CN108689950A - [(6- substitutions-pyrimidine-4-yl oxygen) Ben Ji ]- 3- methoxy-methyl acrylates - Google Patents
[(6- substitutions-pyrimidine-4-yl oxygen) Ben Ji ]- 3- methoxy-methyl acrylates Download PDFInfo
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Abstract
The invention discloses active with inhibition crops germ;(6- substitutions-pyrimidine-4-yl oxygen) Ben Ji ]- 3- methoxy-methyl acrylates, are related to technological field of biochemistry.It has following structure general formula:
Description
Technical field
The present invention relates to technological field of biochemistry, She Ji [(6- substitutions-pyrimidine-4-yl oxygen) Ben Ji ]- 3- methoxy propyls
E pioic acid methyl ester and preparation method thereof.
Background technology
In present agricultural development, disease control is to perplex the hang-up of peasant.If prevented not in time, disease exists
It has developed rapidly in short time, injured area gradually expands.Seriously affect crops harvest.With the generally use of pesticide, farming
The drug resistance of object germ is more and more stronger, efficiently, the development of the pesticide of low toxicity be extremely urgent problem.Therefore, development of new agriculture
Medicine can effectively delay the generation of cause of disease group drug resistance, can also play a key effect to control of plant disease.Methoxyl group propylene
Bactericide of phosphate (phosphinium) ester is a kind of new and effective, wide spectrum, systemic fungicide, derives from natural products Strobilurin, is line
Plastochondria respiration inhibitor.It usually shows very Mycophyta (Ascomycetes, Basidiomycetes, Oomycete and Fungi Imperfecti) disease
Good activity, have to crops protect, treat, rooting out, layer moves and systemic action, meanwhile, methoxy acrylic is sterilized
Agent has high selectivity, substantially pollution-free to environment to crop, people, animal and beneficial organism safety, can be sprayed with cauline leaf,
The modes such as seed treatment use.But equally exist crop plants drug resistance, for this purpose, to methoxy acrylic ester compounds into
Row modification, research and development strobilurin fungicide are very necessary.
Invention content
There is broad spectrum of activity [ the purpose of the present invention is to provide a kind of;(6- substitutions-pyrimidine-4-yl oxygen) Ben Ji ]- 3- first
Oxygroup methyl acrylate, another object are to provide its application in terms of inhibiting crops germ activity.
Purpose to realize the present invention, the present invention have carried out structural modification to methoxy acrylate, synthesis;(6- substitutions-
Pyrimidine-4-yl oxygen) Ben Ji ]- 3- methoxy-methyl acrylates, have following structure general formula:
Wherein, R=H3CO-,
Synthesis [ of the present invention;(6- substitutions-pyrimidine-4-yl oxygen) Ben Ji ]- 3- methoxy-methyl acrylate routes are as follows:
(a) compound 1, toluene, glacial acetic acid, phosphorus pentoxide are added in there-necked flask and are heated to reflux.After reaction, it drops
Water washing is added in temperature, and ethyl acetate extraction separates organic phase, and decompression steams solvent, obtains yellow solid compound 2.Product without
It needs to purify, is directly used in and reacts in next step.
(b) compound 2, trimethyl orthoformate are added in there-necked flask, are stirred at room temperature to complete molten rear be added of solid and are catalyzed
Agent zinc chloride.Stirring heating, controls 80 DEG C -130 DEG C of temperature, cools down after reaction.In reaction system be added ethyl acetate and
Water washing separates organic phase, is concentrated under reduced pressure, obtains compound 3.Product is directly used in and reacts in next step without purification.
(c) reaction, after reaction, compound 4 is mixed at 0 DEG C -10 DEG C or less in compound 3, methanol, sodium methoxide
Without detaching from system, it is directly used as reacting in next step.
(d) at a certain temperature, it is slowly added into compound 4 into Isosorbide-5-Nitrae-dioxane solution of 4,6- dichloro pyrimidines, rises
Temperature is to 50 DEG C -80 DEG C, and decompression while hot filters salt, and filtrate decompression steams solvent, obtains compound 5.
(e) compound 5, methanol, sodium methoxide are heated to reflux and are stirred to react, after the reaction was complete, be cooled to room temperature, be added water and
Ethyl acetate, separates organic phase, and decompression steams organic phase, obtains compound 6.
(f) by compound 5, toluene, different substituent group phenol, potassium carbonate, dimethylformamide (DMF), triethylene two
The mixture of amine (DABCO) composition is in 90 DEG C of -120 DEG C of stirrings.After the reaction was complete, water and ethyl acetate is added, separates organic phase,
Evaporated under reduced pressure obtains compound 7, compound 8, compound 9, compound 10, compound 14, compound 16, compound 18.
(g) by compound 5, toluene, compound 8, either compound 9 or compound 10, potassium carbonate, DMF, DABCO are formed
Mixture stirring, 80 DEG C -130 DEG C reaction 5h-9h.After being cooled to room temperature, water and ethyl acetate is added, separates organic phase, nothing
Aqueous sodium persulfate is dried, and evaporated under reduced pressure, column chromatography obtains compound 11, compound 12, compound 13.
(j) either compound 16 or compound 18 are separately added into iron powder, concentrated hydrochloric acid, second alcohol and water to compound 14,50 DEG C-
It is stirred to react 1h-4h under the conditions of 80 DEG C, adds concentrated hydrochloric acid, the reaction was continued 3h-7h is cooled to room temperature, and water and ethyl acetate is added, point
Go out water phase and be neutralized to alkalinity with saturated solution of sodium carbonate, ethyl acetate extraction is concentrated to dryness, column chromatography obtains yellow chemical combination
Object 15, compound 17, compound 19.
(k) mixture for forming compound 5, toluene, different substituent group naphthols, potassium carbonate, DMF, DABCO is 100
DEG C of -140 DEG C stirrings.After the reaction was complete, water and ethyl acetate is added, separates organic phase, evaporated under reduced pressure obtains compound 20, chemical combination
Object 21, compound 22, compound 23, compound 24.
Advantageous effect of the present invention:The present invention successfully synthesizes a series of Fluoxastrobin analogs, and experiment confirms:They are to cucumber
Withered, peanut foxiness, apple wheel line, wheat line be withered, corn stigma, watermelon anthrax, rice bakanae disease have good inhibiting effect.
It is especially higher to the inhibiting rate of peanut Cercospora bacteria, Botryosphaeria berengeriana f. sp, rhizoctonia cerealis, wherein compound 6, compound
The inhibiting rate of 19 pairs of cucumber fusarium axysporums is higher, and respectively 71.4%, 72.0%;It is higher to peanut Cercospora bacteria inhibiting rate to be
Compound 11, compound 12, compound 21, compound 23, inhibiting rate are respectively 88.0%, 87.1%, 86.2%;To apple wheel
Higher line germ inhibiting rate is compound 7, compound 9, compound 21, compound 10, compound 22, and inhibiting rate is respectively
94.1%, 93.1%, 93.0%, 92.3%, 92.2%;It is higher to rhizoctonia cerealis inhibiting rate be Compound Compound 7,
Compound 9, compound 10, compound 21, compound 20, compound 6, compound 16, compound 8, compound 19, compound
11, compound 24, compound 18, inhibiting rate is respectively 97.2%, 96.4%, 95.5%, 94.1%, 93.3%, 93.1%,
92.4%, 92.2%, 92.0%, 91.7%, 91.1%, 90.1%;Higher to southern corn leaf blight inhibiting rate is compound
10, compound 9, compound 7, compound 19, inhibiting rate are respectively 79.3%, 78.2%, 73.7%, 73.0%;To watermelon charcoal
Subcutaneous ulcer germ inhibiting rate is higher be compound 24, compound 19, compound 18,17 inhibiting rate of compound be respectively 79.1%,
73.4%, 72.1%, 71.5%;Higher to fusarium moniliforme inhibiting rate is compound 10, compound 9, compound 8, change
Close object 7, compound 6, compound 19, compound 20,18 inhibiting rate of compound are respectively 82.8%, 81.3%, 80.9%,
77.8%, 76.9%, 72.3%, 71.2%, 70.1%.Therefore, such compound can effectively inhibit causing a disease on crops
Bacterium has potential using value, development prospect good current crops drug resistance situation more serious situation.
Specific implementation mode
Present invention will be further explained below with reference to specific examples.These embodiments are merely to illustrate the present invention and do not have to
In limitation the scope of protection of present invention.
Embodiment 1:The synthesis of compound 2
Reactor is added in compound 1 (304g, 2mmol), toluene (2L), glacial acetic acid (0.5L), phosphorus pentoxide (500g)
In, heating reflux reaction 6h after the reaction was complete, is cooled to room temperature, is slowly added into ice water, and ethyl acetate extracts 3 times, merges organic
Phase, saturated salt solution extraction, the drying of organic phase anhydrous sodium sulfate are concentrated to dryness, can be directly used in next step without purification
Reaction.It takes out fraction column chromatography and obtains 2 white, needle-shaped crystals of compound.48~50 DEG C of fusing point:1H-NMR (400Hz,
CDCl3):3.72 (s, 2H, CH2), 7.08~7.32 (m, 4H, Ph-H).
Embodiment 2:The synthesis of compound 3
Previous step raw material is taken, trimethyl orthoformate (265g, 2.5mmol), zinc chloride (13.6g, 0.1mol), heating is added
To 110 DEG C of the reaction was continued 4h, cool down after reaction.Ethyl acetate and water washing are added in reaction system, separates organic phase, subtracts
Pressure concentration, obtains compound 3.Product is directly used in and reacts in next step without purification.It takes out fraction column chromatography and obtains compound
3 be greenish yellow solid, 27~29 DEG C of fusing point:1H-NMR (400Hz, CDCl3), 4.13 (S, 3H, CH3), 7.06~7.13 (m, 2H,
Ph-H), 7.18~7.21 (m, 1H, CH), 7.53~7.56 (m, 2H, Ph-H).
Embodiment 3:The synthesis of 4 sodium phenolate of compound
Methanol (2L) is added in upper step raw material, sodium methoxide (130g, 2.4mmol) is added under ice salt bath, continues to be stirred to react
After 2h, reaction solution reduced pressure is directly used in reacts in next step.It takes a small amount of concentrate that dilute hydrochloric acid is added and is neutralized to pH=6, then
It is extracted with ethyl acetate and water, organic phase is concentrated to dryness, and column chromatography purifies to obtain water white transparency oily compounds 4:1H-
NMR (400Hz, CDCl3):3.38 (s, 3H, OCH3), 3.68 (s, 3H, OCH3), 4.95 (s, 1H, CH), 6.76~6.85 (m,
2H, Ph-H), 7.15~7.18 (m, 2H, Ph-H).
Embodiment 4:The synthesis of compound 5
Under room temperature, sodium carbonate (106g, 1mol), 4,6- dichloro pyrimidines (300g, 2mol), Isosorbide-5-Nitrae-dioxane
(2L), is slowly added into the sodium phenolate of compound 4 into above-mentioned reaction solution after stirring, heating reaction is to 60 DEG C, and the reaction was continued 6h takes advantage of
Heat decompression filters salt, and water and ethyl acetate is added after being cooled to room temperature, separates organic phase, and anhydrous sodium sulfate drying is concentrated under reduced pressure, obtains
It is after purification light yellow solid to compound 5.Fusing point:104~106 DEG C.1H-NMR (400Hz, CDCl3):3.60 (s, 3H,
CH3), 3.75 (s, 3H, CH3), 6.79 (s, 1H, CH), 7.17~7.45 (m, 4H, Ph-H), 7.46 (s, 1H, Pyr-H), 8.58
(s, 1H, Pyr-H).
Embodiment 5:The synthesis of compound 6
Compound 5 (1.03g, 3.4mmol), methanol (10ml), sodium methoxide (0.18g, 3.4mmol) are heated to reflux stirring
Reaction after the reaction was complete, is cooled to room temperature, water and ethyl acetate is added, and separates organic phase, and decompression steams organic phase, and column chromatography obtains
To white crystalline powder compound 6 (0.84g, 83%).1H-NMR (400Hz, CDCl3):3.59 (s, 3H, OCH3), 3.73
(s, 3H, OCH3), 3.95 (s, 3H, OCH3), 6.06 (s, 1H, CH), 7.15~7.44 (m, 4H, Ph-H), 7.44 (s, 1H, Pyr-
H), 8.44 (s, 1H, Pyr-H).
Embodiment 6:The synthesis of compound 7
By compound 5 (3.1g 10mmol), toluene (25mL), phenol (1.1g, 12.0mol), potassium carbonate (1.38g,
10mmol), the mixture stirring of DMF (2mL), DABCO (0.2g) composition, 6h is reacted at 100 DEG C.After being cooled to room temperature, water is added
And ethyl acetate, separate organic phase, anhydrous sodium sulfate drying, evaporated under reduced pressure, column chromatography obtain light yellow solid 7 (3.51g,
96%).1H-NMR (400Hz, CDCl3):3.60 (s, 6H, OCH3), 3.75 (s, 6H, OCH3), 6.14 (s, 2H, CH), 6.95~
7.48 (m, 12H, Ph-H), 7.45 (s, 1H, Pyr-H), 8.42 (s, 1H, Pyr-H).
With the preparation of 6 compound 8 of embodiment, o-hydroxy phenol substitutes phenol.Obtain light yellow solid 8 (2.87g, 75%)
1H-NMR (400Hz, CDCl3):3.60 (s, 3H, OCH3), 3.78 (s, 3H, OCH3), 5.80 (s, 1H, OH), 6.20 (s, 1H,
CH), 6.59~7.46 (m, 8H, Ph-H), 7.56 (s, 1H,
Pyr-H), 8.44 (s, 1H, Pyr-H).
With the preparation of 6 compound 9 of embodiment, hydroxyl phenol substitutes phenol, obtains light yellow solid 9 (2.75g, 72%)
1H-NMR (400Hz, CDCl3):3.61 (s, 3H, OCH3), 3.77 (s, 3H, OCH3), 5.80 (s, 1H, OH), 6.23 (s, 1H,
CH), 6.58~7.45 (m, 8H, Ph-H), 7.58 (s, 1H,
Pyr-H), 8.45 (s, 1H, Pyr-H).
With the preparation of 6 compound 10 of embodiment, para hydroxybenzene phenol substitutes phenol, obtain light yellow solid 10 (2.60g,
68%) 1H-NMR (400Hz, CDCl3):3.61 (s, 3H, OCH3), 3.77 (s, 3H, OCH3), 5.80 (s, 1H, OH), 6.21 (s,
1H, CH), 6.58~7.45 (m, 8H, Ph-H), 7.57 (s, 1H, Pyr-H), 8.46 (s, 1H, Pyr-H).
Embodiment 7:The synthesis of compound 11
By compound 5 (1.5g 5mmol), toluene (20mL), compound 8 (1.90g, 5mol), potassium carbonate (0.69g,
5mmol), the mixture stirring of DMF (1mL), DABCO (0.1g) composition, 6h is reacted at 110 DEG C.After being cooled to room temperature, be added water and
Ethyl acetate, separates organic phase, anhydrous sodium sulfate drying, evaporated under reduced pressure, column chromatography obtain yellowish solid 11 (2.55g,
78%) 1H-NMR (400Hz, CDCl3):3.60 (s, 6H, OCH3), 3.75 (s, 6H, OCH3), 6.24 (s, 2H, CH), 7.06~
7.48 (m, 12H, Ph-H), 7.46 (s, 2H, Pyr-H), 8.42 (s, 1H, Pyr-H).
With the preparation of 7 compound 12 of embodiment:Change compound 8 into compound 9, obtain yellowish solid 12 (2.68g,
82%) 1H-NMR (400Hz, CDCl3):3.60 (s, 6H, OCH3), 3.75 (s, 6H, OCH3), 6.23 (s, 2H, CH), 7.08~
7.49 (m, 12H, Ph-H), 7.47 (s, 2H, Pyr-H), 8.41 (s, 1H, Pyr-H).
With the preparation of 7 compound 13 of embodiment:Change compound 8 into compound 10, obtain yellow solid 13 (2.81g,
86%) 1H-NMR (400Hz, CDCl3):3.60 (s, 6H, OCH3), 3.75 (s, 6H, OCH3), 6.22 (s, 2H, CH), 7.05~
7.46 (m, 12H, Ph-H), 7.45 (s, 2H, Pyr-H), 8.40 (s, 1H, Pyr-H).
Embodiment 8:The synthesis of compound 14
With the preparation of 6 compound 7 of embodiment, phenol is o-nitrophenol, obtains yellow solid 14 (3.78g, 92%) 1H-
NMR (400Hz, CDCl3):3.61 (s, 3H, OCH3), 3.77 (s, 3H, OCH3), 6.17 (s, 1H, CH), 7.20~7.44 (m,
6H, Ph-H), 7.48 (s, 1H, Pyr-H), 8.28~8.31 (m, 2H, Ph-H), 8.41 (s, 1H, Pyr-H).
Embodiment 9:The synthesis of compound 15
Compound 14 (2.0g, 5mmol) is separately added into iron powder (0.56g, 10mmol), concentrated hydrochloric acid (2ml), ethyl alcohol (10ml)
With water (2ml), 2h being stirred to react under the conditions of 60 DEG C, adds concentrated hydrochloric acid (2ml), the reaction was continued 5h is cooled to room temperature, water and second is added
Acetoacetic ester separates water phase and is neutralized to alkalinity with saturated solution of sodium carbonate, and ethyl acetate extraction is concentrated to dryness, column chromatography point
Yellow compound 15 (1.74g, 94%) 1H-NMR (400Hz, CDCl is not obtained3):3.62 (s, 3H, OCH3), 3.78 (s, 3H,
OCH3), 6.16 (s, 1H, CH), 7.22~7.46 (m, 6H, Ph-H), 7.47 (s, 1H, Pyr-H), 8.26~8.29 (m, 2H,
Ph-H), 8.40 (s, 1H, Pyr-H).
With the preparation of 6 compound 7 of embodiment, phenol is metanitrophenol, obtains yellow solid 16 (3.70g, 90%) 1H-
NMR (400Hz, CDCl3):3.60 (s, 3H, OCH3), 3.76 (s, 3H, OCH3), 6.17 (s, 1H, CH), 7.18~7.42 (m,
6H, Ph-H), 7.48 (s, 1H, Pyr-H), 8.30~8.33 (m, 2H, Ph-H), 8.43 (s, 1H, Pyr-H).
With the preparation of 9 compound 15 of embodiment, compound 14 changes compound 16 into, obtain yellow solid 17 (1.78g,
96%):1H-NMR (400Hz, CDCl3):3.60 (s, 3H, OCH3), 3.76 (s, 3H, OCH3), 6.15 (s, 1H, CH), 7.23~
7.47 (m, 6H, Ph-H), 7.46 (s, 1H, Pyr-H), 8.25~8.28 (m, 2H, Ph-H), 8.41 (s, 1H, Pyr-H)
With the preparation of 6 compound 7 of embodiment, phenol is p-nitrophenol, obtains yellow solid 18 (3.82g, 93%) 1H-
NMR (400Hz, CDCl3):3.62 (s, 3H, OCH3), 3.78 (s, 3H, OCH3), 6.18 (s, 1H, CH), 7.19~7.43 (m,
6H, Ph-H), 7.48 (s, 1H, Pyr-H), 8.29~8.32 (m, 2H, Ph-H), 8.42 (s, 1H, Pyr-H).
With the preparation of 9 compound 15 of embodiment, compound 14 changes compound 18 into, obtain yellow compound 19 (1.81g,
98%):1H-NMR (400Hz, CDCl3):3.61 (s, 3H, OCH3), 3.77 (s, 3H, OCH3), 6.15 (s, 1H, CH), 7.21~
7.45 (m, 6H, Ph-H), 7.48 (s, 1H, Pyr-H), 8.25~8.28 (m, 2H, Ph-H), 8.43 (s, 1H, Pyr-H).
Embodiment 10:The synthesis of compound 20
By compound 5 (3.1g 10mmol), toluene (25mL), alpha naphthol (1.73g, 12.0mol), potassium carbonate (1.38g,
10mmol), the mixture stirring of DMF (2mL), DABCO (0.2g) composition, 6h is reacted at 120 DEG C.After being cooled to room temperature, water is added
And ethyl acetate, separate organic phase, anhydrous sodium sulfate drying, evaporated under reduced pressure, column chromatography obtain light yellow solid 20 (2.7g,
65%).1H-NMR (400Hz, CDCl3):3.59 (s, 3H, OCH3), 3.74 (s, 3H, OCH3), 6.17 (s, 1H, CH), 6.70~
7.40 (m, 11H, Ph-H), 7.45 (s, 1H, Pyr-H), 8.41 (s, 1H, Pyr-H).
With the preparation of 10 compound 21 of embodiment, naphthols is 2- methyl-1s-naphthols, obtain light yellow solid 21 (2.7g,
65%).1H-NMR (400Hz, CDCl3):1.41 (s, 3H, CH3), 3.61 (s, 3H, OCH3), 3.76 (s, 3H, OCH3), 6.15
(s, 1H, CH), 6.72~7.42 (m, 11H, Ph-H), 7.46 (s, 1H, Pyr-H), 8.42 (s, 1H, Pyr-H).
With the preparation of 10 compound 22 of embodiment, naphthols is 6- methoxyl group -1- naphthols, obtains light yellow solid 22
(2.77g, 62%) 1H-NMR (400Hz, CDCl3):3.65 (s, 3H, OCH3), 3.80 (s, 3H, OCH3), 3.96 (s, 3H,
OCH3), 6.14 (s, 1H, CH), 6.76~7.46 (m, 11H, Ph-H), 7.48 (s, 1H, Pyr-H), 8.46 (s, 1H, Pyr-H).
With the preparation of 10 compound 23 of embodiment, naphthols is 3- methoxyl groups-beta naphthal, obtain light yellow solid 23 (2.9g,
65%) 1H-NMR (400Hz, CDCl3):3.61 (s, 3H, OCH3), 3.78 (s, 3H, OCH3), 4.01 (s, 3H, OCH3), 6.15
(s, 1H, CH), 6.79~7.50 (m, 11H, Ph-H), 7.51 (s, 1H, Pyr-H), 8.52 (s, 1H, Pyr-H).
With the preparation of 10 compound 24 of embodiment, naphthols is 6- methoxyl groups-beta naphthal, obtains light yellow solid 24
(2.68g, 60%) 1H-NMR (400Hz, CDCl3):3.66 (s, 3H, OCH3), 3.81 (s, 3H, OCH3), 3.99 (s, 3H,
OCH3), 6.15 (s, 1H, CH), 6.77~7.47 (m, 11H, Ph-H), 7.49 (s, 1H, Pyr-H), 8.48 (s, 1H, Pyr-H).
1 the compounds of this invention antibacterial activity in vitro of application examples is tested
Experimental method:Antifungal Activity in Vitro test method:A certain amount of test compound is dissolved in dimethyl sulfoxide (DMSO), is made into
The solution is diluted to the test fluid of concentration 500mg/L with tween by certain density solution.The above-mentioned solution of 1mL is drawn, is added to
In 9mL potato dextrose agars (PDA) culture medium, access is black at 25 ± 1 DEG C DEG C for trying strain after culture medium completely solidification
After being cultivated 72 hours under dark situation, colony diameter is measured, and is compared with blank control group, is inhibited in vitro
Rate.It is shown in Table 1.
From table 1 it follows that compound 6-24 is to cucumber fusarium axysporum, peanut Cercospora bacteria, Botryosphaeria berengeriana f. sp, small
Wheat sheath blight fungus, southern corn leaf blight, watermelon anthrax bacteria, fusarium moniliforme have certain inhibitory activity, especially to flower
Raw brown patch germ, Botryosphaeria berengeriana f. sp, the inhibition of rhizoctonia cerealis are preferable, are worth further research.
The experimental result of 1 the compounds of this invention 6-24 Antifungal Activity in Vitro of table test
Claims (2)
1.[(6- substitutions-pyrimidine-4-yl oxygen) Ben Ji ]- 3- methoxy-methyl acrylates, which is characterized in that have following structure logical
Formula:
(I)
Wherein, R=H3CO-,,,,,,,,,,,,,,,,,,。
2. Ru Quanliyaoqiu1Suo Shu [(6- substitutions-pyrimidine-4-yl oxygen) Ben Ji ]- 3- methoxy-methyl acrylates, feature exist
In selecting one of following compound:
。
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| CN110199998A (en) * | 2019-06-27 | 2019-09-06 | 江西鑫邦科技有限责任公司 | A kind of Recompounded pesticide of synergy prevention peanut sclerotium rolfsii |
| CN110527630A (en) * | 2019-05-24 | 2019-12-03 | 浙江工业大学 | One plant of Gibberella fujikuroi mutant strain and application using the breeding of ARTP induced-mutation technique |
| CN115557901A (en) * | 2022-10-21 | 2023-01-03 | 湖北有宜新材料科技有限公司 | Efficient production method of pyrimidofuranone |
| CN116768709A (en) * | 2023-05-30 | 2023-09-19 | 湖南大学 | Efficient synthesis method of 2-hydroxy stilbene compounds |
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Cited By (5)
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| CN110527630A (en) * | 2019-05-24 | 2019-12-03 | 浙江工业大学 | One plant of Gibberella fujikuroi mutant strain and application using the breeding of ARTP induced-mutation technique |
| CN110527630B (en) * | 2019-05-24 | 2021-04-20 | 浙江工业大学 | Aleurites lutescens mutant strain bred by ARTP mutagenesis technology and application thereof |
| CN110199998A (en) * | 2019-06-27 | 2019-09-06 | 江西鑫邦科技有限责任公司 | A kind of Recompounded pesticide of synergy prevention peanut sclerotium rolfsii |
| CN115557901A (en) * | 2022-10-21 | 2023-01-03 | 湖北有宜新材料科技有限公司 | Efficient production method of pyrimidofuranone |
| CN116768709A (en) * | 2023-05-30 | 2023-09-19 | 湖南大学 | Efficient synthesis method of 2-hydroxy stilbene compounds |
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