CN110615784B - Synthesis and application of lactone analogue with flavone skeleton - Google Patents
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- CN110615784B CN110615784B CN201911023549.1A CN201911023549A CN110615784B CN 110615784 B CN110615784 B CN 110615784B CN 201911023549 A CN201911023549 A CN 201911023549A CN 110615784 B CN110615784 B CN 110615784B
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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
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/14—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings
- A01N43/16—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings with oxygen as the ring hetero atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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Abstract
The invention relates to synthesis and application of a lactone analogue with a flavone skeleton. The structural general formula of the compound is (I), wherein: r is 1 Or R 2 Represents hydrogen atom, C1-C5 alkyl, phenyl and halogen substituted phenyl, piperonyl, furan, thiophene and other aromatic heterocyclic rings. O-hydroxyacetophenone and aldehyde or ketone are used as raw materials, and a series of lactone analogs with a flavone parent nucleus structure are synthesized through multi-step reaction. The test on the seed germination activity of the broomrape herb compounds shows that the compounds have better seed germination activity, are parasitic weed seed germinants with wide application prospects, can be practically applied to parasitic weed herbicides, and particularly have the application in the aspect of preventing and controlling parasitic weed broomrape and striga asiatica in agriculture.
Description
Technical Field
The invention relates to synthesis and application of a lactone analogue with a flavone skeleton, in particular to synthesis of a lactone analogue with a flavone parent nucleus structure and application of the lactone analogue in controlling and eliminating parasitic weeds, herba Orobanches and striga asiatica in agriculture.
Background
Strigolactones are a new class of phytohormones discovered behind auxins, cytokinins, gibberellins, abscisic acid, and ethylene. The plant hormones play an important role in regulating and controlling the growth and development of plants, and due to the important physiological action of the plant hormones, the study on the strigolactones compounds is more and more widely concerned.
The first strigol compound (+) -strigol was isolated from cotton root exudates in 1966, but its chemical structure was completely elucidated over a period of twenty years due to its complex structure. From this time onwards a series of strigolactones were isolated. The strigolactones have similar structures, mostly have ABC tricyclic lactone skeletons and are connected with a butenolide ring (ring D) through enol ether bonds. The strigolactones which are separated at present are mainly divided into three types: strigol strigolactone compounds; orobanchol type strigol lactone compounds (representative of the compound Orobanchol) and Non-canonical type strigol lactone compounds. The Strigol and Orobanchol strigolactone compounds differ primarily in their stereochemical differences at the BC ring junction. The Non-canonical type strigolactone compounds are different from the two compounds, and the structural characteristics of the compounds are that the compounds do not have a complete ABC tricyclic framework structure.
Striga asiatica and broomrape herb are parasitic weeds parasitizing on plant root systems, and the hosts of striga asiatica and broomrape herb are crops such as corn, sorghum, husked millet, rice, sugarcane and the like. The broomrape weeds are parasitic weeds mainly distributed in China, the yield of watermelons and melons is reduced by 20% -70% due to the parasitic action of the broomrape weeds in Xinjiang province, and the traditional herbicides are difficult to control the spread of the weeds and can damage hosts of the weeds. The germination of the striga asiatica and broomrape herb seeds depends on a signal molecule released by a host thereof, namely natural striga asiatica lactone compounds (SLs), and because the nutrition required by the growth of the parasitic weeds is basically completely dependent on the host, the self-killing type germination of the parasitic weeds can be induced by artificially synthesized striga asiatica lactone compounds under the condition of lacking the host, so that the purpose of removing the weeds can be realized. However, the structure of the natural strigolactones is complex and difficult to synthesize in large quantities and apply to agricultural production, so that the simplification of the structure thereof to synthesize a series of analogs with equivalent activity and simple structure becomes a hotspot of current research.
Chinese patent CN201810446043.0 discloses strigolactone derivatives, a preparation method and application thereof, and the application relates to the germination inhibition activity of compounds on arabidopsis seeds.
Disclosure of Invention
The invention aims to provide synthesis and application of a novel lactone analogue with a natural flavone skeleton. The method takes o-hydroxyacetophenone and aldehyde or ketone as raw materials, and a series of lactone analogs with flavone parent nucleus structures are synthesized through multi-step reaction. The test result shows that the compound has better seed germination activity, in particular to the biological activity of seed germination of broomrape and broomrape. Is a parasitic weed seed germinator with wide application prospect.
The lactone analogue with the flavone skeleton provided by the invention has the structure shown in (I):
wherein R is 1 Or R 2 Represents C1-C5 alkyl, phenyl, halogen substituted phenyl, piperonyl, furan, thiophene and other aromatic heterocycles.
Preferably, R1 or R2 represents a hydrogen atom, a C1-C5 alkyl group, a phenyl group, a halogen, an alkyl group, or an alkoxy-substituted phenyl group, and an aromatic heterocycle such as furan, thiophene, etc. Preference is given to hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, n-pentyl, phenyl.
Further preferably: 3- (((4 ' -methyl-5 ' -oxo-2 ',5' -dihydrofuran-2 ' -yl) oxy) methylene) 4-chromanone; 2-methyl-3- (((4 ' -methyl-5 ' -oxo-2 ',5' -dihydrofuran-2 ' -yl) oxy) methylene) 4-chromanone; 2-ethyl-3- (((4 ' -methyl-5 ' -oxo-2 ',5' -dihydrofuran-2 ' -yl) oxy) methylene) 4-chromanone; 2-propyl-3- (((4 ' -methyl-5 ' -oxo-2 ',5' -dihydrofuran-2 ' -yl) oxy) methylene) 4-chromanone; 2-butyl-3- (((4 ' -methyl-5 ' -oxo-2 ',5' -dihydrofuran-2 ' -yl) oxy) methylene) 4-chromanone; 2-pentyl-3- (((4 ' -methyl-5 ' -oxo-2 ',5' -dihydrofuran-2 ' -yl) oxy) methylene) 4-chromanone; 2-phenyl-3- (((4 ' -methyl-5 ' -oxo-2 ',5' -dihydrofuran-2 ' -yl) oxy) methylene) 4-chromanone.
The compounds and their acceptable salts are useful as herbicides in agriculture.
The compound and the agriculturally acceptable salt thereof can also be used as an effective component to be mixed with other components to be used as a pesticide composition and used as a herbicide.
The synthesis method of the lactone analogue with the flavone skeleton comprises the following steps:
the invention provides synthesis and biological activity of a novel compound for inducing parasitic weed seeds to undergo suicide germination. The compounds can stimulate seeds to germinate by acting on parasitic weeds such as striga asiatica and broomrape parasitizing in common crop seeds, so that the seeds can not parasitize in host plants to cause death. The invention compares with CN 201810446043.0: 1) The structural types of the compounds involved differ. The invention relates to the design and synthesis of compounds derived from natural flavanone compounds and the germination activity of weed seeds; the compounds of the above application have a significantly different structure from the present invention; 2) The routes and modes of action differ. The application relates to the germination inhibition activity of the compound on arabidopsis seeds, and the invention designs the induced germination activity of the compound on parasitic weed seeds, and the compound and the parasitic weed seeds have obviously different functions.
The lactone analogue with the flavone parent nucleus structure is applied to a parasitic weed seed germinator and a parasitic weed herbicide. The compound has a remarkable induction effect on the germination of parasitic weed seeds in crops in China, so that parasitic weeds cannot be parasitized in host seeds, and the parasitic weeds finally die in a suicide mode. The farmland crop host plant is selected from corn, sorghum, millet, rice, potato, cassava, soybean, sunflower, beet, sugarcane, tomato, cucumber, watermelon, melon, hami melon, papaya and papaya. The parasitic weeds are preferably selected from striga asiatica, broomrape.
In a word, the invention provides a lactone analogue with a natural product flavone parent nucleus structure, and a preparation method and application thereof. O-hydroxyacetophenone and aldehyde or ketone are used as raw materials, and a series of lactone analogs with a flavone parent nucleus structure are synthesized through multi-step reaction. The test on the germination activity of the broomrape seeds shows that the compounds have better seed germination activity and are parasitic weed seed germinants with wide application prospect. Can be practically applied to parasitic weed herbicides. The invention relates to application of flavonoid lactone analogues, in particular to application in the prevention and control of parasitic weed orobanche coerulescens and striga asiatica in agriculture.
Detailed Description
The present invention will be described in detail with reference to examples, but the present invention is not limited to these examples. The experimental methods in the examples, in which specific conditions are not specified, are generally performed under the conditions described in the manual and the conventional conditions, or under the conditions recommended by the manufacturer; the equipment, materials, reagents and the like used are commercially available unless otherwise specified.
Example 1
Scheme 1:
1.36ml of o-hydroxyacetophenone (1.2 eq), 0.96ml of benzaldehyde (1 eq) and 1.29ml of aniline (1.5 eq) were dissolved in 15ml of methanol, followed by addition of 0.72g of iodine and reaction with stirring at 40 ℃ for 20 hours. The reaction was monitored by TLC and after complete consumption of the substrate the reaction was concentrated and directly chromatographed on silica gel (petroleum ether: ethyl acetate =200: 1) to give 1.3g total white solid 1 in 61.5% yield.
0.68g of compound 1 (1 eq) was dissolved in 10ml of toluene, and then 1.21ml of N, N-dimethylformamide dimethyl acetal (3 eq) was added to the reaction system to conduct a reflux reaction at 150 ℃ for 6 to 8 hours and monitored by TLC, and after the reaction was completed, the mixture was directly separated by silica gel column chromatography (petroleum ether: ethyl acetate = 2) to obtain 0.68g of a pale yellow solid 2 in total, with a yield of 80.4%.
0.68g of compound 2 (1 eq) was dissolved in 15ml of tetrahydrofuran: glacial acetic acid: in a mixed solution of water = 1. The organic phase is then dried using anhydrous sodium sulfate and the residue obtained by spin drying the organic phase is the crude product of compound 3. Directly dissolving the crude product of the compound 3 in 15mL of anhydrous tetrahydrofuran, cooling the reaction system to 0 ℃ in ice bath, adding 0.3g of potassium tert-butoxide (1.1 eq) to the reaction system, stirring for 15min, finally dissolving 0.43g of 5-bromo-3-methylfuran-2 (5H) -one (1 eq) in 5mL of anhydrous tetrahydrofuran and slowly dropping into the reaction system for reaction for 12 hours, concentrating the reaction system after the completion of the reaction by TLC and directly performing silica gel column chromatography (petroleum ether: ethyl acetate: dichloromethane = 7.
Scheme 2:
1.32ml of o-hydroxyacetophenone (1 eq), 1.21ml of acetone (1.5 eq) and 1.38ml of pyrrolidine (1.5 eq) are dissolved in 20ml of anhydrous ethanol, and then heated at 120 ℃ for reflux reaction for 24 hours and detected by TLC, and the reaction is stopped when the o-hydroxyacetophenone is completely consumed. The reaction system was concentrated and separated by silica gel column chromatography (petroleum ether: ethyl acetate = 200).
0.77g of sodium ethoxide (2 eq) was dissolved in 20ml of toluene, and 0.84g of ethyl formate (2 eq) was added to the reaction system. 1g of Compound 1 (1 eq) was dissolved in 20ml of toluene and added dropwise to the reaction system over 15min. After 24h of reaction, water was added to quench the reaction and the organic phase was washed with 2M sodium hydroxide solution. The aqueous phase was washed with diethyl ether and adjusted to pH 1 using concentrated hydrochloric acid, after which the aqueous phase was extracted with ethyl acetate. The organic phase is dried by anhydrous magnesium sulfate, and a brown solid product, namely the intermediate 2, is obtained after the organic phase is spin-dried, and is directly used for the next reaction without separation. 1.16g of the crude intermediate 2 (1 eq) was dissolved in 15ml of anhydrous tetrahydrofuran, the reaction was cooled to 0 ℃ in ice, and 0.70g of potassium tert-butoxide (1.1 eq) was added to the reaction and stirred for 15min. Finally, 1.01g of 5-bromo-3-methylfuran-2 (5H) -one (1 eq) was dissolved in 5ml of anhydrous tetrahydrofuran and slowly dropped into the reaction system to react for 12 hours, and after completion of the reaction was checked by TLC, the reaction system was concentrated and subjected to silica gel column chromatography (petroleum ether: ethyl acetate: dichloromethane = 7).
Scheme 3:
1.33ml of o-hydroxyacetophenone (1 eq) and 2.03ml of n-hexanal (1.5 eq) were dissolved in 50ml of anhydrous ethanol, and then 0.14ml of pyrrolidine (0.15 eq) was added to the reaction system. The reaction system is heated to about 120 ℃ and refluxed for 20 hours. And monitoring the reaction process by TLC, and stopping the reaction after the o-hydroxyacetophenone is basically reacted. The reaction was concentrated and directly separated by silica gel column chromatography (petroleum ether: ethyl acetate = 100) to give 1.69g in total of yellow oil 1 in 70% yield. 2.91g of potassium tert-butoxide (2 eq) were dissolved in 15ml of anhydrous ether and the reaction was ice-cooled to 0 ℃. 2.83g of Compound 1 (1 eq) and 2.09ml of ethyl formate were subsequently dissolved in 6ml of absolute ethanol. Slowly adding ethanol solution of the compound 1 and ethyl formate dropwise into the reaction system, stirring for 14 hours at room temperature and monitoring by TLC. And after the reaction is finished, the reaction system is dried in a spinning mode, 20ml of water is added into the reaction system, the water phase is extracted and washed by dichloromethane, after multiple times of extraction, the pH value of the water phase is adjusted to 1-2 by using concentrated hydrochloric acid, and a solid product is separated out. The aqueous phase was extracted with ethyl acetate, and the organic phase was dried over anhydrous magnesium sulfate and spin-dried to give intermediate 2, which was used in the next reaction without purification. 1.07g of the crude intermediate 2 (1 eq) was dissolved in 15ml of anhydrous tetrahydrofuran, and 536mg of potassium tert-butoxide (1.1 eq) was added to the reaction system. The reaction system is iced in ice bath, the reaction temperature is adjusted to 0 ℃, the stirring is carried out for 15min, then 768mg of 5-bromo-3-methylfuran-2 (5H) -one (1 eq) is dissolved in 5ml of anhydrous tetrahydrofuran, and the mixture is slowly dropped into the system to react for 12 hours. After the completion of the TLC detection reaction, the reaction system was concentrated and directly separated by silica gel column chromatography (petroleum ether: ethyl acetate: dichloromethane =7: 1) to obtain 290mg of W-20 as a yellow oil in a total yield of 19.5%. (W-19 was also synthesized according to the route)
Compounds W-1 to W-24 were synthesized according to the three routes described above, and the physicochemical data of the compounds are shown in Table 1, and the NMR data of typical compounds are shown in Table 2.
Table 1: physicochemical Properties and yield of Compound
Table 2: NMR data for typical Compounds
The following is the structure of the synthesized flavonoid lactone analogue:
example 2
The germination activity of seeds of the muskmelon broomrape and the sunflower broomrape is tested on the compounds W-1 to W-24 by the following test methods:
a plastic culture dish with a diameter of 9cm is taken, a piece of filter paper is paved on the bottom layer and is wetted by sterilized distilled water, and then a piece of filter paper with a diameter of 6mm is paved.Uniformly spraying the seed of the orobanche coerulescens on a wet filter paper sheet, the number of seeds on the filter paper sheet is about 25-65. Seal the petri dish with sealing glue and pre-culture the seeds in the dark at room temperature for 3-7 days. Taking a glass fiber filter paper sheet with the diameter of 6mm, placing the glass fiber filter paper sheet into a plastic culture dish, adding 25 mu L of a compound solution to be detected (acetone is used as a solvent), placing a pre-culture seed sheet above the glass fiber filter paper sheet after the acetone is completely volatilized, adding 25 mu L of sterilized distilled water, finally placing the filter paper sheet wetted by the sterilized distilled water in the center of the culture dish for moisturizing, sealing the culture dish by using sealing glue, culturing for ten days at the room temperature in the dark, observing the seed germination condition under a microscope, calculating the germination rate, and taking commercialized GR24 as a reference. Compounds were tested in triplicate for each concentration, four experiments were performed for each concentration and the mean and standard deviation were calculated, and EC for compounds was calculated using SPSS 19.0 50 The value is obtained. The germination activity test method of the broomrape seed is the same as that of the broomrape seed.
TABLE 3 induced germination Activity screening of Compounds W-1 to W-24 on Cucumis melo Orobanchus seeds
TABLE 4 induced germination rate of partial compound Helianthus annuus seed
Claims (3)
1. A lactone analog with flavone parent nucleus structure, and its agriculturally acceptable salt; the concrete structure is as follows:
wherein, the corresponding substituent is:
2. a lactone analog having a flavone core structure, characterized by being selected from the group consisting of: w-12, W-19, W-20, W-21, W-22, W-23 or W-24, and the specific structure is as follows:
3. the composition of the lactone analog with the flavone parent nucleus structure as claimed in claim 1 or 2, characterized in that the composition comprises the effective active ingredients of the lactone analog with the flavone parent nucleus structure in the mass percentage: 0.l-99%.
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| CN114369087B (en) * | 2022-02-07 | 2023-08-22 | 南开大学 | Synthesis and application of lactone analogue with indoline-2-ketone skeleton |
| US11937600B1 (en) | 2023-03-14 | 2024-03-26 | King Faisal University | Seed germination activator for control of broomrape |
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2019
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| EP0139615A2 (en) * | 1983-08-31 | 1985-05-02 | Zyma SA | Flavene and thioflavene derivatives, processes for their manufacture, pharmaceutical preparations that contain such compounds, and the use of the latter |
| JPS61221170A (en) * | 1985-03-28 | 1986-10-01 | Nippon Kayaku Co Ltd | Trifluoromethanesulfonylamide derivative and herbicide containing said derivative as active component |
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