CN105209452A - 4-氨基-6-(杂环基)吡啶-2-甲酸酯和6-氨基-2-(杂环基)嘧啶-4-羧酸酯以及它们作为除草剂的用途 - Google Patents
4-氨基-6-(杂环基)吡啶-2-甲酸酯和6-氨基-2-(杂环基)嘧啶-4-羧酸酯以及它们作为除草剂的用途 Download PDFInfo
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- CN105209452A CN105209452A CN201480027999.7A CN201480027999A CN105209452A CN 105209452 A CN105209452 A CN 105209452A CN 201480027999 A CN201480027999 A CN 201480027999A CN 105209452 A CN105209452 A CN 105209452A
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- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
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- UCDPMNSCCRBWIC-UHFFFAOYSA-N orthosulfamuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)NC=2C(=CC=CC=2)C(=O)N(C)C)=N1 UCDPMNSCCRBWIC-UHFFFAOYSA-N 0.000 description 1
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- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- DLRJIFUOBPOJNS-UHFFFAOYSA-N phenetole Chemical compound CCOC1=CC=CC=C1 DLRJIFUOBPOJNS-UHFFFAOYSA-N 0.000 description 1
- DOQADKIOSUAXBD-UHFFFAOYSA-N phosphane tetrahydrate Chemical compound P.O.O.O.O DOQADKIOSUAXBD-UHFFFAOYSA-N 0.000 description 1
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- LGRFSURHDFAFJT-UHFFFAOYSA-N phthalic anhydride Chemical compound C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
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- RJQUHEYNLDNJLN-UHFFFAOYSA-N picloram-methyl Chemical compound COC(=O)C1=NC(Cl)=C(Cl)C(N)=C1Cl RJQUHEYNLDNJLN-UHFFFAOYSA-N 0.000 description 1
- CWKFPEBMTGKLKX-UHFFFAOYSA-N picolinafen Chemical compound C1=CC(F)=CC=C1NC(=O)C1=CC=CC(OC=2C=C(C=CC=2)C(F)(F)F)=N1 CWKFPEBMTGKLKX-UHFFFAOYSA-N 0.000 description 1
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
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- 238000012545 processing Methods 0.000 description 1
- OYJMHAFVOZPIOY-UHFFFAOYSA-N propan-2-yl 2-chloro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]benzoate Chemical compound C1=C(Cl)C(C(=O)OC(C)C)=CC(N2C(N(C)C(=CC2=O)C(F)(F)F)=O)=C1 OYJMHAFVOZPIOY-UHFFFAOYSA-N 0.000 description 1
- YRGNDQQIUXCCAI-UHFFFAOYSA-N propan-2-yl 4,5,6-trifluoropyridine-2-carboxylate Chemical class CC(C)OC(=O)C1=CC(F)=C(F)C(F)=N1 YRGNDQQIUXCCAI-UHFFFAOYSA-N 0.000 description 1
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- KZOJQMWTKJDSQJ-UHFFFAOYSA-M sodium;2,3-dibutylnaphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S([O-])(=O)=O)=C(CCCC)C(CCCC)=CC2=C1 KZOJQMWTKJDSQJ-UHFFFAOYSA-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
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 1
- FZMKKCQHDROFNI-UHFFFAOYSA-N sulfometuron Chemical compound CC1=CC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(O)=O)=N1 FZMKKCQHDROFNI-UHFFFAOYSA-N 0.000 description 1
- 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
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- 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
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000005622 tetraalkylammonium hydroxides Chemical class 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- VXKWYPOMXBVZSJ-UHFFFAOYSA-N tetramethyltin Chemical compound C[Sn](C)(C)C VXKWYPOMXBVZSJ-UHFFFAOYSA-N 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- XSKZXGDFSCCXQX-UHFFFAOYSA-N thiencarbazone-methyl Chemical compound COC(=O)C1=CSC(C)=C1S(=O)(=O)NC(=O)N1C(=O)N(C)C(OC)=N1 XSKZXGDFSCCXQX-UHFFFAOYSA-N 0.000 description 1
- LOQQVLXUKHKNIA-UHFFFAOYSA-N thifensulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C2=C(SC=C2)C(O)=O)=N1 LOQQVLXUKHKNIA-UHFFFAOYSA-N 0.000 description 1
- AHTPATJNIAFOLR-UHFFFAOYSA-N thifensulfuron-methyl Chemical group S1C=CC(S(=O)(=O)NC(=O)NC=2N=C(OC)N=C(C)N=2)=C1C(=O)OC AHTPATJNIAFOLR-UHFFFAOYSA-N 0.000 description 1
- 125000005323 thioketone group Chemical group 0.000 description 1
- GYICYQJEVCIYJY-UHFFFAOYSA-N thiophen-1-ylidenemethanone Chemical compound O=C=S1C=CC=C1 GYICYQJEVCIYJY-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 1
- IYMLUHWAJFXAQP-UHFFFAOYSA-N topramezone Chemical compound CC1=C(C(=O)C2=C(N(C)N=C2)O)C=CC(S(C)(=O)=O)=C1C1=NOCC1 IYMLUHWAJFXAQP-UHFFFAOYSA-N 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 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
- NKCIVLISTXOILK-UHFFFAOYSA-N triazinane-4,5,6-trione Chemical compound OC1=NN=NC(O)=C1O NKCIVLISTXOILK-UHFFFAOYSA-N 0.000 description 1
- BQZXUHDXIARLEO-UHFFFAOYSA-N tribenuron Chemical compound COC1=NC(C)=NC(N(C)C(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(O)=O)=N1 BQZXUHDXIARLEO-UHFFFAOYSA-N 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
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 229940087291 tridecyl alcohol Drugs 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- AKTQJCBOGPBERP-UHFFFAOYSA-N triflusulfuron Chemical compound FC(F)(F)COC1=NC(N(C)C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2C)C(O)=O)=N1 AKTQJCBOGPBERP-UHFFFAOYSA-N 0.000 description 1
- IMEVJVISCHQJRM-UHFFFAOYSA-N triflusulfuron-methyl Chemical group COC(=O)C1=CC=CC(C)=C1S(=O)(=O)NC(=O)NC1=NC(OCC(F)(F)F)=NC(N(C)C)=N1 IMEVJVISCHQJRM-UHFFFAOYSA-N 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 230000003442 weekly effect Effects 0.000 description 1
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- 239000000080 wetting agent Substances 0.000 description 1
- 235000005765 wild carrot Nutrition 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/10—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing aromatic rings
-
- 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
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/08—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing solids as carriers or diluents
-
- 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
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
-
- 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
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
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Abstract
本申请提供4-氨基-6-(杂环基)吡啶-2-甲酸及其衍生物和6-氨基-2-(杂环基)嘧啶-4-羧酸酯及其衍生物用于控制不期望的植被。不期望的植被例如杂草的产生是农场主在作物、牧场和其他场所中一直遇到的问题。杂草与作物竞争并且不利地影响着作物的收率。使用化学除草剂在防治不期望的植被中是重要的工具。
Description
相关申请的交叉参考
本申请要求2013年3月15日提交的美国临时专利申请61/790,391的权益,将其公开内容明确并入本申请作为参考。
技术领域
本发明涉及除草化合物和组合物以及涉及用于防治不期望植被的方法。
背景技术
不期望的植被例如杂草的产生是农场主在作物、牧场和其他场所中一直遇到的问题。杂草与作物竞争并且不利地影响着作物的收率。使用化学除草剂在防治不期望的植被中是重要的工具。
仍需要新的化学除草剂,该新的化学除草剂具有更宽的杂草控制谱、选择性、对作物的损害最小、贮存稳定性、易操作性、更高的抗杂草活性和/或是解决针对目前使用的除草剂发展出的除草剂耐药的手段。
发明内容
本申请提供式(I)化合物或其N-氧化物或农用盐:
其中
X为N或CY,其中Y为氢、卤素、C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、C1-C3烷氧基、C1-C3烷硫基或C1-C3卤代烷硫基;
R1为OR1′或NR1″R1″′,其中R1′为氢、C1-C8烷基或C7-C10芳基烷基,且R1″和R1″′独立地为氢、C1-C12烷基、C3-C12烯基或C3-C12炔基;
R2为卤素、C1-C4烷基、C1-C4卤代烷基、C2-C4烯基、C2-C4卤代烯基、C2-C4炔基、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷硫基、C1-C4卤代烷硫基、氨基、C1-C4烷基氨基、C2-C4卤代烷基氨基、甲酰基、C1-C3烷基羰基、C1-C3卤代烷基羰基、氰基或式-CR17=CR18-SiR19R20R21的基团,其中R17为氢、F或Cl;R18为氢、F、Cl、C1-C4烷基或C1-C4卤代烷基;且R19、R20和R21独立地为C1-C10烷基、C3-C6环烷基、苯基、取代苯基、C1-C10烷氧基或OH;
R3和R4独立地为氢、C1-C6烷基、C1-C6卤代烷基、C3-C6烯基、C3-C6卤代烯基、C3-C6炔基、甲酰基、C1-C3烷基羰基、C1-C3卤代烷基羰基、C1-C6烷氧基羰基、C1-C6烷基氨基甲酰基、C1-C6烷基磺酰基、C1-C6三烷基甲硅烷基、C1-C6二烷基氧膦基,或者R3和R4与N一起为5-或6元饱和或不饱和环,或者R3和R4一起表示=CR3′(R4′),其中R3′和R4′独立地为氢、C1-C6烷基、C3-C6烯基、C3-C6炔基、C1-C6烷氧基或C1-C6烷基氨基,或者R3′和R4′与=C一起表示5-或6-元饱和环;
A为基团Ar1至Ar28之一:
R5为氢、卤素、C1-C4烷基、C1-C4卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、C1-C3烷硫基、C1-C3卤代烷硫基、氨基、C1-C4烷基氨基或C2-C4卤代烷基氨基。
R6为氢、卤素、C1-C4烷基、C1-C4卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、C1-C3烷硫基、C1-C3卤代烷硫基、氨基、C1-C4烷基氨基或C2-C4卤代烷基氨基;
R6′为氢或卤素;
R6″为氢、卤素、C1-C4烷基、C1-C4卤代烷基、环丙基、卤代环丙基、C2-C4烯基、C2-C4卤代烯基、C2-C4炔基、C1-C3烷氧基、C1-C3卤代烷氧基、C1-C3烷硫基、C1-C3卤代烷硫基、氨基、C1-C4烷基氨基、C2-C4卤代烷基氨基、CN或NO2;
R7和R7′独立地为氢、卤素、C1-C4烷基、C1-C4卤代烷基或C1-C3烷氧基;
R8和R8′独立地为氢、卤素、C1-C4烷基、C1-C4卤代烷基或C1-C3烷氧基;
R9、R9′、R9″和R9″′独立地为氢、卤素、C1-C4烷基、C1-C4卤代烷基或C1-C3烷氧基;
R10为氢、C1-C6烷基、C1-C6卤代烷基、C3-C6烯基、C3-C6卤代烯基、C3-C6炔基、甲酰基、C1-C3烷基羰基、C1-C3卤代烷基羰基或C1-C6三烷基甲硅烷基;
m,当存在时,为0、1或2;和
n,当存在时,为0、1或2;
条件是A不为
还提供了防治不期望的植被的方法,包括施用式(I)化合物或其N-氧化物或农用盐。
发明详述
定义
本申请使用的除草剂和除草活性成分是指当以适当的量施用时防治不期望植被的化合物。
本申请使用的防治不期望的植被是指杀死或预防所述植被,或对所述植被造成其他不利的改变作用,例如,偏离自然生长或发育、调节、脱水、延迟等。
本申请使用的除草有效量或植被防治量为施用以防治相关不期望植被的除草活性成分的量。。
本申请使用的施用除草剂或除草组合物是指将其直接递送至目标植被或递送至该目标植被的所在地或递送至需要防治不期望植被的区域。施用方法包括但不限于出芽前接触土壤或水、出芽后接触不期望的植被或接触与该不期望的植被相邻的区域。
本申请使用的植物和植被包括但不限于休眠的种子、发芽的种子、发芽苗(emergingseedlings)、从无性繁殖体发芽的植物(plantsemergingfromvegetativepropagules)、不成熟的植被和已长成的植被(establishedvegetation)。
本申请使用的农用盐和酯是指表现出除草活性的盐和酯,或植物中、水中或土壤中被或可被转化成所述除草剂的盐和酯。示例性农用酯为通过水解、氧化、代谢或其他手段(例如,在植物、水或土壤中)被或可被转化成相应羧酸的那些酯,该羧酸根据pH可为解离或未解离形式。
适当的盐包括衍生自碱金属或碱土金属的那些盐和衍生自氨和胺的那些盐。优选的阳离子包括钠、钾、镁和下式的铵:
R13R14R15R16N+
其中R13、R14、R15和R16各自独立地表示氢或C1-C12烷基、C3-C12烯基或C3-C12炔基,它们各自任选被一个或多个羟基、C1-C4烷氧基、C1-C4烷基硫基或苯基取代,条件是R13、R14、R15和R16为立体相容的。此外,R13、R14、R15和R16中的任意两个可表示含有1至12个碳原子和最高2个氧原子或硫原子的脂肪族二官能部分。式I化合物的盐可通过用以下物质处理式I化合物来制备:金属氢氧化物例如氢氧化钠;胺例如氨、三乙胺、二乙醇胺、2-甲基硫基丙基胺、二烯丙基胺、2-叔丁氧基乙基胺、吗啉、环十二烷基胺或苄基胺,或;四烷基氢氧化铵或氢氧化胆碱。胺盐经常是式I化合物的优选形式,这是因为它们是水溶性的并且自身容易制备成所期望的水性基除草组合物。
式(I)化合物包括N-氧化物。吡啶N-氧化物可通过氧化相应的吡啶来获得。适当的氧化方法描述在例如Houben-Weyl,MethodenderorganischenChemie[Methodsinorganicchemistry]中(这是第四版的增卷和继卷),E7b卷,p.565f。
除非另有说明,本申请所用的酰基是指甲酰基,C1-C3烷基羰基和C1-C3卤代烷基羰基。C1-C6酰基是指甲酰基,C1-C5烷基羰基和C1-C5卤代烷基羰基(所述基团共含有1至6个碳原子)。
本申请使用的烷基是指饱和的、直链或支链饱和烃部分。除非另有说明,否则意在表示C1-C10烷基。实例包括甲基、乙基、丙基、1-甲基-乙基、丁基、1-甲基-丙基、2-甲基-丙基、1,1-二甲基-乙基、戊基、1-甲基-丁基、2-甲基-丁基、3-甲基-丁基、2,2-二甲基-丙基、1-乙基-丙基、己基、1,1-二甲基-丙基、1,2-二甲基-丙基、1-甲基-戊基、2-甲基-戊基、3-甲基-戊基、4-甲基-戊基、1,1-二甲基-丁基、1,2-二甲基-丁基、1,3-二甲基-丁基、2,2-二甲基-丁基、2,3-二甲基-丁基、3,3-二甲基-丁基、1-乙基-丁基、2-乙基-丁基、1,1,2-三甲基-丙基、1,2,2-三甲基-丙基、1-乙基-1-甲基-丙基和1-乙基-2-甲基-丙基。
本申请使用的“卤代烷基”是指直链或支链烷基基团,在这些基团中,氢原子可部分或全部被卤素原子取代。除非另有说明,意在表示C1-C8基团。实例包括氯甲基、溴甲基、二氯甲基、三氯甲基、氟甲基、二氟甲基、三氟甲基、氯氟甲基、二氯氟甲基、氯二氟甲基、1-氯乙基、1-溴乙基、1-氟乙基、2-氟乙基、2,2-二氟乙基、2,2,2-三氟乙基、2-氯-2-氟乙基、2-氯-2-二氟乙基、2,2-二氯-2-氟乙基、2,2,2-三氯乙基、五氟乙基和1,1,1-三氟丙-2-基。
本申请使用的烯基是指含有双键的不饱和的、直链或支链烃部分。除非另有说明,意在表示C2-C8烯基。烯基可含有多于一个的不饱和键。实例包括乙烯基、1-丙烯基、2-丙烯基、1-甲基乙烯基、1-丁烯基、2-丁烯基、3-丁烯基、1-甲基-1-丙烯基、2-甲基-1-丙烯基、1-甲基-2-丙烯基、2-甲基-2-丙烯基、1-戊烯基、2-戊烯基、3-戊烯基、4-戊烯基、1-甲基-1-丁烯基、2-甲基-1-丁烯基、3-甲基-1-丁烯基、1-甲基-2-丁烯基、2-甲基-2-丁烯基、3-甲基-2-丁烯基、1-甲基-3-丁烯基、2-甲基-3-丁烯基、3-甲基-3-丁烯基、1,1-二甲基-2-丙烯基、1,2-二甲基-1-丙烯基、1,2-二甲基-2-丙烯基、1-乙基-1-丙烯基、1-乙基-2-丙烯基、1-己烯基、2-己烯基、3-己烯基、4-己烯基、5-己烯基、1-甲基-1-戊烯基、2-甲基-1-戊烯基、3-甲基-1-戊烯基、4-甲基-1-戊烯基、1-甲基-2-戊烯基、2-甲基-2-戊烯基、3-甲基-2-戊烯基、4-甲基-2-戊烯基、1-甲基-3-戊烯基、2-甲基-3-戊烯基、3-甲基-3-戊烯基、4-甲基-3-戊烯基、1-甲基-4-戊烯基、2-甲基-4-戊烯基、3-甲基-4-戊烯基、4-甲基-4-戊烯基、1,1-二甲基-2-丁烯基、1,1-二甲基-3-丁烯基、1,2-二甲基-1-丁烯基、1,2-二甲基-2-丁烯基、1,2-二甲基-3-丁烯基、1,3-二甲基-1-丁烯基、1,3-二甲基-2-丁烯基、1,3-二甲基-3-丁烯基、2,2-二甲基-3-丁烯基、2,3-二甲基-1-丁烯基、2,3-二甲基-2-丁烯基、2,3-二甲基-3-丁烯基、3,3-二甲基-1-丁烯基、3,3-二甲基-2-丁烯基、1-乙基-1-丁烯基、1-乙基-2-丁烯基、1-乙基-3-丁烯基、2-乙基-1-丁烯基、2-乙基-2-丁烯基、2-乙基-3-丁烯基、1,1,2-三甲基-2-丙烯基、1-乙基-1-甲基-2-丙烯基、1-乙基-2-甲基-1-丙烯基和1-乙基-2-甲基-2-丙烯基。乙烯基是指具有结构–CH=CH2的基团;1-丙烯基是指具有结构–CH=CH-CH3的基团;和2-丙烯基是指具有–CH2-CH=CH2结构的基团。
本申请使用的炔基表示含有叁键的直链或支链烃部分。除非另有说明,意在表示C2-C8炔基。炔基可含有多于一个的不饱和键。实例包括C2-C6-炔基,例如乙炔基、1-丙炔基、2-丙炔基(或炔丙基)、1-丁炔基、2-丁炔基、3-丁炔基、1-甲基-2-丙炔基、1-戊炔基、2-戊炔基、3-戊炔基、4-戊炔基、3-甲基-1-丁炔基、1-甲基-2-丁炔基、1-甲基-3-丁炔基、2-甲基-3-丁炔基、1,1-二甲基-2-丙炔基、1-乙基-2-丙炔基、1-己炔基、2-己炔基、3-己炔基、4-己炔基、5-己炔基、3-甲基-1-戊炔基、4-甲基-1-戊炔基、1-甲基-2-戊炔基、4-甲基-2-戊炔基、1-甲基-3-戊炔基、2-甲基-3-戊炔基、1-甲基-4-戊炔基、2-甲基-4-戊炔基、3-甲基-4-戊炔基、1,1-二甲基-2-丁炔基、1,1-二甲基-3-丁炔基、1,2-二甲基-3-丁炔基、2,2-二甲基-3-丁炔基、3,3-二甲基-1-丁炔基、1-乙基-2-丁炔基、1-乙基-3-丁炔基、2-乙基-3-丁炔基和1-乙基-1-甲基-2-丙炔基。
本申请使用的烷氧基是指式R-O-的基团,其中R为如上定义的烷基。除非另有说明,意在表示其中R为C1-C8烷基的烷氧基。实例包括甲氧基、乙氧基、丙氧基、1-甲基-乙氧基、丁氧基、1-甲基-丙氧基、2-甲基-丙氧基、1,1-二甲基-乙氧基、戊氧基、1-甲基-丁氧基、2-甲基-丁氧基、3-甲基-丁氧基、2,2-二-甲基-丙氧基、1-乙基-丙氧基、己氧基、1,1-二甲基-丙氧基、1,2-二甲基-丙氧基、1-甲基-戊氧基、2-甲基-戊氧基、3-甲基-戊氧基、4-甲基-戊氧基、1,1-二甲基-丁氧基、1,2-二甲基-丁氧基、1,3-二甲基-丁氧基、2,2-二甲基-丁氧基、2,3-二甲基-丁氧基、3,3-二甲基-丁氧基、1-乙基-丁氧基、2-乙基丁氧基、1,1,2-三甲基-丙氧基、1,2,2-三甲基-丙氧基、1-乙基-1-甲基-丙氧基和1-乙基-2-甲基-丙氧基。
本申请使用的卤代烷氧基是指式R-O-基团,其中R为如上定义的卤代烷基。除非另有说明,意在表示其中R为C1-C8烷基的卤代烷氧基。实例包括氯甲氧基、溴甲氧基、二氯甲氧基、三氯甲氧基、氟甲氧基、二氟甲氧基、三氟甲氧基、氯氟甲氧基、二氯氟甲氧基、氯二氟甲氧基、1-氯乙氧基、1-溴乙氧基、1-氟乙氧基、2-氟乙氧基、2,2-二氟乙氧基、2,2,2-三氟乙氧基、2-氯-2-氟乙氧基、2-氯,2-二氟乙氧基、2,2-二氯-2-氟乙氧基、2,2,2-三氯乙氧基、五氟乙氧基和1,1,1-三氟丙-2-氧基。
本申请使用的烷基硫基是指式R-S-基团,其中R为如上定义的烷基。除非另有说明,意在表示其中R为C1-C8烷基的烷基硫基。实例包括甲基硫基、乙基硫基、丙基硫基、1-甲基乙基硫基、丁基硫基、1-甲基-丙基硫基、2-甲基丙基硫基、1,1-二甲基乙基硫基、戊基硫基、1-甲基丁基硫基、2-甲基丁基硫基、3-甲基丁基硫基、2,2-二o-甲基丙基硫基、1-乙基丙基硫基、己基硫基、1,1-二甲基丙基硫基、1,2-二甲基丙基硫基、1-甲基戊基硫基、2-甲基戊基硫基、3-甲基-戊基硫基、4-甲基-戊基硫基、1,1-二甲基丁基硫基、1,2-二甲基-丁基硫基、1,3-二甲基-丁基硫基、2,2-二甲基丁基硫基、2,3-二甲基丁基硫基、3,3-二甲基丁基硫基、1-乙基丁基硫基、2-乙基丁基硫基、1,1,2-三甲基丙基硫基、1,2,2-三甲基丙基硫基、1-乙基-1-甲基丙基硫基和1-乙基-2-甲基丙基硫基。
本申请使用的卤代烷基硫基是指如上定义的烷基硫基,其中碳原子部分或全部被卤素原子取代。除非另有说明,意在表示其中R为C1-C8烷基的卤代烷基硫基。实例包括氯甲基硫基、溴甲基硫基、二氯甲基硫基、三氯甲基硫基、氟甲基硫基、二氟甲基硫基、三氟甲基硫基、氯氟甲基硫基、二氯氟-甲基硫基、氯二氟甲基硫基、1-氯乙基硫基、1-溴乙基硫基、1-氟乙基硫基、2-氟乙基硫基、2,2-二氟乙基硫基、2,2,2-三氟乙基硫基、2-氯-2-氟乙基硫基、2-氯-2-二氟乙基硫基、2,2-二氯-2-氟乙基硫基、2,2,2-三氯乙基硫基、五氟乙基硫基和1,1,1-三氟丙-2-基硫基。
本申请使用的芳基以及衍生术语例如芳基氧基是指苯基、茚满基或萘基,优选的是苯基。术语"杂芳基"以及衍生术语例如"杂芳基氧基"是指含有一个或多个杂原子即N、O或S的5-或6-元芳族环;这些杂芳族环可与其他芳族系统稠合。所述芳基或杂芳基取代基可为未取代的或被一个或多个选自以下的取代基取代:卤素、羟基、硝基、氰基、甲酰基、C1-C6烷基、C2-C6烯基、C2-C6炔基、C1-C6烷氧基、C1-C6卤代烷基、C1-C6卤代烷氧基、C1-C6酰基、C1-C6烷基硫基、C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、C1-C6烷氧基羰基、C1-C6氨基甲酰基、羟基羰基、C1-C6烷基羰基、氨基羰基、C1-C6烷基氨基羰基、C1-C6二烷基氨基羰基,条件是所述取代基为立体相容的并且满足化学成键和应变能。优选的取代基包括卤素、C1-C2烷基和C1-C2卤代烷基。
本申请使用的烷基羰基是指与羰基键合的烷基。C1-C3烷基羰基和C1-C3卤代烷基羰基是指其中C1-C3烷基与羰基键合的基团(该基团共含有2至4个碳原子)。
本申请使用的烷氧基羰基是指式基团,其中R为烷基。
本申请使用的芳基烷基是指被芳基取代的烷基。C7-C10芳基烷基是指基团中总碳原子数为7至10个的基团。
本申请使用的烷基氨基是指被一个或两个可相同或不同的烷基取代的氨基。
本申请使用的卤代烷基氨基是指其中烷基碳原子被卤素原子部分或完全取代的烷基氨基。
本申请使用的,C1-C6烷基氨基羰基是指其中R为C1-C6烷基的式RNHC(O)-基团,并且C1-C6二烷基氨基羰基是指其中每个R独立地为C1-C6烷基的式R2NC(O)-基团。
本申请使用的烷基氨基甲酰基是指在氮上被烷基取代的氨基甲酰基。
本申请使用的烷基磺酰基是指式基团,其中R为烷基。
本申请使用的氨基甲酰基(也被称作氨甲酰基和氨基羰基)是指式基团。
本申请使用的二烷基氧膦基是指式基团,其中R在每次出现时独立地为烷基。
本申请使用的C1-C6三烷基甲硅烷基是指式–SiR3基团,其中每个R独立地为C1-C6烷基(该基团共含有3至18个碳原子)。
本申请使用的Me是指甲基;OMe是指甲氧基;i-Pr是指异丙基。
本申请使用的术语“卤素”包括衍生术语例如“卤素”是指氟、氯、溴和碘。
本申请使用的植物和植被包括但不限于发芽的种子、发芽苗、从无性繁殖体发芽的植物、不成熟的植被和已长成的植被。
式(I)化合物
本发明提供如上定义的式(I)化合物及其N-氧化物和农用盐。
在一些实施方案中,所述化合物为羧酸或农用酯或盐。在一些实施方案中,所述化合物为羧酸或其甲酯。
在一些实施方案中,所述化合物为式(I)化合物或其N-氧化物或农用盐:
其中
X为N或CY,其中Y为氢、卤素、C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、C1-C3烷氧基、C1-C3烷硫基或C1-C3卤代烷硫基;
R1为OR1′或NR1″R1″′,其中R1′为氢、C1-C8烷基或C7-C10芳基烷基,且R1″和R1″′独立地为氢、C1-C12烷基、C3-C12烯基或C3-C12炔基;
R2为卤素、C1-C4烷基、C1-C4卤代烷基、C2-C4烯基、C2-C4卤代烯基,C2-C4炔基、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷硫基、C1-C4卤代烷硫基、氨基、C1-C4烷基氨基、C2-C4卤代烷基氨基、甲酰基、C1-C3烷基羰基、C1-C3卤代烷基羰基、氰基、或者式-CR17=CR18-SiR19R20R21的基团,其中R17为氢、F或Cl;R18为氢、F、Cl、C1-C4烷基或C1-C4卤代烷基;且R19、R20和R21独立地为C1-C10烷基、C3-C6环烷基、苯基、取代苯基、C1-C10烷氧基或OH;
R3和R4独立地为氢、C1-C6烷基、C1-C6卤代烷基、C3-C6烯基、C3-C6卤代烯基、C3-C6炔基、甲酰基、C1-C3烷基羰基、C1-C3卤代烷基羰基、C1-C6烷氧基羰基、C1-C6烷基氨基甲酰基、C1-C6烷基磺酰基、C1-C6三烷基甲硅烷基、C1-C6二烷基氧膦基,或者R3和R4与N一起为5-或6元饱和环,或者R3和R4一起代表=CR3′(R4′),其中R3′和R4′独立地为氢、C1-C6烷基、C3-C6烯基、C3-C6炔基、C1-C6烷氧基或C1-C6烷基氨基,或者R3′和R4′与=C一起代表5-或6-元饱和环;
A为基团Ar1至Ar24之一:
R5为氢、卤素、C1-C4烷基、C1-C4卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、C1-C3烷硫基、C1-C3卤代烷硫基、氨基、C1-C4烷基氨基或C2-C4卤代烷基氨基。
R6为氢、卤素、C1-C4烷基、C1-C4卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、C1-C3烷硫基、C1-C3卤代烷硫基、氨基、C1-C4烷基氨基或C2-C4卤代烷基氨基;
R6′为氢或卤素;
R6″为氢、卤素、C1-C4烷基、C1-C4卤代烷基、环丙基、卤代环丙基、C2-C4烯基、C2-C4卤代烯基、C2-C4炔基、C1-C3烷氧基、C1-C3卤代烷氧基、C1-C3烷硫基、C1-C3卤代烷硫基、氨基、C1-C4烷基氨基、C2-C4卤代烷基氨基、CN或NO2;
R7和R7′独立地为氢、卤素、C1-C4烷基、C1-C4卤代烷基或C1-C3烷氧基;
R8和R8′独立地为氢、卤素、C1-C4烷基、C1-C4卤代烷基或C1-C3烷氧基;
R9、R9′、R9″和R9″′独立地为氢、卤素、C1-C4烷基、C1-C4卤代烷基或C1-C3烷氧基;
R10为氢、C1-C6烷基、C1-C6卤代烷基、C3-C6烯基、C3-C6卤代烯基、C3-C6炔基、甲酰基、C1-C3烷基羰基、C1-C3卤代烷基羰基或C1-C6三烷基甲硅烷基;
m,当存在时,为0、1或2;和
n,当存在时,为0、1或2;
条件是A不为
在一些实施方案中,m,当存在时,为0或1;且n,当存在时,为0或1。在一些实施方案中,m,当存在时,为0;且n,当存在时,为0。在一些实施方案中,m,当存在时,为1;且n,当存在时,为1。
在一些实施方案中,R1为OR1′,其中R1′为氢、C1-C8烷基或C7-C10芳基烷基。
在一些实施方案中,R2为卤素、C2-C4-烯基、C2-C4-卤代烯基或C1-C4-烷氧基。在一些实施方案中,R2为卤素、C2-C4-烯基或C1-C4-烷氧基。在一些实施方案中,R2为Cl、OMe、乙烯基或1-丙烯基。在一些实施方案中,R2为Cl。在一些实施方案中,R2为OMe。在一实施方案中,R2为乙烯基或1-丙烯基。
在一些实施方案中,R3和R4独立地为氢、C1-C6烷基、C1-C6卤代烷基、C3-C6烯基、C3-C6卤代烯基、C3-C6炔基、甲酰基、C1-C3烷基羰基、C1-C3卤代烷基羰基、C1-C6烷氧基羰基、C1-C6烷基氨基甲酰基,或者R3和R4一起代表=CR3′(R4′),其中R3′和R4′独立地为氢、C1-C6烷基、C3-C6烯基、C3-C6炔基、C1-C6烷氧基或C1-C6烷基氨基。在一些实施方案中,R3和R4独立地为氢、C1-C6烷基、C1-C6卤代烷基、C3-C6烯基、C3-C6卤代烯基、甲酰基、C1-C3烷基羰基、C1-C3卤代烷基羰基,或者R3和R4一起代表=CR3′(R4′),其中R3′和R4′独立地为氢、C1-C6烷基、C1-C6烷氧基或C1-C6烷基氨基。在一些实施方案中,R3和R4中的至少一个为氢。在一些实施方案中,R3和R4均为氢。
在一些实施方案中,X为N、CH或CF。在一些实施方案中,X为N。在一些实施方案中,X为CH。在一些实施方案中,X为CF。
在一些实施方案中:Ar为Ar1、Ar3、Ar4、Ar7、Ar9、Ar10、Ar13、Ar15、Ar16、Ar19、Ar21、Ar22、Ar25或Ar27。
在一些实施方案中:Ar为Ar1、Ar2、Ar3、Ar4、Ar5、Ar6、Ar7、Ar8、Ar15、Ar16、Ar17、Ar18、Ar25、Ar26、Ar27或Ar28。
在一些实施方案中:Ar为Ar1、Ar3、Ar7、Ar9、Ar10、Ar13、Ar15、Ar16、Ar19、Ar21或Ar22。
在一些实施方案中:Ar为Ar2、Ar4、Ar5、Ar6、Ar8、Ar11、Ar12、Ar14、Ar17、Ar18、Ar20、Ar23、Ar24、Ar26或Ar28。
在一些实施方案中:Ar为Ar2、Ar5、Ar6、Ar8、Ar11、Ar12、Ar14、Ar17、Ar18、Ar20、Ar23或Ar24。
在一些实施方案中:Ar为Ar1、Ar2、Ar3、Ar4、Ar6或Ar7。
在一些实施方案中:Ar为Ar15、Ar16、Ar17或Ar18。
在一些实施方案中,R5为氢、卤素、C1-C4烷基、C1-C4卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、C1-C3烷硫基或C1-C3卤代烷硫基。
在一些实施方案中,R5为氢、卤素、C1-C4烷基、C1-C4卤代烷基或C1-C3烷氧基。在一些实施方案中,R5为氢或F。在一些实施方案中,R5为氢。在一些实施方案中,R5为F。
在一些实施方案中,R6为氢或卤素。在一些实施方案中,R6为氢或F。在一些实施方案中,R6为氢。在一些实施方案中,R6为F。
在一些实施方案中,R6′为氢或卤素。在一些实施方案中,R6′为氢或F。在一些实施方案中,R6′为氢。在一些实施方案中,R6′为F。
在一些实施方案中,R6″为氢、卤素、C1-C4烷基、C1-C4卤代烷基、环丙基、C2-C4炔基、CN或NO2。在一些实施方案中,R6″为氢、卤素、C1-C4卤代烷基或环丙基。在一些实施方案中,R6″为氢或卤素。在一些实施方案中,R6″为C1-C4卤代烷基。在一些实施方案中,R6″为CN。在一些实施方案中,R6″为NO2。
在一些实施方案中:
R2为卤素、C2-C4-烯基、C2-C4卤代烯基或C1-C4-烷氧基;
R3和R4均为氢;和
X为N、CH或CF。
在一些实施方案中:
R2为卤素、C2-C4-烯基或C1-C4-烷氧基;
R3和R4均为氢;和
X为N、CH或CF;
Ar为Ar1、Ar3、Ar7、Ar9、Ar10、Ar13、Ar15、Ar16、Ar19、Ar21或Ar22;
R5为氢或F;
R6为氢或F;
R6′为氢;
R7、R7′、R8、R8′、R9、R9′、R9″和R9″′,如果适用于相关的Ar基团,独立地为氢或氟。
在一些实施方案中:
R2为卤素、C2-C4-烯基或C1-C4-烷氧基;
R3和R4均为氢;和
X为N、CH或CF;
Ar为Ar1、Ar2、Ar3、Ar4、Ar5、Ar6、Ar7、Ar8、Ar9、Ar10、Ar11、Ar12、Ar15、Ar16、Ar25、Ar26、Ar27或Ar28;
R5为氢或F;
R6为氢或F;
R6′为氢;
R7、R7′、R8、R8′、R9、R9′、R9″和R9″′,如果适用于相关的Ar基团,独立地为氢或氟。
在一些实施方案中:
R2为氯、甲氧基、乙烯基或1-丙烯基;
R3和R4为氢;和
X为N、CH或CF。
在一些实施方案中:
R2为氯;
R3和R4为氢;和
X为N、CH或CF。
在一些实施方案中:
R2为甲氧基;
R3和R4为氢;和
X为N、CH或CF.
在一些实施方案中:
R2为乙烯基或1-丙烯基;
R3和R4为氢;和
X为N、CH或CF。
在一些实施方案中:
R2为氯、甲氧基、乙烯基或1-丙烯基;
R3和R4为氢;和
X为N。
在一些实施方案中:
R2为氯;
R3和R4为氢;和
X为CH。
在一些实施方案中:
R2为氯、甲氧基、乙烯基或1-丙烯基;
R3和R4为氢;和
X为CF。
示例性化合物
下表1描述了示例性的式(I)化合物,其中
R1为OR1′;
R3和R4为氢;和
R1′、R2、X、Ar、m、R5、R6、R6′、R6″、R7和R7′、R8、R8′和R10为以下组合之一:
表1
*对于化合物107,R8和R8′为经取代的并且各为F。
**对于化合物108,R10为经取代的,并且为Me。
制备化合物的方法
下面提供了合成式(I)化合物的示例性操作。
式(I)的4-氨基-6-(杂环基)吡啶-2-甲酸可按多种方法制备。如方案I中所示的,式(II)的4-氨基-6-氯-吡啶-2-甲酸酯可以经由与硼酸或酯的Suzuki偶联在碱如氟化钾和催化剂如双(三苯基膦)-二氯化钯(II)的存在下在极性质子溶剂混合物如乙腈-水中于例如110℃的温度,例如,在微波反应器中转化成式(III)的4-氨基-6-取代的-吡啶-2-甲酸酯,其中Ar如本文所定义(反应a1)。式(III)的4-氨基-6-取代的-吡啶-2-甲酸酯可以经由在极性质子溶剂如甲醇中与碘化试剂如高碘酸和碘的反应转化成式(IV)的5-碘-4-氨基-6-取代的-吡啶-2-甲酸酯(反应b1)。式(IV)的5-碘-4-氨基-6-取代的-吡啶-2-甲酸酯与锡烷如四甲基锡在催化剂如双(三苯基膦)-二氯钯(II)的存在下在非反应性溶剂如1,2-二氯乙烷中于如120-130℃的温度,例如,在微波反应器中的Stille偶联得到式(I-A)的5-(取代的)-4-氨基-6-取代的-吡啶-2-甲酸酯,其中Z1为烷基、烯基、炔基、卤代烯基和烷基硫基(反应c1)。
备选地,式(II)的4-氨基-6-氯-吡啶-2-甲酸酯可以经由与碘化试剂如高碘酸或碘在极性质子溶剂如甲醇中反应转化成式(V)的5-碘-4-氨基-6-氯-吡啶-2-甲酸酯(反应b2)。式(V)的5-碘-4-氨基-6-氯-吡啶-2-甲酸酯与锡烷如四甲基锡在催化剂如双(三苯基膦)-二氯化钯(II)的存在下在非反应性溶剂如1,2-二氯乙烷中于如120-130℃的温度,例如,在微波反应器中的Stille偶联得到式(VI)的5-(取代的)-4-氨基-6-氯-吡啶-2-甲酸酯,其中Z1为烷基、烯基、炔基、卤代烯基和烷基硫基(反应c2)。式(VI)的5-取代的-4-氨基-6-氯-吡啶-2-甲酸酯在碱如氟化钾和催化剂如双(三苯基膦)-二氯化钯(II)的存在下在极性质子溶剂混合物如乙腈-水中于如110℃的温度,例如,在微波反应器中经由与硼酸或酯的Suzuki偶联可以转化为式(I-A)的5-取代的-4-氨基-6-取代的-吡啶-2-甲酸酯,其中Ar如本文所定义(反应a2)。
方案I
如方案II中所描绘的,式(VII)的4,5,6-三氯-吡啶-2-甲酸酯可以,例如,于回流温度在Dean-Stark条件经由与异丙基醇和浓硫酸的反应转化为相应的式(VIII)的异丙基酯(反应d)。式(VIII)的异丙基酯可以与氟离子源例如氟化铯在极性非质子溶剂如二甲基亚砜(DMSO)于如80℃的温度在Dean-Stark条件下反应,得到式(IX)的4,5,6-三氟-吡啶-2-甲酸异丙基酯(反应e)。式(IX)的4,5,6-三氟-吡啶-2-甲酸异丙基酯可以在极性非质子溶剂如DMSO中以氮源如氨氨化来制备式(X)的4-氨基-5,6-二氟-吡啶-2-甲酸酯(反应f)。式(X)的4-氨基-5,6-二氟-吡啶-2-甲酸酯的6-位的氟取代基可以通过,例如,在二噁烷中在Parr反应器中于例如100℃的温度以氯源如氯化氢处理与氯取代基进行交换制备式(XI)的4-氨基-5-氟-6-氯-吡啶-2-甲酸酯(反应g)。式(XI)的4-氨基-5-氟-6-氯-吡啶-2-甲酸酯可以通过在甲醇中于回流温度与异丙醇钛(IV)反应酯交换成相应的式(XII)的甲基酯(反应h)。
方案II
如方案III中所描绘的,式(XII)的4-氨基-5-氟-6-氯-吡啶-2-甲酸酯可以在极性质子溶剂如甲醇中经由与碘化试剂如高碘酸和碘的反应转化成式(XIII)的3-碘-4-氨基-5-氟-6-氯-吡啶-2-甲酸酯(反应b3)。式(XIII)的3-碘-4-氨基-5-氟-6-氯-吡啶-2-甲酸酯与锡烷如三丁基(乙烯基)锡烷在催化剂如双(三苯基膦)-二氯化钯(II)的存在下在非反应性溶剂如1,2-二氯乙烷中于如120-130℃的温度,例如,在微波反应器中的Stille偶联得到式(XIV)的3-(取代的)-4-氨基-5-氟-6-氯-吡啶-2-甲酸酯,其中R2为烷基、烯基、炔基、卤代烯基和烷基硫基(反应c3)。备选地,式(XIII)的3-碘-4-氨基-5-氟-6-氯-吡啶-2-甲酸酯可以碳酸铯和催化量的碘化铜(I)和1,10-菲咯啉两者在极性质子溶剂如甲醇中于例如65℃的温度进行处理得到式(XIV)的3-(取代的)-4-氨基-5-氟-6-氯吡啶-2-甲酸,其中R2为烷氧基或卤代烷氧基(反应i1),其可以酯化成甲基酯,例如,通过以氯化氢(气体)和甲醇于50℃处理(反应j1)。式(XIV)的3-(取代的)-4-氨基-5-氟-6-氯-吡啶-2-甲酸酯可以经由在碱如氟化钾和催化剂如双(三苯基膦)-二氯化钯(II)的存在下在极性质子溶剂混合物如乙腈-水中于如110℃的温度,例如,在微波反应器中,与硼酸或酯的Suzuki偶联而转化成式(I-B)的4-氨基-6-取代的-吡啶-2-甲酸酯,其中Ar如本文所定义(反应a3)。
备选地,式(XII)的4-氨基-5-氟-6-氯-吡啶-2-甲酸酯可以经由在碱如氟化钾和催化剂如双(三苯基膦)-二氯化钯(II)的存在下在极性质子溶剂混合物如乙腈-水中于如110℃的温度,例如,在微波反应器中与硼酸或酯的Suzuki偶联转化成式(XV)的4-氨基-5-氟-6-取代的-吡啶-2-甲酸酯,其中Ar如本文所定义(反应a4)。式(XV)的4-氨基-5-氟-6-取代的-吡啶-2-甲酸酯可以经由在极性质子溶剂如甲醇中与碘化试剂如高碘酸和碘的反应转化成式(XVI)的3-碘-4-氨基-5-氟-6-取代的-吡啶-2-甲酸酯(反应b4)。式(XVI)的3-碘-4-氨基-5-氟-6-取代的-吡啶-2-甲酸酯与锡烷如三丁基(乙烯基)锡烷在催化剂如双(三苯基膦)-二氯化钯(II)的存在下在非反应性溶剂如1,2-二氯乙烷中于例如120–130℃的温度,例如,在微波反应器中的Stille偶联得到式(I-B)的3-(取代的)-4-氨基-5-氟-6-取代的-吡啶-2-甲酸酯,其中R2为烷基、烯基、炔基、卤代烯基和烷基硫基(反应c4)。备选地,式(XVI)的3-碘-4-氨基-5-氟-6-取代的-吡啶-2-甲酸酯可以碳酸铯和催化量的碘化铜(I)和1,10-菲咯啉两者在极性质子溶剂如甲醇的存在下于例如65℃的温度处理得到式(I-B)的3-(取代的)-4-氨基-5-氟-6-取代的吡啶-2-甲酸,其中R2为烷氧基或卤代烷氧基(反应i2),其可以酯化成甲基酯,例如,通过以氯化氢(气体)和甲醇在如50℃的温度进行处理(反应j2)。
方案III
如方案IV所描绘的,式(XVII)的4-乙酰氨基-6-(三甲基甲锡烷基)-吡啶-2-甲酸酯可以经由与芳基溴或芳基碘在催化剂如双(三苯基膦)-二氯化钯(II)的存在下在溶剂如1,2-二氯乙烷中,例如,于回流温度(反应k)的Stille偶联转化成式(XVIII)的4-乙酰氨基-6-取代的-吡啶-2-甲酸酯,其中Ar如本文所定义。式(I-C)的4-氨基-6-取代的-吡啶-2-甲酸酯,其中Ar如本文所定义,可以经由标准脱保护方法例如氢氯酸气体/甲醇由式(XVIII)的4-乙酰氨基-6-取代的-吡啶-2-甲酸酯合成(反应l)。
方案IV
如方案V所描绘的,2,4-二氯-5-甲氧基嘧啶(XIX)可以经由在极性非质子溶剂如四氢呋喃中与乙烯基溴化镁的反应转化成2,4-二氯-5-甲氧基-6-乙烯基嘧啶(XX)(反应m)。2,4-二氯-5-甲氧基-6-乙烯基嘧啶(XX)可以经由以臭氧,例如,在二氯甲烷:甲醇溶剂混合物中进行处理转化成2,6-二氯-5-甲氧基嘧啶-4-甲醛(XXI)(反应n)。2,6-二氯-5-甲氧基嘧啶-4-甲醛(XXI)可以经由,例如,在甲醇:水溶剂混合物中以溴处理转化成2,6-二氯-5-甲氧基嘧啶-4-甲酸甲基酯(XXII)(反应o)。2,6-二氯-5-甲氧基嘧啶-4-甲酸甲基酯(XXII)可以经由在溶剂如DMSO中以氨(例如,2当量)处理转化成6-氨基-2-氯-5-甲氧基嘧啶-4-甲酸甲基酯(XXIII)(反应p)。最终,式(I-D)的6-氨基-2-取代的5-甲氧基嘧啶-4-甲酸酯,其中Ar如本文所定义,可以经由硼酸或酯与6-氨基-2-氯-5-甲氧基嘧啶-4-甲酸酯(XXIII)在碱如氟化钾和催化剂如双(三苯基膦)-二氯化钯(II)的存在下在极性质子溶剂混合物如乙腈-水中于如110℃的温度,例如,在微波反应器中的Suzuki偶联来制备(反应a5)。
方案V
通过任何这些方法得到的式I-A、I-B、I-C和I-D的化合物可以通过常规方式回收并通过标准方法如重结晶或色谱纯化。式(I)化合物可以从式I-A、I-B、I-C和I-D的化合物使用本领域公知的标准方法制备。
组合物和方法
在一些实施方案中,本申请提供的化合物应用于含有除草有效量的化合物以及至少一种农用辅料或载体的混合物中。示例性的辅料或载体包括对有价值的作物不产生植物性毒素或显著性毒性的那些,例如,在作物存在时施用杂草控制选择性组合物所使用的浓度下,和/或不与本文提供的化合物或其它组合物成分发生化学反应或发生显著的化学反应。可以设计这样的混合物以便于直接施用于杂草或它们的所在地,或者可以是在施用前用另外的载体和辅料稀释的浓缩物或制剂。它们可以是固体,例如,粉剂、颗粒、可水分散的细粒、或可润湿的粉末、或液体,例如,可乳化的浓缩物、溶液、乳液或悬浮液。也可以将它们作为预混物提供或将它们罐混合。
本领域技术人员公知用于制备本公开的除草混合物的适宜农用辅料和载体。这些辅料包括但不限于,作物油浓缩物(矿物油(85%)+乳化剂(15%));壬基酚乙氧基化物;苄基椰油烷基二甲基季铵盐;石油烃、烷基酯、有机酸、和阴离子表面活性剂的共混物;C9-C11烷基聚糖苷;磷酸化的醇乙氧基化物;天然伯醇(C12-C16)乙氧基化物;二-仲-丁基苯酚EO-PO嵌段共聚物;聚硅氧烷-甲基封端物;壬基酚乙氧基化物+脲硝酸铵;乳化的甲基化的种子油;十三烷基醇(合成)乙氧基化物(8EO);牛油胺乙氧基化物(15EO);PEG(400)二油酸酯-99。
可采用的液体载体包括水和有机溶剂。通常使用的有机溶剂包括但不限于石油级分或者烃例如矿物油,芳族溶剂,石蜡油,等;植物油例如大豆油,葡萄籽油,橄榄油,蓖麻油,葵花籽油,椰子油,玉米油,棉花子油,亚麻子油,棕榈油,花生油,红花油,芝麻油,桐油等;以及以上植物油的酯;一元醇或者二元醇、三元醇或者其它较低级的多元醇(含有4-6个羟基)的酯,例如硬脂酸2-乙基己基酯,油酸正丁酯,豆蔻酸异丙基酯,丙二醇二油酸酯,丁二酸二辛基酯,己二酸二丁酯,邻苯二甲酸二辛酯等;单、二和多羧酸的酯等。具体的有机溶剂包括甲苯,二甲苯,石脑油,作物油(cropoil),丙酮,甲基乙基酮,环己酮,三氯乙烯,全氯代乙烯,乙酸乙酯,乙酸戊基酯,乙酸丁基酯,丙二醇单甲基醚和乙二醇单甲基醚,甲醇,乙基醇,异丙基醇,戊基醇,乙二醇,丙二醇,甘油,N-甲基-2-吡咯烷酮,N,N-二甲基烷基酰胺,二甲亚砜,液体肥料等。在一些实施方案中,水是用于稀释浓缩物的载体。
适宜的固体载体包括滑石、叶蜡石粘土、二氧化硅、凹凸棒石粘土(attapulgusclay)、高岭土、硅藻土、白垩、硅藻土、石灰、碳酸钙、膨润土、漂白土、棉籽壳、小麦粉、大豆粉、浮石、木粉、核桃壳粉、木质素等。
在一些实施方案中,在本公开的组合物中使用一种或多种表面活性剂。在一些实施方案中,这类表面活性剂同时在固体和液体组合物中使用,例如,被设计成在施用之前用载体稀释。表面活性剂性质上可以是阴离子的、阳离子的或非离子的,并可用作乳化剂、润湿剂、悬浮剂、或针对其它目的的试剂。常规用于制剂领域且还可用于本申请制剂中的表面活性剂尤其描述在“McCutcheon’sDetergentsandEmulsifiersAnnual,”MCPublishingCorp.,Ridgewood,NewJersey,1998以及“EncyclopediaofSurfactants,”Vol.I-III,ChemicalPublishingCo.,NewYork,1980-81中。典型的表面活性剂包括烷基硫酸酯的盐,例如月桂基硫酸二乙醇铵;烷基芳基磺酸盐,例如十二烷基苯磺酸钙;烷基酚-环氧烷烃加成产物,例如壬基酚-C18乙氧基化物;醇-环氧烷烃加成产物,例如十三烷基醇-C16乙氧基化物;皂,例如硬脂酸钠;烷基萘-磺酸盐,例如二丁基萘磺酸钠;磺基琥珀酸盐的二烷基酯,例如二(2-乙基己基)磺基琥珀酸钠;山梨糖醇酯,例如油酸山梨糖醇酯;季胺,例如月桂基三甲基氯化铵;脂肪酸的聚乙二醇酯,例如聚乙二醇硬脂酸酯;环氧乙烷和环氧丙烷的嵌段共聚物;和磷酸一烷基酯和磷酸二烷基酯的盐;植物油或种子油,例如大豆油、油菜籽/菜籽油、橄榄油、蓖麻油、葵花籽油、椰油、玉米油、棉籽油、亚麻子油、棕榈油、花生油、红花油、芝麻油、桐油等;以及以上植物油的酯,例如甲酯。
有时,这些物质中的一些,例如植物或种子油和它们的酯,可以互换地用作农用辅料,用作液体载体或用作表面活性剂。
通常用于农用组合物中的其它辅料包括增容剂、消泡剂、螯合剂(sequesteringagent)、中和剂和缓冲液、防腐蚀剂、染料、增香剂、铺展剂、渗透助剂、粘着剂、分散剂、增稠剂、防冻剂、抗菌剂等。组合物还可含有其它相容组分,例如,其它除草剂、植物生长调节剂(plantgrowthregulants)、杀真菌剂、杀昆虫剂等,并且可以与液体肥料或固体配制,特别是肥料载体例如硝酸铵、脲等。
活性成分在本公开的除草组合物中的浓度一般为约0.001至约98重量%。通常使用约0.01至约90重量%的浓度。在设计用作浓缩物的组合物中,活性成分的存在浓度一般为约5至约98重量%,优选约10至约90重量%。这类组合物通常在施用前用惰性载体例如水稀释。通常施用于杂草或杂草所在地的经稀释组合物一般含有约0.0001至约1重量%的活性成分并优选含有约0.001至约0.05重量%。
本申请组合物可以通过使用常规地面或高空喷粉机、喷雾器、和粒料施用器,通过添加到灌溉水或稻田水(floodwater),和通过本领域技术人员已知的其它常规方法施用于杂草或它们的所在地。
在一些实施方案中,本文描述的化合物和组合物以芽后施用、芽前施用、水中施用方式施用至淹水的稻田稻子或水体(例如,池塘、湖或溪流)中,或焚毁施用。
在一些实施方案中,本文提供的化合物和组合物用来防治作物以及非作物场所中的杂草,所述作物包括但不限于柑橘属、苹果、橡胶、油类、棕榈、林业、直播稻、水播稻和移植稻、谷物、小麦、大麦、燕麦、黑麦、高粱、玉米/玉米、牧地、牧草地、牧场、休耕地、草皮、乔木和藤本果园、水生植物、或中耕作物(row-crops),以及所述非作物场所例如工业植被管理(IVM)或道路周围。在一些实施方案中,化合物和组合物用来防治木质植物、阔叶和禾本科杂草或莎草。
在一些实施方案中,本申请提供的化合物和组合物用于控制稻子中的不期望的植被。在某些实施方案中,不期望的植被是臂形草(Brachiariaplatyphylla(Groseb.)Nash(阔叶信号草(broadleafsignalgrass),BRAPP),马唐(Digitariasanguinalis(L.)Scop.)(红色马唐(largecrabgrass),DIGSA),稗(Echinochloacrus-galli(L.)P.Beauv.)(稗(barnyardgrass),ECHCG),光头稗(Echinochloacolonum(L.)LINK)(光头稗(junglerice),ECHCO),水田稗(Echinochloaoryzoides(Ard.)Fritsch)(earlywatergrass,ECHOR),水稗(Echinochloaoryzicola)(Vasinger)Vasinger(晚水草(latewatergrass),ECHPH),田间鸭嘴草(IschaemumrugosumSalisb.)(鸭嘴草(saramollagrass),ISCRU),千金子(Leptochloachinensis(L.)Nees)(中国千金子(Chinesesprangletop),LEFCH),丛生千金子(Leptochloafascicularis(Lam.)Gray)(有芒千金子(beardedsprangletop),LEFFA),类黍千金子(Leptochloapanicoides(Presl.)Hitchc.)(亚马逊千金子(Amazonsprangletop),LEFPA),洋野黍(Panicumdichotomiflorum(L.)Michx.)(秋黍(fallpanicum),PANDI),毛花雀稗(PaspalumdilatatumPoir.)(雀稗草(dallisgrass),PASDI),异型莎草(CyperusdifformisL.)(小花莎草(smallflowerflatsedge),CYPDI),油莎草(CyperusesculentusL.)(黄莎草(yellownutsedge),CYPES),碎米莎草(CyperusiriaL.)(米莎草(riceflatsedge),CYPIR),香附子(CyperusrotundusL.)(紫莎草(purplenutsedge),CYPRO),荸荠属物种(Eleocharisspecies)(ELOSS),水虱草(Fimbristylismiliacea(L.)Vahl)(globefringerush,FIMMI),萤蔺(SchoenoplectusjuncoidesRoxb.)(日本纸草(Japanesebulrush),SPCJU),SchoenoplectusmaritimusL.(seaclubrush,SCPMA),水毛花(SchoenoplectusmucronatusL.)(稻田芦苇(ricefieldbulrush),SCPMU),合萌属物种(Aeschynomenespecies)(合萌(jointvetch),AESSS),喜旱莲子草(Alternantheraphiloxeroides(Mart.)Griseb.)(空心莲子草(alligatorweed),ALRPH),泽泻水生车前草属(Alismaplantago-aquaticaL.)(普通水生车前草(commonwaterplantain),ALSPA),苋属物种(Amaranthusspecies)(藜(pigweeds)和苋(amaranths),AMASS),红水苋(AmmanniacoccineaRottb.)(红茎(redstem),AMMCO),旱莲草(Ecliptaalba(L.)Hassk.)(美国假菊(Americanfalsedaisy),ECLAL),沼生异蕊花(Heterantheralimosa(SW.)Willd./Vahl)(鸭沙拉(ducksalad),HETLI),肾形异蕊花(HeterantherareniformisR.&P.)(圆叶异蕊花属(roundleafmudplantain),HETRE),碗仔花(Ipomoeahederacea(L.)Jacq.)(裂叶牵牛(ivyleafmorningglory),IPOHE),美洲母草(Linderniadubia(L.)Pennell)(lowfalsepimpernel,LIDDU),雨久花(MonochoriakorsakowiiRegel&Maack)(雨久花属(monochoria),MOOKA),鸭舌草(Monochoriavaginalis(Burm.F.)C.PreslexKuhth)(雨久花属(monochoria),MOOVA),裸花水竹叶(Murdannianudiflora(L.)Brenan)(鸽草(doveweed),MUDNU),宾夕法尼亚蓼属(PolygonumpensylvanicumL.)(宾夕法尼亚荨麻(Pennsylvaniasmartweed),POLPY),春蓼(PolygonumpersicariaL.)(ladysthumb,POLPE),杠板归(PolygonumhydropiperoidesMichx.)(软蓼(mildsmartweed),POLHP),节节菜(Rotalaindica(Willd.)Koehne)(印度紫水苋菜(Indiantoothcup),ROTIN),慈姑属物种(Sagittariaspecies)(慈姑(arrowhead),SAGSS),田菁(Sesbaniaexaltata(Raf.)Cory/Rydb.ExHill)(大麻田菁属(hempsesbania),SEBEX),或尖瓣花(SphenocleazeylanicaGaertn.)(鹅草(gooseweed),SPDZE)。
在一些实施方案中,本申请提供的化合物和组合物用于控制谷类中的不期望的植被。在某些实施方案中,不期望的植被是大穗看麦娘(AlopecurusmyosuroidesHuds.)(blackgrass,ALOMY),阿披拉草(Aperaspica-venti(L.)Beauv.)(风之草(windgrass),APESV),野燕麦(AvenafatuaL.)(野燕麦(wildoat),AVEFA),旱雀麦(BromustectorumL.)(丘原雀麦草(downybrome),BROTE),多花黑麦草(LoliummultiflorumLam.)(意大利黑麦草(Italianryegrass),LOLMU),小子虉草(PhalarisminorRetz.)(小种金丝雀草(littleseedcanarygrass),PHAMI),早熟禾(PoaannuaL.)(年生蓝草(annualbluegrass),POAAN),金狗尾草(Setariapumila(Poir.)Roemer&J.A.Schultes)(黄色狗尾草(yellowfoxtail),SETLU),狗尾草(Setariaviridis(L.)Beauv.)(绿色狗尾草(greenfoxtail),SETVI),丝路蓟(Cirsiumarvense(L.)Scop.)(加拿大蓟(Canadathistle),CIRAR),猪殃殃(GaliumaparineL.)(八仙草(catchweedbedstraw),GALAP),地肤(Kochiascoparia(L.)Schrad.)(地肤属(kochia),KCHSC),紫花野芝麻(LamiumpurpureumL.)(紫色枯荨麻(purpledeadnettle),LAMPU),母菊(MatricariarecutitaL.)(野甘菊(wildchamomile),MATCH),同花母菊(Matricariamatricarioides(Less.)Porter)(香甘菊(pineappleweed),MATMT),虞美人(PapaverrhoeasL.)(普通罂粟(commonpoppy),PAPRH),卷茎蓼(PolygonumconvolvulusL.)(野生荞麦(wildbuckwheat),POLCO),刺沙蓬(SalsolatragusL.)(俄罗斯蓟(Russianthistle),SASKR),繁缕(Stellariamedia(L.)Vill.)(普通繁缕(commonchickweed),STEME),阿拉伯婆婆纳(VeronicapersicaPoir.)(波斯婆婆纳(Persianspeedwell),VERPE),野生堇菜(ViolaarvensisMurr.)(田地紫罗兰(fieldviolet),VIOAR),或三色堇(ViolatricolorL.)(野生紫罗兰(wildviolet),VIOTR)。
在一些实施方案中,本申请提供的化合物和组合物用于控制牧场和牧地中的不期望的植被。在某些实施方案中,不期望的植被是豚草(AmbrosiaartemisiifoliaL.)(普通豚草(commonragweed),AMBEL),钝叶决明(Cassiaobtusifolia)(sicklepod,CASOB),斑点矢车菊(Centaureamaculosaauct.nonLam.)(spottedknapweed,CENMA),丝路蓟(Cirsiumarvense(L.)Scop.)(加拿大蓟(Canadathistle),CIRAR),田旋花(ConvolvulusarvensisL.)(野生旋花(fieldbindweed),CONAR),乳浆大戟(EuphorbiaesulaL.)(乳浆大戟(leafyspurge),EPHES),刺莴苣(LactucaserriolaL./Torn.)(多刺莴苣(pricklylettuce),LACSE),长叶车前(PlantagolanceolataL.)(鹿角车前(buckhornplantain),PLALA),钝叶酸模(RumexobtusifoliusL.)(阔叶羊蹄(broadleafdock),RUMOB),刺金午时花(SidaspinosaL.)(刺黄花稔(pricklysida),SIDSP),野欧白芥(SinapisarvensisL.)(野生芥菜(wildmustard),SINAR),苣荬菜(SonchusarvensisL.)(多年生苣荬菜(perennialsowthistle),SONAR),一枝黄花属物种(Solidagospecies)(秋麒麟草属(goldenrod),SOOSS),药用蒲公英(TaraxacumofficinaleG.H.WeberexWiggers)(蒲公英(dandelion),TAROF),白车轴草(TrifoliumrepensL.)(白三叶草(whiteclover),TRFRE),或异株荨麻(UrticadioicaL.)(普通荨麻(commonnettle),URTDI)。
在一些实施方案中,本申请提供的化合物和组合物用于控制中耕作物中发现的不期望的植被。在某些实施方案中,不期望的植被是大穗看麦娘(AlopecurusmyosuroidesHuds.)(黑草(blackgrass),ALOMY),野燕麦(AvenafatuaL.)(野燕麦(wildoat),AVEFA),臂形草(Brachiariaplatyphylla(Groseb.)Nash)(阔叶信号草(broadleafsignalgrass),BRAPP),马唐(Digitariasanguinalis(L.)Scop.)(大马唐草(largecrabgrass),DIGSA),稗(Echinochloacrus-galli(L.)P.Beauv.)(稗草(barnyardgrass),ECHCG),光头稗(Echinochloacolonum(L.)Link)(光头稗(junglerice),ECHCO),多花黑麦草(LoliummultiflorumLam.)(意大利黑麦草(Italianryegrass),LOLMU),洋野黍(PanicumdichotomiflorumMichx.)(秋黍(fallpanicum),PANDI),稷(PanicummiliaceumL.)(野生小米黍(wild-prosomillet),PANMI),大狗尾草(SetariafaberiHerrm.)(大狗尾草(giantfoxtail),SETFA),狗尾草(Setariaviridis(L.)Beauv.)(绿色狗尾草(greenfoxtail),SETVI),詹森草(Sorghumhalepense(L.)Pers.)(詹森草(Johnsongrass),SORHA),蜀黍(Sorghumbicolor(L.)Moenchssp.Arundinaceum)(shattercane,SORVU),油莎草(CyperusesculentusL.)(黄莎草(yellownutsedge),CYPES),香附子(CyperusrotundusL.)(紫莎草(purplenutsedge),CYPRO),苘麻(AbutilontheophrastiMedik.)(绒毛叶(velvetleaf),ABUTH),苋属物种(Amaranthusspecies)(藜(pigweeds)和苋(amaranths),AMASS),豚草(AmbrosiaartemisiifoliaL.)(普通豚草(commonragweed),AMBEL),多年生豚草(AmbrosiapsilostachyaDC.)(西方豚草(westernragweed),AMBPS),三裂叶豚草(AmbrosiatrifidaL.)(大豚草(giantragweed),AMBTR),叙利亚马利筋(AsclepiassyriacaL.)(普通乳草(commonmilkweed),ASCSY),藜草(ChenopodiumalbumL.)(普通灰菜(commonlambsquarters),CHEAL),丝路蓟(Cirsiumarvense(L.)Scop.)(加拿大蓟(Canadathistle),CIRAR),圆叶鸭跖草(CommelinabenghalensisL.)(饭包草(Benghaldayflower),COMBE),曼陀罗(DaturastramoniumL.)(曼陀罗(jimsonweed),DATST),胡萝卜(DaucuscarotaL.)(野生胡萝卜(wildcarrot),DAUCA),白苞猩猩草(EuphorbiaheterophyllaL.)(野生一品红(wildpoinsettia),EPHHL),野塘蒿(ErigeronbonariensisL.或Conyzabonariensis(L.)Cronq.)(毛飞蓬(hairyfleabane),ERIBO),加拿大蓬(ErigeroncanadensisL.)(加拿大飞蓬(Canadianfleabane),ERICA),向日葵(HelianthusannuusL.)(普通向日葵(commonsunflower),HELAN),小花假牵牛(Jacquemontiatamnifolia(L.)Griseb.)(小花牵牛花(smallflowermorningglory),IAQTA),碗仔花(Ipomoeahederacea(L.)Jacq.)(裂叶牵牛(ivyleafmorningglory),IPOHE),小白花牵牛(IpomoealacunosaL.)(白牵牛(whitemorningglory),IPOLA),刺莴苣(LactucaserriolaL./Torn.)(多刺莴苣(pricklylettuce),LACSE),马齿苋(PortulacaoleraceaL.)(普通马齿苋(commonpurslane),POROL),刺金午时花(SidaspinosaL.)(刺黄花稔(pricklysida),SIDSP),野欧白芥(SinapisarvensisL.)(野生芥菜(wildmustard),SINAR),东方龙葵(SolanumptychanthumDunal)(东方龙葵(easternblacknightshade),SOLPT)或苍耳(XanthiumstrumariumL.)(普通苍耳(commoncocklebur),XANST)。
在一些实施方案中在,在芽后操作中使用约1至约4,000克/公顷(g/ha)的施用率。在一些实施方案中,在芽前操作中使用约1至约4,000g/ha的施用率。
在一些实施方案中,本文提供的化合物、组合物和方法与一种或多种其他除草剂联用防治更广泛范围的不期望的植被。当与其他除草剂联用时,本申请的化合物可以与一种或多种其他除草剂配制、与一种或多种其他除草剂罐混合或者与一种或多种其他除草剂相继使用。可以与本申请描述的组合物和方法联合使用的一些除草剂包括但不限于:4-CPA,4-CPB,4-CPP,2,4-D,2,4-D胆碱盐,2,4-D酯和胺,2,4-DB,3,4-DA,3,4-DB,2,4-DEB,2,4-DEP,3,4-DP,2,3,6-TBA,2,4,5-T,2,4,5-TB,乙草胺(acetochlor),三氟羧草醚(acifluorfen),苯草醚(aclonifen),丙烯醛(acrolein),甲草胺(alachlor),草毒死(allidochlor),禾草灭(alloxydim),烯丙醇(allylalcohol),五氯戊酮酸(alorac),特津酮(ametridione),莠灭净(ametryn),特草嗪酮(amibuzin),氨唑草酮(amicarbazone),磺嘧磺隆(amidosulfuron),环丙嘧啶酸(aminocyclopyrachlor),氯氨吡啶酸(aminopyralid),甲基胺草磷(amiprofos-methyl),杀草强(amitrole),氨基磺酸铵(ammoniumsulfamate),莎稗磷(anilofos),疏草隆(anisuron),磺草灵(asulam),莠去通(atraton),莠去津(atrazine),唑啶草酮(azafenidin),四唑嘧磺隆(azimsulfuron),叠氮净(aziprotryne),燕麦灵(barban),BCPC,氟丁酰草胺(beflubutamid),草除灵(benazolin),bencarbazone,氟草胺(benfluralin),呋草磺(benfuresate),苄嘧磺隆(bensulfuron-methyl),地散磷(bensulide),杀草丹(benthiocarb),噻草平(bentazon-sodium),胺酸杀(benzadox),双苯嘧草酮(benzfendizone),苄草胺(benzipram),双环磺草酮(benzobicyclon),吡草酮(benzofenap),氟草黄(benzofluor),新燕灵(benzoylprop),噻草隆(benzthiazuron),氟吡草酮(bicyclopyrone),治草醚(bifenox),双丙氨酰膦(bilanafos),双草醚(bispyribac-sodium),硼砂(borax),除草定(bromacil),糠草腈(bromobonil),溴丁酰草胺(bromobutide),杀草全(bromofenoxim),溴苯腈(bromoxynil),溴莠敏(brompyrazon),丁草胺(butachlor),氟丙嘧草酯(butafenacil),抑草膦(butamifos),丁烯草胺(butenachlor),丁噻咪草酮(buthidazole),丁噻隆(buthiuron),地乐胺(butralin),丁苯草酮(butroxydim),炔草隆(buturon),丁草特(butylate),二甲胂酸(cacodylicacid),苯酮唑(cafenstrole),氯酸钙(calciumchlorate),氰氨化钙(calciumcyanamide),克草胺酯(cambendichlor),卡巴草灵(carbasulam),长杀草(carbetamide),特噁唑威(carboxazole),草败死(chlorprocarb),氟酮唑草(carfentrazone-ethyl),CDEA,CEPC,氯硝醚(chlomethoxyfen),草灭平(chloramben),丁酰草胺(chloranocryl),炔禾灵(chlorazifop),可乐津(chlorazine),氯溴隆(chlorbromuron),氯炔灵(chlorbufam),乙氧苯隆(chloreturon),伐草克(chlorfenac),燕麦酯(chlorfenprop),氟咪杀(chlorflurazole),氯芴素(chlorflurenol),氯草敏(chloridazon),氯嘧磺隆(chlorimuron),草枯醚(chlornitrofen),三氯丙酸(chloropon),氯麦隆(chlorotoluron),枯草隆(chloroxuron),羟敌草腈(chloroxynil),氯苯胺灵(chlorpropham),绿磺隆(chlorsulfuron),氯酞酸(chlorthal),草克乐(chlorthiamid),吲哚酮草酯(cinidon-ethyl),环庚草醚(cinmethylin),醚磺隆(cinosulfuron),咯草隆(cisanilide),烯草酮(clethodim),碘氯啶酯(cliodinate),炔草酯(clodinafop-propargyl),氯丁草(clofop),异噁草酮(clomazone),稗草胺(clomeprop),调果酸(cloprop),环丁烯草酮(cloproxydim),二氯吡啶酸(clopyralid),氯酯磺草胺(cloransulam-methyl),CMA,硫酸铜(coppersulfate),CPMF,CPPC,醚草敏(credazine),甲酚(cresol),苄草隆(cumyluron),氰草净(cyanatryn),氰草津(cyanazine),草灭特(cycloate),环丙嘧磺隆(cyclosulfamuron),噻草酮(cycloxydim),环莠隆(cycluron),氰氟草酯(cyhalofop-butyl),牧草快(cyperquat),环丙津(cyprazine),三环塞草胺(cyprazole),环酰草胺(cypromid),香草隆(daimuron),茅草枯(dalapon),棉隆(dazomet),敌草乐(delachlor),甜菜安(desmedipham),敌草净(desmetryn),燕麦敌(di-allate),麦草畏(dicamba),敌草腈(dichlobenil),氯全隆(dichloralurea),苄胺灵(dichlormate),2,4-滴丙酸(dichlorprop),精2,4-滴丙酸(dichlorprop-P),禾草灵(diclofop),(diclosulam),二乙除草双(diethamquat),乙酰甲草胺(diethatyl),氟苯戊烯酸(difenopenten),枯莠隆(difenoxuron),野燕枯(difenzoquat),吡氟酰草胺(diflufenican),二氟吡隆(diflufenzopyr),噁唑隆(dimefuron),哌草丹(dimepiperate),克草胺(dimethachlor),异戊净(dimethametryn),二甲吩草胺(dimethenamid),二甲吩草胺(dimethenamid-P),敌灭生(dimexano),敌米达松(dimidazon),敌乐胺(dinitramine),地乐特(dinofenate),丙硝酚(dinoprop),戊硝酚(dinosam),地乐酚(dinoseb),特乐酚(dinoterb),草乃敌(diphenamid),杀草净(dipropetryn),敌草快(diquat),disul,dithiopyr,diuron,DMPA,DNOC,DSMA,EBEP,甘草津(eglinazine),草藻灭(endothal),磺唑草(epronaz),EPTC,抑草蓬(erbon),禾草畏(esprocarb),丁氟消草(ethalfluralin),ethbenzamide,胺苯磺隆(ethametsulfuron),噻二唑隆(ethidimuron),抑草威(ethiolate),ethobenzamid,乙氧苯草胺(etobenzamid),乙呋草磺(ethofumesate),氯氟草醚(ethoxyfen),乙氧嘧磺隆(ethoxysulfuron),硝草酚(etinofen),乙胺草醚(etnipromid),乙氧苯酰草(etobenzanid),EXD,酰苯磺威(fenasulam),涕丙酸(fenoprop),噁唑禾草灵(fenoxaprop),精噁唑禾草灵(fenoxaprop-P-ethyl),精噁唑禾草灵(fenoxaprop-P-ethyl)+双苯恶唑酸(isoxadifen-ethyl),fenoxasulfone,氯苯氧乙醇(fenteracol),噻唑禾草灵(fenthiaprop),四唑草胺(fentrazamide),非草隆(fenuron),硫酸亚铁(ferroussulfate),麦草氟酯(flamprop),强氟燕灵(flamprop-M),啶嘧磺隆(flazasulfuron),双氟磺草胺(florasulam),吡氟禾草灵(fluazifop),精吡氟禾草灵(fluazifop-P-butyl),异丙吡草酯(fluazolate),氟酮磺隆(flucarbazone),氟吡磺隆(flucetosulfuron),氟消草(fluchloralin),氟噻草胺(flufenacet),氟苯吡草(flufenican),氟哒嗪草酯(flufenpyr-ethyl),唑嘧磺草胺(flumetsulam),三氟噁嗪(flumezin),氟亚胺草酯(flumiclorac-pentyl),丙炔氟草胺(flumioxazin),炔草胺(flumipropyn),伏草隆(fluometuron),消草醚(fluorodifen),乙羧氟草醚(fluoroglycofen),唑啶草(fluoromidine),氟除草醚(fluoronitrofen),氟苯隆(fluothiuron),氟胺草唑(flupoxam),flupropacil,四氟丙酸(flupropanate),氟啶磺隆(flupyrsulfuron),氟草同(fluridone),氟咯草酮(flurochloridone),氯氟吡氧乙酸(fluroxypyr),呋草酮(flurtamone),达草氟(fluthiacet),氟磺胺草醚(fomesafen),甲酰胺磺隆(foramsulfuron),膦铵素(fosamine),氟呋草醚(furyloxyfen),草丁膦(glufosinate),草铵膦(glufosinate-ammonium),草甘膦(glyphosate),氟硝磺酰胺(halosafen),氯吡嘧磺隆(halosulfuron-methyl),卤草定(haloxydine),氟吡甲禾灵(haloxyfop-methyl),精吡氟氯禾灵(haloxyfop-P-methyl),氟氯吡啶酯(halauxifen-methyl),六氯丙酮(hexachloroacetone),六氟盐(hexaflurate),六嗪酮(hexazinone),咪草酸(imazamethabenz),咪草啶酸(imazamox),甲咪唑烟酸(imazapic),灭草烟(imazapyr),灭草喹(imazaquin),咪唑乙烟酸(imazethapyr),唑吡嘧磺隆(imazosulfuron),茚草酮(indanofan),三嗪茚草胺(indaziflam),碘草腈(iodobonil),碘甲烷(iodomethane),碘磺隆(iodosulfuron),iofensulfuron,碘苯腈(ioxynil),抑草津(ipazine),ipfencarbazone,丙草定(iprymidam),丁咪胺(isocarbamid),异草定(isocil),丁嗪草酮(isomethiozin),异草完隆(isonoruron),氮革草(isopolinate),异丙乐灵(isopropalin),异丙隆(isoproturon),异恶隆(isouron),异噁酰草胺(isoxaben),异噁氯草酮(isoxachlortole),异噁氟草酮(isoxaflutole),异噁草醚(isoxapyrifop),特安灵(karbutilate),ketospiradox,乳氟禾草灵(lactofen),环草定(lenacil),利谷隆(linuron),MAA,MAMA,MCPA酯和胺,酚硫杀(MCPA-thioethyl),MCPB,2甲4氯丙酸(mecoprop),精2甲4氯丙酸(mecoprop-P),丁硝酚(medinoterb),苯噻酰草胺(mefenacet),氟磺酰草胺(mefluidide),灭莠津(mesoprazine),甲基二磺隆(mesosulfuron),甲基磺草酮(mesotrione),威百亩(metam),噁唑酰草胺(metamifop),苯嗪草酮(metamitron),吡草胺(metazachlor),双醚氯吡嘧磺隆(metazosulfuron),氟哒草(metflurazon),噻唑隆(methabenzthiazuron),氟烯硝草(methalpropalin),灭草定(methazole),甲硫苯威(methiobencarb),methiozolin,灭草恒(methiuron),醚草通(methometon),盖草津(methoprotryne),溴甲烷(methylbromide),异硫氰酸甲酯(methylisothiocyanate),苯丙隆(methyldymron),色满隆(metobenzuron),溴谷隆(metobromuron),异丙甲草胺(metolachlor),磺草唑胺(metosulam),甲氧隆(metoxuron),嗪草酮(metribuzin),甲磺隆(metsulfuron),草达灭(molinate),庚酰草胺(monalide),特噁唑隆(monisouron),单氯代乙酸(monochloroaceticacid),绿谷隆(monolinuron),灭草隆(monuron),伐草快(morfamquat),MSMA,萘丙胺(naproanilide),敌草胺(napropamide),napropamide-M,萘草胺(naptalam),草不隆(neburon),烟嘧磺隆(nicosulfuron),吡氯草胺(nipyraclofen),甲磺乐灵(nitralin),除草醚(nitrofen),三氟甲草醚(nitrofluorfen),达草灭(norflurazon),草完隆(noruron),八氯酮(OCH),坪草丹(orbencarb),邻-二氯苯(ortho-dichlorobenzene),嘧苯胺磺隆(orthosulfamuron),炔丙噁唑草(oxadiargyl),噁草灵(oxadiazon),噁杀草敏(oxapyrazon),环丙氧磺隆(oxasulfuron),氯噁嗪草(oxaziclomefone),乙氧氟草醚(oxyfluorfen),吡草醚(paraflufen-ethyl),对伏隆(parafluron),百草枯(paraquat),克草猛(pebulate),壬酸(pelargonicacid),二甲戊乐灵(pendimethalin),五氟磺草胺(penoxsulam),五氯酚(pentachloro苯酚),甲氯酰草胺(pentanochlor),环戊恶草酮(pentoxazone),黄草伏(perfluidone),烯草胺(pethoxamid),棉胺宁(phenisopham),甜菜宁(phenmedipham),乙基甜菜宁(phenmedipham-ethyl),稀草隆(phenobenzuron),乙酸苯汞(phenylmercuryacetate),氨氯吡啶酸(picloram),氟吡草胺(picolinafen),唑啉草酯(pinoxaden),哌草磷(piperophos),亚砷酸钾(potassiumarsenite),叠氮化钾(potassiumazide),氰酸钾(potassiumcyanate),丙草胺(pretilachlor),甲基氟嘧磺隆(primisulfuron-methyl),环丙腈津(procyazine),氨氟乐灵(prodiamine),氟唑草胺(profluazol),环丙氟灵(profluralin),环苯草酮(profoxydim),甘扑津(proglinazine),调环酸钙(prohexadione-calcium),扑灭通(prometon),扑草净(prometryn),毒草安(propachlor),敌稗(propanil),喔草酯(propaquizafop),扑灭津(propazine),苯胺灵(propham),异丙草胺(propisochlor),丙苯磺隆(propoxycarbazone),嗪咪唑嘧磺隆(propyrisulfuron),炔苯酰草胺(propyzamide),甲硫磺乐灵(prosulfalin),苄草丹(prosulfocarb),氟丙磺隆(prosulfuron),扑灭生(proxan),广草胺(prynachlor),比达农(pydanon),双唑草腈(pyraclonil),吡草醚(pyraflufen-ethyl),磺酰草吡唑(pyrasulfotole),pyrazogyl,吡唑特(pyrazolynate),吡嘧磺隆(pyrazosulfuron-ethyl),苄草唑(pyrazoxyfen),嘧啶肟草醚(pyribenzoxim),稗草丹(pyributicarb),氯草定(pyriclor),6-氯-3-苯基-4-哒嗪醇(pyridafol),哒草特(pyridate),环酯草醚(pyriftalid),肟啶草(pyriminobac),吡丙醚(pyrimisulfan),嘧硫草醚(pyrithiobac-methyl),罗克杀草砜(pyroxasulfone),啶磺草胺(pyroxsulam),二氯喹啉酸(quinclorac),氯甲喹啉酸(quinmerac),灭藻醌(quinoclamine),氯藻胺(quinonamid),喹禾灵(quizalofop),精喹禾灵(quizalofop-P-ethyl),硫氰苯胺(rhodethanil),玉嘧磺隆(rimsulfuron),苯嘧磺草胺(saflufenacil),S-异丙甲草胺(S-metolachlor),另丁津(sebuthylazine),密草通(secbumeton),稀禾定(sethoxydim),环草隆(siduron),西玛津(simazine),西玛通(simeton),西草净(simetryn),SMA,亚砷酸钠(sodiumarsenite),叠氮化钠(sodiumazide),氯酸钠(sodiumchlorate),磺草酮(sulcotrione),草克死(sulfallate),甲磺草胺(sulfentrazone),甲嘧磺隆(sulfometuron),草硫膦(sulfosate),磺酰磺隆(sulfosulfuron),硫酸(sulfuricacid),吖庚磺酯(sulglycapin),灭草灵(swep),三氯醋酸(TCA),牧草胺(tebutam),丁唑隆(tebuthiuron),特呋三酮(tefuryltrione),环磺酮(tembotrione),吡喃草酮(tepraloxydim),特草定(terbacil),特草灵(terbucarb),特丁草胺(terbuchlor),甲氧去草净(terbumeton),特丁津(terbuthylazine),去草净(terbutryn),四氟隆(tetrafluron),甲氧噻草胺(thenylchlor),赛氟隆(thiazafluron),噻唑烟酸(thiazopyr),噻二唑草胺(thidiazimin),赛苯隆(thidiazuron),噻酮磺隆(thiencarbazone-methyl),噻吩磺隆(thifensulfuron),禾草丹(thiobencarb),仲草丹(tiocarbazil),嘧草胺(tioclorim),苯吡唑草酮(topramezone),苯草酮(tralkoxydim),triafamone,野麦畏(tri-allate),醚苯磺隆(triasulfuron),三嗪氟草胺(triaziflam),苯磺隆(tribenuron),杀草畏(tricamba),绿草定(triclopyr)酯和胺,灭草环(tridiphane),草达津(trietazine),三氟啶磺隆(trifloxysulfuron),氟乐灵(trifluralin),氟胺磺隆(triflusulfuron),三氟苯氧丙酸(trifop),三氟禾草肟(trifopsime),三羟基三嗪(trihydroxyltriazine),三甲隆(trimeturon),茚草酮(tripropindan),草达克(tritac),三氟甲磺隆(tritosulfuron),灭草猛(vernolate)和二甲苯草胺(xylachlor)。
本公开的化合物和组合物一般与已知除草剂安全剂组合使用以增强它们的选择性,除草剂安全剂例如解草嗪(benoxacor)、禾草丹(benthiocarb)、云薹素内酯(brassinolide)、解毒喹(cloquintocet,例如,mexyl)、解草胺腈(cyometrinil)、香草隆(daimuron)、烯丙酰草胺(dichlormid)、二环酮(dicyclonon)、哌草丹(dimepiperate)、乙拌磷(disulfoton)、解草唑(fenchlorazole-ethyl)、解草啶(fenclorim)、解草胺(flurazole)、氟草肟(fluxofenim)、解草噁唑(furilazole)、超敏蛋白(harpinproteins)、双苯噁唑酸(isoxadifen-ethyl)、吡唑解草酯(mefenpyr-diethyl)、MG191、MON4660、萘二甲酸酐(NA)、解草腈(oxabetrinil)、R29148和N-苯基磺酰基苯甲酸酰胺。
本文描述的化合物、组合物和方法用于在以下作物中防治不期望的植被:草甘膦-耐受性-、草铵膦-耐受性-、麦草畏-耐受性-、苯氧基茁长素-耐受性-、吡啶基氧基茁长素-耐受性-、芳氧苯氧丙酸酯-耐受性-、乙酰辅酶A羧化酶(ACCase)抑制剂-耐受性-、咪唑啉酮-耐受性-、乙酰乳酸合成酶(ALS)抑制剂-耐受性-、4-羟基苯基-丙酮酸二氧酶(HPPD)抑制剂-耐受性-、原卟啉原氧化酶(PPO)抑制剂-耐受性-、三嗪-耐受性-和溴草腈-耐受性-作物(例如,但不限于,大豆,棉花,低芥酸油菜/油菜,稻子,谷类,玉米,草皮,等),例如,结合草甘膦,草铵膦,麦草畏,苯氧基茁长素,吡啶基氧基茁长素,芳氧苯氧丙酸酯,ACCase抑制剂,咪唑啉酮,ALS抑制剂,HPPD抑制剂,PPO抑制剂,三嗪和溴草腈。组合物和方法可以用于在如下的作物中防治不期望植被,该作物具有赋予对多种化学性质和/或多种模式作用的抑制剂的耐受性的多重或叠加性质。
本申请提供的化合物和组合物还可用于防治除草剂抗性或耐受性的杂草。示例性的抗性或耐受性杂草包括但不限于对以下呈抗性或耐受性的生物类型:乙酰乳酸合成酶(ALS)抑制剂、光合系统II抑制剂、乙酰辅酶A羧化酶(ACCase)抑制剂、合成茁长素、光合系统I抑制剂、5-烯醇丙酮莽草酸-3-磷酸合酶(EPSP)合成酶抑制剂、微管组装抑制剂抑制剂、脂质合成抑制剂、原卟啉原氧化酶(PPO)抑制剂、类胡萝卜素生物合成抑制剂、极长链脂肪酸(VLCFA)抑制剂、八氢番茄红素脱氢酶(PDS)抑制剂、谷氨酰氨合成酶抑制剂、4-羟基苯基-丙酮酸二氧酶(HPPD)抑制剂、有丝分裂抑制剂、纤维素生物合成抑制剂,具多重作用模式的除草剂例如快杀稗,以及未经分类的除草剂例如芳基氨基丙酸类、野燕枯、草多索以及有机砷类。具有抗性或耐受性的示例性杂草包括但不限于,对于多种除草剂具有抗性或耐受性的生物型,对于多种化合物类别具有抗性或耐受性的生物型,对于多种除草剂作用模式具有抗性或耐受性的生物型
所述实施方案以及以下实施例是用于示例目的,且无意于限制请求保护的范围。有关本文所述组合物的其它修饰、用途或组合对于本领域普通技术人员而言将是显而易见的,而不脱离请求保护的主题的精神和范围。
前体的合成
制备1:4-氨基-3,6-二氯吡啶-2-甲酸甲基酯(头部A)
如Fields等人,WO2001051468A1中所述制备。
制备2:4-氨基-3,6-二氯-5-氟吡啶-2-甲酸甲基酯(头部B)
如Fields等人,TetrahedronLetters2010,51,79-81中所述制备。
制备3:2,6-二氯-5-甲氧基-4-乙烯基嘧啶
在室温,历时一小时(h)向商购2,6-二氯-5-甲氧基嘧啶(100克(g),0.55摩尔(mol))于无水四氢呋喃中的溶液中滴加1摩尔当量(M)浓度的乙烯基溴化镁/四氢呋喃溶剂(124g,0.94mol)。然后将混合物在室温搅拌4h。通过加入丙酮(200毫升(mL))淬灭过量的格氏试剂,同时将混合物的温度维持在低于20℃。之后,立即加入2,3-二氯-5,6-二氰基-对苯醌(DDQ;151g,0.67mol)并搅拌过夜。有黄色固体析出。过滤所述固体并用乙酸乙酯(500mL)洗涤。减压浓缩滤液并将所得粗制化合物用乙酸乙酯(2升(L))稀释。将所得未溶解的黑色半固体通过用乙酸乙酯过滤来分离。将其进一步减压浓缩得到粗制化合物,将其通过柱色谱法来纯化。将化合物用5%至10%乙酸乙酯/己烷混合物洗脱得到标题化合物(70g,60%):mp60–61℃;1HNMR(CDCl3)δ3.99(s,3H),5.85(d,1H),6.75(d,1H),6.95(dd,1H)。
制备4:2,6-二氯-5-甲氧基-嘧啶-4-甲醛
将2,6-二氯-5-甲氧基-4-乙烯基嘧啶(50g,0.24mol)于二氯甲烷:甲醇(4:1,2L)中的溶液冷却至-78℃。使臭氧气体鼓泡通过,保持5h。将反应用二甲基硫化物(50mL)淬灭。将混合物缓慢温热至室温并在40℃减压浓缩得到标题化合物(50.5g,100%);高效液相色谱(HPLC;85%乙腈,用0.1%体积/体积(v/v)乙酸缓冲)。
制备5:2,6-二氯-5-甲氧基-嘧啶-4-甲酸甲基酯
制备2,6-二氯-5-甲氧基-嘧啶-4-甲醛(50g,0.24mol)于甲醇(1L)和水(60mL)中的溶液。向溶液中加入碳酸氢钠(400g)。在搅拌下,在0℃,历时45分钟(min)向嘧啶溶液中滴加2M溴(192g,1.2mol)于甲醇/水(600mL,9:1)中的溶液。继续在相同的温度搅拌1h。之后,将混合物在室温搅拌4h。在搅拌的同时,将反应混合物随后倒在碎冰(2L)、亚硫酸氢钠(50g)和氯化钠(NaCl;200g)的混合物上。将产物用乙酸乙酯(1Lx2)萃取,并将合并的有机层用硫酸钠干燥并过滤。减压蒸发溶剂产生稠密物,其在经长时间静置后固化,得到标题化合物(50.8g,87%);ESIMSm/z238([M+H]+)。
制备6:6-氨基-2-氯-5-甲氧基-嘧啶-4-甲酸甲基酯(头部C)
制备2,6-二氯-5-甲氧基-嘧啶-4-甲酸甲基酯(25g,0.1mol)和二甲基亚砜(DMSO)的溶液。在0–5℃,向该溶液中加入氨(2当量)的DMSO溶液。将该混合物在相同的0–5℃温度搅拌10至15分钟。之后,将混合物用乙酸乙酯稀释,并过滤出所得固体。将乙酸乙酯滤液用盐水溶液洗涤并用硫酸钠干燥。浓缩后,得到粗制产物。将粗制产物在最少量的乙酸乙酯中搅拌并过滤得到纯的化合物。从滤液得到更多的纯化合物,浓缩后,将其通过快速色谱法来纯化。这得到标题化合物(11g,50%):mp158℃;1HNMR(DMSO-d6)δ3.71(s,3H),3.86(s,3H),7.65(brs,1H),8.01(brs,1H)。
制备7:4-氨基-3,6-二氯-5-碘吡啶-2-甲酸甲基酯
将4-氨基-3,6-二氯吡啶-2-甲酸甲基酯(10.0g,45.2mmol),高碘酸(3.93g,17.2毫摩尔(mmol))和碘(11.44g,45.1mmol)溶解在甲醇(30mL)中并在60℃回流搅拌27h。浓缩反应混合物,用乙醚稀释并用饱和亚硫酸氢钠水溶液洗涤两次。将水层用乙醚萃取一次并将合并的有机层用无水硫酸钠干燥。浓缩产物并通过快速色谱法(硅胶,0-50%乙酸乙酯/己烷)来纯化得到标题化合物,其为浅黄色固体(12.44g,79%):mp130.0–131.5℃;1HNMR(400MHz,CDCl3)δ5.56(s,2H),3.97(s,3H);13CNMR(101MHz,CDCl3)δ163.80,153.00,152.75,145.63,112.12,83.91,53.21;EIMSm/z346。
制备8:4-氨基-3,6-二氯-5-甲基吡啶-2-甲酸甲基酯(头部D)
将4-氨基-3,6-二氯-5-碘吡啶-2-甲酸甲基酯(8.1g,23.4mmol)、四甲基锡烷(8.35g,46.7mmol)和二(三苯基膦)钯(II)二氯化物(2.5g,3.5mmol)于1,2-二氯乙烷(40mL)中的混合物在BiotageInitiator微波炉中在120℃照射30min,外部从侧面用红外(IR)-温度传感器监测。将反应混合物直接负载在硅胶柱上并通过快速色谱法(硅胶,0-50%乙酸乙酯/己烷)来纯化,得到标题化合物,其为橙色固体(4.53g,83%):mp133–136℃;1HNMR(400MHz,CDCl3)δ4.92(s,2H),3.96(s,3H),2.29(s,3H);13CNMR(101MHz,CDCl3)δ164.34,150.24,148.69,143.94,117.01,114.60,53.02,14.40;ESIMSm/z236([M+H]+),234([M-H]-).
制备9:6-氨基-2,5-二氯嘧啶-4-甲酸甲基酯(头部E)
如Epp等人,WO2007082076A1中所述来制备。
制备10:4-氨基-6-氯-5-氟-3-甲氧基吡啶-2-甲酸甲基酯(头部F)
如Epp等人,WO2013003740A1中所述来制备。
制备11:4-氨基-6-氯-5-氟-3-乙烯基吡啶-2-甲酸甲基酯(头部G)
将4-氨基-6-氯-5-氟-3-碘吡啶-2-甲酸甲基酯(7.05g,21.33mmol,如Epp等人,WO2013003740A1中所述来制备)和乙烯基三-正丁基锡(7.52mL,25.6mmol)悬浮在1,2-二氯乙烷(71.1mL)中并将混合物用氩气脱气10min。然后加入二(三苯基膦)钯(II)二氯化物(1.497g,2.133mmol)并将反应混合物在70℃搅拌过夜(澄清的橙色溶液)。将反应通过气相色谱-质谱(GC-MS)来监测。20h后,浓缩反应混合物,吸附在硅藻土上并通过柱色谱法(SiO2,己烷/乙酸乙酯梯度)来纯化,得到标题化合物,其为浅棕色固体(3.23g,65.7%):mp99–100℃;1HNMR(400MHz,CDCl3)δ6.87(dd,J=18.1,11.6Hz,1H),5.72(dd,J=11.5,1.3Hz,1H),5.52(dd,J=18.2,1.3Hz,1H),4.79(s,2H),3.91(s,3H);19FNMR(376MHz,CDCl3)δ-138.79(s);EIMSm/z230。
制备12:4-氨基-3,5,6-三氯吡啶-2-甲酸甲基酯(头部H)
如Finkelstein等人,WO2006062979A1中所述来制备。
制备13:4-氨基-6-溴-3-氯-5-氟吡啶-2-甲酸甲基酯(头部I)
如Arndt等人,US20120190857A1中所述来制备。
制备14:4-氨基-3-氯-5-氟-6-(三甲基锡烷基)吡啶-2-甲酸甲基酯(头部J)
将4-氨基-6-溴-3-氯-5-氟吡啶-2-甲酸甲基酯(500mg,1.8mmol),1,1,1,2,2,2-六甲基二锡烷(580mg,1.8mmol)和二(三苯基膦)-钯(II)氯化物(120mg,0.18mmol)合并在无水二噁烷(6mL)中,用氮气流喷洗10min,然后加热至80℃,保持2h。将冷却的混合物与乙酸乙酯(25mL)和饱和NaCl(25mL)一起搅拌15min。分离出有机相,用硅藻土过滤,干燥(Na2SO4)并蒸发。将残余物吸收在乙酸乙酯(4mL)中,搅拌并用己烷(15mL)逐份处理。将乳白色溶液从所产生的固体中滗出,用玻璃棉过滤并蒸发得到标题化合物,其为灰白色固体(660mg,100%):1HNMR(400MHz,CDCl3)δ4.63(d,J=29.1Hz,1H),3.97(s,2H),0.39(s,4H);19FNMR(376MHz,CDCl3)δ-130.28;EIMSm/z366。
制备15:4-乙酰胺基-3-氯-6-(三甲基锡烷基)-吡啶-2-甲酸甲基酯(头部K)
如Balko等人,WO2003011853A1中所述来制备。
制备16:4-乙酰胺基-3,6-二氯吡啶-2-甲酸甲基酯(头部L)
如Fields等人,WO2001051468A1中所述来制备。
制备17:4-氨基-3-氯-6-碘吡啶-2-甲酸甲基酯(头部M)
如Balko等人,WO2007082098A2中所述来制备。
制备18:4-乙酰胺基-3-氯-6-碘吡啶-2-甲酸甲基酯(头部N)
如Balko等人,WO2007082098A2中所述来制备。
制备19:4-氨基-6-溴-3,5-二氟吡啶-2-甲酸甲基酯(头部O)
如Fields等人,WO2001051468A1中所述来制备。
制备20:6-氨基-2-氯-5-乙烯基嘧啶-4-甲酸甲基酯(头部P)
如Epp等人,US20090088322中所述来制备。
制备21:2,2,5-三氟-6-碘苯并[d][1,3]二氧杂环戊烯
2,2,6-三氟苯并[d][1,3]二氧杂环戊烯-5-胺(8.0g,42mmol)添加至浓盐酸(浓HCl;200mL)中,冷却至5℃,剧烈搅拌并经10min滴加亚硝酸钠(4.3g,63mmol)在水(10mL)中的溶液处理。于5–10℃持续搅拌30min并且将混合物小心地倒入碘化钠(19g,130mmol)在水(200mL)中的溶液中,以二氯甲烷(100mL)快速搅拌。20min后,混合物以10%亚硫酸氢钠溶液(NaHSO3;20mL)处理并再搅拌20min。分离各相并且水相以二氯甲烷(75mL)萃取。合并的有机相以饱和NaCl洗涤(30mL),干燥(Na2SO4)并蒸发。剩余物通过色谱在硅胶上以己烷纯化得到标题化合物,为澄清液体(6g,51%):1HNMR(400MHz,CDCl3)δ7.41(d,J=5.0Hz,1H),6.90(d,J=6.6Hz,1H);19FNMR(376MHz,CDCl3)δ-49.63(s),-95.24(s);EIMSm/z302.
制备22:4,4,5,5-四甲基-2-(2,2,6-三氟苯并[d][1,3]二氧杂环戊烯-5-基)-1,3,2-二氧杂硼杂环戊烷
2,2,5-三氟-6-碘苯并[d][1,3]二氧杂环戊烯(1.0g,3.3mmol)溶解于无水四氢呋喃(10mL),冷却至5℃并以异丙基氯化镁-氯化锂复合物溶液(1.3M;2.7mL,3.5mmol)处理。混合物于5–15℃搅拌1h,以2-异丙氧基-4,4,5,5-四甲基-1,3,2-二氧杂硼杂环戊烷(720μL,660mg,3.5mmol)处理并搅拌20min。反应通过添加饱和氯化铵(NH4Cl;5mL)淬灭,并与乙酸乙酯(20mL)和饱和NaCl(10mL)混合。分离的有机相以饱和NaCl洗涤(10mL),干燥(Na2SO4)并蒸发得到标题化合物,为白色固体(1.0g,100%):1HNMR(400MHz,CDCl3)δ7.37(d,J=4.3Hz,1H),6.81(d,J=7.7Hz,1H),1.35(s,12H);19FNMR(376MHz,CDCl3)δ-49.96(s),-104.21(s));EIMSm/z302.
制备23:2,2,5-三氟-4-碘苯并[d][1,3]二氧杂环戊烯
将仲丁基锂(1.4M在环己烷中;6.1mL,8.5mmol)添加至已经预冷却至-40℃的无水四氢呋喃(15mL)中。将溶液冷却至-75℃,以2,2,5-三氟苯并[d][1,3]二氧杂环戊烯(1.5g,8.5mmol)处理并于该温度搅拌90min。该溶液经由导管快速转移至碘(2.8g,11mmol)在四氢呋喃(25mL)中的搅拌溶液中,将混合物冷却至-75℃。混合物搅拌1h,期间温度上升至-20℃。该反应通过添加饱和NH4Cl(10mL)淬灭并且然后与10%NaHSO3(15mL)和乙酸乙酯(30mL)混合。有机相以饱和NaCl洗涤(10mL),干燥(Na2SO4)并蒸发。该物质通过快速色谱以己烷纯化得到标题化合物,为澄清液体(1.5g,58%):1HNMR(400MHz,CDCl3)δ6.97(dd,J=8.8,4.0Hz,1H),6.81(dd,J=11.7,5.4Hz,1H);19FNMR(376MHz,CDCl3)δ-49.06,-103.15;EIMSm/z302.
制备24:5-溴-4-氯-2,2-二氟苯并[d][1,3]二氧杂环戊烯
2,2,6,6-四甲基哌啶(2.1mL,1.8g,12mmol)溶解于无水四氢呋喃(15mL),冷却至-75℃并以正丁基锂(n-BuLi,2.5M;4.8mL,12mmol)处理,并于-75℃搅拌混合物30min。添加5-溴-2,2-二氟苯并[d][1,3]二氧杂环戊烯(2.0g,8.4mmol),并于-75℃搅拌混合物2h。添加1,1,2-三氯-1,2,2-三氟乙烷(2.4mL,3.8g,20mmol)并持续搅拌1.5h。添加饱和NH4Cl(10mL),并且震荡混合物与二乙醚(30mL)和水(20mL)。乙醚相以饱和NaCl洗涤(10mL),干燥(Na2SO4)并真空蒸发。剩余物通过色谱在硅胶上以己烷纯化并且然后通过反相HPLC使用75%乙腈再纯化得到标题化合物,为澄清液体(640mg,28%):1HNMR(400MHz,CDCl3)δ7.38(dd,J=8.5,5.1Hz,1H),6.90(dd,J=9.0,4.7Hz,1H);EIMSm/z332.
制备25:2-(4-氯-2,2-二氟苯并[d][1,3]二氧杂环戊烯-5-基)-4,4,5,5-四甲基-1,3,2-二氧杂硼杂环戊烷
5-溴-4-氯-2,2-二氟苯并[d][1,3]二氧杂环戊烯(1.0g,3.7mmol)溶解于无水四氢呋喃(12mL)中,冷却至-20~-30℃并以异丙基氯化镁-氯化锂复合物溶液(1.3M;3.1mL,4.1mmol)分份处理。于-20至0℃90min后,添加2-异丙氧基-4,4,5,5-四甲基-1,3,2-二氧杂硼杂环戊烷(830μL,750mg,4.1mmol),并于0–20℃持续搅拌90min。反应通过添加饱和NH4Cl(10mL)淬灭,并且混合物以乙酸乙酯萃取(30mL)。水相再次以乙酸乙酯(15mL)萃取,并且合并的有机相以饱和NaCl(15mL)洗涤,干燥(Na2SO4)并蒸发得到标题化合物,为白色固体(1.2g,ca.100%):1HNMR(400MHz,CDCl3)δ7.52(d,J=8.1Hz,1H),6.99–6.94(m,1H),1.36(s,12H);19FNMR(376MHz,CDCl3)δ-49.62(s);EIMSm/z318.
制备26:4-氟苯并[d][1,3]二氧杂环戊烯-2-硫酮
3-氟苯-1,2-二醇(5.0g,39mmol)和硫光气(3.3mL,5.0g,42mmol)混合在氯仿(50mL)中,冷却至10℃并且经30min滴加氢氧化钠(10%溶液;36g,90mmol)处理,伴随强烈搅拌。在环境温度搅拌2h后,真空除去氯仿,并且所形成的固体通过过滤收集并以水洗涤。固体溶解于乙酸乙酯(100mL),溶液以水(30mL)和饱和NaCl(30mL)洗涤,干燥(Na2SO4)并蒸发。粗的固体通过色谱在硅胶上以0–30%乙酸乙酯-己烷纯化得到标题化合物(1.5g,77%):mp58–59℃;1HNMR(400MHz,CDCl3)δ7.28(m,1H),7.12(m,2H);19FNMR(376MHz,CDCl3)δ-131.32;EIMSm/z170.
制备27:5-溴-2,2,4-三氟苯并[d][1,3]二氧杂环戊烯
4-氟苯并[d][1,3]二氧杂环戊烯-2-硫酮(4.8g,28mmol)溶解于二氯甲烷(75mL),冷却至-30℃并以氟化氢(HF)-吡啶(70重量百分比(wt%)溶液;18mL,20g,140mmol)处理。经30min分份添加1,3-二溴-5,5-二甲基咪唑烷-2,4-二酮(9.7g,34mmol)。于-20至-30℃搅拌混合物2h并且然后与5%NaHSO3溶液(20mL)搅拌10min。分离有机相,干燥(Na2SO4),并且二氯甲烷通过在大气压下蒸馏经过200毫米(mm)Vigreux柱小心地除去。当大部分二氯甲烷已经从顶部取出时,将压力降低至约150毫米汞柱(mmHg)。持续蒸馏并且收集于45–55℃沸腾的级分,得到标题化合物,为澄清液体(3.2g,45%):1HNMR(400MHz,CDCl3)δ7.28(dd,J=8.6,6.2Hz,1H),6.81(dd,J=8.6,1.3Hz,1H);19FNMR(376MHz,CDCl3)δ-49.25(s),-126.72(s);EIMSm/z254.
制备28:4,4,5,5-四甲基-2-(2,2,4-三氟苯并[d][1,3]二氧杂环戊烯-5-基)-1,3,2-二氧杂硼杂环戊烷
5-溴-2,2,4-三氟苯并[d][1,3]二氧杂环戊烯(4.0g,16mmol)溶解于20mL无水四氢呋喃中,冷却至-20℃并经10min以异丙基氯化镁-氯化锂复合物(1.3M在四氢呋喃中;13mL,17mmol)分份处理。于-20至0℃搅拌30min后,添加2-异丙氧基-4,4,5,5-四甲基-1,3,2-二氧杂硼杂环戊烷(3.1g,17mmol),并于10–15℃持续搅拌1h。在以饱和NH4Cl溶液(10mL)处理后,混合物以乙酸乙酯稀释(50mL)。有机相以饱和NaCl洗涤(15mL),干燥(Na2SO4)并蒸发得到标题化合物,为棕色固体(3.5g,72%):1HNMR(400MHz,CDCl3)δ7.46(d,J=26.5Hz,1H),6.90(dd,J=18.5,4.5Hz,1H),1.35(s,12H);19FNMR(376MHz,CDCl3)δ-49.70(s),-126.00(s);EIMSm/z302.
制备29:2-(2,2-二氟-4-甲基苯并[d][1,3]二氧杂环戊烯-5-基)-5,5-二甲基-1,3,2-二氧杂硼杂环己烷
5-溴-2,2-二氟-4-甲基苯并[d][1,3]二氧杂环戊烯(如Nakamura,Yuji;Mitani,Shigeru;Tsukuda,Shintar,WO2007069777中所描述的制备;1.0g,4.0mmol)与1,1'-双(二苯基膦)二茂铁二氯-钯(II)复合物和二氯甲烷(330mg,0.40mmol)、乙酸钾(1.2g,12mmol)和5,5,5',5'-四甲基-2,2'-二(1,3,2-二氧杂硼杂环己烷)(950mg,4.2mmol)于无水DMSO(10mL)中混合,加热至80℃保持4h并且然后静置过夜。混合物与乙酸乙酯(50mL)和水(30mL)一起振荡。有机相以水洗涤,以饱和NaCl洗涤,干燥(Na2SO4),并蒸发。剩余物通过色谱在硅胶上以5–50%乙酸乙酯-己烷纯化得到标题化合物(540mg,48%):1HNMR(400MHz,CDCl3)δ7.55–7.48(m,1H),6.88–6.79(m,1H),5.51–5.47(m,1H),3.83–3.64(m,5H),1.02(d,J=4.9Hz,7H);19FNMR(376MHz,CDCl3)δ-49.91(d,J=7.1Hz);EIMSm/z284.
制备30:1-溴-2-(2-溴-1,1,2,2-四氟乙氧基)-3-氟苯
2-溴-6-氟苯酚(10.2g,53mmol)、碳酸钾(7.3g,53mmol),1,2-二溴-四氟乙烷(21g,80mmol)和1-丁硫醇(1.1g,12mmol)混合于无水N,N-二甲基甲酰胺(75mL)中并在搅拌高压反应器中加热至50℃。冷却后,内含物与1.0M氢氧化钠(NaOH;100mL)混合并以二乙醚(80mL份)萃取三次。合并的萃取物以水(15mL)、2.0MNaOH(45mL)洗涤,干燥(Na2SO4)并通过旋转蒸发浓缩。该物质通过硅胶色谱纯化以己烷洗脱得到标题化合物,为澄清液体(15g,76%):1HNMR(400MHz,CDCl3)δ7.48–7.39(m,1H),7.22–7.14(m,2H);EIMSm/z368.
制备31:2,2,3,3,7-五氟-2,3-二氢苯并呋喃
1-溴-2-(2-溴-1,1,2,2-四氟乙氧基)-3-氟苯(14g,38mmol)、铜粉(12.2g,192mmol)和2,2’-联吡啶(610mg,3.9mmol)混合于无水DMSO(55mL)中并加热至150℃保持1.5h。施加真空(约20mm)至反应器并顶部去除蒸馏液直到釜温达到100℃。含有产物和DMSO的蒸馏液以1:1二乙醚-戊烷(30mL)稀释并以水洗涤(3x5mL),干燥,并在1个大气压(atm)下通过200mmVigreux柱蒸馏以除去大部分溶剂,施加真空(约20mmHg)并且在60–65℃收集级分得到标题化合物,为澄清液体(5.1g,64%):1HNMR(400MHz,CDCl3)δ7.40–7.31(m,2H),7.25–7.17(m,1H);EIMSm/z210.
制备32:2,2,3,3,7-五氟-6-碘-2,3-二氢苯并呋喃
2,2,3,3,7-五氟-2,3-二氢苯并呋喃(500mg,2.4mmol)分份添加至在无水四氢呋喃(7mL)中从二丙胺(380mg,3.8mmol)和2.5Mn-BuLi(1.4mL,3.6mmol)制备的二异丙基氨化锂(LDA)的-70℃溶液中。于-70℃40min后,经15min添加碘(1.0g,4.0mmol)在四氢呋喃(5mL)中的溶液。于-70℃20min后,混合物升温至-20℃并通过添加饱和NH4Cl淬灭。混合物以10%NaHSO3(15mL)处理,搅拌10min并以二乙醚(15mL每份)萃取两次。合并的萃取物经干燥(Na2SO4)并蒸发。剩余物通过反相HPLC纯化,以85%乙腈-水洗脱,得到标题化合物(200mg,25%):1HNMR(400MHz,CDCl3)δ7.25(dd,J=8.1,4.8Hz,1H),6.63(dd,J=8.0,1.1Hz,1H),4.13(s,3H);EIMSm/z336.
制备33:5-溴-2,2-二氟-4-甲氧基苯并[d][1,3]二氧杂环戊烯
LDA的溶液从二异丙基胺(4.2g,41mmol)和n-BuLi(2.5M;15.4mL,38mmol)在无水四氢呋喃(100mL)中制备。溶液冷却至-70℃并以5-溴-2,2-二氟苯并[d][1,3]二氧杂环戊烯(7.0g,30mmol)分份处理。于-70℃2h后,分份添加硼酸三甲基酯(4.3g,41mmol),于-70℃搅拌1.5h并且然后升温至环境温度过夜。混合物冷却至-30至-40℃并以28%过乙酸小心地处理。混合物于-30℃搅拌30min,温热至5–10℃,并以10%NaHSO3(100mL)溶液处理并搅拌20min。混合物通过添加6MHCl酸化并以饱和NaCl溶液(75mL)稀释。混合物以乙酸乙酯(2x100mL)萃取并且合并的萃取物以饱和NaCl洗涤(50mL),干燥(Na2SO4)并旋转蒸发。粗苯酚溶解于无水DMSO(50mL)中,以95%NaH(750mg,30mmol)处理并搅拌30min,得到澄清溶液。分份添加甲基碘(5.0g,35mmol)并于20℃搅拌混合物20h。添加另外的200mgNaH并再持续搅拌1h。混合物倒入水(100mL)中并以二乙醚(2x75mL)萃取。合并的萃取物以水(2x20mL)、以饱和NaCl(20mL)洗涤,干燥(Na2SO4)并蒸发。粗物质通过色谱在硅胶上以0–20%乙酸乙酯-己烷梯度纯化得到标题化合物,为澄清液体(2.5g,31%):1HNMR(400MHz,CDCl3)δ7.25(d,J=8.5Hz,1H),6.63(d,J=8.5Hz,1H),4.13(s,3H);19FNMR(376MHz,CDCl3)δ-49.66;EIMSm/z266.
制备34:2-(2,2-二氟-4-甲氧基苯并[d][1,3]二氧杂环戊烯-5-基)-4,4,5,5-四甲基-1,3,2-二氧杂硼杂环戊烷
2-(2,2-二氟-4-甲氧基苯并[d][1,3]二氧杂环戊烯-5-基)-4,4,5,5-四甲基-1,3,2-二氧杂硼杂环戊烷(1.1g,4.1mmol)溶解于无水四氢呋喃(10mL),冷却至0–5℃并以异丙基氯化镁-氯化锂溶液(1.3M;3.5mL,4.5mmol)分份处理。于0–5℃搅拌混合物1h,以2-异丙氧基-4,4,5,5-四甲基-1,3,2-二氧杂硼杂环戊烷(840mg,4.5mmol)处理并于20℃搅拌90min。混合物以饱和NH4Cl(5mL)处理并搅拌10min。混合物以乙酸乙酯萃取(30mL)并且萃取物以饱和NaCl洗涤(10mL),干燥(Na2SO4)并旋转蒸发得到标题化合物,为油状物,其静置时凝固(1.2g,93%):1HNMR(400MHz,CDCl3)δ7.42(d,J=8.0Hz,1H),6.72(d,J=8.0Hz,1H),4.06(s,3H),1.34(s,12H);19FNMR(376MHz,CDCl3)δ-50.09;EIMSm/z314.
制备35:3,5-二氟苯-1,2-二醇
3,5-二氟-2-甲氧基苯酚(1.0g,6.3mmol,如Jones,LynH.;Randall,Amy;Barba,Oscar;Selby,MatthewD.,Organic&BiomolecularChemistry2007,5,3431-3433中所描述的制备)溶解于无水二氯甲烷(11mL)中,冷却至-20~-30℃并以在二氯甲烷中的三溴化硼(BBr3)溶液(1.0M;13mL,13mmol)分份处理。除去冷却浴并于20℃搅拌混合物搅拌20h。混合物冷却至-30℃,以水(3mL)分份处理并且然后升温至20℃。添加6MHCl(10mL)和乙酸乙酯(30mL),并搅拌混合物20min,得到两个澄清的相。水相以乙酸乙酯萃取(20mL),并且合并的有机相以饱和NaCl洗涤(10mL),干燥(Na2SO4)并旋转蒸发得到标题化合物,为油状物,其在静置时固化(720mg,78%):1HNMR(400MHz,CDCl3)δ6.51(ddd,J=9.5,2.8,2.1Hz,1H),6.45(ddd,J=10.3,8.7,2.9Hz,1H),5.71(s,1H),5.06(s,1H);19FNMR(376MHz,CDCl3)δ-119.56,-136.16;EIMSm/z146.
制备36:4,6-二氟苯并[d][1,3]二氧杂环戊烯-2-硫酮
3,5-二氟苯-1,2-二醇(670mg,4.6mmol)于无水氯仿(8mL)中搅拌,以硫光气(580mg,5.0mmol)处理,冷却至5–10℃,并且经45min滴加10%NaOH溶液(4.2g,11mmol)处理。30min后,挥发物通过旋转蒸发除去并且剩余固体通过过滤收集并以水洗涤。固体溶解于乙酸乙酯(30mL),以水(2x20mL)洗涤,以饱和NaCl(1x10mL)洗涤,干燥(Na2SO4),并蒸发。剩余物通过色谱在具有0–20%乙酸乙酯-己烷梯度的硅胶上纯化得到标题化合物(710mg,82%):1HNMR(400MHz,CDCl3)δ6.95(ddd,J=6.8,2.3,1.4Hz,1H),6.89(td,J=9.5,2.3Hz,1H);19FNMR(376MHz,CDCl3)δ-109.99(s),-127.93(s);EIMSm/z188.
制备37:2,2,4,6-四氟苯并[d][1,3]二氧杂环戊烯
4,6-二氟苯并[d][1,3]二氧杂环戊烯-2-硫酮(9.0g,48mmol)溶解于聚乙烯瓶中的无水二氯甲烷(100mL)中,冷却至-30至-35℃并以70%吡啶-氟化氢复合物(68g,480mmol)处理。混合物保持在该温度下并经1h以N-碘琥珀酰亚胺(32g,144mmol)分份处理。混合物搅拌3h,同时升温至5℃。冷却至-30℃后,混合物以20%NaHSO3(75mL)分份处理,伴随剧烈搅拌。混合物通过硅藻土过滤以除去深色固体。分离的水相以二氯甲烷(75mL)萃取,并且合并的萃取物以水洗涤(2x50mL)并以饱和NaCl洗涤(1x50mL)。溶剂通过大气压蒸馏经过300mmVigreux柱而除去。剩余物在310mmHg蒸馏,并且级分于40-45℃收集,含有标题化合物,为澄清液体(1.3g,14%):1HNMR(400MHz,CDCl3)δ6.71(m,1H),6.68(m,1H);19FNMR(376MHz,CDCl3)δ-49.47,-113.41,-131.95;EIMSm/z194.
制备38:2,2,4,6-四氟-5-碘苯并[d][1,3]二氧杂环戊烯
2,2,4,6-四氟苯并[d][1,3]二氧杂环戊烯(500mg,2.6mmol)溶解于无水四氢呋喃(7mL),冷却至-70℃,于-70℃滴加以仲-BuLi(1.3M;2.1mL,2.7mmol)处理并搅拌1h。经10min滴加碘(1.1g,4.4mmol)在四氢呋喃(5mL)中的溶液处理该混合物。于-70℃2h后,混合物以饱和NH4Cl处理,以乙醚萃取,干燥(Na2SO4)并蒸发。该物质通过反相HPLC以85%乙腈-水纯化,得到标题化合物(250mg;30%):1HNMR(400MHz,CDCl3)δ6.80–6.77(d,J=8.7Hz,1H),6.77–6.75(d,J=8.7Hz,1H);19FNMR(376MHz,CDCl3)δ-48.72,-99.73,-132.62;EIMSm/z320.
制备39:4,6-二氟苯并[d][1,3]二氧杂环戊烯
3,5-二氟苯-1,2-二醇(10g,69mmol)溶解于无水N,N-二甲基甲酰胺(100mL)中,以碳酸铯(56g,170mmol)处理并于20℃搅拌30min。添加溴氯甲烷(12g,90mmol)并加热混合物并于60℃搅拌19h。冷却后,混合物与水(100mL)和二乙醚(100mL)一起震荡。水相再次以乙醚(50mL)萃取。合并的萃取物以水(2x20mL)洗涤,以饱和NaCl(1x10mL)洗涤并干燥(Na2SO4)。通过大气压蒸馏通过300mmVigreux柱除去大部分乙醚。压力减低至75mmHg并且产物于70–90℃蒸馏得到标题化合物,为浓稠油状物(3.0g,28%):1HNMR(400MHz,CDCl3)δ6.45(m,1H),6.42(d,J=2.4Hz,1H),6.39(d,J=2.4Hz,1H),6.02(s,2H);19FNMR(376MHz,CDCl3)δ-117.99,-135.90;EIMSm/z158.
制备40:4,6-二氟-5-碘苯并[d][1,3]二氧杂环戊烯
4,6-二氟苯并[d][1,3]二氧杂环戊烯(300mg,1.9mmol)和N-碘琥珀酰亚胺(640mg,2.9mmol)混合于无水乙腈(5mL)中,以三氟乙酸(430mg,3.8mmol)处理并搅拌20h。混合物与NaHSO3溶液(100mg,在2mL水中)一起搅拌并且然后与乙酸乙酯(30mL)和饱和NaCl(5mL)一起震荡。有机相以饱和NaCl(5mL)洗涤,干燥(Na2SO4)并蒸发。该物质通过色谱在硅胶上以0–5%乙酸乙酯-己烷梯度纯化得到标题化合物,为白色固体(410mg,76%):mp65–66℃.1HNMR(400MHz,CDCl3)δ6.54(dd,J=6.9,1.6Hz,1H),6.07(s,2H);19FNMR(376MHz,CDCl3)δ-99.31,-117.98;EIMSm/z284.
制备41:4,4,5,5-四甲基-2-(2-甲基苯并[d][1,3]二氧杂环戊烯-5-基)-1,3,2-二氧杂硼杂环戊烷
5-溴-2-甲基苯并[d][1,3]二氧杂环戊烯(1.0g,4.7mmol,如Matyus,Peter;Magyar,Kalman;Pihlavista,Marjo;Gyires,Klara;Haider,Norbert;Wang,Yinghua;Woda,Patrick;Dunkel,Petra;Toth-Sarudy,Eva;Turos,Gyoergy,WO2010029379中所描述的制备)溶解于无水四氢呋喃(10mL),冷却至-70℃并经5min以n-BuLi(2.5M;2.1mL,4.7mmol)处理。1h后,添加2-异丙氧基-4,4,5,5-四甲基-1,3,2-二氧杂硼杂环戊烷(1.1g,6.0mmol)并且在-70至-30℃搅拌混合物90min。添加饱和NH4Cl(5mL)后,混合物与乙酸乙酯(40mL)和饱和NaCl(10mL)一起震荡,干燥(Na2SO4)并蒸发。该物质通过色谱在硅胶上以0–30%乙酸乙酯-己烷梯度纯化得到标题化合物(730mg,59%):1HNMR(400MHz,CDCl3)δ7.33(dd,J=7.7,1.1Hz,1H),7.18(d,J=0.9Hz,1H),6.77(d,J=7.8Hz,1H),6.25(q,J=5.0Hz,1H),1.66(d,J=4.9Hz,3H),1.32(s,12H);EIMSm/z262.
制备42:2-(苯并[d][1,3]氧硫杂环戊烯-5-基)-4,4,5,5-四甲基-1,3,2-二氧杂硼杂环戊烷
5-溴苯并[d][1,3]氧硫杂环戊烯(1.0g,4.6mmol,如Cabiddu,Salvatore;Cerioni,Giovanni;Cocco,MariaTeresa;Maccioni,Antonio;Plumitallo,Antonio,JournalofHeterocyclicChemistry1982,19,135-139中所描述的制备)溶解于无水四氢呋喃(12mL)中,冷却至-70℃,以n-BuLi(2.5M;1.9mL,4.8mmol)分份处理并于-70℃搅拌30min。添加4,4,5,5-四甲基-1,3,2-二氧杂硼杂环戊烷(900mg,4.8mmol)并持续搅拌1.5h,同时温度升温至-30℃。混合物以饱和NH4Cl(5mL)处理并以乙酸乙酯萃取(2x25mL)。合并的萃取物以饱和NaCl洗涤(10mL),干燥(Na2SO4)并蒸发得到标题化合物,其不经纯化而使用(1.2g,99%):1HNMR(400MHz,CDCl3)δ7.62(d,J=1.1Hz,1H),7.48(dd,J=8.0,1.3Hz,1H),6.82(d,J=8.1Hz,1H),5.69(s,2H),1.32(s,12H);EIMSm/z264.
制备43:2,2-二氟-5-甲氧基-6-硝基苯并[d][1,3]二氧杂环戊烯
2,2,5-三氟-6-硝基苯并[d][1,3]二氧杂环戊烯(2.5g,11mmol)溶解于无水甲醇(20mL),以30%甲醇钠溶液(3.1g,17mmol)处理,并于20℃搅拌1h。在过量的甲醇化物通过添加乙酸中和后,挥发物通过旋转蒸发除去。剩余物吸收于乙酸乙酯(50mL)中,以饱和NaHCO3(10mL)、饱和NaCl(10mL)洗涤,干燥(Na2SO4)并蒸发。该物质通过色谱在硅胶上以0–30%乙酸乙酯-己烷梯度纯化得到标题化合物,为白色固体(1.8g,70%):mp84–85℃.1HNMR(400MHz,CDCl3)δ7.71(s,1H),6.89(s,1H),3.98(s,3H);19FNMR(376MHz,CDCl3)δ-49.90(s);EIMSm/z233.
制备44:2,2-二氟-6-甲氧基苯并[d][1,3]二氧杂环戊烯-5-胺
2,2-二氟-5-甲氧基-6-硝基苯并[d][1,3]二氧杂环戊烯(1.7g,7.3mmol)溶解于乙酸乙酯(50mL)中并以5%钯/碳(200mg)和氢(40-50磅/平方英寸(psi))在振荡器上处理。90min后,催化剂通过过滤除去,溶剂通过蒸发除去并且产物经真空干燥,得到标题化合物,为棕色固体(1.5g,qt(定量)):1HNMR(400MHz,CDCl3)δ6.63(s,1H),6.50(s,1H),3.82(s,3H),3.76(d,J=23.0Hz,2H);19FNMR(376MHz,CDCl3)δ-50.32(s);EIMSm/z203.
制备45:2,2-二氟-5-碘-6-甲氧基苯并[d][1,3]二氧杂环戊烯
2,2-二氟-6-甲氧基苯并[d][1,3]二氧杂环戊烯-5-胺(1.4g,6.9mmol)溶解于二氯甲烷(5mL)中并分份添加至快速搅拌的浓HCl(75mL),形成松散的白色浆液。混合物冷却至0–5℃,并以亚硝酸钠(710mg,10mmol)在水(10mL)中分份处理。40min后,该混合物作为细流倒入碘化钠(3.1g,21mmol)在水(75mL)中的溶液,并且与二氯甲烷(50mL)一起快速搅拌。45min后,混合物与15%NaHSO3溶液(20mL)一起搅拌10min。分离的水相以二氯甲烷(30mL)萃取,并且合并的萃取物以饱和NaCl洗涤(15mL),干燥(Na2SO4)并蒸发。该物质通过色谱在硅胶上以0–15%乙酸乙酯-己烷梯度纯化得到标题化合物,为白色固体(1.8g,83%):mp50–51℃;1HNMR(400MHz,CDCl3)δ7.45(s,1H),6.69(s,1H),3.86(s,3H);19FNMR(376MHz,CDCl3)δ-49.81(s);EIMSm/z314.
制备46:2-(2,2-二氟-6-甲氧基苯并[d][1,3]二氧杂环戊烯-5-基)-4,4,5,5-四甲基-1,3,2-二氧杂硼杂环戊烷
2,2-二氟-5-碘-6-甲氧基苯并[d][1,3]二氧杂环戊烯(1.6g,5.0mmol)溶解于无水四氢呋喃(15mL)中,冷却至0–5℃并以异丙基氯化镁锂(1.3M;4.1mL,5.3mmol)分份处理。50min后,添加2-异丙氧基-4,4,5,5-四甲基-1,3,2-二氧杂硼杂环戊烷(1.0g,5.4mmol)并于15–20℃持续搅拌40min。混合物以饱和NH4Cl(10mL)处理并且然后与饱和NaCl(10mL)和乙酸乙酯(20mL)混合。有机相以饱和NaCl洗涤(10mL),干燥(Na2SO4)并蒸发得到标题化合物,为浓稠油状物,其不经进一步纯化而使用(1.4g,89%):1HNMR(400MHz,CDCl3)δ7.35(s,1H),6.65(s,1H),3.81(s,3H),1.34(s,12H);19FNMR(376MHz,CDCl3)δ-50.17(s);EIMSm/z314.
制备47:2-(6-氯-2,2-二氟苯并[d][1,3]二氧杂环戊烯-5-基)-4,4,5,5-四甲基-1,3,2-二氧杂硼杂环戊烷
5-溴-6-氯-2,2-二氟苯并[d][1,3]二氧杂环戊烯(1.0g,3.7mmol)溶解于无水四氢呋喃(7mL),冷却至0–5℃并以异丙基氯化镁氯化锂(1.3M;3.0mL,3.9mmol)分份处理。30min后,添加2-异丙氧基-4,4,5,5-四甲基-1,3,2-二氧杂硼杂环戊烷(730mg,4.0mmol),并于10–15℃持续搅拌45min。添加饱和NH4Cl(10mL),并且混合物与乙酸乙酯(20mL)和饱和NaCl(10mL)一起振荡。有机相以饱和NaCl洗涤(10mL),干燥(Na2SO4)并蒸发得到标题化合物,为白色固体(1.2g,qt):1HNMR(400MHz,DMSO-d6)δ7.64(s,1H),7.53(s,1H),1.30(s,12H);19FNMR(376MHz,DMSO-d6)δ-48.97(s);EIMSm/z318.
制备48:2-(7-甲氧基苯并[d][1,3]二氧杂环戊烯-5-基)-4,4,5,5-四甲基-1,3,2-二氧杂硼杂环戊烷
6-溴-4-甲氧基苯并[d][1,3]二氧杂环戊烯(1.5g,6.5mmol,如Shirasaka,Tadashi;Takuma,Yuki;Imaki,Naoshi.SyntheticCommunications1990,20,1223-1232所述制备)溶解于无水四氢呋喃(25mL),冷却至5℃并以异丙基氯化镁氯化锂(1.3M;5.2mL,6.8mmol)处理。于10℃50min后,将温度升温至40℃并搅拌5h。混合物冷却至20℃,并以2-异丙氧基-4,4,5,5-四甲基-1,3,2-二氧杂硼杂环戊烷(1.3g,7.1mmol)处理并搅拌3h。混合物以饱和NH4Cl(2mL)处理,接着以1MHCl(8mL)和乙酸乙酯(20mL)处理,并且然后搅拌10min。有机相以饱和NaCl洗涤(10mL),干燥(Na2SO4)并蒸发。该产物通过快速色谱以二氯甲烷纯化得到标题化合物,为白色固体(600mg;33%):mp86–88℃;1HNMR(400MHz,CDCl3)δ7.01(d,J=0.5Hz,1H),6.97(d,J=0.8Hz,1H),5.98(s,2H),3.93(s,4H),1.33(s,12H);EIMSm/z278.
制备49:6-溴-4-氟苯并[d][1,3]二氧杂环戊烯-2-硫酮
5-溴-3-氟苯-1,2-二醇(2.0g,9.7mmol,根据Lu,Hejun;Tang,PengCho;Chen,Yiqian;Wang,Shenglan;Wang,Hua;Zhang,Lei;Li,Jun,WO2011140936A1制备)溶解于氯仿(25mL)中,以硫光气(1.2g,11mmol)处理并冷却至0–5℃。滴加氢氧化钠(10%水溶液,8.9g,22mmol),伴随剧烈搅拌30min。1h后,真空除去氯仿并且通过添加6MHCl将pH调节至2。由此形成的固体吸收在乙酸乙酯(120mL)中,以饱和NaCl洗涤(30mL),干燥(Na2SO4)并蒸发。该物质通过快速色谱纯化使用0–30%乙酸乙酯-己烷梯度得到标题化合物,为褐色固体(1.5g,62%):mp41–42℃;1HNMR(400MHz,CDCl3)δ7.35–7.30(m,1H),7.29(d,J=1.6Hz,1H);19FNMR(376MHz,CDCl3)δ-128.93;EIMSm/z248/250.
制备50:6-溴-2,2,4-三氟苯并[d][1,3]二氧杂环戊烯
6-溴-4-氟苯并[d][1,3]二氧杂环戊烯-2-硫酮(6.9g,28mmol)溶解于无水二氯甲烷(150mL),冷却至-40℃并以氢氟酸吡啶盐(70重量%HF;39g,273mmol)处理。分份添加N-碘琥珀酰亚胺(19g,84mmol),同时保持温度低于-30℃。混合物于-35~-0℃搅拌30min并且然后升温至20℃并搅拌30min。施加外部冷却保持温度低于35℃,混合物以NaHSO3(8g)在水(50mL)中的溶液分份处理并搅拌15min。混合物以额外的水(200mL)处理来溶解固体。有机相以饱和NaCl洗涤(30mL),干燥(Na2SO4)。大部分溶剂通过大气压蒸馏经过7盘Oldershaw柱除去,并且当釜体积为约50mL时,持续蒸馏经过200mmVigreux柱直到顶部温度达到75℃。冷却至环境温度后,将压力降低至50mmHg并且产品经顶部于75-80℃通过简单蒸馏头取出,得到标题化合物,为淡粉色液体(5.3g,74%):1HNMR(400MHz,CDCl3)δ7.11(dd,J=9.0,1.7Hz,1H),7.07(m,1H);19FNMR(376MHz,CDCl3)δ-49.56,-132.65;EIMSm/z254.
制备51:4,4,5,5-四甲基-2-(2,2,7-三氟苯并[d][1,3]二氧杂环戊烯-5-基)-1,3,2-二氧杂硼杂环戊烷
6-溴-2,2,4-三氟苯并[d][1,3]二氧杂环戊烯(2.0g,7.8mmol)溶解于无水四氢呋喃(10mL),冷却至-5至0℃并以异丙基氯化镁氯化锂复合物(1.3M;6.3mL,8.2mmol)分份处理。除去冷却浴并且搅拌混合物30min。添加2-异丙氧基-4,4,5,5-四甲基-1,3,2-二氧杂硼杂环戊烷(1.6g,8.4mmol),搅拌混合物1h并且然后以饱和NH4Cl(5mL)处理。混合物以乙酸乙酯(40mL)和饱和NaCl(10mL)稀释并且pH通过添加HCl调节至2。有机相以饱和NaCl洗涤(5mL),干燥(Na2SO4)并蒸发得到标题化合物,其不经进一步纯化而使用(2g,85%):1HNMR(400MHz,CDCl3)δ7.36(d,J=9.8Hz,1H),7.29(d,J=6.5Hz,1H),1.33(s,12H);19FNMR(376MHz,CDCl3)δ-49.79,-136.26;EIMSm/z302.
制备52:3-溴-6-氟苯-1,2-二醇
3-溴-6-氟-2-羟基苯甲醛(9.0g,41mmol,根据Castro,AlfredC.;Depew,KristopherM.;Grogan,MichaelJ.;Holson,EdwardB.;Hopkins,BrianT.;Johannes,CharlesW.;Keaney,GreggF.;Koney,NiiO.;Liu,Tao;Mann,DavidA.;Nevalainen,Marta;Peluso,Stephane;Perez,LawrenceBlas;Snyder,DanielA.;Tibbitts,ThomasT.,WO2008024337A2制备)在1.0MNaOH(47mL)中搅拌并以过氧化氢(6%;49g,86mmol)处理。施加外部冷却以保持温度控制在低于50℃。2h彻底搅拌后,混合物与NaHSO3在50mL水中的溶液一起搅拌并以乙酸乙酯(2x75mL)萃取。合并的萃取物以饱和NaCl洗涤(20mL),干燥(Na2SO4)并蒸发。儿茶酚衍生物,为深橙色液体,不经进一步纯化用于后续步骤(8.9g,qt):EIMSm/z206.
制备53:4-溴-7-氟苯并[d][1,3]二氧杂环戊烯-2-硫酮
3-溴-6-氟苯-1,2-二醇(8.9g,43mmol)溶解于氯仿(100mL)中,冷却至0–5℃并以硫光气(5.4g,47mmol)处理。经30min分份添加氢氧化钠水溶液(10wt%;40g,99mmol),伴随剧烈搅拌。于5–15℃持续搅拌60min,并且然后通过旋转蒸发除去大部分氯仿。通过添加1MHCl将pH调节至2并且沉淀的硫酮吸收在乙酸乙酯(150mL)中。有机相以水(25mL)、饱和NaCl(25mL)洗涤、干燥(Na2SO4)并蒸发。粗产物通过快速色谱纯化,以0–20%乙酸乙酯-己烷梯度洗脱得到标题化合物,为褐色固体(6.2g,58%):mp72–76℃;1HNMR(400MHz,CDCl3)δ7.40(dd,J=9.2,4.1Hz,1H),7.04(t,J=9.1Hz,1H);19FNMR(376MHz,CDCl3)δ-132.68;EIMSm/z248.
制备54:4-溴-2,2,7-三氟苯并[d][1,3]二氧杂环戊烯
4-溴-7-氟苯并[d][1,3]二氧杂环戊烯-2-硫酮(6.1g,25mmol)溶解于无水二氯甲烷(100mL)中,冷却至-30~-40℃并以氢氟酸吡啶盐(70wt%;35g,245mmol)处理。于-25~-35℃分份添加N-碘琥珀酰亚胺并且让混合物升温至20℃并搅拌2h。深色混合物冷却至0℃并以15%NaHSO3溶液(30mL)处理,伴随搅拌。20min后,混合物以二氯甲烷(75mL)和水(200mL)稀释以溶解固体。有机相以饱和NaCl洗涤(25mL)并干燥(Na2SO4)。通过大气压蒸馏经过450mmVigreux柱除去溶剂。产物于30-40mmHg在80-90℃引出,得到标题化合物,为澄清液体(3.0g,47%):1HNMR(400MHz,CDCl3)δ7.18(dd,J=9.3,4.2Hz,1H),6.85(t,J=9.3Hz,1H);19FNMR(376MHz,CDCl3)δ-49.08,-136.17;EIMSm/z254.
制备55:4,4,5,5-四甲基-2-(2,2,7-三氟苯并[d][1,3]二氧杂环戊烯-4-基)-1,3,2-二氧杂硼杂环戊烷
4-溴-2,2,7-三氟苯并[d][1,3]二氧杂环戊烯(2.0g,7.8mmol)溶解于无水四氢呋喃(12ml)中,冷却至-5℃并以异丙基氯化镁氯化锂复合物(1.3M;6.3mL,8.2mmol)处理。混合物于5至15℃搅拌2h,以2-异丙氧基-4,4,5,5-四甲基-1,3,2-二氧杂硼杂环戊烷(1.6g,8.4mmol)处理并于10至20℃搅拌2h。混合物以饱和NH4Cl(5mL)处理,搅拌10min并且然后以1MHCl(10mL)和乙酸乙酯(75mL)振荡。有机相以饱和NaCl洗涤(10mL),干燥(Na2SO4)并蒸发得到标题化合物,为白色固体(2.3g,98%):1HNMR(400MHz,CDCl3)δ7.41(dd,J=8.7,5.3Hz,1H),6.88(dd,J=9.5,8.8Hz,1H),1.36(s,12H);19FNMR(376MHz,CDCl3)δ-49.07,-131.31;EIMSm/z302.
制备56:(2,2-二氟-7-(4,4,5,5-四甲基-1,3,2-二氧杂硼杂环戊烷-2-基)苯并[d][1,3]二氧杂环戊烯-4-基)三甲基硅烷
(2,2-二氟苯并[d][1,3]二氧杂环戊烯-4-基)三甲基硅烷(5.0g,22mmol,如Gorecka,Joanna;Leroux,Frederic;Schlosser,Manfred,EuropeanJournalofOrganicChemistry2004,1,64-68中所描述的制备)添加至仲-BuLi(1.4M;10mL,14mmol)在无水四氢呋喃(28mL)中的冷却至-75℃的搅拌溶液。于-75℃2h,添加2-异丙氧基-4,4,5,5-四甲基-1,3,2-二氧杂硼杂环戊烷(4.2g,23mmol),并且于-75℃搅拌混合物90min。混合物以饱和NH4Cl(5mL)处理并温热至20℃。混合物与水(75mL)混合,以6MHCl酸化并以二乙醚(100mL)萃取。有机相以饱和NaCl洗涤(15mL),干燥(Na2SO4)并蒸发得到标题化合物(估计纯度为60%),其不经纯化而使用:1HNMR(400MHz,CDCl3)δ7.39(d,J=7.5Hz,1H),7.07(d,J=7.5Hz,1H),1.36(s,,12H),0.33(s,9H);19FNMR(376MHz,CDCl3)δ-49.33;EIMSm/z356.
制备57:4-溴-5-氟苯-1,2-二醇
向在50mL圆底烧瓶中的CH2Cl2(30mL)添加4-溴-5-氟-2-甲氧基苯酚(2g,9.05mmol)。反应混合物在冰/水浴中冷却至0℃。经由注射器经5min缓慢地添加三溴化硼(1.027mL,10.86mmol),并且除去冰/水浴。让反应混合物升温至室温并搅拌18h。反应混合物置于冰/水浴并且经由注射器缓慢地添加甲醇(30mL)。除去冰/水浴后,反应混合物升温至室温。反应混合物转移至分液漏斗,以乙酸乙酯(200mL)稀释并以水(200mL)洗涤。有机层经Na2SO4干燥并过滤。浓缩有机溶液得到4-溴-5-氟苯-1,2-二醇,为深棕色油状物(1.8g,96%):1HNMR(400MHz,CDCl3)δ7.03(d,J=6.5Hz,1H),6.72(dd,J=8.3,3.5Hz,1H);19FNMR(376MHz,CDCl3)δ-115.91(s);ESIMSm/z207([M+H]+),206([M-H]-).
制备58:5-溴-6-氟苯并[d][1,3]二氧杂环戊烯
向在50mL烧瓶中的N,N-二甲基甲酰胺(25mL)添加4-溴-5-氟苯-1,2-二醇(2g,9.66mmol)、碳酸铯(4.72g,14.49mmol)和溴氯甲烷(1.875g,14.49mmol)。反应混合物于室温搅拌1h并且然后加热至80℃的外部温度保持3h。冷却后,反应混合物以Et2O(75mL)稀释并以水洗涤(50mL),接着以饱和NaCl溶液洗涤(50mL)。有机层经MgSO4干燥并过滤。浓缩有机溶液得到5-溴-6-氟苯并[d][1,3]二氧杂环戊烯,为浅橙色固体(1.8g,85%):1HNMR(400MHz,CDCl3)δ6.94(d,J=5.9Hz,1H),6.67(d,J=7.9Hz,1H),6.00(s,2H);19FNMR(376MHz,CDCl3)δ-113.82(s);ESIMSm/z220([M+H]+),218([M-H]-).
制备59:5-溴-2,2-二甲基苯并[d][1,3]二氧杂环戊烯
向在250mL圆底烧瓶中的苯(50mL)添加4-溴苯-1,2-二醇(1g,5.29mmol)、2,2-二甲氧基丙烷(2.204g,21.16mmol)和对苯磺酸一水合物(0.050g,0.265mmol)。烧瓶配有Dean-Stark分离器并加热至回流保持18h。冷却后,反应混合物转移至分液漏斗并以2NNaOH溶液(100mL)和饱和NaCl溶液(100mL)洗涤。有机层经MgSO4干燥,过滤,并浓缩得到5-溴-2,2-二甲基苯并[d][1,3]二氧杂环戊烯,为深棕色油状物(767mg,63%):1HNMR(400MHz,CDCl3)δ6.91–6.85(m,2H),6.62–6.57(m,1H),1.66(s,6H);13CNMR(101MHz,CDCl3)δ146.81(s),144.25(s),123.64(s),121.02(s),112.05(s),109.40(s),108.46(s),25.83(s);ESIMSm/z230([M+H]+),228([M-H]-).
制备60:2-(2,2-二甲基苯并[d][1,3]二氧杂环戊烯-5-基)-4,4,5,5-四甲基-1,3,2-二氧杂硼杂环戊烷
向DMSO(10mL)添加乙酸钾(1.671g,17.03mmol)、4,4,4',4',5,5,5',5'-八甲基-2,2'-二(1,3,2-二氧杂硼杂环戊烷)(1.729g,6.81mmol)、5-溴-2,2-二甲基苯并[d][1,3]二氧杂环戊烯(1.3g,5.68mmol)和PdCl2(dppf)(0.415g,0.568mmol)。将反应加热至外部温度80℃保持18h。冷却后,反应混合物倒入冰水(50mL)。冰水混合物转移至分液漏斗并以乙酸乙酯(50mL)完成两次萃取。合并有机层,经Na2SO4干燥,并过滤。溶液使用乙酸乙酯作为溶液浓缩至5g的上。浸润的Celite装载至TeledyneIsco纯化体系上并通过硅胶色谱纯化使用0–30%乙酸乙酯:己烷得到2-(2,2-二甲基苯并[d][1,3]二氧杂环戊烯-5-基)-4,4,5,5-四甲基-1,3,2-二氧杂硼杂环戊烷,为红色半固体(767mg,49%):1HNMR(400MHz,CDCl3)δ7.31(dt,J=6.6,3.3Hz,1H),7.15(s,1H),6.74(d,J=7.7Hz,1H),1.66(s,6H),1.32(s,12H);13CNMR(101MHz,CDCl3)δ129.21(s),113.78(s),108.15(s),83.59(s),25.86(s),24.82(s);ESIMSm/z277([M+H]+),275([M-H]-).
制备61:2-(6-氟苯并[d][1,3]二氧杂环戊烯-5-基)-4,4,5,5-四甲基-1,3,2-二氧杂硼杂环戊烷
2-(6-氟苯并[d][1,3]二氧杂环戊烯-5-基)-4,4,5,5-四甲基-1,3,2-二氧杂硼杂环戊烷如制备60中所描述的从5-溴-6-氟苯并[d][1,3]二氧杂环戊烯制备,得到棕色油状物(74%):1HNMR(400MHz,CDCl3)δ7.08(d,J=4.6Hz,1H),6.55(t,J=6.4Hz,1H),5.97(d,J=2.1Hz,2H),1.24(s,12H);13CNMR(101MHz,CDCl3)δ131.70,131.37,128.34,113.38,101.93,98.12,97.80,83.51,24.80;ESIMSm/z267([M+H]+),265([M-H]-).
制备62:2-(2,2-二氟苯并[d][1,3]二氧杂环戊烯-5-基)-4,4,5,5-四甲基-1,3,2-二氧杂硼杂环戊烷
在氮气下向烘干的三颈圆底烧瓶添加5-溴-2,2-二氟苯并[d][1,3]二氧杂环戊烯(2.516g,10.6mmol)和无水四氢呋喃(26mL)。将溶液冷却至0℃。缓慢地添加异丙基氯化镁-氯化锂复合物(1.3M;10mL,13.0mmol)并搅拌1h。添加2-异丙氧基-4,4,5,5-四甲基-1,3,2-二氧杂硼杂环戊烷(2.2mL,10.62mmol),并且搅拌反应混合物1h。反应以饱和氯化铵水溶液淬灭并以乙酸乙酯萃取三次。合并的有机层以盐水洗涤并经无水硫酸镁干燥。溶液经过滤并浓缩,得到2-(2,2-二氟苯并[d][1,3]二氧杂环戊烯-5-基)-4,4,5,5-四甲基-1,3,2-二氧杂硼杂环戊烷,为黄色油状物(2.54g,84%):1HNMR(400MHz,CDCl3)δ7.56(dd,J=8.0,1.0Hz,1H),7.47(d,J=0.6Hz,1H),7.06(dd,J=7.9,0.4Hz,1H),1.34(s,12H);19FNMR(376MHz,CDCl3)δ-50.18;EIMSm/z284.
制备63:2-(苯并[d][1,3]二氧杂环戊烯-4-基)-4,4,5,5-四甲基-1,3,2-二氧杂硼杂环戊烷
苯并[d][1,3]二氧杂环戊烯(3.05g,25mmol)溶解于四氢呋喃(50mL)并使用四氢呋喃/液氮浴冷却至-108℃。滴加仲丁基锂(1.4M在己烷中;19.64mL,27.5mmol),保持温度低于-100℃。然后.反应混合物于-100℃至-108℃的温度搅拌2h,确保完全去质子化。然后将2-异丙氧基-4,4,5,5-四甲基-1,3,2-二氧杂硼杂环戊烷(4.65g,25.00mmol)滴加至反应混合物,保持温度低于-100℃。反应混合物然后升温至室温并在二乙醚和水之间分配。有机相再以水萃取一次并且合并水相并以HCl酸化至pH4。产物以二乙醚萃取并且有机相经干燥并真空浓缩。产物通过快速色谱(硅胶)纯化,得到标题化合物,为白色固体(2.14g,34.5%):1HNMR(300MHz,CDCl3)δ7.21(dd,J=7.6,1.4Hz,1H),6.90(dd,J=7.7,1.5Hz,1H),6.82(t,J=7.6Hz,1H),6.02(s,2H),1.36(s,12H);EIMSm/z248.
制备64:2-(2,2-二氟苯并[d][1,3]二氧杂环戊烯-4-基)-4,4,5,5-四甲基-1,3,2-二氧杂硼杂环戊烷
2,2-二氟苯并[d][1,3]二氧杂环戊烯(6g,38.0mmol)溶解于四氢呋喃(100mL)中并冷却至-75℃。滴加仲丁基锂(1.4M在环己烷中;29.8mL,41.7mmol),保持温度低于-65℃。然后于-75℃搅拌反应混合物1h,确保完全脱质子化。然后将2-异丙氧基-4,4,5,5-四甲基-1,3,2-二氧杂硼杂环戊烷(7.06g,38.0mmol)滴加至反应混合物,保持温度低于-65℃。然后将反应混合物升温至室温并于室温静置2h,然后在二乙醚和水之间分配。水相然后以12NHCl酸化至pH3。产物以二乙醚萃取并且有机相经干燥并真空浓缩,得到标题化合物,为灰白色固体(7.06g,65.5%):1HNMR(300MHz,CDCl3)δ7.43(dd,J=7.5,1.5Hz,1H),7.13(dd,J=7.9,1.5Hz,1H),7.05(t,J=7.7Hz,1H),1.37(s,12H);EIMSm/z284.
制备65:4-氯-2,2-二氟苯并[d][1,3]二氧杂环戊烯
2,2-二氟苯并[d][1,3]二氧杂环戊烯(6.3g,39.8mmol)溶解于四氢呋喃(66mL)中并冷却至-78℃。滴加正丁基锂(2.5M溶液在己烷中;16.74mL,41.8mmol),保持温度低于-70℃。反应混合物然后于-78℃搅拌1h以确保完全脱质子化。将1,2,2-三氟三氯乙烷(14.93g,80mmol)溶解于四氢呋喃(33mL)中并冷却至-65℃。将该锂化物经由导管转移至1,2,2-三氟三氯乙烷的溶液中,转移速率允许温度在添加期间保持在-60℃至-65℃之间。反应混合物然后升温至室温并且在二乙醚和水之间分配。有机相经浓缩并且产物通过100g的硅胶使用己烷作为溶剂快速色谱纯化,得到标题化合物,为澄清油状物(5.74g,74.8%):1HNMR(400MHz,CDCl3)δ7.08(dd,J=8.2,1.4Hz,1H),7.03(t,J=8.0Hz,1H),6.97(dd,J=7.9,1.5Hz,1H);EIMSm/z192.
制备66:2-(7-氯-2,2-二氟苯并[d][1,3]二氧杂环戊烯-4-基)-4,4,5,5-四甲基-1,3,2-二氧杂硼杂环戊烷
4-氯-2,2-二氟苯并[d][1,3]二氧杂环戊烯(3g,15.58mmol)溶解于四氢呋喃(50mL)中并冷却至-75℃。滴加正丁基锂(2.5M在己烷中;6.86mL,17.14mmol),保持温度低于-65℃。反应混合物然后于-75℃搅拌1h以确保完全脱质子化。然后将2-异丙氧基-4,4,5,5-四甲基-1,3,2-二氧杂硼杂环戊烷(3.19g,17.14mmol)滴加至反应混合物,保持温度低于-65℃。然后让反应混合物升温至室温,添加至二乙醚(200mL)并以水(2x100mL)萃取。合并水相并且以浓HCl酸化至pH4。产物以二乙醚萃取并且有机相经干燥并真空浓缩,得到标题化合物,为灰白色固体(3.82g,77%):1HNMR(400MHz,CDCl3)δ7.38(d,J=8.4Hz,1H),7.06(d,J=8.4Hz,1H),1.36(s,12H);EIMSm/z318.
制备67:2-(2,2-二氟苯并[d][1,3]二氧杂环戊烯-5-基)-4,4,5,5-四甲基-1,3,2-二氧杂硼杂环戊烷
向5-溴-2,2-二氟苯并[d][1,3]二氧杂环戊烯(1.5g,6.3mmol)在N,N-二甲基甲酰胺(12.7mL)中的溶液添加4,4,4',4',5,5,5',5'-八甲基-2,2'-双(1,3,2-二氧杂硼杂环戊烷)(1.6g,6.3mmol)、乙酸钾(1.9g,19.0mmol)和(1,1'-双(二苯基膦基)二茂铁)-二氯钯(II)(0.3g,0.32mmol)。反应混合物于80℃加热18h,然后反应混合物以Et2O稀释并以水洗涤。分离有机层,经Na2SO4干燥,过滤,真空浓缩,并且通过硅胶色谱纯化以0–100%丙酮/己烷洗脱,得到棕色油状物(0.9g,50%):1HNMR(400MHz,DMSO-d6)δ7.55(d,J=8.0Hz,1H),7.53(s,1H),7.43(d,J=8.0Hz,1H),1.30(s,12H);19FNMR(376MHz,DMSO-d6)δ-49.26(s);EIMSm/z284.
制备68:乙酸2,3-二氢-1H-茚-2-基酯
于0℃在氮气氛下将乙酰氯(87.86g,1119.40mmol)滴加至2,3-二氢-1H-茚-2-醇(15g,111.94mmol)。反应混合物在室温搅拌16h。过量的乙酰氯经减压蒸馏除去。剩余物以乙酸乙酯稀释(450mL),以NaHCO3饱和溶液(3x50mL)、盐水(30mL)洗涤,经Na2SO4干燥并减压浓缩得到标题化合物(16.2g,82%),其不经进一步纯化用于后续步骤。
制备69:乙酸5-溴-2,3-二氢-1H-茚-2-基酯
向乙酸2,3-二氢-1H-茚-2-基酯(16g,90.09mmol)在无水DMF(160mL)中的0℃溶液分份添加N-溴琥珀酰亚胺(17.8g,99.09mmol),并且混合物于室温搅拌48h。反应混合物然后以乙酸乙酯(450mL)稀释,以冰冷的水(4x50mL)和盐水(100mL)洗涤,经Na2SO4干燥并减压浓缩。剩余物通过柱色谱使用乙酸乙酯/己烷(硅胶,100-200筛目)纯化得到标题化合物(9.8g,42%)。
制备70:5-溴-2,3-二氢-1H-茚-2-醇
向乙酸5-溴-2,3-二氢-1H-茚-2-基酯(9g,35.43mmol)在THF(100mL)中的0℃溶液滴加NaOH(2.12g,53.15mmol)在水(25mL)中的溶液。反应混合物在室温搅拌16h。反应混合物然后经浓缩,以6NHCl溶液中和并以乙酸乙酯萃取(2x50mL)。合并的有机层以盐水洗涤(50mL),经Na2SO4干燥并减压浓缩。剩余物通过柱色谱纯化(乙酸乙酯/己烷,硅胶100-200筛目)得到标题化合物(4.5g,56%)。
制备71:5-(4,4,5,5-四甲基-1,3,2-二氧杂硼杂环戊烷-2-基)-2,3-二氢-1H-茚-2-醇
向5-溴-2,3-二氢-1H-茚-2-醇(4.5g,21.22mmol)在二噁烷(54mL)中的溶液添加联硼酸频那醇酯(6.44g,25.47mmol)和乙酸钾(8.3g,84.90mmol)。反应混合物以氩气冲洗20min然后添加Pd(dppf)Cl2(0.755g,1.061mmol)。反应混合物于110℃搅拌4h,然后冷却至室温,经短垫过滤并以乙酸乙酯洗涤(100mL)。滤液经减压浓缩。剩余物通过柱色谱纯化(乙酸乙酯/己烷,硅胶100-200筛目)得到标题化合物(3.8g,69%)。
式(I)化合物的合成
实施例1:4-氨基-3-氯-6-(1,3-二氢异苯并呋喃-5-基)-5-氟吡啶-2-甲酸甲基酯
于23℃将叔丁基亚硝酸酯(1.3mL,11mmol,1.5当量)添加至过苯甲酸酸酐(36mg,0.15mmol,0.02当量)、联硼酸频哪醇酯(1.9g,7.4mmol,1.0当量)和1,3-二氢异苯并呋喃-5-胺(1.0g,7.4mmol,1.0当量)在乙腈(25mL)中的搅拌溶液中。所得均匀的橙色/棕色溶液于23℃搅拌3h。添加活性碳并且黑色混合物经重力过滤并通过旋转蒸发浓缩得到1.9g深棕色油状物,其表现为与2-(1,3-二氢异苯并呋喃-5-基)-4,4,5,5-四甲基-1,3,2-二氧杂硼杂环戊烷(~30%纯度)一致,通过粗品1HNMR分析。
于23℃向粗的2-(1,3-二氢异苯并呋喃-5-基)-4,4,5,5-四甲基-1,3,2-二氧杂硼杂环戊烷(估计为570mg,2.3mmol,1.1当量)添加至4-氨基-3,6-二氯-5-氟吡啶-2-甲酸甲基酯(500mg,2.1mmol,1.0当量)、二氯[双(三苯基膦基)]-钯(II)(150mg,0.21mmol,0.10当量)和碳酸钠(240mg,2.3mmol,1.1当量),接着添加水:乙腈(7.0mL)的1:1混合物。所得深橙色/棕色混合物加热至85℃并搅拌4h。冷却的反应混合物以水稀释(150mL)并以二氯甲烷萃取(4x70mL)。合并的有机层经干燥(硫酸镁),重力过滤,并通过旋转蒸发浓缩。剩余物通过反相色谱纯化(5%乙腈至100%乙腈梯度)得到标题化合物,为橙色粉末(150mg,22%):mp153–156℃;IR(纯膜)3468(m),3334(s),3205(m),2952(m),2856(m),1735(s),1623(s),1579(w)cm-1;1HNMR(400MHz,CDCl3)δ7.81–7.86(m,2H),7.33(d,J=8Hz,1H),5.16(brd,J=4Hz,1H),4.89(brs,2H),3.97(s,3H);ESIMSm/z323[(M+H)+].
实施例2(偶联1):4-氨基-6-(苯并[d][1,3]二氧杂环戊烯-4-基)-3-氯-5-氟吡啶-2-甲酸甲基酯
4-氨基-3,6-二氯-5-氟吡啶-2-甲酸甲基酯(1.5g,6.28mmol)、2-(苯并[d][1,3]二氧杂环戊烯-4-基)-4,4,5,5-四甲基-1,3,2-二氧杂硼杂环戊烷(2.024g,8.16mmol)、氟化钾(0.875g,15.06mmol;注:相关的实施例使用氟化铯)和双(三苯基膦)氯化钯(II)(0.440g,0.628mmol)混合于乙腈(13mL)和水(4.5mL)中。反应混合物然后在微波中于110℃于封盖小瓶中受辐照20min,以外部IR-传感器从容器外侧监控温度。冷却的反应混合物在乙酸乙酯和水之间分配。有机相经干燥并浓缩至1.2g的硅胶上。该混合物施用至硅胶柱顶部并且产物以7–60%己烷/乙酸乙酯梯度溶剂体系洗脱得到标题化合物,为白色固体(1.4g,68.7%):mp146–148℃;1HNMR(400MHz,CDCl3)δ7.16–7.09(m,1H),6.98–6.85(m,2H),6.01(s,2H),4.91(brs,2H),3.98(s,3H);ESIMSm/z325([M+H]+).
在该实施例中使用的制备方法在表2中称为“偶联1”。
实施例3(偶联2):4-氨基-3-氯-6-(2,2,4-三氟苯并-[d][1,3]二氧杂环戊烯-5-基)吡啶-2-甲酸甲基酯
4-乙酰胺基-3,6-二氯吡啶-2-甲酸甲基酯(600mg,2.3mmol)、氟化铯(690mg,4.5mmol)、4,4,5,5-四甲基-2-(2,2,4-三氟苯并[d][1,3]二氧杂环戊烯-5-基)-1,3,2-二氧杂硼杂环戊烷(980mg,3.0mmol)和双(三苯基膦)氯化钯(II)(110mg,0.16mmol)合并于1:1乙腈-水(6mL)中并经由微波(BiotageInitiator)于115℃加热30min,以外部IR-传感器从容器外侧监控温度。混合物以水(10mL)和乙酸乙酯(25mL)振荡。有机相以饱和NaCl洗涤(5mL),经Na2SO4干燥并蒸发。剩余物通过色谱在硅胶上以5–30%乙酸乙酯-己烷纯化得到固体,其经反相高效液相色谱进一步纯化以70/30/0.10v/v/v乙腈/水/乙酸洗脱得到250mg的酰胺。该物质溶解于甲醇(10mL),以乙酰氯(2mL)小心地处理并且于回流加热1h。冷却后,挥发物经真空除去并且剩余物以乙酸乙酯(15mL)和饱和NaHCO3(5mL)溶液搅拌15min。有机相以饱和NaCl溶液洗涤(5mL),经Na2SO4干燥并真空蒸发得到标题化合物,为白色固体(195mg,24%):mp153–155℃;1HNMR(400MHz,CDCl3)δ7.77(dd,J=8.6,7.1Hz,1H),7.14(d,J=1.9Hz,1H),6.97(dd,J=8.6,0.9Hz,1H),4.87(s,2H),4.00(s,3H);19FNMR(376MHz,CDCl3)δ-49.37(s),-138.91(s);ESIMSm/z361([M+H]+),359([M-H]-).
在该实施例中使用的制备方法在表2中称为“偶联2”。
实施例4(偶联3):4-氨基-3-氯-6-(2,3-二氢苯并呋喃-6-基)-5-氟吡啶-2-甲酸甲基酯
三苯磺酸3,3',3”-膦三基酯(0.209g,0.418mmol)、氟化钾(0.365g,6.28mmol)、4-氨基-3-氯-6-(2,3-二氢苯并呋喃-6-基)-5-氟吡啶-2-甲酸甲基酯、二乙氧基钯(0.047g,0.209mmol)和2-(2,3-二氢苯并呋喃-6-基)-4,4,5,5-四甲基-1,3,2-二氧杂硼杂环戊烷(0.541g,2.196mmol)混合于5-mL微波小瓶中。混合水(比率:3.00,体积:3mL)和乙腈(比例:1.000,体积:1mL)并且然后添加至微波小瓶中。反应小瓶经封盖并且置于BiotageInitiator微波反应器中于150℃保持6min,以外部IR-传感器从容器外侧监控温度。冷却后,产物作为固体沉淀。另外的物质存在于乙腈混合物中。固体以水洗涤并干燥得到4-氨基-3-氯-6-(2,3-二氢苯并呋喃-6-基)-5-氟吡啶-2-甲酸甲基酯,为白色固体(250mg,37%):mp150–154℃;1HNMR(400MHz,CDCl3)δ7.42(dt,J=7.7,1.6Hz,1H),7.33(s,1H),7.28(s,1H),4.88(s,2H),4.62(q,J=8.4Hz,2H),3.98(d,J=3.0Hz,3H),3.31–3.18(m,2H);13CNMR(101MHz,CDCl3)δ164.99,160.32,147.23,144.65,140.38,140.24,134.32,134.26,128.69,124.76,121.43,121.37,114.64,109.71,109.65,71.39,52.90,29.69;ESIMSm/z233([M+H]+),231([M-H]-).
在该实施例中使用的制备方法在表2中称为“偶联3".
实施例5(偶联4):4-氨基-3-氯-6-(2,2,5-三氟苯并[d][1,3]二氧杂环戊烯-4-基)吡啶-2-甲酸甲基酯
4-乙酰胺基-3-氯-6-(三甲基甲锡烷基)吡啶-2-甲酸甲基酯(710mg,1.8mmol)和2,2,5-三氟-4-碘苯并[d][1,3]二氧杂环戊烯(500mg,1.7mmol)混合于无水N,N-二甲基甲酰胺(7mL)中并以氮气流排气25min。添加双(三苯基膦)-氯化钯(II)(120mg,0.17mmol)和碘化亚铜(32mg,0.17mmol)并将混合物加热至80℃保持5h。混合物与乙酸乙酯(30mL)和水(15mL)混合并且分开的有机相以水(10mL)、饱和NaCl(10mL)洗涤,干燥并蒸发。剩余物通过色谱在硅胶上以0–50%乙酸乙酯-己烷梯度纯化得到115mg的酰胺中间体。该物质溶解于甲醇(25mL),以乙酰氯处理(3–4mL)并加热至60℃保持2h。挥发物经真空除去并且剩余物与饱和NaHCO3(10mL)和乙酸乙酯(20mL)一起搅拌30min。分离有机相,以饱和NaCl洗涤(5mL),干燥(Na2SO4),蒸发得到标题化合物,为白色固体(130mg,20%):1HNMR(400MHz,DMSO-d6)δ7.52(dd,J=8.9,4.0Hz,1H),7.22(dd,J=11.0,9.0Hz,1H),7.06(d,J=1.4Hz,1H),6.99(s,2H),3.88(s,3H);19FNMR(376MHz,DMSO-d6)δ-48.09,-121.60;ESIMSm/z361([M+H]+),359([M-H]-).
在该实施例中使用的制备方法在表2中称为“偶联4”。
实施例6(偶联5):4-氨基-5-氟-3-甲氧基-6-(2,2,6-三氟苯并[d][1,3]二氧杂环戊烯-5-基)吡啶-2-甲酸甲基酯
向4-氨基-6-氯-5-氟-3-甲氧基吡啶-2-甲酸甲基酯(300mg,1.279mmol)在乙腈(1mL)和水(3mL)中的混合物添加氟化钾(149mg,2.56mmol)、乙酸钯(II)(28.7mg,0.128mmol)和三(3-磺酸基苯基)膦四水合物,钠盐(150mg,0.256mmol)。反应混合物然后于120℃在微波反应器中加热20min。冷却的反应混合物然后以二氯甲烷稀释并以水洗涤。分离各相并且浓缩有机物。剩余物通过反相色谱纯化(100gC18)以50/50乙腈-水(0.1%三氟乙酸)洗脱,得到标题化合物,为灰白色固体(251mg,52.5%)。
在该实施例中使用的制备方法在表2中称为“偶联5”。
实施例7:4-氨基-6-(7-溴-2,2-二氟苯并[d][1,3]二氧杂环戊烯-4-基)-3-氯-5-氟吡啶-2-甲酸甲基酯
4-氨基-3-氯-6-(2,2-二氟-7-(三甲基甲硅烷基)苯并[d][1,3]二氧杂环戊烯-4-基)-5-氟吡啶-2-甲酸甲基酯(400mg,0.92mmol)于1,2-二氯乙烷(5mL)中搅拌,以溴(1.0g,6.5mmol)处理并于20–25℃搅拌4h。溶液以10%NaHSO3溶液(30mL)搅拌并以乙酸乙酯萃取(35mL)。有机相以饱和NaCl洗涤(5mL),干燥(Na2SO4)并蒸发得到标题化合物,为白色固体(370mg,92%):mp168–170℃;1HNMR(400MHz,CDCl3)δ7.35(m,1H),5.02(s,1H),3.99(s,3H);19FNMR(376MHz,CDCl3)δ-49.23,-137.58;ESIMSm/z439([M+H]+),437([M-H]-).
实施例8:4-氨基-3-氯-6-(2,2-二氟-7-碘苯并-[d][1,3]二氧杂环戊烯-4-基)-5-氟吡啶-2-甲酸甲基酯
在1,2-二氯乙烷(5mL)中的4-氨基-3-氯-6-(2,2-二氟-7-(三甲基甲硅烷基)苯并[d][1,3]二氧杂环戊烯-4-基)-5-氟吡啶-2-甲酸甲基酯(400mg,0.92mmol)以一氯化碘(900mg,5.5mmol)处理并于20℃搅拌20h。混合物与10wt%NaHSO3溶液(30mL)和乙酸乙酯(30mL)混合。水相以乙酸乙酯萃取(15mL),并且合并的有机相以饱和NaCl(10mL)洗涤,干燥(Na2SO4)并蒸发得到标题化合物,为白色固体(430mg,96%):mp156–159℃;1HNMR(400MHz,CDCl3)δ7.50(d,J=8.6Hz,1H),7.23(d,J=8.6Hz,1H),5.02(s,2H),3.99(s,3H);19FNMR(376MHz,CDCl3)δ-49.22,-137.49;ESIMSm/z487([M+H]+),485([M-H]-).
实施例9(水解):4-氨基-6-(苯并[d][1,3]二氧杂环戊烯-4-基)-3-氯-5-氟吡啶-2-甲酸
向含有4-氨基-6-(苯并[d][1,3]二氧杂环戊烯-4-基)-3-氯-5-氟吡啶-2-甲酸甲基酯(0.150g,0.462mmol)的反应小瓶添加甲醇(9.24mL)和2N氢氧化钠(0.924mL,1.848mmol)。反应混合物于室温搅拌过夜,以2NHCl中和至pH3,并在氮气流下浓缩。将形成的沉淀滤出,以水洗涤,并干燥得到标题化合物,为白色固体(0.107g,74.6%):mp171–173℃;1HNMR(400MHz,DMSO-d6)δ7.08–7.00(m,2H),6.99–6.93(m,2H),6.93(brs,2H),6.06(s,2H);ESIMSm/z311.2([M+H]+),309.1([M-H]-).
在该实施例中使用的制备方法在表2中称为“水解”。
实施例10:制备4-氨基-3-氯-5-氟-6-(2-羟基-2,3-二氢-1H-茚-5-基)吡啶-2-甲酸甲基酯
5-(4,4,5,5-四甲基-1,3,2-二氧杂硼杂环戊烷-2-基)-2,3-二氢-1H-茚-2-醇(3.8g,14.61mmol)、头部B(3.4g,14.61mmol)和氟化铯(CsF;4.44g,29.23mmol)在乙腈/水(75mL:25mL)至的化合物以氩气冲洗20min,然后添加Pd(PPh3)2Cl2(1.0g,1.46mmol)。反应混合物于110℃搅拌2h,然后冷却至室温,经短垫过滤并以乙酸乙酯洗涤(100mL)。滤液经减压浓缩。剩余物通过柱色谱纯化(乙酸乙酯/己烷和硅胶100–200筛目)得到标题化合物(1.8g,36%).
实施例11:制备4-氨基-3-氯-5-氟-6-(2-氟-2,3-二氢-1H-茚-5-基)吡啶-2-甲酸甲基酯
向4-氨基-3-氯-5-氟-6-(2-羟基-2,3-二氢-1H-茚-5-基)吡啶-2-甲酸甲基酯(0.5g,1.48mmol)在二氯甲烷(15mL)中的-78℃溶液添加(1.9g,8.92mmol)。反应混合物升温至室温并搅拌16h。混合物然后以二氯甲烷稀释(15mL),以冷的饱和NaHCO3溶液(2x10mL)、盐水(10mL)洗涤,经Na2SO4干燥并减压浓缩。剩余物通过柱色谱纯化(乙酸乙酯/己烷和硅胶230–400筛目)得到标题化合物(0.145g,28%):1HNMR(300MHz,DMSO-d6)δ7.71(s,1H),7.64(d,J=8.1Hz,1H),7.41(d,J=7.8Hz,1H),6.92(s,2H),5.64–5.45(m,1H),3.88(s,3H),3.39–3.09(m,4H);ESIMSm/z339[(M+H)+].
实施例12:制备4-氨基-3-氯-5-氟-6-(2-氧代-2,3-二氢-1H-茚-5-基)吡啶-2-甲酸甲基酯
向4-氨基-3-氯-5-氟-6-(2-羟基-2,3-二氢-1H-茚-5-基)吡啶-2-甲酸甲基酯(1.0g,2.97mmol)在二氯甲烷(25mL)中的0℃溶液添加氯铬酸吡啶(1.27g,5.95mmol)。反应混合物在室温搅拌6h,经短垫过滤并以二氯甲烷洗涤(50mL)。滤液经Na2SO4干燥并减压浓缩。剩余物通过柱色谱纯化(乙酸乙酯/己烷和硅胶100–200筛目)得到标题化合物(0.5g,56%):ESIMSm/z335[(M+H)+].
实施例13:制备4-氨基-3-氯-6-(2,2-二氟-2,3-二氢-1H-茚-5-基)-5-氟吡啶-2-甲酸甲基酯
向4-氨基-3-氯-5-氟-6-(2-氧代-2,3-二氢-1H-茚-5-基)吡啶-2-甲酸甲基酯(0.5g,1.497mmol)在二氯甲烷(50mL)中的-78℃溶液添加二乙基氨基三氟化硫(DAST;1.4g,8.98mmol)。反应混合物于室温搅拌16h。混合物然后以二氯甲烷(50mL)稀释,以冰冷的饱和NaHCO3溶液(2x10mL)、盐水洗涤,经Na2SO4干燥并减压浓缩。剩余物通过柱色谱纯化(乙酸乙酯/己烷和硅胶100–200筛目)得到标题化合物(0.105g,18%):1HNMR(400MHz,DMSO-d6)δ7.77(d,J=6Hz,2H),7.31(d,J=8.4Hz,1H),4.89(s,2H),3.98(s,3H),3.52–3.43(m,4H);ESIMSm/z357[(M+H)+].
表2.化合物编号、结构、制备和外观
表3.表1中的化合物的分析数据
除草活性的实施例
除草性评估是按0至100等级目测的,其中0表示无活性,100表示植物完全死亡。数据如表4中所示。
表4:防治百分比评级转化表
评级 | %防治 |
A | 95-100 |
B | 85-94 |
C | 75-84 |
D | 60-74 |
E | 45-59 |
F | 30-44 |
G | 0-29 |
实施例A.评价芽后除草活性
芽后测试I:测试用种子品种是从供应商获得的并且种植在装有无土基质混合物(Metro-MixSunGroHorticulture)的5"-圆形花盆中。在施用前的8-12天(d),种植芽后处理物并在装备有补充光源(以提供16小时光照)的24-29℃温室中培养。所有花盆都是表面灌溉。
将每种化合物约10毫克(mg)溶解在1.3mL丙酮-DMSO(97:3,体积/体积(v/v))中并用4.1mL含有0.02%TritonX-155的水-异丙醇-作物油浓缩物(78:20:2,v/v/v)稀释。将处理物用上面的制剂溶剂连续稀释,从而得到在2.7mL/花盆中递送的1.85、0.926、0.462和0.231毫克/毫升(mg/mL)的测试化合物(大致相当于分别为4.0、2.0、1.0和0.5kg/ha)。
所配制的化合物是用空气压缩喷雾器以2-4磅/平方英寸(psi)施用的。处理后,将花盆送回到温室中,在整个实验期间都放置在温室中。所有花盆都根据需要地下灌溉,从而提供最佳的生长条件。所有花盆都通过地下灌溉用PetersPeat-Lite肥料(20-10-20)每周施肥一次。
在处理物芽后施用后的10天获得植物毒性评级。所有评估是按0至100等级目测的,其中0表示无活性,100表示植物完全死亡,并且如表4所示。
所测试的化合物中的一些、所采用的施用率、所测试的植物品种和结果在表5中给出。
表5.对主要阔叶杂草和禾本科杂草以及作物品种的芽后测试I除草活性
AVEFA:野燕麦(wildoats)(野燕麦(Avenafatua))
ECHCG:稗草(barnyardgrass)(稗(Echinochloacrus-galli))
HELAN:向日葵(sunflower)(向日葵(Helianthusannuus))
IPOHE:裂叶牵牛(ivyleafmorningglory)(碗仔花(Ipomoeahederecea))
SETFA:大狗尾草(giantfoxtail)(大狗尾草(Setariafaberi))
kgai/ha:千克活性成分/公顷
n/t:未测试
实施例B.评估芽前除草活性
芽前测试I将测试用种子品种种植在装有砂壤土的圆塑料花盆(直径5-英寸)。种植后,在施用化合物前的16小时将所有花盆地下灌溉。
将化合物溶解在丙酮和DMSO的97:3v/v混合物中并在最终施用溶液中稀释至适当的浓度,所述施用溶液含有59:23:15:1.0:1.5v/v比例的水、丙酮、异丙醇、DMSO和Agri-dex(作物油浓缩物)以及0.02%w/v(重量/体积)的TritonX-155,从而获得含有最高施用率的喷雾溶液。将所述高施用率用上述施用溶液连续稀释,从而以最高施用率的1/2X、1/4X和1/8X的施用率(分别相当于4.0、2.0、1.0和0.5kg/ha)递送所述化合物。
将配制的化合物(2.7mL)均匀施用/移液至土壤表面,然后掺加水(15mL)。处理后,将花盆送回到温室中,在整个实验期间都放置在温室中。将所述温室设定为约15h光照时间,在白天温室维持在约23-29℃,夜晚期间维持在22-28℃。通过表面灌溉有规律地添加养料和水并根据需要用顶部金属卤化物1000-瓦灯泡提供补充照明。
处理后的14天获得除草效果评级。所有评估都是相对于适当的对照按0至100等级进行的,其中0表示无除草效果,100表示植物死亡或没有从土壤中发芽,并且如表4中所示。
所测试的化合物中的一些、所采用的施用率、所测试的植物品种和结果提供在表6中。
表6.对主要阔叶杂草和禾本科杂草以及作物品种的芽前测试I除草活性
AVEFA:野燕麦(wildoats)(野燕麦(Avenafatua))
ECHCG:稗草(barnyardgrass)(稗(Echinochloacrus-galli))
HELAN:向日葵(sunflower)(向日葵(Helianthusannuus))
IPOHE:裂叶牵牛(ivyleafmorningglory)(碗仔花(Ipomoeahederecea))
SETFA:大狗尾草(giantfoxtail)(大狗尾草(Setariafaberi))
kgai/ha:千克活性成分/公顷
实施例C.评估芽后除草活性
芽后测试II:将期望测试的植物种类的种子或小坚果种植在装在塑料花盆的SunGro360栽培混合物中,该混合物通常具有6.0至6.8的pH和约30%的有机物含量,花盆的表面积为64平方厘米(cm2)。当需要确保良好发芽和健康植物时,应用杀真菌处理和/或其他化学或物理处理。使所述植物在具有约15h光照时间的温室中生长7-21天,其中所述温室的温度白天维持在约23-29℃,夜间维持在22-28℃。有规律地添加养料和水并根据需要用顶部金属卤化物1000-瓦灯泡提供补充照明。当所述植物达到第一或第二片真叶阶段时将该植物用于测试。
根据每种测试化合物待测试的最高施用率确定化合物的量,称取该量并装在25mL玻璃小瓶中,溶解在4mL丙酮和DMSO的97:3v/v混合物中,从而获得浓缩的原液。如果测试化合物不易溶解,则将所述化合物进行温热和/或对其进行超声。将所得的浓缩的原液用20mL含有48.5:39:10:1.5:1.0:0.02v/v比例的丙酮、水、异丙醇、DMSO、Atplus411F作物油浓缩物和X-155表面活性剂的水性混合物稀释,从而获得含有最高施用率的喷雾溶液。通过以下方式获得其他施用率:将12mL最高施用率溶液连续稀释成含有2mL丙酮和DMSO的97:3v/v混合物和10mL含有48.5:39:10:1.5:1.0:0.02v/v比例的丙酮、水、异丙醇、DMSO、Atplus411F作物油浓缩物和TritonX-155表面活性剂的溶液,从而获得高施用率的1/2X、1/4X、1/8X和1/16X施用率。化合物的需求量基于施用率为187升/公顷(L/ha)时的12mL施用体积。将配制的化合物施用于植物材料,采用的是顶部Mandel轨道喷雾器,该喷雾器装备有8002E喷嘴,该喷嘴经校准在0.503平方米施用面积内以187L/ha递送,喷雾高度为平均植物株冠高度之上18英寸(43cm)。按相同的方式用空白溶剂喷洒对照植物。
将经处理的植物和对照植物放置在如上所述的温室中并通过地下灌溉浇水,从而防止测试化合物冲走。14天后,目测测试植物的状况,并与未经处理的植物的状况相比,按0至100%的等级评分,其中0%对应于无损害,100对应于完全杀死,并如表4中所示。
所测试的化合物中的一些、所采用的施用率、所测试的植物品种和结果提供在表7中。
表7.对主要阔叶杂草和作物品种的芽后测试II除草活性
ABUTH:绒毛叶(velvetleaf)(苘麻((Abutilontheophrasti))
AMARE:红根藜草(redrootpigweed)(反枝苋(Amaranthusretroflexus))
BRSNN:低芥酸油菜(oilseedrape,canola)(油菜(Brassicanapus))
CHEAL:灰菜(lambsquarters)(藜草(Chenopodiumalbum))
EPHHL:野生一品红(wildpoinsettia)(白苞猩猩草(Euphorbiaheterophylla))
HELAN:向日葵(sunflower)(向日葵(Helianthusannuus))
gai/ha:克活性成分/公顷
n/t:未测试
表8.对主要禾本科杂草和莎草杂草的芽后测试II除草活性
ECHCG:稗草(barnyardgrass)(稗(Echinochloacrus-galli))
CYPES:黄莎草(yellownutsedge)(油莎草(Cyperusesculentus))
ORYSA:稻(rice)(稻(Oryzasativa))
SETFA:大狗尾草(giantfoxtail)(大狗尾草(Setariafaberi))
TRZAS:春小麦(wheat,spring)(小麦(Triticumaestivum))
ZEAMX:玉米(maize,corn)(玉米(Zeamays))
gai/ha:克活性成分/公顷
n’t:未测试
实施例D.在小麦和大麦中评估芽后除草活性
芽后测试III.将期望测试的植物种类的种子种植在装在塑料花盆的SunGro306栽培混合物中,该混合物通常具有6.0至6.8的pH和约30%的有机物含量,花盆的表面积为103.2平方厘米(cm2)。当需要确保良好发芽和健康植物时,应用杀真菌处理和/或其他化学或物理处理。使所述植物在具有约14小时(h)光照时间的温室中生长7-36天(d),其中所述温室的温度白天维持在约18℃,夜间维持在17℃。有规律地添加养料和水并根据需要用顶部金属卤化物1000-瓦灯泡提供补充照明。当所述植物达到第二或第三片真叶阶段时将该植物用于测试。
根据每种测试化合物待测试的最高施用率确定化合物的量,称取该量并装在25mL玻璃小瓶中,溶解在4mL丙酮和DMSO的97:3v/v混合物中,从而获得浓缩的原液。如果测试化合物不易溶解,则将所述化合物进行温热和/或对其进行超声。将所得的浓缩的原液用20mL含有48:39:10:1.5:1.5:0.02v/v比例的丙酮、水、异丙醇、DMSO、Agri-Dex作物油浓缩物和X-77表面活性剂的水性混合物稀释,从而获得含有最高施用率的喷雾溶液。通过以下方式获得其他施用率:将12mL高施用率溶液连续稀释成含有2mL丙酮和DMSO的97:3v/v混合物和10mL含有48:39:10:1.5:1.5:0.02v/v比例的丙酮、水、异丙醇、DMSO、Agri-Dex作物油浓缩物和X-77表面活性剂的溶液,从而获得高施用率的1/2X、1/4X、1/8X和1/16X施用率。化合物的需求量基于施用率为187升/公顷(L/ha)时的12mL施用体积。将配制的化合物施用于植物,采用的是顶部Mandel轨道喷雾器,该喷雾器装备有8002E喷嘴,该喷嘴经校准在0.503平方米使用面积内以187L/ha递送,喷雾高度为平均植物株冠高度之上18英寸(43cm)。按相同的方式用空白溶剂喷洒对照植物。
将经处理的植物和对照植物放置在如上所述的温室中并通过地下灌溉浇水,从而防止测试化合物冲走。21天后,目测测试植物的状况,并与未经处理的植物的状况相比,按0%至100%的等级评分,其中0%对应于无损害,100%对应于完全杀死,并示于表4中。
通过采用公认的如J.BerksoninJournaloftheAmericanStatisticalSociety,48,565(1953)和由D.Finneyin“ProbitAnalysis”CambridgeUniversityPress(1952)所描述的概率分析,可将具体化合物在不同施用率的除草损伤用于计算GR20、GR50、GR80和GR90值,其被定义为生长减少因子,该生长减少因子分别对应于提供20%、50%、80%或90%的植物生长减少(GR)所需的有效剂量。将概率分析应用于使用以下实施例中解释的方法从多个施用率的单个化合物收集的数据。一些施用率的数据和所有施用率的分析采集在下表中。
所测试的化合物中的一些、所采用的施用率、所测试的植物品种和结果提供在表9至13中。
表9:除草性化合物在小麦和大麦中的活性
表10:除草性化合物在小麦和大麦中的活性
表11:除草性化合物在小麦和大麦中的活性
表12:除草性化合物在小麦和大麦中的活性
表13:除草性化合物在小麦和大麦中的活性
ALOMY:黑草(black-grass)(大穗看麦娘(lopecurusmyosuroides))
APESV:常绿草(bentgrass)(阿披拉草(Aperaspica-venti))
BROTE:丘原雀麦草(downybrome)(旱雀麦(Bromustectorum))
HORVS:春大麦(barley,spring)(玉米(Zeamays))
TRZAS:春小麦(wheat,spring)(Hordeumvulgare)
LOLSS:黑麦草,包括意大利黑麦草(Italianryegrass)(多花黑麦草(Loliummultiflorum)),硬质黑麦草(rigidryegrass)(硬直黑麦草(Loliumrigidum))、一年生黑麦草(annualryegrass)(Loliummultiflorumsubsp.Gaudini)
PHAMI:lessercanarygrass(Phalarisminor)
SETVI:greenfoxtail(Setariaviridis)
KCHSC:kochia(Kochiascoparia)
LAMPU:紫色枯荨麻(purpledeadnettle)(紫花野芝麻(Lamiumpurpureum))
GALAP:cleavers(Galiumaparine)
SINAR:野生芥菜(wildmustard)(野欧白芥(Sinapisarvensis))
VERPE:波斯婆婆纳(bird’s-eyespeedwell)(阿拉伯婆婆纳(veronicapersica))
BRSNW:冬加拿大油菜(oilseedrape,winter;canola,winter)(欧洲油菜(Brassicanapus))
PAPRH:普通罂粟(commonpoppy)(虞美人(Papaverrhoeas))
SASKR:俄罗斯蓟(Russianthistle)(俄罗斯蓟(Salsolaiberica))
CIRAR:加拿大蓟(Canadathistle)(丝路蓟(Cirsiumarvense))
VIOTR:野生三色堇(wildpansy)(三色堇(Violatricolor))
AVEFA:野燕麦(wildoats)(野燕麦(Avenafatua))
MATCH:野甘菊(wildchamomile)(母菊(MatricariarecutitaL.))
gai/ha:克活性成分/公顷
NT:未测试
GR20:植物生长的20%生长减少
GR50:植物生长的50%生长减少
GR80:植物生长的80%生长减少
GR90:植物生长的90%生长减少
实施例E.评价在直播稻中的芽后除草活性
将所需测试植物品种的种子或果仁种植入土壤基质中,该土壤基质通过以80至20的比例混合壤土(43%泥浆,19%粘土和38%的沙子,pH值约8.1,并且有机物质含量为约1.5%)和河沙制备。该土壤基质容纳在表面积为139.7cm2的塑料盆中。当需要确保良好的萌芽和健康的植物时,施用杀真菌剂处理物和/或其他的化学或物理处理物。该植物在温室中生长10–17d,约14h的光照周期,白天期间保持在约29℃,夜间约26℃。有规律地添加营养剂和水,并且如有需要以顶部金属卤化物1000瓦灯提供补充光照。当它们达到第二或第三真叶阶段时,施用植物进行测试。
由待测试的最高施用率确定的称重量的各测试化合物置于25mL玻璃小瓶中并溶于4mL的丙酮和DMSO的97:3v/v混合物中,得到12X储备液。如果测试化合物不容易溶解,将混合物加热和/或超声。将该浓缩的储备液添加至喷雾溶液中,使得最终的丙酮和DMSO浓度分别为16.2%和0.5%。喷雾溶液通过添加10mL的1.5%(v/v)Agri-dex作物油浓缩物的水性混合物稀释至合适的最终浓度。最终的喷雾溶液含有1.25%(v/v)Agri-dex作物油浓缩物。化合物要求基于12mL施用体积,施用率为187升每公顷(L/ha)。以配有8002E喷嘴的顶部Mandel轨道喷雾器将配制的化合物施用至植物材料,该喷雾器校准为以高出平均植物株冠高度18英寸(43cm)的喷雾高度向0.503平方米的施用面积上递送187L/ha。对照植物以相同的方法用溶剂空白喷雾。
经处理的植物和对照植物置于上述的温室中并且通过地下灌溉浇水以防止冲刷掉测试化合物。20–22d后,测试植物的状况与未处理的植物的状况的比较在视觉上确定,并且以0-100百分比的尺度评分,其中0对应于无损伤,100对应于完全杀死,并且如表4中所指示。
通过应用在如下文献中描述的广泛接受的概率分析:J.Berkson,JournaloftheAmericanStatisticalSociety,48,565(1953)和D.Finney,“ProbitAnalysis”CambridgeUniversityPress(1952),特定化合物在各个施用率的除草损伤可以用来计算GR20、GR50、GR80和GR90数值,其定义为生长减少因子,对应于分别得到20%、50%、80%和90%的植物生长减少(GR)所需的除草剂的有效剂量。使用下列实施例中解释的方法将概率分析应用至从多剂量施用率的各个化合物所采集的数据。一些剂量施用率的数据和所有剂量施用率的分析捕捉在下表中。
一些施用的施用率和施用比例、测试的植物品种、和结果在表14中给出。
表14:除草性化合物在直播稻中的活性
BRAPP:阔叶信号草(broadleafsignalgrass)(臂形草(Brachiariaplatyphylla))
CYPDI:小花具节莎草根(small-flowerflatsedge)(异型莎草(Cyperusdifformis))
CYPES:黄莎草(yellownutsedge)(油莎草(Cyperusesculentus))
CYPIR:米莎草(riceflatsedge)(碎米莎草(Cyperusiria))
DIGSA:大马唐草(largecrabgrass),马唐(Digitariasanguinalis)
ECHCG:稗草(barnyardgrass),(稗(Echinochloacrus-galli))
ECHCO:光头稗(junglerice),(光头稗(Echinochloacolonum))
LEFCH:中国千金子(Chinesesprangletop)(千金子(Leptochloachinensis))
SCPJU:日本纸草(Japanesebulrush),萤蔺(Schoenoplectusjuncoides)
SEBEX:大麻田菁属(hempsesbania)(田菁(esbaniaexaltata))
ORYSK:稻(Oryzasativa)
ORYSJ:稻(Oryzasativa)
gai/ha:克活性成分/公顷
Claims (21)
1.式(I)化合物:
其中
X为N或CY,其中Y为氢、卤素、C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、C1-C3烷氧基、C1-C3烷基硫基或C1-C3卤代烷基硫基;
R1为OR1′或NR1″R1″′,其中R1′为氢、C1-C8烷基或C7-C10芳基烷基,和R1″和R1″′独立地为氢、C1-C12烷基、C3-C12烯基或C3-C12炔基;
R2为卤素、C1-C4烷基、C1-C4卤代烷基、C2-C4烯基、C2-C4卤代烯基、C2-C4炔基、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷基硫基、C1-C4卤代烷基硫基、氨基、C1-C4烷基氨基、C2-C4卤代烷基氨基、甲酰基、C1-C3烷基羰基、C1-C3卤代烷基羰基、氰基或式-CR17=CR18-SiR19R20R21的基团,其中R17为氢、F或Cl;R18为氢、F、Cl、C1-C4烷基或C1-C4卤代烷基;和R19、R20和R21独立地为C1-C10烷基、C3-C6环烷基、苯基、取代的苯基、C1-C10烷氧基或OH;
R3和R4独立地为氢、C1-C6烷基、C1-C6卤代烷基、C3-C6烯基、C3-C6卤代烯基、C3-C6炔基、甲酰基、C1-C3烷基羰基、C1-C3卤代烷基羰基、C1-C6烷氧基羰基、C1-C6烷基氨基甲酰基、C1-C6烷基磺酰基、C1-C6三烷基甲硅烷基、C1-C6二烷基氧膦基或R3和R4与N一起为5-或6-元饱和环或不饱和环,或者R3和R4一起代表=CR3′(R4′),其中R3′和R4′独立地为氢、C1-C6烷基、C3-C6烯基、C3-C6炔基、C1-C6烷氧基或C1-C6烷基氨基,或者R3′和R4′与=C一起代表5-或6-元饱和环;
A为基团Ar1至Ar28之一:
R5为氢、卤素、C1-C4烷基、C1-C4卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、C1-C3烷硫基、C1-C3卤代烷硫基、氨基、C1-C4烷基氨基或C2-C4卤代烷基氨基;
R6为氢、卤素、C1-C4烷基、C1-C4卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、C1-C3烷硫基、C1-C3卤代烷硫基、氨基、C1-C4烷基氨基或C2-C4卤代烷基氨基;
R6′为氢或卤素;
R6″为氢、卤素、C1-C4烷基、C1-C4卤代烷基、环丙基、卤代环丙基、C2-C4烯基、C2-C4卤代烯基、C2-C4炔基、C1-C3烷氧基、C1-C3卤代烷氧基、C1-C3烷硫基、C1-C3卤代烷硫基、氨基、C1-C4烷基氨基、C2-C4卤代烷基氨基、CN或NO2;
R7和R7′独立地为氢、卤素、C1-C4烷基、C1-C4卤代烷基或C1-C3烷氧基;
R8和R8′独立地为氢、卤素、C1-C4烷基、C1-C4卤代烷基或C1-C3烷氧基;
R9、R9′、R9″和R9″′独立地为氢、卤素、C1-C4烷基、C1-C4卤代烷基或C1-C3烷氧基;
R10为氢、C1-C6烷基、C1-C6卤代烷基、C3-C6烯基、C3-C6卤代烯基、C3-C6炔基、甲酰基、C1-C3烷基羰基、C1-C3卤代烷基羰基或C1-C6三烷基甲硅烷基;
m,当存在时,为0、1或2;和
n,当存在时,为0、1或2;
或其N-氧化物或农用盐;
条件是A不为
2.权利要求1的化合物,其中
X为N或CY,其中Y为氢、卤素、C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、C1-C3烷氧基、C1-C3烷硫基或C1-C3卤代烷硫基;
R1为OR1′或NR1″R1″′,其中R1′为氢、C1-C8烷基或C7-C10芳基烷基,且R1″和R1″′独立地为氢、C1-C12烷基、C3-C12烯基或C3-C12炔基;
R2为卤素、C1-C4烷基、C1-C4卤代烷基、C2-C4烯基、C2-C4卤代烯基、C2-C4炔基、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷硫基、C1-C4卤代烷硫基、氨基、C1-C4烷基氨基、C2-C4卤代烷基氨基、甲酰基、C1-C3烷基羰基、C1-C3卤代烷基羰基、氰基或式-CR17=CR18-SiR19R20R21的基团,其中R17为氢、F或Cl;R18为氢、F、Cl、C1-C4烷基或C1-C4卤代烷基;且R19、R20和R21独立地为C1-C10烷基、C3-C6环烷基、苯基、取代苯基、C1-C10烷氧基或OH;
R3和R4独立地为氢、C1-C6烷基、C1-C6卤代烷基、C3-C6烯基、C3-C6卤代烯基、C3-C6炔基、甲酰基、C1-C3烷基羰基、C1-C3卤代烷基羰基、C1-C6烷氧基羰基、C1-C6烷基氨基甲酰基、C1-C6烷基磺酰基、C1-C6三烷基甲硅烷基、C1-C6二烷基氧膦基,或者R3和R4与N一起为5-或6-元饱和环,或者R3和R4一起代表=CR3′(R4′),其中R3′和R4′独立地为氢、C1-C6烷基、C3-C6烯基、C3-C6炔基、C1-C6烷氧基或C1-C6烷基氨基,或者R3′和R4′与=C一起代表5-或6-元饱和环;
A为基团Ar1、Ar2、Ar3、Ar4、Ar5、Ar6、Ar7、Ar8、Ar9、Ar10、Ar11、Ar12、Ar13、Ar14、Ar15、Ar16、Ar17、Ar18、Ar19、Ar20、Ar21、Ar22、Ar23或Ar24之一;
R5为氢、卤素、C1-C4烷基、C1-C4卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、C1-C3烷硫基、C1-C3卤代烷硫基、氨基、C1-C4烷基氨基或C2-C4卤代烷基氨基。
R6为氢、卤素、C1-C4烷基、C1-C4卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、C1-C3烷硫基、C1-C3卤代烷硫基、氨基、C1-C4烷基氨基或C2-C4卤代烷基氨基;
R6′为氢或卤素;
R6″为氢、卤素、C1-C4烷基、C1-C4卤代烷基、环丙基、卤代环丙基、C2-C4烯基、C2-C4卤代烯基、C2-C4炔基、C1-C3烷氧基、C1-C3卤代烷氧基、C1-C3烷硫基、C1-C3卤代烷硫基、氨基、C1-C4烷基氨基、C2-C4卤代烷基氨基、CN或NO2;
R7和R7′独立地为氢、卤素、C1-C4烷基、C1-C4卤代烷基或C1-C3烷氧基;
R8和R8′独立地为氢、卤素、C1-C4烷基、C1-C4卤代烷基或C1-C3烷氧基;
R9、R9′、R9″和R9″′独立地为氢、卤素、C1-C4烷基、C1-C4卤代烷基或C1-C3烷氧基;
R10为氢、C1-C6烷基、C1-C6卤代烷基、C3-C6烯基、C3-C6卤代烯基、C3-C6炔基、甲酰基、C1-C3烷基羰基、C1-C3卤代烷基羰基或C1-C6三烷基甲硅烷基;
m,当存在时,为0、1或2;和
n,当存在时,为0、1或2;
或其N-氧化物或农用盐;
条件是A不为
3.权利要求2的化合物,其中Ar为Ar1、Ar2、Ar3、Ar4、Ar5、Ar6、Ar7、Ar8、Ar15、Ar16、Ar17或Ar18。
4.权利要求1-2中任一项的化合物,其中m,当存在时,为0或1,其中n,当存在时,为0或1。
5.权利要求1-4中任一项的化合物,其中R1为OR1′。
6.权利要求1-5中任一项的化合物,其中R2为卤素、C2-C4-烯基、C2-C4卤代烯基或C1-C4-烷氧基。
7.权利要求1-6中任一项的化合物,其中R2为Cl、甲氧基、乙烯基或1-丙烯基。
8.权利要求1-7中任一项的化合物,其中R3和R4均为氢。
9.权利要求1-8中任一项的化合物,其中X为N、CH或CF。
10.权利要求1-9中任一项的化合物,其中R5为氢或卤素。
11.权利要求10的化合物,其中R5为氢或F。
12.权利要求1-11中任一项的化合物,其中R6为氢或F。
13.权利要求1-12中任一项的化合物,其中R6′为氢。
14.权利要求1-13中任一项的化合物,其中:
R2为卤素、C2-C4-烯基或C1-C4-烷氧基;
R3和R4为氢;和
X为N、CH或CF;
Ar为Ar1、Ar3、Ar7、Ar9、Ar10、Ar13、Ar15、Ar16、Ar19、Ar21或Ar22;
R5为氢或F;
R6为氢或F;
R6′为氢;
R7、R7′、R8、R8′、R9、R9′、R9″和R9″′,如果可应用于相关的Ar基团,独立地为氢或氟;
15.权利要求1-14中任一项的化合物,其中:
R2为氯;
R3和R4为氢;和
X为N、CH或CF。
16.权利要求1-14中任一项的化合物,其中:
R2为甲氧基;
R3和R4为氢;和
X为N、CH或CF。
17.权利要求1-14中任一项的化合物,其中:
R2为乙烯基或1-丙烯基;
R3和R4为氢;和
X为N、CH或CF。
18.除草组合物,其包含权利要求1-17中任一项的化合物和农用助剂或载体。
19.权利要求18的组合物,进一步包含至少一种其它除草化合物。
20.权利要求18或19的组合物,进一步包含除草安全剂。
21.一种防治不期望的植被的方法,包括施用除草有效量的权利要求1-17中任一项的化合物或权利要求18-20中任一项的除草组合物。
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