CN105153177A - Furan chroman oxime alkene/propargyl ether and preparation method and application thereof - Google Patents
Furan chroman oxime alkene/propargyl ether and preparation method and application thereof Download PDFInfo
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- CN105153177A CN105153177A CN201510622482.9A CN201510622482A CN105153177A CN 105153177 A CN105153177 A CN 105153177A CN 201510622482 A CN201510622482 A CN 201510622482A CN 105153177 A CN105153177 A CN 105153177A
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- chroman
- furo
- propargyl ether
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- alkene
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- 0 CC(C)(C1)OC2=C1CCC1=C2[O+]CCC1=*OCC#C Chemical compound CC(C)(C1)OC2=C1CCC1=C2[O+]CCC1=*OCC#C 0.000 description 1
- WJGPNUBJBMCRQH-UHFFFAOYSA-N CC(C)(C1)Oc2c1cccc2O Chemical compound CC(C)(C1)Oc2c1cccc2O WJGPNUBJBMCRQH-UHFFFAOYSA-N 0.000 description 1
- KWNZTOIFNJIZJN-UHFFFAOYSA-N CC(C)(C1)Oc2c1cccc2OCCC#N Chemical compound CC(C)(C1)Oc2c1cccc2OCCC#N KWNZTOIFNJIZJN-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
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- 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
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
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- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
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- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
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- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
The invention relates to furan chroman oxime alkene/propargyl ether shown in the chemical structural formula I/II (please see the formula in the specification). R in the formula is selected from hydrogen, C1-C2 alkyl groups, and C3-C4 straight chain or C3-C4 branched chain alkyl groups. The furan chroman oxime alkene/propargyl ether is used in preparation of sterilizing agents.
Description
Technical field
The present invention relates to preparation method and the application of new compound, specifically furo chroman oxime alkene/propargyl ether preparation with as the application preparing sterilant.
Background technology
Found first oximino ether bactericide frost urea mould (Cymoxan) from 1974 so far, [there is the progress of bioactive oximinoether about the active compound of this class formation continues to bring out.Modern, 2008,7 (2): 6-10].Become oxime by choosing the activated lead compound of tool, and introducing becomes oxime ether to be one of study hotspot of New pesticides discovery compared with the heterocycle of high biological activity.Willow likes equality [Chinese patent CN98112665.0; Central China Normal University's journal (natural science edition), 2004,38 (1): 66-68] 4 kind 3 is described, 3-dimethyl-1-(1,2,4-triazol-1-yl) Diacetylmonoxime benzylic ether preparation and under 100mg/L dosage, to the mycelia of Pyricularia oryzae, Rhizoctonia solani Kuhn, Sclerotinia sclerotiorum, cotton rhizoctonia solani and fusarium graminearum, there is germicidal action.
Chinese invention patent describes 1-(1,2,4-triazol-1-yl) ketoxime ether and oxime ether acid amides and fungicidal activity [1-(1 thereof, 2,4-triazol-1-yl) ketoxime ether and as the application preparing sterilant, Chinese invention patent, ZL201110112389.5,2013.3.13 authorize; 1-(1,2,4-triazolyl) ketoxime ether-acylamide and application thereof, Chinese invention patent, ZL201110154877.2,2013.6.12 authorize].
Chinese patent [201010553848.9] describes researches and develops the application of a series of compound in preparation non-amino formate ester agricultural chemicals based on benzofuranol, Chinese patent [ZL201010533786.5] describes a series of 4-(cumarone-5-base) preparation of-2-benzyl imino thiazole and the application as antitumor drug thereof, Chinese patent [CN102786515A] describes a series of 2-(2,2-dimethyl-2,3-Dihydrobenzofuranes-5-base) morpholine preparation method and as prepare thymoleptic application.Chinese patent describes the non-amino formate ester agricultural chemicals or other functional compounds researched and developed based on benzofuranol, the Chinese invention patent of the preparation and application of particular compound: 4-(cumarone-5-base)-2-benzyl imino thiazole and the application as antitumor drug thereof, ZL201010533786.5,2012.7.25 authorize; 4-(cumarone-5-base)-2-virtue aminothiazole and preparation method thereof and application, ZL201010553848.9,2012.7.4 authorize; 5-[2-(benzyl imino-) thiazole-4-yl] furans phenolic ether is as the application preparing sterilant, and ZL201110102467.3,2013.3.27 authorize; 4-(cumarone-5-base)-2-benzyl imino thiazole is as the application preparing weedicide, and ZL201110102443.8,2013.6.5 authorize; 5-[2-(benzyl imino-) thiazole-4-yl] furans phenolic ether and as the application preparing sterilant, ZL201110102455.0,2013.6.12 authorize; Have 5-(2-virtue aminothiazole-4-base) benzofuranol ether compound and the preparation method of weeding activity, ZL201210016277.4,2014.8.13 authorize; 2-(2,2-dimethyl-2,3-Dihydrobenzofuranes-5-base) morpholine and preparation method thereof and application, ZL201210106643.5,2014.7.23 authorize; 4-(cumarone-5-base)-2-phenylamino thiazole is as the application of sterilant, and ZL201310111413.2,2014.5.28 authorize; 2-(2-benzyl hydrazono-)-4-(cumarone-5-base) thiazole and preparation method thereof and application, ZL201310109794.0,2015.4.1 authorize; 2-(1,2,4-triazole-1-methyl)-2-(cumarone-5-base)-DOX and application thereof, CN201310247669.6,2013.6.20; N-[4-(cumarone-5-base) thiazol-2-yl] acid amides and preparation method thereof and application, CN201310308471.4,2013.7.22.
Summary of the invention
The object of the present invention is to provide furo chroman oxime alkene/propargyl ether (I and II):
In formula, R is selected from: hydrogen, C
1~ C
2alkyl, C
3~ C
4straight chain or C
3~ C
4branched-chain alkyl.
Furo chroman oxime alkene/propargyl ether is the object of the present invention is to provide to be selected from following compounds:
The object of the present invention is to provide the preparation method of furo chroman oxime alkene/propargyl ether, it is characterized in that obtaining furo chroman oxime alkene/propargyl ether with benzofuranol through following reaction:
In formula, R is selected from: hydrogen, C
1~ C
2alkyl, C
3~ C
4straight chain or C
3~ C
4branched-chain alkyl; X is selected from: chlorine, bromine or iodine.
The furo chroman oxime alkene/propargyl ether that the object of the present invention is to provide is applied preparing in sterilant.
Embodiment
Following examples are intended to the present invention instead of limitation of the invention further are described.
Embodiment 1
The preparation of 3-((2,2-dimethyl-2,3-Dihydrobenzofuranes-7-base) oxygen base) propionitrile (G)
50mmol benzofuranol, 500mmol vinyl cyanide, 5mmol salt of wormwood, the 5mmol trimethyl carbinol, nitrogen protection.Backflow 48h; Add 4mmol85% phosphoric acid cancellation reaction; Underpressure distillation recover acrylonitrile 14.27g, adds methylene dichloride and dissolves stirring, suction filtration, 50mL2mol/L sodium hydroxide and the washing of 3mLDMSO mixing solutions, the back extraction again of 50mL methylene dichloride; Saturated common salt is washed, anhydrous sodium sulfate drying, and methylene dichloride is reclaimed in underpressure distillation, obtains white crystal 3-((2,2-dimethyl-2,3-Dihydrobenzofuranes-7-base) oxygen base) propionitrile, yield 75.1%, m.p.56 ~ 58 DEG C;
1hNMR (400MHz, DMSO) δ: 1.42 (s, 6H, 2 × CH
3), 2.97 (t, J=6.0Hz, 2H, CNCH
2), 3.00 (s, 2H, CH
2), 4.15 (s, 2H, OCH
2), 6.71 ~ 6.84 (m, 3H, C
6h
3).
Embodiment 2
The preparation of 2,2-dimethyl-7,8-dihydro-2H-furo [3,2-h] chroman-6 (3H)-one (B)
20mmol3-((2,2-dimethyl-2,3-Dihydrobenzofuranes-7-base) oxygen base) propionitrile (G), 30mL concentrated hydrochloric acid, backflow 2h; Reaction solution is poured in 100mL frozen water, leaves standstill, suction filtration; Filter cake is dissolved in 200mL5% sodium hydrogen carbonate solution, washed with dichloromethane 3 times, the sodium hydrogen carbonate solution of 5% is stripped, and the hydrochloric acid of 18% adjusts pH7, separates out solid, suction filtration, drying, obtains orange solid 3-((2,2-dimethyl-2,3-Dihydrobenzofuranes-7-base) oxygen base) propionic acid (F), yield 80%;
30mL polyphosphoric acid (PPA), is stirred to 60 DEG C, adds 20mmolF, reaction 1.5h; Temperature of reaction is down to 10 DEG C, adds 100mL frozen water, stirs 0.5h; 150mL extraction into ethyl acetate, 200mL2mol/L sodium hydroxide washs, and ethyl acetate is reclaimed in underpressure distillation, greenish yellow solid 2,2-dimethyl-7, the 8-dihydro-2H-furo [3 of pillar layer separation, 2-h] chroman-6 (3H)-one, yield 36.5%, m.p.138 ~ 140 DEG C;
1hNMR (400MHz, CDCl
3) δ: 1.54 (s, 6H, 2 × CH
3), 2.82 (t, J=6.4Hz, 2H, COCH
2), 3.07 (s, 2H, CH
2), 4.60 (t, J=6.4Hz, 2H, OCH
2), 6.82 (d, J=7.9Hz, 1H, C
6h
2), 7.43 (d, J=7.9Hz, 1H, C
6h
2).
Embodiment 3
The preparation of 2,2-dimethyl-7,8-dihydro-2H-furo [3,2-h] chroman-6 (3H)-one oxime (C)
0.87g (4mmol) B, 0.42g (6mmol) oxammonium hydrochloride, 0.66g (8mmol) sodium-acetate, 10mL ethanol, back flow reaction 2h.After stopped reaction, suction filtration recovery of acetic acid sodium while hot.A large amount of ethanol is reclaimed in underpressure distillation.Add certain water gaging, cooling is separated out.Suction filtration, drying obtains greenish yellow solid 2,2-dimethyl-7,8-dihydro-2H-furo [3,2-h] chroman-6 (3H)-one oxime.Yield 90.5%, m.p.190 ~ 192 DEG C;
1hNMR (400MHz, CDCl
3) δ: 1.53 (s, 6H, 2 × CH
3), 3.06 (s, 2H, ArCH
2), 3.18 (t, J=6.3Hz, 2H, CNCH
2), 4.39 (t, J=6.3Hz, 2H, OCH
2), 6.87 (d, J=8.1Hz, 1H, C
6h
2), 7.76 (d, J=8.1Hz, 1H, C
6h
2).
Embodiment 4
The preparation of 2,2-dimethyl-7,8-dihydro-2H-furo [3,2-h] chroman-6 (3H) oxime propargyl ether
1mmolC, 1.05mmol propargyl bromide, 0.1mmol Tetrabutyl amonium bromide (TBAB), 0.17gKI, 20mL toluene, drips 2.0g20% sodium hydroxide, within 10 minutes, drips off, be warming up to 60 DEG C, and TLC follows the tracks of, reaction 3h; Revolve to steam and reclaim toluene, saturated common salt is washed, anhydrous sodium sulfate drying; Pillar layer separation, obtains faint yellow solid 2,2-dimethyl-7,8-dihydro-2H-furo [3,2-h] chroman-6 (3H) oxime propargyl ether, yield 80.3%, m.p.85 ~ 87 DEG C.
1HNMR(400MHz，CDCl
3)δ：1.52(s，6H，2×CH
3)，2.48(t，J＝2.4Hz，1H，CCH)，2.95(t，J＝6.2Hz，2H，CNCH
2)，3.03(s，2H，ArCH
2)，4.28(t，J＝6.2Hz，2H，OCH
2)，4.77(d，J＝2.4Hz，2H，OCH
2)，6.74(d，J＝8.0Hz，1H，C
6H
2)，7.43(d，J＝8.0Hz，1H，C
6H
2)。
Embodiment 5
The preparation of 2,2-dimethyl-7,8-dihydro-2H-furo [3,2-h] chroman-6 (3H) oxime allyl ethers
Operate according to embodiment 4, reaction 3h, obtains pale yellow oily liquid body 2,2-dimethyl-7,8-dihydro-2H-furo [3,2-h] chroman-6 (3H) oxime allyl ethers, yield 79.8%;
1hNMR (400MHz, CDCl
3) δ: 1.51 (s, 6H, 2 × CH
3), 2.95 (t, J=6.2Hz, 2H, CNCH
2), 3.02 (s, 2H, ArCH
2), 4.28 (t, J=6.2Hz, 2H, OCH
2), 4.68 (d, J=5.7Hz, 2H, OCH
2), 5.23 (d, J=11.3Hz, 1H, CHCH
2), 5.30 (s, 1H, CHCH
2), 6.00 ~ 6.10 (m, 1H, CH
2cH), 6.73 (d, J=8.0Hz, 1H, C
6h
2), 7.41 (d, J=8.0Hz, 1H, C
6h
2).
Embodiment 6
The fungicidal activity of furo chroman oxime alkene/propargyl ether measures
1 test objective
Furo chroman oxime alkene/propargyl ether virulence to various pathogenic bacteria under for examination concentration at indoor measurement, its fungicidal activity of preliminary assessment.
2 test conditionss
2.1 for examination target
Wheat powdery mildew (Blumeriagraminis) is preserved spore with stem and leaf of Wheat and is for experiment.
2.2 culture condition
Culture condition for examination target and the rear target of test is temperature 25 ± 5 DEG C, relative humidity 75 ± 5%
2.3 plant and instrument
Beaker, transfer pipet, graduated cylinder, culture dish, high-pressure sterilizing pot, constant temperature biochemical cultivation case, greenhouse etc.
3 test design
3.1 test medicine
Furo chroman oxime alkene/propargyl ether (I and II):
In formula, R is selected from: hydrogen, C
1~ C
2alkyl, C
3~ C
4straight chain or C
3~ C
4branched-chain alkyl.
3.2 experimental concentration
Broad Bean Leaves method and pot-culture method drug concentration establish 500mg/L
3.3 medicament preparations
Former medicine: take aequum with ten thousand/electronic balance;
Solvent: DMF (DMF), 0.2%;
Emulsifying agent: Tween80,0.1%;
General sieve measures: accurately take 0.0500g sample, dissolves, add the sterilized water 98.8ml containing 0.1%Tween80 emulsifying agent, stir, be mixed with 500mg/L strength solution for subsequent use with 0.20mLDMF.
4 test methods
With reference to " pesticide bioactivity evaluates SOP ".
Wheat powdery mildew: adopt pot-culture method with reference to the raw standard method NY/T1156.4-2006 that surveys; seedling is selected to grow to the susceptible variety stem and leaf of Wheat of 2 leaf ~ 3 leaf phases; with spray method by 500mg/L compound medicine liquid spray on stem and leaf of Wheat; naturally dry; evenly shake off to be inoculated on stem and leaf of Wheat by the Powdery Mildew Fresh spores produced in morbidity wheat leaf blade upper 24 hour, often process is no less than 3 basins, the strain of every basin 10; protectiveness test is inoculation in 24 hours after chemicals treatment, cultivates under then putting suitable condition.According to blank incidence classification investigation, calculate prevention effect.
Solvent control is established in test.
5 investigation methods and evaluated biological activity method
5.1 investigation method
The incidence of the rear routine observation record blade of process, plant and mycelial growth situation, according to disease index and hyphal diameter, calculate preventive effect and inhibiting rate.
Growth inhibition ratio (%)=(contrast colony diameter-process colony diameter) × 100/ (contrast colony diameter-6mm).
Wheat powdery mildew; Investigate according to the classification of blank incidence.Adopt following stage division:
0 grade: anosis;
1 grade: lesion area accounts for less than 5% of one-piece blade area; 3 grades: lesion area accounts for 6% ~ 15% of one-piece blade area; 5 grades: lesion area accounts for 16% ~ 25% of one-piece blade area; 7 grades: lesion area accounts for 26% ~ 50% of one-piece blade area; 9 grades: lesion area accounts for more than 50% of one-piece blade area.
According to enquiry data, calculate disease index and formula (2) the calculating prevention effect of each process by formula (1).
In formula: X represents disease index, Ni represents the sick number of sheets at different levels, and i represents relative level numerical value, and N represents the total number of sheets of investigation.
In formula: P represents prevention effect, CK represents blank disease index, and PT represents chemicals treatment disease index.
6 Activity Results
General sieve result: 2,2-dimethyl-7,8-dihydro-2H-furo [3,2-h] chroman-6 (3H) oxime propargyl ether and 2,2-dimethyl-7,8-dihydro-2H-furo [3,2-h] chroman-6 (3H) oxime allyl ethers is all 80.0% to the anti-efficiency of wheat powdery mildew.
Activity Results shows: furo chroman oxime alkene/propargyl ether has good fungicidal activity, can be used for preparing sterilant.
Claims (4)
1. the furo chroman oxime alkene/propargyl ether shown in chemical structural formula chemical structural formula I/ II:
In formula, R is selected from: hydrogen, C
1~ C
2alkyl, C
3~ C
4straight chain or C
3~ C
4branched-chain alkyl.
2. furo chroman oxime alkene/propargyl ether according to claim 1 is selected from following compound:
3. the preparation method of furo chroman oxime alkene/propargyl ether according to claim 1, is characterized in that obtaining furo chroman oxime alkene/propargyl ether with benzofuranol through following reaction:
In formula, R as claimed in claim 1; X is selected from: chlorine, bromine or iodine.
4. the furo chroman oxime alkene/propargyl ether described in claim 1 or 2 is preparing the application of killing in the sterilant of wheat powdery mildew.
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|---|---|---|---|
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107098916A (en) * | 2017-06-22 | 2017-08-29 | 湖南大学 | 7‑（Pyridine methylene）Dihydrofuran and chromanone and preparation method and application |
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| AU771089B2 (en) * | 1999-02-22 | 2004-03-11 | Bristol-Myers Squibb Company | C-21 modified epothilones |
| CN101486713B (en) * | 2009-02-09 | 2013-05-15 | 沈阳药科大学 | Furo[2,3-h] chromene compound and use for preventing platelet aggregation |
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Non-Patent Citations (1)
| Title |
|---|
| 李婉等: "基于呋喃酚的三唑类化合物的合成与生物活性", 《中国化学会全国第十届有机合成化学学术研讨会》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107098916A (en) * | 2017-06-22 | 2017-08-29 | 湖南大学 | 7‑（Pyridine methylene）Dihydrofuran and chromanone and preparation method and application |
| CN107098916B (en) * | 2017-06-22 | 2019-04-12 | 湖南大学 | 7- (pyridine methylene) dihydrofuran and chromanone and the preparation method and application thereof |
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