WO2019196908A1 - 一种吡唑喹唑啉二酮类化合物及其应用和一种农药除草剂 - Google Patents
一种吡唑喹唑啉二酮类化合物及其应用和一种农药除草剂 Download PDFInfo
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- WO2019196908A1 WO2019196908A1 PCT/CN2019/082279 CN2019082279W WO2019196908A1 WO 2019196908 A1 WO2019196908 A1 WO 2019196908A1 CN 2019082279 W CN2019082279 W CN 2019082279W WO 2019196908 A1 WO2019196908 A1 WO 2019196908A1
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- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- IOMMMLWIABWRKL-WUTDNEBXSA-N nazartinib Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCC[C@H]1N1C2=C(Cl)C=CC=C2N=C1NC(=O)C1=CC=NC(C)=C1 IOMMMLWIABWRKL-WUTDNEBXSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- PIDFDZJZLOTZTM-KHVQSSSXSA-N ombitasvir Chemical compound COC(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@H]1C(=O)NC1=CC=C([C@H]2N([C@@H](CC2)C=2C=CC(NC(=O)[C@H]3N(CCC3)C(=O)[C@@H](NC(=O)OC)C(C)C)=CC=2)C=2C=CC(=CC=2)C(C)(C)C)C=C1 PIDFDZJZLOTZTM-KHVQSSSXSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000000447 pesticide residue Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- CMPQUABWPXYYSH-UHFFFAOYSA-N phenyl phosphate Polymers OP(O)(=O)OC1=CC=CC=C1 CMPQUABWPXYYSH-UHFFFAOYSA-N 0.000 description 1
- CMPQUABWPXYYSH-UHFFFAOYSA-L phenyl phosphate(2-) Polymers [O-]P([O-])(=O)OC1=CC=CC=C1 CMPQUABWPXYYSH-UHFFFAOYSA-L 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920005646 polycarboxylate Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical compound O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 238000006462 rearrangement reaction Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 235000002020 sage Nutrition 0.000 description 1
- 235000013580 sausages Nutrition 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- KSAVQLQVUXSOCR-UHFFFAOYSA-M sodium lauroyl sarcosinate Chemical compound [Na+].CCCCCCCCCCCC(=O)N(C)CC([O-])=O KSAVQLQVUXSOCR-UHFFFAOYSA-M 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 235000020354 squash Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 229960005404 sulfamethoxazole Drugs 0.000 description 1
- JLKIGFTWXXRPMT-UHFFFAOYSA-N sulphamethoxazole Chemical compound O1C(C)=CC(NS(=O)(=O)C=2C=CC(N)=CC=2)=N1 JLKIGFTWXXRPMT-UHFFFAOYSA-N 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical class NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 239000013008 thixotropic agent Substances 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
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000000725 trifluoropropyl group Chemical group [H]C([H])(*)C([H])([H])C(F)(F)F 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 230000002087 whitening effect Effects 0.000 description 1
Classifications
-
- 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
-
- 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
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
-
- 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
- A01N43/60—1,4-Diazines; Hydrogenated 1,4-diazines
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/84—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/18—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, directly attached to a heterocyclic or cycloaliphatic ring
-
- 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
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds
- A01N57/16—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing heterocyclic radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
-
- 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
- C07D405/14—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 three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/02—Heterocyclic radicals containing only nitrogen as ring hetero atoms
Definitions
- the invention relates to the field of pesticides, in particular to a pyrazoloquinazolinedione compound and application thereof, and a pesticide herbicide.
- weeds such as valerian, crabgrass, foxtail, and ginseng in rice fields have serious resistance to the main rice field herbicides currently on the market; the sage, leeks, maidens, and japan in the wheat fields
- the resistant populations of major weeds such as aphis, brome, wheat, and wild oats have also developed into dominant weeds, resulting in increasing use of herbicides in rice fields or wheat fields in some provinces and municipalities, which not only increases the cost of prevention, Moreover, it caused frequent incidents of phytotoxicity and excessive pesticide residues.
- HPPD p-hydroxyphenylpyruvate dioxygenase
- Triketones represented by mesotrione
- the HPPD-inhibiting herbicides entered the market at a relatively late date compared with AHAS-, PPO- and ACCase-suppressing herbicides, but did not hinder the rapid occupation of the "stars" in the market, especially It is a triketone herbicide, mesotrione (also known as mesotrione) developed by Syngenta, which has occupied the top five sales of herbicides for many years.
- mesotrione also known as mesotrione
- mesotrione has gradually replaced other types of herbicides, making it the most widely used and most effective cornfield herbicide.
- mesotrione still has some self-deficiencies, such as its poor safety against other large crops such as rice and wheat, and mesotrione against a variety of grass weeds (such as ordinary weeds).
- the control effect of foxtail and golden foxtail is poor. It is also reported in the literature that weeds are prone to greening after the use of mesotrione.
- HPPD herbicide that can be used in rice fields in combination with broad-spectrum and ultra-efficient herbicidal activity. In particular, it has no excellent resistance to malignant weeds such as resistant alfalfa and Qianjin. Effective herbicide.
- WO 2017/140612 A1 discloses a class of quinazolindione-6-carbonyl derivatives as HPPD inhibitors.
- the compounds described in the prior art do not exhibit sufficient safety against crops such as rice and wheat, so that they cannot be directly used in rice fields for weed control.
- the object of the present invention is to overcome the aforementioned drawbacks of the prior art and to provide a new class of pyrazole quinazolinedione which can be used for controlling weeds in crops, particularly rice fields, with high safety. Class compounds to achieve excellent herbicidal effects.
- a first aspect of the present invention provides a pyrazoloquinazolinedione compound having a structure represented by the formula (I).
- X is selected from C 1-12 alkyl group, 1-6 groups selected from the halogen atoms of the C 1-12 alkyl group substituted by a C 1-3 alkoxy-substituted alkyl group of C 2-12, C 2-12 alkenyl, C 2-12 alkynyl, more selected from O, N, S, at least one heteroatom in the C 2-12 cycloalkyl group, containing selected from O, N, S a C 2-6 cycloalkyl substituted C 3-12 alkyl group of at least one hetero atom;
- Y is selected from the group consisting of H, C 1-6 alkyl
- Z is H or a group represented by the formula (I-1), wherein, in the formula (I-1), R 1 and R 2 are the same or different and each is independently selected from a C 1-6 alkyl group.
- C 1-12 alkyl means an alkyl group having a total of 1 to 12 carbon atoms, and includes a linear alkyl group, a branched alkyl group or a cycloalkyl group, for example, the total number of carbon atoms is 1, 2, 3, 4 a linear alkyl group, a branched alkyl group or a cycloalkyl group of 5, 6, 7, 8, 9, 10, 11 or 12, which may be, for example, methyl, ethyl, n-propyl, isopropyl or n-butyl Base, isobutyl, tert-butyl, n-pentyl, isopentyl, n-hexyl, cyclopropyl, methylcyclopropyl, ethylcyclopropyl, cyclobutyl, methylcyclobutyl, ethyl ring Butyl, cyclopentyl, methylcyclopentyl, ethyl
- C 1-12 alkyl group substituted by 1 to 6 halogen-substituted atoms means an alkyl group having a total of 1 to 12 carbon atoms, and includes a linear alkyl group, a branched alkyl group and a cycloalkyl group, and 1 to 6 H in the alkyl group of C 1-12 are substituted by a halogen atom selected from halogen, for example, 1, 2, 3, 4, 5 or 6 H of the C 1-12 alkyl group is selected from Any one or more of fluorine, chlorine, bromine and iodine may be substituted, for example, trifluoromethyl, difluoromethyl, monofluoromethyl, monofluoroethyl, difluoroethyl, trifluoroethyl , monofluoropropyl, difluoropropyl, trifluoropropyl, and the like.
- C 2-12 alkyl group substituted by a C 1-3 alkoxy group means a group having a total of 2 to 12 carbon atoms, and the structural formula of the group can be represented by -R 1 OR 2 , wherein R The sum of the number of carbon atoms in 1 and R 2 is 2 to 12, and R 1 is directly bonded to the core structure of the compound of the structure of the formula (I) of the present invention.
- alkenyl group of C 2-12 means a hydrocarbon group having a total of 2 to 12 carbon atoms, and at least one ethylenic bond in the hydrocarbon group.
- alkynyl group of C 2-12 means a hydrocarbon group having a total of 2 to 12 carbon atoms, and at least one acetylene bond in the hydrocarbon group.
- the "C 2-12 cycloalkyl group having at least one hetero atom selected from O, N, and S” means a cycloalkyl group having a total of 2 to 12 carbon atoms, and the atom forming the ring contains an O group selected from At least one hetero atom in N, S, and each atom forming a ring may have an alkyl substituent, and the number of carbon atoms contained in the alkyl substituent is included in the total number of carbon atoms.
- it may be a three-membered ring, a four-membered ring, a five-membered ring, a six-membered ring, a seven-membered ring, an eight-membered ring, a nine-membered ring, a ten-membered ring, an eleven-membered ring or a twelve-membered ring, and a cycloalkyl group.
- H in the above may be optionally substituted or unsubstituted with a substituent, and if substituted, each of the substituents is independently selected from at least one of an alkyl group, a halogen, a hydroxyl group, a nitro group and a fluorenyl group.
- C 3-12 alkyl group substituted by a C 2-6 cycloalkyl group having at least one hetero atom selected from O, N, S means a group having a total of 3 to 12 carbon atoms, and The group contains at least one C 2-6 cycloalkyl group including at least one hetero atom selected from O, N, S, and the number of carbon atoms in the cycloalkyl group is included in the total number of carbon atoms described above.
- X is selected from alkyl of 1-8 C, made by 1-6 atoms selected from halo substituted C 1-8 alkyl, substituted by a C 1-3 alkoxy C 2-8 alkyl group, C 2-8 alkenyl group, C 2-8 alkynyl group, C 2-8 cycloalkyl group containing at least one O atom, C 3 substituted by C 2-6 cycloalkyl group containing at least one O atom -8 alkyl;
- Y is selected from the group consisting of H, C 1-4 alkyl
- Z is H or a group represented by the formula (I-1), wherein, in the formula (I-1), R 1 and R 2 are the same or different and each is independently selected from a C 1-4 alkyl group.
- Z is H.
- X is selected from C 1-12 alkyl group, 1-6 groups selected from the halogen atoms of the C 1-12 alkyl group substituted by a C 1-3 alkoxy-substituted alkyl group of C 2-12, C 2-12 alkenyl, C 2-12 alkynyl, more selected from O, N, S, at least one heteroatom in the C 2-12 cycloalkyl group, containing selected from O, N, S a C 2-6 cycloalkyl substituted C 3-12 alkyl group of at least one hetero atom;
- Y is selected from the group consisting of H, C 1-6 alkyl
- X is selected from alkyl of 1-8 C, made by 1-6 atoms selected from halo substituted C 1-8 alkyl, substituted by a C 1-3 alkoxy C 2-8 alkyl group, C 2-8 alkenyl group, C 2-8 alkynyl group, C 2-8 cycloalkyl group containing at least one O atom, C 3 substituted by C 2-6 cycloalkyl group containing at least one O atom -8 alkyl;
- Y is selected from the group consisting of H, C 1-4 alkyl
- X is selected from C 1-12 alkyl group, 1-6 groups selected from the halogen atoms of the C 1-12 alkyl group substituted by a C 1-3 alkoxy-substituted alkyl group of C 2-12, C 2-12 alkenyl, C 2-12 alkynyl, more selected from O, N, S, at least one heteroatom in the C 2-12 cycloalkyl group, containing selected from O, N, S a C 2-6 cycloalkyl substituted C 3-12 alkyl group of at least one hetero atom;
- Y is selected from the group consisting of H, C 1-6 alkyl
- Z is a group represented by the formula (I-1), and in the formula (I-1), R 1 and R 2 are the same or different and each is independently selected from a C 1-3 alkyl group.
- X is selected from alkyl of 1-8 C, made by 1-6 atoms selected from halo substituted C 1-8 alkyl, substituted by a C 1-3 alkoxy C 2-8 alkyl group, C 2-8 alkenyl group, C 2-8 alkynyl group, C 2-6 cycloalkyl group containing at least one O atom, C 3 substituted by C 2-6 cycloalkyl group containing at least one O atom -8 alkyl;
- Y is selected from the group consisting of H, C 1-4 alkyl
- Z is a group represented by the formula (I-1), and in the formula (I-1), R 1 and R 2 are the same or different and each is independently selected from a C 1-3 alkyl group.
- the pyrazoloquinazolinedione compound of the present invention is selected from at least one of the following compounds:
- the pyrazoloquinazolinedione compound provided by the present invention has excellent crop safety and excellent herbicidal effect.
- the pyrazoloquinazolinedione compound introduced by the present invention incorporating an alkyl-substituted carbamate fragment is effective not only for the rice field weed effect, but also significantly safer than the prior art compound for rice. .
- the method for synthesizing the pyrazoloquinazolinedione compound represented by the formula (I) is not particularly limited, and those skilled in the art can obtain a suitable preparation according to the synthesis method of the compound structure in the chemical field provided by the present invention.
- pyrazoloquinazolinedione compound of the formula (I) of the present invention can be synthesized according to the following synthetic route:
- the starting materials in the above synthetic routes can be prepared, for example, by the method described in CN104557739A.
- the synthesis method of the product may be, for example, dissolving the raw material in a solvent, adding oxalyl chloride, and stirring the reaction at a low temperature. After the reaction is completed, the solvent is removed, and the remaining solid is dissolved in a solvent for use. At a low temperature, the pyrazolone was dissolved in a solvent, and triethylamine was added. After stirring, the acid chloride solution dissolved in the solvent was added dropwise to the reaction system, and the reaction was monitored by TLC. After the reaction is completed, a saturated NaHCO 3 solution is added to the reaction system, and the combined organic layers are extracted, dried and concentrated to obtain a product.
- the synthesis method of the product may be, for example, adding a raw material, acetonitrile to a flask, stirring, and adding Et 3 N and acetone cyanohydrin.
- the reaction was monitored by TLC. After the reaction was completed, a HCl solution was added to the reaction mixture, stirring was continued, and solids were filtered off with suction.
- a second aspect of the invention provides the use of the pyrazoloquinazolinedione compound of the first aspect for controlling weeds.
- the weed is selected from at least one of broadleaf weeds, grass weeds, and sedge weeds.
- the weeds include foxtail, valerian, thousand gold, crabgrass, squash, leeks, gray vegetables, ramie, brome, wild oats, maiden, japan, ryegrass, Rice, Cassia, Morning Glory, Xanthium, Sedge, Big Nest, Amaranthus, Pseudosalt, Sausage, Purslane, Hedgehog, Bidens, Shuangsui, Rice At least one of Lee's Wo, water bamboo leaves, wild sage, Alisma, Yujiu, yarrow, ragweed, flamingo, and sedge.
- the broadleaf weeds include amaranth, gray cabbage, ramie, rice balsam, cassia grass, morning glory, Xanthium, amaranth, pseudo-acid syrup, calf, dent At least one of cockroach, hedgehog, water bamboo leaves, wild sage, diarrhea, rain long flower, comfrey, ragweed and sedge.
- the sedge includes flamingo, sedge, and the like.
- the grass weeds include foxtail, valerian, thousand gold, crabgrass, stalked wheat, brome, wild oats, maiden, japan, ryegrass, sedge At least one of the big nest vegetables, the Bidens, the double-spotted gar, and the rice Lee.
- a third aspect of the invention provides the use of the pyrazoloquinazolinedione compound of the first aspect as a pesticide herbicide.
- a fourth aspect of the invention provides a pesticide herbicide comprising an active ingredient and an auxiliary agent, the active ingredient comprising at least one of the pyrazoloquinazolinedione compounds described in the above first aspect kind.
- the active ingredient is contained in an amount of from 1 to 99.9999% by weight.
- the active ingredient further comprises a safener.
- the safener can be various types of safeners conventionally used in the art.
- the safener may be pyrazolyl ester, detoxified quinone, dibenzoxazole acid, cyclopropanesulfonamide, naphthalic anhydride, chlorfenate, R-28725, benzamide, oxaloacetone, At least one of sulfamethoxazole, oxazolidine, chlorpyrifos, BAS-145138, furazosalazine, quinoline derivative, 2,4-D, a novel antidote T, and gibberellin.
- the pesticide herbicide is in a form selected from the group consisting of at least one of an emulsifiable concentrate, a suspending agent, a wettable powder, a powder, a granule, a liquid, a bait, a mother liquor, and a mother powder.
- the suspending agent may, for example, include a dry suspending agent, a dispersible oil suspending agent, and an aqueous emulsion.
- Excipients in the pesticide herbicides of the present invention include, but are not limited to, surfactants, protective colloids, binders, thickeners, thixotropic agents, penetrants, chelating agents, dyes, colorants, polymers, and the like, for example It can also be other conventional auxiliaries that act as carriers.
- a carrier herein refers to one or more organic, inorganic, natural, or synthetic materials. They aid in the administration of the active ingredient, which is generally inert and must be agriculturally acceptable, especially acceptable for treatment plants.
- the carrier may be solid, such as: clay, natural or synthetic silicates, silica, resins, waxes, solid fertilizers, etc.; or liquid, such as: water, alcohols, ketones, petroleum fractions, aromatic hydrocarbons or Wax hydrocarbons, chlorinated hydrocarbons, liquefied gases, and the like.
- the components of the surfactants of the present invention include emulsifiers, dispersants or wetting agents which may be ionic or nonionic. Examples which may be mentioned are: polyacrylates, lignosulfonates, phenolsulfonic or naphthalenesulfonates, ethylene oxide and aliphatic alcohols or with aliphatic acids or with aliphatic amines and substituted phenols (especially Is a polymer of alkylphenol or aryl phenol), sulfonic acid succinate, taurine derivative and phosphate ester of alcohol or polyhydroxyethylated phenol phosphate, alkyl sulfonate, alkyl aryl Sulfonate, alkyl sulfate, lauryl ether sulfate, fatty alcohol sulfate, and sulfated hexadecane-seven-octadecyl alcohol and sulfated fatty alcohol glycol ether, in addition
- the method for preparing the pesticide herbicide is not particularly limited, and those skilled in the art can prepare by using a conventional preparation method in the field of pesticides to form a corresponding reagent.
- the pesticide herbicides of the present invention include, but are not limited to, those used in crops by, for example, spraying.
- the pyrazoloquinazolinedione compound provided by the invention and the pesticide herbicide containing the pyrazoloquinazolinedione compound have all the advantages of the HPPD herbicide, and are environmentally friendly, and the crop is safe and low in dosage. Good timeliness, wide spectrum of killing, and high safety.
- the pyrazol quinazolinedione compounds provided by the present invention exhibit excellent crop safety against corn, wheat and rice.
- the pyrazoloquinazolinedione compound provided by the invention has high herbicidal activity against broadleaf weeds, grass weeds and sedge weeds, especially for the weeds in rice fields.
- grass weeds in the paddy field Herb, Qiangjin, Shuangsui, foxtail, crabgrass, rice, Lishihe, etc.
- broadleaf weeds water bamboo leaves, wild sage, diarrhea, rain Flowers, comfrey, ragweed, etc.; sedge (firefly, sedge, etc.).
- the present invention also provides the following three comparative compounds:
- test targets are as shown in Table 2 - Table 6.
- Post-emergence stem and leaf spray take 7cm inner diameter paper cup, install composite soil (garden soil: seedling substrate, 1:2, v/v) to 3/4, directly weed, cover soil 0.2cm, wait until length 4-5 Leaf period alternate.
- the compound of the present invention and the aforementioned comparative compounds D1, D2, and D3 are all applied to the greenhouse after the application of the automatic spray tower at a dose of 12 g/mu, and then transferred to the greenhouse for cultivation (25 degrees-28 degrees, humidity 70). %), the results of the survey after 30 days.
- the growth inhibition rate evaluation method was a visual method, and was specifically rated according to the conditions shown in Table 1, and the test results are shown in Table 2 - Table 6.
- the compound of the present invention exhibits good herbicidal activity against common grasses and broadleaf weeds in the herbicidal test experiment, and has a good control effect against valerian and foxtail, and the control agent D1. , D2, D3 have considerable herbicidal activity.
- the compound of the present invention is safe for corn and wheat. Further, the compound in which the carbamate fragment is attached in the present invention is also very safe for two kinds of rice (indica and japonica), and the crop safety is obviously superior to the control compound. It can be used to control malignant weeds such as valerian in paddy fields.
- control agents D1, D2 and D3 were not safe for testing japonica and japonica rice, and were almost completely inhibited, and could not be used for weed control in paddy fields.
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Abstract
本发明涉及农药除草剂领域,公开了一种吡唑喹唑啉二酮类化合物及其应用和一种农药除草剂,该化合物具有式(I)所示的结构。本发明提供的吡唑喹唑啉二酮类化合物具有优异的作物安全性和优异的除草效果。
Description
本发明涉及农药领域,具体涉及一种吡唑喹唑啉二酮类化合物及其应用、一种农药除草剂。
杂草抗药性的爆发性增长已经成为现代农业可持续发展所面临的一个关键挑战,而创制新型超高效除草剂是解决这一挑战的根本途径。
截至目前,我国正式报道的抗性杂草种类超过40种,是世界上抗性杂草危害最为严重的五个国家之一。特别是在我国几类重要的农作物田中,杂草抗药性的问题已经呈现出愈演愈烈的趋势。
例如,水稻田中的稗草、马唐、狗尾草、千金子等杂草对目前市面上的主要稻田除草剂均产生了严重的抗药性;小麦田中的播娘蒿、荠菜、看麦娘、日本看麦娘、雀麦、节节麦、野燕麦等主要杂草的抗性种群也已经发展成为优势杂草,导致部分省市区域的稻田或麦田除草剂用量不断加大,不仅增加了防治成本,而且导致药害事件频发、农药残留超标。
因此,为了实现“减量增效、绿色发展”的发展要求,创制出作用机制新颖的超高效除草剂以替代传统除草剂,是防治抗性杂草、实现减量增效和绿色发展的根本途径。
靶向对羟苯基丙酮酸双加氧酶(HPPD)的除草剂因其高效、低毒、环境友好以及抗性风险低等特点被广泛使用。
截止目前,靶向HPPD所开发成功的除草剂多达数十种,以结构分类大致可以归为三大类:
1、以硝磺草酮(Mesotrione)为代表的三酮类;
2、以苯唑草酮(Topramezone)为代表的吡唑类;
3、以异噁氯草酮(Isoxachlortole)为代表的异噁唑类。
经过农药市场销售额调查,HPPD抑制类除草剂进入市场时间与AHAS-、PPO-以及ACCase-抑制类除草剂相比起步虽晚,但不妨碍其中的“明星分子”对市场的迅速占领,特别是由先正达公司研发的三酮类除草剂-硝磺草酮(又名:甲基磺草酮),连续多年占领除草剂销售额前五。在抗性杂草多发的玉米田中,硝磺草酮已经逐渐代替了其他类型的除草剂,成为使用最广和最为有效的玉米田除草剂。
然而,硝磺草酮仍然存在着一些自身不足,例如其对其它的一些大宗作物如水稻、小麦等安全性较差,同时硝磺草酮对多种禾本科杂草(如普发性杂草狗尾草和金狗尾草等)防效较差,也有文献报道使用硝磺草酮后杂草易出现返青现象等。
我国农业生产实际中还没有兼备广谱性和超高效除草活性且能够用于水稻田的HPPD除草剂,尤其是还没有对抗性稗草、千金子等多种难防除的恶性杂草具有优异防效的除草剂。
因此,为满足我国农业生产中的现实需求,创制出对水稻安全的新型超高效HPPD除草剂具有十分重要的意义。
另外,WO2017/140612A1公开了一类喹唑啉二酮-6-羰基衍生物作为HPPD抑制剂。然而,该现有技术中记载的化合物对水稻、小麦等作物并没有表现出足够的安全性,使得它们不能直接用于水稻田进行杂草的防治。
发明内容
本发明的目的是为了克服现有技术存在的前述缺陷,提供一类新的、具有高的安全性的能够用于防除作物(特别是水稻田)中的杂草的吡唑喹唑啉二酮类化合物以实现优异的除草效果。
为了实现前述发明目的,本发明的第一方面提供了一种吡唑喹唑啉二酮类化合物,该化合物 具有式(I)所示的结构,
其中,在式(I)中,
X选自C
1-12的烷基、由1-6个选自卤素的原子取代的C
1-12的烷基、由C
1-3的烷氧基取代的C
2-12的烷基、C
2-12的烯基、C
2-12的炔基、含有选自O、N、S中的至少一种杂原子的C
2-12的环烷基、由含有选自O、N、S中的至少一种杂原子的C
2-6的环烷基取代的C
3-12的烷基;
Y选自H、C
1-6的烷基;
Z为H或式(I-1)所示的基团,其中,在式(I-1)中,R
1和R
2相同或不同,各自独立地选自C
1-6的烷基。
以下对本发明的术语进行解释。
“C
1-12的烷基”表示碳原子总数为1-12的烷基,包括直链烷基、支链烷基或者环烷基,例如可以为碳原子总数为1、2、3、4、5、6、7、8、9、10、11或12的直链烷基、支链烷基或者环烷基,例如可以为甲基、乙基、正丙基、异丙基、正丁基、异丁基、叔丁基、正戊基、异戊基、正己基、环丙基、甲基环丙基、乙基环丙基、环丁基、甲基环丁基、乙基环丁基、环戊基、甲基环戊基、乙基环戊基、环己基、甲基环己基、乙基环己基等。
“由1-6个选自卤素的原子取代的C
1-12的烷基”表示碳原子总数为1-12的烷基,包括直链烷基、支链烷基和环烷基,并且该C
1-12的烷基中的1-6个H由选自卤素的卤原子取代,例如该C
1-12的烷基中的1、2、3、4、5或6个H由选自氟、氯、溴、碘中的任意一个或者多个卤原子取代,例如可以为三氟甲基、二氟甲基、一氟甲基、一氟乙基、二氟乙基、三氟乙基、一氟丙基、二氟丙基、三氟丙基等。
“由C
1-3的烷氧基取代的C
2-12的烷基”表示碳原子总数为2-12的基团,且该基团的结构式可以表示为-R
1OR
2,其中,R
1和R
2中的碳原子数之和为2-12,且R
1直接与本发明的式(I)所示结构的化合物的母核结构连接。
“C
2-12的烯基”表示碳原子总数为2-12的烃基,且该烃基中至少有一个烯键。
“C
2-12的炔基”表示碳原子总数为2-12的烃基,且该烃基中至少有一个炔键。
“含有选自O、N、S中的至少一种杂原子的C
2-12的环烷基”表示碳原子总数为2-12的环烷基,且形成环的原子中含有选自O、N、S中的至少一种杂原子,并且形成环的各个原子上可以含有烷基取代基,该烷基取代基中含有的碳原子数包括在前述碳原子总数范围内。例如可以为三元环、四元环、五元环、六元环、七元环、八元环、九元环、十元环、十一元环或十二元环,并且,环烷基中的H可以任意地被取代基取代或者未取代,若被取代,其中的取代基各自独立地选自烷基、卤素、羟基、硝基和巯基中的至少一种。
“由含有选自O、N、S中的至少一种杂原子的C
2-6的环烷基取代的C
3-12的烷基”表示碳原子总数为3-12的基团,且该基团中含有至少一个包括选自O、N、S中的至少一种杂原子的C
2-6的环烷基,该环烷基中的碳原子数包括在前述碳原子总数范围内。
根据一种优选的具体实施方式,在式(I)中,
X选自C
1-8的烷基、由1-6个选自卤素的原子取代的C
1-8的烷基、由C
1-3的烷氧基取代的C
2-8的烷基、C
2-8的烯基、C
2-8的炔基、含有至少一个O原子的C
2-8的环烷基、由含有至少一个O原子的C
2-6的环烷基取代的C
3-8的烷基;
Y选自H、C
1-4的烷基;
Z为H或式(I-1)所示的基团,其中,在式(I-1)中,R
1和R
2相同或不同,各自独立地选自C
1-4的烷基。
优选情况下,在式(I)中,Z为H。
根据一种特别优选的具体实施方式,在式(I)中,
X选自C
1-12的烷基、由1-6个选自卤素的原子取代的C
1-12的烷基、由C
1-3的烷氧基取代的C
2-12的烷基、C
2-12的烯基、C
2-12的炔基、含有选自O、N、S中的至少一种杂原子的C
2-12的环烷基、由含有选自O、N、S中的至少一种杂原子的C
2-6的环烷基取代的C
3-12的烷基;
Y选自H、C
1-6的烷基;
Z为H。
根据另一种特别优选的具体实施方式,在式(I)中,
X选自C
1-8的烷基、由1-6个选自卤素的原子取代的C
1-8的烷基、由C
1-3的烷氧基取代的C
2-8的烷基、C
2-8的烯基、C
2-8的炔基、含有至少一个O原子的C
2-8的环烷基、由含有至少一个O原子的C
2-6的环烷基取代的C
3-8的烷基;
Y选自H、C
1-4的烷基;
Z为H。
根据还有一种特别优选的具体实施方式,在式(I)中,
X选自C
1-12的烷基、由1-6个选自卤素的原子取代的C
1-12的烷基、由C
1-3的烷氧基取代的C
2-12的烷基、C
2-12的烯基、C
2-12的炔基、含有选自O、N、S中的至少一种杂原子的C
2-12的环烷基、由含有选自O、N、S中的至少一种杂原子的C
2-6的环烷基取代的C
3-12的烷基;
Y选自H、C
1-6的烷基;
Z为式(I-1)所示的基团,且在式(I-1)中,R
1和R
2相同或不同,各自独立地选自C
1-3的烷基。
根据还有一种特别优选的具体实施方式,在式(I)中,
X选自C
1-8的烷基、由1-6个选自卤素的原子取代的C
1-8的烷基、由C
1-3的烷氧基取代的C
2-8的烷基、C
2-8的烯基、C
2-8的炔基、含有至少一个O原子的C
2-6的环烷基、由含有至少一个O原子的C
2-6的环烷基取代的C
3-8的烷基;
Y选自H、C
1-4的烷基;
Z为式(I-1)所示的基团,且在式(I-1)中,R
1和R
2相同或不同,各自独立地选自C
1-3的烷基。
特别优选情况下,本发明所述的吡唑喹唑啉二酮类化合物选自以下化合物中的至少一种:
本发明提供的吡唑喹唑啉二酮类化合物具有优异的作物安全性和优异的除草效果。
特别优选地,本发明提供的引入了烷基取代的氨基甲酸片段的吡唑喹唑啉二酮类化合物不仅对稻田杂草效果有效,而且明显比现有技术的化合物对水稻的安全性更高。
本发明对合成式(I)所示的吡唑喹唑啉二酮类化合物的方法没有特别的限定,本领域技术人员根据本发明提供的化合物结构结合化学领域内的合成方法能够获得合适的制备式(I)所示的吡唑喹唑啉二酮类化合物的方法,本发明在此不再一一赘述。
例如,本发明的式(I)所示的吡唑喹唑啉二酮类化合物可以根据如下合成路线合成:
上述合成路线中的起始原料例如可以利用CN104557739A中所描述的方法制备。
在上述合成路线中,在酯化反应中,产物的合成方法例如可以为:将原料溶于溶剂中,加草酰氯,低温下搅拌反应。待反应完毕,脱干溶剂,剩余固体用溶剂溶解备用。低温下,将吡唑酮溶于溶剂中,并加入三乙胺,搅拌后,将用溶剂溶解的酰氯溶液滴加到反应体系中,TLC监测反应。待反应完毕,向反应体系中加入饱和NaHCO
3溶液,萃取合并有机层,干燥浓缩进行柱层析得到产物。
在上述合成路线中,在重排反应中,产物的合成方法例如可以为:将原料、乙腈加入到烧瓶中,搅拌,加入Et
3N和丙酮氰醇。TLC监测反应,待反应完成后,向反应体系中加入HCl溶液,继续搅拌,析出固体抽滤。
本发明的第二方面提供第一方面所述的吡唑喹唑啉二酮类化合物在防治杂草中的应用。
优选地,所述杂草选自阔叶杂草、禾本科杂草和莎草科杂草中的至少一种。
进一步优选地,所述杂草包括狗尾草、稗草、千金子、马唐、节节麦、苋菜、灰菜、苘麻、雀麦、野燕麦、看麦娘、日本看麦娘、黑麦草、饭包草、决明草、牵牛花、苍耳、莎草、大巢菜、反枝苋、假酸浆、鳢肠、马齿苋、刺苋、鬼针草、双穗雀稗、稻李氏禾、水竹叶、野慈姑、泽泻、雨久花、鸭跖草、鸭舌草、萤蔺、异型莎草等中的至少一种。
优选地,在本发明中,所述阔叶杂草包括苋菜、灰菜、苘麻、饭包草、决明草、牵牛、苍耳、反枝苋、假酸浆、鳢肠、马齿苋、刺苋、水竹叶、野慈姑、泽泻、雨久花、鸭跖草、鸭舌草和莎草中的至少一种。所述莎草包括萤蔺、异型莎草等。
优选地,在本发明中,所述禾本科杂草包括狗尾草、稗草、千金子、马唐、节节麦、雀麦、野燕麦、看麦娘、日本看麦娘、黑麦草、莎草、大巢菜、鬼针草、双穗雀稗、稻李氏禾中的至少一种。
本发明的第三方面提供第一方面所述的吡唑喹唑啉二酮类化合物作为农药除草剂的应用。
本发明的第四方面提供一种农药除草剂,该农药除草剂由活性成分和辅料组成,所述活性成分包括前述第一方面中所述的吡唑喹唑啉二酮类化合物中的至少一种。
优选地,在所述农药除草剂中,所述活性成分的含量为1~99.9999重量%。
根据一种优选的具体实施方式,所述活性成分中进一步包括安全剂。所述安全剂可以为本领域内常规使用的各种类型的安全剂。
例如,所述安全剂可以为吡唑解草酯、解毒喹、双苯噁唑酸、环丙磺酰胺、萘二甲酸酐、氯草烯安、R-28725、苯叉酰胺、解草酮、解草胺腈、解草唑、解草啶、BAS-145138、呋喃解草唑、喹啉衍生物、2,4-D、新型解毒剂T和赤霉素中的至少一种。
优选情况下,所述农药除草剂的剂型选自乳油、悬浮剂、可湿性粉剂、粉剂、粒剂、水剂、毒饵、母液和母粉中的至少一种。
所述悬浮剂例如可以包括干悬浮剂、可分散油悬浮剂和水乳剂。
本发明的所述农药除草剂中的辅料包括但不限于表面活性剂、保护胶体、粘合剂、增稠剂、触变剂、渗透剂、螯合剂、染料、着色剂和聚合物等,例如还可以为充当载体的其它常规助剂。
本文中的载体表示一种或多种有机物、无机物、天然产物或合成的物质。它们有助于活性成分的施用,该载体一般是惰性的且必须是农业上可以接受的,特别是可以被处理植物所接受的。载体可以是固体的,如:陶土、天然或合成的硅酸盐、二氧化硅、树脂、蜡、固体肥料等;或者是液 体的,如:水,醇类、酮类、石油馏分、芳烃或蜡烃、氯代烃、液化气等。
本发明所述表面活性剂的成分包括乳化剂,分散剂或润湿剂,它们可以是离子型的或非离子型的。可提及的实例是:聚丙烯酸盐、木质素磺酸盐、苯酚磺酸或萘磺酸盐、环氧乙烷与脂肪族醇或与脂肪族酸或与脂肪族胺与取代的苯酚(特别是烷基苯酚或芳基苯酚)的聚合物、磺酸琥珀酸盐、牛磺酸衍生物及醇的磷酸酯或多羟基乙基化的苯酚磷酸酯、烷基磺酸酯盐、烷基芳基磺酸盐、烷基硫酸盐、月桂基醚硫酸盐、脂肪醇硫酸盐、以及硫酸化十六-十七-十八烷醇以及硫酸化脂肪醇乙二醇醚,此外还有萘或萘磺酸与苯酚和甲醛的缩合物、聚氧乙烯辛基苯甲醚、乙氧基化异辛基醚、辛基酚或壬基酚、烷基苯基聚乙二醇醚、三丁基苯基聚乙二醇醚、三硬酯基苯基聚乙二醇醚、烷基芳基聚醚醇、醇和脂肪醇/氧化乙烯缩合物、乙氧基化蓖麻油、聚氧乙烯烷基醚、乙氧基化聚氧丙烯、月桂醇聚乙二醇醚缩醛、山梨醇酯、木素亚硫酸盐废液、以及蛋白质、变性蛋白、多糖、疏水改性淀粉、聚乙烯醇、聚羧酸盐、聚氧烷基化物、聚乙烯胺、聚乙烯吡咯烷酮以及共聚物。
本发明对制备所述农药除草剂的方法没有特别的限制,本领域技术人员可以采用农药领域内常规的制备方法进行制备以形成相应的试剂。
本发明所述的农药除草剂包括但不限于通过例如喷雾的方法用于农作物。
本发明提供的吡唑喹唑啉二酮类化合物及含有该吡唑喹唑啉二酮类化合物的农药除草剂具有HPPD类除草剂的全部优点,并且具有环境友好,后茬作物安全、用量低、时效性好、杀草谱广、安全性高等优点。
特别地,本发明提供的吡唑喹唑啉二酮类化合物对玉米、小麦和水稻表现出了优良的作物安全性。
本发明提供的吡唑喹唑啉二酮类化合物对阔叶杂草、禾本科杂草和莎草科杂草均具有很高的除草活性,尤其是对水稻田内杂草的防效显著,例如对水稻田中的禾本科杂草(稗草、千金子、双穗雀稗、狗尾草、马唐、稻李氏禾等);阔叶杂草(水竹叶、野慈姑、泽泻、雨久花、鸭跖草、鸭舌草等);莎草(萤蔺、异型莎草等)。
在本文中所披露的范围的端点和任何值都不限于该精确的范围或值,这些范围或值应当理解为包含接近这些范围或值的值。对于数值范围来说,各个范围的端点值之间、各个范围的端点值和单独的点值之间,以及单独的点值之间可以彼此组合而得到一个或多个新的数值范围,这些数值范围应被视为在本文中具体公开。
以下提供本发明的部分具体化合物的制备方法,本领域技术人员不应理解为对本发明的限制。在没有特别说明的情况下,使用的各种原料均来自商购。
化合物1的合成:
将1g的中间体a加入到50mL单颈瓶中,加入18mL干燥的THF,室温下缓慢滴加1.8g的SOCl
2,滴加完毕后75℃回流反应约1.5h,TLC跟踪反应进程,反应结束后脱干溶剂。加入20mL干燥的CHCl
3,0.7g的2,5-二甲基-2,4-二氢-3H-吡唑-3-酮,0.61g的Et
3N,反应约0.5h,TLC跟踪至酰氯消失。反应完毕后用20mL水洗一次,每次用10mL的1摩尔/升的HCl洗2次,每次用10mL的饱和NaHCO
3洗2次,无水Na
2SO
4干燥,过柱得中间体b。
将0.7g式化合物b加入到50mL两颈瓶中,加入28mL无水乙腈,N
2保护下加入0.38g的Et
3N,0.018g(10%当量)的丙酮氰醇。室温下反应8h,TLC跟踪至反应原料消失。反应完毕后脱干乙腈,加入约30mL的CHCl
3。每次用10mL的1摩尔/升的盐酸洗三次,饱和氯化钠每次10mL洗3次,有机层用无水硫酸钠干燥。减压脱去溶剂得浅黄色油状物,所得油状物用10mL甲醇重结晶,得到化合物1。
化合物2的合成:
将10mmol的中间体a加入到50mL单颈瓶中,加入18mL干燥的THF,室温下缓慢滴加15mmol的SOCl
2,滴加完毕后75℃回流反应约1.5h,TLC跟踪反应进程,反应结束后脱干溶剂。加入20mL干燥的CHCl
3,15mmol的5-环丙基-2-甲基-2,4-二氢-3H-吡唑-3-酮,15mmol的Et
3N,反应约0.5h,TLC跟踪至酰氯消失。反应完毕后用20mL水洗一次,每次用10mL的1摩尔/升的HCl洗2次,每次用10mL的饱和NaHCO
3洗2次,无水Na
2SO
4干燥,过柱,得中间体c。
将5mmol中间体c加入到50mL两颈瓶中,加入28mL无水乙腈,N
2保护下加入10mmol的Et
3N,0.05mmol(10%当量)的丙酮氰醇。室温下反应8h,TLC跟踪至反应原料消失。反应完毕后脱干乙腈,加入约30mL的CHCl
3。每次用10mL的1摩尔/升的盐酸洗三次,饱和氯化钠每次10mL洗3次,有机层用无水硫酸钠干燥。减压脱去溶剂得浅黄色油状物,所得油状物用10mL甲醇重结晶,得到化合物2。
化合物5合成:
在冰浴下,将1mmol化合物1溶于干燥的二氯甲烷中,加入Et
3N(1.5mmol),并缓慢向反应体系中加入N,N-二甲基氨基甲酰氯(1.5mmol)溶液,室温反应。当反应完成后,向反应体系中加入饱和碳酸氢钠溶液(15ml),二氯甲烷萃取(10mL×3),合并有机相,减压蒸馏,拌样柱层析分离提纯得到化合物5。
采用前述相似的方法合成本发明的其他化合物,部分化合物的表征数据如下:
化合物1收率:62%.
1H NMR(400MHz,CDCl
3)δ7.47(d,J=8.8Hz,1H),7.18(d,J=8.8Hz,1H),3.65(s,3H),3.64(s,3H),3.47(s,3H),2.78(s,3H),1.71(s,3H).
化合物2收率:73%.
1H NMR(400MHz,CDCl
3)δ7.56(d,J=8.8Hz,1H),7.14(d,J=8.8Hz,1H),3.69(s,3H),3.58(s,3H),3.47(s,3H),2.78(s,3H),0.98–0.90(m,1H),0.83–0.75(m,2H),0.55–0.45(m,2H).
化合物3收率:66%.
1H NMR(400MHz,CDCl
3)δ7.45(d,J=8.8Hz,1H),7.21(s,1H),7.17(d,J=8.8Hz,1H),3.65(s,3H),3.64(s,3H),3.47(s,3H),2.78(s,3H).
化合物4收率:89%.,
1H NMR(400MHz,CDCl
3)δ7.49(d,J=7.6Hz,1H),7.10(d,J=7.6Hz,1H),3.62(s,3H),3.60(s,3H),3.46(s,3H),3.23(s,6H),2.74(s,3H),2.16(s,3H).
化合物5收率:78%.
1H NMR(400MHz,CDCl
3)δ7.50(d,J=8.8Hz,1H),7.07(d,J=8.8Hz, 1H),3.61(s,3H),3.60(s,3H),3.46(s,3H),3.19(q,J=7.2Hz,2H),3.04(q,J=7.2Hz,2H),2.76(s,3H),2.18(s,3H),1.08(t,J=7.2Hz,3H),1.05–1.01(t,J=7.2Hz,3H).
化合物6收率:70%.
1H NMR(400MHz,CDCl
3)δ7.53(d,J=8.8Hz,1H),7.10(d,J=8.8Hz,1H),3.61(s,3H),3.59(s,3H),3.46(s,3H),3.19(q,J=7.2Hz,2H),3.04(q,J=7.2Hz,2H),2.76(s,3H),1.08(t,J=7.2Hz,3H),1.05–1.01(t,J=7.2Hz,3H),0.98–0.90(m,1H),0.83–0.75(m,2H),0.55–0.45(m,2H).
化合物7收率:65%.,
1H NMR(400MHz,CDCl
3)δ7.55(d,J=7.6Hz,1H),7.08(d,J=7.6Hz,1H),3.62(s,3H),3.60(s,3H),3.45(s,3H),3.23(s,3H),3.07(q,J=8.4Hz,2H),2.76(s,3H),2.18(s,3H),1.17(t,J=7.2Hz,3H).
化合物8收率:70%.,
1H NMR(400MHz,CDCl
3)δ7.53(d,J=7.6Hz,1H),7.07(d,J=7.6Hz,1H),3.61(s,3H),3.59(s,3H),3.46(s,3H),3.29–3.21(m,5H),2.76(s,3H),2.18(s,3H),1.75–1.61(m,2H),0.87(t,J=7.6Hz,3H).
化合物9收率:69%.
1H NMR(400MHz,CDCl
3)δ7.45(d,J=8.8Hz,1H),7.16(d,J=8.8Hz,1H),4.12(q,J=6.8Hz,2H),3.63(s,3H),3.62(s,3H),2.77(s,3H),1.70(s,3H),1.28(t,J=7.2Hz,3H).
化合物10收率:63%.
1H NMR(400MHz,CDCl
3)δ7.56(d,J=8.8Hz,1H),7.15(d,J=8.8Hz,1H),4.12(q,J=6.8Hz,2H),3.61(s,3H),3.59(s,3H),2.82(s,3H),1.28(t,J=6.8Hz,3H),0.98–0.90(m,1H),0.83–0.75(m,2H),0.55–0.45(m,2H).
化合物11收率:66%.
1H NMR(400MHz,CDCl
3)δ7.46(d,J=8.8Hz,1H),7.20(s,1H),7.16(d,J=8.8Hz,1H),4.12(q,J=6.8Hz,2H),3.63(s,3H),3.60(s,3H),2.78(s,3H),1.27(t,J=7.2Hz,3H).
化合物12收率:65%.,
1H NMR(400MHz,CDCl
3)δ7.50(d,J=8.8Hz,1H),7.08(d,J=8.8Hz,1H),4.12(q,J=7.2Hz,2H),3.62(s,3H),3.60(s,3H),3.23(s,6H),2.34(s,3H),1.98(s,3H),1.18(t,J=7.6Hz,3H).
化合物13收率:68%.
1H NMR(400MHz,CDCl
3)δ7.49(d,J=8.8Hz,1H),7.08(d,J=8.8Hz,1H),4.12(q,J=7.2Hz,2H),3.61(s,3H),3.59(s,3H),3.18(q,J=7.2Hz,2H),3.03(q,J=7.2Hz,2H),2.75(s,3H),2.21(s,3H),1.27(t,J=7.2Hz,3H),1.08(t,J=7.2Hz,3H),1.01(t,J=7.2Hz,3H).
化合物14收率:74%.
1H NMR(400MHz,CDCl
3)δ7.54(d,J=8.8Hz,1H),7.09(d,J=8.8Hz,1H),4.11(q,J=7.2Hz,2H),3.61(s,3H),3.59(s,3H),3.18(q,J=7.2Hz,2H),3.03(q,J=7.2Hz,2H),2.82(s,3H),1.27(t,J=7.2Hz,3H),1.08(t,J=7.2Hz,3H),1.02(t,J=7.2Hz,3H),0.98–0.90(m,1H),0.83–0.75(m,2H),0.55–0.45(m,2H).
化合物15收率:73%.,
1H NMR(400MHz,CDCl
3)δ7.50(d,J=8.8Hz,1H),7.10(d,J=8.8Hz,1H),4.12(q,J=7.2Hz,2H),3.61(s,3H),3.58(s,3H),3.23(s,3H),3.15(q,J=12.8Hz,2H),2.75(s,3H),2.21(s,3H),1.14–0.97(m,6H).
化合物16收率:78%.,
1H NMR(400MHz,CDCl
3)δ7.51(d,J=8.8Hz,1H),7.08(d,J=8.8Hz,1H),4.10(q,J=6.8Hz,2H),3.62(s,3H),3.56(s,3H),3.24(s,3H),3.20–2.88(m,2H),2.74(s,3H),2.22(s,3H),1.75–1.61(m,2H),1.18(t,J=7.6Hz,3H),1.01(t,J=7.2Hz,3H).
化合物17收率:72%.
1H NMR(400MHz,CDCl
3)δ7.46(d,J=8.8Hz,1H),7.16(d,J=8.8Hz,1H),4.05–3.99(m,2H),3.64(s,3H),3.62(s,3H),2.77(s,3H),1.75–1.69(m,5H),0.99(t,J=7.4Hz,3H).
化合物18收率:64%.
1H NMR(400MHz,CDCl
3)δ7.58(d,J=8.8Hz,1H),7.17(d,J=8.8Hz,1H),4.05–3.99(m,2H),3.64(s,3H),3.62(s,3H),2.84(s,3H),1.77–1.66(m,2H),1.05–0.94(m,4H),0.88–0.80(m,2H),0.58–0.50(m,2H).
化合物19收率:77%.
1H NMR(400MHz,CDCl
3)δ7.45(d,J=8.8Hz,1H),7.20(s,1H),7.17(d,J=8.8Hz,1H),4.05–3.99(m,2H),3.64(s,3H),3.62(s,3H),2.80(s,3H),1.77–1.66(m,2H),1.00(t,J=7.2Hz,3H).
化合物20收率:69%.,
1H NMR(400MHz,CDCl
3)δ7.49(d,J=8.8Hz,1H),7.09(d,J=8.8Hz,1H),4.05–3.97(m,2H),3.62(s,3H),3.59(s,3H),3.23(s,6H),2.74(s,3H),2.21(s,3H),1.75–1.66(m, 2H),0.99(t,J=7.2Hz,3H).
化合物21收率:79%.
1H NMR(400MHz,CDCl
3)δ7.49(d,J=8.8Hz,1H),7.08(d,J=8.8Hz,1H),4.05–3.97(m,2H),3.61(s,3H),3.59(s,3H),3.18(q,J=7.1Hz,2H),3.03(q,J=7.2Hz,2H),2.75(s,3H),2.22(s,3H),1.75–1.64(m,2H),1.08(t,J=7.2Hz,3H),1.03–0.95(m,6H).
化合物22收率:83%.
1H NMR(400MHz,CDCl
3)δ7.55(d,J=8.8Hz,1H),7.06(d,J=8.8Hz,1H),4.05–3.97(m,2H),3.61(s,3H),3.59(s,3H),3.18(q,J=7.2Hz,2H),3.03(q,J=7.2Hz,2H),2.75(s,3H),1.75–1.64(m,2H),1.08(t,J=7.2Hz,3H),1.03–0.90(m,7H),0.83–0.75(m,2H),0.55–0.45(m,2H).
化合物23收率:73%.,
1H NMR(400MHz,CDCl
3)δ7.48(d,J=8.8Hz,1H),7.08(d,J=8.8Hz,1H),4.05–3.98(m,2H),3.61(s,3H),3.58(s,3H),3.23(s,3H),3.07(q,J=7.6Hz,2H),2.74(s,3H),2.21(s,3H),1.75–1.64(m,2H),1.16(t,J=7.2Hz,3H),0.99(t,J=7.2Hz,3H).
化合物24收率:76%.,
1H NMR(400MHz,CDCl
3)δ7.46(d,J=9.2Hz,1H),7.09(d,J=9.2Hz,1H),4.05–3.97(m,2H),3.62(s,3H),3.59(s,3H),3.26–3.19(m,4H),3.04(t,J=7.6Hz,1H),2.75(s,3H),2.20(s,3H),1.74–1.62(m,4H),0.91–0.80(m,6H).
化合物25收率:69%.
1H NMR(400MHz,CDCl
3)δ7.43(d,J=8.8Hz,1H),7.13(d,J=8.8Hz,1H),5.35–5.24(m,1H),3.64(s,3H),3.58(s,3H),2.75(s,3H),1.71(s,3H),1.52(d,J=6.8Hz,6H).
化合物26收率:89%.
1H NMR(400MHz,CDCl
3)δ7.53(d,J=8.8Hz,1H),7.11(d,J=8.8Hz,1H),5.33–5.23(m,1H),3.60(s,3H),3.57(s,3H),2.79(s,3H),1.52(d,J=6.8Hz,6H),1.00–0.92(m,1H),0.83–0.76(m,2H),0.56–0.47(m,2H).
化合物27收率:79%.
1H NMR(400MHz,CDCl
3)δ7.45(d,J=8.8Hz,1H),7.21(s,1H),7.12(d,J=8.8Hz,1H),5.33–5.23(m,1H),3.60(s,3H),3.57(s,3H),2.79(s,3H),1.52(d,J=6.8Hz,6H).
化合物28收率:79%.,
1H NMR(400MHz,CDCl
3)δ7.47(d,J=9.6Hz,1H),7.03(d,J=9.6Hz,1H),5.35–5.22(m,1H),3.61(s,3H),3.54(s,3H),3.23(s,6H),2.72(s,3H),2.22(s,3H),1.52(d,J=12.0Hz,6H).
化合物29收率:87%.
1H NMR(400MHz,CDCl
3)δ7.47(d,J=8.8Hz,1H),7.04(d,J=8.8Hz,1H),5.35–5.22(m,1H),3.61(s,3H),3.55(s,3H),3.18(q,J=7.2Hz,2H),3.03(q,J=7.2Hz,2H),2.73(s,3H),2.23(s,3H),1.51(d,J=6.8Hz,6H),1.08(t,J=7.2Hz,3H),1.01(t,J=7.2Hz,3H).
化合物30收率:73%.
1H NMR(400MHz,CDCl
3)δ7.53(d,J=8.8Hz,1H),7.03(d,J=8.8Hz,1H),5.33–5.22(m,1H),3.61(s,3H),3.57(s,3H),3.18(q,J=7.2Hz,2H),3.03(q,J=7.2Hz,2H),2.72(s,3H),1.51(d,J=6.8Hz,6H),1.08(t,J=7.2Hz,3H),1.03–0.92(m,4H),0.83–0.76(m,2H),0.56–0.47(m,2H).
化合物31收率:80%.,
1H NMR(400MHz,CDCl
3)δ7.46(d,J=8.4Hz,1H),7.04(d,J=8.4Hz,1H),5.35–5.22(m,1H),3.62(s,3H),3.57(s,3H),3.23(s,3H),3.07(q,J=7.6Hz,2H),2.73(s,3H),2.21(s,3H),1.51(d,J=6.8Hz,6H),1.17(t,J=7.2Hz,3H).
化合物32收率:77%.,
1H NMR(400MHz,CDCl
3)δ7.47(d,J=9.2Hz,1H),7.03(d,J=9.2Hz,1H),5.35–5.22(m,1H),3.63(s,3H),3.57(s,3H),3.27–3.19(m,4H),3.01(t,J=9.6Hz,1H),2.75(s,3H),2.23(s,3H),1.74–1.62(m,2H),1.51(d,J=7.2Hz,6H),0.90(t,J=7.2Hz,3H).
化合物33收率:65%.
1H NMR(400MHz,CDCl
3)δ7.44(d,J=8.8Hz,1H),7.13(d,J=8.8Hz,1H),5.11–5.00(m,1H),3.64(s,3H),3.59(s,3H),2.75(s,3H),2.17–2.03(m,1H),1.97–1.84(m,1H),1.72(s,3H),1.50(d,J=6.8Hz,3H),0.88(t,J=7.6Hz,3H).
化合物34收率:77%.
1H NMR(400MHz,CDCl
3)δ7.54(d,J=8.4Hz,1H),7.12(d,J=8.4Hz,1H),5.11–5.00(m,1H),3.60(s,3H),3.58(s,3H),2.80(s,3H),2.16–2.04(m,1H),1.97–1.84(m,1H),1.50(d,J=6.8Hz,3H),1.01–0.94(m,1H),0.88(t,J=7.2Hz,3H),0.83–0.77(m,2H),0.58–0.48(m,2H).
化合物35收率:72%.
1H NMR(400MHz,CDCl
3)δ7.45(d,J=8.4Hz,1H),7.19(s,1H),7.12(d,J=8.4Hz,1H),5.11–5.00(m,1H),3.61(s,3H),3.58(s,3H),2.80(s,3H),2.16–2.04(m,1H),1.97– 1.84(m,1H),1.51(d,J=6.8Hz,3H),0.89(t,J=7.2Hz,3H).
化合物36收率:80%.,
1H NMR(400MHz,CDCl
3)δ7.47(d,J=8.8Hz,1H),7.03(d,J=8.8Hz,1H),5.10–5.00(m,1H),3.60(s,3H),3.56(s,3H),3.23(s,6H),2.72(s,3H),2.23(s,3H),2.17–1.81(m,2H),1.47(d,J=6.8Hz,3H),0.87(t,J=7.2Hz,3H).
化合物37收率:74%.
1H NMR(400MHz,CDCl
3)δ7.47(d,J=8.4Hz,1H),7.04(d,J=8.4Hz,1H),5.10–4.99(m,1H),3.60(s,3H),3.55(s,3H),3.16(q,J=7.2Hz,2H),3.01(q,J=7.2Hz,2H),2.72(s,3H),2.25(s,3H),2.17–2.03(m,1H),1.94–1.81(m,1H),1.48(d,J=7.2Hz,3H),1.05(t,J=7.2Hz,3H),1.00(t,J=7.2Hz,3H),0.86(t,J=7.2Hz,3H).
化合物38收率:79%.
1H NMR(400MHz,CDCl
3)δ7.54(d,J=8.4Hz,1H),7.07(d,J=8.4Hz,1H),5.10–4.98(m,1H),3.60(s,3H),3.55(s,3H),3.16(q,J=7.2Hz,2H),3.01(q,J=7.2Hz,2H),2.70(s,3H),2.16–1.81(m,2H),1.48(d,J=7.2Hz,3H),1.05(t,J=7.2Hz,3H),1.01–0.94(m,4H),0.86(t,J=7.2Hz,3H),0.83–0.77(m,2H),0.58–0.48(m,2H).
化合物39收率:70%.,
1H NMR(400MHz,CDCl
3)δ7.47(d,J=8.8Hz,1H),7.03(d,J=8.8Hz,1H),5.10–5.00(m,1H),3.61(s,3H),3.55(s,3H),3.23(s,3H),3.07(q,J=7.2Hz,2H),2.74(s,3H),2.25(s,3H),2.17–2.03(m,1H),1.94–1.81(m,1H),1.48(d,J=7.2Hz,3H),1.17(t,J=6.8Hz,3H),0.86(t,J=7.2Hz,3H).
化合物40收率:85%.,
1H NMR(400MHz,CDCl
3)δ7.46(d,J=8.4Hz,1H),7.04(d,J=8.4Hz,1H),5.10–4.99(m,1H),3.61(s,3H),3.54(s,3H),3.29–3.17(m,4H),3.04(t,J=7.2Hz,1H),2.74(s,3H),2.23(s,3H),2.17–1.61(m,4H),1.48(d,J=7.2Hz,3H),0.87(t,J=7.2Hz,6H).
化合物41收率:86%.
1H NMR(400MHz,CDCl
3)δ7.45(d,J=8.8Hz,1H),7.16(d,J=8.8Hz,1H),4.05(t,J=7.2Hz 2H),3.64(s,3H),3.62(s,3H),2.77(s,3H),1.71(s,3H),1.69–1.62(m,2H),1.46–1.36(m,2H),0.96(t,J=7.2Hz,3H).
化合物42收率:87%.
1H NMR(400MHz,CDCl
3)δ7.56(d,J=8.8Hz,1H),7.15(d,J=8.8Hz,1H),4.08–4.02(m,2H),3.61(s,3H),3.59(s,3H),2.82(s,3H),1.71–1.61(m,2H),1.46–1.35(m,2H),0.96(t,J=5.6Hz,3H),0.94–0.91(m,1H),0.83–0.76(m,2H),0.55–0.46(m,2H).
化合物43收率:72%.
1H NMR(400MHz,CDCl
3)δ7.46(d,J=8.8Hz,1H),7.19(s,1H),7.15(d,J=8.8Hz,1H),4.08–4.03(m,2H),3.61(s,3H),3.59(s,3H),2.82(s,3H),1.71–1.61(m,2H),1.46–1.36(m,2H),0.96(t,J=5.7Hz,3H).
化合物44收率:71%.,
1H NMR(400MHz,CDCl
3)δ7.49(d,J=8.8Hz,1H),7.07(d,J=8.8Hz,1H),4.05(t,J=7.2Hz,2H),3.61(s,3H),3.59(s,3H),3.23(s,6H),2.74(s,3H),2.21(s,3H),1.69–1.60(m,2H),1.46–1.35(m,2H),0.96(t,J=7.2Hz,3H).
化合物45收率:77%.
1H NMR(400MHz,CDCl
3)δ7.49(d,J=8.4Hz,1H),7.08(d,J=8.4Hz,1H),4.05(t,J=7.2Hz,2H),3.62(s,3H),3.59(s,3H),3.18(q,J=7.2Hz,2H),3.03(q,J=7.2Hz,2H),2.75(s,3H),2.22(s,3H),1.69–1.60(m,2H),1.46–1.35(m,2H),1.08(t,J=7.2Hz,3H),1.02(t,J=7.2Hz,3H),0.96(t,J=7.2Hz,3H).
化合物46收率:75%.
1H NMR(400MHz,CDCl
3)δ7.53(d,J=8.4Hz,1H),7.08(d,J=8.4Hz,1H),4.05(t,J=7.2Hz,2H),3.60(s,3H),3.57(s,3H),3.18(q,J=7.2Hz,2H),3.03(q,J=7.2Hz,2H),2.75(s,3H),1.69–1.60(m,2H),1.46–1.35(m,2H),1.08(t,J=7.2Hz,3H),1.02(t,J=7.2Hz,3H),0.99–0.91(m,4H),0.83–0.76(m,2H),0.55–0.46(m,2H).
化合物47收率:65%.,
1H NMR(400MHz,CDCl
3)δ7.48(d,J=8.8Hz,1H),7.07(d,J=8.8Hz,1H),4.08–4.02(m,2H),3.62(s,3H),3.59(s,3H),3.23(s,3H),3.07(q,J=7.2Hz,2H),2.75(s,3H),2.21(s,3H),1.68–1.59(m,2H),1.46–1.35(m,2H),1.17(t,J=7.2Hz,3H),0.96(t,J=12.8Hz,3H).
化合物48收率:83%.,
1H NMR(400MHz,CDCl
3)δ7.49(d,J=8.8Hz,1H),7.08(d,J=8.8Hz,1H),4.05(t,J=7.2Hz,2H),3.62(s,3H),3.59(s,3H),3.26–3.01(m,5H),2.74(s,3H),2.22(s,3H),1.68–1.53(m,4H),1.46–1.35(m,2H),0.96(t,J=6.8Hz,3H),0.88(t,J=7.2Hz,3H).
化合物49收率:86%.
1H NMR(400MHz,CDCl
3)δ7.48(d,J=8.8Hz,1H),7.18(d,J=8.8Hz, 1H),4.77(t,J=5.2Hz,1H),4.66(t,J=5.2Hz,1H),4.49(t,J=5.2Hz,1H),4.43(t,J=5.2Hz,1H),3.64(s,3H),3.63(s,3H),2.77(s,3H),1.71(s,3H).
化合物50收率:74%.
1H NMR(400MHz,CDCl
3)δ7.58(d,J=8.8Hz,1H),7.17(d,J=8.8Hz,1H),4.77(t,J=5.2Hz,1H),4.66(t,J=5.2Hz,1H),4.49(t,J=5.2Hz,1H),4.43(t,J=5.2Hz,1H),3.63(s,3H),3.60(s,3H),2.82(s,3H),0.99–0.90(m,1H),0.85–0.74(m,2H),0.56–0.47(m,2H).
化合物51收率:67%.
1H NMR(400MHz,CDCl
3)δ7.48(d,J=8.8Hz,1H),7.20(s,1H),7.16(d,J=8.8Hz,1H),4.77(t,J=5.2Hz,1H),4.66(t,J=5.2Hz,1H),4.49(t,J=5.2Hz,1H),4.43(t,J=5.2Hz,1H),3.63(s,3H),3.60(s,3H),2.80(s,3H).
化合物52收率:83%.,
1H NMR(400MHz,CDCl
3)δ7.51(d,J=8.8Hz,1H),7.11(d,J=8.8Hz,1H),4.80–4.62(m,2H),4.52–4.41(m,2H),3.61(s,3H),3.59(s,3H),3.23(s,6H),2.74(s,3H),2.21(s,3H).
化合物53收率:78%.
1H NMR(400MHz,CDCl
3)δ7.52(d,J=8.8Hz,1H),7.11(d,J=8.8Hz,1H),4.76(t,J=5.2Hz,1H),4.64(t,J=5.2Hz,1H),4.49(t,J=5.2Hz,1H),4.43(t,J=5.2Hz,1H),3.61(s,3H),3.60(s,3H),3.17(q,J=7.2Hz,2H),3.03(q,J=7.2Hz,2H),2.75(s,3H),2.23(s,3H),1.08(t,J=7.2Hz,3H),1.01(t,J=7.2Hz,3H).
化合物54收率:76%.
1H NMR(400MHz,CDCl
3)δ7.55(d,J=8.8Hz,1H),7.13(d,J=8.8Hz,1H),4.76(t,J=5.2Hz,1H),4.64(t,J=5.2Hz,1H),4.49(t,J=5.2Hz,1H),4.43(t,J=5.2Hz,1H),3.61(s,3H),3.60(s,3H),3.17(q,J=7.2Hz,2H),3.03(q,J=7.2Hz,2H),2.75(s,3H),1.08(t,J=7.2Hz,3H),1.01(t,J=7.2Hz,3H),0.99–0.90(m,1H),0.85–0.74(m,2H),0.56–0.47(m,2H).
化合物55收率:71%.,
1H NMR(400MHz,CDCl
3)δ7.52(d,J=9.2Hz,1H),7.11(d,J=9.2Hz,1H),4.80–4.62(m,2H),4.52–4.40(m,2H),3.62(s,3H),3.60(s,3H),3.22(s,3H),3.06(q,J=7.2Hz,2H),2.75(s,3H),2.23(s,3H),1.17(t,J=7.2Hz,3H).
化合物56收率:82%.,
1H NMR(400MHz,CDCl
3)δ7.52(d,J=8.8Hz,1H),7.11(d,J=8.8Hz,1H),5.36–5.18(m,1H),5.12–4.84(m,2H),4.03–3.86(m,4H),3.60(s,3H),3.28–3.19(m,4H),3.04(t,J=7.2Hz,1H),2.75(s,3H),2.23(s,3H),1.67–1.48(m,2H),0.87(t,J=7.2Hz,3H).
化合物57收率:79%.
1H NMR(400MHz,CDCl
3)δ7.50(d,J=8.8Hz,1H),7.20(d,J=8.8Hz,1H),6.13(td,J=56.7,28.4Hz,1H),4.49(td,J=13.2,4.6Hz,2H),3.61(s,3H),3.60(s,3H),2.76(s,3H),1.70(s,3H).
化合物58收率:57%.
1H NMR(400MHz,CDCl
3)δ7.61(d,J=8.8Hz,1H),7.18(d,J=8.8Hz,1H),6.32–6.00(m,1H),4.56–4.42(m,2H),3.63(s,3H),3.60(s,3H),2.81(s,3H),0.97–0.89(m,1H),0.84–0.78(m,2H),0.55–0.48(m,2H).
化合物59收率:75%.
1H NMR(400MHz,CDCl
3)δ7.49(d,J=8.8Hz,1H),7.20(s,1H),7.16(d,J=8.8Hz,1H),6.32–6.00(m,1H),4.56–4.42(m,2H),3.63(s,3H),3.60(s,3H),2.81(s,3H).
化合物60收率:82%.,
1H NMR(400MHz,CDCl
3)δ7.54(d,J=8.8Hz,1H),7.12(d,J=8.8Hz,1H),6.32–6.00(m,1H),4.56–4.42(m,2H),3.61(s,3H),3.59(s,3H),3.23(s,6H),2.74(s,3H),2.22(s,3H).
化合物61收率:69%.
1H NMR(400MHz,CDCl
3)δ7.54(d,J=8.8Hz,1H),7.12(d,J=8.8Hz,1H),6.15(tt,J=56.8,4.8Hz,1H),4.50(td,J=13.2,4.8Hz,2H),3.62(s,3H),3.61(s,3H),3.18(q,J=7.2Hz,2H),3.04(q,J=7.2Hz,2H),2.74(s,3H),2.22(s,3H),1.08(t,J=7.2Hz,3H),1.01(t,J=7.2Hz,3H).
化合物62收率:86%.
1H NMR(400MHz,CDCl
3)δ7.58(d,J=8.8Hz,1H),7.17(d,J=8.8Hz,1H),6.32–6.00(m,1H),4.56–4.42(m,2H),3.62(s,3H),3.60(s,3H),3.18(q,J=7.2Hz,2H),3.04(q,J=7.2Hz,2H),2.75(s,3H),1.08(t,J=7.2Hz,3H),1.01(t,J=7.2Hz,3H),0.97–0.89(m,1H),0.84–0.78(m,2H),0.55–0.48(m,2H).
化合物63收率:68%.,
1H NMR(400MHz,CDCl
3)δ7.53(d,J=8.8Hz,1H),7.11(d,J=8.8Hz,1H),6.15(tt,J=56.8,4.8Hz,1H),4.50(td,J=13.2,4.8Hz,2H),3.62(s,3H),3.61(s,3H),3.23(s,3H), 3.07(q,J=7.2Hz,2H),2.74(s,3H),2.23(s,3H),1.17(t,J=7.2Hz,3H).
化合物64收率:81%.,
1H NMR(400MHz,CDCl
3)δ7.54(d,J=8.8Hz,1H),7.12(d,J=8.8Hz,1H),6.32–5.99(m,1H),4.56–4.42(m,2H),3.62(s,3H),3.60(s,3H),3.31–3.14(m,4H),3.04(t,J=7.2Hz,1H),2.75(s,3H),2.22(s,3H),1.67–1.44(m,2H),0.88(t,J=7.2Hz,3H).
化合物65收率:76%.
1H NMR(400MHz,CDCl
3)δ7.51(d,J=8.8Hz,1H),7.21(d,J=8.8Hz,1H),4.82(q,J=8.4Hz,2H),3.65(s,3H),3.64(s,3H),2.76(s,3H),1.71(s,3H).
化合物66收率:78%.
1H NMR(400MHz,CDCl
3)δ7.62(d,J=8.8Hz,1H),7.19(d,J=8.8Hz,1H),4.82(q,J=8.4Hz,2H),3.64(s,3H),3.60(s,3H),2.81(s,3H),0.97–0.89(m,1H),0.83–0.77(m,2H),0.55–0.49(m,2H).
化合物67收率:82%.
1H NMR(400MHz,CDCl
3)δ7.51(d,J=8.8Hz,1H),7.21(s,1H)7.22(d,J=8.8Hz,1H),4.82(q,J=8.4Hz,2H),3.64(s,3H),3.60(s,3H),2.82(s,3H).
化合物68收率:84%.,
1H NMR(400MHz,CDCl
3)δ7.55(d,J=9.2Hz,1H),7.12(d,J=9.2Hz,1H),4.82(q,J=8.4Hz,2H),3.62(s,3H),3.60(s,3H),3.23(s,6H),2.74(s,3H),2.24(s,3H).
化合物69收率:80%.
1H NMR(400MHz,CDCl
3)δ7.55(d,J=8.8Hz,1H),7.13(d,J=8.8Hz,1H),4.83(q,J=8.4Hz,2H),3.62(s,3H),3.61(s,3H),3.16(q,J=7.2Hz,2H),3.00(q,J=7.2Hz,2H),2.75(s,3H),2.27(s,3H),1.06(t,J=7.2Hz,3H),0.99(t,J=7.2Hz,3H).
化合物70收率:84%.
1H NMR(400MHz,CDCl
3)δ7.58(d,J=8.8Hz,1H),7.15(d,J=8.8Hz,1H),4.85(q,J=8.4Hz,2H),3.64(s,3H),3.60(s,3H),3.16(q,J=7.2Hz,2H),3.01(q,J=7.2Hz,2H),2.76(s,3H),1.06(t,J=7.2Hz,3H),1.02–0.89(m,4H),0.83–0.77(m,2H),0.55–0.49(m,2H).
化合物71收率:81%.,
1H NMR(400MHz,CDCl
3)δ7.56(d,J=8.4Hz,1H),7.14(d,J=8.4Hz,1H),4.83(q,J=8.4Hz,2H),3.62(s,3H),3.61(s,3H),3.23(s,3H),3.07(q,J=7.6Hz,2H),2.75(s,3H),2.26(s,3H),1.17(t,J=7.2Hz,3H).
化合物72收率:73%.,
1H NMR(400MHz,CDCl
3)δ7.55(d,J=8.8Hz,1H),7.13(d,J=8.8Hz,1H),4.84(q,J=8.4Hz,2H),3.63(s,3H),3.61(s,3H),3.30(t,J=8.4Hz,1H),3.23(s,3H),3.08(t,J=8.4Hz,1H),2.74(s,3H),2.27(s,3H),1.68–1.47(m,2H),0.87(t,J=7.2Hz,3H).
化合物73收率:76%.
1H NMR(400MHz,CDCl
3)δ7.47(d,J=8.8Hz,1H),7.17(d,J=8.8Hz,1H),4.62(t,J=6.0Hz,1H),4.51(t,J=6.0Hz,1H),4.23(t,J=7.2Hz,2H),3.63(s,3H),3.63(s,3H),2.77(s,3H),2.20–2.05(m,2H),1.70(s,3H).
化合物74收率:68%.
1H NMR(400MHz,CDCl
3)δ7.57(d,J=8.8Hz,1H),7.16(d,J=8.8Hz,1H),4.62(t,J=6.0Hz,1H),4.50(t,J=6.0Hz,1H),4.23(t,J=7.2Hz,2H),3.62(s,3H),3.59(s,3H),2.82(s,3H),2.20–2.04(m,2H),0.98–0.89(m,1H),0.82–0.76(m,2H),0.55–0.46(m,2H).
化合物75收率:69%.
1H NMR(400MHz,CDCl
3)δ7.46(d,J=8.8Hz,1H),7.21(s,1H)7.16(d,J=8.8Hz,1H),4.62(t,J=6.0Hz,1H),4.50(t,J=6.0Hz,1H),4.23(t,J=7.2Hz,2H),3.62(s,3H),3.60(s,3H),2.82(s,3H),2.20–2.04(m,2H).
化合物76收率:71%.,
1H NMR(400MHz,CDCl
3)δ7.51(d,J=9.2Hz,1H),7.10(d,J=9.2Hz,1H),4.62(t,J=6.0Hz,1H),4.50(t,J=6.0Hz,1H),4.23(t,J=7.2Hz,2H),3.61(s,3H),3.59(s,3H),3.23(s,6H),2.74(s,3H),2.22–2.05(m,5H).
化合物77收率:68%.
1H NMR(400MHz,CDCl
3)δ7.50(d,J=8.8Hz,1H),7.09(d,J=8.8Hz,1H),4.62(t,J=6.0Hz,1H),4.50(t,J=6.0Hz,1H),4.23(t,J=7.2Hz,2H),3.62(s,3H),3.59(s,3H),3.18(q,J=7.2Hz,2H),3.03(q,J=7.2Hz,2H),2.75(s,3H),2.22(s,3H),2.18–2.04(m,2H),1.08(t,J=7.2Hz,3H),1.02(t,J=7.2Hz,3H).
化合物78收率:75%.
1H NMR(400MHz,CDCl
3)δ7.54(d,J=8.8Hz,1H),7.11(d,J=8.8Hz,1H),4.62(t,J=6.0Hz,1H),4.49(t,J=6.0Hz,1H),4.24(t,J=7.2Hz,2H),3.64(s,3H),3.59(s,3H),3.18(q,J=7.2Hz,2H),3.03(q,J=7.2Hz,2H),2.75(s,3H),2.18–2.04(m,2H),1.08(t,J=7.2Hz,3H),1.03–0.89(m,4H),0.82–0.76(m,2H),0.55–0.46(m,2H).
化合物79收率:63%.,
1H NMR(400MHz,CDCl
3)δ7.50(d,J=8.8Hz,1H),7.10(d,J=8.8Hz, 1H),4.62(t,J=6.4Hz,1H),4.50(t,J=6.4Hz,1H),4.23(t,J=7.2Hz,2H),3.61(s,3H),3.59(s,3H),3.23(s,3H),3.07(q,J=7.2Hz,2H),2.75(s,3H),2.21(s,3H),2.18–2.04(m,2H),1.17(t,J=7.2Hz,3H).
化合物80收率:69%.,
1H NMR(400MHz,CDCl
3)δ7.49(d,J=8.4Hz,1H),7.08(d,J=8.4Hz,1H),4.62(t,J=6.0Hz,1H),4.50(t,J=6.0Hz,1H),4.23(t,J=7.2Hz,2H),3.62(s,3H),3.59(s,3H),3.31–3.06(m,5H),2.74(s,3H),2.21(s,3H),2.18–2.04(m,2H),1.67–1.33(m,2H),0.87(t,J=7.2Hz,3H).
化合物81收率:78%.
1H NMR(400MHz,CDCl
3)δ7.47(d,J=8.8Hz,1H),7.18(d,J=8.8Hz,1H),4.39–4.28(m,2H),3.63(s,3H),3.61(s,3H),2.75(s,3H),2.60–2.46(m,2H),1.69(s,3H).
化合物82收率:70%.
1H NMR(400MHz,CDCl
3)δ7.52(d,J=8.8Hz,1H),7.16(d,J=8.8Hz,1H),4.41–4.30(m,2H),3.62(s,3H),3.61(s,3H),2.75(s,3H),2.64–2.49(m,2H),1.01–0.91(m,1H),0.83–0.77(m,2H),0.55–0.46(m,2H).
化合物83收率:65%.
1H NMR(400MHz,CDCl
3)δ7.48(d,J=8.8Hz,1H),7.20(s,1H),7.17(d,J=8.8Hz,1H),4.39–4.28(m,2H),3.63(s,3H),3.61(s,3H),2.75(s,3H),2.60–2.46(m,2H).
化合物84收率:73%.,
1H NMR(400MHz,CDCl
3)δ7.52(d,J=8.8Hz,1H),7.10(d,J=8.8Hz,1H),4.38–4.31(m,2H),3.62(s,3H),3.60(s,3H),3.23(s,6H),2.74(s,3H),2.62–2.48(m,2H),2.21(s,3H).
化合物85收率:68%.
1H NMR(400MHz,CDCl
3)δ7.52(d,J=8.8Hz,1H),7.10(d,J=8.8Hz,1H),4.38–4.31(m,2H),3.61(s,3H),3.60(s,3H),3.19(q,J=7.2Hz,2H),3.04(q,J=7.2Hz,2H),2.75(s,3H),2.62–2.47(m,2H),2.20(s,3H),1.08(t,J=7.2Hz,3H),1.02(t,J=7.2Hz,3H).
化合物86收率:69%.
1H NMR(400MHz,CDCl
3)δ7.55(d,J=8.8Hz,1H),7.13(d,J=8.8Hz,1H),4.38–4.31(m,2H),3.61(s,3H),3.60(s,3H),3.20(q,J=7.2Hz,2H),3.05(q,J=7.2Hz,2H),2.75(s,3H),2.62–2.47(m,2H),1.08(t,J=7.2Hz,3H),1.02–0.89(m,4H),0.83–0.77(m,2H),0.55–0.46(m,2H).
化合物87收率:73%.,
1H NMR(400MHz,CDCl
3)δ7.52(d,J=9.2Hz,1H),7.10(d,J=9.2Hz,1H),4.38–4.31(m,2H),3.62(s,3H),3.60(s,3H),3.23(s,3H),3.07(q,J=7.2Hz,2H),2.74(s,3H),2.62–2.47(m,2H),2.22(s,3H),1.17(t,J=7.6Hz,3H).
化合物88收率:78%.,
1H NMR(400MHz,CDCl
3)δ7.52(d,J=8.8Hz,1H),7.10(d,J=9.2Hz,1H),4.38–4.30(m,2H),3.61(s,3H),3.59(s,3H),3.30–3.15(m,4H),3.04(t,J=7.2Hz,1H),2.75(s,3H),2.62–2.47(m,2H),2.20(s,3H),1.64–1.46(m,2H),0.87(t,J=7.2Hz,3H).
化合物89收率:83%.
1H NMR(400MHz,CDCl
3)δ7.45(d,J=8.4Hz,1H),7.16(d,J=8.4Hz,1H),4.31(t,J=5.2Hz,2H),3.68(t,J=5.2Hz,2H),3.63(s,3H),3.62(s,3H),3.37(s,3H),2.76(s,3H),1.70(s,3H).
化合物90收率:84%.
1H NMR(400MHz,CDCl
3)δ7.56(d,J=8.8Hz,1H),7.15(d,J=8.8Hz,1H),4.33(t,J=5.6Hz,2H),3.69(t,J=5.6Hz,2H),3.61(s,3H),3.59(s,3H),3.37(s,3H),2.82(s,3H),0.99–0.89(m,1H),0.83–0.75(m,2H),0.56–0.47(m,2H).
化合物91收率:73%.
1H NMR(400MHz,CDCl
3)δ7.46(d,J=8.8Hz,1H),7.20(s,1H),7.17(d,J=8.8Hz,1H),4.33(t,J=5.6Hz,2H),3.69(t,J=5.6Hz,2H),3.61(s,3H),3.59(s,3H),3.37(s,3H),2.76(s,3H).
化合物92收率:78%.,
1H NMR(400MHz,CDCl
3)δ7.50(d,J=9.2Hz,1H),7.09(d,J=9.2Hz,1H),4.33(t,J=5.6Hz,2H),3.67(t,J=5.6Hz,2H),3.62(s,3H),3.60(s,3H),3.36(s,3H),3.23(s,6H),2.75(s,3H),2.22(s,3H).
化合物93收率:59%.
1H NMR(400MHz,CDCl
3)δ7.50(d,J=8.8Hz,1H),7.08(d,J=8.8Hz,1H),4.33(t,J=5.6Hz,2H),3.67(t,J=5.6Hz,2H),3.62(s,3H),3.59(s,3H),3.36(s,3H),3.18(q,J=7.2Hz,2H),3.03(q,J=7.2Hz,2H),2.75(s,3H),2.23(s,3H),1.08(t,J=7.2Hz,3H),1.01(t,J=7.2Hz,3H).
化合物94收率:70%.
1H NMR(400MHz,CDCl
3)δ7.56(d,J=8.8Hz,1H),7.04(d,J=8.8Hz,1H),4.34(t,J=5.6Hz,2H),3.67(t,J=5.6Hz,2H),3.64(s,3H),3.58(s,3H),3.36(s,3H),3.18(q,J=7.2Hz,2H),3.03(q,J=7.2Hz,2H),2.74(s,3H),1.08(t,J=7.2Hz,3H),1.01(t,J=7.2Hz,3H),0.99–0.89(m,1H),0.83–0.75(m,2H),0.56–0.47(m,2H).
化合物95收率:81%.,
1H NMR(400MHz,CDCl
3)δ7.50(d,J=7.6Hz,1H),7.07(d,J=7.6Hz,1H),4.33(t,J=5.6Hz,2H),3.67(t,J=5.6Hz,2H),3.61(s,3H),3.59(s,3H),3.36(s,3H),3.23(s,3H),3.07(q,J=7.2Hz,2H),2.74(s,3H),2.22(s,3H),1.17(t,J=7.2Hz,3H).
化合物96收率:73%.,
1H NMR(400MHz,CDCl
3)δ7.49(d,J=8.8Hz,1H),7.06(d,J=8.8Hz,1H),4.34(t,J=5.6Hz,2H),3.67(t,J=5.6Hz,2H),3.62(s,3H),3.59(s,3H),3.36(s,3H),3.30–3.15(m,4H),3.05(t,J=7.2Hz,1H),2.75(s,3H),2.23(s,3H),1.70–1.43(m,2H),0.87(t,J=7.2Hz,3H).
化合物97收率:80%.
1H NMR(400MHz,CDCl
3)δ7.46(d,J=8.8Hz,1H),7.17(d,J=8.8Hz,1H),6.01–5.89(m,1H),5.31(d,J=17.2Hz,1H),5.21(d,J=10.4Hz,1H),4.68(d,J=5.6Hz,2H),3.63(s,3H),3.62(s,3H),2.77(s,3H),1.70(s,3H).
化合物98收率:79%.
1H NMR(400MHz,CDCl
3)δ7.57(d,J=8.8Hz,1H),7.16(d,J=8.8Hz,1H),6.02–5.89(m,1H),5.31(d,J=17.2Hz,1H),5.22(d,J=10.4Hz,1H),4.68(d,J=5.6Hz,2H),3.62(s,3H),3.60(s,3H),2.82(s,3H),0.98–0.91(m,1H),0.85–0.76(m,2H),0.56–0.43(m,2H).
化合物99收率:80%.
1H NMR(400MHz,CDCl
3)δ7.45(d,J=8.8Hz,1H),7.20(s,1H),7.16(d,J=8.8Hz,1H),6.02–5.90(m,1H),5.31(d,J=17.2Hz,1H),5.22(d,J=10.4Hz,1H),4.68(d,J=5.6Hz,2H),3.62(s,3H),3.60(s,3H),2.78(s,3H).
化合物100收率:81%.,
1H NMR(400MHz,CDCl
3)δ7.50(d,J=8.4Hz,1H),7.09(d,J=8.4Hz,1H),6.00–5.88(m,1H),5.32–5.18(m,2H),4.68(d,J=5.8Hz,2H),3.63(s,3H),3.59(s,3H),3.23(s,6H),2.74(s,3H),2.21(s,3H).
化合物101收率:78%.
1H NMR(400MHz,CDCl
3)δ7.50(d,J=8.8Hz,1H),7.09(d,J=8.8Hz,1H),5.99–5.87(m,1H),5.28(d,J=17.2Hz,1H),5.20(d,J=10.4Hz,1H),4.68(d,J=5.8Hz,2H),3.62(s,3H),3.60(s,3H),3.18(q,J=7.2Hz,2H),3.03(q,J=7.2Hz,2H),2.75(s,3H),2.21(s,3H),1.07(t,J=7.2Hz,3H),1.02(t,J=7.2Hz,3H).
化合物102收率:90%.
1H NMR(400MHz,CDCl
3)δ7.53(d,J=8.8Hz,1H),7.08(d,J=8.8Hz,1H),6.00–5.87(m,1H),5.30(d,J=17.2Hz,1H),5.22(d,J=10.4Hz,1H),4.68(d,J=5.8Hz,2H),3.64(s,3H),3.59(s,3H),3.18(q,J=7.2Hz,2H),3.03(q,J=7.2Hz,2H),2.75(s,3H),1.07(t,J=7.2Hz,3H),1.02(t,J=7.2Hz,3H),0.98–0.91(m,1H),0.85–0.76(m,2H),0.56–0.43(m,2H).
化合物103收率:66%.,
1H NMR(400MHz,CDCl
3)δ7.51(d,J=9.2Hz,1H),7.10(d,J=9.2Hz,1H),6.00–5.88(m,1H),5.28(d,J=17.2Hz,1H),5.20(d,J=10.4Hz,1H),4.68(d,J=6.0Hz,2H),3.62(s,3H),3.59(s,3H),3.23(s,3H),3.07(q,J=7.6Hz,2H),2.74(s,3H),2.20(s,3H),1.17(t,J=7.6Hz,3H).
化合物104收率:67%.,
1H NMR(400MHz,CDCl
3)δ7.52(d,J=8.4Hz,1H),7.10(d,J=8.4Hz,1H),6.01–5.88(m,1H),5.32–5.24(m,1H),5.24–5.18(m,1H),4.68(d,J=6.0Hz,2H),3.62(s,3H),3.60(s,3H),3.23(s,3H),3.14(t,J=7.2Hz,1H),3.01(t,J=7.2Hz,1H),2.75(s,3H),2.21(s,3H),1.69–1.41(m,2H),0.87(t,J=7.2Hz,3H).
化合物105收率:79%.
1H NMR(400MHz,CDCl
3)δ7.48(d,J=8.8Hz,1H),7.19(d,J=8.8Hz,1H),4.84(d,J=2.0Hz,2H),3.65(s,3H),3.63(s,3H),2.78(s,3H),2.19(t,J=2.4Hz,1H),1.70(s,3H).
化合物106收率:68%.
1H NMR(400MHz,CDCl
3)δ7.58(d,J=8.4Hz,1H),7.17(d,J=8.4Hz,1H),4.84(d,J=2.0Hz,2H),3.64(s,3H),3.59(s,3H),2.83(s,3H),2.19(t,J=2.4Hz,1H),1.00–0.87(m,1H),0.83–0.72(m,2H),0.55–0.44(m,2H).
化合物107收率:80%.
1H NMR(400MHz,CDCl
3)δ7.46(d,J=8.4Hz,1H),7.21(s,1H),7.18(d,J=8.4Hz,1H),4.84(d,J=2.0Hz,2H),3.64(s,3H),3.59(s,3H),2.83(s,3H),2.19(t,J=2.3Hz,1H).
化合物108收率:87%.,
1H NMR(400MHz,CDCl
3)δ7.52(d,J=8.8Hz,1H),7.11(d,J=8.8Hz,1H),4.84(d,J=2.4Hz,2H),3.62(s,3H),3.60(s,3H),3.23(s,6H),2.75(s,3H),2.20(s,3H),2.19(t,J=2.4Hz,1H).
化合物109收率:77%.
1H NMR(400MHz,CDCl
3)δ7.52(d,J=8.8Hz,1H),7.11(d,J=8.8Hz,1H),4.84(d,J=2.4Hz,2H),3.62(s,3H),3.61(s,3H),3.18(q,J=7.2Hz,2H),3.04(q,J=7.2Hz,2H),2.77(s,3H),2.21(s,3H),2.19(t,J=2.4Hz,1H),1.08(t,J=7.2Hz,3H),1.02(t,J=7.2Hz,3H).
化合物110收率:69%.
1H NMR(400MHz,CDCl
3)δ7.56(d,J=8.8Hz,1H),7.13(d,J=8.8Hz,1H),4.84(d,J=2.4Hz,2H),3.63(s,3H),3.61(s,3H),3.18(q,J=7.2Hz,2H),3.04(q,J=7.2Hz,2H),2.75(s,3H),2.19(t,J=2.4Hz,1H),1.08(t,J=7.2Hz,3H),1.01–0.87(m,4H),0.83–0.72(m,2H),0.55–0.44(m,2H).
化合物111收率:77%.,
1H NMR(400MHz,CDCl
3)δ7.52(d,J=9.2Hz,1H),7.10(d,J=9.2Hz,1H),4.84(d,J=2.4Hz,2H),3.62(s,3H),3.60(s,3H),3.23(s,3H),3.12–3.01(m,2H),2.75(s,3H),2.21(s,3H),2.19(t,J=2.4Hz,1H),1.17(t,J=7.6Hz,3H).
化合物112收率:69%.,
1H NMR(400MHz,CDCl
3)δ7.52(d,J=8.8Hz,1H),7.10(d,J=8.8Hz,1H),4.84(d,J=2.4Hz,2H),3.62(s,3H),3.59(s,3H),3.24–3.16(m,4H),3.08(t,J=6.0Hz,1H),2.74(s,3H),2.21(s,3H),2.19(t,J=2.4Hz,1H),1.66–1.49(m,2H),0.87(t,J=7.6Hz,3H).
化合物113收率:75%.
1H NMR(400MHz,CDCl
3)δ7.45(d,J=8.8Hz,1H),7.15(d,J=8.8Hz,1H),5.36–5.24(m,1H),4.66(d,J=6.8Hz,2H),3.63(s,3H),3.61(s,3H),2.78(s,3H),1.85(s,3H),1.75–1.67(m,6H).
化合物114收率:70%.
1H NMR(400MHz,CDCl
3)δ7.57(d,J=8.8Hz,1H),7.15(d,J=8.8Hz,1H),5.39–5.27(m,1H),4.67(d,J=6.8Hz,2H),3.65(s,3H),3.59(s,3H),2.78(s,3H),1.79(s,3H),1.66(s,3H),1.01–0.88(m,1H),0.83–0.72(m,2H),0.55–0.44(m,2H).
化合物115收率:74%.
1H NMR(400MHz,CDCl
3)δ7.44(d,J=8.8Hz,1H),7.21(s,1H),7.15(d,J=8.8Hz,1H),5.36–5.24(m,1H),4.66(d,J=6.8Hz,2H),3.64(s,3H),3.61(s,3H),2.78(s,3H),1.79(s,3H),1.66(s,3H).
化合物116收率:72%.,
1H NMR(400MHz,CDCl
3)δ7.47(d,J=9.2Hz,1H),7.06(d,J=9.2Hz,1H),5.26(t,J=6.8Hz,1H),4.66(d,J=6.8Hz,2H),3.62(s,3H),3.60(s,3H),3.23(s,6H),2.75(s,3H),2.21(s,3H),1.86(s,3H),1.71(s,3H).
化合物117收率:73%.
1H NMR(400MHz,CDCl
3)δ7.48(d,J=8.8Hz,1H),7.07(d,J=8.8Hz,1H),5.26(t,J=6.8Hz,1H),4.66(d,J=6.8Hz,2H),3.61(s,3H),3.59(s,3H),3.17(q,J=7.2Hz,2H),3.02(q,J=7.2Hz,2H),2.76(s,3H),2.22(s,3H),1.85(s,3H),1.71(s,3H),1.07(t,J=7.2Hz,3H),1.01(t,J=7.2Hz,3H).
化合物118收率:65%.
1H NMR(400MHz,CDCl
3)δ7.54(d,J=8.8Hz,1H),7.08(d,J=8.8Hz,1H),5.26(t,J=6.8Hz,1H),4.67(d,J=6.8Hz,2H),3.62(s,3H),3.59(s,3H),3.17(q,J=7.2Hz,2H),3.02(q,J=7.2Hz,2H),2.75(s,3H),1.85(s,3H),1.71(s,3H),1.07(t,J=7.2Hz,3H),1.03–0.87(m,4H),0.83–0.72(m,2H),0.55–0.44(m,2H).
化合物119收率:65%.,
1H NMR(400MHz,CDCl
3)δ7.47(d,J=8.2Hz,1H),7.06(d,J=8.2Hz,1H),5.28–5.24(m,1H),4.66(d,J=6.8Hz,2H)3.61(s,3H),3.59(s,3H),3.23(s,3H),3.07(q,J=7.2Hz,2H),2.75(s,3H),2.22(s,3H),1.85(s,3H),1.71(s,3H),1.17(t,J=7.2Hz,3H).
化合物120收率:80%.,
1H NMR(400MHz,CDCl
3)δ7.48(d,J=8.8Hz,1H),7.07(d,J=8.8Hz,1H),5.26(t,J=6.8Hz,1H),4.66(d,J=6.8Hz,2H),3.61(s,3H),3.59(s,3H),3.27–3.20(m,4H),3.04(t,J=6.0Hz,1H),2.76(s,3H),2.23(s,3H),1.85(s,3H),1.71(s,3H),1.65–1.49(m,2H),0.87(t,J=7.2Hz,3H).
化合物121收率:70%.
1H NMR(400MHz,CDCl
3)δ7.42(d,J=8.8Hz,1H),7.12(d,J=8.8Hz,1H),3.65–3.59(m,4H),3.53(s,3H),2.69(s,3H),1.87(s,3H),1.19–1.10(m,2H),0.78–0.68(m,2H).
化合物122收率:76%.
1H NMR(400MHz,CDCl
3)δ7.54(d,J=8.6Hz,1H),7.12(d,J=8.6Hz, 1H),3.66–3.53(m,7H),2.79(s,3H),1.24–1.17(m,2H),0.98–0.91(m,1H),0.82–0.76(m,4H),0.53–0.48(m,2H).
化合物123收率:69%.
1H NMR(400MHz,CDCl
3)δ7.43(d,J=8.8Hz,1H),7.22(s,1H),7.12(d,J=8.8Hz,1H),3.66–3.53(m,7H),2.79(s,3H),1.20–1.11(m,2H),0.78–0.68(m,2H).
化合物124收率:85%.,
1H NMR(400MHz,CDCl
3)δ7.45(d,J=8.8Hz,1H),7.05(d,J=8.8Hz,1H),3.60(s,3H),3.57(s,3H),2.82–2.74(m,4H),2.70(s,3H),2.68(s,3H),2.19(s,3H),1.29–1.14(m,2H),0.81–0.71(m,2H).
化合物125收率:64%.
1H NMR(400MHz,CDCl
3)δ7.47(d,J=8.8Hz,1H),7.05(d,J=8.8Hz,1H),3.65–3.59(m,4H),3.57(s,3H),3.18(q,J=7.2Hz,2H),3.04(q,J=7.2Hz,2H),2.72(s,3H),2.20(s,3H),1.23–1.17(m,2H),1.08(t,J=7.2Hz,3H),1.01(t,J=7.2Hz,3H),0.78–0.71(m,2H).
化合物126收率:72%.
1H NMR(400MHz,CDCl
3)δ7.53(d,J=8.8Hz,1H),7.06(d,J=8.8Hz,1H),3.65–3.59(m,7H),3.18(q,J=7.2Hz,2H),3.04(q,J=7.2Hz,2H),2.74(s,3H),1.08(t,J=7.2Hz,3H),1.01(t,J=7.2Hz,3H),1.24–1.17(m,2H),0.98–0.91(m,1H),0.82–0.76(m,4H),0.53–0.48(m,2H).
化合物127收率:86%.,
1H NMR(400MHz,CDCl
3)δ7.46(d,J=8.4Hz,1H),7.05(d,J=8.4Hz,1H),3.60(s,3H),3.56(s,3H),3.10(dq,J=36.9,7.1Hz,2H),2.86–2.74(m,2H),2.71(m,3H),2.65(s,2H),2.23(s,2H),2.15(s,1H),1.19(m,2H),1.03(dt,J=34.9,7.1Hz,3H),0.81–0.66(m,2H).
化合物128收率:88%.,
1H NMR(400MHz,CDCl
3)δ7.47(d,J=8.4Hz,1H),7.05(d,J=8.4Hz,1H),3.65–3.59(m,7H),3.27–3.20(m,4H),3.06(t,J=6.0Hz,1H),2.73(s,3H),2.20(s,3H),1.65–1.49(m,2H),1.23–1.17(m,2H),0.87(t,J=7.2Hz,3H).0.78–0.71(m,2H).
化合物129收率:66%.
1H NMR(400MHz,CDCl
3)δ7.43(d,J=8.8Hz,1H),7.12(d,J=8.8Hz,1H),5.32–5.20(m,1H),3.63(s,3H),3.58(s,3H),2.91–2.80(m,2H),2.73(s,3H),2.39–2.30(m,2H),1.96–1.73(m,2H),1.70(s,3H).
化合物130收率:60%.
1H NMR(400MHz,CDCl
3)δ7.53(d,J=8.8Hz,1H),7.11(d,J=8.8Hz,1H),5.29–5.18(m,1H),3.59(s,3H),3.57(s,3H),2.92–2.81(m,2H),2.78(s,3H),2.41–2.29(m,2H),1.95–1.69(m,2H),0.99–0.89(m,1H),0.82–0.74(m,2H),0.54–0.46(m,2H).
化合物131收率:86%.,
1H NMR(400MHz,CDCl
3)δ7.46(d,J=8.4Hz,1H),7.03(d,J=8.4Hz,1H),5.27–5.17(m,1H),3.61(s,3H),3.55(s,3H),3.23(s,6H),2.90–2.77(m,2H),2.72(s,3H),2.41–2.29(m,2H),2.21(s,3H),1.94–1.73(m,2H),
化合物132收率:84%.
1H NMR(400MHz,CDCl
3)δ7.47(d,J=8.8Hz,1H),7.04(d,J=8.8Hz,1H),5.27–5.17(m,1H),3.61(s,3H),3.55(s,3H),3.18(q,J=7.2Hz,2H),3.04(q,J=7.2Hz,2H),2.90–2.77(m,2H),2.72(s,3H),2.41–2.29(m,2H),2.21(s,3H),1.94–1.73(m,2H),1.08(t,J=7.2Hz,3H),1.02(t,J=7.2Hz,3H).
化合物133收率:73%.
1H NMR(400MHz,CDCl
3)δ7.54(d,J=8.8Hz,1H),7.06(d,J=8.8Hz,1H),5.25–5.15(m,1H),3.63(s,3H),3.57(s,3H),3.18(q,J=7.2Hz,2H),3.04(q,J=7.2Hz,2H),2.90–2.77(m,2H),2.72(s,3H),2.41–2.29(m,2H),1.94–1.73(m,2H),1.08(t,J=7.2Hz,3H),1.03–0.89(m,4H),0.82–0.74(m,2H),0.54–0.46(m,2H).
化合物134收率:85%.,
1H NMR(400MHz,CDCl
3)δ7.47(d,J=8.4Hz,1H),7.04(d,J=8.4Hz,1H),5.27–5.17(m,1H),3.62(s,3H),3.55(s,3H),3.23(s,3H),3.07(q,J=7.6Hz,2H),2.90–2.77(m,2H),2.73(s,3H),2.41–2.29(m,2H),2.21(s,3H),1.94–1.73(m,2H),1.17(t,J=7.6Hz,3H).
化合物135收率:75%.,
1H NMR(400MHz,CDCl
3)δ7.47(d,J=8.4Hz,1H),7.04(d,J=8.4Hz,1H),5.27–5.17(m,1H),3.62(s,3H),3.55(s,3H),3.22(s,3H),3.19(t,J=7.6Hz,1H),2.98(t,J=7.6Hz,1H),2.90–2.77(m,2H),2.73(s,3H),2.41–2.29(m,2H),2.21(s,3H),1.94–1.73(m,2H),1.65–1.48(m,2H),0.87(t,J=7.2Hz,3H).
化合物136收率:70%.
1H NMR(400MHz,CDCl
3)δ7.43(d,J=8.8Hz,1H),7.13(d,J=8.8Hz,1H),5.48–5.38(m,1H),3.63(s,3H),3.59(s,3H),2.76(s,3H),2.21–2.11(m,2H),2.05–1.95(m,2H), 1.93–1.83(m,2H),1.71(s,3H),1.68–1.58(m,2H).
化合物137收率:74%.
1H NMR(400MHz,CDCl
3)δ7.54(d,J=8.8Hz,1H),7.11(d,J=8.8Hz,1H),5.48–5.37(m,1H),3.60(s,3H),3.59(s,3H),2.80(s,3H),2.23–2.11(m,2H),2.06–1.96(m,2H),1.93–1.83(m,2H),1.67–1.58(m,2H),1.00–0.92(m,1H),0.81–0.75(m,2H),0.54–0.47(m,2H).
化合物138收率:71%.,
1H NMR(400MHz,CDCl
3)δ7.47(d,J=8.4Hz,1H),7.06(d,J=8.4Hz,1H),5.46–5.36(m,1H),3.62(s,3H),3.56(s,3H),3.22(s,6H),2.73(s,3H),2.22(s,3H),2.18–2.09(m,2H),2.04–1.95(m,2H),1.92–1.82(m,2H),1.67–1.57(m,2H),
化合物139收率:73%.
1H NMR(400MHz,CDCl
3)δ7.47(d,J=8.8Hz,1H),7.05(d,J=8.8Hz,1H),5.46–5.36(m,1H),3.62(s,3H),3.56(s,3H),3.18(q,J=7.2Hz,2H),3.04(q,J=7.2Hz,2H),2.73(s,3H),2.22(s,3H),2.18–2.09(m,2H),2.04–1.95(m,2H),1.92–1.82(m,2H),1.67–1.57(m,2H),1.08(t,J=7.2Hz,3H),1.01(t,J=7.2Hz,3H).
化合物140收率:77%.
1H NMR(400MHz,CDCl
3)δ7.54(d,J=8.8Hz,1H),7.07(d,J=8.8Hz,1H),5.46–5.36(m,1H),3.62(s,3H),3.56(s,3H),3.18(q,J=7.2Hz,2H),3.04(q,J=7.2Hz,2H),2.73(s,3H),2.18–2.09(m,2H),2.04–1.82(m,4H),1.67–1.57(m,2H),1.08(t,J=7.2Hz,3H),1.03–0.92(m,4H),0.81–0.75(m,2H),0.54–0.47(m,2H).
化合物141收率:69%.,
1H NMR(400MHz,CDCl
3)δ7.47(d,J=8.8Hz,1H),7.05(d,J=8.8Hz,1H),5.46–5.36(m,1H),3.62(s,3H),3.56(s,3H),3.21(s,3H),3.05(q,J=7.6Hz,2H),2.73(s,3H),2.22(s,3H),2.18–2.09(m,2H),2.04–1.95(m,2H),1.92–1.82(m,2H),1.67–1.57(m,2H),1.17(t,J=7.6Hz,3H).
化合物142收率:73%.,
1H NMR(400MHz,CDCl
3)δ7.47(d,J=8.8Hz,1H),7.06(d,J=8.8Hz,1H),5.46–5.36(m,1H),3.62(s,3H),3.58(s,3H),3.29–3.16(m,4H),3.03(t,J=7.6Hz,1H),2.75(s,3H),2.22(s,3H),2.18–2.09(m,2H),2.04–1.95(m,2H),1.92–1.82(m,2H),1.67–1.48(m,4H),0.87(t,J=7.2Hz,3H).
化合物143收率:72%.
1H NMR(400MHz,CDCl
3)δ7.43(d,J=8.8Hz,1H),7.12(d,J=8.8Hz,1H),4.93–4.84(m,1H),3.64(s,3H),3.58(s,3H),2.75(s,3H),2.53–2.40(m,2H),1.91–1.82(m,2H),1.71(s,3H),1.70–1.64(m,3H),1.46–1.25(m,3H).
化合物144收率:74%.
1H NMR(400MHz,CDCl
3)δ7.53(d,J=8.8Hz,1H),7.11(d,J=8.8Hz,1H),4.94–4.83(m,1H),3.59(s,3H),3.57(s,3H),2.80(s,3H),2.53–2.41(m,2H),1.90–1.82(m,2H),1.72–1.64(m,3H),1.45–1.23(m,3H),1.00–0.92(m,1H),0.82–0.76(m,2H),0.55–0.48(m,2H).
化合物145收率:72%.
1H NMR(400MHz,CDCl
3)δ7.47(d,J=8.4Hz,1H),7.04(d,J=8.4Hz,1H),4.94–4.81(m,1H),3.62(s,3H),3.55(s,3H),3.17(q,J=7.2Hz,2H),3.03(q,J=7.2Hz,2H),2.72(s,3H),2.53–2.40(m,2H),2.23(s,3H),1.90–1.81(m,2H),1.72–1.61(m,3H),1.46–1.25(m,3H),1.08(t,J=7.2Hz,3H),1.01(t,J=7.2Hz,3H).
化合物146收率:80%.
1H NMR(400MHz,CDCl
3)δ7.46(d,J=8.8Hz,1H),7.17(d,J=8.8Hz,1H),3.97(d,J=7.2Hz,2H),3.63(s,3H),3.62(s,3H),2.77(s,3H),1.71(s,3H),1.36–1.27(m,1H),0.52–0.46(m,2H),0.46–0.40(m,2H).
化合物147收率:73%.
1H NMR(400MHz,CDCl
3)δ7.56(d,J=8.8Hz,1H),7.15(d,J=8.8Hz,1H),3.97(d,J=7.2Hz,2H),3.62(s,3H),3.60(s,3H),2.82(s,3H),1.39–1.26(m,1H),1.00–0.91(m,1H),0.83–0.77(m,2H),0.54–0.43(m,6H).
化合物148收率:82%.,
1H NMR(400MHz,CDCl
3)δ7.50(d,J=9.2Hz,1H),7.10(d,J=9.2Hz,1H),3.97(d,J=7.2Hz,2H),3.62(s,3H),3.59(s,3H),3.23(s,6H),2.75(s,3H),2.23(s,3H),1.36–1.24(m,1H),0.50–0.42(m,4H).
化合物149收率:77%.
1H NMR(400MHz,CDCl
3)δ7.50(d,J=8.0Hz,1H),7.09(d,J=8.0Hz,1H),3.97(d,J=7.2Hz,2H),3.62(s,3H),3.60(s,3H),3.17(q,J=7.2Hz,2H),3.03(q,J=7.2Hz,2H),2.75(s,3H),2.24(s,3H),1.36–1.24(m,1H),1.08(t,J=7.2Hz,3H),1.01(t,J=7.2Hz,3H),0.49–0.42(m,4H).
化合物150收率:65%.
1H NMR(400MHz,CDCl
3)δ7.57(d,J=8.8Hz,1H),7.07(d,J=8.8Hz,1H),3.97(d,J=7.2Hz,2H),3.62(s,3H),3.59(s,3H),3.17(q,J=7.2Hz,2H),3.03(q,J=7.2Hz,2H),2.82(s,3H),1.39–1.26(m,1H),1.08(t,J=7.2Hz,3H),1.02–0.91(m,4H),0.83–0.77(m,2H),0.54–0.42(m,6H).
化合物151收率:63%.,
1H NMR(400MHz,CDCl
3)δ7.50(d,J=8.8Hz,1H),7.10(d,J=8.8Hz,1H),3.98(d,J=7.2Hz,2H),3.62(s,3H),3.60(s,3H),3.23(s,3H),3.07(q,J=7.6Hz,2H),2.74(s,3H),2.24(s,3H),1.36–1.24(m,1H),1.17(t,J=7.6Hz,3H),0.52–0.42(m,4H).
化合物152收率:78%.,
1H NMR(400MHz,CDCl
3)δ7.50(d,J=9.2Hz,1H),7.09(d,J=9.2Hz,1H),3.98(d,J=7.2Hz,2H),3.62(s,3H),3.60(s,3H),3.29–3.15(m,4H),3.07(t,J=7.6Hz,1H),2.75(s,3H),2.23(s,3H),1.68–1.48(m,2H),1.36–1.24(m,1H),0.87(t,J=7.2Hz,3H),0.50–0.42(m,4H).
化合物153收率:69%.
1H NMR(400MHz,CDCl
3)δ7.45(d,J=8.8Hz,1H),7.15(d,J=8.8Hz,1H),4.13(d,J=7.2Hz,2H),3.63(s,3H),3.61(s,3H),2.76(s,3H),2.06–1.80(m,7H),1.71(s,3H).
化合物154收率:67%.
1H NMR(400MHz,CDCl
3)δ7.55(d,J=8.8Hz,1H),7.14(d,J=8.8Hz,1H),4.13(d,J=7.2Hz,2H),3.60(s,6H),2.81(s,3H),2.08–1.77(m,7H),0.99–0.91(m,1H),0.85–0.75(m,2H),0.59–0.47(m,2H).
化合物155收率:68%.
1H NMR(400MHz,CDCl
3)δ7.48(d,J=7.8Hz,1H),7.07(d,J=7.8Hz,1H),4.13(d,J=7.2Hz,2H),3.61(s,3H),3.57(s,3H),3.16(q,J=7.2Hz,2H),3.01(q,J=7.2Hz,2H),2.79–2.70(m,4H),2.23(s,3H),2.05–1.93(m,2H),1.83–1.85(m,4H),1.06(t,J=6.8Hz,3H),1.00(t,J=7.0Hz,3H).
化合物156收率:74%.
1H NMR(400MHz,CDCl
3)δ7.49(d,J=7.8Hz,1H),7.04(d,J=7.8Hz,1H),4.13(d,J=7.2Hz,2H),3.61(s,3H),3.57(s,3H),3.16(q,J=7.2Hz,2H),3.01(q,J=7.2Hz,2H),2.79–2.70(m,4H),,2.05–1.93(m,2H),1.83–1.85(m,4H),1.06(t,J=6.8Hz,3H),1.00(t,J=7.0Hz,3H),1.00–0.92(m,1H),0.82–0.76(m,2H),0.55–0.48(m,2H).
化合物157收率:69%.
1H NMR(400MHz,CDCl
3)δ7.46(d,J=8.8Hz,1H),7.17(d,J=8.8Hz,1H),4.06(d,J=7.6Hz,2H),3.64(s,3H),3.62(s,3H),2.77(s,3H),2.45–2.32(m,1H),1.75–1.63(m,7H),1.57–1.47(m,2H),1.40–1.29(m,2H).
化合物158收率:82%.
1H NMR(400MHz,CDCl
3)δ7.56(d,J=8.8Hz,1H),7.15(d,J=8.8Hz,1H),4.05(d,J=7.6Hz,2H),3.61(s,3H),3.60(s,3H),2.82(s,3H),2.47–2.33(m,1H),1.78–1.64(m,4H),1.57–1.46(m,2H),1.39–1.28(m,2H),0.99–0.91(m,1H),0.86–0.76(m,2H),0.58–0.47(m,2H).
化合物159收率:73%.,
1H NMR(400MHz,CDCl
3)δ7.48(d,J=8.4Hz,1H),7.07(d,J=8.4Hz,1H),4.05(d,J=7.6Hz,2H),3.62(s,3H),3.59(s,3H),3.23(s,6H),2.75(s,3H),2.44–2.32(m,1H),2.24(s,3H),1.75–1.63(m,4H),1.57–1.45(m,2H),1.44–1.26(m,2H),
化合物160收率:67%.
1H NMR(400MHz,CDCl
3)δ7.49(d,J=8.8Hz,1H),7.08(d,J=8.8Hz,1H),4.05(d,J=7.6Hz,2H),3.62(s,3H),3.59(s,3H),3.17(q,J=7.2Hz,2H),3.01(q,J=7.2Hz,2H),2.75(s,3H),2.44–2.32(m,1H),2.24(s,3H),1.75–1.62(m,4H),1.57–1.45(m,2H),1.44–1.26(m,2H),1.06(t,J=7.2Hz,3H),1.01(t,J=7.2Hz,3H).
化合物161收率:69%.
1H NMR(400MHz,CDCl
3)δ7.53(d,J=8.8Hz,1H),7.07(d,J=8.8Hz,1H),4.06(d,J=7.6Hz,2H),3.62(s,3H),3.57(s,3H),3.17(q,J=7.2Hz,2H),3.03(q,J=7.2Hz,2H),2.75(s,3H),2.44–2.32(m,1H),1.75–1.62(m,4H),1.57–1.45(m,2H),1.44–1.26(m,2H),1.06(t,J=7.2Hz,3H),1.02–0.91(m,4H),0.86–0.76(m,2H),0.58–0.47(m,2H).
化合物162收率:81%.,
1H NMR(400MHz,CDCl
3)δ7.49(d,J=8.8Hz,1H),7.08(d,J=8.8Hz,1H),4.05(d,J=7.6Hz,2H),3.61(s,3H),3.59(s,3H),3.23(s,3H),3.07(q,J=7.6Hz,2H),2.74(s,3H),2.44–2.32(m,1H),2.23(s,3H),1.75–1.62(m,4H),1.57–1.45(m,2H),1.44–1.26(m,2H),1.17(t,J=7.2Hz,3H).
化合物163收率:69%.,
1H NMR(400MHz,CDCl
3)δ7.48(d,J=8.4Hz,1H),7.07(d,J=8.4Hz,1H),4.05(d,J=7.6Hz,2H),3.62(s,3H),3.59(s,3H),3.28–3.19(m,4H),3.11–2.98(m,1H),2.75(s,3H),2.44–2.32(m,1H),2.22(s,3H),1.75–1.45(m,8H),1.44–1.26(m,2H),0.87(t,J=6.8Hz,3H).
化合物164收率:70%.
1H NMR(400MHz,CDCl
3)δ7.45(d,J=8.8Hz,1H),7.16(d,J=8.8Hz,1H),3.94(d,J=7.4Hz,2H),3.64(s,3H),3.62(s,3H),2.77(s,3H),1.90–1.79(m,1H),1.73–1.62(m,8H),1.23–1.03(m,5H).
化合物165收率:73%.
1H NMR(400MHz,CDCl
3)δ7.56(d,J=8.8Hz,1H),7.15(d,J=8.8Hz,1H),3.94(d,J=7.2Hz,2H),3.61(s,3H),3.60(s,3H),2.82(s,3H),1.89–1.78(m,1H),1.75–1.61(m,5H),1.25–1.15(m,3H),1.13–1.02(m,2H),1.01–0.91(m,1H),0.84–0.78(m,2H),0.55–0.48(m,2H).
化合物166收率:74%.
1H NMR(400MHz,CDCl
3)δ7.49(d,J=8.4Hz,1H),7.07(d,J=8.4Hz,1H),3.93(d,J=7.2Hz,2H),3.61(s,3H),3.58(s,3H),3.16(q,J=7.2Hz,2H),3.00(q,J=7.2Hz,2H),2.75(s,3H),2.24(s,3H),1.89–1.79(m,1H),1.75–1.68(m,2H),1.67–1.58(m,3H),1.27–1.11(m,4H),1.08–1.04(m,4H),1.00(t,J=7.2Hz,3H).
化合物167收率:66%.
1H NMR(400MHz,CDCl
3)δ7.46(d,J=8.8Hz,1H),7.15(d,J=8.8Hz,1H),5.79–5.69(m,1H),4.30(q,J=7.6Hz,1H),4.06–3.92(m,3H),3.64(s,3H),3.61(s,3H),2.75(s,3H),2.42–2.32(m,1H),2.25–2.15(m,1H),1.70(s,3H).
化合物168收率:69%.
1H NMR(400MHz,CDCl
3)δ7.56(d,J=8.8Hz,1H),7.14(d,J=8.8Hz,1H),5.79–5.68(m,1H),4.30(q,J=7.6Hz,1H),4.05–3.95(m,3H),3.60(s,3H),3.59(s,3H),2.80(s,3H),2.41–2.32(m,1H),2.25–2.14(m,1H),0.98–0.90(m,1H),0.84–0.75(m,2H),0.52–0.47(m,2H).
化合物169收率:67%.
1H NMR(400MHz,CDCl
3)δ7.50(d,J=8.8Hz,1H),7.07(d,J=8.8Hz,1H),5.78–5.68(m,1H),4.30(q,J=7.6Hz,1H),4.06–3.93(m,3H),3.62(s,3H),3.58(s,3H),3.21(q,J=7.2Hz,2H),3.08(q,J=7.2Hz,2H),2.73(s,3H),2.39–2.30(m,1H),2.25–2.18(m,1H),2.17(s,3H),1.10(t,J=7.2Hz,3H),1.03(t,J=7.2Hz,3H).
化合物170收率:66%.
1H NMR(400MHz,CDCl
3)δ7.56(d,J=8.8Hz,1H),7.07(d,J=8.8Hz,1H),5.78–5.68(m,1H),4.30(q,J=7.6Hz,1H),4.06–3.93(m,3H),3.62(s,3H),3.58(s,3H),3.21(q,J=7.2Hz,2H),3.08(q,J=7.2Hz,2H),2.73(s,3H),2.39–2.30(m,1H),2.25–2.18(m,1H),1.10(t,J=7.2Hz,3H),1.03(t,J=7.2Hz,3H),0.98–0.90(m,1H),0.84–0.75(m,2H),0.52–0.47(m,2H).
化合物171收率:69%.
1H NMR(400MHz,CDCl
3)δ7.45(d,J=8.8Hz,1H),7.14(d,J=8.8Hz,1H),5.20–5.10(m,1H),4.12–4.05(m,2H),3.64(s,3H),3.59(s,3H),3.54–3.48(m,2H),2.92–2.80(m,2H),2.74(s,3H),1.71(s,3H),1.64–1.55(m,2H).
化合物172收率:76%.
1H NMR(400MHz,CDCl
3)δ7.55(d,J=8.8Hz,1H),7.12(d,J=8.8Hz,1H),5.20–5.09(m,1H),4.13–4.04(m,2H),3.59(s,3H),3.58(s,3H),3.54–3.47(m,2H),2.91–2.82(m,2H),2.79(s,3H),1.64–1.53(m,2H),1.00–0.90(m,1H),0.83–0.76(m,2H),0.55–0.46(m,2H).
化合物173收率:82%.,
1H NMR(400MHz,CDCl
3)δ7.48(d,J=8.4Hz,1H),7.06(d,J=8.4Hz,1H),5.20–5.08(m,1H),4.14–4.04(m,2H),3.62(s,3H),3.56(s,3H),3.52(t,J=11.6Hz,2H),3.23(s,6H),2.92–2.79(m,2H),2.74(s,3H),2.19(s,3H),1.59–1.52(m,2H).
化合物174收率:73%.
1H NMR(400MHz,CDCl
3)δ7.48(d,J=8.4Hz,1H),7.06(d,J=8.4Hz,1H),5.20–5.08(m,1H),4.14–4.04(m,2H),3.62(s,3H),3.56(s,3H),3.51(t,J=11.6Hz,2H),3.19(q,J=7.2Hz,2H),3.07(q,J=7.2Hz,2H),2.92–2.79(m,2H),2.72(s,3H),2.19(s,3H),1.59–1.52(m,2H),1.09(t,J=7.2Hz,3H),1.02(t,J=7.2Hz,3H).
化合物175收率:69%.
1H NMR(400MHz,CDCl
3)δ7.53(d,J=8.4Hz,1H),7.05(d,J=8.4Hz,1H),5.20–5.08(m,1H),4.14–4.04(m,2H),3.62(s,3H),3.56(s,3H),3.51(t,J=11.6Hz,2H),3.19(q,J=7.2Hz,2H),3.07(q,J=7.2Hz,2H),2.92–2.79(m,2H),2.72(s,3H),1.59–1.52(m,2H),1.09(t,J=7.2Hz,3H),1.02(t,J=7.2Hz,3H),1.00–0.90(m,1H),0.83–0.76(m,2H),0.55–0.46(m,2H).
化合物176收率:89%.,
1H NMR(400MHz,CDCl
3)δ7.48(d,J=9.2Hz,1H),7.06(d,J=9.2Hz,1H),5.20–5.08(m,1H),4.14–4.04(m,2H),3.62(s,3H),3.56(s,3H),3.51(t,J=11.6Hz,2H),3.23(s,3H),3.07(q,J=7.6Hz,2H),2.92–2.79(m,2H),2.72(s,3H),2.19(s,3H),1.59–1.52(m,2H),1.17(t,J=7.2Hz,3H).
化合物177收率:89%.,
1H NMR(400MHz,CDCl
3)δ7.48(d,J=8.4Hz,1H),7.06(d,J=8.4Hz,1H),5.20–5.08(m,1H),4.14–4.04(m,2H),3.62(s,3H),3.56(s,3H),3.51(t,J=11.6Hz,2H),3.29–3.21(m,4H),3.11–2.98(m,1H),2.92–2.79(m,2H),2.74(s,3H),2.20(s,3H),1.59–1.52(m,2H),1.68–1.48(m,2H),0.87(t,J=7.2Hz,3H).
化合物178收率:68%.
1H NMR(400MHz,CDCl
3)δ7.45(d,J=8.4Hz,1H),7.15(d,J=8.4Hz,1H),4.35(d,J=7.2Hz,2H),4.05–3.88(m,2H),3.81–3.71(m,1H),3.63(s,3H),3.61(s,3H),2.76(s,3H),2.12–1.96(m,2H),1.94–1.59(m,5H).
化合物179收率:64%.
1H NMR(400MHz,CDCl
3)δ7.55(d,J=8.8Hz,1H),7.13(d,J=8.8Hz,1H),4.42–4.31(m,2H),4.00–3.90(m,2H),3.78–3.70(m,1H),3.60(s,3H),3.59(s,3H),2.81(s,3H),2.12–1.96(m,2H),1.94–1.83(m,1H),1.74–1.63(m,1H),0.97–0.88(m,1H),0.85–0.75(m,2H),0.58–0.48(m,2H).
化合物180收率:69%.
1H NMR(400MHz,CDCl
3)δ7.45(d,J=8.4Hz,1H),7.15(d,J=8.4Hz,1H),4.35(d,J=7.2Hz,2H),4.05–3.88(m,2H),3.81–3.71(m,1H),3.63(s,3H),3.61(s,3H),3.19(q,J=7.2Hz,2H),3.07(q,J=7.2Hz,2H),2.76(s,3H),2.19(s,3H),2.12–1.96(m,2H),1.94–1.59(m,2H),1.09(t,J=7.2Hz,3H),1.02(t,J=7.2Hz,3H).
化合物181收率:75%.
1H NMR(400MHz,CDCl
3)δ7.54(d,J=8.4Hz,1H),7.12(d,J=8.4Hz,1H),4.35(d,J=7.2Hz,2H),4.05–3.88(m,2H),3.81–3.71(m,1H),3.63(s,3H),3.61(s,3H),3.19(q,J=7.2Hz,2H),3.07(q,J=7.2Hz,2H),2.76(s,3H),2.12–1.96(m,2H),1.94–1.59(m,2H),1.09(t,J=7.2Hz,3H),1.02(t,J=7.2Hz,3H),0.97–0.88(m,1H),0.85–0.75(m,2H),0.58–0.48(m,2H).
化合物182收率:69%.
1H NMR(400MHz,CDCl
3)δ7.47(d,J=8.8Hz,1H),7.18(d,J=8.8Hz,1H),4.22–4.15(m,1H),4.12–4.05(m,1H),3.98–3.91(m,1H),3.87–3.74(m,2H),3.66–3.59(m,7H),2.80–2.72(m,4H),2.06–1.96(m,1H),1.82–1.74(m,1H),1.71(s,3H).
化合物183收率:70%.
1H NMR(400MHz,CDCl
3)δ7.58(d,J=8.8Hz,1H),7.16(d,J=8.8Hz,1H),4.22–4.15(m,1H),4.12–4.05(m,1H),3.98–3.91(m,1H),3.86–3.74(m,2H),3.63–3.58(m,7H),2.81(s,3H),2.79–2.72(m,1H),2.09–1.95(m,1H),1.84–1.71(m,1H),1.01–0.90(m,1H),0.84–0.75(m,2H),0.56–0.46(m,2H).
化合物184收率:86%.,
1H NMR(400MHz,CDCl
3)δ7.50(d,J=9.2Hz,1H),7.10(d,J=9.2Hz,1H),4.22–4.15(m,1H),4.12–4.04(m,1H),3.98–3.90(m,1H),3.84–3.74(m,2H),3.64–3.57(m,7H),3.23(s,6H),2.78–2.71(m,4H),2.21(s,3H),2.04–1.92(m,1H),1.80–1.68(m,1H),
化合物185收率:80%.
1H NMR(400MHz,CDCl
3)δ7.51(d,J=8.8Hz,1H),7.09(d,J=8.8Hz,1H),4.22–4.15(m,1H),4.12–4.04(m,1H),3.98–3.90(m,1H),3.84–3.74(m,2H),3.64–3.57(m,7H),3.19(q,J=7.2Hz,2H),3.06(q,J=7.2Hz,2H),2.78–2.71(m,4H),2.20(s,3H),2.04–1.92(m,1H),1.80–1.68(m,1H),1.08(t,J=7.2Hz,3H),1.02(t,J=7.2Hz,3H).
化合物186收率:69%.
1H NMR(400MHz,CDCl
3)δ7.57(d,J=8.8Hz,1H),7.06(d,J=8.8Hz,1H),4.22–4.15(m,1H),4.12–4.04(m,1H),3.98–3.90(m,1H),3.84–3.74(m,2H),3.64–3.57(m,7H),3.19(q,J=7.2Hz,2H),3.06(q,J=7.2Hz,2H),2.78–2.71(m,4H),2.04–1.92(m,1H),1.80–1.68(m,1H),1.08(t,J=7.2Hz,3H),1.03–0.90(m,4H),0.84–0.75(m,2H),0.56–0.46(m,2H).
化合物187收率:77%.,
1H NMR(400MHz,CDCl
3)δ7.51(d,J=9.2Hz,1H),7.09(d,J=9.2Hz,1H),4.22–4.04(m,2H),3.98–3.90(m,1H),3.84–3.74(m,2H),3.64–3.57(m,7H),3.23(s,3H),3.07(q,J=7.2Hz,2H),2.78–2.71(m,4H),2.20(s,3H),2.04–1.92(m,1H),1.80–1.68(m,1H),1.17(t,J=7.2Hz,3H).
化合物188收率:79%.,
1H NMR(400MHz,CDCl
3)δ7.50(d,J=8.4Hz,1H),7.09(d,J=8.4Hz, 1H),4.22–4.04(m,2H),3.98–3.90(m,1H),3.84–3.74(m,2H),3.64–3.57(m,7H),3.29–3.18(m,4H),3.11–2.98(m,1H),2.78–2.71(m,4H),2.20(s,3H),2.04–1.92(m,1H),1.80–1.50(m,3H),0.87(t,J=7.2Hz,3H).
化合物189收率:74%.
1H NMR(400MHz,CDCl
3)δ7.47(d,J=8.8Hz,1H),7.17(d,J=8.8Hz,1H),4.00(d,J=7.2Hz,2H),3.99–3.93(m,2H),3.64(s,3H),3.62(s,3H),3.39–3.31(m,2H),2.77(s,3H),2.15–2.05(m,1H),1.71(s,3H),1.62–1.55(m,2H),1.54–1.45(m,2H).
化合物190收率:69%.
1H NMR(400MHz,CDCl
3)δ7.57(d,J=8.8Hz,1H),7.15(d,J=8.8Hz,1H),4.00(d,J=7.2Hz,2H),3.98–3.92(m,2H),3.61(s,3H),3.59(s,3H),3.38–3.30(m,2H),2.81(s,3H),2.15–2.04(m,1H),1.62–1.55(m,2H),1.54–1.45(m,2H),0.99–0.91(m,1H),0.82–0.76(m,2H),0.53–0.46(m,2H).
化合物191收率:77%.,
1H NMR(400MHz,CDCl
3)δ7.50(d,J=9.2Hz,1H),7.09(d,J=9.2Hz,1H),4.06–3.98(m,2H),3.98–3.91(m,2H),3.62(s,3H),3.59(s,3H),3.38–3.29(m,2H),3.23(s,6H),2.75(s,3H),2.19(s,3H),2.11–2.01(m,1H),1.59–1.41(m,4H),
化合物192收率:66%.
1H NMR(400MHz,CDCl
3)δ7.50(d,J=8.8Hz,1H),7.09(d,J=8.8Hz,1H),4.06–3.98(m,2H),3.98–3.91(m,2H),3.62(s,3H),3.59(s,3H),3.38–3.29(m,2H),3.19(q,J=7.2Hz,2H),3.06(q,J=7.2Hz,2H),2.75(s,3H),2.19(s,3H),2.11–2.01(m,1H),1.59–1.41(m,4H),1.08(t,J=7.2Hz,3H),1.02(t,J=7.2Hz,3H).
化合物193收率:69%.
1H NMR(400MHz,CDCl
3)δ7.55(d,J=8.8Hz,1H),7.03(d,J=8.8Hz,1H),4.06–3.98(m,2H),3.98–3.91(m,2H),3.62(s,3H),3.59(s,3H),3.38–3.29(m,2H),3.19(q,J=7.2Hz,2H),3.06(q,J=7.2Hz,2H),2.75(s,3H),2.11–2.01(m,1H),1.59–1.41(m,4H),1.08(t,J=7.2Hz,3H),1.02(t,J=7.2Hz,3H),0.99–0.91(m,1H),0.82–0.76(m,2H),0.53–0.46(m,2H).
化合物194收率:88%.,
1H NMR(400MHz,CDCl
3)δ7.50(d,J=8.8Hz,1H),7.09(d,J=8.8Hz,1H),4.06–3.99(m,2H),3.98–3.91(m,2H),3.62(s,3H),3.59(s,3H),3.38–3.29(m,2H),3.23(s,3H),3.07(q,J=7.2Hz,2H),2.75(s,3H),2.20(s,3H),2.12–2.02(m,1H),1.59–1.41(m,4H),1.17(t,J=12.8Hz,3H).
化合物195收率:81%.,
1H NMR(400MHz,CDCl
3)δ7.49(d,J=8.8Hz,1H),7.08d,J=8.8Hz,1H),4.06–3.99(m,2H),3.98–3.91(m,2H),3.62(s,3H),3.59(s,3H),3.38–3.17(m,6H),3.11–2.98(m,1H),2.75(s,3H),2.20(s,3H),2.12–2.02(m,1H),1.65–1.41(m,6H),0.87(t,J=7.2Hz,3H).
本发明还提供如下3个对比化合物:
化合物D1收率:65%.
1H NMR(600MHz,CDCl
3)δ7.54(d,J=8.4Hz,1H),7.37(dt,J=3.2,1.4Hz,2H),7.36–7.32(m,2H),7.17(d,J=7.2Hz,1H),3.68(s,3H),3.66(s,3H),2.76(s,3H),2.18(s,3H),1.79(s,3H).
化合物D2收率:92%.
1HNMR(600MHz,CDCl
3)δ7.88(d,J=7.8Hz,2H),7.63(dd,J=8.4,8.4Hz,1H),7.54–7.45(m,3H),7.36–7.31(m,3H),7.20–7.12(m,2H),3.77(s,3H),3.63(s,3H),2.68(s,3H),2.16(s,3H),1.80(s,3H).
化合物D3收率89%,
1HNMR(600MHz,CDCl
3)δ7.86(d,J=7.0Hz,2H),7.61(t,J=7.8Hz,1H),7.52–7.45(m,3H),7.36–7.31(m,3H),7.17(d,J=8.4Hz,1H),7.14(d,J=6.0Hz,1H),5.83(s,2H),3.84(s,3H),3.62(s,3H),2.69(s,3H),2.15(s,3H),1.80(s,3H).
测试例
初筛试验(盆栽法):供试靶标为如表2-表6中所示。
苗后茎叶喷雾:取内径7cm纸杯,装复合土(菜园土:育苗基质,1:2,v/v)至3/4处,直接播种杂草,覆土0.2cm,待长至4-5叶期备用。本发明的化合物和前述对比化合物D1、D2、D3均按照12克/亩的剂量在自动喷雾塔施药后,待作物叶面药液晾干后移入温室培养(25度-28度,湿度70%),30天后调查结果。
生长抑制率评价方法为目测法,具体根据表1所示的情况进行评级,测试结果如表2-表6中所示。
表1
(%) | 评价(抑制、畸形、白化等) | 生长抑制率级别 |
0-5 | 对杂草或作物生长无影响,无药效症状。 | 0 |
5-29 | 对杂草或作物生长有轻微影响,无明显药效症状 | 1 |
30-49 | 对杂草或作物生长有抑制,无明显药效症状。 | 2 |
50-69 | 对杂草或作物长有影响,有明显药效症状。 | 3 |
70-89 | 杂草或作物受到严重生长抑制。 | 4 |
80-100 | 杂草或作物死亡。 | 5 |
表2
化合物 | 稗草 | 狗尾草 | 马唐 | 苋菜 | 藜 | 苘麻 |
1 | 5 | 5 | 5 | 5 | 5 | 5 |
2 | 5 | 5 | 5 | 4 | 5 | 5 |
5 | 5 | 4 | 3 | 4 | 5 | 3 |
9 | 5 | 5 | 4 | 5 | 4 | 4 |
10 | 5 | 5 | 4 | 5 | 3 | 3 |
13 | 5 | 5 | 3 | 4 | 3 | 3 |
17 | 5 | 5 | 5 | 4 | 3 | 3 |
18 | 5 | 5 | 5 | 4 | 4 | 3 |
21 | 4 | 4 | 3 | 4 | 4 | 3 |
25 | 5 | 5 | 5 | 5 | 4 | 5 |
26 | 5 | 5 | 4 | 4 | 3 | 3 |
29 | 5 | 4 | 3 | 4 | 4 | 5 |
33 | 5 | 5 | 4 | 3 | 4 | 4 |
34 | 5 | 4 | 4 | 5 | 4 | 5 |
37 | 5 | 4 | 3 | 3 | 4 | 5 |
41 | 4 | 3 | 4 | 4 | 3 | 3 |
42 | 5 | 3 | 3 | 5 | 4 | 3 |
45 | 4 | 3 | 3 | 5 | 3 | 3 |
49 | 5 | 5 | 5 | 4 | 3 | 3 |
50 | 5 | 5 | 4 | 4 | 5 | 4 |
53 | 4 | 3 | 3 | 3 | 3 | 3 |
57 | 5 | 5 | 5 | 4 | 3 | 3 |
58 | 5 | 5 | 3 | 3 | 3 | 2 |
61 | 4 | 4 | 3 | 4 | 4 | 3 |
65 | 5 | 4 | 5 | 4 | 3 | 3 |
66 | 5 | 5 | 3 | 5 | 3 | 3 |
69 | 4 | 3 | 3 | 4 | 3 | 3 |
73 | 5 | 5 | 4 | 4 | 4 | 5 |
74 | 5 | 5 | 5 | 4 | 4 | 3 |
77 | 5 | 5 | 3 | 4 | 3 | 3 |
81 | 5 | 5 | 4 | 3 | 4 | 5 |
82 | 5 | 5 | 4 | 4 | 4 | 3 |
85 | 5 | 5 | 3 | 4 | 3 | 4 |
89 | 4 | 5 | 5 | 4 | 3 | 5 |
90 | 5 | 5 | 5 | 3 | 3 | 3 |
93 | 4 | 3 | 3 | 4 | 4 | 3 |
97 | 5 | 5 | 4 | 4 | 4 | 4 |
98 | 5 | 5 | 5 | 4 | 4 | 2 |
101 | 5 | 4 | 4 | 4 | 3 | 3 |
105 | 5 | 4 | 5 | 4 | 3 | 4 |
106 | 5 | 5 | 4 | 5 | 3 | 3 |
109 | 5 | 4 | 3 | 4 | 3 | 4 |
113 | 4 | 3 | 4 | 4 | 3 | 3 |
114 | 5 | 4 | 3 | 5 | 4 | 3 |
117 | 4 | 4 | 3 | 5 | 3 | 3 |
121 | 5 | 5 | 5 | 4 | 3 | 4 |
122 | 5 | 4 | 5 | 4 | 3 | 3 |
125 | 5 | 5 | 5 | 4 | 3 | 3 |
129 | 5 | 5 | 4 | 4 | 3 | 4 |
130 | 5 | 5 | 5 | 4 | 4 | 5 |
132 | 4 | 3 | 3 | 3 | 4 | 3 |
136 | 5 | 5 | 4 | 4 | 4 | 4 |
137 | 4 | 3 | 3 | 4 | 3 | 3 |
139 | 3 | 3 | 3 | 4 | 3 | 3 |
143 | 3 | 4 | 4 | 4 | 3 | 4 |
144 | 3 | 3 | 3 | 4 | 3 | 4 |
145 | 3 | 2 | 2 | 3 | 3 | 2 |
146 | 5 | 5 | 5 | 4 | 3 | 3 |
147 | 5 | 5 | 4 | 5 | 4 | 3 |
149 | 3 | 3 | 3 | 4 | 3 | 3 |
153 | 5 | 4 | 4 | 4 | 3 | 3 |
154 | 5 | 4 | 4 | 5 | 4 | 5 |
155 | 4 | 3 | 4 | 3 | 3 | 4 |
157 | 3 | 3 | 3 | 3 | 3 | 3 |
158 | 3 | 3 | 3 | 4 | 3 | 3 |
160 | 3 | 2 | 3 | 3 | 2 | 3 |
164 | 3 | 3 | 2 | 3 | 3 | 2 |
165 | 4 | 3 | 3 | 2 | 3 | 4 |
166 | 2 | 3 | 3 | 3 | 3 | 3 |
167 | 5 | 5 | 5 | 4 | 4 | 5 |
168 | 5 | 5 | 5 | 4 | 3 | 5 |
169 | 5 | 4 | 3 | 4 | 3 | 5 |
171 | 5 | 5 | 5 | 4 | 3 | 4 |
172 | 5 | 5 | 4 | 4 | 3 | 3 |
174 | 4 | 4 | 3 | 4 | 3 | 3 |
178 | 4 | 4 | 2 | 4 | 3 | 3 |
179 | 5 | 4 | 4 | 4 | 3 | 3 |
180 | 3 | 3 | 3 | 3 | 3 | 2 |
182 | 5 | 4 | 4 | 4 | 3 | 3 |
183 | 5 | 5 | 5 | 4 | 3 | 3 |
185 | 4 | 4 | 3 | 4 | 4 | 3 |
189 | 5 | 5 | 5 | 5 | 3 | 4 |
190 | 5 | 4 | 5 | 5 | 3 | 5 |
192 | 5 | 4 | 4 | 3 | 4 | 3 |
D1 | 5 | 5 | 5 | 5 | 5 | 5 |
D2 | 5 | 5 | 5 | 5 | 5 | 5 |
D3 | 4 | 5 | 5 | 5 | 5 | 5 |
表3:部分化合物对玉米的安全性评价
化合物 | 玉米 |
1 | 1 |
2 | 1 |
5 | 1 |
9 | 1 |
10 | 1 |
13 | 0 |
17 | 1 |
18 | 1 |
21 | 0 |
26 | 0 |
29 | 0 |
33 | 0 |
34 | 1 |
37 | 1 |
41 | 1 |
42 | 1 |
45 | 0 |
49 | 1 |
50 | 1 |
53 | 0 |
57 | 1 |
61 | 1 |
65 | 1 |
66 | 1 |
69 | 0 |
74 | 1 |
77 | 0 |
81 | 1 |
82 | 1 |
85 | 0 |
93 | 0 |
97 | 1 |
98 | 1 |
101 | 0 |
105 | 1 |
106 | 1 |
109 | 0 |
114 | 1 |
117 | 0 |
121 | 1 |
122 | 1 |
125 | 0 |
129 | 1 |
132 | 0 |
136 | 1 |
137 | 1 |
139 | 0 |
143 | 0 |
144 | 1 |
145 | 0 |
147 | 1 |
149 | 0 |
153 | 1 |
154 | 1 |
155 | 0 |
157 | 1 |
160 | 0 |
164 | 0 |
166 | 0 |
167 | 1 |
169 | 0 |
171 | 1 |
172 | 0 |
174 | 1 |
178 | 1 |
180 | 0 |
183 | 1 |
185 | 1 |
192 | 0 |
D1 | 1 |
D2 | 3 |
D3 | 2 |
表4:部分化合物对小麦的安全性评价
化合物 | 小麦 |
5 | 1 |
13 | 1 |
21 | 1 |
25 | 1 |
53 | 0 |
61 | 0 |
69 | 1 |
73 | 1 |
77 | 1 |
82 | 1 |
85 | 1 |
89 | 1 |
90 | 1 |
93 | 1 |
101 | 0 |
109 | 1 |
113 | 1 |
125 | 1 |
132 | 0 |
137 | 1 |
139 | 0 |
143 | 1 |
144 | 1 |
145 | 0 |
149 | 1 |
155 | 1 |
160 | 1 |
165 | 1 |
166 | 1 |
168 | 1 |
169 | 1 |
174 | 1 |
178 | 1 |
180 | 0 |
182 | 1 |
185 | 1 |
189 | 1 |
190 | 1 |
192 | 0 |
D1 | 5 |
D2 | 4 |
D3 | 3 |
表5:部分化合物对籼稻的安全性评价
化合物 | 籼稻 |
5 | 1 |
13 | 0 |
21 | 0 |
29 | 1 |
45 | 0 |
53 | 0 |
58 | 1 |
61 | 0 |
69 | 0 |
77 | 1 |
85 | 0 |
90 | 1 |
93 | 1 |
101 | 1 |
109 | 1 |
117 | 1 |
125 | 1 |
130 | 1 |
132 | 1 |
139 | 0 |
143 | 1 |
145 | 0 |
146 | 1 |
149 | 0 |
155 | 1 |
158 | 1 |
160 | 0 |
166 | 0 |
169 | 1 |
171 | 1 |
174 | 0 |
179 | 1 |
180 | 0 |
185 | 1 |
192 | 1 |
D1 | 5 |
D2 | 5 |
D3 | 5 |
表6:部分化合物对粳稻的安全性评价
化合物 | 粳稻 |
5 | 0 |
13 | 1 |
21 | 0 |
29 | 0 |
33 | 1 |
37 | 0 |
41 | 1 |
45 | 0 |
53 | 0 |
58 | 1 |
61 | 1 |
69 | 0 |
77 | 1 |
85 | 0 |
93 | 0 |
98 | 1 |
101 | 1 |
113 | 1 |
117 | 0 |
125 | 1 |
132 | 0 |
139 | 0 |
145 | 1 |
149 | 0 |
155 | 0 |
157 | 1 |
160 | 0 |
164 | 1 |
166 | 1 |
169 | 1 |
174 | 0 |
180 | 1 |
182 | 1 |
185 | 1 |
192 | 0 |
D1 | 5 |
D2 | 5 |
D3 | 5 |
由上述结果可知,本发明的化合物在除草测试实验中,对常见的禾本科和阔叶杂草均表现出良好的除草活性,特别对稗草和狗尾草具有很好的防治效果,与对照药剂D1、D2、D3具有相当的除草活性。
同时,本发明的化合物对玉米、小麦安全,进一步地,本发明中连接了氨基甲酸酯片段后的化合物对两种水稻(籼稻和粳稻)也非常安全,作物安全性明显优于对照化合物,能够用于水稻田防除稗草等恶性杂草。
并且,对照药剂D1、D2和D3对测试籼稻和粳稻不具有安全性,几乎完全抑制,不能用于水稻田进行杂草防治。
以上详细描述了本发明的优选实施方式,但是,本发明并不限于此。在本发明的技术构思范围内,可以对本发明的技术方案进行多种简单变型,包括各个技术特征以任何其它的合适方式进行组合,这些简单变型和组合同样应当视为本发明所公开的内容,均属于本发明的保护范围。
Claims (10)
- 根据权利要求1所述的化合物,其中,在式(I)中,X选自C 1-8的烷基、由1-6个选自卤素的原子取代的C 1-8的烷基、由C 1-3的烷氧基取代的C 2-8的烷基、C 2-8的烯基、C 2-8的炔基、含有至少一个O原子的C 2-8的环烷基、由含有至少一个O原子的C 2-6的环烷基取代的C 3-8的烷基;Y选自H、C 1-4的烷基;Z为H或式(I-1)所示的基团,其中,在式(I-1)中,R 1和R 2相同或不同,各自独立地选自C 1-4的烷基。
- 根据权利要求1或2所述的化合物,其中,在式(I)中,Z为H。
- 根据权利要求1或2所述的化合物,其中,在式(I)中,Z为式(I-1)所示的基团,且在式(I-1)中,R 1和R 2相同或不同,各自独立地选自C 1-3的烷基。
- 权利要求1-5中任意一项所述的吡唑喹唑啉二酮类化合物在防治杂草中的应用;优选地,所述杂草选自阔叶杂草、禾本科杂草和莎草科杂草中的至少一种。
- 权利要求1-5中任意一项所述的吡唑喹唑啉二酮类化合物作为农药除草剂的应用。
- 一种农药除草剂,该农药除草剂由活性成分和辅料组成,所述活性成分包括权利要求1-5中任意一项所述的吡唑喹唑啉二酮类化合物中的至少一种。
- 根据权利要求8所述的农药除草剂,其中,所述活性成分的含量为1~99.9999重量%。
- 根据权利要求8或9所述的农药除草剂,其中,所述农药除草剂的剂型选自乳油、悬浮剂、可湿性粉剂、粉剂、粒剂、水剂、毒饵、母液和母粉中的至少一种。
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