CN1328264C - EBF analogues containing oxadiazine and preparation method and application thereof - Google Patents
EBF analogues containing oxadiazine and preparation method and application thereof Download PDFInfo
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- CN1328264C CN1328264C CNB2004100984914A CN200410098491A CN1328264C CN 1328264 C CN1328264 C CN 1328264C CN B2004100984914 A CNB2004100984914 A CN B2004100984914A CN 200410098491 A CN200410098491 A CN 200410098491A CN 1328264 C CN1328264 C CN 1328264C
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Abstract
The present invention discloses an EBF analogue which contains oxadiazine and a preparation method and application thereof. The EBF analogue which contains oxadiazine, which is provided by the present invention, has the structural formula I, wherein R1 stands for hydrogen, C1 to C10 alkyl, C5 to C6 cycloalkyl, alkylogen, phenyl, 3, 7-dimethyl-2, 6-octadiene, halogeno benzene, nitrophenyl, halonitrobenzene, pyridyl, halopyridine, halopyridine methylene, halogenating thiazole methylene, or-COR2, and R2 stands for C1 to C10 alkyl, C5 to C6 cycloalkyl, phenyl, halogeno benzene, alkylphenyl, alkoxy phenyl, nitrophenyl, halonitrobenzene, pyridyl, halopyridine or halogenating thiazolyl. The compound of the present invention has the good chemical ability for killing aphids. Compared with EBF, the molecular weight is large, and the stability is high. The compound of the present invention can be widely used in agricultural production.
Description
Technical field
The present invention relates to contain [instead]-β-farnesene analogue of oxadiazine ring and preparation method thereof, and the application of this compound in the anti-medicine that eliminates aphis of preparation.
Background technology
Aphid is that a worldwide class is of a great variety, and the Agricultural pests that distributed pole is wide are spreaded all over all parts of the country.It not only directly influences growth and development of plant, causes the decline of yield and quality, the more important thing is that it still is the communication media of multiple virus, and at present known have at least 159 kinds of aphids can pass the band plant virus, occupies first of world's infection insect.For the Prevention Technique of aphid, Chinese scholars has all been done number of research projects, and particularly the reinforcement of people's environmental consciousness in recent years reaches the pay attention to day by day to crop safety, makes the Study of Prevention Technology of aphid enter a new period.The advantage that though biological control has is environmentally friendly, be beneficial to benign ecological cycles, but it is just powerless when running into the insect pest wildness, therefore developing a class has low consumption, efficiently reaches specific optionally compound, simultaneously have the constructional feature of biological source insecticide again, will have good application and development prospect in future.
[instead]-β-farnesene (E-β-farnesene is called for short EBF) is the main component of most of aphid alarm pheromoneses, and the escape that can scatter when aphid smells its smell stops the infringement to farm crop.Because EBF does not have aphid activity extremely, and molecular weight is less, has conjugated double bond, volatile and oxidized under field condition, poor stability is unfavorable for its effective application in agriculture production.
Existing [instead]-β-farnesene analogue is disclosed in the following document: (Structure-activity relationships of analogs of the aphid alarm pheromone such as Bowers in 1977, (E)-β-farnesene J.Insect.Physiol.1977,23:697-701), (Somefluorine-containing pheromone analogues Pestic.Sci.1986 such as Briggs in 1986,17:441-448), (the chemical journal 1987 of insect pheromone research (intending the plain research of aphid warning) such as Li Zhengming in 1987,45 (11): 1124-1128), (the aphid alarm pheromones analogue insect journals 1988 of several biologically actives such as Zhang Zhongning in 1988,31 (4): 435-438), (Structure-activity studies on aphid alarmpheromone derivatives and their fields ude against transmission of BarleyYellow Dwarf Virus.Pestic.Sci. such as Dawson, 1988,22; 17-30); nineteen ninety-five yellow rose-tinted clouds etc. (aphid is guarded against the synthetic applied chemistry 1995 of plain analogue; 12 (3): 82-84) and Yang Xin's tinkling of pieces of jade in 2004 etc. (design of [instead]-β-farnesene analogue, synthesize and bioactivity research SCI 2004; 25 (9): 1657～1661), these documents have all related to the preparation of aphid alarm pheromones [instead]-β-farnesene analogue.
Summary of the invention
The purpose of this invention is to provide [instead]-β-farnesene analogue of a kind of novel De Han oxadiazine ring and preparation method thereof.
[instead] provided by the present invention-β-farnesene analogue, its structural formula are formula I,
Wherein, R
1Be that hydrogen, carbon atom are the alkyl of 1-10, cycloalkyl, haloalkyl, the phenyl, 3 that carbon atom is 5-6,7-dimethyl-2,6-octadienyl, halogenophenyl, nitrophenyl, halogenated nitrobenzene, pyridyl, halogenated pyridyl, haloperidid methylene radical, halo thiazole methylene radical or-COR
2, wherein, R
2Be that carbon atom is the alkyl of 1-10, cycloalkyl, phenyl, halogenophenyl, alkyl phenyl, alkoxyl phenyl, nitrophenyl, halogenated nitrobenzene, pyridyl, halogenated pyridyl or the halo thiazolyl that carbon atom is 5-6.
Wherein, haloperidid methylene radical chloro-pyridine methylene radical preferably; Work as R
1Be-COR
2The time, R
2Methyl, ethyl, propyl group, sec.-propyl, butyl, the tertiary butyl, cyclohexyl, phenyl, halogenophenyl, alkyl phenyl, nitrophenyl, chloronitrobenzene, pyridyl, halogenated pyridyl or halo thiazolyl etc. specifically.
Compound provided by the present invention can be prepared according to following several method:
First method: the R in compound of Formula I
1Be that hydrogen, carbon atom are the alkyl of 1-10, cycloalkyl, haloalkyl, the phenyl, 3 that carbon atom is 5-6,7-dimethyl-2, when 6-octadienyl, halogenophenyl, nitrophenyl, halogenated nitrobenzene, pyridyl or halogenated pyridyl, can be in the presence of alkaline matter, in anhydrous organic solvent by 1-chloro-3,7-dimethyl-2,6-octadiene and formula II compound carry out condensation reaction, obtain described compound.
Reaction equation is:
Wherein, formula II compound can pass through document (Pest Management Science[J], 2001,57:165-176) method of Jie Shaoing is prepared.
Second method: the R in compound of Formula I
1During for the haloperidid methylene radical, can adopt the method preparation that comprises the steps: 1) in the presence of alkaline matter, in anhydrous organic solvent by 1-chloro-3,7-dimethyl-2,6-octadiene and 4-nitro imino--1,3,5 oxadiazines carry out condensation reaction, obtain 3-(3,7-dimethyl-2, the 6-octadiene)-and 4-nitro imino--1,3,5 oxadiazines; 2) by 3-(3,7-dimethyl-2,6-octadiene)-4-nitro imino--1,3,5 oxadiazines and 3-chloromethyl-6-chloro-pyridine carries out condensation reaction and obtains described compound in organic solvent in the presence of alkaline matter.
Reaction equation is:
The third method: the R in compound of Formula I
1For-COR
2, wherein, R
2Be that carbon atom is when being the alkyl of 1-10, cycloalkyl that carbon atom is 5-6, phenyl, halogenophenyl, alkyl phenyl, alkoxyl phenyl, nitrophenyl, halogenated nitrobenzene, pyridyl, halogenated pyridyl or halo thiazolyl, can be in the presence of alkaline matter, in anhydrous organic solvent by 1-chloro-3,7-dimethyl-2,6-octadiene and formula III compound carry out condensation reaction, obtain described compound.
Reaction equation is:
Wherein, the formula III compound can be prepared by the method that WO9806710 introduces.
The 4th kind of method: the R in compound of Formula I
1For-COR
2, wherein, R
2Be that carbon atom is when being the alkyl of 1-10, cycloalkyl that carbon atom is 5-6, phenyl, halogenophenyl, alkyl phenyl, alkoxyl phenyl, nitrophenyl, halogenated nitrobenzene, pyridyl, halogenated pyridyl or halo thiazolyl, can adopt the method preparation that comprises the steps: 1) in the presence of alkaline matter, in anhydrous organic solvent by 1-chloro-3,7-dimethyl-2,6-octadiene and 4-nitro imino--1,3,5 oxadiazines carry out condensation reaction, obtain 3-(3,7-dimethyl-2, the 6-octadiene)-and 4-nitro imino--1,3,5 oxadiazines; 2) by 3-(3,7-dimethyl-2,6-octadiene)-4-nitro imino--1,3,5 oxadiazines and formula IV compound carry out condensation reaction and obtain described compound in organic solvent in the presence of alkaline matter.
Reaction equation:
In these preparation methods, used organic solvent comprises hydrocarbon or its halogenated product of aliphatics, alicyclic or aromatics, such as, benzene,toluene,xylene, chlorobenzene, dichlorobenzene, sherwood oil, hexane, hexanaphthene, methylene dichloride, chloroform, tetracol phenixin etc.; Ethers is as ether, diisopropyl ether, tetrahydrofuran (THF) or glycol dimethyl ether or ethylene glycol diethyl ether etc.; Ketone is as acetone, butanone or mibk etc.; Nitrile is as acetonitrile, propionitrile or butyronitrile etc.; Amides, as N, dinethylformamide, N,N-dimethylacetamide, N-methyl-formylaniline, N-Methyl pyrrolidone or HMPA etc.; The ester class is as methyl acetate or ethyl acetate etc.; The sulfoxide class is as dimethyl sulfoxide (DMSO); Alcohols, as methyl alcohol, ethanol, just-or Virahol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether etc.Preferred solvent is toluene, benzene, second eyeball, sherwood oil, N, dinethylformamide.
Described alkaline matter is an organic or inorganic alkali, is preferably salt of wormwood, pyridine, triethylamine, yellow soda ash, sodium methylate, sodium hydride etc.Described organic solvent is toluene, benzene, DMF, acetonitrile or sherwood oil, is preferably toluene, acetonitrile or DMF.
Setting-up point can carry out in wide relatively scope, and usually, reaction is at-10 ℃ to 120 ℃, preferably carries out under the temperature between 30 ℃ to 100 ℃.
The purification process of compound of the present invention is fairly simple, after reaction finishes, adopts conventional column chromatography method to separate and gets final product.
It is the control of aphids agent of activeconstituents that another object of the present invention provides with the The compounds of this invention.
The inventor confirms that by experiment The compounds of this invention has excellent chemical killing aphis activity, and aphid is had direct chemical prevention effect, can be prepared as the control of aphids agent.
In needs, can also add acceptable carrier in one or more pesticide preparation in the control of aphids agent, described carrier comprises thinner conventional in the pesticide preparation, vehicle, weighting agent, tackiness agent, wetting agent, absorption enhancer, tensio-active agent, lubricant, stablizer etc.The formulation of the control of aphids agent of making also is various, can be pulvis, emulsion etc.
Compound of the present invention is on the active skeleton structure of the warning that keeps aphid alarm pheromones [instead]-β-farnesene basis, introducing has the nitrogen heterocyclic ring active structure that fine chemistry kills the aphid effect, the gained compound has good chemistry to aphid and kills activity, and compare with EBF, molecular weight is big, good stability can be used widely in agriculture production.
Embodiment
Embodiment 1, preparation compound 3-(3,7-dimethyl-2,6-octadiene)-4-nitro-imine base-5-methyl isophthalic acid, 3,5 oxadiazines (compound 1201)
In the there-necked flask of 100mL, drop into 5g 3-methyl-4-nitro-imine base-1,3,5 oxadiazines, 1.5g salt of wormwood and 50mL acetonitrile stir, and contain 5.3g 1-chloro-3,7-dimethyl-2 to wherein dripping, the 7mL acetonitrile solution of 6-octadiene dropwises, in 40 ℃ of reaction 5h.Reaction solution is cooled to room temperature, filters, with acetonitrile washing solid, filtrate is sloughed solvent after merging, and separates (ethyl acetate: sherwood oil=1: 10, v/v, wash-out) through silica gel column chromatography then and gets white solid 7.2g, productive rate 80.3%.
Embodiment 2, preparation compound 3-(3,7-dimethyl-2,6-octadiene)-4-nitro-imine base-5-ethyl-1,3,5 oxadiazines (compound 1202)
The preparation method is with embodiment 1, and its difference is: with 3-ethyl-4-nitro-imine base-1,3,5 oxadiazines are reaction raw materials, and solvent for use is an acetonitrile, and used alkaline matter is a salt of wormwood, and temperature of reaction is 40 ℃, and the reaction times is 8h.
The purge process of reaction after product is identical with embodiment 1, obtains product 6.2g, and productive rate is 75%
Embodiment 3, preparation compound 3-(3,7-dimethyl-2,6-octadiene)-4-nitro-imine base-5-sec.-propyl-1,3,5 oxadiazines (compound 1203)
The preparation method is with embodiment 1, and its difference is: with 3-sec.-propyl-4-nitro-imine base-1,3,5 oxadiazines are reaction raw materials, and solvent for use is an acetonitrile, and used alkaline matter is a salt of wormwood, and temperature of reaction is 40 ℃, and the reaction times is 6h.
The purge process of reaction after product is identical with embodiment 1, obtains product 7.8g, and productive rate is 70.0%.
Embodiment 4, preparation compound 3-(3,7-dimethyl-2,6-octadiene)-4-nitro-imine base-5-n-propyl-1,3,5 oxadiazines (compound 1204)
The preparation method is with embodiment 1, and its difference is: with 3-n-propyl-4-nitro-imine base-1,3,5 oxadiazines are reaction raw materials, and solvent for use is an acetonitrile, and used alkaline matter is a triethylamine, and temperature of reaction is 60 ℃, and the reaction times is 8h.
The purge process of reaction after product is identical with embodiment 1, obtains product 7.2g, and productive rate is 74%.
Embodiment 5, preparation compound 3-(3,7-dimethyl-2,6-octadiene)-4-nitro-imine base-1,3,5 oxadiazines (compound 1205)
In the there-necked flask of 100mL, drop into 5g 4-nitro-imine base-1,3,5 oxadiazines, 1.5g yellow soda ash and 50ml toluene stir, and are warming up to 80 ℃, contain 5.5g 1-chloro-3 to wherein dripping, 7-dimethyl-2, the 7mL toluene solution of 6-octadiene dropwises insulation reaction 4h.Reaction solution is cooled to room temperature, filters, with the toluene wash solid, filtrate is sloughed solvent after merging, and separates (ethyl acetate: sherwood oil=1: 5, v/v, wash-out) through silica gel column chromatography then and gets yellow thick liquid 4.8g, productive rate 55.0%.
The purge process of reaction after product is identical with embodiment 1, obtains product 6.2g, and productive rate is 75%.
Embodiment 6, preparation compound 3-(3,7-dimethyl-2,6-octadiene)-4-nitro-imine base-5-(6-chloro-3-pyridylmethyl) 1,3,5 oxadiazines (1206)
In the there-necked flask of 50mL, drop into embodiment 2 gained compound 3-(3,7-dimethyl-2, the 6-octadiene)-4-nitro-imine base-1,3,5 oxadiazine 3.0g, 1.5mL triethylamine and 10mL DMF (N, dinethylformamide), stirring at room, drip 2.0g3-chloromethyl-6-chloro-pyridine, dropwise the back in 60 ℃ of reaction 8h.In reaction solution impouring frozen water, use the 30ml chloroform extraction then, the chloroform solution that anhydrous sodium sulfate drying obtains, precipitation gets the 2.0g crude product then.Separate (ethyl acetate: sherwood oil=1: 8, v/v, wash-out) through silica gel column chromatography and get 1.8g pale yellow oily liquid body, productive rate 44.0%.
Embodiment 7, preparation compound 3-(3,7-dimethyl-2,6-octadiene)-4-nitro-imine base-5-ethanoyl-1,3,5 oxadiazines (1207)
Method one:
In the there-necked flask of 50mL, drop into embodiment 2 gained compound 3-(3,7-dimethyl-2,6-octadiene)-4-nitro-imine base-1,3,5 oxadiazine 2.9g, 1.5mL triethylamine and 10ml DMF, stirring at room drips the 1.0g Acetyl Chloride 98Min., dropwises the back in 50 ℃ of reaction 10h.In reaction solution impouring frozen water, use the 30ml chloroform extraction then, the chloroform solution that anhydrous sodium sulfate drying obtains, precipitation gets the 2.5g crude product then.Separate (ethyl acetate: sherwood oil=1: 8, v/v, wash-out) through silica gel column chromatography and get 1.3g pale yellow oily liquid body, productive rate 42.3%.
Method two:
In the there-necked flask of 100mL, drop into 5.4g 3-ethanoyl-4-nitro-imine base-1,3,5 oxadiazines; 1.5g sodium methylate and 50mL toluene stir, and contain 5.3g 1-chloro-3,7-dimethyl-2 to wherein dripping; the 7mL toluene solution of 6-octadiene dropwises, in 90 ℃ of reaction 4h.Reaction solution is cooled to room temperature, filters, with the toluene wash solid, filtrate is sloughed solvent after merging, and separates (ethyl acetate: sherwood oil=1: 8, v/v, wash-out) through silica gel column chromatography then and gets weak yellow liquid 3.86g, productive rate 40.3%.
The physico-chemical property of table 1. part of compounds and H
1-NMR data
The killing aphis activity of embodiment 8, The compounds of this invention
Former medicine of positive control medicament Provado and embodiment 1-7 gained compound sample are mixed with 4 concentration to be measured with acetone respectively, the hand-held micro-dropper that with the drop amount is 0.0307 μ l drips to the turnip aphid back with the soup point, each concentration is handled 20 of aphids, makes blank with the acetone drop.Aphid after the processing gently moves in the synthetic glass test box (diameter 5cm, high 1cm) with fresh clean rape leave with writing brush, adds preservative film, adds a cover, and tightens with bungee, preserves under 22 ℃ of room temperatures, reexamines death toll after 48 hours.Test-results sees Table 2.The result shows that compound of the present invention has significant lethal effect to aphid.
The killing aphis activity test result of The compounds of this invention under table 2. different concns
| Numbering | The mortality ratio of aphid (%) under the different concns | |||
| 1000mg/L | 500mg/L | 250mg/L | 125mg/L | |
| Blank | 16.7 | |||
| Positive control | 90.3 | 78.4 | 70.8 | 63.1 |
| 1201 | 60.3 | 55.0 | 50.1 | 41.7 |
| 1202 | 91.6 | 80.0 | 77.9 | 55.1 |
| 1203 | 91.4 | 83.3 | 71.4 | 66.7 |
| 1204 | 59.8 | 50.0 | 46.7 | 33.3 |
| 1205 | 57.7 | 39.7 | 35.7 | 23.2 |
| 1206 | 65.7 | 62.5 | 60.8 | 44.8 |
| 1207 | 59.0 | 39.7 | 35.7 | 41.3 |
Claims (23)
1, structural formula is the compound of formula I,
Wherein, R
1Be that hydrogen, carbon atom are the alkyl of 1-10, cycloalkyl, haloalkyl, the phenyl, 3 that carbon atom is 5-6,7-dimethyl-2,6-octadienyl, halogenophenyl, nitrophenyl, halogenated nitrobenzene, pyridyl, halogenated pyridyl, haloperidid methylene radical, halo thiazole methylene radical or-COR
2, wherein, R
2Be that carbon atom is the alkyl of 1-10, cycloalkyl, phenyl, halogenophenyl, alkyl phenyl, alkoxyl phenyl, nitrophenyl, halogenated nitrobenzene, pyridyl, halogenated pyridyl or the halo thiazolyl that carbon atom is 5-6.
2, compound according to claim 1 is characterized in that: described R
1Be carbon atom be the alkyl of 1-10, cycloalkyl that carbon atom is 5-6, haloalkyl, phenyl, halogenophenyl, nitrophenyl, halogenated nitrobenzene, pyridyl, halogenated pyridyl, chloro-pyridine methylene radical, halo thiazole methylene radical or-COR
2, wherein, R
2Be methyl, ethyl, propyl group, sec.-propyl, butyl, the tertiary butyl, cyclohexyl, phenyl, halogenophenyl, alkyl phenyl, nitrophenyl, chloronitrobenzene, pyridyl, halogenated pyridyl or halo thiazolyl.
3, work as R in the preparation claim 1
1Be that hydrogen, carbon atom are the alkyl of 1-10, cycloalkyl, haloalkyl, the phenyl, 3 that carbon atom is 5-6,7-dimethyl-2, the method of 6-octadienyl, halogenophenyl, nitrophenyl, halogenated nitrobenzene, pyridyl or halogenated pyridyl up-to-date style I compound, be in the presence of alkaline matter, in anhydrous organic solvent by 1-chloro-3,7-dimethyl-2,6-octadiene and formula II compound carry out condensation reaction, obtain described compound
4, method according to claim 3 is characterized in that: described alkaline matter is selected from salt of wormwood, pyridine, triethylamine, yellow soda ash, sodium methylate or sodium hydride; Described organic solvent is toluene, benzene, DMF, acetonitrile or sherwood oil.
5, method according to claim 4 is characterized in that: described organic solvent is toluene, DMF or acetonitrile.
6, according to claim 3 or 4 or 5 described methods, it is characterized in that: the temperature of described condensation reaction is-10 ℃-120 ℃.
7, method according to claim 6 is characterized in that: the temperature of described condensation reaction is 30 ℃-100 ℃.
8, prepare in the claim 1 when R1 be the method for haloperidid methylene radical up-to-date style I compound, comprise the steps: 1) in the presence of alkaline matter, in anhydrous organic solvent by 1-chloro-3,7-dimethyl-2,6-octadiene and 4-nitro imino--1,3,5 oxadiazines carry out condensation reaction, obtain 3-(3,7-dimethyl-2, the 6-octadiene)-and 4-nitro imino--1,3,5 oxadiazines; 2) by 3-(3,7-dimethyl-2,6-octadiene)-4-nitro imino--1,3,5 oxadiazines and 3-chloromethyl-6-chloro-pyridine carries out condensation reaction and obtains described compound in organic solvent in the presence of alkaline matter.
9, method according to claim 8 is characterized in that: described alkaline matter is selected from salt of wormwood, pyridine, triethylamine, yellow soda ash, sodium methylate or sodium hydride; Described organic solvent is toluene, benzene, DMF, acetonitrile or sherwood oil.
10, method according to claim 9 is characterized in that: described organic solvent is toluene, acetonitrile or DMF.
11, according to Claim 8 or 9 or 10 described methods, it is characterized in that: the temperature of described condensation reaction is-10 ℃-120 ℃.
12, method according to claim 11 is characterized in that: the temperature of described condensation reaction is 30 ℃-100 ℃.
13, work as R in the preparation claim 1
1For-COR
2, wherein, R
2Be that carbon atom is the alkyl of 1-10, the method for cycloalkyl, phenyl, halogenophenyl, alkyl phenyl, alkoxyl phenyl, nitrophenyl, halogenated nitrobenzene, pyridyl, halogenated pyridyl or halo thiazolyl up-to-date style I compound that carbon atom is 5-6, be in the presence of alkaline matter, in anhydrous organic solvent by 1-chloro-3,7-dimethyl-2,6-octadiene and formula III compound carry out condensation reaction, obtain described compound
Formula (III).
14, method according to claim 13 is characterized in that: described alkaline matter is selected from salt of wormwood, pyridine, triethylamine, yellow soda ash, sodium methylate or sodium hydride; Described organic solvent is toluene, benzene, DMF, acetonitrile or sherwood oil.
15, method according to claim 14 is characterized in that: described organic solvent is acetonitrile, DMF or toluene.
16, according to claim 13 or 14 or 15 described methods, it is characterized in that: the temperature of described condensation reaction is-10 ℃-120 ℃.
17, method according to claim 16 is characterized in that: the temperature of described condensation reaction is 30 ℃-100 ℃.
18, work as R in the preparation claim 1
1For-COR
2, wherein, R
2Be that carbon atom is the alkyl of 1-10, the method for cycloalkyl, phenyl, halogenophenyl, alkyl phenyl, alkoxyl phenyl, nitrophenyl, halogenated nitrobenzene, pyridyl, halogenated pyridyl or halo thiazolyl up-to-date style I compound that carbon atom is 5-6, comprise the steps: 1) in the presence of alkaline matter, in anhydrous organic solvent by 1-chloro-3,7-dimethyl-2,6-octadiene and 4-nitro imino--1,3,5 oxadiazines carry out condensation reaction, obtain 3-(3,7-dimethyl-2, the 6-octadiene)-and 4-nitro imino--1,3,5 oxadiazines; 2) by 3-(3,7-dimethyl-2,6-octadiene)-4-nitro imino--1,3,5 oxadiazines and formula IV compound carry out condensation reaction and obtain described compound in organic solvent in the presence of alkaline matter,
Formula (IV).
19, method according to claim 18 is characterized in that: described alkaline matter is selected from salt of wormwood, pyridine, triethylamine, yellow soda ash, sodium methylate or sodium hydride; Described organic solvent is toluene, benzene, DMF, acetonitrile or sherwood oil.
20, method according to claim 19 is characterized in that: described organic solvent is toluene, acetonitrile or DMF.
21, according to claim 18 or 19 or 20 described methods, it is characterized in that: the temperature of described condensation reaction is-10 ℃-120 ℃.
22, method according to claim 21 is characterized in that: the temperature of described condensation reaction is 30 ℃-100 ℃.
23, with the described compound of claim 1 be the control of aphids agent of activeconstituents.
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| [反]-β-法尼烯类似物的设计、合成与生物活性研究 杨新玲等，高等学校化学学报，第25卷第9期 2004;蚜虫警戒素类似物的合成 黄锦霞等，应用化学，第12卷第3期 1995 * |
| 蚜虫警戒素类似物的合成 黄锦霞等，应用化学，第12卷第3期 1995 * |
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| CN1631883A (en) | 2005-06-29 |
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