O)H, C(═O)OH, C(═O)NR x R y , (C 1 -C 6 alkyl)NR x R y , C(═O)(C 1 -C 6 alkyl), C(═O)O(C 1 -C 6 alkyl), C(═O)(C 1 -C 6 haloalkyl), C(═O)O(C 1 -C 6 haloalkyl), C(═O)(C 3 -C 6 cycloalkyl), C(═O)O(C 3 -C 6 cycloalkyl), C(═O)(C 2 -C 6 alkenyl), C(═O)O(C 2 -C 6 alkenyl), (C 1 -C 6 alkyl)O(C 1 -C 6 alkyl), (C 1 -C 6 alkyl)S(C 1 -C 6 alkyl), C(═O)(C 1 -C 6 alkyl)C(═O)O(C 1 -C 6 alkyl), phenyl, phenoxy, Si(C 1 -C 6 alkyl) 3 , S(═O) n R x R y , and Het-1;

(g) R4 is H, C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C(═O)H, C(═O)(C 1 -C 6 alkyl), C(═O)O(C 1 -C 6 alkyl), C(═O)(C 3 -C 6 cycloalkyl), C(═O)O(C 3 -C 6 cycloalkyl), C(═O)(C 2 -C 6 alkenyl), C(═O)O(C 2 -C 6 alkenyl), (C 1 -C 6 alkyl)O(C 1 -C 6 alkyl), (C 1 -C 6 alkyl)S(C 1 -C 6 alkyl), C(═O)(C 1 -C 6 alkyl)C(═O)O(C 1 -C 6 alkyl), phenyl, C 1 -C 6 alkylphenyl, C 1 -C 6 alkyl-O-phenyl, C(═O)Het-1, Het-1, C 1 -C 6 alkylHet-1, or C 1 -C 6 alkyl-O-Het-1,

(h) R5 is a 2 to 4 membered saturated or unsaturated hydrocarbyl linkage where said linkage may also be substituted with F, Cl, Br, I, CN, NO 2 , oxo, NR x R y , C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl, C 3 -C 6 cycloalkoxy, C 3 -C 6 halocycloalkoxy, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 2 -C 6 alkenyl, C 3 -C 6 cycloalkenyl, C 2 -C 6 alkynyl, S(═O) n (C 1 -C 6 alkyl), S(═O) n (C 1 -C 6 haloalkyl), OSO 2 (C 1 -C 6 alkyl), OSO 2 (C 1 -C 6 haloalkyl), C(═O)H, C(═O)OH, C(═O)NR x R y , (C 1 -C 6 alkyl)NR x R y , C(═O)(C 1 -C 6 alkyl), C(═O)O(C 1 -C 6 alkyl), C(═O)(C 1 -C 6 haloalkyl), C(═O)O(C 1 -C 6 haloalkyl), C(═O)(C 3 -C 6 cycloalkyl), C(═O)O(C 3 -C 6 cycloalkyl), C(═O)(C 2 -C 6 alkenyl), C(═O)O(C 2 -C 6 alkenyl), (C 1 -C 6 alkyl)O(C 1 -C 6 alkyl), (C 1 -C 6 alkyl)S(C 1 -C 6 alkyl), C(═O)(C 1 -C 6 alkyl)C(═O)O(C 1 -C 6 alkyl), phenyl, phenoxy, and Het-1,

wherein each alkyl, cycloalkyl, cycloalkoxy, alkoxy, alkenyl, alkynyl, phenyl, phenoxy, and Het-1, are optionally substituted with one or more substituents independently selected from F, Cl, Br, I, CN, NO 2 , oxo, NR x R y , C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl, C 3 -C 6 cycloalkoxy, C 3 -C 6 halocycloalkoxy, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 2 -C 6 alkenyl, C 3 -C 6 cycloalkenyl, C 2 -C 6 alkynyl, S(═O) n (C 1 -C 6 alkyl), S(═O) n (C 1 -C 6 haloalkyl), OSO 2 (C 1 -C 6 alkyl), OSO 2 (C 1 -C 6 haloalkyl), C(═O)H, C(═O)OH, C(═O)NR x R y , (C 1 -C 6 alkyl)NR x R y , C(═O)(C 1 -C 6 alkyl), C(═O)O(C 1 -C 6 alkyl), C(═O)(C 1 -C 6 haloalkyl), C(═O)O(C 1 -C 6 haloalkyl), C(═O)(C 3 -C 6 cycloalkyl), C(═O)O(C 3 -C 6 cycloalkyl), C(═O)(C 2 -C 6 alkenyl), C(═O)O(C 2 -C 6 alkenyl), (C 1 -C 6 alkyl)O(C 1 -C 6 alkyl), (C 1 -C 6 alkyl)S(C 1 -C 6 alkyl), C(═O)(C 1 -C 6 alkyl)C(═O)O(C 1 -C 6 alkyl), phenyl, halophenyl, phenoxy, and Het-1;

(i) n=0, 1, or 2;

(j) R x and R y are independently selected from H, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, S(═O) n (C 1 -C 6 alkyl), S(═O) n (C 1 -C 6 haloalkyl), OSO 2 (C 1 -C 6 alkyl), OSO 2 (C 1 -C 6 haloalkyl), C(═O)H, C(═O)(C 1 -C 6 alkyl), C(═O)O(C 1 -C 6 alkyl), C(═O)(C 1 -C 6 haloalkyl), C(═O)O(C 1 -C 6 haloalkyl), C(═O)(C 3 -C 6 cycloalkyl), C(═O)O(C 3 -C 6 cycloalkyl), C(═O)(C 2 -C 6 alkenyl), C(═O)O(C 2 -C 6 alkenyl), (C 1 -C 6 alkyl)O(C 1 -C 6 alkyl), (C 1 -C 6 alkyl)S(C 1 -C 6 alkyl), C(═O)(C 1 -C 6 alkyl)C(═O)O(C 1 -C 6 alkyl), and phenyl,

wherein each alkyl, cycloalkyl, cycloalkoxy, alkoxy, alkenyl, alkynyl, phenyl, phenoxy, and Het-1, are optionally substituted with one or more substituents independently selected from F, Cl, Br, I, CN, NO 2 , oxo, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl, C 3 -C 6 cycloalkoxy, C 3 -C 6 halocycloalkoxy, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 2 -C 6 alkenyl, C 3 -C 6 cycloalkenyl, C 2 -C 6 alkynyl, S(═O) n (C 1 -C 6 alkyl), S(═O) n (C 1 -C 6 haloalkyl), OSO 2 (C 1 -C 6 alkyl), OSO 2 (C 1 -C 6 haloalkyl), C(═O)H, C(═O)OH, C(═O)(C 1 -C 6 alkyl), C(═O)O(C 1 -C 6 alkyl), C(═O)(C 1 -C 6 haloalkyl), C(═O)O(C 1 -C 6 haloalkyl), C(═O)(C 3 -C 6 cycloalkyl), C(═O)O(C 3 -C 6 cycloalkyl), C(═O)(C 2 -C 6 alkenyl), C(═O)O(C 2 -C 6 alkenyl), (C 1 -C 6 alkyl)O(C 1 -C 6 alkyl), (C 1 -C 6 alkyl)S(C 1 -C 6 alkyl), C(═O)(C 1 -C 6 alkyl)C(═O)O(C 1 -C 6 alkyl), phenyl, halophenyl, phenoxy, and Het-1,

or R x and R y together can optionally form a 5- to 7-membered saturated or unsaturated cyclic group which may contain one or more heteroatoms selected from nitrogen, sulfur, and oxygen, and where said cyclic group can contain >C═O or >C═S, and where said cyclic group may be substituted with F, Cl, Br, I, CN, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl, C 3 -C 6 cycloalkoxy, C 3 -C 6 halocycloalkoxy, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 2 -C 6 alkenyl, C 3 -C 6 cycloalkenyl, C 2 -C 6 alkynyl, S(═O) n (C 1 -C 6 alkyl), S(═O) n (C 1 -C 6 haloalkyl), OSO 2 (C 1 -C 6 alkyl), OSO 2 (C 1 -C 6 haloalkyl), C(═O)(C 1 -C 6 alkyl), C(═O)O(C 1 -C 6 alkyl), C(═O)(C 1 -C 6 haloalkyl), C(═O)O(C 1 -C 6 haloalkyl), C(═O)(C 3 -C 6 cycloalkyl), C(═O)O(C 3 -C 6 cycloalkyl), C(═O)(C 2 -C 6 alkenyl), C(═O)O(C 2 -C 6 alkenyl), (C 1 -C 6 alkyl)O(C 1 -C 6 alkyl), (C 1 -C 6 alkyl)S(C 1 -C 6 alkyl), C(═O)(C 1 -C 6 alkyl)C(═O)O(C 1 -C 6 alkyl), phenyl, substituted phenyl, phenoxy, and Het-1; and

(k) 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.

2. A process according to claim 1 wherein said composition said molecule said Ar 1 is a substituted phenyl wherein said substituted phenyl has one or more substituents independently selected from C 1 -C 6 haloalkyl and C 1 -C 6 haloalkoxy.

3. A process according to claim 1 wherein said composition said molecule said Ar 1 is a substituted phenyl wherein said substituted phenyl, has one or more substituents independently selected from CF 3 , OCF 3 , and OCF 2 CF 3 .

4. A process according to claim 1 wherein said composition said molecule said Ar 2 is a phenyl.

5. A process according to claim 1 wherein said composition said molecule said R1 is H or C 1 -C 6 alkyl.

6. A process according to claim 1 wherein said composition said molecule said R1 is H or CH 3 .

7. A process according to claim 1 wherein said composition said molecule said R2 is H.

8. A process according to claim 1 wherein said composition said molecule said R3 is C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 alkylphenyl, C 1 -C 6 alkylHet-1, C 1 -C 6 alkyl-O—C(═O)C 1 -C 6 alkyl-O—C 1 -C 6 alkyl, C 1 -C 6 alkyl-O—C(═O)C 1 -C 6 alkyl-O—C 1 -C 6 alkyl-O—C 1 -C 6 alkyl, C 1 -C 6 alkyl-O—C(═O)C 1 -C 6 alkyl-O—C 1 -C 6 haloalkyl, C 1 -C 6 alkyl-O—C(═O)C 1 -C 6 alkyl-N(R x )C(═O)—O-phenyl, C 1 -C 6 alkyl-O—C(═O)C 1 -C 6 alkyl-N(R x )C(═O)—O—C 1 -C 6 alkylphenyl, C 1 -C 6 alkylC(═O)N(R x )C 1 -C 6 alkyl, C 1 -C 6 alkylC(═O)N(R x )C 1 -C 6 alkylHet-1C(═O)—O—C 1 -C 6 alkyl, C 1 -C 6 alkylC(═O)N(R x )C 1 -C 6 alkylHet-1, C 1 -C 6 alkylC(═O)Het-1, C 1 -C 6 alkylC(═O)N(R x )C 1 -C 6 alkyl(N(R x )(R y ))(C(═O)OH), C 1 -C 6 alkylC(═O)N(R x )C 1 -C 6 alkylN(R x )(R y ), C 1 -C 6 alkylC(═O)N(R x )C 1 -C 6 alkylN(R x )C(═O)—O—C 1 -C 6 alkyl, C 1 -C 6 alkylC(═O)N(R x )C 1 -C 6 alkyl(N(R x )C(═O)—O—C 1 -C 6 alkyl)(C(═O)OH), C 1 -C 6 alkylC(═O)Het-1C(═O)—O—C 1 -C 6 alkyl, C 1 -C 6 alkyl-O—C(═O)—O—C 1 -C 6 alkyl, C 1 -C 6 alkyl-O—C(═O)C 1 -C 6 alkyl, C 1 -C 6 alkyl-O—C(═O)C 3 -C 6 cycloalkyl, C 1 -C 6 alkyl-O—C(═O)Het-1, or C 1 -C 6 alkyl-O—C(═O)C 1 -C 6 alkyl-N(R x )C(═O)—O—C 1 -C 6 alkyl

wherein each alkyl, alkenyl, alkynyl, phenyl, and Het-1 are optionally substituted with one or more substituents independently selected from F, Cl, Br, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 haloalkoxy, S(═O) n (C 1 -C 6 alkyl), C(═O)OH, C(═O)O(C 1 -C 6 alkyl), phenyl, Si(C 1 -C 6 alkyl) 3 , and S(═O)—NR x R y .

9. A process according to claim 1 wherein said composition said molecule said R4 is phenyl, C 1 -C 6 alkylphenyl, or C 1 -C 6 alkyl-O-phenyl, wherein each alkyl and phenyl are optionally substituted with one or more substituents independently selected from F, Cl, NR x R y , C 1 -C 6 alkyl, or C 1 -C 6 alkoxy.

10. A process according to claim 1 wherein said composition said molecule

Ar 1 is a substituted phenyl wherein said substituted phenyl, has one or more C 1 -C 6 haloalkoxy;

Ar 2 is a phenyl;

R1 is H;

R2 is H;

R3 is C 1 -C 6 alkylHet-1 wherein said alkyl and Het-1 are optionally substituted with one or more substituents independently selected from F, Cl, Br, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 haloalkoxy, S(═O) n (C 1 -C 6 alkyl), C(═O)OH, C(═O)O(C 1 -C 6 alkyl), phenyl, Si(C 1 -C 6 alkyl) 3 , and S(═O)—R x R y ,

R4 is phenyl, wherein said phenyl is optionally substituted with one or more substituents independently selected from F, Cl, NR x R y , C 1 -C 6 alkyl, or C 1 -C 6 alkoxy; and

n=0, 1, or 2;

R x and R y are independently selected from H and phenyl, wherein said phenyl, may be optionally substituted with one or more substituents independently selected from F and Cl; and

Het-1 is wherein 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.

11. A process according to claim 1 wherein said composition said molecule is selected from one of the following structures

Structure

10C

11C

12C

13C

14C

15C

16C

17C

18C

19C

20C

21C

22C

23C

24C

25C

26C

27C

28C

29C

30C

31C

32C

33C

34C

35C

36C

37C

38C

39C

40C

41C

42C

43C

44C

45C

46C

47C

48C

49C

50C

51C

52C

53C

54C

55C

56C

57C

58C

59C

60C

61C

62C

63C

64C

65C

66C

67C

68C

69C

70C

71C

72C

73C

74C

75C

76C

77C

78C

79C

80C

88C

89C

90C

91C

92C

93C

94C

95C

96C

97C

98C

99C

100C

101C

105C

106C

107C

108C

111C

112C

113C

114C

115C

116C

117C

118C

119C

120C

121C

122C

123C

124C

125C

126C

127C

128C

129C

130C

131C

132C

133C

134C

135C

136C

137C

138C

139C

140C

141C

142C

143C

144C

145C

146C

147C

148C

149C

150C

151C

152C

153C

154C

155C

156C

157C

158C

159C

160C

161C

162C

163C

164C

165C

166C

167C

168C

169C

170C

171C

172C

173C

174C

175C

176C

177C

178C

179C

180C

181C

182C

183C

184C

185C

186C

187C

188C

189C

190C

191C

192C

193C

194C

195C

196C

197C

198C

199C

200C

201C

202C

203C

204C

205C

206C

207C

208C

209C

210C

211C

212C

213C

214C

215C

216C

217C

218C

219C

220C

221C

222C

223C

224C

225C

226C

227C

228C

229C

230C

231C

232C

233C

234C

235C

236C

237C

238C

239C

Assignments (1)

CHANGE OF NAME Recorded Nov 8, 2021

From: DOW AGROSCIENCES LLC

To: CORTEVA AGRISCIENCE LLC

Reel/Frame 058044/0184 →