CN101434578A - Synthesis and use of mesaconitine esterification derivative and salt thereof - Google Patents
Synthesis and use of mesaconitine esterification derivative and salt thereof Download PDFInfo
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Abstract
The invention discloses a method for synthesizing a sulfated derivative and a salt (with a compound with structure shown as the picture) from a natural diterpenoid alkaloid in aconitum plants and an application thereof, pertaining to the technical field of helminthic synthesis. A preparation method of the compound sulfated derivative and the salt thereof comprises the steps that an aconitine solution is dissolved in a dry pyridine and subjected to alkaline treatment, chloroform extraction and steaming and concentration after being added with a sulfate reagent for a chemical reaction, thus obtaining the sulfated derivative of aconitine; and then the salt of the compound of the sulfated derivative is obtained by the means of directly adding dropwise with an acid solution. The synthesizing method is simple and convenient and has relatively low cost and high transformation rate. The compound obtained from synthesis has relatively good desinsection activity and can be used for developing pesticide. In the formula, R1 refers to alkanoyl, fatty acyl, sulfonyl or aromaticacyl radical such as acetyl, propionyl, benzoyl, caproyl, methanesulfonyl, p-chlorobenzene formyl, and the like; R2 refers to hydrogen atoms or alkanoyl, fatty acyl, sulfonyl or aromaticacyl radical such as acetyl, propionyl, benzoyl, caproyl, methanesulfonyl, p-chlorobenzene formyl, and the like; and R3 refers to hydrogen atoms or alkanoyl, fatty acyl, sulfonyl or aromaticacyl radical such as acetyl, propionyl, benzoyl, caproyl, methanesulfonyl, p-chlorobenzene formyl, and the like.
Description
(1) technical field
The present invention relates to the synthetic method and the pesticidal applications of mesaconitine esterified derivative and salt thereof, belong to the insecticidal materials synthesis technical field.
(2) technical background
Mesaconitine is a kind of C-19 type diterpene alkaloid that extraction separation obtains in the sub-root of the Ranunculaceae aconitum plant rhizome of Chinese monkshood (Chinese medicine monkshood), and its structural formula is shown in figure (I).The medicinal history of the existing two thousand years of Chinese medicine monkshood, its effect mainly contains analgesia, cardiac stimulant, recuperating deplered YANG and rescuing the patient from collapse etc., finds that simultaneously it has good insecticidal activity.Along with the rise that the plant insecticide of environmental protection is studied, alkaloidal insecticidal activity is found and attention by increasing people in the Aconitum class plant.
Discover that monkshood and diterpene alkaloid thereof have insecticidal effect preferably to the multiple kinds of crops insect.Ethanol, the ether extract of the discovery rhizome of Chinese monkshoods such as Ding Wei have certain preventive effect to mythimna separata.Discovery rhizome of Chinese monkshood methanol extracts such as Du Xiaoying have certain poisoning and repellent activity to red flour beetle, housefly.Yu Dagang has also applied for the rhizome of Chinese monkshood liquid patent of composite herbal medicine agricultural chemicals as one of prescription.Gao Zhanlin finds that the acetone immersion liquid of the northern rhizome of Chinese monkshood (Aconitum kusnezoffii) has higher biological activity to rhopalosiphum padi, spiraea aphid and turnip aphid, all shows notable synergistic to Provado and omethoate.Chen Li etc. discover that the melon leaf rhizome of Chinese monkshood has obvious insecticidal activity to small cabbage moth and oblique mosquito noctuid.Discovery Root of Nakedstamen Monkshood methanol extracts such as Wang Haili are about 72% to the antifeedant activity of Autographa spp.
Diterpene alkaloid is the insecticidal activity position of monkshood.Discovery monkshood steeping fluids such as Ma Jianlie (main component is a diterpene alkaloid) have the better prevention effect to insects such as black peach aphid, cabbage caterpillar, abraxas mirandas.Discovery aconite alkaloids such as Liu Changzhong have toxic action and prevention effect preferably to black peach aphid.Hao Jun is good to be waited by the field efficacy experiment, and the result shows that 0.15% rhizome of Chinese monkshood total alkali all has higher lethality as sterilant to aphid and cabbage caterpillar etc.Jiang Honghua etc. show that to the field control effectiveness test of 800 times of liquid of napelline missible oil (concentration is 1.9ppm) of 0.15% it is suitable to the preventive effect of cabbage caterpillar with 10% chlorine cyanogen chrysanthemum buttermilk, 2000 times of liquid of oil (concentration is 50ppm).Discovery Methyllycaconitines (Methyllycaconitine) such as Jennings KR have stronger insecticidal activity, and it can combine with the cholinocepter of insect is efficient.Discovery diterpene alkaloids such as Ulubelen A have stronger repellent action to insect.Hispanic Reina M and Gonza ' lez-Coloma A etc. have carried out comparatively detailed research aspect the insecticidal activity of natural diterpene alkaloid.They will belong to (Consolida) plant from Aconitum (Aconitum), staggerweed (Delphinium) and Root of Rocket Consolida and separate 23 kinds of diterpene alkaloid (C that obtain
20) and 44 kinds diterpene alkaloid (C falls
19), spodoptera (Spodoptera littoralis) and colorado potato bug (Leptinotarsa decemlineata) are carried out food refusal and cytotoxicity research, the result shows that the diterpene alkaloid of different structure shows different insecticidal activities, C to different insects
19Fall diterpene alkaloid and compare C
20Diterpene alkaloid has stronger activity, wherein to the colorado potato bug antifeedant activity the strongest be diacetylcardiopetaline, 18-hydroxy-14-O-methylgadesine and 14-O-acetyldelectinine, to the spodoptera antifeedant activity the strongest be 19-oxodihydroatisine (EC
50＜0.2 μ g/cm
2), to the cytotoxicity of colorado potato bug the strongest be napelline (aconitine).
In recent years, focus mostly in the research of the insecticidal activity of the natural diterpene alkaloid that biology total alkali runic thing and extraction separation are obtained both at home and abroad for the insecticidal activity research of diterpene alkaloid.Diterpene alkaloid is carried out structural modification (or structure of modification) though research has been carried out for many years, and the activity that all is primarily aimed at its medicinal use is the research point, is that the research of purpose does not appear in the newspapers to change its insecticidal activity.As HuaXi college of pharmacy, SiChuan University Wang Feng roc seminar discovery, structure of modification and the pharmacologically actives such as antitumor and analgesia thereof of diterpene alkaloid have been carried out comparatively deep research.Wherein, Wang Jianli is to N atom, the C of lappaconitine and bulleyaconitine A
8Position and C
14Structural modification has been carried out in the position, has inquired into C
19The chemical reaction method of diterpene alkaloid structural modification and rule.Utilization oxygenant KMnO such as Northwest Normal University high dawn
4Structure to natural diterpene alkaloid talatisamine (talastisamine) is transformed, and has obtained 4 non-natural products such as lactan type, imines type and acidylate type.The king of pharmaceutical chemistry research department of China Medicine University such as refined etc. pays first element derivative to the pass of the plain acidylate modification of pass pair first back discovery its acetylize, propionylization and adjacent chlorobenzoylization has significant protective effect to the rat ventricular that napelline brings out.
Mesaconitine is rhizome of Chinese monkshood type C
19Diterpene alkaloid finds that by the insecticidal activity test it has insecticidal activity to planthopper and aphid.In close relations between its structure, insecticidal activity and the toxicity, the substituting group kind is different with number, the difference of substituting group position etc. can cause that all their insecticidal activity and toxicity change.According to its C
3Position, C
13Position, C
15There are the characteristics of hydroxyl the position, can carry out esterification to it and modify, and changes its insecticidal activity.
Domestic and international research result shows that monkshood and diterpene alkaloid thereof have insecticidal effect preferably to the multiple kinds of crops insect, but the insecticidal activity research of mesaconitine structural modification and modified outcome thereof does not appear in the newspapers.Therefore, the rhizome of Chinese monkshood type diterpene alkaloid in the monkshood is the natural plant active component that an agricultural chemicals lead compound structure innovation and a class of optimizing research got a good chance of, had the symptom of a trend, and the Biocidal agricultural chemicals that can be used as new and effective low toxicity is researched and developed.
(3) summary of the invention:
1, Fa Ming purpose: a kind of synthetic method with mesaconitine esterified derivative of insecticidal activity is provided.
2, technical scheme: realize that the means that the present invention adopts are that mesaconitine is dissolved in pyridine, add esterifying reagent, under ice bath or room temperature condition, react, can synthesize esterified derivative; Perhaps directly react synthetic esterified derivative as solvent with esterifying reagent.
The present invention is dissolved in pyridine with mesaconitine, can generate esterified derivative in 6～30 hours with the reaction of the esterifying reagent of 1～5 times of molar weight.The esterifying reagent that uses has acid anhydrides or acyl chlorides such as diacetyl oxide, propionic anhydride, methane sulfonyl chloride, o-chlorobenzoyl chloride, parachlorobenzoyl chloride, Benzoyl chloride, positive caproyl chloride.Quaternization system pH to 8～10.The extracting process that adopts is all transferred to alkaloid in the little polar solvent, layer.Solvent reclaims with Rotary Evaporators by the mode of underpressure distillation.The product that obtains may be the simplification compound, only need carry out simple purification process, as recrystallization; Product also may be the alkaloid mixture of multiple esterification, should carry out column chromatography for separation to it according to polar difference.All alkaloids utilize wave spectrums such as infrared chromatography, electron impact ionization mass spectrometry, nucleus magnetic resonance to unite and characterize and analyze.
Compound is dissolved in the solvent, and dropping inorganic acid or organic acid can directly obtain its salt.
(4) concrete enforcement:
Embodiment 1:
At normal temperatures, 1:3 takes by weighing mesaconitine in molar ratio: propionic anhydride.Earlier mesaconitine is dissolved in the 0.5ml dry pyridine, adds propionic anhydride again, behind the magnetic agitation 10h, under condition of ice bath, slowly drip saturated sodium carbonate solution and transfer reacting liquid pH value to 9.0,5mL chloroform extraction three times, combined chloroform layer; The chloroform layer water that obtains of extraction is given a baby a bath on the third day after its birth time, saturated sodium-chloride water solution give a baby a bath on the third day after its birth time back with anhydrous sodium sulfate drying 12h after, the evaporated under reduced pressure chloroform.Obtain purer propionyl mesaconitine.
Adopt the insecticidal activity of dip method test mesaconitine derivative: from the small cabbage moth of outdoor collection, select 3 more consistent instar larvaes of build, put into culture dish, 10 in every ware to small cabbage moth.After test compound small amount of acetone, methyl alcohol mixed liquor (1:1) dissolving, be made into the test liquid of 100g/L and 1000g/L respectively with the aqueous solution that contains 0.1% soil temperature-80, the examination worm of picking out is poured in the strainer, immersing soup took out after 5 seconds, being poured on filter paper swashes line number second, to draw unnecessary soup, put into culture dish, raise with fresh Plantula Brassicae chinensis leaf.Examination worm after the processing places under 26 ℃ of constant temperature, observes behind the 24h, touches polypide with dissecting needle, and motionless is dead.
The mesaconitine derivative of propionyl modification in dip method experiment during 100mg/L 3 age small cabbage moth mortality ratio be 30%, during 1000mg/mL 3 age small cabbage moth mortality ratio be 70%; The mortality ratio of aphid is 20% during 500mg/L.
Product records molten point: 118～120 ℃;
Product structure confirms with mass spectrometric detection, EI-MS m/z:688 (M
+).
Nuclear-magnetism detects,
1H-NMR (CDCl
3, 600MHz) δ (ppm): 8.03 (2H, d, J=5.76Hz, Ar-H), 7.57 (1H, dd, J
1=7.14Hz, J
2=14.64Hz, Ar-H), 7.45 (2H, dd, J
1=7.92Hz, J
2=15.6Hz, Ar-H), 4.90 (2H, ddd, J
1=5.40, J
2=13.14Hz, J
3=26.82Hz H-14), 4.47 (2H, dd, J
1=2.88Hz, J
2=5.22Hz, 15-H β), 4.34 (1H, d, J=2.88Hz, OH-15 α), 4.08 (1H, d, J=7.14Hz, H-6), 3.88 (1H, s, OH-13 β), 3.79 (1H, d, J=8.88Hz, H-3), 3.27 (3H, s, OCH
3), 3.20 (3H, s, OCH
3), 3.19 (3H, s, OCH
3), 3.13 (1H, dd, J
1=6.90Hz, J
2=10.80Hz, H-1), 3.09 (1H, s, H-17), 2.36 (3H, s, N-CH
3), 1.40 (3H, s, OAc), 1.16 (3H, t, J=7.50Hz, O=CCH
2 CH 3 ).
Embodiment 2:
Take by weighing mesaconitine 101.8mg at normal temperatures, be dissolved among the pyridine 5ml, ice bath adds parachlorobenzoyl chloride 0.5ml down, reaction 14h is 9.6 with saturated sodium carbonate alkalinisation treatment reaction solution up to reacting liquid pH value under the condition of ice bath, and chloroform 3 * 6mL extracts, the combined chloroform layer, and with distinguishing water and saturated sodium-chloride washing chloroform layer, behind the anhydrous sodium sulfate drying 12h, chloroform is reclaimed in underpressure distillation.Obtain crude product 126.8mg; silica gel 5g column chromatography V (chloroform): V (methyl alcohol)=20:1; add 1% triethylamine in the eluent and obtain product 68.1mg, the mesaconitine esterification modified derivative of 13,15 hydroxyls of acetylize again behind 3 hydroxyls of propionylization of yield 46.5% white powder dress.
Take by weighing the former medicine of certain mass with analytical balance (0.0001g), add the solvent (DMF) that contains 0.1% tween 1, be mixed with 5% preparation.Take by weighing the preparation of certain mass, adding distil water (topical application dilution acetone) dilution is mixed with the soup of measuring desired concn.Estimate SOP (sterilant volume) according to the initiative pesticide bioactivity, general sieve concentration is selected 500mg/L.
Adopting the quantitative spray method of culture dish seedling worm to measure compound screens the paddy rice brown paddy plant hopper: the paddy rice seedling is fixed in the culture dish with white quartz sand, connects and use CO
2Anaesthetize 3 mid-term in age nymph, place under the POTTER spray tower spraying.The spraying back covers with the transparent plastics cup, is put in the observation ward behind the mark.Check result behind the 72h.To the mesaconitine derivative of chlorobenzoyl modification when the 500mg/L 3 age planthopper better cytotoxicity is arranged.
If adopt pickling process to measure the insecticidal activity of compound to aphis craccivora: the broad bean blade is cut off two ends, and the back side is placed on the fritter cotton up, places in the plastic culture dish, adds less water, connects aphis craccivora and becomes aphid to produce aphid.Remove into aphid behind the 24h, continue behind the cultivation 2d blade behind the abundant 5s of infiltration, to be placed on the cotton natural airing again in soup.Check result behind the 24h.To the mesaconitine derivative of chlorobenzoyl modification in the quantitative spray method experiment of culture dish seedling worm during 500mg/L the aphis craccivora mortality ratio in 3 ages be 30%.
Product records molten point: 93-96 ℃;
Product structure confirms with mass spectrometric detection, EI-MS m/z:908M
+);
Nuclear-magnetism detects,
1H-NMR (CDCl
3, 600MHz) δ (ppm): 8.09 (2H, d, J=7.38Hz), 7.98 (2H, d, J=8.64Hz, Ar-H), 7.93 (2H, d, J=8.64Hz, Ar-H), 7.59 (1H, dd, J
1=7.80Hz, J
2=14.82Hz, Ar-H), 7.47 (2H, dd, J
1=7.80Hz, J
2=15.42Hz, Ar-H), 7.43 (2H, d, J=8.64Hz, Ar-H), 7.34 (4H, m, Ar-H), 4.58 (1H, dd, J
1=2.76Hz, J
2=5.16Hz, 15-H β), 4.34 (1H, d, J=2.82Hz, OH-15 α), 4.14 (1H, d, J=6.84Hz, H-6), 3.87 (1H, d, J=9.00Hz, H-3), 3.52 (3H, s, OCH
3), 3.28 (3H, s, OCH
3), 3.25 (1H, s), 3.23 (3H, s, OCH
3), 3.12 (3H, s, OCH
3), 3.02 (1H, d, J=8.82Hz), 2.95 (2H, s), 2.43 (3H, sN-CH3), 2.38 (1H, d, J=6.78Hz), 1.45 (3H, s, OAc).
Embodiment 3:
At normal temperatures, take by weighing mesaconitine 92.4mg, be dissolved in the dry pyridine, dripping positive caproyl chloride 0.3mL reaction 15h under the condition of ice bath, is 9.0 with saturated sodium carbonate alkalinisation treatment reaction solution up to reacting liquid pH value under the condition of ice bath, and chloroform 3 * 6ml extracts, the combined chloroform layer, and water, saturated sodium-chloride water solution are washed chloroform layer respectively, and behind the anhydrous sodium sulfate drying 12h, chloroform is reclaimed in underpressure distillation.Obtain crude product 103.2mg, cross post (V (sherwood oil): V (and ethyl acetate=95:5) product 63.2mg, the positive hexanoyl derivative of white powder mesaconitine.Yield 59.2%
If adopt pickling process to measure the insecticidal activity of compound to aphis craccivora: the broad bean blade is cut off two ends, and the back side is placed on the fritter cotton up, places in the plastic culture dish, adds less water, connects aphis craccivora and becomes aphid to produce aphid.Remove into aphid behind the 24h, continue behind the cultivation 2d blade behind the abundant 5s of infiltration, to be placed on the cotton natural airing again in soup.Check result behind the 24h.The mesaconitine derivative of positive hexanoyl modification when 500mg/L 3 age planthopper cytotoxicity is preferably arranged.
Product records molten point: 76-78 ℃.
Product structure confirms with mass spectrometric detection, EI-MS m/z:730 (M
+)
Nuclear-magnetism detects,
1H-NMR (CDCl
3, 600MHz) δ (ppm): 8.03 (2H, d, J=7.20Hz, Ar-H), 7.57 (1H, dd, J
1=7.29Hz, J
2=14.58Hz, Ar-H), 7.45 (2H, t, J=7.80Hz, Ar-H), 4.90 (2H, ddd, J
1=4.98Hz, J
2=12.18Hz, J
3=23.22Hz, 14-H β),, 4.47 (1H, dd, J
1=2.82Hz, J
2=4.98Hz, H-15 β), 4.35 (1H, d, J=2.82Hz, OH-15 α), 4.07 (1H, d, J=7.20Hz), 3.88 (1H, s, OH-13 β),, 3.79 (1H, d, J=8.82Hz), 3.73 (3H, s, OCH
3), 3.31 (1H, d, J=5.22Hz), 3.27 (3H, s, OCH
3), 3.20 (6H, d, J=4.80Hz, 2 * OCH
3), 3.13 (1H, dd, J
1=6.78Hz, J
2=10.8Hz), 3.09 (1H, s), 2.94 (3H, m), 2.89 (1H, s), 2.64 (1H, d, J=11.20Hz), 2.42 (1H, m), 2.36 (3H, s, N-CH
3), 1.40 (3H, s, OAc), 1.66-1.26 (8H, m, O=C
(CH 2 ) 4 CH
3), 0.90 (3H, dd, J
1=7.02Hz, J
2=13.80Hz, O=C (CH
2)
4 CH 3 ).
Embodiment 4:
The 100mg mesaconitine is dissolved in the dry pyridine solution of 2mL, adds methane sulfonyl chloride 0.05mL, room temperature reaction under the normal pressure, the thin-layer chromatography monitoring reacted completely in about 20 hours.Reaction solution is poured in the 3mL frozen water, after ammoniacal liquor adjusting pH value is 9.2, used chloroform extraction 3 times, (5mL/ time), the extraction liquid anhydrous sodium sulfate drying, underpressure distillation obtains white solid 122mg, and productive rate is about 100%.
If adopt pickling process to measure the insecticidal activity of compound to aphis craccivora: the broad bean blade is cut off two ends, and the back side is placed on the fritter cotton up, places in the plastic culture dish, adds less water, connects aphis craccivora and becomes aphid to produce aphid.Remove into aphid behind the 24h, continue behind the cultivation 2d blade behind the abundant 5s of infiltration, to be placed on the cotton natural airing again in soup.Check result behind the 24h.The mesaconitine derivative of positive hexanoyl modification when 500mg/L to 3 age planthopper higher cytotoxicity is arranged.
Product structure confirms with mass spectrometric detection, EI-MS m/z:788.3 (M
+)
Nuclear-magnetism detects,
1H-NMR (CDCl
3, 600MHz) δ (ppm): 8.06-7.46 (5H, m, Ar-H), 5.23 (1H, d, J=5.2, H-14 β), 4.75 (1H, DD, J
1=12.8, J
2=6.7,3-H), 4.51 (1H, dd, J
1=7.7, J
2=1.8, H-15 β), 4.26 (1H, d, J=2.94, OH-15 α), 3.71,3.31,3.27,3.20 (each 3H, s, 3 * OCH
3), 3.10,3.02 (each 3H, s, 2 * SO
2-CH
3), 2.33 (3H, s, N-CH
3), 1.37 (3H, s, OAc).
Embodiment 5:
Mesaconitine 100mg is dissolved in the pyridine, and dripping hydrochloric acid obtains the hydrochloride 92mg of mesaconitine.Ethyl acetate extraction and recrystallization obtain the hydrochloride white needle-like crystals.Fusing point 176-178 ℃.
Adopting the quantitative spray method of culture dish seedling worm to measure compound screens the paddy rice brown paddy plant hopper: the paddy rice seedling is fixed in the culture dish with white quartz sand, connects and use CO
2Anaesthetize 3 mid-term in age nymph, place under the POTTER spray tower spraying.The spraying back covers with the transparent plastics cup, is put in the observation ward behind the mark.Check result behind the 72h.To the mesaconitine derivative of chlorobenzoyl modification when the 500mg/L 3 age planthopper higher cytotoxicity is arranged.
Embodiment 6:
Mesaconitine 100mg is dissolved in the pyridine, drips Hydrogen bromide, obtain the bromate 85mg of mesaconitine.Ethyl acetate extraction and recrystallization obtain the bromate white needle-like crystals.Fusing point 172-173 ℃
Adopting the quantitative spray method of culture dish seedling worm to measure compound screens the paddy rice brown paddy plant hopper: the paddy rice seedling is fixed in the culture dish with white quartz sand, connects and use CO
2Anaesthetize 3 mid-term in age nymph, place under the POTTER spray tower spraying.The spraying back covers with the transparent plastics cup, is put in the observation ward behind the mark.Check result behind the 72h.To the mesaconitine derivative of chlorobenzoyl modification when the 500mg/L 3 age planthopper higher cytotoxicity is arranged.
Claims (5)
1, mesaconitine esterified derivative and salt thereof are compound and the salt thereof with following general formula.
R in the formula
1For ethanoyl, propionyl, benzoyl, positive caproyl, methane sulfonyl, to alkyloyls such as chlorobenzene formacyl, fatty acyl group, alkylsulfonyl or aromaticacyl radical; R
2For hydrogen atom or ethanoyl, propionyl, benzoyl, positive caproyl, methane sulfonyl, to alkyloyls such as chlorobenzene formacyl, fatty acyl group, alkylsulfonyl or aromaticacyl radical; R
3For hydrogen atom or ethanoyl, propionyl, benzoyl, positive caproyl, methane sulfonyl, to alkyloyls such as chlorobenzene formacyl, fatty acyl group, alkylsulfonyl or aromaticacyl radical.
2, the synthetic method of mesaconitine esterified derivative as claimed in claim 1 is characterized in that the esterifying reagent of mesaconitine and mol ratio 1:1～1:5 is reacted 6～30 hours alkaloidal esterified derivatives of synthetic napelline type in the pyridine of room temperature or ice bath.Perhaps directly make solvent, add tosic acid and carry out esterification modification building-up reactions as catalyzer with esterifying reagent.With saturated aqueous sodium carbonate quaternization liquid to pH value is 8～10, after alkaloid is transferred in the chloroform, chloroform is recycled in the mode of underpressure distillation.Obtain single creature alkali esterified derivative or alkaloid mixture.The mixture that obtains is purified by methods such as recrystallization or silica gel column chromatographies again.
3, the esterified derivative synthetic method of mesaconitine as claimed in claim 2 is characterized in that described esterifying reagent is acid anhydrides or acyl chlorides such as diacetyl oxide, propionic anhydride, o-chlorobenzoyl chloride, parachlorobenzoyl chloride, Benzoyl chloride, positive caproyl chloride.As being only applicable to acid anhydrides as esterifying reagent of solvent, and esterification is simultaneously modified 2 above hydroxyls or same alkaloid is carried out the situation that two or more esterifications are modified with esterifying reagent.
4, the synthetic method of the salt of the esterified derivative of mesaconitine as claimed in claim 1 is characterized in that the mesaconitine esterified derivative of acquisition as described in right 2 or 3 is dissolved in the solvent, and dropping inorganic acid or organic acid can directly obtain the salt of its compound.
5, as the application of claims 1 described mesaconitine esterification modified derivative and salt thereof, it is characterized in that using as insecticidal materials.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102047885A (en) * | 2010-10-20 | 2011-05-11 | 华南理工大学 | Aconitine plant source pesticide water dispersible granules and preparing method thereof |
| CN102977019A (en) * | 2011-09-06 | 2013-03-20 | 高峰 | New C19 diterpenoid alkaloid in Aconitum hemsleyanum var. janyuanum and applications thereof in preparation of anticancer drugs |
| CN103749456A (en) * | 2013-12-25 | 2014-04-30 | 贵州大学 | Application of diterpene alkaloid compound and preparation to prevention of crop virus diseases |
| CN104098511A (en) * | 2013-04-15 | 2014-10-15 | 长沙富能生物技术有限公司 | New technology for utilizing structure modification method for half synthesis of lappaconitine |
-
2008
- 2008-12-24 CN CN 200810147987 patent/CN101434578A/en active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102047885A (en) * | 2010-10-20 | 2011-05-11 | 华南理工大学 | Aconitine plant source pesticide water dispersible granules and preparing method thereof |
| CN102977019A (en) * | 2011-09-06 | 2013-03-20 | 高峰 | New C19 diterpenoid alkaloid in Aconitum hemsleyanum var. janyuanum and applications thereof in preparation of anticancer drugs |
| CN104098511A (en) * | 2013-04-15 | 2014-10-15 | 长沙富能生物技术有限公司 | New technology for utilizing structure modification method for half synthesis of lappaconitine |
| CN103749456A (en) * | 2013-12-25 | 2014-04-30 | 贵州大学 | Application of diterpene alkaloid compound and preparation to prevention of crop virus diseases |
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