WO2002048137A2

WO2002048137A2 - Substituted heterocyclic phthalic acid diamide arthropodicides

Info

Publication number: WO2002048137A2
Application number: PCT/US2001/047572
Authority: WO
Inventors: George Philip Lahm; Thomas Paul Selby
Original assignee: E. I. Du Pont De Nemours And Company
Priority date: 2000-12-11
Filing date: 2001-12-05
Publication date: 2002-06-20
Also published as: EP1341780A2; AU2002228938A1; JP2004515547A; WO2002048137A3

Abstract

Compounds of (I), and their N-oxides and agriculturally suitable salts, are disclosed which are useful for controlling invertebrate pests (Formula) wherein J is selected from the group consisting of J-1, J-2, J-3, J-4, J-5, J-6, J-7 and J-8 (I) and R1, R2, R3, R4, R5, R7, R9 and n are as defined in the disclosure.Also disclosed are compositions for controlling an invertebrate pest comprising a biologically effective amount of a compound of (I) and methods for controlling an invertebrate pest comprising contacting the invertebrate pest or its environment with a biologically effective amount of a compound of (I) (e.g., as a composition described herein).

Description

SUBSTITUTED HETEROCYCLIC PHTHALIC ACID DIAMIDE ARTHROPODICIDES

BACKGROUND OF THE INVENTION This invention relates to certain heterocyclic phthalic acid diamides, their N-oxides, agriculturally suitable salts and compositions, and methods of their use as arthropodicides in both agronomic and nonagronomic environments.

The control of invetebrate pests is extremely important in achieving high crop efficiency. Damage by invertebrate pests to growing and stored agronomic crops can cause significant reduction in productivity and thereby result in increased costs to the consumer. The control of invertebrate pests in forestry, greenhouse crops, ornamentals, nursery crops, stored food and fiber products, livestock, household, and public and animal health is also important. Many products are commercially available for these purposes, but the need continues for new compounds that are more effective, less costly, less toxic, environmentally safer or have different modes of action. EP919542 discloses phthalic acid diamides of Formula i as insecticides

wherein, inter alia,

Z¹ and Z² are O or S; and

R¹, R² and R³ are, among others, H, alkyl or substituted alkyl. WOO 1/02354 discloses phthalic acid diamides of Formula ii as insecticides

wherein, inter alia,

Q is an optionally substituted hetero cycle containing O, S or ; Z¹ and Z² are O or S; and R¹, R² and R³ are, among others, H, alkyl or substituted alkyl. SUMMARY OF THE INVENTION

This invention pertains to compounds of Formula I and N-oxides and agriculturally suitable salts thereof

wherein

J is selected from the group consisting of J-l, J-2, J-3, J-4, J-5, J-6, J-7 and J-8

R¹ is H, Ci-C₆ alkyl, C₂-C6 alkoxycarbonyl or C2-C6 alkylcarbonyl;

R² is H or Cι-C₆ alkyl;

R³ is H; C_rC₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₃-C₆ cycloalkyl, or C₄-C₈ cycloalkylalkyl, each optionally substituted with one or more substituents selected from the group consisting of halogen, CN, NO₂, hydroxy, C1-C4 alkyl, C_!-C4 alkoxy, C₁-C4 haloalkoxy, C_]-C₄ alkylthio, C1-C4 alkylsulfmyl, C1-C4 alkylsulfonyl, C^-C^ alkoxycarbonyl or C₂-Cg alkylcarbonyl; one R⁴ group is attached to the phenyl ring at the 3-position or 6-position, and said R⁴ is C_rC4 alkyl, C_rC₄ haloalkyl, halogen, CN, NO₂, C_!-C₄ alkoxy, C_rC₄ haloalkoxy, -C4 alkylthio, -C4 alkylsulfmyl, C₁-C4 alkylsulfonyl, C1-C4 haloalkylthio, C1-C₄ haloalkylsulfinyl, or C1-C4 haloalkylsulfonyl; and an optional second R⁴ is H, C_]_-C₆ alkyl, C₂-Cg alkenyl, C₂-C6 alkynyl, C3-C6 cycloalkyl, C^-Cg haloalkyl, C2-Cg haloalkenyl, C2-C6 haloalkynyl, C3-C6 halocycloalkyl, halogen, CN, NO₂, hydroxy, C1-C4 alkoxy, C1-C4 haloalkoxy,

C1-C4 alkylthio, C1-C4 alkylsulfinyl, C₁-C4 alkylsulfonyl, C1-C4 haloalkylthio, C1-C₄ haloalkylsulfinyl, C1-C₄ haloalkylsulfonyl, C1-C4 alkylamino, C2-Cg dialkylamino, C₃-C6 cycloalkylamino, C1-C4 alkoxyalkyl, C1-C4 hydroxyalkyl, C(O)R¹⁰, CO₂R¹⁰, C^ RⁱOR^ll, NR^RH, NCR^COR¹⁰, N(R )CO₂R¹⁰ or C₃-C₆ trialkylsilyl;

R⁵ is H, Ci-C₄ alkyl, C_rC₄ haloalkyl, or

Y is N, CH, CF, CC1, CBr or Cl; each R⁶ and R⁷ is independently H, C^-Cg alkyl, C3-C6 cycloalkyl, Cj-Cg haloalkyl, halogen, CN, C₁-C4 alkoxy, C1-C₄ haloalkoxy or C1-C₄ haloalkylthio;

R⁹ is H, C_rC₆ alkyl, C_rC₆ haloalkyl, C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₃-C₆ alkynyl or C₃-C6 haloalkynyl; provided R⁷ and R⁹ are not both H; R¹⁰ is H or Cr-C- alkyl or C1-C haloalkyl; R¹1 is H or -C4 alkyl; and n is 1 or 2.

This invention also pertains to a composition for controlling an invertebrate pest comprising a biologically effective amount of a compound of Formula I and at least one additional component selected from the group consisting of surfactants, solid diluents and liquid diluents. This invention also pertains to a composition comprising a biologically effective amount of a compound of Formula I and an effective amount of at least one additional biologically active compound or agent.

This invention also pertains to a method for controlling an invertebrate pest comprising contacting the invertebrate pest or its environment with a biologically effective amount of a compound of Formula I (e.g., as a composition described herein). This invention also relates to such method wherein the invertebrate pest or its environment is contacted with a biologically effective amount of a compound of Formula I or a composition comprising a compound of Formula I and a biologically effective amount of at least one additional compound or agent for controlling invertebrate pests. DETAILS OF THE INVENTION

In the above recitations, the term "alkyl", used either alone or in compound words such as "alkylthio" or "haloalkyl" includes straight-chain or branched alkyl, such as methyl, ethyl, /.-propyl, t^'-propyl, or the different butyl, pentyl or hexyl isomers. "Alkenyl" can include straight-chain or branched alkenes such as 1 -propenyl, 2-propenyl, and the different butenyl, pentenyl andhexenyl isomers. "Alkenyl" also includes polyenes such as 1,2-propadienyl and 2,4-hexadienyl. "Alkynyl" includes straight-chain or branched alkynes such as 1-propynyl, 2-propynyl and the different butynyl, pentynyl and hexynyl isomers. "Alkynyl" can also include moieties comprised of multiple triple bonds such as 2,5-hexadiynyl. "Alkoxy" includes, for example, methoxy, ethoxy, «-propyloxy, isopropyloxy and the different butoxy, pentoxy and hexyloxy isomers. "Alkoxyalkyi" denotes alkoxy substitution on alkyl. Examples of "alkoxyalkyi" include CH₃OCH2, CH₃OCH₂CH₂, CH₃CH₂OCH₂, CH₃CH₂CH₂CH₂OCH₂ and CH₃CH₂OCH₂CH₂. "Alkylthio" includes branched or straight-chain alkylthio moieties such as methylthio, ethylthio, and the different propylthio, butylthio, pentylthio and hexylthio isomers.

"Cycloalkyl" includes, for example, cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl. "Cycloalkylalkyi" indicates an alkyl group substituted with a cycloalky group and includes, for example, cyclopropylmethyl, cyclobutylethyl, cyclopentylpropyl and cyclohexylmethyl. The term "heteroaromatic ring" denotes fully aromatic rings in which at least one ring atom is not carbon and can contain 1 to 4 heteroatoms independently selected from the group consisting of nitrogen, oxygen and sulfur, provided that each heteroaromatic ring contains no more than 4 nitrogens, no more than 2 oxygens and no more than 2 sulfurs (where aromatic indicates that the Hϋckel rule is satisfied). The heteroaromatic ring can be attached through any available carbon or nitrogen by replacement of hydrogen on said carbon or nitrogen. The term "halogen", either alone or in compound words such as "haloalkyl", includes fluorine, chlorine, bromine or iodine. Further, when used in compound words such as "haloalkyl", said alkyl may be partially or fully substituted with halogen atoms which may be the same or different. Examples of "haloalkyl" include F₃C, CICH2, CF3CH2 and CF₃CC1₂. The terms "haloalkenyl", "haloalkynyl", "haloalkoxy", and the like, are defined analogously to the term "haloalkyl". Examples of "haloalkenyl" include (C1)₂C=CHCH₂ and CF₃CH₂CH=CHCH₂. Examples of "haloalkynyl" include HC≡CCHCl, CF₃C≡C, CC1₃C≡C and FCH₂C≡CCH₂. Examples of "haloalkoxy" include CF₃O, CCl₃CH₂O, HCF₂CH₂CH₂O and CF₃CH₂O.

The total number of carbon atoms in a substituent group is indicated by the "Cj-C_j" prefix where i and j are numbers from 1 to 6. For example, C1-C₃ alkylsulfonyl designates methylsulfonyl through propylsulfonyl; C₂ alkoxyalkyi designates CH₃OCH₂; C₃ alkoxyalkyi designates, for example, CH₃CH(OCH₃), CH₃OCH₂CH₂ or CH₃CH₂OCH₂; and C4 alkoxyalkyi designates the various isomers of an alkyl group substituted with an alkoxy group containing a total of four carbon atoms, examples including CH3CH₂CH₂OCH₂ and CH3CH2OCH2CH2. In the above recitations, when a compound of Formula I contains a heteroaromatic ring, all substituents are attached to this ring through any available carbon or nitrogen by replacement of a hydrogen on said carbon or nitrogen. When a group contains a substituent which can be hydrogen, for example R³, then, when this substituent is taken as hydrogen, it is recognized that this is equivalent to said group being unsubstituted.

Compounds of this invention can exist as one or more stereoisomers. The various stereoisomers include enantiomers, diastereomers, atropisomers and geometric isomers. One skilled in the art will appreciate that one stereoisomer may be more active and/or may exhibit beneficial effects when enriched relative to the other stereoisomer(s) or when separated from the other stereoisomer(s). Additionally, the skilled artisan knows how to separate, enrich, and/or to selectively prepare said stereoisomers. Accordingly, the compounds ofthe invention may be present as a mixture of stereoisomers, individual stereoisomers, or as an optically active form.

The present invention comprises of compounds selected from Formula I, N-oxides and agriculturally suitable salts thereof. One skilled in the art will appreciate that not all nitrogen containing heterocycles can form N-oxides since the nitrogen requires an available lone pair for oxidation to the oxide; one skilled in the art will recognize those nitrogen containing heterocycles which can form N-oxides. One skilled in the art will also recognize that tertiary amines can form N-oxides. Synthetic methods for the preparation of N-oxides of heterocycles and tertiary amines are very well known by one skilled in the art including the oxidation of heterocycles and tertiary amines with peroxy acids such as peracetic and m-chloroperbenzoic acid (MCPB A), hydrogen peroxide, alkyl hydroperoxides such as t-butyl hydroperoxide, sodium perborate, and dioxiranes such as dimethydioxirane. These methods for the preparation of N-oxides have been extensively described and reviewed in the literature, see for example: T. L. Gilchrist in Comprehensive Organic Synthesis, vol. 7, pp 748-750, S. V. Ley, Ed., Pergamon Press; M. Tisler and B. Stanovnik in Comprehensive Heterocyclic Chemistry, vol. 3, pp 18-19, A. J. Boultonand A. McKillop, Eds., Pergamon Press; M. R. Grimmett and B. R. T. Keene Advances in Heterocyclic Chemistry, vol.43, pp 139-151, A. R. Katritzky, Ed., Academic Press; M. Tisler and B. Stanovnik in Advances in Heterocyclic Chemistry, vol. 9, pp 285-291, A. R. Katritzky and A. J. Boulton, Eds., Academic Press; and G. W. H. Cheeseman and E. S. G. Werstiuk in A dvances in Heterocyclic Chemistry, vol. 22, pp 390-392, A. R. Katritzky and A. J. Boulton, Eds., Academic Pres s .

The salts ofthe compounds ofthe invention include acid-addition salts with inorganic or organic acids such as hydrobromic, hydrochloric, nitric, phosphoric, sulfuric, acetic, butyric, fumaric, lactic, maleic, malonic, oxalic, propionic, saHcylic, tartaric, 4-toluenesulfonic or valeric acids.

Of note are compounds of Formula I wherein R⁵ is rVMrV

The wavy line represents the rema σinder of the J group to which said R⁵ moiety is attached.

Preferred compounds for reasons of better activity, cost and/or ease of synthesis are: Preferred 1. Compounds of Formula I wherein V is N. Preferred 2. Compounds of Formula I wherein V is CH, CF, CC1 or CBr. Preferred 3. Compounds of Preferred 1 or Preferred 2 wherein

R¹ and R² are both H;

R³ is C_rC₄ alkyl optionally substituted with halogen, CN, OCH₃, S(O)_pCH ; one R⁴ group is attached to the phenyl ring at the 3-position and said R⁴ is CH₃, CF₃, OCF₃, OCHF₂, S(O)_pCF₃, S(O)_pCHF₂, CN or halogen; a second R⁴ is H, F, Cl, Br, I or CF₃;

R⁶ is C_rC₄ alkyl, C₁-C₄ haloalkyl, halogen or CN; R⁷ is H, CH₃, CF₃, OCHF₂ or halogen; and p is 0, 1 or 2. Preferred 4. Compounds of Preferred 3 wherein J is J-l;

R³ is C1-C₄ alkyl; one R⁴ group is attached to the phenyl ring at the 3-position and said R⁴ is

CH₃, Cl, Br orI; a second R⁴ is H, F, Cl, Br, I or CF₃; R6 is Cl or Br; and

R⁷ is halogen or CF3. Preferred 5. Compounds of Preferred 4 wherein V is N;

R³ is methyl, ethyl, isopropyl or tertiary butyl; one R⁴ group is attached to the phenyl ring at the 3-position and said R⁴ is

CH₃ or I; R⁶ is Cl or Br; and R⁷ is Br, Cl or CF₃. Preferred 6. Compounds of Preferred 3 wherein J is J-2;

R³ is C_rC₄ alkyl; one R⁴ group is attached to the phenyl ring at the 3-position and said R⁴ is CH₃, CL Br or l; a second R⁴ is H, F, Cl, Br, I or CF₃;

R⁶ is Cl or Br; and

R⁹ is CF₃, CHF₂, CH₂CF₃, CF₂CHF₂. Preferred 7. Compounds of Preferred 3 wherein J is J-3; R³ is C_rC₄ alkyl; one R⁴ group is attached to the phenyl ring at the 3-position and said R⁴ is

CH₃, CL Br orl; a second R⁴ is H, F, Cl, Br, I or CF₃; R⁶ is Cl or Br; and R⁷ is halogen or CF₃.

Preferred 8. Compounds of Preferred 3 wherein J is J-4;

R³ is C_!-C₄ alkyl; one R⁴ group is attached to the phenyl ring at the 3-position and said R⁴ is CH₃, CL Br orl; a second R⁴ is H, F, Cl, Br, I or CF ; R⁶ is Cl or Br; and R⁷ is CF₃. Preferred 9. Compounds of Preferred 3 wherein J is J-5;

R³ is C_rC₄ alkyl; one R⁴ group is attached to the phenyl ring at the 3-position and said R⁴ is

CH₃, CL Br or l; a second R⁴ is H, F, Cl, Br, I or CF₃; R⁶ is Cl or Br; and

R9 is CF₃, CHF₂, CH₂CF₃, CF₂CHF₂. Preferred 10. Compounds of Preferred 3 wherein J is J-6;

CH₃, CL Br orl; a second R⁴ is H, F, Cl, Br, I or CF₃; R⁶ is Cl or Br; and R⁷ is halogen or CF₃. Preferred 11. Compounds of Preferred 3 wherein J is J-7;

R³ is C_rC₄ alkyl; one R⁴ group is attached to the K-ring at the 2-position and said R⁴ is CH3, Cl or Br; a second R⁴ is H, F, Cl, Br, I or CF₃; R⁶ is Cl or Br; R⁷ is H, halogen or CF₃.and R9 is H, CF₃, CHF₂, CH₂CF₃, CF₂CHF₂.

Preferred 12. Compounds of Preferred 3 wherein J is J-8;

R³ is C_rC₄ alkyl; one R⁴ group is attached to the phenyl ring at the 3-position and said R⁴ is CH₃, CL Brorl; a second R⁴ is H, F, Cl, Br, I or CF₃; R⁶ is Cl or Br; R⁷ is H, halogen or CF3.and R9 is H, CF₃, CHF₂, CH₂CF₃, CF₂CHF₂. Specifically preferred are compounds selected from the group consisting of:

N^!-[ 1 -(3-chloro-2-pvridinyl)-3-(trifluoromethyl)- lH-pyrazol-5-y l]-3-methyl-N²-( 1 - methylethyl)- 1 ,2-benzenedicarboxamide,

N -[ 1 -(3-bromo- 1 -(3-chloro-2-pyridinyl)- lH-pyrazol-5-y l]-3-methyl-N²-( 1 - methylethyl)- 1 ,2-benzenedicarboxamide, N^/-[l-(3-chloro-2-pvridmyl)-3-( fluoromethyl)-lH-ρyrazol-5-yl]-3-iodo-N²-(l- methylethyl)- 1 ,2-benzenedicarboxamide, and

Nⁱ-[l-(3-bromo-l-(3-chloro-2-pyridinyl)-lH-pyrazol-5-yl]-3-iodo-N²-(l- methylethyl)-l ,2-benzenedicarboxamide. The preferred compositions ofthe present invention are those that comprise the above preferred compounds.

The preferred methods of use are those involving the above preferred compounds. Of note are compounds of Formula Id and N-oxides and agriculturally suitable salts thereof

Id

wherein

J is selected from the group consisting of

J-59 J-60 J-61 J-62

R¹ is H, C^-Cg alkyl, C₂-C6 alkoxycarbonyl or C₂-Cg alkylcarbonyl;

R² is H or C_rC₆ alkyl;

R³ is H; Cj-Cg alkyl, C -C6 alkenyl, C₂-Cg alkynyl, or C3-C₆ cycloalkyl, each optionally substituted with one or more substituents selected from the group consisting of halogen, CN, NO₂, hydroxy, C₁-C4 alkyl, -C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, -C₄ alkylsulfmyl, C₁-C4 alkylsulfonyl, C₂-C6 alkoxycarbonyl, C₂-Cg alkylcarbonyl, C3-C6 trialkylsilyl, or a phenyl, phenoxy or 5- or 6-membered heteroaromatic ring, each ring optionally substituted with one to three substituents independently selected from the group consisting of Cj -C alkyl, C₂-C4 alkenyl, C₂-C alkynyl, C₃-C5 cycloalkyl, C1-C₄ haloalkyl, C₂-C4 haloalkenyl, C₂-C4 haloalkynyl, C₃-C6 halocycloalkyl, halogen, CN, NO₂, C1-C4 alkoxy, C₁-C4 haloalkoxy, C₁-C4 alkylthio, C₁-C₄ alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 alkylamino, C₂-Cg dialkylamino, C₃-C₆ cycloallcylamino, C -Cg (alJ-yl)cycloalkylamino, C₂-C₄ alkylcarbonyl, C₂-C6 alkoxycarbonyl, C₂-Cg alkylamino carbonyl, C₃-Cg dialkylaminocarbonyl or C₃-C6 trialkylsilyl; C^ alkoxy; Cι~C alkylamino; C₂-C₃ cUalkylamino; C₃- C₆ cycloalkylamino; C₂-C₆ alkoxycarbonyl or C₂-Cg alkylcarbonyl; eachR⁴ is independently H, Ci-Cg alkyl, C₂-Cg alkenyl, C₂-Cg alkynyl, C₃-C6 cycloalkyl, C^-Cg haloalkyl, C1-C4 alkoxyalkyi, CN, halogen, C1-C4 alkoxy, C_!-C₄ haloalkoxy, S(O)_nR¹², C^ hydroxyalkyl, C(O)R¹⁰, CHO, CO₂R¹⁰, C(O)NR^1θR¹¹, NO₂, NR^lOR^ll or N(R^u)CO₂R¹⁰; each R⁶ is independently Cj-Cg alkyl, C_j-Cg haloalkyl, halogen, CN, C1-C4 alkoxy,

C₁-C4 haloalkoxy or C1-C4 haloalkylthio; R⁷ is C1-C4 alkyl, C₂-C alkenyl, C₂-C4 alkynyl, C₃-C6 cycloalkyl, -C4 haloalkyl, C₂-C4 haloalkenyl, C₂-C4 haloalkynyl, C3-C6 halocycloalkyl, halogen, CN, NO₂, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C4 alkylthio, C1-C4 alkylsulfinyl, Cy C₄ alkylsulfonyl, C1-C4 alkylamino, C₂-Cg dialkylamino, C₃-C6 cycloalkylamino, C3-C6 (alkyl)cycloalkylamino, C₂-C₄ alkylcarbonyl, C₂-Cg alkoxycarbonyl, C -Cg alkylaminocarbonyl, C3-C₈ dialkylaminocarbonyl or C₃- Cg trialkylsilyl; R⁸ is H, C^-Cg alkyl, C €6 haloalkyl, halogen, C₁-C4 alkoxy or C1-C₄ haloalkoxy; R⁹ is C₂-C₆ alkyl, C_rC₆ haloalkyl, C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₃-C₆ alkynyl or C₃-C6 haloalkynyl; R¹⁰ is H or -C4 alkyl or C_!-C₄ haloalkyl; R¹¹ is H OT C!-C₄ alkyl; R¹² is C_!-C₄ alkyl or Ci-C haloalkyl; n is 0, 1 or 2; and

X is , CH, CF, CCl or CBr. Of particular note are selected compounds of Formulald: Selection A. Compounds of Formulal d wherein X is N. Selection B. Compounds of Formulald wherein X is CH, CF, CC1 or CBr. Selection C. The compounds of Selection A or Selection B wherein

J is J-59;

R¹, R² andR⁸ are all H;

R³ is Cι-C₄ alkyl optionally substituted with halogen, CN, OCH₃, S(O)_pCH₃; one R⁴ is CH₃, CF₃, OCF₃, OCHF₂, S(O)_pCF₃, S(O)_pCHF₂, CN or halogen; a second R⁴ is H, F, Cl, Br, I or CF₃ ;

R⁶ is CH3, CF₃ or halogen; and ' p is 0, 1 or 2. Selection D. Compounds of Selection C wherein R³ is C_rC₄ alkyl; one R⁴ is CH₃, Cl orBr; a second R⁴ is H, F, Cl, Br, I or CF ; R⁶ is CF₃; and R⁷ is Cl or Br. Selection E. The compounds of Selection A or Selection B wherein

J is J-60;

R¹ and R² are both H;

R³ is C_rC₄ alkyl optionally substituted with halogen, CN, OCH₃, S(O)_pCH₃; one R⁴ is CH₃, CF₃, OCF₃, OCHF₂, S(O)_pCF₃, S(O)_pCHF₂, CN or halogen; a second R⁴ is H, F, Cl, Br, I or CF₃ ;

R⁹ is C₂-Cg alkyl or Cj-Cg haloalkyl; and p is 0, lor 2. Selection F. Compounds of Selection E wherein R³ is C_rC₄ alkyl; one R⁴ is CH₃, Cl orBr; a second R⁴ is H, F, Cl, Br, I or CF₃;

R⁹ is CF₃, CHF₂, CH₂CF₃, CF₂CHF₂; and

R⁷ is Cl or Br. Selection G. The compounds of Selection A or Selection B wherein

J is J-61;

R¹, R andR⁸ are all H;

R³ is C_rC₄ alkyl optionally substituted with halogen, CN, OCH₃, S(O)_pCH₃; one R⁴ is CH₃, CF₃, OCF₃, OCHF₂, S(O)_pCF₃, S(O)_pCHF₂, CN or halogen; a second R⁴ is H, F, Cl, Br, I or CF₃;

R⁶ is CH₃, CF₃ or halogen; and p is 0, 1 or 2. Selection H. Compounds of Selection G wherein

R³ is C_rC₄ alkyl; one R⁴ is CH₃, Cl orBr; a second R⁴ is H, F, Cl, Br, I or CF₃;

R⁶ is CF₃; and

R⁷ is Cl or Br. Selection I. The compounds of Selection A or Selection B wherein J is J-62;

R¹, R² and R⁸ are all H;

R³ is C_rC₄ alkyl optionally substituted with halogen, CN, OCH₃, S(O)_pCH ; one R⁴ is CH₃, CF₃, OCF₃, OCHF₂, S(O)_pCF₃, S(O)_pCHF₂, CN or halogen; a second R⁴ is H, F, Cl, Br, I or CF₃; R⁶ is CH₃, CF₃ or halogen; and p is 0, 1 or 2. Selection J. Compounds of Selection I wherein

R³ is C_rC₄ alkyl; one R⁴ is CH₃, Cl or Br; a second R⁴ is H, F, Cl, Br, I or CF₃; R⁶ is CF₃; and R⁷ is Cl or Br. Also of note are compositions comprising a biologically effective amount of a compound of Formula Id and at least one additional component selected from the group consisting of surfactants, solid diluents and Hquid diluents. Also of note are said compositions further comprising at least one additional biologically active compound or agent. Selected compositions are those comprising the selected compounds above. Also of note is a method for controlling lepidopteran, homopteran and coleopteran insects comprising contacting the insects or their environment with a biologically effective amount of a compound of Formula Id, its N-oxide or an agriculturally suitable salt thereof. Selected methods are those comprising the selected compounds above.

The compounds of Formula I can be prepared by one or more of the following methods and variations described in Schemes 1 and 2. The definitions of J, R¹, R², R³, R⁴ and n in the compounds of Formulae 1-9 are as defined above in the Summary ofthe Invention.

Phthalic acid diamides of formula lb and Ic can be made by the method described in Scheme 1. Heating a phthalic anhydride of formula 2 with an aminoheterocycle of Formula H₂Ν-J in an inert solvent such as glacial acetic acid affords a phthalimide of Formula 3. Ring-opening of phthalimide 3 with an amine ofthe Formula HNR²R³ in an inert solvent such as dioxane or tetrahydrofuran at room temperture or heating at reflux gives a phthalic acid diamide of formula lb. Alkylation of a compound of formula lb with a suitable alkylating agent (e.g. an alkyl halide or an alkyl methane- or 4-toluene-sulfonate) or acylating agent (e.g. an alkylchloroformate or acid chloride) in the presence of a base such as sodium hydride or H-butyl lithium in an inert solvent such as tefrahydrofuran or

N,N-dimethylformamide affords a phthaHc acid diamide of formula Ic wherein R¹ is a substituent other than hydrogen. PhthaHc anhydrides of Formula 2 can be made by methods taught in/. Org. Chem., 1987, 52, 129, J. Am. Chem. Soc, 1929, 51, 1865, and/. Am. Chem. Soc, 1941, 63, 1542. Aminoheterocycles of formula H₂Ν-J can be made by methods as described in Rodd's Chemistry of Organic Compounds: HeterocycHc Compounds, volume IN, parts C, F and IJ (1989), Comprehensive Heterocyclic Chemistry, volumes 2, 3,4,5 and 6 (1984) and Comprehensive Heterocyclic Chemistry II, volumes 3, 4, 5 and 6 (1996). Scheme 1

lb Ic

Another method for making compounds of Formula I is summarized in Scheme 2. Lithiation of a benzamide of Formula 4 with «-butyl lithium in an inert solvent such as tefrahydrofuran followed by reaction with a carbamoyl chloride of Formula 5 provides a phthalic acid diamide of Formula I wherein R¹ is other than hydrogen. Reaction of a benzamide of Formula 4 with «-butyl lithium in an inert solvent such as tefrahyclrofuran foHowed by reaction with an isocyanate of Formula 6 provides a phthaHc acid diamide of Formula I wherein R¹ is hydrogen. Alternatively, Hthiation of a benzamide of Formula 7 with w-butyl lithium in an inert solvent such as tefrahydrofuran foUowed by reaction with a carbamoyl chloride chloride of Formula 8 provides a phthalic acid diamide of Formula I wherein R² is other than hydrogen. Reaction of a benzamide of Formula 7 with n-butyl lithium in an inert solvent such as tefrahydrofuran followed by reaction with an isocyanate of Formula 9 provides a phthalic acid diamide of Formula 1 wherein R² is hydrogen.

Benzamides of Formulae 4 and 7 are readily made from the corresponding benzoic acids via a benzoyl chloride intermediate or by direct coupling of a benzoic acid and amine in the presence of a suitable acid/amine coupling agent such as 1,3- cHcyclohexylcarbodiimide or 1,1 '-carbonyldiimidazole in an inert solvent such as dichloromethane or N,N-&methylformamide. Benzoic acids are readily converted to the acid chlorides on treatment with thionyl chloride or oxalyl chloride in an inert solvent such as dichloromethane or toluene. The benzoyl chloride is subsequently coupled with an amine of formula HΝR² R³ or HΝ R¹ J in an inert solvent such as tefrahydrofuran or dichloromethane. An additional base such as tertiary amines, pyridine or polymer-bound bases may be used to neutralize the hydrochloric acid produced in the reaction.

Scheme 2

or or 0=C=N— R³ 0=C=N — J

It is recognized that some reagents and reaction conditions described above for preparing compounds of Formula I may not be compatible with certain functionaHties present in the intermediates. In these instances, the incorporation of protection and deprotection sequences or functional group interconversions into the synthesis will aid in obtaining the desired products. The use and choice ofthe protecting groups will be apparent to one skilled in chemical synthesis (see, for example, Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 2nd ed.; Wiley: New York, 1991). One skilled in the art will recognize that, in some cases, after the introduction of a given reagent as it is depicted in any individual scheme, it may be necessary to perform additional routine synthetic steps not described in detail to complete the synthesis of compounds of Formula I. One skilled in the art will also recognize that it may be necessary to perform a combination ofthe steps illustrated in the above schemes in an order other than that implied by the particular sequence presented to prepare the compounds of Formula I.

One skilled in the art will also recognize that compounds of Formula I and the intermediates described herein can be subjected to various electtophilic, nucleophiHc, radical, organometallic, oxidation, and reduction reactions to add substituents or modify existing substituents.

Without further elaboration, it is believed that one skilled in the art using the preceding description can utilize the present invention to its fullest extent. The foUowing Examples are, therefore, to be construed as merely illustrative and not limiting ofthe disclosure in any way whatsoever. Percentages are by weight except for chromatographic solvent mixtures or where otherwise indicated. Parts and percentages for chromatographic solvent mixtures are by volume unless otherwise indicated. ^H NMR spectra are reported in ppm downfield from tetramethylsilane; s is singlet, d is doublet, t is triplet, q is quartet, m is multiplet, dd is doublet of doublets, dt is doublet of triplets, br s is broad singlet.

EXAMPLE 1 Step A: Preparation of 5-Nifro-2-(2.2.2-trifluoroethoxy)pyridine

To a solution of 2,2,2-trifluoroethanol (5 g, 50 mmol) stirring in 50 mL of tetrahydrofuran, sodium hydride (2 g of ca. 60% oil dispersion, ca. 50 mmol) was added portionwise with foaming and an exotherm. After formation of a solution and stirring at room temperature, 2-chloro-5-nitropyridine (5 g, 32 mmol) was added portionwise, accompanied by an exotherm. After stirring at room temperature overnight, the reaction mixture was partitioned between 100 mL of ethyl acetate and 75 mL of water. The organic layer was separated, washed with brine and dried over magnesium sulfate. Evaporation of solvent in vacuo gave an orange oil. A solid was crystaLHzed from hexanes, filtered and dried to give 5 g of 5-nitro-2-(2,2,2-trifluoroemoxy)pyridine (used directly in the next step). 1HNMR (CDC1₃): 9.07 (s, IH), 8.45 (d, IH), 7.01 (d, IH), 4.9 (q, 2H) ppm. Step B: Preparation of 5-Ammo-2-(2.2.2-trifluoroethoxy)pyridine

To a solution of 5 g of 5-nifro-2-(2,2,2-trifluoroethoxy)pyridine in 75 mL of ethyl acetate, 0.5 g of 10% paUadium on carbon was added under nitrogen and the mixture was aUowed to shake on a paar hydrogenator under hydrogen at 3.1 X 10⁵ Pa for 4 hours at room temperature. The reaction mixture was filtered through ceHte and the ceHte washed thoroughly with ethyl acetate. Evaporation of solvent in vacuo gave a dark oil. A soHd was triturated from hexane, filtered and dried to afford 3.3 g of 5-amino-2-(2,2,2- trifluoroethoxy)pyridine, isolated as a crude dark solid.

1H NMR (CDCfe): 7.60 (s, IH), 7.05 (d, IH), 6.70 (d, IH), 4.65 (q, 2H) 3.44 (br s, NH₂) ppm.

Step C: Preparation of 3-iodo-N-(2.2.2-trifluoroethoxy)pyridin-5-yl phmalimide

A stirred solution of 3-iodophthaHc anhydride (1.3g, 4J mmol) and 5-amino-2-(2,2,2- trifluoroemoxy)pyridine (l.lg, 5.7 mmol) stirring in 15 mL of glacial acetic acid was heated at reflux for 3 hrs. The solvent was removed in vacuo and the remaining residue partitioned between 100 mL of ethyl acetate and 75 mL of water. The organic layer was separated, washed with aqueous sodium bicarbonate and brine and dried over magnesium sulfate. Evaporation of solvent in vacuo gave a solid residue which was suspended in hexanes and filtered to afford 2 g of 3-iodo-N-(2,2,2-trifluoroethoxy)pyridin-5-yl phtnalimide, isolated as a crude solid and used directly in the next step.

1H ΝMR (CDC1₃): 8.3 (s, IH), 8.2 (d, IH), 7.95 (d, IH), 7.75 (d, IH) 7.5 (t, IH), 7.01 (d, lH), 4.8 (q, 2H) ppm. Step D: Preparation of 3-Iodo-N -α -methyletfaylVN -[6-r2.2.2-trifluoroethoxyV3- pyrid yl]-!.2-benzenedicarboxamide and ό-Iodo-N^-fl-me ylethylVN -^- (2.2.2-trifluoroethoxy)-3-pyridinyl]- 1.2-benzenedicarboxamide To a stirred solution of 3-iodo-N-(2,2,2-trifluoroethoxy)pyridin-5-yl phthalimide (0.5 g, 1.1 mmol) in 10 mL of 1 ,4-dioxane, isopropylamine (1.5 g, 25 mmol) was added and the reaction solution heated near reflux overnight. The reaction mixture was partitioned between 100 mL of ethyl acetate and 75 mL of water. The organic layer was separated, washed with water and brine, and dried over magnesium sulfate. Evaporation of solvent in vacuo gave a soHd residue which was chromatograghed on siHca gel to afford 27 mg of 3-iodo-N²-(l -methylethyl)-N -[6-(2,2,2-trifluoroethoxy)-3-ρvridinyl]- 1 ,2- benzenedicarboxamide [ p: 220-225 °C; ⁱHΝMR φMSO-Dg): δ 10.25 (s, IH), 8.46 (s, IH), 8.2 (d, IH), 8.05 (d, IH), 8.0 (d, IH), 7.65 (d, IH), 7.25 (t, IH), 7.0 (d, IH), 4.96 (q, 2H), 3.95 (m, IH), 1.07 (d, 6H)] and 25 mg of 6-iodo-N²-(l-methylethyl)-N^-[6-(2,2,2- trifluoroethoxy)-3 -pyridinyl]- 1, 2-benzenedicarboxamide [mp: 200-203 °C; ^ΪHΝMR (DMSO-D₆): δ 8.8 (s, IH), 8.4 (s, IH), 8.05 (d, IH), 7.85 (d, IH), 7.35 (d, IH), 7.05 (t, IH), 6.85 (d, IH), 6.35 (d, IH), 4J5 (q, 2H), 4.1 (m, IH), 1.1 (d, 6H)].

EXAMPLE 2 Step A: Preparation of l-(2-Chlorophenyl)-5-(2-furanyl)-3-(trifluoromethyl)-lH- pyrazole To a solution containing 4,4,4-triπuoro-l-(2-furyl)-l,3- butanedione (30.0 g, 146 mmol) in glacial acetic acid (65 mL) was added sodium acetate (12.1 g, 148 mmol). The mixture was cooled to about 25 °C, 2-chlorophenylhydrazine hydrochloride (25.6 g, 145 mmol) was added portionwise and, foΗowing a mild exotherm, the mixture was heated to 60 °C for 4 h, then cooled to 25 °C. The mixture was diluted with dichloromethane (400 mL) and the organic phase was washed with water (3x250 mL), saturated aqueous sodium carbonate (2x250 mL) and brine, then dried over magnesium sulfate and evaporated under reduced pressure to yield 43.2 g ofthe title compound as a brown oil. 1HΝMR (CDC1₃): δ 7.6 (m,5Η), 6.9 (IH), 5.7 (d, IH). Ste B: Preparation of l-(2-ChlorophenylV3-rtrifluoromethyl)-lH-pyrazole-5- carboxylic acid

To a suspension containing the title compound of Step A (43.2 g, 138 mmol) in acetonitrile (415 mL) was added sodium dihydrogenphosphate monohydrate (92.4 g, 669 mmol) over about 0.25 h. After stirring at room temperature for 0.5 h, the mixture was cooled to about 5 °C and a solution containing sodium chlorite (181 J g, 2.0 mmol) in 430 mL of water was added dropwise over 1 h while keeping the reaction temperature at less than 10 °C. [ Note: an aqueous sodium hydroxide scrubber was attached to scrub an evolving yeUow off-gas.] Following completion of addition the suspension was stirred at 5 °C for about 1 h, at 25 °C overnight, then acidified to pΗ = 1 by dropwise addition of concentrated hydrochloric acid (150 mL), then extracted with ethyl acetate (1x500 mL, then 2x250 mL). The combined ethyl acetate extracts were added dropwise to an aqueous sodium metasufite solution (228.5 g in 1.05 L water) at a reaction temperature of less than 20 °C. The suspension was partitioned and the aqueous layer extracted with ethyl acetate (2x100 mL). The organic layers were combined, dried over magnesium sulfate and evaporated under reduced pressure. The residue was triturated with hexane:diethyl ethert (99:1, 100 mL) to yield 32.9 g ofthe title compound as a soHd. 1HNMR (DMSO-D₆): δ 13.9 (bs,lH), 7J(m,5H).

Step C: Preparation of l-(2-chlorophenylV3-ftrifluoromethylVlH-pyra7:n1-5-arrιine To a solution ofthe title compound of Step B (1.0 g, 3.44 mmol, 1.0 equivalent) in chloroform (20 mL), in a 50 mL round bottom flask was added thionyl chloride (1.26 mL, 17.2 mmol, 5.0 equivalents) and anhydrous N,N-dimethylformamide (2 drops). The resulting mixture was refluxed for 18 hours under a nitrogen atmosphere. After 18 hours the reaction was shown to be complete from an aliquot (0.5 mL) that was added to methanol (2 mL) and potassium carbonate and shaken for 5 minutes. No carboxyHc acid was detected from the aΗquot and only the methyl ester derivative was present (thin-layer chromatography (TLC) analysis R = 0.75, 1:1 ethyl acetate.-hexanes). The mixture was then concentrated under reduced pressure and dried in vacuo for 4 hours. The resulting pale yeUow oil was diluted with chloroform (30 mL) and transferred to a 100 mL round bottom flask. To the flask was added tefrabutylammonium bromide (3.0 mg, 0.01 mmol, 0.003 equivalents) at 0 °C foUowed by a solution of sodium azide (0.9 g, 13.8 mmol, 4.0 equiv) in water (5 mL). The mixture was stirred vigorously for 2 hours, after which the organic layer was separated and washed with water (2 x 20 mL), brine (20 mL), dried (Na₂SO4), and filtered into a 100 mL round bottom flask. To the flask was added trifluoroacetic acid (0.69 mL, 8.94 mmol, 2.6 equivalents) and the mixture was stirred at reflux for 42 hours. To monitor the reaction, an aliquot (0.5 mL) was added to chloroform (1 mL) and washed with saturated sodium bicarbonate (2 mL). By TLC analysis after 6 h, both the acyl azide (R_/ = 0.90, 2:1 ethyl acetate-.hexanes) and product (R_/ = 0.45, 2:1 ethyl acetate-.hexanes) were present. The mixture was then allowed to cool, washed with saturated sodium bicarbonate (2 x 15 mL), dried (Na₂SO₄), and concentrated under reduced pressure. Column chromatography (2:1 ethyl acetate:hexanes) provided 0.68 g ofthe title compound as a pale yellow soΗd in an overaU yield of 76 %. The 1H NMR spectrum was consistant with the structure. ΗNMR (CDC1₃): δ 7.52-7.35 (4Η, m), 6.96 (IH, br), 6.60 (IH, s).

Step D: Preparation of 2- [ 1 -( 2-ChlorophenylV 3 -ftrifluoromethyl)- lH-pyrazol-5-y 1] -4- iodo- lH-isoindole- 1.3(2H)-dione

To a solution ofthe title compound of Step C (1J g, 6.51 mmol, 1.0 equivalent) in glacial acetic acid (9 mL) in a 75 mL sealed tube reaction vessel was added 3-iodophthaΗc anhydride (1.78 g, 6.51 mmol, 1.0 equivalent). The reaction vessel was sealed and heated at 130 °C for 6h, then allowed to cool to room temperature. The mixture was transferred to a 250 mL separatory funnel and water was added (50 mL), upon which a white precipitate formed. The product was extracted with ether (2 x 50 mL), and the combined extracts were washed with water (3 x 50 mL), brine (50 mL), dried a₂SO4), and concentrated under reduced pressure to yield 2.46 g ofthe title compound as a white solid. This material was used in the next step without purification.

Step E: Preparation of N²-[ 1 -(2-Chlorophenyl)-3- trifluoromethyl)- lH-pyrazol-5-yl]-

3-iodo-N^-(l-methylethylVl .2-benzenedicarboxamide and N^-[l-(2- CMorophenyl)-3-(^trifluoromethyl)-lH-pyrazol-5-yl]-3-iodo-N -(l- methylethyl)- 1.2-benzenedicarboxamide

To the neat crude material from Step D (110 mg) in a 1.2 mL glass vial was added isopropyl amine (0.5 mL). After 2 minutes the reaction was complete by TLC. The isopropyl amine was removed to give a crude oil which was purified by preparative TLC (1:2 ethyl acetate-.hexanes) to afford 24 mg of N²-[l-(2-Chlorophenyl)-3-(trifluoromethyl)- lH-pyrazol-5-yl]-3-iodo-N -(l-methylethyl)-l,2-benzenedicarboxamide (yield 18%) (mp 234-235 °C); TLC analysis R_/ = 0.32, (1:1 ethyl acetate :hexanes); 1HΝMR (CDC1₃): δ 7.88 (1Η, d), 7.66 (1Η, br), 7.57-7.52 (2Η, m), 7.50-7.43 (3H, m), 7.16-7.11 (2H, m), 5.98 (IH, bd), 4.10 (IH, m), 1.17 (6H, d); and 37 mg of N?-[l-(2-Chlorophenyl)-3-(trifluoromethyl)- lH-pyrazol-5-yl]-3-iodo-N²-(l-memylethyl)-l,2-benzenedicarboxamide (yield 29%); (mp 226-228 °C); TLC analysis R = 0.58, (1 : 1 ethyl acetate:hexanes) 1H ΝMR (CDC1₃): δ 8.94 (1Η, s), 7.93 (1Η, d), 7.78 (1Η, d), 7.63-7.47 (4Η, m), 7.17 (IH, t), 7.12 (IH, s), 6.63 (IH, bd), 4.07 (IH, m), 1.18 (6H, d).

By the procedures described herein together with methods known in the art, the foUowing compounds of Tables 1 to 25 can be prepared. The foUowing abbreviations are used in the Tables: t is tertiary, s is secondary, n is normal, is iso, c is cyclo, Me is methyl, Et is ethyl, Pr is propyl, /^'-Pr is isopropyl, t-Bu is tertiary butyl, Ph is phenyl and CΝ is cyano.

Table 1

_R4a R⁴° R⁷ R³ R6 _R4a _R4b R⁷ R³ ≠ _R4a _R4b R⁷ R³ R6

CH₃ F CF₃ Me Cl Cl F CF₃ Me Cl Br F CF₃ Me Cl

CH₃ F CF₃ Et Cl Cl F CF₃ Et Cl Br F CF₃ Et Cl

CH₃ F CF₃ i-Pr Cl Cl F CF₃ i-Pr Cl Br F CF₃ i-Pr Cl

CH₃ F CF₃ t-Bu Cl Cl F CF₃ t-Bu Cl Br F CF₃ t-Bu Cl

CH₃ F CF₃ Me Br Cl F CF₃ Me Br Br F CF₃ Me Br

CH₃ F CF₃ Et Br Cl F CF₃ Et Br Br F CF₃ Et Br

CH₃ F CF₃ i-Pr Br Cl F CF₃ i-Pr Br Br F CF₃ i-Pr Br

CH₃ F CF₃ t-Bu Br Cl F CF₃ t-Bu Br Br F CF₃ t-Bu Br

CH₃ F Cl Me Cl Cl F Cl Me Cl Br F Cl Me Cl

CH₃ F Cl Et Cl Cl F Cl Et Cl Br F Cl Et Cl

CH₃ F Cl i-Pr Cl Cl F Cl i-Pr Cl Br F Cl i-Pr Cl

CH₃ F Cl t-Bu Cl Cl F Cl t-Bu Cl Br F Cl t-Bu Cl

CH₃ F Cl Me Br Cl F Cl Me Br Br F Cl Me Br

CH₃ F Cl Et Br Cl F Cl Et Br Br F Cl Et Br

CH₃ F Cl i-Pr Br Cl F Cl i-Pr Br Br F Cl i-Pr Br

CH₃ F Cl t-Bu Br Cl F Cl t-Bu Br Br F Cl t-Bu Br

CH₃ F Br Me Cl Cl F Br Me Cl Br F Br Me Cl

CH₃ F Br Et Cl Cl F Br Et Cl Br F Br Et Cl

CH₃ F Br i-Pr Cl Cl F Br i-Pr Cl Br F Br i-Pr Cl

CH₃ F Br t-Bu Cl Cl F Br t-Bu Cl Br F Br t-Bu Cl

CH₃ F Br Me Br Cl F Br Me Br Br F Br Me Br

CH₃ F Br Et Br Cl F Br Et Br Br F Br Et Br

CH₃ F Br i-Pr Br Cl F Br i-Pr Br Br F Br i-Pr Br

CH₃ F Br t-Bu Br Cl F Br t-Bu Br Br F Br t-Bu Br

CH₃ Cl CF₃ Me Cl Cl Cl CF₃ Me Cl Br Cl CF₃ Me Cl _R4a _R4b R⁷ R³ Rθ _R4a _R4b R⁷ R³ R6 _R4a _R4b R⁷ R³ R6

CH₃ Cl CF₃ • Et Cl Cl Cl CF Et Cl Br Cl CF₃ Et Cl

CH₃ 01 CF₃ i-Pr Cl Cl Cl CF₃ i-Pr Cl Br Cl CF₃ i-Pr Cl

CH₃ 01 CF₃ t-Bu Cl 01 Cl CF₃ t-Bu Cl Br Cl CF₃ t-Bu Cl

CH₃ Cl CF₃ Me Br 01 Cl CF₃ Me Br Br Cl CF₃ Me Br

CH₃ 01 CF₃ Et Br Cl Cl CF₃ Et Br Br Cl CF₃ Et Br

CH₃ Cl ^CF3 i-Pr Br Cl Cl CF₃ i-Pr Br Br Cl CF₃ i-Pr Br

CH₃ Cl CF₃ t-Bu Br Cl Cl CF₃ t-Bu Br Br Cl CF₃ t-Bu Br

CH₃ Cl Cl Me Cl Cl Cl Cl Me Cl Br Cl 01 Me Cl

CH₃ Cl Cl Et Cl Cl Cl Cl Et Cl Br Cl 01 Et Cl

CH₃ Cl Cl i-Pr Cl 01 Cl Cl i-Pr Cl Br Cl Cl i-Pr Cl

CH₃ Cl Cl t-Bu 01 Cl Cl 01 t-Bu 01 Br 01 Cl t-Bu Cl

CH₃ Cl Cl Me Br 01 Cl Cl Me Br Br 01 Cl Me Br

CH₃ 01 Cl Et Br Cl Cl Cl Et Br Br Cl Cl Et Br

CH₃ Cl Cl i-Pr Br Cl Cl Cl i-Pr Br Br Cl Cl i-Pr Br

CH₃ Cl Cl t-Bu Br Cl 01 Cl t-Bu Br Br 01 01 t-Bu Br

CH₃ Cl Br Me Cl Cl Cl Br Me Cl Br 01 Br Me Cl

CH₃ Cl Br Et 01 Cl Cl Br Et 01 Br 01 Br Et Cl

CH₃ 01 Br i-Pr Cl Cl Cl Br i-Pr Cl Br Cl Br i-Pr Cl

CH₃ 01 Br t-Bu 01 Cl Cl Br t-Bu Cl Br Cl Br t-Bu Cl

CH₃ Cl Br Me Br 01 01 Br Me Br Br Cl Br Me Br

CH₃ Cl Br Et Br Cl Cl Br Et Br Br Cl Br Et Br

CH₃ Cl Br i-Pr Br Cl Cl Br i-Pr Br Br Cl Br i-Pr Br

CH₃ Cl Br t-Bu Br Cl Cl Br t-Bu Br Br Cl Br t-Bu Br

CH₃ Br CF₃ Me Cl Cl Br CF₃ Me Cl Br Br CF₃ Me Cl

CH₃ Br CF₃ Et Cl Cl Br CF₃ Et 01 Br Br CF₃ Et Cl

CH₃ Br CF₃ i-Pr 01 Cl Br CF₃ i-Pr Cl Br Br CF₃ i-Pr 01

CH₃ Br CF₃ t-Bu 01 01 Br CF₃ t-Bu Cl Br Br CF₃ t-Bu Cl

CH₃ Br CF₃ Me Br Cl Br CF₃ Me Br Br Br CF₃ Me Br

CH₃ Br CF₃ Et Br Cl Br CF₃ Et Br Br Br CF₃ Et Br

CH₃ Br CF₃ i-Pr Br Cl Br CF₃ i-Pr Br Br Br CF₃ i-Pr Br

CH₃ Br CF₃ t-Bu Br 01 Br CF₃ t-Bu Br Br Br CF₃ t-Bu Br

CH₃ Br Cl Me Cl Cl Br 01 Me Cl Br Br Cl Me Cl

CH₃ Br Cl Et Cl Cl Br Cl Et Cl Br Br 01 Et Cl

CH₃ Br Cl i-Pr Cl Cl Br Cl i-Pr Cl Br Br Cl i-Pr Cl

CH₃ Br Cl t-Bu 01 Cl Br 01 t-Bu Cl Br Br Cl t-Bu Cl

CH₃ Br Cl Me Br Cl H CF₃ Me Cl Br Br Cl Me Br

CH₃ Br Cl Et Br Cl H CF₃ Et 01 Br Br Cl Et Br

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G G m m pq G G G G pq pq pq pq G G G G u pq pq pq pq pq pq a pq G G G G pq £ q Pq G G

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_R4a _R4b R⁷ R³ R6 _R4a _R4b R⁷ R³ R6 _R4a _R4b R⁷ R³ R6

CH CF₃ CF₃ t-Bu Cl Cl CF₃ t-Bu Cl Br CF₃ CF₃ i-Bu Cl

CH₃ CF₃ CF Me Br Cl CF₃ Me Br Br CF₃ CF₃ Me Br

CH₃ CF₃ CF₃ Et Br Cl CF₃ Et Br Br CF₃ CF₃ Et Br

CH₃ CF₃ CF₃ i-Pr Br Cl CF₃ i-Pr Br Br CF₃ CF₃ i-Pr Br

CH₃ CF₃ CF₃ t-Bu Br Cl CF₃ t-Bu Br Br CF₃ CF₃ t-Bu Br

CH₃ CF₃ 01 Me Cl Cl Cl Me 01 Br CF₃ Cl Me Cl

CH₃ CF₃ 01 Et Cl Cl Cl Et Cl Br CF₃ Cl Et 01

CH₃ CF₃ 01 i-Pr Cl Cl Cl i-Pr Cl Br CF₃ Cl i-Pr Cl

CH₃ CF₃ Cl t-Bu Cl Cl Cl t-Bu Cl Br CF₃ Cl t-Bu 01

CH₃ CF₃ Cl Me Br Cl Cl Me Br Br CF₃ Cl Me Br

CH₃ CF₃ Cl Et Br Cl Cl Et Br Br CF₃ Cl Et Br

CH₃ CF₃ 01 i-Pr Br Cl 01 i-Pr Br Br CF₃ Cl i-Pr Br

CH₃ CF₃ Cl t-Bu Br Cl Cl t-Bu Br Br CF₃ Cl t-Bu Br

CH₃ CF₃ Br Me Cl Cl Br Me Cl Br CF₃ Br Me 01

CH₃ CF₃ Br Et Cl Cl Br Et Cl Br CF₃ Br Et Cl

CH₃ CF₃ Br i-Pr Cl Cl Br i-Pr Cl Br CF₃ Br i-Pr Cl

CH₃ CF₃ Br t-Bu Cl 01 Br t-Bu 01 Br CF₃ Br t-Bu Cl

CH₃ CF₃ Br Me Br Cl Br Me Br Br CF₃ Br Me Br

CH₃ CF₃ Br Et Br 01 Br Et Br Br CF₃ Br Et Br

CH₃ CF₃ Br i-Pr Br 01 Br i-Pr Br Br CF₃ Br i-Pr Br

CH₃ CF₃ Br t-Bu Br Cl Br t-Bu Br Br CF₃ Br t-Bu Br

CH₃ Cl Cl κ-Pr Cl Cl CF₃ CF₃ Me Cl I Cl CF₃ Me 01

CH₃ Cl 01 M-BU Cl Cl CF₃ CF₃ Et 01 I Cl CF₃ Et Cl

CH₃ Cl Cl s-Bu Cl Cl CF₃ CF₃ i-Pr Cl I Cl CF₃ i-Pr Cl

CH₃ Cl Cl i-Bu Cl Cl CF₃ CF t-Bu Cl I 01 CF₃ t-Bu Cl

CH₃ H CF₃ Me Cl Cl CF₃ CF₃ Me Br I Cl CF₃ Me Br

CH₃ H CF₃ Et Cl Cl CF₃ CF₃ Et Br I 01 CF₃ Et Br

CH₃ H CF₃ i-Pr Cl 01 CF₃ CF₃ i-Pr Br I Cl CF₃ i-Pr Br

CH₃ H CF₃ t-Bu Cl 01 CF₃ CF₃ t-Bu Br I Cl CF₃ t-Bu Br

CH₃ H CF₃ Me Br Cl CF₃ Cl Me Cl I Cl 01 Me Cl

CH₃ H CF₃ Et Br Cl CF₃ 01 Et Cl I Cl 01 Et Cl

CH₃ H CF₃ i-Pr Br Cl CF₃ 01 i-Pr Cl I Cl Cl i-Pr 01

CH₃ H CF₃ t-Bu Br Cl CF₃ Cl t-Bu Cl I Cl Cl t-Bu 01

CH₃ H Cl Me Cl Cl CF₃ Cl Me Br I 01 Cl Me Br

CH₃ H Cl Et Cl Cl CF₃ Cl Et Br I Cl Cl Et Br

CH₃ H Cl i-Pr Cl Cl CF₃ 01 i-Pr Br I Cl Cl i-Pr Br

CH₃ H Cl t-Bu Cl Cl CF₃ Cl i-Bu Br I Cl Cl t-Bu Br _R4a _R4b R⁷ R³ R6 _R4a _R4b R⁷ R³ R6 _R4a _R4b R⁷ R³ R6

CH₃ H Cl Me Br Cl CF₃ Br Me 01 I Cl Br Me Cl

CH₃ H Cl Et Br Cl CF₃ Br Et 01 I Cl Br Et Cl

CH₃ H Cl i-Pr Br 01 CF₃ Br i-Pr 01 I Cl Br i-Pr Cl

CH₃ H Cl t-Bu Br Cl CF₃ Br t-Bu 01 I Cl Br t-Bu Cl

CH₃ H Br Me Cl Cl CF₃ Br Me Br I Cl Br Me Br

CH₃ H Br Et Cl Cl CF₃ Br Et Br I Cl Br Et Br

CH₃ H Br i-Pr Cl Cl CF₃ Br i-Pr Br I Cl Br i-Pr Br

CH₃ H Br t-Bu Cl Cl CF₃ Br t-Bu Br I Cl Br t-Bu Br

CH₃ H Br Me Br 01 01 01 «-Pr 01 I H CF₃ Me Cl

CH₃ H Br Et Br 01 Cl Cl «-Bu 01 I H CF₃ Et Cl

CH₃ H Br i-Pr Br Cl Cl Cl s-Bu Cl I H CF₃ i-Pr Cl

CH₃ H Br t-Bu Br 01 Cl 01 i-Bu Cl I H CF₃ t-Bu Cl

Table 2

R³ _R4a _R4b R⁷ R6 R³ _R4a R⁴° R⁷ R6

Et 3-Me H OCHF₂ F Et 3-C1 H OCHF₂ F i-Pr 3-Me H CF₃ F i-Pr 3-C1 H CF₃ F t-Bu 3-Me H C₂F₅ F t-Bu 3-C1 H C₂F₅ F propargyl 3-Me H C₂F₅ F propargyl 3-C1 H C₂F₅ F c-propyl 3-Me H CF₃ F c-propyl 3-C1 H CF₃ F i-Pr 3-Me H Me F i-Pr 3-C1 H Me F t-Bu 3-Me 5-Br CN F t-Bu 3-C1 5-Br CN F

Me 3-Me H CF₃ Cl Me 3-01 H CF₃ Cl

Et 3-Me 5-Me OCF₃ Cl Et 3-C1 5-Me OCF₃ Cl i-Pr 3-Me H OCF₃ Cl i-Pr 3-C1 H OCF3 Cl t-Bu 3-Me 5-C1 Br Cl t-Bu 3-C1 5-Cl Br Cl

Me 3-Me H Br Cl Me 3-C1 H Br Cl

Et 3-Me H Cl Cl Et 3-01 H Cl Cl i-Pr 3-Me 5-Br Cl Cl i-Pr 3-01 5-Br 01 Cl t-Bu 3-Me H I Cl t-Bu 3-C1 H I Cl propargyl 3-Me H CF₃ Cl propargyl 3-C1 H CF₃ Cl c-propyl 3-Me H OCF₃ Cl c-propyl 3-01 H OCF3 Cl i-Pr 3-Me 5-C1 CF₃ Cl i-Pr 3-C1 5-Cl CF3 Cl t-Bu 3-Me H SCF₃ Cl t-Bu 3-C1 H SCF3 Cl

Me 3-Me 5-C1 SCHF₂ Cl Me 3-C1 5-Cl SCHF₂ Cl

Et 3-Me H OCHF₂ 01 Et 3-C1 H OCHF₂ Cl i-Pr 3-Me H CF₃ Cl i-Pr 3-C1 H CF3 Cl i-Bu 3-Me H C F₅ Cl i-Bu 3-C1 H C₂F₅ Cl propargyl 3-Me H C₂F₅ Cl propargyl 3-C1 H C₂F₅ 01 c-propyl 3-Me H CF₃ Cl c-propyl 3-C1 H CF₃ Cl i-Pr 3-Me H Me Cl i-Pr 3-C1 H Me Cl t-Bu 3-Me 5-Br CN Cl t-Bu 3-C1 5-Br CN Cl

Me 3-Me H CF₃ CF₃ Me 3-C1 H CF₃ CF₃

Et 3-Me 5-Me OCF₃ CF₃ Et 3-C1 5-Me OCF3 CF₃ i-Pr 3-Me H OCF₃ CF₃ i-Pr 3-C1 H OCF3 CF₃ t-Bu 3-Me 5-Cl Br CF₃ t-Bu 3-C1 5-Cl Br CF₃

Me 3-Me H Br CF₃ Me 3-C1 H Br CF₃

Et 3-Me H 01 CF₃ Et 3-C1 H 01 CF₃ i-Pr 3-Me 5-Br 01 CF₃ i-Pr 3-C1 5-Br Cl CF₃ t-Bu 3-Me H I CF₃ i-Bu 3-C1 H I CF₃ propargyl 3-Me H CF₃ CF₃ propargyl 3-01 H CF₃ CF₃ c-propyl 3-Me H OCF₃ CF₃ c-propyl 3-01 H OCF3 CF₃

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CH₃ Br 01 Me Cl Cl Br Cl Me Cl Br Br Cl Me Cl

CH₃ Br Cl Et Cl Cl Br Cl Et Cl Br Br Cl Et Cl

CH₃ Br Cl i-Pr Cl Cl Br Cl i-Pr Cl Br Br Cl i-Pr Cl

CH₃ Br Cl i-Bu Cl Cl Br Cl i-Bu Cl Br Br Cl i-Bu Cl

CH₃ Br Cl Me Br Cl H CF₃ Me Cl Br Br Cl Me Br

CH₃ Br Cl Et Br Cl H CF₃ Et Cl Br Br Cl Et Br

CH₃ Br Cl i-Pr Br Cl H CF₃ i-Pr Cl Br Br Cl i-Pr Br _R4a _R4b R⁷ R3 R6 _R4a _R4b R⁷ R3 R6 _R4a _R4b R⁷ R3 R6

CH₃ Br Cl i-Bu Br Cl H CF₃ i-Bu Cl Br Br Cl i-Bu Br

CH₃ Br Br Me Cl Cl H CF₃ Me Br Br Br Br Me Cl

CH₃ Br Br Et Cl Cl H CF₃ Et Br Br Br Br Et Cl

CH₃ Br Br i-Pr Cl Cl H CF₃ i-Pr Br Br Br Br i-Pr Cl

CH₃ Br Br i-Bu Cl Cl H CF₃ i-Bu Br Br Br Br i-Bu 01

CH₃ Br Br Me Br Cl H 01 Me 01 Br Br Br Me Br

CH₃ Br Br Et Br Cl H 01 Et Cl Br Br Br Et Br

CH₃ Br Br i-Pr Br Cl H 01 i-Pr 01 Br Br Br i-Pr Br

CH₃ Br Br i-Bu Br Cl H Cl i-Bu 01 Br Br Br i-Bu Br

CH₃ CF₃ Me Cl Cl H Cl Me Br Br CF₃ Me Cl

CH₃ CF₃ Et Cl Cl H Cl Et Br Br CF₃ Et Cl

CH₃ CF₃ i-Pr Cl Cl H Cl i-Pr Br Br CF₃ i-Pr Cl

CH₃ CF₃ i-Bu Cl Cl H Cl i-Bu Br Br CF₃ i-Bu Cl

CH₃ CF₃ Me Br Cl H Br Me Cl Br CF₃ Me Br

CH₃ CF₃ Et Br Cl H Br Et 01 Br CF₃ Et Br

CH₃ CF₃ i-Pr Br Cl H Br i-Pr ' 01 Br CF₃ i-Pr Br

CH₃ CF₃ i-Bu Br Cl H Br i-Bu Cl Br CF₃ i-Bu Br

CH₃ Cl Me Cl Cl H Br Me Br Br Cl Me Cl

CH₃ Cl Et Cl 01 H Br Et Br Br Cl Et Cl

CH₃ Cl i-Pr Cl 01 H Br i-Pr Br Br 01 i-Pr Cl

CH₃ Cl i-Bu Cl 01 H Br i-Bu Br Br Cl i-Bu 01

CH₃ Cl Me Br 01 Br Cl Me Br Br Cl Me Br

CH₃ Cl Et Br Cl Br Cl Et Br Br Cl Et Br

CH₃ Cl i-Pr Br Cl Br Cl i-Pr Br Br Cl i-Pr Br

CH₃ Cl i-Bu Br Cl Br 01 i-Bu Br Br 01 i-Bu Br

CH₃ Br Me Cl 01 Br Br Me Cl Br Br Me Cl

CH₃ Br Et Cl Cl Br Br Et Cl Br Br Et Cl

CH₃ Br i-Pr Cl Cl Bi; Br i-Pr Cl Br Br i-Pr Cl

CH₃ Br i-Bu 01 Cl Br Br i-Bu Cl Br Br i-Bu Cl

CH₃ Br Me Br Cl Br Br Me Br Br Br Me Br

CH₃ Br Et Br 01 Br Br Et Br Br Br Et Br

CH₃ Br i-Pr Br Cl Br Br i-Pr Br Br Br i-Pr Br

CH₃ Br i-Bu Br Cl Br Br i-Bu Br Br Br i-Bu Br

CH₃ CF₃ CF₃ Me Cl Cl I CF₃ Me Cl Br CF₃ CF₃ Me Cl

CH₃ CF₃ CF₃ Et Cl Cl I CF₃ Et Cl Br CF₃ CF₃ Et 01

CH₃ CF₃ CF₃ i-Pr Cl Cl I CF₃ i-Pr Cl Br CF₃ CF₃ i-Pr Cl

CH CF₃ CF₃ i-Bu Cl Cl I CF₃ i-Bu Cl Br CF₃ CF₃ i-Bu Cl IΛ t- li li

H CJ fc a $ a 3 α. 3 1 a ft^* 3 a ft § 5 3 a 3

5 3 a ft^* 3 a S 3 a S 3 a s 3

3 fc δ δ δ δ o o o o o o o to ffl ffl ffl pq to to ffl δ δ δ δ δ δ δ δ o o o o o o o o δ δ δ δ 8 fc δ 8 δ δ δ 8 fc 8 δ δ δ δ δ fc 8 δ δ o o o o o o o o o o o o

3 l fc to ffl pq ffl pq lff pq ffl ffl ffl ffl ffl pq ffl ffl ffl to ffl ffl ffl li

P-! pq ffl ffl ffl G G G ffl to to ffl G G G G ffl ffl to ffl G G G G ffl pq ffl pq G o G G to ffl ffl ffl

3 3 3 fc 1 a S 3 a 5 3 a ξ 3 pq a 3

S 3 1 a s 3

3 a ft^* 3 a s 3

3 a s 3

3 1 a s 3

3 tr- fc δ δ δ δ o o o o o o o o to ffl ffl ffl ffl ffl ffl m 8 fc δ δ δ δ fc o δ δ o o o o o o o o

% δ δ δ δ δ 8 fc δ 8 fc δ 8 δ δ δ δ δ δ fc o o u o o u o o o o o o o υ υ o o o o o o o o υ o o o υ g

3 3 3 3 s 3 3 3 3 3 fc a ft pq a pq a ξ 3

3 a 3 a g pq f q

— - t K *P $ a 5 p a 5 « 1 a * *<•». 3 o fc δ δ δ δ o o o o o o o ffl ffl ffl pq ffl ffl ffl ffl G G O G δ 8 fc δ 8 δ δ δ δ o υ o o co

^ δ δ δ δ 8 δ δ δ δ δ fc o δ δ δ δ δ δ fc 8 δ δ G G G G ffl ffi tn ffi a c a a ffl ffi ffi ffi t- cd fc 3 3 3 3 3 ffl 8 3 3 3 3 3 8 ffl 3 3 3 8 ffl 3 3 3 3 3 3 3 3 3 3 3 3 8 ffi 3 8 ffi ffl 8 ffi 8 3 3 o

_R4a _R4b R⁷ R3 R6 _R4a _R4b R⁷ R3 R6 _R4a _R4b R⁷ R3 R6

CH₃ H 01 Et Br Cl CF₃ Br Et Cl I Cl Br Et Cl

CH₃ H Cl i-Pr Br 01 CF Br i-Pr Cl I Cl Br i-Pr Cl

CH₃ H Cl i-Bu Br 01 CF₃ Br i-Bu Cl I Cl Br i-Bu Cl

^CH3 H Br Me Cl Cl CF₃ Br Me Br I Cl Br Me Br

CH₃ H Br Et 01 Cl CF₃ Br Et Br I Cl Br Et Br

CH₃ H Br i-Pr Cl Cl CF₃ Br i-Pr Br I Cl Br i-Pr Br

CH₃ H Br i-Bu Cl Cl CF₃ Br i-Bu Br I Cl Br i-Bu Br

CH₃ H Br Me Br Cl Cl Cl n-Vr Cl I H CF₃ Me Cl

CH₃ H Br Et Br Cl Cl Cl M-BU 01 I H CF₃ Et Cl

CH₃ H Br i-Pr Br 01 Cl 01 s-Bu Cl I H CF₃ i-Pr Cl

CH₃ H Br i-Bu Br Cl Cl 01 i-Bu Cl I H CF₃ i-Bu Cl

Table 8

R3 _R4a _R4b R⁷ R6 R3 _R4a _R4b R⁷ R6

Et 3-Me H OCHF₂ F Et 3-Cl H OCHF₂ F i-Pr 3-Me H CF₃ F i-Pr 3-Cl H CF₃ F i-Bu 3-Me H C₂F₅ F i-Bu 3-Cl H C₂F₅ F propargyl 3-Me H C₂F₅ F propargyl 3-Cl H C₂F₅ F c-propyl 3-Me H CF₃ F c-propyl 3-Cl H CF₃ F i-Pr 3-Me H Me F i-Pr 3-Cl H Me F i-Bu 3-Me 5-Br CN F i-Bu 3-Cl 5-Br CN F

Me 3-Me H CF₃ Cl Me 3-Cl H CF₃ Cl

Et 3-Me 5-Me OCF₃ Cl Et 3-Cl 5-Me OCF3 Cl i-Pr 3-Me H OCF3 Cl i-Pr 3-Cl H OCF3 01 i-Bu 3-Me 5-Cl Br Cl i-Bu 3-Cl 5-Cl Br Cl

Me 3-Me H Br Cl Me 3-Cl H Br Cl

Et 3-Me H Cl Cl Et 3-Cl H 01 Cl i-Pr 3-Me 5-Br Cl Cl i-Pr 3-Cl 5-Br 01 Cl i-Bu 3-Me H I Cl i-Bu 3-Cl H I Cl propargyl 3-Me H CF₃ Cl propargyl 3-Cl H CF₃ Cl c-propyl 3-Me H OCF3 Cl c-propyl 3-Cl H OCF3 01 i-Pr 3-Me 5-Cl CF₃ Cl i-Pr 3-Cl 5-Cl CF₃ Cl t-Bu 3-Me H SCF₃ Cl t-Bu 3-Cl H SCF₃ Cl

Me 3-Me 5-Cl SCHF₂ Cl Me 3-Cl 5-Cl SCHF₂ 01

Et 3-Me H OCHF₂ Cl Et 3-Cl H OCHF₂ 01 i-Pr 3-Me H CF₃ Cl i-Pr 3-Cl H CF₃ Cl i-Bu 3-Me H C₂F₅ Cl i-Bu 3-Cl H C₂F₅ 01 propargyl 3-Me H C₂F₅ Cl propargyl 3-Cl H C₂F₅ Cl c-propyl 3-Me H CF₃ Cl c-propyl 3-Cl H CF₃ Cl i-Pr 3-Me H Me Cl i-Pr 3-Cl H Me Cl i-Bu 3-Me 5-Br CN Cl i-Bu 3-Cl 5-Br CN 01

Me 3-Me H CF₃ CF₃ Me 3-Cl H CF₃ CF₃

Et 3-Me 5-Me OCF3 CF₃ Et 3-Cl 5-Me OCF3 CF₃ i-Pr 3-Me H OCF3 CF₃ i-Pr 3-Cl H OCF3 CF₃ i-Bu 3-Me 5-Cl Br CF₃ i-Bu 3-Cl 5-Cl Br CF₃

Me 3-Me H Br CF₃ Me 3-Cl H Br CF₃

Et 3-Me H Cl CF₃ Et 3-Cl H Cl CF₃ i-Pr 3-Me 5-Br Cl CF₃ i-Pr 3-Cl 5-Br Cl CF₃ i-Bu 3-Me H I CF₃ i-Bu 3-Cl H I CF₃ propargyl 3-Me H CF₃ CF₃ propargyl 3-Cl H CF₃ CF₃ c-propyl 3-Me H OCF3 CF₃ c-propyl 3-Cl H OCF3 CF₃

Ul Ul ϊ Ui u> » ffi t ffi a a ffl ffi flf ffi ffi ffi a ffi ffi o in Q ffi ffi ffi Cd ffi ffi Q fif 1 ffi ffi ffi ffi ffi f to a fi o ffi o %

J TJ TJ Tj TJ j TJ w Cd flf Cd Cd Cd Cd lff Cd Cd Cd Cd Cd Cd Cd

•I 11 ffl ^W Cd ffl ^w O 9J O 9J O 9J O 9J O 9J O 9J O 9J O 9J O 9J O 9J ft

-J oo

ON ON ON ON ON ON rø ό CJ ό ό δ δ ό ό δ ό ό ό 6 ό ό ό ό ό ό ό ό δ ό ό ό δ δ ό ό ό δ ό ό δ δ δ δ ^

Ul Ul Ul Ui Ul Ul Ui Ul ffi ffi ffi ffi ffl i ffi 1 ff ffl ffi ffi ffl ffi ffi fif 1 o ffi Ω ffi ffi flf ffi ffi o ffi ffi ffl ffi ffi iff ffi ffi ffi ffi o

TJ J TJ TJ TJ J TJ w ffl ^ω ffl Cd ^ω ^W ffl Cd -t « ^ω T ω ffl ffl ^{κ ω} ffl Cd ⁱ ffl

O 9J O 9J O 9J O 9J 9J O 9J O 9J O 9J O 9J O 9J ft

ffl m m pq ffl m m pq m ffl pq pq pq pq m CN cN CN cN CN cN CN O O|O|CΛ|∞|∞|W-g§ f ffff

U fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc

3 ! fcl O O o o o o o o o o o o o o o o o o o o o o o o o o o o o o u u o vo o vό o o o ό v vo vo v ό vό o ό vo vό ό o vo v o o vo vo vo vό O vo

3 3 3 fc ^ a ft ffl ^ a ft ffl ^ ft ffl a ft ffl a ft f? W tf p? pq ft pq « f rS i ^ I pq t pq ft ffl ffl 3

O fcl G G G G G G G G G G G G υ G G G G G G G m pEj pq ffl ffl ffl ffl ffl m m m pq m pq pq ffl

CN CN CN CN cN CN CN cN

^■a S § S S & & & & f f I r & δ δ s s § g g g | g | | § § § § g § g s

c i ιS .s ,s ,a ,S ιS ιS ιS 'S ιS .S ιS ι≤ .≤ .--i ,£ ιS ^i--" vo vo vo vo vό vo vo vo vό vo vo vo vό vo vo vo vo vo vo vo vo vo vό vo vo vό vo vo vo vo vo vo vό vσ vo vo t-

3 i 3 3 fcl to ξ ft ffl ft i f O ff ^ ffl ft fl ? ω a — tf J-i ^p ϊp³ s a -j_» ft• 3 l m ω i ft i 3

5 a -t ffl ft ffl ft I a 3 ft ffl o

R3 _R4a _R4b R⁷ R6 R3 _R4a R * R⁷ R6

Et 6-Me H C₂F₅ Br Et 6-C1 H C₂F₅ Br i-Pr 6-Me H C₂F₅ Br i-Pr 6-C1 H C₂F₅ Br i-Bu 6-Me H C₂F₅ Br i-Bu 6-C1 H C₂F₅ Br

Me 6-Me H /.-C3F7 Br Me 6-01 H «-C₃F₇ Br

Et 6-Me H «-C₃F₇ Br Et 6-C1 H «-C₃F₇ Br i-Pr 6-Me H «-C₃F₇ Br i-Pr 6-C1 H «-C₃F₇ Br i-Bu 6-Me H «-C3F₇ Br i-Bu 6-C1 H n-C F₇ Br

Me 6-Me H i-C₃F₇ Br Me 6-C1 H i-C₃F₇ Br

Et 6-Me H i-C₃F₇ Br Et 6-C1 H i-C₃F₇ Br i-Pr 6-Me H i-C₃F₇ Br i-Pr 6-C1 H i-C₃F₇ Br i-Bu 6-Me H i-C₃F₇ Br i-Bu 6-C1 H i-C₃F₇ Br

Me 6-Me H CN Br Me 6-01 H CN Br

Et 6-Me H CN Br Et 6-C1 H CN Br i-Pr 6-Me H CN Br i-Pr 6-C1 H CN Br i-Bu 6-Me H CN Br i-Bu 6-C1 H CN Br

Me 6-Me H OCHF₂ CF₃ Me 6-C1 H OCHF₂ CF₃

Et 6-Me H OCHF₂ CF₃ Et 6-C1 H OCHF₂ CF₃ i-Pr 6-Me H OCHF₂ CF₃ i-Pr 6-C1 H OCHF₂ CF₃ i-Bu 6-Me H OCHF₂ CF₃ i-Bu 6-C1 H OCHF₂ CF₃

Me 6-Me H SCHF₂ CF₃ Me 6-C1 H SCHF₂ CF₃

Et 6-Me H SCHF₂ CF₃ Et 6-C1 H SCHF₂ CF₃ i-Pr 6-Me H SCHF₂ CF₃ i-Pr 6-01 H SCHF₂ CF₃ i-Bu 6-Me H SCHF₂ CF₃ i-Bu 6-C1 H SCHF₂ CF3

Me 6-Me H OCF₃ CF₃ Me 6-C1 H OCF3 CF₃

Et 6-Me H OCF3 CF₃ Et 6-C1 H OCF3 CF₃ i-Pr 6-Me H OCF3 CF₃ i-Pr 6-C1 H OCF3 CF₃ i-Bu 6-Me H OCF3 CF₃ t-Bu 6-C1 H OCF3 CF₃

Me 6-Me H SCF₃ CF₃ Me 6-C1 H SCF3 CF₃

Et 6-Me H SCF3 CF₃ Et 6-01 H SCF₃ CF₃ i-Pr 6-Me H SCF3 CF₃ i-Pr 6-01 H SCF3 CF₃ i-Bu 6-Me H SCF3 CF₃ i-Bu 6-C1 H SCF3 CF₃

Me 6-Me H C₂F₅ CF₃ Me 6-C1 H C F₅ CF₃

Et 6-Me H C₂F₅ CF₃ Et 6-C1 H C₂F₅ CF₃ i-Pr 6-Me H C₂F₅ CF₃ i-Pr 6-C1 H C₂F₅ CF₃ i-Bu 6-Me H C₂F₅ CF₃ i-Bu 6-C1 H C₂F₅ CF₃

Me 6-Me H n-C₃F₇ CF₃ Me 6-C1 H n-C₃F₇ CF₃

Et 6-Me H «-C₃F₇ CF₃ Et 6-01 H «-C₃F₇ CF3

O O O O O O O O O O O O O O O O O O O O O O O Ω Ω Ω Ω ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ft

0 0 O O θ ^ OΛ O ON ^t3 Λ O\ O OΛ C3 O O O O CΛ ON O ^ OΛ ON C^ O -Λ θN

O O O O O Q O O Q Q Q Q O O O Q Q O O O Q Q O O O O O O O O O O O O O O O I Ift cs

Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi β

TJ TJ Tj Tj TJ TJ hcj Tj TJ TJ TJ TJ hcj TJ hcJ hcJ hcJ hrJ hcJ TJ hcJ hrJ hcJ Tj TJ TI TJ hcJ TJ TJ TJ TJ TJ TI

OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ ft ON

ON O ON;ON ^;ON OΛi^ O CDN C^ t-Ti OΛ OiΛ ON ON OΛ ^iON OΛ ^iC^^ i j

O O O O O O O O O O Q Q O O O O O Q O O Q O Q Q O O O O O O O O O ft

g g g g s Ω aΩ s l 9 Ω aΩ ^QΩ ^QΩ ^QO ^QO Ω cΩ cΩl ⁰Ω ⁰Ω ⁰Ω ⁰Ω o o o o o

O 9J OJ 9J O 9J 9J O 9J O 9J O 9J . g g g s g g 8 S S § § § «g ft torø .torø .torø .torø torø torø torø torø rø

O O O O O O O O O O O Q Q Q O O O O O O O O O O O O O O O O O O τj Tj Tj Tj Tj |c*

ffl EP ES g w ø J ES &> w J rø ffl rø ør Cd rø Cd ..

3 'I 3 ff

3 E T? r l

3 T 3 E? Cd

3 E? ør ^ω E? ES ϋ 2 3 '-ⁱ 3 3 E T? 3

δ ό δ ό ό ό δ δ ό δ δ δ δ Q ό ό δ δ δ ό ό δ δ δ ό δ ό δ δ δ δ ό ό ό έ'

O O O O O O O O O O O Q O Q Q O O O O O O O O O O O O O O O O O O O O O O ^ & a a a a o o o Q .0.0. . ι ι _.δ c) _ιS' ₁S^> -? .<? S « S S S a S S h rι f) fι ^χ* i! *S5SS « § g $ s s $ S I 5 J 5 j? 11 to 1to 1to 1to to 1.to11to to 1 a s s a | R.

O O O O O O O O O O O Q Q O O O Q O O O O O O O O O O O O O O O Tj Ti Tj Tj Ti l ,

fcl m ffl m ffl to ffl ffl ffl ffl m m m m ffl m m m m m ffl m m m ffl ffl ffl ffl ffl m m m ffl fc fc fc fc o o o o

ffl

H fcl CJ 0 0 O 0 ∞ ∞ ∞ ∞ ^{o o o o vl ζΛ ∞ u u u u} k k κ x; -~ -^ -^ -~ O O O O α. j o o o o o o o o o o o o o o o o o o o o o o o o o o υ o o o o o o o o o

3 I fcl g o o o o o υ o g g o o o o o o υ o o o g g o o g g g g g g g g g g g o vo o o vo vo o vo vo vo o ό ό vό vό vό ό vo o v vo vo vό vo vo v v o o o o o o vo vo vo

fcl I pq ft

S w °? ft f9 a ft ffl a ft cp

" - oo

a a a a s a s s s & δ & & & & & & -S

o o o o o o o g o o o g o o g g g o o o o o g o g g o o o υ o o o o o g sι fi ιS fi S fi S ιS ιS s a a s -. ι2 a S ι2 S δ ι2 s a iH S ι2 5 £ ιS a iH iS a a S ι2 ₁2

t-

o

R3 R⁴a g4b sZ ≠ ώ g4a R4b EZ R

Et 6-Me 01 SCHF₂ CF₃ Et 6-C1 Cl SCHF₂ CF₃ i-Pr 6-Me Cl SCHF₂ CF₃ i-Pr 6-C1 Cl SCHF₂ CF₃ i-Bu 6-Me Cl SCHF₂ CF₃ i-Bu 6-C1 Cl SCHF₂ CF₃

Me 6-Me Cl OCF₃ CF₃ Me 6-C1 01 0CF3 CF₃

Et 6-Me Cl 0CF3 CF₃ Et 6-C1 Cl 0CF3 CF₃ i-Pr 6-Me Cl 0CF3 CF₃ i-Pr 6-C1 Cl 0CF3 CF₃ i-Bu 6-Me Cl 0CF3 CF₃ i-Bu 6-C1 Cl 0CF3 CF₃

Me 6-Me Cl SCF3 CF₃ Me 6-C1 Cl SCF3 CF₃

Et 6-Me Cl SCF3 CF₃ Et 6-C1 Cl SCF3 CF₃ i-Pr 6-Me Cl SCF3 CF₃ i-Pr 6-C1 Cl SCF3 CF₃ i-Bu 6-Me Cl SCF3 CF₃ i-Bu 6-C1 Cl SCF3 CF₃

Me 6-Me Cl C₂F₅ CF₃ Me 6-C1 01 C_{2 5} CF₃

Et 6-Me Cl C₂F₅ CF₃ Et 6-C1 Cl C₂F₅ CF₃ i-Pr 6-Me Cl C₂F₅ CF₃ i-Pr 6-C1 Cl C₂F₅ CF₃ i-Bu 6-Me Cl C₂F₅ CF₃ i-Bu 6-C1 Cl C₂F₅ CF₃

Me 6-Me Cl H-C3F7 CF₃ Me 6-C1 Cl «-C₃F₇ CF₃

Et 6-Me Cl K-C3F-7 CF3 Et 6-C1 Cl «-C3F₇ CF₃ i-Pr 6-Me Cl «-C₃F₇ CF₃ i-Pr 6-01 01 «-C₃F₇ CF₃ i-Bu 6-Me 01 «-C₃F₇ CF₃ i-Bu 6-01 01 n-C₃F₇ CF₃

Me 6-Me 01 i-C₃F₇ CF₃ Me 6-C1 Cl i-C₃F₇ CF₃

Et 6-Me Cl i-C₃F₇ CF₃ Et 6-C1 Cl i-C₃F₇ CF₃ i-Pr 6-Me Cl i-C₃F₇ CF₃ i-Pr 6-01 Cl i-C₃F₇ CF₃ i-Bu 6-Me 01 i-C₃F₇ CF₃ i-Bu 6-C1 Cl i-C₃F₇ CF₃

Me 6-Me 01 CN CF₃ Me 6-C1 Cl CN CF₃

Et 6-Me 01 CN CF Et 6-C1 Cl CN CF₃ i-Pr 6-Me Cl CN CF₃ i-Pr 6-01 Cl CN CF₃ i-Bu 6-Me Cl CN CF₃ i-Bu 6-01 Cl CN CF₃

55 fc fc

ft, ft c r-

ε- -Λ

"^1 ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffl ffl ffi ffi ffi ffi ffi ffi ffl ffi ffl ffi

t- ό $ ^{μ l} 3 vo 3v 3o 3vo 3o 3vo 3vo 3o 3o 3vo 3v v3o 3v v3o 3 3vo 3vo 3vo v3o v3o 3v 3 3vo 3vo 3vo

90

CN

MM MM MM MM MM MM MM MM MM MM 5 55 5 5 5555 55 G G G G G G G G

>n fc fc fc fe r£, _CL. r£. r£. ₁--. .

& ? ? ? ? §^• §^■ s δ

"^| ffi ffi ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffi ffi ffi ffi ffl ffl ffl ffl ffl ffi ffl ffl ffl ffl ffl ffl ffl

fcl o u o o o o o o o o o u u u u o o o u u o u o o u o u o o o u o o u o u

VO o vo VO VO VO vo vo vo vό vo o vo o o vo v vo vo vo vo o v o o vo vo vo o VO VO VO O

3 3 3 cl 5: 3 - s® to - ft 5 ffl ^ a ft 3 o f ffl pq ft ffl ft ffl a ft ffl ^ a ft 3 S W 5: 3 s - a-T £ ft ffl * to

OO HrH HM τ"i MM H HM MM MM MM MM MM MM ^χι

55 55 5 5 555 56 5

^ fc fc fc fc fc fc Fj fj G G G G G G G G G G G G G G G G G G G G G G G G G G G G

t— t— CN CN CN CN CN CN CN CN t — - c— r — r— t — r- - r— r—

CO CO CO CO ^ θ rθ <n ιn «n <n fc fc fc fc r£. r£_J r . r£. _t_ ₁_ ^ftϊ ^•Λ o-Λ o o o o G O GO GO OG 8 8co 8& 8co δ O δO δO δO cδo δco δco δco Oft,Oft₎ Oft,fOt.& i s ■

-. & s ~t & ι ε; & i Y T" E; & ^*■-•» &&&55

fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc ω <u tu ω ω c <iJ θ (iJ o ω o cD ω u ω r- (4 3 VO 3VO 3VO 3VO 3VO 3VO V3O 3VO 3VO 3VO 3VO 3VO 3VO 3VO 3VO 3VO V3 3VO V3O 3VO 3VO. V 3O 3VO 3VO 3VO 3VO 3VO 3VO 3VO 3VO 3VO 3VO 3VO 3VO 3VO 3VO

3 f a ft o? a ft p a ft ^pp a to 41 JH ^ l cl ft ^p? a ft fl ffl ^ a ft ^pp ^t-> f a ftJH ffl3 ^-⁾ al ft ffl5 ^t- a*- o

i g4a R4b E⁷ ≠ X S³. g4a R E⁷ R6 X i-Bu 6-Me H CN a CH i-Bu 6-C1 H CN Cl CH

Me 6-Me H OCHF₂ Br CH Me 6-C1 H OCHF₂ Br CH

Et 6-Me H OCHF₂ Br CH Et 6-C1 H OCHF₂ Br CH i-Pr 6-Me H OCHF₂ Br CH i-Pr 6-C1 H OCHF₂ Br CH i-Bu 6-Me H OCHF₂ Br CH i-Bu 6-01 H OCHF₂ Br CH

Me 6-Me H SCHF₂ Br CH Me 6-01 H SCHF₂ Br CH

Et 6-Me H SCHF₂ Br CH Et 6-01 H SCHF₂ Br CH i-Pr 6-Me H SCHF₂ Br CH i-Pr 6-01 H SCHF₂ Br CH i-Bu 6-Me H SCHF₂ Br CH i-Bu 6-C1 H SCHF₂ Br CH

Me 6-Me H OCF₃ Br CH Me 6-C1 H OCF3 Br CH

Et 6-Me H OCF3 Br CH Et 6-01 H OCF3 Br CH i-Pr 6-Me H OCF3 Br CH i-Pr 6-01 H OCF3 Br CH i-Bu 6-Me H OCF3 Br CH i-Bu 6-01 H OCF3 Br CH

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ffl ffl ffl ffl Ω Ω Ω Ω ^ffl ffl ffl ffl Ω Ω Ω Ω ^ffl ffl ffl ffl Ω Ω Ω Ω ffl ffl ffl ffl O O O W W W ffl O ft

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Hi U s 3 3 3 a. Pi\ a 3 1 a S *!--. 3 1 a ft^* pq a s 3 3 3 ft^* 3 a ft^* i a s 3 3 1 a S 3 3 1 a s 3 3

fj δ δ δ δ δ δ 8 fc δ a ffl a ffl ffl a a ffl ffi ffi in a a ta a a ffi a ffi !u a ffi a ta G G G G

3 1 cl m lff ffl ffl ffl ffl ffl to o o o o o o o o o o o o o o o o o o o o o o o o f 5 ffl 8 5 ffl 8 o fcl S li ffl ffl ffl ffl o o o o o ffl ffl ffl ffl G o G G ffl ffl ffl ffl G G G G ffl ffl ffl to G G G G

II m ffl m ffl m ffl ffl ffl a a a a a a ffl in a ffi a ffl a a ffi a ffi a a a a a a a fc fc fc fc

t- fcl o o o o 5 5 5 5 ffl 8 5 5 5 8 ffl § 8 ffi 5 5 5 3 ffi 8 3 3 3 ffi 8 8 ffi 5 5 ffl 8 5 ffl 8 5 5

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9 9 9 9 Ω Ω Ω Ω Ω Ω Ω Ω 9 9 9 9 9 9 9 9 Ω Ω Ω Ω Ω Ω Ω Ω 9 9 lft

ffi ffi ffi ffi ffl H? H? H? H? H? H? _H? _H? _H? ffl ffl ffl ffl ^W ffl rø rø rø rø rø rø rø rø rø rø rø ft

O O O O O Q O Q Q Q O Q O O Q O O Q O Q O O O O O O O O O S TJ STJ STJ STJ STJ raTJ STJ Sτ_ ατ_ raT] HTSJ ST] raTJ lτ-S_ Sτ_ HτS_ ώT] HTJ HTS_ tTS] BT_ raT] STJ πT αTJ ShJ STJ STJ ST. SJ ΞJ ftI _*I to to to to to to to to to to to to to to to to to to to to to to to to to to to to to

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3fl E? rø Cd TJ w Cd ø

3 3 3 ft ι-T E «*S CD H ro- T rø Cd s E? r ffl rø

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3 T 3 f

w ω w w w w w ω Q o W ffl w w O Q o ω ω w ro o Q O o ω ω ω lrø O o o o o Q Q θ Q o Q 9 9 9 9 9 Ω Ω Ω Ω Ω ° Ω ^o 9 9 lft

ffi ffi ffi ffi Tj hd TJ TJ TJ Tj rø Tj Q O Q R

Q Q ^Q Ω ^{Q Q Q Q} Q Ω ^{Q Q} Q Ω ^{Q Q} Q ^Q D Q ^{Q Q} Q Q D Q Q Q 9 „

S Tj H Tj S Tj H TJ S TJ α TJ S TJ ώ τj ώ^ιτj ώτj raτj ra^ιτj Hhι3 ώhcj Shι ώτι Hrø hrj τj rø τi τj ιτj rø h!_ τj h!- τι τj τj τj Kι or. J tO IO iO tO rO tO iO tO tO tO iO O tO tO tO tO tO tO tO tO tO tO tO tO tO W

p! " CD ø " C ø 1-r D £; " CD g^* •* ffi H * (0

^{ffl ffl ffl ffl} H? H? ^ffl » Ω Ω Ω Ω ^{ω ω ffl ffl} Ω Ω Ω Ω ^{ω w M W} Ω Ω Ω ^{ω ffl ffl} ft

Table 11

l P R4b S_. R_. g4a R4b ? R6

Me 3-Me H CF₃ F Me 3-Cl H CF₃ F

Et 3-Me 5-Me CHF₂ F Et 3-Cl 5-Me CHF₂ F i-Pr 3-Me H CHF₂ F i-Pr 3-Cl H CHF₂ F i-Bu 3-Me 5-Cl CH₂CF₃ F i-Bu 3-Cl 5-Cl CH₂CF₃ F

Me 3-Me H CH₂CF₃ F Me 3-Cl H CH₂CF₃ F

Et 3-Me H CF₂CHF₂ F Et 3-Cl H CF₂CHF₂ F i-Pr 3-Me 5-Br CF₂CHF₂ F i-Pr 3-Cl 5-Br CF₂CHF₂ F i-Bu 3-Me H Et F i-Bu 3-Cl H Et F propargyl 3-Me H CF₃ F propargyl 3-Cl H CF₃ F c-propyl 3-Me H CHF₂ F c-propyl 3-Cl H CHF₂ F i-Pr 3-Me 5-Cl CF₃ F i-Pr 3-Cl 5-Cl CF₃ F t-Bu 3-Me H «-C₃F₇ F t-Bu 3-Cl H «-C₃F₇ F

Me 3-Me 5-Cl i-C₃F₇ F Me 3-Cl 5-Cl i-C₃F₇ F

Et 3-Me H i-Pr F Et 3-Cl H i-Pr F i-Pr 3-Me H CF₃ F i-Pr 3-Cl H CF₃ F i-Bu 3-Me H _. C₂F₅ F i-Bu 3-Cl H C₂F₅ F propargyl 3-Me H C₂F₅ F propargyl 3-Cl H C₂F₅ F c-propyl 3-Me H CF₃ F c-propyl 3-Cl H CF₃ F i-Pr . 3-Me H «-Pr F i-Pr 3-Cl H rc-Pr F i-Bu 3-Me 5-Br CH₂CH₂C1 F i-Bu 3-Cl 5-Br CH₂CH₂C1 F

Me 3-Me H CF₃ Cl Me 3-Cl H CF₃ Cl

Et 3-Me 5-Me CHF₂ Cl Et 3-Cl 5-Me CHF₂ Cl i-Pr 3-Me H CHF₂ Cl i-Pr 3-Cl H CHF₂ Cl i-Bu 3-Me 5-Cl CH₂CF₃ Cl i-Bu 3-Cl 5-Cl CH₂CF₃ Cl

Me 3-Me H CH₂CF₃ Cl Me 3-Cl H CH₂CF₃ Cl

Et 3-Me H CF₂CHF₂ Cl Et 3-Cl H CF₂CHF₂ Cl i-Pr 3-Me 5-Br CF₂CHF₂ Cl i-Pr 3-Cl 5-Br CF₂CHF₂ Cl i-Bu 3-Me H Et Cl f-Bu 3-Cl H Et Cl

U ffl ffl 9 ffl o ffl ffl ffl ffl ffl ffl ^ffl ffl S ffl ^P ffl ffl ^ ffl ffl ffl ^P ffl 9 _{ffl ffl ffl ffl ffl ffl} ^ _ffl ^ _ffl 8

3 I fcl o o o o o o o o o o o o o o o o o o o o o o o o o υ o o o o o o o o o co co co co o co co co co co co co

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*J ffl ffl 9 ffi 9 ffi ffl ffl ffl ffl ffl T ffi S ffi 9 ffi ffi ffi ffl ffi 9 ffl 9 ffi ffi ffi ffi ffi ffl ^ρ9 ffi S ffi 9

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rø τj rø rø τj rø rø rø rø rø τj rø rø hrj τj hrj hrj τj hi hrj τj τj ^IωI ω ¹ 1w ^IωI 1ro ¹ω1 ω 1 ¹w1 ¹ω1 ¹ro1 ω ¹1 ⁱwt ^IwI ⁱωt ⁱωt l O ON

4-.

ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl _ro ffl ffl ffi ffi iff ffi ^ fif ω ffi

II r#

rø ES f ro rø cro τ H,^j rø ^■■* CgD -roj røHr E^ iCfD gro" τ HTj E <^■S*^■ i ffif i¬

C gD έro_! rø>- E^rtS fCD rώ_ τ HTj E^ iC?D rtffl τ if^j E ^rtS (ifI ffl rø t ed

3 T 3 ""« 3 i 3 3 ^ ^■"« ft

k k k k k k k k k k k k k k k k k k k k k k k k k k k k k k k k k k k k k \

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TJ ø j TJ T hcjl h Trj! hrj TJ

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Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω lfa

J-. J~ i- i. i- O O

,9^{. O} ,9 £ 9 9 w w rø^J rø^J^ , ^9 TJ ^O 9^J ό rj ^O T^JJ ^O ό T^JJ ^O ό rø^J ^ t u % ³ ώ³ £ r u % ώ r u %r % ui ^I røI £ rø 1 £ rø 1 E ^IIp όO 9TJ' όO 9TJ oO 9TJ όO 9TJ ? E? ? S * 5? * rø .9rø .rø .9rø ^w *w ^s * , 9 , %9 , %9 , ^9 <-^£_< <-^£, I Irøvo

-4 -4 -4 -J -4 -J -J to to to to hrj Tj Tj Tj hj hcj -J -4 -4 -4 -J — J

o o o o o o o o o o Ω Ω Ω Ω Ω Ω ^ ^ ^ Ω ^ ^ Ω Ω ^ Ω rø rø rø rø rø rø rø rø rø rø ft

R³. R4a K* s_. R⁶. E³. g4a R4b s2 s i-Bu 6-Me H i-C₃F₇ Cl i-Bu 6-C1 H i-C₃F₇ Cl

Me 6-Me H Et Cl Me 6-C1 H Et Cl

Et 6-Me H Et 01 Et 6-C1 H Et Cl i-Pr 6-Me H Et Cl i-Pr 6-C1 H Et Cl i-Bu 6-Me H Et Cl t-Bu 6-C1 H Et Cl

Me 6-Me H CHF₂ Br Me 6-C1 H CHF₂ Br

Et 6-Me H CHF₂ Br Et 6-01 H CHF₂ Br i-Pr 6-Me H CHF₂ Br i-Pr 6-C1 H CHF₂ Br i-Bu 6-Me H CHF₂ Br i-Bu 6-C1 H CHF₂ Br

Me 6-Me H «-Pr Br Me 6-01 H «-Pr Br

Et 6-Me H «-Pr Br Et 6-C1 H «-Pr Br i-Pr 6-Me H «-Pr Br i-Pr 6-C1 H κ-Pr Br i-Bu 6-Me H »-Pr Br i-Bu 6-C1 H n-Pr Br

Me 6-Me H CF₃ Br Me 6-C1 H CF₃ Br

Et 6-Me H CF₃ Br Et 6-01 H CF₃ Br i-Pr 6-Me H CF₃ Br i-Pr 6-C1 H CF₃ Br i-Bu 6-Me H CF₃ Br i-Bu 6-C1 H CF₃ Br

Me 6-Me H i-Pr Br Me 6-01 H i-Pr Br

Et 6-Me H i-Pr Br Et 6-C1 H i-Pr Br i-Pr 6-Me H i-Pr Br i-Pr 6-01 H i-Pr Br i-Bu 6-Me H i-Pr Br i-Bu 6-C1 H i-Pr Br

Me 6-Me H C₂F₅ Br Me 6-C1 H C₂F₅ Br

Et 6-Me H C₂F₅ Br Et 6-01 H C₂F₅ Br i-Pr 6-Me H C₂F₅ Br i-Pr 6-C1 H C₂F₅ Br i-Bu 6-Me H C₂F₅ Br i-Bu 6-C1 H C₂F₅ Br

Me 6-Me H JI-C3F7 Br Me 6-C1 H n-C3F Br

Et 6-Me H «-C₃F₇ Br Et 6-C1 H «-C₃F₇ Br i-Pr 6-Me H «-C₃F₇ Br i-Pr 6-C1 H «-C₃F₇ Br i-Bu 6-Me H «-C₃F₇ Br i-Bu 6-C1 H «-C₃F₇ Br

Me 6-Me H i-C₃F₇ Br Me 6-01 H i-C₃F₇ Br

Me 6-Me H Et Br Me 6-C1 H Et Br

Et 6-Me H Et Br Et 6-C1 H Et Br i-Pr 6-Me H Et Br i-Pr 6-C1 H Et Br i-Bu 6-Me H Et Br i-Bu 6-C1 H Et Br

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Ω Ω Ω Ω Ω ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffl ffl ffl ffl ffl Irø.

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o o o σN σ^ σN ON O^ ON σN N ι-Λ ^ ON O^ N O o^ O σN N O ON σ σN ON O o σ^ ON σ σ tON σ^ ^ ON

O O O O Q Q O O O Q Q Q O CJ O Q O Q O Q O O O Q O O Q O O O O O Q Q O O O ft I 50

Ω Ω Ω Ω Ω ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi _*.

E?

TJ Tj rø TJ Tj TJ TJ TJ rø rø o rø TJ TJ TJ TJ TJ TJ hcj TJ TJ TJ hcj Tj hcj TJ TJ Tj hcj TJ Tj TJ TJ hcj TJ TJ vX OJ OJ OJ OJ OJ J J ^" OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ ^{l uN}

R2 R R4b R.. ≠ E g4a R4b R.. ≠

Et 6-Me Cl K-Pr F Et 6-C1 01 «-Pr F i-Pr 6-Me Cl n-Pr F i-Pr 6-C1 Cl «-Pr F i-Bu 6-Me Cl n-Pr F i-Bu 6-01 Cl n-Pr F

Me 6-Me Cl CF₃ F. Me 6-C1 Cl CF₃ F

Et 6-Me Cl CF₃ F Et 6-C1 Cl CF₃ F i-Pr 6-Me Cl CF₃ F i-Pr 6-C1 Cl CF₃ F i-Bu 6-Me Cl CF₃ F i-Bu 6-C1 Cl CF₃ F

Me 6-Me Cl i-Pr . , F Me 6-01 Cl i-Pr F

Et 6-Me Cl i-Pr F Et 6-01 Cl i-Pr F i-Pr 6-Me Cl i-Pr F i-Pr 6-01 Cl i-Pr F i-Bu 6-Me Cl i-Pr F t-Bu 6-C1 Cl i-Pr F

Me 6-Me 01 C₂F₅ F Me 6-01 Cl C₂F₅ F

Et 6-Me 01 C₂F₅ F Et 6-C1 Cl C₂F₅ F i-Pr 6-Me Cl C₂F₅ F i-Pr 6-C1 Cl C₂F₅ F i-Bu 6-Me Cl C₂F₅ F i-Bu 6-01 01 C₂F₅ F

Me 6-Me Cl «-C₃F₇ F Me 6-C1 01 «-C₃F₇ F

Et 6-Me Cl «-C₃F₇ F Et 6-C1 Cl n-C₃F₇ F i-Pr 6-Me Cl «-C₃F₇ F i-Pr 6-C1 Cl «-C₃F₇ F i-Bu 6-Me Cl «-C₃F₇ F i-Bu 6-C1 Cl «-C₃F₇ F

Me 6-Me Cl i-C₃F₇ F Me 6-C1 Cl i-C₃F₇ F

Et 6-Me Cl i-C₃F₇ F Et 6-C1 Cl i-C₃F₇ F i-Pr 6-Me Cl i-C₃F₇ F i-Pr 6-C1 Cl i-C₃F₇ F i-Bu 6-Me Cl i-C₃F₇ F i-Bu 6-C1 Cl i-C₃F₇ F

Me 6-Me Cl Et F Me 6-01 Cl Et F

Et 6-Me Cl Et F Et 6-01 Cl Et F i-Pr 6-Me Cl Et F i-Pr 6-C1 Cl Et F i-Bu 6-Me Cl Et .. F t-Bu 6-C1 Cl Et F

Me 6-Me Cl CHF₂ Cl Me 6-C1 Cl CHF₂ Cl

Et 6-Me Cl CHF₂ Cl Et 6-C1 Cl CHF₂ Cl i-Pr 6-Me Cl CHF₂ 01 i-Pr 6-C1 Cl CHF₂ Cl i-Bu 6-Me Cl CHF₂ 01 i-Bu 6-C1 Cl CHF₂ Cl

Me 6-Me Cl H-Pr . ci Me 6-01 Cl n-Pr Cl

Et 6-Me Cl n-Pr Cl Et 6-01 01 «-Pr Cl i-Pr 6-Me Cl «-Pr CI i-Pr 6-C1 Cl n-Pr CI i-Bu 6-Me Cl H-Pr 01 i-Bu 6-C1 01 n-Pr Cl

Me 6-Me Cl CF₃ Cl Me 6-01 01 CF₃ Cl

Et 6-Me Cl CF₃ Cl Et 6-C1 Cl CF₃ Cl fcl G G G G G G G G G G G G G G G G G G G G G G m m m m m m m ffl ffl ffl ffl P^ m

3 I fcl o o O O O O O O O O o o o o o o

VO VO vό o o l gl gl gl ol ol oi o ■ o ■ g I g 1 o l gl ol ol ol ol ol vό vό vό vό vό vό vό vό vό vό vo VO vo VO vό vό vό vό vo vό vό vό vό vό vo vό vo vό vό vό vό vό vό

3 3 a 5 s pq ft ffl u5 "Hi ft ϋ - ffl? ώ I H _T A 3 fl - ft.l ffl5 j! a« * ft - 3 f ffl? a ^ *ai ₍ftfr f5 -. 3 3 fl a ft ^p? pq S ft ? ffl 2 pq ft ffl q

D fcl G G G G G G G G G O G G G G G G G G G G G ffl ffl m m m ffl m m m ffl ffl m m m

r— t— t — — 1 — r — r—

CO CO Si Si CN CN CN CN f fc fc fc fc r^ i^ ^ ^ ft ft ft ft ft ft ft ft ,. fcl c -H

Ei R R

^| o G G G G G G G G G G G G G G G G G G G G G G G G G G G G G O G G G G G

t- ό

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CN

B g4 R4b E2 BS E R^a g4b R9 R6 i-Bu 6-Me Cl i-Pr Br i-Bu 6-C1 Cl i-Pr Br

Me 6-Me CI C₂F₅ Br Me 6-CI CI C₂F₅ Br

Et 6-Me Cl C₂F₅ Br Et 6-C1 Cl C₂F₅ Br i-Pr 6-Me Cl C₂?5 Br i-Pr 6-CI Cl C₂F₅ Br i-Bu 6-Me Cl C₂F₅ Br i-Bu 6-CI Cl C₂F₅ Br

Me 6-Me Cl n-C₃F₇ Br Me 6-CI 01 n-C₃F₇ Br

Et 6-Me Cl «-C₃F₇ Br Et 6-CI Cl n-C₃F₇ Br i-Pr 6-Me Cl n-C₃F₇ Br i-Pr 6-CI Cl n-C₃F₇ Br i-Bu 6-Me Cl n-C₃F₇ Br i-Bu 6-CI Cl n-C₃F₇ Br

Me 6-Me Cl i-C₃F₇ Br Me 6-CI Cl i-C₃F₇ Br

Et 6-Me Cl i-C₃F₇ Br Et 6-CI Cl i-C₃F₇ Br i-Pr 6-Me Cl i-C₃F₇ Br i-Pr 6-CI Cl i-C₃F₇ Br i-Bu 6-Me Cl i-C₃F₇ Br t-Bu 6-CI Cl i-C₃F₇ Br

Me 6-Me 01 Et Br Me 6-01 Cl Et Br

Et 6-Me 01 Et Br Et 6-CI Cl Et Br i-Pr 6-Me 01 Et Br i-Pr 6-01 01 Et Br i-Bu 6-Me 01 Et Br i-Bu 6-01 Cl Et Br

Me 6-Me 01 CHF₂ CF₃ Me 6-01 Cl CHF₂ CF₃

Et 6-Me 01 CHF₂ CF₃ Et 6-CI Cl CHF₂ CF₃ i-Pr 6-Me 01 CHF₂ CF₃ i-Pr 6-CI Cl CHF₂ CF₃ i-Bu 6-Me Cl CHF₂ CF₃ i-Bu 6-CI Cl CHF₂ CF₃

Me 6-Me Cl n-Pr CF₃ Me 6-CI Cl n-Pr CF₃

Et 6-Me Cl n-Pr CF₃ Et 6-01 01 n-Pr CF₃ i-Pr 6-Me Cl n-Pr CF₃ i-Pr 6-CI Cl n-Pr CF₃ i-Bu 6-Me Cl n-Pr CF₃ i-Bu 6-01 Cl n-Pr CF₃

Me 6-Me Cl CF₃ CF₃ Me 6-CI Cl CF₃ CF₃

Et 6-Me 01 CF₃ " CF₃ Et 6-01 Cl CF₃ CF₃ i-Pr 6-Me 01 CF₃ CF₃ i-Pr 6-01 Cl CF₃ CF₃ i-Bu 6-Me 01 CF₃ CF₃ ' i-Bu 6-01 Cl CF₃ CF₃

Me 6-Me 01 i-Pr CF₃ Me 6-CI Cl i-Pr CF₃

Et 6-Me 01 i-Pr CF₃ Et 6-CI CI i-Pr CF₃ i-Pr 6-Me 01 i-Pr "CF₃ i-Pr 6-CI Cl i-Pr CF₃ i-Bu 6-Me 01 i-Pr CF₃ i-Bu 6-01 Cl i-Pr CF₃

Me 6-Me Cl C₂F₅ CF₃ Me 6-01 Cl C₂F₅ CF₃

Et 6-Me 01 C₂F₅ CF₃ Et 6-01 Cl C₂F₅ CF₃ i-Pr 6-Me 01 C₂F₅ CF₃ i-Pr 6-CI Cl C₂F₅ CF₃ i-Bu 6-Me Cl C₂F₅ CF₃ i-Bu 6-01 Cl C₂F₅ CF₃ E? w

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3 R4a R4b 12 ≠ X E. R a R^ B2 R6 X i-Bu 6-Me H C₂F₅ Cl CH i-Bu 6-CI H C₂F₅ Cl CH

Me 6-Me H n-C₃F₇ Cl CH Me 6-CI H n-C₃F₇ Cl CH

Et 6-Me H «-C₃F₇ Cl CH Et 6-CI H n-C₃F₇ Cl CH i-Pr 6-Me H n-C₃F₇ Cl CH i-Pr 6-01 H n-C₃F₇ Cl CH i-Bu 6-Me H n-C₃F₇ Cl CH i-Bu 6-01 H n-C₃F₇ Cl CH

Me 6-Me H i-C₃F₇ Cl CH Me 6-CI H i-C₃F₇ Cl CH

Et 6-Me H i-C₃F₇ Cl CH Et 6-CI H i-C₃F₇ Cl CH i-Pr 6-Me H i-C₃F₇ Cl CH i-Pr 6-CI H i-C₃F₇ Cl CH i-Bu 6-Me H i-C₃F₇ Cl CH i-Bu 6-CI H i-C₃F₇ CI CH

Me 6-Me H Et 01 CH Me 6-01 H Et Cl CH

Et 6-Me H Et 01 CH Et 6-01 H Et Cl CH i-Pr 6-Me H Et 01 CH i-Pr 6-CI H Et Cl CH i-Bu 6-Me H Et 01 CH i-Bu 6-01 H Et Cl CH

Me 6-Me H CHF₂ Br CH Me 6-01 H CHF₂ Br CH

Et 6-Me H CHF₂ Br CH Et 6-01 H CHF₂ Br CH i-Pr 6-Me H CHF₂ Br CH i-Pr 6-01 H CHF₂ Br CH i-Bu 6-Me H CHF₂ Br CH i-Bu 6-CI H CHF₂ Br CH

Me 6-Me H n-Pr Br CH Me 6-CI H «-Pr Br CH

Et 6-Me H n-Pr Br CH Et 6-CI H n-Pr Br CH i-Pr 6-Me H n-Pr Br CH i-Pr 6-CI H n-Pr Br CH i-Bu 6-Me H n-Pr Br CH i-Bu 6-CI H «-Pr Br CH

Me 6-Me H CF₃ Br CH Me 6-CI H CF₃ Br CH

Et 6-Me H CF₃ Br CH Et 6-01 H CF₃ Br CH i-Pr 6-Me H CF₃ Br CH i-Pr 6-01 H CF₃ Br CH t-Bu 6-Me H CF₃ Br CH i-Bu 6-CI H CF₃ Br CH

Me 6-Me H i-Pr Br CH Me 6-CI H i-Pr Br CH

Et 6-Me H i-Pr Br CH Et 6-01 H i-Pr Br CH i-Pr 6-Me H i-Pr Br CH i-Pr 6-01 H i-Pr Br CH t-Bu 6-Me H i-Pr Br CH t-Bu 6-01 H i-Pr Br CH

Me 6-Me H C₂F₅ Br CH Me 6-01 H C₂F₅ Br CH

Et 6-Me H C₂F₅ Br CH Et 6-01 H C₂F₅ Br CH i-Pr 6-Me H C₂F₅ Br ^• CH i-Pr 6-01 H C₂F₅ Br CH i-Bu 6-Me H C₂F₅ Br CH i-Bu 6-01 H C₂F₅ Br CH

Me 6-Me H n-C₃F₇ Br CH Me 6-01 H n-C₃F₇ Br CH

Et 6-Me H »-C₃F₇ Br CH Et 6-01 H n-C₃F₇ Br CH i-Pr 6-Me H n-C₃F₇ Br CH i-Pr 6-01 H n-C₃F₇ Br CH i-Bu 6-Me H n-C₃F₇ Br CH t-Bu 6-01 H n-C₃F₇ Br CH R³- g4a Rfb R£ ≠ X S³. R4a R4b R9 R6 X

Me 6-Me H i-C₃F₇ Br CH Me 6-CI H i-C₃F₇ Br CH

Et 6-Me H i-C₃F₇ Br CH Et 6-CI H i-C₃F₇ Br CH i-Pr 6-Me H i-C₃F₇ Br CH i-Pr 6-01 H i-C₃F₇ Br CH i-Bu 6-Me H i-C₃F₇ Br CH t-Bu 6-CI H '-C3F7 Br CH

Me 6-Me H Et Br CH Me 6-CI H Et Br CH

Et 6-Me H Et Br CH Et 6-CI H Et Br CH i-Pr 6-Me H Et Br CH i-Pr 6-CI H Et Br CH i-Bu 6-Me H Et Br CH i-Bu 6-CI H Et Br CH

Me 6-Me H CHF₂ CF₃ CH Me 6-CI H CHF₂ CF₃ CH

Et 6-Me H CHF₂ CF₃ CH Et 6-CI H CHF₂ CF₃ CH i-Pr 6-Me H CHF₂ CF₃ CH i-Pr 6-CI H CHF₂ CF₃ CH i-Bu 6-Me H CHF₂ CF₃ CH i-Bu 6-CI H CHF₂ CF₃ CH

Me 6-Me H n-Pr CF₃ CH Me 6-CI H n-Pr CF₃ CH

Et 6-Me H n-Pr CF₃ CH Et 6-01 H n-Pr CF₃ CH i-Pr 6-Me H n-Pr CF₃ CH i-Pr 6-CI H n-Pr CF₃ CH i-Bu 6-Me H n-Pr CF₃ CH i-Bu 6-CI H n-Pr CF₃ CH

Me 6-Me H CF₃ CF₃ CH Me 6-01 H CF₃ CF₃ CH

Et 6-Me H CF₃ CF₃ CH Et 6-CI H CF₃ CF₃ CH i-Pr 6-Me H CF₃ CF₃ CH i-Pr 6-01 H CF₃ CF₃ CH i-Bu 6-Me H CF₃ CF₃ CH i-Bu 6-01 H CF₃ CF₃ CH

Me 6-Me H i-Pr CF₃ CH Me 6-01 H i-Pr CF₃ CH

Et 6-Me H i-Pr CF₃ CH Et 6-CI H i-Pr CF₃ CH i-Pr 6-Me H i-Pr CF₃ CH i-Pr 6-CI H i-Pr CF₃ CH i-Bu 6-Me H i-Pr CF₃ CH i-Bu 6-CI H i-Pr CF₃ CH

Me 6-Me H C₂F₅ CF₃ CH Me 6-CI H C₂F₅ CF₃ CH

Et 6-Me H C₂F₅ CF₃ CH Et 6-CI H C₂F₅ CF₃ CH i-Pr 6-Me H C₂F₅ CF₃ CH i-Pr 6-CI H C₂F₅ CF₃ CH i-Bu 6-Me H C₂F₅ CF₃ CH i-Bu 6-CI H C₂F₅ CF₃ CH

Me 6-Me H n-C₃F₇ CF₃ CH' Me 6-CI H n-C₃F₇ CF₃ CH

Et 6-Me H n-C₃F₇ CF₃ CH Et 6-CI H n-C₃F₇ CF₃ CH i-Pr 6-Me H Λ-C3F7 CF₃ CH i-Pr 6-CI H n-C₃F₇ CF₃ CH i-Bu 6-Me H ^' n-C₃F₇ CF₃ CH i-Bu 6-CI H n-C₃F₇ CF₃ CH

Me 6-Me H i-C₃F₇ CF₃ CH Me 6-CI H i-C₃F₇ CF₃ CH

Et 6-Me H i-C₃F₇ CF₃ CH Et 6-CI H i-C₃F₇ CF₃ CH i-Pr 6-Me H i-C₃F₇ CF₃ CH i-Pr 6-CI H i-C₃F₇ CF₃ CH i-Bu 6-Me H i-C₃F₇ CF₃ CH i-Bu 6-01 H i-C₃F₇ CF₃ CH

Me 6-Me H Et CF₃ CH Me 6-CI H Et CF₃ CH si g4a Ed-l ? E_. X g4a St* -. R_. X

Et 6-Me H Et CF₃ CH Et 6-CI H Et CF₃ CH i-Pr 6-Me H Et CF₃ CH i-Pr 6-CI H Et CF₃ CH i-Bu 6-Me H Et CF₃ CH i-Bu 6-01 H Et CF₃ CH

Me 6-Me Cl CHF₂ F CH Me 6-CI 01 CHF₂ F CH

Et 6-Me Cl CHF₂ F CH Et 6-CI 01 CHF₂ F CH i-Pr 6-Me Cl CHF₂ F CH i-Pr 6-01 01 CHF₂ F CH i-Bu 6-Me Cl CHF₂ F CH i-Bu 6-CI Cl CHF₂ F CH

Me 6-Me Cl n-Pr F CH Me 6-CI Cl n-Pr F CH

Et 6-Me 01 n-Pr F CH Et 6-CI Cl n-Pr F CH i-Pr 6-Me 01 π-Pr F CH i-Pr 6-CI Cl n-?r F CH i-Bu 6-Me Cl n-Pr F CH t-Bu 6-CI Cl n-Pr F CH

Me 6-Me Cl CF₃ F CH Me 6-CI Cl CF₃ F CH

Et 6-Me Cl CF₃ F CH Et 6-CI Cl CF₃, F CH i-Pr 6-Me Cl CF₃ F CH i-Pr 6-CI Cl CF₃ F CH i-Bu 6-Me Cl CF₃ F CH i-Bu 6-CI Cl CF₃ F CH

Me 6-Me Cl i-Pr F CH Me 6-CI Cl i-Pr F CH

Et 6-Me Cl i-Pr F CH Et 6-01 01 i-Pr F CH i-Pr 6-Me Cl i-Pr F CH i-Pr 6-CI Cl i-Pr F CH i-Bu 6-Me Cl i-Pr F CH i-Bu 6-CI Cl i-Pr F CH

Me 6-Me Cl C₂F₅ F CH Me 6-CI Cl C₂F₅ F CH

Et 6-Me Cl C₂F₅ F CH Et 6-CI Cl C₂F₅ F CH i-Pr 6-Me Cl C₂F₅ F CH i-Pr 6-CI Cl C₂F₅ F CH i-Bu 6-Me 01 C₂F₅ F CH i-Bu 6-CI Cl C_{2 5} F CH

Me 6-Me Cl n-C₃F₇ F CH Me 6-01 Cl n-C₃F₇ F CH

Et 6-Me 01 n-C₃F₇ F CH Et 6-01 Cl n-C₃F₇ F CH i-Pr 6-Me Cl «-C₃F₇ F CH i-Pr 6-01 Cl n-C₃F₇ F CH i-Bu 6-Me 01 n-C₃F₇ F CH i-Bu 6-CI 01 n-C₃F₇ F CH

Me 6-Me Cl -C₃F₇ F CH Me 6-01 Cl i-C₃F₇ F CH

Et 6-Me Cl i-C₃F₇ F CH Et 6-01 Cl i-C₃F₇ F CH i-Pr 6-Me Cl i-C₃F₇ F CH i-Pr 6-01 Cl i-C₃F₇ F CH i-Bu 6-Me Cl i-C₃F₇ F CH i-Bu 6-01 Cl i-C₃F₇ F CH

Me 6-Me Cl ^' Et F - CH Me 6-CI Cl Et F CH

Et 6-Me Cl Et F CH Et 6-CI Cl Et F CH i-Pr 6-Me Cl Et F CH i-Pr 6-01 Cl Et F CH i-Bu 6-Me Cl Et F CH i-Bu 6-CI Cl Et F CH

Me 6-Me 01 CHF₂ 01 CH Me 6-01 Cl CHF₂ Cl CH

Et 6-Me Cl CHF₂ Cl CH Et 6-CI Cl CHF₂ Cl CH El g4a g4b &_. X R3 g4a R4b E2 ≠ X i-Pr 6-Me Cl CHF₂ 01 CH i-Pr 6-CI Cl CHF₂ Cl CH t-Bu 6-Me Cl CHF₂ 01 CH i-Bu 6-CI 01 CHF₂ Cl CH

Me 6-Me Cl n-Pr 01 CH Me 6-CI 01 n-Pr Cl CH

Et 6-Me Cl n-Pr Cl CH Et 6-CI 01 n-Pr Cl CH i-Pr 6-Me Cl n-Pr Cl CH i-Pr 6-01 Cl n-Pr Cl CH i-Bu 6-Me Cl n-Pr Cl CH i-Bu 6-CI Cl n-Pr Cl CH

Me 6-Me Cl CF₃ Cl CH Me 6-CI Cl CF₃ Cl CH

Et 6-Me Cl CF₃ Cl CH Et 6-CI Cl CF₃ Cl CH i-Pr 6-Me 01 CF₃ Cl CH i-Pr 6-CI Cl CF₃ Cl CH i-Bu 6-Me Cl CF₃ Cl CH i-Bu 6-CI Cl CF₃ Cl CH

Me 6-Me Cl i-Pr Cl CH Me 6-CI Cl i-Pr 01 CH

Et 6-Me Cl i-Pr Cl CH Et 6-CI Cl i-Pr 01 CH i-Pr 6-Me Cl i-Pr Cl CH i-Pr 6-CI Cl i-Pr 01 CH i-Bu 6-Me Cl i-Pr Cl CH i-Bu 6-CI Cl i-Pr 01 CH

Me 6-Me Cl C₂F₅ Cl CH Me 6-CI Cl C_{2 5} 01 CH

Et 6-Me Cl C_{2 5} Cl CH Et 6-CI 01 C₂F₅ Cl CH i-Pr 6-Me Cl C₂F₅ Cl CH i-Pr 6-CI Cl C₂F₅ Cl CH i-Bu 6-Me Cl C₂F₅ Cl CH i-Bu 6-01 01 C₂F₅ Cl CH

Me 6-Me Cl n-C₃F₇ Cl CH Me 6-01 Cl n-C₃F₇ Cl CH

Et 6-Me Cl n-C₃F₇ Cl CH Et 6-CI 01 "-C3 7 Cl CH i-Pr 6-Me Cl , n-C₃F₇ Cl CH i-Pr 6-CI Cl «-C₃F₇ Cl CH i-Bu 6-Me Cl n-C₃F₇ Cl CH i-Bu 6-01 01 "-C3 7 Cl CH

Me 6-Me Cl i-C₃F₇ 01 CH Me 6-01 01 i-C₃F₇ Cl CH

Et 6-Me 01 i-C₃F₇ 01 CH Et 6-01 Cl i-C₃F₇ Cl CH i-Pr 6-Me Cl i-C₃F₇ Cl CH i-Pr 6-CI Cl i-C₃F₇ Cl CH i-Bu 6-Me Cl i-C₃F₇ Cl CH i-Bu 6-01 Cl i-C₃F₇ Cl CH

Me 6-Me Cl Et Cl CH Me 6-01 Cl Et Cl CH

Et 6-Me Cl Et Cl CH Et 6-01 Cl Et Cl CH i-Pr 6-Me Cl Et Cl CH i-Pr 6-01 Cl Et Cl CH i-Bu 6-Me 01 Et 01 CH i-Bu 6-01 Cl Et Cl CH

Me 6-Me Cl CHF₂ Br CH Me 6-01 Cl CHF₂ Br CH

Et 6-Me Cl ^' CHF₂ Br CH Et 6-01 Cl CHF₂ Br CH i-Pr 6-Me Cl CHF₂ Br CH i-Pr 6-CI Cl CHF₂ Br CH i-Bu 6-Me Cl CHF₂ Br CH i-Bu 6-CI Cl CHF₂ Br CH

Me 6-Me Cl n-Pr Br CH Me 6-CI Cl n-Pr Br CH

Et 6-Me Cl n-Pr Br CH Et 6-CI Cl n-Pr Br CH i-Pr 6-Me Cl n-Pr Br CH i-Pr 6-CI 01 n-Pr Br CH δ β røι-1^' E^rtS ^CD S τJ ES s f?> ffl 3 δ i-T E^ it? ffl rø rø $ $ ES ώ _H? ES ώ J ES §£ ffl J ES ffl

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O O O O O O O O Q Q Q Q Q Q Ω Ω O Q Q Ω O O Q O Q Q O Q Q Q O O O

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Ω Ω Ω Ω Si a a a J rø ør y HH. OJ J OJ oJ o O ,o to O ? hcj t to O 333 i v- Ω Ω <"^J vθ hcj r TI J M TcjJ « hrj o E? ft vo to to g to § to 8 ^w TJ Tj rø TJ j Tj rø ft

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999 Ω 9 9 9 9 ^Ω ffl 99 9 9 9 9 9 9 9 9 9 9 9 9 ^Ω 9 ^Ω9 999999999 ι ro E? rø « E? W I fJ iro røi-t^' E^ if! ro rø^' ES ! ro τj ES ^ ro rø^' ES i! ro . ES ^ ro rø^' rø fi f fi C il ^ C a" •^■♦ ffi j? πf ** ffi *i *+ CO & H f c ffi ffl 3 3 ES ω rø.

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Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω O O O O O O O O O O O O O O Q Q Q O Q Q Q O Q O

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k k k k k k k k k k k k k k k k k k k k k k k k k k k k k k k k k k k k k ft

ffl ffl ffi ffi ffi ffi ffi ffi ffi ffl ffl ffl ffl ffi ffi ffi ffl Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω

o ~. v a r rø rø 9 9 9 9 ? O ø rø ,Q A. to O to O to o to o

U rø Tl rø V , TJ Tj rø l U 8 § € @ E ES ES ES <° ? J? o o o o to to rø Tl Ui Ui E? E? ft -4

rø TI rø rø rø rø ft

9 9 9 9 9 9 9 9 9 9 ffl ffl tn ffl ffi ffi ffi ffl ffi ffi ffi ffl IX

S ώ ζ ES f ro rø ES if ro ^ ES lff ES sf o ω ffl

3 EP r rø ES ffl rø ES ffl rø^' ES rø

3 3 rø rø ft

Os Os Os Os Os Os Os Os Os Os Os Os Os Os Os Os Os Os Os Os Os Os Os Os Os Os Os Os Os Os Os Os Os Os Os Os Os o o o o o π o π o o o o o o o o o o o o o o o o o o o o o o o o o o o o o ft

ffl ffl ffl K K K ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω & o a a a

7- O O O Ω Ω r rø TJ W W o o o o o o O O to o to t to t? E? E? T Tl ø rø rø rø Irøvo to t to to ^ørt -ørJ - rø4 -4ør r rø r rø rø rø rø E? E? i

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rø TJ rø Tj _^ O O O O O O O Q O Q Q Q Q Q Q Q Q Q Q Q ft I ON

Ω rø Ωrø Ωrø Ωrø Ωrø Ωrø Ωrø Ωrø Ωrø Ωrø Ωrø Ωrø Ωrø Ωrø Ωrø Ωrø Ωrø Ωffi Ωffi Ωffi Ωffi Ωffi Ωffi Ωffi Ωffi Ωffi Ωffi Ωffl Ωffi Ωffi Ωffi Ωffi Ωffl ffi ffi ffi IX

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o o Q Ω Ω Ω Ω Ω Ω ^ Ω Ω Ω ^ ^ ^ ^ ^ ^ Ω Ω rø rø rø rø rø rø rø rø rø rø rø rø rø rø rø Ift

_^ θN θN OΛ O θ θ\ ^ ON σN I-^ OΛ θN θΛ ON θN θΛ θN θ ^ ON θ σN θN θN θ θ θN ^ N θN σN θΛ θN σ σ θN

O O O O O O Q Ω Ω Ω Ω Ω Ω O Q Q O Q Q O O O O O Q O O Q O O Ω O O O O O O ft P

K K HH HH ffi ffi ffi W H HM HH H HH ffi

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O O O O O O O O O O O O O O O O O O O O O O Π O O O O O O O O O O O O O O O O O Q Q O O O Q O O O O Ω θ y rø rø rø rø y y rø rø τj y y y j lX

R _R4a _R4b R9 R6 X R3 .4a _R4b R9 Rθ X i-Pr 6-Me H n-C₃F₇ Cl CC1 i-Pr 6-CI H n-C₃F₇ 01 CC1 i-Bu 6-Me H n-C₃F₇ Cl CC1 i-Bu 6-01 H n-C₃F₇ Cl CC1

Me 6-Me H i-C₃F₇ Cl CC1 Me 6-CI H i-C₃F₇ Cl CC1

Et 6-Me H i-C₃F₇ Cl CC1 Et 6-CI H i-C₃F₇ Cl CC1 i-Pr 6-Me H i-C₃F₇ Cl CC1 i-Pr 6-CI H i-C₃F₇ 01 CC1 i-Bu 6-Me H i-C₃F₇ Cl CC1 i-Bu 6-CI H i-C₃F₇ Cl CC1

Me 6-Me H Et Cl CC1 Me 6-01 H Et Cl CC1

Et 6-Me H Et Cl CC1 Et 6-01 H Et Cl CC1 i-Pr 6-Me H Et Cl CC1 i-Pr 6-CI H Et Cl CC1 i-Bu 6-Me H Et Cl CC1 i-Bu 6-01 H Et Cl CC1

Table 13

_R4a _R4b R7 R R6 _R4a _R4b R7 R3 R6 _R4a _R4b R7 R R6

CH₃ F CF₃ Me 01 01 F CF₃ Me Cl Br F CF₃ Me Cl

CH₃ F CF₃ Et Cl 01 F CF₃ Et Cl Br F CF₃ Et Cl

CH₃ F CF₃ i-Pr Cl Cl F CF₃ i-Pr Cl Br F CF₃ i-Pr Cl

CH₃ F CF₃ i-Bu Cl Cl F CF₃ t-Bu Cl Br F CF₃ i-Bu Cl

CH₃ F CF₃ Me Br Cl F CF₃ Me Br Br F CF₃ Me Br

CH₃ F CF₃ Et Br Cl F CF₃ Et Br Br F ^CF3 Et Br

CH₃ F CF₃ i-Pr Br Cl F CF i-Pr Br Br F CF₃ i-Pr Br

CH₃ F CF₃ i-Bu Br Cl F CF₃ i-Bu Br Br F CF₃ i-Bu Br

CH₃ F Cl Me Cl 01 F Cl Me Cl Br F Cl Me Cl

CH₃ F Cl Et Cl Cl F Cl Et Cl Br F Cl Et Cl

CH₃ F Cl i-Pr Cl 01 F Cl i-Pr Cl Br F Cl i-Pr Cl

CH₃ F Cl i-Bu 01 Cl F Cl i-Bu Cl Br F Cl i-Bu Cl

CH₃ F Cl Me Br Cl F Cl Me Br Br F Cl Me Br

CH₃ F Cl Et Br Cl F Cl Et Br Br F Cl Et Br IΛ t-

S

H fc s 3 ffl CJ a 5 3 a s 3 3

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5 3 a 3

S 3 a 3

5 3 1 a ft co fc G G ffl pq ffl ffl m m ffl ffl υ fc δ δ δ δ δ δ fc 8 o o o o o o υ o m m m ffl m ffl m m δ δ fc fc fc fc fc fc fc fc fc fc

% o o o o o g o g o o o o o o o o g g o o ffl ffl cα Si Si S Si fc ffl to ffl ffl ffl ffl ffl m ffl ffl ffl ffl to to to ffl ffl ffl m ffl pq ffl ffl ffl to ffl ffl to ffl ffl ffl ffl ffl ffl to m o . i! ffl ffl G G G G m ffl ffl ffl G g G G to m m ffl G G G G m ffl ffl ffl G G G G ffl ffl m to G G

CN fc G G ffl ffl ffl ffl m ffl ffl pq δ δ 8 fc fc 8 fc 8 δ δ S o o o o o pq ffl ffl m m ffl ffl m δ δ fc fc fc fc fc fc fc fc ft fc o O o o o o o o o o o o o o o o ffl pq cα fc o o u o o o o o o o o o o o o o o o o υ o o o o o o o o o o o

3 3 fc 3 1 a 3

5 3 a 3

S pq a 3

5 3 a s 3 3 a s 3 3 to s pq J. a 3

5 pq 1 a s 3

3 1 to co fc G o ffl ffl ffl ffl to m ffl ffl fc g 8 fc δ fc g δ δ δ δ o o o o o o ffl ffl m ffl ffl ffl ffl ffl δ δ fj fc fc fc fc fc fc fc fc fc fc o o o o o o o o o o υ o o o υ o o O o o m m t- 3 1 co co co co fcl ffl 8 5 5 5 5 5 5 5 5 5 5 ffl 8 8 ffl 5 5 5 5 5 5 8 ffl ffl 8 5 ffl 8 ffl 8 8 ffl 5 5 5 5 5 5 ffl 8 5 ffl 8 ffl 8 5 o

9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 ft 1

O o O O O o o o 9 9 9 9 9 9 9 9 Cd Cd ffl Cd o Cd ι-t r ω ω o O o o o O O 9 9 9 9 9 ft δ 3 E? ES cf δ 3 5 ES cf δ 3 5 ES cf δ 3 E? ES cf δ 3 5 ES cf 3 δ 5 ES f δ 3 5 ES f δ 3 S ES f 3 δ S ES cf 3 δ ft

O o o o O o o O o O o O O o o O O O o O o o O O O O o o o o o O O o o O o ft ro Cd ro ro ffl ffl ffl ffl flf ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl Cd Cd Cd Cd ffl ffl Cd Cd Cd

O O O o Cd Cd ro Cd Cd W Cd Cd O o o o o o o O 9 9 9 9 9 9 9 9 O Q O O 9 9 9 9 9 t ft

ω Cd ro Cd Cd W Cd Cd Ω Q Ω O EP Cd w Cd ⁱi Q Ω Q Q Cd w Cd ffl o Ω Q Q o Ω Q Ω EP Cd ffl ω O ft ffl ffl ω ω w ω ω w EP ffl Cd Cd fl w EP ffl Cd ω Cd

T f T ^W B? ω ω ffl •I B? ro w ffl Cd ω Cd ω ffl w ffl ω ffl ft

BP BP ffl Cd r Cd BP ffl w lff d Cd ι-» o ⁱi ffl C

T $ Cd ffl ffl ω ro ro Cd

T %

O O O O O O O O 9 9 9 9 9 9 9 9 Cd ω Cd Cd EP ro Cd ffl O o o O o o O O 9 9 9 9 9 ^

fc 9 fc c J O9 f J O9 fc J O9 c fc J O9f J O9 fc J O9 fc J O9J

O9J O9J O9J O9J O9J O9J O9J ftI P

K Ω "^ Ω^^ Ω Ω^^ O9J O9J O9J O9J O9J O9J O9J O9 O9J O9J O9J O9J O9J O9J O9J O9J O9J O9J O9J 9J O9J O9J O9 9 , ._ .-. _M « ,1 >_ I lftάr¹ _ω 9 Ω ^H- Ω^H- Ω^HI Ω^H1 5¹1^{j ω I}I ^{ω 1}1 ^{ω 1}1 ^{ω 1}1 ^{ω I}I ^{ω 1}1 ^{ω H}-t Ω ^>-* Ω-' Ω^h-, Ω^,-^α Ω^>- Ω^h-' Ω^>-^J Ω^>-' θ9J O9J O9J O9J O9J O9J O9J O9J ^ffl ffl ^ ω ffl• ffl■ ffl ffl T ffl 1 |1rø-4₁

C gD 3 δ3 3ro rø₁1 δ3 δ i-i E^S fCD δ rø ES f δ ø rø E "S^■ f CD δ ø τ HtJ E ^ ffig δ ø δ E "S i ffif δ ø δ H ES f & δ ø δ ι-r E <-*^■ j ffi δ ø δ >1 ^rtE C§J: ft I "

Ω Ω Ω Ω Ω ^{κ ffl ffl ffl} Ω Ω Ω Ω Ep ^ffl EP EP Ω Ω Ω Ω ^{ω ffl ffl ffl} Ω Ω Ω Ω ^w B? ^{ffl ffl} Ω Ω Ω Ω ft

0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 ft

O ΩJ OΩJ OΩJ OΩJ OQJ _{M M M M M M M M M} „ _{M H M M M M M M M M} HI I-H W H HW 1 ^Hi ^H, ^l-, ^H, H, | *! l fl t

O ΩJ O9J O9J O9J O9J ff¹-¹ ffl ^l"> ffl -¹ f ^ ffl ^ ffl ^ ffl -* ffl o ^ o^ o- o- o- o- o- o- O9J O9J 9J O9J O9J 9J O9J O9J ffl¹-¹ ffl -• ffl -« ffl -¹ ffl -¹ ffl -¹ ffl "« ffl -ⁱ |li^;;-^dJ J g CD ώ rø 11 ES fi CD øffl ^ H E *S+ f CO øro rø H ES+ f CO ffl ^ E "^S f ffi ffl rø i-T E "^S ^ ffi øffl rø ES tf CO øffl rø ES f CO ffl ø rø Ht E ^rtS if ffi øro rø ι-r E «^■S+ if ffi ft ' **>

H? Ω Ω Ω Ω H? H? H? H? Ω Ω Ω Ω H? H? H? H? Ω Ω Ω Ω H? H? H? H? Ω Ω Ω Ω H? ^{ffl ffl ffl} Ω Ω Ω ° ft

HH i-H Hi ι-ι >-H ro ro ro ro ro ro ro ro ro ro ro ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl Cd ffl ffl ffl ro ro r-

Ω "— ^ Ω^^ Ω"-^ Ω Ω^^{^} o9j o9j o9J O9J O9J O9J 9J O9J O9J O9J O9J O9J O9J 9J O9J 9J O9J 9J O9J O9O9J O9J O9J O9J - - ft l άr*

O 9J OJ O9J OJ OJ ^ffl ^ H?» H ^? H ^? H? H ^? H?^• H?^• Ω — Ω — Ω ^ Ω ^ Ω ^ ^ Ω ^ Ω ^ O9J 9J O9J 9J 9J O9J OJ O9J ^ffl ^ H? H? H? H? H? ^ω ^ s T^j l I^?d -4, CO p_j > ffl Ω Ω

g4a R4b EZ El R6 g _R44aa _R4b _R7 _R3 _R6 _R4a R4T> R7 R R6

CH H CF₃ Et Cl Cl CF CF Et Br Cl CF₃ Et Br

CH₃ H CF₃ i-Pr 01 Cl CF₃ CF i-Pr Br Cl CF₃ i-Pr Br

CH₃ H CF₃ i-Bu Cl 01 CF CF₃ i-Bu Br 01 CF₃ i-Bu Br

CH₃ H CF₃ Me Br Cl CF₃ Cl Me Cl Cl Cl Me Cl

CH₃ H CF₃ Et Br Cl CF₃ Cl Et Cl Cl 01 Et Cl

CH₃ H CF₃ i-Pr Br 01 CF₃ Cl i-Pr 01 01 Cl i-Pr Cl

CH₃ H CF₃ i-Bu Br 01 CF Cl i-Bu Cl Cl Cl i-Bu Cl

CH₃ H Cl Me 01 01 CF₃ Cl Me Br Cl Cl Me Br

CH₃ H Cl Et Cl Cl CF₃ Cl Et Br Cl Cl Et Br

CH₃ H Cl i-Pr Cl Cl CF Cl i-Pr Br 01 Cl i-Pr Br

CH₃ H Cl i-Bu Cl Cl CF₃ 01 i-Bu Br Cl Cl i-Bu Br

CH₃ H Cl Me Br Cl CF₃ Br Me Cl Cl Br Me Cl

CH₃ H Cl Et Br Cl CF₃ Br Et Cl Cl Br Et Cl

CH₃ H Cl i-Pr Br Cl CF₃ Br i-Pr Cl Cl Br i-Pr Cl

CH₃ H Cl i-Bu Br 01 CF₃ Br i-Bu Cl Cl Br i-Bu Cl

CH₃ H Br Me Cl 01 CF₃ Br Me Br Cl Br Me Br

CH₃ H Br Et Cl Cl CF₃ Br Et Br 01 Br Et Br

CH₃ H Br i-Pr Cl Cl CF₃ Br i-Pr Br 01 Br i-Pr Br

CH₃ H Br i-Bu Cl 01 CF3 Br i-Bu Br 01 Br i-Bu Br

CH₃ H Br Me Br Cl 01 01 n-Pr Cl H CF₃ Me Cl

CH₃ H Br Et Br Cl Cl Cl n-Bu 01 H CF₃ Et Cl

CH₃ H Br i-Pr Br Cl Cl Cl s-Bu Cl H CF₃ i-Pr Cl

CH₃ H Br i-Bu Br Cl 01 01 i-Bu Cl H CF₃ i-Bu Cl

Table 14

fi! R^4a E4b R7 R6 El R^4a R4b EZ E⁶.

Me 3-Me H CF₃ F Me 3-Cl H CF₃ F

Et 3-Me 5-Me OCF3 F Et 3-Cl 5-Me 0CF3 F

ffl ffl ffl Q ffl o ffl ffl ffl ro ffl ffl o ffl ffl T* ffl ffl ffl ffl ffl ffl Q ffl Q ffl ffl ffl to ffl ffl ό ffl ffl ω fc

^ω ffl ffl ro ω ω Cd ω Cd ω Cd Cd B? ω Cd EP 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 Q Ift ts>

5 ES cf § i 1rø OJ

Irø

O ό 6 6 ό ό ό ό ό ό ό ό o ό ό ό O ό ό ό ό ό ό ό O ό ό ό ό ό ό 1 p

ffl ffl ffl Ω ffl o ffl ffl ffl ro ι-t ffl ffl o ffl ffl to ffl ffl ffl ffl ffl ffi Ω ffl O ffi ffl ffl to ffl ffl ό ffl Ϊ ffi ro fc

E? Cd Cd BP EP Cd ^{κ ω ω} ^W ^W E? Cd Cd d W 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 Ω Ift

t-h k CD

W HM MM *^M _"^M ^^ MM ^^ MM HM MM *^ H^ MM MM ^μ*M *^ MM MM HH HM MM HM MM Hπ MM MM MM MM ^^ HM MM ^W . '^l ^^ MM r^^ l It*d ». fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc td ft i cy

<— • 51 .2 S S oo oo oo oo O O O O t -4 -J -4 -4 -J -4 -4 -J to to to to to to to to

0N 0Λ ^ 0N 0N 0 0N 0N σN 0N 0N 0N O\ 0Λ 0N σN 0 0Λ 0N 0N 0N σN σN 0N S N 0N σN σN 0N 0N 0N 0N OJ OJ OJ OJ JHH l l l l l l l t l l l l l l l l l l l l l l l l l l l l l l l l l l l l l JiΥ

Q Q Q Q Q D Q Q Q Q Q Q Q Q G Q Q Q Q Q Q Q Q Q Q Q Q Q Q Q Q Q Q Q Q Q Q l

Q n n n $ ^ $ h h h Sⁱ Sⁱ Sⁱ Sⁱ ^ ^ ^ ^ ^ ^ ^ ^ Q Ω Ω Ω Ω Ω Ω Ω n ^ Ω _t

% « ^ ^w^ ^ -% ^•% ^•«, j j? j S S 55 S S S 55 .a € s. s ^ ^ ? Ift to -4 — 4 — J -4 —J -J -4 -4 to to to to to to to to

•— rø rø rø rø rø rø rø rø rø rø rø rø rø rø rø rø rø rø rø rø rø rø rø rø rø rø rø rø rø rø ør rø W 11 W it W ⁱi W ⁱi | Irø O

R _R4a _R4b R7 R6 R3 _R4a _R4b R7 R6

Et 6-Me H OCHF₂ Cl Et 6-CI H OCHF2 Cl i-Pr 6-Me H OCHF₂ Cl i-Pr 6-CI H OCHF₂ Cl i-Bu 6-Me H OCHF₂ 01 i-Bu 6-CI H OCHF₂ Cl

Me 6-Me H SCHF₂ Cl Me 6-CI H SCHF₂ Cl

Et 6-Me H SCHF₂ Cl Et 6-CI H SCHF₂ Cl i-Pr 6-Me H SCHF₂ Cl i-Pr 6-CI H SCHF₂ 01 i-Bu 6-Me H SCHF₂ Cl i-Bu 6-CI H SCHF₂ Cl

Me 6-Me H OCF₃ Cl Me 6-CI H OCF3 Cl

Et 6-Me H OCF3 Cl Et 6-CI H OCF3 Cl i-Pr 6-Me H OCF3 Cl i-Pr 6-CI H OCF3 Cl i-Bu 6-Me H OCF3 01 i-Bu 6-CI H OCF3 01

Me 6-Me H SCF₃ Cl Me 6-CI H SCF3 01

Et 6-Me H SCF₃ Cl Et 6-CI H SCF3 Cl i-Pr 6-Me H SCF₃ 01 i-Pr 6-CI H SCF3 Cl i-Bu 6-Me H SCF₃ Cl i-Bu 6-CI H SCF₃ Cl

Me 6-Me H C₂F₅ Cl Me 6-CI H C₂F₅ Cl

Et 6-Me H C₂F₅ Cl Et 6-CI H C F₅ Cl i-Pr 6-Me H C F₅ Cl i-Pr 6-CI H C₂F₅ Cl t-Bu 6-Me H C₂F₅ Cl i-Bu 6-CI H C₂F₅ Cl

Me 6-Me H n-C₃F₇ Cl Me 6-01 H n-C₃F₇ Cl

Et 6-Me H n-C₃F₇ 01 Et 6-CI H n-C₃F₇ Cl i-Pr 6-Me H n-C₃F₇ Cl i-Pr 6-CI H n-C₃F₇ Cl i-Bu 6-Me H n-C₃F₇ Cl i-Bu 6-CI H n-C₃F₇ Cl

Me 6-Me H i-C₃F₇ Cl Me 6-CI H i-C₃F₇ Cl

Et 6-Me H i-C₃F₇ Cl Et 6-01 H i-C₃F₇ Cl i-Pr 6-Me H i-C₃F₇ Cl i-Pr 6-CI H i-C₃F₇ Cl i-Bu 6-Me H i-C₃F₇ Cl i-Bu 6-CI H i-C₃F₇ Cl

Me 6-Me H CN Cl Me 6-CI H CN Cl

Et 6-Me H CN Cl Et 6-01 H CN Cl i-Pr 6-Me H CN Cl i-Pr 6-CI H CN Cl i-Bu 6-Me H CN Cl i-Bu 6-CI H CN Cl

Me 6-Me H OCHF₂ Br Me 6-CI H OCHF₂ Br

Et 6-Me H OCHF₂ Br Et 6-CI H OCHF₂ Br i-Pr 6-Me H OCHF₂ Br i-Pr 6-CI H OCHF₂ Br i-Bu 6-Me H OCHF₂ Br i-Bu 6-CI H OCHF₂ Br

Me 6-Me H SCHF₂ Br Me 6-CI H SCHF₂ Br

Et 6-Me H SCHF₂ Br Et 6-CI H SCHF₂ Br

•5? W ώ j ES f ώ g ES f ώ E? W

3 ffl E? rø Cd

3 E? rø Cd rø

3 gD δ δ E "S f CD Ja røK ES _tfCD δ Jfj δ ι-r ft I ^J

ON ON ON ON ON ON ON ON ON ON ON ON ON V. Os Os Os Os Os OS Os Os Os Os Os fD CD Λ Ϊ Ϊ C^ CD O CD CB CD C O C CD Λ ls c^ rt fD O cϊ fD β CD O CD O Λ fD fD ϊ CD CD CD I ft p

p-l ^M HH W ffi ffi ffi ffi ffi W ffi Irø.

&

o o o oo oo oo oo O O O O v J-. ai ai a■

§ 88 O OJ OOJ OOJ ,9J OOJ OOJ O

TJ TI TI TJ hcj to8to8to8to8to8to8to to88838

t- 9o o9J O9J O9J O9J 9J O9J O9J iJ9o o9J O9J ffl¹-¹ ffl -¹ ffl^| ffl -* ffl ^ ffl -• -ffl¹ ffl "^, ffl -« ffl' ffl -• ffl -¹ ffl ^ w ^ "w* ffl Cd ^ro Cd

1 ro Cd Cd

1 ro Cd Cd ro 1 1 ft ON

VO

O Q Q O Q Q O O Q O O O O ft

ffi ffl ffl ffi ffi ffi ffi ffl ffi ffi ffi ffi ffi ffl ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffl ffi ffi ffi ffl ffi ffl ffl ffi ffi ffi ffi PL

O o_o ΓoN

TJ hrj TJ TJ TJ TJ TJ TJ rø TJ hcj ro cd cd cd cd cd cd cd ro ro ro cd ro ro rø ro ffl ffl ro ro cd ro cd ro ro ro ft

3 ro' δ Ht E ¹S- CD ∞ g- i E <^■* _if ffi or ø _T nfJ <t W^■*d dd or r o δ ES if or

3 e 3 EP ø

$ ør ϊ ES f r

3 Λ _jj T πfJ E «"S*^■ C gD Cd

3 E? rø ώ pg,

ON ON ON ON ON ft

O Clϊ Cι5 0 G> O CΪ D Cl> Ct lϊ CΪ Ct C^ O Ct CD C CD O Cl> O O CD Cl> C^ I 3

O O O O O O Q Q Q O O Q O O O O K ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffl ffi ft

00 00 00 _ --. _ oo oo oo oo O O O O -•. a a o³ o³ R 8 8 R 9 9 9 9 Ω Ω Ω Ω o o o o ^ < r- o 00 OO 00 O to n o

Tj TJ 9 TJ 3 TJ 3 hrj 3 Tj 3 Tj 3 % % % % % % % % * * * * '? ? _* * * OJ rj τι rø Tl o TJ o rø f rø ϊ r> o TJ Ui rø rø Ift to to to to to to to to -4

Tj hcj Mcj hcj hcj hcj hcj hcj hcj hcj hcj _^ hcj O hcj O Mcj Q Tj O hcj O Hij O Mcj O Tj O Tj Π hcj Q hcj Π hcj Π hcj O hcj O hcj O hcj O hcj O hcj _^ hcj o c hc 3j o u hcj π y hcj

OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ ft υ o δ g" δ t-f E •*S ^ « δ a δ ii E "S o^ ero δii ES ^D »ro δ HT E <ιS- i «f —ro rø i-t^' rø W W

3 ør H Cd

3 δ π E *^S i CfD gώ^* rø ^μ-f E "S^• i^D ώ ? δ ^μf E "S Oif cro. ft^{1 J}

Q Q O O Q Q n O O O O O O O Q Q Q O O I Ift p

8 O .5J5 OJ5 OJ. o8J55 "-"

TJ TJ TJ TJ TJ hcj hrj TJ hcj TJ TJ TJ hrj _^ hcj O hcj O O Hcj O hjj O Mcj O Mcj O Mcj O hcj O Tj O Tj O hcj Q hcj O hrj O hcj O hcj O hcj O hcj O hcj Q Tj Q hcj Q Tj

OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ ft

ro E? rø « ø Cd rø Cd rø Cd r rø or .

3 3 E? r

3 3 3 ø 3 rø S ø Cd δf ^rffl* aδ s 3δs δi^!--r! E^ iSffi 3 tδi δi ι-t E^S lffiM'¹ rø

O^ N σN σN ON O O σ^ ON ON O ON O σ^ o σN O^ σ σ^ σN O σN σ σN O^ o^ σ^ o o^ σN σN O ON

Cϊ O CD C^ C O O CΪ CD CΪ CD Ϊϊ Clϊ C O CΪ CD CΪ CΪ O CB cϊ CΪ CD D C CD

Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω rø rø rø rø rø rø rø rø rø rø rø rø rø rø rø rø ft u

C gD δ ø δ E i CfD δ p; δ i-f E ^rtS f CD

ft 1 °J

O ON O C^ OΛ ON Λ ON ON ^ σN O CJN ON CΛ O αN ON ON αN OΛ i-Λ ON αN ON OΛ C^

Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω lέ"

O O O O O O Q O O O O O O O Q O O O Q O O O O O O O O O O O O O O O O O o ft

rø-Ugt U'gl U'gl U'Si OδJ OδJ OδJ OaJ δJ OδJ O _ ^^ δJ OStolrø toirø toSrø toSrø tolrø tolrø r tlrø tolrøaaaarø rø rø øirø rø rø rø U -4 -4 -4 -4 -4 -J -4 -4'Sl U'Si'Ugl U'Sl ^ R.

Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω r^ø r^ø r^ø r^ø r^ø r^ø r^ø r^ø rø r^ø rø r^ø r^ø r^ø r^ø r^ø ft

r. t- IΛ t- ^1 o o o o o o o o o o to ffl ffl m ffl to to m ffl ffl ffl ffl ffl m q lff ffl m m flf ffl m r-. m ffl

fc r- r- r- fc fc r- fc r- t- r— CN CN CN CN cN cN cN CN fc fc fc fc fc fc fc fc fc [__, ___ , o co co co co o o in i i i i fc fc fc fc rf. ffl & a a a a a h h h ft ft

H ^ U o o G G G a a ft ft ^, ft, ^tf, ft co To co co 70 u u o o G CJ S K ft

% g g o o g g g g g g g g g g g g g g g g g g g g g g g g g g g g g g g g

3 I o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o

ϋl o o o o o o o o ffl q ffl ffl m m m ffl ffl ffl m m m ffl q ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl

tjo o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o

3 I

t-

3 3 3 3 3 3 3 s. a ft ffl ft fflo? ^ a ft o ffl? a _- ft. 3 ffl a ft ffl to ft ffl a ft ffl 2 a * ffl s a ft ffl ■J, o

δ E _tf δ δ ES f δ δ E ^ δ ES if δ δ ES if δ δ ES if δ δ ES if δ δ ES if δ δ ES if δ δ Irø.

k ffi kffi kffi ffik %ffi %ffi %ffi %ffi CD %ffi ffi ffik %ffi. kD CD %ffi %ffi %ffi ffik %CD kffi %ffi ffik %ffi CkD kffi %ffi ffi %ff ffk ffi fkfi %ffi CkD kffi kCD Ck •f- i i D P

O O O O O O Q O Q O O O O O O O O O O O O O O O O O Q O Q O Q O O Q O O O

\%

§ §

rø g δ rø ES f ør S if δ rø ES j δ rø E if TJ ES i δ ør W

^W ? rø w

3 rø rø Cd

3 5 Ift

ON ON ON ON ON ON ON ON ON ON ON ON ON ON ON ON O ON ON ON ON ON ON ON ON ON ON ON ON 0\ ON ON ON ON o o o O o O O O O O O o O O O o O O o o O o O o o O O O O O o ft

o o o O O O o O o O o O o O o O O o O O o O O o O o O o o o O O PS

ffl ffl lff ffl ffl ffl

R4a R EZ R6 I.! g4a R4b EZ R6 i-Bu 6-Me Cl CN CF₃ i-Bu 6-CI Cl CN CF₃

Table 15

R g4a R4b sZ R⁶. X R R4a R4b Z R6 X

Me 6-Me H OCHF₂ F CH Me 6-CI H OCHF₂ F CH

Et 6-Me H OCHF₂ F CH Et 6-CI H OCHF₂ F CH i-Pr 6-Me H OCHF₂ F CH i-Pr 6-CI H OCHF₂ F CH i-Bu 6-Me H OCHF₂ F CH i-Bu 6-CI H OCHF₂ F CH

Me 6-Me H SCHF₂ F CH Me 6-CI H SCHF₂ F CH

Et 6-Me H SCHF₂ F CH Et 6-01 H SCHF₂ F CH i-Pr 6-Me H SCHF₂ F CH i-Pr 6-CI H SCHF₂ F CH i-Bu 6-Me H SCHF₂ F CH i-Bu 6-CI H SCHF₂ F CH

Me 6-Me H OCF₃ F CH Me 6-CI H OCF3 F CH

Et 6-Me H OCF3 F CH Et 6-CI H OCF3 F CH i-Pr 6-Me H OCF3 F CH i-Pr 6-CI H OCF3 F CH i-Bu 6-Me H OCF3 F CH i-Bu 6-01 H OCF3 F CH

Me 6-Me H SCF₃ F CH Me 6-CI H SCF₃ F CH

Et 6-Me H SCF₃ F CH Et 6-CI H SCF3 F CH i-Pr 6-Me H SCF₃ F CH i-Pr 6-01 H SCF3 F CH i-Bu 6-Me H SCF3 F CH i-Bu 6-CI H SCF3 F CH

Me 6-Me H C₂F₅ F CH Me 6-CI H C₂F₅ F CH

Et 6-Me H C₂F₅ F CH Et 6-CI H C₂F₅ F CH i-Pr 6-Me H C₂F₅ F CH i-Pr 6-CI H C₂F₅ F CH i-Bu 6-Me H C₂F₅ F CH i-Bu 6-CI H C₂F₅ F CH

Me 6-Me H n-C₃F₇ F CH Me 6-CI H n-C₃F₇ F CH

Et 6-Me H n-C₃F₇ F CH Et 6-CI H n-C₃F₇ F CH i-Pr 6-Me H B-C3F7 F CH i-Pr 6-CI H n-C₃F₇ F CH

iffif δ δ i-r S " f CD cδ ft¹

k k k k k k k k k k k k k k k k k k k k k k k k k k k k k k k k k k k k k i ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi Irøj-;

! * o o o O O O O to to o i . J oo oo oo oo O O O O 8 g « S S S S 8 n O SO Oh OS O O O O

Tj TJ Tj Tj TJ TJ rø Tj Ui U $i _> _} 533555„a_?_. to5_.toBlJto _.to to to8toSto8 a a a a.s * ^■£ € § R

Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω rø rø rø rø rø rø rø rø rø ft

9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 ιx

Uθ

1.1 ^ δ δHi ffl" ffig ή røHi E^rtS fffi δ^ διι E"S fffi δiS røH E" iffi δrt δH E"S ifffi δ|S δHr E"S iffi δβ δHr E"S fffi δrt røHi E"S fffi δs2 røi-ι E Cg δ^ lι rø.

Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω lp

Irø

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9 ffl ffl9 ffi9 ffi9 ffl9 9ffl 9flf ffl9 9ffl 9ffl ffl9 9lff 9fc 9ffl 9fc 9ffl 9fc 9ffi 9ffl 9ffl 9ffl 9ffl 9ffl 9ffl 9ffl 9ffl 9ffl 9fc 9ffl 9fc 9ffl 9ffl 9ffl fl9f 9fc 9ffl 9fc ι

ώ g4a R4b E2 ≠ X R.. g4a R 9 R_. X

Et 6-Me Cl n-C₃F₇ Br CH Et 6-CI Cl n-C F₇ Br CH i-Pr 6-Me Cl n-C₃F₇ Br CH i-Pr 6-CI Cl n-C₃F₇ Br CH t-Bu 6-Me Cl n-C₃F₇ Br CH i-Bu 6-CI Cl n-C₃F₇ Br CH

Me 6-Me Cl i-C F₇ Br CH Me 6-CI Cl i-C₃F₇ Br CH

Et 6-Me Cl i-C₃F₇ Br CH Et 6-CI Cl i-C₃F₇ Br CH i-Pr 6-Me Cl i-C₃F₇ Br CH i-Pr 6-CI Cl i-C₃F₇ Br CH i-Bu 6-Me Cl i-C₃F₇ Br CH i-Bu 6-CI Cl Z-C3F7 Br CH

Me 6-Me Cl Et Br CH Me 6-CI Cl Et Br CH

Et 6-Me Cl Et Br CH Et 6-CI Cl Et Br CH i-Pr 6-Me Cl Et Br CH i-Pr 6-CI Cl Et Br CH t-Bu 6-Me Cl Et Br CH t-Bu 6-CI Cl Et Br CH

Me 6-Me Cl CHF₂ CF₃ CH Me 6-CI Cl CHF₂ CF₃ CH

Et 6-Me Cl CHF₂ CF₃ CH Et 6-CI Cl CHF₂ CF₃ CH i-Pr 6-Me Cl CHF₂ CF₃ CH i-Pr 6-CI Cl CHF₂ CF₃ CH t-Bu 6-Me Cl CHF₂ CF₃ CH t-Bu 6-CI Cl CHF₂ CF₃ CH

Me 6-Me Cl n-Pr CF₃ CH Me 6-CI Cl n-Pr CF₃ CH

Et 6-Me Cl n-Pr CF₃ CH Et 6-CI Cl n-Pr CF₃ CH i-Pr 6-Me Cl n-Pr CF₃ CH i-Pr 6-CI Cl n-Pr CF₃ CH i-Bu 6-Me Cl n-Pr CF₃ CH i-Bu 6-CI Cl n-Pr CF₃ CH

Me 6-Me Cl CF₃ CF₃ CH Me 6-CI Cl CF₃ CF₃ CH

Et 6-Me Cl CF₃ CF₃ CH Et 6-CI Cl CF₃ CF₃ CH i-Pr 6-Me Cl CF₃ CF₃ CH i-Pr 6-CI Cl CF₃ CF₃ CH i-Bu 6-Me Cl CF₃ CF₃ CH i-Bu 6-CI Cl CF₃ CF₃ CH

Me 6-Me Cl i-Pr CF₃ CH Me 6-CI Cl i-Pr CF₃ CH

Et 6-Me Cl i-Pr CF₃ CH Et 6-CI Cl z-Pr CF₃ CH i-Pr 6-Me Cl i-Pr CF₃ CH i-Pr 6-CI Cl i-Pr CF₃ CH t-Bu 6-Me Cl i-Pr CF₃ CH t-Bu 6-CI Cl i-Pr CF₃ CH

Me 6-Me Cl C₂F₅ CF₃ CH Me 6-CI Cl C₂F₅ CF₃ CH

Et 6-Me Cl C₂F₅ CF₃ CH Et 6-CI Cl C₂F₅ CF₃ CH i-Pr 6-Me Cl C₂F₅ CF₃ CH i-Pr 6-CI Cl C₂F₅ CF₃ CH t-Bu 6-Me Cl C_{2 5} CF₃ CH i-Bu 6-CI Cl C₂F₅ CF₃ CH

Me 6-Me Cl n-C₃F₇ CF₃ CH Me 6-CI Cl n-C₃F₇ CF₃ CH

Et 6-Me Cl n-C₃F₇ CF₃ CH Et 6-CI Cl n-C₃F₇ CF₃ CH i-Pr 6-Me Cl n-C₃F₇ CF₃ CH i-Pr 6-CI Cl n-C₃F₇ CF₃ CH t-Bu 6-Me Cl n-C₃F₇ CF₃ CH i-Bu 6-CI Cl n-C₃F₇ CF₃ CH

Me 6-Me Cl i-C₃F₇ CF₃ CH Me 6-CI Cl i-C₃F₇ CF₃ CH

Et 6-Me Cl i-C₃F₇ CF₃ CH Et 6-CI Cl i-C₃F₇ CF₃ CH ES 2 ώ ES 2 ώ ES 2 ro

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ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi Ω Ω Ω Ω Ω Ω \

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hrj hcj TJ TJ TJ Tj TJ TJ Tj TJ TJ Tj TJ Tj hcJ Tj Tj TJ Tj TJ TJ TJ TJ TJ TJ rø Tj TJ TJ TJ TJ TJ TJ Tj TJ TJ OJ OJ OJ OJ OJ OJ I Ift Os

hrj hj Hj Hj hrj hcj Mcj Tj hcj Mcj Tj Hrj Hjj Mcj Hjrt Hrj Hj Hrj HH Mcj Q hcj Q hcj Tj O hcj O hcj Q rø 99 a 888 88 i* o δ ► E^S ^D δ ∑3 δ E ^rtS t CD δ -i δ >1 ES _t CD δi δ i-r E^S iClD øδ δ ML ES CD ø tJd δ Ht E "S 2 ffi ø w Hf E ^rtS t ffi ro ø E t øώ Hi E^ ^ffi δ lft o*. Os Os O Os Os Os Os Os Os Os Os Os Os Os

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^ι ^« g e § g fc fc fc fc f s ε. ε. u U U ft ft ft CN CN

CJ J O CJ o o υ O o ^ft W W W

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o o o O o o o υ υ o o o o o o o O υ o O O O o o o o vo VO o VO VO O VO VO VO o v vo VO VO o o vo vo vo vo vo ό vό

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Table 18

R9 is CHF₂ R⁹ is CH CF₃ R⁹ is CFoCHFτ

R3 _R4a _R4b R6 R3 _R4a _R4b R6 R3 _R4a _R4b R6

Me CH₃ H Cl Me CH₃ H Cl Me CH₃ H Cl

Et CH₃ H Cl Et CH₃ H Cl Et CH₃ H Cl i-Pr CH₃ H Cl i-Pr CH₃ H Cl i-Pr CH₃ H Cl i-Bu CH₃ H Cl i-Bu CH₃ H Cl t-Bu CH₃ H Cl

Me CH₃ H Br Me CH₃ H Br Me CH₃ H Br

Et CH₃ H Br Et CH₃ H Br Et CH₃ H Br i-Pr CH₃ H Br i-Pr CH₃ H Br i-Pr CH₃ H Br t-Bu CH₃ H Br i-Bu CH₃ H Br i-Bu CH₃ H Br

Me CH₃ F Cl Me CH₃ F Cl Me CH₃ F Cl

Et CH₃ F Cl Et CH₃ F Cl Et CH₃ F Cl i-Pr CH₃ F Cl i-Pr CH₃ F Cl i-Pr CH₃ F Cl i-Bu CH₃ F Cl t-Bu CH₃ F Cl i-Bu CH₃ F Cl

Me CH₃ F Br Me CH₃ F Br Me CH₃ F Br

Et CH₃ F Br Et CH₃ F Br Et CH₃ F Br i-Pr CH₃ F Br i-Pr CH₃ F Br i-Pr CH₃ F Br i-Bu CH₃ F Br i-Bu CH₃ F Br i-Bu CH₃ F Br

Me CH₃ Cl Cl Me CH₃ Cl Cl Me CH₃ Cl Cl

Et CH₃ Cl Cl Et CH₃ Cl Cl Et CH₃ Cl Cl i-Pr CH₃ Cl Cl i-Pr CH₃ Cl Cl i-Pr CH₃ Cl Cl i-Bu CH₃ Cl Cl i-Bu CH₃ Cl Cl t-Bu CH₃ Cl Cl

Me CH₃ Cl Br Me CH₃ Cl Br Me CH₃ Cl Br

Et CH₃ Cl Br Et CH₃ Cl Br Et CH₃ Cl Br i-Pr CH₃ Cl Br i-Pr CH₃ Cl Br i-Pr CH₃ Cl Br i-Bu CH₃ Cl Br i-Bu CH₃ Cl Br i-Bu CH₃ Cl Br

Me CH₃ Br Cl Me CH₃ Br Cl Me CH₃ Br Cl

Et CH₃ Br Cl Et CH₃ Br Cl Et CH₃ Br

Cl

3 3 fc 5 a a ft 5 a 3 3 3 3 ft 3 1 a ft 3 1 a ft 3 a ft 3 a 3 ft PQ a ft s a 3 ft 3

3 3 3 3

^Cλ.1 ft 3 1 a 5 3 a 5 a 3 ft ffl

— - 1 a ft 3 a ft •— - 3 1 a 3 ft PQ a s 3 3 a 3 ft 3 3

c G G m to ffl ffl G G G G ffl ffl ffl ffl G G G G ffl m m ffl o o o o o o o to to to ffl G

δ δ δ 8 δ 8 fc δ 8 fc o G G G fc fc fc fc fc fc ft ft G

3 ffl 8 3 ffl 8 3 3 3 3 5 ffl 8 8 ffl 5 5 5 o o o o o υ o o o

3 3 3 3 3 3

fi 3 a 3

§ p w 5 ffl fc ε. *P 3 a s 3 a 3

5 3

E ^H* 2iffi δ cl ^ C2D δ y ι_C E "S* [ ffi p 3δj T ES i? πT E^rtS iC?D pj E ¹S- i ffi δ £ 32 δ 1 rø Cd ι 3 w 3 w W

3 ^|-ι 0 w rø 5 ft

ro ω o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o lft I ¹rø vo

Ω

T hCJ Hτj Hj HJ M^ Hι Hτ Hc H-j OJ OJ OJ OJ OJ OJ OJ OJ ffl ffl ffl ffl ffl ffl ffl ffl ffi ffi ffi ffi ffi _ffi _ffi _ffi o o Irø.

Ito

o o o o o Q ^{ffl W ffl W} Q O o o w ω ω ω o Q Ω Ω w ro ro w o o o o ro 1 ro1 ro1 ro1 o o Irø

45-

O O O Q Q W ffl W ffl Q Q Q Q ffl ffl ffl ffl Q O Q ffl ffl ffl W O Q O Q ffl W ffl ffl Q O |rd

_ rø <+ 2 G δ ø δ ES i2 CD δ ø δ E "S^{^} i? CD δ ø δ ES i CD δ ø δ ES i CD δ p) δ I-T E "^S i CD δ pj δ E "S+ i ffi δ ø δ ES Ci?D δ _j δ i-f E "S+ t ffi δ ?! δ i-t ft '

Ω Ω H? H? H? H? Ω Ω Ω Ω H? H? H? H? Ω Ω Ω Ω Ω Ω Ω Ω H? H? H? H? Ω Ω Ω Ω 5^, 5^, 5^, H? Ω Ω ft

3 3 c^" l ft ffl W ffl a ft ffl 3 3 ffl w ft ffl w ft .3 o 3 w ft ffl .-T fc 3

W ffl

1-.I G G li li li pq ffl m m G G G G ffl ffl ffl (-3 G G G G m m m m G G G G ffl ffl ffl ffl

fc fc fc fc fc G G G G G G G G m m m m M ffl M ffl

_f ffl f ffl _{ffl ffl ffl ffl ffl ffl ffl} ffl ffl l

« _fl ffl ffl fl ff _ffl ffl _{ffl ffl ffl ffl ffl} ffl _{ffl flf ffl ffl} ffl

^| G G ι_3 m m m G G G G m ι-3 m m G G G G m m ^ m G G G G m m m m

fc fc fc fc fc fc G G G G G G G G m m m m m m M M

m m m ffl ffl ffl ffl ffl m m ffl ffl m ffl ffl m m ffl m m ffl m m m ffl m ffl m m ffl

ft J_JHM 3 '-a' to a -π* * _fti"< 5ffl "-r _to! .a*-H.j *ft-j 5ffl ^,_r -|to! a«-___. ^ft_iM ^ffl '-* 3 to a _■__ ft fc ffl i-* _ toB a - .T.__ ft fc *-. ^p ^? 3 _ ω_i a * ,ι_.- ft rfc *-< ^p r?r 3 _to3 a .-T ^f & rg

Table 19

R⁹ is CHF₂ R⁹ is CHoCF₃ R⁹ is CFoCHF

R R4a R4b Rθ Sf! g4a R4b ≠ R R4a R4 R-!

Me CH₃ H Cl Me CH₃ H Cl Me CH₃ H Cl

Et CH₃ H Cl Et CH₃ H Cl Et CH₃ H Cl i-Pr CH₃ H Cl i-Pr CH₃ H Cl i-Pr CH₃ H Cl i-Bu CH₃ H Cl t-Bu CH₃ H Cl i-Bu CH₃ H Cl

Me CH₃ H Br Me CH₃ H Br Me CH₃ H Br

Et CH₃ H Br Et CH₃ H Br Et CH₃ H Br i-Pr CH₃ H Br i-Pr CH₃ H Br i-Pr CH₃ H Br i-Bu CH₃ H Br t-Bu CH₃ H Br t-Bu CH₃ H Br

Me CH₃ F Cl Me CH₃ F Cl Me CH₃ F Cl

Et CH₃ F Cl Et CH₃ F Cl Et CH₃ F Cl i-Pr CH₃ F Cl i-Pr CH₃ F Cl i-Pr CH₃ F Cl i-Bu CH₃ F Cl i-Bu CH₃ F Cl i-Bu CH₃ F Cl

Me CH₃ F Br Me CH₃ F Br Me CH₃ F Br

Et CH₃ F Br Et CH₃ F Br Et CH₃ F Br i-Pr CH₃ F Br i-Pr CH₃ F Br i-Pr CH₃ F Br i-Bu CH₃ F Br i-Bu CH₃ F Br t-Bu CH₃ F Br

Me CH₃ Cl Cl Me CH₃ Cl Cl Me CH₃ Cl Cl

Et CH₃ Cl Cl Et CH₃ Cl Cl Et CH₃ Cl Cl i-Pr CH₃ Cl Cl i-Pr CH₃ Cl Cl i-Pr CH₃ Cl Cl t-Bu CH₃ Cl Cl t-Bu CH₃ Cl Cl t-Bu CH₃ Cl Cl

Me CH₃ Cl Br Me CH₃ Cl Br Me CH₃ Cl Br

Et CH₃ Cl Br Et CH₃ Cl Br Et CH₃ Cl Br i-Pr CH₃ Cl Br i-Pr CH₃ Cl Br i-Pr CH₃ Cl Br i-Bu CH₃ Cl Br t-Bu CH₃ Cl Br t-Bu CH₃ Cl Br

Me CH₃ Br Cl Me CH₃ Br Cl Me CH₃ Br Cl

Et CH₃ Br Cl Et CH₃ Br Cl Et CH₃ Br Cl i-Pr CH₃ Br Cl i-Pr CH₃ Br Cl i-Pr CH₃

Br Cl to to to to G G

G G G G G G

3 3 ffl 3 a 3 3

5 3 3 a 3 ft 3 3 a 3

5 3 3 a ft s 3 a 5 3 3 to 5 3 3 a s 5 3 a s 4 3 a

4 G ffl ffl to to G G G G ffl ffl ffl to G G G G ffl ffl m ffl ffl ffl ffl ffl G G G G ffl to ffl ffl G G

3 3 3 3 3 3 3

3 3 a ft •-— 3 3 a 3

5 3 3 a $ 3 3 a ft 3 3 a ft 3 3 a ft 3 3 a 5 3 3 a 3 ft 3 3 a

G ffl to ffl^* ffl G G G ffl ffl Q ffl G G G G to to ffl to G G G G to ffl to ffl G G G G G c oo δ G f in ffi fl i ffi ffi ffi ffl ffl ffl to fc f fc o δ δ 8 fc δ c o δ G G G G fc fc 5 in fl f ff

3 | i G G G o G G G σ G G G G G G G G G G G G G G o G G G G G G G G G G ffl to

3 3 3 3 3 3

14 3 3 a ft — - 3 3 a δ 3 3 a 5 3 3 a ft p 3 a ft 3 3

3 3 W $ 3 3 a 3

5 fc 3

3 R pp 3 to

PHI G ffl m ffl ffl G G G G to m ffl ffl G G G G m to m m G o G ffl PQ ffl ffl G G G G G G

Cd rø W Cd r

3 3 5 w ES s T? ø

3 t? w Cd

3 3 δ T CD δ δ *% ES _. tfD δ c δ ES l f

3 3i Ti-r ^ ffi_? δi δ 1 ES 2D J-j tl^O

ro cd cd cd cd cd cd ffl ffl cd cd cd ro ro ro ro ro cd ro ω ro ro ro ro ro ro ffl W ffl

_? S? _? !_? !-? _? _P S^:, Ω Ω Ω Ω Ω Ω Ω Ω rø TJ Tj

ffl ffl ffl W O O O O W Cd W W O O O O W W W W O O O O ffl W W W O lrø

₀ ro δr E ^rtS i ffi< Cd rø Cd

3 EP 3 E? rø ø

3 ω E? W

3 ω Ei? r ^κ rø W Cd

3 E? W ro

3 Irø.

3 T 3 H 3 n 3 "

ro ffl ro ro ro ro ro ffl ffl c rø vo

1 1 1 ro1 1 1 ro1 1 1 ro1 ro1 ro1 1ro 1 1 ffl1 ffl1 1d ro1 ro1 1ro c1d ro1 ro1 ro1 c1d c1d 1ro ro1 p|^- o ffl 1 HH H HH HH HH HH HH HH Cd ω W ω ro ro W ro Q O O O Q O O Tj hH hrJ TJ h^ vo

w ω ω ro o o o Q ω ω ω ω o o o o ro ro ro ω o o o Q ro ro w ffl o |rø

3 H 3 'I

9 Ω Ω Ω ^{w w ω w} 5^{) W w ω} Ω Ω Ω Ω ^{ω w ω ω} Ω Ω Ω Ω 5^J S^j S³ 5^, Ω lft

rø 2 CD δ ø δ E ^S 2 CD δ ø δ Hi E -S+ 2 ffi δ a" δ i-f E -S+ ffi2 δ cj δ H| E ^rtS _i? CD δ Jr δ i-f E -S+ _t ffi? δ ø δ Hi W Irø

3 •"*

^■9 fc Ωfc Ωfc 9fc 9fc 9fc 9fc 9fc 9fc 9fc 9fc Ωfc Ωfc 9fc 9fc 9fc 9fc 9fc 9fc 9fc 9fc 9fc 9fc 9fc 9fc 9fc

ffl W Q O O O Q Q O O Tj Tj Tj TJ Tj TJ TJ TJ ffi ffi ffi ffi ffi ffi ffi ffi

Q Q ^ ^ Q Q Q Q ^ ^ Q Q Q Q SP ff S ^ffl Ω Ω Ω Ω ft ON

Ω Ω -? ^{w ω κ} Ω Ω Ω Ω ^{w κ} -? -? Ω Ω Ω Ω ^w -? H? Ω Ω Ω Ω ft

t ^rts 2ffi ώ H^ E^S iffi ro 0 1 E "S 2ffi m 0 ώ ώ St _rø >-, ro 0 ES 2 0_ro δ l ES 2 ro ES 2^ E3 2ff Hώ ES 2 ro ;ς w

3 T_| " ffi 0 H^ ^l- ffi pj Ht ^ i 3 i Tf ^Λ (( S if ' «

ω 1 ω 1 O Ω Ω ff !-r !-rⁱ 9 9 Ω Ω ^ω H? H7^t H? Ω Ω Ω Ω H? H? H? H? Ω Ω Ω Ω H? H? H? H? Ω Ω ft

O O O O Ω Ω Ω Ω O Ω Ω Ω Ω Ω OaJ OaJ OaJ OaJ OaJ OaJ OaJ OaJ OaJ OaJ OaJ OaJ OaJ OaJ OaJ OaJ OaJ OaJ OaJ OaJ OaJ OaJ i Ift Irø

9

Ω Ω Ω Ω Ω Ω ffi ffi ffi ffi ffi ffi ffi ffi Iffi

O9J O9J O9J O9J O9J O9J O9J O9J O H- O H- O H- O H- O I— O 1— I Ift _jy' |feJ

Ω Ω ^ -? ^ H? Ω Ω Ω Ω H H? H? H? HV H? H? Hy Ω Ω Ω Ω H? H H? H? Ω Ω Ω Ω H H H H Ω Ω ft

E π÷ i2ffi δ a" E "S+ ffi δ ø δ Hf E ¹S- ffi δ pi δ HI E ^rt ^ CD δ -_j Hr E-S^H- iffi δ » if "E i2 β δ p_j Ht E <-S* ^ ffi Z_j i-T E -* ffi! δ - 3T ^ E ^rtS i ffi δ _ 3; 'l ft I OJ

Ω H? H? H H Ω Ω Ω Ω H ^ffl H? H? H H? ^ffl _? Ω Ω Ω Ω -? H H? t Ω Ω Ω Ω H? ^{ffl W} Hf Ω Ω lft

w ro ij δl-r E-S^H- ^CD firo τlJ' E¹S- ffi2 aώ" % if s "+ ffi gώ' nT E^S iC? gro' Hr E-S^H- ffi ώ I ^ 1^{U rt}w tH _fflT % Hf -+ 2 ffi ώ g" H^ E 1- ^ ffi ro δ ft

H? E? Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω ft rø

_0 vo

Ω

W C T 1d J

1 ^J rø ^Tj Ti Ω Ω Ω rø rø rø rø w 1 ffl ffl1 ffl1 ffl ffl Cd

1 ffl1 1 1 1 Tj Tj rø rø TJ Tj rø TJ

OJ OJ OJ OJ OJ OJ OJ OJ ffi ffi ffi ffl ffl ffl PL

o o μ— i o o H-* o μ—t o h—t o o i o H-* o H-* ro ro μ-{ ω ω o o o o ω μ-t ω μ-t ω ^t ω Η o μ—t o μ— - o μ— ι o ω μ-t ω H ω μ-t ro μ-t o μ— ι o μ-^ o μ— ι o μ—t ω ω μ-t i I C OJN

rø c &o 0 dd 0 Cd Cd rø rø-ι^' E "S* t fif? p r

3 ι 3 ω ι ro; πT ^rtES C2D £ό^ ^rtES i fl)_' £ώ δ ii E ^rt i CD_' ro ₄ ^U E ^rtS (it_' ro 1-1 W W w

3 EP o

3 to ft

W ro o θ O O O Q Q O O Q Q Q O O O O O Q O O O O O O O O O O O θ |ft jrø

VO

Iffl po τi h^H θ o o o 9 9 9 9 9 9 9 t

H ι? Hι? Hι? Sι⁾ rø rø rø rø rø rø rø rø Ω ^ Ω^ Iftσ'fej

^v^ ^{θ Q} Ω Ω ^{κ ω w w} Ω Ω Ω Ω ^{κ ω ω ω} Ω Ω Ω Ω ^{w w ω ffl} Ω Ω Ω Ω ^{ffl ffl ffl ffl} Ω Ω lft

E 1S- iffi δ g' if E "S^H" i ffi δ HI E <^■S* ffii δ 1 If E ^rtS i tH δ rt if E ^rtS 2 (I δ if ^ 11 ^ ^Λ (2I δ _j δ Hf E "* ffii δ pj i E ^rtS ^ ffi δ g" δ Hf E ^C5* ^ ffi Zj | ft I OJ

cd cd cd w cd w w ffl ω ω o o o o o o o o o o o o o o o o o o o o o o o o o o lft

Q- Ω >— rø rø rø rø rø rø rø rø OQJ OQJ O9J OQJ OQJ OJ O9J O9J ffl ffl ffl ffi ffi ffi ffl ffi rø rø rø rø rø rø rø rø ι-i '-ι | Ift α*

Ω Ω HF H ^{ffl ffl} Ω Ω Ω Ω Ω Ω Ω Ω H^ ^ffl ^ ^ffl Ω Ω Ω Ω Hf ^{ffl ffl} ^ Ω Ω Ω Ω ∞ ∞ ^ ∞ Ω Ω lft

ffl δ ES s? δ δ ES i? δ δ ES _.? δ δ ES 2 δ δ ES 2 δ δ ES 2 δ δ ES ; δ ft

ffl ffl cd ffl cd ffl ffl ffl ffl cd cd ro ro ffl cd ffl ffl ffl ro cd cd cd ro ro ro ro ro ro ro ro Ift rø

1

O O O O O O O O TJ TJ TJ TJ TJ TJ TJ TJ ro ro ro ro ffl ffl PL .^■--

W 1 1Cd C1d Cld Ofc Ofc O^ Ofc Wl C1d C1d Cld Ofc Ofc Ofc Ofc Cld C1d C1d ffll Ofc Ofc OH OHⁱ C1d C1d W W OHⁱ Oi--- l|røO.

Cd E? rø _? s? rø Cd rø ES 3 ω rø rø ffl EP rø Cd δ ES 2 δ δ ES _|2 δ δ |!

3 3 T 3 ι ft

Cd Cd Cd ffl ffl Cd Cd Cd Cd Cd ϋd Cd Cd Cd Cd ffl Cd Cd ffl ffl ffl ffl Cd

cd ro ro ro ro w ro w Ω Ω Ω Ω Ω Ω Ω

5^{3 ffl ffl ffl} Ω Ω Ω Ω ^{ω ω ω ω} Ω Ω Ω Ω ^{w ω ω ω} Ω Ω Ω Ω ^{ω ω ω ω} Ω Ω ft

ro ro ro ro ro ro ro ro ro ro ro ro or ro cd ro ro ro ro ro ro ro ro ro ro ro ro ro ro ro | Ift 3

9 9 9 9 9 9 .9 .9 » ffl ffl W « W W « Ω Ω Ω Ω Ω Ω fe

^{ffl ffl ffl ffl} Ω Ω Ω Ω ^{w ω ω ω} Ω Ω Ω Ω ^{ω ω ω} 5^:l Ω Ω Ω Ω ^{w w w w} Ω Ω ft

a a a a a O 8J a 8 a O aJ 8 a a a a a 8 a a a 8 8 a a a 8 a

ro ω ω O O o o o O O O rø rø Tj TJ TJ

1 rø TJ rø ffl ffi ffi ffi ffi ffi ffi ffi

O O O ro Cd Cd ro Q O O O ro ro Cd ffl O O O O ffl ffl ffl H? Q Ω Ω O ft

Cd Cd ϊ? O Ω O o Cd SF W ω O Ω O Ω ffl « ffl Q Ω O O t? ro Cd Cd o Ω o Ω ro Cd Cd Cd O ft

to ES cf δ 3 to ES δ 3 5 ES cf δ 3 5 ES cf δ 3 5 ES f c δ 3 to ES δ 3 5 ES cf δ 3 to ES 1 δ 3 5 ES δ 3 ft

o Q Q Cd Cd r

H? ro Ω Ω O w o or Cd Cd ω ffl w Ω O Q O Cd Cd Cd Cd Q o Cd Cd Cd ^W O ft

Ω O H? ω ω H? o o o ω W W εp ffl ω w ffl o Ω o o H? ^ω ω ffl Q O ω w w 2 O ft

G G G G G m ffl m m o o

g fc fc fc fc fc fc fc fc O

o m ffl ffl ffl ffl ffl ffl ffl PQ ffl

3 ^wd j 2 a H 3 a 5 ffl a ft ^p ft % J ¹ ^ ω a -H- 3 3 3 3 ffl ft ffl S w ft ffl 3 w ft ffl w

pi| f-. m m m o o o o ffl m m fδ G G G G ffl ffl ffl to 0 0 0 ϋ to to to to U 0 a U co co co co co co co co _ _ __ι _

V_O S l G ft ft ft ft ft ft ft ft ffl ffl ffl ffl

OO ffil δ δ δ δ δ s δ 5 ^{u u υ ϋ h h} υ

3 I __ -_ -_ _rt

PHI ^•^^■.i G G G G G G G G G G G G G G G G G G G G G G G G G G G G G G G G G m m

ffl l

^i H^ G G G H^ m m S G G G G m m m m G G G G m ffl m m G G G G G G G G G G

SI ^| ffi ffi ffi ffi ffi ^ g ^ g g g g g r3 ^ ^ rg s m ffl ffl ft ft ft ft G o ft ft ft ft ffl ffl t- cό

PHI fcl O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O ffl ffl

o ^ ^ffl _ra ft ^ffl ^ a ft c? ^ a ft ^ffl a ft ^ffl 3 s ^ ^ ^ ^fe ^ s ^ ^P s ^ ^p? 3 s

3 3 ftl 3 3 to s 3

3 3 a 3 ft PQ 3 a s 3

3 3 a 3

5 3 3 a ft 3 3 a 3

5 3 3 a s 3

3

3 3 3 3 3 3 3 3 °JI 3 3 to 5 3 3 a ft pp 3 a 5 3 3 a ft pp 3 to 5 ffl t

— - 3 a f 3 3 to ft p

fc fc fc fc fc o o o o o o o o

ffl ffl m ffl ffl ffl ffl m ffl ffl ffl ffl m

3 3 3 3

3 3 a 5 3 3 a s 3 3 a s 3

Table 22

R⁹ is CHF₂ R⁹ is CH CF R⁹ is CF CHF

R _R4a _R4b R6 R3 _R4a _R4b R6 R _R4a _R4b R6

Me CH₃ H Cl Me CH₃ H Cl Me CH₃ H Cl

Et CH₃ H Cl Et CH₃ H Cl Et CH₃ H Cl i-Pr CH₃ H Cl i-Pr CH₃ H Cl i-Pr CH₃ H Cl t-Bu CH₃ H Cl i-Bu CH₃ H Cl i-Bu CH₃ H Cl

Me CH₃ H Br Me CH₃ H Br Me CH₃ H Br

Me CH₃ F Cl Me, CH₃ F Cl Me CH₃ F Cl

Et CH₃ F Cl Et CH₃ F Cl Et CH₃ F Cl i-Pr CH₃ F Cl i-Pr CH₃ F Cl i-Pr CH₃ F Cl t-Bu CH₃ F Cl t-Bu CH₃ F Cl t-Bu CH₃ F Cl

Me CH₃ F Br Me CH₃ F Br Me CH₃ F Br

Et CH₃ F Br Et CH₃ F Br Et CH₃ F Br i-Pr CH₃ F Br i-Pr CH₃ F Br i-Pr CH₃ F Br t-Bu CH₃ F Br i-Bu CH₃ F Br i-Bu CH₃ F Br

Me CH₃ Cl Cl Me CH₃ Cl Cl Me CH₃ Cl Cl

Et CH₃ Cl Cl Et CH₃ Cl Cl Et CH₃ Cl Cl i-Pr CH₃ Cl Cl i-Pr CH₃ Cl Cl i-Pr CH₃ Cl Cl t-Bu CH₃ Cl Cl t-Bu CH₃ Cl Cl i-Bu CH₃ Cl Cl

Me CH₃ Cl Br Me CH₃ Cl Br Me CH₃ Cl Br

Et CH₃ Cl Br Et CH₃ Cl Br Et CH₃ Cl Br i-Pr CH₃ Cl Br i-Pr CH₃ Cl Br i-Pr CH₃ Cl Br t-Bu CH₃ Cl Br i-Bu CH₃ Cl Br i-Bu CH₃ Cl Br

Me CH₃ Br Cl Me CH₃ Br Cl Me CH₃ Br Cl

Et CH₃ Br Cl Et CH₃ Br Cl Et CH₃ Br

Cl ^1 l Si l

G G ffl to m m G G G G ffl m m i-I G G G G m m ^ m rø ffl ffl ffl G G G G m to to to U

.CNI ffl co co co co

5 f m m flf fc fc i ffi ffi ffi ffi ffi ffi _^ffi

H % m m fl fc fc fcco fcco fcco fcco ff

O O O O O O O J CNI ft a 3 I

PHI 14 3335533553333335533533 ^{O O O O O O O O O U O} o

3 3 3 3 4 ft 3 ffl 3 w ft ffl w ft A ffl -A w ft 4 a ft ffl S ^ft ft ffl w ft ffl p £ ^pf ft ; a ft ffl ^

P4 O ffl ffl ffl m G G G G rø m pq m o o o o m m m ffl ffl ffl to to G G G G m ll H, m m m G

^i G m m m iS G G G G m m m m G G G G m m m m G G G G o G o G m w m fS o

co co co co co co co co _, -_- _-, -_. ffl f | fL_j fl_j ^ [l_j |l₍ J ^* 3 ^*

SI 14 ffl ffl ffl ffl ffl ^ [l_j o o o o o o o fc fc fc fc fc fc fc fc ςj

t- 3 I .co co co co co co co co co co o co

Pi\ 14 δ S S^' B^' S^' 5^' B^' 5^' S 5^' S^' B^' 5^' 5 if δ^" B B^" δ if δ if S if if i ^{D ϋ ϋ ϋ ϋ a ϋ ϋ ϋ} o l\ ft^, m5 tD aii ft_H ^p3ρ (u a^ ft< ^pρ (u a^ ftj- ^p_5p o aii ft< fflJ-_ aj aii ftJH ffl^ ftJr^< j^p3?_. ffl5 ^'p³ M ft ^pp ^ ft 3

IΛ t- ^i G G m m m a G G G G ffl m m pH G G G G G G G G ^ a m m G G G G m m m ffl

CNI ffl

H cf fc fc fc fc fc fc CJ ^ll δ δ δ δ δ δ δ δ ^ fc fc fc fc fc fc fc r_j ft ft[ tl G G G o G o G m

14 ^σ o o o o o o o o o o o o o o o o o m ffl S fi m m ffl fi m

3 3 3 3 3 ii 3

14 tf ffl w ft ffl ffl ft 3 ) 3 ^ffl 3 ffl ft ffl S to ft ω -u A ffl ffl ft ffl a ft ffl W ft ffl ^ a ft* m 3 5 <->

^i G G m m _{ffl ffl} G G G G m' m _ffl & G G G G & m m m G G G G _ffl m m p-i G G G G G

fcl -S -H -H _Hi _Hi _Hi _Hi _Hi _Hi _Hi ii li li l_H li CO CO CO CO CO CO CO CO _ _i _i ___< o ol ^| o o ffl ffl ffl ffl lff ffl ffl ffl m ffl m ffl ι-^{| M} ι-^| >--^| ι-ι ι-ι « « ft ft ft ft ft

CN ffll

3 I ___{< ι [}

PHI ^"^ G o G G G G G o o G G o G G G G G G o o G o G G G G G G G G G G G G ffl

SI J^H ! a ϊ ξ. 3 H & a _** ξ Jr. ^ 3 ! & δ _*÷ ^ f. H 3 & a I a I s I s ^ Ή 3³ _ΛHI 3 3 3^s I

^i o m m ffl ffl G G G G m m ffl ffl G m ffl m ffl G G m m ffl a G

δ ør

3 ES δ 3 ES c δ 3 5 ES cf δ 3 to ES cf δ 3 to ES cf Cd

3 ES cf 3 δ to ES cf 3 δ to Ift

Cd ffl ffl Cd O O O Q Cd Cd Cd s? O O O O Cd ro ro ro Q O o Cd ffl Cd Cd O Ift

Cd

3 ϊ ES cf 3 δ 5 ES 3 δ 5 ES c ffi S

3 δ 5 ES cf ffli

3 5 ES cf 3 δ 5 ES 3 δ δ ES cf 3 δ to Ift

ffl Cd Cd

ffl Cd ffl ffl o O Ω ffl « ffl HS o Ω ω ffl Ω 9 Q Q ^ω ffl ffl ffl ft 1 Os

ro

3 s ES cf δ 3 HP ES c 1 5 ES δ 3 to ES δ 3 5 ES δ 3 5 ES cf δ 3 to ES cf δ 3 5 Ift

EP w Cd 0__ E W lff

3 E? ffl CD w δ ES 2 CD pwj Ht w " f2fi ι 3 EP W

3 ffl EP W

a a Ω ffi Ω ffi Ω ffl Ω ffl Ω ffl Ω ffl Ω ffl Ω ffl Ω ffl Ω flf Ω ffl Ω Ω fc Ωfc Ωfc Ωfc Ωfc Ωfc Ωfc Ωfc Ωfc Ωfc Ωfc Ωfc Ωfc

ffl ffl flf O O O O O O O O Tj Tj Tj Tj Tj rø rø ffi ffi ffi ffi ffi ffi ffi ffi

Ω Ω Ω S? S? E? E? o o o o w 1 ro w1 ro1 o*-= o o o w ω w ro o o o o PL ON

O o w w w ^ffl Ω Ω Ω ∞ ^ ^ S' Ω Ω Ω ^ ^ ^ ^ Ω Ω Ω Ω lft

o o o o o o o o o Ω Ω ffl ffl ffl ffl

Ω Ω Ω rø rø rø rø o o o o

o o o ω ω ω ω o o o o o o o o w w ω ro o o o Ω E? EP - ι? Ω Ω Ω Ω ^{ω M W W} Ω |ft

÷j S I td ÷j g s Cd

3 EP w I w 3 E ι? ES g δ S 2 ro δ ES 2 ro δ ffl

3 δ ^|-ι ES 2 Cd W irø.

3 0 2 ro δ E

3 3 T 3 3 "I cf Cd

Ω Ω Ω 5⁾ 5^, ι? ι? Ω Ω Ω Ω ^ ^ ^ S ff S^< S⁽ S^:) Ω Ω Ω Ω 5- ιϊ⁾ 5- 5' Ω Ω Ω Ω 5- 5' -ϊ^, _? Ω ft I

ES l?> ro ES 2 ES l_' ro ES ιf_' ro ES 2 ro ES 2 ro ES 2 ώ ES 2 ro ES 2 ro |rø

Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω a a a a a a a a a a a a a a a a a a a a

ffl ffl ffl ffl ffl ffl ffl ffl Tj hrj TI Tl Tl Tl Tl TJ HI ro td c cd

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a m m m G G G G G G G G m a ffl to ϋ ϋ ϋ ϋ to to to to ϋ o

8 δ δ δ δ δ δ δ δ fc fc fc fc fc fc fc fc G o G G G G o o m m

o o o o o o o o m m m ffl m m ffl m m ffl m m m m m ffl m m

* p-.- 1 ^p 3pr &^u .a* ___*> £f^t -ϊ-¹ 3^p rρr & ω a * ,w* ft & ,__-« c 3 ■-^» & ω .a*_J_*» ft_r^ 3M ^μ_r & s *___*__> Jftr. 3m &3 to ^ .* -__*» ^z 3^ρp &3 to .^* ,__*_, ^ Jr. ^m 3 &3 ω s-_-_. ft_ fci-ι rρr _ to^*_ «a -__> ft ,!M 3^p M?r _ toa a .j_>

^l ffl m m ffl o o o o m m m m o G G o m m ffl ffl o o o o m m m m

fc ^rj G o G ft ft

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^ ^pQ ^ a ft ^ ^ a ft ffl a ft ffl ^ a ft ^pp a ft ? a ft ^pρ a ft ffl ft ^pp p ^p ^ a

^| G f-. ffl m ffl G G G G m m m ffl G G G G ffl m ffl m G G G G m m m m G G G G G G

^'flfll 8 ffi ffi ffi ffi ffi ffi ffi ffi m ffl m ffl ffl m m m δ δ δ δ δ δ ^ t- l t4 g o o o o o o g g g o o o o o o g g o g g o o o o g g g g g o o o m m

o 3 -a J- ^"=^" Si ^"^ -_l jH S dj SH ^*-ⁱ t _₁ _H 3 t_> - _H π' O j_l JH 3 (J l

S ^t? s a ^ ^ a ^ ^ s ^ h | s ^ ⁽? | a ^f f? a ^{f (}? | a ^{, (}? | a ^ i^]? | a

ro ro cd ro ro ro ro ro ro ro ro ro c W W Cd ffl

1 1 1 1 1 1 1 1 1 1 1 1 1d 1 1 c 1d c1d ffl1 ffl1 ro1 ro1 ro1 ro1 c1d ffl1 ro1 ro1 I Ift 3 ft

Ω

_? _? _? _? _? _? _? _? Ω Ω Ω Ω Ω Ω Ω Ω rø rø rø rø rø Ift Ito

ro 1 ro1 ro1 ω o o Q o ω ω w ro o o Q o ro 1 « ^{ffl ffl} Ω Ω Ω Ω ^{w w w ffl} Ω lft

ro 1 c1d ro1 c1d ro1 c1d

^{ffl ffl ffl ffl} Ω Ω Ω Ω ^{ffl ffl W} H? Ω Ω Ω Ω -? H? -? -? Ω Ω Ω Ω HS H? ι_f ^, _? Ω lft

δ g^* if E -+ δ iC" E ^IS 2 ffi J_So^* E «-S*^• 2 ffi gd" E -S+ ff2 £ 3_" T <E-S*^■ ffi_t? p 3-d_j i ^*-f^* "ES C2D pά_jι |!

3 T

3 T 3 -i i I

Ω Ω Ω Ω H? -? H? H? HV ι? H? H? Ω Ω Ω Ω Hf H? ^ H? Ω Ω Ω Ω H? H? HV ffl Ω |ft

ES ^ ES _rf δ δ w Cd

0 Er W Cd

3 ES Cd

3 EP w _cf δ δ ES l li«..

3 T 3 T

O ^ ^ ^{ffl ffl} Ω Ω Ω Ω π ^{ffl ffl W} Ω Ω Ω Ω ^{ω ro ω ω} Ω Ω Ω Ω ft

O O W W Cd Cd Ω Ω o o Cd ro ro ro Ω Ω Ω ^{w ω w w} Ω Ω Ω Ω Ift

ES cf 3 δ δ ES cf 1 to ES cf 3 δ

ro ro ro ft #.ltos

Cd ffl o Ω Ω Q ω w Cd ffl o O o o w ro Cd Cd o O Cd SP W Cd O o Q Ω Cd flf ffl Cd O O ft

δ ES cf δ 3 5 ES cf δ 3 S ES cf δ 3 5 ES δ 3 to ft

o O o O O o o O o o o a a 8 8 8 a a 8 8 8 a 8 a a 8 8 a a 8 8 8 8 ft P

VO o Q o Q Ω Ω ffi ffi ffi ffi ffi fif ffi ffi 9 9 9 9 9 9 9 9 ft -4 cr'iorj

ES δ 3 δ ES cf i 5 ES δ 3 δ ES 1 3 to ES cf δ 3 5 ES cf 3 5 ES cf δ 3 5 ES 1 3 ffl 5 ES δ 3 to ft

o Ω SF s? cd E? Q o o Ω 5* ffl flf ω Cd Cd Cd O Q Ω Q W H? ε? s? Q Ω Ω Ω Cd ffl w H? Q O ft

W W O O O O Q O O O O Q Q O O Q Q O O O Q O O O O O O O O O O O O O θ |ft rø VO

Cd or Q TJ TJ TJ

1 Tj Tj Tj Tj W Cd Cd ro o Cd Cd Cd O TJ Ω Ω y Ω y Ω y Ω Ω Ω

1 1 r y w y ffi ffi ffi ffi ffi ffi w ilto

Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω 5^, ^ 5³ -? Ω Ω Ω Ω 5^, S^, S^, 5³ Ω Ω Ω Ω EP S³ -^* ₁ ^* 5^, Ω Ω Ω Ω ι? -? lft

ES l«.

o o o Q Q ro ro ffl W Q Q O Q ffl ω ro w o o o o w w ω ω o o Q o w ffl ω ro o lrø-.

ES l? ω rø ES l ffl rø ES ^ w rø !3 l? ffl rø ES ^ rø rø ES l ffl rø

Cd ffl W W W W W W W ffl O Q O Q O O O Q O O O O O O O O O O O O O O O O O o

Q Q Mc M.j Mrj MrJ hEJ hr. h^H MiH. Q Q Q Q Q Q Q

Ω Ω _? £? E? E? Ω Ω Ω Ω Ω Ω Ω Ω _? _? E? ^ Ω Ω Ω Ω _? _? 5' E? Ω Ω Ω Ω S' S' 5⁾ _? Ω Ω ft

cd ffl ffl ffl ffl ro ro ro ro ro ro ro cd cd ro ro ro ro cd ro ro ro Cd ffl ϋd Cd ffl Cd Cd Cd

O O O O O O O O hrl hrJ Tl hcl hrJ hcJ TJ Tl Cd Cd Cd Cd Cd Cd

ι H? ι? ιp Ω Ω Ω H? -? ιp H? Ω Ω Ω Ω H? ^ ι? H? Ω Ω Ω Ω ^ω H H? H? Ω Ω |ft

δ δ E ^ δ E ^ δ E ^ δ δ E i? δ δ ES i2 δ ES t| δ ES ^ δ ft

ro ro ro ro ro ro ro ro ro ro ro ro ro ro ro ro ro ro ro ffl ffl cd ffl cd ffl cd ffl ffl cd ^ffl ft | ¹rø VO O ro ro ro ro ro ro ffl ffl O O O O O O O O TJ TJ TJ TJ TJ TJ VO ft

HS -? H? _? Ω Ω Ω Ω ιi^* -? -? -? Ω Ω Ω Ω HS H? ι? -? Ω Ω Ω Ω Hp H? _? Hp Ω Ω |ft

g ώ^* δ ι_r E <-5>^■ ^ CD yw πt E^S ffi2 aώ" ► ^* E -S+ «2 ώ s' lf iS- ffi2 gώ' δl-r EcS+ 2ffi gώ^* i^^* E <-S>^■ 2D ^ώ δHr E-SH- ffi2 aώ- ,-r l ι l^!w

or ro ro ro ro cd ro ro or ro ro ro ro ro ro ro ro ffl ro cd ro ro ro

9 9 9 9 9 9 9 ^ffl s* _? ^{ffl ffl ffl ffl}

E^d S^f 5³ S⁾ 9 9 Ω Ω S^< EP 5' H? 9 Ω Ω Ω 5' S^, 5' 5' Ω Ω Ω Ω 5^< 5- 5' S^, Ω Ω ft

δ ES ϋ δ δ ES i? δ δ ES 2 δ δ W Cd W Cd

3 rø 3 δ ES i? δ δ ES 2 | ft!

o o o ro Cd s? 6? Ω Ω Ω Ω -? H? H? H? Ω Ω Ω Ω H? H? Cd Cd Ω Ω Ω Ω ft

o o o w ffl ^{ffl ffl} Ω Ω Ω Ω Sr^{, w ω ω} Ω Ω Ω Ω ^{ω ω ω w} Ω Ω Ω Ω ft

o o O O O o O o o o 8 8 8 8 a a 8 a 8 a a a a a 8 a a 8 a a a 8 8 a a I 1ft 3 o ffi ffi ffi 9 9 9 9 9 9 9 9 -^ Cd Cd ω Cd ffl & | ,lto%

ro ro Q o Q O ffl ffl ω H? O O O O ro s? ε? &? O O Q ffl ffl Cd Cd Ω o o o ro W Cd Cd Ω ft

S ES δ 3 S ES 1 δ 3 5 ES δ 3 5 ES cf δ 3 5 ES cf 3 δ 5 ES cf δ 3 HP ES cf

t o

o o Ω Cd ro ro ro o o o o ro ffl Cd Cd Cd ro 1 ro ffl Ω O O Q Cd Cd Cd Cd Ω O O O Cd ro Cd Cd ft

5 ES cf δ 3 5 ES 1 δ 3 to ES cf 3 δ 5 ES cf δ ^-ι.

3 to ES cf δ 3 to ES cf δ 3 ϊ ES 1 δ 3 to ES cf δ 3 5 ES cf δ 3 Ift

o Q Q Cd Cd Cd J? O o Q Ω ω w w Cd ffl ro Ω O Q w W ffl Cd Q Q o ro Cd ω ω o Ift

G G G G m ^ ffl to G G

fc fc fc fc fc fc fc fc J O

m m ffl ffl m ffl m ffl m m

3 3 3 3 3 3

^•Ed I w ft

•A ffl -A ft ffl w ft ffl w ft w ft A ffl VA W ft ffl W ft 3 3 a 3

$ 3 3 a

^i G m m m m rt g r. r! -H m m m ffl g g g ffl ffl ffl ffl G G G G m ffl ffl to o υ o o o o col fc fc fc fc fc fc fc fc li li li li

CN f ffl ffl o %\ ffl fl δ δ δ δ δ δ δ δ ^u ° ° ^{ϋ h h}

CN 3

3 I _H li li li 14 O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O ffl ffl

co i J5 tu +i ^jH -. ω •__ J¹ J^*. ω ^' •_- .IT¹ J^". ) *_ jH _^*_ ω ._- .H ^**_ > - J- 3 o *_ jH ^*"? «" ,3 .3 ^"5 <> _ι

^ _π ^ ^ ^ρp ^ ^ ^{fe p}p _H s ^ s ^fe p 3 s ft ffl ^ a ft ffl ft ^pp ft ^pp ^ρ ffl | a

p.| m G G G G (-3 m (-3 ffl G G G G (-. ffl ffl ffl G G G G (-3 m ffl m G G G G G G G G G G

C I co co co co co co co co

I e-. ffl ffi ffi ffi ffi g ^ g g g g ^ ^ ^ ^ ^ m ^ ^ rS ^ fc fc fc fc o g ft ft ft ft ffl m t- cό 3 I ov

PH! 14 G G G G G G G G G G G G G G G G G G G G G G G G G G G G G G G G G m ffl

o I Λ CD .* H-*I iz-ι 3 jr & ω ._* +-> J .Jrr.¹ 3 u. & » * j-ii J ^r.^* 3 __. & ω J_> J _r-< _ fr? tU i JH 5 <_I J_.

^ ^p? ^ ft p ^ ft ^p ^ ft o? ^ a ft a ft ffl | a ΛJH T ft ffl J ω ^B a _ ■r_- . J ftfr¹ ._^* <-) .__ .^"-< _-. to .- ffl a ft ^pp a

R⁹ is CHF₂ R is CH2E3 R⁹ is CF 2C 2

R3 _R4a _R4b R6 R3 _R4a _R4b ≠ R3 _R4a _R4b R6 t-Bu Br Br Cl t-Bu Br F Cl t-Bu Br Cl Cl

Me Br Br Br Me Br F Br Me Br Cl Br

Et Br Br Br Et Br F Br Et Br Cl Br i-Pr Br Br Br f-Pr Br F Br i-Pr Br Cl Br t-Bu Br Br Br t-Bu Br F Br t-Bu Br Cl Br

Me Br Cl Me Br Cl Cl Me Br Br Cl

Et Br Cl Et Br Cl Cl Et Br Br Cl i-Pr Br Cl i-Pr Br Cl Cl i-Pr Br Br Cl t-Bu Br Cl t-Bu Br Cl Cl t-Bu Br Br Cl

Me Br Br Me Br Cl Br Me Br Br Br

Et Br Br Et Br Cl Br Et Br Br Br i-Pr Br Br i-Pr Br Cl Br i-Pr Br Br Br t-Bu Br Br t-Bu Br Cl Br t-Bu Br Br Br

Me Br F Cl Me Br I Cl Me Br CF₃ Cl

Et Br F Cl Et Br I Cl Et Br CF₃ Cl i-Pr Br F Cl ∑-Pr Br I Cl i-Pr Br CF₃ Cl t-Bu Br F Cl t-Bu Br I Cl t-Bu Br CF₃ Cl

Me Br F Br Me Br I Br Me Br CF₃ Br

Et Br F Br Et Br I Br Et Br CF₃ Br i-Pr Br F Br z'-Pr Br I Br i-Pr Br CF₃ Br t-Bu Br F Br t-Bu Br I Br t-Bu Br CF₃ Br

Me Br Cl Cl Me Br Br Cl Me Br Cl

Et Br Cl Cl Et Br Br Cl Et Br Cl i-Pr Br Cl Cl -Pr Br Br Cl t-Pr Br Cl t-Bu Br Cl Cl t-Bu Br Br Cl t-Bu Br Cl

Me Br Cl Br Me Br Br Br Me Br Br

Et Br Cl Br Et Br Br Br Et Br Br i-Pr Br Cl Br i-Pr Br Br Br /-Pr Br Br t-Bu Br Cl Br

t-Bu Br Br Br t-Bu Br Br

Formulation/Utility

Compounds of this invention will generally be used as a formulation or composition with an agriculturally suitable carrier comprising at least one of a liquid diluent, a solid diluent or a surfactant. The formulation or composition ingredients are selected to be consistent with the physical properties ofthe active ingredient, mode of application and environmental factors such as soil type, moisture and temperature. Useful formulations include liquids such as solutions (including emulsifiable concentrates), suspensions, emulsions (including micro emulsions and/or suspoemulsions) and the like which optionally can be thickened into gels. Useful formulations further include solids such as dusts, powders, granules, pellets, tablets, films, and the like which can be water-dispersible ("wettable") or water-soluble. Active ingredient can be (micro)encapsulated and farther formed into a suspension or solid formulation; alternatively the entire formulation of active ingredient can be encapsulated (or "overcoated"). Encapsulation can control or delay release ofthe active ingredient. Sprayable formulations can be extended in suitable media and used at spray volumes from about one to several hundred liters per hectare. High-strength compositions are primarily used as intermediates for further formulation.

The formulations will typically contain effective amounts of active ingredient, diluent and surfactant within the following approximate ranges that add up to 100 percent by weight.

Weight Percent

Active mgredient Diluent Surfactant

Water-Dispersible and Water-soluble 5-90 0-94 1-15 Granules, Tablets and Powders.

Suspensions, Emulsions, Solutions 5-50 40-95 0-15 (including Emulsifiable Concentrates)

Dusts 1-25 70-99 0-5

Granules and Pellets 0.01-99 5-99.99 0-15

High Strength Compositions 90-99 0-10 0-2

Typical solid diluents are described in Watkins, et al., Handbook of Insecticide Dust Diluents and Carriers, 2nd Ed., Dorland Books, Caldwell, New Jersey. Typical liquid diluents are described in Marsden, Solvents Guide, 2nd Ed., Interscience, New York, 1950. McCutcheon 's Detergents and Emulsifiers Annual, Allured Publ. Corp., Ridgewood, New Jersey, as well as Sisely and Wood, Encyclopedia of Surface Active Agents, Chemical Publ. Co., Inc., New York, 1964, list surfactants and recommended uses. All formulations can contain minor amounts of additives to reduce foam, caking, corrosion, microbiological growth and the like, or thickeners to increase viscosity.

Surfactants include, for example, polyethoxylated alcohols, polyethoxylated alkylphenols, polyethoxylated sorbitan fatty acid esters, dialkyl sulfosuccinates, alkyl sulfates, alkylbenzene sulfonates, organosilicones, N,N-dialkyltaurates, Hgni sulfonates, naphthalene sulfonate formaldehyde condensates, polycarboxylates, and polyoxy- ethylene/polyoxypropylene block copolymers. Solid diluents include, for example, clays such as bentonite, montmorillonite, attapulgite and kaolin, starch, sugar, silica, talc, diatomaceous earth, urea, calcium carbonate, sodium carbonate and bicarbonate, and sodium sulfate. Liquid diluents include, for example, water, N₅N-dimethylformamide, dimethyl sulfoxide. N-alkylpyrrolidone, ethylene glycol, polypropylene glycol, propylene carbonate, dibasic esters, paraffins, alkylbenzenes, alkylnaphthalenes, oils of olive, castor, linseed, tung, sesame, corn, peanut, cotton-seed, soybean, rape-seed and coconut, fatty acid esters, ketones such as cyclohexanone, 2-heptanone, isophorone and 4-hydroxy-4-methyl-2-pentanone, and alcohols such as methanol, cyclohexanol, decanol. benzyl and tefrahydrofurfuryl alcohol.

Solutions, clucling emulsifiable concentrates, can be prepared by simply mixing the ingredients. Dusts and powders can be prepared by blending and, usually, grmding as in a hammer mill or fluid-energy mill. Suspensions are usually prepared by wet-milling; see, for example, U.S. 3,060,084. Granules and pellets can be prepared by spraying the active material upon preformed granular carriers or by agglomeration techniques. See Browning, "Agglomeration", Chemical Engineering, December 4, 1967, pp 147-48, Perry's Chemical Engineer's Handbook, 4th Ed., McGraw-Hill, New York, 1963, pages 8-57 and following, and PCT Publication WO 91/13546. Pellets can be prepared as described in U.S. 4,172,714. Water-dispersible and water-soluble granules can be prepared as taught in U.S. 4,144,050, U.S. 3,920,442 and DE 3,246,493. Tablets can be prepared as taught in U.S. 5,180,587, U.S. 5,232,701 and U.S. 5,208,030. Films can be prepared as taught in GB 2,095,558 and U.S. 3,299,566.

For further information regarding the art of formulation, see T. S. Woods, "The Formulator's Toolbox - Product Forms for Modern Agriculture" in Pesticide Chemistry and Bioscience, The Food-Environment Challenge, T. Brooks and T. R. Roberts, Eds., Proceedings ofthe 9th International Congress on Pesticide Chemistry, The Royal Society of Chemistry, Cambridge, 1999, pp. 120-133. See also U.S. 3,235,361, Col. 6, line 16 through Col. 7, line 19 and Examples 10-41; U.S. 3,309,192, Col. 5, line 43 through Col. 7, line 62 and Examples 8, 12, 15, 39, 41, 52, 53, 58, 132, 138-140, 162-164, 166, 167 and 169-182; U.S. 2,891,855, Col. 3, line 66 through Col. 5, line 17 and Examples 1-4; Klingman, Weed Control as a Science, John Wiley and Sons, Inc., New York, 1961, pp 81-96; and Hance et al., Weed Control Handbook, 8th Ed., Blackwell Scientific Publications, Oxford, 1989. In the following Examples, all percentages are by weight and all formulations are prepared in conventional ways. Compound numbers refer to compounds in Index Table A.

Example A Wettable Powder

Compound 6 65.0% dodecylphenol polyethylene glycol ether 2.0% sodium Hgninsulfonate 4.0% sodium silicoaluminate 6.0% montmorillonite (calcined) 23.0% . Example B Granule

Compound 6 10.0% attapulgite granules (low volatile matter, 0.71/0.30 mm; U.S.S. No. 25-50 sieves) 90.0%.

Example C Extruded Pellet

Compound 6 25.0% anhydrous sodium sulfate 10.0% crude calcium Hgninsulfonate 5.0% sodium alkylnaphthalenesulfonate 1.0% calcium/magnesium bentonite 59.0%.

Example D Emulsifiable Concentrate Compound 6 20.0% blend of oil soluble sulfonates and polyoxyethylene ethers 10.0% isophorone 70.0%.

Compounds of this invention are characterized by favorable metabolic and/or soil residual patterns and exhibit activity conttolling a spectrum of agronomic and non- agronomic invertebrate pests. (In the context of this disclosure "invertebrate pest control" means inhibition of invertebrate pest development (including mortality) that causes significant reduction in feeding or other injury or other damage caused by the pest; related expressions are defined analogously.) As referred to in this disclosure, the term "invertebrate pest" includes arthropods, gastropods and nematodes of economic importance as pests. The term "arthropod" includes insects, mites, spiders, scorpions, centipedes, milhpedes, pill bugs and symphylans. The term "gastropod" includes snails, slugs and other Stylommatophora. The term "nematode" includes all ofthe helminths, such as: roundworms, heartworms, and phytophagous nematodes (Nematoda), flukes (Tematoda), Acanthocephala, and tapeworms (Cestoda). Those skilled in the art will recognize that not all compounds are equally effective against all pests. Compounds of this invention display activity against economically important agronomic, forest, greenhouse, nursery, ornamentals, food and fiber, public and animal health, domestic and commercial structure, household, and stored product pests. These include larvae ofthe order Lepidoptera, such as armyworms, cutworms, loopers, and heliothines in the family Noctuidae (e.g., fall armyworm (Spodopterafugiperda J. E. Smith), beet armyworm (Spodoptera exigua Hύbner), black cutworm (Agrotis ipsilon Hufnagel), cabbage looper (Trichoplusia ni Hϊibner), tobacco budworm (Heliothis virescens Fabricius)); borers, casebearers, webworms, coneworms, cabbageworms and skeletonizers from the family Pyralidae (e.g., European corn borer (Ostrinia nubilalis Hύbner), navel orangeworm (Amyelois transitella Walker), corn root webworm (Crambus caliginosellus Clemens), sod webworm (Herpetogramma licarsisalis Walker)); leafrollers, budworms, seed worms, and fruit worms in the family Tortricidae (e.g., codling moth (Cydia pomonella Linnaeus), grape berry moth (Endopiza viteana Clemens), oriental fruit moth (Grapholita molesta Busck)); and many other economically important lepidoptera (e.g., diamondback moth (Plutella xylostella Linnaeus), pink bollworm (Pectinophora gossypiella Saunders), gypsy moth (Lymantria dispar Linnaeus)); nymphs and adults ofthe order Blattodea including cockroaches from the families Blattellidae and Blattidae (e.g., oriental cockroach (Blatta orientalis Linnaeus), Asian cockroach (Blatella asahinai Mizukubo), German cockroach (Blattella germanica Linnaeus), brownbanded cockroach (Supella longipalpa Fabricius), American cockroach (Periplaneta americana Linnaeus), brown cockroach (Periplaneta brunnea Burmeister), Madeira cockroach (Leucophaea maderae Fabricius)); fohar feeding larvae and adults ofthe order Coleoptera including weevils from the families Anthribidae, Bruchidae, and Curcuhonidae (e.g., boll weevil (Anthonomus grandis Boheman), rice water weevil (Lissorhoptrus oryzophilus Kuschel), granary weevil (Sitophilus granarius Linnaeus), rice weevil (Sitophilus oryzae Linnaeus)); flea beetles, cucumber beetles, rootworms, leaf beetles, potato beetles, and leafminers in the family ChrysomeUdae (e.g., Colorado potato beetle (Leptinotarsa decemlineata Say), western corn rootworm (Diabrotica virgifera virgifera LeConte)); chafers and other beetles from the family Scaribaeidae (e.g., Japanese beetle (Popillia japonica Newman) and European chafer (Rhizotrogus majalis Razoumowsky)); carpet beetles from the family Dermestidae; wireworms from the family Elateridae; bark beetles from the family Scolytidae and flour beetles from the family

Tenebrionidae. In addition it includes: adults and larvae ofthe order Dermaptera including earwigs from the family Forf culidae (e.g., European earwig (Forflcula auricularia Linnaeus), black earwig (Chelisoches morio Fabricius)); adults and nymphs ofthe orders Hemiptera and Homoptera such as, plant bugs from the family Miridae, cicadas from the family Cicadidae, leafhoppers (e.g. Empoasca spp.) from the family Cicadellidae, planthoppers from the families Fulgoroidae and Delphacidae, treehoppers from the family Membracidae, psyllids from the family Psyllidae, whiteflies from the family Aleyrodidae, aphids from the family Aphididae, phylloxera from the family Phylloxeridae, mealybugs from the family Pseudococcidae, scales from the families Coccidae, Diaspididae and Margarodidae, lace bugs from the family Tingidae, stink bugs from the family Pentatomidae, cinch bugs (e.g., Blissus spp.) and other seed bugs from the family Lygaeidae, spittlebugs from the family Cercopidae squash bugs from the family Coreidae, and red bugs and cotton stainers from the family Pyrrhocoridae. Also included are adults and larvae ofthe order Acari (mites) such as spider mites and red mites in the family Tetranychidae (e.g., European red mite (Panonychus ulmi Koch), two spotted spider mite (Tetranychus urticae Koch), McDaniel mite (Tetranychus mcdanieli McGregor)), flat mites in the family Tenuipalpidae (e.g., citrus flat mite (Brevipalpus lewisi McGregor)), rust and bud mites in the family Eriophyidae and other fohar feeding mites and mites important in human and animal health, i.e. dust mites in the family Epidermoptidae, follicle mites in the family Demodicidae, grain mites in the family Glycyphagidae, ticks in the order Ixodidae (e.g., deer tick (Ixodes scapularis Say), Australian paralysis tick (Ixodes holocyclus Neumann), American dog tick (Dermacentor variabilis Say), lone star tick (Amblyomma americanum Linnaeus) and scab and itch mites in the families Psoroptidae, Pyemotidae, and Sarcoptidae; adults and immatures of the order Orthoptera including grasshoppers, locusts and crickets (e.g., migratory grasshoppers (e.g., Melanoplus sanguinipes Fabricius, M. differentialis Thomas), American grasshoppers (e.g., Schistocerca americana Drury), desert locust (Schistocerca gregaria Forskal), migratory locust (Locusta migratoria Linnaeus), house cricket (Acheta domesticus Linnaeus), mole crickets (Gryllotalpa spp.)); adults and immatures ofthe order Diptera including leafminers, midges, fruit flies (Tephritidae), frit flies (e.g., Oscinellafrit Linnaeus), soil maggots, house flies (e.g., Musca domestica Linnaeus), lesser house flies (e.g., Fannia canicularis Linnaeus, F.femoralis Stein), stable flies (e.g., Stomoxys calcitrans Linnaeus), face flies, horn flies, blow flies (e.g., Chrysomya spp., Phormia spp.), and other muscoid fly pests, horse flies (e.g., Tabanus spp.), bot flies (e.g., Gastrophilus spp., Oestrus spp.), cattle grubs (e.g., Hypoderma spp.), deer flies (e.g., Chrysops spp.), keds (e.g., Melophagus ovinus Linnaeus) and other Brachycera, mosquitoes (e.g., Aedes spp., Anopheles spp., Culex spp.), black flies (e.g., Prosimulium spp., Simulium spp.), biting midges, sand flies, sciarids, and other Nematocera; adults and immatures ofthe order Thysanoptera including onion thrips (Thrips tabaci Lindeman) and other fohar feeding thrips; insect pests ofthe order Hymenoptera including ants (e.g., red carpenter ant (Camponotus ferrugineus Fabricius), black carpenter ant (Camponotus pennsylvanicus De Geer), Pharaoh ant (Monomorium pharaonis Linnaeus), little fire ant (Wasmannia auropunctata Roger), fire ant (Solenopsis geminata Fabricius), red imported fire ant (Solenopsis invicta Buren), Argentine ant (Iridomyrmex humilis Mayr), crazy ant

(Paratrechina longicornis Latreille), pavement ant (Tetramorium caespitum Linnaeus), cornfield ant (Lasius alienus Fδrster), odorous house ant (Tapinoma sessile Say)), bees (mclucling carpenter bees), hornets, yellow jackets and wasps; insect pests ofthe order Isoptera including the eastern subterranean termite (Reticulitermes flavipes Kollar), western subterranean termite (Reticulitermes hesperus Banks), Formosan subterranean termite

(Coptotermes formosanus Shiraki), West Indian drywood termite (Incisitermes immigrans Snyder) and other termites of economic importance; insect pests ofthe order Thysanura such as silverfish (Lepisma saccharina Linnaeus) and firebrat (Thermobia domestica Packard); insect pests ofthe order Mallophaga and including the head louse (Pediculus humanus capitis De Geer), body louse (Pediculus humanus humanus Linnaeus), chicken body louse (Menacanthus stramineus Nitszch), dog biting louse (Trichodectes canis De Geer), fluff louse (Goniocotes gallinae De Geer), sheep body louse (Bovicola ovis Schrank), short-nosed cattle louse (Haematopinus ewγsternus Nitzsch), long-nosed cattle louse (Linognathus vituli Linnaeus) and other sucking and chewing parasitic lice that attack man and animals; insect pests ofthe order Siphonopteramcluding the oriental rat flea (Xenopsylla cheopis Rothschild), cat flea (Ctenocephalides felis Bouche), dog flea (Ctenocephalides canis Curtis), hen flea (Ceratophyllus gallinae Schrank), sticktight flea (Echidnophaga gallinacea Westwood), human flea (Pulex irritans Linnaeus) and other fleas afflicting mammals and birds. Additional arthropod pests covered include: spiders in the order Araneae such as the brown recluse spider (Loxosceles reclusa Gertsch & Mulaik) and the black widow spider (Latrodectus mactans Fabricius), and centipedes in the order Scutigeromorpha such as the house centipede (Scutigera coleoptrata Linnaeus). Activity also includes members ofthe Classes Nematoda, Cestoda, Trematoda, and Acanthocephala including economically important members ofthe orders Strongylida, Ascaridida, Oxyurida, Rhabditida, Spirurida, and Enoplida such as but not limited to economically important agricultural pests (i.e. root knot nematodes in the genus Meloidogyne, lesion nematodes in the genus Pratylenchus, stubby root nematodes in the genus Trichodorus, etc.) and animal and human health pests (i.e. all economically important flukes, tapeworms, and roundworms, such as Strongylus vulgaris in horses, Toxocara canis in dogs, Haemonchus contortus in sheep, Dirofllaria immitis Leidy in dogs, Anoplocephala perfoliata in horses, Fasciola hepatica Linnaeus in ruminants, etc.).

Compounds ofthe invention show particularly high activity against pests in the order Lepidoptera (e.g., Alabama argillacea Hύbner (cotton leaf worm), Archips argyrospila Walker (fruit tree leaf roller), A. rosana Linnaeus (European leaf roller) and other Archips species, Chilo suppressalis Walker (rice stem borer), Cnaphalocrosis medinalis Guenee (rice leaf roller), Crambus caliginosellus Clemens (corn root webworm), Crambus teterrellus Zincken (bluegrass webworm), Cydia pomonella Linnaeus (codling moth), Earias insulana Boisduval (spiny bollworm), Earias vittella Fabricius (spotted bollworm), Helicoverpa annigera Hύbner (American bollworm), Helicoverpa zea Boddie (corn earworm), Heliothis virescens Fabricius (tobacco budworm), Herpetogramma licarsisalis Walker (sod webworm), Lobesia botrana Denis & Schiffermύller (grape berry moth), Pectinophora gossypiella Saunders (pink bollworm), Phyllocnistis citrella Stainton (citrus leafininer), Pieris brassicae Linnaeus (large white butterfly), Pieris rapae Linnaeus (small white butterfly), Plutella xylostella Linnaeus (diamondback moth), Spodoptera exigua Hύbner (beet armyworm), Spodoptera litura Fabricius (tobacco cutworm, cluster caterpiUar), Spodoptera frugiperda J. E. Smith (fall armyworm), Trichoplusia ni Hύbner (cabbage looper) and Tuta absoluta Meyrick (tomato leafminer)). Compounds of he invention also have commercially significant activity on members from the order Homoptera mcluding: Acyrthisiphon pisum Harris (pea aphid), Aphis craccivora Koch (cowpea aphid), Aphis fabae Scopoli (black bean aphid), Aphis gossypii Glover (cotton aphid, melon aphid), Aphis pomi De Geer (apple aphid), Aphis spiraecola Patch (spirea aphid), Aulacorthum solani Kaltenbach (foxglove aphid), Chaetosiphonfragaefolii Cockerell (strawberry aphid), Diuraphis noxia Kurdjumov/Mordvilko (Russian wheat aphid), Dysaphis plantaginea Paaserini (rosy apple aphid), Eriosoma lanigerum Hausmann (woolly apple aphid), Hyalopterus pruni Geoffroy (mealy plum aphid), Lipaphis erysimi Kaltenbach (turnip aphid), Metopolophium dirrhodum Walker (cereal aphid), Macrosipum euphorbiae Thomas (potato aphid), Myzus persicae Suker (peach-potato aphid, green peach aphid), Nasonovia rϊbisnigri Mosley (lettuce aphid), Pemphigus spp. (root aphids and gall aphids), Rhopalosiphum maidis Fitch (corn leaf aphid), Rhopalosiphum padi Linnaeus (bird cherry- oat aphid), Schizaphis graminum Rondani (greenbug), Sitobion avenae Fabricius (English grain aphid), Therioaphis maculata Buckton (spotted alfalfa aphid), Toxoptera aurantii

Boyer de Fonscolombe (black citrus aphid), and Toxoptera citricida Kirkaldy (brown citrus aphid); Adelges spp. (adelgids); Phylloxera devastatrix Pergande (pecan phylloxera); Bemisia tabaci Gennadius (tobacco whitefly, sweetpotato whitefly), Bemisia argentifolii Bellows & Perring (silverleaf whitefly), Dialeurodes citri Ashmead (citrus whitefly) and Trialeurodes vaporariorum Westwood (greenhouse whitefly); Empoasca fabae Harris

(potato leafhopper), Laodelphax striatellus Fallen (smaller brown planthopper), Macrolestes quadrilineatus Forbes (aster leafhopper), Nephotettix cinticeps Uhler (green leafhopper), Nephotettix nigropictus Stal (rice leafhopper), Nilaparvata lugens Stal (brown planthopper), Peregrinus maidis Ashmead (corn planthopper), Sogatellafurcifera Horvath (white-backed planthopper), Sogatodes orizicola Muir (rice delphacid), Typhlocyba pomaria McAtee white apple leafhopper, Erythroneoura spp. (grape leafhoppers); Magicidada septendecim Linnaeus (periodical cicada); Icerya purchasi Maskell (cottony cushion scale), Quadraspidiotu perniciosus Comstock (San Jose scale); Planococcus citri Risso (citrus mealybug); Pseudococcus spp. (other mealybug complex); Cacopsylla pyricola Foerster (pear psylla), Trioza diospyri Ashmead (persimmon psylla). These compounds also have activity on members from the order Hemiptera including: Acrosternum hilare Say (green stink bug), Anasa tristis De Geer (squash bug), Blissus leucopterus leucopterus Say (chinch bug), Corythuca gossypii Fabricius (cotton lace bug), Cyrtopeltis modesta Distant (tomato bug), Dysdercus suturellus Herrich-Schaffer (cotton stainer), Euchistus servus Say (brown stink bug), Euchistus variolarius Pahsot de Beauvois (one-spotted stink bug), Graptosthetus spp. (complex of seed bugs), Leptoglossus corculus Say (leaf-footed pine seed bug), Lygus lineolaris Pahsot de Beauvois (tarnished plant bug), Nezara viridula Linnaeus (southern green stink bug), Oebalus pugnax Fabricius (rice stink bug), Oncopeltus fasciatus Dallas (large milkweed bug), Pseudatomoscelis seriatus Reuter (cotton fleahopper). Other insect orders controlled by compounds ofthe invention include Thysanoptera (e.g., Frankliniella occidentalis Pergande (western flower thrip), Scirthothrips citri Moulton (citrus thrip), Sericothrips variabilis Beach (soybean thrip), and Thrips tabaci Lindeman (onion thrip); and the order Coleoptera (e.g., Leptinotarsa decemlineata Say (Colorado potato beetle),

Epilachna varivestis Mulsant (Mexican bean beetle) and wireworms ofthe genera Agriotes, Athous or Limonius).

Compounds of this invention can also be mixed with one or more other biologically active compounds or agents including insecticides, fungicides, nematocides, bactericides, acaricides, growth regulators such as rooting stimulants, chemosterilants, semiochemicals, repellents, attractants, pheromones. feeding stimulants, other biologically active compounds or entomopathogenic bacteria, virus or fungi to form a multi-component pesticide giving an even broader spectrum of agricultural utility. Thus compositions ofthe present invention can further comprise a biologically effective amount of at least one additional biologically active compound or agent. Examples of such biologically active compounds or agents with which compounds of this invention can be formulated are: insecticides such as abamectin, acephate, acetamiprid, avermectin, azadirachtin, azinphos-methyl, bifenthrin, binfenazate, buprofezin, carbofuran, chlorfenapyr, chlorfluazuron, chlo yrifos, chlorpyrifos-methyl, chromafenozide, clothianidin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, cypermethrin, cyromazine, deltamethrin, diafenthiuron, diazinon, diflubenzuron, dimethoate, diofenolan, emamectin, endosulfan, esfenvalerate, ethiprole, fenothicarb, fenoxycarb, fenpropathrin, fenproximate, fenvalerate, fipronil, flonicamid, flucythrinate, tau-fluvalinate, flufenoxuron, fonophos, halofenozide, hexaflumuron, imidacloprid, indoxacarb, isofenphos, lufenuron, malathion, metaldehyde, methamidophos, methidathion, methomyl, methoprene, methoxychlor, monocrotophos, methoxyfenozide, nithiazin, novaluron, oxamyl, parathion, parathion-methyl, peivmethrin, phorate, phosalone, phosmet, phosphamidon, pirimicarb, profenofos, pymetrozine, pyridalyl, pyriproxyfen, rotenone, spinosad, sulprofos, tebufenozide, teflubenzuron, tefluthrin, terbufos, tetrachlorvinphos, thiacloprid, thiamethoxam, thiodicarb, thiosultap-sodium, ttalomethrin, trichlorfon and triflumuron; fungicides such as acibenzolar, azoxystrobin, benomyl, blasticidin-S, Bordeaux m ture • (tribasic copper sulfate), bromuconazole, carpropamid, captafol, captan, carbendazim, chloroneb, chlorothalonil, copper oxychloride, copper salts, cyflufenamid, cymoxanil, cyproconazole, cyprodinil, (S)-3,5-dicl oro-N-(3-chloro-l-ethyl-l-methyl-2-oxopropyl)-4- methylbenzamide (RH 7281), diclocymet (S-2900), diclomezine, dicloran, difenoconazole, (S)-3,5-dihydro-5-me yl-2-(methylmio)-5-phenyl-3-(phenylammo)-4H-imiαa^

(RP 407213), dimethomorph, dimoxystrobin, diniconazole, diniconazole-M, dodine, edifenphos, epoxiconazole, famoxadone, fenamidone, fenarimol, fenbuconazole, fencaramid (SZX0722), fenpiclonil, fenpropidin, fenpropimorph, fentin acetate, fentin hydroxide, fluazinam, fludioxonil, flumetover (RPA 403397), fluquinconazole, flusilazole, flutolanil, flutriafol, folpet, fosetyl-aluminum, furalaxyl, furametapyr (S-82658), hexaconazole, ipconazole, iprobenfos, iprodione, isoprothiolane, kasugamycin, kresoxim-methyl, mancozeb, maneb, mefenoxam, mepronil, metalaxyl, metconazole, metomino- sfrobin fenominostrobin (SSF-126), myclobutanil, neo-asozin (ferric methanearsonate), oxadixyl, penconazole, pencycuron, probenazole, prochloraz, propamocarb, propiconazole, pyrifenox, pyraclostrobin, pyrimethanil, pyroquilon, quinoxyfen, spiroxamine, sulfur, tebuconazole, tetraconazole, thiabendazole, thifluzamide, thiophanate-methyl, thiram, tiadinil, triadimefon, triadimenol, tricyclazole, trifloxystrobin, triticonazole, validamycin and vinclozolin; nematocides such as aldicarb, oxamyl and fenamiphos; bactericides such as streptomycin; acaricides such as amitraz, chinomethionat, chlorobenzilate, cyhexatin, dicofol, dienochlor, etoxazole, fenazaquin, fenbutatin oxide, fenpropathrin, fenpyroximate, hexythiazox, propargite, pyridaben and tebufenpyrad; and biological agents such as Bacillus thuringiensis mcluding ssp. aizawai and kurstaki, Bacillus thuringiensis delta endotoxin, baculovirus, and entomopathogenic bacteria, virus and fungi.

A general reference for these agricultural protectants is The Pesticide Manual, 12th Edition, C. D. S. Tomlin, Ed., British Crop Protection Council, Farnham, Surrey, U.K., 2000.

Of note are combinations of a compound of Formula 1 d with the biologically active compounds above.

Preferred insecticides and acaricides for mixing with compounds of this invention include pyrethroids such as cypermethrin, cyhalothrin, cyfluthrin and beta-cyfluthrin, esfenvalerate, fenvalerate and tralomethrin; carbamates such as fenothicarb, methomyl, oxamyl and thiodicarb; neonicotinoids such as clothianidin, imidacloprid and thiacloprid, neuronal sodium channel blockers such as indoxacarb, insecticidal macrocychc lactones such as spinosad, abamectin, avermectin and emamectin; γ-aminobutyric acid (GABA) antagonists such as endosulfan, ethiprole and fipronil; insecticidal ureas such as flufenoxuron and triflumuron, juvenile hormone mimics such as diofenolan and pyriproxyfen; pymetrozine; and amitraz. Preferred biological agents for mixing with compounds of this invention include Bacillus thuringiensis and Bacillus thuringiensis delta endotoxin as well as naturally occurring and genetically modified viral insecticides including members ofthe family Baculoviridae as well as entomophagous fungi. Of note are combinations of a compound of Formula Id with the preferred insecticides and acaricides above. Most preferred mi-xtures include a rrnxture of a compound of this invention with cyhalothrin; a mixture of a compound of this invention with beta-cyfluthrin; a rrnxture of a compound of this invention with esfenvalerate; a mixture of a compound of this invention with methomyl; a mixture of a compound of this invention with imidacloprid; a mixture of a compound of this invention with thiacloprid; a ntixture of a compound of this invention with indoxacarb; a mixture of a compound of this invention with abamectin; a mixture of a compound of this invention with endosulfan; a mixture of a compound of this invention with ethiprole; a rnixture of a compound of this invention with fipronil; a mixture of a compound of this invention with flufenoxuron; a nmture of a compound of this invention with pyriproxyfen; a mixture of a compound of this invention with pymetrozine; a rn ture of a compound of this invention with amitraz; a mixture of a compound of this invention with Bacillus thuringiensis and a mixture of a compound of this invention with Bacillus thuringiensis delta endotoxin. In certain instances, combinations with other invertebrate pest control compounds or agents having a similar spectrum of control but a different mode of action will be particularly advantageous for resistance management. Thus, compositions ofthe present invention can further comprise an biologically effective amount of at least one additional invertebrate pest control compounds or agents having a similar spectrum of control but a different mode of action. Contacting a plant genetically modified to express a plant protection compound (e.g., protein) or the locus ofthe plant with a biologically effective amount of a compound of invention can also provide a broader spectrum of plant protection and be advantageous for resistance management.

Invertebrate pests are controlled and protection of agronomic, horticultural and specialty crops, animal and human health is achieved by applying one or more ofthe compounds of this invention, in an effective amount, to the environment ofthe pests including the agronomic and/or nonagronomic locus of infestation, to the area to be protected, or directly on the pests to be controlled. Thus, the present invention further comprises a method for the control of fohar- and soil-inhabiting invertebrates and protection of agronomic and/or nonagronomic crops, comprising contacting the invertebrates or their environment with a biologically effective amount of one or more of the compounds of the invention, or with a composition comprising at least one such compound or a composition comprising at least one such compound and an effective amount of at least one additional biologically active compound or agent. A preferred method of contact is by spraying. Alternatively, a granular composition comprising a compound ofthe invention can be apphed to the plant foliage or the soil. Compounds of this invention are effective in dehvery through plant uptake by contacting the plant with a composition comprising a compound of this invention apphed as a soil drench of a hquid formulation, a granular formulation to the soil, a nursery box treatment or a dip of transplants. Other methods of contact include apphcation of a compound or a composition ofthe invention by direct and residual sprays, aerial sprays, seed coats, micrpencapsulations, systemic uptake, baits, eartags, boluses, foggers, fumigants, aerosols, dusts and many others. The compounds of this invention can be incorporated into baits that are consumed by the invertebrates or within devices such as traps and the like. Granules or baits comprising between 0.01-5% active ingredient, 0.05-10% moisture retaining agent(s) and 40-99% vegetable flour are effective in controlling soil insects at very low apphcation rates, particularly at doses of active ingredient that are lethal by ingestion rather than by direct contact.

The compounds of this invention can be applied in their pure state, but most often apphcation will be of a formulation comprising one or more compounds with suitable carriers, diluents, and surfactants and possibly in combination with a food depending on the contemplated end use. A preferred method of apphcation involves spraying a water dispersion or refined oil solution ofthe compounds. Combinations with spray oils, spray oil concentrations, spreader stickers, adjuvants, other solvents, and synergists such as piperonyl butoxide often enhance compound efficacy.

The rate of apphcation required for effective control (i.e. "biologically effective amount") will depend on such factors as the species of invertebrate to be controlled, the pest's hfe cycle, hfe stage, its size, location, time of year, host crop or animal, feeding behavior, mating behavior, ambient moisture, temperature, and the like. Under normal circumstances, apphcation rates of about 0.01 to 2 kg of active ingredient per hectare are sufficient to control pests in agronomic ecosystems, but as little as 0.0001 kg/hectare may be sufficient or as much as 8 kg/hectare may be required. For nonagronomic applications, effective use rates will range from about 1.0 to 50 mg/square meter but as little as 0J mg/square meter may be sufficient or as much as 150 mg/square meter may be required. One skilled in the art can easily determine the biologically effective amount necessary for the desired level of invertebrate pest control. The following TESTS demonstrate the control efficacy of compounds of this invention on specific pests. "Control efficacy" represents inhibition of arthropod development (including mortality) that causes significantly reduced feeding. The pest control protection afforded by the compounds is not limited, however, to these species. See Index Tables A-B for compound descriptions. The following abbreviations are used in the Index Tables which follow: Me is methyl, t^'-Pr is isopropyl, Ph is phenyl. The abbreviation "dec" indicates that the compound appeared to decompose on melting. The abbreviation "Ex." stands for "Example" and is followed by a number indicating in which example the compound is prepared. INDEX TABLE A

Compound R R4 R7 X Y m.p. °C

1 (Ex. 1) t-Pr 3-1 OCH₂CF₃ CH CH N 220-225

2 (Ex. 1) i-Pr 6-1 OCH₂CF₃ CH CH N 200-203

3 i-Pr 3-Me OCH₂CF₃ CH CH N 205-210

4 i-Pr 6-Me OCH₂CF₃ CH CH N 193-196

INDEX TABLE B

Compound R3 R4 Q X Y Z m.p. °C

5 i-Pr 3-1 Ph N CH CMe 193-194

6 i-Pr 6-1 NPh N CH CMe 216-218

7 i-Pr 3-1 NMe N CH CMe 220-222

8 i-Pr 6-1 NMe N CH CMe 233-234

9 i-Pr 3-1 NMe N CH C-cyclopropyl 222-224

10 i-Pr 6-1 NMe N CH C-cyclopropyl 215-217 ll(Ex. 2) i-Pr 6-1 N(2-ClPh) N CH CCF₃ 234-235

12 (Ex. 2) i-Pr 3-1 N(2-ClPh) N CH CCF₃ 226-228 BIOLOGICAL EXAMPLES OF THE INVENTION

TEST A For evaluating control of diamondback moth (Plutella xylostella) the test unit consisted of a small open container with a 12-14-day-old radish plant inside. This was pre-infested with 10-15 neonate larvae on a piece of insect diet by use of a core sampler to remove a plug from a sheet of hardened insect diet having many larvae growing on it and transfer the plug containing larvae and diet to the test unit. The larvae moved onto the test plant as the diet plug dried out.

Test compounds were formulated using a solution containing 10% acetone, 90% water and 300 ppm X-77® Spreader Lo-Foam Formula non-ionic surfactant containing alkylarylpolyoxyethylene, free fatty acids, glycols and isopropanol (Loveland Industries, Inc.), unless otherwise indicated. The formulated compounds were apphed in 1 mL of hquid through a SUJ2 atomizer nozzle with 1/8 JJ custom body (Spraying Systems Co.) positioned 1.27 cm (0.5 inches) above the top of each test unit. All experimental compounds in this screen were sprayed at 50 ppm and rephcated three times. After spraying ofthe formulated test compound, each test unit was allowed to dry for 1 hour and then a black, screened cap was placed on top. The test units were held for 6 days in a growth chamber at 25 °C and 70% relative humidity. Plant feeding damage was then visually assessed.

Ofthe compounds tested, the following provided excellent levels of plant protection (10% or less feeding damage): 1, 2, 3, 4, 6, 7, 9, 10.

TEST B

For evaluating control of fall armyworm (Spodoptera frugiperda) the test unit consisted of a small open container with a 4-5-day-old corn (maize) plant inside. This was pre-infested with 10-15 1-day-old larvae on a piece of insect diet by use of a core sampler as described for Test A.

Test compounds were formulated and sprayed at 50 ppm as described for Test A. The apphcations were replicated three times. After spraying, the test units were maintained in a growth chamber and then visually rated as described for Test A.

Ofthe compounds tested, the foUowing provided exceUent levels of plant protection (10% or less feeding damage): 1, 9.

TEST C

For evaluating control of tobacco budworm (Heliothis virescens) the test unit consisted of a small open container with a 6-7 day old cotton plant inside. This was pre-infested with

8 2-day-old larvae on a piece of insect diet by use of a core sampler as described for Test A. Test compounds were formulated and sprayed at 50 ppm as described for Test A. The apphcations were replicated three times. After spraying, the test units were maintained in a growth chamber and then visually rated as described for Test A. Ofthe compounds tested, the foUowing provided exceUent levels of plant protection (10% or less feeding damage): 1, 3, 7, 9.

Claims

CLAIMS What is claimed is: 1. A compound of Formula I and N-oxides and agriculturally suitable salts thereof

wherein

R¹ is H, Cι-C₆ alkyl, C₂-Cg alkoxycarbonyl or C₂-Cg alkylcarbonyl;

R² is H or C_rC₆ alkyl;

R is H; C_rC₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₃-C₆ cycloalkyl, or C₄-C₈ cycloalkylalkyl, each optionally substituted with one or more substituents selected from the group consisting of halogen, CΝ, ΝO₂, hydroxy, C₁-C4 alkyl, -C4 alkoxy, C₁-C4 haloalkoxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C₂-Cg alkoxycarbonyl or C₂-Cg alkylcarbonyl; one R⁴ group is attached to the phenyl ring at the 3-position or 6-position, and said R⁴ is C₁-C₄ alkyl, C₁-C haloalkyl, halogen, CN, NO₂, C₁-C4 alkoxy, C1-C4 haloalkoxy, C₁-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 haloalkylthio, C1-C₄ haloalkylsulfinyl, or C₁-C4 haloalkylsulfonyl; and an optional second R⁴ is H, Cj-Cg alkyl, C₂-C₆ alkenyl, C₂-C6 alkynyl, C₃-Cg cycloalkyl, Cι-C₆ haloalkyl, C₂-C6 haloalkenyl, C₂-C6 haloalkynyl, C₃-Cg halocycloalkyl, halogen, CN, NO₂, hydroxy, C1-C4 alkoxy, C1-C4 haloalkoxy, C₁-C₄ alkylthio, C1-C4 alkylsulfinyl, C₁-C₄ alkylsulfonyl, C1-C4 haloalkylthio,

C1-C₄ haloalkylsulfinyl, C1-C₄ haloalkylsulfonyl, C₁-C₄ alkylamino, C₂-Cg dialkylamino, C₃-Cg cycloalkylamino, C1-C4 alkoxyalkyi, C₁-C4 hydroxyalkyl, C(O)R¹⁰ _! CO₂R¹⁰, C(O)NR¹⁰Rⁿ, NR^R¹¹, NfRⁱ^CORⁱ^ N^ⁱ^COaR¹⁰ or C₃-C,5 trialkylsilyl; R⁵ is H, C_rC₄ alkyl, C_rC₄ haloalkyl, or

V is N, CH, CF, CC1, CBr or CI; each R⁶ and R⁷ is independently H, C^Cg alkyl, C₃-Cg cycloalkyl, Cι-C₆ haloalkyl, halogen, CN, C1-C4 alkoxy, Ci -C4 haloalkoxy or C1-C4 haloalkylthio; R⁹ is H, C_rC₆ alkyl, C_rC₆ haloalkyl, C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₃-C₆ alkynyl or C₃-Cg haloalkynyl; provided R⁷ and R⁹ are not both H; R¹⁰ is H or -C₄ alkyl or -C4 haloalkyl; R¹¹ is H or C_!-C₄ alkyl; and n is 1 or 2.

2. The compound of Claim 1 wherein V is N.

3. The compound of Claim 1 wherein V is CH, CF, CC1 or CBr.

4. The compound of Claim 2 or Claim 3 wherein R¹ and R² are both H;

R³ is -C₄ alkyl optionally substituted with halogen, CN, OCH₃, S(O)_pCH₃; one R⁴ group is attached to the phenyl ring at the 3-position and said R⁴ is CH , CF₃,

OCF₃, OCHF₂, S(O)_pCF₃, S(O)_pCHF₂, CN or halogen; a second R⁴ is H, F, Cl, Br, I or CF₃; R⁶ is C1-C4 alkyl, C₁-C4 haloalkyl, halogen or CN; R⁷ is H, CH₃, CF₃, OCHF₂ or halogen; and p is 0, 1 or 2.

5. The compound of Claim 4 wherein J is J-l;

R³ is C_rC₄ alkyl; one R⁴ group is attached to the phenyl ring at the 3-position and said R⁴ is CH , Cl, Br or I; a second R⁴ is H, F, Cl, Br, I or CF₃; R⁶ is Cl or Br; and

R⁷ is halogen or CF₃.

6. The compound of Claim 5 wherein V is N;

R³ is methyl, ethyl, isopropyl or tertiary butyl; one R⁴ group is attached to the phenyl ring at the 3-position and said R⁴ is CH₃ or I;

R⁶ is Cl or Br; and R⁷ is Br, Cl or CF₃.

7. The compound of Claim 6 selected from the group consisting of: N^/-[l-(3-chloro-2-ρvridmyl)-3-(trifluorome1hyl)-lH-pvrazol-5-yl]-3-methyl-N^ methylethyl)- 1 ,2-benzenedicarboxamide,

N -[l-(3-bromo-l-(3-chloro-2-pyridinyl)-lH-pyrazol-5-yl]-3-methyl-N²-(l- methylethyl)- 1 ,2-benzenedicarboxamide,

N -[l-(3-chloro-2-ρyriα yl)-3-(1rifluoromethyl)-lH-pyrazol-5-yl]-3-iodo-N²-(l- methylethyl)-l ,2-benzenedicarboxamide, and N^[l-(3-bromo-l-(3-chloro-2-pyridinyl)-lH-pyrazol-5-yl]-3-iodo-N²-(l- methylethyl)- 1 ,2-benzenedicarboxamide.

8. The compound of Claim 4 wherein J is J-2;

R³ is C_rC₄ alkyl; one R⁴ group is attached to the phenyl ring at the 3-position and said R⁴ is CΗ₃, Cl, Br or I; a second R⁴ is H, F, Cl, Br, I or CF₃;

R⁶ is Cl or Br; and

R⁹ is CF₃, CHF₂, CH₂CF₃, CF₂CHF₂.

9. The compound of Claim 4 wherein

J is J-3; R³ is C_rC₄ alkyl; one R⁴ group is attached to the phenyl ring at the 3-position and said R⁴ is CH₃, Cl, Br or I; a second R⁴ is H, F, Cl, Br, I or CF₃; R⁶ is Cl or Br; and

R⁷ is halogen or CF .

10. The compound of Claim 4 wherein

J is J-4;

R³ is C_rC₄ alkyl; one R⁴ group is attached to the phenyl ring at the 3-position and said R⁴ is CH₃, Cl, Br or I; a second R⁴ is H, F, Cl, Br, I or CF₃;

R⁶ is Cl or Br; and

R⁷ is CF₃.

11. The compound of Claim 4 wherein

J is J-5;

R⁶ is Cl or Br; and

R⁹ is CF₃, CHF₂, CH₂CF₃, CF₂CHF₂.

12. The compound of Claim 4 wherein J is J-6; R³ is C_rC₄ alkyl; one R⁴ group is attached to the phenyl ring at the 3-position and said R⁴ is CH₃, Cl, Br or I; a second R⁴ is H, F, Cl, Br, I or CF₃;

R⁶ is Cl or Br; and R⁷ is halogen or CF₃.

13. The compound of Claim 4 wherein J is J-7;

R3 is C_rC₄ alkyl; one R⁴ group is attached to the K-ring at the 2-position and said R⁴ is CH₃, Cl or Br; a second R⁴ is H, F, Cl, Br, I or CF₃ ;

R⁶ is Cl or Br: R⁷ is H, halogen or CF₃.and

R⁹ is H, CF₃, CHF₂, CH₂CF₃, CF₂CHF₂.

14. The compound of Claim 4 wherein J is J-8; R is C_rC₄ alkyl; one R⁴ group is attached to the phenyl ring at the 3-position and said R⁴ is CH₃, Cl, Br or I; a second R⁴ is H, F, Cl, Br, I or CF₃; R⁶ is Cl or Br; R⁷ is H, halogen or CF₃.and

R⁹ is H, CF₃, CHF₂, CH₂CF₃, CF₂CHF₂.

15. A composition for confrolling an invertebrate pest comprising a biologically effective amount of a compound of Claim 1 and at least one additional component selected from the group consisting of a surfactant, a solid dUuent or a liquid dnuent.

16. The composition of Claim 15 further comprising an effective amount of at least one additional biologically active compound or agent.

17. The composition of Claim 16 wherein at least one additional biologically active compound or agent is selected from arthropodicides ofthe group consisting of pyrethroids, carbamates, neonicotinoids, neuronal sodium channel blockers, insecticidal macrocychc lactones, γ-aminobutyric acid (GAB A) antagonists, insecticidal ureas and juvenile hormone mimics.

18. The composition of Claim 16 wherein at least one additional biologicaUy active compound or agent is selected from insecticide, nematocide, acaricide or biological agents in the group consisting of abamectin, acephate, acetamiprid, avermectin, azadirachtin, azinphos-methyl, bifenthrin, binfenazate, buprofezin, carbofuran, chlorfenapyr, chlorfluazuron, chlorpyrifos, chlorpyrifos-methyl, chromafenozide, clotMartidin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, cypermethrin, cyromazine, deltamethrin, diafenthiuron, diazinon, diflubenzuron, dimethoate, diofenolan, emamectin, endosulfan, esfenvalerate, ethiprole, fenothicarb, fenoxycarb, fenpropathrin, fenproximate, fenvalerate, fipronU, flonicamid, flucythrinate, tau-fluvalinate, flufenoxuron, fonophos, halofenozide, hexaflumuron, imidacloprid, indoxacarb, isofenphos, lufenuron, malathion, metaldehyde, methamidophos, methidathion, methomyl, methoprene, methoxychlor, monocrotophos, methoxyfenozide, nithiazin, novaluron, oxamyl, parathion, parathion-methyl, permethrin, phorate, phosalone, phosmet, phosphamidon, p imicarb, profenofos, pymetrozine, pyridalyl, pyriproxyfen, rotenone, spinosad, sulprofos, tebufenozide, teflubenzuron, tefluthrin, terbufos, tetrachlorvinphos, tbiacloprid, thiamethoxam, thiodicarb, thiosultap-sodium, fralomethrin, trichlorfon and triflumuron, aldicarb, oxamyl, fenamiphos, amitraz, chinomethionat, chlorobenzilate, cyhexatin, dicofol, dienochlor, etoxazole, fenazaquin, fenbutatin oxide, fenpropathrin, fenpyroximate, hexythiazox, propargite, pyridaben, tebufenpyrad; Bacillus thuringiensis i, Bacillus thuringiensis delta endotoxin, baculovirus, and entomopathogenic bacteria, virus and fungi.

19. The composition of Claim 18 wherein at least one additional biologicaUy active compound or agent is selected from insecticide, nematocide, acaricide or biological agents in the group consisting of cypermethrin, cyhalothrin, cyfluthrin and beta-cyfluthrin, esfenvalerate, fenvalerate, fralomethrin, fenothicarb, methomyl, oxamyl, thiodicarb, clothianidin, imidacloprid, thiacloprid, indoxacarb, spinosad, abamectin, avermectin, emamectin, endosulfan, ethiprole, fipronU, flufenoxuron, triflumuron, diofenolan, pyriproxyfen, pymetrozine, amitraz, Bacillus thuringiensis, Bacillus thuringiensis delta endotoxin and entomophagous fungi.

20. A method for controlling an invertebrate pest comprising contacting the invertebrate pest or its environment with a biologically effective amount of a compound of Claim 1 or a composition of Claim 17.