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Title:
ARTHROPODICIDAL AMIDES
Document Type and Number:
WIPO Patent Application WO/1993/018038
Kind Code:
A1
Abstract:
Insecticidal compounds of the formula (I) wherein G, X, Y and Q are as defined in the text, agricultural compositions containing them and a method for using the compounds to control arthropods in agronomic and nonagronomic environments.

Inventors:
LOWDER PATRICK DOYLE (US)
Application Number:
PCT/US1993/001532
Publication Date:
September 16, 1993
Filing Date:
February 26, 1993
Export Citation:
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Assignee:
DU PONT (US)
International Classes:
C07D307/81; A01N47/38; C07C251/86; C07D211/18; C07D211/20; C07D211/46; C07D211/70; C07D211/74; C07D273/04; C07D401/12; C07D471/04; C07D491/04; C07D491/052; (IPC1-7): A01N47/38; C07D231/00; C07D231/06; C07D311/00; C07D491/052
Foreign References:
EP0443162A11991-08-28
GB1570635A1980-07-02
EP0438690A21991-07-31
EP0386892A21990-09-12
EP0333131A11989-09-20
Other References:
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY vol. 25, no. 5, 1977, WASHINGTON US pages 987 - 992 K. WELLINGA ET AL '1-Phenylcarbamoyl-2-pyrazolines: A new class of insecticides. 1. Synthesis and insecticidal properties of 3-phenyl-1-phenylcarbamoyl-2-pyrazolines'
CHEMICAL ABSTRACTS, vol. 90, no. 9, 26 February 1979, Columbus, Ohio, US; abstract no. 72105u, A. FRAVOLINI ET AL 'Synthesis and pharmacological activity of benzothiopyranopyrazole and benzothiopyranoisoxazole carboxamides' page 509 ;
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Claims:
1. A compound of the formula wherein : Q is selected from the group Ql Q2 Q3 Q4 Q5 Q6 A is H; E is selected from the group H and 0^^ alkyl; or A and E can be taken together to form CH , CH2CH2, 0, S S(O), S(0)2, NR7, 0CH2, SCH2, NfR7)CE substituted CH2, and substituted Ch2CH2 . A substitu .s independently selected from 1.
2. „ .alogen and.
3. methyl; M is selected from the group H and C1C3 alkyl; c ' and M can be taken together as CH2CH2, CH2CH :. or CH2CH2CH2CH2 each group optionally substitutec with one or more members independently selected from the group halogen, N02, CN, CiCs alkyl, ^05 haloalkyl, OH, OR6 and C02R19; G is selected * om the group Gl G2 G3 G being G2 or G3 when Q is Ql, A and E are not taken together and R3 is J; 7 is selected from the group 0 and S; Y is selected from the group H; ^Cg alkyl; benzyl; C2C6 alkenyl; C2C6 alkynyl; CiCg alkyl substituted by halogen, CxC3 alkoxy, C^^ haloalkoxy, CN, N02, S(0)rR30, C(0)R30, C(0)2R30, and phenyl optionally substituted by halogen, CN, CJLC2 haloalkyl and C1C2 haloalkoxy; C3C6 cycloalkyl; C3C6 halocycloalkyl; C C6 cycloalkylalkyl; CHO; C2C6 alkylcarbonyl; C2C6 alkoxycarbonyl; C2C6 haloalkylcarbonyl; C(0)R33; C(0)2R33; CiCg alkylthio; CjtCg haloalkylthio; phenylthio; RlxOC(0)N(R12)S; R13(R14)NS; N=CR9R10; OR8 and NR8R9; Z is selected from the group CH2, 0, S and NR29; R1 and R2 are independently selected from the group H, cι~c6 alkyl, C^C haloalkyl, C2C6 alkenyl, C2C6 haloalkenyl, C2C6 alkynyl, C3C6 haloalkynyl, C2C6 alkoxyalkyl, C2C6 alkylthioalkyl, C^Cg nitroalkyl, C2Cg cyanoalkyl, C3C8 alkoxy¬ carbonylalkyl, C3C6 cycloalkyl, C3C6 halocyclo alkyl, halogen, CN, N3, SCN, N02, OR16, SR17, S(0)R16, S(0)2R16, OC(0)R16, OS(0)2R16, C(0)2R16, C(0)R16, C(0)NR16R17, S(0)2NR16R17, NR16R17, NR17C(0)R16, 0C(0)NHR16, NR17C(O)NHR16, NR17S(0) R16, phenyl optionally substituted with 1 to 3 substituents independently selected from W, and benzyl optionally substituted with 1 to 3 substituents independently selected from W; or when m or n is 2, (Rx) can be taken together, or (R2)2 can be taken together as OCH20, 0CF20, OCH2CH20, CH2C(CH3)20, CF2CF20 or OCF2CF20 to form a cyclic bridge; provided that when R1 or R2 is S(0)R16, S(0)2R16r 0C(0)R16 or OS(0)2R16 then R16 is other than H; and R1 being other than haloalkyl and haloalkoxy when G is Gl, Q is Ql, A and E are not taken together and R3 is optionally substituted phenyl, optionally substituted alkyl, or C(0)2(C1C6 alkyl); R3 is selected from the group H, J, N3, N02, halogen, N(R21)R22, C(R31)=N0R32, C^Cg alkyl, CiC haloalkyl, C2Cg alkenyl, C2C6 haloalkenyl, C2C6 alkynyl, C2C6 alkoxyalkyl, C3C8 alkoxycarbonyl¬ alkyl, C(0)R16, C(0)2R16, OR18, C(0)NR16R17, C(S)NR16R17, C(S)R16, C(S)SR16, CN, Si(R26) (R27)R25, SR25, S(0)R25, S(0)2R25, P(0) (OR25)2, phenyl optionally substituted with (R15)p, and benzyl optionally substituted with 1 to 3 substituents independently selected from W; or R3 is C C6 epoxyalkyl optionally substituted with one or more members independently selected from the group C1C3 alkyl, CN, C(0)R23, C(0)2R23 and pheny optionally substituted withW; or R3 is C1Cg alkyl substituted with one or more members independently selected from the group C(0)N(R2 )R34, C(0)R24, SR25, S(0)R25, S(0)2R25, SCN, CN, CJ.C2 haloalkoxy, Si (R26) (R27)R28, N(R21)R22, N02, OC(0)R24, P(0) (OR25)2 and J; J is selected from the group saturated, partially unsaturated or aromatic 5 or 6membered . heterocyclic ring, bonded through carbon or nitrogen, containing 14 heteroatoms independently selected from the group consisting of 02 oxygen, 02 sulfur and 04 nitrogen, this substituent optionally containing one carbonyl and optionally substituted with one or more members independently selected from W; R4 and R5 are independently selected from the group H, CLCi alkyl, C(0)R19 and C2C alkoxycarbonyl; R6 is selected from the group H, C1C4 alkyl, C(0)R19 and C(0)2R19; R7 is selected from the group H, C1C4 alkyl, C^^ haloalkyl, C2C4 alkenyl, C2C4 haloalkenyl, SR16, S(0)R16, S(0)2R16, C(0)R16, C(0)2R16, C(0)NR16R20, C(S)NR16R20, C(S)R16, C(S)0R16, P (0) (OR16)2, P(S) (OR16)2, P(O) (R16)OR16, P (0) (R16)SR20, optionally substituted phenyl, and optionally substituted benzyl wherein the optional phenyl and benzyl substituent(s) are independently selected from F, Cl, Br, CH3, CF3 or OCF3; provided that when R7 is other than C(0)R16, C(0)NR16R20 or C(S)NR16R20 then R16 is other than H; R8 is selected from the group H, C1C alkyl, C1C haloalkyl, C C alkenyl, C2C4 alkynyl, S02NR17R18, S(0)2R16, C(0)R16, C(0)NR16R20, C(0)2R16, phenyl optionally substituted with halogen or C1C4 alkoxy, and benzyl optionally substituted with halogen; provided that when R8 is S(0)2R16, R16 is other than H; R9 is selected from the group H, C^C^ alkyl and C(0)R16; R10 is selected from the group H, CxC4 alkyl, Cj^C^ haloalkyl, and phenyl optionally substituted with one or more members independently selected from the group halogen, CN, N02, CF3 and OCF3; or R9 and R10 can be taken together as CH2CH2CH2, —CH2CH2CH2CH2_ or —CH2CH2CH2CH2CH2—; R11 is CiCg alkyl; R12 is C1C4 alkyl; R13 and R14 are independently C1C4 alkyl; or R13 and R14 can be taken together as CH2CH2CH2CH2CH2 or CH2CH2OCH2CH2; R15 is selected from the group CxCg alkyl, CiCg haloalkyl, C2C6 alkenyl, C2C6 haloalkenyl, C2C6 alkynyl, C3Cg haloalkynyl, C C6 alkoxyalkyl, C2C6 alkylthioalkyl, Cj^C nitroalkyl, C C6 cyanoalkyl, C3C8 alkoxycarbonylalkyl, C3C6 cycloalkyl, C3Cg halocycloalkyl, halogen, CN, N3, SCN, N02, OR16, SR16, S(0)R16, S(0)2R16, OC(0)R16, OS(0)2R16, C(0)2R16, C(0)R16, C(0)NR16R17, S(0)2NR16R17, NR16R17, NR17C(0)R16, OC(0)NHR16, NR17C(0)NHR16, NR17S(0)2R16. phenyl optionally substituted with 1 to 3 substituents independently selected from W, and benzyl optionally substituted with 1 to 3 substituents independently selected from W; or when p is 2, (R15)2 can be taken together as 0CH20, OCF 0, OCH2CH20, CH2C(CH3)20, CF2CF20 or OCF2CF20 to form a cyclic bridge; provided that when R15 is S(0)R16, S(0)2R16, OC(0)R16 or OS(0)2R16 then R16 is other than H; R16 is selected from the group H, CiCg alkyl, C1C6 haloalkyl, C C6 alkenyl, C2C6 haloalkenyl, C2C6 alkynyl, C3C6 haloalkynyl, C C6 alkoxyalkyl, C2C6 alkylthioalkyl, C^C nitroalkyl, C2C6 cyanoalkyl, C3C8 alkoxycarbonylalkyl, C3C6" cycloalkyl, C3Cg halocycloalkyl, optionally substituted phenyl, and optionally substituted benzyl wherein the optional phenyl and benzyl substituents are 1 to 3 substituents independently selected from W; R17 is selected from the group H and C1C4 alkyl; or R16 and R17, when attached to the same atom, can be taken together as (CH2)4, (CH2)5, or CH2CH2OCH2CH2; R18 is selected from the group H, C1C4 alkyl, C2C4 alkenyl, C2C4 alkynyl, C2C4 alkylcarbonyl, C2C4 alkoxycarbonyl and ^04 alkylsulfonyl; R19 is CxC3 alkyl; R20 is selected from the group H, C1C4 alkyl, C2C4 alkenyl and C2C alkynyl; R21 is selected from the group H, C2C7 alkylcarbonyl, C2C7 alkoxycarbonyl, optionally substituted C!C4 alkyl, optionally substituted C2C4 alkenyl, and optionally substituted C2C4 alkynyl, all of these optional substituents being independently selected from C!C2 alkoxy, CN, C(0)R28 and C(0)2R25; R22 is selected from the group H, C1C3 alkyl, phenyl optionally substituted with at least one member independently selected from W, and benzyl optionally substituted with at least one member independently selected from W; R23 is selected from the group H, OfC^ alkyl, C2C alkenyl and C2C4 alkynyl; R24 is selected from the group H and C1C2 alkyl; R25 j_s selected from the group ^^ alkyl and phenyl optionally substituted with at least one member independently selected from W; R26 is C C3 alkyl; R27 is C1C3 alkyl; R28 is selected from the group H, C1C3 alkyl and phenyl optionally substituted with at least one member independently selected from W; R29 is selected from the group H, C^ C^ alkyl, C C4 alkylcarbonyl and C2C4 alkoxycarbonyl; R30 is CiC3 alkyl; R31 is selected from the group H, Cl, C^C^ alkyl, ^04 alkoxy, ^02 alkylthio and CN; R32 is selected from the group H, C1 .4. alkyl, C2C3 alkylcarbonyl and C2C3 alkoxycarbonyl; R33 s phenyl, optionally substituted with at least one member independently selected from W; R34 is selected from the group H and CxC2 alkyl; W is selected from the group halogen, CN, N02, C1C2 alkyl, C1C2 haloalkyl, C1C2 alkoxy, C1C2 haloalkoxy, C1C2 alkylthio, C1C2 haloalkylthio, C1C2 alkylsulfonyl and CxC2 haloalkylsulfonyl; m is 1 to 3; n is 1 to 3; p is 1 to 3; and is 0, 1 or 2.
4. 2 A compound according to Claim 1 wherein: R1 is selected from the group H, CiCg alkyl, CiC haloalkyl, C2C6 alkenyl, C2C6 haloalkenyl, C2C6 alkynyl, C3C6 haloalkynyl, C2C6 alkoxyalkyl, C C6 alkylthioalkyl, CxCg nitroalkyl, C2C6 cyanoalkyl, C3C8 alkoxycarbonylalkyl, C3C6 cycloalkyl, C3Cg halocycloalkyl, halogen, CN, SCN, N02, OR16, SR16, S(0)2R16, C(0)2R16, C(0)R16, phenyl optionally substituted with 1 to 3 substituents independently selected from W, and benzyl optionally substituted with 1 to 3 substituents independently selected from W; with one R1 substituent in the 4position, or when m is 2 then (Rx) can be taken together as CH2C(CH3)20, OCH2CH20, OCF2CF20, or CF2CF20 to form a 5 or 6membered fused ring; R2 is selected from the group H, Cj^C alkyl, C^Cg haloalkyl, C2C6 alkenyl, C2Cg haloalkenyl, C2C6 alkynyl, C3Cg haloalkynyl, C2C6 alkoxyalkyl, C2C6 alkylthioalkyl, CiCg nitroalkyl, C2C6 cyanoalkyl, C3C8 alkoxycarbonylalkyl, C3Cg cycloalkyl, C3Cg halocycloalkyl, halogen, CN, SCN, N02, OR16, SR16, S(0)2R16, OC(0)R16, OS(0)2R16, C(0)2R16, C(0)R16, C(0)NR16R17, S(0)2NR16R17, NR16R17, phenyl optionally substituted with 1 to 3 substituents independently selected from W, and benzyl optionally substituted with 1 to 3 substituents independently selected from W; R3 is selected from the group H, C1C alkyl, C3C4 alkoxycarbonylalkyl, C(0)2R16, C(0)R16, and phenyl optionally substituted by one or more substituents independently selected from (R15)p; R15 is selected from the group CLCg alkyl, C^C haloalkyl, C2Cg alkenyl, C C6 haloalkenyl, C2C6 alkynyl, C3Cg haloalkynyl, C2C6 alkoxyalkyl, C2C6 alkylthioalkyl, CiCg nitroalkyl, C2C6 cyanoalkyl, C3C8 alkoxycarbonylalkyl, C3C6 cycloalkyl, C3C6 halocycloalkyl, halogen, CN, SCN, N02, OR16, SR16, S(0)2R16, OC(0)R16, OS(0)2R16, C(0)2R16, C(0)R16, C(0)NR16R17, S(O)2NRx6R17, NR16R17, phenyl optionally substituted with 1 to 3 substituents independently selected from W, and benzyl optionally substituted with 1 to 3 substituents independently selected from W; • R16 is selected from the group CJIC4 alkyl, C1C2 haloalkyl, C3C4 alkenyl and propargyl; R17 is selected from the group H and CH3; and m is 1 or 2.
5. A compound according to Claim 2 wherein G is Gl and R4 and R5 are each H.
6. A compound according to Claim 2 wherein G is G2 and R4 and R5 are each H.
7. A compound according to Claim 3 wherein Q is selected from the group Ql, Q2 and Q5.
8. A compound according to Claim 4 wherein Q is selected from Ql, Q2 and Q5.
9. A compound according to Claim 4 selected from the group consisting of: methyl 2,3dihydro7(tri¬ fluoromethyl)2[[4(trifluoromethyl)1piperidinyl amino]carbonyl] [1]benzopyrano[4,3c]pyrazole3a(4H) carboxylate; 3,4bis(4chlorophenyl)4,5dihydroN[4 (trifluoromethyl)1piperidinyl]lHpyrazole1 carboxamide; methyl 7chloro2,5dihydro2[[[4(tri¬ fluoromethyl)1piperidinyl]amino]carbonyl]indeno[1,2 e] [1,3,4]oxadiazine4a(3H)carboxylate; and 2(5fluoro 2,3dihydro2methyllHindenlylidene)N[4(trifluoro¬ methyl)1piperidinyl]hydrazinecarboxamide.
10. An arthropodicidal composition comprising an arthropodically effective amount of a compound according to any one of Claims 1 to 7 and a carrier therefor.
11. A method for controlling arthropods comprising contacting them or their environment with an arthro¬ podically effective amount of a compound according to any one of Claims 1 to 7.
Description:
TITLE ARTHROPODICIDAL AMIDES EP-A-443,162 discloses insecticidal pyrazoline cyclohexyl amides but neither describes nor suggests the particular compounds of this invention.

SUMMARY OF THE INVENTION This invention pertains to amides of Formula I including all geometric and stereoisomers, suitable salt thereof, useful compositions containing them and use of these compounds to control arthropods in both agronomic and nonagronomic environments. The term "compounds" wil be understood to include all such isomers and salts thereof. The compounds are:

wherein:

Q is selected from the group

Q-l Q-2

Q-3 Q-4

Q-5 Q-6

A is H;

E is selected from the group H and Cι~C 3 alkyl; or A and E can be taken together to form -CH 2 -, -CH 2 CH -, -0-, -S-, -S(O)-, -S(0) 2 -, -NR 7 -, -OCH 2 -, -SCH 2 -, -N(R 7 )CH 2 -, substituted -CH 2 -, and substituted -CH 2 CH 2 - the substituents independently selected from 1-2 halogen and 1-2 methyl; M is selected from the group H and 0 3 ^ 3 alkyl; or E and M can be taken together as -CH 2 CH 2 -, -CH 2 CH 2 CH 2 - or -CH 2 CH 2 CH 2 CH 2 - each group optionally substituted with one or more members independently selected from the group halogen, N0 2 , CN, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, OH, OR 6 and C0 2 R 19 ; G is selected from the group

-l G-2 G-3

G being G-2 or G-3 when Q is Q-l, A and E are not taken together and R 3 is J; X is selected from the group 0 and S; Y is selected from- the group H; (-^-Cg alkyl; benzyl; c 2 ~^ 6 alkenyl; C 2 -C 6 alkynyl; C^Cg alkyl substituted by halogen, C- L -C3 alkoxy, C -C- } haloalkoxy, CN, N0 2 , S(0) r R 30 , C(0)R 30 , C(0) 2 R 3 °, and phenyl optionally substituted by halogen, CN C 1 -C haloalkyl and C 1 -C 2 haloalkoxy; C3-C 6 cycloalkyl; C 3 -C 6 halocycloalkyl; C -C 6 cycloalkylalkyl; CHO; C -C 6 alkylcarbonyl; C 2 -C 6 alkoxycarbonyl; C 2 -C 6 haloalkylcarbonyl; C(0)R 33 ; C(0) 2 R 33 ; C- jL -Cg alkylthio; C^-C haloalkylthio; phenylthio; R 13 -OC (O)N(R 12 ) S-; R 13 (R 14 )NS-; N=CR 9 R 10 ; OR 8 and NR 8 R 9 ;

Z is selected from the group CH , 0, S and NR 29 ; R 1 and R 2 are independently selected from the group Ci-C alkyl, C^C haloalkyl, C 2 -C 6 alkenyl, C 2 -C haloalkenyl, C 2 -C 6 alkynyl, C 3 -C 6 haloalkynyl, C 2 -C 6 alkoxyalkyl, C 2 -C 6 alkylthioalkyl, C 1 -C 6 nitroalkyl, C 2 -Cg cyanoalkyl, C 3 -C 8 alkoxy- carbonylalkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 halocyclo¬ alkyl, halogen, CN, N 3 , SCN, N0 2 , OR 16 , SR 17 , S(0)R 16 , S(0) 2 R 16 , OC(0)R 16 , OS(0) 2 R 16 , C(0) 2 R 16 , C(0)R 16 , C(0)NR 16 R 17 , S (O) 2 NR 16 R 17 , NR 16 R 17 ,

NR 17 C(0)R 16 , OC(0)NHR 16 , NR 17 C (O)NHR 16 , NR 17 S (0) 2 R 16 , phenyl optionally substituted with to 3 substituents independently selected from , and benzyl optionally substituted with 1 to 3 substituents independently selected from W; or when m or n is 2, (R 1 ) 2 can be taken together, o (R 2 ) 2 can be taken together as -OCH 2 0-, -OCF 2 0-, -OCH 2 CH 2 0-, -CH 2 C(CH 3 ) 2 0-, -CF 2 CF 2 0- or -OCF 2 CF 2 0- to form a cyclic bridge; provided that when R 1 o

R 2 is S(0)R 16 , S(0) 2 R 16 , OC(O)R 16 or OS(0) 2 R 16 then R 16 is other than H; and R 1 being other than haloalkyl and haloalkoxy when G is G-l, Q is Q-l, A and E are not taken together and R 3 is optionally substituted phenyl, optionally

' substituted alkyl, or C(0) (C 1 -C 6 alkyl); R 3 is selected from the group H, J, N 3 , N0 , halogen, N(R 21 )R 22 , haloalkyl, C 2 -C 6 alkenyl, C -C 6 haloalkenyl, C 2 -C 6 alkynyl, C 2 -Cg alkoxyalkyl, C 3 -C 8 alkoxycarbonyl- alkyl, C(0)R 16 , C(0) 2 R 16 , OR 18 , C(0)NR 16 R 17 , C(S)NR 16 R 17 , C(S)R 16 , C(S)SR 16 , CN, Si(R 26 ) (R 27 )R 25 , SR 25 , S(0)R 25 , S(0) 2 R 25 , -P(0) (OR 25 ) 2 , phenyl optionally substituted with (R 15 ) p , and benzyl optionally substituted with 1 to 3 substituents independently selected from W; or R 3 is C 2 -Cg epoxyalkyl optionally substituted with one or more members independently selected from the group C- J -C 3 alkyl, CN, C(0)R 23 , C(O) 2 R 23 and phenyl optionally substituted with ; or R 3 is C^-C alkyl substituted with one or more members independently selected from the group C(0)N(R 24 )R 34 , C(0)R 24 , SR 25 , S(0)R 25 , S(0) 2 R 25 , SCN, CN, C 1 -C 2 haloalkoxy. Si(R 26 ) (R 27 )R 28 , N(R 21 )R 22 , N0 2 , OC(0)R 24 , -P(0) (0R 25 ) 2 and J;

J is selected from the group saturated, partially unsaturated or aromatic 5- or 6-membered heterocyclic ring, bonded through carbon or nitrogen, containing 1-4 heteroatoms independently selected from the group consisting of 0-2 oxygen, 0-2 sulfur and 0-4 nitrogen, this substituent optionally containing one carbonyl and optionally substituted with one or more members independently selected from ;

R 4 and R 5 are independently selected from the group C 2 -C 4 alkyl, C(0)R 19 and C 2 -C alkoxycarbonyl;

R 6 is selected from the group H, ^-0 4 alkyl, C(0)R 19 and C(0) 2 R 19 ; R 7 is selected from the group H, C 2 -C 4 alkyl, C 1 -C 4 haloalkyl, C 2 -C 4 alkenyl, C 2 -C 4 haloalkenyl, SR 16 S(0)R 16 , S(0) 2 R 16 , C(0)R 16 , C(0) 2 R 16 , C(0)NR 16 R 20 , C(S)NR 16 R 20 , C(S)R 16 , C(S)OR 16 , -P (O) (OR 16 ) 2 , -P(S) (OR 16 ) 2 , -P(O) (R 16 )OR 16 , -P(O) (R 16 )SR 20 , optionally substituted phenyl, and optionally substituted benzyl wherein the optional phenyl and benzyl substituent(s) are independently selected from F, Cl, Br, CH 3 , CF 3 or OCF 3 ; provided that when R 7 is other than C(0)R 16 , C(0)NR 16 R 20 or C(S)NR l <>R 20 then R 16 is other than

H;

R 8 is selected from the group H, C 1 -C 4 alkyl, ^-0 4 haloalkyl, C 2 -C 4 alkenyl, C -C 4 alkynyl, S0 2 NR 17 R 18 , S(0) 2 R 16 , C(0)R 16 , C(0)NR 16 R 20 , C(0) 2 R 16 , phenyl optionally substituted with halogen or C- j _-C 4 alkoxy, and benzyl optionally substituted with halogen; provided that when R 8 S(0) 2 R 16 , R 16 is other than H;

R 9 is selected from the group H, ^-0 4 alkyl and C(0)R 16 ;

R 10 is selected from the group H, 0 3^ -0 4 alkyl, C ; ..-C 4 haloalkyl, and phenyl optionally substituted wit one or more members independently selected from the group halogen, CN, N0 2 , CF 3 and OCF 3 ; or R 9 and R 10 can be taken together as -CH 2 CH 2 CH 2 -, —CH 2 CH 2 CH 2 CH _ or —CH 2 CH 2 CH CH 2 CH 2 —;

R 11 is Ci-Cg alkyl;

R 12 is C- X -C 4 alkyl;

R 13 and R 14 are independently C \ -Ci_, alkyl; or

R 13 and R 14 can be taken together as -CH 2 CH 2 CH 2 CH 2 CH 2 - or -CH2CH2OCH2CH2-; R 15 is selected from the group C^C alkyl, Ci-C haloalkyl, C 2 -C 6 alkenyl, C 2 -Cg haloalkenyl, C 2 -Cg alkynyl, C3~C 6 haloalkynyl, C -C 6 alkoxyalkyl,

C 2 -C 6 alk lthioalkyl , Ci-C nitroalkyl, C 2 -C 6 cyanoalkyl, C 3 -C 8 alkoxy carbonylalkyl , C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl, halogen, CN, N 3 , SCN, N0 2 , OR 16 , SR 16 , S (0) R 16 , S (0) 2 R 16 , OC (0) R 16 , OS (0) 2 R 16 , C (0) 2 R 16 , C (0) R 16 , C (0) NR 16 R 17 ,

S(0) 2 NR 16 R 17 , NR 16 R 17 , NR 17 C(O)R 16 , 0C(0)NHR 16 , NR 17 C(0)NHR 16 , NR 17 S(0) 2 R 16 , phenyl optionally substituted with 1 to 3 substituents independently selected from , and benzyl optionally substituted with 1 to 3 substituents independently selected from W; or when p is 2, (R 15 ) can be taken together as -OCH 2 0-, -0CF 2 0-, -0CH 2 CH 2 0-, -CH 2 C(CH 3 ) 2 0-, -CF 2 CF 2 0- or -OCF 2 CF 2 0- to form a cyclic bridge; provided that when R 15 is S(0)R 16 , S(0) 2 R 16 , OC(0)R 16 or OS(0) 2 R 16 then R 16 is other than H; R 16 is selected from the group H, Cx-Cg alkyl, C-^C haloalkyl, C 2 -Cg alkenyl, C 2 -Cg haloalkenyl, C 2 -Cg alkynyl, C 3 -Cg haloalkynyl, C 2 -C 6 alkoxyalkyl, c 2 ~ c 6 alkylthioalkyl, C^-CQ nitroalkyl, C 2 -C 6 cyanoalkyl, C 3 -C 8 alkoxycarbonylalkyl, C 3 -Cg cycloalkyl, C 3 -Cg halocycloalkyl, optionally substituted phenyl, and optionally substituted benzyl wherein the optional phenyl and benzyl substituents are 1 to 3 substituents independently selected from ; R 17 is selected from the group H and C- -C alkyl; or

P 15 and R 17 , when attached to the same atom, can be taken together as -(CH 2 ) 4 -, -(CH 2 ) 5 -, or -CH 2 CH 2 OCH 2 CH 2 -;

R 18 is selected from the group H, C 1 -C 4 alkyl, C 2 -C alkenyl, C -C 4 alkynyl, C 2 -C alkylcarbonyl, C 2 -C alkoxycarbonyl and ^-0 4 alkylsulfonyl;

R 19 is Cx-Cg alkyl;

R 20 is selected from the group H, ^-0 4 alkyl, C 2 -C 4 alkenyl and C 2 -C 4 alkynyl; R 21 is selected from the group H, C 2 -C 7 alkylcarbonyl C -C 7 alkoxycarbonyl, optionally substituted ^-0 alkyl, optionally substituted C 2 -C 4 alkenyl, and optionally substituted C -C 4 alkynyl, all of thes optional substituents being independently selected from C 1 -C 2 alkoxy, CN, C(0)R 28 and

C(0) 2 R 25 ;

R 22 is selected from the group H, C- j :-C 3 alkyl, phenyl optionally substituted with at least one member independently selected from , and benzyl optionally substituted with at least one member independently selected from W;

R 23 is selected from the group H, ^-0 4 alkyl, C 2 -C 4 alkenyl and C 2 -C alkynyl;

R 24 is selected from the group H and C 1 -C 2 alkyl; R 25 is selected from the group ^-0 3 alkyl and phenyl optionally substituted with at least one member independently selected from ;

R 26 is C ! -C 3 alkyl;

R 27 is C -0 2 alkyl; R 28 is selected from the group H, ^-0 3 alkyl and phenyl optionally substituted with at least one member independently selected from W;

R 29 is selected from the group H, C 1 -C 4 alkyl, C -C 4 alkylcarbonyl and C 2 -C alkoxycarbonyl;

R 30 is Ci- -Cs alkyl;

R3 1 is selected from the group H, Cl, C x -C 4 alkyl, c i~ c 4 alkoxy, C;L-C 2 alkylthio and CN; R32 s selected from the group H, C-^-C^ alkyl, C 2 -C 3 alkylcarbonyl and C 2 -C 3 alkoxycarbonyl;

R 33 is phenyl, optionally substituted with at least one member independently selected from ; R 34 is selected from the group H and C 1 -C alkyl; W is selected from the. group halogen, CN, N0 2 , C 1 -C 2 alkyl, C 1 -C 2 haloalkyl, C x -C 2 alkoxy, C 1 -C 2 haloalkoxy, C 1 -C 2 alkylthio, - -C 2 haloalkylthio,

C 1 -C alkylsulfonyl and C- J .-C 2 haloalkylsulfonyl; m is 1 to 3; n is 1 to 3; p is 1 to 3; and r is 0, 1 or 2.

Exemplary values of J include:

J-4 J-5 J-6

σ-7 J-8 J-9

J-10 J-ll J-12

J-13 J-14 J-15

J-16 J-17 J-18

J-19 J-20

Preferred for reasons including ease of synthesis and/or greater arthropodicidal efficacy are the followin compounds.

Preferred Compounds A are those wherein:

R 1 is selected from the group H, C^C alkyl, C^-Cg haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C alkynyl, C 3 -C 6 haloalkynyl, C 2 -C 6 alkoxyalkyl,

C 2 -C 6 alkylthioalkyl, C^Cg nitroalkyl, C 2 -C 6 cyanoalkyl, C 3 -C 8 alkoxycarbonylalkyl, C 3 -C 6 cycloalkyl, C 3 -Cg halocycloalkyl, halogen, CN, SCN, N0 2 , OR 16 , SR 16 , S(0) 2 R 16 , C(0) 2 R , C(0)R 16 ,

phenyl optionally substituted with 1 to 3 substituents independently selected from W, and benzyl optionally substituted with 1 to 3 substituents independently selected from W; with one R 1 substituent in the 4-position, or when m is 2 then (R 1 ) 2 can be taken together as -CH 2 C(CH 3 ) 2 0-, -OCH 2 CH 2 0-, -OCF 2 CF 2 0-, or -CF CF 2 0- to form a 5- or 6-membered fused ring; R 2 is selected from the group H, C- j^ -C alkyl, Cj ^ -Cg haloalkyl, C -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -Cg alkynyl, C 3 -Cg haloalkynyl, C 2 -Cg alkoxyalkyl, C 2 -C 6 alkylthioalkyl, Cx-Cg nitroalkyl, C 2 -C 6 cyanoalkyl, C 3 -C 8 alkoxycarbonylalkyl, C 3 -Cg cycloalkyl, C 3 -C 6 halocycloalkyl, halogen, CN, SCN, N0 2 , OR 16 , SR 16 , S(0) 2 R 16 , OC(0)R 16 ,

OS(0) 2 R 16 , C(0) 2 R 16 , C(0)R 16 , C(0)NR 16 R 17 , S(0) 2 NR 16 R 17 , NR 16 R 17 , phenyl optionally substituted with 1 to 3 substituents independently selected from , and benzyl optionally substituted with 1 to 3 substituents independently selected from W; R 3 is selected from the group H, C^-C^ alkyl, C 3 -C 4 alkoxycarbonylalkyl, C(0) R 16 , C(0)R 16 , and phenyl optionally substituted by one or more substituents independently selected from (R 15 ) p ;

R 15 is selected from the group Cx-Cg alkyl, Cx-C haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl, C 3 -C 6 haloalkynyl, C 2 -Cg alkoxyalkyl, C 2 -C 6 alkylthioalkyl, Cx-C nitroalkyl, C 2 -C 6 cyanoalkyl, C 3 -C 8 alkoxycarbonylalkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl, halogen, CN, SCN, N0 2 , OR 16 , SR 16 , S(0) 2 R 16 , OC(0)R 16 , OS(0) 2 R 16 , C(0) 2 R 16 , C(0)R 16 , C(0)NR 16 R 17 , S(0) 2 NR 16 R 17 , NR 16 R 17 , phenyl optionally substituted with 1 to 3

substituents independently selected from , and benzyl optionally substituted with 1 to 3 substituents independently selected from ; R 16 is selected from the group C- X -C 4 alkyl, Ci-C 2 haloalkyl, C 3 -C alkenyl and propargyl;

R 17 is selected from the group H and CH 3 ; and m is 1 or 2.

Preferred Compounds B are those of Preferred A wherein G is G-l, R 4 is H and R 5 is H. Preferred Compounds C are those of Preferred A wherein G is G-2, R is H and R 5 is H. Preferred Compounds D are those of Preferred B wherein Q is Q-l. Preferred Compounds E .are those of Preferred B wherein Q is Q-2. Preferred Compounds F are those of Preferred B wherein Q is Q-5. Preferred Compounds G are those of Preferred C wherein Q is Q-l. Preferred Compounds H are those of Preferred C wherein Q is Q-2. Preferred Compounds I are those of Preferred C wherein Q is Q-5.

Specifically preferred are the compounds of Preferre C which are:

(J) methyl 2,3-dihydro-7-(trifluoromethyl)-2-[ [4- (trifluoromethyl)-1-piperidinylamino]carbonyl]- [l]benzopyrano[4,3-c]-pyrazole-3a(4H)- carboxylate; (K) 3,4-bis(4-chlorophenyl)-4,5-dihydro-N-[4-

(trifluoromethyl)-1-piperidinyl]-lH-pyrazole-1- carboxamide; (L) methyl 7-chloro-2,5-dihydro-2-[[[4- (trifluoro¬ methyl)-1-piperidinyl]amino]carbonyl]-indeno[1,2 e] [1,3,4]oxadiazine-4a(3H)-carboxylate; and

(M) 2-(5-fluoro-2,3-dihydro-2-methyl-lH-inden-l- ylidene)-N-[4-(trifluoromethyl)-1-piperidinyl]- hydrazinecarboxamide.

In the above definitions, the term "alkyl", used either alone or in compound words such as "alkylthio" or "haloalkyl", denotes straight chain or branched alkyl, such as methyl, ethyl, n-propyl, isopropyl or the different butyl, pentyl, hexyl isomers. "Alkoxy" denotes methoxy, ethoxy, n-propyloxy, isopropyloxy and the different butoxy or pentoxy isomers. "Alkenyl" denotes straight chain or branched alkenes, such as vinyl, 1-propenyl, 2-propenyl, 3-propenyl and the different butenyl, pentenyl and hexenyl isomers. "Alkynyl" denotes straight chain or branched alkynes, such as ethynyl, 1-propynyl, 3-propynyl and the different butynyl, pentynyl and hexynyl isomers. "Alkylthio" denotes methylthio, ethylthio and the different propylthio, butylthio, pentylthio and hexylthio isomers.

"Alkylsulfinyl", "alkylsulfonyl", "alkylamino", and the like, are defined analogously to the above examples. "Cycloalkyl" denotes cyclopropyl, cyclobutyl, cyclopentyl and σyclohexyl. The term "halogen", either alone or in compound words such as "haloalkyl", denotes fluorine, chlorine, bromine or iodine. Further, when used in compound words such as "haloalkyl" said alkyl can be partially or fully substituted with halogen atoms, which can be the same or different. Examples of haloalkyl include CH 2 CH 2 F, CF 2 CF 2 and CH 2 CHFC1. The terms "halocycloalkyl", "haloalkenyl" and "haloalkynyl" are defined analogously to the term "haloalkyl".

The total number of carbon atoms in a substituent group is indicated by the "Ci-C j " prefix where i and j are numbers from 1 to 8. For example, ^-€ 3 alkylsulfonyl includes methylsulfonyl through propylsulfonyl; C 2 alkoxyalkoxy designates 0CH 2 0CH 3 ; C 4 alkoxyalkoxy designates the various isomers of an alkoxy group

substituted with a second alkoxy group containing a tota of 4 carbon atoms, examples including OCH OCH CH 2 CH 3 and OCH 2 CH 2 OCH 2 CH 3 ; C 2 cyanoalkyl designates CH 2 CN and C 3 cyanoalkyl includes CH 2 CH 2 CN and CH(CN)CH 3 ; C 2 alkylcarbonyl designates C(0)CH 3 and C 4 alkylcarbonyl includes C(0)CH 2 CH 2 CH 3 and C(0)CH(CH 3 ) 2 ; C 2 alkoxycarbony designates C(0)0CH 3 and C 4 alkoxycarbonyl includes C(0)OCH 2 CH 2 CH 3 and C(0)0CH(CH 3 ) 2 ; and as a final example, C 3 alkoxycarbonylalkyl designates CH C0 2 CH 3 and C 4 alkoxycarbonylalkyl includes CH 2 CH C0 2 CH 3 , CH 2 C0 2 CH 2 CH 3 a CH(CH 3 )C0 2 CH 3 .

Compounds of Formula I may exist as one or more stereoisomers. The various stereoisomers include enantiomers, diastereomers and geometric isomers. One skilled in the art will appreciate that one stereoisomer may be the more active. One skilled in the art knows ho to separate said enantiomers, diastereomers and geometri isomers. Accordingly, the present invention comprises racemic mixtures, individual stereoisomers, and opticall active mixtures, as well as agriculturally suitable salt of the compounds of Formula I.

DETAILS OF THE INVENTION Compounds of Formula I are prepared according to Schemes 1 through 18 with substituents as previously defined, unless otherwise noted.

Compounds of Formula I are prepared by the reaction of acyl derivatives of Formula II (Q-l, Q-2, Q-3, Q-4, Q-5 (Z=CH 2 ) and Q-6) with compounds of Formula III as illustrated in Scheme 1. Typical reactions involve the combination of equimolar amounts of II and III in the presence of a base such as an alkali metal, tertiary amine, metal hydride and the like in conventional organi solvents including ether, tetrahydrofuran, 1,2-dimethoxy ethane, methylene chloride, chloroform, N,N-dimethyl-

formamide and dimethylsulfoxide. The reaction can be conducted at temperatures in the range of -100°C to 100°C.

SCHEME 1

X L base

II

L - Br, Cl, N N

The acyl derivatives of Formula II (Q-l, Q-2 and Q-5 (Z=CH 2 ) ) can be prepared according to Scheme 2 by reaction of the appropriate amine with acylating agents such as phosgene, carbonyldiimidazole, substituted phenylchloroformates and the like (Helv. Chem. Acta, 1972, ϋϋ, 388; Ann. Chem. , 1961, 648. 72; and J. Am. Chem. Soc. , 1948, J7J1, 3439) . Typical reactions involve the combination of equimolar amounts of Formula V compounds and Formula IV compounds in the presence of a base such as an alkali metal, tertiary amine, metal hydride and the like in conventional organic solvents including ether, tetrahydrofuran, 1,2-dimethoxyethane, methylene chloride and chloroform. The reaction can be conducted at temperatures in the range of -100°C to 100°C.

SCHEME 2

x

Λ ■ <^-~- l Base - ^

Q + L L 1 ► II

I

H

IV

I 1 = I or

1 - W-Ph-0

Alternatively, compounds of Formula I (Q-l, Q-2, Q-5 (Z=CH 2 ) ) can be prepared by the reaction of Formula V compounds with isocyanates of Formula VI. Typical reactions involve the combination of equimolar amounts o V and VI in a conventional organic solvent such as but not limited to ethyl acetate, methylene chloride, chloroform, benzene or toluene. A base such as an alkal metal, tertiary amine, • alkali metal alkoxide or metal hydride can be used. Scheme 3 illustrates this transformation. SCHEME 3

Q G—NCX

I

H

V VI

The synthesis of compounds of Formula VI is well known to those skilled in the art. Reaction of compound of Formula III (Y=H) with compounds of Formula IV as illustrated in Scheme 4 readily provides compounds of Formula VI (Fieser & Fieser, Reagents for Organic Synthesis. Vol. 1, 1967).

SCHEME 4

H V. ^- Q, O

? NCX

Y ♦ G— VI III IV y - H

Syntheses of Formula V (Q-l) compounds are described in U.S. 4,070,365 and WO 88/01004. In those documents, amines of Formula V are reacted with phenyl isocyanates to afford the desired amides. The syntheses of compounds of Formula VII (Q-2, Z=CH 2 ) and Formula VIII (Q-5) are described in WO 91/17983 and WO 90/07495, respectively.

VII VIII

Formula VII (Z=CH 2 ) compounds are formed by reduction of pyridazinones (R 4 =R 5 =0) . Formula VIII compounds are hydrazones whose syntheses are well-known to those skilled in the art.

Compounds of Formula II (Q-3) are prepared according to methods described in WO 88/05046. These materials are formed by 1,3-dipolar cycloadditions of a nitrile ylides; a reaction well-known to those skilled in the art.

Compounds of Formula .1 (Q-2, Z = 0, S and NR 29 ) can be prepared by the reaction of semicarbazones of Formula IX with compounds of Formula X. Typical reactions involve the combination of an excess in molar amounts of

a Formula X compound (1.1 molar equivalents to 40 molar equivalents) with 1 equivalent of a Formula IX compound in the presence of less than one molar equivalent of an acid catalyst (0 equivalents to 0.9 equivalents) . Typical acid catalysts include alkyl or aryl sulfonic acids (such as methyl, camphor or p-toluene) and mineral acids (such as hydrochloric or sulfuric) . Conventional, polar organic solvents such as acetonitrile, dimethylformamide, tetrahydrofuran, methanol or ethanol can be used. The reaction temperature can vary from 0°C to the reflux temperature of the particular solvent bein used and the reaction is usually complete in less than 2 hours. Scheme 5 illustrates this transformation.

SCHEME 5

IX

Formula IX compounds can be prepared by the reaction of compounds of Formula XI with semicarbazides of Formul XII. An acid catalyst such as hydrochloric, sulfuric or p-toluene sulfonic acid may be used in this reaction. Reaction temperatures can range from 0 to 150°C with the reflux temperature of the particular solvent generally being preferred. Suitable solvents include, but are not limited to, methanol, ethanol, isopropanol, tetra-

hydrofuran and dioxane. Scheme 6 illustrates this transformation.

SCHEME 6

XI XII

Compounds of Formula XI where Z is 0 can be prepared by the α-hydroxylation of ketones of Formula XIII using procedures that are well-known to one skilled in the art (see J, Am, Chem. SOC, 1974, 96, 5944; Tetrahedron Let . r 1988, 29, 2835; and J. Org- Chem-, 1986, 51, 2402) . Scheme 7 illustrates this transformation.

SCHEME 7

Numerous alternative procedures exist for the preparation of α- ydroxy etones of Formula XI. Such procedures are well-known to one skilled in the art (March, Advanced Organic Chemistry, 3rd Edition, 1985,

1164) . Compounds of Formula XI where Z is 0, R 3 is aryl and E is H are benzoins whose preparations are well-known to one skilled in the art. α-Keto sulfides of Formula XI where Z is S can be prepared from ketones of Formula XIII using procedures

known in the art (J. Am. Chem. Soc. r 1985, 107, 4175; J. Org. Chem.. 1988, 53, 3125) . α-Amino ketones of Formula XI where Z is NR 29 can be prepared from ketones of Formula XIII using procedures known in the art (J, Chem. SPC, 1959, 1479; Synthesis, 1972, 191) .

The starting ketones of Formula XIII are known in th art or can be obtained by methods analogous to known procedures. Those skilled in the art will recognize the Formula XIII compounds to include deoxybenzoins, indanones, tetralones, chromanones, thiochromanones, benzofuran-3-ones, isochromanones and others.

One skilled in the art will recognize that the transformation of Formula XIII compounds into Formula XI compounds may require the use of protecting groups to prevent unwanted side reactions of functionalities that may be sensitive to the reaction conditions (for example an amino group attached to an indanone may require a protecting group to render it unreactive in an α-hydroxylation of the carbonyl group) .

Semicarbazides of Formula XII where X is 0 or S can be prepared by using the procedure shown in Scheme 8.

Compounds of Formula VI are treated with an excess o a molar amount of hydrazine or hydrazine hydrate in an anhydrous aprotic solvent at a temperature between -100° and 100°C. Typical solvents include but are not limited to ether, methylene chloride, chloroform, toluene and tetrahydrofuran.

SCHEME 8

NH 2 NH 2

VI XII or

NH 2 NH 2 H 2 0

Compounds of the Formula II (Q-4, Z = 0, S and NR 29 ) can be prepared from compounds of the Formula XIII through conventional methodology generally used for the conversion of esters to their corresponding acid chlorides as illustrated in Scheme 9. SCHEME 9

The preparation of compounds of Formula XIII, where Q is Q-4 and Z is CH 2 , is disclosed in WO 91/17983.

Formula XIII derivatives (where A is equal to H, Z = O, S, or NR 29 ) can be prepared by the reaction of Formula XIV compounds with an equimolar or greater amount of a Formula XV compound in the presence of an acid catalyst (with 0.05 to 0.2 molar equivalents preferred). The reaction can be carried out in a variety of polar organic solvents, including, but not limited to, tetrahydrofuran, acetonitrile, methanol or ethanol at a temperature between 0 and 90°C with the preferred temperature being

the reflux temperature of the solvent. This reaction is illustrated by Scheme 10.

SCHEME 10

CO^ > CH CH XIV (A is H)

Compounds of Formula XIV where Z is O can be prepare by treatment. of Formula XVI compounds with a carboxylic acid such as formic, acetic or benzoic acid in the presence of 0 to 2.0 equivalents of a base including, bu not limited to, potassium carbonate, sodium carbonate or sodium hydroxide. Suitable solvents for the reaction include, but are not limited to, ethanol, tetrahydrofura or dimethylformamide. The ester formed in the initial reaction is subsequently hydrolyzed to the alcohol XIV (Z is 0) using a base such as sodium ethoxide in a solvent such as ethanol. Thiols of the Formula XIV (where Z is S) can be prepared using analogous procedure starting with a thiocarboxylic acid (such as thiolacetic acid) . The preparation of Formula XIV compounds (Z is 0 or S) is illustrated by Scheme 11.

SCHEME 11

C0 2 CH 2 CH 3 COoCi oCH-

XVI

XVIII

CO CHΛCH XVIII

wherein

Z is 0 or S; and

L 2 is H, alkyl or aryl. Compounds of Formula XIV where Z is NR 29 can be prepared using procedures analogous to those shown in Scheme 11 using either ammonia or a primary amine (R 29 NH 2 ) in place of the carboxylic or thiocarboxylic acid. Compounds of Formula XVI can be prepared from compounds of the Formula XIX by the reaction with an equimolar amount of compounds of Formula XX in conventional organic solvents such as, but not limited to, ether, tetrahydrofuran, methanol, ethanol, methylene chloride, benzene and toluene. Typical reaction temperatures can range from room temperature to the reflux temperature of the particular solvent utilized and

the reaction is usually complete in 24 hours. Scheme 12 illustrates this reaction.

SCHEME 12

XIX XX

Formula XIX compounds can be prepared from Formula XXI derivatives by a diazotization/reduction reaction well documented in the literature (see Organic Functiona Group Preparation, 1983, 452-453 and references cited therein) . Scheme 13 illustrates this transformation.

SCHEME 13

(R 2 )

XXI

Formula XXI compounds are known in the art or can be obtained by methods analogous to known procedures. Thos skilled in the art will recognize Formula XXI compounds to be substituted anilines. Compounds of the Formula I where Q is Q-6 and A is H can be prepared in a conventional three-step process whereby Formula XXII esters are saponified, converted to the acid chloride and reacted with an appropriately substituted amine. Scheme 14 illustrates this method.

SCHEME 14

XXII

III

Formula XXII compounds can be prepared by the reaction of Formula XXIII hydrazines with esters of the Formula XXIV. The reaction can be conducted in the presence or the absence of an acid or base in an unreactive solvent such as methanol, ethanol, methylene chloride, chloroform, tetrahydrofuran and dioxane, but not limited to these. -The temperature of the reaction can be varied from 0°C to the reflux temperature of the particular solvent. The reaction is usually complete in 24 h. Scheme 15 illustrates this transformation. SCHEME 15

XXIII XXIV

Compounds of the Formula XXIII can be prepared by the reaction of Formula XXV derivatives with a reagent such as 0-(2,4-dinitrophenyl)hydroxylamine (XXVI) in the presence of a base such as sodium carbonate, sodium bicarbonate or potassium carbonate in a nonreactive

solvent such as, but not limited to, dimethylformamide, dimethylsulfoxide, tetrahydrofuran and dioxane. The reaction temperature can vary from 0 to 100°C with 25°C being preferred. The reaction is usually complete in 24 hours. This procedure is analogous to that described in J. Med. Chem., 1984, 27, 1103. Scheme 16 illustrates these transformations.

SCHEME 16

XXIII

Compounds of the Formula XXV can be prepared by a two-step procedure whereby Formula XXVII compounds are reacted with appropriately substituted amines of Formula XXVIII in the presence of a base such as sodium or potassium carbonate in a solvent such as dimethyl¬ formamide, dimethylsulfoxide, tetrahydrofuran and the like. The temperature of the reaction can vary from about 25 to 150°C and the reaction is usually complete in 48 h. In the subsequent step the amine can be protected and the ortho-nitro substituent can be removed by hydrogenation and reductive diazotization (Tetrahedron Lett. 1989, 929) . Scheme 17 illustrates these transformations.

SCHEME 17

XXVII XXVIII

XXIX

1) H 2 , Pd;

2) NaN0 2 , H 2 S0 4

3) Cu, EtOH, NaO

XXV

One skilled in the art will recognize Formula XXVIII compounds as substituted amines, the preparations of which are in the literature (J. Chem. Soc, Chem. Commun. r 1987, 897; Synth. Comιm.n. r 1980, 10, 107) .

Compounds of the Formula I (where Q is Q-6 and A and E are taken together) are easily recognized by those skilled in the art as dihydroindoles and tetrahydroquino- lines, preparations of which are well documented in the literature (J. Meri. Chem., 1984 1439) .

The preparation of compounds of Formula III (where G is G-2 and G-3 and Y is H) is shown in Scheme 18. The preparation of nitrosoamines of Formula XXXI from compounds of Formula XXX is readily accomplished by known literature methods (Sandier and Karo, "Organic Functional Group Preparations," 1968, vol. 2, 424-450). Reduction of nitrosoamines of Formula XXXI is readily accomplished by known literature methods (Sandier and Karo, Organic Functional Group Preparations, 1968, vol. 1, 374-376) .

Amines of Formula XXX are known to those skilled in the art as piperidines and tetrahydropyridines. The syntheses of these derivatives are found throughout the literature (see Fieser and Fieser, Reagents for Organic Synthesis, vol. 1, 1967, 981; Liebigs Ann. Chem. r 1972, 1M, 21-27) .

Formula I compounds, where Y is other than H, can be prepared by standard alkylation, acylation or sulferiylation methods well documented in the literature. It is recognized that in many of the transformations described it is necessary to utilize appropriate protecting groups to prevent unwanted side reactions or use reagents that do not affect functional groups other than those desired to be changed. One skilled in the ar will be able to select appropriate protecting groups and reagents to this end.

EXAMPLE l Step A: methyl 2.3-dihydro-2- tlH-imidazo-1-ylcarbonyl )- 7- .trifluoromethyl)-m-benzopyranoT4 r 3-clpyrazole-

3a(4H)-carbo ylate To a suspension of methyl 2,3,3a,4-tetrahydro-7- (trifluoromethyl)-[l]-benzopyrano[4,3-c]pyrazole-3a- carboxylate hydrochloride (2.0 g, 0.006 mol) in dichloromethane (40 mL) was added triethylamine (0.66 g, 0.0065 mol). The suspension became a clear solution. After 5 minutes, N,N'-carbonyldiimidazole (1.5 g,

0.009 mol) was added in one portion. After 1 h., a whit precipitate had formed. The reaction was partitioned

between water and methylene chloride. The organic phase was washed with concentrated aqueous sodium bicarbonate solution then dried over anhydrous sodium sulfate. Filtration and concentration under reduced pressure gave an oil that was triturated with ether to give 1.82 g of the title compound as a white solid, mp. 208-209°C. X H NMR (CDC1 3 ) δ 3.8(s, 3H) , 4.3 (ABq, 2H) , 4.6 (ABq, 2H) , 7.1(s, IH), 7.3 (s, IH), 7.8(s, IH) , 8.0(d, IH) , 8.6(s, IH) . Step B: l-nitroso-4- .trifluoromethyl)piperidine

To a solution (100 mL) of 10% sulfuric acid in water was added 4-(trifluoromethyl)piperidine (10 g, 0.072 mol) and the resulting solution was cooled to 0°C. An aqueous solution of sodium nitrite (6.5 g, 0.094 mol) was added and the reaction was stirred for 48 hours. The reaction mixture was then continuously extracted with ether for 4 hours. The organic phase was dried with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to leave the title compound as a yellow oil (5.2 g). --E NMR δ 1.6(m, IH) , 1.8(m, IH) , 2.0(m, IH) , 2.2 (m, IH) , 2. (m, IH) , 2.6(dt, IH) , 3.7 (dt, IH) , 4.9(d, IH) , 5.1(d, IH) . Step C: 4-(trifluoromethyl)-1-piperidinamine hydrochloride Lithium aluminum hydride (4.0 g, 0.105 mol) was suspended in diethylether (150 mL) . A solution of the product of Step B (5.2 g, 0.031 mol) in diethyl ether (15 mL) was added at room temperature over 10 min. The reaction was heated at reflux for 2 hours. After cooling to 0°C the mixture was diluted with 100 mL wet ether and then quenched slowly with 25% aqueous sodium hydroxide solution. The aqueous phase was washed three times with ether, dried over anhydrous potassium carbonate and filtered. A 1M solution of anhydrous hydrogen chloride

in ether (100 mL) was added which provided a white precipitate that was filtered and dried to give the title compound (4.2 g) ^-H NMR (DMSO-d 6 ) δ 1.6(m, 2H) , 1.9(m, 2H) , 2.5(m, IH) , 2.7 (t, 2H) , 3.4 (d, 2H) , 7.0 (brs, 2H) . Step D: methyl 2.3-dihydro-7- <trifluoromethyl)-2-T T4- ■trifluoromethyl)-1-piperidinylaminolcarbonyl!-Til- benzopyrano. .3-cl-pyrazole-3a t4H)-πarboxya e

To a solution of the product from Step C (1.0 g, 0.0049 mol) in 1,2-dichloroethane (10 mL) was added triethylamine (1.0 g, 0.0098 mol). To this solution was added the product of Step A (1.5 g, 0.0039 mol) in one portion and the resulting mixture was heated to reflux for 18 hours. The mixture was partioned between dichloromethane and water and the organic phase dried over sodium sulfate. After filtration, the organic phase was concentrated under reduced pressure and subjected to silica gel chromatography using 13:9 hexanes : ethyl acetate to give 0.32 g of the title compound as a white solid, mp 219-220°C. -R NMR (CDC1 3 ) δ 2.0 (m, 5H) , 2.7 (m, 2H), 3.3 (m, 2H) , 3.8(s, 3H) , 4.1 (ABq, 2H) , 4.7 (ABq, 2H) , 7.0(s, IH) , 7.2(s, IH) , 7.3(d, IH) , 7.7(d, IH) IR (cm -1 ) 3188, 1739, 1672.

By the general procedures described herein, or obvious modification thereof, the compounds of Tables 1 through 3 can be prepared.

Key to Tables 1-3

K =

K-7 K-8 K-9

K-10 K-ll K-12

The abbreviations Me, Et, i-Pr, and Ph have the following meaning: Me = -CH 3 ; Et = -CH 2 CH 3 ; i-Pr = -CH(CH 3 ) 2 ; and

Each line of Tables 1-3 defines four separate compounds. For example. Table 1, line 1, column 1 describes a compound wherein Y is H, column 2 describes one compound where Y is Me, column 3 describes one compound where Y is COOMe and column 4 describes one compound where Y is COMe. Thus, each line of each page of Tables 1-3 describes four separate compounds.

.Z&B ELI

Y

K-K-2 R 1 =CF 3 ; R 2 =C1; R 3 -Me; Y- R 1 =OCF 3 ; R 2 =C1; R 3 =Me; Y= R 1 =CF 3 ; R 2 =F; R 3 -Me; Y= R 1 =OCF 3 ; R 2 »F; R 3 «Me; Y«= R 1 =CF 3 ; R 2 =C1; R 3 =Et; y= R 1 =OCF 3 ; R 2 =C1; R 3 =Et; γ= R 1 =CF 3 ; R 2 =F; R 3 =Et; γ= R 1 =OCF 3 ; R 2 =F; R 3 =Et; γ=

K=K-3 R 1 =CF 3 ; R 2 «=C1; R 3 -4-Cl-P ; γ= R 1 =0CF 3 ; R 2 «=C1; R 3 =4-Cl-P ; γ= R X =CF3; R 2 =C1; R 3 =4-F-P ; γ= R 1 =OCF 3 ; R 2 »C1; R 3 -4-F-P ; Y- R 1 =CF 3 R 2 =C1; R 3 -P ; Y= R 1 -OCF 3 ; R 2 «C1; R 3 -P ; Y= R 1 »CF 3 ; R 2 -F; R 3 -4-Cl-Ph; Y«= R 1 =OCE 3 ; R 2 =F; R 3 -4-Cl-Ph; Y= R 1 =CF 3 ; R 2 =F; R 3 =4-F-Ph; Y= R 1 =OCF 3 ; R 2 =F; R 3 -4-F-Ph; Y= R 1 «=CF 3 ; R 2 =F; R 3 »Ph; Y= R 1 «=OCF 3 ; R 2 =F; R 3 -Ph; Y=

K-K-4 R 1 -CF 3 ; R 2 «6-C1; R 3 -COOMe; Y- R 1 -OCF 3 ; R 2 -6-Cl; R 3 =COOMe; Y- R 1 »CF 3 ; R 2 =6-C1; R 3 -4-Cl-P ; Y-= R 1 «=OCF 3 ; R 2 -6-Cl; R 3 -4-Cl-Ph; Y« R 1 =CF 3 ; R 2 «6-C1; R 3 -4-F-Ph; Y= R 1 =OCF 3 ; R 2 -6-Cl; R 3 =4-F-Ph; Y= R 1 =CF 3 ; R 2 =6-F; R 3 =COOMe; Y= R 1 - CF 3 ; R 2 «6-F; R 3 -COOMe; Y* R 1 =CF 3 ; R 2 -6-F; R 3 =4-Cl-Ph; Y* R 1 «=0CF 3 ; R 2 =6-F; R 3 -4-Cl-Ph; Y- R 1 =CF 3 ; R 2 =6-F; R 3 =4-F-Ph; Y= R 1 -OCF 3 ; R 2 -6-F; R 3 -4-F-P ; Y- R 1 =CF 3 ; R 2 =6-CF 3 ; R 3 =COOMe; Y- R 1 =OCF 3 ; R 2 «6-CF 3 ; R 3 -COOMe; Y= R 1 -CF 3 ; R 2 =6-CF 3 ; R 3 =4-Cl-Ph; Y= R 1 =OCF 3 ; R 2 =6-CF 3 ; R 3 -4-Cl-Ph; Y= R 1 =CF 3 ; R 2 -6-CF 3 ; R 3 -4-F-Ph; Y- R 1 -OCF 3 ; R 2 «6-CF 3 ; R 3 -4-F-P ; Y- R 1 -CF 3 ; R 2 -5-F; R 3 «COOMe; Y- R 1 =OCF 3 ; R 2 -5-F; R 3 =COOMe; Y- R 1 =CF 3 ; R 2 -5-F; R 3 -4-Cl-Ph; Y- R 1 =OCF 3 ; R 2 =5-F; R 3 =4-Cl-Ph; Y«= R 1 =CF 3 ; R 2 -5-F; R 3 »4-F-P ; Y» R 1 -OCF 3 ; R 2 -5-F R 3 -4-F-Ph; Y- R 1 -CF 3 ; R 2 -5-Cl; R 3 -COOMe; Y- R 1 «=OCF 3 ; R 2 »5-C1; R 3 -COOMe; Y- R 1 =CF 3 ; R 2 =5-C1; R 3 =4-Cl-Ph; Y= R 1 =OCF 3 ; R =5-C1; R 3 =4-Cl-Ph; Y= R 1 =CF 3 ; R 2 =5-C1; R 3 »=4-F-Ph; Y= R 1 =OCF 3 ; R 2 =5-C1; R 3 «=4-F-P ; Y= R 1 =CF 3 ; R 2 =6-C1; R 3 -Me; Y=

K-K-4 R 1 =OCF 3 ; R 2 =6-C1; R 3 »Me; Y= R 1 -CF 3 ; R 2 =6-F; R 3 -Me; Y= R 1 -OCF 3 ; R 2 -6-F; R 3 -Me; Y- R X =CF 3 ; R 2 =6-CF 3 ; R 3 =Me; Y= R 1 -0CF 3 ; R 2 -6-CF 3 ; R 3 -Me; Y= R 1 =CF 3 ; R 2 -5-Cl; R 3 -Me; Y= R 1 «OCF 3 3;' R 2 -5-Cl; R 3 -Me; Y= R^CF- 3,;' R 2 =5-F; R 3 -Me; Y= R 1 «=0CF 3 ; R 2 -5-F; R 3 -Me; Y- R X =CF 3 ; R 2 =6-C1; R 3 =i-Pr; Y= R 1 =0CF 3 ; R 2 =6-C1; R 3 -i-Pr; Y= R 1 =CF 3 ; R 2 -6-F; R 3 -i-Pr; Y= R.-= .CF 3 ; R 2 =6-F; R 3 -i-Pr; Y= R 1 =CF 3 ; R 2 =6-CF 3 ; R 3 =i-Pr; Y= R 1 =0CF 3 ; R 2 -6-CF 3 ; R 3 =*i-Pr; Y= R 1 =CF 3 ; R 2 =5-C1; R 3 =i-Pr; Y= R 1 =0CF 3 ; R=5-C1; R 3 -i-Pr; Y= R 1 -CF 3 ; R 2 «5-F; R 3 «i-Pr; Y«= R 1 =0CF 3 ; R -5-F; R 3 -i-Pr; Y=

K-K-5 R 1 =CF 3 ; R 2 -6-Cl; R 3 -C00Me; Y» R 1 =0CF 3 ; R 2 -6-Cl; R 3 «C00Me; Y= R 1 -CF 3 ; R 2 =6-C1; R 3 -4-Cl-P ; Y- X =0CF3; R 2 =6-C1; R 3 -4-Cl-Ph; Y= R 1 =CF 3 ; R 2 =6-C1; R 3 -4-F-P ; Y= R 1 =0CF 3 ; R 2 -6-Cl; R 3 -4-F-Ph; Y= R 1 =CF 3 ; R 2 =6-F; R 3 =C00Me; Y= R 1 =0CF 3 ; R 2 =6-F; R 3 =COOMe; Y= R 1 =CF 3 ; R 2 =6-F; R 3 =4-Cl-Ph; Y= R 1 =0CF 3 ; R 2 -6-F; R 3 =4-Cl-P ; Y= R 1 =CF 3 ; R 2 =6-F; R 3 =4-F-Ph; Y= R 1 =0CF 3 ; R 2 -6-F; R 3 =4-F-Ptι; Y=

K-K-5

83 R1=CF 3 ; R 2 =6-CF 3 ; R 3 =C00Me; Y=

84 R 1 =OCF 3 ; R 2 «=6-CF 3 ; R 3 »COOMe; Y=

85 R 1 -CF 3 ; R 2 =6-CF 3 ; R 3 -4-Cl-Ph; Y-

86 R 1 =0CF 3 ; R 2 =6-CF 3 ; R 3 -4-Cl-Ph; Y=

87 R1=CF 3 ; R 2 =6-CF 3 ; R 3 =4-F-Ph; Y-

88 R X =OCF 3 ; R 2 =6-CF 3 ; R 3 =*=4-F-Ph; Y=

89 R »l X ==rCF 3 ; R *2-^_δ R _--F; R°=COOMe; Y=

90 R 1 -OCF 3 ; R 2 -5-F; R 3 -COOMe; Y-

91 R 1 =CF 3 ; R 2 =5-F; R 3 -4-Cl-Ph; Y-

92 R 1 =OCF 3 ; R 2 =5-F; R 3 =4-Cl-P ; Y=

93 R 1 =CF 3 ; R 2 =5-F; R 3 =4-F-Ph; Y-

94 R 1 =OCF 3 ; R 2 =5-F; R 3 -4-F-P ; Y-

95 R1=CF 3 ; R 2 =5-C1; R 3 =COOMe; Y-

96 R 1 =OCF 3 ; R 2 =5-C1; R 3 =COOMe; Y-

97 R 1 =CF 3 ; R 2 =5-C1; R 3 -4-Cl-Ph; Y-

98 R J -=OCF 3 ; R ? 2 ==5ς--,C1; R- 3 --a4--mCl --Pτ ; Y-

99 R 1 =CF 3 ; R 2 =5-C1; R 3 =4-F-P ; Y"

100 R 1 -OCF 3 ; R 2 -5-Cl; R 3 -4-F-Ph; Y-

101 R 1 =CF 3 ; R 2 «=6-C1; R 3 =Me; Y=

102 R 1 =OCF 3 ; R 2 =6-C1; R 3 =Me; Y-

103 R 1 -=CF 3 ; R 2 =6-F; R 3 -Me; Y-

104 R 1 =OCF 3 ; R 2 -6-F; R 3 =Me; Y"

105 R 1 =CF 3 ; R 2 =6-CF 3 ; R 3 =Me; Y-

106 R 1 =OCF 3 ; R 2 =6-CF 3 ; R 3 =Me; Y=

107 R 1 =CF 3 R 2 =5-C1; R 3 =Me; Y=

108 R 1 =OCF 3 ; R 2 =5-C1; R 3 =Me; Y=

109 R1=CF 3 ; R 2 =5-F; R 3 -Me; Y-

110 R 1 =OCF 3 ; R 2 =5-F; R 3 -Me; Y=

111 R 1 =CF 3 ; R 2 =6-C1; R 3 =i-Pr; Y=

112 R 1 =OCF 3 ; R 2 -6-Cl; R 3 -i-Pr; Y=

113 R1=CF 3 ; R 2 =6-F; R 3 =i-Pr; Y-

114 R 1 =OCF 3 ; R 2 =6-F; R 3 =i-Pr; Y=

K-K-5

115 R 1 =CF 3 ; R 2 =6-CF 3 ; R 3 =i-Pr; Y= 116 R 1 «OCF 3 ; R 2 =6-CF 3 ; R 3 -i-Pr; Y- 117 R!«=CF 3 ; R 2 -5-Cl; R 3 -i-Pr; Y- 118 R 1 = CF 3 ; R 2 ~5-C1; R 3 =i-Pr; Y= 119 R 1 =CF 3 ; R 2 =5-F; R 3 =i-Pr; Y= 120 R 1 -OCF 3 ; R 2 -5-F; R 3 -i-Pr; Y-

K=K-6

121 R 1 =CF 3 ; R 2 =C1; R 3 «4-Cl-P ; Y~ 122 R .1-==OCF. R 2^ = =rC1 R 3 -=4-Cl-Ph; Y= 123 R >1-==,CF 3 ; R 2" = = r C1 l 3 =4-F-P ; Y= 124 R 1 =OCF 3 ; R 2 =C1; R 3 -4-F-Ph; Y= 125 R 1 =CF 3 ; R 2 =F; R 3 =4-Cl-P ; Y= 126 R 1 =OCF 3 ; R 2 =F; R 3 =4-Cl-P ; Y= 127 R 1 =CF 3 ,* R 2 =F; R 3 =4-F-Ph; Y= 128 R 1 =0CF 3 ; R 2 -F; R 3 =4-F-Ph; Y= 129 R 1 =CF 3 ; R 2 =CF 3 ; R 3 =4-Cl-Ph; Y= 130 R 1 -OCF 3 ; R 2 =CF 3 ; R 3 -4-Cl-Ph; Y= 131 R 1 =CF 3 ; R 2 -CF 3 ; R 3 -4-F-Ph; Y«= 132 R 1 =OCF 3 ; R 2 =CF 3 ; R 3 =4-F-P ; Y=

K=K-7

133 R 1 =CF 3 ; R 2 =C1; R 3 =4-Cl-P ; Y= 134 R 1 =OCF 3 ; R 2 =C1; R 3 =4-Cl-P ; Y= 135 R 1 =CF 3 ; R 2 =C1; R 3 «=4-F-Ph; Y= 136 R 1 =OCF 3 ; R 2 =C1; R 3 =4-F-Ph; Y= 137 R 1 =CF 3 ; R 2 =F; R 3 «=4-Cl-Ph; Y= 138 R 1 =OCF 3 ; R 2 =F; R 3 =4-Cl-P ; Y= 139 R .1 J -==,CF 3 ; 140 R 1 =OCF 3 ; R 2 =F; R 3 =4-F-P ; Y= 141 R 1 =CF 3 ; R 2 =CF 3 ; R 3 =4-Cl-Ph; Y= 142 R 1 =OCF 3 ; R 2 =CF 3 ; R 3 =4-Cl-Ph; Y= 143 R 1 =CF 3 ,- R 2 =CF 3 ; R 3 -4-F-Ph; Y= 144 R 1 =OCF 3 ; R 2 =CF 3 ; R 3 «4-F-Pϊι; Y=

K-K-8

Z-CH 2

145 R 1 -CF 3 ; R 2 ~5-C1; R 3 -COOMe; Y» 146 R 1 -OCF 3 ; R 2 -5-Cl; R 3 -COOMe; Y- 147 R 1 -CF 3 ; R 2 »5-F; R 3 «COOMe; Y= 148 R 1 =OCF 3 ; R 2 -5-F; R 3 »COOMe; Y= 149 R 1 =CF 3 ; R 2 -5-CF 3 ; R 3 =COOMe; Y= 150 R 1 =OCF 3 ; R 2 -5-CF 3 ; R 3 =COOMe; Y= 151 R 1 -CF 3 ; R 2 «4-C1; R =COOMe; Y= 152 R 1 =OCF 3 ; R 2 -4-Cl; R =COOMe; Y» 153 R 1 -CF 3 ; R 2 =4-F; R 3 =COOMe; Y= 154 R 1 =OCF 3 ; R 2 -4-F; R 3 =COOMe; Y= 155 R 1 =CF 3 ; R 2 -5-Cl; R 3 =4-Cl-Ph; Y«= 156 R 1 =OCF 3 ; R 2 =5-C1; R 3 =4-Cl-Ph; Y= 157 R1=CF 3 ; R 2 «=5-F; R 3 -4-Cl-Ph; Y= 158 R1«=0CF 3 ; R 2 -5-F; R 3 «4-Cl-Ph; Y«= 159 R 1 -CF 3 ; R 2 -5-CF 3 ; R 3 -4-Cl-Ph; Y= 160 R 1 =OCF 3 ; R 2 »5-CF 3 ; R 3 «4-Cl-Ph; Y= 161 R 1 *»CF 3 ; R 2 -4-Cl; R 3 -4-Cl-Ph; Y- 162 R 1 =OCF 3 ; R 2 -=4-Cl; R 3 -4-Cl-Ph; Y- 163 R 1 =CF 3 ; R 2 =4-F; R 3 -4-Cl-Ph; Y= 164 R 1 =OCF 3 ; R 2 -4-F; R 3 -4-Cl-Ph; Y- 165 R 1 =CF 3 ; R 2 -5-Cl; R 3 -4-F-P ; Y= 166 R 1 =OCF 3 ; R 2 -=5-Cl; R 3 -4-F-Ph; Y= 167 R 1 -CF 3 ; R 2 -5-F; R 3 -4-F-Ph; Y* 168 169 R 1 =CF 3 ; R 2 =5-CF 3 ; R 3 -4-F-Ph; Y« 170 R!=OCF 3 ; R 2 »5-CF 3 ; R 3 -4-F-P ; Y= 171 R1=CF 3 ; R 2 «-4-Cl; R 3 -4-F-Ph; Y- 172 R!=OCF 3 ; R 2 ~4-C1; R 3 «=4-F-P ; Y= 173 R1=CF 3 ; R 2 =4-F; R 3 -4-F-Ph; Y= 174 R 1 =OCF 3 ; R 2 «4-F; R 3 «=4-F-Ph; Y=

K-K-8

Z=CH 2

175 R1.=CF 3 ; R 2 «5-C1; R 3 -Me; 176 R1-OCF 3 ; R 2 -5-Cl; R 3 -Me; 177 R A =CF 3 ; R 2 =5-F; R 3 «Me; 178 R 1 =OCF 3 ; R 2 -5-F; R 3 -Me; 179 R X =CF 3 ; R 2 =5-CF 3 ; R 3 -Me; 180 R 1 =OCF 3 ; R 2 =5-CF 3 ; R 3 -Me; 181 R X =CF 3 ; R 2 =4-C1; R 3 -Me; 182 R x *=OCF 3 ; R 2 -4-Cl; R 3 -Me; 183 R X =CF 3 ; R 2 =4-F; R 3 =Me; 184 R =OCF 3 ; R 2 =4-F; R 3 =Me; 185 R X =CF 3 ; R 2 =5-C1; R 3 =i-Pr; 186 R x «OCF 3 ; R 2 -5-Cl; R 3 =*i-Pr; 187 R X =CF 3 ; R 2 =5-F; R 3 =z-Pr; 188 R x =OCF 3 ; R 2 -5-F; R 3 -i-Pr; 189 R X =CF 3 ; R 2 =5-CF 3 ; R 3 =i-Pr; 190 R x =OCF 3 ; R 2 =5-CF 3 ; R 3 «=i-Pr; 191 R X »CF 3 ; R 2 «=4-C1; R 3 =i-Pr; 192 R x =OCF 3 ; R 2 =4-C1; R 3 -i-Pr; 193 R »\ X =.CF 3 ; R 2" = =4,_-F; R }3--- 7 -_-rPr; 194 R =OCF 3 ; R 2 -4-F; R 3 =i-Pr; K=K-8 Z=0

195 R »CF 3 ; R 2 -5-Cl; R 3 «=COOMe; Y= 196 R x =OCF 3 ; R 2 =5-C1; R 3 =COOMe; Y= 197 R X =CF 3 ; R 2 «5-F; R 3 =COOMe; Y- 198 R x =OCF 3 ; R 2 -5-F; R 3 =COOMe; Y= 199 R X =CF 3 ; R 2 =5-CF 3 ; R 3 =COOMe; Y= 200 R =OCF 3 ; R 2 =5-CF 3 ; R 3 =COOMe; Y-= 201 R1-=CF 3 ; R 2 «=4-C1; R 3 =COOMe; Y= 202 R=OCF 3 ; R 2 =4-C1; R 3 =COOMe; Y= 203 R X =CF 3 ; R 2 =4-F; R 3 =COOMe; Y=

K-K-8 Z-0

204 R -OCF 3 ; R 2 -4-F; R 3 -COOMe; Y-

205 R X «=CF 3 ; R 2 «5-C1; R 3 -4-Cl-P ; Y=

206 R x =OCF 3 ; R 2 -5-Cl; R 3 -4-Cl-Ph; Y-

207 R X =CF 3 ; R 2 -5-F; R 3 -4-Cl-Ph; Y-

208 R x =OCF 3 R 2 «5-F; R 3 -4-Cl-Ph; Y-

209 R X =CF 3 ; R 2 =5-CF 3 ; R 3 «4-Cl-Ph; Y=

210 R x =OCF 3 ; R 2 =5-CF 3 ; R 3 -4-Cl-Ph; Y«

211 R X =CF 3 ; R 2 =4-C1; R 3 «4-Ci-Ph; Y=

212 R x =OCF 3 ; R 2 =4-C1; R 3 =4-Cl-Ph; Y=

213 R X =CF 3 ; R 2 =4-F; R 3 -4-Cl-P ; Y=

214 R x =OCF 3 ; R 2 -4-F; R 3 -4-Cl-Ph; Y=

215 R =CF 3 ; R 2 «5-C1; R 3 -4-F-Ph; Y=

216 R x =0CF 3 ; R 2 »5-C1; R 3 -4-F-Ph; Y-

217 R =CF 3 ; R 2 =5-F; R 3 -4-F-Ph; Y*=

218 R x =0CF 3 ; R 2 =5-F; R 3 =4-F-Ph; Y=

219 R X =CF 3 ; R 2 =5-CF 3 ; R 3 «4-F-Ph; Y-

220 R -OCF 3 ; R 2 -5-CF 3 ; R 3 -4-F-Ph; Y-

221 R X -CF 3 ; R 2 «4-C1; R 3 «4-F-Ph; Y-

222 R x «OCF 3 ; R 2 -4-Cl; R 3 -4-F-Ph; Y«-

223 R =CF 3 ; R 2 -4-F; R 3 -4-F-Ph; Y-

224 R x =OCF 3 ; R 2 -4-F; R 3 «4-F-Ph; Y«=

225 R X =CF 3 ; R 2 -5-Cl; R 3 -Me; Y-

226 R x «-OCF 3 ; R 2 -5-Cl; R 3 -Me; Y«=

227 R X «CF 3 ; R 2 -5-F; R 3 -Me; Y *

228 R x =OCF 3 ; R 2 -5-F; R 3 -Me; Y=

229 R X =CF 3 ; R 2 -5-CF 3 ; R 3 -Me; Y-

230 R x =OCF 3 ; R 2 =5-CF 3 ; R 3 -Me; Y=

231 R =CF 3 ; R 2 =4-C1; R 3 «Me; Y=

232 R x =OCF 3 ; R 2 -4-Cl; R 3 -Me; Y=

233 R X -CF 3 ; R 2 -4-F; R 3 -Me; Y«

234 R x =OCF 3 ; R 2 -4-F; R 3 »Me; Y=

K=K-8 Z=0

235 R =CF 3 ; R 2 =5-C1; R 3 =i-Pr; Y= 236 R x =OCF 3 ; R 2 =5-C1; R 3 =i-Pr; Y»= 237 R X =CF 3 ; R 2 =5-F; R 3 »i-Pr; Y- 238 R x =OCF 3 ; R 2 -5-F; R 3 -i-Pr; Y- 239 R X =CF 3 ; R 2 -5-CF 3 ; R 3 -i-Pr; Y= 240 R =OCF 3 ; R 2 =5-CF 3 ; R 3 =i-Pr; Y- 241 R -CF 3 ; R 2 -4-Cl; R 3 -ά-Pr; Y- 242 R =OCF 3 ; R 2 -4-Cl; R 3 -i-Pr; Y= 243 R X =CF3; R 2 =4-F; R 3 =i-Pr; Y= 244 R 1 -=OCF 3 ; R 2 «=4-F; R «=i-Pr; Y-

K-K-8

Z-N-H

245 R1-=CF 3 ; R 2 =5-C1; R 3 =COOMe; Y= 246 R x =OCF 3 ; R 2 -5-Cl; R 3 =COOMe; Y= 247 R X =CF 3 ; R 2 -5-F; R 3 =COOMe; Y= 248 R =OCF 3 ; R 2 =5-F; R 3 =COOMe; Y= 249 R X =CF 3 ; R 2 =5-CF 3 R 3 =COOMe; Y= 250 R x =OCF 3 ; R 2 -=5-CF 3 ; R 3 =COOMe; Y= 251 R X -CF 3 ; R 2 -4-Cl; R 3 -COOMe; Y= 252 R x =OCF 3 ; R 2 -4-Cl; R 3 -=COOMe; Y- 253 R X =CF 3 ; R 2 -4-F; R 3 =COOMe; Y- 254 R x =OCF 3 ; R 2 -4-F; R 3 »=COOMe; Y- 255 R X =CF 3 ; R 2 =5-C1; R 3 =4-Cl-P ; Y= 256 R x =OCF 3 ; R ? 2^_=5c_- ( C1; R 3- 3 --«-4ι--πCl —-τP ; Y= 257 R X =CF 3 ; R 2 -5-F; R 3 -4-Cl-Ph; Y«= 258 R -OCF 3 ; R 2 -5-F; R 3 -4-Cl-Ph; Y= 259 R =CF 3 ; R 2 =5-CF 3 ; R 3 =4-Cl-P ; Y= 260 R x =OCF 3 ; R 2 =5-CF 3 ; R 3 =4-Cl-P ; Y= 261 R =CF 3 ; R 2 =4-C1; R 3 =4-Cl-Ph; Y= 262 R x =OCF 3 ; R 2 =4-C1; R 3 -4-Cl-Ph; Y= 263 R1=CF 3 ; R 2 =4-F; R 3 =4-Cl-Ph; Y=

K=K-8

Z-N-H

264 R x =OCF 3 ; R 2 =4-F; R 3 =*4-Cl-Ph; Y= 265 R1=CF 3 ; R 2 =5-C1; R 3 -4-F-P ; Y= 266 R x =OCF 3 ; R 2 =5-C1; R 3 =4-F-Ph; Y= 267 R -CF 3 ; R 2 -5-F; R 3 =4-F-Ph; Y- 268 R x =OCF 3 ; R 2 =5-F; R 3 =4-F-Ph; Y= 269 R X =CF 3 ; R 2 «=5-CF 3 ; R 3 =4-F-Ph; Y- 270 R x =OCF 3 ; R 2 =5-CF 3 ; R 3 =4-F-Ph; Y= 271 R X =CF 3 ; R 2 =4-C1; R 3 =4-F-Ph; Y= 272 R x =OCF 3 ; R 2 =4-C1; R 3 =4-F-Ph; Y= 273 R 1=CF 3 ; R 2 =4-F; R 3 =4-F-Ph; Y= 274 R x =OCF 3 ; R 2 «=4-F; R 3 =4-F-P ; Y= 275 R X =CF 3 ; R 2 «=5-C1; R 3 =Me; Y= 276 R x =OCF 3 ; R 2 =5-C1; R 3 «Me; Y= 277 R1=-CF 3 ; R 2 =»5-F; R 3 -Me; Y= 278 R x =OCF 3 ; R 2 =5-F; R 3 »Me; Y- 279 R X =CF 3 ; R 2 «5-CF 3 ; R 3 -Me; Y= 280 R =OCF 3 ; R 2 «=5-CF 3 ; R 3 -Me; Y= 281 R X =CF 3 ; R -4-Cl; R 3 -Me; Y« 282 R x =OCF 3 ; R 2 =4-C1; R 3 -Me; Y= 283 R X =CF 3 ; R 2 =4-F; R 3 «Me; Y- 284 R x -OCF 3 ; R -4-F; R 3 -Me; Y«= 285 R X =CF 3 ; R 2 =5-C1; R 3 =i-Pr; Y= 286 R x =OCF 3 ; R 2 =5-C1; R 3 =i-Pr; Y= 2S7 R =CF 3 ; R 2 =5-F; R 3 =i-Pr; Y= 288 R x =OCF 3 ; R 2 =5-F; R 3 =i-Pr; Y= 289 R X =CF 3 ; R 2 =5-CF 3 ; R 3 =i-Pr; Y= 290 R x =OCF 3 ; R 2 =5-CF 3 ; R 3 ==i-Pr; Y= 291 R =CF 3 ; R 2 =4-C1; R 3 =i-Pr; Y= 292 R x =OCF 3 ; R 2 =4-C1; R 3 =i-Pr; Y= 293 R =CF 3 ; R 2 =4-F; R 3 =i-Pr; Y= 294 R x =OCF 3 ; R 2 -4-F; R 3 =i-Pr; Y=

K-K-9

295 R X =CF 3 ; R 2 -5-Cl; R 3 «4-Cl-Ph; Y- 296 R x =OCF 3 ; R 2 -5-Cl; R 3 -4-Cl-Ph; Y= 297 R X «=CF 3 ; R 2 =5-F; R 3 «=4-Cl-Ph; Y= 298 R x =OCF 3 ; R 2 =5-F; R 3 =4-Cl-P ; Y= 299 R =CF 3 ; R 2 =4-C1; R 3 =4-Cl-P ; Y= 300 R x =OCF 3 ; R 2 =4-C1; R 3 -4-Cl-P ; Y- 301 R X =CF 3 ; R 2 =4-F; R 3 -4-Cl-Ph; Y= 302 R=OCF 3 ; R 2 =»4-F; R 3 «4-Cl-Ph; Y- 303 R1=CF 3 ; R 2 -5-Cl; R 3 =4-F-Ph; Y= 304 R x =OCF 3 ; R 2 =5-C1; R 3 =4-F-Ph; Y= 305 R X =CF 3 ; R 2 =»5-F; R 3 «=4-F-P ; Y- 306 R x =OCF 3 ; R 2 =5-F; R 3 =4-F-Ph; Y= 307 R X -CF 3 ; R 2 -4-Cl; R 3 -4-F-P ; Y= 308 R x =OCF 3 ; R 2 =4-C1; R 3 =4-F-Ph; Y= 309 R X =CF 3 ; R 2 =4-F; R 3 -4-F-P ; Y- 310 R =OCF 3 ; R 2 =4-F R 3 »4-F-Ph; Y= 311 R X =CF 3 ; R 2 «=5-C1; R 3 -Me; Y- 312 R x =OCF 3 ; R 2 =5-C1; R 3 «Me; Y- 313 R=CF 3 ; R 2 »5-F; R 3 -Me; Y- 314 R x =OCF 3 ; R 2 =5-F; R 3 -Me; Y= 315 R X =CF 3 ; R 2 =4-C1; R 3 «Me; Y= 316 R x = CF 3 ; R 2 =4-C1; R 3 =Me; Y= 317 R X =CF 3 ; R 2 =4-F; R 3 -Me; Y= 318 R x =OCF 3 ; R 2 -=4-F; R 3 =Me; Y= 319 R X =CF 3 ,* R 2 -5-Cl; R 3 -Et; Y= 320 R =OCF 3 ; R 2 =5-C1; R 3 =Et; Y- 321 R X =CF 3 ; R 2 =5-F; R 3 -=Et; Y» 322 R x =OCF 3 ; R 2 =5-F; R 3 =Et; Y= 323 R=CF 3 ; R 2 =4-C1; R 3 =Et; Y= 324 R»=OCF 3 ; R 2 =4-C1; R 3 -Et; Y= 325 R1=CF 3 ; R 2 «4-F; R 3 -Et; Y= 326 R x =OCF 3 ; R 2 -4-F; R 3 =Et; Y=

K-K-9

327 R X =CF 3 ; R 2 «=5-C1; R 3 -i-Pr; Y- 328 R x =OCF 3 ; R 2 =5-C1; R 3 =I-Pr; Y= 329 R X =CF 3 ; R 2 =5-F; R 3 »i-Pr; Y= 330 R =OCF 3 ; R 2 =5-F; R 3 =i-Pr; Y- 331 R1=CF 3 ; R 2 =*4-C1; R 3 =°i-Pr; Y- 332 R =OCF 3 ; R 2 -4-Cl; R 3 «=i-Pr; Y- 333 R X =CF 3 ; R 2 =4-F; R =i-Pr; Y- 334 R x =OCF 3 ; R 2 =4-F; R 3 -i-Pr; Y>=

K-K-10

335 R ,l==rCF 3 ; R"=5-C1; R°=Me; Y= 336 R x =OCF 3 ; R 2 =5-C1; R 3 «Me; Y= 337 R »1 X -=CF 3 ; R 2^-=5R--ιF; R J «Me; Y- 338 R x =OCF 3 ; R 2 -5-F; R 3 -Me; Y- 339 R =CF 3 ; R 2 =4-C1; R 3 =Me; Y= 340 R x =OCF 3 ; R 2 -4-Cl; R 3 -Me; Y- 341 R X =CF 3 ; R 2 -4-F; R 3 -Me; Y- 342 R x =OCF 3 ; R 2 -4-F; R 3 -Me; Y- 343 R X *=CF 3 ; R 2 -5-Cl; R 3 -Et; Y= 344 R x -OCF 3 ; R 2 -5-Cl; R 3 -Et; Y- 345 R1=CF 3 ; R 2 =5-F; R 3 -Et; Y- 346 R x «=OCF 3 ; R 2 -5-F; R 3 -Et; Y- 347 R l=CF 3 ; R «=4-C1; R 3 -Et; Y- 348 R x =OCF 3 ; R 2 =4-C1; R 3 =Et; Y= 349 R1=CF 3 ; R 2 =4-F; R 3 =Et; Y= 350 R =0CF 3 ; R 2 =4-F; R 3 =Et; Y"

K-K-11

351 R -CF 3 ; R 2 =4-F; R 3 =4-F-Ph; Y=

352 R x =OCF 3 ; R 2 =4-F; R 3 -4-F-Ph; Y=

353 R X =CF 3 ; R 2 -4-Cl; R 3 -4-F-Ph; Y-=

354 R x =OCF 3 ; R 2 -4-Cl; R 3 -4-F-Ph; Y-

355 R X -CF 3 ; R 2 -4-F; R 3 -4-Cl-Ph; Y-

356 R x =OCF 3 ; R 2 «4-F; R 3 -4-Cl-P ; Y=

357 R X =CF 3 ; R 2 -4-Cl; R 3 -4-Cl-Ph; Y-

358 R x =OCF 3 ; R 2 «4-C1; R 3 -4-Cl-P ; Y-

K-K-12

359 R X =CF 3 ; R 2 =5-F; R 3 «=4-F-Ph; Y=

360 R x =OCF 3 ; R 2 =5-F; R 3 =4-F-P ; Y=

361 R X =CF 3 ; R 2 =5-C1; R 3 =4-F-P ; Y«

362 R>=OCF 3 ; R 2 «*5-C1; R 3 «4-F-Ph; Y=

363 R X -CF 3 ; R 2 =5-F; R 3 -4-Cl-Ph; Y-

364 R x =OCF 3 ; R 2 -5-F; R 3 =4-Cl-Ph; Y=

365 R X -CF 3 ; R 2 -5-Cl; R 3 -4-Cl-Ph; Y-

366 R x =OCF 3 ; R 2 =5-C1; R 3 «4-Cl-Ph; Y«=

I&3H 2.

K-K-l

1 R X «=CF 3 ; R 2 «C1; R 3 =4-Cl-Ph; Y*

2 R x «OCF 3 ; R 2 =C1; R 3 =4-Cl-Ph Y=

3 R =CF 3 ; R 2 =C1; R 3 «=4-F-Ph; Y«

4 R x -OCF 3 ; R 2 «=C1; R 3 -4-F-Ph; Y*

5 R X =CF 3 ; R 2 =C1; R 3 =Ph; Y=

6 R «=OCF 3 ; R 2 -C1; R 3 -P ; Y-

7 R =CF 3 ; R 2 «F; R 3 «4-Cl-Ph; Y-

8 R x =OCF 3 R 2 =F; R 3 =4-Cl-Ph; Y=

9 R -CF 3 ; R 2 -F; R 3 -4-F-Ph; Y-

10 R x =OCF 3 ; R 2 =F; R 3 -4-F-Ph; Y=

11 R X -CF 3 ; R 2 =F; R 3 -Ph; Y-

12 R x -OCF 3 ; R 2 -F; R 3 -Ph; Y-

K-K-2

13 R X -CF 3 ; R 2 -C1; R 3 -Me; Y-

14 R x »OCF 3 ; R 2 -C1; R 3 -Me; Y-

15 R X "CF 3 ; R 2 -F; R 3 -Me; Y-

16 R x -OCF 3 ; R 2 «F; R 3 -Me; Y-

17 R -CF 3 ; R 2 =C1; R 3 -Et; Y-

18 R x =OCF 3 ; R 2 «=C1; R 3 -Et; Y-

19 R X -CF 3 ; R 2 =F; R 3 =Et; Y=

20 R x -OCF 3 ; R 2 =F; R 3 -Et; Y-

K=K-3

21 R -CF 3 ; R 2 -C1; R 3 -4-Cl-Ph; Y*

22 R *=OCF 3 ; R 2 =C1; R 3 «4-Cl-Ph; Y=

23 R X -CF 3 ; R 2 =»C1; R 3 -4-F-Ph; Y»

K-K-3 R x =OCF 3 ; R 2 *=C1; R 3 -4-F-P ; Y- R X -CF 3 ; R 2 -=C1; R 3 «Ph; Y= R x =OCF 3 ; R C1; R 3 -P ; Y- R X -CF 3 ; R 2 -F; R 3 -4-Cl-Ph; Y- R x =OCF 3 ; R 2 =F; R 3 =4-Cl-Ph; Y= R X =CF 3 ; R 2 =F; R 3 -4-F-P ; Y= R =OCF 3 ; R 2 -F; R 3 -4-F-P ; Y-= R X -CF 3 ; R 2 =F; R 3 -Ph; Y= R x -OCF 3 ; R 2 »F; R 3 -Ph; Y-

K«K-4 R X =CF 3 ; R 2 =6-C1; R 3 =COOMe; Y= R OCF 3 ; R 2 -6-Cl; R 3 =COOMe; Y- R X -CF 3 ; R 2 -6-Cl; R 3 -4-Cl-Ph; Y» R x =OCF 3 ; R 2 -6-Cl; R 3 -4-Cl-Ph; Y»= R X -CF 3 ; R 2 -6-Cl; R 3 -4-F-Ph; Y= R -OCF 3 ; R 2 -6-Cl; R 3 -4-F-P ; Y- R X -CF 3 ; R 2 -6-F; R 3 -COOMe; Y- R x -OCF 3 ; R 2 -6-F; R 3 -COOMe; Y*= R X -CF 3 ; R 2 -6-F; R 3 -4-Cl-Ph; Y- R x =OCF 3 ; R 2 -6-F; R 3 -4-Cl-P ; Y= R X -CF 3 ; R 2 -6-F; R 3 -4-F-Ph; Y» R x -OCF 3 ; R 2 -6-F; R 3 -4-F-Ph; Y= R =CF 3 ; R 2 -6-CF 3 ; R 3 -COOMe; Y«= R x =OCF 3 ; R 2 =6-CF 3 ; R 3 -COOMe; Y= R X -CF 3 ,* R 2 -6-CF 3 ; R 3 -4-Cl-Ph; Y» R x =OCF 3 ; R 2 -6-CF 3 ; R 3 -4-Cl-P ; Y- R X =CF 3 ; R 2 -6-CF 3 ; R 3 -4-F-P ; Y= R X HDCF 3 ; R 2 -6-CF 3 ; R 3 -4-F-Ph; Y- R X -CF 3 ; R 2 -5-F; R 3 -COOMe; Y- R x -OCF 3 R 2 -5-F; R 3 »COOMe; Y- R X -CF 3 ; R 2 -5-F; R 3 -4-Cl-Ph; Y= R x =OCF 3 ; R 2 =»5-F; R 3 -4-Cl-Ph; Y=

K-K-4 R X -CF 3 ; R 2 -5-F; R 3 -4-F-P ; Y- R x =OCF 3 ; R 2 -5-F; R 3 -4-F-Ph; Y- R X =CF 3 ; R 2 -5-Cl; R 3 «=COOMe; Y- R x =OCF 3 ; R 2 -5-Cl; R 3 «COOMe; Y- R X -CF 3 ; R 2 -5-Cl; R 3 -4-Cl-P ; Y= R -OCF 3 ; R 2 -5-Cl; R 3 -4-Cl-Ph; Y- R X -CF 3 ; R -5-Cl; R 3 -4-F-Ph; Y- R x =OCF 3 ; R 2 «=5-C1; R 3 -4-F-Ph; Y= R X =>CF 3 ; R 2 «6-C1; R 3 -Me; Y- R =OCF 3 ; R 2 =6-C1; R 3 -Me; Y-= R =CF 3 ; R 2 =*6-F; R 3 «Me; Y= R x «=OCF 3 ; R 2 -6-F; R 3 -Me; Y- R X -CF 3 ; R 2 -6-CF 3 ; R 3 -Me; Y- R x =0CF 3 ; R 2 =6-CF 3 ; R 3 -Me; Y- R X =CF 3 ; R 2 -5-Cl; R 3 -Me; Y- R x -0CF 3 ; R 2 -5-Cl; R 3 -Me; Y- R «CF 3 ; R 2 -5-F; R 3 -Me; Y- R x -OCF 3 ; R 2 -5-F; R 3 -Me; Y- R X -CF 3 ; R 2 -6-Cl; R 3 -i-Pr; Y- R x «OCF 3 ; R 2 -6-Cl; R 3 «-i-Pr; Y- R X =CF 3 ; R 2 -»6-F; R 3 -i-Pr; Y- R x =OCF 3 ; R 2 «6-F; R 3 -i-Pr; Y- R X -CF 3 ; R 2 -6-CF 3 ; R 3 -i-Pr; Y= R x -0CF 3 ; R 2 -6-CF 3 ; R 3 «i-Pr; Y- R X »=CF 3 ; R 2 «5-C1; R 3 -i-Pr; Y= R x «OCF 3 ; R 2 -5-Cl; R 3 -i-Pr; Y- R X =CF 3 ; R 2 -5-F; R 3 =i-Pr; Y= R x =0CF 3 ; R -5-F; R 3 =i-Pr; Y-

K-K-5 R X =CF 3 ; R 2 -6-Cl; R 3 =COOMe; Y* R x =OCF 3 ; R 2 -6-Cl; R 3 »COOMe; Y» R X =CF 3 ; R 2 «6-C1 R 3 -4-Cl-P ; Y=

K-K-5

86 R x =OCF 3 ; R 2 -6-Cl; R 3 -4-Cl-Ph; Y=

87 R X «=CF 3 ; R 2 ~6-C1; R 3 -4-F-Ph; Y-

88 R x =OCF 3 ; R 2 -6-Cl; R 3 -4-F-Ph; Y-

89 R X -CF 3 ; R 2 «6-F; R 3 =COOMe; Y«=

90 R x -OCF 3 ; R 2 -6-F; R 3 «COOMe; Y-

91 R1-CF 3 ; R 2 -6-F; R 3 -4-Cl-Ph; Y-

92 R!-=OCF 3 ; R 2 -6-F; R 3 =4-Cl-P ; Y"

93 R X «CF 3 ; R 2 -6-F; R 3 -4-F-P ; Y"

94 R x «=OCF 3 ; R 2 -6-F; R 3 =4-F-P ; Y"

95 R1-=CF 3 ; R 2 -6-CF 3 ; R 3 »=COOMe; Y-

96 R x -=OCF 3 ; R 2 -6-CF 3 ; R 3 =COOMe; Y-

97 R X -CF 3 ; R 2 -6-CF 3 ; R 3 -4-Cl-Ph; Y-

98 R x -OCF 3 ; R 2 -6-CF 3 ; R 3 «4-Cl-P ; Y-

99 R1=CF 3 ; R 2 =6-CF 3 ; R 3 -4-F-PJI; Y=

100 R!-OCF 3 ; R 2 =6-CF 3 ; R 3 «4-F-Ph; Y=

101 R X =CF 3 R 2 -5-F; R 3 «COOMe; Y-

102 R x =OCF 3 ; R 2 -5-F; R 3 -COOMe; Y-

103 Rl-»CF 3 ; R 2 -5-F; R 3 -4-Cl-Ph; Y=

104 R x «OCF 3 ; R -5-F; R 3 -4-Cl-Ph; Y-

105 R!«CF 3 ; R 2 -5-F; R 3 «4-F-Ph; Y=

106 Rl-=OCF 3 ; R 2 -5-F; R 3 =4 F-P Y-

107 R X =-CF 3 ; R 2 -5-Cl; R 3 =COOMe; Y-

108 R x «=0CF 3 ; R 2 »5-C1; R 3 =CO0Me; Y«=

109 R X -CF 3 ; R 2 -5-Cl; R 3 «4-Cl-Ph; Y-

110 R x -OCF 3 ; R 2 -5-Cl; R 3 «*4-Cl-Ph; Y«=

111 R X =CF 3 ; R 2 =5-C1; R 3 =4-F-P ; Y-

112 R x «OCF 3 ; R 2 -5-Cl; R 3 -4-F-Ph; Y-

113 R1-CF 3 ; R 2 «6-C1; R 3 «Me; Y-

114 R =OCF 3 ; R 2 «6-C1; R 3 »Me; Y-

115 R1=CF 3 ; R 2 =6-F; R 3 «Me; Y-

116 R x =OCF 3 ; R 2 -6-F; R 3 -Me; Y-

117 R =»CF 3 ; R 2 -6-CF 3 ; R 3 -Me; Y=

K-K-5

118 R x -OCF 3 ; R 2 -6-CF 3 ; R 3 -Me Y- 119 R1-=CF 3 ; R 2 -5-Cl; R 3 -Me; Y- 120 R x -OCF 3 ; R 2 -5-Cl; R 3 -Me; Y- 121 R -=CF 3 ; R 2 -5-F; R 3 -Me; Y- 122 R x =OCF 3 ; R 2 -5-F; R 3 -Me; Y- 123 R X -CF 3 ; R 2 -6-Cl; R 3 -i-Pr; Y* 124 R -OCF 3 ; R 2 -6-Cl; R 3 -i-Pr; Y- 125 R X -CF 3 ; R 2 -6-F; R 3 -i-Pr; Y- 126 R x «OCF 3 ; R 2 -6-F; R 3 -i-Pr; Y= 127 R X -CF 3 ; R 2 -6-CF 3 ; R 3 -i-Pr; Y- 128 R x =OCF 3 ; R 2 =6-CF 3 ; R 3 -»i-p r ; Y= 129 R X -CF 3 ; R 2 -5-Cl; R 3 «i-Pr; Y- 130 R -OCF 3 ; R 2 -5-Cl; R 3 -i-Pr; Y- 131 R X -CF 3 ; R 2 -5-F; R 3 -i-Pr; Y= 132 R -=OCF 3 ; R 2 -5-F; R 3 -i-Pr; Y-

K-K-6

133 R X -CF 3 ; R 2 -C1; R 3 «4-Cl-Ph; Y- 134 R x «=OCF 3 ; R 2 -C1; R 3 -4-Cl-Ph; Y- 135 R X -CF 3 ; R 2 »C1; R 3 -4-F-Ph; Y- 136 R x -OCF 3 ; R 2 -C1; R 3 -4-F-P ; Y= 137 R «CF 3 R 2 =F; R 3 -4-Cl-Ph; Y- 138 R x -OCF 3 ; R 2 -F; R 3 -4-Cl-Ph; Y- 139 R X -CF 3 ; R 2 =F; R 3 =4-F-Ph; Y- 140 R -OCF 3 ; R 2 -F; R 3 «4-F-Ph; Y- 141 R X -CF 3 ; R 2 -CF 3 ; R 3 «4-Cl-Ph; Y* 142 R x =OCF 3 ; R 2 =CF 3 ; R 3 -4-Cl-Ph Y= 143 R X -CF 3 ; R 2 -=CF 3 ; R 3 =4-F-Ph; Y- 144 R x =OCF 3 ; R 2 =CF 3 ; R 3 «4-F-Ph; Y*

K»K-7

145 R X =CF 3 ; R 2 «=C1; R 3 «4-Cl-Ph; Y- 146 R x «=OCF 3 ; R 2 =C1; R 3 -4-Cl-Ph; Y- 147 R X =CF 3 ; R 2 =C1; R 3 «-4-F-Ph; Y=

K-K-7

148 R x -OCF 3 ; R 2 -C1; R 3 «4-F-Ph; Y- 149 R X -CF 3 ; R 2 -F; R 3 -4-Cl-Ph; Y- 150 R x -OCF 3 ; R 2 «F; R 3 -4-Cl-Ph; Y- 151 R1-CF 3 ; R 2 -F; R 3 -4-F-Ph; Y- 152 R x -OCF 3 ; R 2 ~F; R 3 -4-F-Ph; Y= 153 R X -CF 3 ; R 2 -CF 3 ; R 3 -4-Cl-Ph; Y- 154 R x =OCF 3 ; R 2 -CF 3 ; R 3 -4-Cl-Ph; Y- 155 R X -CF 3 ; R 2 -CF 3 ; R 3 -4-F-Ph; Y~ 156 R x -OCF 3 ; R 2 ~CF 3 ; R 3 -4-F-Ph; Y-

K-K-8

Z-CH 2

157 R1-CF 3 ; R 2 -5-Cl; R 3 -COOMe; 158 R x -OCF 3 ; R 2 -5-Cl; R 3 -COOMe; 159 R X -CF 3 ; R 2 -5-F; R 3 -COOMe; 160 R x -OCF 3 ; R 2 -5-F; R 3 -C0OMe; 161 R X =CF 3 ; R 2 -5-CF 3 ; R 3 -=COOMe; 162 R x -OCF 3 ; R 2 «5-CF 3 ; R 3 -COOMe; 163 R X -CF 3 ; R 2 «4-C1; R 3 -COOMe; 164 R -OCF 3 ; R 2 -4-Cl; R 3 -COOMe; 165 R -CF 3 ; R 2 -4-F; R 3 «COOMe; 166 R x -OCF 3 ; R 2 -4-F; R 3 «COOMe; 167 R X -CF 3 ; R 2 -5-Cl; R 3 -4-Cl-P ; 168 R x -OCF 3 ; R 2 -5-Cl; R 3 «4-Cl-Ph; 169 R X -CF 3 ; R 2 ~5-F; R 3 -4-Cl-Ph; 170 R x -OCF 3 ; R 2 -5-F; R 3 -4-Cl-Ph; 171 R X -CF 3 ; R -5-CF 3 ; R 3 -4-Cl-Ph; 172 R x -OCF 3 ; R 2 -5-CF 3 ; R 3 -4-Cl-Ph; 173 R X -CF 3 ; --vPh; 174 R x -OCF 3 ; R 2 -4-Cl; R 3 -4-Cl-Ph; 175 R -CF 3 ; R 2 -4-F; R 3 -4-Cl-Ph; 176 R x -OCF 3 ; R 2 -4-F; R 3 -4-Cl-Ph; 177 R X »CF 3 ; R 2 -5-Cl; R 3 «4-F-Ph;

K-K-8

Z-CH 2

178 R =0CF 3 ; R 2 =5-C1; R 3 -»4-F-P ; Y- 179 R X -CF 3 ; R 2 -5-F; R 3 -4-F-Ph; Y- 180 R x =OCF 3 ; R 2 -5-F; R 3 =4-F-Ph; Y= 181 R X -CF 3 ; R 2 -5-CF 3 ; R 3 -4-F-Ph; Y= 182 R x »OCF 3 ; R 2 -5-CF 3 ; R 3 -4-F-Ph; Y- 183 R1=CF 3 ; R 2 =4-C1; R 3 -4-F-P ; Y= 184 R x =OCF 3 ; R 2 -4-Cl; R 3 -4-F-Ph; Y- 185 R1»CF 3 ; R 2 -4-F; R 3 -4-F-P ; Y- 186 R x -OCF 3 ; R 2 -4-F; R 3 -4-F-P ; Y- 187 R =CF 3 ; R 2 =5-C1; R 3 -Me; Y= 188 R x =0CF 3 ; R 2 -5-Cl; R 3 -Me; Y= 189 R X »CF 3 ; R 2 =5-F; R 3 -Me; Y«= 190 R1=OCF 3 ; R 2 =5-F; R 3 =Me; Y= 191 R =CF 3 ; R 2 -5-CF 3 ; R 3 -Me; Y- 192 R x =OCF 3 ; R 2 =5-CF 3 ; R 3 «Me; Y* 193 R X =>CF 3 ; R 2 =4-C1; R 3 =Me; Y= 194 R!-OCF 3 ; R 2 -4-Cl; R 3 «Me; Y= 195 R1-CF 3 ; R 2 -4-F; R 3 -Me; Y= 196 R1=0CF 3 ; R 2 -4-F; R 3 -Me; Y= 197 R1«.CF 3 ; R 2 -5-Cl; R 3 -i-Pr; Y- 198 R x -OCF 3 ; R 2 -5-Cl; R 3 -i-Pr; Y- 199 R X =CF 3 ; R 2 -5-F; R 3 =i-Pr; Y= 200 R1-0CF 3 R 2 -5-F; R 3 -i-Pr; Y« 201 R X -CF 3 ; R 2 -5-CF 3 R 3 -i-Pr Y- 202 R!-OCF 3 ; R 2 -5-CF 3 ; R 3 -i-Pr; Y- 203 R X -CF 3 ; R «4-C1; R 3 -i-Pr; Y» 204 R1«-OCF 3 ; R 2 -4-Cl; R 3 -i-Pr; Y= 205 R X =CF 3 ; R 2 =4-F; R 3 -=i-Pr; Y= 206 R x =0CF 3 ; R 2 *=4-F; R 3 =i-Pr; Y=

K-K-8 Z-0

207 R X «CF 3 ; R 2 =»5-C1; R 3 -COOMe; Y-

208 R x -OCF 3 ; R 2 »5-C1; R 3 -COOMe; Y-

209 R X =CF 3 ; R 2 =5-F; R 3 =COOMe; Y-

210 R -OCF 3 ; R 2 -5-F; R 3 -COOMe; Y-

211 R X -CF 3 ; R 2 -5-CF 3 ; R 3 -COOMe; Y-

212 R«OCF 3 ; R 2 -5-CF 3 ; R 3 -COOMe; Y-

213 R X -CF 3 ; R 2 -4-Cl; R 3 -COOMe; Y-

214 R x -OCF 3 ; R 2 -4-Cl; R 3 -COOMe; Y-

215 R=CF 3 ; R 2 -4-F; R 3 =COOMe; Y=

216 R x =OCF 3 ; R 2 -4-F; R 3 «=COOMe; Y-

217 R X »CF 3 ; R 2 -5-Cl; R 3 -4-Cl-Ph; Y-

218 R?-=OCF3; R 2 -5-Cl; R 3 -4-Cl-Ph; Y=

219 R X -CF 3 ; R 2 »5-F; R 3 -4-Cl-P ; Y-

220 R -OCF 3 ; R 2 -5-F; R 3 -4-Cl-P ; Y-

221 R X -CF 3 ; R 2 -5-CF 3 ; R 3 -4-Cl-Ph; Y-

222 R x - CF 3 ; R 2 -5-CF 3 ; R 3 -4-Cl-P ; Y-

223 R X -CF 3 ; R 2 -4-Cl; R 3 -4-Cl-Ph; Y-

224 R x -OCF 3 ; R-4-Cl; R 3 -4-Cl-Ph; Y-

225 R 1 -CF 3 ; R 2 -4-F; R 3 -4-Cl-Ph; Y-

226 R x -OCF 3 R 2 -4-F; R 3 -4-Cl-Ph; Y-

227 R X -CF 3 ; R 2 -5-Cl; R 3 -4-F-Ph; Y-

228 R x =OCF 3 ; R 2 -5-Cl; R 3 =4-F-Ph; Y-

229 R X =CF 3 ; R 2 -5-F; R 3 -4-F-Ph; Y=

230 R x -OCF 3 ; R 2 -5-F; R 3 -4-F-P ; Y-

231 R X =CF 3 ; R 2 »5-CF 3 ; R 3 -4-F-Ph; Y=

232 R x =OCF 3 ; R 2 =5-CF 3 ; R 3 =4-F-P ; Y=

233 R X -CF 3 ; R 2 -4-Cl; R 3 «4-F-P ; Y=

234 R x «OCF 3 ; R 2 -4-Cl; R 3 «4-F-Ph Y=

235 R X -CF 3 ; R 2 -4-F; R 3 «-4-F-Ph; Y=

236 R x -OCF 3 ; R 2 »4-F; R 3 -4-F-Ph; Y-

237 R X »CF 3 ; R 2 =5-C1; R 3 -Me; Y=

K-K-8 Z«0

238 R =OCF 3 ; R 2 «5-C1; R 3 «Me; Y= 239 R -CF 3 ; R 2 -5-F; R 3 -Me; Y-x 240 R x -OCF 3 ; R 2 -5-F; R 3 -Me; Y- 241 R1=CF 3 ; R 2 -5-CF 3 ; R 3 -Me; Y= 242 R l=0CF 3 ; R 2 -5-CF 3 ; R 3 -Me; Y= 243 R X «CF 3 ; R 2 -4-Cl; R 3 -Me; Y«= 244 R!-=OCF 3 ; R 2 -4-Cl; R 3 -Me; Y«= 245 R1=CF 3 ; R 2 -4-F; R 3 «Me; Y= 246 R!-=OCF 3 ; R 2 -4-F; R 3 -Me; Y= 247 R X -CF 3 ; R 2 -5-Cl; R 3 -i-Pr; Y= 248 R «0CF 3 ; R 2 -5-Cl; R 3 -i-Pr; Y= 249 R1-CF 3 ; R 2 -5-F; R 3 -i-Pr; Y= 250 R x -OCF 3 ; R 2 -5-F; R 3 =i-Pr; Y- 251 R X -CF 3 ; R 2 -5-CF 3 ; R 3 -i-Pr; Y= 252 R!-OCF 3 ; R 2 -5-CF 3 ; R 3 -i-Pr; Y- 253 R X -CF 3 ; R 2 -4-Cl; R 3 -i-Pr; Y- 254 R1»OCF 3 ; R 2 «4-C1; R 3 -i-Pr; Y- 255 R X =CF 3 ; R 2 =4-F; R 3 =i-Pr; Y= 256 R 1 -=OCF 3 ; R 2 "«4-F; R 3 «i-Pr; Y=

K-K-8

Z=N-H

257 R X =CF 3 ; R 2 =5-C1; R 3 «COOMe; Y- 258 R x =OCF 3 ; R 2 -5-Cl; R 3 -COOMe; Y= 259 R X -CF 3 ; R -5-F; R 3 -COOMe; Y- 260 R «OCF 3 ; R 2 -5-F; R 3 -COOMe; Y= 261 R1.=CF 3 ; R 2 «5-CF 3 ; R 3 =COOMe; Y= 262 R -OCF 3 ; R 2 «=5-CF 3 ; R 3 =COOMe; Y- 263 R X =*CF 3 ; R 2 -4-Cl; R 3 =COOMe; Y= 264 R1=OCF 3 ; R 2 =4-C1; R 3 =COOMe; Y= 265 R X =CF 3 ; R 2 -4-F; R 3 «=COOMe; Y- 266 R -=OCF 3 ; R 2 -4-F; R 3 -COOMe; Y«

K-K-8

Z-N-H

267 R X "CF 3 ; R 2 -5-Cl; R 3 -4-Cl-Ph Y- 268 R x «OCF 3 ; R 2 -5-Cl; R 3 -4-Cl-Ph; Y- 269 R1-CF 3 ; R 2 «5-F; R 3 «4-Cl-P ; Y- 270 R-OCF 3 ; R 2 -5-F; R 3 -4-Cl-Ph; Y- 271 R1=CF 3 ; R 2 »5-CF 3 ; R 3 -4-Cl-Ph; Y- 272 R-OCF 3 ; R 2 -5-CF 3 ; R 3 -4-Cl-Ph; Y- 273 R X =CF 3 ; R 2 -4-Cl; R 3 -4-Cl-P ; Y- 274 R x -OCF 3 ; R 2 «4-C1; R 3 -4-Cl-P ; Y- 275 R X =CF 3 ; R 2 -4-F; R 3 -4-Cl-Ph; Y- 276 R x -OCF 3 ; R 2 -4-F; R 3 -4-Cl-P ; Y- 277 R X -CF 3 ; R 2 -5-Cl; R 3 -4-F-Ph; Y- 278 R x «OCF 3 ; R 2 -5-Cl; R 3 -4-F-P ; Y- 279 R X =CF 3 ; R 2 «5-F; R 3 «4-F-P ; Y= 280 R -=OCF 3 ; R 2 -5-F; R 3 «4-F-P ; Y- 281 R X -CF 3 ; R 2 -5-CF 3 ; R 3 -4-F-Ph; Y- 282 R x «OCF 3 ; R 2 -5-CF 3 ; R 3 -4-F-Ph; Y<= 283 R X =CF 3 ; R -4-Cl; R 3 -4-F-Ph; Y- 284 R x -OCF 3 ; R 2 -4-Cl; R 3 -4-F-Ph; Y- 285 R X =CF 3 ; R Ϊ 2- ώ -_4Λ_-IF; R 3°-Λ4--Fp_-tPh; Y" 286 R x -OCF 3 ; R 2 -4-F; R 3 -4-F-Ph; Y- 287 R X =CF 3 ; R 2 -5-Cl; R 3 «*te; Y= 288 R x -OCF 3 ; R 2 -5-Cl; R 3 «Me; Y- 289 R 1»CF 3 ; R 2 -5-F; R 3 -Me; Y- 290 R x -OCF 3 ; R 2 -5-F; R 3 -Me; Y- 291 R X =CF 3 ; R 2 -5-CF 3 ; R 3 «Me; Y- 292 R -OCF 3 ; R 2 -5-CF 3 ; R 3 -Me; Y- 293 R X -CF 3 ; R 2 -4-Cl; R 3 -Me; Y= 294 R x «OCF 3 ; R 2 -4-Cl; R 3 -=Me; Y-= 295 R1 « CF 3 ; R 2 «4-F; R 3 -Me; Y- 296 R x =OCF 3 ; R 2 =4-F; R 3 -Me; Y= 297 R! « =CF 3 ; R 2 =5-C1; R 3 =i-Pr; Y=

K-K-8

Z-N-H

298 R x -OCF 3 ; R 2 -5-Cl; R 3 -i-Pr; Y= 299 R X -CF 3 ; R 2 -5-F; R 3 -i-Pr; Y- 300 R x -OCF 3 ; R 2 -5-F; R 3 -i-Pr; Y- 301 R X -CF 3 ; R 2 -5-CF 3 ; R 3 -i-Pr; Y- 302 R x «OCF 3 ; R 2 -5-CF 3 ; R 3 -i-Pr; Y- 303 R X -CF 3 ; R 2 «*4-C1; R 3 -i-Pr; Y- 304 R x =OCF 3 ; R 2 -4-Cl; R 3 -i-Pr; Y= 305 R X -CF 3 ; R 2 -4-F; R 3 -i-Pr; Y- 306 R =OCF 3 ; R 2 =4-F; R 3 -i-Pr; Y-

K-K-9

307 R1=CF 3 ; R 2 -5-Cl; R 3 -4-Cl-P ; Y* 308 R x -OCF 3 ; R 2 -5-Cl; R 3 «4-Cl-Ph; Y- 309 R -CF 3 ; R 2 -5-F; R 3 «4-Cl-Ph; Y= 310 R x =OCF 3 ; R 2 -5-F; R 3 «4-Cl-Ph; Y« 311 R X -=CF 3 ; R 2 =4-C1; R 3 =4-Cl-Ph; Y- 312 R x -OCF 3 ; R 2 -4-Cl; R 3 «4-Cl-Ph; Y- 313 R 1-CF 3 ; R 2 -4-F; R 3 -4-Cl-Ph; Y- 314 R x =OCF 3 ; R 2 -4-F; R 3 «4-Cl-Ph; Y- 315 R X -CF 3 ; R 2 -5-Cl; R 3 «4-F-Ph; Y- 316 R x -OCF 3 ? R 2 -5-Cl; R 3 -4-F-Ph; Y- 317 R X -CF 3 ; R 2 -5-F; R 3 -4-F-Ph; Y- 318 R x *OCF 3 ; R * 2 "--5*--F; R 3°_-«-4i--Fp_-tPh; Y- 319 R1-CF 3 -; R 2 -4-Cl; R 3 «4-F-Ph; Y- 320 R x -OCF 3 ; R 2 -4-Cl; R 3 -4-F-P ; Y- 321 R X =CF 3 ; R 2 -4-F;. R 3 «4-F-Ph; Y- 322 R x =OCF 3 ; R ;2- c κ ->4ι_-Fι ; R 3°--«-4ι--Fp---.rPh Y= 323 R X -CF 3 ; R 2 -5-Cl; R 3 «Me; Y « 324 R =OCF 3 ; R 2 -5-Cl; .R 3 -Me; Y" 325 R1=CF 3 ; R 2 -5-F; R 3 -Me; Y= 326 R x *-OCF 3 ; R 2 -5-F; R 3 -Me; Y « = 327 R l « -CF 3 ; R 2 -4-Cl; R 3 -Me; Y=

K-K-9

328 R -0CF 3 ; R 2 «4-C1; R 3 -Me; Y- 329 R X =CF 3 ; R 2 =4-F; R 3 «Me; Y-x 330 R x «0CF 3 ; R 2 -4-F; R 3 -Me; Y- 331 R X -CF 3 ; R -5-Cl; R 3 «Et; Y- 332 R!-=OCF 3 ; R 2 =5-C1; R 3 -Et; Y= 333 R X «CF 3 ; R 2 =5-F; R 3 -Et; Y= 334 R!-OCF 3 ; R 2 -5-F; R 3 -Et; Y- 335 R X =CF 3 ; R 2 »4-C1; R 3 =Et; Y= 336 R X «0CF3; R 2 -4-Cl; R 3 «Et; Y= 337 R1«CF 3 ; R 2 -4-F; R 3 =Et; Y= 338 R x =OCF 3 ; R 2 =4-F; R 3 -=Et; Y«= 339 R X =CF 3 ; R 2 =5-C1; R 3 -i-Pr; Y= 340 R1-OCF 3 ; R 2 -5-Cl; R 3 -i-Pr; Y- 341 R =CF 3 ; R 2 -5-F; R 3 -i-Pr; Y- 342 R X =CF 3 ; R 2 =5-F; R 3 =i-Pr; Y* 343 R X «CF 3 ; R 2 -»4-Cl; R 3 -i-Pr; Y= 344 R x =OCF 3 ; R 2 -4-Cl; R 3 -i-Pr; Y- 345 R =CF 3 ; R 2 =4-F; R 3 =ά-Pr; Y= 346 R x «=OCF 3 ; R 2 -4-F; R 3 =i-Pr Y«=

K-K-10

347 R=CF 3 ; R 2 =5-C1; R 3 «Me; Y= 348 R1«OCF 3 ; R 2 -5-Cl; R 3 -Me Y= 349 R X =CF 3 ; R 2 =5-F; R 3 =Me; Y= 350 R x -OCF 3 ; R 2 -5-F; R 3 -Me; Y= 351 R X =CF 3 ; R 2 -4-Cl; R 3 -Me; Y- 352 R x =OCF 3 ; R 2 =4-C1; R 3 -Me; Y= 353 R»CF 3 ; R 2 -4-F; R 3 -Me; Y= 354 R x =OCF 3 ; R 2 -4-F; R 3 -Me; Y« 355 R X =CF 3 ; R 2 =5-C1; R 3 =Et; Y= 356 R x =OCF 3 ; R 2 =5-C1; R 3 -Et; Y» 357 R=CF 3 ; R 2 -5-F; R 3 «=Et Y= 358 R1-=OCF 3 ; R 2 -5-F; R 3 -Et; Y=

K-K-10

359 R -CF 3 ; R 2 -4-Cl; R 3 -Et; Y- H Me COOMe C 360 R x - CF 3 ; R 2 -4-Cl; R 3 -Et; Y« H Me COOMe C 361 R X <-CF 3 ; R 2 -4-F; R 3 «Et; Y- H Me COOMe C 362 R x -OCF 3 ; R 2 -4-F; R 3 -Et; Y- H Me COOMe C

K-K-ll

363 R1«CF 3 ; R 2 -4-F; R 3 -4-F-Ph; Y- 364 R x -OCF 3 ; R 2 -4-F; R 3 «4-F-Ph; Y- 365 R1«-CF 3 ; R 2 =4-C1; R 3 -4-F-Ph; Y- 366 R1=0CF 3 ; R 2 -4-Cl; R 3 -=4-F-Ph; Y= 367 «CF 3 ; R---4-F; ^ 3 -4-Cl-P ; Y« 368 R =OCF 3 ; R 2 =4-F; R 3 =4-Cl-Ph; Y= 369 R X -CF 3 ; R 2 -4-Cl; R 3 -4-Cl-P ; Y- 370 R x -OCF 3 ; R 2 -4-Cl; R 3 -4-Cl-Ph; Y«=

K-K-12

371 R X «CF 3 ; R 2 -5-F; R 3 -4-F-Ph; Y- 372 R x =OCF 3 ; R 2 -5-F; R 3 -4-F-Ph; Y» 373 R =CF 3 ; R 2 -5-Cl; R 3 -4-F-Ph; Y- 374 R x =OCF 3 ; R 2 -=5-Cl; R 3 -4-F-Ph; Y= 375 R X =CF 3 ; R 2 -5-F; R 3 -4-Cl-P ; Y* 376 R x =0CF 3 ; R 2 »5-F; R 3 -4-Cl-Ph; Y= 377 R X -CF 3 ; R 2 -5-Cl; R 3 -4-Cl-Ph; Y- 378 R1-OCF 3 ; R 2 =5-C1; R 3 -4-Cl-Ph; Y=

T BLE 3

K K-1 R X =CF 3 ; R 2 =C1; R 3 *»4-Cl-Ph; Y" R x »OCF 3 ; R 2 -C1; R 3 -4-Cl-Ph; Y- R X =CF 3 ; R 2 =C1; R 3 -4-F-Ph; Y= R x = CF 3 ; R 2 =C1; R 3 =4-F-Ph; Y- R X -CF 3 ; R C1; R 3 -P ; Y- R »OCF 3 ; R 2 =C1; R 3 -P ; Y*- R »CF 3 ; R 2 =F; R 3 «4-Cl-P ; Y* R «OCF 3 ; R 2 =F; R 3 -4-Cl-Ph; Y- R X =CF 3 ; R 2 =F; R 3 -4-F-Ph; Y- R =OCF 3 ; R 2 =F; R 3 =4-F-Ph; Y= R X -CF 3 ; R 2 -F; R 3 -Ph; Y- R x =OCF 3 ; R 2 =F; R 3 -Ph; Y=

K-K-2 R X =CF 3 ; R 2 -C1; R 3 -Me; Y- R x =OCF 3 ; R 2 =C1; R 3 =Me; Y- R X =CF 3 ; R 2 -F; R 3 =Me; Y- R x "=OCF 3 ; R 2 -F; R 3 -Me; Y" R X =CF 3 ; R 2 =C1; R 3 =Et; Y= R x «OCF 3 ; R 2 -C1; R 3 -Et; Y- R X =CF 3 ; R 2 -F; R Et; Y- R x =OCF 3 ; R 2 =F; R 3 =Et; Y*

R-K-3 R =CF 3 ; R 2 =C1; R 3 =4-Cl-Ph; Y= R x =OCF 3 ; R 2 =C1; R 3 -4-Cl-P ; Y* R X =CF 3 ; R =C1; R 3 -4-F-P ; Y-

K-K-3

24 R x -OCF 3 ; R 2 =C1; R 3 «4-F-Ph;

25 R X -CF 3 ; R 2 -C1; R 3 -Ph;

26 R x -OCF 3 ; R 2 -C1; R 3 -P ;

27 R X -CF 3 ; R 2 -F; R 3 -4-Cl-Ph;

28 R x -OCF 3 ? R 2 -F; R 3 -4-Cl-Ph;

29 R X »CF 3 ; R 2 «=F; R 3 «=4-F-Ph;

30 R x =OCF 3 ; R 2 =F; R 3 =4-F-P ;

31 R X =CF 3 ; R 2 =F; R 3 -Ph;

32 R -OCF 3 ; R 2 *=F; R 3 -Ph;

K-K-4

33 R X =CF 3 ; R 2 =6-C1; R 3 =COOMe; Y=

34 R x =OCF 3 ; R 2 -6-Cl; R 3 =COOMe; Y"

35 R X =CF 3 ; R 2 «=6-C1; R 3 »4-Cl-P ; Y«=

36 R x =0CF 3 ; R 2 =6-C1; R 3 -»4-Cl-Ph; Y=

37 R X ~CF 3 ; R 2 -6-Cl; R 3 =4-F-Ph; Y=

38 R x =OCF 3 ; R 2 »6-C1; R 3 «4-F-Ph; Y=

39 R X -CF 3 ; R 2 -6-F; R 3 »COOMe; Y-

40 R x «OCF 3 ; R 2 -6-F; R 3 =COOMe; Y«

41 R X =»CF 3 ; R 2 -6-F; R 3 *=4-Cl-Ph; Y«

42 R x «OCF 3 ; R 2 -6-F; R 3 -4-Cl-Ph; Y=

43 R X »CF 3 ; R 2 -6-F; R 3 «4-F-Ph; Y-

44 R x =OCF 3 ; R 2 -6-F; R 3 «4-F-Ph; Y«=

45 R X -CF 3 ; R 2 «6-CF 3 ; R 3 =COOMe; Y-

46 R -OCF 3 ; R «6-CF 3 ; R 3 -COOMe; Y-

47 R X -CF 3 ; R 2 -6-CF 3 ; R 3 -4-Cl-P ; Y-

48 R x >=OCF 3 ; R 2 -6-CF 3 ; R 3 -4-Cl-P ; Y-

49 R X =CF 3 ; R 2 =6-CF 3 ; R 3 -4-F-Ph; Y=

50 R x =OCF 3 ; R 2 »6-CF 3 ; R 3 =4-F-Ph; Y=

51 R X =CF 3 ; R 2 =5-F; R 3 =COOMe; Y<=

52 R x =OCF 3 ; R 2 =5-F; R 3 =COOMe; Y=

53 R X -CF 3 ; R 2 -5-F; R 3 «4-Cl-Ph; Y-

54 R =OCF 3 ; R 2 =5-F; R 3 -4-Cl-P ; Y=

K-K-4 R X =CF 3 ; R 2 =5-F; R 3 =4-F-Ph; Y= R«OCF 3 ; R 2 -5-F; R 3 «4-F-P ; Y» R X =CF 3 ; R 2 «=5-C1; R 3 =COOMe; Y= R x =OCF 3 ; R 2 =5-Cl; R 3 =COOMe; Y= R X -CF 3 ; R 2 -5-Cl; R 3 -4-Cl-Ph; Y~ R x =OCF 3 ; R 2 -5-Cl; R 3 =4-Cl-Ph; Y«= R X -CF 3 ; R 2 -5-Cl; R 3 -4-F-Ph; Y= R x « CF 3 ; R 2 -5-Cl; R 3 =4-F-P ; Y= R X ««CF 3 ; R 2 -6-Cl; R 3 -Me; Y= R x =OCF 3 ; R 2 =6-C1; R 3 =Me; Y= R =CF 3 ; R 2 =6-F; R 3 »Me; Y= R x =OCF 3 ; R 2 =6-F; R 3 «Me; Y= Y- R X =CF 3 ; R 2 -6-CF 3 ; R 3 =Me; Y= R=OCF 3 ; R 2 =6-CF 3 ; R 3 -Me; Y= R X =CF 3 ; R 2 =5-C1; R 3 =Me; = R x =OCF 3 ; R 2 =5-C1; R 3 »Me; Y= R=CF 3 ; R 2 =5-F; R 3 -Me Y= R x »OCF 3 ; R 2 -5-F; R 3 «Me; Y- R=CF 3 ; R 2 =6-C1; R- -Pr; Y= R x - CF 3 ; R 2 -6-Cl; R 3 =i-Pr; Y= R X =CF 3 ; R 2 =6-F; R 3 -i-Pr; Y= R x =OCF 3 ; R 2 =6-F; R 3 -i-Pr; Y= R X =CF 3 ; R 2 «=6-CF 3 ; R 3 »i-Pr; Y= R x =OCF 3 ; R 2 =6-CF 3 ; R 3 =i-Pr; Y= R X =CF 3 ; R 2 =5-C1; R 3 »i-Pr; Y= R x «OCF 3 ; R 2 -5-Cl; R 3 -1-Pr; Y- X =C ^ R 2 «=5-F; R 3 -»i-Pr; Y«= R x = CF 3 ; R 2 «=5-F; R 3 -i-Pr; Y=

K=K-5 R X -CF 3 ; R 2 =6-C1; R 3 =COOMe,- Y= R=OCF 3 ; R 2 =6-C1; R°=COOMe; Y= R X =CF 3 ; R 2 =6-C1; R 3 =4-Cl-Ph; Y=

K-K-5

86 R x -OCF 3 ; R 2 -6-Cl; R 3 -4-Cl-Ph; Y-

87 R X «CF 3 ; R 2 -6-Cl; R 3 -4-F-Ph; Y-

88 R x «-OCF 3 ; R 2 -6-Cl; R 3 -4-F-Ph; Y-

89 R X «=CF 3 ; R 2 -6-F; R 3 «COOMe; Y=

90 R x ~OCF 3 ; R 2 -6-F; R 3 -CO0Me; Y-

91 R X =CF 3 ; R 2 -6-F; R 3 =4-Cl-Ph; Y=

92 R x -0CF 3 ; R 2 -6-F; R 3 -4-Cl-Ph; Y-

93 R «CF 3 ; R 2 «6-F; R 3 -4-F-Ph; Y=

94 R x =OCF 3 ; R 2 -6-F; R 3 «4-F-Ph; Y=

95 R X =CF 3 ; R 2 «6-CF 3 ; R 3 =COOMe; Y«=

96 R x =OCF 3 ; R 2 »6-CF 3 ; R 3 «COOMe; Y«=

97 R X =CF 3 ; R 2 =6-CF 3 ; R 3 -4-Cl-Ph; Y=

98 R x =OCF 3 ; R 2 «6-CF 3 ; R 3 -4-Cl-Ph; Y-

99 R 1 -CF 3 ; R 2 -6-CF 3 ; R 3 -4-F-Ph; Y-

100 R x OCF 3 ; R 2 -6-CF 3 ; R 3 »4-F-Ph; Y=

101 R X »CF 3 ; R »5-F; R 3 -COOMe; Y==

102 R x =OCF 3 ; R 2 -5-F; R 3 -COOMe; Y-

103 R X «CF 3 ; R 2 -5-F; R 3 -4-Cl-P ; Y-

104 R x -OCF 3 ; R 2 -5-F; R 3 -4-Cl-Ph; Y-

105 R X -CF 3 ; R 2 -5-F; R 3 -4-F-Ph; Y»

106 R x =»OCF 3 ; R 2 -5-F; R 3 -4-F-P ; Y-

107 R X =CF 3 ; R =5-C1; R 3 =COOMe; Y=

108 R =OCF 3 ; R 2 -5-Cl; R 3 -COOMe; Y-

109 R X =CF 3 ; R 2 -5-Cl; R 3 -4-Cl-Ph; Y-

110 R x *OCF 3 ; R 2 -5-Cl; R 3 -4-Cl-Ph; Y-

111 R X -CF 3 ; R 2 -5-Cl; R 3 -4-F-Ph; Y-

112 R x -0CF 3 ; R 2 -5-Cl; R 3 -4-F-Ph; Y-

113 R X «CF 3 ; R 2 -6-Cl; R 3 -Me; Y-

114 R x =OCF 3 ; R 2 -=6-Cl; R 3 -Me; Y«=

115 R X =CF 3 ; R 2 -6-F; R 3 -Me; Y=

116 R =OCF 3 ; R -6-F; R 3 -Me; Y=

117 R =CF 3 ; R 2 -6-CF 3 ; R 3 -Me; Y«=

K-K-5

118 R x =OCF 3 ; R 2 »6-CF 3 ; R 3 -Me; Y= 119 R X -CF 3 ; R 2 -5-Cl; R 3 -Me; Y- 120 R x -OCF 3 ; R 2 -5-Cl; R 3 -Me; Y= 121 R X =CF 3 ; R 2 -5-F; R 3 -Me; Y= 122 R x »OCF 3 ; R 2 -5-F; R 3 «*Me; Y- 123 R X -CF 3 ; R 2 -6-Cl; R 3 -i-Pr; Y- 124 R =OCF 3 ; R 2 -6-Cl; R 3 -i-Pr; Y= 125 R X =CF 3 ; R 2 -6-F; R 3 -i-Pr; Y- 126 R X HDCF 3 ; R 2 -6-F; R 3 -i-Pr; Y- 127 R X =CF 3 ; R 2 =6-CF 3 ; R 3 =i-Pr; Y= 128 . R =OCF 3 ; R 2 =6-CF 3 ; R 3 =i-Pr; Y«= 129 R X =CF 3 ; R 2 -5-Cl; R 3 «i-Pr; Y- 130 .R x =OCF 3 ; R 2 =5-C1; R 3 =i-Pr; Y= 131 R X -CF 3 ; R 2 -5-F; R 3 -i-Pr; Y= 132 R x =OCF 3 ; R 2 =5-F; R 3 =i-Pr; Y«

K-K-6

133 R X -CF 3 ; R 2 -C1; R 3 -4-Cl-Ph; Y- 134 R x =OCF 3 ; R 2 -C1; R 3 -4-Cl-P ; Y- 135 R -CF 3 ; R 2 «C1; R 3 -4-F-Ph; Y- 136 R x =OCF 3 ; R 2 =C1; R 3 -4-F-Ph; Y= 137 R =CF 3 ; R 2 -F; R 3 =4-Cl-Ph; Y« 138 R x -OCF 3 ; R 2 -F; R 3 -4-Cl-Ph; Y-= 139 R X -CF 3 ; R 2 -F; R 3 -4-F-Ph; Y- 140 R =OCF 3 ; R 2 -F; R 3 -4-F-Ph Y- 141 R X -CF 3 ; R 2 -CF 3 ; R 3 «4-Cl-Ph; Y= 142 R x =OCF 3 ; R 2 -CF 3 ; R 3 «4-Cl-Ph; Y- 143 R1-CF 3 ; R 2 -CF 3 ; R 3 -4-F-P ; Y- 144 R x -OCF 3 ; R 2 =CF 3 ; R 3 -4-F-P ; Y=

K-K-7

145 R X =CF 3 ; R 2 =C1; R 3 -4-Cl-Ph; Y- 146 R x «=OCF 3 ; R 2 -C1; R 3 -4-Cl-Ph; Y- 147 R1- » CF 3 ; R 2 =C1; R 3 -4-F-P ; Y~

K-K-7

148 R x =0CF 3 ; R 2 -»C1; R 3 «4-F-Ph; Y» 149 R =CF 3 ; R 2 «=F; R 3 -4-Cl-Ph; Y- 150 R x =0CF 3 R 2 =F; R 3 «4-Cl-Ph; Y= 151 R X «CF 3 ; R 2 =F; R 3 «4-F-Ph; Y- 152 R =0CF 3 ; R 2 >=F; R 3 -4-F-Ph; Y<- 153 R X =CF 3 ; R 2 -CF 3 ; R 3 -4-Cl-Ph; Y- 154 R x =OCF 3 ; R 2 »CF 3 ; R 3 =4-Cl-Ph; Y= 155 R X =CF 3 ; R 2 =CF 3 ; R 3 «=4-F-Ph; Y- 156 R x =OCF 3 ; R 2 =CF 3 ; R 3 =4-F-Ph; Y»

K=K-8

Z-CH 2

157 R X =CF 3 ; R 2 =5-C1; R 3 «COOMe; Y* 158 R x «OCF 3 ; R 2 -5-Cl; R 3 -COOMe; Y- 159 R X -CF 3 ; R 2 =5-F; R 3 -=COOMe; Y- 160 R =OCF 3 ; R 2 -5-F; R 3 =COOMe; Y= 161 R X -CF 3 ; R 2 -5-CF 3 ; R 3 -COOMe; Y- 162 R "OCF 3 ; R 2 -5-CF 3 ; R 3 »=COOMe; Y- 163 R X =CF 3 ; R =4-C1; R 3 =COOMe; Y= 164 R x =OCF 3 ; R 2 =4-C1; R 3 =COOMe; Y- 165 R X -CF 3 ; R 2 -4-F; R 3 =COOMe; Y= 166 R x «OCF 3 R 2 «4-F; R 3 «=COOMe; Y" 167 R X -CF 3 ; R 2 -5-Cl; R 3 -4-Cl-Ph; Y- 168 R -OCF 3 ; R 2 -5-Cl; R 3 -4-Cl-Ph; Y- 169 R X =CF 3 ; R 2 =5-F; R 3 -4-Cl-Ph; Y= 170 171 R -CF 3 ; R 2 -5-CF 3 ; R 3 -4-Cl-Ph; Y- 172 R x =OCF 3 ; R 2 -5-CF 3 ; R 3 -4-Cl-P ; Y- 173 R X =CF 3 ; R 2 -4-Cl; R 3 =4-Cl-Ph; Y- 174 R x =OCF 3 ; R 2 =4-C1; R 3 -4-Cl-Ph; Y«= 175 R X =CF 3 ; R 2 «4-F; R 3 -4-Cl-P ; Y= 176 R x =OCF 3 ; R 2 =4-F; R 3 =4-Cl-Ph; Y= 177 R X -CF 3 ; R 2 =5-C1; R 3 -4-F-Ph; Y«=

K-K-8 Z=CH 2

178 R x -OCF 3 ; R ■.2^--5S--.Cl; R 3-= 5 «-44_-FF_-'Ph; Y- 179 R 1-CF 3 ; R 2 «5-F; R 3 -4-F-Ph; Y- 180 R x «OCF 3 ; R 2 -5-F; R 3 -4-F-Ph; Y- 181 R X -CF 3 ; R 2 -5-CF 3 ; R 3 -4-F-PH; Y- 182 R x "=OCF 3 ; R 2 =5-CF 3 ; R 3 =4-F-P ; Y= 183 R -CF 3 ; R 2 «4-C1; R 3 -4-F-P ; Y- 184 R x «OCF 3 ; R 2 -4-Cl; R 3 -4-F-Ph; Y- 185 R1=CF 3 ; R 2 -4-F; R 3 =4-F-Ph; Y= 186 R x =OCF 3 ; R 2 «4-F; R 3 =4-F-Ph; Y- 187 R =CF 3 ; R 2 -5-Cl; R 3 -Me; Y- 188 R CF 3 ; R =5-C1; R 3 «Me; Y= 189 R X =CF 3 ; R 2 =5-F; R 3 «Me; Y- 190 R x «=OCF 3 ; R 2 -5-F; R 3 -Me; Y- 191 R X =CF 3 ; R 2 -5-CF 3 ; R 3 -Me; Y= 192 R x =OCF 3 ; R 2 -5-CF 3 ; R 3 -Me; Y= 193 R « CF 3 ; R 2 -4-Cl; R 3 -Me; Y«= 194 R x «OCF 3 ; R 2 -4-Cl; R 3 -Me; Y- 195 R1=CF 3 ; R 2 -4-F; R 3 -Me; Y- 196 R x «OCF 3 ; R 2 «=4-F; R 3 -Me; Y= 197 R X -CF 3 ; R 2 -5-Cl; R 3 -i-Pr; Y- 198 R x =OCF 3 ; R 2 «5-C1; R 3 «i-Pr; Y= 199 R X =CF 3 ; R 2 -5-F; R 3 -I-Pr; Y- 200 R x -OCF 3 ; R 2 -5-F; R -»i-Pr; Y- 2G1 R =CF 3 ; R 2 =5-CF 3 ; R 3 -i-Pr; Y= 202 R x =OCF 3 ; R 2 -5-CF 3 ; R 3 =»i-Pr; Y= 203 R!=CF 3 ; R -4-Cl; R 3 -i-Pr; Y- 204 R x =OCF 3 ; R 2 -4-Cl; R 3 =i-Pr; Y= 205 R1=CF 3 ; R 2 -4-F; R 3 -i-Pr; Y- 206 R x =OCF 3 ; R 2^«-,-4l_-FF; Rj°-«i-f-_Prr Y=

K-K-8 Z=0

207 R X =CF 3 ; R 2 -5-Cl; R 3 «*COOMe; Y= 208 R1-OCF 3 ; R 2 -5-Cl; R 3 -COOMe; Y« 209 R1=CF 3 ; R 2 »5-F; R 3 «=COOMe; Y= 210 R x *=OCF 3 ; R 2 -5-F; R 3 -COOMe; Y- 211 R X =CF 3 ; R 2 -5-CF 3 ; R 3 -COOMe; Y- 212 R =OCF 3 ; R 2 -5-CF 3 ; R 3 =COOMe; Y- 213 R X =CF 3 ; R 2 »4-C1; R 3 -COOMe; Y- 214 R x =OCF 3 ; R 2 -=4-Cl; R 3 =COOMe; Y= 215 R =CF 3 ; R 2 «=4-F; R 3 =COOMe; Y= 216 R!=OCF 3 ; R 2 -4-F; R 3 =COOMe; Y= 217 R X =CF 3 ; R -5-Cl; R 3 -4-Cl-P ; Y= 218 ,R -OCF 3 ; R 2 -5-Cl; R 3 -4-Cl-Ph; Y«= 219 R X >«CF 3 ; R 2 -5-F; R 3 -4-Cl-P ; Y= 220 R x =OCF 3 ; R 2 -5-F; R 3 -4-Cl-Ph; Y- 221 R X =CF 3 R 2 =5-CF 3 ; R 3 «-4-Cl-Ph; Y- 222 R x «OCF 3 ; R 2 -5-CF 3 ; R 3 «4-Cl-Ph; Y- 223 R1=-CF 3 ; R 2 -4-Cl; R 3 -4-Cl-Ph; Y- 224 R1-*OCF 3 ; R 2 -4-Cl; R 3 -4-Cl-P ; Y- 225 R X =CF 3 ; R 2 -4-F; R 3 «4-Cl-Ph; Y*= 226 R x =OCF 3 ; R 2 -4-F; R 3 -4-Cl-Ph; Y= 227 R X -CF 3 ; R 2 -5-Cl; R 3 -4-F-Ph; Y- 228 R! « OCF 3 ; R 2 -5-Cl; R 3 -4-F-Ph; Y-= 229 R -CF 3 ; R 2 -5-F; R 3 «4-F-Ph; Y- 230 R x -OCF 3 ; R 2 -5-F; R 3 -4-F-Ph; Y- 231 R1-CF 3 ; R 2 -5-CF 3 ; R 3 -4-F-Ph; Y- 232 R =OCF 3 ; R 2 =5-CF 3 ; R 3 »4-F-Ph; Y- 233 R X -CF 3 ; R 2 -4-Cl; R 3 -4-F-Ph; Y«= 234 R x -OCF 3 ; R 2 -4-Cl; R 3 -4-F-Ph; Y- 235 R X -CF 3 ; R 2 -4-F; R 3 =4-F-Ph; Y- 236 237 R =CF 3 ; R 2 =5-C1; R 3 -Me; Y-

K-K-8 Z-O

238 R =OCF 3 ; R 2 -5-Cl; R 3 -Me; Y- 239 R =CF 3 ; R 2 -5-F; R 3 -Me; Y- 240 R x =OCF 3 ; R 2 -5-F; R 3 -Me; Y= 241 R X =CF 3 ; R 2 -5-CF 3 ; R 3 -Me; Y- 242 R x -OCF 3 ; R 2 -5-CF 3 ; R 3 -Me; Y- 243 R X =CF 3 ; R 2 -4-Cl; R 3 -Me; Y= 244 R x -OCF 3 ; R 2 -4-Cl; R 3 -Me; Y= 245 R X =CF 3 ; R 2 -4-F; R 3 =Me; Y= 246 R x =OCF 3 ; R 2 =4-F; R 3 -Me; Y= 247 R X -CF 3 ; R 2 -5-Cl; R 3 -i-Pr; Y= 248 R x =OCF 3 ; R 2 -5-Cl; R 3 -i-Pr; Y- 249 R X -CF 3 ; R 2 =5-F; R=i-Pr Y= 250 R x =OCF 3 ; R 2 =5-F; R 3 =i-Pr; Y= 251 R=CF 3 ; R 2 -5-CF 3 ; R 3 »i-Pr; Y- 252 R x =OCF 3 ; R 2 =5-CF 3 ; R 3 =i-Pr; Y- 253 R -CF 3 ; R 2 -4-Cl; R 3 -i-Pr; Y- 254 R x =OCF 3 ; R 2 -4-Cl; R 3 -i-Pr; Y- 255 R X =CF 3 ; R 2 -4-F; R 3 -i-Pr; Y- 256 R x =OCF 3 ; R 2 -4-F; R 3 =i-Pr; Y=

K-K-8

Z-N-H

257 R1=CF 3 ; R 2 -5-Cl; R 3 -COOMe; Y= 258 R x =OCF 3 ; R 2 =5-C1; R 3 =COOMe; Y- 259 R X =CF 3 ; R 2 -5-F; R 3 =COOMe; Y= 260 R x =OCF 3 ; R 2 -5-F; R 3 -COOMe; Y= 261 R-CF 3 R 2 -5-CF 3 ; R 3 =COOMe; Y= 262 R x =OCF 3 ; R 2 =5-CF 3 ; R 3 =COOMe; Y= 263 R1=CF 3 ; R 2 =4-C1; R 3 =COOMe; Y= 264 R x =OCF 3 ; R 2 -4-Cl; R 3 -COOMe; Y= 265 R =CF 3 ; R 2 -4-F; R 3 -COOMe; Y= 266 R x -OCF 3 ; R 2 -4-F; R 3 -COOMe; Y=

K-K-8

Z-N-H

267 R -CF 3 ; R 2 -5-Cl; R 3 -4-Cl-Ph; Y«= 268 R x =OCF 3 ; R 2 -5-Cl; R 3 =4-Cl-Ph; Y«= 269 R X -CF 3 ; R 2 -5-F; R 3 -4-Cl-Ph; Y= 270 R x -OCF 3 ; R 2 -5-F; R 3 -4-Cl-Ph; Y- 271 R X -CF 3 ; R 2 -5-CF 3 ; R 3 -4-Cl-P ; Y= 272 R x =OCF 3 ; R 2 -5-CF 3 ; R 3 -4-Cl-P Y= 273 R X -CF 3 ; R 2 =4-C1; R 3 -4-Cl-Ph; Y= 274 R x -OCF 3 ; R 2 =4-C1; R 3 =4-Cl-Ph; Y= 275 R X =CF 3 ; R <2' ή ---.4Λ_-;F; R 3 J --»-4ι_-πCl --τP ; Y= 276 R x -OCF 3 ; R 2 -4-F; R 3 -4-Cl-Ph; Y= 277 R X -CF 3 ; R 2 -5-Cl; R 3 -4-F-P ; Y« 278 R x =OCF 3 ; R 2 -5-Cl; R 3 -4-F-Ph; Y« 279 R X =CF 3 ; R 2 =5-F; R 3 =4-F-Ph; Y= 280 R x =OCF 3 ; R 2 =5-F; R 3 =4-F-Ph; Y= 281 R X =CF 3 ; R 2 =5-CF 3 ; R 3 -4-F-P ; Y= 282 R =OCF 3 ; R 2 -5-CF 3 ; R 3 -4-F-P ; Y= 283 R-CF 3 ; R 2 -4-Cl; R 3 -4-F-P ; Y- 284 R x =OCF 3 ; R 2 =4-C1; R 3 -4-F-Ph; Y- 285 R X -CF 3 ; R 2 -4-F; R 3 -4-F-Ph; Y«= 286 R x -OCF 3 ; R 2 -4-F; R 3 -4-F-Ph; Y= 287 R1=CF 3 ; R 2 -5-Cl; R 3 -Me; Y= 288 R-OCF 3 ; R 2 -5-Cl; R 3 -Me; Y= 289 R X -CF 3 ; R 2 -5-F; R 3 -Me; Y= 290 R x =OCF 3 ; R 2 -5-F; R 3 -Me; Y= 291 R X =CF 3 ; R 2 -5-CF 3 ; R 3 -Me; Y= 292 R x =OCF 3 ; R 2 =5-CF 3 ; R 3 =Me; Y= 293 R X =CF 3 ; R 2 =4-C1; R 3 -Me; Y= 294 R =OCF 3 ; R 2 -4-Cl; R 3 -Me; Y= 295 R 1=CF 3 ; R 2 -4-F; R 3 -Me; Y= 296 R x «=OCF 3 ; R 2 =4-F; R 3 -Me Y= 297 R X =CF 3 ; R 2 =5-C1; R 3 -i-Pr; Y=

K-K-8 Z-N-H

298 R x =OCF 3 ; R 2 -5-Cl; R 3 -i-Pr; Y=

299 R X =CF 3 ; R 2 -5-F; R 3 -i-Pr; Y*

300 R x =OCF 3 ; R 2 -5-F; R 3 -i-Pr; Y-

301 R X -CF 3 ; R 2 -5-CF 3 ; R 3 -i-Pr; Y»

302 R x =OCF 3 ; R 2 =5-CF 3 ; R 3 -i-Pr; Y*>

303 R X -CF 3 ; R 2 -4-Cl; R 3 -i-Pr; Y=

304 R -OCF 3 ; R 2 -4-Cl; R 3 -i-Pr; Y-

305 R X =CF 3 ; R 2 =4-F; R =i-Pr; Y=

306 R=OCF 3 ; R 2 -4-F; R 3 -i-Pr; Y-

K-K-9

307 R X =CF 3 ; R 2 =5-C1; R 3 -4-Cl-Ph; Y-

308 R x -OCF 3 ; R 2 =5-C1; R 3 -4-Cl-Ph; Y-

309 R X =CF 3 ; R 2 =5-F; R 3 =4-Cl-Ph; Y=

310 R x =OCF 3 ; R 2 -5-F; R 3 -4-Cl-Ph; Y=

311 R X =CF 3 ; " R 2 =4-C1; R 3 -4-Cl-Ph; Y-

312 R-OCF 3 ; R 2 =4-C1; R 3 -4-Cl-Ph; Y-

313 R X -CF 3 ; R 2 =4-F; R 3 -4-Cl-P ; Y-

314 R x -OCF 3 ; R 2 =4-F; R 3 -4-Cl-Ph; Y-

315 R X =CF 3 ; R 2 =5-C1; R 3 -4-F-Ph; Y-

316 R x =OCF 3 ; R 2 -5-Cl; R 3 -4-F-P ; Y«=

317 R X =CF 3 ; R 2 -5-F; R 3 -4-F-P ; Y-

318 R=OCF 3 ; R 2 -5-F; R 3 -4-F-Ph; Y-

319 R 1 -CF 3 ? R 2 -4-Cl; R 3 =4-F-Ph; Y-

320 R x -OCF 3 ; R 2 »4-C1; R 3 -4-F-P ; Y-

321 R X =CF 3 ; R 2 -4-F; R 3 -4-F-P ; Y-

322 R x =OCF 3 ; R 2 -4-F; R 3 -4-F-P ; Y>=

323 R X =CF 3 ; R 2 =5-C1; R 3 -Me; Y=

324 R x =OCF 3 ; R 2 -5-Cl; R 3 -Me; Y=

325 R X =CF 3 ; R 2 =5-F; R 3 -Me; Y=

326 R x =OCF 3 ; R 2 =5-F; R 3 -Me; Y-

327 R X =CF 3 ; R 2 =4-C1; R 3 -Me; Y=

K-K-9

328 R *=OCF 3 ; R -4-Cl; R 3 -Me; Y- 329 R X -CF 3 R 2 -4-F; R 3 -Me; = 330 R -OCF 3 ; R 2 -4-F; R 3 -Me; Y- 331 R X -CF 3 ; R 2 -5-Cl; R 3 «Et; Y= 332 R x =OCF 3 ; R 2 -5-Cl R 3 -Et; Y» 333 R 1-CF 3 ; R 2 -5-F; R 3 -Et; Y«= 334 R x =OCF 3 ; R 2 -5-F; R 3 -Et; Y- 335 R1=CF 3 ; R 2 -4-Cl; R 3 -Et; Y" 336 R x -OCF 3 ; R 2 -4-Cl; R 3 -Et; Y- 337 R1=CF 3 ; R 2 »4-F; R 3 =Et; Y= 338 R l-=OCF 3 ; R 2 =4-F; R 3 =Et; Y= 339 R -CF 3 ; R 2 =5-C1; R 3 -i-Pr Y- 340 R1-OCF 3 ; R 2 -5-Cl; R 3 -i-Pr; Y- 341 R X -CF 3 ; R ? 2 ^--R5--Fi ; R 3-'--i'--P-.r; Y= 342 R X -CF 3 ; R 2 -5-F; R 3 -i-Pr; Y- 343 R X -CF 3 ; R 2 -4-Cl; R 3 -i-Pr; Y- 344 R!.=OCF 3 ; R 2 -4-Cl; R 3 -i-Pr; Y- 345 R X -CF 3 ; R 2 -4-F; R 3 -i-Pr; Y« 346 R x -OCF 3 ; R 2 -4-F; R 3 -i-Pr; Y-

K-K-10

347 R1-CF 3 ; R 2 -5-Cl; R 3 -Me; Y- 348 R x «OCF 3 ; R 2 -5-Cl; R 3 -Me; Y- 349 R X -CF 3 ; R 2 -5-F; R 3 -Me; Y- 350 R x -0CF 3 ; R -5-F; R 3 -Me; Y= 351 R -CF 3 ; R 2 =4-C1; R 3 =Me; Y= 352 R1-=OCF 3 ; R 2 -4-Cl; R 3 -Me; Y- 353 R X -CF 3 ; R 2 -4-F; R 3 -Me; Y χ = 354 R x =OCF 3 ; R 2 -4-F; R 3 -Me; Y- 355 R X =CF 3 ; R 2 -5-Cl; R 3 -Et; Y= 356 R x -OCF 3 ; R 2 -5-Cl; R 3 -Et; Y= 357 R =CF 3 ; R 2 =5-F; R 3 -Et; Y= 358 R -0CF 3 ; R 2 -5-F; R 3 -Et; Y=

K-K-10

359 R X -CF 3 ; R 2 -4-Cl; R 3 =Et; Y- H Me COOMe COM 360 R x =OCF 3 ; R 2 -4-Cl; R 3 -Et; Y- H Me COOMe COM 361 R X -CF 3 ; R 2 -4-F; R 3 -Et; Y- H Me COOMe COM 362 R x -OCF 3 ; R 2 -4-F; R 3 -Et; Y- H Me COOMe COM

K-K-ll

363 R X =CF 3 ; R 2 -4-F; R 3 -4-F-Ph; Y= 364 R x -OCF 3 ; R 2 -4-F; R 3 -4-F-Ph; Y- 365 R -CF 3 ; R 2 -4-Cl; R 3 -4-F-Ph; Y- 366 R x -OCF 3 ; R 2 -4-Cl; R 3 -4-F-P ; Y= 367 R1-=CF 3 ; R 2 -4-F? R 3 -4-Cl-Ph; Y= 368 R x =OCF 3 ; R 2 -4-F; R 3 -4-Cl-Ph; Y- 369 R X -CF 3 ; R 2 -4-Cl; R 3 -4-Cl-Ph; Y= 370 R x -OCF 3 ; R 2 =4-C1; R 3 -4-Cl-Ph; Y=

K-K-12

371 R1=CF 3 ; R 2 =5-F; R 3 -4-F-P ; Y= 372 R x -OCF 3 ; R 2 -5-F; R 3 -4-F-P ; Y- 373 R -CF 3 ; R 2 -5-Cl; R 3 -4-F-Ph; Y- 374 R x -OCF 3 ; R 2 -5-Cl; R 3 -4-F-P ; Y- 375 R =CF 3 ; R 2 -5-F; R 3 -4-Cl-Ph; Y- 376 R x -OCF 3 ; R 2 -5-F; R 3 -4-Cl-Ph; Y- 377 R X =CF 3 ; Rϊ 2 ^=-5ς--ιCl; R 3 °--«44--rClι--tPh; Y- 378 R x -OCF 3 ; R 2 -5-Cl; R 3 -4-Cl-Ph; Y-

Formulation/Utility

Compounds of this invention will generally be used i formulation with an agriculturally suitable carrier comprising a liquid or solid diluent or an organic solvent. Use formulations include dusts, granules, baits, pellets, solutions, suspensions, emulsions, wettable powders, emulsifiable concentrates, dry flowables and the like, consistent with the physical properties of the active ingredient, mode of applicatio and environmental factors such as soil type, moisture a temperature. 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 which add up to 100 weight percent.

Weight Percent

Wettable Powders

Oil Suspensions, Emulsions, Solutions, (including Emulsifiable Concentrates)

Dusts

Granules, Baits and Pellets

High Strength Compositions

Typical solid diluents are described in atkins, et al., Handbook of Insecticide Dust Diluents and Carriers, 2nd Ed., Dorland Books, Caldwell, New Jersey. Typical liquid diluents and solvents are described in Marsden, Solvents Guide, 2nd Ed., Interscience, New Yor

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 ormulations can contain minor amounts of additives to reduce foam, caking, corrosion, microbiological growth, etc. Solutions are prepared by simply mixing the ingredients. Fine solid compositions are made by blending and, usually, grinding as in a hammer mill or fluid energy mill. Water-dispersible granules can be produced be agglomerating a fine powder composition; see for example, Cross et al., Pesticide Formulations,. Washington, D.C, 1988, pp 251-259. Suspensions are prepared by wet-milling; see, for example, U.S.

3,060,084. Granules and pellets can be made by spraying the active material upon preformed granular carriers or by agglomeration techniques. See Browning, "Agglomeration", Chemical Engineering, December 4, 1967, pp 147—148, Perry 's Chemical Engineer 's Handbook, 4th Ed., McGraw-Hill, New York, 1963, pages 8—57 and following, and WO 91/13546. Pellets can be prepared as described in U.S. 4,172,714. Water-dispersible and water-soluble granules can also be prepared as taught in DE 3,246,493.

For further information regarding the art of form'ulation, see 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 worked up in conventiona ways. Compound numbers refer to compounds in Index Tabl A.

Example A

Wettable Powder

Compound 1 65.0% dodecylphenol polyethylene glycol ether 2.0% sodium ligninsulfonate 4.0% sodium silicoaluminate 6.0% montmorillonite (calcined) 23.0%

Example 3 Granule

Compound 1 10.0% attapulgite granules (low volative matter, 0.71/0.30 mm; U.S.S. No.

25-50 sieves) 90.0% Example

Ex ruded Pellet

Compound 1 25.0% anhydrous sodium sulfate 10.0% crude calcium ligninsulfonate 5.0% sodium alkylnaphthalenesulfonate 1.0% calcium/magnesium bentonite 59.0%

Example D

Emulsifiable Concentrate

Compound 1 20.0% blend of oil soluble sulfonates and polyoxyethylene ethers 10.0% isophorone 70.0% The compounds of this invention exhibit activity against a wide spectrum of foliar-feeding, fruit-feeding

seed-feeding, aquatic and soil-inhabiting arthropods (ter includes insects, mites and nematodes) which are pests of growing and stored agronomic crops, forestry, greenhouse crops, ornamentals, nursery crops, stored food and fiber products, livestock, household, and public and animal health. Those skilled in the art will appreciate that not all compounds are equally effective against all pests. Nevertheless, all of the compounds of this invention display activity against pests that include: eggs, larvae and adults of the Order Lepidoptera; eggs, foliar-feeding, fruit-feeding, root-feeding, seed-feeding larvae and adults of the Order Coleoptera; eggs, immatures and adults of the Orders Hemiptera and Homoptera; eggs, larvae, nymphs and adults of the Order Acari; eggs, immatures and adults of the Orders

Thysanoptera, Orthoptera and Dermaptera; eggs, immatures and adults of the Order Diptera; and eggs, junveniles and adults of the Phylum Ne ata. The compounds of this invention are also active against pests of the Orders Hymenoptera, Isoptera, Phthiraptera, Siphonoptera,

Blattaria, Thysanaura and Pscoptera; pests belonging to the Class Arachnida and Phylum Platyhelminthes. See WO 90/10623 and WO 92/00673 for more detailed pest descriptions. Compounds of this invention can also be mixed with one or more other insecticides, fungicides, nematocides, bactericides, acaricides, semiochemicals, repellants, attractants, pheromones, feeding stimulants or other biologically active compounds to form a multi-component pesticide giving an even broader spectrum of agricultural protection. Examples of other agricultural protectants with which compounds of this invention can be formulated are: insecticides such as monocrotophos, carbofuran, tetrachlorvinphos, malathion, parathion—methyl, methomyl,

chlordimeform, diazinon, deltamethrin, oxamyl, fenvalerate, esfenvalerate, permethrin, profenofos, sulprofos, triflumuron, diflubenzuron, methoprene, buprofezin, thiodicarb, acephate, azinphosmethyl, chlorpyrifos, dimethoate, fipronil, flufenprox, fonopho isofenphos, methidathion, methamidophos, phosmet, phosphamidon, phosalone, pirimicarb, phorate, terbufos, trichlorfon, methoxychlor, bifenthrin, biphenate, cyfluthrin, fenpropathrin, fluvalinate, fluσythrinate, tralomethrin, metaldehyde and rotenone; fungicides suc as carbendazim, thiuram, dodine, maneb, chloroneb, benomyl, cymoxanil, fenpropidine, fenpropi orph, triadimefon, captan, thiophanate-methyl, thiabendazole, phosethyl-Al, chlorothalonil, dichloran> metalaxyl, captafol, iprodione, oxadixyl, vinclozolin, kasugamycin, myclobutanil, tebuconazole, difenoconazole, diniconazol fluquinconazole, ipconazole, metconazole, penconazole, propiconazole, uniconzole, flutriafol, prochloraz, pyrifenox, fenarimol, triadimenol, diclobutrazol, coppe oxychloride, furalaxyl, folpet, flusilazol, blasticidin S, diclomezine, edifenphos, isoprothiolane, iprobenfos, mepronil, neo-asozin, pencycuron, probenazole, pyroquilon, tricyclazole, validamycin, and flutolanil; nematocides such as aldoxycarb, fenamiphos and fosthietan; bactericides such as oxytetracyline, streptomycin and tribasic copper sulfate; acaricides such as binapacryl, oxythioquinox, chlorobenzilate, dicofol, dienochlor, cyhexatin, hexythiazox, amitraz, propargite, tebufenpyrad and fenbutatin oxide; and biological agents such as Bacillus thuringiensis, baculovirus and avermectin B.

In certain instances, combinations with other arthropodicides having a similiar spectrum of control b

a different mode of action will be particularly advantageous for resistance management.

Arthropod pests are controlled and protection of agronomic crops, animal and human health is achieved by applying one or more of the compounds of this invention, in an effective amount, to the environment of the pests including the agronomic and/or nonagronomic locus of infestation, to the area to be protected, or directly on the pests to be controlled. A preferred method of application is by spraying. Alternatively, granular formulations of these compounds can be applied to the plant foliage or the soil. Other methods of application include direct and residual sprays, aerial sprays, systemic uptake, baits, eartags, boluses, foggers, fumigants, aerosols, and many others.. The compounds' can be incorporated into baits that are consumed by the arthropods or in devices such as traps and the like.

The compounds of this invention can be applied in their pure state, but most often application 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 application involves spraying a water dispersion or refined oil solution of the compounds. Combinations with spray oils, spray oil concentrations, spreader stickers, adjuvants, and synergists and other solvents such as piperonyl butoxide often enhance compound efficacy.

The rate of application required for effective control will depend on such factors as the species of arthropod to be controlled, the pest's life cycle, life stage, its size, location, time of year, host crop or animal, feeding behavior, mating behavior, ambient moisture, temperature, and the like. Under normal

circumstances, application rates of about 0.01 to 2 kg o active ingredient per hectare are sufficient to control pests in agronomic ecosystems, but as little as 0.001 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 0.1 mg/square meter may be sufficient or as much as 150 mg/square meter may be required. The following Tests demonstrate the control efficacy of compounds of this invention on specific pests. The pest control protection afforded by the compounds is not limited, however, to these species. See Index Table A for compound descriptions.

INDEX TABLE A

TEST A Fall Armyworm

Test units, each consisting of an 8-ounce (230 mL) plastic cup containing a layer of wheat germ diet, approximately 0.5 cm thick, were prepared. Ten third- instar larvae of fall armyworm (Spodoptera frugiperda) were placed into a cup. Solutions of each of the test compounds (acetone/distilled water 75/25 solvent) were sprayed into the cups, a single solution per set of three cups. Spraying was accomplished by passing the cups, on a conveyer belt, directly beneath a flat fan hydraulic nozzle which discharged the spray at a rate of 0.5 pounds of active ingredient per acre (about 0.55 kg/ha) at 30 p.s.i. (207 kPa) . The cups were then covered and held at 27°C and 50% relative humidity for 72 hours, after which time readings were taken. Of the compounds tested, the following resulted in greater than or equal to 80% mortality: 1 and 3*. TEST B

Tobacco Budworm

The test procedure of Test A was repeated for efficacy against third-instar larvae of the tobacco budworm (Heliothis virescens) except that mortality was assessed at 48 hours. Of the compounds tested, the following resulted in greater than or equal to 80% mortality: 3*.

TEST C Southern Corn Rootworm Test units, each consisting of an 8-ounce (230 mL) plastic cup containing 1 sprouted corn seed, were prepared. Sets of three test units were sprayed as described in Test A with individual solutions of the test compounds. After the spray on the cups had dried, five

third-instar larvae of the southern corn rootworm (Diabrotica undecimpunctata howardi) were placed into ea cup. A moistened dental wick was inserted into each cup to prevent drying and the cups were then covered. The cups were then held at 27°C and 50% relative humidity fo 48 hours, after which time mortality readings were taken. Of the compounds tested, the following resulted in great than or equal to 80% mortality: 3*.

TEST D Aster L a hopper

Test units were prepared from a series of 12-ounce (350 mL) cups, each containing oat (Avena sativa) seedlings in a 1-inch (2.54 cm) layer of sterilized soil The test units were sprayed as described in Test A with individual solutions of the below-listed compounds. • Aft the oats had dried from the spraying, between 10 and 15 adult aster leafhoppers (Mascrosteles fascifrons) were aspirated into each of the covered cups. The cups were held at 27°C and 50% relative humidity for 48 hours, aft which time mortality readings were taken. Of the compounds tested, the following resulted in greater than or equal to 80% mortality: 3*.

T_E≤T_E Boll Weevil Five adult boll weevils (Anthonomus grandis) were placed into each of a series of 9 ounce (260 L) cups. The test procedure employed was then otherwise the same in Test A with three cups per treatment. Mortality readings were taken 48 hours after treatment. Of the compounds tested, no mortality levels greater than or equal to 80% were observed. *Tested at 0.125 lbs.