CN114369087A - Synthesis and application of lactone analogue with indoline-2-ketone skeleton - Google Patents
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Abstract
The invention relates to synthesis and application of a lactone analogue with an indoline-2-ketone skeleton. The structural general formula of the compound is shown as a formula (I), wherein: r1 represents a substituted halogen atom, fluorine, chlorine, bromine or an unsubstituted hydrogen atom, and R2 represents a methyl to N-pentyl group substituted on the N atom and an aromatic ring or benzyl group substituent. Halogen-substituted indoline-2-ketone or indoline-2, 3-diketone is taken as a raw material, and the lactone analogue with the indoline-2-ketone parent nucleus structure is obtained through 2-3 steps of synthesis. The broomrape seeds are used as control objects, and the series of compounds are applied to carry out seed germination activity test, have better seed germination activity and can be applied to parasitic plantsSeeds of the raw broomrape germinate and develop parasitic broomrape 'suicide' type herbicides. The invention also comprises the application of the compound in preventing and treating parasitic weed diseases such as broomrape, striga asiatica and the like by combining the compound with agriculturally acceptable auxiliary agents, synergistic agents or commercial herbicides.
Description
Technical Field
The invention relates to synthesis of a lactone analogue with an indoline-2-ketone skeleton and application thereof in preventing and controlling parasitic weeds, namely broomrape and striga asiatica in agriculture.
Background
The strigolactones are identified as a novel plant hormone in 2008 after auxin, gibberellin, cytokinin, abscisic acid, gibberellin and ethylene. The plant hormones play a crucial role in regulating and controlling the growth and development of plants. Because of their important physiological and biochemical effects, the study of these compounds has also received a great deal of attention from chemists and biologists worldwide.
The first compound (+) -Strigol ((+) -Strigol) which stimulates the germination of parasitic weed striga asiatica was extracted from the root secretions of cotton by Cook in 1966, the approximate configuration of the compound was obtained in 1972, and the absolute configuration of the compound was finally determined by X-ray in 1985. After 30 years, scientists continuously extract strigolactones natural products which stimulate the germination of root parasitic plant seeds from secretions of high-grade plants such as corn, sorghum, cowpea and the like. Through configuration research on a series of natural products, researchers find that the compounds mostly have ABC tricyclic lactone frameworks and are connected with butenolide (D ring) through enol ether bonds. The natural strigolactone analogs isolated at present are mainly classified into strigol and orosoh. The main difference between these two classes of compounds is the stereochemical configuration at the BC fused ring.
The rostellular and striga metals are one of the parasitic angiosperms and are widely distributed throughout the world. The two types of plants with parasitic weed hosts have various varieties and high propagation speed, and cause serious harm to crops and economic crops. It is statistical that 5000 more than ten thousand hectares are occupied in metal-destroyed land in only one foot of africa, and the economic loss caused by the metal-destroyed land is as high as 30 more billion dollars. The temperature required for seed germination of the broomrape genus is lower than that of the striga metal, and thus the broomrape genus is mainly distributed in subtropical or temperate regions, for example, asia, oceania, mediterranean, etc. According to investigation, 23 broomrape genera exist in China, and are mainly distributed in northwest areas of China, wherein the broomrape genera are the most in Sinkiang. The host plants of Orobanchum are mainly cereals, Artemisia, melon and other plants. Taking the orobanche coerulescens as an example, in Xinjiang, due to the parasitic of the orobanche coerulescens on host plants such as melons, watermelons and the like, the yield of the melons and watermelons is greatly reduced, and the reduction range is about 20-70%. Because of the consistency of the growth cycle of the parasitic weeds of the broomrape and the striga and the host plant, spraying herbicides such as glyphosate does not provide good control over the spread of such weeds and may damage the host plant. The germination of strigola asiatica and broomrape herb seeds is dependent on strigolactone analogs secreted by their host plants. Therefore, the application of the natural strigolactone analogues stimulates the seeds of strigola and broomrape to separate from the host plant and germinate in advance, and finally, the seeds die in a suicide mode due to lack of nutrition and moisture, thereby achieving the purpose of preventing and controlling weeds. However, the structure of the natural strigolactone analogue is complex, and a large amount of manpower and material resources are consumed in the separation and purification process, so that the natural strigolactone analogue is difficult to be applied to agricultural production. Therefore, the search for highly active structurally simplified analogs is a problem to be solved.
Chinese patent CN 201911023549.1 discloses the synthesis and application of a lactone analog with a flavone skeleton. The compound has a structural general formula as follows:
the compound has better seed germination activity, is a parasitic weed seed germinator with wide application prospect, can be practically applied to parasitic weed herbicides, and particularly has application in the prevention and control aspect of parasitic weed orobanche and striga asiatica in agriculture.
Disclosure of Invention
The invention aims to provide synthesis and application of a novel lactone analogue with an indoline-2-ketone framework. Halogen-substituted indoline-2-ketone or indoline-2, 3-diketone is taken as a raw material, and a series of lactone analogs with indoline-2-ketone parent nucleus structures are synthesized through 2-3 steps of reaction. The test on the germination activity of the broomrape seeds shows that the compound has better seed germination activity, particularly the biological activity of the broomrape seeds germination, and is a parasitic weed seed germination agent with wide application prospect.
The analogue with indoline-2-ketone skeleton provided by the invention has the structure shown in (I):
wherein: r1Represents a substituted halogen atom, fluorine, chlorine, bromine or an unsubstituted hydrogen atom, R2Represents methyl to N-pentyl substituted on the N atom and aromatic ring or benzyl substituents.
Preferably, R1Is a halogen substituent (comprising fluorine, chlorine and bromine atoms) on the benzene ring of the indole ring. R2Is an aromatic ring such as C1-C5 alkyl substituent on indole N, alkoxy substituted benzyl or substituted phenyl and the like. Preferred are a fluorine atom, a chlorine atom, a bromine atom, a methyl group, an ethyl group, an n-propyl group, an n-butyl group, a phenyl group, a 4-methylphenyl group, a 2, 6-dichlorophenyl group and a benzyl group. Wherein R is1Preferably hydrogen, fluorine, chlorine, bromine，R2Is composed ofN-an alkyl substitution,Naryl, the preferred substituents being methyl, ethyl, n-propyl, n-butyl, phenyl, 4-methylphenyl, 2, 6-dichlorophenyl, benzyl.
The specific compound is as follows: 7/6/5-halogen-substituted, N-alkyl-substituted, N-aryl-substituted 3- (((4 ' -methyl-5 ' -oxo-2 ', 5 ' -dihydrofuran-2 ' -yl) oxy) methylene) indolin-2-one, designated 7/6/5-halo-substituted-N-substistuted-3- (((4-methyl-5-oxo-2,5-dihydrofuran-2-yl) oxy) methyl) indolin-2-one, wherein the substituents 7/6/5-halogen-substituted, N-alkyl-substituted, N-aryl, etc. are within the ranges described above (claim 2).
The analogue with indoline-2-ketone skeleton provided by the invention is the following compound:
7-bromo-3- (((4 ' -methyl-5 ' -oxo-2 ', 5 ' -dihydrofuran-2 ' -yl) oxy) methylene) indolin-2-one; 5-chloro-3- (((4 ' -methyl-5 ' -oxo-2 ', 5 ' -dihydrofuran-2 ' -yl) oxy) methylene) indolin-2-one; 6-chloro-3- (((4 ' -methyl-5 ' -oxo-2 ', 5 ' -dihydrofuran-2 ' -yl) oxy) methylene) indolin-2-one; 3- (((4 ' -methyl-5 ' -oxo-2 ', 5 ' -dihydrofuran-2 ' -yl) oxy) methylene) indolin-2-one;N-phenyl-3- (((4 ' -methyl-5 ' -oxo-2 ', 5 ' -dihydrofuran-2 ' -yl) oxy) methylene) indolin-2-one;N-4-methylphenyl-3- (((4 ' -methyl-5 ' -oxo-2 ', 5 ' -dihydrofuran-2 ' -yl) oxy) methylene) indolin-2-one;N-2, 6-dichlorophenyl-3- (((4 ' -methyl-5 ' -oxo-2 ', 5 ' -dihydrofuran-2 ' -yl) oxy) methylene) indolin-2-one;N-methyl-3- (((4 ' -methyl-5 ' -oxo-2 ', 5 ' -dihydrofuran-2 ' -yl) oxy) methylene) indolin-2-one;N-ethyl-3- (((4 ' -methyl-5 ' -oxo-2 ', 5 ' -dihydrofuran-2 ' -yl) oxy) methylene) indolin-2-one;N-n-propyl-3- (((4 ' -methyl-5 ' -oxo-2 ', 5 ' -dihydrofuran-2 ' -yl) oxy) methylene) indolin-2-one;N-n-butyl-3- (((4 ' -methyl-5 ' -oxo-2 ', 5 ' -dihydrofuran-2 ' -yl) oxy) methylene) indolin-2-one;N-benzyl-3- (((4 ' -methyl-5 ' -oxo-2 ', 5 ' -dihydrofuran-2 ' -yl) oxy) methylene) indolin-2-one.
The synthesis method of the lactone analogue with indoline-2-ketone skeleton provided by the invention comprises the following steps:
scheme 1: synthesis of the final Compound
Scheme 2: synthesis of the D Ring
The lactone analogue with indoline-2-ketone parent nucleus can be applied to ecological-friendly parasitic weed herbicides and seed germinants thereof. The compound has obvious induction effect on parasitic weed seeds in crops and economic crops in China, so that the parasitic weed seeds are induced to germinate before the host seeds and then break away from the host plants to finally cause the parasitic weeds to die. The farmland 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 selected from striga asiatica and broomrape herb.
The compounds and their acceptable salts are useful as herbicides in agriculture.
The compound and the agriculturally acceptable salt thereof can be used as an effective component to be combined with other components to be used as a pesticide composition and used as a herbicide.
The invention provides synthesis and biological activity of a novel compound for inducing plant parasitic seeds to generate suicide germination. The compound acts on parasitic weeds such as striga asiatica or broomrape which are parasitic on common crop seeds to stimulate the seeds to germinate before the host plant seeds, so that the seeds cannot be parasitic to cause death. The present invention is different from CN 201911023549.1 in the structural types of the related compounds (1). The invention relates to a design and synthesis method of indoline-2-ketone compounds with anti-tumor activity and the germination activity of weed seeds; the compounds of the above patents have a significantly different structure from the present invention; (2) the synthesis cost is different: the synthesis steps of the invention are simplified into 2-3 steps, and the synthesis cost of the compounds is greatly reduced because the raw materials are cheap and easy to obtain.
The invention provides a preparation method and application of a lactone analogue with an indoline-2-ketone parent nucleus. Halogen-substituted indoline-2-ketone or indoline-2, 3-diketone is taken as a raw material, and a series of lactone analogs with indoline-2-ketone parent nucleus structures are synthesized through 2-3 steps of reaction. Tests on the seed germination activity of the broomrape of the compound show that the compound has better seed germination activity, is a parasitic weed seed germination agent with wide application prospect, and can be practically applied to the control of parasitic weeds. The invention relates to application of indoline-2-ketone lactone analogues, in particular to application in the field of control of parasitic weeds, namely striga asiatica and broomrape 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:
in a dry 100mL round bottom flask, NaH (1 eq, 60% in oil) was dissolved in 20mL xylene solution, and the reaction was heated at 130 ℃. After heating for 15 minutes, the 5/6/7 th halogen-substituted indolin-2-one (1, 1 eq) was slowly added to the reaction system in portions, and then the reaction system was refluxed. After refluxing for 1 h, dimethyl sulfate (1 eq) was slowly added to the reaction system, and then the reaction was continued at 130 ℃ for another hour. After the reaction was completed, the reaction system was cooled to room temperature, and then extracted with ethyl acetate. And washing the collected organic phase with saturated salt water, drying with anhydrous sodium sulfate, filtering, and desolventizing to obtain a crude product. The crude product was isolated by column chromatography (PE: EA =2:1, v/v) to yield pure intermediate 2 (orange solid, yield 55%).
Into a previously dried 100mL round bottom flask, isatin (1 eq), anhydrous potassium carbonate (2.5 eq) and alkyl bromide or aryl bromide (1.2 eq) were added in this order and dissolved in 20mL of a solution of ldmf. The reaction system was heated at 70 ℃ for 12 h (wherein methyl iodide, ethyl bromide and n-propyl bromide were reacted and the reaction system was stirred at room temperature for 12 h). After the reaction was completed, the reaction system was cooled to room temperature, and then poured into an ice-cold aqueous solution of sodium chloride. And (3) carrying out suction filtration on the solid-liquid mixture by using a Buchner funnel, sequentially washing the collected orange solid by using water and n-hexane, and then recrystallizing by using a 95% ethanol solution to obtain an intermediate 2', wherein the yield is 90%. The product can be directly used for the next reaction without further purification.
The intermediate 2' obtained in the previous step is dissolved in 20mL of hydrazine hydrate solution, and then is refluxed at 120 ℃ for 4 hours under the protection of argon. And after the reaction is finished, cooling the reaction system to room temperature, extracting the reaction system by using ethyl acetate, washing the collected organic phase by using water and saturated saline solution, drying the organic phase by using anhydrous sodium sulfate, and performing suction filtration and desolventizing to obtain a crude product. The crude product was purified by column chromatography (PE: EA =6:1, v/v) to give a tan intermediate 3' with a yield of 76%.
The intermediate 2, 3' obtained above and a commercial intermediate (1 eq) were charged into a 50mL round-bottomed flask, and 1mL of anhydrous methanol, 1mL of ethyl formate and 1mL of a sodium methoxide solution (30% by weight aqueous solution) were added and stirred at room temperature until the system became a solid phase. After the reaction is finished, the pH value of the reaction system is adjusted to 2 by using 1M dilute hydrochloric acid, the reaction system is extracted by using ethyl acetate, the collected organic phase is washed by water and saturated saline solution, dried by anhydrous sodium sulfate, filtered and desolventized to obtain a crude product 4. Crude 4(1 eq) was dissolved in 15mL of anhydrous tetrahydrofuran solution, anhydrous potassium carbonate (2 eq) was added, and after stirring at room temperature for 10 minutes, a solution of D-ring in tetrahydrofuran (1.1 eq, 5mL) was added, and the mixture was stirred at room temperature overnight. After the reaction is finished, extracting the reaction system by using ethyl acetate, washing the collected organic phase by using water and saturated saline solution, drying by using anhydrous sodium sulfate, and carrying out suction filtration and desolventizing to obtain a crude product. The crude product is separated and purified by column chromatography (PE: EA: DCM =6: 1:2, v/v) to obtain the product 5, and the yield is 13.1-45.9%.
Scheme 2:
to a 250mL round bottom flask dried in advance, glyoxal (40% wt aqueous solution, 1.4 eq) and methylmalonic acid (1 eq) were added in this order and dissolved in 90mL of water. Then 20d of concentrated sulfuric acid was added to the reaction system, and the mixture was refluxed for 16 hours. And after the reaction is finished, cooling the reaction system to room temperature, extracting the reaction system by using ethyl acetate, washing the collected organic phase by using water and saturated saline solution, drying the organic phase by using anhydrous sodium sulfate, and performing suction filtration and desolventizing to obtain a crude product. The crude product was purified by column chromatography (PE: EA =2:1, v/v) to give an orange intermediate, 5-hydroxy-3-methylfuran-2-one, in 60% yield.
The intermediate (1 eq) obtained in the previous step was dissolved in 20mL of anhydrous dichloromethane, and the reaction system was placed at 0 ℃, carbon tetrabromide (1.4 eq) and triphenylphosphine (1.4 eq) were added in succession, slowly in portions, and then the system was gradually returned to room temperature and stirred for 2.5 h. And (3) after the reaction is finished, spin-drying the reaction system, and performing column chromatography separation and purification (PE: EA =6: 1-3:1, v/v) to obtain a yellow oily liquid, namely the product D ring, wherein the yield is 58%.
The compounds 1-22 are synthesized according to the three routes, and the physicochemical data of the compounds are shown in Table 1.
Table 1: physicochemical Properties and yield of Compound
TABLE 2 NMR data for typical compounds
The structure of the synthetic indoline-2-ketone lactone analogue is as follows:
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 disposable plastic culture dish with the 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 the diameter of 6mm is paved. The seed of the melon is sprinkled on the wet filter paper sheet, the number of the seed of the filter paper sheet is about 25-65. The petri dish was sealed with a sealing compound and the seeds were pre-incubated 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 in a plastic culture dish, adding 25 mu L of a compound solution to be detected (using acetone as a solvent), taking a pre-culture seed sheet after the acetone is completely volatilized, placing the pre-culture seed sheet above the pre-culture seed sheet, 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 with sealing glue, culturing the pre-culture seed sheet in a dark place for ten days, observing the seed germination condition under a microscope, calculating the germination rate, and using commercialized GR24 as a control. 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 19.050The value is obtained.
TABLE 3 induced germination activity screening of compounds 1-22 on seeds of Orobanchus melo
EC of part of the Compounds of Table 450Value determination
Claims (8)
1. A lactone analogue with an indolin-2-ketone parent nucleus structure is characterized in that the structure is shown as a general formula (I), and agriculturally acceptable salts thereof:
wherein: r1Represents a substituted halogen atom, fluorine, chlorine, bromine or an unsubstituted hydrogen atom, R2Represents alkyl of C1-C5 substituted on the N atom, phenyl, 2,6, -dichlorophenyl and benzyl.
2. The lactone analog having an indolin-2-one core structure of claim 1, wherein:
R1is hydrogen, fluorine, chlorine or bromine; r2Is methyl, ethyl, n-propyl, n-butyl, phenyl, 4-methylphenyl, 2, 6-dichlorophenyl or benzyl.
3. The lactone analog having an indolin-2-one core structure according to claim 1, wherein the specific compound name is: 7/6/5-a halogen substitution, wherein,N-an alkyl substitution,N-aryl substituted 3- (((4 ' -methyl-5 ' -oxo-2 ', 5 ' -dihydrofuran-2 ' -yl) oxy) methylene) indolin-2-one; english system name 7/6/5-halogen sublittated-N-substitated-3- (((4-methyl-5-oxo-2,5-dihydrofuran-2-yl) oxy) methyl) indolin-2-one, wherein 7/6/5-halogen is substituted,N-an alkyl substitution,Nthe substituents such as aryl are in the range described in claim 2.
4. The lactone analog having an indolin-2-one core structure of claim 1, wherein the specific compound is: 7-bromo-3- (((4 ' -methyl-5 ' -oxo-2 ', 5 ' -dihydrofuran-2 ' -yl) oxy) methylene) indolin-2-one; 5-chloro-3- (((4 ' -methyl-5 ' -oxo-2 ', 5 ' -dihydrofuran-2 ' -yl) oxy) methylene) indolin-2-one; 6-chloro-3- (((4 ' -methyl-5 ' -oxo-2 ', 5 ' -dihydrofuran-2 ' -yl) oxy) methylene) indolin-2-one; 3- (((4' -methyl-5 ' -oxo-2 ', 5 ' -dihydrofuran-2 ' -yl) oxy) methylene) indolin-2-one;N-phenyl-3- (((4 ' -methyl-5 ' -oxo-2 ', 5 ' -dihydrofuran-2 ' -yl) oxy) methylene) indolin-2-one;N-4-methylphenyl-3- (((4 ' -methyl-5 ' -oxo-2 ', 5 ' -dihydrofuran-2 ' -yl) oxy) methylene) indolin-2-one;N-2, 6-dichlorophenyl-3- (((4 ' -methyl-5 ' -oxo-2 ', 5 ' -dihydrofuran-2 ' -yl) oxy) methylene) indolin-2-one;N-methyl-3- (((4 ' -methyl-5 ' -oxo-2 ', 5 ' -dihydrofuran-2 ' -yl) oxy) methylene) indolin-2-one;N-ethyl-3- (((4 ' -methyl-5 ' -oxo-2 ', 5 ' -dihydrofuran-2 ' -yl) oxy) methylene) indolin-2-one;N-n-propyl-3- (((4 ' -methyl-5 ' -oxo-2 ', 5 ' -dihydrofuran-2 ' -yl) oxy) methylene) indolin-2-one;N-n-butyl-3- (((4 ' -methyl-5 ' -oxo-2 ', 5 ' -dihydrofuran-2 ' -yl) oxy) methylene) indolin-2-one;N-benzyl-3- (((4 ' -methyl-5 ' -oxo-2 ', 5 ' -dihydrofuran-2 ' -yl) oxy) methylene) indolin-2-one.
5. The method for preparing the lactone analogue with the indoline-2-ketone parent nucleus structure as claimed in claim 1, which is characterized in that the product is finally obtained by nucleophilic substitution, Wolff-Kishner-Huang Minlon reduction reaction and Williamson ether synthesis reaction by taking halogen substituted indoline-2-ketone or indoline-2, 3-diketone as raw materials;
the synthetic route is as follows:
the synthesis of the D ring is shown below:
6. use of the lactone analog having an indolin-2-one core structure according to any one of claims 1 to 4 for seed germination and parasitic weed control of parasitic weeds.
7. Use according to claim 6, wherein the farmland host plants are selected from the group consisting essentially of corn, sorghum, millet, rice, potato, cassava, soybean, sunflower, sugarbeet, sugarcane, tomato, cucumber, watermelon, melon, cantaloupe, papaya; the parasitic weeds are selected from striga asiatica and broomrape.
8. The composition comprising the lactone analog having indolin-2-one nucleus structure as an effective active ingredient and an auxiliary according to any one of claims 1 to 4, wherein the effective active ingredient comprises: 0.1-99% by mass.
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| CN110615784A (en) * | 2019-10-25 | 2019-12-27 | 南开大学 | Synthesis and application of lactone analogue with flavone skeleton |
| CN113072544A (en) * | 2021-01-25 | 2021-07-06 | 浙江农林大学 | Compound capable of promoting seed germination of parasitic plants prepared based on indole-3-carboxylic acid and preparation method thereof |
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| CN110615784A (en) * | 2019-10-25 | 2019-12-27 | 南开大学 | Synthesis and application of lactone analogue with flavone skeleton |
| CN113072544A (en) * | 2021-01-25 | 2021-07-06 | 浙江农林大学 | Compound capable of promoting seed germination of parasitic plants prepared based on indole-3-carboxylic acid and preparation method thereof |
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