CN112661732B - Furanol derivative and preparation method and application thereof - Google Patents
Furanol derivative and preparation method and application thereof Download PDFInfo
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Abstract
The invention relates to a furan phenol derivative shown in a structural formula I or II, a preparation method thereof and application thereof as a bactericide or an insecticide.Wherein R is 1 ～R 5 Selected from: C1-C2 alkyl, C3-C4 straight-chain alkyl or C3-C5 allyl; y is selected from: o or NH.
Description
Technical Field
The invention relates to a preparation method and application of a novel compound, in particular to a furan phenol derivative and application thereof in preparing bactericides and pesticides.
Background
Benzofuran compounds widely exist in the nature, are heterocyclic compounds with wide biological activities, and derivatives thereof have biological activities of killing insects, sterilizing, weeding, resisting tumors and the like. In 1960 s, FMC and bayer in germany developed carbofuran, and developed their more potent low-toxicity derivatives, benfuracarb, carbosulfan and furbenline, successively.
Mitsuyasu et al [ US,4394383,1983-07-19] describe carbamate derivatives containing a benzofuran structure wherein compound 1 has a pesticidal activity against house flies consistent with that of furadan, which is far less toxic to mammals than furadan. Narayana et al [ US4608371,1986-08-26] describe the synthesis of benzofuran ring-containing carbamate derivatives and their insecticidal activity: wherein the mortality rate of the compound 2 to leafhoppers reaches 100% at 100 mg/L.
Huang et al [ Journal of Agricultural and Food Chemistry,2009,57 (6): 2447-2456] describe benzofurans containing bishydrazide structures, wherein compound 3 has 100% insecticidal activity against myxoplasma at 200 mg/L.
Methoxy acrylic acid ester bactericides, kresoxim-methyl and trifloxystrobin, were developed by Nohua corporation (now of the Santa Clara company) in 1998 and were brought to the market by Bayer corporation in 2001. Kresoxim-methyl (also known as phenothrin, phenoxypyraclostrobin, 4) chemical name: (E) -methyl 2-methoxyimino- (2- (o-methylphenoxymethyl) phenyl) acetate. Trifloxystrobin (trade name Flint, 5) chemical name: methyl (2Z) -2-methoxyimino-2- [2- [ [1- [3- (trifluoromethyl) phenyl ] ethyleneamino ] oxymethyl ] phenyl ] acetate.
The activity test shows that the compound has broad-spectrum antifungal activity and good bactericidal activity against fusarium oxysporum, botrytis cinerea, gibberella wheat, alternaria mali, erysiphe necator, and Rhizoctonia solani, wherein the inhibition rate of the compound 6 against the 6 fungi is above 77%.
Jiang Wentao [ organic chemistry, 2014,34 (4): 774-782] synthesizes a series of Strobilurin compounds with benzene rings as side chains, wherein the compounds 9-11 have good inhibition activity on wheat scab, and the inhibition rates are respectively 60.0%, 50.0% and 56.3%, which are equivalent to the activity of positive control trifloxystrobin (53.3%).
The invention aims to develop a furanol derivative bactericide or pesticide.
Disclosure of Invention
The invention solves the technical problem of providing a kind of furan phenol derivatives, a preparation method thereof and application thereof as bactericide or pesticide. In order to solve the technical problems of the invention, the invention provides the following technical scheme:
according to a first aspect of the technical scheme, the invention provides a furan phenol derivative shown in a structural formula I or II:
wherein R is 1 ～R 5 Selected from the group consisting of: C1-C2 alkyl, C3-C4 straight-chain alkyl, C3-C5 allyl; y is selected from: o or NH.
In a first aspect of the present invention, there is also provided a furanol derivative of formula i selected from the group consisting of compounds of formulas ia and ib:
wherein R is 1 ～R 3 Selected from: C1-C2 alkyl, C3-C4 straight-chain alkyl, C3-C5 allyl.
The first aspect of the present invention further provides a furanol derivative represented by formula ii selected from compounds represented by formulas iia and iib:
wherein R is 1 ～R 5 Selected from: C1-C2 alkyl, C3-C4 straight-chain alkyl, C3-C5 allyl.
The first aspect of the present invention further provides a class of furanol derivatives selected from the following compounds:
according to a second aspect of the technical scheme, the invention provides a preparation method of a furan phenol derivative, wherein the preparation reaction of compounds shown in formulas IA and IB is as follows:
wherein R is 1 ～R 3 Selected from: C1-C2 alkyl, C3-C4 straight-chain alkyl, C3-C5 allyl; x is selected from: chlorine, bromine or iodine.
In a second aspect of the present invention, a process for preparing a furan phenol derivative is provided, wherein the preparation of the compounds of formulae IIA and IIB is as follows:
wherein R is selected from: C1-C2 alkyl, C3-C4 straight-chain alkyl; r is R 1 ～R 5 Selected from: C1-C2 alkyl, C3-C4 straight-chain alkyl, C3-C5 allyl; x is selected from: chlorine, bromine or iodine.
The third aspect of the technical proposal of the invention is to provide a furan phenol oxime compound shown in a formula III
Wherein R is 3 ～R 5 Selected from: C1-C2 alkyl, C3-C4 straight-chain alkyl, C3-C5 allyl.
The fourth aspect of the technical scheme of the invention is a preparation method of furan phenol oxime compounds shown in a formula III, which is characterized in that the preparation reaction is as follows:
wherein R is 3 ～R 5 Selected from: C1-C2 alkyl, C3-C4 straight-chain alkyl, C3-C5 allyl.
The fifth aspect of the technical scheme of the invention is the application of the furan phenol oxime compound shown in the formula III in preparing the furan phenol derivative shown in the formula IIA, and the preparation reaction is as follows:
wherein R is selected from: C1-C2 alkyl, C3-C4 straight-chain alkyl; r is R 1 ～R 5 Selected from: C1-C2 alkyl, C3-C4 straight-chain alkyl, C3-C5 allyl; x is selected from: chlorine, bromine or iodine.
According to a sixth aspect of the technical scheme, the invention provides application of the furan phenol derivative in preparing bactericides or pesticides.
The beneficial technical effects are as follows:
the furan phenol derivatives (I and II) are compounds with bactericidal activity or insecticidal activity.
Detailed Description
The following examples are intended to illustrate the invention and are not intended to be limiting.
Example 1
Preparation of 7-methoxy-2, 2-dimethyl-5-acetyl 2, 3-dihydrobenzofuran
26mmol of anhydrous zinc chloride, 50mL of dichloromethane, 26mmol of acetyl chloride is dropwise added at 0 ℃,20 mmol of 7-methoxy-2, 2-dimethyl-2, 3-dihydrobenzofuran (dissolved in 20mL of dichloromethane) is slowly dropwise added after dropwise addition, and the reaction is carried out for 1.0h in an ice bath. Adding sodium bicarbonate solution to regulate pH to neutrality, water washing, desolventizing, and column chromatographic separation to obtain white solid 7-methoxy-2, 2-dimethyl-5-acetyl-2, 3-dihydrobenzofuran in the m.p. 104-106 deg.c and yield of 50.8 wt% calculated as 7-methoxy-2, 2-dimethyl-2, 3-dihydrobenzofuran. 1 H NMR(400MHz，CDCl 3 ) Delta: 7.43 (s, 2H, benzofuran ring), 3.92 (s, 3H, OCH) 3 )，3.07(s，2H，CH 2 )，2.54(s，3H，CH 3 )，1.54(s，6H，2×CH 3 ). 1- (7-methoxy-2, 2-dimethyl-2, 3-dihydrobenzofuran-5-yl) ethanone oxime was prepared as in example 2.
Example 2
Preparation of 1- (7-methoxy-2, 2-dimethyl-2, 3-dihydrobenzofuran-5-yl) ethanone oxime (IIIa)
5mmol of 7-methoxy-2, 2-dimethyl-5-acetyl-2, 3-dihydrobenzofuran (example 1), 7.5mmol of hydroxylamine hydrochloride, 10mmol of sodium acetate, 15mL of ethanol, and reflux with heating for 3.0h. Filtering to remove inorganic salt solid, desolventizing, extracting with dichloromethane, washing with saturated sodium chloride solution, desolventizing to obtain white solid (E) -7-methoxy-2, 2-dimethyl-2, 3-dihydro-5-benzofuranyl glyoxime, wherein the m.p.127-129 ℃ is reached, and the yield is 98.8%. 1 H NMR(400MHz，CDCl 3 ) Delta: 7.44 (s, 1H, NOH), 7.08 (s, 1H, benzofuran ring 6-H), 7.03 (s, 1H, benzofuran ring 4-H), 3.90 (s, 3H, OCH) 3 )，3.05(s，2H，CH 2 )，2.27(s，3H，CH 3 )，1.52(s，6H，2×CH 3 ). Methyl (E) -2- (2- (((((E) -1- (7-methoxy-2, 2-dimethyl-2, 3-dihydrobenzofuran-5-yl) ethylene) amino) oxy) methyl) phenyl) -2- (methoxyimino) acetate was prepared as in example 5.
Example 3
(E) Preparation of methyl-2- (2- (((2, 2-dimethyl-2, 3-dihydrobenzofuran-7-yl) oxy) methyl) phenyl) -2- (methoxyimino) acetate (Ia)
1.0mmol of 2, 2-dimethyl-2, 3-dihydrobenzofuran-7-ol, 1.1mmol of potassium carbonate, 5mL of acetonitrile, 0.6mmol of potassium iodide, 1.05mmol of methyl (E) -2-bromomethyl-alpha-methoxyiminophenylacetate, stirring at room temperature, heating to reflux, reacting for 3h, desolventizing under reduced pressure, extracting with ethyl acetate, washing with water, drying with anhydrous sodium sulfate, desolventizing, separating by column chromatography (V Petroleum ether ∶V Acetic acid ethyl ester =8:1) to give (E) -methyl 2- (2- (((2, 2-dimethyl-2, 3-dihydrobenzofuran-7-yl) oxy) methyl) phenyl) -2- (methoxyimino) acetate (ia), a white solid in 85% yield; m.p.98-100 deg.c; 1 HNMR(400MHz，CDCl 3 )δ：7.62～7.14(m，4H，C 6 H 4 )，6.78～6.59(m，3H，C 6 H 3 )，5.03(s，2H，OCH 2 )，4.05(s，3H，NOCH 3 )，3.86(s，3H，OCH 3 )，3.02(s，2H，CH 2 )，1.52(s，6H，2×CH 3 )； 13 C NMR(101MHz，CDCl 3 )δ：163.25，149.33，147.91，143.31，135.84，129.56，128.89，128.50，128.12，127.50，127.42，120.18，118.05，113.95，87.32，69.06，63.80，52.98，43.30，28.28。
example 4
(E) Preparation of (E) -2- (2- (((2, 2-dimethyl-2, 3-dihydrobenzofuran-7-yl) oxy) methyl) phenyl) -2- (methoxyimino) acethylamine (Ib)
0.5mmol of compound Ia, 5mmol of methylamine in water, 5mL of methanol are reacted for 6h under reflux, desolventizing and separating by column chromatography to obtain (E) -2- (2- (((2, 2-dimethyl-2, 3-dihydrobenzofuran-7-yl) oxy) methyl) phenyl) -2- (methoxyimino) acethylmethylamine (Ib) as a pale yellow viscous liquid with the yield of 98.0%; 1 H NMR(400MHz，CDCl 3 )δ：7.57～7.22(m，4H，C 6 H 4 )，6.81(s，1H，NH)，6.79～6.65(m，3H，C 6 H 3 )，5.07(s，2H，OCH 2 )，3.96(s，3H，NOCH 3 )，3.05(s，2H，CH 2 )，2.92(d，J＝4.9Hz，3H，NCH 3 )，1.54(s，3H，2×CH 3 )； 13 C NMR(101MHz，CDCl 3 )δ：163.13，151.34，147.72，143.31，135.72，129.44，128.81，128.67，128.31，127.61，127.44，120.36，117.93，113.77，87.30，69.43，63.17，43.30，28.29，26.29。
example 5
(E) Preparation of methyl (IIa) 2- (2- (((((E) -1- (7-methoxy-2, 2-dimethyl-2, 3-dihydrobenzofuran-5-yl) ethylene) amino) oxy) methyl) phenyl) -2- (methoxyimino) acetate
1mmol (E) -1- (7-methoxy-2, 2-dimethyl-2, 3-dihydrobenzofuran-5-yl) ethanone oxime (example 2), 1.1mmol sodium methoxide, 5mL DMF, stirring at room temperature, 1.05mmol methyl (E) -2-bromomethyl- α -methoxyiminophenylacetate, TLC monitoring, adding 5mL water, dichloromethane extraction, washing with water, drying over anhydrous sodium sulfate, desolventizing, column chromatography separation (petroleum ether: ethyl acetate=4:1) to give (E) -2- (2- ((((((E) -1- (7-methoxy-2, 2-dimethyl-2, 3-dihydrobenzofuran-5-yl) ethylene) amino) oxy) methyl) phenyl) -2- (methoxyimino) acetic acid methyl ester (IIa) in 76.8% yield as a viscous liquid; 1 H NMR(400MHz，CDCl 3 )δ：7.53～7.15(m，4H，C 6 H 4 )，7.04(s，1H，C 6 H 2 )，7.01(s，1H，C 6 H 2 )，5.10(s，2H，OCH 2 )，4.02(s，3H，NOCH 3 )，3.87(s，3H，OCH 3 )，3.80(s，3H，COOCH 3 )，3.01(s，2H，CH 2 )，2.17(s，3H，CH 3 )，1.50(s，6H，2×CH 3 )； 13 C NMR(101MHz，CDCl 3 )δ：163.27，155.13，149.62，148.42，144.20，136.37，129.74，129.34，129.28，128.65，128.45，127.82，127.51，115.77，109.04，88.26，74.41，63.72，55.87，52.80，43.12，28.18，12.98。
example 6
(E) Preparation of (E) -2- (2- (((((E) -1- (7-methoxy-2, 2-dimethyl-2, 3-dihydrobenzofuran-5-yl) ethylene) amino) oxy) methyl) phenyl) -2- (methoxyimino) acethylamine (IIb)
The compound IIa obtained in example 5 was selected as starting material and prepared in accordance with the procedure of example 4 to give (E) -2- (2- ((((E) -1- (7-methoxy-2, 2-dimethyl-2, 3-dihydrobenzofuran-5-yl) ethyleneamino) oxy) methyl) phenyl) -2- (methoxyimino) ethyl)Acyl methylamine (IIb), white solid, yield 86.9%; m.p.73-75 ℃; 1 HNMR(400MHz，CDCl 3 )δ：7.48～7.03(m，4H，C 6 H 4 )，7.08(s，1H，C 6 H 2 )，7.06(s，1H，C 6 H 2 )，6.75(d，J＝4.3Hz，1H，NH)，5.09(s，2H，OCH 2 )，3.95(s，3H，NOCH 3 )，3.88(s，3H，OCH 3 )，3.02(s，2H，CH 2 )，2.86(d，J＝5.0Hz，3H，NCH 3 )，2.17(s，3H，CH 3 )，1.50(s，6H，2×CH 3 )； 13 C NMR(101MHz，CDCl 3 )δ：162.99，155.15，151.32，148.46，144.27，136.46，129.52，129.42，129.27，128.68，128.57，127.90，127.53，115.79，109.04，88.33，74.47，63.27，55.94，43.17，28.22，26.23，13.05。
example 7
Determination of Fungicide Activity of Fungicide derivatives
1 purpose of test
Furanol derivatives were tested for virulence against various pathogenic bacteria at the concentrations tested in the room, and their bactericidal activity was initially evaluated.
2 test conditions
2.1 test targets
The Botrytis cinerea (Botrytis cinerea), the brown spot germ (Alternaria alternata), the brown spot germ (Gibberella zeae), the sclerotium germ (Sclerotonia sclerotiorum) and the phytophthora capsici leonian (Phytophythora capsici) are all stored in a refrigerator (4-8 ℃), inoculated into a culture dish from a test tube inclined plane 2-3 days before the test, and cultured at a proper temperature for the test. The experimental media were potato agar medium (PDA).
2.2 culture conditions
The culture conditions of the tested target and the target after the test are that the temperature is 25+/-5 ℃ and the relative humidity is 65+/-5%
2.3 instrumentation
Beaker, pipette, measuring cylinder, culture dish, autoclave, constant temperature biochemical incubator, etc.
3 test design
3.1 test agents: example compounds.
3.2 test concentration
The concentration of the in-vitro medicament is set to 25mg/L; the concentration of the corn rust germ and wheat powdery mildew germ agent is set to 500mg/L.
3.3 preparation of pharmaceutical formulations
The raw materials are as follows: weighing the required amount by a ten-thousandth electronic balance; solvent: n, N-Dimethylformamide (DMF), 0.2%; emulsifying agent: tween80, 0.1%;
and (3) common screen measurement: accurately weighing 0.0500g sample, dissolving with 0.20mL LDMF, adding 98.8mL sterile water containing 0.1% Tween80 emulsifier, stirring well, and preparing into 500mg/L solution for use.
4 test method
Reference is made to "evaluation of pesticide biological Activity SOP".
Botrytis cinerea, alternaria tabaci, alternaria wheat, sclerotinia sclerotiorum and Phytophthora capsici: with reference to the standard method of biological measurement NY/T1156.2-2006, a medicated culture medium method is adopted: 2mL of each 500mg/L compound solution was added to 38mL of PDA cooled to 45℃to prepare a plate of a drug-containing medium having a final concentration of 25 mg/L. Then 6.5mm diameter mycelium blocks were removed from the edges of the cultured test pathogen colonies and transferred to a medicated medium, and each treatment was repeated 4 times. After the treatment, the colony is cultured in a constant temperature biochemical incubator at 28 ℃ for 4 days, and the colony diameter is measured to calculate the growth inhibition rate.
5 evaluation of Bactericide Activity
After treatment, the disease condition and the hypha growth condition of the leaves and plants are observed and recorded regularly, and the control effect and the inhibition rate are calculated according to the disease index and the hypha diameter.
The in vitro bactericidal activity and the in vivo bactericidal activity of the furanol derivative are shown in the following table:
"-": unmeasured test
The inhibition rates of the excellent compound IIb on phytophthora capsici and gibberella wheat are 38.46% and 57.97% respectively. The control effect of excellent compounds Ib and IIb on powdery mildew of wheat is 90% and 95% respectively; the control effect of excellent compounds Ia, ib and IIb on corn rust disease bacteria is 90%, 95% and 100% respectively.
The furan phenol derivative has good bactericidal activity and can be used for preparing bactericides in agriculture.
Example 8
Furofen derivative insecticidal Activity assay
1 test target
The broad bean aphid (Aphis fabae) line was raised indoors with broad bean seedlings for years of sensitive strain, and the test insects were 3-day-old myzus persicae. Armyworm (Mythimna sepatara) is a sensitive strain raised for years with fresh corn leaves; the test larvae were 3-instar larvae.
2 culture conditions
The culture conditions of the target to be tested and the target after the test are that the temperature is 25+/-5 ℃, the relative humidity is 65+/-5%, and the illumination period is 12/12h (L/D).
3 test agent (raw drug): furofen derivatives.
4, preparing raw materials: weighing the required amount by a ten-thousandth electronic balance; solvent: n, N-Dimethylformamide (DMF), 0.2%; emulsifying agent: tween80,0.2%; adding clear water to dilute to the required concentration. Furofen derivative insecticidal activity common screen: the test concentration was 500mg/L.
5 test methods reference "evaluation of pesticide biological Activity SOP".
The broad bean aphid common screen adopts an impregnation method: the broad bean seedlings with 3-day-old broad bean Aphis citrifolia are cut off, immersed in the prepared liquid medicine for 10 seconds, taken out, inserted onto a sponge absorbing enough water, covered with Ma Dengzhao, and treated for 2 times. After the treatment, the mixture is placed in an observation room for cultivation, the observation is carried out at regular time, the death condition is checked and recorded after 72 hours, and the death rate is calculated.
The comprehensive toxicity test method of the armyworm adopts a Potter spraying method, fresh and tender corn leaves are cut into segments with basically consistent sizes, and the segments are placed in a culture dish (phi 90 mm) which is filled with filter paper in advance. Then, 10 larvae of myxoplasma 3 years old are inoculated in a dish, and the larvae are put under a Potter spray tower for quantitative spraying, the spraying liquid amount is 1mL, and the repetition is carried out for 3 times per concentration. After the treatment is finished, the vessel cover is covered, the vessel cover is placed in an observation chamber for culture, the vessel cover is observed regularly, and the death condition of the test insects is checked and recorded after 72 hours.
6 toxic Activity
Poisoning activity of preferred compounds: at an active ingredient concentration of 500mg/L, the mortality rate of the compound IIb to aphids after 72 hours of treatment is 98.6%.
The furan phenol derivative has good insecticidal activity and can be used for preparing insecticide in agriculture.
Claims (7)
1. Furanol derivatives shown in structural formula I or II:
wherein R is 1 ～R 5 Selected from: a methyl group; y is selected from: o or NH;
the furan phenol derivative shown in the formula I is selected from compounds shown in the formula Ia or Ib; the furan phenol derivative shown in the formula II is selected from compounds shown in the formula IIb:
2. the process for producing a furan phenol derivative as claimed in claim 1, wherein the compounds represented by formulae la and lb are produced by the following reaction:
wherein R is 1 ～R 3 Selected from the group consisting of: a methyl group; x is selected from: chlorine, bromine or iodine.
3. The process for producing a furan phenol derivative as defined in claim 1, wherein the compound represented by the formula IIb is produced by the reaction:
wherein R is selected from: a methyl group; r is R 1 ～R 5 Selected from: a methyl group; x is selected from: chlorine, bromine or iodine;
the preparation reaction of the furan phenol oxime compound III is as follows:
wherein R is 3 ～R 5 Selected from: methyl group.
4. Use of a compound la according to claim 1 for the preparation of a bactericide against powdery mildew of wheat or maize rust.
5. Use of a compound ib according to claim 1 for the preparation of a bactericide against alternaria alternata, botrytis cinerea, erysiphe graminis or maize rust.
6. The use of a compound IIb according to claim 1 for the preparation of bactericides for the control of Alternaria wheat germ, alternaria alternata or Alternaria zeae.
7. The use of a compound IIb according to claim 1 for the preparation of a broad bean aphid insecticide.
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