CN110520414B - 取代的n-(-1,3,4-噁二唑-2-基)芳基羧酰胺及其作为除草剂的用途 - Google Patents
取代的n-(-1,3,4-噁二唑-2-基)芳基羧酰胺及其作为除草剂的用途 Download PDFInfo
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- CN110520414B CN110520414B CN201880023342.1A CN201880023342A CN110520414B CN 110520414 B CN110520414 B CN 110520414B CN 201880023342 A CN201880023342 A CN 201880023342A CN 110520414 B CN110520414 B CN 110520414B
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- alkyl
- methyl
- ethyl
- oxadiazol
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- YPMAQKXGDCKXPE-WCCKRBBISA-M sodium;[(3s)-3-amino-3-carboxypropyl]-methylphosphinate Chemical compound [Na+].CP([O-])(=O)CC[C@H](N)C(O)=O YPMAQKXGDCKXPE-WCCKRBBISA-M 0.000 description 1
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- PQTBTIFWAXVEPB-UHFFFAOYSA-N sulcotrione Chemical compound ClC1=CC(S(=O)(=O)C)=CC=C1C(=O)C1C(=O)CCCC1=O PQTBTIFWAXVEPB-UHFFFAOYSA-N 0.000 description 1
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- ZDXMLEQEMNLCQG-UHFFFAOYSA-N sulfometuron methyl Chemical group COC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(C)=CC(C)=N1 ZDXMLEQEMNLCQG-UHFFFAOYSA-N 0.000 description 1
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- RJKCKKDSSSRYCB-UHFFFAOYSA-N tebutam Chemical compound CC(C)(C)C(=O)N(C(C)C)CC1=CC=CC=C1 RJKCKKDSSSRYCB-UHFFFAOYSA-N 0.000 description 1
- IUQAXCIUEPFPSF-UHFFFAOYSA-N tembotrione Chemical compound ClC1=C(COCC(F)(F)F)C(S(=O)(=O)C)=CC=C1C(=O)C1C(=O)CCCC1=O IUQAXCIUEPFPSF-UHFFFAOYSA-N 0.000 description 1
- 229960000195 terbutaline Drugs 0.000 description 1
- 229960000351 terfenadine Drugs 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000004192 tetrahydrofuran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 239000004308 thiabendazole Substances 0.000 description 1
- 235000010296 thiabendazole Nutrition 0.000 description 1
- WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 description 1
- 229960004546 thiabendazole Drugs 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000000858 thiocyanato group Chemical group *SC#N 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- DQFPEYARZIQXRM-LTGZKZEYSA-N tralkoxydim Chemical compound C1C(=O)C(C(/CC)=N/OCC)=C(O)CC1C1=C(C)C=C(C)C=C1C DQFPEYARZIQXRM-LTGZKZEYSA-N 0.000 description 1
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- 229960005294 triamcinolone Drugs 0.000 description 1
- YMXOXAPKZDWXLY-QWRGUYRKSA-N tribenuron methyl Chemical group COC(=O)[C@H]1CCCC[C@@H]1S(=O)(=O)NC(=O)N(C)C1=NC(C)=NC(OC)=N1 YMXOXAPKZDWXLY-QWRGUYRKSA-N 0.000 description 1
- 229940047183 tribulus Drugs 0.000 description 1
- NFACJZMKEDPNKN-UHFFFAOYSA-N trichlorfon Chemical compound COP(=O)(OC)C(O)C(Cl)(Cl)Cl NFACJZMKEDPNKN-UHFFFAOYSA-N 0.000 description 1
- IEDVJHCEMCRBQM-UHFFFAOYSA-N trimethoprim Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(N)=NC=2)N)=C1 IEDVJHCEMCRBQM-UHFFFAOYSA-N 0.000 description 1
- 229960001082 trimethoprim Drugs 0.000 description 1
- RVKCCVTVZORVGD-UHFFFAOYSA-N trinexapac-ethyl Chemical group O=C1CC(C(=O)OCC)CC(=O)C1=C(O)C1CC1 RVKCCVTVZORVGD-UHFFFAOYSA-N 0.000 description 1
- YNWVFADWVLCOPU-MAUPQMMJSA-N uniconazole P Chemical compound C1=NC=NN1/C([C@@H](O)C(C)(C)C)=C/C1=CC=C(Cl)C=C1 YNWVFADWVLCOPU-MAUPQMMJSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/10—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles
- C07D271/113—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
Abstract
本发明公开了式(I)的N‑(‑1,3,4‑噁二唑‑2‑基)芳基羧酰胺或其盐(I)及其作为除草剂的用途。
Description
本发明涉及除草剂的技术领域,特别是杂环取代的芳基羧酰胺在有用的植物作物中用于选择性防治阔叶杂草和禾本科杂草的领域。
杂环取代的芳基羧酰胺的除草性能是已知的。
根据这些化合物的杂环部分,现有技术的除草剂可分为四唑和三唑取代的芳基羧酰胺以及噁二唑取代的芳基羧酰胺。
文献WO 2012/028579 A1公开了在苯环的2位、3位和4位被取代的N-(四唑-4-基)苯甲酰胺和N-(三唑-3-基)苯甲酰胺,它们具有除草活性。文献WO 2014/184015 A1也公开了具有除草活性的N-(四唑-4-基)苯甲酰胺和N-(三唑-3-基)苯甲酰胺,并且在WO 2014/184015中所公开的化合物在苯环上在2位、3位、4位和5位、6位被取代。
文献WO 2011/035874 A1公开了噁二唑取代的苯甲酰胺化合物,即N-(1,2,5-噁二唑-3-基)苯基苯甲酰胺,其在苯环的2位、3位和4位被取代,并且具有除草活性。此外,N-(1,2,5-噁二唑-3-基)苯基苯甲酰胺由EP 0 173 657 A1已知。
文献WO 2012/126932 A1也公开了N-(1,3,4-噁二唑-2-基)苯甲酰胺,其中苄基(芳基部分)在每一种情况下也只是在2位、3位和4位被取代,即由WO 2012/126932 A1已知的具有除草活性的化合物在苯基部分的5位和6位未被取代。
关于本申请方面,另一篇文献WO 2017/102275 A1——其为根据54条(3)款EPC的文献——公开了另一Q4=1,3,4-噁二唑-2-基的N-(1,3,4-噁二唑-2-基)苯甲酰胺。在WO2017/102275 A1中要求保护的化合物由苯基取代基(称为R2)区分,其具有二胺结构。从本发明的范围排除了在WO 2017/102275 A1的列表(表IV,第113页)中指定的两种化合物。
此外,从本发明的范围排除了在WO 2017/102275 A1中使用的起始材料,即3-氨基-4-溴-6-氟-2-甲基-N-(5-甲基-1,3,4-噁二唑-2-基)苯甲酰胺。结合WO 2017/102275A1中的实施例3公开的这种化合物在本发明的基团Y的位置上具有氨基基团,而不是具有二酰胺结构的基团。
除了上述三种化合物,本发明的范围还排除了另外六种市售可得的化合物。对于这六种化合物,在现有技术中没有发现使用这些化合物作为除草剂。
然而,已知的N-(1,3,4-噁二唑-2-基)苯甲酰胺的除草活性往往不足。
因此,本发明的目的是提供其它的具有改善的除草活性的N-(1,3,4-噁二唑-2-基)苯甲酰胺。
该目的通过权利要求1的N-(-1,3,4-噁二唑-2-基)芳基羧酰胺实现,即通过式(I)的N-(-1,3,4-噁二唑-2-基)芳基羧酰胺或其盐实现
其中取代基具有以下含义:
A代表N或C-Y,
R代表氢、卤素、(C1-C6)-烷基、R1O-(C1-C6)-烷基、CH2R6、(C3-C7)-环烷基、卤代-(C1-C6)-烷基、(C1-C6)-烷氧基-(C1-C6)-烷基、(C2-C6)-烯基、卤代-(C2-C6)-烯基、(C2-C6)-炔基、卤代-(C2-C6)-炔基、OR1、NHR1、甲氧基羰基、乙氧基羰基、甲氧基羰基甲基、乙氧基羰基甲基、甲基羰基、三氟甲基羰基、二甲基氨基、乙酰基氨基、甲基硫基(methylsulfenyl)、甲基亚磺酰基、甲基磺酰基
或者
代表杂芳基、杂环基、苄基或苯基,各自被s个选自卤素、硝基、氰基、(C1-C6)-烷基、卤代-(C1-C6)-烷基、(C3-C6)-环烷基、S(O)n-(C1-C6)-烷基、(C1-C6)-烷氧基、卤代-(C1-C6)-烷氧基和(C1-C6)-烷氧基-(C1-C4)-烷基的基团取代,
X代表硝基、卤素、氰基、甲酰基、氰硫基、(C1-C6)-烷基、卤代-(C1-C6)-烷基、(C2-C6)-烯基、卤代-(C2-C6)-烯基、(C2-C6)-炔基、卤代-(C3-C6)-炔基、(C3-C6)-环烷基、卤代-(C3-C6)-环烷基、(C3-C6)-环烷基-(C1-C6)-烷基、卤代-(C3-C6)-环烷基-(C1-C6)-烷基、COR1、COOR1、OCOOR1、NR1COOR1、C(O)N(R1)2、NR1C(O)N(R1)2、OC(O)N(R1)2、C(O)NR1OR1、OR1、OCOR1、OSO2R2、S(O)nR2、SO2OR1、SO2N(R1)2、NR1SO2R2、NR1COR1、(C1-C6)-烷基-S(O)nR2、(C1-C6)-烷基-OR1、(C1-C6)-烷基-OCOR1、(C1-C6)-烷基-OSO2R2、(C1-C6)-烷基-CO2R1、(C1-C6)-烷基-SO2OR1、(C1-C6)-烷基-CON(R1)2、(C1-C6)-烷基-SO2N(R1)2、(C1-C6)-烷基-NR1COR1、(C1-C6)-烷基-NR1SO2R2、NR1R2、P(O)(OR5)2、CH2P(O)(OR5)2、(C1-C6)-烷基-杂芳基、(C1-C6)-烷基-杂环基,
其中两个最后提及的基团各自彼此独立地被s个选自卤素、(C1-C6)-烷基、卤代-(C1-C6)-烷基、S(O)n-(C1-C6)-烷基、(C1-C6)-烷氧基、卤代-(C1-C6)-烷氧基的基团取代,并且其中杂环基带有n个氧代基团,
Y代表氢、硝基、卤素、氰基、氰硫基、(C1-C6)-烷基、卤代-(C1-C6)-烷基、(C2-C6)-烯基、卤代-(C2-C6)-烯基、(C2-C6)-炔基、卤代-(C2-C6)-炔基、(C3-C6)-环烷基、(C3-C6)-环烯基、卤代-(C3-C6)-环烷基、(C3-C6)-环烷基-(C1-C6)-烷基、卤代-(C3-C6)-环烷基-(C1-C6)-烷基、COR1、COOR1、OCOOR1、NR1COOR1、C(O)N(R1)2、NR1C(O)N(R1)2、O(CH2)2-NH(CO)NMe2、O(CH2)2-NH(CO)NHCO2Et、OC(O)N(R1)2、CO(NOR1)R1、NR1SO2R2、NR1COR1、OR1、OSO2R2、S(O)nR2、SO2OR1、SO2N(R1)2、N=S(O)R7R8、S(R9)=NR10、S(O)(R9)=NR10、(C1-C6)-烷基-S(O)nR2、C(R11)=NOR12、(C1-C6)-烷基-OR1、(C1-C6)-烷基-OCOR1、(C1-C6)-烷基-OSO2R2、(C1-C6)-烷基-CO2R1、(C1-C6)-烷基-CN、(C1-C6)-烷基-SO2OR1、(C1-C6)-烷基-CON(R1)2、(C1-C6)-烷基-SO2N(R1)2、(C1-C6)-烷基-NR1COR1、(C1-C6)-烷基-NR1SO2R2、N(R1)2、P(O)(OR5)2、CH2P(O)(OR5)2、(C1-C6)-烷基-苯基、(C1-C6)-烷基-杂芳基、(C1-C6)-烷基-杂环基、苯基、杂芳基或杂环基,
其中最后六个基团各自彼此独立地被s个选自卤素、硝基、氰基、(C1-C6)-烷基、卤代-(C1-C6)-烷基、(C3-C6)-环烷基、S(O)n-(C1-C6)-烷基、(C1-C6)-烷氧基、卤代-(C1-C6)-烷氧基、(C1-C6)-烷氧基-(C1-C4)-烷基和氰基甲基的基团取代,并且其中杂环基带有n个氧代基团,
Z代表氢、硝基、卤素、氰基、氰硫基、(C1-C6)-烷基、(C1-C6)-烷氧基、卤代-(C1-C6)-烷基、(C2-C6)-烯基、卤代-(C2-C6)-烯基、(C2-C6)-炔基、卤代-(C2-C6)-炔基、(C3-C6)-环烷基、卤代-(C3-C6)-环烷基、(C3-C6)-环烷基-(C1-C6)-烷基、卤代-(C3-C6)-环烷基-(C1-C6)-烷基、R1(O)C、R1(R1ON=)C、R1O(O)C、(R1)2N(O)C、R1O、(R1)2N、R1(O)C(R1)N、R2(O)2S(R1)N、R2O(O)C(R1)N、(R1)2N(O)C(R1)N、R2(O)nS、R1O(O)2S、(R1)2N(O)2S、(R5O)2(O)P、R1(O)C-(C1-C6)-烷基、R1O(O)C-(C1-C6)-烷基、(R1)2N(O)C-(C1-C6)-烷基、NC-(C1-C6)-烷基、R1O-(C1-C6)-烷基、(R1)2N-(C1-C6)-烷基、R1(O)C(R1)N-(C1-C6)-烷基、R2(O)2S(R1)N-(C1-C6)-烷基、R2O(O)C(R1)N-(C1-C6)-烷基、(R1)2N(O)C(R1)N-(C1-C6)-烷基、R2(O)nS-(C1-C6)-烷基、R1O(O)2S-(C1-C6)-烷基、(R1)2N(O)2S-(C1-C6)-烷基、(R5O)2(O)P-(C1-C6)-烷基、苯基、杂芳基、杂环基、苯基-(C1-C6)-烷基、杂芳基-(C1-C6)-烷基、杂环基-(C1-C6)-烷基,
其中六个最后提及的基团各自彼此独立地被s个选自卤素、硝基、氰基、氰硫基、(C1-C6)-烷基、卤代-(C1-C6)-烷基、R1O、(R1)2N、R2(O)nS、R1O(O)2S、(R1)2N(O)2S和R1O-(C1-C6)-烷基的基团取代,并且
其中杂环基带有n个氧代基团,
条件是基团Y和Z中的至少一个不代表氢,即在化合物(1)的基团Y和Z的位置上,只有Y或者只有Z可代表氢,
V和W彼此独立地选自氢、氰基-S1、卤素、硝基、(C1-C8)-烷基、(C3-C7)-环烷基、(C3-C7)-环烷基-(C1-C4)-烷基,
其中两个上述基团中的(C3-C7)-环烷基未被取代或者被选自氟、氯、溴和碘的卤素部分或全部卤化,
(C2-C8)-烯基、(C2-C8)-炔基、(C1-C8)-卤代烷基、(C1-C3)-烷基氨基、(C1-C3)-二烷基氨基、(C1-C3)-烷基氨基-S(O)n、(C1-C3)-烷基羰基、(C1-C8)-烷氧基、(C1-C4)-烷氧基-(C1-C4)-烷基、(C1-C4)-烷氧基-(C1-C4)-烷氧基-S1、(C1-C4)-烷硫基-(C1-C4)-烷基、(C1-C4)-烷硫基-(C1-C4)-烷硫基-S1、(C2-C6)-烯氧基、(C2-C6)-炔氧基、(C1-C6)-卤代烷氧基、(C1-C4)-卤代烷氧基-(C1-C4)-烷基、(C1-C4)-卤代烷氧基-(C1-C4)-烷氧基-S1、S2-S(O)n-S1、苯氧基-S1和杂环氧基-S1,
其中杂环氧基代表通过氧连接的饱和得或部分不饱和的或芳族的5元或6元单环或8元、9元或10元双环的杂环,其具有1、2、3或4个选自O、N和S的杂原子作为环原子,并且
其中苯氧基和杂环氧基中的环基团未被取代或者被1、2、3或4个相同或不同的选自S3的基团取代,
条件是在每种情况下基团V和W中的至少一个不代表氢,即在化合物(1)的基团V和W的位置上,只有V或者只有W可代表氢,
S1代表共价键或(C1-C4)-烷二基,
S2代表(C1-C6)-烷基、(C3-C7)-环烷基、(C1-C6)-卤代烷基、(C2-C6)-烯基、(C2-C6)-卤代烯基、(C2-C6)-炔基、(C2-C6)-卤代炔基、苯基或杂环基,其中杂环基代表饱和的或部分不饱和的或芳族的5元或6元单环的杂环,其具有1、2、3或4个选自O、N和S的杂原子作为环原子,其中苯基和杂环基未被取代或者被1、2、3或4个相同或不同的选自卤素、(C1-C6)-烷基、(C1-C4)-卤代烷基、(C1-C4)-烷氧基和(C1-C4)-卤代烷氧基的基团取代,
S3代表卤素、硝基、(C1-C6)-烷基、(C3-C7)-环烷基、(C3-C7)-卤代环烷基、(C1-C6)-卤代烷基、(C2-C6)-烯基、(C2-C6)-卤代烯基、(C2-C6)-炔基、(C2-C6)-卤代炔基、(C1-C6)-烷氧基、(C1-C4)-烷氧基-(C1-C4)-烷基、(C1-C4)-烷硫基-(C1-C4)-烷基、(C1-C4)-卤代烷氧基-(C1-C4)-烷基、(C1-C4)-烷氧基-(C1-C4)-烷氧基、(C3-C7)-环烷氧基或(C1-C6)-卤代烷基氧基,
R1代表氢、(C1-C6)-烷基、(C1-C6)-卤代烷基、(C2-C6)-烯基、(C2-C6)-卤代烯基、(C2-C6)-炔基、(C2-C6)-卤代炔基、(C3-C6)-环烷基、(C3-C6)-环烯基、(C3-C6)-卤代环烷基、(C1-C6)-烷基-O-(C1-C6)-烷基、(C3-C6)-环烷基-(C1-C6)-烷基、苯基、苯基-(C1-C6)-烷基、杂芳基、(C1-C6)-烷基-杂芳基、杂环基、(C1-C6)-烷基-杂环基、(C1-C6)-烷基-O-杂芳基、(C1-C6)-烷基-O-杂环基、(C1-C6)-烷基-NR3-杂芳基、(C1-C6)-烷基-NR3-杂环基,
其中,除氢外,上述基团R1被s个选自氰基、卤素、硝基、氰硫基、OR3、S(O)nR4、N(R3)2、NR3OR3、COR3、OCOR3、SCOR4、NR3COR3、NR3SO2R4、CO2R3、COSR4、CON(R3)2和(C1-C4)-烷氧基-(C2-C6)-烷氧基羰基的基团取代,并且
其中杂环基带有n个氧代基团,
R2代表(C1-C6)-烷基、(C1-C6)-卤代烷基、(C2-C6)-烯基、(C2-C6)-卤代烯基、(C2-C6)-炔基、(C2-C6)-卤代炔基、(C3-C6)-环烷基、(C3-C6)-环烯基、(C3-C6)-卤代环烷基、(C1-C6)-烷基-O-(C1-C6)-烷基、(C3-C6)-环烷基-(C1-C6)-烷基、苯基、苯基-(C1-C6)-烷基、杂芳基、(C1-C6)-烷基-杂芳基、杂环基、(C1-C6)-烷基-杂环基、(C1-C6)-烷基-O-杂芳基、(C1-C6)-烷基-O-杂环基、(C1-C6)-烷基-NR3-杂芳基、(C1-C6)-烷基-NR3-杂环基,
其中上述基团R2被s个选自氰基、卤素、硝基、氰硫基、OR3、S(O)nR4、N(R3)2、NR3OR3、COR3、OCOR3、SCOR4、NR3COR3、NR3SO2R4、CO2R3、COSR4、CON(R3)2和(C1-C4)-烷氧基-(C2-C6)-烷氧基羰基的基团取代,并且
其中杂环基带有n个氧代基团,
R3代表氢、(C1-C6)-烷基、(C2-C6)-烯基、(C2-C6)-炔基、(C3-C6)-环烷基或(C3-C6)-环烷基-(C1-C6)-烷基,
R4代表(C1-C6)-烷基、(C2-C6)-烯基、(C2-C6)-炔基,
R5代表甲基或乙基,
R6代表乙酰氧基、乙酰氨基、N-甲基乙酰氨基、苯甲酰氧基、苯甲酰氨基、N-甲基苯甲酰氨基、甲氧基羰基、乙氧基羰基、苯甲酰基、甲基羰基、哌啶基羰基、吗啉基羰基、三氟甲基羰基、氨基羰基、甲基氨基羰基、二甲基氨基羰基、(C1-C6)-烷氧基、(C3-C6)-环烷基,或者代表杂芳基、杂环基或苯基,在每种情况下被s个选自甲基、乙基、甲氧基、三氟甲基和卤素的基团取代,
R7和R8各自彼此独立地代表(C1-C6)-烷基、卤代-(C1-C6)-烷基、(C3-C6)-环烷基、(C3-C6)-环烷基-(C1-C6)-烷基、(C1-C6)-烷氧基-(C1-C6)-烷基、苯基、杂芳基或杂环基,
其中三个最后提及的基团各自被s个选自硝基、卤素、氰基、氰硫基、(C1-C6)-烷基、卤代-(C1-C6)-烷基、(C3-C6)-环烷基、R1O(O)C、(R1)2N(O)C、R1O、(R1)2N、R2(O)nS、R1O(O)2S、(R1)2N(O)2S和R1O-(C1-C6)-烷基的基团取代,并且
其中杂环基带有n个氧代基团,
或者
R7和R8与它们所连接的硫原子一起形成3元或8元不饱和、部分饱和或饱和的环,除碳原子和sulfoximino的硫原子外,其在每种情况下均含有m个选自N(R1)、O和S(O)n的环成员,
其中该环在每种情况下由s个选自硝基、卤素、氰基、氰硫基、(C1-C6)-烷基、卤代-(C1-C6)-烷基、(C3-C6)-环烷基、R1O(O)C、(R1)2N(O)C、R1O、(R1)2N、R2(O)nS、R1O(O)2S、(R1)2N(O)2S和R1O-(C1-C6)-烷基的基团取代,并且
其中该环带有n个氧代基团,
R9代表被s个选自卤素、(C3-C6)-环烷基和R11O的基团取代的(C1-C6)-烷基,
R10代表氢、氰基、R11(O)C或(R11)2N(O)C,
R11代表氢、(C1-C6)-烷基或卤代-(C1-C6)-烷基,
R12代表氢、氰基、(C1-C6)-烷基、(C3-C6)-环烷基、卤代-(C1-C6)-烷基、OR8、SR8或NR8R9,
m代表0、1或2,
n代表0、1或2,并且
s代表0、1、2或3,
条件是排除下列化合物
-4-溴-3[[(二乙基氨基)羰基]氨基]-6-氟-2-甲基-N-(5-甲基-1,3,4-噁二唑-2-基)苯甲酰胺,
-4-溴-3[[(乙基甲基氨基)羰基]氨基]-6-氟-2-甲基-N-(5-甲基-1,3,4-噁二唑-2-基)苯甲酰胺,以及
-3-氨基-4-溴-6-氟-2-甲基-N-(5-甲基-1,3,4-噁二唑-2-基)苯甲酰胺,以及
-4-溴-2,6-二氟-2-N-(5-甲基-1,3,4-噁二唑-2-基)苯甲酰胺,
-4-溴-2,6-二氟-2-N-(5-环丙基-1,3,4-噁二唑-2-基)苯甲酰胺,
-3-氨基-6-氟-2-甲基-N-(5-甲基-1,3,4-噁二唑-2-基)苯甲酰胺,
-2-氨基-6-氟-2-N-(5-甲基-1,3,4-噁二唑-2-基)-3硝基苯甲酰胺,
-2,6-二氟-N-(5-甲基-1,3,4-噁二唑-2-基)-3硝基苯甲酰胺,以及
-3-氨基-2,6-二氟-N-(5-甲基-1,3,4-噁二唑-2-基)苯甲酰胺。
本发明的N-(1,3,4-噁二唑-2-基)芳基羧酰胺与已知的N-(1,3,4-噁二唑-2-酰基)芳基羧酰胺不同,特别是在苯基部分的5位和6位有额外的取代基。
本发明的核心涉及这样令人惊讶的发现,即在N-(1,3,4-噁二唑-2-酰基)芳基羧酰胺中,在苯基的5位和6位的苯基取代基与其他取代基结合时,对于除草活性具有出乎意料的高相关性。
在式(I)及其后的所有式中,具有多于两个碳原子的烷基可以是直链或支链的。烷基为例如甲基、乙基、正丙基或异丙基、正丁基、异丁基、叔丁基或2-丁基、戊基、己基如正己基、异己基和1,3-二甲基丁基。卤素为氟、氯、溴或碘。
杂环基为饱和的、部分饱和的或完全不饱和的含有3至6个环原子的环基团,其中1至4个环原子选自氧、氮和硫,另外其还可被苯并环稠合。例如,杂环基为哌啶基、吡咯烷基、四氢呋喃基、二氢呋喃基和氧杂环丁基(oxetanyl)。
杂芳基为含有3至6个环原子的芳族环基团,其中1至4个环原子选自氧、氮和硫,并且其还可被苯并环稠合。例如,杂芳基为苯并咪唑-2-基、呋喃基、咪唑基、异噁唑基、异噻唑基、噁唑基、吡嗪基、嘧啶基、哒嗪基、吡啶基、苯并噁唑基、噻唑基、吡咯基、吡唑基、苯硫基、1,2,3-噁二唑基、1,2,4-噁二唑基、1,2,5-噁二唑基、1,3,4-噁二唑基、1,2,4-三唑基、1,2,3-三唑基、1,2,5-三唑基、1,3,4-三唑基、1,2,4-三唑基、1,2,4-噻二唑基、1,3,4-噻二唑基、1,2,3-噻二唑基、1,2,5-噻二唑基、2H-1,2,3,4-四唑基、1H-1,2,3,4-四唑基、1,2,3,4-噁三唑基、1,2,3,5-噁三唑基、1,2,3,4-噻三唑基和1,2,3,5-噻三唑基。
当基团被多个基团多取代时,这应理解为意指该基团被一个或多个相同或不同的选自所述基团的基团所取代。
取决于取代基的性质和它们的连接方式,通式(I)的化合物可以立体异构体的形式存在。例如,如果存在一个或多个不对称取代的碳原子,则可存在对映异构体和非对映异构体。如果n是1(亚砜),也可存在立体异构体。可以由在制备中所得的混合物使用常规分离方法例如色谱分离法获得立体异构体。也可以使用具有光学活性的起始原料和/或助剂,通过使用立体选择性反应来选择性地制备立体异构体。本发明也涉及由通式(I)所涵盖但并未明确定义的所有立体异构体及其混合物。
优选的通式(I)的化合物,其中A代表N或C-Y,其中
R代表氢、卤素、(C1-C4)-烷基、卤代-(C1-C4)-烷基或(C1-C4)-烷氧基-(C1-C4)-烷基,
X代表硝基、卤素、氰基、(C1-C6)-烷基、卤代-(C1-C6)-烷基、(C3-C6)-环烷基、OR1、S(O)nR2、(C1-C6)-烷基-S(O)nR2、(C1-C6)-烷基-OR1、(C1-C6)-烷基-CON(R1)2、(C1-C6)-烷基-SO2N(R1)2、(C1-C6)-烷基-NR1COR1、(C1-C6)-烷基-NR1SO2R2、(C1-C6)-烷基-杂芳基、(C1-C6)-烷基-杂环基,
其中两个最后提及的基团各自被s个选自卤素、(C1-C6)-烷基、卤代-(C1-C6)-烷基、S(O)n-(C1-C6)-烷基、(C1-C6)-烷氧基、卤代-(C1-C6)-烷氧基的基团取代,并且其中杂环基带有n个氧代基团,
Y代表氢、硝基、卤素、氰基、氰硫基、(C1-C6)-烷基、卤代-(C1-C6)-烷基、(C2-C6)-烯基、卤代-(C2-C6)-烯基、(C2-C6)-炔基、卤代-(C2-C6)-炔基、(C3-C6)-环烷基、(C3-C6)-环烯基、卤代-(C3-C6)-环烷基、(C3-C6)-环烷基-(C1-C6)-烷基、卤代-(C3-C6)-环烷基-(C1-C6)-烷基、COR1、COOR1、OCOOR1、NR1COOR1、C(O)N(R1)2、OC(O)N(R1)2、CO(NOR1)R1、NR1SO2R2、NR1COR1、OR1、OSO2R2、S(O)nR2、SO2OR1、SO2N(R1)2、N=S(O)R7R8、S(R9)=NR10、S(O)(R9)=NR10、(C1-C6)-烷基-S(O)nR2、C(R11)=NOR12、(C1-C6)-烷基-OR1、(C1-C6)-烷基-OCOR1、(C1-C6)-烷基-OSO2R2、(C1-C6)-烷基-CO2R1、(C1-C6)-烷基-CN、(C1-C6)-烷基-SO2OR1、(C1-C6)-烷基-CON(R1)2、(C1-C6)-烷基-SO2N(R1)2、(C1-C6)-烷基-NR1COR1、(C1-C6)-烷基-NR1SO2R2、N(R1)2、P(O)(OR5)2、CH2P(O)(OR5)2、(C1-C6)-烷基-苯基、(C1-C6)-烷基-杂芳基、(C1-C6)-烷基-杂环基、苯基、杂芳基或杂环基,
其中六个最后提及的基团各自被s个选自卤素、硝基、氰基、(C1-C6)-烷基、卤代-(C1-C6)-烷基、(C3-C6)-环烷基、S(O)n-(C1-C6)-烷基、(C1-C6)-烷氧基、卤代-(C1-C6)-烷氧基、(C1-C6)-烷氧基-(C1-C4)-烷基和氰基甲基的基团取代,并且其中杂环基带有n个氧代基团,
Z代表氢、硝基、卤素、氰基、(C1-C6)-烷基、(C1-C6)-烷氧基、卤代-(C1-C6)-烷基、(C2-C6)-烯基、卤代-(C2-C6)-烯基、(C2-C6)-炔基、卤代-(C2-C6)-炔基、(C3-C6)-环烷基、卤代-(C3-C6)-环烷基、(C3-C6)-环烷基-(C1-C6)-烷基、卤代-(C3-C6)-环烷基-(C1-C6)-烷基、R1(O)C、R1(R1ON=)C、R1O(O)C、(R1)2N(O)C、R1O、(R1)2N、R1(O)C(R1)N、R2(O)2S(R1)N、R2O(O)C(R1)N、(R1)2N(O)C(R1)N、R2(O)nS、R1O(O)2S、(R1)2N(O)2S、(R5O)2(O)P、R1(O)C-(C1-C6)-烷基、R1O(O)C-(C1-C6)-烷基、(R1)2N(O)C-(C1-C6)-烷基、NC-(C1-C6)-烷基、R1O-(C1-C6)-烷基、(R1)2N-(C1-C6)-烷基、R1(O)C(R1)N-(C1-C6)-烷基、R2(O)2S(R1)N-(C1-C6)-烷基、R2O(O)C(R1)N-(C1-C6)-烷基、(R1)2N(O)C(R1)N-(C1-C6)-烷基、R2(O)nS-(C1-C6)-烷基、R1O(O)2S-(C1-C6)-烷基、(R1)2N(O)2S-(C1-C6)-烷基、(R5O)2(O)P-(C1-C6)-烷基、苯基、杂芳基、杂环基、苯基-(C1-C6)-烷基、杂芳基-(C1-C6)-烷基、杂环基-(C1-C6)-烷基,
其中六个最后提及的基团各自被s个选自卤素、硝基、氰基、氰硫基、(C1-C6)-烷基、卤代-(C1-C6)-烷基、R1O、(R1)2N、R2(O)nS、R1O(O)2S、(R1)2N(O)2S和R1O-(C1-C6)-烷基的基团取代,并且其中杂环基带有n个氧代基团,
条件是基团Y和Z中的至少一个不代表氢,
V代表氢、卤素、氰基、硝基、(C1-C4)-烷基或(C1-C4)-卤代烷基,
W代表卤素、氰基、硝基、(C1-C4)-烷基或(C1-C4)-卤代烷基,
其中R1至R12和m、n以及s各自彼此独立地如权利要求1所定义,
条件是排除下列化合物
-3-氨基-4-溴-6-氟-2-甲基-N-(5-甲基-1,3,4-噁二唑-2-基)苯甲酰胺,
-4-溴-2,6-二氟-2-N-(5-甲基-1,3,4-噁二唑-2-基)苯甲酰胺,
-4-溴-2,6-二氟-2-N-(5-环丙基-1,3,4-噁二唑-2-基)苯甲酰胺,
-3-氨基-6-氟-2-甲基-N-(5-甲基-1,3,4-噁二唑-2-基)苯甲酰胺,
-2-氨基-6-氟-2-N-(5-甲基-1,3,4-噁二唑-2-基)-3硝基苯甲酰胺,
-2,6-二氟-N-(5-甲基-1,3,4-噁二唑-2-基)-3硝基苯甲酰胺,以及
-3-氨基-2,6-二氟-N-(5-甲基-1,3,4-噁二唑-2-基)苯甲酰胺,
其中R1至R12和m、n以及s各自彼此独立地如上所定义。
特别优选的通式(I)的化合物,其中A代表N或C-Y,
其中
R代表氢、甲基、乙基、三氟甲基、甲氧基甲基或卤素,
X代表硝基、氟、氯、溴、碘、甲基、乙基、正丙基、异丙基、环丙基、三氟甲基、二氟甲基、氯二氟甲基、二氯氟甲基、甲氧基、乙氧基、甲基硫烷基、甲基亚磺酰基、甲基磺酰基、乙基硫烷基、乙基亚磺酰基、乙基磺酰基、甲氧基甲基、乙氧基甲基、甲氧基乙基、甲氧基乙氧基甲基、环丙基甲氧基、甲硫基甲基、甲基亚磺酰基甲基或甲基磺酰基甲基,
Y代表氢、硝基、氟、氯、溴、碘、氰基、(C1-C6)-烷基、卤代-(C1-C6)-烷基、OR1、S(O)nR2、SO2N(R1)2、N(R1)2、NR1SO2R2、NR1COR1、(C1-C6)-烷基-S(O)nR2、(C1-C6)-烷基-OR1、(C1-C6)-烷基-CON(R1)2、(C1-C6)-烷基-SO2N(R1)2、(C1-C6)-烷基-NR1COR1、(C1-C6)-烷基-NR1SO2R2、(C1-C6)-烷基-苯基、(C1-C6)-烷基-杂芳基、(C1-C6)-烷基-杂环基、苯基、杂芳基或杂环基,
其中六个最后提及的基团各自被s个选自卤素、硝基、氰基、(C1-C6)-烷基、卤代-(C1-C6)-烷基、(C3-C6)-环烷基、S(O)n-(C1-C6)-烷基、(C1-C6)-烷氧基、卤代-(C1-C6)-烷氧基、(C1-C6)-烷氧基-(C1-C4)-烷基和氰基甲基的基团取代,并且
其中杂环基带有n个氧代基团,
Z代表氢、硝基、氰基、氟、氯、溴或碘、甲基、乙基、正丙基、异丙基、环丙基、三氟甲基、二氟甲基、氯二氟甲基、二氯氟甲基、三氯甲基、五氟乙基、七氟异丙基、甲氧基、乙氧基、甲基硫烷基、甲基亚磺酰基、甲基磺酰基、乙基硫烷基、乙基亚磺酰基、乙基磺酰基或1H-1,2,4-三唑-1-基,
条件是基团Y和Z中的至少一个不代表氢,
V代表氢、氟、甲基或三氟甲基(CF3),
W代表氟,
其中R1至R12和m、n以及s各自彼此独立地如上所定义。
特别优选的通式(I)的N-(1,3,4-噁二唑-2-基)芳基羧酰胺,其中A代表C-Y,其中
V代表氢,
W代表氟,
并且基团R、X、Y和Z以及R1至R12和m、n和s各自彼此独立地如上所定义。
甚至更优选通式(I)的N-(1,3,4-噁二唑-2-基)芳基羧酰胺,其中A代表C-Y,其中
R代表氢、甲基、乙基、三氟甲基、甲氧基甲基或氯,
X代表硝基、氟、氯、溴、碘、甲基、乙基、正丙基、异丙基、环丙基、三氟甲基、二氟甲基、氯二氟甲基、二氯氟甲基、甲氧基、乙氧基、甲基硫烷基、甲基亚磺酰基、甲基磺酰基、乙基硫烷基、乙基亚磺酰基、乙基磺酰基、甲氧基甲基、乙氧基甲基、甲氧基乙基、甲氧基乙氧基甲基、环丙基甲氧基、甲硫基甲基、甲基亚磺酰基甲基或甲基磺酰基甲基,
Y代表氢、硝基、卤素、氰基、氰硫基、(C1-C6)-烷基、卤代-(C1-C6)-烷基、(C2-C6)-烯基、卤代-(C2-C6)-烯基、(C2-C6)-炔基、卤代-(C2-C6)-炔基、(C3-C6)-环烷基、(C3-C6)-环烯基、卤代-(C3-C6)-环烷基、(C3-C6)-环烷基-(C1-C6)-烷基、卤代-(C3-C6)-环烷基-(C1-C6)-烷基、COR1、COOR1、OCOOR1、NR1COOR1、C(O)N(R1)2、OC(O)N(R1)2、CO(NOR1)R1、NR1SO2R2、NR1COR1、OR1、OSO2R2、S(O)nR2、SO2OR1、SO2N(R1)2、N=S(O)R7R8、S(R9)=NR10、S(O)(R9)=NR10、(C1-C6)-烷基-S(O)nR2、C(R11)=NOR12、(C1-C6)-烷基-OR1、(C1-C6)-烷基-OCOR1、(C1-C6)-烷基-OSO2R2、(C1-C6)-烷基-CO2R1、(C1-C6)-烷基-CN、(C1-C6)-烷基-SO2OR1、(C1-C6)-烷基-CON(R1)2、(C1-C6)-烷基-SO2N(R1)2、(C1-C6)-烷基-NR1COR1、(C1-C6)-烷基-NR1SO2R2、N(R1)2、P(O)(OR5)2、CH2P(O)(OR5)2、(C1-C6)-烷基-苯基、(C1-C6)-烷基-杂芳基、(C1-C6)-烷基-杂环基、苯基、杂芳基或杂环基,
其中最后六个基团各自彼此独立地被s个选自卤素、硝基、氰基、(C1-C6)-烷基、卤代-(C1-C6)-烷基、(C3-C6)-环烷基、S(O)n-(C1-C6)-烷基、(C1-C6)-烷氧基、卤代-(C1-C6)-烷氧基、(C1-C6)-烷氧基-(C1-C4)-烷基和氰甲基的基团取代,并且其中杂环基带有n个氧代基团,
Z代表氢、硝基、卤素、氰基、(C1-C6)-烷基、(C1-C6)-烷氧基、卤代-(C1-C6)-烷基、(C2-C6)-烯基、卤代-(C2-C6)-烯基、(C2-C6)-炔基、卤代-(C2-C6)-炔基、(C3-C6)-环烷基、卤代-(C3-C6)-环烷基、(C3-C6)-环烷基-(C1-C6)-烷基、卤代-(C3-C6)-环烷基-(C1-C6)-烷基、R1(O)C、R1(R1ON=)C、R1O(O)C、(R1)2N(O)C、R1O、(R1)2N、R1(O)C(R1)N、R2(O)2S(R1)N、R2O(O)C(R1)N、(R1)2N(O)C(R1)N、R2(O)nS、R1O(O)2S、(R1)2N(O)2S、(R5O)2(O)P、R1(O)C-(C1-C6)-烷基、R1O(O)C-(C1-C6)-烷基、(R1)2N(O)C-(C1-C6)-烷基、NC-(C1-C6)-烷基、R1O-(C1-C6)-烷基、(R1)2N-(C1-C6)-烷基、R1(O)C(R1)N-(C1-C6)-烷基、R2(O)2S(R1)N-(C1-C6)-烷基、R2O(O)C(R1)N-(C1-C6)-烷基、(R1)2N(O)C(R1)N-(C1-C6)-烷基、R2(O)nS-(C1-C6)-烷基、R1O(O)2S-(C1-C6)-烷基、(R1)2N(O)2S-(C1-C6)-烷基、(R5O)2(O)P-(C1-C6)-烷基、苯基、杂芳基、杂环基、苯基-(C1-C6)-烷基、杂芳基-(C1-C6)-烷基、杂环基-(C1-C6)-烷基,
其中六个最后提及的基团各自被s个选自卤素、硝基、氰基、氰硫基、(C1-C6)-烷基、卤代-(C1-C6)-烷基、R1O、(R1)2N、R2(O)nS、R1O(O)2S、(R1)2N(O)2S和R1O-(C1-C6)-烷基的基团取代,并且其中杂环基带有n个氧代基团,
条件是基团Y和Z中的至少一个不代表氢,
V代表氢,
W代表氟,并且
R1至R12和m、n和s各自彼此独立地如权利要求1所定义,
条件是排除了下列化合物
-3-氨基-4-溴-6-氟-2-甲基-N-(5-甲基-1,3,4-噁二唑-2-基)苯甲酰胺,
-4-溴-2,6-二氟-2-N-(5-甲基-1,3,4-噁二唑-2-基)苯甲酰胺,
-4-溴-2,6-二氟-2-N-(5-环丙基-1,3,4-噁二唑-2-基)苯甲酰胺,
-3-氨基-6-氟-2-甲基-N-(5-甲基-1,3,4-噁二唑-2-基)苯甲酰胺,
-2-氨基-6-氟-2-N-(5-甲基-1,3,4-噁二唑-2-基)-3硝基苯甲酰胺,
-2,6-二氟-N-(5-甲基-1,3,4-噁二唑-2-基)-3硝基苯甲酰胺,
-3-氨基-2,6-二氟-N-(5-甲基-1,3,4-噁二唑-2-基)苯甲酰胺。
甚至更优选的式(I)的N-(1,3,4-噁二唑-2-基)芳基羧酰胺,其中A代表C-Y,其中
R代表氢、甲基、乙基、三氟甲基、甲氧基甲基或氯;
X代表硝基、氟、氯、溴、碘、甲基、乙基、正丙基、异丙基、环丙基、三氟甲基、二氟甲基、氯二氟甲基、二氯氟甲基、甲氧基、乙氧基、甲基硫烷基、甲基亚磺酰基、甲基磺酰基、乙基硫烷基、乙基亚磺酰基、乙基磺酰基、甲氧基甲基、乙氧基甲基、甲氧基乙基、甲氧基乙氧基甲基、环丙基甲氧基、甲硫基甲基、甲基亚磺酰基甲基或甲基磺酰基甲基,
Y代表氢、硝基、氟、氯、溴、碘、氰基、(C1-C6)-烷基、卤代-(C1-C6)-烷基、OR1、S(O)nR2、SO2N(R1)2、N(R1)2、NR1SO2R2、NR1COR1、(C1-C6)-烷基-S(O)nR2、(C1-C6)-烷基-OR1、(C1-C6)-烷基-CON(R1)2、(C1-C6)-烷基-SO2N(R1)2、(C1-C6)-烷基-NR1COR1、(C1-C6)-烷基-NR1SO2R2、(C1-C6)-烷基-苯基、(C1-C6)-烷基-杂芳基、(C1-C6)-烷基-杂环基、苯基、杂芳基或杂环基,
其中六个最后提及的基团各自被s个选自卤素、硝基、氰基、(C1-C6)-烷基、卤代-(C1-C6)-烷基、(C3-C6)-环烷基、S(O)n-(C1-C6)-烷基、(C1-C6)-烷氧基、卤代-(C1-C6)-烷氧基、(C1-C6)-烷氧基-(C1-C4)-烷基和氰基甲基的基团取代,并且
其中杂环基带有n个氧代基团,
Z代表氢、硝基、氰基、氟、氯、溴或碘、甲基、乙基、正丙基、异丙基、环丙基、三氟甲基、二氟甲基、氯二氟甲基、二氯氟甲基、三氯甲基、五氟乙基、七氟异丙基、甲氧基、乙氧基、甲基硫烷基、甲基亚磺酰基、甲基磺酰基、乙基硫烷基、乙基亚磺酰基、乙基磺酰基或1H-1,2,4-三唑-1-基,
条件是基团Y和Z中的至少一个不代表氢,
V代表氢,
W代表氟,并且
R1至R12和m、n以及s各自彼此独立地如上所定义,其中特别地,对于基团R1和R2:
R1代表氢、(C1-C6)-烷基或(C1-C6)-卤代烷基;
其中除氢外,上述基团R1被s个选自氰基、卤素和硝基的基团取代,R2代表(C1-C6)-烷基或(C1-C6)-卤代烷基,
其中上述基团R2被s个选自氰基、卤素和硝基的基团取代,并且
s代表0、1、2或3,
条件是排除下列化合物
-3-氨基-4-溴-6-氟-2-甲基-N-(5-甲基-1,3,4-噁二唑-2-基)苯甲酰胺,
-4-溴-2,6-二氟-2-N-(5-甲基-1,3,4-噁二唑-2-基)苯甲酰胺,
-3-氨基-6-氟-2-甲基-N-(5-甲基-1,3,4-噁二唑-2-基)苯甲酰胺,
-2,6-二氟-N-(5-甲基-1,3,4-噁二唑-2-基)-3硝基苯甲酰胺,以及
-3-氨基-2,6-二氟-N-(5-甲基-1,3,4-噁二唑-2-基)苯甲酰胺。
本发明的一个特定方面涉及式(I)的N-(1,3,4-噁二唑-2-基)芳基羧酰胺,其中取代基具有以下含义:
A代表C-Y,
R代表氢、甲基、乙基、三氟甲基或甲氧基甲基,
X代表氟、氯、溴、碘、甲基、乙基、正丙基、异丙基或环丙基,
Y代表S(O)nR2,
Z代表三氟甲基、二氟甲基或五氟乙基,
V代表氢,
W代表氟,以及
R2代表(C1-C6)-烷基、(C1-C6)-卤代烷基,
其中上述基团R2被s个选自氰基、卤素、硝基的基团取代,
n代表0、1或2,
s代表0、1、2或3。
关于广义定义的取代基Y=S(O)nR2其中n=0、n=1或n=2,最优选的是甲基硫烷基(SMe)、甲基亚磺酰基(甲基亚砜(SOMe))、甲基磺酰基(SO2Me)、乙基硫烷基(SEt)、乙基亚磺酰基(乙基亚砜(SOEt))和乙基磺酰基(SO2Et)其中R2=甲基(Me)或R2=乙基(Et)。
最优选Y的三种甲基取代物,即Y=SMe、Y=SOMe、Y=SO2Me。
因此,在上述特定方面的上下文中,特别优选的式(I)的N-(1,3,4-噁二唑-2-基)芳基羧酰胺,其中取代基具有以下含义:
A代表C-Y,
R代表甲基,
X代表氯或甲基,
Y代表SMe、SOMe或SO2Me,
Z代表三氟甲基或氯,
V代表氢,
W代表氟。
下面的表格汇编具体地公开了六个根据上述特定方面最优选的通式(I)的化合物,其中如下式所示,A代表C-Y,X代表氯或甲基,Y代表甲基硫烷基、甲基亚磺酰基或甲基磺酰基,Z代表三氟甲基,V代表氢,W代表氟以及R代表甲基:
此外,优选的式(I)的N-(-1,3,4-噁二唑-2-基)芳基羧酰胺,其中A代表C-Y,其中
R代表氢、甲基、乙基、三氟甲基或甲氧基甲基,
X代表F、Cl、Br、CH3、乙基、正丙基、异丙基、CF3、O-CH2-环丙基、SMe或SO2Me,
Y代表H、F、Cl、Me、乙基、丙基、异丙基、CH2OMe、CH2OEt、CH2OCH2CHF2、CH2OCH2CF3、CH2OCH2CF2CHF2、CH2O-环戊基、CH2O-四氢呋喃-3-基、CH2OCH2-四氢呋喃-2-基、CH2OCH2-四氢呋喃-3-基、CH2PO(OMe)2、COOMe、CONMe2、CONMe(OMe)、NH2、NHMe、NMe2、NHEt、NH(CH2)2OMe、NH(CH2)2OEt、OH、OMe、OEt、OiPr、O(CH2)2OMe、O(CH2)3OMe、O(CH2)4OMe、OCH2CHF2、OCH2(CO)NMe2、O(CH2)2-(CO)-NMe2、O(CH2)2-NH(CO)NMe2、O(CH2)2-NH(CO)NHCO2Et、O(CH2)2-NHCO2Me、O(CH2)2-NHSO2Me、OCH2-NHSO2cPr、O(CH2)2NHSO2Me、O(CH2)-5-2,4-二甲基-2,4-二氢-3H-1,2,4-三唑-3-酮、O(CH2)-3,5-二甲基-1,2-噁唑-4-基、O(CH2)-5-吡咯烷-2-酮、O(CH2)2-O(3,5-二-甲氧基嘧啶-2-基、SMe、SEt、S(CH2)2OMe、SO(CH2)2OMe、SO2(CH2)2OMe、S(O)Me、S(O)Et、SO2Me、SO2Et、SO2(CH2)2OMe、4,5-二氢-1,2-噁唑-3-基、5-氰基甲基-4,5-二氢-1,2-噁唑-3-基、[1,4]二噁烷-2-基甲氧基、吡唑-1-基、4-甲氧基吡唑-1-基、1,2,3-三唑-1-基、5-(甲氧基甲基)-4,5-二氢-1,2-噁唑-3-基或5-氰基甲基-4,5-二氢-1,2-噁唑-3-基
并且
Z代表F、Cl、Br、I、CF3、NO2、SMe、SEt、SOMe、SOEt、SO2Me、SO2Et、吡唑-1-基或1H-1,2,4-三唑-1-基,
条件是排除下列化合物
-3-氨基-4-溴-6-氟-2-甲基-N-(5-甲基-1,3,4-噁二唑-2-基)苯甲酰胺,以及
-4-溴-2,6-二氟-2-N-(5-甲基-1,3,4-噁二唑-2-基)苯甲酰胺。
或者,优选的式(I)的N-(1,3,4-噁二唑-2-基)芳基羧酰胺,其中A代表N(而不是C-Y),其中
V代表氢,
W代表氟,
Z代表CF3,
并且基团R、X和Y以及R1至R12和m、n和s各自彼此独立地如上所定义。
在下面指定的所有式中,除非定义不同,否则取代基和符号具有与式(I)中所述的相同含义。
根据本发明的化合物可以例如通过方案1所示的方法制备,通过苯甲酰或烟酰氯(II)与2-氨基-1,3,4-噁二唑(III)的碱催化反应:
方案1
原则上,式(II)的苯甲酰氯或其母体苯甲酸是已知的,并且可通过例如US 6,376,429 B1、EP 1 585 742 A1、WO2014/184015、WO2014/184016、WO2013/083859和EP 1 202978 A1中所述的方法制备。
根据本发明的化合物也可通过方案2所述的方法制备,通过使式(IV)的苯甲酸或烟酸与2-氨基-1,3,4-噁二唑(III)反应:
方案2
对于活化反应,可使用通常用于酰胺化反应的脱水试剂,例如1,1’-羰基二咪唑(CDI)、二环己基碳二亚胺(DCC)、2,4,6-三丙基-1,3,5,2,4,6-三噁三膦烷2,4,6-三氧化物(T3P)等。
发明化合物还可通过在方案3中所述的方法制备,通过使式V的化合物环化:
方案3
环化可以通过Synth.Commun.31(12),1907-1912(2001)或Indian J.Chem.,Section B:Organic Chemistry Including Medicinal Chemistry;Vol.43(10),2170-2174(2004)中所记载的方法来进行。
方案4
方案3中所用的式V的化合物可由式VII的酰基异氰酸酯与式VI的酰肼通过Synth.Commun.25(12),1885-1892(1995)中所记载的方法制备。
改变反应步骤的顺序可能是合适的。例如,带有亚砜的苯甲酸不能直接转化为它们的酸性氯化物。此处,一个选择是首先在硫醚阶段制备酰胺,然后将硫醚氧化成亚砜。
可通过上述反应合成的式(I)的化合物和/或其盐的集合也可以并行的方式制备,在这种情况下,这可以手动、半自动或全自动的方式完成。可以例如使反应、后处理或产物和/或中间体的纯化自动化进行。总而言之,这应理解为意指如例如D.Tiebes在Combinatorial Chemistry-Synthesis,Analysis,Screening(编辑:Günther Jung),Wiley,1999,1-34页中所记载的过程。
为并行进行反应和后处理,可使用多个市售可得的仪器,例如购自BarnsteadInternational,Dubuque,Iowa 52004-0797,USA的Calpyso反应模块,或购自Radleys,Shirehill,Saffron Walden,Essex,CB 113AZ,England的反应站,或购自PerkinElmer,Waltham,Massachusetts 02451,USA的多探针(MultiPROBE)自动化工作站。为了对式(I)的化合物及其盐或制备过程中产生的中间体进行并行纯化,可利用的仪器包括例如购自ISCO,Inc.,4700Superior Street,Lincoln,NE 68504,USA的色谱设备。
精细的设备形成模块化过程,其中各工作步骤均是自动的,但在各工作步骤之间必须进行手动操作。这可通过使用半集成或全集成自动化系统而避免,其中所述各自动化模块由例如机器人操控。这类自动化系统可由例如Caliper,Hopkinton,MA 01748,USA获得。
单个或多个合成步骤的进行可通过使用聚合物支撑的试剂/清除树脂来支持。专业文献记载了一系列实验方案,例如在ChemFiles,Vol 4,No.1,Polymer-SupportedScavengers and Reagents for Solution-Phase Synthesis(Sigma-Aldrich)中。
除了本文所述的方法之外,通式(I)的化合物及其盐也可通过固相负载法全部或部分地进行制备。为此,将所述合成中的或适用于相应步骤的合成中的各中间体或全部中间体结合至合成树脂上。固相负载合成法在技术文献中有充分地描述,例如Barry A.Bunin在“The Combinatorial Index”,Verlag Academic Press,1998和CombinatorialChemistry–Synthesis,Analysis,Screening(Günther Jung编),Verlag Wiley,1999中。使用固相负载合成法可以进行多种方案,其由文献已知,或者对于它们的部分,其可通过手动或自动的方式进行。反应可使用例如IRORI技术,在购自Nexus Biosystems,12140Community Road,Poway,CA92064,USA的微反应器中进行。
在固相和液相中,单个或几个合成步骤的实施都可以通过使用微波技术来支持。专业文献,例如Microwaves in Organic and Medicinal Chemistry(编辑:C.O.Kappe和A.Stadler),Verlag Wiley,2005中记载了一系列实验方案。
通过本文所述方法的制备获得物质集合形式(称为库)的式(I)的化合物及其盐。本发明还提供包含至少两种式(I)的化合物及其盐的库。
本发明的式(I)的化合物(和/或其盐),在下文中统称“本发明的化合物”,其在对抗广谱的经济上重要的单子叶和双子叶一年生有害植物方面具有优异的除草功效。活性成分也能有效地作用于由根茎、根状茎及其他多年生器官发芽并难以防治的多年生有害植物。
因此,本发明还提供了一种用于防治不想要的植物或调节植物生长(优选在植物作物中)的方法,其中将一种或多种本发明的化合物施用于植物(例如有害植物,如单子叶或双子叶杂草或不想要的作物植物)、种子(例如谷物、种子或无性繁殖体如块茎或带芽的枝条部位)或植物生长区域(例如栽培区域)。本发明的化合物可例如在播种前(如果合适,还可掺入土壤中)、出苗前或出苗后施用。可通过本发明的化合物防治的单子叶和双子叶杂草植物群的一些代表性的具体实例如下,但该列举不限于特定的属种。
单子叶有害植物属:山羊草属(Aegilops)、冰草属(Agropyron)、剪股颖属(Agrostis)、看麦娘属(Alopecurus)、阿披拉草属(Apera)、燕麦属(Avena)、臂形草属(Brachiaria)、雀麦属(Bromus)、蒺藜草属(Cenchrus)、鸭拓草属(Commelina)、狗牙根属(Cynodon)、莎草属(Cyperus)、龙爪茅属(Dactyloctenium)、马唐属(Digitaria)、稗属(Echinochloa)、荸荠属(Eleocharis)、蟋蟀草属(Eleusine)、画眉草属(Eragrostis)、野黍属(Eriochloa)、羊茅属(Festuca)、飘拂草属(Fimbristylis)、异蕊花属(Heteranthera)、白茅属(Imperata)、鸭嘴草属(Ischaemum)、千金子属(Leptochloa)、黑麦草属(Lolium)、雨久花属(Monochoria)、黍属(Panicum)、雀稗属(Paspalum)、虉草属(Phalaris)、梯牧草属(Phleum)、早熟禾属(Poa)、筒轴茅属(Rottboellia)、慈姑属(Sagittaria)、莞草属(Scirpus)、狗尾草属(Setaria)、高粱属(Sorghum)。
双子叶杂草属:苘麻属(Abutilon)、苋属(Amaranthus)、豚草属(Ambrosia)、单花葵属(Anoda)、春黄菊属(Anthemis)、Aphanes、蒿属(Artemisia)、滨藜属(Atriplex)、雏菊属(Bellis)、鬼针草属(Bidens)、荠属(Capsella)、飞廉属(Carduus)、决明属(Cassia)、矢车菊属(Centaurea)、藜属(Chenopodium)、蓟属(Cirsium)、旋花属(Convolvulus)、曼陀罗属(Datura)、山蚂蝗属(Desmodium)、刺酸模属(Emex)、糖芥属(Erysimum)、大戟属(Euphorbia)、鼬瓣花属(Galeopsis)、牛膝菊属(Galinsoga)、拉拉藤属(Galium)、木槿属(Hibiscus)、番薯属(Ipomoea)、地肤属(Kochia)、野芝麻属(Lamium)、独行菜属(Lepidium)、母草属(Lindernia)、母菊属(Matricaria)、薄荷属(Mentha)、山靛属(Mercurialis)、粟米草属(Mullugo)、勿忘草属(Myosotis)、罂粟属(Papaver)、牵牛属(Pharbitis)、车前属(Plantago)、蓼属(Polygonum)、马齿苋属(Portulaca)、毛茛属(Ranunculus)、萝卜属(Raphanus)、蔊菜属(Rorippa)、节节菜属(Rotala)、酸模属(Rumex)、猪毛菜属(Salsola)、千里光属(Senecio)、田菁属(Sesbania)、黄花棯属(Sida)、白芥属(Sinapis)、茄属(Solanum)、苦苣菜属(Sonchus)、尖瓣花属
(Sphenoclea)、繁缕属(Stellaria)、薄公英属(Taraxacum)、菥蓂属(Thlaspi)、三叶草属(Trifolium)、荨麻属(Urtica)、婆婆纳属(Veronica)、堇菜属(Viola)和苍耳属(Xanthium)。
如果在萌芽前将本发明的化合物施用于土壤表面,则可以完全阻止杂草幼苗的出苗,或者杂草生长至其达到子叶期、但随后其停止生长并最终在三至四周后彻底死亡。
如果在出苗后将所述活性化合物施用于植物的绿色部位,则在处理后生长停止,有害植物停留在施用时间点的生长期,或在一段时间后彻底死亡,从而以这种方式,在非常早期并以持久的方式消除对作物植物有害的杂草竞争。
尽管本发明的化合物在对抗单子叶和双子叶杂草方面具有显著的除草活性,但对经济上重要的作物中的作物植物,如果有损害的话,仅具有可忽略的损害,这取决于本发明的具体化合物的结构及其施用率,所述作物植物为例如以下属的双子叶作物:落花生属(Arachis)、甜菜属(Beta)、芸苔属(Brassica)、黄瓜属(Cucumis)、南瓜属(Cucurbita)、向日葵属(Helianthus)、胡萝卜属(Daucus)、大豆属(Glycine)、棉属(Gossypium)、番薯属(Ipomoea)、莴苣属(Lactuca)、亚麻属(Linum)、番茄属(Lycopersicon)、烟草属(Nicotiana)、菜豆属(Phaseolus)、豌豆属(Pisum)、茄属(Solanum)、蚕豆属(Vicia),或以下属的单子叶作物:葱属(Allium)、凤梨属(Ananas)、天门冬属(Asparagus)、燕麦属(Avena)、大麦属(Hordeum)、稻属(Oryza)、黍属(Panicum)、甘蔗属(Saccharum)、黑麦属(Secale)、高粱属(Sorghum)、小黑麦属(Triticale)、小麦属(Triticum)、玉蜀黍属(Zea),特别是玉蜀黍属和小麦属。由于这些原因,本发明化合物特别适用于选择性防治植物作物(例如农业上有用的植物或观赏植物)中的不想要的植物生长。
此外,本发明的化合物(根据其具体结构和采用的施用率)在作物植物中具有显著的生长调节性能。它们利用调节作用干预植物自身的新陈代谢,从而可例如通过引发脱水和矮化生长用于可控制的影响植物成分并促进采收。此外,在所述方法中,它们还适用于一般性防治和抑制不想要的营养生长(vegetative growth),而不会杀死植物。抑制营养生长由于例如可减少或完全防止倒伏而对许多单子叶和双子叶作物起到重要作用。
由于活性化合物的除草和植物生长调节性能,其也可用于防治基因修饰的植物或通过常规诱变而改性的植物作物中的有害植物。通常,转基因植物的特征在于具有特别有利的性质,例如对某些农药、特别是某些除草剂的抗性;对植物病害或植物病害的病原体——如某些昆虫或微生物(如真菌、细菌或病毒)——的抗性。其他特定的特性涉及,例如,采收物的数量、质量、存储性、组成和具体成分。例如,已知转基因植物具有增加的淀粉含量或改变的淀粉品质量,或在采收物中具有不同的脂肪酸组成。
关于转基因作物,优选将本发明的化合物用于经济上重要的有用植物和观赏植物的转基因作物中,所述作物例如谷类,如小麦、大麦、黑麦、燕麦、粟/高粱、水稻和玉米,或甜菜、棉花、大豆、油菜、马铃薯、番茄、豌豆和其他蔬菜类作物。优选地,本发明的化合物可以用作有用植物作物的除草剂,所述植物作物对除草剂的植物毒性作用具有抗性或通过基因工程对其有抗性。
优选将本发明的化合物及其盐用在经济上重要的有用植物及观赏性植物的转基因作物中,例如谷类如小麦、大麦、黑麦、燕麦、粟/高粱、稻、木薯和玉米,或者甜菜、棉花、大豆、油菜、马铃薯、番茄、豌豆及其他蔬菜类作物。优选地,本发明的化合物可在对除草剂的植物毒性效果具有抗性或已通过基因工程产生抗性的有用植物作物中用作除草剂。
产生与现有植物相比具有改进性能的新植物的常规方法包括,例如常规育种方法和产生突变体。
或者,具有改进特性的新植物可借助重组方法产生(参见例如EP-A-0221044、EP A0131624)。例如,已记载了以下一些情况:
-对作物植物进行基因修饰以使植物中合成的淀粉改性(例如WO 92/11376、WO92/14827、WO 91/19806),
-转基因作物植物,其对草铵膦类(参见例如EP-A-0242236、EP-A-0242246)或草甘膦类(WO 92/00377)或磺酰脲类(EP-A-0257993、US-A-5013659)特定的除草剂具有抗性,
-能产生苏云金芽孢杆菌(Bacillus thuringiensis)毒素(Bt毒素)的转基因作物植物,例如棉花,其使得植物能抵抗特定的害虫(EP-A-0142924、EP-A-0193259),
-具有改进的脂肪酸组成的转基因作物植物(WO 91/013972),
-具有新的组分或次级代谢产物——例如新的植物抗毒素,其使抗病能力增强——的基因修饰的作物植物(EPA 0309862、EPA 0464461),
-光呼吸作用降低的基因修饰植物,其具有更高的产量和更高的胁迫耐受性(EPA0305398),
-产生制药上或诊断上重要的蛋白质的转基因作物植物(“分子制药(molecularpharming)”),
-以产量更高或品质更好为特征的转基因作物植物,
-以例如上述新性质的结合(“基因叠加(gene stacking)”)为特征的转基因作物植物。
原则上,用于制备具有改变性质的新转基因植物的大量分子生物技术是已知的,参见,例如I.Potrykus和G.Spangenberg(eds.)Gene Transfer to Plants,Springer LabManual(1995),Springer Verlag Berlin,Heidelberg或者Christou,"Trends in PlantScience"1(1996)423-431。
为了进行这类基因操作,可以将可通过DNA序列重组而发生突变或序列改变的核酸分子引入质粒中。例如,借助标准方法,可进行碱基交换、移除部分序列或添加天然或合成序列。为了将DNA片段彼此连接,可将接合部分或连接体放在片段上,参见例如,Sambrooket al.,1989,Molecular Cloning,A Laboratory Manual,第2版,Cold Spring HarborLaboratory Press,Cold Spring Harbor,NY;或Winnacker"Gene und Klone"[Genes andclones],VCH Weinheim,第2版,1996。
例如,产生具有降低的基因产物活性的植物细胞可以通过下述方法实现:通过表达至少一种相应的反义RNA、用于实现共抑制效应的正义RNA,或者通过表达至少一种对上述基因产物的转录物进行特异性裂解而适当地构建的核酶。为此,可以首先使用包含基因产物的所有编码序列——包括所有可能存在的任何侧翼序列——的DNA分子,也可以使用仅含有部分编码序列的DNA分子,在这种情况下,这些部分必须足够长以便在细胞中产生反义效应。也可以使用与所述基因产物的编码序列具有高度同源性但并不完全相同的DNA序列。
当在植物中表达核酸分子时,所合成的蛋白质可定位于植物细胞的任何所需的区室中。然而,为了实现在特定区室中的定位,可以例如将编码区与确保在特定区室中定位的DNA序列连接。这样的序列是本领域技术人员已知的(参见,例如Braun et al.,EMBO J.11(1992),3219-3227;Wolter et al.,Proc.Natl.Acad.Sci.USA 85(1988),846-850;Sonnewald et al.,Plant J.1(1991),95-106)。核酸分子也可以在植物细胞的细胞器中表达。
转基因植物细胞可通过已知技术再生以得到完整的植株。原则上,转基因植物可以为任何所需的植物物种的植物,即不仅可为单子叶植物,也可为双子叶植物。
因此,可以通过过表达、阻抑或抑制同源(=天然)基因或基因序列,或者通过表达异源(=外源)基因或基因序列而获得性质改变的转基因植物。
优选将本发明的化合物用于对以下物质具有抗性的转基因作物中:生长调节剂例如麦草畏(dicamba);或者抑制主要植物酶的除草剂,所述酶为例如乙酰乳酸合酶(ALS)、EPSP合酶、谷氨酰胺合酶(GS)或羟基苯丙酮酸双加氧酶(HPPD);或选自磺酰脲、草甘膦、草铵膦或苯甲酰基异噁唑和类似活性化合物的除草剂。
当将本发明的活性化合物用于转基因作物时,不仅产生了在其他作物中观察到的对有害植物的作用,而且还通常在施用于特定的转基因作物时产生特殊作用,例如改变或特别是拓宽的可防治的杂草谱、改变的施用时可使用的施用率、优选与转基因作物对其具有抗性的除草剂的良好的结合性,以及对转基因作物植物的生长和产量的影响。
因此,本发明还提供本发明的化合物作为除草剂用于防治转基因作物植物中的有害植物的用途。
本发明的化合物可以可湿性粉剂、可乳化浓缩剂、可喷雾溶液剂、撒粉产品或颗粒剂的形式以常规制剂使用。因此,本发明还提供包含本发明的化合物的除草组合物和植物生长调节组合物。
根据所需的生物和/或物理化学参数,本发明的化合物可以多种方式进行配制。可能的制剂包括,例如:可湿性粉剂(WP)、水溶性粉剂(SP)、水溶性浓缩剂、可乳化浓缩剂(EC)、乳剂(EW)(如水包油乳剂和油包水乳剂)、可喷雾溶液剂、悬浮液浓缩剂(SC)、油基分散剂或水基分散剂、油混溶性溶液剂、胶囊悬浮剂(CS)、撒粉产品(DP)、拌种产品、用于撒播和土壤施用的颗粒剂、微颗粒形式的颗粒剂(GR)、喷雾颗粒剂、吸收性颗粒剂和吸附性颗粒剂、水分散性颗粒剂(WG)、水溶性颗粒剂(SG)、ULV制剂、微胶囊剂和蜡剂。
这些各个制剂类型原则上是已知的,并记载于例如以下文献中:Winnacker-Küchler,"Chemische Technologie"[Chemical Technology],第7卷,C.Hanser VerlagMunich,第4版,1986;Wade van Valkenburg,"Pesticide Formulations",Marcel Dekker,N.Y.,1973;K.Martens,"Spray Drying"Handbook,第3版,1979,G.Goodwin Ltd.London。
所需的制剂助剂,例如惰性物质、表面活性剂、溶剂和其他添加剂同样也是已知的,并记载于例如以下文献中:Watkins,"Handbook of Insecticide Dust Diluents andCarriers",第2版,Darland Books,Caldwell N.J.;H.v.Olphen,"Introduction to ClayColloid Chemistry",第2版,J.Wiley&Sons,N.Y.;C.Marsden,"Solvents Guide",第2版,Interscience,N.Y.1963;McCutcheon's"Detergents and Emulsifiers Annual",MCPubl.Corp.,Ridgewood N.J.,Sisley and Wood,"Encyclopedia of Surface ActiveAgents",Chem.Publ.Co.Inc.,N.Y.1964; [Interface-active Ethylene Oxide Adducts],Wiss.Verlagsgesellschaft,Stuttgart1976;Winnacker-Küchler,"Chemische Technologie"[Chemical Engineering],第7卷,C.Hanser Verlag Munich,第4版,1986。
基于这些制剂,也可以制备与其他农药活性物质(例如杀昆虫剂、杀螨剂、除草剂和杀真菌剂)以及与安全剂、肥料和/或生长调节剂的结合物,例如以成品制剂或桶混物的形式。合适的安全剂为例如吡唑解草酯(mefenpyr-diethyl)、环丙磺酰胺(cyprosulfamide)、双苯噁唑酸(isoxadifen-ethyl)、解毒喹(cloquintocet-mexyl)和烯丙酰草胺(dichlormid)。
可湿性粉剂为可均匀分散于水中的制剂,除所述活性成分——稀释剂或惰性物质除外——外,其还含有离子型和/或非离子型表面活性剂(湿润剂、分散剂),所述表面活性剂为例如聚乙氧基化烷基酚、聚乙氧基化脂肪醇、聚乙氧基化脂肪胺、脂肪醇聚乙二醇醚硫酸盐、烷基磺酸盐、烷基苯磺酸盐、木素磺酸钠、2,2’-二萘基甲烷-6,6’-二磺酸钠、二丁基萘磺酸钠或油酰基甲基牛磺酸钠。为了制备所述可湿性粉剂,例如在常规设备(例如锤磨机、鼓风磨机和空气喷射磨机)中将除草活性化合物精细研磨,并同时或随后与制剂助剂相混合。
可乳化浓缩剂通过下述过程制备:将活性化合物溶于有机溶剂(例如丁醇、环己酮、二甲基甲酰胺、二甲苯或其他相对高沸点的芳香族化合物或烃类)或有机溶剂的混合物中,并加入一种或多种离子型和/或非离子型表面活性剂(乳化剂)。可用的的乳化剂的实例为:烷基芳基磺酸钙,如十二烷基苯磺酸钙;或非离子型乳化剂,如脂肪酸聚乙二醇酯、烷基芳基聚乙二醇醚、脂肪醇聚乙二醇醚、环氧丙烷-环氧乙烷缩合产物、烷基聚醚、脱水山梨糖醇酯(例如脱水山梨糖醇脂肪酸酯)或聚氧乙烯脱水山梨糖醇酯(例如聚氧乙烯脱水山梨糖醇脂肪酸酯)。
撒粉产品通过将活性化合物与细分散的固体物质一起研磨而获得,所述固体物质例如滑石、天然粘土(如高岭土、膨润土和叶蜡石)或硅藻土。
悬浮浓缩剂可为水基或油基的。它们可以例如通过使用市售的砂磨机进行湿法研磨,并任选加入已在上文其他制剂类型中所列的表面活性剂而制备。
乳剂例如水包油乳剂(EW),可以通过例如搅拌器、胶体研磨机和/或静态混合器,使用含水有机溶剂以及任选地例如已在上文其他制剂类型中所列的表面活性剂来制备。
颗粒剂可以通过将所述活性化合物喷洒在吸附性颗粒状惰性材料上,或通过粘合剂将活性化合物浓缩剂施用到载体表面而制备,所述载体例如砂、高岭土或颗粒状惰性材料,所述粘合剂例如聚乙烯醇、聚丙烯酸钠或矿物油。也可以将合适的活性成分以制备肥料颗粒——如果需要,作为与肥料的混合物——的常规方式制备成颗粒。
水分散性颗粒剂通常通过常规方法,例如喷雾-干燥法、流化床制粒法、盘式制粒法、在不使用固体惰性物质的情况下在高速混合器中混合并挤出而制备。
关于盘式颗粒、流化床颗粒、挤出颗粒和喷雾颗粒的制备,参见例如以下文献中的方法:"Spray-Drying Handbook"第3版,1979,G.Goodwin Ltd.,London,J.E.Browning,"Agglomeration",Chemical and Engineering 1967,第147页及之后的页;"Perry'sChemical Engineer's Handbook",第5版,McGraw-Hill,New York 1973,第8-57页。
关于作物保护组合物制剂的其他细节,参见例如G.C.Klingman,"Weed Controlas a Science",John Wiley and Sons,Inc.,New York,1961,第81-96页和J.D.Freyer,S.A.Evans,"Weed Control Handbook",第5版,Blackwell Scientific Publications,Oxford,1968,第101-103页。
所述农用化学品制剂通常含有0.1至99重量%、尤其是0.1至95重量%的本发明的化合物。
在可湿性粉剂中,活性化合物的浓度为例如约10至90重量%,达到100重量%的余量物质由常规制剂成分组成。在可乳化浓缩物中,活性化合物的浓度可为约1至90重量%,优选5至80重量%。粉尘型制剂含有1至30重量%的活性成分,通常优选5至20重量%的活性成分;可喷雾溶液剂含有约0.05至80重量%、优选2至50重量%的活性成分。在水分散性颗粒剂中,活性化合物的含量部分地取决于所述活性化合物是以液体形式还是以固体形式存在,以及所使用的颗粒助剂、填料等。在水分散性颗粒剂中,活性化合物的含量例如为1至95重量%,优选10至80重量%。
此外,所提及的活性化合物制剂任选地包含各种常规的粘着剂、湿润剂、分散剂、乳化剂、渗透剂、防腐剂、抗冻剂和溶剂、填料、载体和染料、消泡剂、蒸发抑制剂和影响pH值及粘度的试剂。
基于这些制剂,也可制备与其他农药活性物质(例如杀昆虫剂、杀螨剂、除草剂和杀真菌剂)以及与安全剂、肥料和/或生长调节剂的结合物,例如以成品制剂或桶混物的形式。
可以与本发明的化合物以混合制剂或桶混形式结合使用的活性化合物为,例如,已知的基于抑制以下物质的活性化合物:例如,乙酰乳酸合成酶、乙酰辅酶A羧化酶、纤维素合成酶、烯醇式丙酮酰莽草酸-3-磷酸合成酶、谷氨酰胺合成酶、对羟基苯基丙酮酸双加氧酶、八氢番茄红素去饱和酶、光合体系I、光合体系II、原卟啉原氧化酶,如例如记载于WeedResearch 26(1986)第441-445页或"The PesticideManual",第15版,The British CropProtection Council and the Royal Soc.of Chemistry,2009和其中引用的文献中。可以与本发明的化合物结合的已知的除草剂或植物生长调节剂的实例包括以下的活性成分(化合物以国际标准化组织(ISO)规定的通用名表示,或以化学名称或其编号表示),并且总包括所有使用形式,例如酸、盐、酯和异构体如立体异构体和光学异构体。这些包括例如一种使用形式和在一些情况下的多种使用形式:
乙草胺(acetochlor)、苯并噻二唑(acibenzolar)、苯并噻二唑甲酯(acibenzolar-S-methyl)、三氟羧草醚(acifluorfen)、三氟羧草醚钠(acifluorfen-sodium)、苯草醚(aclonifen)、甲草胺(alachlor)、草毒死(allidochlor)、禾草灭(alloxydim)、枯杀达(alloxydim-sodium)、莠灭净(ametryne)、氨唑草酮(amicarbazone)、乙酰胺(amidochlor)、酰嘧磺隆(amidosulfuron)、环丙嘧啶酸(aminocyclopyrachlor)、氯氨吡啶酸(aminopyralid)、杀草强(amitrole)、氨基磺酸铵(ammonium sulfamate)、环丙嘧啶醇(ancymidol)、莎稗磷(anilofos)、磺草灵(asulam)、莠去津(atrazine)、唑啶草酮(azafenidin),四唑嘧磺隆(azimsulfuon)、叠氮津(aziprotryne)、氟丁酰草胺(beflubutamid)、草除灵(benazolin)、草除灵乙酯(benazolin-ethyl)、bencarbazone、乙丁氟灵(benfluralin)、呋草黄(benfuresate)、地散磷(bensulide)、苄嘧磺隆(bensulfuron)、苄嘧磺隆(bensulfuron-methyl)、灭草松(bentazone)、双苯嘧草酮(benzfendizone)、双环磺草酮(benzobicyclon),吡草酮(benzofenap)、氟磺胺草(benzofluor)、新燕灵(benzoylprop)、氟吡草酮(bicyclopyrone)、甲羧除草醚(bifenox)、双丙氨膦(bilanafos)、双丙氨膦钠盐(bilanafos-sodium)、双草醚(bispyribac)、双草醚钠(bispyribac-sodium)、除草定(bromacil)、溴丁酰草胺(bromobutide)、溴酚肟(bromofenoxim)、溴苯腈(bromoxynil)、莠谷隆(bromuron)、特克草(buminafos)、羟草酮(busoxinone)、丁草胺(butachlor)、氟丙嘧草酯(butafenacil)、抑草磷(butamifos)、丁烯草胺(butenachlor)、仲丁灵(butralin)、丁氧环酮(butroxydim)、丁草敌(butylate)、唑草胺(cafenstrole)、双酰草胺(carbetamide)、唑酮草酯(carfentrazone)、唑酮草酯(carfentrazone-ethyl)、甲氧除草醚(chlomethoxyfen)、草灭畏(chloramben)、炔禾灵(chlorazifop)、炔禾灵丁酯(chlorazifop-butyl)、氯溴隆(chlorbromuron)、氯炔灵(chlorbufam)、伐草克(chlorfenac)、双氯酚酸钠(chlorfenac-sodium)、燕麦酯(chlorfenprop)、氯甲丹(chlorflurenol)、氯甲丹(chlorflurecol-methyl)、氯草敏(chloridazon)、氯嘧磺隆(chlorimuron)、氯嘧磺隆(chlorimuron-ethyl)、矮壮素(chlormequat-chloride)、草枯醚(chlornitrofen)、4-氯邻苯二甲酸(chlorophthalim)、氯酞酸二甲酯(chlorthal-dimethyl)、绿麦隆(chlorotoluron)、氯磺隆(chlorsulfuron)、吲哚酮草酯(cinidon)、吲哚酮草酯(cinidon-ethyl)、环庚草醚(cinmethylin)、醚磺隆(cinosulfuron)、烯草酮(clethodim)、炔草酸(clodinafop)、炔草酯(clodinafop-propargyl)、杀雄嗪酸(clofencet)、异噁草松(clomazone)、氯甲酰草胺(clomeprop)、调果酸(cloprop)、二氯吡啶酸(clopyralid)、氯酯磺草胺(cloransulam)、氯酯磺草胺(cloransulam-methyl)、苄草隆(cumyluron)、氨基氰(cyanamide)、氰草津(cyanazine)、环丙酰胺酸(cyclanilide)、环草敌(cycloate)、环丙嘧磺隆(cyclosulfamuron)、噻草酮(cycloxydim)、环莠隆(cycluron)、氰氟草酯(cyhalofop)、氰氟草丁酯(cyhalofop-butyl)、莎草快(cyperquat)、环丙津(cyprazine)、环唑草胺(cyprazole)、2,4-D、2,4-DB、杀草隆(daimuron/dymron)、茅草枯(dalapon)、丁酰肼(daminozide)、棉隆(dazomet)、正癸醇(n-decanol)、甜菜安(desmedipham)、敌草净(desmetryn)、detosyl-pyrazolate(DTP)、燕麦敌(diallate)、麦草畏(dicamba)、敌草腈(dichlobenil)、2,4-滴丙酸(dichlorprop)、精2,4-滴丙酸(dichlorprop-P)、二氯苯氧基丙酸(diclofop)、禾草灵甲酯(diclofop-methyl)、精禾草灵甲酯(diclofop-P-methyl)、双氯磺草胺(diclosulam)、乙酰甲草酸(diethatyl)、乙酰甲草胺(diethatyl-ethyl)、枯莠隆(difenoxuron)、野燕枯(difenzoquat)、吡氟酰草胺(diflufenican)、二氟吡隆(diflufenzopyr)、氟吡草腙钠(diflufenzopyr-sodium)、噁唑隆(dimefuron)、敌草克(dikegulac-sodium)、哌草丹(dimepiperate)、二甲草胺(dimethachlor)、异戊乙净(dimethametryn)、二甲吩草胺(dimethenamid)、精甲酚噻草胺(dimethenamide-P)、噻节因(dimethipin)、dimetrasulfuron、氨氟灵(dinitramine)、地乐酚(dinoseb)、特乐酚(dinoterb)、双苯酰草胺(diphenamid)、异丙净(dipropetryn)、敌草快(diquat)、敌草快(diquat dibromide)、氟硫草定(dithiopyr)、敌草隆(diuron)、二硝酚(DNOC)、草止津(eglinazine-ethyl)、茵多酸(endothal)、扑草灭(EPTC)、戊草丹(esprocarb)、乙丁烯氟灵(ethalfluralin)、胺苯磺隆(ethametsulfuron)、胺苯磺隆(ethametsulfuron-methyl)、乙烯利(ethephon)、磺噻隆(ethidimuron)、乙嗪草酮(ethiozin)、乙氧呋草黄(ethofumesate)、氟乳醚(ethoxyfen)、氯氟草醚乙酯(ethoxyfen-ethyl)、乙氧嘧磺隆(ethoxysulfuron)、乙氧苯草胺(etobenzanid)、F-5331(即N[2-氯-4-氟-5[4-(3-氟丙基)-4,5-二氢-5-氧代-1H-四唑-1-基]苯基]乙磺酰胺)、F-7967(即3-[7-氯-5-氟-2-(三氟甲基)-1H-苯并咪唑-4-基]-1-甲基-6-(三氟甲基)嘧啶-2,4(1H,3H)-二酮)、涕丙酸(fenoprop)、噁唑禾草灵(fenoxaprop)、精噁唑禾草灵(fenoxaprop-P)、噁唑禾草灵乙酯(fenoxaprop-ethyl)、精噁唑禾草灵乙酯(fenoxaprop-P-ethyl)、fenoxasulfone、四唑酰草胺(fentrazamide)、非草隆(fenuron)、麦草氟(flamprop)、高效麦草氟异丙酯(flamprop-M-isopropyl)、高效麦草氟甲酯(flamprop-M-methyl)、啶嘧磺隆(flazasulfuron)、双氟磺草胺(florasulam)、吡氟禾草灵(fluazifop)和精吡氟禾草灵(fluazifop-P),吡氟禾草灵丁酯(fluazifop-butyl)、精吡氟禾草灵丁酯(fluazifop-P-butyl)、异丙吡草酯(fluazolate)、氟唑磺隆(flucarbazone)、氟酮磺隆(flucarbazone-sodium)、氟吡磺隆(flucetosulfuron)、氯乙氟灵(fluchloralin)、氟噻草胺(flufenacet,thiafluamide)、氟哒嗪草酯(flufenpyr)、氟哒嗪草酯(flufenpyr-ethyl)、氟节胺(flumetralin)、唑嘧磺草胺(flumetsulam)、氟烯草酸(flumiclorac)、氟烯草酸(flumiclorac-pentyl)、丙炔氟草胺(flumioxazin)、炔草胺(flumipropyn)、氟草隆(fluometuron)、三氟硝草醚(fluorodifen)、乙羧氟草醚(fluoroglycofen)、乙羧氟草醚乙酯(fluoroglycofen-ethyl)、氟胺草唑(flupoxam)、氟丙嘧草酯(flupropacil)、四氟丙酸(flupropanoate)、氟啶磺隆(flupyrsulfuron)、氟啶嘧磺隆(flupyrsulfuron-methyl-sodium))、抑草丁(flurenol)、抑草丁丁酯(flurenol-butyl)、氟啶草酮(fluridone)、氟咯草酮(flurochloridone)、氟草烟(fluroxypyr)、甲基庚酯(fluroxypyr-meptyl)、呋嘧醇(flurprimidol)、呋草酮(flurtamone)、嗪草酸(fluthiacet)、嗪草酸甲酯(fluthiacet-methyl)、噻唑草酰胺(fluthiamide)、氟磺胺草醚(fomesafen)、甲酰氨磺隆(foramsulfuron)、氯吡脲(forchlorfenuron)、杀木膦(fosamine)、呋氧草醚(furyloxyfen)、赤霉素(gibberillic acid)、草铵膦(glufosinate)、草铵膦铵(glufosinate-ammonium)、精草铵膦(glufosinate-P)、精草铵膦铵(glufosinate-P-ammonium)、精草铵膦钠(glufosinate-P-sodium)、草甘膦(glyphosate)、草甘膦异丙胺盐(glyphosate-isopryplammonium)、H-9201(即邻-(2,4-二甲基-6-硝基苯)邻-乙基异丙基硫代氨基磷酸酯)、氟硝磺酰胺(halosafen)、氯吡嘧磺隆(halosulfuron)、氯吡嘧磺隆甲酯(halosulfuron-methyl)、氟吡禾灵(haloxyfop)、精氟吡禾灵(haloxyfop-P)、氟吡禾灵乙氧基乙酯(haloxyfop-ethoxyethyl)、精氟吡禾灵乙氧基乙酯(haloxyfop-P-ethoxyethyl)、氟吡禾灵甲酯(haloxyfop-methyl)、精氟吡禾灵甲酯(haloxyfop-P-methyl)、环嗪酮(hexazinone)、HW-02(即1-(二甲氧基磷酸)乙基(2,4-二氯苯氧基)乙酸乙酯)、咪草酸(imazamethabenz)、咪草酸甲酯(imazamethabenz-methyl)、甲氧咪草烟(imazamox)、甲氧咪草烟铵(imazamox-ammonium)、甲咪唑烟酸(imazapic)、灭草烟(imazapyr)、灭草烟异丙基铵(imazapyr-isopropylammonium)、咪唑喹啉酸(imazaquin)、咪唑喹啉酸铵(imazaquin-ammonium)、咪唑乙烟酸(imazethapyr)、唑吡嘧磺隆(imazosulfuron)、抗倒胺(inabenfide)、茚草酮(indanofan)、碘甲磺隆(indaziflam)、吲哚乙酸(indoleacetic acid(IAA))、4-吲哚-3-基丁酸(IBA)、碘甲磺隆(iodosulfuron)、碘甲磺隆甲酯钠(iodosulfuron-methyl-sodium)、碘苯腈(ioxynil)、三哇苯胺除草剂(ipfencarbazone)、丁脒酰胺(isocarbamid)、异丙乐灵(isopropalin)、异丙隆(isoproturon)、异噁隆(isouron)、异噁酰草胺(isoxaben)、异噁氯草酮(isoxachlortole)、异噁唑草酮(isoxaflutole)、异噁草醚(isoxapyrifop)、KUH-043(即3-({[5-(二氟甲基)-1-甲基-3-(三氟甲基)-1H-吡唑-4-基]甲基}磺酰基)-5,5-二甲基-4,5-二氢-1,2-噁唑)、特胺灵(karbutilate)、1H、ketospiradox、乳氟禾草灵(lactofen)、环草定(lenacil)、利谷隆(linuron)、马来酰肼(maleic hydrazide)、MCPA、MCPB、MCPB-甲酯(MCPB-methyl)、MCPB-乙酯(MCPB-ethyl)和MCPB-钠(MCPB-sodium)、2-甲-4-氯丙酸(mecoprop)、2-甲-4-氯丙酸钠(mecoprop-sodium)、2-甲-4-氯丙酸丁氧酯(mecoprop-butotyl)、精2-甲-4-氯丙酸丁氧酯(mecoprop-P-butotyl)、精2-甲-4-氯丙酸二甲氨(mecoprop-P-dimethylammonium)、精2-甲-4-氯丙酸-2-乙基己酯(mecoprop-P-2-ethylhexyl)、精2-甲-4-氯丙酸钾(mecoprop-P-potassium)、苯噻酰草胺(mefenacet)、氯磺酰草胺(mefluidide)、甲哌啶(mepiquat-chloride)、甲磺胺磺隆(mesosulfuron)、甲磺胺磺隆甲酯(mesosulfuron-methyl)、甲基磺草酮(mesotrione)、甲基苯噻隆(methabenzthiazuron)、威百亩(metam)、噁唑酰草胺(metamifop)、苯嗪草酮(metamitron)、吡唑草胺(metazachlor)、双醚氯吡嘧磺隆(metazosulfuron)、灭草唑(methazole)、methiopyrsulfuron、methiozolin、苯草酮(methoxyphenone)、甲基杀草隆(methyldymron)、1-甲基环丙烯(1-methylcyclopropene)、异硫氰酸甲酯(methylisothiocyanate)、吡喃隆(metobenzuron)、吡喃隆(metobenzuron)、溴谷隆(metobromuron)、异丙甲草胺(metolachlor)、S-异丙甲草胺(S-metolachlor)、磺草唑胺(metosulam)、甲氧隆(metoxuron)、嗪草酮(metribuzin)、甲磺隆(metsulfuron)、甲磺隆(metsulfuron-methyl)、禾草敌(molinate)、庚酰草胺(monalide)、单脲(monocarbamide)、甲酰胺硫酸盐(monocarbamide dihydrogensulfate)、绿谷隆(monolinuron)、单嘧磺隆(monosulfuron)、单嘧磺隆酯(monosulfuron esters)、灭草隆(monuron)、MT 128(即6-氯-N-[(2E)-3-氯丙烯-2-烯-1-基]-5-甲基-N-苯吡啶-3-胺)、MT-5950(即N[3-氯-4-(1-甲基乙基)苯基]2-甲基戊酰胺)、NGGC-011、萘丙胺(naproanilide)、敌草胺(napropamide)、萘草胺(naptalam)、NC-310(即4-(2,4-二氯苯甲酰基)-1-甲基-5-苄氧基吡唑)、草不隆(neburon)、烟嘧磺隆(nicosulfuron)、氟氯草胺(nipyraclofen)、甲磺乐灵(nitralin)、除草醚(nitrofen)、复硝酚钠(nitrophenolate-sodium(异构体混合物))、硝氟草醚(nitrofluorfen)、正壬酸(nonanoic acid)、氟草敏(norflurazon)、坪草丹(orbencarb)、嘧苯胺磺隆(orthosulfamuron)、氨磺乐灵(oryzalin)、丙炔噁草酮(oxadiargyl)、噁草酮(oxadiazon)、环氧嘧磺隆(oxasulfuron)、噁嗪草酮(oxaziclomefone)、乙氧氟草醚(oxyfluorfen)、多效唑(paclobutrazole)、百草枯(paraquat)、百草枯(paraquatdichloride)、壬酸(pelargonic acid(nonanoic acid))、二甲戊灵(pendimethalin)、4-(叔丁基)-N-(1-乙基-丙基)-2,6-二硝基-苯胺(pendralin)、五氟磺草胺(penoxsulam)、甲氯酰草胺(pentanochlor)、环戊噁草酮(pentoxazone)、黄草伏(perfluidone)、烯草胺(pethoxamid)、棉胺宁(phenisopham)、甜菜宁(phenmedipham)、甜菜宁-乙酯(phenmedipham-ethyl)、氨氯吡啶酸(picloram)、氟吡酰草胺(picolinafen)、唑啉草酯(pinoxaden)、哌草磷(piperophos)、pirifenop、pirifenop-butyl、丙草胺(pretilachlor)、氟嘧磺隆(primisulfuron)、氟嘧磺隆甲酯(primisulfuron-methyl)、烯丙苯噻唑(probenazole)、氟唑草胺(profluazole)、环丙氰津(procyazine)、氨氟乐灵(prodiamine)、环丙氟灵(profluraline)、环苯草酮(profoxydim)、调环酸(prohexadione)、调环酸(prohexadione-calcium)、茉莉酮(prohydrojasmone)、扑灭通(prometon)、扑草净(prometryn)、毒草胺(propachlor)、敌稗(propanil)、噁草酸(propaquizafop)、扑灭津(propazine)、苯胺灵(propham)、异丙草胺(propisochlor)、丙苯磺隆(propoxycarbazone)、丙苯磺隆钠(propoxycarbazone-sodium)、嗪咪唑嘧磺隆(propyrisulfuron)、炔苯酰草胺(propyzamide)、磺亚胺草(prosulfalin)、苄草丹(prosulfocarb)、氟磺隆(prosulfuron)、丙炔草胺(prynachlor)、双唑草腈(pyraclonil)、吡草醚(pyraflufen)、吡草醚乙酯(pyraflufen-ethyl)、pyrasulfotole、吡唑特(pyrazolynate(pyrazolate))、吡嘧磺隆(pyrazosulfuron)、吡嘧磺隆(pyrazosulfuron-ethyl)、苄草唑(pyrazoxyfen)、异丙酯草醚(pyribambenz)、异丙酯草醚异丙酯(pyribambenz-isopropyl)、嘧啶肟草醚(pyribenzoxim)、稗草丹(pyributicarb)、达草止(pyridafol)、哒草特(pyridate)、环酯草醚(pyriftalid)、嘧草醚(pyriminobac)、嘧草醚甲酯(pyriminobac-methyl)、pyrimisulfan、嘧草硫醚(pyrithiobac)、嘧草硫醚钠(pyrithiobac-sodium)、异噁草酮(pyroxasulfone)、甲氧磺草胺(pyroxsulam)、二氯喹啉酸(quinchlorac)、氯甲喹啉酸(quinmerac)、灭藻醌(quinoclamine)、喹禾灵(quizalofop)、喹禾灵乙酯(quizalofop-ethyl)、精喹禾灵(quizalofop-P)、精喹禾灵乙酯(quizalofop-P-ethyl)、喹禾糠酯(quizalofop-P-tefuryl)、砜嘧磺隆(rimsulfuron)、苯嘧磺草胺(saflufenacil)、仲丁通(secbumeton)、烯禾啶(sethoxydim)、环草隆(siduron)、西玛津(simazine)、西草净(simetryn)、SN-106279(即(2R)-2-({7-[2-氯-4-(三氟甲基)苯氧基]-2-萘基}氧)丙酸甲酯)、磺草酮(sulcotrione)、草克死(sulfallate(CDEC))、甲磺草胺(sulfentrazone)、甲嘧磺隆(sulfometuron)、甲嘧磺隆(sulfometuron-methyl)、草硫膦(sulfosate(glyphosate-trimesium))、磺酰磺隆(sulfosulfuron)、SYN-523、SYP-249(即1-乙氧基-3-甲基-1-氧代丁-3-烯-2-基5-[2-氯-4-(三氟甲基)苯氧基]-2-硝基苯甲酸酯)、SYP-300(即1-[7-氟-3-氧代-4-(丙-2-炔-1-基)-3,4-二氢-2H-1,4-苯并噁嗪-6-基]-3-丙基-2-硫代咪唑啉-4,5-二酮、牧草胺(tebutam)、丁噻隆(tebuthiuron)、四氯硝基苯(tecnazene)、tefuryltrione、环磺酮(tembotrione)、吡喃草酮(tepraloxydim)、特草定(terbacil)、特草灵(terbucarb)、特丁草胺(terbuchlor)、特丁通(terbumeton)、特丁津(terbuthylazine)、特丁净(terbutryne)、噻吩草胺(thenylchlor)、氟噻草胺(thiafluamide)、噻氟隆(thiazafluron)、噻唑烟酸(thiazopyr)、噻二唑草胺(thidiazimin)、噻苯隆(thidiazuron)、噻酮磺隆(thiencarbazone)、噻酮磺隆甲酯(thiencarbazone-methyl)、噻吩磺隆(thifensulfuron)、噻吩磺隆甲酯(thifensulfuron-methyl)、禾草丹(thiobencarb)、仲草丹(tiocarbazil)、苯吡唑草酮(topramezone)、三甲苯草酮(tralkoxydim)、野燕畏(triallate)、醚苯磺隆(triasulfuron)、三嗪氟草胺(triaziflam)、triazofenamide、苯磺隆(tribenuron)、苯磺隆甲酯(tribenuron-methyl)、三氯乙酸(trichloroacetic acid(TCA))、三氯吡氧乙酸(triclopyr)、灭草环(tridiphane)、草达津(trietazine)、三氟啶磺隆(trifloxysulfuron)、三氟啶磺隆钠(trifloxysulfuron-sodium)、氟乐灵(trifluralin)、氟胺磺隆(triflusulfuron)、氟胺磺隆甲酯(triflusulfuron-methyl)、三甲隆(trimeturon)、抗倒酯(trinexapac)、抗倒酯(trinexapac-ethyl)、三氟甲磺隆(tritosulfuron)、tsitodef、烯效唑(uniconazole)、精烯效唑(uniconazole-P)、灭草敌(vernolate)、ZJ-0862(即3,4-二氯-N-{2-[(4,6-二甲氧基嘧啶-2-基)氧]苄基}苯胺)和以下化合物
为了应用,如果合适,市售形式的制剂以常规方式用水稀释,例如在可湿性粉剂、可乳化缩合物、分散剂和水分散性颗粒剂的情况下。粉尘型制剂、用于土壤施用的颗粒剂或用于撒播的颗粒剂和可喷雾溶液剂通常在施用前不再用其他惰性物质稀释。
式(I)的化合物的所需施用率根据外界条件(尤其包括温度、湿度和所用的除草剂类型)而变化。所述施用率可在宽泛范围内变化,例如0.001至1.0kg/ha或更多的活性物质,但优选0.005至750g/ha。
以下实施例来说明本发明:
A.化学实施例
制备2,4-二氯-6-氟-N-(5-甲基-1,3,4-噁二唑-2-基)-3-(甲基硫烷基)苯甲酰胺(实施例编号2-242)
1:制备1,3-二氯-5-氟-2-(甲基硫烷基)苯
在氮气气氛下,在0℃下,将9.5g(67mmol)碘甲烷添加到11.0g(55.8mmol)2,6-二氯-4-氟苯硫醇和11.6g(84mmol)K2CO3于50ml DMF的混合物中。在室温下搅拌12小时后,将反应混合物倒入冰上,然后用叔丁基甲基醚萃取。将有机相用水洗涤两次,并用饱和NaCl溶液洗涤一次,经硫酸钠干燥并浓缩。
收率:10.55g(90%);呈略淡黄色的油。
2:制备2,4-二氯-6-氟-3-(甲基硫烷基)苯甲酸
在-78℃下,将20ml(50mmol)2.5M nBuLi溶液滴加到10.55g(50mmol)1,3-二氯-5-氟-2-(甲基硫烷基)苯于100ml THF(无水)中的溶液中。在-78℃下搅拌1小时后,通入过量的CO2。随后,使反应混合物升温至室温,然后倒入500ml 1M氢氧化钠水溶液中。然后,用叔丁基甲基醚洗涤该混合物。使用2M HCl溶液将水相酸化至pH为4,然后用叔丁基甲基醚萃取。有机相用硫酸钠干燥,过滤并浓缩。
收率:10g(39mmol;78%)
1H-NMR(40MHz;DMSO-d6):7.63ppm(d,1H);2.42(s,3H)。
3:制备2,4-二氯-6-氟-N-(5-甲基-1,3,4-噁二唑-2-基)-3-(甲基硫烷基)苯甲酰胺(实施例编号2-242)
在0℃下,将448mg(0.309ml,3.53mmol)草酰氯滴加到600mg(2.35mmol)2,4-二氯-6-氟-3-(甲基硫烷基)苯甲酸和326mg(3.29mmol)2-氨基-5-甲基-1,3,4-噁二唑于20ml吡啶的溶液中。在0℃下1小时后,将反应混合物升温至室温并在室温下搅拌14小时。然后,将混合物浓缩,并向残余物中分别加入20ml二氯甲烷和水。相分离后,有机相使用硫酸钠干燥,过滤并浓缩。残余物通过柱色谱法(硅胶,庚烷/乙酸乙酯)纯化。
收率:165mg(纯度90%;19%)
1H-NMR(40MHz;DMSO-d6):12.59ppm(bs,1H),7.86ppm(d,1H),2.41ppm(s,3H)。
制备2,4-二氯-6-氟-N-(5-甲基-1,3,4-噁二唑-2-基)-3-(甲基亚磺酰基)苯甲酰胺(实施例编号2-243)
在0℃下,将107mg(0.465mmol)间氯过氧苯甲酸加入115mg(0.274mmol)2,4-二氯-6-氟-N-(5-甲基-1,3,4-噁二唑-2-基)-3-(甲基硫烷基)苯甲酰胺(实施例编号2-242)于20ml二氯甲烷的溶液中。室温下搅拌2天后,加入亚硫酸盐水溶液。萃取后,将有机相浓缩并通过柱色谱法(HPLC;乙腈/水)纯化。
收率:32mg(纯度95%;31%)
H-NMR(40MHz;DMSO-d6):11.60ppm(bs,1H),7.24ppm(d,1H);3.07ppm(s,3H)。
所用的缩写表示:
Et=乙基Me=甲基n-Pr=正丙基i-Pr=异丙基
c-Pr=环丙基Ph=苯基Ac=乙酰基Bz=苯甲酰基
表1:通式(I)的化合物,其中A代表CY,W代表氟并且V和R代表氢
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表2:通式(I)的化合物,其中A代表CY,V代表氢,W代表氟并且R代表甲基
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表3:通式(I)的化合物,其中A代表CY,V代表氢,W代表氟并且R代表乙基
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表4:通式(I)的化合物,其中A代表CY,V代表氢,W代表氟并且R代表三氟甲基
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表5:通式(I)的化合物,其中A代表CY,V代表氢,W代表氟并且R代表CH2OMe
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表6:通式(I)的化合物,其中A代表CY,V代表氢,W代表氟
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表7:通式(I)的化合物,其中A代表氮,V代表氢,W代表氟
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表8:根据本发明的通式(I)的化合物,其中A代表CY,Z代表三氟甲基并且R代表甲基
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B.制剂实施例
a)撒粉产品通过以下方式获得:将10重量份的式(I)的化合物和/或其盐与90重量份作为惰性物质的滑石混合,并将该混合物在锤磨机中粉碎。
b)易分散于水中的可湿性粉剂通过以下方式获得:将25重量份的式(I)的化合物和/或其盐、64重量份的作为惰性物质的含高岭土的石英、作为湿润剂和分散剂的10重量份的木素磺酸钾和1重量份的油酰基甲基牛磺酸钠混合,将该混合物在销盘式研磨机(pinned-disk mill)中研磨。
c)易分散于水中的分散浓缩剂通过以下方式获得:将20重量份的式(I)的化合物和/或其盐与6重量份的烷基酚聚乙二醇醚(X 207)、3重量份的异十三烷醇聚乙二醇醚(8EO)和71重量份的石蜡矿物油(沸程例如约255至高于277℃)混合,并将该混合物在球磨机中研磨至细度小于5微米。
d)可乳化浓缩剂通过以下方式获得:将15重量份的式(I)的化合物和/或其盐、75重量份作为溶剂的环己酮和10重量份作为乳化剂的乙氧基化壬基苯酚混合。
e)水分散性颗粒剂通过将下述物质混合,将混合物在销盘式研磨机中研磨,并在流化床中通过喷雾施用作为制粒液体的水而使粉末粒化而获得:
75重量份的式(I)的化合物和/或其盐,
10重量份的木素磺酸钙,
5重量份的十二烷基硫酸钠,
3重量份的聚乙烯醇,和
7重量份的高岭土。
f)水分散性颗粒剂还通过以下方式获得:在胶体研磨机中将下述物质均化并预粉碎:
25重量份的式(I)的化合物和/或其盐,
5重量份的2,2’-二萘基甲烷-6,6’-二磺酸钠,
2重量份的油酰基甲基牛磺酸钠,
1重量份的聚乙烯醇,
17重量份的碳酸钙,和
50重量份的水,
随后,在砂磨机中研磨该混合物,并在喷雾塔中通过单相喷嘴将所得悬浮液雾化并干燥。
C.生物实施例
1.对抗有害植物的出苗前除草作用
将单子叶和双子叶杂草植物和作物植物的种子置于装有砂质壤土的木纤维盆中,并用土壤覆盖。然后,将配制为可湿性粉剂(WP)或可乳化浓缩剂(EC)形式的本发明化合物,在添加0.2%湿润剂的情况下,以含水悬浮液或乳液的形式,在相当于600至800l/ha的水施用率下施用至覆盖土壤的表面。处理后,将盆置于温室中并保持在对试验植物而言良好的生长条件下。在3周的测试期后,通过与未处理的对照组比较而目测评估对试验植物的损害(除草活性百分比(%):100%功效=植物已死亡;0%功效=与对照植物相同)。
在本试验中,例如编号2-242和2-243的化合物在320g/ha的施用率下各自对以下杂草显示出至少80%的功效:稗草(Echinochloa crusgalli)、狗尾草(Setaria viridis)、反枝苋(Amaranthus retroflexus)、繁缕(Stellaria media)、阿拉伯婆婆纳(Veronicapersica)和三色堇(Viola tricolor)。
2.对有害植物的出苗后除草作用
将单子叶和双子叶杂草植物和作物植物的种子置于装有砂质壤土的木纤维盆中,并用土壤覆盖,并于温室中在良好的生长条件下培育。播种后2至3周,在单叶期处理试验植物。然后,将配制为可湿性粉剂(WP)或可乳化浓缩剂(EC)形式的本发明化合物,在添加0.2%湿润剂的情况下,以含水悬浮液或乳液的形式,在相当于600至800l/ha的水施用率下喷雾至植物的绿色部位。在将试验植物置于最佳生长条件的温室中约3周后,通过与未处理的对照组比较而目测评估制剂的作用(除草活性百分比(%):100%功效=植物已死亡;0%功效=与对照植物相同)。
在本试验中,例如编号2-242和2-243的化合物在80g/ha的施用率下各自对以下杂草显示出至少80%的功效:稗草(Echinochloa crus galli)、狗尾草(Setaria viridis)、苘麻(Abutilon theophrasti)、反枝苋(Amaranthus retroflexus)、繁缕(Stellariamedia)和三色堇(Viola tricolor)。
Claims (15)
1.一种式(I)的N-(1,3,4-噁二唑-2-基)芳基羧酰胺或其盐
其中,取代基具有以下含义:
A代表C-Y,
R代表氢、甲基或乙基,
X代表氟、氯、溴、甲基、乙基、正丙基或异丙基,
Y代表S(O)nR2,
Z代表卤素或卤代-(C1-C6)-烷基,
V代表氢,
W代表氟,
R2代表(C1-C6)-烷基,并且
n代表0、1或2。
2.如权利要求1所述的N-(1,3,4-噁二唑-2-基)芳基羧酰胺,其特征在于
Y代表S(O)nR2,并且
Z代表三氟甲基、二氟甲基或五氟乙基。
3.如权利要求1所述的N-(1,3,4-噁二唑-2-基)芳基羧酰胺,其特征在于
X代表F、Cl、Br、CH3、乙基、正丙基或异丙基,
Y代表S(O)Me、S(O)Et、SO2Me或SO2Et,并且
Z代表F、Cl、Br、I或CF3。
4.如权利要求1所述的N-(1,3,4-噁二唑-2-基)芳基羧酰胺,其特征在于
A代表C-Y,
R代表氢、甲基或乙基,
X代表氟、氯、溴、甲基、乙基、正丙基或异丙基,
Y代表S(O)nR2,
Z代表F、Cl、Br或CF3,
V代表氢,
W代表氟,
R2代表甲基或乙基,并且
n代表1或2。
5.化合物2,4-二氯-6-氟-N-(5-甲基-1,3,4-噁二唑-2-基)-3-(甲基亚磺酰基)苯甲酰胺,或其盐。
6.一种除草剂组合物,其特征在于包含除草有效量的至少一种权利要求1所述的式(I)的化合物。
7.如权利要求6所述的除草剂组合物,其与制剂助剂混合。
8.如权利要求6所述的除草剂组合物,其包含至少一种选自杀昆虫剂、杀螨剂、除草剂、杀真菌剂、安全剂和生长调节剂的其他农药活性物质。
9.如权利要求8所述的除草剂组合物,其包含安全剂。
10.如权利要求9所述的除草剂组合物,其包含环丙磺酰胺、解毒喹、吡唑解草酯或双苯噁唑酸。
11.如权利要求6所述的除草剂组合物,其包含另一种除草剂。
12.一种防治不想要的植物的方法,其特征在于将有效量的至少一种如权利要求1所述的式(I)的化合物或如权利要求6所述的除草剂组合物施用于植株或不想要的植物的位点。
13.如权利要求1所述的式的(I)化合物或如权利要求6所述的除草剂组合物用于防治不想要的植物的用途。
14.如权利要求13所述的用途,其特征在于将式(I)的化合物用于在有用植物作物中防治不想要的植物。
15.如权利要求14所述的用途,其特征在于有用植物为转基因有用植物。
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WO2020219792A1 (en) * | 2019-04-26 | 2020-10-29 | Purdue Research Foundation | Cf3-, ocf3-, scf3- and sf5-containing antibacterial agents |
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Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103596946A (zh) * | 2011-03-22 | 2014-02-19 | 拜耳知识产权有限责任公司 | N-(1,3,4-噁二唑-2-基)芳基甲酰胺及其作为除草剂的用途 |
WO2014144710A1 (en) * | 2013-03-15 | 2014-09-18 | The University Of Chicago | Methods and compositions for bacteria infections |
CN104428297A (zh) * | 2012-04-27 | 2015-03-18 | 巴斯夫欧洲公司 | 取代的n-(四唑-5-基)-和n-(三唑-5-基)芳基羧酰胺化合物及其作为除草剂的用途 |
WO2017102275A1 (en) * | 2015-12-17 | 2017-06-22 | Basf Se | Benzamide compounds and their use as herbicides |
Family Cites Families (29)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
MA19269A1 (fr) * | 1980-09-16 | 1982-04-01 | Lilly Co Eli | Perfectionnement relatif a des derives de n-arylbenzamides . |
EP0131624B1 (en) | 1983-01-17 | 1992-09-16 | Monsanto Company | Plasmids for transforming plant cells |
BR8404834A (pt) | 1983-09-26 | 1985-08-13 | Agrigenetics Res Ass | Metodo para modificar geneticamente uma celula vegetal |
IT1196237B (it) | 1984-08-29 | 1988-11-16 | Enichimica Secondaria | Composti eterociclici ad attivita' erbicida |
BR8600161A (pt) | 1985-01-18 | 1986-09-23 | Plant Genetic Systems Nv | Gene quimerico,vetores de plasmidio hibrido,intermediario,processo para controlar insetos em agricultura ou horticultura,composicao inseticida,processo para transformar celulas de plantas para expressar uma toxina de polipeptideo produzida por bacillus thuringiensis,planta,semente de planta,cultura de celulas e plasmidio |
ATE80182T1 (de) | 1985-10-25 | 1992-09-15 | Monsanto Co | Pflanzenvektoren. |
DE3765449D1 (de) | 1986-03-11 | 1990-11-15 | Plant Genetic Systems Nv | Durch gentechnologie erhaltene und gegen glutaminsynthetase-inhibitoren resistente pflanzenzellen. |
EP0305398B1 (en) | 1986-05-01 | 1991-09-25 | Honeywell Inc. | Multiple integrated circuit interconnection arrangement |
US5013659A (en) | 1987-07-27 | 1991-05-07 | E. I. Du Pont De Nemours And Company | Nucleic acid fragment encoding herbicide resistant plant acetolactate synthase |
IL83348A (en) | 1986-08-26 | 1995-12-08 | Du Pont | Nucleic acid fragment encoding herbicide resistant plant acetolactate synthase |
DE3733017A1 (de) | 1987-09-30 | 1989-04-13 | Bayer Ag | Stilbensynthase-gen |
EP0472722B1 (en) | 1990-03-16 | 2003-05-21 | Calgene LLC | Dnas encoding plant desaturases and their uses |
ATE212670T1 (de) | 1990-06-18 | 2002-02-15 | Monsanto Technology Llc | Erhöhter stärkegehalt in pflanzen |
DE69132939T2 (de) | 1990-06-25 | 2002-11-14 | Monsanto Technology Llc | Glyphosattolerante pflanzen |
DE4107396A1 (de) | 1990-06-29 | 1992-01-02 | Bayer Ag | Stilbensynthase-gene aus weinrebe |
SE467358B (sv) | 1990-12-21 | 1992-07-06 | Amylogene Hb | Genteknisk foeraendring av potatis foer bildning av staerkelse av amylopektintyp |
DE4104782B4 (de) | 1991-02-13 | 2006-05-11 | Bayer Cropscience Gmbh | Neue Plasmide, enthaltend DNA-Sequenzen, die Veränderungen der Karbohydratkonzentration und Karbohydratzusammensetzung in Pflanzen hervorrufen, sowie Pflanzen und Pflanzenzellen enthaltend dieses Plasmide |
CN1126208A (zh) | 1995-05-03 | 1996-07-10 | 华东理工大学 | 2-酰胺基-5-芳基-1,3,4-噁二唑化合物及其合成与应用 |
DE19846792A1 (de) | 1998-10-10 | 2000-04-13 | Hoechst Schering Agrevo Gmbh | Benzoylcyclohexandione, Verfahren zur ihrer Herstellung und ihre Verwendung als Herbizide und Pflanzenwachstumsregulatoren |
DE19935218A1 (de) | 1999-07-27 | 2001-02-01 | Aventis Cropscience Gmbh | Isoxazolyl-substituierte Benzoylcyclohexandione, Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide und Pflanzenwachstumsregulatoren |
DE10301110A1 (de) | 2003-01-09 | 2004-07-22 | Bayer Cropscience Gmbh | Substituierte Benzoylderivate als Herbizide |
MX2012003377A (es) | 2009-09-25 | 2012-05-08 | Bayer Cropscience Ag | N-(1,2,5-oxadiazol-3-il)benzamidas y su utilizacion como herbicidas. |
PT2611785E (pt) | 2010-09-01 | 2014-09-09 | Bayer Ip Gmbh | Amidas de ácido n-(tetrazol-5-il)- e n-(triazol-5- il)arilcarboxílico e sua utilização como herbicidas |
JP5781467B2 (ja) | 2012-04-12 | 2015-09-24 | 有限会社シモダ技術研究所 | グラウト製造装置及びグラウト製造方法 |
US9562002B2 (en) * | 2013-01-15 | 2017-02-07 | Board Of Regents, The University Of Texas System | STAT3 inhibitor |
CA2910707A1 (en) | 2013-05-15 | 2014-11-20 | Basf Se | Substituted n-(tetrazol-5-yl)- and n-(triazol-5-yl)arylcarboxamide compounds and their use as herbicides |
WO2014184015A1 (en) | 2013-05-15 | 2014-11-20 | Basf Se | Substituted n-(tetrazol-5-yl)- and n-(triazol-5-yl)arylcarboxamide compounds and their use as herbicides |
HUE047821T2 (hu) | 2015-03-17 | 2020-05-28 | Bayer Cropscience Ag | N-(l,3,4-oxadiazol-2-il)aril-karbonsav-amidok sói és ezek alkalmazása herbicidként |
CN108349912B (zh) | 2015-08-25 | 2021-06-08 | 拜耳作物科学股份公司 | 取代的酮肟苯甲酰胺 |
-
2018
- 2018-03-22 EA EA201992259A patent/EA201992259A1/ru unknown
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- 2018-03-22 EP EP18712609.9A patent/EP3601242A1/de not_active Withdrawn
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- 2018-03-22 MX MX2019011774A patent/MX2019011774A/es unknown
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- 2018-04-02 UY UY0001037647A patent/UY37647A/es unknown
-
2019
- 2019-10-29 ZA ZA2019/07150A patent/ZA201907150B/en unknown
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103596946A (zh) * | 2011-03-22 | 2014-02-19 | 拜耳知识产权有限责任公司 | N-(1,3,4-噁二唑-2-基)芳基甲酰胺及其作为除草剂的用途 |
CN104428297A (zh) * | 2012-04-27 | 2015-03-18 | 巴斯夫欧洲公司 | 取代的n-(四唑-5-基)-和n-(三唑-5-基)芳基羧酰胺化合物及其作为除草剂的用途 |
WO2014144710A1 (en) * | 2013-03-15 | 2014-09-18 | The University Of Chicago | Methods and compositions for bacteria infections |
WO2017102275A1 (en) * | 2015-12-17 | 2017-06-22 | Basf Se | Benzamide compounds and their use as herbicides |
Non-Patent Citations (1)
Title |
---|
"Registry数据库";ACS;《American Chmical Society(ACS) STNext》;20160911;CAS RN:1990730-06-7;1979442-23-3等 * |
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