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, OSO.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 CHCHCHCH 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, OSO.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 CHCHCHCH 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, OSO.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 CHCHCHCH 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: TABLE-US-00005 TABLE 1 I NO. X Y Z 1 CF.sub.3 F 2 CF.sub.3 Cl 3 CF.sub.3 Br 4 CF.sub.3 I 5 CF.sub.3 Me 6 CF.sub.3 Et 7 CF.sub.3 8 CF.sub.3 CN 9 CF.sub.3 10 CF.sub.3 11 CF.sub.3 12 CF.sub.3 OMe 13 CF.sub.3 OEt 14 CF.sub.3 15 CF.sub.3 OH 16 CF.sub.3 NH.sub.2 17 CF.sub.3 NHMe 18 CF.sub.3 N(Me).sub.2 19 CF.sub.3 20 CF.sub.3 21 CF.sub.3 22 CF.sub.3 23 CF.sub.3 24 CF.sub.3 25 CF.sub.3 26 CF.sub.3 SMe 27 CF.sub.3 SEt 28 CF.sub.3 SOEt 29 CF.sub.3 SO.sub.2Et 30 CF.sub.3 Ph 31 CF.sub.3 32 CF.sub.3 33 CF.sub.3 34 CF.sub.3 35 CF.sub.3 36 CF.sub.3 37 CF.sub.3 38 CF.sub.3 39 CF.sub.3 40 CF.sub.3 41 CF.sub.3 42 CF.sub.3 43 CF.sub.3 44 CF.sub.3 F 45 CF.sub.3 Cl 46 CF.sub.3 Br 47 CF.sub.3 I 48 CF.sub.3 Me 49 CF.sub.3 Et 50 CF.sub.3 51 CF.sub.3 CN 52 CF.sub.3 53 CF.sub.3 54 CF.sub.3 55 CF.sub.3 OMe 56 CF.sub.3 OEt 57 CF.sub.3 58 CF.sub.3 OH 59 CF.sub.3 NH.sub.2 60 CF.sub.3 NHMe 61 CF.sub.3 N(Me).sub.2 62 CF.sub.3 63 CF.sub.3 64 CF.sub.3 65 CF.sub.3 66 CF.sub.3 67 CF.sub.3 68 CF.sub.3 69 CF.sub.3 SMe 70 CF.sub.3 SEt 71 CF.sub.3 SOEt 72 CF.sub.3 SO.sub.2Et 73 CF.sub.3 Ph 74 CF.sub.3 75 CF.sub.3 76 CF.sub.3 77 CF.sub.3 78 CF.sub.3 79 CF.sub.3 80 CF.sub.3 81 CF.sub.3 82 CF.sub.3 83 CF.sub.3 84 CF.sub.3 85 CF.sub.3 86 CF.sub.3 87 CF.sub.3 Me 88 CF.sub.3 Me 89 CF.sub.3 Me 90 CF.sub.3 Me 91 CF.sub.3 Me 92 CF.sub.3 Me 93 CF.sub.3 Me 94 CF.sub.3 Me 95 CF.sub.3 Me 96 CF.sub.3 Me 97 CF.sub.3 Me 98 CF.sub.3 Me 99 CF.sub.3 Me 100 CF.sub.3 Me 101 CF.sub.3 Me 102 CF.sub.3 Me 103 CF.sub.3 Me 104 CF.sub.3 Me 105 CF.sub.3 Me 106 CF.sub.3 Me 107 CF.sub.3 Me 108 CF.sub.3 Me 109 CF.sub.3 Me 110 CF.sub.3 Me 111 CF.sub.3 Me 112 CF.sub.3 Me 113 CF.sub.3 Me 114 CF.sub.3 Me 115 CF.sub.3 116 CF.sub.3 117 CF.sub.3 118 CF.sub.3 119 CF.sub.3 120 CF.sub.3 121 CF.sub.3 122 CF.sub.3 123 CF.sub.3 124 CF.sub.3 125 CF.sub.3 126 CF.sub.3 127 CF.sub.3 128 CF.sub.3 129 CF.sub.3 130 CF.sub.3 131 CF.sub.3 132 CF.sub.3 133 CF.sub.3 134 CF.sub.3 135 CF.sub.3 136 CF.sub.3 137 CF.sub.3 138 CF.sub.3 SEt 139 CF.sub.3 SEt 140 CF.sub.3 SEt 141 CF.sub.3 SEt 142 CF.sub.3 SEt 143 CF.sub.3 SEt 144 CF.sub.3 SEt 145 CF.sub.3 SEt 146 CF.sub.3 SEt 147 CF.sub.3 SEt 148 CF.sub.3 SEt 149 CF.sub.3 SEt 150 CF.sub.3 SEt 151 CF.sub.3 SEt 152 CF.sub.3 SEt 153 CF.sub.3 SEt 154 CF.sub.3 SEt 155 CF.sub.3 SEt 156 CF.sub.3 157 CF.sub.3 158 CF.sub.3 159 CF.sub.3 160 CF.sub.3 161 CF.sub.3 162 CF.sub.3 163 CF.sub.3 164 CF.sub.3 165 CF.sub.3 166 CF.sub.3 167 CF.sub.3 168 CF.sub.3 169 CF.sub.3 170 CF.sub.3 171 CF.sub.3 172 CF.sub.3 173 CF.sub.3 174 CF.sub.3 NH.sub.2 175 CF.sub.3 NH.sub.2 176 CF.sub.3 NH.sub.2 177 CF.sub.3 NH.sub.2 178 CF.sub.3 NH.sub.2 179 CF.sub.3 NH.sub.2 180 CF.sub.3 NH.sub.2 181 CF.sub.3 NH.sub.2 182 CF.sub.3 NH.sub.2 183 CF.sub.3 NH.sub.2 184 CF.sub.3 NH.sub.2 185 CF.sub.3 NH.sub.2 186 CF.sub.3 NH.sub.2 187 CF.sub.3 NH.sub.2 188 CF.sub.3 NH.sub.2 189 CF.sub.3 NH.sub.2 190 CF.sub.3 NH.sub.2 191 CF.sub.3 NH.sub.2 192 CF.sub.3 NHMe 193 CF.sub.3 NHMe 194 CF.sub.3 NHMe 195 CF.sub.3 NHMe 196 CF.sub.3 NHMe 197 CF.sub.3 NHMe 198 CF.sub.3 NHMe 199 CF.sub.3 NHMe 200 CF.sub.3 NHMe 201 CF.sub.3 NHMe 202 CF.sub.3 NHMe 203 CF.sub.3 NHMe 204 CF.sub.3 NHMe 205 CF.sub.3 NHMe 206 CF.sub.3 NHMe 207 CF.sub.3 NHMe 208 CF.sub.3 NHMe 209 CF.sub.3 NHMe 210 CF.sub.3 211 CF.sub.3 212 CF.sub.3 213 CF.sub.3 214 CF.sub.3 215 CF.sub.3 216 CF.sub.3 217 CF.sub.3 218 CF.sub.3 219 CF.sub.3 220 CF.sub.3 221 CF.sub.3 222 CF.sub.3 223 CF.sub.3 224 CF.sub.3 225 CF.sub.3 226 CF.sub.3 227 CF.sub.3 228 CF.sub.2CF.sub.3 Me 229 CF.sub.2CF.sub.3 Me 230 CF.sub.3 Me 231 CF.sub.3 Me 232 CF.sub.3 Me 233 CF.sub.3 Me 234 CF.sub.3 Me 235 CF.sub.3 Me 236 CF.sub.3 Me 237 CF.sub.3 Me 238 CF.sub.3 Me 239 CF.sub.3 Me 240 CF.sub.3 Me 241 CF.sub.3 Me 242 CF.sub.3 Me 243 CF.sub.3 Me 244 CF.sub.3 Me 245 CF.sub.3 Me 246 CF.sub.3 Me 247 CF.sub.3 Me 248 CF.sub.3 Me 249 CF.sub.3 Me 250 CF.sub.3 Me 251 CF.sub.3 Me 252 CF.sub.3 Me 253 CF.sub.3 Me 254 CF.sub.3 Me 255 CF.sub.3 Me 256 CF.sub.3 Me 257 CF.sub.3 Me 258 CF.sub.3 Me 259 CF.sub.3 Me 260 CF.sub.3 Me 261 CF.sub.3 Me 262 CF.sub.3 Me 263 CF.sub.3 Me 264 CF.sub.3 Me 265 CF.sub.3 Me 266 CF.sub.3 Me 267 CF.sub.3 Me 268 CF.sub.3 Me 269 CF.sub.3 Me 270 CF.sub.3 Me 271 CF.sub.3 Me 272 CF.sub.3 Me 273 CF.sub.3 Me 274 CF.sub.3 Me 275 CF.sub.3 Me 276 CF.sub.3 Me 277 CF.sub.3 Me 278 CF.sub.3 Me 279 CF.sub.3 Me 280 CF.sub.3 Me 281 CF.sub.3 Me 282 CF.sub.3 Me 283 CF.sub.3 Me 284 CF.sub.3 Me 285 CF.sub.3 Me 286 CF.sub.3 Me 287 CF.sub.3 Me 288 CF.sub.3 Me 289 CF.sub.3 Me 290 CF.sub.3 Me 291 CF.sub.3 Me 292 CF.sub.3 Me 293 CF.sub.3 Me 294 CF.sub.3 Me 295 CF.sub.3 Me 296 CF.sub.3 Me 297 CF.sub.3 Me 298 CF.sub.3 Me 299 CF.sub.3 Me 300 CF.sub.3 Me 301 CF.sub.3 Me 302 CF.sub.3 Me 303 CF.sub.3 Me 304 CF.sub.3 Me 305 CF.sub.3 Me 306 CF.sub.3 Me 307 CF.sub.3 Me 308 CF.sub.3 Me 309 CF.sub.3 Me 310 CF.sub.3 Me 311 CF.sub.3 Me 312 CF.sub.3 Me 313 CF.sub.3 Me 314 CF.sub.3 Me 315 CF.sub.3 Me 316 CF.sub.3 Me 317 CF.sub.3 Me 318 CF.sub.3 Me 319 CF.sub.3 Me 320 CF.sub.3 Me 321 CF.sub.3 Me 322 CF.sub.3 Me 323 CF.sub.3 Me 324 CF.sub.3 Me 325 CF.sub.3 Me 326 CF.sub.3 Me 327 CF.sub.3 Me 328 CF.sub.3 Me 329 CF.sub.3 Me 330 CF.sub.3 Me 331 CF.sub.3 Me 332 CF.sub.3 Me 333 CF.sub.3 Me 334 CF.sub.3 Me 335 CF.sub.3 Me 336 CF.sub.3 Me 337 CF.sub.3 Me 338 CF.sub.3 Me 339 CF.sub.3 Me 340 CF.sub.3 Me 341 CF.sub.3 Me 342 CF.sub.3 Me 343 CF.sub.3 Me 344 CF.sub.3 Me 345 CF.sub.3 Me 346 CF.sub.3 Me 347 CF.sub.3 Me 348 CF.sub.3 Me 349 CF.sub.3 Me 350 CF.sub.3 Me 351 CF.sub.3 Me 352 CF.sub.3 Me 353 CF.sub.3 Me 354 CF.sub.3 Me 355 CF.sub.3 Me 356 CF.sub.3 Me 357 CF.sub.3 Me 358 CF.sub.3 Me 359 CF.sub.3 Me 360 CF.sub.3 Me 361 CF.sub.3 Me 362 CF.sub.3 Me 363 CF.sub.3 Me 364 CF.sub.3 Me 365 CF.sub.3 Me 366 CF.sub.3 Me 367 CF.sub.3 Me 368 CF.sub.3 Me 369 CF.sub.3 Me 370 CF.sub.3 Me 371 CF.sub.3 Me 372 CF.sub.3 Me 373 CF.sub.3 Me 374 CF.sub.3 Me 375 CF.sub.3 Me 376 CF.sub.3 Me 377 CF.sub.3 Me 378 CF.sub.3 Me 379 CF.sub.3 Me 380 CF.sub.3 Me 381 CF.sub.3 Me 382 CF.sub.3 Me 383 CF.sub.3 Me 384 CF.sub.3 Me 385 CF.sub.3 Me 386 CF.sub.3 Me 387 CF.sub.3 Me 388 CF.sub.3 CHF.sub.2 389 CF CF.sub.3 390 CF.sub.3 CHO 391 CF.sub.3 392 CF.sub.3 393 CF.sub.3 394 CF.sub.3 395 CF.sub.3 396 CF.sub.3 397 CF.sub.3 F 398 CF.sub.3 399 CF.sub.3 Me 400 CF.sub.3 401 CF.sub.3 402 CF.sub.3 403 CF.sub.3 404 CF.sub.3 405 CF.sub.3 406 CF.sub.3 407 CF.sub.3 408 CF.sub.3 Me 409 CF.sub.3 410 CF.sub.3 411 CF.sub.3 412 CF.sub.3 413 CF.sub.3 414 CF.sub.3 Br.

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: ##STR01490## 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, and (iii) an agriculturally acceptable formulation auxiliary.

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. 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 useful crop, wherein the useful crop is a transgenic crop or a crop treated by gene editing technique.

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. 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.

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

(1) 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.

(2) 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.

(3) TABLE-US-00001 TABLE 1 Structures and .sup.1HNMR data of Compounds I NO. X Y Z .sup.1HNMR 1 CF.sub.3 F .sup.1H NMR (500 MHz, DMSO-d.sub.6) 14.50 (s, 1H), 7.97 (d, J = 7.5 Hz, 2H), 7.77 (d, J = 1.5 Hz, 2H). 2 CF.sub.3 Cl .sup.1H NMR (500 MHz, DMSO-d.sub.6 14.42 (s, 1H), 8.25 (d, J = 7.5 Hz, 2H), 7.75 (d, J = 7.5 Hz, 2H). 3 0 CF.sub.3 Br .sup.1H NMR (500 MHz, DMSO-d.sub.6) 14.45 (s, 1H), 8.20 (d, J = 8.0 Hz, 2H), 7.94 (d, J = 8.0 Hz, 2H). 4 CF.sub.3 I .sup.1H NMR (500 MHz, DMSO-d.sub.6) 14.42 (s, 1H), 8.25 (d, J = 8.0 Hz, 2H), 7.95 (d, J = 8.0 Hz, 2H). 5 CF.sub.3 Me .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 CF.sub.3 Et .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 CF.sub.3 CN .sup.1H NMR (500 MHz, DMSO-d.sub.6) 14.42 (s, 1H), 8.25 (d, J = 8.0 Hz, 2H), 7.85 (d, J = 8.0 Hz, 2H). 9 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 CF.sub.3 0 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 CF.sub.3 OMe .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 CF.sub.3 OEt .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 CF.sub.3 OH .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 CF.sub.3 NH.sub.2 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 CF.sub.3 NHMe .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 0 CF.sub.3 N(Me).sub.2 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d.sub.6) Hz, 2H), 7.96 (d, J = 8.0 Hz, 2H), 2.95 (s, 6H) 21 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 CF.sub.3 0 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 CF.sub.3 SMe .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 CF.sub.3 SEt .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 CF.sub.3 SOEt .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 CF.sub.3 SO.sub.2Et .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 CF.sub.3 Ph .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 0 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 00 CF.sub.3 01 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 02 CF.sub.3 03 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 04 CF.sub.3 05 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 06 CF.sub.3 07 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 08 CF.sub.3 09 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 0 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 CF.sub.3 F .sup.1H NMR (500 MHz, DMSO-d.sub.6) 14.49 (s, 1H), 7.96-7.68 (m, 2H), 7.09 (s, 1H). 45 CF.sub.3 Cl .sup.1H NMR (500 MHz. DMSO-d.sub.6) 14.42 (s, 1H), 9.20 (s, 1H), 8.48 (s, 1H), 7.97 (t, J = 58.5 Hz, 1H). 46 CF.sub.3 Br .sup.1H NMR (500 MHz, DMSO-d.sub.6) 14.42 (s, 1H), 9.20 (s, 1H), 8.47 (s, 1H), 7.96 (t, J = 58.5 Hz, 1H). 47 CF.sub.3 I .sup.1H NMR (500 MHz, DMSO-d.sub.6) 14.42 (s, 1H), 9.18 (s, 1H), 8.44 (s, 1H), 7.95 (t, J = 58.5 Hz, 1H). 48 0 CF.sub.3 Me .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 CF.sub.3 Et .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 CF.sub.3 CN .sup.1H NMR (500 MHz, DMSO-d6) 14.49 (s, 1H), 9.12 (s, 1H), 8.41 (s, 1H), 7.94 (t, J = 58.5 Hz, 1H). 52 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d6) 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 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 CF.sub.3 0 .sup.1H NMR (500 MHz, DMSO-d6) 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 CF.sub.3 OMe .sup.1H NMR (500 MHz, DMSO-d6) 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 CF.sub.3 OEt .sup.1H NMR (500 MHz, DMSO-d6) 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 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d6) 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 CF.sub.3 OH .sup.1H NMR (500 MHz, DMSO-d6) 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 CF.sub.3 NH.sub.2 .sup.1H NMR (500 MHz, DMSO-d6) 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 CF.sub.3 NHMe .sup.1H NMR (500 MHz, DMSO-d6) 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 CF.sub.3 N(Me).sub.2 .sup.1H NMR (500 MHz, DMSO-d6) 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 CF.sub.3 0 .sup.1H NMR (500 MHz, DMSO-d6) 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 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d6) 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 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d6) 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 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d6) 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 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d6) 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 CF.sub.3 0 .sup.1H NMR (500 MHz, DMSO-d6) 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 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d6) 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 CF.sub.3 SMe .sup.1H NMR (500 MHz, DMSO-d6) 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 CF.sub.3 SEt .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 CF.sub.3 SOEt .sup.1H NMR (500 MHz, DMSO-d6) 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 CF.sub.3 SO.sub.2Et .sup.1H NMR (500 MHz, DMSOd6) 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 CF.sub.3 Ph .sup.1H NMR (500 MHz, DMSO-d6) 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 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d6) 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 0 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d6) 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 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d6) 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 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d6) 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 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d6) 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 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d6) 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 0 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d6) 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 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d6) 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 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d6) 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 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d6) 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 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d6) 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 0 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d6) 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 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d6) 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 CF.sub.3 Me .sup.1H NMR (500 MHz, DMSO-d6) 14.45 (s, 1H), 7.97-7.91 (m, 2H), 7.38-7.28 (m, 2H), 2.16 (s, 3H). 88 CF.sub.3 Me .sup.1H NMR (500 MHz, DMSO-d6) 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 CF.sub.3 Me .sup.1H NMR (500 MHz, DMSO-d6) 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 CF.sub.3 Me .sup.1H NMR (500 MHz, DMSO-d6) 14.49 (s, 1H), 7.58-7.45 (m, 2H), 7.38-7.35 (m, 1H), 2.12 (s, 3H). 91 CF.sub.3 Me .sup.1H NMR (500 MHz, DMSO-d6) 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 CF.sub.3 Me .sup.1H NMR (500 MHz, DMSO-d6) 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 0 CF.sub.3 Me .sup.1H NMR (500 MHz, DMSO) 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 CF.sub.3 Me .sup.1H NMR (500 MHz, DMSO-d6) 14.50 (s, 1H), 8.23-8.19 (m, 1H), 7.13-7.09 (m, 1H), 2.17 (s, 3H). 95 CF.sub.3 Me .sup.1H NMR (500 MHz, DMSO-d6) 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 CF.sub.3 Me .sup.1H NMR (500 MHz, DMSO-d6) 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 CF.sub.3 Me .sup.1H NMR (500 MHz, DMSO-d6) 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 CF.sub.3 Me .sup.1H NMR (500 MHz, DMSO-d6) 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 CF.sub.3 Me .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 CF.sub.3 Me .sup.1H NMR (500 MHz, DMSO-d6) 14.53 (s, 1H), 6.60 (s, 1H), 3.87 (s, 3H), 2.39 (s, 3H), 2.20 (s, 3H). 101 CF.sub.3 Me .sup.1H NMR (500 MHz, DMSO-d6) 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 CF.sub.3 Me .sup.1H NMR (500 MHz, DMSO-d6) 14.48 (s, 1H), 7.86 (t, J = 57.5 Hz, 1H), 7.10 (s, 1H), 2.34 (s, 3H). 103 00 CF.sub.3 Me .sup.1H NMR (500 MHz, DMSO-d6) 14.49 (s, 1H), 7.06 (s, 1H), 2.35 (s, 3H), 1.87 (s, 3H). 104 01 CF.sub.3 Me .sup.1H NMR (500 MHz, DMSO-d6) 14.48 (s, 1H), 7.87 (s, 1H), 7.20 (s, 1H), 2.13 (s, 3H). 105 02 CF.sub.3 Me .sup.1H NMR (500 MHz, DMSO-d6) 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 03 CF.sub.3 Me .sup.1H NMR (500 MHz, DMSO-d6) 14.46 (s, 1H), 7.97 (s, 1H), 2.37 (s, 3H), 2.32 (s, 3H). 107 04 CF.sub.3 Me .sup.1H NMR (500 MHz, DMSO-d6) 14.44 (s, 1H), 9.20 (s, 1H), 8.10 (s, 1H), 2.34 (s, 3H). 108 05 CF.sub.3 Me .sup.1H NMR (500 MHz, DMSO-d6) 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 06 CF.sub.3 Me .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 07 CF.sub.3 Me .sup.1H NMR (500 MHz, DMSO-d6) 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 08 CF.sub.3 Me .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 09 CF.sub.3 Me .sup.1H NMR (500 MHz, DMSO-d6) 14.46 (s, 1H), 8.14-8.08 (m. 1H), 7.53-7.48 (m, 1H), 2.27 (s, 3H). 113 0 CF.sub.3 Me .sup.1H NMR (500 MHz, DMSO-d6) 14.46 (s, 1H), 8.14-8.08 (m, 1H), 7.53-7.48 (m, 1H), 2.27 (s, 3H). 114 CF.sub.3 Me .sup.1H NMR (500 MHz, DMSO-d6) 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 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d6) 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 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d6) 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 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d6) 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 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d6) 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 0 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d6) 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 CF.sub.3 .sup.1H NMR (500 MHz. DMSO-d6) 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 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d6) 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 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d6) 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 CF.sub.3 .sup.1H NMR (500 MHz. DMSO-d.sub.6) 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 0 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d6) 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 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d6) 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 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d6) 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 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d6) 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 0 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d6) 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 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d6) 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 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d6) 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 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d6) 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 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d6) 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 0 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d6) 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 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d6) 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 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d6) 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 CF.sub.3 SEt .sup.1H NMR (500 MHz, DMSO-d6) 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 CF.sub.3 SEt .sup.1H NMR (500 MHz, DMSO-d6) 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 0 CF.sub.3 SEt .sup.1H NMR (500 MHz, DMSO-d6) 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 CF.sub.3 SEt .sup.1H NMR (500 MHz, DMSO-d6) 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 CF.sub.3 SEt .sup.1H NMR (500 MHz, DMSO-d6) 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 CF.sub.3 SEt .sup.1H NMR (500 MHz, DMSO-d6) 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 CF.sub.3 SEt .sup.1H NMR (500 MHz, DMSO-d6) 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 CF.sub.3 SEt .sup.1H NMR (500 MHz, DMSO-d6) 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 CF.sub.3 SEt .sup.1H NMR (500 MHz, DMSO-d6) 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 CF.sub.3 SEt .sup.1H NMR (500 MHz, DMSO-d6) 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 CF.sub.3 SEt .sup.1H NMR (500 MHz, DMSO-d6) 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 CF.sub.3 SEt .sup.1H NMR (500 MHz, DMSO-d6) 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 0 CF.sub.3 SEt .sup.1H NMR (500 MHz, DMSO-d6) 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 CF.sub.3 SEt .sup.1H NMR (500 MHz, DMSO-d6) 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 CF.sub.3 SEt .sup.1H NMR (500 MHz, DMSO-d6) 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 CF.sub.3 SEt .sup.1H NMR (500 MHz. DMSO-d6) 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 CF.sub.3 SEt .sup.1H NMR (500 MHz, DMSO-d6) 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 CF.sub.3 SEt .sup.1H NMR (500 MHz, DMSO-d6) 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 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d6) 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 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 0 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 0 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d.sub.6)) 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 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 00 CF.sub.3 01 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 02 CF.sub.3 03 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 04 CF.sub.3 05 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 06 CF.sub.3 07 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 08 CF.sub.3 09 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 0 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 CF.sub.3 NH.sub.2 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 14.51 (s, 1H), 7.82-7.74 (m, 2H), 7.35-7.27 (m, 2H), 6.84 (s, 2H). 175 CF.sub.3 NH.sub.2 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 1451 (s, 1H). 7.75 (d, J = 7.5 Hz, 2H), 7.50 (d, J = 7.5 Hz, 2H), 6.84 (s, 2H). 176 CF.sub.3 NH.sub.2 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 14.48 (s, 1H), 7.58-7.50 (m, 2H), 7.38-7.35 (m, 1H), 6.84 (s, 2H). 177 CF.sub.3 NH.sub.2 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 CF.sub.3 NH.sub.2 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 CF.sub.3 NH.sub.2 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 CF.sub.3 NH.sub.2 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 14.49 (s, 1H), 8.22-8.19 (m, 1H), 7.13-7.09 (m, 1H), 6.85 (s, 2H). 181 CF.sub.3 NH.sub.2 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 0 CF.sub.3 NH.sub.2 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 CF.sub.3 NH.sub.2 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 CF.sub.3 NH.sub.2 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 CF.sub.3 NH.sub.2 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 CF.sub.3 NH.sub.2 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 14.48 (s, 1H), 6.84 (s, 2H), 6.60 (s, 1H), 3.87 (s, 3H), 2.39 (s, 3H). 187 CF.sub.3 NH.sub.2 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 14.48 (s, 1H), 7.87 (s, 1H), 7.20 (s, 1H), 6.84 (s, 2H). 188 CF.sub.3 NH.sub.2 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 CF.sub.3 NH.sub.2 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 14.46 (s, 1H), 7.97 (s, 1H), 6.86 (s, 2H), 2.37 (s, 3H). 190 CF.sub.3 NH.sub.2 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 14.44 (s, 1H), 9.20 (s, 1H), 8.10 (s, 1H), 6.84 (s, 2H) 191 CF.sub.3 NH.sub.2 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 0 CF.sub.3 NHMe .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 CF.sub.3 NHMe .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 CF.sub.3 NHMe .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 CF.sub.3 NHMe .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 CF.sub.3 NHMe .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 CF.sub.3 NHMe .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 CF.sub.3 NHMe .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 CF.sub.3 NHMe .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 CF.sub.3 NHMe .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 CF.sub.3 NHMe .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 0 CF.sub.3 NHMe .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 CF.sub.3 NHMe .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 CF.sub.3 NHMe .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 CF.sub.3 NHMe .sup.1H NMR (500 MHz, DMSO-d.sub.6) 14.46 (s, 1H), 7.94 (s, 1H), 7.25 (s, 1H), 5.95 (s, 1H), 2.70 (s, 3H). 206 CF.sub.3 NHMe .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 CF.sub.3 NHMe .sup.1H NMR (500 MHz, DMSO-d.sub.6) 14.46 (s, 1H), 7.96 (s, 1H), 5.93 (s, 1H), 2.71 (s, 3H), 2.34 (s, 3H). 208 CF.sub.3 NHMe .sup.1H NMR (500 MHz, DMSO-d.sub.6) 14.46 (s, 1H), 9.20 (s, 1H), 8.07 (s, 1H), 5.95 (s, 1H), 2.79 (s, 3H). 209 CF.sub.3 NHMe .sup.1H NMR (500 MHz. DMSO-d.sub.6) 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 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 0 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 0 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 0 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 14.48 (s, 1H), 9.94 (s, 1H), 7.87 (s, 1H), 7.20 (s, 1H), 2.07 (s, 3H). 224 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 14.46 (s, 1H), 9.94 (s, 1H), 7.97 (s, 1H), 2.37 (s, 3H), 2.07 (s, 3H), 226 0 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 14.44 (s, 1H), 9.94 (s, 1H), 9.20 (s, 1H), 8.10 (s, 1H), 2.07 (s, 3H). 227 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 CF.sub.3 Me .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 CF.sub.3 Me .sup.1H NMR (500 MHz, DMSO-d.sub.6) 14.50 (s, 1H), 8.07-7.55 (m, 2H), 7.10 (s, 1H), 2.34 (s, 3H). 230 CF.sub.3 Me 231 CF.sub.3 Me 232 CF.sub.3 Me 233 CF.sub.3 Me 234 0 CF.sub.3 Me 235 CF.sub.3 Me 236 CF.sub.3 Me 237 CF.sub.3 Me 238 CF.sub.3 Me 239 CF.sub.3 Me 240 CF.sub.3 Me 241 CF.sub.3 Me 242 CF.sub.3 Me 243 CF.sub.3 Me 244 00 CF.sub.3 Me 245 01 CF.sub.3 Me 246 02 CF.sub.3 Me 247 03 CF.sub.3 Me 248 04 CF.sub.3 Me 249 05 CF.sub.3 Me 250 06 CF.sub.3 Me 251 07 CF.sub.3 Me 252 08 CF.sub.3 Me 253 09 CF.sub.3 Me 254 0 CF.sub.3 Me 255 CF.sub.3 Me 256 CF.sub.3 Me 257 CF.sub.3 Me 258 CF.sub.3 Me 259 CF.sub.3 Me 260 CF.sub.3 Me 261 CF.sub.3 Me 262 CF.sub.3 Me 263 CF.sub.3 Me 264 0 CF.sub.3 Me 265 CF.sub.3 Me 266 CF.sub.3 Me 267 CF.sub.3 Me 268 CF.sub.3 Me 269 CF.sub.3 Me 270 CF.sub.3 Me 271 CF.sub.3 Me 272 CF.sub.3 Me 273 CF.sub.3 Me 274 0 CF.sub.3 Me 275 CF.sub.3 Me 276 CF.sub.3 Me 277 CF.sub.3 Me 278 CF.sub.3 Me 279 CF.sub.3 Me 280 CF.sub.3 Me 281 CF.sub.3 Me 282 CF.sub.3 Me 283 CF.sub.3 Me 284 0 CF.sub.3 Me 285 CF.sub.3 Me 286 CF.sub.3 Me 287 CF.sub.3 Me 288 CF.sub.3 Me 289 CF.sub.3 Me 290 CF.sub.3 Me 291 CF.sub.3 Me 292 CF.sub.3 Me 293 CF.sub.3 Me 294 0 CF.sub.3 Me 295 CF.sub.3 Me 296 CF.sub.3 Me 297 CF.sub.3 Me 298 CF.sub.3 Me 299 CF.sub.3 Me 300 CF.sub.3 Me 301 CF.sub.3 Me .sup.1H NMR (500 MHz, Chloroform-d) 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 CF.sub.3 Me 303 CF.sub.3 Me 304 0 CF.sub.3 Me 305 CF.sub.3 Me 306 CF.sub.3 Me 307 CF.sub.3 Me 308 CF.sub.3 Me 309 CF.sub.3 Me 310 CF.sub.3 Me 311 CF.sub.3 Me 312 CF.sub.3 Me 313 CF.sub.3 Me .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 0 CF.sub.3 Me 315 CF.sub.3 Me 316 CF.sub.3 Me 317 CF.sub.3 Me 318 CF.sub.3 Me 319 CF.sub.3 Me 320 CF.sub.3 Me 321 CF.sub.3 Me 322 CF.sub.3 Me 323 CF.sub.3 Me 324 0 CF.sub.3 Me 325 CF.sub.3 Me 326 CF.sub.3 Me 327 CF.sub.3 Me 328 CF.sub.3 Me 329 CF.sub.3 Me 330 CF.sub.3 Me 331 CF.sub.3 Me 332 CF.sub.3 Me 333 CF.sub.3 Me 334 0 CF.sub.3 Me .sup.1H NMR (500 MHz, DMSO-d.sub.6) 14.42 (s, 1H) 8.09-8.06 (m, 2H), 2.15 (s, 3H). 335 CF.sub.3 Me 336 CF.sub.3 Me 337 CF.sub.3 Me 338 CF.sub.3 Me 339 CF.sub.3 Me 340 CF.sub.3 Me 341 CF.sub.3 Me 342 CF.sub.3 Me 343 CF.sub.3 Me 344 00 CF.sub.3 Me 345 01 CF.sub.3 Me 346 02 CF.sub.3 Me 347 03 CF.sub.3 Me 348 04 CF.sub.3 Me 349 05 CF.sub.3 Me 350 06 CF.sub.3 Me 351 07 CF.sub.3 Me 352 08 CF.sub.3 Me 353 09 CF.sub.3 Me 354 0 CF.sub.3 Me 355 CF.sub.3 Me 356 CF.sub.3 Me 357 CF.sub.3 Me 358 CF.sub.3 Me 359 CF.sub.3 Me 360 CF.sub.3 Me 361 CF.sub.3 Me 362 CF.sub.3 Me 363 CF.sub.3 Me 364 0 CF.sub.3 Me 365 CF.sub.3 Me 366 CF.sub.3 Me 367 CF.sub.3 Me 368 CF.sub.3 Me 369 CF.sub.3 Me 370 CF.sub.3 Me 371 CF.sub.3 Me 372 CF.sub.3 Me 373 CF.sub.3 Me 374 0 CF.sub.3 Me 375 CF.sub.3 Me 376 CF.sub.3 Me 377 CF.sub.3 Me 378 CF.sub.3 Me 379 CF.sub.3 Me 380 CF.sub.3 Me 381 CF.sub.3 Me 382 CF.sub.3 Me 383 CF.sub.3 Me 384 0 CF.sub.3 Me 385 CF.sub.3 Me 386 CF.sub.3 Me 387 CF.sub.3 Me 388 CF.sub.3 CHF.sub.2 .sup.1H NMR (500 MHz, DMSO-d6) 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 CF.sub.3 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d6) 14.32 (s, 1H), 9.12 (s, 1H), 8.44 (s, 1H), 7.91 (t, J = 59.1 Hz, 1H). 390 CF.sub.3 CHO .sup.1H NMR (500 MHz, DMSO-d6) 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 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d6) 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 CF.sub.3 0 .sup.1H NMR (500 MHz, DMSO-d6) 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 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d6) 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 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d6) 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 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d6) 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 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d6) 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 CF.sub.3 F .sup.1H NMR (500 MHz, DMSO-d.sub.6) 14.38 (s, 1H), 7.92-7.88 (dd, J = 9.0, 5.5 Hz, 2H), 7.38-7.28 (m, 2H). 398 0 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 CF.sub.3 Me .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 CF.sub.3 0 .sup.1H NMR (500 MHz. DMSO-d.sub.6) 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 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d6) 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 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 14.29 (s, 1H), 8.07-8.03 (m, 2H), 5.33 (s, 1H), 4.93 (s, 1H), 1.96 (s, 3H). 407 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 CF.sub.3 Me .sup.1H NMR (500 MHz, Chloroform-d) 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 0 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 CF.sub.3 .sup.1H NMR (500 MHz, Chloroform-d) 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 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d6) 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 CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 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 0 CF.sub.3 Br .sup.1H NMR (500 MHz, DMSO-d.sub.6) 14.36 (s, 1H), 8.19-8.16 (m, 1H), 7.13-7.10 (m, 1H).

(4) 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) NO. M M-1 M-2 M-3 M-4 M-5 M-6 M-7 M-8 M-9 00 M-10 01 M-11 02 M-12 03 M-13 04 M-14 05 M-15 06 M-16 07 M-17 08 M-18 09 M-19 0 M-20 M-21 M-22 M-23 M-24 M-25 M-26 M-27 M-28 M-29 0 M-30 M-31 M-32 M-33 M-34 M-35 M-36 M-37 M-38 M-39 0 M-40 M-41 M-42 M-43 M-44 M-45 M-46 M-47 M-48 M-49 0 M-50 M-51 M-52 M-53 M-54 M-55 M-56 M-57 M-58 M-59 0 M-60 M-61 M-62 M-63 M-64 M-65 M-66 M-67 M-68 M-69 0 M-70 M-71 M-72 M-73 M-74 M-75 M-76 M-77 M-78 M-79 0 M-80 M-81 M-82 M-83 M-84 M-85 M-86 M-87 M-88 M-89 0 M-90 M-91 M-92 M-93 M-94 M-95 M-96 M-97 M-98 M-99 0 M-100 M-101 M-102 M-103 M-104 M-105 M-106 M-107 M-108 M-109 00 M-110 01 M-111 02 M-112 03 M-113 04 M-114 05 M-115 06 M-116 07 M-117 08 M-118 09 M-119 0 M-120 M-121 M-122 M-123 M-124 M-125 M-126 M-127 M-128 M-129 0 M-130 M-131 M-132 M-133 M-134 M-135 M-136 M-137 M-138 M-139 0 M-140 M-141 M-142 M-143 M-144 M-145 M-146 M-147 M-148 M-149 0 M-150 M-151 M-152 M-153 M-154 M-155 M-156 M-157 M-158 M-159 0 M-160 M-161 M-162 M-163 M-164 M-165 M-166 M-167 M-168 M-169 0 M-170 M-171 M-172 M-173 M-174 M-175 M-176 M-177 M-178 M-179 0 M-180 M-181 M-182 M-183 M-184 M-185 M-186 M-187 M-188 M-189 0 M-190 M-191 M-192 M-193 M-194 M-195 M-196 M-197 Me M-198 Et M-199 M-200 CN M-201 M-202 0 M-203 M-204 M-205 M-206 M-207 M-208 M-209 M-210 M-211 M-212 00 M-213 01 M-214 02 M-215 03 M-216 04 M-217 05

(5) TABLE-US-00003 TABLE 3 Structures of some derivative compounds I-1 NO. X Y Z M .sup.1HNMR 1-1 06 CF.sub.3 Me M-1 1-2 07 CF.sub.3 Me M-2 1-3 08 CF.sub.3 Me M-7 1-4 09 CF.sub.3 Me M-12 1-5 0 CF.sub.3 Me M-24 1-6 CF.sub.3 Me M-27 1-7 CF.sub.3 Me M-29 1-8 CF.sub.3 Me M-37 1-9 CF.sub.3 Me M-40 1-10 CF.sub.3 Me M-52 1-11 CF.sub.3 Me M-53 1-12 CF.sub.3 Me M-54 1-13 CF.sub.3 Me M-58 1-14 CF.sub.3 Me M-60 1-15 0 CF.sub.3 Me M-63 1-16 CF.sub.3 Me M-77 1-17 CF.sub.3 Me M-79 1-18 CF.sub.3 Me M-88 1-19 CF.sub.3 Me M-92 1-20 CF.sub.3 Me M-104 1-21 CF.sub.3 Me M-108 1-22 CF.sub.3 Me M-119 1-23 CF.sub.3 Me M-120 1-24 CF.sub.3 Me M-121 1-25 0 CF.sub.3 Me M-123 1-26 CF.sub.3 Me M-125 1-27 CF.sub.3 Me M-126 1-28 CF.sub.3 Me M-127 1-29 CF.sub.3 Me M-128 1-30 CF.sub.3 Me M-131 1-31 CF.sub.3 Me M-132 1-32 CF.sub.3 Me M-150 1-33 CF.sub.3 Me M-156 1-34 CF.sub.3 Me M-160 1-35 0 CF.sub.3 Me M-162 1-36 CF.sub.3 Me M-165 1-37 CF.sub.3 Me M-168 1-38 CF.sub.3 Me M-198 1-39 CF.sub.3 Me M-199 1-40 CF.sub.3 Me M-200 1-41 CF.sub.3 Me M-203 1-42 CF.sub.3 Me M-204 1-43 CF.sub.3 Me M-205 1-44 CF.sub.3 Me M-207 1-45 0 CF.sub.3 Me M-208 1-46 CF.sub.3 Me M-209 1-47 CF.sub.3 Me M-211 1-48 CF.sub.3 Me M-212 1-49 CF.sub.3 Me M-216 1-50 CF.sub.3 Me M-1 1-51 CF.sub.3 Me M-2 1-52 CF.sub.3 Me M-7 1-53 CF.sub.3 Me M-12 1-54 CF.sub.3 Me M-24 1-55 0 CF.sub.3 Me M-27 1-56 CF.sub.3 Me M-29 1-57 CF.sub.3 Me M-37 1-58 CF.sub.3 Me M-40 1-59 CF.sub.3 Me M-52 1-60 CF.sub.3 Me M-53 1-61 CF.sub.3 Me M-54 1-62 CF.sub.3 Me M-58 1-63 CF.sub.3 Me M-60 1-64 CF.sub.3 Me M-63 1-65 0 CF.sub.3 Me M-77 1-66 CF.sub.3 Me M-79 1-67 CF.sub.3 Me M-88 1-68 CF.sub.3 Me M-92 1-69 CF.sub.3 Me M-104 1-70 CF.sub.3 Me M-108 1-71 CF.sub.3 Me M-119 1-72 CF.sub.3 Me M-120 1-73 CF.sub.3 Me M-121 1-74 CF.sub.3 Me M-123 1-75 0 CF.sub.3 Me M-125 1-76 CF.sub.3 Me M-126 1-77 CF.sub.3 Me M-127 1-78 CF.sub.3 Me M-128 1-79 CF.sub.3 Me M-131 1-80 CF.sub.3 Me M-132 1-81 CF.sub.3 Me M-150 1-82 CF.sub.3 Me M-156 1-83 CF.sub.3 Me M-160 1-84 CF.sub.3 Me M-162 1-85 0 CF.sub.3 Me M-165 1-86 CF.sub.3 Me M-168 1-87 CF.sub.3 Me M-198 1-88 CF.sub.3 Me M-199 1-89 CF.sub.3 Me M-200 1-90 CF.sub.3 Me M-203 1-91 CF.sub.3 Me M-204 1-92 CF.sub.3 Me M-205 1-93 CF.sub.3 Me M-207 1-94 CF.sub.3 Me M-208 1-95 00 CF.sub.3 Me M-209 1-96 01 CF.sub.3 Me M-211 1-97 02 CF.sub.3 Me M-212 1-98 03 CF.sub.3 Me M-216 1-99 04 CF.sub.3 Me M-7 1-100 05 CF.sub.3 Me M-58 1-101 06 CF.sub.3 Me M-123 1-102 07 CF.sub.3 Me M-125 1-103 08 CF.sub.3 Me M-160 1-104 09 CF.sub.3 Me M-165 1-105 0 CF.sub.3 Me M-205 1-106 CF.sub.3 M-217 .sup.1H NMR (500 MHz, DMSO-d6) 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).

(6) 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.

(7) 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.

(8) Examples of representative compounds are as follows, and the synthesis methods of other compounds are similar, and the detailed description is omitted here.

(9) 1. Synthesis of Intermediate a

(10) (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).

(11) (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.

(12) ##STR00913##
2. Synthesis of Compound 2

(13) 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%).

(14) ##STR00914##
3. Synthesis of Compound 3

(15) 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%).

(16) ##STR00915##
4. Synthesis of Compound 4

(17) 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%).

(18) ##STR00916##
5. Synthesis of Compound 5

(19) 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%).

(20) ##STR00917##

(21) 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.2CH.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%).

(22) ##STR00918##

(23) 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.

(24) ##STR00919##
6. Synthesis of Compound 8

(25) 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.

(26) ##STR00920##

(27) 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.

(28) ##STR00921##
7. Synthesis of Compound 12

(29) (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.

(30) (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%.

(31) ##STR00922##
8. Synthesis of Compound 16

(32) (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%.

(33) (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%.

(34) ##STR00923##
9. Synthesis of Compound 25

(35) (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%.

(36) (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%.

(37) ##STR00924##
10. Synthesis of Compound 27

(38) 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%).

(39) ##STR00925##

(40) 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.

(41) ##STR00926##
11. Synthesis of Compound 31

(42) 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.2CH.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%).

(43) ##STR00927##

(44) 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.

(45) ##STR00928##
12. Synthesis of Intermediate c

(46) 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.

(47) ##STR00929##

(48) 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.

(49) ##STR00930##

(50) 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.

(51) ##STR00931##

(52) 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.

(53) ##STR00932##
13. Synthesis of Compound 46

(54) 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%).

(55) ##STR00933##
14. Synthesis of Compound 48

(56) 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%).

(57) ##STR00934##

(58) 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.2CH.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%).

(59) ##STR00935##

(60) 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.

(61) ##STR00936##
Evaluation of Biological Activity:

(62) The activity level standard of plant destruction (i.e. growth inhibition rate) is as follows: Level 5: growth control rate is above 85%; Level 4: growth control rate is greater than or equal to 60% and less than 85%; Level 3: growth control rate is greater than or equal to 40% and less than 60%; Level 2: growth control rate is greater than or equal to 20% and less than 40%; Level 1: growth control rate is greater than or equal to 5% and less than 20%; Level 0: growth control rate is less than 5%.

(63) The above described growth inhibition rates are fresh weight inhibition rates.

(64) 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.

(65) 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.
Experiment of Pre-Emergence Test:

(66) 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.

(67) 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.

(68) Transplanted rice safety evaluation and weed control effect evaluation in rice field:

(69) 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.

(70) 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.

(71) 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.

(72) 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.

(73) 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).