PYRIDAZINOL COMPOUND, DERIVATIVE THEREOF, PREPARATION METHOD THEREFOR, HERBICIDAL COMPOSITION AND USE THEREOF

Abstract

The present invention belongs to the technical field of pesticides, and in particular relates to a pyridazinol compound, a derivative thereof, a preparation method therefor, a herbicidal composition and the use thereof. The pyridazinol compound is as represented by general formula I,

##STR00001##

wherein X represents

##STR00002##

and the ring is an unsubstituted or substituted aryl or unsubstituted or substituted heterocyclyl containing a carbon atom at the 1-position; Y represents haloalkyl; and Z represents halogen, cyano, hydroxy, etc. The derivative refers to an agriculturally acceptable derivative of the hydroxyl group at the 4-position of the pyridazine ring in the general formula I, including a salt, an ester, an oxime, a hydroxylamine and an ether derivative, etc. The compound, the derivative thereof and the composition thereof have good herbicidal activity and crop safety.

Claims

1. A pyridazinol compound of Formula I or a derivative thereof: ##STR00937## wherein, X represents ##STR00938## and the ring is an aryl or heterocyclyl containing a carbon atom at the 1-position; Y represents haloalkyl; Z represents halogen, cyano, hydroxy, formyl, aryl, heterocyclyl; alkyl, alkenyl, alkynyl, cycloalkyl, OR″, SR″, SOR″ or SO.sub.2R″ with or without halogen; or amino which is unsubstituted or substituted by one or two groups selected from R″, COR″, CON(R″).sub.2, COOR″, SO.sub.2R″, -alkyl-SO.sub.2R″ and OR″, wherein each of the group contains or does not contain a halogen; the “aryl”, “heterocyclyl”, “aryloxy” and “heterocyclyloxy” are respectively unsubstituted or substituted by at least one of the following groups: halogen, nitro, cyano, thiocyano, cyanoalkyl, sulfhydryl, hydroxy, hydroxyalkyl, carboxyl, carboxyalkyloxy, formyl, azide, trialkylsilyl, dialkylphosphono; heterocyclyl, heterocyclylalkyl, aryl or arylalkyl, each of which is unsubstituted or substituted; alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl, cycloalkenylalkyl, alkyl-substituted cycloalkyl, OR″, SR″, -alkyl-OR″, —O-alkyl-OR″, -alkyl-SR″, COR″, -alkyl-COR″, —O-alkyl-COR″, COOR″, -alkyl-COOR″, —O-alkyl-COOR″, COSR″, SOR″, SO.sub.2R″, —O—SO.sub.2R″, -alkyl-SO.sub.2R″, OCOR″, -alkyl-OCOR″ or SCOR″ with or without halogen; amino, aminocarbonyl, aminocarbonylalkyl or aminosulfonyl, each of which is unsubstituted or substituted by one or two groups selected from R″, COR″, CON(R″).sub.2, COOR″, SO.sub.2R″, -alkyl-SO.sub.2R″ and OR″, wherein each of the group contains or does not contain a halogen; or any two adjacent carbon atoms in the ring are connected with —CH.sub.2CH.sub.2CH.sub.2—, —OCH.sub.2CH.sub.2—, —OCH.sub.2O—, —OCH.sub.2CH.sub.2O— or —CH═CH—CH═CH— group to form a fused ring, wherein each of the group contains or does not contain a halogen; R″ each independently represents alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl; or heterocyclyl, heterocyclylalkyl, aryl or arylalkyl, each of which is unsubstituted or substituted.

2. The pyridazinol compound or derivative thereof according to claim 1, wherein X represents ##STR00939## and the ring is an aryl or heterocyclyl group containing a carbon atom at the 1-position; Y represents halo C1-C8 alkyl; Z represents halogen, cyano, hydroxy, formyl, aryl, heterocyclyl; C1-C8 alkyl, C2˜C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, OR″, SR″, SOR″ or SO.sub.2R″ with or without halogen; or amino which is unsubstituted or substituted by one or two groups selected from R″, COR″, CON(R″).sub.2, COOR″, SO.sub.2R″, —(C1-C8)alkyl-SO.sub.2R″ and OR″, wherein each of the group contains or does not contain a halogen; the “aryl”, “heterocyclyl”, “aryloxy” and “heterocyclyloxy” are respectively unsubstituted or substituted by at least one of the following groups: halogen, nitro, cyano, thiocyano, cyano C1-C8 alkyl, sulfhydryl, hydroxy, hydroxy C1-C8 alkyl, carboxyl, carboxyalkyloxy, formyl, azide, tri-C1-C8 alkylsilyl, di-C1-C8 alkylphosphono; heterocyclyl, heterocyclyl C1-C8 alkyl, aryl or aryl C1-C8 alkyl, each of which is unsubstituted or substituted; C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkyl C1-C8 alkyl, C3-C8 cycloalkenyl C1-C8 alkyl, C1-C8 alkyl-substituted C3-C8 cycloalkyl, OR″, SR″, —(C1-C8)alkyl-OR″, —O—(C1-C8)alkyl-OR″, —(C1-C8)alkyl-SR″, COR″, —(C1-C8)alkyl-COR″, —O—(C1-C8)alkyl-COR″, COOR″, —(C1-C8)alkyl-COOR″, —O—(C1-C8)alkyl-COOR″, COSR″, SOR″, SO.sub.2R″, —O—SO.sub.2R″, —(C1-C8)alkyl-SO.sub.2R″, OCOR″, —(C1-C8)alkyl-OCOR″ or SCOR″ with or without halogen; amino, aminocarbonyl, aminocarbonyl C1-C8 alkyl or aminosulfonyl, each of which is unsubstituted or substituted by one or two groups selected from R″, COR″, CON(R″).sub.2, COOR″, SO.sub.2R″, —(C1-C8)alkyl-SO.sub.2R″ and OR″, wherein each of the group contains or does not contain a halogen; or any two adjacent carbon atoms in the ring are connected with —CH.sub.2CH.sub.2CH.sub.2—, —OCH.sub.2CH.sub.2—, —OCH.sub.2O—, —OCH.sub.2CH.sub.2O— or —CH═CH—CH═CH— group to form a fused ring, wherein each of the group contains or does not contain a halogen; R″ each independently represents C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenyl C1-C8 alkyl; or heterocyclyl, heterocyclyl C1-C8 alkyl, aryl or aryl C1-C8 alkyl, each of which is unsubstituted or substituted by at least one group selected from halogen, cyano, C1-C8 alkyl, halo C1-C8 alkyl, C2-C8 alkenyl and C1-C8 alkoxy; the derivative refers to an agriculturally acceptable derivative of the hydroxyl group at the 4-position of the pyridazine ring in the general formula I.

3. The pyridazinol compound or derivative thereof according to claim 1, wherein X represents ##STR00940## and the ring is an aryl or heterocyclyl group containing a carbon atom at the 1-position; Y represents halo C1-C6 alkyl; Z represents halogen, cyano, hydroxy, formyl, aryl, heterocyclyl; C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, OR″, SR″, SOR″ or SO.sub.2R″ with or without halogen; or amino which is unsubstituted or substituted by one or two groups selected from R″, COR″, CON(R″).sub.2, COOR″, SO.sub.2R″, —(C1-C6)alkyl-SO.sub.2R″ and OR″, wherein each of the group contains or does not contain a halogen; the “aryl”, “heterocyclyl”, “aryloxy” and “heterocyclyloxy” are respectively unsubstituted or substituted by 1˜5 of the following groups: halogen, nitro, cyano, thiocyano, cyano C1-C6 alkyl, sulfhydryl, hydroxy, hydroxy C1-C6 alkyl, carboxyl, carboxyalkyloxy, formyl, azide, tri-C1-C6 alkylsilyl, di-C1-C6 alkylphosphono; heterocyclyl, heterocyclyl C1-C6 alkyl, aryl or aryl C1-C6 alkyl, each of which is unsubstituted or substituted; C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkyl C1-C6 alkyl, C3-C6 cycloalkenyl C1-C6 alkyl, C1-C6 alkyl-substituted C3-C6 cycloalkyl, OR″, SR″, —(C1-C6)alkyl-OR″, —O—(C1-C6)alkyl-OR″, —(C1-C6)alkyl-SR″, COR″, —(C1-C6)alkyl-COR″, —O—(C1-C6)alkyl-COR″, COOR″, —(C1-C6)alkyl-COOR″, —O—(C1-C6)alkyl-COOR″, COSR″, SOR″, SO.sub.2R″, —O—SO.sub.2R″, —(C1-C6)alkyl-SO.sub.2R″, OCOR″, —(C1-C6)alkyl-OCOR″ or SCOR″ with or without halogen; amino, aminocarbonyl, aminocarbonyl C1-C6 alkyl or aminosulfonyl, each of which is unsubstituted or substituted by one or two groups selected from R″, COR″, CON(R″).sub.2, COOR″, SO.sub.2R″, —(C1-C6)alkyl-SO.sub.2R″ and OR″, wherein each of the group contains or does not contain a halogen; or any two adjacent carbon atoms in the ring are connected with —CH.sub.2CH.sub.2CH.sub.2—, —OCH.sub.2CH.sub.2—, —OCH.sub.2O—, —OCH.sub.2CH.sub.2O— or —CH═CH—CH═CH— group to form a fused ring, wherein each of the group contains or does not contain a halogen; R″ each independently represents C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C6 alkyl; or heterocyclyl, heterocyclyl C1-C6 alkyl, aryl or aryl C1-C6 alkyl, each of which is unsubstituted or substituted by 1-5 groups selected from halogen, cyano, C1-C6 alkyl, halo C1-C6 alkyl, C2-C6 alkenyl and C1-C6 alkoxy; the derivative refers to an agriculturally acceptable derivative of the hydroxyl group at the 4-position of the pyridazine ring in the general formula I, including a salt, an ester, an oxime, a hydroxylamine and an ether derivative.

4. The pyridazinol compound or derivative thereof according to claim 1, wherein X represents ##STR00941## the ring is phenyl, ##STR00942## or ##STR00943## containing a carbon atom at the 1-position, which is respectively unsubstituted or substituted by 1-3 groups selected from fluorine, chlorine, bromine, cyano, C1-C6 alkyl, C2-C6 alkenyl, halo C1-C6 alkyl, or any two adjacent carbon atoms in the ring are connected with —OCH.sub.2O— group to form a fused ring, wherein the —OCH.sub.2O— group contains or does not contain a halogen; Y represents trifluoromethyl or pentafluoroethyl; Z represents halogen, cyano, hydroxy, formyl, aryl, heterocyclyl, C1-C6 alkyl, halo C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C1-C6 alkoxy, halo C1-C6 alkoxy, aryloxy, heterocyclyloxy, C1-C6 alkylsulfanyl, C1-C6 alkylsulfoxide, C1-C6 alkylsulfonyl; or amino which is unsubstituted or substituted by one or two groups selected from C1-C6 alkyl, C1-C6 alkylcarbonyl, C1-C6 alkylaminocarbonyl, C1-C6 alkoxycarbonyl, C3-C6 cycloalkyloxycarbonyl, C1-C6 alkylsulfonyl, aryl and aryl C1-C2 alkyl; the “aryl” is phenyl which is unsubstituted or substituted by 1-3 groups selected from fluorine, cyano and C1-C6 alkoxy; the “heterocyclyl” is ##STR00944## or ##STR00945## each of which is unsubstituted or substituted by 1-3 groups selected from C1-C6 alkyl.

5. The pyridazinol compound or derivative thereof according to claim 1, which is selected from any one of Table 1-3.

6. A method for preparing the pyridazinol compound or derivative thereof according to claim 1, comprising the following steps: (1) subjecting a compound of Formula II and a halogenating reagent to halogenation reaction to obtain a compound of Formula I′; (2) subjecting a compound of Formula I′ to hydroxyl protection reaction to obtain a compound of Formula I-1′; (3) subjecting a compound of Formula I-1′ to substitution reaction, deprotection reaction in sequence to obtain a compound of Formula I″; the reaction route is as follows: ##STR00946## wherein Q.sub.1 and Hal each independently represent halogen; Q.sub.2 represents a group other than halogen in the substituent Z according to claim 1; X and Y are described in claim 1; L-represents TMS-, TBDMS-, TBDPS-, TBS-, PMB- or SEM-.

7. The method for preparing the pyridazinol compound or derivative thereof according to claim 6, wherein in the step (1), the halogenation reaction is carried out in the presence of an initiator and a solvent; the step (2) is carried out in the presence of a base and a solvent; in the step (3), the type of substitution reaction is Suzuki, Buchwald, copper-catalyzed or nucleophilic substitution, and the deprotection reaction is carried out in the presence of trifluoroacetic acid, hydrochloric acid, hydrobromic acid, hydroiodic acid, DDQ or H.sub.2.

8. A herbicidal composition comprising (i) the pyridazinol compound of Formula I or derivative thereof according to claim 1.

9. A method for controlling a weed comprising applying a herbicidally effective amount of at least one of the pyridazinol compounds and derivatives thereof according to claim 1 to a plant or a weed area.

10. Use of at least one of the pyridazinol compounds and derivatives thereof according to claim 1 for controlling a weed.

11. The method for preparing the pyridazinol compound or derivative thereof according to claim 6, wherein Q.sub.1 and Hal each independently represent F, Cl, Br or I.

12. The method for preparing the pyridazinol compound or derivative thereof according to claim 7, wherein in the step (1), the halogenation reagent is Cl.sub.2, Br.sub.2, I.sub.2, NBS, NCS, NIS, dichlorohydantoin, dibromohydantoin, selective fluorine reagent or hexabromoethane, the initiator is AIBN or BPO, and the solvent is CCl.sub.4, AcOH/H.sub.2O, MeCN, DMF, NMP or AcOH.

13. The method for preparing the pyridazinol compound or derivative thereof according to claim 7, wherein in the step (2), the solvent is selected from at least one of MeCN, DMF, DMSO, dioxane, dichloromethane, dichloroethane and ethyl acetate, and the base is inorganic base or organic base.

14. The herbicidal composition according to claim 8, further comprising (ii) one or more additional herbicides and/or safeners.

15. The herbicidal composition according to claim 14, further comprising (iii) an agriculturally acceptable formulation auxiliary.

16. A method for controlling a weed comprising applying a herbicidally effective amount of the herbicidal composition according to claim 8 to a plant or a weed area.

17. Use of the herbicidal composition according to claim 8 for controlling a weed.

18. The use for controlling a weed according to claim 10, wherein the pyridazinol compound or derivative thereof being used for preventing and/or controlling a weed in a useful crop, wherein the useful crop is a transgenic crop or a crop treated by gene editing technique.

19. The use for controlling a weed according to claim 17, wherein the herbicidal composition being used for preventing and/or controlling a weed in a useful crop, wherein the useful crop is a transgenic crop or a crop treated by gene editing technique.

Description

SPECIFIC MODE FOR CARRYING OUT THE INVENTION

[0109] The following embodiments are used to illustrate the present invention in detail and should not be taken as any limit to the present invention. The scope of the invention would be explained through the Claims.

[0110] In view of economics, variety and biological activity of a compound, we preferably synthesized several compounds, part of which are listed in the following table 1-3. The structure and information of a certain compound are shown in Table 1-3. The compounds in Table 1-3 are listed for further explication of the present invention, other than any limit therefor. The subject of the present invention should not be interpreted by those skilled in the art as being limited to the following compounds.

TABLE-US-00001 TABLE 1 Structures and .sup.1HNMR data of Compounds I [00047] NO. X Y Z .sup.1HNMR 1 [00048] CF.sub.3 F .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.50 (s, 1H), 7.97 (d, J = 7.5 Hz, 2H), 7.77 (d, J = 1.5 Hz, 2H). 2 [00049] CF.sub.3 Cl .sup.1H NMR (500 MHz, DMSO-d.sub.6 δ 14.42 (s, 1H), 8.25 (d, J = 7.5 Hz, 2H), 7.75 (d, J = 7.5 Hz, 2H). 3 [00050] CF.sub.3 Br .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.45 (s, 1H), 8.20 (d, J = 8.0 Hz, 2H), 7.94 (d, J = 8.0 Hz, 2H). 4 [00051] CF.sub.3 I .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.42 (s, 1H), 8.25 (d, J = 8.0 Hz, 2H), 7.95 (d, J = 8.0 Hz, 2H). 5 [00052] CF.sub.3 Me .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.40 (s, 1H), 8.25 (d, J = 8.0 Hz, 2H), 7.94 (d, J = 8.0 Hz, 2H), 2.15 (s, 3H). 6 [00053] CF.sub.3 Et .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.42 (s, 1H), 8.25 (d, J = 8.0 Hz, 2H), 7.95 (d, J = 8.0 Hz, 2H), 2.81 (q, J = 8.0 Hz, 2H), 1.30 (t, J = 8.0 Hz, 3H). 7 [00054] CF.sub.3 [00055] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.49 (s, 1H), 8.16 (d, J = 7.5 Hz, 2H), 7.92 (d, J = 7.5 Hz, 2H), 1.70-1.67 (m, 1H), 1.35-1.32 (m, 2H), 0.89-0.85 (m, 2H). 8 [00056] CF.sub.3 CN .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.42 (s, 1H), 8.25 (d, J = 8.0 Hz, 2H), 7.85 (d, J = 8.0 Hz, 2H). 9 [00057] CF.sub.3 [00058] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.43 (s, 1H), 8.20 (d, J = 8.0 Hz, 2H), 7.92 (d, J = 8.0 Hz, 2H), 6.91-6.78 (m, 1H), 6.62-6.56 (m, 1H), 5.77 (dd, 12.0, 2.5 Hz, 1H). 10 [00059] CF.sub.3 [00060] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.50 (s, 1H), 8.21 (d, J = 8.0 Hz, 2H), 7.92 (d, J = 8.0 Hz, 2H), 5.30 (s, 1H), 4.91 (s, 1H), 1.94 (s, 3H). 11 [00061] CF.sub.3 [00062] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.42 (s, 1H), 8.20 (d, J = 8.0 Hz, 2H), 7.84 (d, J = 8.0 Hz, 2H), 3.56 (s, 1H). 12 [00063] CF.sub.3 OMe .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.45 (s, 1H), 8.23 (d, J = 8.0 Hz, 2H), 7.97 (d, J = 8.0 Hz, 2H), 4.03 (s, 3H). 13 [00064] CF.sub.3 OEt .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.45 (s, 1H), 8.24 (d, J = 8.0 Hz, 2H), 7.97 (d, J = 8.0 Hz, 2H), 4.29 (q, J = 7.5 Hz, 2H), 1.45 (t, J = 7.5 Hz, 3H). 14 [00065] CF.sub.3 [00066] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.43 (s, 1H), 8.23 (d, J = 8.0 Hz, 2H), 7.96 (d, J = 8.0 Hz, 2H), 4.89 (q, J = 8.0 Hz, 2H). 15 [00067] CF.sub.3 OH .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.39 (s, 1H), 14.18 (s, 1H), 8.00 (d, J = 8.0 Hz, 2H), 7.92 (d, J = 8.0 Hz, 2H). 16 [00068] CF.sub.3 NH.sub.2 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.35 (s, 1H), 8.31 (d, J = 8.0 Hz, 2H), 7.94 (d, J = 8.0 Hz, 2H), 6.84 (s, 2H). 17 [00069] CF.sub.3 NHMe .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.50 (s, 1H), 7.99 (d, J = 7.5 Hz, 2H), 7.75 (d, J = 7.5 Hz, 2H), 5.95 (s, 1H), 2.72 (s, 3H). 18 [00070] CF.sub.3 N(Me).sub.2 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.43 (s, 1H), 8.20 (d, J = 8.0 Hz, 2H), 7.96 (d, J = 8.0 Hz, 2H), 2.89 (s, 6H) 19 [00071] CF.sub.3 [00072] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.45 (s, 1H), 9.94 (s, 1H), 8.20 (d, J = 8.0 Hz, 2H), 7.96 (d, J = 8.0 Hz, 2H), 2.07 (s, 3H) 20 [00073] CF.sub.3 [00074] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ Hz, 2H), 7.96 (d, J = 8.0 Hz, 2H), 2.95 (s, 6H) 21 [00075] CF.sub.3 [00076] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.50 (s, 1H), 10.29 (s, 1H), 8.06 (d, J = 8.0 Hz, 2H), 7.74 (d, J = 8.0 Hz, 2H), 7.44-7.36 (m, 2H), 7.31-7.24 (m, 2H), 7.02 (tt, J = 7.5, 2.0 Hz, 1H). 22 [00077] CF.sub.3 [00078] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.43 (s, 1H), 8.22 (d, J = 8.0 Hz, 2H), 7.94 (d, J = 8.0 Hz, 2H), 3.91-3.86 (m, 2H), 2.48 (t, J = 5.5 Hz, 2H), 2.06 1.98 (m, 2H). 23 [00079] CF.sub.3 [00080] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.44 (s, 1H), 8.23 (d, J = 8.0 Hz, 2H), 7.92 (d, J = 8.0 Hz, 2H), 4.06 (t, J = 5.5 Hz, 2H), 2.46 (t, J = 6.5 Hz, 2H), 1.85-1.61 (m, 4H). 24 [00081] CF.sub.3 [00082] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.43 (s, 1H), 8.20 (d, J = 8.0 Hz, 2H), 7.96 (d, J = 8.0 Hz, 2H), 5.91 (s, 1H), 2.15 (s, 3H), 2.10 (s, 3H). 25 [00083] CF.sub.3 [00084] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.45 (s, 1H), 8.21 (d, J = 8.0 Hz, 2H), 7.96 (d, J = 8.0 Hz, 2H), 7.70 (d, J = 4.0 Hz, 1H), 7.53 (d, J = 2.5 Hz, 1H), 6.45 (dd, J = 4.0, 2.5 Hz, 1H). 26 [00085] CF.sub.3 SMe .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.45 (s, 1H), 8.23 (d, J = 8.0 Hz, 2H), 7.97 (d, J = 8.0 Hz, 2H), 2.57 (s, 3H). 27 [00086] CF.sub.3 SEt .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.46 (s, 1H), 8.24 (d, J = 8.0 Hz, 2H), 7.96 (d, J = 8.0 Hz, 2H), 3.07 (q, J = 7.5 Hz, 2H), 1.11 (t, J = 7.5 Hz, 3H). 28 [00087] CF.sub.3 SOEt .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.45 (s, 1H), 7.96 (d, J = 8.0 Hz, 2H), 7.74 (d, J = 8.0 Hz, 2H), 2.61 (q, J = 8.0 Hz, 2H), 1.33 (t, J = 8.0 Hz, 3H). 29 [00088] CF.sub.3 SO.sub.2Et .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.50 (s, 1H), 8.25 (d, J = 8.0 Hz, 2H), 7.96 (d, J = 8.0 Hz, 2H), 3.57 (q, J = 7.5 Hz, 2H), 1.17 (t, J = 7.5 Hz, 3H). 30 [00089] CF.sub.3 Ph .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.44 (s, 1H), 8.23 (d, J = 8.0 Hz, 2H), 7.92 (d, J = 8.0 Hz, 2H), 7.35-7.23 (m, 5H). 31 [00090] CF.sub.3 [00091] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.54 (s, 1H), 8.23 (d, J = 8.0 Hz, 2H), 7.92 (d, J = 8.0 Hz, 2H), 7.35-7.23 (m, 4H). 32 [00092] CF.sub.3 [00093] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.46 (s, 1H), 8.24 (d, J = 8.0 Hz, 2H), 7.94 (d, J = 8.0 Hz, 2H), 7.91 (d, J = 8.0 Hz, 2H), 7.49 (d, J = 8.0 Hz, 2H). 33 [00094] CF.sub.3 [00095] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.40 (s, 1H), 8.74-8.70 (m, 1H), 8.06-7.99 (m, 2H), 7.91-7.88 (m, 1H), 7.86-7.78 (m, 3H), 7.53-7.49 (m, 1H). 34 [00096] CF.sub.3 [00097] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.44 (s, 1H), 8.64 (dd, J = 5.0, 1.5 Hz, 1H), 8.50 (d, J = 1.5 Hz, 1H), 8.28 (d, J = 8.0 Hz, 2H), 7.96 (d, J = 8.0 Hz, 2H), 7.78 (d, J = 8.0 Hz, 1H), 7.54 (dd, J = 8.0, 5.0 Hz, 1H). 35 [00098] CF.sub.3 [00099] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.45 (s, 1H), 8.68 (d, J = 5.0 Hz, 2H), 8.08-8.01 (m, 2H), 7.75-7.73 (m, 4H). 36 [00100] CF.sub.3 [00101] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.45 (s, 1H), 8.68 (d, J = 5.0 Hz, 2H), 7.87-7.81 (m, 3H), 7.77 (s, 1H), 3.95 (s, 3H). 37 [00102] CF.sub.3 [00103] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.45 (s, 1H), 8.23 (d, J = 8.0 Hz, 2H), 7.93 (d, J = 8.0 Hz, 2H), 7.78 (dd, J = 5.0, 2.0 Hz, 1H), 7.15-7.14 (m, 2H). 38 [00104] CF.sub.3 [00105] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.50 (s, 1H), 8.22 (d, J = 8.0 Hz, 2H), 7.93 (d, J = 8.0 Hz, 2H), 7.61-7.60 (m, 1H), 7.55 (s, 1H), 7.09 (d, J = 5.0 Hz, 1H). 39 [00106] CF.sub.3 [00107] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.50 (s, 1H), 8.96 (s, 1H), 8.23 (s, 1H), 8.00-7.93 (m, 2H), 7.86-7.80 (m, 2H). 40 [00108] CF.sub.3 [00109] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.46 (s, 1H), 8.04-7.98 (m, 2H), 7.86-7.80 (m, 3H), 6.97- 6.95 (m, 1H), 6.66-6.62 (m, 1H). 41 [00110] CF.sub.3 [00111] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.55 (s, 1H), 8.05 (d, J = 8.0 Hz, 2H), 7.74 (d, J = 8.0 Hz, 2H), 7.50 (d, J = 7.5 Hz, 2H), 6.49-6.47 (m, 1H). 42 [00112] CF.sub.3 [00113] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.45 (s, 1H), 8.23 (d, J = 8.0 Hz, 2H), 7.92 (d, J = 8.0 Hz, 2H), 7.28 (t, J = 7.5 Hz, 2H), 7.06-7.02 (m, 1H), 7.00 (d, J = 8.0 Hz, 2H). 43 [00114] CF.sub.3 [00115] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.48 (s, 1H), 8.06 (d, J = 8.0 Hz, 2H), 7.74 (d, J = 8.0 Hz, 2H), 7.61 (d, J = 7.5 Hz, 1H), 6.14 (d, J = 7.5 Hz, 1H), 3.76 (s, 3H). 44 [00116] CF.sub.3 F .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.49 (s, 1H), 7.96-7.68 (m, 2H), 7.09 (s, 1H). 45 [00117] CF.sub.3 Cl .sup.1H NMR (500 MHz. DMSO-d.sub.6) δ 14.42 (s, 1H), 9.20 (s, 1H), 8.48 (s, 1H), 7.97 (t, J = 58.5 Hz, 1H). 46 [00118] CF.sub.3 Br .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.42 (s, 1H), 9.20 (s, 1H), 8.47 (s, 1H), 7.96 (t, J = 58.5 Hz, 1H). 47 [00119] CF.sub.3 I .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.42 (s, 1H), 9.18 (s, 1H), 8.44 (s, 1H), 7.95 (t, J = 58.5 Hz, 1H). 48 [00120] CF.sub.3 Me .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.24 (s, 1H), 9.12 (s, 1H), 8.41 (s, 1H), 7.94 (t, J = 58.5 Hz, 1H), 2.16 (s, 3H). 49 [00121] CF.sub.3 Et .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.51 (s, 1H), 9.12 (s, 1H), 8.41 (s, 1H), 7.94 (t, J = 58.5 Hz, 1H), 2.70 (q, J = 8.0 Hz, 2H), 1.22 (t, J = 8.0 Hz, 3H). 50 [00122] CF.sub.3 [00123] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.30 (s, 1H), 9.08 (s, 1H), 8.35 (s, 1H), 7.90 (t, J = 58.5 Hz, 1H), 1.69 (s, 1H), 1.50-1.28 (m, 2H), 0.88-0.85 (m, 2H). 51 [00124] CF.sub.3 CN .sup.1H NMR (500 MHz, DMSO-d6) δ 14.49 (s, 1H), 9.12 (s, 1H), 8.41 (s, 1H), 7.94 (t, J = 58.5 Hz, 1H). 52 [00125] CF.sub.3 [00126] .sup.1H NMR (500 MHz, DMSO-d6) δ 14.42 (s, 1H), 9.17 (s, 1H), 8.41 (s, 1H), 7.90 (t, J = 59.0 Hz, 1H), 7.06 (dd, J = 17.0, 3.5 Hz, 1H), 6.64-6.58 (m, 1H), 5.52 (dd, J = 17.0, 3.5 Hz, 1H). 53 [00127] CF.sub.3 [00128] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.38 (s, 1H), 9.10 (s, 1H), 8.40 (s, 1H), 7.93 (t, J = 58.5 Hz, 1H), 5.32 (s, 1H), 4.91 (s, 1H), 1.97 (s, 3H). 54 [00129] CF.sub.3 [00130] .sup.1H NMR (500 MHz, DMSO-d6) δ 14.48 (s, 1H), 9.12 (s, 1H), 8.41 (s, 1H), 7.94 (t, J = 58.5 Hz, 1H), 4.43 (s, 1H). 55 [00131] CF.sub.3 OMe .sup.1H NMR (500 MHz, DMSO-d6) δ 14.48 (s, 1H), 9.10 (s, 1H), 8.40 (s, 1H), 7.93 (t, J = 58.5 Hz, 1H), 3.86 (s, 3H). 56 [00132] CF.sub.3 OEt .sup.1H NMR (500 MHz, DMSO-d6) δ 14.48 (s, 1H), 9.10 (s, 1H), 8.42 (s, 1H), 7.93 (t, J = 58.5 Hz, 1H), 4.10 (q, J = 8.0 Hz, 2H), 1.34 (t, J = 8.0 Hz, 3H). 57 [00133] CF.sub.3 [00134] .sup.1H NMR (500 MHz, DMSO-d6) δ 14.48 (s, 1H), 9.10 (s, 1H), 8.40 (s, 1H), 7.93 (t, J = 58.5 Hz, 1H), 5.05 (q, J = 8.0 Hz, 2H). 58 [00135] CF.sub.3 OH .sup.1H NMR (500 MHz, DMSO-d6) δ 14.43 (s, 1H), 14.48 (s, 1H), 9.10 (s, 1H), 8.40 (s, 1H), 7.93 (t, J = 58.5 Hz, 1H). 59 [00136] CF.sub.3 NH.sub.2 .sup.1H NMR (500 MHz, DMSO-d6) δ 14.48 (s, 1H), 9.16 (s, 1H), 8.56 (s, 1H), 7.96 (t, J = 58.5 Hz, 1H), 6.88 (s, 2H). 60 [00137] CF.sub.3 NHMe .sup.1H NMR (500 MHz, DMSO-d6) δ 14.42 (s, 1H), 9.14 (s, 1H), 8.56 (s, 1H), 7.96 (t, J = 58.5 Hz, 1H), 5.95 (s, 1H), 2.69 (s, 3H). 61 [00138] CF.sub.3 N(Me).sub.2 .sup.1H NMR (500 MHz, DMSO-d6) δ 14.50 (s, 1H). 9.10 (s, 1H), 8.36 (s, 1H), 7.93 (t, J = 58.5 Hz, 1H), 2.95 (s, 6H). 62 [00139] CF.sub.3 [00140] .sup.1H NMR (500 MHz, DMSO-d6) δ 14.42 (s, 1H), 9.61 (s, 1H), 9.09 (s, 1H), 8.48 (s, 1H), 7.97 (t, J = 59.0 Hz, 1H), 2.07 (s, 3H). 63 [00141] CF.sub.3 [00142] .sup.1H NMR (500 MHz, DMSO-d6) δ 14.49 (s, 1H), 9.10 (s, 1H), 8.36 (s, 1H), 7.93 (t, J = 58.5 Hz, 1H), 7.08 (s, 1H), 3.18 (s, 6H). 64 [00143] CF.sub.3 [00144] .sup.1H NMR (500 MHz, DMSO-d6) δ 14.49 (s, 1H), 10.29 (s, 1H), 9.10 (s, 1H), 8.36 (s, 1H), 7.93 (t, J = 58.5 Hz, 1H), 7.40-7.32 (m, 3H), 7.28-7.24 (m, 2H). 65 [00145] CF.sub.3 [00146] .sup.1H NMR (500 MHz, DMSO-d6) δ 14.48 (s, 1H), 9.17 (s, 1H), 8.36 (s, 1H), 7.94 (t, J = 58.5 Hz, 1H), 3.55-3.52 (m, 2H), 2.19-2.02 (m, 2H), 1.86-1.83 (m, 2H). 66 [00147] CF.sub.3 [00148] .sup.1H NMR (500 MHz, DMSO-d6) δ 14.48 (s, 1H), 9.13 (s, 1H), 8.34 (s, 1H), 7.89 (t, J = 58.5 Hz, 1H), 3.55-3.52 (m, 2H), 2.28-2.25 (m, 2H), 1.80- 1.59 (m, 4H). 67 [00149] CF.sub.3 [00150] .sup.1H NMR (500 MHz, DMSO-d6) δ 14.48 (s, 1H), 9.16 (s, 1H), 8.32 (s, 1H), 7.91 (t, J = 58.5 Hz, 1H), 5.85 (s, 1H), 2.20 (s, 3H), 1.96 (s, 3H). 68 [00151] CF.sub.3 [00152] .sup.1H NMR (500 MHz, DMSO-d6) δ 14.48 (s, 1H), 9.13 (s, 1H), 8.34 (s, 1H), 7.93 (t, J = 58.5 Hz, 1H) 7.85-7.63 (m, 2H), 7.13 (s, 1H). 69 [00153] CF.sub.3 SMe .sup.1H NMR (500 MHz, DMSO-d6) δ 14.48 (s, 1H), 9.17 (s, 1H), 8.39 (s, 1H), 7.91 (t, J = 58.5 Hz, 1H), 2.48 (s, 3H), 70 [00154] CF.sub.3 SEt .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.28 (s, 1H), 9.16 (s, 1H), 8.42 (s, 1H), 7.93 (t, J = 58.5 Hz, 1H), 3.06 (q, J = 7.5 Hz, 2H), 1.07 (t, J = 7.5 Hz, 3H). 71 [00155] CF.sub.3 SOEt .sup.1H NMR (500 MHz, DMSO-d6) δ 14.50 (s, 1H), 9.16 (s, 1H), 8.42 (s, 1H), 7.93 (t, J = 58.5 Hz, 1H), 2.61 (q, J = 8.0 Hz, 2H), 1.33 (t, J = 8.0 Hz, 3H). 72 [00156] CF.sub.3 SO.sub.2Et .sup.1H NMR (500 MHz, DMSOd6) δ 14.49 (s, 1H), 9.16 (s, 1H), 8.42 (s, 1H), 7.93 (t, J = 58.5 Hz, 1H), 3.51 (q, J = 8.0 Hz, 2H), 1.32 (t, J = 8.0 Hz, 3H). 73 [00157] CF.sub.3 Ph .sup.1H NMR (500 MHz, DMSO-d6) δ 14.47 (s, 1H), 9.16 (s, 1H), 8.42 (s, 1H), 7.93 (t, J = 58.5 Hz, 1H), 7.57-7.53 (m, 2H), 7.46-7.35 (m, 3H). 74 [00158] CF.sub.3 [00159] .sup.1H NMR (500 MHz, DMSO-d6) δ 14.49 (s, 1H), 9.16 (s, 1H), 8.42 (s, 1H), 7.93 (t, J = 58.5 Hz, 1H), 7.48-7.39 (m, 2H), 7.23-7.13 (m, 2H). 75 [00160] CF.sub.3 [00161] .sup.1H NMR (500 MHz, DMSO-d6) δ 14.43 (s, 1H), 9.16 (s, 1H), 8.42 (s, 1H), 7.93 (t, J = 58.5 Hz, 1H), 7.55-7.49 (m, 2H), 7.33-7.26 (m, 2H). 76 [00162] CF.sub.3 [00163] .sup.1H NMR (500 MHz, DMSO-d6) δ 14.48 (s, 1H), 9.16 (s, 1H), 8.59-8.55 (m, 1H), 8.42 (s, 1H), 7.92-7.71 (m, 3H), 7.40-7.35 (m, 1H), 77 [00164] CF.sub.3 [00165] .sup.1H NMR (500 MHz, DMSO-d6) δ 14.45 (s, 1H), 9.16 (s, 1H), 8.79 (s, 1H), 8.59-8.55 (m, 2H), 8.42 (s, 1H), 7.93 (t, J = 58.5 Hz, 1H), 7.48-7.45 (m, 1H). 78 [00166] CF.sub.3 [00167] .sup.1H NMR (500 MHz, DMSO-d6) δ 14.48 (s, 1H), 9.16 (s, 1H), 8.68 (d, J = 5.0 Hz, 2H), 8.43 (s, 1H), 7.93 (t, J = 58.5 Hz, 1H), 7.66 (d, J = 5.0 Hz, 2H), 79 [00168] CF.sub.3 [00169] .sup.1H NMR (500 MHz, DMSO-d6) δ 14.49 (s, 1H), 9.17 (s, 1H), 8.42 (s, 1H), 7.93 (t, J = 58.5 Hz, 1H), 7.89 (s, 1H), 6.85 (s, 1H), 3.92 (s, 3H). 80 [00170] CF.sub.3 [00171] .sup.1H NMR (500 MHz, DMSO-d6) δ 14.46 (s, 1H), 9.14 (s, 1H), 8.41 (s, 1H), 7.98-7.66 (m, 2H), 7.39-7.36 (m, 1H), 7.13-7.10 (m, 1H). 81 [00172] CF.sub.3 [00173] .sup.1H NMR (500 MHz, DMSO-d6) δ 14.49 (s, 1H), 9.16 (s, 1H), 8.40 (s, 1H), 7.92 (t, J = 58.5 Hz, 1H), 7.78-7.71 (m, 1H), 7.65 (s, 1H), 7.25-7.20 (m, 1H). 82 [00174] CF.sub.3 [00175] .sup.1H NMR (500 MHz, DMSO-d6) δ 14.46 (s, 1H), 9.16 (s, 1H), 9.10 (s, 1H), 8.40 (s, 1H), 7.93 (t, J = 58.5 Hz, 1H), 7.78 (s, 1H). 83 [00176] CF.sub.3 [00177] .sup.1H NMR (500 MHz, DMSO-d6) δ 14.48 (s, 1H), 9.17 (s, 1H), 8.42 (s, 1H), 7.97-7.68 (m, 2H), 6.94-6.90 (m, 1H), 6.61-6.58 (m, 1H). 84 [00178] CF.sub.3 [00179] .sup.1H NMR (500 MHz, DMSO-d6) δ 14.46 (s, 1H), 9.16 (s, 1H), 8.40 (s, 1H), 7.92 (t, J = 58.5 Hz, 1H), 7.55-7.44 (m, 2H), 6.47-6.43 (m, 1H). 85 [00180] CF.sub.3 [00181] .sup.1H NMR (500 MHz, DMSO-d6) δ 14.48 (s, 1H), 9.18 (s, 1H), 8.42 (s, 1H), 7.94 (t, J = 58.5 Hz, 1H), 7.32-7.12 (m, 3H), 7.04-6.84 (m, 2H). 86 [00182] CF.sub.3 [00183] .sup.1H NMR (500 MHz, DMSO-d6) δ 14.49 (s, 1H), 9.16 (s, 1H), 8.40 (s, 1H), 7.92 (t, J = 58.5 Hz, 1H), 7.29 (d, J = 5.5 Hz, 1H), 6.25 (d, J = 5.5 Hz, 1H), 3.76 (s, 3H). 87 [00184] CF.sub.3 Me .sup.1H NMR (500 MHz, DMSO-d6) δ 14.45 (s, 1H), 7.97-7.91 (m, 2H), 7.38-7.28 (m, 2H), 2.16 (s, 3H). 88 [00185] CF.sub.3 Me .sup.1H NMR (500 MHz, DMSO-d6) δ 14.42 (s. 1H), 7.76 (d, J = 7.5 Hz, 2H), 7.51 (d, J = 7.5 Hz, 2H), 2.15 (s, 3H). 89 [00186] CF.sub.3 Me .sup.1H NMR (500 MHz, DMSO-d6) δ 14.50 (s, 1H), 7.72 (d, J = 7.5 Hz, 2H), 7.45 (d, J = 7.5 Hz, 2H), 2.25 (s, 3H). 90 [00187] CF.sub.3 Me .sup.1H NMR (500 MHz, DMSO-d6) δ 14.49 (s, 1H), 7.58-7.45 (m, 2H), 7.38-7.35 (m, 1H), 2.12 (s, 3H). 91 [00188] CF.sub.3 Me .sup.1H NMR (500 MHz, DMSO-d6) δ 14.42 (s, 1H), 8.74 (d, J = 5.0 Hz, 1H), 8.20 (d, J = 8.0 Hz, 1H), 8.02-7.99 (m, 1H), 7.62-7.56 (m, 1H), 2.16 (s, 3H). 92 [00189] CF.sub.3 Me .sup.1H NMR (500 MHz, DMSO-d6) δ 14.42 (s, 1H), 8.75 (s, 1H), 8.51 (d, J = 5.0 Hz, 1H), 8.33 (d, J = 5.0 Hz, 1H), 7.57-7.52 (m, 1H), 2.17 (s, 3H). 93 [00190] CF.sub.3 Me .sup.1H NMR (500 MHz, DMSO) δ 14.51 (s, 1H), 8.51 (d, J = 6.0 Hz, 2H), 8.45 (d, J = 6.0 Hz, 2H), 2.05 (s, 3H). 94 [00191] CF.sub.3 Me .sup.1H NMR (500 MHz, DMSO-d6) δ 14.50 (s, 1H), 8.23-8.19 (m, 1H), 7.13-7.09 (m, 1H), 2.17 (s, 3H). 95 [00192] CF.sub.3 Me .sup.1H NMR (500 MHz, DMSO-d6) δ 14.49 (s, 1H), 8.67 (s, 1H), 8.46-8.42 (m, 1H), 8.24-8.20 (m, 1H), 2.15 (s,3H). 96 [00193] CF.sub.3 Me .sup.1H NMR (500 MHz, DMSO-d6) δ 14.53 (s, 1H), 8.78 (s, 1H), 8.11 (d, J = 8.0. 1H), 7.83 (d, J = 8.0 Hz, 1H), 2.18 (s, 3H). 97 [00194] CF.sub.3 Me .sup.1H NMR (500 MHz, DMSO-d6) δ 14.46 (s, 1H), 8.58 (s, 1H), 7.80 (d, J = 8.0,1H), 7.71 (d, J = 8.0 Hz, 1H), 2.20 (s, 3H). 98 [00195] CF.sub.3 Me .sup.1H NMR (500 MHz, DMSO-d6) δ 14.45 (s, 1H), 8.53 (s, 1H), 7.89 (d, J = 8.0 Hz, 1H), 7.51 (d, J = 8.0 Hz, 1H), 2.15 (s, 3H). 99 [00196] CF.sub.3 Me .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.43 (s, 1H), 8.43-8.40 (m 1H), 7.81-7.78 (m, 1H), 7.69 (d, J = 5.0 Hz, 1H), 2.13 (s, 3H). 100 [00197] CF.sub.3 Me .sup.1H NMR (500 MHz, DMSO-d6) δ 14.53 (s, 1H), 6.60 (s, 1H), 3.87 (s, 3H), 2.39 (s, 3H), 2.20 (s, 3H). 101 [00198] CF.sub.3 Me .sup.1H NMR (500 MHz, DMSO-d6) δ 14.45 (s, 1H), 7.84 (t, J = 57.0 Hz, 1H), 7.00 (s, 1H), 2.39 (s, 3H), 2.35 (s, 3H). 102 [00199] CF.sub.3 Me .sup.1H NMR (500 MHz, DMSO-d6) δ 14.48 (s, 1H), 7.86 (t, J = 57.5 Hz, 1H), 7.10 (s, 1H), 2.34 (s, 3H). 103 [00200] CF.sub.3 Me .sup.1H NMR (500 MHz, DMSO-d6) δ 14.49 (s, 1H), 7.06 (s, 1H), 2.35 (s, 3H), 1.87 (s, 3H). 104 [00201] CF.sub.3 Me .sup.1H NMR (500 MHz, DMSO-d6) δ 14.48 (s, 1H), 7.87 (s, 1H), 7.20 (s, 1H), 2.13 (s, 3H). 105 [00202] CF.sub.3 Me .sup.1H NMR (500 MHz, DMSO-d6) δ 14.48 (s, 1H), 7.84 (t, J = 57.5 Hz, 1H), 7.64 (d, J = 7.5 Hz, 1H), 6.66 (d, J = 7.5 Hz, 1H), 2.34 (s, 3H). 106 [00203] CF.sub.3 Me .sup.1H NMR (500 MHz, DMSO-d6) δ 14.46 (s, 1H), 7.97 (s, 1H), 2.37 (s, 3H), 2.32 (s, 3H). 107 [00204] CF.sub.3 Me .sup.1H NMR (500 MHz, DMSO-d6) δ 14.44 (s, 1H), 9.20 (s, 1H), 8.10 (s, 1H), 2.34 (s, 3H). 108 [00205] CF.sub.3 Me .sup.1H NMR (500 MHz, DMSO-d6) δ 14.52 (s, 1H), 8.43 (dd, J = 7.0, 5.0 Hz, 1H), 8.02-7.98 (m, 1H), 7.75 (dd, J = 8.0, 7.0 Hz, 1H), 2.16 (s, 3H). 109 [00206] CF.sub.3 Me .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.49 (s, 1H), 8.44 (d. J = 5.0 Hz. 1H). 8.23 (s, 1H), 7.82 (d, J = 5.0 Hz. 1H), 2.25 (s, 3H). 110 [00207] CF.sub.3 Me .sup.1H NMR (500 MHz, DMSO-d6) δ 14.46 (s, 1H), 8.83 (d, J = 2.5 Hz, 1H), 8.71 (d, J = 2.5 Hz, 1H), 8.06-8.02 (m, 1H), 2.25 (s, 3H). 111 [00208] CF.sub.3 Me .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.47 (s, 1H), 8.47 (dd, J = 5.0, 2.5 Hz, 1H), 7.90-7.80 (m, 2H), 2.24 (s, 3H). 112 [00209] CF.sub.3 Me .sup.1H NMR (500 MHz, DMSO-d6) δ 14.46 (s, 1H), 8.14-8.08 (m. 1H), 7.53-7.48 (m, 1H), 2.27 (s, 3H). 113 [00210] CF.sub.3 Me .sup.1H NMR (500 MHz, DMSO-d6) δ 14.46 (s, 1H), 8.14-8.08 (m, 1H), 7.53-7.48 (m, 1H), 2.27 (s, 3H). 114 [00211] CF.sub.3 Me .sup.1H NMR (500 MHz, DMSO-d6) δ 14.49 (s, 1H), 8.60 (d, J = 7.0 Hz, 1H), 8.33 (dd, J = 7.0, 2.5 Hz, 1H), 2.27 (s, 3H). 115 [00212] CF.sub.3 [00213] .sup.1H NMR (500 MHz, DMSO-d6) δ 14.46 (s, 1H), 7.81-7.76 (m, 2H), 7.35-7.27 (m, 2H), 1.70-1.67 (m, 1H), 1.35-1.32 (m, 2H), 0.89-0.85 (m, 2H). 116 [00214] CF.sub.3 [00215] .sup.1H NMR (500 MHz, DMSO-d6) δ 14.49 (s, 1H), 7.75 (d, J = 7.5 Hz, 2H), 7.50 (d, J = 7.5 Hz, 2H), 1.70-1.66 (m, 1H), 1.34-1.31 (m, 2H), 0.89-0.85 (m, 2H). 117 [00216] CF.sub.3 [00217] .sup.1H NMR (500 MHz, DMSO-d6) δ 14.48 (s, 1H), 7.55-7.45 (m, 2H), 7.38-7.32 (m, 1H), 1.70-1.67 (m, 1H), 1.35-1.32 (m, 2H), 0.87-0.83 (m, 2H). 118 [00218] CF.sub.3 [00219] .sup.1H NMR (500 MHz, DMSO-d6) δ 14.42 (s, 1H), 8.74 (d, J = 5.0. 1H), 8.20 (d, J = 8.0 Hz, 1H), 8.02-7.99 (m, 1H), 7.62-7.56 (m, 1H), 1.70-1.66 (m, 1H), 1.34-1.31 (m, 2H), 0.89-0.85 (m, 2H). 119 [00220] CF.sub.3 [00221] .sup.1H NMR (500 MHz, DMSO-d6) δ 14.45 (s, 1H), 8.82 (s, 1H), 8.41 (d, J = 5.0, 1H), 8.05 (d, J = 7.5, 1H), 7.46 (dd, J = 7.0, 5.0 Hz, 1H), 1.70-1.66 (m, 1H), 1.34-1.31 (m, 2H), 0.89-0.85 (m, 2H). 120 [00222] CF.sub.3 [00223] .sup.1H NMR (500 MHz. DMSO-d6) δ 14.51 (s, 1H). 8.66 (d, J = 5.0 Hz, 2H), 7.86 (d, J = 5.0 Hz, 2H), 1.69-1.64 (m, 1H), 1.34-1.31 (m, 2H), 0.89-0.85 (m, 2H). 121 [00224] CF.sub.3 [00225] .sup.1H NMR (500 MHz, DMSO-d6) δ 14.50 (s, 1H), 8.23-8.19 (m, 1H), 7.13-7.09 (m, 1H), 1.70-1.66 (m, 1H), 1.34-1.31 (m, 2H), 0.85-0.82 (m, 2H). 122 [00226] CF.sub.3 [00227] .sup.1H NMR (500 MHz, DMSO-d6) δ 14.48 (s, 1H), 8.67 (s, 1H), 8.44-8.40 (m, 1H), 8.24-8.20 (m, 1H), 1.70-1.66 (m, 1H), 1.33-1.30 (m, 2H), 0.85- 0.83 (m, 2H). 123 [00228] CF.sub.3 [00229] .sup.1H NMR (500 MHz. DMSO-d.sub.6) δ 14.52 (s, 1H), 9.14 (s, 1H), 8.11 (d, J = 6.5 Hz, 1H), 7.83 (d, J = 8.0 Hz, 1H), 1.70-1.66 (m, 1H), 1.34-1.31 (m, 2H), 0.90-0.85 (m, 2H). 124 [00230] CF.sub.3 [00231] .sup.1H NMR (500 MHz, DMSO-d6) δ 14.49 (s, 1H), 8.75 (s, 1H), 7.82 (d, J = 6.5 Hz, 1H), 7.70 (d, J = 8.0 Hz, 1H), 1.70-1.65 (m, 1H), 1.33-1.29 (m, 2H), 0.85-0.82 (m, 2H). 125 [00232] CF.sub.3 [00233] .sup.1H NMR (500 MHz, DMSO-d6) δ 14.46 (s, 1H), 8.82 (s, 1H), 7.89 (d, J = 8.0 Hz, 1H), 7.51 (d, J = 6.5 Hz, 1H), 1.70-1.66 (m, 1H), 1.34-1.31 (m, 2H), 0.85-0.82 (m, 2H). 126 [00234] CF.sub.3 [00235] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.52 (s, 1H), 8.45-8.40 (m, 1H), 7.80 (d, J = 8.0 Hz, 1H), 7.69 (d, J = 5.0 Hz, 1H), 1.70-1.67 (m, 1H), 1.35-1.32 (m, 2H), 0.87-0.83 (m, 2H). 127 [00236] CF.sub.3 [00237] .sup.1H NMR (500 MHz, DMSO-d6) δ 14.53 (s, 1H), 6.60 (s, 1H), 3.87 (s, 3H), 2.39 (s, 3H), 1.70-1.67 (m, 1H), 1.35-1.32 (m, 2H), 0.87-0.83 (m, 2H) 128 [00238] CF.sub.3 [00239] .sup.1H NMR (500 MHz, DMSO-d6) δ 14.50 (s, 1H). 7.87 (s, 1H), 7.22 (s, 1H), 1.70-1.67 (m, 1H), 1.35-1.32 (m, 2H), 0.88-0.83 (m, 2H) 129 [00240] CF.sub.3 [00241] .sup.1H NMR (500 MHz, DMSO-d6) δ 14.49 (s, 1H), 7.84 (t, J = 57.5 Hz, 1H), 7.12 (s, 1H), 2.40 (s, 3H), 2.23-2.18 (m, 1H), 1.02-0.98 (m, 2H), 0.77- 0.73 (m, 2H). 130 [00242] CF.sub.3 [00243] .sup.1H NMR (500 MHz, DMSO-d6) δ 14.49 (s, 1H), 7.98 (s, 1H), 2.37 (s, 3H), 1.70-1.66 (m, 1H), 1.35-1.31 (m, 2H), 0.87-0.83 (m, 2H). 131 [00244] CF.sub.3 [00245] .sup.1H NMR (500 MHz, DMSO-d6) δ 14.44 (s, 1H), 9.20 (s, 1H), 8.10 (s, 1H), 1.70-1.67 (m, 1H), 1.35-1.32 (m, 2H), 0.87-0.83 (m, 2H) 132 [00246] CF.sub.3 [00247] .sup.1H NMR (500 MHz, DMSO-d6) δ 14.52 (s, 1H), 8.40 (dd, J = 7.0, 5.0 Hz, 1H), 8.00-7.96 (m, 1H), 7.60 (dd, J = 7.0, 5.0 Hz, 1H), 1.70-1.65 (m, 1H), 1.35-1.32 (m, 2H), 0.87-0.84 (m, 2H). 133 [00248] CF.sub.3 [00249] .sup.1H NMR (500 MHz, DMSO-d6) δ 14.46 (s, 1H), 8.34 (d, J = 5.0 Hz, 1H), 8.22 (s, 1H), 7.80 (d, J = 5.0 Hz, 1H), 1.70-1.67 (m, 1H), 1.35-1.32 (m, 2H), 0.87-0.83 (m, 2H). 134 [00250] CF.sub.3 [00251] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.46 (s, 1H), 8.83 (d, J = 2.5 Hz, 1H), 8.71 (d, J = 2.5 Hz, 1H), 8.06-8.02 (m, 1H), 1.70-1.67 (m, 1H), 1.35-1.32 (m, 2H), 0.87-0.83 (m, 2H). 135 [00252] CF.sub.3 [00253] .sup.1H NMR (500 MHz, DMSO-d6) δ 14.49 (s, 1H), 8.45 (dd, J = 5.0, 2.5 Hz, 1H), 7.90-7.85 (m, 2H), 1.70-1.67 (m, 1H), 1.35-1.32 (m, 2H), 0.87- 0.83 (m, 2H). 136 [00254] CF.sub.3 [00255] .sup.1H NMR (500 MHz, DMSO-d6) δ 14.53 (s, 1H), 8.22 (dd, J = 7.0, 5.0 Hz, 1H), 7.45 (d, J = 8.0 Hz, 1H), 1.70-1.67 (m, 1H), 1.35-1.30 (m, 2H), 0.87- 0.83 (m, 2H) 137 [00256] CF.sub.3 [00257] .sup.1H NMR (500 MHz, DMSO-d6) δ 14.52 (s, 1H), 8.60 (d, J = 7.0 Hz, 1H), 8.33 (dd, J = 7.0, 2.5 Hz, 1H), 1.70-1.67 (m, 1H), 1.35-1.32 (m, 2H), 0.87- 0.83 (m, 2H). 138 [00258] CF.sub.3 SEt .sup.1H NMR (500 MHz, DMSO-d6) δ 14.53 (s, 1H), 7.91-7.83 (m, 2H), 7.35-7.27 (m, 2H), 3.07 (q, J = 8.0 Hz, 2H), 1.11 (t, J = 8.0 Hz, 3H). 139 [00259] CF.sub.3 SEt .sup.1H NMR (500 MHz, DMSO-d6) δ 14.46 (s, 1H), 7.85-7.78 (m, 2H), 7.51-7.45 (m, 2H), 3.05 (q, J = 8.0 Hz, 2H), 1.21 (t, J = 8.0 Hz, 3H). 140 [00260] CF.sub.3 SEt .sup.1H NMR (500 MHz, DMSO-d6) δ 14.46 (s, 1H), 7.64-7.60 (m, 1H), 7.53-7.48 (m, 1H), 7.39-7.35 (m, 1H), 3.03 (q, J = 8.0 Hz, 2H), 1.12 (t, J = 8.0 Hz, 3H). 141 [00261] CF.sub.3 SEt .sup.1H NMR (500 MHz, DMSO-d6) δ 14.48 (s, 1H), 8.74 (d, J = 5.0 Hz, 1H), 8.23-8.18 (m, 1H), 8.02-7.99 (m, 1H), 7.62-7.56 (m, 1H), 3.00 (q, J = 8.0 Hz, 2H), 1.11 (t, J = 8.0 Hz, 3H). 142 [00262] CF.sub.3 SEt .sup.1H NMR (500 MHz, DMSO-d6) δ 14.45 (s, 1H), 8.82 (s, 1H), 8.41 (d, J = 5.0, 1H), 8.08-8.02 (m, 1H), 7.49-7.44 (m, 1H), 3.02 (q, J = 8.0 Hz, 2H), 1.12 (t, J = 8.0 Hz, 3H). 143 [00263] CF.sub.3 SEt .sup.1H NMR (500 MHz, DMSO-d6) δ 14.51 (s, 1H), 8.66 (d, J = 5.0 Hz, 2H), 7.86 (d, J = 5.0 Hz, 2H), 3.08 (q, J = 8.0 Hz, 2H), 1.21 (t, J = 8.0 Hz, 3H). 144 [00264] CF.sub.3 SEt .sup.1H NMR (500 MHz, DMSO-d6) δ 14.50 (s, 1H), 8.23-8.19 (m, 1H), 7.13-7.09 (m, 1H), 3.04 (q, J = 8.0 Hz, 2H), 1.11 (t, J = 8.0 Hz, 3H). 145 [00265] CF.sub.3 SEt .sup.1H NMR (500 MHz, DMSO-d6) δ 14.51 (s, 1H), 8.67 (s, 1H), 8.46-8.42 (m, 1H), 8.24-8.20 (m, 1H), 3.05 (q, J = 8.0 Hz, 2H), 1.12 (t, J = 8.0 Hz, 3H) 146 [00266] CF.sub.3 SEt .sup.1H NMR (500 MHz, DMSO-d6) δ 14.53 (s, 1H), 9.14 (s, 1H), 8.11 (d, J = 5.0 Hz, 1H), 7.83 (d, J = 8.0 Hz, 1H), 3.04 (q, J = 5.0 Hz, 2H), 1.12 (t, J = 8.0 Hz, 3H) 147 [00267] CF.sub.3 SEt .sup.1H NMR (500 MHz, DMSO-d6) δ 14.45 (s, 1H), 8.73 (s, 1H), 7.78 (d, J = 5.0 Hz, 1H), 7.71 (d, J = 5.0 Hz, 1H), 3.04 (q, J = 8.0 Hz, 2H), 1.13 (t, J = 8.0 Hz, 3H) 148 [00268] CF.sub.3 SEt .sup.1H NMR (500 MHz, DMSO-d6) δ 14.48 (s, 1H), 8.83 (s, 1H), 7.88 (d, J = 8.0 Hz, 1H), 7.51 (d, J = 8.0 Hz, 1H), 3.04 (q, J = 6.5 Hz, 2H), 1.11 (t, J = 8.0 Hz, 3H) 149 [00269] CF.sub.3 SEt .sup.1H NMR (500 MHz, DMSO-d6) δ 14.50 (s, 1H), 8.45-8.40 (m 1H), 7.80 (d, J = 8.0 Hz, 1H), 7.69 (d, J = 5.0 Hz, 1H), 3.06 (q, J = 8.0 Hz, 2H), 1.12 (t, J = 8.0 Hz, 3H) 150 [00270] CF.sub.3 SEt .sup.1H NMR (500 MHz, DMSO-d6) δ 14.45 (s, 1H), 6.60 (s, 1H), 3.87 (s, 3H), 2.38 (s, 3H), 3.05 (q, J = 8.0 Hz, 2H), 1.11 (t, J = 8.0 Hz, 3H) 151 [00271] CF.sub.3 SEt .sup.1H NMR (500 MHz, DMSO-d6) δ 14.48 (s, 1H), 7.87 (s, 1H), 7.21 (s, 1H), 3.04 (q, J = 8.0 Hz, 2H), 1.11 (t, J = 8.0 Hz, 3H) 152 [00272] CF.sub.3 SEt .sup.1H NMR (500 MHz, DMSO-d6) δ 14.50 (s, 1H), 7.84 (t, J = 57.5 Hz, 1H), 7.05 (s, 1H), 3.00 (q, J = 8.0 Hz, 2H), 2.42 (s, 3H), 1.31 (t, J = 8.0 Hz, 3H). 153 [00273] CF.sub.3 SEt .sup.1H NMR (500 MHz. DMSO-d6) δ 14.49 (s, 1H), 7.97 (s, 1H), 2.35 (s, 3H), 3.03 (q, J = 8.0 Hz, 2H), 1.11 (t, J = 8.0 Hz, 3H) 154 [00274] CF.sub.3 SEt .sup.1H NMR (500 MHz, DMSO-d6) δ 14.54 (s, 1H), 9.20 (s, 1H), 8.10 (s, 1H), 3.04 (q, J = 8.0 Hz, 2H), 1.11 (t, J = 8.0 Hz, 3H) 155 [00275] CF.sub.3 SEt .sup.1H NMR (500 MHz, DMSO-d6) δ 14.52 (s, 1H), 8.40 (dd, J = 7.0, 5.0 Hz, 1H), 8.00-7.96 (m, 1H), 7.60 (dd, J = 8.0, 5.0 Hz. 1H), 3.03 (q, J = 8.0 Hz, 2H), 1.11 (t, J = 8.0 Hz, 3H) 156 [00276] CF.sub.3 [00277] .sup.1H NMR (500 MHz, DMSO-d6) δ 14.46 (s, 1H), 7.89-7.81 (m, 2H), 7.35-7.27 (m, 2H), 5.30 (s, 1H), 4.90 (s, 1H), 2.06 (s, 3H). 157 [00278] CF.sub.3 [00279] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.48 (s, 1H), 7.82 (d, J = 7.5 Hz, 2H), 7.50 (d, J = 7.5 Hz, 2H), 5.29 (s, 1H), 4.91 (s, 1H), 2.03 (s, 3H). 158 [00280] CF.sub.3 [00281] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.49 (s, 1H), 7.74-7.70 (m, 1H), 7.53-7.48 (m, 1H), 7.39-7.35 (m, 1H), 5.29 (s, 1H), 4.91 (s, 1H), 1.93 (s, 3H). 159 [00282] CF.sub.3 [00283] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.48 (s, 1H), 8.74 (d, J = 5.0 Hz, 1H), 8.23-8.18 (m, 1H), 8.02-7.99 (m, 1H), 7.62-7.56 (m, 1H), 5.31 (s, 1H), 4.92 (s, 1H), 1.93 (s, 3H). 160 [00284] CF.sub.3 [00285] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.49 (s, 1H), 8.82 (s, 1H), 8.41 (d, J = 5.0 Hz, 1H), 8.05 (d, J = 7.5 Hz, 1H), 7.46 (d, J = 5.0 Hz, 1H), 5.31 (s, 1H). 4.91 (s, 1H), 1.94 (s, 3H). 161 [00286] CF.sub.3 [00287] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.49 (s, 1H), 8.66 (d, J = 5.0 Hz, 2H), 7.86 (d, J = 5.0 Hz, 2H), 5.29 (s, 1H), 4.91 (s, 1H), 1.95 (s, 3H). 162 [00288] CF.sub.3 [00289] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.48 (s, 1H), 8.23-8.19 (m, 1H), 7.13-7.09 (m, 1H), 5.29 (s, 1H), 4.91 (s, 1H), 1.93 (s, 3H). 163 [00290] CF.sub.3 [00291] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.49 (s, 1H), 8.66 (s, 1H), 8.46-8.42 (m, 1H), 8.24-8.20 (m, 1H), 5.29 (s, 1H), 4.91 (s, 1H), 1.95 (s, 3H). 164 [00292] CF.sub.3 [00293] .sup.1H NMR (500 MHz, DMSO-d.sub.6)) δ 14.53 (s, 1H), 9.14 (s, 1H), 8.10 (d, J = 5.0 Hz, 1H), 7.82 (d, J = 8.0 Hz, 1H), 5.31 (s, 1H), 4.90 (s, 1H), 1.93 (s, my 165 [00294] CF.sub.3 [00295] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.49 (s, 1H), 8.73 (s, 1H), 7.78 (d, J = 5.0 Hz, 1H), 7.71 (d, J = 8.0 Hz, 1H), 5.29 (s, 1H), 4.91 (s, 1H), 1.93 (s, 3H). 166 [00296] CF.sub.3 [00297] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.50 (s, 1H), 8.82 (s, 1H), 7.87 (d, J = 8.0 Hz, 1H), 7.51 (d, J = 5.0 Hz, 1H), 5.30 (s, 1H), 4.91 (s, 1H), 1.93 (s, 3H). 167 [00298] CF.sub.3 [00299] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.48 (s, 1H), 8.45-8.40 (m, 1H), 7.80 (d, J = 8.0 Hz, 1H), 7.69 (d, J = 5.0 Hz, 1H), 5.29 (s, 1H), 4.91 (s, 1H), 1.93 (s, 3H). 168 [00300] CF.sub.3 [00301] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.45 (s, 1H), 6.60 (s, 1H), 3.87 (s, 3H), 2.38 (s, 3H), 5.30 (s, 1H), 4.91 (s, 1H), 1.94 (s, 3H). 169 [00302] CF.sub.3 [00303] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.49 (s, 1H), 7.87 (s, 1H), 7.21 (s, 1H), 5.29 (s, 1H), 4.91 (s, 1H), 1.93 (s,3H). 170 [00304] CF.sub.3 [00305] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.51 (s, 1H), 7.84 (t, J = 57.5 Hz, 1H), 7.04 (s, 1H), 5.18 (s, 1H), 4.87 (s, 1H), 2.41 (s, 3H), 2.06 (s, 3H). 171 [00306] CF.sub.3 [00307] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.46 (s, 1H), 7.97 (s, 1H), 5.30 (s, 1H), 4.91 (s, 1H), 2.35 (s, 3H), 1.94 (s, 3H). 172 [00308] CF.sub.3 [00309] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.44 (s, 1H), 9.21 (s, 1H), 8.10 (s, 1H), 5.29 (s, 1H), 4.90 (s, 1H), 1.93 (s, 3H). 173 [00310] CF.sub.3 [00311] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.52 (s, 1H), 8.40 (dd, J = 7.0, 5.0 Hz, 1H), 8.00-7.96 (m, 1H), 7.60 (dd, J = 8.0, 5.0 Hz, 1H), 5.30 (s, 1H), 4.91 (s, 1H), 1.93 (s, 3H). 174 [00312] CF.sub.3 NH.sub.2 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.51 (s, 1H), 7.82-7.74 (m, 2H), 7.35-7.27 (m, 2H), 6.84 (s, 2H). 175 [00313] CF.sub.3 NH.sub.2 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 1451 (s, 1H). 7.75 (d, J = 7.5 Hz, 2H), 7.50 (d, J = 7.5 Hz, 2H), 6.84 (s, 2H). 176 [00314] CF.sub.3 NH.sub.2 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.48 (s, 1H), 7.58-7.50 (m, 2H), 7.38-7.35 (m, 1H), 6.84 (s, 2H). 177 [00315] CF.sub.3 NH.sub.2 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.52 (s, 1H), 8.73 (d, J = 5.0 Hz, 1H), 8.20 (d, J = 8.0 Hz, 1H), 8.02-7.99 (m, 1H), 7.62-7.56 (m, 1H), 6.84 (s, 2H) 178 [00316] CF.sub.3 NH.sub.2 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.45 (s, 1H), 8.80 (s, 1H), 8.40 (d, J = 5.0 Hz, 1H), 8.03 (d, J = 5.0 Hz. 1H), 7.49-7.45 (m, 1H), 6.83 (s, 2H). 179 [00317] CF.sub.3 NH.sub.2 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.48 (s, 1H), 8.65 (d, J = 5.0 Hz, 2H), 7.80 (d, J = 5.0 Hz, 2H), 6.85 (s, 2H). 180 [00318] CF.sub.3 NH.sub.2 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.49 (s, 1H), 8.22-8.19 (m, 1H), 7.13-7.09 (m, 1H), 6.85 (s, 2H). 181 [00319] CF.sub.3 NH.sub.2 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.52 (s, 1H), 8.65 (s, 1H), 8.46-8.42 (m, 1H), 8.25-8.21 (m, 1H), 6.84 (s, 2H). 182 [00320] CF.sub.3 NH.sub.2 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.48 (s, 1H), 9.15 (s, 1H), 8.11 (d, J = 8.0 Hz, 1H), 7.82 (d, J = 5.0 Hz, 1H), 6.86 (s, 2H). 183 [00321] CF.sub.3 NH.sub.2 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.46 (s, 1H), 8.73 (s, 1H), 7.80 (d, J = 8.0 Hz, 1H), 7.71 (d, J = 8.0 Hz, 1H), 6.83 (s, 2H). 184 [00322] CF.sub.3 NH.sub.2 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.45 (s, 1H), 8.83 (s, 1H), 7.89 (d, J = 8.0 Hz, 1H), 7.51 (d, J = 8.0 Hz, 1H), 6.84 (s, 2H). 185 [00323] CF.sub.3 NH.sub.2 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.53 (s, 1H), 8.43-8.40 (m 1H), 7.80 (d, J = 8.0 Hz, 1H), 7.69 (d, J = 5.0 Hz, 1H), 6.84 (s, 2H). 186 [00324] CF.sub.3 NH.sub.2 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.48 (s, 1H), 6.84 (s, 2H), 6.60 (s, 1H), 3.87 (s, 3H), 2.39 (s, 3H). 187 [00325] CF.sub.3 NH.sub.2 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.48 (s, 1H), 7.87 (s, 1H), 7.20 (s, 1H), 6.84 (s, 2H). 188 [00326] CF.sub.3 NH.sub.2 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.51 (s, 1H), 7.84 (t, J = 57.5 Hz, 1H), 7.04 (s, 1H), 6.86 (s, 2H), 2.41 (s, 3H), 189 [00327] CF.sub.3 NH.sub.2 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.46 (s, 1H), 7.97 (s, 1H), 6.86 (s, 2H), 2.37 (s, 3H). 190 [00328] CF.sub.3 NH.sub.2 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.44 (s, 1H), 9.20 (s, 1H), 8.10 (s, 1H), 6.84 (s, 2H) 191 [00329] CF.sub.3 NH.sub.2 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.52 (s, 1H), 8.43 (dd, J = 7.0, 5.0 Hz, 1H), 8.02-7.98 (m, 1H), 7.79-7.75 (m, 1H), 6.86 (s, 2H). 192 [00330] CF.sub.3 NHMe .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.52 (s, 1H), 7.92-7.84 (m, 2H), 7.35-7.27 (m, 2H), 5.95 (s, 1H), 2.71 (s, 3H). 193 [00331] CF.sub.3 NHMe .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.48 (s, 1H), 7.86-7.80 (m, 2H), 7.51-7.45 (m, 2H), 5.93 (s, 1H), 2.70 (s, 3H). 194 [00332] CF.sub.3 NHMe .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.49 (s, 1H), 7.65-7.61 (m, 1H), 7.55-7.51 (m, 1H), 7.39- 7.35 (m, 1H), 5.93 (s, 1H), 2.71 (s, 3H). 195 [00333] CF.sub.3 NHMe .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.48 (s, 1H), 8.74-8.71 (m, 1H), 8.20 (d, J = 8.0 Hz, 1H), 8.02- 7.98 (m, 1H), 7.62-7.56 (m, 1H), 5.96 (s, 1H), 2.72 (s, 3H). 196 [00334] CF.sub.3 NHMe .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 1 4.49 (s, 1H), 8.91 (s, 1H), 8.41-8.38 (m, 1H), 8.13-8.10 (m, 1H), 7.46-7.42 (m, 1H), 5.93 (s, 1H), 2.70 (s, 3H). 197 [00335] CF.sub.3 NHMe .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.45 (s, 1H), 8.66 (d, J = 5.0 Hz, 2H), 7.92 (d, J = 5.0 Hz, 2H), 5.95 (s, 1H), 2.70 (s, 3H). 198 [00336] CF.sub.3 NHMe .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.49 (s, 1H), 8.20-8.15 (m, 1H), 7.12-7.09 (m, 1H), 5.93 (s, 1H), 2.69(s, 3H). 199 [00337] CF.sub.3 NHMe .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.49 (s, 1H), 8.67 (s, 1H), 8.45-8.40 (m, 1H), 8.25-8.21 (m, 1H), 5.95 (s, 1H), 2.71 (s, 3H). 200 [00338] CF.sub.3 NHMe .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.49 (s, 1H), 9.16 (s, 1H), 8.13-8.09 (m 1H), 7.83 (d, J = 8.0 Hz. 1H), 5.95 (s, 1H), 2.70 (s, 3H). 201 [00339] CF.sub.3 NHMe .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.50 (s, 1H), 8.80 (s, 1H), 7.87-7.84 (m, 1H), 7.72 (d, J = 8.0 Hz, 1H), 5.93 (s, 1H), 2.72 (s, 3H). 202 [00340] CF.sub.3 NHMe .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.39 (s, 1H), 8.94 (s, 1H), 7.96-7.92 (m, 1H), 7.52 (d, J = 50 Hz, 1H), 5.93 (s, 1H), 2.70 (s, 3H). 203 [00341] CF.sub.3 NHMe .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.46 (s, 1H), 8.43 (d, J = 5.0 Hz, 1H), 7.92-7.87 (m, 1H), 7.82-7.76 (m, 1H), 5.95 (s, 1H), 2.71 (s, 3H). 204 [00342] CF.sub.3 NHMe .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.46 (s, 1H), 6.62 (s, 1H), 5.95 (s, 1H), 3.87 (s, 3H), 2.70 (s, 3H), 2.39 (s, 3H). 205 [00343] CF.sub.3 NHMe .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.46 (s, 1H), 7.94 (s, 1H), 7.25 (s, 1H), 5.95 (s, 1H), 2.70 (s, 3H). 206 [00344] CF.sub.3 NHMe .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.48 (s, 1H), 7.84 (t, J = 57.5 Hz, 1H), 6.99 (s, 1H), 5.95 (s, 1H), 2.78 (s, 3H), 2.40 (s, 3H). 207 [00345] CF.sub.3 NHMe .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.46 (s, 1H), 7.96 (s, 1H), 5.93 (s, 1H), 2.71 (s, 3H), 2.34 (s, 3H). 208 [00346] CF.sub.3 NHMe .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.46 (s, 1H), 9.20 (s, 1H), 8.07 (s, 1H), 5.95 (s, 1H), 2.79 (s, 3H). 209 [00347] CF.sub.3 NHMe .sup.1H NMR (500 MHz. DMSO-d.sub.6) δ 14.49 (s, 1H), 8.43-8.40 (m, 1H), 7.99-7.94 (m, 1H), 7.74-7.70 (m, 1H), 5.95 (s, 1H), 2.70 (s, 3H). 210 [00348] CF.sub.3 [00349] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.40 (s, 1H), 9.94 (s, 1H), 7.89-7.81 (m, 2H), 7.35-7.27 (m, 2H), 2.07 (s, 3H). 211 [00350] CF.sub.3 [00351] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.51 (s, 1H), 9.94 (s, 1H), 7.75 (d, J = 7.5 Hz, 2H), 7.50 (d, J = 7.5 Hz, 2H), 2.07 (s, 3H). 212 [00352] CF.sub.3 [00353] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.48 (s, 1H), 9.93 (s, 1H), 7.58-7.50 (m, 2H), 7.36-7.34 (m, 1H), 2.07 (s, 3H). 213 [00354] CF.sub.3 [00355] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.52 (s, 1H), 9.94 (s, 1H), 8.73 (d, J = 5.0 Hz, 1H), 8.19 (d, J = 8.0 Hz, 1H), 8.02-7.99 (m, 1H), 7.62-7.56 (m, 1H), 2.07 (s, 3H). 214 [00356] CF.sub.3 [00357] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.45 (s, 1H), 9.94 (s, 1H), 8.80 (s, 1H), 8.38 (d, J = 5.0 Hz, 1H), 8.03 (d, J = 5.0 Hz, 1H), 7.49-7.45 (m, 1H), 2.07 (s, 3H). 215 [00358] CF.sub.3 [00359] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.48 (s, 1H), 9.94 (s, 1H), 8.64 (d, J = 5.0 Hz, 2H), 7.80 (d, J = 5.0 Hz, 2H), 2.07 (s, 3H). 216 [00360] CF.sub.3 [00361] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.49 (s, 1H), 9.92 (s, 1H), 8.22-8.19 (m, 1H), 7.13-7.09 (m, 1H), 2.06 (s, 3H). 217 [00362] CF.sub.3 [00363] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.52 (s, 1H), 9.94 (s, 1H), 8.65 (s, 1H), 8.46-8.42 (m, 1H), 8.25-8.21 (m, 1H), 2.06 (s, 3H). 218 [00364] CF.sub.3 [00365] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.48 (s, 1H), 9.94 (s, 1H), 9.15 (s, 1H), 8.10 (d, J = 8.0 Hz, 1H), 7.82 (d, J = 8.0 Hz, 1H), 2.07 (s, 3H). 219 [00366] CF.sub.3 [00367] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.46 (s, 1H), 9.94 (s, 1H), 8.73 (s, 1H), 7.78 (d, J = 8.0 Hz, 1H), 7.71 (d, J = 8.0 Hz, 1H), 2.07 (s, 3H). 220 [00368] CF.sub.3 [00369] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.45 (s, 1H), 9.94 (s, 1H), 8.83 (s, 1H), 7.89 (d, J = 8.0 Hz, 1H), 7.51 (d, J = 8.0 Hz, 1H), 2.07 (s, 3H) 221 [00370] CF.sub.3 [00371] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.53 (s, 1H), 9.92 (s, 1H), 8.43-8.40 (m 1H), 7.80 (d, J = 8.0 Hz, 1H), 7.69 (d, J = 5.0 Hz, 1H), 2.08 (s, 3H). 222 [00372] CF.sub.3 [00373] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.43 (s, 1H), 9.94 (s, 1H), 6.60 (s, 1H), 3.87 (s, 3H), 2.39 (s, 3H), 2.07 (s, 3H). 223 [00374] CF.sub.3 [00375] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.48 (s, 1H), 9.94 (s, 1H), 7.87 (s, 1H), 7.20 (s, 1H), 2.07 (s, 3H). 224 [00376] CF.sub.3 [00377] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.49 (s, 1H), 9.54 (s, 1H), 7.85 (t, J = 57.5 Hz, 1H), 7.03 (s, 1H), 2.44 (s, 3H), 2.07 (s, 3H). 225 [00378] CF.sub.3 [00379] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.46 (s, 1H), 9.94 (s, 1H), 7.97 (s, 1H), 2.37 (s, 3H), 2.07 (s, 3H), 226 [00380] CF.sub.3 [00381] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.44 (s, 1H), 9.94 (s, 1H), 9.20 (s, 1H), 8.10 (s, 1H), 2.07 (s, 3H). 227 [00382] CF.sub.3 [00383] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.52 (s, 1H), 9.94 (s, 1H), 8.42 (dd, J = 7.0, 5.0 Hz, 1H), 8.02- 7.98 (m, 1H), 7.77-7.73 (m, 1H), 2.07 (s, 3H). 228 [00384] CF.sub.3 Me .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.49 (s, 1H), 7.98 (d, J = 7.5 Hz, 2H), 7.75 (d, J = 7.5 Hz, 2H), 2.28 (s, 3H). 229 [00385] CF.sub.3 Me .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.50 (s, 1H), 8.07-7.55 (m, 2H), 7.10 (s, 1H), 2.34 (s, 3H). 230 [00386] CF.sub.3 Me 231 [00387] CF.sub.3 Me 232 [00388] CF.sub.3 Me 233 [00389] CF.sub.3 Me 234 [00390] CF.sub.3 Me 235 [00391] CF.sub.3 Me 236 [00392] CF.sub.3 Me 237 [00393] CF.sub.3 Me 238 [00394] CF.sub.3 Me 239 [00395] CF.sub.3 Me 240 [00396] CF.sub.3 Me 241 [00397] CF.sub.3 Me 242 [00398] CF.sub.3 Me 243 [00399] CF.sub.3 Me 244 [00400] CF.sub.3 Me 245 [00401] CF.sub.3 Me 246 [00402] CF.sub.3 Me 247 [00403] CF.sub.3 Me 248 [00404] CF.sub.3 Me 249 [00405] CF.sub.3 Me 250 [00406] CF.sub.3 Me 251 [00407] CF.sub.3 Me 252 [00408] CF.sub.3 Me 253 [00409] CF.sub.3 Me 254 [00410] CF.sub.3 Me 255 [00411] CF.sub.3 Me 256 [00412] CF.sub.3 Me 257 [00413] CF.sub.3 Me 258 [00414] CF.sub.3 Me 259 [00415] CF.sub.3 Me 260 [00416] CF.sub.3 Me 261 [00417] CF.sub.3 Me 262 [00418] CF.sub.3 Me 263 [00419] CF.sub.3 Me 264 [00420] CF.sub.3 Me 265 [00421] CF.sub.3 Me 266 [00422] CF.sub.3 Me 267 [00423] CF.sub.3 Me 268 [00424] CF.sub.3 Me 269 [00425] CF.sub.3 Me 270 [00426] CF.sub.3 Me 271 [00427] CF.sub.3 Me 272 [00428] CF.sub.3 Me 273 [00429] CF.sub.3 Me 274 [00430] CF.sub.3 Me 275 [00431] CF.sub.3 Me 276 [00432] CF.sub.3 Me 277 [00433] CF.sub.3 Me 278 [00434] CF.sub.3 Me 279 [00435] CF.sub.3 Me 280 [00436] CF.sub.3 Me 281 [00437] CF.sub.3 Me 282 [00438] CF.sub.3 Me 283 [00439] CF.sub.3 Me 284 [00440] CF.sub.3 Me 285 [00441] CF.sub.3 Me 286 [00442] CF.sub.3 Me 287 [00443] CF.sub.3 Me 288 [00444] CF.sub.3 Me 289 [00445] CF.sub.3 Me 290 [00446] CF.sub.3 Me 291 [00447] CF.sub.3 Me 292 [00448] CF.sub.3 Me 293 [00449] CF.sub.3 Me 294 [00450] CF.sub.3 Me 295 [00451] CF.sub.3 Me 296 [00452] CF.sub.3 Me 297 [00453] CF.sub.3 Me 298 [00454] CF.sub.3 Me 299 [00455] CF.sub.3 Me 300 [00456] CF.sub.3 Me 301 [00457] CF.sub.3 Me .sup.1H NMR (500 MHz, Chloroform-d) δ 14.38 (s, 1H), 7.57 (d, J = 8.0 Hz, 1H), 7.53 (dd, J = 8.5, 6.0 Hz, 1H), 7.39-7.32 (m, 1H), 2.17 (s, 3H). 302 [00458] CF.sub.3 Me 303 [00459] CF.sub.3 Me 304 [00460] CF.sub.3 Me 305 [00461] CF.sub.3 Me 306 [00462] CF.sub.3 Me 307 [00463] CF.sub.3 Me 308 [00464] CF.sub.3 Me 309 [00465] CF.sub.3 Me 310 [00466] CF.sub.3 Me 311 [00467] CF.sub.3 Me 312 [00468] CF.sub.3 Me 313 [00469] CF.sub.3 Me .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.54 (s, 1H), 7.97 (s, 1H), 7.88 (d, J = 8.0 Hz, 1H), 7.58 (d, J = 8.0 Hz, 1H), 2.17 (5.3H). 314 [00470] CF.sub.3 Me 315 [00471] CF.sub.3 Me 316 [00472] CF.sub.3 Me 317 [00473] CF.sub.3 Me 318 [00474] CF.sub.3 Me 319 [00475] CF.sub.3 Me 320 [00476] CF.sub.3 Me 321 [00477] CF.sub.3 Me 322 [00478] CF.sub.3 Me 323 [00479] CF.sub.3 Me 324 [00480] CF.sub.3 Me 325 [00481] CF.sub.3 Me 326 [00482] CF.sub.3 Me 327 [00483] CF.sub.3 Me 328 [00484] CF.sub.3 Me 329 [00485] CF.sub.3 Me 330 [00486] CF.sub.3 Me 331 [00487] CF.sub.3 Me 332 [00488] CF.sub.3 Me 333 [00489] CF.sub.3 Me 334 [00490] CF.sub.3 Me .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.42 (s, 1H) 8.09-8.06 (m, 2H), 2.15 (s, 3H). 335 [00491] CF.sub.3 Me 336 [00492] CF.sub.3 Me 337 [00493] CF.sub.3 Me 338 [00494] CF.sub.3 Me 339 [00495] CF.sub.3 Me 340 [00496] CF.sub.3 Me 341 [00497] CF.sub.3 Me 342 [00498] CF.sub.3 Me 343 [00499] CF.sub.3 Me 344 [00500] CF.sub.3 Me 345 [00501] CF.sub.3 Me 346 [00502] CF.sub.3 Me 347 [00503] CF.sub.3 Me 348 [00504] CF.sub.3 Me 349 [00505] CF.sub.3 Me 350 [00506] CF.sub.3 Me 351 [00507] CF.sub.3 Me 352 [00508] CF.sub.3 Me 353 [00509] CF.sub.3 Me 354 [00510] CF.sub.3 Me 355 [00511] CF.sub.3 Me 356 [00512] CF.sub.3 Me 357 [00513] CF.sub.3 Me 358 [00514] CF.sub.3 Me 359 [00515] CF.sub.3 Me 360 [00516] CF.sub.3 Me 361 [00517] CF.sub.3 Me 362 [00518] CF.sub.3 Me 363 [00519] CF.sub.3 Me 364 [00520] CF.sub.3 Me 365 [00521] CF.sub.3 Me 366 [00522] CF.sub.3 Me 367 [00523] CF.sub.3 Me 368 [00524] CF.sub.3 Me 369 [00525] CF.sub.3 Me 370 [00526] CF.sub.3 Me 371 [00527] CF.sub.3 Me 372 [00528] CF.sub.3 Me 373 [00529] CF.sub.3 Me 374 [00530] CF.sub.3 Me 375 [00531] CF.sub.3 Me 376 [00532] CF.sub.3 Me 377 [00533] CF.sub.3 Me 378 [00534] CF.sub.3 Me 379 [00535] CF.sub.3 Me 380 [00536] CF.sub.3 Me 381 [00537] CF.sub.3 Me 382 [00538] CF.sub.3 Me 383 [00539] CF.sub.3 Me 384 [00540] CF.sub.3 Me 385 [00541] CF.sub.3 Me 386 [00542] CF.sub.3 Me 387 [00543] CF.sub.3 Me 388 [00544] CF.sub.3 CHF.sub.2 .sup.1H NMR (500 MHz, DMSO-d6) δ 14.42 (s, 1H), 9.16 (s, 1H), 8.45 (s, 1H), 7.94 (t, J = 59.0 Hz, 1H), 7.25 (t, J = 54.5 Hz, 1H). 389 [00545] CF.sub.3 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d6) δ 14.32 (s, 1H), 9.12 (s, 1H), 8.44 (s, 1H), 7.91 (t, J = 59.1 Hz, 1H). 390 [00546] CF.sub.3 CHO .sup.1H NMR (500 MHz, DMSO-d6) δ 14.37 (s, 1H), 10.32 (s, 1H), 9.24 (s, 1H), 8.46 (s, 1H), 7.97 (t, J = 58.5 Hz, 1H). 391 [00547] CF.sub.3 [00548] .sup.1H NMR (500 MHz, DMSO-d6) δ 14.32 (s, 1H), 9.13 (s, 1H), 8.46 (s, 1H), 7.96 (t, J = 59.0 Hz, 1H), 6.62 (s, 1H), 4.09 (q, J = 7.0 Hz, 2H), 1.21 (t, J = 7.0 Hz, 3H). 392 [00549] CF.sub.3 [00550] .sup.1H NMR (500 MHz, DMSO-d6) δ 14.32 (s, 1H), 9.12 (s, 1H), 8.45 (s, 1H), 7.96 (t, J = 59.0 Hz, 1H), 6.62 (s, 1H), 3.99 (t, J = 6.5 Hz, 2H), 1.63- 1.56 (m, 2H), 0.89 (t, J = 7.5 Hz, 3H). 393 [00551] CF.sub.3 [00552] .sup.1H NMR (500 MHz, DMSO-d6) δ 14.32 (s, 1H), 9.16 (s, 1H), 8.59 (s, 1H), 7.96 (t, J = 59.0 Hz, 1H), 6.62 (s, 1H), 4.27-4.16 (m, 1H), 1.19 (s, 6H). 394 [00553] CF.sub.3 [00554] .sup.1H NMR (500 MHz, DMSO-d6) δ 14.32 (s, 1H), 9.12 (s, 1H), 8.45 (s, 1H), 7.96 (t, J = 59.0 Hz, 1H), 6.62 (s, 1H), 4.57-4.51 (m, 1H), 2.14- 1.07 (m, 10H). 395 [00555] CF.sub.3 [00556] .sup.1H NMR (500 MHz, DMSO-d6) δ 14.32 (s, 1H), 9.12 (s, 1H), 8.49 (s, 1H), 7.96 (t, J = 59.0 Hz, 1H), 6.62 (s, 1H), 3.86 (q, J = 7.0 Hz, 2H), 1.37 (t, J = 7.5 Hz, 3H). 396 [00557] CF.sub.3 [00558] .sup.1H NMR (500 MHz, DMSO-d6) δ 14.39 (s, 1H), 9.12 (s, 1H), 8.49 (s, 1H), 7.96 (t, J = 59.0 Hz, 1H), 3.39-3.36 (m, 4H), 1.97-1.93 (m, 4H). 397 [00559] CF.sub.3 F .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.38 (s, 1H), 7.92-7.88 (dd, J = 9.0, 5.5 Hz, 2H), 7.38-7.28 (m, 2H). 398 [00560] CF.sub.3 [00561] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.33 (s, 1H), 7.89-7.79 (m, 2H), 7.34-7.28 (m, 2H), 7.26- 7.23 (m, 2H), 6.91-6.87 (m, 2H), 6.22 (s, 1H), 4.32 (s, 2H), 3.79 (s, 3H). 399 [00562] CF.sub.3 Me .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.41 (s, 1H), 7.81 (d, J = 2.0 Hz, 1H), 7.71 (d, J = 7.5 Hz, 1H), 7.61 (dd, J = 7.5, 2.0 Hz, 1H), 2.41 (s, 3H), 2.34 (s, 3H). 400 [00563] CF.sub.3 [00564] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.39 (s, 1H), 7.43 (d, J = 7.5 Hz, 1H), 7.13-7.05 (m, 2H), 2.31 (s, 3H), 2.20-2.16 (m, 1H), 1.01-0.96 (m, 2H), 0.78-0.74 (m, 2H). 401 [00565] CF.sub.3 [00566] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.38 (br, 1H), 7.62-7.55 (m, 2H), 7.39-7.32 (m, 1H), 5.35 (s, 1H), 4.96 (s, 1H), 1.96 (s, 3H). 402 [00567] CF.sub.3 [00568] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.36 (br, 1H), 7.56 (d, J = 8.0 Hz, 1H), 7.52 (dd, J = 8.5, 6.0 Hz, 1H), 7.39-7.32 (m, 1H), 1.73 (s, 1H), 1.32 (m, 2H), 0.92-0.80 (m, 2H). 403 [00569] CF.sub.3 [00570] .sup.1H NMR (500 MHz. DMSO-d.sub.6) δ 14.34 (br, 1H), 7.97 (d, J = 2.0 Hz, 1H), 7.88 (dd, J = 8.5, 2.0 Hz, 1H), 7.62 (d, J = 8.5 Hz, 1H), 5.34 (s, 1H), 4.94 (s, 1H), 1.94 (s, 3H). 404 [00571] CF.sub.3 [00572] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.38 (br, 1H), 7.95 (d, J = 2.0 Hz, 1H), 7.88-7.83 (m, 1H), 7.56 (d, J = 8.5 Hz, 1H), 1.76-1.68 (m, 1H), 1.35-1.20 (m, 2H), 0.94-0.84 (m, 2H). 405 [00573] CF.sub.3 [00574] .sup.1H NMR (500 MHz, DMSO-d6) δ 14.37 (br, 1H), 8.79 (d, J = 7.5 Hz, 1H), 8.37 (d, J = 7.5 Hz, 1H), 7.81 (t, J = 7.5 Hz, 1H), 2.31-2.28 (m, 1H), 1.62- 1.56 (m, 2H), 1.42-1.35 (m, 2H). 406 [00575] CF.sub.3 [00576] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.29 (s, 1H), 8.07-8.03 (m, 2H), 5.33 (s, 1H), 4.93 (s, 1H), 1.96 (s, 3H). 407 [00577] CF.sub.3 [00578] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.36 (s, 1H), 7.35-7.27 (m, 2H), 2.17-2.11 (m, 1H), 0.99-0.95 (m, 2H), 0.75-0.71 (m, 2H). 408 [00579] CF.sub.3 Me .sup.1H NMR (500 MHz, Chloroform-d) δ 14.37 (br, 1H), 8.09 (s, 1H), 8.0 (d, J = 8.5 Hz, 1H), 7.5 (d, J = 8.5 Hz, 1H), 2.18 (s, 3H). 409 [00580] CF.sub.3 [00581] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.44 (s, 1H), 8.01 (s, 1H), 7.90 (d, J = 8.5 Hz, 1H), 7.68 (d, J = 8.5 Hz, 1H), 5.35 (s, 1H), 4.96 (s, 1H), 1.99 (s, 3H). 410 [00582] CF.sub.3 [00583] .sup.1H NMR (500 MHz, Chloroform-d) δ 14.43 (br, 1H), 8.01 (s, 1H), 7.90 (d, J = 8.5 Hz, 1H), 7.53 (d, J = 8.5 Hz, 1H), 1.11 (m, 1H), 1.36 (m, 2H), 0.91 (m, 2H). 411 [00584] CF.sub.3 [00585] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.34 (s, 1H), 8.57 (d, J = 5.0 Hz, 1H), 8.24 (s, 1H), 8.07 (dd, J = 5.0, 1.5 Hz, 1H), 5.35 (s, 1H), 4.96 (s, 1H), 1.99 (s, 3H). 412 [00586] CF.sub.3 [00587] .sup.1H NMR (500 MHz, DMSO-d6) δ 14.38 (s, 1H), 9.41 (s, 1H), 8.88 (d, J = 2.5 Hz, 1H), 8.56 (d, J = 2.5 Hz, 1H), 5.14 (s, 1H), 4.73 (s, 1H), 1.95 (s, 3H). 413 [00588] CF.sub.3 [00589] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.39 (s, 1H), 9.54 (s, 1H), 8.98 (s, 1H), 7.80 (d, J = 8.0 Hz, 1H), 7.62 (d, J = 8.0 Hz, 1H), 5.69 (s, 1H), 5.17 (s, 1H), 5.09 (s, 1H), 4.86 (s, 1H), 2.06 (s, 3H), 2.01 (s, 3H). 414 [00590] CF.sub.3 Br .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 14.36 (s, 1H), 8.19-8.16 (m, 1H), 7.13-7.10 (m, 1H).

TABLE-US-00002 TABLE 2 The structures of the group M in the derivative compounds I-1 (X, Y, Z groups are shown in Table 1) [00591] NO. M M-1 [00592] M-2 [00593] M-3 [00594] M-4 [00595] M-5 [00596] M-6 [00597] M-7 [00598] M-8 [00599] M-9 [00600] M-10 [00601] M-11 [00602] M-12 [00603] M-13 [00604] M-14 [00605] M-15 [00606] M-16 [00607] M-17 [00608] M-18 [00609] M-19 [00610] M-20 [00611] M-21 [00612] M-22 [00613] M-23 [00614] M-24 [00615] M-25 [00616] M-26 [00617] M-27 [00618] M-28 [00619] M-29 [00620] M-30 [00621] M-31 [00622] M-32 [00623] M-33 [00624] M-34 [00625] M-35 [00626] M-36 [00627] M-37 [00628] M-38 [00629] M-39 [00630] M-40 [00631] M-41 [00632] M-42 [00633] M-43 [00634] M-44 [00635] M-45 [00636] M-46 [00637] M-47 [00638] M-48 [00639] M-49 [00640] M-50 [00641] M-51 [00642] M-52 [00643] M-53 [00644] M-54 [00645] M-55 [00646] M-56 [00647] M-57 [00648] M-58 [00649] M-59 [00650] M-60 [00651] M-61 [00652] M-62 [00653] M-63 [00654] M-64 [00655] M-65 [00656] M-66 [00657] M-67 [00658] M-68 [00659] M-69 [00660] M-70 [00661] M-71 [00662] M-72 [00663] M-73 [00664] M-74 [00665] M-75 [00666] M-76 [00667] M-77 [00668] M-78 [00669] M-79 [00670] M-80 [00671] M-81 [00672] M-82 [00673] M-83 [00674] M-84 [00675] M-85 [00676] M-86 [00677] M-87 [00678] M-88 [00679] M-89 [00680] M-90 [00681] M-91 [00682] M-92 [00683] M-93 [00684] M-94 [00685] M-95 [00686] M-96 [00687] M-97 [00688] M-98 [00689] M-99 [00690] M-100 [00691] M-101 [00692] M-102 [00693] M-103 [00694] M-104 [00695] M-105 [00696] M-106 [00697] M-107 [00698] M-108 [00699] M-109 [00700] M-110 [00701] M-111 [00702] M-112 [00703] M-113 [00704] M-114 [00705] M-115 [00706] M-116 [00707] M-117 [00708] M-118 [00709] M-119 [00710] M-120 [00711] M-121 [00712] M-122 [00713] M-123 [00714] M-124 [00715] M-125 [00716] M-126 [00717] M-127 [00718] M-128 [00719] M-129 [00720] M-130 [00721] M-131 [00722] M-132 [00723] M-133 [00724] M-134 [00725] M-135 [00726] M-136 [00727] M-137 [00728] M-138 [00729] M-139 [00730] M-140 [00731] M-141 [00732] M-142 [00733] M-143 [00734] M-144 [00735] M-145 [00736] M-146 [00737] M-147 [00738] M-148 [00739] M-149 [00740] M-150 [00741] M-151 [00742] M-152 [00743] M-153 [00744] M-154 [00745] M-155 [00746] M-156 [00747] M-157 [00748] M-158 [00749] M-159 [00750] M-160 [00751] M-161 [00752] M-162 [00753] M-163 [00754] M-164 [00755] M-165 [00756] M-166 [00757] M-167 [00758] M-168 [00759] M-169 [00760] M-170 [00761] M-171 [00762] M-172 [00763] M-173 [00764] M-174 [00765] M-175 [00766] M-176 [00767] M-177 [00768] M-178 [00769] M-179 [00770] M-180 [00771] M-181 [00772] M-182 [00773] M-183 [00774] M-184 [00775] M-185 [00776] M-186 [00777] M-187 [00778] M-188 [00779] M-189 [00780] M-190 [00781] M-191 [00782] M-192 [00783] M-193 [00784] M-194 [00785] M-195 [00786] M-196 [00787] M-197 Me M-198 Et M-199 [00788] M-200 CN M-201 [00789] M-202 [00790] M-203 [00791] M-204 [00792] M-205 [00793] M-206 [00794] M-207 [00795] M-208 [00796] M-209 [00797] M-210 [00798] M-211 [00799] M-212 [00800] M-213 [00801] M-214 [00802] M-215 [00803] M-216 [00804] M-217 [00805]

TABLE-US-00003 TABLE 3 Structures of some derivative compounds I-1 NO. X Y Z M .sup.1HNMR 1-1 [00806] CF.sub.3 Me M-1  1-2 [00807] CF.sub.3 Me M-2  1-3 [00808] CF.sub.3 Me M-7  1-4 [00809] CF.sub.3 Me M-12  1-5 [00810] CF.sub.3 Me M-24  1-6 [00811] CF.sub.3 Me M-27  1-7 [00812] CF.sub.3 Me M-29  1-8 [00813] CF.sub.3 Me M-37  1-9 [00814] CF.sub.3 Me M-40  1-10 [00815] CF.sub.3 Me M-52  1-11 [00816] CF.sub.3 Me M-53  1-12 [00817] CF.sub.3 Me M-54  1-13 [00818] CF.sub.3 Me M-58  1-14 [00819] CF.sub.3 Me M-60  1-15 [00820] CF.sub.3 Me M-63  1-16 [00821] CF.sub.3 Me M-77  1-17 [00822] CF.sub.3 Me M-79  1-18 [00823] CF.sub.3 Me M-88  1-19 [00824] CF.sub.3 Me M-92  1-20 [00825] CF.sub.3 Me M-104 1-21 [00826] CF.sub.3 Me M-108 1-22 [00827] CF.sub.3 Me M-119 1-23 [00828] CF.sub.3 Me M-120 1-24 [00829] CF.sub.3 Me M-121 1-25 [00830] CF.sub.3 Me M-123 1-26 [00831] CF.sub.3 Me M-125 1-27 [00832] CF.sub.3 Me M-126 1-28 [00833] CF.sub.3 Me M-127 1-29 [00834] CF.sub.3 Me M-128 1-30 [00835] CF.sub.3 Me M-131 1-31 [00836] CF.sub.3 Me M-132 1-32 [00837] CF.sub.3 Me M-150 1-33 [00838] CF.sub.3 Me M-156 1-34 [00839] CF.sub.3 Me M-160 1-35 [00840] CF.sub.3 Me M-162 1-36 [00841] CF.sub.3 Me M-165 1-37 [00842] CF.sub.3 Me M-168 1-38 [00843] CF.sub.3 Me M-198 1-39 [00844] CF.sub.3 Me M-199 1-40 [00845] CF.sub.3 Me M-200 1-41 [00846] CF.sub.3 Me M-203 1-42 [00847] CF.sub.3 Me M-204 1-43 [00848] CF.sub.3 Me M-205 1-44 [00849] CF.sub.3 Me M-207 1-45 [00850] CF.sub.3 Me M-208 1-46 [00851] CF.sub.3 Me M-209 1-47 [00852] CF.sub.3 Me M-211 1-48 [00853] CF.sub.3 Me M-212 1-49 [00854] CF.sub.3 Me M-216 1-50 [00855] CF.sub.3 Me M-1  1-51 [00856] CF.sub.3 Me M-2  1-52 [00857] CF.sub.3 Me M-7  1-53 [00858] CF.sub.3 Me M-12  1-54 [00859] CF.sub.3 Me M-24  1-55 [00860] CF.sub.3 Me M-27  1-56 [00861] CF.sub.3 Me M-29  1-57 [00862] CF.sub.3 Me M-37  1-58 [00863] CF.sub.3 Me M-40  1-59 [00864] CF.sub.3 Me M-52  1-60 [00865] CF.sub.3 Me M-53  1-61 [00866] CF.sub.3 Me M-54  1-62 [00867] CF.sub.3 Me M-58  1-63 [00868] CF.sub.3 Me M-60  1-64 [00869] CF.sub.3 Me M-63  1-65 [00870] CF.sub.3 Me M-77  1-66 [00871] CF.sub.3 Me M-79  1-67 [00872] CF.sub.3 Me M-88  1-68 [00873] CF.sub.3 Me M-92  1-69 [00874] CF.sub.3 Me M-104 1-70 [00875] CF.sub.3 Me M-108 1-71 [00876] CF.sub.3 Me M-119 1-72 [00877] CF.sub.3 Me M-120 1-73 [00878] CF.sub.3 Me M-121 1-74 [00879] CF.sub.3 Me M-123 1-75 [00880] CF.sub.3 Me M-125 1-76 [00881] CF.sub.3 Me M-126 1-77 [00882] CF.sub.3 Me M-127 1-78 [00883] CF.sub.3 Me M-128 1-79 [00884] CF.sub.3 Me M-131 1-80 [00885] CF.sub.3 Me M-132 1-81 [00886] CF.sub.3 Me M-150 1-82 [00887] CF.sub.3 Me M-156 1-83 [00888] CF.sub.3 Me M-160 1-84 [00889] CF.sub.3 Me M-162 1-85 [00890] CF.sub.3 Me M-165 1-86 [00891] CF.sub.3 Me M-168 1-87 [00892] CF.sub.3 Me M-198 1-88 [00893] CF.sub.3 Me M-199 1-89 [00894] CF.sub.3 Me M-200 1-90 [00895] CF.sub.3 Me M-203 1-91 [00896] CF.sub.3 Me M-204 1-92 [00897] CF.sub.3 Me M-205 1-93 [00898] CF.sub.3 Me M-207 1-94 [00899] CF.sub.3 Me M-208 1-95 [00900] CF.sub.3 Me M-209 1-96 [00901] CF.sub.3 Me M-211 1-97 [00902] CF.sub.3 Me M-212 1-98 [00903] CF.sub.3 Me M-216 1-99 [00904] CF.sub.3 Me M-7  1-100 [00905] CF.sub.3 Me M-58  1-101 [00906] CF.sub.3 Me M-123 1-102 [00907] CF.sub.3 Me M-125 1-103 [00908] CF.sub.3 Me M-160 1-104 [00909] CF.sub.3 Me M-165 1-105 [00910] CF.sub.3 Me M-205 1-106 [00911] CF.sub.3 [00912] M-217 .sup.1H NMR (500 MHz, DMSO-d6) δ 9.04 (s, 1H), 8.36 (s, 1H), 7.96 (t, J = 59.0 Hz, 1H), 7.88 (s, 1H), 7.32 (d, J = 8.5 Hz, 2H), 6.98-6.93 (m, 2H), 5.50 (s, 2H), 3.74 (s, 3H), 2.96 (s, 6H).

[0111] The method for preparing the compound of the invention will be explained in detail in the following program and embodiment. The material is commercial available or prepared through known method reported in the literature or shown in the route. Those skilled in the art should understand that the compound of the invention can also be synthesized by other synthetic route. Although the detailed material and reaction condition in the synthetic route have been explicated in the following text, it is still easy to be replaced by other similar material and condition. Isomer of the compound, for example, that produced with the variation of the preparation method of the present invention is included in the scope of the present invention. In addition, the following preparation method can be further modified according to the disclosures of the present invention by using common chemical method known to those skilled in the art, for example, protection of suitable group in the process of the reaction, etc.

[0112] The following method of application can be used to improve further understanding of the preparation method of the present invention. The specific material, class and condition have been determined to be further explication of the present invention, not to be any limit of the reasonable scope thereof. Reagents of the following synthetic compound showed in the table can either be purchased from the market or easily prepared by those skilled in the art.

[0113] Examples of representative compounds are as follows, and the synthesis methods of other compounds are similar, and the detailed description is omitted here.

[0114] 1. Synthesis of Intermediate a

[0115] (1) Compound a-1 (1 g, 4.69 mmol), Compound a-2 (1.0 g, 7.0 mmol), and potassium carbonate (1.9 g, 14.0 mmol) were placed in the round bottom flask, added with 1,4-dioxane (10 mL)/water (2 mL) and then subjected to replacement with nitrogen for three times, added with Pd(dppf)Cl.sub.2CH.sub.2Cl.sub.2 (0.16 g) quickly and subjected to replacement with nitrogen for three times, then the reaction solution was subjected to replacement with nitrogen for three times again, and finally the reaction was carried out at 100° C. for 16 hours. The completion of the reaction was determined by HPLC, then the reaction system was concentrated, and separated by column chromatography to obtain 0.88 g (3.1 mmol, yield: 67%) of Compound a-3 (white solid).

[0116] (2) Compound a-3 (0.88 g, 3.1 mmol) was placed in the round bottom flask, added with 8 mL of water and sodium hydroxide (0.37 g, 9.3 mmol), and the reaction was carried out at 100° C. for 12 h. After the reaction, the temperature of the reaction system was reduced to room temperature. The reaction solution was extracted with 30 mL of dichloromethane for three times, the aqueous phase was adjusted to pH 2 with 1N HCl solution, and a white solid was precipitated. A filter cake was obtained by filtration, and then dried to obtain 0.65 g (2.4 mmol, yield 79%) of Compound a.

##STR00913##

[0117] 2. Synthesis of Compound 2

[0118] 1 g of Compound a was dissolved in 10 mL of CCl.sub.4, NCS (1.5 eq) and AIBN (0.05 eq) were added respectively. The temperature was raised to 70° C. for overnight reaction. The completion of the reaction was determined by LCMS. The post processing was: the reaction solution was concentrated to remove the solvent, the crude product was dispersed with water by stirring for 15 minutes, then a filter cake was obtained by filtration and dried to obtain Product 2 (0.75 g, yield: 67%).

##STR00914##

[0119] 3. Synthesis of Compound 3

[0120] 50 g (1.0 eq) of Compound a was placed into the reactor, added with 500 mL of AcOH/H.sub.2O (5:1) as a solvent, and added dropwise with Br.sub.2 (2.5 eq) at room temperature, then stirred overnight at room temperature. The completion of the reaction was determined by LCMS, the reaction solution was concentrated to obtain a solid, the solid was dispersed fully with water by stirring for half an hour, then a filter cake was obtained by filtration, and dried to obtain white solid 3 (55 g, yield: 83%).

##STR00915##

[0121] 4. Synthesis of Compound 4

[0122] 1 g of Compound a was dissolved in 10 mL of CCl.sub.4, NCS (1.5 eq) and AIBN (0.05 eq) were added respectively. The temperature was raised to 70° C. for overnight reaction. The completion of the reaction was determined by LCMS. The post processing was: the reaction solution was concentrated to remove the solvent, the crude product was dispersed with water by stirring for 15 minutes, a filter cake was obtained by filtration and dried to obtain Product 4 (0.8 g, yield: 59%).

##STR00916##

[0123] 5. Synthesis of Compound 5

[0124] 55 g of Compound 3 was added to 500 mL of MeCN, K.sub.2CO.sub.3 (2.5 eq) and b-1 (1.5 eq) were added. The temperature was raised to 70° C. for overnight reaction. The consumption of raw materials was detected by LCMS. The post processing was: the reaction solution was cooled and filtered, the mother liquor was concentrated, mixed and subjected to column chromatography to obtain Product b (41 g, yield: 57%).

##STR00917##

[0125] 0.6 g of Compound b (1 eq), 5-1 (1.5 eq), and K.sub.2CO.sub.3 (3 eq) were dissolved in dioxane/H.sub.2O=10:1 (6 mL), subjected to replacement with nitrogen for three times quickly, added with Pd(dppf)Cl.sub.2—CH.sub.2Cl.sub.2 (0.05 eq), then subjected to replacement with nitrogen for three times again. The temperature was raised to 120° C. for overnight reaction. The consumption of raw materials was detected by LCMS. The reaction solution was concentrated, mixed and subjected to column chromatography to obtain Product 5-2 (0.18 g, yield: 37.5%).

##STR00918##

[0126] 0.18 g of Compound 5-2 was dissolved in TFA (2.0 mL). The temperature was raised to 50° C. for overnight reaction. The completion of the reaction was determined by LCMS. The reaction solution was concentrated, dispersed with water by stirring, and filtered to obtain a filter cake, and the filter cake was dissolved in DMSO, and Product 5 (0.075 g, yield: 59.7%) was obtained by Preparative reversed-phase HPLC.

##STR00919##

[0127] 6. Synthesis of Compound 8

[0128] 0.6 g of Compound b (1 eq), CuCN (1.5 eq), and NiBr (0.1 eq) were dissolved in NMP (6 mL) and reacted under microwave condition at 140° C. for 3 hours. The consumption of raw materials was detected, then the reaction solution was filtered, and Product 8-1 (0.13 g, yield: 25%) was obtained from the mother liquor through Preparative reversed-phase HPLC.

##STR00920##

[0129] 0.13 g of Compound 8-1 was dissolved in TFA (2 mL), heated to 50° C. for overnight reaction. The completion of the reaction was determined by LCMS, then the reaction solution was concentrated, dispersed with water by stirring, then filtered to obtain a filter cake. The filter cake was dissolved in DMSO, and Product 8 (0.08 g, yield: 87%) was obtained by Preparative reversed-phase HPLC.

##STR00921##

[0130] 7. Synthesis of Compound 12

[0131] (1) 1 equivalent of Compound b was dissolved in 5 volumes of methanol, then 10 equivalents of sodium methoxide solution was added, the temperature was raised to 60° C. and reacted for 3 hours. After the completion of the In-Process Control, the temperature was reduced, the methanol in the reaction solution was removed by rotary-evaporation, 5 volumes of water was added, extracted twice with 10 volumes of ethyl acetate, the organic phases were combined and Product 12-1 was obtained with a yield of 89% by rotary evaporation of the organic phase.

[0132] (2) The obtained Product 12-1 was dissolved in 5 volumes of trifluoroacetic acid, the temperature was raised to 50° C. for 10 hours' reaction. After the completion of the In-Process Control, the temperature was reduced to room temperature, the trifluoroacetic acid in the system was removed by vacuum, then 5 volumes of water was added dropwise to the system slowly, stirred continually for 15 minutes after a solid precipitation appeared, filtered to obtain a solid, and the solid was dried to obtain Product 12 with a yield of 78%.

##STR00922##

[0133] 8. Synthesis of Compound 16

[0134] (1) 1 equivalent of Compound b was dissolved in 10 volumes of dioxane solution, 1.5 equivalents of p-methoxybenzylamine, 2.0 equivalents of cesium carbonate and 0.05 equivalents of BINAP were added, then subjected to replacement with nitrogen for three times, added with 5% mass of Pd.sub.2(dba).sub.3, heated to 120° C. under nitrogen protection and reacted for 16 hours at 120° C., finally the reaction was terminated after the completion of the In-Process Control. The temperature was reduced to room temperature, the reaction solution was filtered to remove the insoluble solids, the dioxane solution was removed by vacuum, then 5 volumes of water was added, extracted twice with 10 volumes of ethyl acetate, the organic phases were combined, rotary-evaporated, mixed with silica gel, and purified by column chromatography to obtain Product 16-1 with a yield of 62%.

[0135] (2) The obtained Product 16-1 was dissolved in 5 volumes of trifluoroacetic acid, the temperature was raised to 50° C. and reacted for 5 hours. After the completion of the In-Process Control, the temperature was reduced to room temperature. Trifluoroacetic acid in the system was removed by vacuum, and 5 volumes of water was added dropwise to the system slowly, stirred continually for 20 minutes after a solid precipitation appeared, then filtered to obtain a solid, the solid was purified by Preparative reversed-phase HPLC to obtain Product 16 with a yield of 80%.

##STR00923##

[0136] 9. Synthesis of Compound 25

[0137] (1) Compound 25-1 was prepared by referring to the synthetic method of compound b, then 1 equivalent of Compound 25-1 was dissolved in 10 volumes of dioxane solution, 2.0 equivalents of pyrazole was added, then 3.0 equivalents of N,N-Diisopropylethylamine and 0.05 equivalents of Xantphos were added. The above reaction system was subjected to replacement with nitrogen for three times, then added with 5% mass Pd.sub.2(dba).sub.3, heated to 120° C. under nitrogen protection and reacted for 20 hours at 120° C., finally the reaction was terminated after the completion of the In-Process Control. The temperature was reduced to room temperature, the insoluble solids in the reaction solution were removed by filtration, the dioxane solution was removed by vacuum, 5 volumes of water was added, extracted twice with 10 volumes of ethyl acetate, the organic phases were combined, rotary-evaporated, mixed with silica gel, and purified by column chromatography to obtain Product 25-2 with a yield of 54%.

[0138] (2) The obtained Product 25-2 was dissolved in 5 volumes of trifluoroacetic acid, the temperature was raised to 50° C. and reacted for 16 hours. After the completion of the In-Process Control, the temperature was reduced to room temperature. Trifluoroacetic acid in the system was removed by vacuum, and 5 volumes of water was added dropwise to the system slowly, stirred continually for 30 minutes after a solid precipitation appeared, then filtered to obtain a solid, and the solid was purified by Preparative reversed-phase HPLC to obtain Product 25 with a yield of 85%.

##STR00924##

[0139] 10. Synthesis of Compound 27

[0140] 0.6 g of compound b (1 eq), DIPEA (3 eq), Xantphos (0.05 eq) and Pd.sub.2(dba).sub.3 (0.05 eq) were dissolved in dioxane (6 mL), subjected to replacement with nitrogen for three times, then added with compound 27-1 (2 eq) quickly, heated to 120° C. for overnight reaction. After the completion of the reaction was determined, the reaction solution was concentrated, mixed with silica gel, and subjected to column chromatography to obtain Product 27-2 (0.32 g, yield: 59%).

##STR00925##

[0141] 0.32 g of Product 27-2 was dissolved in TFA (4 mL), heated to 50° C. for overnight reaction. After the completion of the reaction was determined by LCMS, the reaction solution was concentrated, dispersed with water by stirring, filtered to obtain a filter cake, and the filter cake was dissolved in DMSO. Product 27 (0.13 g, yield: 56%) was obtained by Preparative reversed-phase HPLC.

##STR00926##

[0142] 11. Synthesis of Compound 31

[0143] 0.6 g of Compound b (1 eq), 31-1 (1.5 eq) and K.sub.2CO.sub.3 (3 eq) were dissolved in dioxane/H.sub.2O=5:1 (6 mL), and subjected to replacement with nitrogen for three times quickly, added with Pd(dppf)Cl.sub.2—CH.sub.2Cl.sub.2 (0.05 eq), then the reaction solution was subjected to replacement with nitrogen for three times again, and finally heated to 120° C. for overnight reaction. The consumption of raw materials was detected by LCMS, the reaction solution was concentrated, mixed with silica gel, and subjected to column chromatography to obtain Product 31-2 (0.42 g, yield: 92%).

##STR00927##

[0144] 0.42 g of Compound 31-2 was dissolved in TFA (5 mL), heated to 50° C. for overnight reaction. After the completion of the reaction was determined by LCMS, the reaction solution was concentrated, dispersed with water by stirring, filtered to obtain a filter cake, and the filter cake was dissolved in DMSO, Product 31 (0.31 g, yield: 78%) was obtained by Preparative reversed-phase HPLC.

##STR00928##

[0145] 12. Synthesis of Intermediate c

[0146] Raw material c-1 was added to 10 volumes of DMF, c-2 (1.5 eq) and cesium carbonate (2 eq) were added, the temperature was raised to 120° C. for 2 hours' reaction, and C02 was generated during the reaction. After the completion of the reaction was determined by HPLC, the temperature was reduced to room temperature, cesium carbonate was removed by filtration, and the mother liquor was used directly in the next step.

##STR00929##

[0147] Bis(pinacolato)diboron (1.2 eq) and potassium acetate (1.5 eq) were added to the mother liquor of the previous step, subjected to replacement with nitrogen, then palladium catalyst (5%) was added under nitrogens protection, the temperature was raised to 100° C. and reacted for 16 hours. After the completion of the reaction was determined by HPLC, the temperature was reduced to room temperature, and the reaction solution was used directly in the next step.

##STR00930##

[0148] 1 volume of water was added to the reaction solution of the previous step, then intermediate c-5 and potassium carbonate (3 eq) were added, subjected to replacement of nitrogen, then palladium catalyst (5%) was added under nitrogen protection, the temperature was raised to 120° C. and reacted for 18 hours. After the completion of the reaction was determined by HPLC, 20 volumes of water was added to the reaction solution, extracted with ethyl acetate until no product was present in the aqueous phase, the organic phase was concentrated, mixed with silica gel, and purified by column chromatography (petroleum ether:ethyl acetate=5:1) to obtain Product c-6.

##STR00931##

[0149] Compound c-6 was dissolved in 10 volumes of DMSO, potassium acetate (5 eq) was added, then the reaction system was raised to 120° C. and reacted for 16 hours. After the completion of the reaction was determined by HPLC, the temperature was reduced to room temperature, then 20 volumes of water was poured, extracted three times with DCM, the aqueous phase was adjusted to pH=4 with 1M hydrochloric acid, a large amount of solids were precipitated, and the reaction system was stirred continually for 30 minutes, filtered to give a filter cake, and the filter cake was dried to obtain Product c.

##STR00932##

[0150] 13. Synthesis of Compound 46

[0151] 1 g of Compound c was dissolved in 10 mL of CCl.sub.4, NBS (1.5 eq) and AIBN (0.05 eq) were added respectively. The temperature was raised to 80° C. for overnight reaction. The completion of the reaction was determined by LCMS. The post processing was: the reaction solution was concentrated to remove the solvent, the crude product was dispersed with water by stirring for 15 minutes, a filter cake was obtained by filtration and dried to obtain Product 46 (1 g, yield: 78%).

##STR00933##

[0152] 14. Synthesis of Compound 48

[0153] 10 g of Compound 46 was added to 500 mL of MeCN, K.sub.2CO.sub.3 (2.5 eq) and b-1 (1.5 eq) were added and the temperature was raised to 70° C. for overnight reaction. The consumption of raw materials was detected by LCMS. The post processing was: the temperature of the reaction solution was reduced, the reaction solution was filtered to obtain a mother liquor, and the mother liquor was concentrated, mixed with silica gel, and subjected to column chromatography to obtain Product d (9.8 g, yield: 73%).

##STR00934##

[0154] 0.6 g of Compound d (1 eq), 48-1 (1.5 eq) and NaOH (3 eq) were dissolved in dioxane/H.sub.2O=10:1 (6 mL), subjected to replacement with nitrogen for three times quickly, then added with Pd(dppf)Cl.sub.2—CH.sub.2Cl.sub.2 (0.05 eq), and the reaction solution was subjected to replacement with nitrogen for three times again, finally heated to 120° C. and reacted for 24 hours. The consumption of raw materials was detected by LCMS, the reaction solution was concentrated, mixed with silica gel, and subjected to column chromatography to obtain Product 48-2 (0.2 g, yield: 38.6%).

##STR00935##

[0155] 0.2 g of Compound 48-2 was dissolved in TFA (2 mL), heated to 50° C. for overnight reaction. The completion of the reaction was determined by LCMS, then the reaction solution was concentrated, dispersed with water by stirring, filtered to obtain a filter cake, and the filter cake was dissolved in DMSO, Product 48 (0.08 g, yield: 57%) was obtained by Preparative reversed-phase HPLC.

##STR00936##

[0156] Evaluation of Biological Activity:

[0157] The activity level standard of plant destruction (i.e. growth inhibition rate) is as follows:

[0158] Level 5: growth control rate is above 85%;

[0159] Level 4: growth control rate is greater than or equal to 60% and less than 85%;

[0160] Level 3: growth control rate is greater than or equal to 40% and less than 60%;

[0161] Level 2: growth control rate is greater than or equal to 20% and less than 40%;

[0162] Level 1: growth control rate is greater than or equal to 5% and less than 20%;

[0163] Level 0: growth control rate is less than 5%.

[0164] The above described growth inhibition rates are fresh weight inhibition rates.

[0165] Experiment of post-emergence test: monocotyledonous and dicotyledonous weed seeds as well as main crop seeds (i.e., wheat, corn, rice, soybean, cotton, oilseed rape, millet and sorghum) were put into a plastic pot loaded with soil, then covered with 0.5-2 cm of soil, and the seeds were allowed to grow in good greenhouse environment. The test plants were treated at 2-3 leaf stage 2-3 weeks after sowing. The test compounds of the invention were dissolved in acetone respectively, then added with Tween-80 and diluted by a certain amount of water to give solutions with certain concentrations, and added with 80% vegetable oil methyl ester synergist at 1500 g/ha. The solution was sprayed to the plants with a sprayer. The plants were cultured in the greenhouse. The experiment results of weed controlling effect after 3 weeks were listed in Table 4.

TABLE-US-00004 TABLE 4 Experiment on weed control effect of compounds of Formula I in Post-emergence stage (1200 g/ha) Compound Descurainia Capsella Sinapis NO. sophia bursa-pastoris arvensis 5 5 5 5 6 5 5 5 7 5 5 5 9 5 5 5 10 5 5 5 12 5 4 5 16 4 4 4 17 4 3 4 18 3 3 4 45 5 5 5 46 5 3 5 47 5 N 5 48 5 5 5 49 5 5 5 50 5 5 5 52 3 3 5 53 5 5 5 59 5 5 5 60 N N 3 70 N 3 5 87 5 5 5 88 5 5 5 89 5 5 5 90 5 5 5 91 5 5 5 92 5 5 5 93 5 5 5 94 5 5 5 95 5 5 5 96 5 5 5 97 5 5 5 98 5 5 5 99 5 5 5 109 5 5 5 110 5 5 5 111 5 5 5 112 5 5 5 113 5 5 5 114 5 5 5 115 5 5 5 116 5 5 5 117 5 5 5 118 5 5 5 119 5 5 5 120 5 5 5 121 5 5 5 122 5 5 5 123 5 5 5 124 5 5 5 125 5 5 5 126 5 5 5 132 5 5 5 133 5 5 5 134 5 5 5 135 5 5 5 136 5 5 5 137 5 5 5 138 3 3 5 156 5 5 5 157 5 5 5 158 5 5 5 159 5 5 5 160 5 5 5 161 5 5 5 162 5 5 5 163 5 5 5 164 5 5 5 165 5 5 5 166 5 5 5 167 5 5 5 168 5 5 5 169 5 5 5 171 5 5 5 172 5 5 5 173 5 5 5 228 5 5 5 301 5 3 5 313 5 5 5 334 5 5 5 388 4 3 5 389 N 3 5 393 N N 3 395 N N 3 399 5 5 5 400 5 5 5 401 5 4 5 402 5 5 5 403 3 5 5 404 5 5 5 406 N N 5 407 5 5 5 408 N N 5 409 3 3 5 410 5 3 5 411 N 3 5 412 N 3 5 414 3 N 5 Note: N means no data.

[0166] Experiment of Pre-Emergence Test:

[0167] Seeds of monocotyledonous and dicotyledonous weeds and main crops (e.g. wheat, corn, rice, soybean, cotton, oilseed rape, millet and sorghum) were put into a plastic pot loaded with soil and covered with 0.5-2 cm of soil. The test compounds of the present invention was dissolved with acetone, then added with Tween-80, diluted by a certain amount of water to reach a certain concentration, and sprayed immediately after sowing. The obtained seeds were incubated for 4 weeks in the greenhouse after spraying and the test results were observed. It was observed that the herbicides of the present invention mostly had excellent effect at dose of 250 g/ha, especially to weeds such as Echinochloa crusgalli, Digitaria sanguinalis and Abutilon theophrasti, etc., and many compounds had good selectivity for corn, wheat, rice, soybean, oilseed rape, etc.

[0168] It is found in the experiment that the compounds of the present invention generally have good weed control efficacy, especially for major broadleaf weeds such as Abutilon theophrasti and Bidens bipinnata, etc., which are widely occurred in corn, rice and wheat fields, and have excellent commercial value. Above all, it is noted that the compound of the invention have extremely high activity to broadleaf weeds, which are resistant to ALS inhibitor, like Lithospermum arvense, Galium spurium and Stellaria media, etc.

[0169] Transplanted rice safety evaluation and weed control effect evaluation in rice field:

[0170] Rice field soil was loaded into a 1/1,000,000 ha pot. The seeds of Echinochloa crusgalli, Scirpus juncoides and Bidens tripartite were sowed and gently covered with soil, then left to stand still in greenhouse in the state of 0.5-1 cm of water storage. The tuber of Sagittaria trifolia L. was planted in the next day or 2 days later. It was kept at 3-4 cm of water storage thereafter. The weeds were treated by dripping the WP or SC water diluents prepared according to the common preparation method of the compounds of the present invention with pipette homogeneously to achieve specified effective amount when Echinochloa crusgalli, Scirpus juncoides and Bidens tripartite reached 0.5 leaf stage and Sagittaria trifolia L. reached the time point of primary leaf stage.

[0171] In addition, the rice field soil that loaded into the 1/1,000,000 ha pot was leveled to keep water storage at 3-4 cm depth. The 3 leaf stage rice (japonica rice) was transplanted at 3 cm of transplanting depth the next day. The compound of the present invention was treated by the same way after 5 days of transplantation.

[0172] The fertility condition of Echinochloa crusgalli, Scirpus juncoides, Bidens tripartite and Sagittaria trifolia L. 14 days after the treatment of the compound of the invention and the fertility condition of rice 21 days after the treatment of the compound of the invention respectively with the naked eye. Evaluate the weed control effect with 0-5 activity standard level. It has been found that many of the compounds of the present invention have excellent activity and selectivity.

[0173] Note: The seeds of Echinochloa crusgalli, Scirpus juncoides and Bidens tripartite were collected from Heilongjiang Province of China. Tests indicated that the weeds were resistant to common rate of pyrazosulfuron-ethyl.

[0174] At the same time, the compounds and the compositions of the present invention have good selectivity to many gramineae grasses such as Zoysia japonica, bermuda grass, tall fescue, bluegrass, ryegrass and seashore paspalum, etc., and are able to control many important grass weeds and broadleaf weeds. The compounds also show excellent selectivity and commercial value in the tests on wheat, corn, rice, sorghum, millet, sugarcane, soybean, cotton, oil sunflower, potato, fruit trees, and vegetables in different herbicide application methods (such as pre-emergence and post-emergence).