US 12,568,972 B2Granted

Pyridazinol compounds and derivatives, preparation methods, herbicidal compositions and applications thereof

AssigneeQingdao Kingagroot Chemical Compound Co., Ltd.

InventorsLei Lian, Yurong Zheng, Rongbao Hua, Jianfeng Wang, Xuegang Peng, Qi Cui

Life of this patent

Estimating the term…

Abstract

The invention belongs to the technical field of agricultural chemicals, and in particular relates to a pyridazinol compound represented by the Formula I, a derivative, preparation method, herbicidal composition and use thereof. The compound, derivative and herbicidal composition thereof have very high herbicidal activity and selectivity, and are safe for crops,

Claims24

Dependent claims

A herbicidally active pyridazinol compound of Formula I or a derivative thereof:

wherein, X is halogenated alkyl;
A is selected from unsubstituted or substituted C2-C8 alkenyl, unsubstituted or substituted C2-C8 alkynyl, unsubstituted or substituted C3-C8 cycloalkyl, unsubstituted or substituted C3-C8 cycloalkenyl, unsubstituted or substituted C3-C8 cycloalkyl-C1-C8 alkyl, unsubstituted or substituted
unsubstituted or substituted 5- to 14-membered heteroaryl, and unsubstituted or substituted 5- to 14-membered aliphatic heterocyclyl;
wherein,
when being substituted, said C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, or C3-C8 cycloalkyl-C1-C8 alkyl is substituted with one or more substituents independently selected from halogen, cyano, nitro, azido, aryl, and heteroaryl, said aryl or heteroaryl is unsubstituted or independently substituted with 1-5 groups selected from halogen, cyano, nitro, hydroxy, carboxyl, sulfhydryl, amino, and a halogen-containing or not containing group selected from C1-C8 alkyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkyl-C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C1-C8 alkoxy, C1-C8 alkylcarbonyl, C1-C8 alkoxycarbonyl, C1-C8 alkylsulfonyl, C1-C8 alkylamino, and C1-C8 alkylcarbonyloxy, —(CH2)n-O—(CH2)p-, —(CH2)n-S—(CH2)p-, —(CH2)n-NR3-(CH2)p-, R—O—, R—O—(CH2)p-O—, R—O—(CH2)p-S—, R—S—, R—S—(CH2)p-O—, R—S—(CH2)p-S—, R—O—(C═O)—(CH2)q-(O)m-, R—O—(CH2)n-(C═O)—(O)m-, R—O—(CH2)n-(C═O)—, R—S—(C═S)—(CH2)q-(S)m-, R—S—(CH2)n-(C═S)—(S)m-, R—S—(CH2)n-(C═S)—, R—O—(C═O)—(CH2)q-(S)m-, R—O—(CH2)n-(C═O)—(S)m-, R—O—(C═S)—(CH2)q-(O)m-, R—O—(CH2)n-(C═S)—(O)m-, R—O—(CH2)n-(C═S)—, R—S—(C═O)—(CH2)q-(O)m-, R—S—(CH2)n-(C═O)—(O)m-, R—S—(CH2)n-(C═O)—, R—O—(C═S)—(CH2)q-(S)m-, R—O—(CH2)n-(C═S)—(S)m-, R—S—(C═O)—(CH2)q-(S)m-, R—S—(CH2)n-(C═O)—(S)m-, R—S—(C═S)—(CH2)q-(O)m-, R—S—(CH2)n-(C═S)—(O)m-, R—(C═O)—, R—(C═S)—, R—(C═O)—O—, R—(C═S)—S—, R—(C═O)—S—, R—(C═S)—O—, R—SO—(O)m-, R—SO—(S)m-, R—SO—(NR3)m-, R—SO2-(O)m-, R—SO2-(S)m-, R—SO2(NR3)m-, R1 R2N—, R1 R2N—O—(CH2)q-(O)m-, R1 R2N—(CH2)n-O—, R1 R2N—O—(CH2)q-(S)m-, R1 R2N—O—(CH2)q-(NR3)m-, R1 R2N—(C═O)—(CH2)q-(O)m-, R1 R2N—(CH2)n-(C═O)—(O)m-, R1 R2N—(CH2)n-(C═O)—, R1 R2N—(C═O)—(CH2)q-(S)m-, R1 R2N—(CH2)n-(C═O)—(S)m-, R1 R2N—(C═O)—(CH2)q-(NR3)m-, R1 R2N—(CH2)n-(C═O)—(NR3)m-, R1 R2N—SO2-(CH2)q-(O)m-, R1 R2N—(CH2)n-SO2-(O)m-, R1 R2N—(CH2)n-SO2-, R1 R2N—SO2-(CH2)q-(S)m-, R1 R2N—(CH2)n-SO2-(S)m-, R1 R2N—SO2-(CH2)q-(NR3)m-, R1 R2N—(CH2)n-SO2-(NR3)m-, R1 R2P(O)—, R1 R2R3SiO—, R1 R2R3Si—(CH═CH)m-, R1 R2C═N—(O)m-, and R1 R2C═N—NH—;
when being substituted, each of said
5- to 14-membered heteroaryl or 5- to 14-membered aliphatic heterocyclyl is independently substituted with one or more substituents selected from halogen, cyano, nitro, azido, a halogen-containing or not containing group selected from C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, and C3-C8 cycloalkyl-C1-C8 alkyl, aryl, aryl-C1-C8 alkyl, heteroaryl, heteroaryl-C1-C8 alkyl, aliphatic heterocyclyl, and aliphatic heterocyclyl-C1-C8 alkyl, each of said aryl, aryl-C1-C8 alkyl, heteroaryl, heteroaryl-C1-C8 alkyl, aliphatic heterocyclyl, or aliphatic heterocyclyl-C1-C8 alkyl is unsubstituted or substituted with 1-5 groups independently selected from halogen, cyano, nitro, hydroxy, carboxyl, sulfhydryl, amino, and a halogen-containing or not containing group selected from C1-C8 alkyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkyl-C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C1-C8 alkoxy, C1-C8 alkylcarbonyl, C1-C8 alkoxycarbonyl, C1-C8 alkylsulfonyl, C1-C8 alkylamino, and C1-C8 alkylcarbonyloxy, R—O—(CH2)n-, R—O—(CH2)p-O—(CH2)q-, R—O—(CH2)p-S—(CH2)q-, R—S—(CH2)n-, R—S—(CH2)p-O—(CH2)q-, R—S—(CH2)p-S—(CH2)q-, R—O—(CH2)n-(C═O)—(CH2)q-(O)m-, R—S—(CH2)n-(C═S)—(CH2)q-, R—O—(CH2)n-(C═S)—(CH2)q-, R—S—(CH2)n-(C═O)—(CH2)q-, R—S—(C═S)—(CH2)q-(S)m-, R—O—(CH2)n-(C═O)—(CH2)q-(S)m-, R—O—(C═S)—(CH2)q-(O)m-, R—S—(C═O)—(CH2)q-(O)m-, R—O—(C═S)—(CH2)q-(S)m-, R—S—(C═O)—(CH2)q-(S)m-, R—S—(C═S)—(CH2)q-(O)m-, R—S—(CH2)n-(C═S)—(S)m-, R—O—(CH2)n-(C═S)—(O)m-, R—S—(CH2)n-(C═O)—(O)m-, R—O—(CH2)n-(C═S)—(S)m-, R—S—(CH2)n-(C═O)—(S)m-, R—S—(CH2)n-(C═S)—(O)m-, R—(C═O)—(CH2)n-, R—(C═S)—, R—(C═O)—(CH2)n-O—(CH2)q-, R—(C═S)—(CH2)n-S—, R—(C═O)—(CH2)n-S—, R—(C═S)—(CH2)n-O—, R—(C═S)—S—(CH2)q-, R—(C═O)—S—(CH2)q-, R—(C═S)—O—(CH2)q-, R—SO—(O)m-, R—SO—(S)m-, R—SO—(NR3)m-, R—SO2-(CH2)n-(O)m-, R—SO2-(S)m-, R—SO2-(CH2)n-(NR3)m-, R—SO—(CH2)n-, R1 R2N—(CH2)n-, R1 R2N—(CH2)n-O—(CH2)q-, R1 R2N—(C═O)—(CH2)q-(O)m-, R1 R2N—(CH2)n-(C═O)—(CH2)q-, R1 R2N—(CH2)n-(C═O)—(O)m-, R1 R2N—(CH2)n-(C═O)—(S)m-, R1 R2N—(CH2)n-(C═O)—(NR3)m-, R1 R2N—(CH2)n-SO2-(CH2)q-(O)m-, R1 R2N—(CH2)n-SO2-(S)m-, R1 R2N—(CH2)n-SO2-(NR3)m-, R1 R2N—(C═O)—(CH2)n-(O)m-, R1 R2N—(C═O)—(CH2)n-(S)m-, R1 R2N—(C═O)—(CH2)n-(NR3)m-, R1 R2N—SO2-(CH2)q-(S)m-, R1 R2N—SO2-(CH2)q-(NR3)m-, R1 R2N—(CH2)n-O—, R1 R2N—O—(CH2)q-, R1 R2P(O)—(O)m-, R1 R2R3SiO—, R1 R2R3Si—(CH═CH)m-, R1 R2C═N—(O)m-, and R1 R2C═N—NH—;
m is 0 or 1, n and q are independently an integer from 0 to 6, p is an integer from 1 to 6;
R is hydrogen, a halogen-containing or not containing group selected from C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, and C3-C8 cycloalkyl-C1-C8 alkyl, aryl, aryl-C1-C8 alkyl, heteroaryl, or heteroaryl-C1-C8 alkyl, each of said aryl, aryl-C1-C8 alkyl, heteroaryl, or heteroaryl-C1-C8 alkyl is unsubstituted or substituted with 1-5 groups substituents independently selected from halogen, cyano, nitro, hydroxy, carboxyl, sulfhydryl, amino, and a halogen-containing or not containing group selected from C1-C8 alkyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkyl-C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C1-C8 alkoxy, C1-C8 alkylcarbonyl, C1-C8 alkoxycarbonyl, C1-C8 alkylsulfonyl, C1-C8 alkylamino, and C1-C8 alkylcarbonyloxy;
R1, R2, R3 are each independently hydrogen, nitro, hydroxy, amino, a halogen-containing or not containing group selected from C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkyl-C1-C8 alkyl, C1-C8 alkoxy, C2-C8 alkenyloxy, C2-C8 alkynyloxy, C3-C8 cycloalkyloxy, C1-C8 alkoxy-C1-C8 alkyl, C1-C8 alkoxycarbonyl, C1-C8 alkylcarbonyl-C1-C8 alkyl, C1-C8 alkylsulfanylcarbonyl, C1-C8 alkylsulfonyl, C1-C8 alkylsulfonyl-C1-C8 alkyl, C1-C8 alkylcarbonyl, C1-C8 alkylcarbonyloxy, C1-C8 alkylamino, C1-C8 alkylaminocarbonyl, C1-C8 alkoxyaminocarbonyl, C1-C8 alkoxycarbonyl-C1-C8 alkyl, C1-C8 alkylaminocarbonyl-C1-C8 alkyl, triC1-C8 alkylsilyl, and diC1-C8 alkylphosphonyl, aryl, aryl-C1-C8 alkyl, aryloxy, aryl-C1-C8 alkyloxy, aryloxy-C1-C8 alkyl, arylcarbonyl, arylsulfonyl, heteroaryl, heteroaryl-C1-C8 alkyl, heteroaryloxy, heteroaryl-C1-C8 alkyloxy, heteroaryloxy-C1-C8 alkyl, heteroarylcarbonyl, heteroarylsulfonyl, aliphatic heterocyclyl, aliphatic heterocyclyl-C1-C8 alkyl, aliphatic heterocyclyloxy, aliphatic heterocyclyl-C1-C8 alkyloxy, aliphatic heterocyclyloxy-C1-C8 alkyl, aliphatic heterocyclylcarbonyl, or aliphatic heterocyclylsulfonyl, each of said aryl, aryl-C1-C8 alkyl, aryloxy, aryl-C1-C8 alkyloxy, aryloxy-C1-C8 alkyl, arylcarbonyl, arylsulfonyl, heteroaryl, heteroaryl-C1-C8 alkyl, heteroaryloxy, heteroaryl-C1-C8 alkyloxy, heteroaryloxy-C1-C8 alkyl, heteroarylcarbonyl, heteroarylsulfonyl, aliphatic heterocyclyl, aliphatic heterocyclyl-C1-C8 alkyl, aliphatic heterocyclyloxy, aliphatic heterocyclyl-C1-C8 alkyloxy, aliphatic heterocyclyloxy-C1-C8 alkyl, aliphatic heterocyclylcarbonyl, or aliphatic heterocyclylsulfonyl is unsubstituted or substituted with 1-5 groups independently selected from halogen, cyano, nitro, hydroxy, carboxyl, sulfhydryl, amino, and a halogen-containing or not containing group selected from C1-C8 alkyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkyl-C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C1-C8 alkoxy, C1-C8 alkylcarbonyl, C1-C8 alkoxycarbonyl, C1-C8 alkylsulfonyl, C1-C8 alkylamino, and C1-C8 alkylcarbonyloxy;
or R1 R2N— forms a 5- to 6-membered heterocyclyl;
or
wherein A is phenyl or 7- to 14-membered aryl, which is substituted with one or more substituents independently selected from azido, halogenated C1-C8 alkyl, a halogen-containing aryl, a halogen-containing aryl-C1-C8 alkyl, a halogen-containing or not containing group selected from C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, and C3-C8 cycloalkyl-C1-C8 alkyl, heteroaryl, heteroaryl-C1-C8 alkyl, aliphatic heterocyclyl, and aliphatic heterocyclyl-C1-C8 alkyl, each of said heteroaryl, heteroaryl-C1-C8 alkyl, aliphatic heterocyclyl, or aliphatic heterocyclyl-C1-C8 alkyl is unsubstituted or substituted with 1-5 groups independently selected from halogen, cyano, nitro, hydroxy, carboxyl, sulfhydryl, amino, and a halogen-containing or not containing group selected from C1-C8 alkyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkyl-C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C1-C8 alkoxy, C1-C8 alkylcarbonyl, C1-C8 alkoxycarbonyl, C1-C8 alkylsulfonyl, C1-C8 alkylamino, and C1-C8 alkylcarbonyloxy, R—O—(CH2)n-, R—O—(CH2)p-O—(CH2)q-, R—O—(CH2)p-S—(CH2)q-, R—S—(CH2)n-, R—S—(CH2)p-O—(CH2)q-, R—S—(CH2)p-S—(CH2)q-, R—O—(CH2)n-(C═O)—(CH2)q-(O)m-, R—S—(CH2)n-(C═S)—(CH2)q-, R—O—(CH2)n-(C═S)—(CH2)q-, R—S—(CH2)n-(C═O)—(CH2)q-, R—S—(C═S)—(CH2)q-(S)m-, R—O—(CH2)n-(C═O)—(CH2)q-(S)m-, R—O—(C═S)—(CH2)q-(O)m-, R—S—(C═O)—(CH2)q-(O)m-, R—O—(C═S)—(CH2)q-(S)m-, R—S—(C═O)—(CH2)q-(S)m-, R—S—(C═S)—(CH2)q-(O)m-, R—S—(CH2)n-(C═S)—(S)m-, R—O—(CH2)n-(C═S)—(O)m-, R—S—(CH2)n-(C═O)—(O)m-, R—O—(CH2)n-(C═S)—(S)m-, R—S—(CH2)n-(C═O)—(S)m-, R—S—(CH2)n-(C═S)—(O)m-, R—(C═O)—(CH2)n-, R—(C═S)—, R—(C═O)—(CH2)n-O—(CH2)q-, R—(C═S)—(CH2)n-S—, R—(C═O)—(CH2)n-S—, R—(C═S)—(CH2)n-O—, R—(C═S)—S—(CH2)q-, R—(C═O)—S—(CH2)q-, R—(C═S)—O—(CH2)q-, R—SO—(O)m-, R—SO—(S)m-, R—SO—(NR3)m-, R—SO2-(CH2)n-(O)m-, R—SO2-(S)m-, R—SO2-(CH2)n-(NR3)m-, R—SO—(CH2)n-, R1 R2N—(CH2)n-, R1 R2N—(CH2)n-O—(CH2)q-, R1 R2N—(C═O)—(CH2)q-(O)m-, R1 R2N—(CH2)n-(C═O)—(CH2)q-, R1 R2N—(CH2)n-(C═O)—(O)m-, R1 R2N—(CH2)n-(C═O)—(S)m-, R1 R2N—(CH2)n-(C═O)—(NR3)m-, R1 R2N—(CH2)n-SO2-(CH2)q-(O)m-, R1 R2N—(CH2)n-SO2-(S)m-, R1 R2N—(CH2)n-SO2-(NR3)m-, R1 R2N—(C═O)—(CH2)n-(O)m-, R1 R2N—(C═O)—(CH2)n-(S)m-, R1 R2N—(C═O)—(CH2)n-(NR3)m-, R1 R2N—SO2-(CH2)q-(S)m-, R1 R2N—SO2-(CH2)q-(NR3)m-, R1 R2N—(CH2)n-O—, R1 R2N—O—(CH2)q-, R1 R2P(O)—(O)m-, R1 R2R3SiO—, R1 R2R3Si—(CH═CH)m-, R1 R2C═N—(O)m-, and R1 R2C═N—NH—;
wherein the derivative is an agriculturally acceptable salt or a compound derivatized from 4-hydroxy of the pyridazine ring of the Formula I, further wherein the compound derivatized from 4-hydroxy of the pyridazine ring of the Formula I is selected from an ester, an oxime, and a hydroxylamine thereof.

11 more elements

A herbicidally active pyridazinol compound of Formula I or a derivative thereof,

wherein X and A are shown below:
No.
X
A
20
CF3
21
CF3
22
CF3
23
CF3
24
CF3
25
CF3
50
CF3
51
CF3
63
CF3
64
CF3
65
CF3
67
CF3
84
CF3
85
CF3
86
CF3
87
CF3
88
CF3
92
CF3
95
CF3
96
CF3
97
CF3
98
CF3
99
CF3
100
CF3
102
CF3
103
CF3
104
CF3
106
CF3
107
CF3
108
CF3
109
CF3
110
CF3
111
CF3
112
CF3
113
CF3
114
CF3
115
CF3
116
CF3
119
CF3
120
CF3
121
CF3
122
CF3
123
CF3
124
CF3
125
CF3
126
CF3
127
CF3
128
CF3
129
CF3
130
CF3
131
CF3
132
CF3
133
CF3
134
CF3
135
CF3
136
CF3
137
CF3
138
CF3
139
CF3
140
CF3
141
CF3
142
CF3
143
CF3
144
CF3
145
CF3
146
CF3
147
CF3
148
CF3
149
CF3
150
CF3
151
CF3
152
CF3
155
CF3
156
CF3
159
CF3
160
CF3
164
CF3
165
CF3
166
CF3
167
CF3
168
CF3
169
CF3
170
CF3
171
CF3
172
CF3
173
CF3
174
CF3
175
CF3
176
CF3
177
CF3
178
CF3
180
CF3
181
CF3
182
CF3
183
CF3
184
CF3
185
CF3
186
CF3
187
CF3
188
CF3
189
CF3
190
CF3
191
CF3
192
CF3
193
CF3
194
CF3
195
CF3
196
CF3
197
CF3
198
CF3
199
CF3
200
CF3
201
CF3
202
CF3
203
CF3
204
CF3
205
CF3
206
CF3
207
CF3
208
CF3
209
CF3
210
CF3
211
CF3
212
CF3
213
CF3
214
CF3
215
CF3
216
CF3
217
CF3
218
CF3
219
CF3
220
CF3
221
CF3
222
CF3
223
CF3
224
CF3
225
CF3
226
CF3
227
CF3
228
CF3
229
CF3
230
CF3
231
CF3
232
CF3
233
CF3
234
CF3
235
CF3
236
CF3
237
CF3
238
CF3
239
CF3
240
CF3
241
CF3
242
CF3
243
CF3
244
CF3
245
CF3
246
CF3
247
CF3
248
CF3
249
CF3
250
CF3
251
CF3
252
CF3
253
CF3
254
CF3
255
CF3
256
CF3
257
CF3
258
CF3
259
CF3
260
CF3
261
CF3
262
CF3
263
CF3
264
CF3
265
CF3
266
CF3
267
CF3
268
CF3
269
CF3
270
CF3
271
CF3
272
CF3
273
CF3
274
CF3
275
CF3
276
CF3
277
CF3
278
CF3
279
CF3
280
CF3
281
CF3
282
CF3
283
CF3
284
CF3
285
CF3
286
CF3
287
CF3
288
CF3
289
CF3
290
CF3
291
CF3
292
CF3
293
CF3
294
CF3
295
CF3
296
CF3
297
CF3
298
CF3
299
CF3
300
CF3
301
CF3
302
CF3
303
CF3
304
CF3
305
CF3
306
CF3
307
CF3
308
CF3
309
CF3
310
CF3
311
CF3
312
CF3
313
CF3
314
CF3
315
CF3
316
CF3
317
CF3
318
CF3
319
CF3
320
CF3
321
CF3
322
CF3
323
CF3
324
CF3
325
CF3
326
CF3
327
CF3
328
CF3
329
CF3
330
CF3
331
CF3
332
CF3
333
CF3
334
CF3
335
CF3
336
CF3
337
CF3
338
CF3
339
CF3
340
CF3
341
CF3
342
CF3
343
CF3
344
CF3
345
CF3
346
CF3
347
CF3
348
CF3
349
CF3
350
CF3
351
CF3
352
CF3
353
CF3
354
CF3
355
CF3
356
CF3
357
CF3
358
CF3
359
CF3
360
CF3
361
CF3
362
CF3
363
CF3
364
CF3
365
CF3
366
CF3
367
CF3
368
CF3
369
CF3
374
CF3
375
CF3
376
CF3
377
CF3
378
CF3
379
CF3
381
CF3
382
CF3
383
CF3
386
CF3
387
CF3
388
CF3
389
CF3
390
CF3
391
CF3
392
CF3
393
CF3
394
CF3
395
CF3
396
CF3
397
CF3
398
CF3
399
CF3
400
CF3
401
CF3
402
CF3
403
CF3
404
CF3
405
CF3
406
CF3
407
CF3
408
CF3
409
CF3
410
CF3
411
CF3
412
CF3
413
CF3
414
CF3
415
CF3
416
CF3
417
CF3
418
CF3
419
CF3
420
CF3
421
CF3
422
CF3
423
CF3
424
CF3
425
CF3
426
CF3
427
CF3
428
CF3
429
CF3
430
CF3
431
CF3
432
CF3
433
CF3
434
CF3
435
CF3
436
CF3
437
CF3
438
CF3
439
CF3
440
CF3
441
CF3
442
CF3
443
CF3
444
CF3
445
CF3
446
CF3
447
CF3
448
CF3
449
CF3
450
CF3
451
CF3
452
CF3
453
CF3
454
CF3
455
CF3
456
CF3
457
CF3
458
CF3
459
CF3
460
CF3
461
CF3
462
CF3
463
CF3
464
CF3
465
CF3
466
CF3
467
CF3
468
CF3
469
CF3
470
CF3
471
CF3
472
CF3
473
CF3
474
CF3
475
CF3
476
CF3
477
CF3
478
CF3
479
CF3
480
CF3
481
CF3
482
CF3
483
CF3
484
CF3
485
CF3
486
CF3
487
CF3
488
CF3
489
CF3
490
CF3
491
CF3
492
CF3
493
CF3
494
CF3
495
CF3
496
CF3
497
CF3
498
CF3
499
CF3
500
CF3
501
CF3
502
CF3
503
CF3
504
CF3
505
CF3
506
CF3
507
CF3
508
CF3
509
CF3
510
CF3
511
CF3
512
CF3
513
CF3
514
CF3
515
CF3
516
CF3
517
CF3
518
CF3
519
CF3
520
CF3
521
CF3
522
CF3
523
CF3
524
CF3
525
CF3
526
CF3
527
CF3
528
CF3
529
CF3
530
CF3
531
CF3
532
CF3
533
CF3
534
CF3
535
CF3
536
CF3
537
CF3
538
CF3
539
CF3
540
CF3
541
CF3
542
CF3
543
CF3
544
CF3
545
CF3
546
CF3
547
CF3
548
CF3
549
CF3
550
CF3
551
CF3
552
CF3
553
CF3
554
CF3
555
CF3
556
CF3
557
CF3
558
CF3
559
CF3
560
CF3
561
CF3
562
CF3
563
CF3
564
CF3
565
CF3
566
CF3
567
CF3
568
CF3
569
CF3
570
CF3
572
CF3
578
CF3
579
CF3
580
CF3
581
CF3
582
CF3
583
CF3
584
CF3
585
CF3
586
CF3
587
CF3
588
CF3
589
CF3
590
CF3
591
CF3
592
CF3
593
CF3
594
CF3
595
CF3
596
CF3
597
CF3
598
CF3
599
CF3
600
CF3
601
CF3
602
CF3
603
CF3
604
CF3
605
CF3
606
CF3
607
CF3
608
CF3
609
CF3
610
CF3
611
CF3
612
CF3
613
CF3
614
CF3
615
CF3
616
CF3
617
CF3
618
CF3
619
CF3
620
CF3
622
CF3
623
CF3
624
CF3
625
CF3
626
CF3
627
CF3
628
CF3
629
CF3
630
CF3
631
CF3
632
CF3
633
CF3
634
CF3
635
CF3
636
CF3
637
CF3
638
CF3
639
CF3
640
CF3
641
CF3
642
CF3
643
CF3
644
CF3
645
CF3
646
CF3
647
CF3
648
CF3
649
CF3
650
CF3
651
CF3
652
CF3
653
CF3
654
CF3
655
CF3
656
CF3
657
CF3
658
CF3
659
CF3
660
CF3
661
CF3
662
CF3
663
CF3
664
CF3
665
CF3
666
CF3
667
CF3
668
CF3
669
CF3
670
CF3
671
CF3
672
CF3
673
CF3
674
CF3
675
CF3
676
CF3
677
CF3
678
CF3
679
CF3
680
CF3
681
CF3
682
CF3
683
CF3
684
CF3
685
CF3
686
CF3
687
CF3
688
CF3
689
CF3
690
CF3
691
CF3
692
CF3
693
CF3
694
CF3
695
CF3
696
CF3
697
CF3
698
CF3
699
CF3
700
CF3
701
CF3
702
CF3
703
CF3
704
CF3
705
CF3
706
CF3
707
CF3
708
CF3
709
CF3
710
CF3
711
CF3
712
CF3
713
CF3
714
CF3
715
CF3
716
CF3
717
CF3
718
CF3
719
CF3
720
CF3
721
CF3
722
CF3
723
CF3
724
CF3
725
CF3
726
CF3
727
CF3
728
CF3
729
CF3
730
CF3
731
CF3
733
CF3
734
CF3
735
CF3
737
CF3
738
CF3
743
CF3
746
CF3
749
CF3
751
CF3
752
CF3
761
CF3
762
CF3
763
CF3
764
CF3
767
CF3
768
CF3
769
CF3
770
CF3
771
CF3
773
CF3
774
CF3
775
CF3
776
CF3
777
CF3
778
CF3
779
CF3
780
CF3
781
CF3
782
CF3
783
CF3
784
CF3
785
CF3
786
CF3
787
CF3
788
CF3
789
CF3
790
CF3
791
CF3
792
CF3
793
CF3
794
CF3
795
CF3
796
CF3
797
CF3
798
CF3
799
CF3
800
CF3
801
CF3
802
CF3
803
CF3
804
CF3
805
CF3
806
CF3
807
CF3
808
CF3
809
CF3
810
CF3
811
CF3
812
CF3
813
CF3
814
CF3
815
CF3
816
CF3
817
CF3
818
CF3
819
CF3
820
CF3
821
CF3
822
CF3
823
CF3
824
CF3
825
CF3
826
CF3
827
CF3
828
CF3
829
CF3
830
CF3
831
CF3
832
CF3
833
CF3
834
CF3
835
CF3
836
CF3
837
CF3
838
CF3
839
CF3
840
CF3
841
CF3
842
CF3
843
CF3
844
CF3
845
CF3
846
CF3
847
CF3
848
CF3
849
CF3
850
CF3
851
CF3
852
CF3
853
CF3
854
CF3
855
CF3
856
CF3
857
CF3
858
CF3
859
CF3
860
CF3
861
CF3
862
CF3
863
CF3
864
CF3
865
CF3
866
CF3
867
CF3
868
CF3
869
CF3
870
CF3
871
CF3
872
CF3
873
CF3
874
CF3
875
CF3
876
CF3
877
CF3
878
CF3
879
CF3
880
CF3
881
CF3
882
CF3
883
CF3
884
CF3
885
CF3
886
CF3
887
CF3
888
CF3
889
CF3
890
CF3
891
CF3
892
CF3
893
CF3
894
CF3
895
CF3
896
CF3
897
CF3
898
CF3
899
CF3
900
CF3
901
CF3
902
CF3
903
CF3
904
CF3
905
CF3
906
CF3
907
CF3
908
CF3
909
CF3
910
CF3
911
CF3
912
CF3
913
CF3
914
CF3
915
CF3
916
CF3
917
CF3
918
CF3
919
CF3
920
CF3
921
CF3
922
CF3
923
CF3
924
CF3
925
CF3
926
CF3
927
CF3
928
CF3
929
CF3
930
CF3
931
CF3
932
CF3
933
CF3
934
CF3
935
CF3
936
CF3
937
CF3
938
CF3
939
CF3
940
CF3
941
CF3
942
CF3
943
CF3
944
CF3
945
CF3
946
CF3
947
CF3
948
CF3
949
CF3
950
CF3
951
CF3
952
CF3
953
CF3
954
CF3
955
CF3
956
CF3
957
CF3
958
CF3
959
CF3
960
CF3
961
CF3
962
CF3
963
CF3
964
CF3
965
CF3
966
CF3
967
CF3
968
CF3
969
CF3
970
CF3
971
CF3
972
CF3
973
CF3
974
CF3
975
CF3
976
CF3
977
CF3
978
CF3
979
CF3
980
CF3
981
CF3
982
CF3
983
CF3
984
CF3
985
CF3
986
CF3
987
CF3
988
CF3
989
CF3
990
CF3
991
CF3
992
CF3
993
CF3
994
CF3
995
CF3
996
CF3
997
CF3
998
CF3
999
CF3
1000
CF3
1001
CF3
1002
CF3
1003
CF3
1004
CF3
1005
CF3
1006
CF3
1007
CF3
1008
CF3
1009
CF3
1010
CF3
1011
CF3
1012
CF3
1013
CF3
1014
CF3
1015
CF3
1016
CF3
1017
CF3
1018
CF3
1019
CF3
1020
CF3
1021
CF3
1022
CF3
1023
CF3
1024
CF3
1025
CF3
1026
CF3
1027
CF3
1028
CF3
1029
CF3
1030
CF3
1031
CF3
1032
CF3
1033
CF3
1034
CF3
1035
CF3
1036
CF3
1037
CF3
1038
CF3
1039
CF3
1040
CF3
1041
CF3
1042
CF3
1043
CF3
1044
CF3
1045
CF3
1046
CF3
1047
CF3
1048
CF3
1049
CF3
1050
CF3
1051
CF3
1052
CF3
1053
CF3
1054
CF3
1055
CF3
1056
CF3
1057
CF3
1058
CF3
1059
CF3
1060
CF3
1061
CF3
1062
CF3
1063
CF3
1064
CF3
1065
CF3
1066
CF3
1067
CF3
1068
CF3
1069
CF3
1070
CF2CF3
1071
CF2CF3
1072
CF2CF3
1073
CH2F
1074
CH2F
1075
CH2F
1076
CH2F
1077
CH2F
1078
CH2F
1079
CHF2
1080
CHF2
1081
CF2CF3
1082
CF2CF3
1083
CF2CF3
1084
CH2F
1085
CHF2
1086
CHF2
1089
CHF2
1096
CF2CF3
1097
CF2CF3
1098
CF3
1099
CF3
1100
CF3
1101
CF3
1102
CF3
1107
CF3
1109
CF3
1110
CF3
1111
CF3
1112
CF3
1113
CF3
1114
CF3
1115
CF3
1116
CF3
1117
CF3
1118
CF3
1119
CF3
1120
CF3
1121
CF3
1122
CF3
1123
CF3
1124
CF3
1125
CF3
1126
CF3
1127
CF3
1128
CF3
1129
CF3
1130
CF3
1131
CF3
1132
CF3
1133
CF3
1134
CF3
1135
CF3
1136
CF3
1137
CF3
1138
CF3
1139
CF3
1140
CF3
1141
CF3
1142
CF3
1143
CF3
1144
CF3
1145
CF3
1146
CF3
1147
CF3
1148
CF3
1149
CF3
1150
CF3
1151
CF3
1152
CF3
1153
CF3
1154
CF3
1155
CF3
1156
CF3
1157
CF3
1158
CF3
1159
CF3
1160
CF3
1161
CF3
1162
CF3
1163
CF3
1164
CF3
1165
CF3
1166
CF3
1167
CF3
1168
CF3
1169
CF3
1170
CF3
1171
CF3
1172
CF3
1173
CF3
1174
CF3
1175
CF3
1176
CF3
1177
CF3
1178
CF3
1179
CF3
1180
CF3
1181
CF3
1182
CF3
1183
CF3
1184
CF3
1185
CF3
1186
CF3
1187
CF3
1188
CF3
1189
CF3
1190
CF3
1191
CF3
1192
CF3
1193
CF3
1194
CF3
1195
CF3
1196
CF3
1197
CF3
1198
CF3
1199
CF3
1200
CF3
1201
CF3
1202
CF3
1203
CF3
1204
CF3
1205
CF3
1206
CF3
1207
CF3
1208
CF3
1209
CF3
1210
CF3
1211
CF3
1212
CF3
1213
CF3
1214
CF3
1215
CF3
1216
CF3
1217
CF3
1218
CF3
1219
CF3
1220
CF3
1221
CF3
1222
CF3
1223
CF3
1224
CF3
1225
CF3
1226
CF3
1227
CF3
1228
CF3
1229
CF3
1230
CF3
1231
CF3
1232
CF3
1233
CF3
1234
CF3
1235
CF3
1236
CF3
1237
CF3
1238
CF3
1239
CF3
1240
CF3
1241
CF3
1242
CF3
1243
CF3
1244
CF3
1245
CF3
1246
CF3
1247
CF3
1248
CF3
1249
CF3
1250
CF3
1251
CF3
1252
CF3
1253
CF3
1254
CF3
1255
CF3
1256
CF3
1257
CF3
1258
CF3
1259
CF3
1260
CF3
1261
CF3
1262
CF3
1263
CF3
1264
CF3
1265
CF3
1266
CF3
1267
CF3
1268
CF3
1269
CF3
1270
CF3
1271
CF3
1272
CF3
1273
CF3
1274
CF3
1275
CF3
1276
CF3
1277
CF3
1278
CF3
1279
CF3
1280
CF3
1281
CF3
1282
CF3
1283
CF3
1284
CF3
1285
CF3
1286
CF3
1287
CF3
1288
CF3
1289
CF3
1290
CF3
1291
CF3
1292
CF3
1293
CF3
1294
CF3
1295
CF3
1296
CF3
1297
CF3
1298
CF3
1299
CF3
1300
CF3
1301
CF3
1302
CF3
1303
CF3
1304
CF3
1305
CF3
1306
CF3
1307
CF3
1308
CF3
1309
CF3
1310
CF3
1311
CF3
1312
CF3
1313
CF3
1314
CF3
1315
CF3
1316
CF3
1317
CF3
1318
CF3
1319
CF3
1320
CF3
1321
CF3
1322
CF3
1323
CF3
1324
CF3
1325
CF3
1326
CF3
1327
CF3
1328
CF3
1329
CF3
1330
CF3
1331
CF3
1332
CF3
1333
CF3
1334
CF3
1335
CF3
1336
CF3
1337
CF3
1338
CF3
1339
CF3
1340
CF3
1341
CF3
1342
CF3
1343
CF3
1344
CF3
1345
CF3
1346
CF3
1347
CF3
1348
CF3
1349
CF3
1350
CF3
1351
CF3
1352
CF3
1353
CF3
1354
CF3
1355
CF3
1356
CF3
1357
CF3
1358
CF3
1359
CF3
1360
CF3
1361
CF3
1362
CF3
1363
CF3
1364
CF3
1365
CF3
1366
CF3
1367
CF3
1368
CF3
1369
CF3
1370
CF3
1371
CF3
1372
CF3
1373
CF3
1374
CF3
1375
CF3
1376
CF3
1377
CF3
1378
CF3
1379
CF3
1380
CF3
1381
CF3
1382
CF3
1383
CF3
1384
CF3
1385
CF3
1386
CF3
1387
CF3
1388
CF3
1389
CF3
1390
CF3
1391
CF3
1392
CF3
1393
CF3
1394
CF3
1395
CF3
1396
CF3
1397
CF3
1398
CF3
1399
CF3
1400
CF3
1401
CF3
1402
CF3
1403
CF3
1404
CF3
1405
CF3
1406
CF3
1407
CF3
1408
CF3
1409
CF3
1410
CF3
1411
CF3
1412
CF3
1413
CF3
1414
CF3
1415
CF3
1416
CF3
1417
CF3
1418
CF3
1419
CF3
1420
CF3
1421
CF3
1422
CF3
1423
CF3
1424
CF3
1425
CF3
1426
CF3
1427
CF3
1428
CF3
1429
CF3
1430
CF3
1431
CF3
1432
CF3
1433
CF3
1434
CF3
1435
CF3
1436
CF3
1437
CF3
1438
CF3
1439
CF3
1440
CF3
1441
CF3
1442
CF3
1443
CF3
1444
CF3
1445
CF3
1446
CF3
1447
CF3
1448
CF3
1449
CF3
1450
CF3
1451
CF3
1452
CF3
1453
CF3
1454
CF3
1455
CF3
1456
CF3
1457
CF3
1458
CF3
1459
CF3
1460
CF3
1461
CF3
1462
CF3
1463
CF3
1464
CF3
1465
CF3
1466
CF3
1467
OCH3
1468
CF3
1469
CF3
1470
CF2CF3
1471
CH2F
1472
CHF2
1473
CF2CF3
1474
CH2F
1475
CHF2
1476
CF2CF3
1477
CH2F
1478
OCHF2
1479
CF2CF3
1480
CF2CF3
1481
CF2CF3
1482
CF2CF3
1483
Ph
1484
CF2CF3
1485
CF2CF3
1486
CF2CF3
1487
CN
1488
CF2CF3
1489
CF2CF3
1490
CF2CF3
1491
CF2CF3
1492
CF2CF3
1493
CF3
1494
CF3
1495
CF3
1496
CF3
1497
CF3
1498
CF3
1499
CF3
1500
CF3
1501
OCF3
1502
CF3
1503
CF3
1504
CF3
1505
CF3
1506
CF3
1507
CONH2
1508
CF3
1509
CF3
1512
CF3
1522
CF3
1523
CF3
1524
CF3
1526
CF3
1527
OH
1528
CF3
1529
CF3
1530
CF3
1531
CF3
1532
CF3
1534
OCF3
1535
CF3
1536
CN
1537
CF3
1538
CF3
1539
CF3
1540
CF3
1541
CF3
1542
CF3
1543
CF2CF3
1544
CF3
1545
CF3
1546
CF3
1547
CHF2
1548
CF3
1549
CF3
wherein the derivative is an agriculturally acceptable salt or a compound derivatized from 4-hydroxy of the pyridazine ring of the Formula I, further wherein the compound derivatized from 4-hydroxy of the pyridazine ring of the Formula I is selected from an ester, an oxime, and a hydroxylamine thereof.

2,800 more elements

A compound as shown in Formula I-1:

wherein, M is (thio)formyl, C1-C18 alkyl(thio)carbonyl, wherein said (thio)formyl or C1-C18 alkyl(thio)carbonyl is unsubstituted or substituted with a substituent independently selected from:
halogen, amino, C3-C8 cycloalkyl, C1-C8 alkoxycarbonyl, C1-C8 alkylcarbonyloxy, C1-C8 alkylcarbonyl, hydroxy(methyl)phosphinyl, and an unsubstituted or halogenated or C1-C8 alkoxy substituted group selected from phenyl, phenylsulfanyl, phenyloxy, and benzyloxy;
an unsubstituted or phenyl substituted group of C1-C18 alkoxy(thio)carbonyl or C1-C18 alkylsulfanyl(thio)carbonyl;
C3-C8 cycloalkylsulfanyl(thio)carbonyl;
phenyl-C1-C8 alkylsulfanyl(thio)carbonyl;
C2-C8 alkenyl(thio)carbonyl, wherein said C2-C8 alkenyl(thio)carbonyl unsubstituted or substituted with a substituent selected from:
C1-C8 alkoxy, phenyl and halogenated phenyl;
(thio)benzoyl, wherein said (thio)benzoyl is unsubstituted or substituted with a substituent selected from:
halogen, hydroxy, C1-C8 alkyl, C1-C8 alkoxy, cyano, halogenated C1-C8 alkoxy, C1-C8 alkylcarbonyloxy, C1-C8 alkylcarbonylamino, amino and amino substituted with 1 or 2 C1-C8 alkyl;
halogenated sulfanyl formyl;
3- to 8-membered heterocyclyl(thio)carbonyl, wherein said 3- to 8-membered heterocyclyl(thio)carbonyl is unsubstituted or substituted with a substituent selected from C1-C8 alkyl, halogen, and C1-C8 alkylsulfanyl;
fused 5- to 14-membered bicyclic or tricyclic heterocyclyl(thio)carbonyl;
amino(thio)formyl, wherein said amino(thio)formyl is unsubstituted or substituted with a substituent selected from C1-C8 alkyl and C1-C8 alkoxy;
an unsubstituted or halogen or C1-C8 alkylsulfonyl substituted group selected from C1-C8 alkylsulfoxide, C1-C8 alkylsulfonyl, and C3-C8 cycloalkylsulfonyl;
phenylsulfonyl, benzylsulfonyl, naphthylsulfonyl, wherein each of said phenylsulfonyl, benzylsulfonyl or naphthylsulfonyl is unsubstituted or substituted with a substituent independently selected from:
halogen, nitro, C1-C8 alkyl, halogenated C1-C8 alkyl, halogenated C1-C8 alkoxy, C1-C8 alkylcarbonyl, C1-C8 alkylsulfonyl, aminoformyl, phenoxy and halogenated phenoxy;
5- to 10-membered heteroarylsulfonyl, wherein said 5- to 10-membered heteroarylsulfonyl is unsubstituted or substituted with C1-C8 alkyl or phenoxy;
C1-C8 alkylaminosulfonyl that is unsubstituted or substituted with halogen;
di(C1-C8 alkyl) phosphoryl;
C1-18alkyl substituted with a substituent independently selected from C1-C8 alkoxycarbonyl and C1-C8 alkoxycarbonyloxy;
an unsubstituted or halogenated or C1-C8 alkoxy substituted group selected from phenyl, benzyl, and benzoyl-C1-C8 alkyl;
wherein,
R11 and R22 are independently selected from hydrogen, C1-C18 alkyl, wherein said C1-C18 alkyl is unsubstituted or substituted with a substituent selected from C1-C8 alkoxy and C1-C8 alkylsulfanyl, and an unsubstituted or halogenated C1-C8 alkyl substituted group selected from phenyl and 5- to 6-membered heteroaryl;
or R11 and R12 forms a 5- to 6-membered saturated carbocyclic ring or a 5- to 6-membered saturated heterocyclic ring;
R11′ and R22′ independently is C1-C18 alkyl;
Het is selected from
Ra and Rb independently are hydrogen or C1-C6 alkyl;
wherein, X is halogenated alkyl;
A is selected from alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl, aryl, heteroaryl, and aliphatic heterocyclyl, each of which is unsubstituted or substituted;
wherein,
when being substituted, each of said alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, or cycloalkylalkyl is independently substituted with one or more substituents selected from halogen, cyano, nitro, azido, unsubstituted or substituted aryl, unsubstituted or substituted heteroaryl, —(CH2)n-O—(CH2)p-, —(CH2)n-S—(CH2)p-, —(CH2)n-NR3-(CH2)p-, R—O—, R—O—(CH2)p-O—, R—O—(CH2)p-S—, R—S—, R—S—(CH2)p-O—, R—S—(CH2)p-S—, R—O—(CH2)n-(C═O)—(CH2)q-(O)m-, R—S—(CH2)n-(C═S)—(CH2)q-(S)m-, R—O—(CH2)n-(C═O)—(CH2)q-(S)m-, R—O—(CH2)n-(C═S)—(CH2)q-(O)m-, R—S—(CH2)n-(C═O)—(CH2)q-(O)m-, R—O—(CH2)n-(C═S)—(CH2)q-(S)m-, R—S—(CH2)n-(C═O)—(CH2)q-(S)m-, R—S—(CH2)n-(C═S)—(CH2)q-(O)m-, R—(C═O)—, R—(C═S)—, R—(C═O)—(CH2)n-O—, R—(C═S)—(CH2)n-S—, R—(C═O)—(CH2)n-S—, R—(C═S)—(CH2)n-O—, R—SO—(CH2)n-(O)m-, R—SO—(CH2)n-(S)m-, R—SO—(CH2)n-(NR3)m-, R—SO2-(CH2)n-(O)m-, R—SO2-(CH2)n-(S)m-, R—SO2-(CH2)n-(NR3)m-SR1R2N—, R1 R2N—(CH2)n-O—(CH2)q-(O)m-, R1 R2N—(CH2)n-O—(CH2)q-(S)m-, R1 R2N—(CH2)n-O—(CH2)q-(NR3)m-, R1 R2N—(CH2)n-(C═O)—(CH2)q-(O)m-, R1 R2N—(CH2)n-(C═O)—(CH2)q-(S)m-, R1 R2N—(CH2)n-(C═O)—(CH2)q-(NR3)m-, R1 R2N—(CH2)n-SO2-(CH2)q-(O)m-, R1 R2N—(CH2)n-SO2-(CH2)q-(S)m-, R1 R2N—(CH2)n-SO2-(CH2)q-(NR3)m-, R1 R2P(O)—(O)m-, R1 R2R3SiO—, R1 R2R3Si—(CH═CH)m-, R1 R2C═N—(O)m-, and R1 R2C═N—NH—;
when being substituted, each of said aryl, heteroaryl, or aliphatic heterocyclyl is substituted with one or more substituents selected from halogen, cyano, nitro, azido, a halogen-containing or not containing group selected from alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, and cycloalkylalkyl, a group selected from aryl, arylalkyl, heteroaryl, heteroarylalkyl, aliphatic heterocyclyl, and aliphatic heterocyclylalkyl, which is unsubstituted or substituted, R—O—(CH2)n-, R—O—(CH2)p-O—(CH2)q-, R—O—(CH2)p-S—(CH2)q-, R—S—(CH2)n-, R—S—(CH2)p-O—(CH2)q-, R—S—(CH2)p-S—(CH2)q-, R—O—(CH2)n-(C═O)—(CH2)q-(O)m-, R—S—(CH2)n-(C═S)—(CH2)q-(S)m-, R—O—(CH2)n-(C═O)—(CH2)q-(S)m-, R—O—(CH2)n-(C═S)—(CH2)q-(O)m-, R—S—(CH2)n-(C═O)—(CH2)q-(O)m-, R—O—(CH2)n-(C═S)—(CH2)q-(S)m-, R—S—(CH2)n-(C═O)—(CH2)q-(S)m-, R—S—(CH2)n-(C═S)—(CH2)q-(O)m-, R—(C═O)—(CH2)n-, R—(C═S)—(CH2)n-, R—(C═O)—(CH2)n-O—(CH2)q-, R—(C═S)—(CH2)n-S—(CH2)q-, R—(C═O)—(CH2)n-S—(CH2)q-, R—(C═S)—(CH2)n-O—(CH2)q-, R—SO—(CH2)n-(O)m-, R—SO—(CH2)n-(S)m-, R—SO—(CH2)n-(NR3)m-, R—SO2-(CH2)n-(O)m-, R—SO2-(CH2)n-(S)m-, R—SO2-(CH2)n-(NR3)m-, R1 R2N—(CH2)n-, R1 R2N—(CH2)n-O—(CH2)q-(O)m-, R1 R2N—(CH2)n-O—(CH2)q-(S)m-, R1 R2N—(CH2)n-O—(CH2)q-(NR3)m-, R1 R2N—(CH2)n-(C═O)—(CH2)q-(O)m-, R1 R2N—(CH2)n-(C═O)—(CH2)q-(S)m-, R1 R2N—(CH2)n-(C═O)—(CH2)q-(NR3)m-, R1 R2N—(CH2)n-SO2-(CH2)q-(O)m-, R1 R2N—(CH2)n-SO2-(CH2)q-(S)m-, R1 R2N—(CH2)n-SO2-(CH2)q-(NR3)m-, R1 R2PO3-(O)m-(CH2)q-, R1 R2R3SiO—(CH2)q-, R1 R2R3Si—(CH═CH)m-(CH2)q-, R1 R2C═N—(O)m-(CH2)n-, and R1 R2C═N—NH—(CH2)n-;
m is 0 or 1, n and q are independently an integer from 0 to 8, p is an integer from 1 to 8;
R is hydrogen, a halogen-containing or not containing group selected from alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, and cycloalkylalkyl, or a group selected from aryl, arylalkyl, heteroaryl, and heteroarylalkyl, which is unsubstituted or substituted;
R1, R2, R3 are each independently hydrogen, nitro, hydroxy, amino, a halogen-containing or not containing group selected from alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl, alkoxy, alkenyloxy, alkynyloxy, cycloalkyloxy, alkoxyalkyl, alkoxycarbonyl, alkylsulfanylcarbonyl, alkylsulfonyl, alkylsulfonylalkyl, alkylcarbonyl, alkylcarbonylalkyl, alkylcarbonyloxy, alkylamino, alkylaminocarbonyl, alkoxyaminocarbonyl, alkoxycarbonylalkyl, alkylaminocarbonylalkyl, trialkylsilyl, and dialkylphosphonyl, or a group selected from aryl, arylalkyl, aryloxy, arylalkyloxy, aryloxyalkyl, arylcarbonyl, arylsulfonyl, heteroaryl, heteroarylalkyl, heteroaryloxy, heteroarylalkyloxy, heteroaryloxyalkyl, heteroarylcarbonyl, heteroarylsulfonyl, aliphatic heterocyclyl, aliphatic heterocyclylalkyl, aliphatic heterocyclyloxy, aliphatic heterocyclylalkoxy, aliphatic heterocyclyloxyalkyl, aliphatic heterocyclylcarbonyl, and aliphatic heterocyclylsulfonyl, which is unsubstituted or substituted;
or R1 R2N— forms a 5- to 6-membered heterocyclyl.

33 more elements

Dependencies are inferred from the claim text.

Facts

Application: 16/966,667Filed 1 Feb 2019
Priority: CN 201810104963.42 Feb 2018
Published: US 2022/0312770 A16 Oct 2022
Granted: 10 Mar 2026
Term ends: Not estimatedThe source records don’t support an estimate.

Classification34 codes

A01N 57/32
Having phosphorus-to-nitrogen bonds: containing heterocyclic radicals
A01N 43/58
Having rings with two nitrogen atoms as the only ring hetero atoms: 1,2-Diazines; Hydrogenated 1,2-diazines
A01N 43/60
Having rings with two nitrogen atoms as the only ring hetero atoms: 1,4-Diazines; Hydrogenated 1,4-diazines
A01N 43/647
Having rings with three nitrogen atoms as the only ring hetero atoms: triazoles; Hydrogenated triazoles

Family

US 2022/0312770 A1Pre-grant publication · published 6 Oct 2022
US 12,568,972 B2This patent

From the US filing history. Foreign family members aren’t listed.

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Abstract

A herbicidally active pyridazinol compound of Formula I or a derivative thereof:

wherein, X is halogenated alkyl;
A is selected from unsubstituted or substituted C2-C8 alkenyl, unsubstituted or substituted C2-C8 alkynyl, unsubstituted or substituted C3-C8 cycloalkyl, unsubstituted or substituted C3-C8 cycloalkenyl, unsubstituted or substituted C3-C8 cycloalkyl-C1-C8 alkyl, unsubstituted or substituted
unsubstituted or substituted 5- to 14-membered heteroaryl, and unsubstituted or substituted 5- to 14-membered aliphatic heterocyclyl;
wherein,
when being substituted, said C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, or C3-C8 cycloalkyl-C1-C8 alkyl is substituted with one or more substituents independently selected from halogen, cyano, nitro, azido, aryl, and heteroaryl, said aryl or heteroaryl is unsubstituted or independently substituted with 1-5 groups selected from halogen, cyano, nitro, hydroxy, carboxyl, sulfhydryl, amino, and a halogen-containing or not containing group selected from C1-C8 alkyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkyl-C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C1-C8 alkoxy, C1-C8 alkylcarbonyl, C1-C8 alkoxycarbonyl, C1-C8 alkylsulfonyl, C1-C8 alkylamino, and C1-C8 alkylcarbonyloxy, —(CH2)n-O—(CH2)p-, —(CH2)n-S—(CH2)p-, —(CH2)n-NR3-(CH2)p-, R—O—, R—O—(CH2)p-O—, R—O—(CH2)p-S—, R—S—, R—S—(CH2)p-O—, R—S—(CH2)p-S—, R—O—(C═O)—(CH2)q-(O)m-, R—O—(CH2)n-(C═O)—(O)m-, R—O—(CH2)n-(C═O)—, R—S—(C═S)—(CH2)q-(S)m-, R—S—(CH2)n-(C═S)—(S)m-, R—S—(CH2)n-(C═S)—, R—O—(C═O)—(CH2)q-(S)m-, R—O—(CH2)n-(C═O)—(S)m-, R—O—(C═S)—(CH2)q-(O)m-, R—O—(CH2)n-(C═S)—(O)m-, R—O—(CH2)n-(C═S)—, R—S—(C═O)—(CH2)q-(O)m-, R—S—(CH2)n-(C═O)—(O)m-, R—S—(CH2)n-(C═O)—, R—O—(C═S)—(CH2)q-(S)m-, R—O—(CH2)n-(C═S)—(S)m-, R—S—(C═O)—(CH2)q-(S)m-, R—S—(CH2)n-(C═O)—(S)m-, R—S—(C═S)—(CH2)q-(O)m-, R—S—(CH2)n-(C═S)—(O)m-, R—(C═O)—, R—(C═S)—, R—(C═O)—O—, R—(C═S)—S—, R—(C═O)—S—, R—(C═S)—O—, R—SO—(O)m-, R—SO—(S)m-, R—SO—(NR3)m-, R—SO2-(O)m-, R—SO2-(S)m-, R—SO2(NR3)m-, R1 R2N—, R1 R2N—O—(CH2)q-(O)m-, R1 R2N—(CH2)n-O—, R1 R2N—O—(CH2)q-(S)m-, R1 R2N—O—(CH2)q-(NR3)m-, R1 R2N—(C═O)—(CH2)q-(O)m-, R1 R2N—(CH2)n-(C═O)—(O)m-, R1 R2N—(CH2)n-(C═O)—, R1 R2N—(C═O)—(CH2)q-(S)m-, R1 R2N—(CH2)n-(C═O)—(S)m-, R1 R2N—(C═O)—(CH2)q-(NR3)m-, R1 R2N—(CH2)n-(C═O)—(NR3)m-, R1 R2N—SO2-(CH2)q-(O)m-, R1 R2N—(CH2)n-SO2-(O)m-, R1 R2N—(CH2)n-SO2-, R1 R2N—SO2-(CH2)q-(S)m-, R1 R2N—(CH2)n-SO2-(S)m-, R1 R2N—SO2-(CH2)q-(NR3)m-, R1 R2N—(CH2)n-SO2-(NR3)m-, R1 R2P(O)—, R1 R2R3SiO—, R1 R2R3Si—(CH═CH)m-, R1 R2C═N—(O)m-, and R1 R2C═N—NH—;
when being substituted, each of said
5- to 14-membered heteroaryl or 5- to 14-membered aliphatic heterocyclyl is independently substituted with one or more substituents selected from halogen, cyano, nitro, azido, a halogen-containing or not containing group selected from C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, and C3-C8 cycloalkyl-C1-C8 alkyl, aryl, aryl-C1-C8 alkyl, heteroaryl, heteroaryl-C1-C8 alkyl, aliphatic heterocyclyl, and aliphatic heterocyclyl-C1-C8 alkyl, each of said aryl, aryl-C1-C8 alkyl, heteroaryl, heteroaryl-C1-C8 alkyl, aliphatic heterocyclyl, or aliphatic heterocyclyl-C1-C8 alkyl is unsubstituted or substituted with 1-5 groups independently selected from halogen, cyano, nitro, hydroxy, carboxyl, sulfhydryl, amino, and a halogen-containing or not containing group selected from C1-C8 alkyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkyl-C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C1-C8 alkoxy, C1-C8 alkylcarbonyl, C1-C8 alkoxycarbonyl, C1-C8 alkylsulfonyl, C1-C8 alkylamino, and C1-C8 alkylcarbonyloxy, R—O—(CH2)n-, R—O—(CH2)p-O—(CH2)q-, R—O—(CH2)p-S—(CH2)q-, R—S—(CH2)n-, R—S—(CH2)p-O—(CH2)q-, R—S—(CH2)p-S—(CH2)q-, R—O—(CH2)n-(C═O)—(CH2)q-(O)m-, R—S—(CH2)n-(C═S)—(CH2)q-, R—O—(CH2)n-(C═S)—(CH2)q-, R—S—(CH2)n-(C═O)—(CH2)q-, R—S—(C═S)—(CH2)q-(S)m-, R—O—(CH2)n-(C═O)—(CH2)q-(S)m-, R—O—(C═S)—(CH2)q-(O)m-, R—S—(C═O)—(CH2)q-(O)m-, R—O—(C═S)—(CH2)q-(S)m-, R—S—(C═O)—(CH2)q-(S)m-, R—S—(C═S)—(CH2)q-(O)m-, R—S—(CH2)n-(C═S)—(S)m-, R—O—(CH2)n-(C═S)—(O)m-, R—S—(CH2)n-(C═O)—(O)m-, R—O—(CH2)n-(C═S)—(S)m-, R—S—(CH2)n-(C═O)—(S)m-, R—S—(CH2)n-(C═S)—(O)m-, R—(C═O)—(CH2)n-, R—(C═S)—, R—(C═O)—(CH2)n-O—(CH2)q-, R—(C═S)—(CH2)n-S—, R—(C═O)—(CH2)n-S—, R—(C═S)—(CH2)n-O—, R—(C═S)—S—(CH2)q-, R—(C═O)—S—(CH2)q-, R—(C═S)—O—(CH2)q-, R—SO—(O)m-, R—SO—(S)m-, R—SO—(NR3)m-, R—SO2-(CH2)n-(O)m-, R—SO2-(S)m-, R—SO2-(CH2)n-(NR3)m-, R—SO—(CH2)n-, R1 R2N—(CH2)n-, R1 R2N—(CH2)n-O—(CH2)q-, R1 R2N—(C═O)—(CH2)q-(O)m-, R1 R2N—(CH2)n-(C═O)—(CH2)q-, R1 R2N—(CH2)n-(C═O)—(O)m-, R1 R2N—(CH2)n-(C═O)—(S)m-, R1 R2N—(CH2)n-(C═O)—(NR3)m-, R1 R2N—(CH2)n-SO2-(CH2)q-(O)m-, R1 R2N—(CH2)n-SO2-(S)m-, R1 R2N—(CH2)n-SO2-(NR3)m-, R1 R2N—(C═O)—(CH2)n-(O)m-, R1 R2N—(C═O)—(CH2)n-(S)m-, R1 R2N—(C═O)—(CH2)n-(NR3)m-, R1 R2N—SO2-(CH2)q-(S)m-, R1 R2N—SO2-(CH2)q-(NR3)m-, R1 R2N—(CH2)n-O—, R1 R2N—O—(CH2)q-, R1 R2P(O)—(O)m-, R1 R2R3SiO—, R1 R2R3Si—(CH═CH)m-, R1 R2C═N—(O)m-, and R1 R2C═N—NH—;
m is 0 or 1, n and q are independently an integer from 0 to 6, p is an integer from 1 to 6;
R is hydrogen, a halogen-containing or not containing group selected from C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, and C3-C8 cycloalkyl-C1-C8 alkyl, aryl, aryl-C1-C8 alkyl, heteroaryl, or heteroaryl-C1-C8 alkyl, each of said aryl, aryl-C1-C8 alkyl, heteroaryl, or heteroaryl-C1-C8 alkyl is unsubstituted or substituted with 1-5 groups substituents independently selected from halogen, cyano, nitro, hydroxy, carboxyl, sulfhydryl, amino, and a halogen-containing or not containing group selected from C1-C8 alkyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkyl-C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C1-C8 alkoxy, C1-C8 alkylcarbonyl, C1-C8 alkoxycarbonyl, C1-C8 alkylsulfonyl, C1-C8 alkylamino, and C1-C8 alkylcarbonyloxy;
R1, R2, R3 are each independently hydrogen, nitro, hydroxy, amino, a halogen-containing or not containing group selected from C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkyl-C1-C8 alkyl, C1-C8 alkoxy, C2-C8 alkenyloxy, C2-C8 alkynyloxy, C3-C8 cycloalkyloxy, C1-C8 alkoxy-C1-C8 alkyl, C1-C8 alkoxycarbonyl, C1-C8 alkylcarbonyl-C1-C8 alkyl, C1-C8 alkylsulfanylcarbonyl, C1-C8 alkylsulfonyl, C1-C8 alkylsulfonyl-C1-C8 alkyl, C1-C8 alkylcarbonyl, C1-C8 alkylcarbonyloxy, C1-C8 alkylamino, C1-C8 alkylaminocarbonyl, C1-C8 alkoxyaminocarbonyl, C1-C8 alkoxycarbonyl-C1-C8 alkyl, C1-C8 alkylaminocarbonyl-C1-C8 alkyl, triC1-C8 alkylsilyl, and diC1-C8 alkylphosphonyl, aryl, aryl-C1-C8 alkyl, aryloxy, aryl-C1-C8 alkyloxy, aryloxy-C1-C8 alkyl, arylcarbonyl, arylsulfonyl, heteroaryl, heteroaryl-C1-C8 alkyl, heteroaryloxy, heteroaryl-C1-C8 alkyloxy, heteroaryloxy-C1-C8 alkyl, heteroarylcarbonyl, heteroarylsulfonyl, aliphatic heterocyclyl, aliphatic heterocyclyl-C1-C8 alkyl, aliphatic heterocyclyloxy, aliphatic heterocyclyl-C1-C8 alkyloxy, aliphatic heterocyclyloxy-C1-C8 alkyl, aliphatic heterocyclylcarbonyl, or aliphatic heterocyclylsulfonyl, each of said aryl, aryl-C1-C8 alkyl, aryloxy, aryl-C1-C8 alkyloxy, aryloxy-C1-C8 alkyl, arylcarbonyl, arylsulfonyl, heteroaryl, heteroaryl-C1-C8 alkyl, heteroaryloxy, heteroaryl-C1-C8 alkyloxy, heteroaryloxy-C1-C8 alkyl, heteroarylcarbonyl, heteroarylsulfonyl, aliphatic heterocyclyl, aliphatic heterocyclyl-C1-C8 alkyl, aliphatic heterocyclyloxy, aliphatic heterocyclyl-C1-C8 alkyloxy, aliphatic heterocyclyloxy-C1-C8 alkyl, aliphatic heterocyclylcarbonyl, or aliphatic heterocyclylsulfonyl is unsubstituted or substituted with 1-5 groups independently selected from halogen, cyano, nitro, hydroxy, carboxyl, sulfhydryl, amino, and a halogen-containing or not containing group selected from C1-C8 alkyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkyl-C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C1-C8 alkoxy, C1-C8 alkylcarbonyl, C1-C8 alkoxycarbonyl, C1-C8 alkylsulfonyl, C1-C8 alkylamino, and C1-C8 alkylcarbonyloxy;
or R1 R2N— forms a 5- to 6-membered heterocyclyl;
or
wherein A is phenyl or 7- to 14-membered aryl, which is substituted with one or more substituents independently selected from azido, halogenated C1-C8 alkyl, a halogen-containing aryl, a halogen-containing aryl-C1-C8 alkyl, a halogen-containing or not containing group selected from C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, and C3-C8 cycloalkyl-C1-C8 alkyl, heteroaryl, heteroaryl-C1-C8 alkyl, aliphatic heterocyclyl, and aliphatic heterocyclyl-C1-C8 alkyl, each of said heteroaryl, heteroaryl-C1-C8 alkyl, aliphatic heterocyclyl, or aliphatic heterocyclyl-C1-C8 alkyl is unsubstituted or substituted with 1-5 groups independently selected from halogen, cyano, nitro, hydroxy, carboxyl, sulfhydryl, amino, and a halogen-containing or not containing group selected from C1-C8 alkyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkyl-C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C1-C8 alkoxy, C1-C8 alkylcarbonyl, C1-C8 alkoxycarbonyl, C1-C8 alkylsulfonyl, C1-C8 alkylamino, and C1-C8 alkylcarbonyloxy, R—O—(CH2)n-, R—O—(CH2)p-O—(CH2)q-, R—O—(CH2)p-S—(CH2)q-, R—S—(CH2)n-, R—S—(CH2)p-O—(CH2)q-, R—S—(CH2)p-S—(CH2)q-, R—O—(CH2)n-(C═O)—(CH2)q-(O)m-, R—S—(CH2)n-(C═S)—(CH2)q-, R—O—(CH2)n-(C═S)—(CH2)q-, R—S—(CH2)n-(C═O)—(CH2)q-, R—S—(C═S)—(CH2)q-(S)m-, R—O—(CH2)n-(C═O)—(CH2)q-(S)m-, R—O—(C═S)—(CH2)q-(O)m-, R—S—(C═O)—(CH2)q-(O)m-, R—O—(C═S)—(CH2)q-(S)m-, R—S—(C═O)—(CH2)q-(S)m-, R—S—(C═S)—(CH2)q-(O)m-, R—S—(CH2)n-(C═S)—(S)m-, R—O—(CH2)n-(C═S)—(O)m-, R—S—(CH2)n-(C═O)—(O)m-, R—O—(CH2)n-(C═S)—(S)m-, R—S—(CH2)n-(C═O)—(S)m-, R—S—(CH2)n-(C═S)—(O)m-, R—(C═O)—(CH2)n-, R—(C═S)—, R—(C═O)—(CH2)n-O—(CH2)q-, R—(C═S)—(CH2)n-S—, R—(C═O)—(CH2)n-S—, R—(C═S)—(CH2)n-O—, R—(C═S)—S—(CH2)q-, R—(C═O)—S—(CH2)q-, R—(C═S)—O—(CH2)q-, R—SO—(O)m-, R—SO—(S)m-, R—SO—(NR3)m-, R—SO2-(CH2)n-(O)m-, R—SO2-(S)m-, R—SO2-(CH2)n-(NR3)m-, R—SO—(CH2)n-, R1 R2N—(CH2)n-, R1 R2N—(CH2)n-O—(CH2)q-, R1 R2N—(C═O)—(CH2)q-(O)m-, R1 R2N—(CH2)n-(C═O)—(CH2)q-, R1 R2N—(CH2)n-(C═O)—(O)m-, R1 R2N—(CH2)n-(C═O)—(S)m-, R1 R2N—(CH2)n-(C═O)—(NR3)m-, R1 R2N—(CH2)n-SO2-(CH2)q-(O)m-, R1 R2N—(CH2)n-SO2-(S)m-, R1 R2N—(CH2)n-SO2-(NR3)m-, R1 R2N—(C═O)—(CH2)n-(O)m-, R1 R2N—(C═O)—(CH2)n-(S)m-, R1 R2N—(C═O)—(CH2)n-(NR3)m-, R1 R2N—SO2-(CH2)q-(S)m-, R1 R2N—SO2-(CH2)q-(NR3)m-, R1 R2N—(CH2)n-O—, R1 R2N—O—(CH2)q-, R1 R2P(O)—(O)m-, R1 R2R3SiO—, R1 R2R3Si—(CH═CH)m-, R1 R2C═N—(O)m-, and R1 R2C═N—NH—;
wherein the derivative is an agriculturally acceptable salt or a compound derivatized from 4-hydroxy of the pyridazine ring of the Formula I, further wherein the compound derivatized from 4-hydroxy of the pyridazine ring of the Formula I is selected from an ester, an oxime, and a hydroxylamine thereof.

11 more elements

Facts

Application

16/966,667Filed 1 Feb 2019

Priority

CN 201810104963.42 Feb 2018

Published

US 2022/0312770 A16 Oct 2022

Granted

10 Mar 2026

Term ends

Not estimatedThe source records don’t support an estimate.

Classification34 codes

A01N 57/32
Having phosphorus-to-nitrogen bonds: containing heterocyclic radicals
A01N 43/58
Having rings with two nitrogen atoms as the only ring hetero atoms: 1,2-Diazines; Hydrogenated 1,2-diazines
A01N 43/60
Having rings with two nitrogen atoms as the only ring hetero atoms: 1,4-Diazines; Hydrogenated 1,4-diazines
A01N 43/647
Having rings with three nitrogen atoms as the only ring hetero atoms: triazoles; Hydrogenated triazoles