CN110156651A - A kind of propargite haptens and its synthetic method and application - Google Patents
A kind of propargite haptens and its synthetic method and application Download PDFInfo
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- CN110156651A CN110156651A CN201910310447.1A CN201910310447A CN110156651A CN 110156651 A CN110156651 A CN 110156651A CN 201910310447 A CN201910310447 A CN 201910310447A CN 110156651 A CN110156651 A CN 110156651A
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- C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
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- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
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Abstract
The purpose of the present invention is to provide a kind of propargite haptens and its synthetic method and applications, by combining the design feature of propargite to design a kind of synthetic method of propargite haptens, and it is applied to synthesis propargite artificial antigen, it is anti-Japanese to induce immune animal to generate, establish the various immunoassay methods of propargite.The synthetic method of propargite haptens of the present invention is as follows: (1) 4-TBP and 1,2- epoxy -4- vinyl cyclohexane reaction prepare intermediate product I；(2) intermediate product I is reacted with thionyl chloride prepares intermediate product II；(3) intermediate product II prepares intermediate product III with reacting for propilolic alcohol；(4) intermediate product III is reacted with 3- mercaptopropionic acid prepares haptens IV.The propargite haptens of synthesis had both utmostly remained the feature structure of propargite, so that the immunogenicity of propargite haptens is remarkably reinforced, and has the carboxyl that can be coupled with carrier, provided basis for the subsequent various immunoassay methods for establishing propargite.
Description
Technical field
The invention belongs to the technical fields of food safety detection, and in particular to a kind of propargite haptens and its synthetic method
And application.
Background technique
Propargite also known as propargite, it is the organosulfur acaricide of efficient one kind, low toxicity, wide spectrum, lasting period length, Ke Yiyou
Effect prevention and treatment mite class harm, has special efficacy to adult mite and deutonymph, can be used for preventing and treating cotton, vegetables, apple, citrus, tea, flowers and other crops
Various harmful mites.Have many advantages, such as control efficiency it is good, it is at low cost, be not likely to produce drug resistance.It is low to people and animals' toxicity, to natural enemy and warp
Ji insect such as ladybug, Chrysopa, honeybee and silkworm is safe.Since its drug effect is significant, it is not likely to produce drug resistance and well received.It is few
The pesticide residue of amount not will lead to acute poisoning, but propargite is eaten for a long time and remains exceeded vegetables and fruits, may produce to human health
Raw certain adverse effect, there are security risks.
The detection method of existing propargite mainly has high performance liquid chromatography (HPLC), gas chromatography (GC), liquid phase-
Mass spectrometry (LC-MS) method, gas chromatography-mass spectrometry (GC-MS) etc., instrument equipment operation in above-mentioned detection method
It is complicated, at high cost, high to operator's technical requirements, and cannot show immediately as a result, not being suitable for food, commodity inspection, epidemic prevention, poultry
It herds the producer and quick on-line checking and monitoring is carried out to object of suspicion.
Compared with above-mentioned detection method, immunology detection technology have it is economical, quickly, technical essential it is low, it is easy to operate and
The features such as on-site test can be achieved.Immunoassay detection technique developed in the fields of environment and food inspection in recent years
A kind of novel quick and precisely detection method, has been increasingly becoming the main of the quick selective mechanisms of countries in the world noxious residual chemicals
One of method.
When establishing immunological detection method and application detection method detection propargite residual quantity, key technology is energy
The antibody of high specificity, high sensitivity is enough got, and to realize this target, precondition must exactly prepare suitable alkynes
Mite spy's haptens.But it is domestic at present not yet for the relevant report of propargite haptens.
Summary of the invention
To solve the above-mentioned problems, it the purpose of the present invention is to provide a kind of propargite haptens and its synthetic method and answers
With and being applied to synthesis by combining the design feature of propargite to design a kind of synthetic method of propargite haptens
Propargite artificial antigen establishes the various immunoassay methods of propargite so that immune animal be induced to generate antibody.
Technical scheme is as follows:
A kind of propargite haptens, structure are as follows:
A kind of synthetic method of propargite haptens, which comprises the steps of:
1) 4-TBP and 1 are taken, the mixing of 2- epoxy -4- vinyl cyclohexane is added alkali after stirring and solvent is anti-
It answers, obtains intermediate product I；
2) it takes toluene and thionyl chloride to mix, is cooled to 0 DEG C and starts to stir, be added intermediate product I, it is anti-under condition of ice bath
It answers, obtains intermediate product II, refrigerate；
3) toluene, triethylamine and propilolic alcohol mixing are taken, leads to nitrogen, stirs under condition of ice bath, a dropping step 2) it is obtained in
Between product II, first ice bath reaction is rear to react at room temperature, and ethyl acetate is added later and pure water extracts organic layer repeatedly, obtains intermediate production
Object III；
4) intermediate product III, 3- mercaptopropionic acid made from step 3), benzoin dimethylether and methylene chloride mixing are taken, is stirred
It mixes, ultraviolet lighting, haptens IV is obtained after reaction；
The synthetic route of all of above reaction is as follows:
Wherein, OH-Represent hydroxide；SOCl2Represent thionyl chloride；TEA represents triethylamine；I, II, III are respectively represented
Three compounds as above, IV are propargite haptens.
Wherein, the dosage molar ratio of 4-TBP described in step 1) and 1,2- epoxy -4- vinyl cyclohexane is
1.0:(1.0-1.2)；The alkali includes sodium hydroxide or potassium hydroxide；The solvent includes toluene or purified water；
The dosage molar ratio of intermediate product I described in step 2) and thionyl chloride is 1.0:(1.0-1.5)；Intermediate product I
Mass volume ratio with toluene is 1.0g:(1.0ml-5.0ml)；
The dosage molar ratio of intermediate product I described in step 3), propilolic alcohol and triethylamine is 1.0:(1.5-2.0): (1.5-
2.0)；Temperature is controlled when the dropwise addition intermediate product II at 0~5 DEG C；
The dosage molar ratio of the mercaptopropionic acid of intermediate product III, 3- described in step 4) and styrax monomethyl ether is 1.0:
(1.5-3.0): 0.1；The ultraviolet wavelength is 254~365nm.
Preferred embodiment is as follows:
Step 1) weighs 4-TBP and 1, and 2- epoxy -4- vinyl cyclohexane is placed in there-necked flask, is stirred at room temperature
To dissolved clarification, alkali and solvent is added, is stirred to react；After completion of the reaction, it is washed 3 times with 5% sodium hydroxide solution；Organic phase is with anhydrous
Sodium sulphate dries, filters, and filtrate column chromatography for separation obtains intermediate product I；
Preferably, wherein the reaction dissolvent includes but is not limited to one of benzene,toluene,xylene and water or a variety of；
The alkali includes but is not limited to one of potassium hydroxide, sodium hydroxide and potassium carbonate or a variety of；It is highly preferred that the tertiary fourth of 4-
The molar ratio of base phenol and 1,2- epoxy -4- vinyl cyclohexane is 1.0:1.2；Each raw material dosage is controlled in above range
It is interior, be on the one hand conducive to the yield for further increasing compound 1, be on the one hand conducive to avoid raw material excess waste；
Toluene and thionyl chloride are placed in two mouthfuls of reaction flasks by step 2), are cooled to 0 DEG C of stirring, intermediate product is added by several times
I, ice bath reaction；Refrigerator cold-storage is placed, and is directly used in the next step, is obtained intermediate product II.
It is highly preferred that the molar ratio of material intermediate product I used and thionyl chloride is 1.0:1.2；It is highly preferred that object used
Expect the mass volume ratio of intermediate product I and toluene are as follows: 1.0g:2.0ml；
Toluene, triethylamine and propilolic alcohol are once placed in there-necked flask by step 3), nitrogen protection, are stirred under ice bath, are added dropwise
Made intermediate product II in step 2；Drop continues to stir 30min under ice bath after finishing, then is warming up to and is stirred at room temperature；After completion of the reaction,
Ethyl acetate and purified water is added, stirs liquid separation, takes organic layer；Water layer is extracted with ethyl acetate again, merges organic layer；Organic layer
It is dried, filtered with anhydrous sodium sulfate, filtrate is distilled to doing, and intermediate product III is obtained；
It is highly preferred that the molar ratio of material intermediate product I used, propilolic alcohol and triethylamine are 1.0:1.5:2.0；
Step 4) successively sets made intermediate product III, 3- mercaptopropionic acid of step 3, benzoin dimethylether and methylene chloride
In single port bottle, dissolved clarification, ultraviolet lighting is stirred at room temperature；The direct column chromatography for separation of reaction solution after completion of the reaction obtains haptens IV；
It is highly preferred that the molar ratio of material intermediate product III, 3- mercaptopropionic acid used and styrax monomethyl ether is 1.0:
2.0:0.1；Irradiation ultraviolet wavelength 254nm, 365nm or 254nm and 365nm used is used simultaneously, it is highly preferred that 254nm and
365nm is used simultaneously.
A kind of application of propargite haptens, the propargite haptens are used to prepare propargite artificial immunity antigen；Alkynes
Mite spy's haptens is applied to the immunoassay of propargite residue detection in food.
Technical effect of the invention is as follows:
The invention discloses a kind of propargite haptens and its synthetic method and application, synthesis with 4-TBP and
1,2- epoxy -4- vinyl cyclohexane is that starting material reacts to obtain final goal object, the propargite haptens of synthesis by 4 steps
Both the feature structure of propargite had utmostly been remained, so that the immunogenicity of propargite haptens is remarkably reinforced, and having can
With the carboxyl being coupled with carrier, basis is provided for the subsequent various immunoassay methods for establishing propargite；Propargite half is anti-
It is former to go immune animal with propargite artificial antigen that is obtaining after carrier conjugation, it is special to be more advantageous to stimulation animal immune response generation
Stronger, the higher antibody of sensitivity of property, provides basis for the subsequent various immunoassay methods for establishing propargite；
The present invention rationally designs the synthetic method of propargite haptens, the raw material used according to the design feature of propargite
Cheap and easy to get, experimental implementation is simple, and reaction condition is mild；The purity and high income for the propargite haptens that the present invention synthesizes are closed
At amino acids anti-mite agent haptens yield up to 35% or more.
Specific embodiment
Below by way of specific case study on implementation, the present invention is described in further detail, it should be understood that these embodiments are only used
In illustrating the present invention rather than limit the scope of the invention, after the present invention has been read, those skilled in the art couple
It is as defined in the appended claims that the modification of various equivalent forms of the invention falls within the application.
From An Naiji chemical reagents corporation, No. CAS is 24650-42-8, product for benzoin dimethylether buying in the present invention
Number is D070132, if remaining raw materials and reagents of the invention are the raw material of conventional market, reagent without specified otherwise.
Embodiment 1
A kind of preparation method of propargite haptens, includes the following steps:
(1) 4-TBP and 1,2- epoxy -4- vinyl cyclohexane reaction prepare intermediate product I:
4-TBP (1.00g, 6.66mmol) and 1,2- epoxy -4- vinyl are sequentially added into 50ml single port bottle
Hexamethylene (1.00g, 8.00mmol), is stirred at room temperature to dissolved clarification；Add potassium hydroxide (75mg, 1.33mmol) and toluene
(1.00ml) is warming up to 105 DEG C of stirring 18h；It is down to and is stirred at room temperature, be added toluene (20ml), with 5% sodium hydroxide solution
(60ml) is washed in three times, takes organic layer；Organic layer is dried, filtered with anhydrous sodium sulfate, takes filtrate；Filtrate column chromatography, is washed
De- agent is petroleum ether: ethyl acetate, volume ratio 10:1；Target liquid is separated, solvent is distilled off, obtains colorless and transparent oily object
1.7g, as intermediate product I, yield: 93%.
(2) intermediate product I is reacted with thionyl chloride prepares intermediate product II
Toluene (1.10ml) and thionyl chloride (0.18ml, 2.40mmol) are sequentially added into 50ml single port bottle, at room temperature
Stir 5min；It is cooled to 0~5 DEG C of stirring, point 4~6 addition intermediate product I (550mg, 2.00mmol) in 30min；It adds
Continue 0~5 DEG C of stirring 5h afterwards, then put refrigerator cold-storage (0~5 DEG C) 18h, obtains the toluene solution of intermediate product II, be directly used in down
Step reaction.
(3) intermediate product II prepares intermediate product III with reacting for propilolic alcohol
Toluene (1.00ml), triethylamine (400mg, 4.00mmol) and propilolic alcohol are sequentially added into 50ml single port bottle
(168mg, 3.00mmol), nitrogen protection stir 30min at room temperature；It is cooled to 0~5 DEG C of stirring, is dripped in 30min
State the toluene solution of intermediate product II；Continue 0~5 DEG C of stirring 30min after dripping off, is warmed to room temperature stirring 3h；Add into reaction solution
Entering ethyl acetate (20ml) and purified water (20ml), stir liquid separation, takes organic layer, water layer uses ethyl acetate (20ml) to extract again,
Merge organic layer；Organic layer is dried, filtered with anhydrous sodium sulfate, and filtrate column chromatography, eluant, eluent is petroleum ether: ethyl acetate, body
Product is than being 10:1；Target liquid is separated, solvent is distilled off, obtains colorless and transparent oily object 0.58g, as intermediate product III, step
(2) and (3) merge yield: 81.1%.
(4) intermediate product III is reacted with 3- mercaptopropionic acid prepares haptens IV
Sequentially added into 50ml single port bottle intermediate product III (440mg, 1.17mmol), 3- mercaptopropionic acid (250mg,
2.36mmol), benzoin dimethylether (30mg, 0.12mmol) and methylene chloride (8.80ml), are stirred at room temperature to dissolved clarification；Ultraviolet light
Irradiation, wavelength 254nm and 365nm, light application time 6h；By the direct column chromatography of reaction solution, eluant, eluent is petroleum ether: ethyl acetate,
Volume ratio is 2:1；Target liquid is separated, solvent is distilled off, obtains colorless and transparent oily object 268mg, as haptens IV, yield:
47.5%.
Embodiment 2
A kind of preparation method of propargite haptens, includes the following steps:
(1) 4-TBP and 1,2- epoxy -4- vinyl cyclohexane reaction prepare intermediate product I:
Sodium hydroxide (350mg, 8.66mmol) and purified water (13.00ml), room temperature are sequentially added into 50ml single port bottle
It stirs to dissolved clarification；It is added 4-TBP (1.00g, 6.66mmol), is stirred at room temperature to dissolved clarification；1,2- is added dropwise in 3~5min
Epoxy -4- vinyl cyclohexane (1.00g, 8.00mmol) is stirred at room temperature to dissolved clarification, reacts at room temperature 18h；Reaction solution is filtered,
Filter cake is washed in two times with purified water (40ml), then is washed with n-hexane (20ml), and gained filter cake room temperature is dried；White solid
1.65g, as intermediate product I, yield: 90.3%.
(2) intermediate product I is reacted with thionyl chloride prepares intermediate product II
Toluene (1.10ml) and thionyl chloride (0.22ml, 3.00mmol) are sequentially added into 50ml single port bottle, at room temperature
Stir 5min；It is cooled to 0~5 DEG C of stirring, point 4~6 addition intermediate product I (550mg, 2.00mmol) in 30min；It adds
Continue 0~5 DEG C of stirring 5h afterwards, then put refrigerator cold-storage (0~5 DEG C) 18h, obtains the toluene solution of intermediate product II, be directly used in down
Step reaction.
(3) intermediate product II prepares intermediate product III with reacting for propilolic alcohol
Toluene (1.00ml), triethylamine (400mg, 4.00mmol) and propilolic alcohol are sequentially added into 50ml single port bottle
(168mg, 3.00mmol), nitrogen protection stir 30min at room temperature；It is cooled to 0~5 DEG C of stirring, is dripped in 30min
State the toluene solution of intermediate product II；Continue 0~5 DEG C of stirring 30min after dripping off, is warmed to room temperature stirring 3h；Add into reaction solution
Entering ethyl acetate (20ml) and purified water (20ml), stir liquid separation, takes organic layer, water layer uses ethyl acetate (20ml) to extract again,
Merge organic layer；Organic layer is dried, filtered with anhydrous sodium sulfate, and filtrate column chromatography, eluant, eluent is petroleum ether: ethyl acetate, body
Product is than being 10:1；Target liquid is separated, solvent is distilled off, obtains colorless and transparent oily object 0.50g, as intermediate product III, step
(2) and (3) merge yield: 66.3%.
(4) intermediate product III is reacted with 3- mercaptopropionic acid prepares haptens IV
Sequentially added into 50ml single port bottle intermediate product III (440mg, 1.17mmol), 3- mercaptopropionic acid (250mg,
2.36mmol), benzoin dimethylether (30mg, 0.12mmol) and methylene chloride (8.80ml), are stirred at room temperature to dissolved clarification；Ultraviolet light
Irradiation, wavelength 365nm, light application time 6h；By the direct column chromatography of reaction solution, eluant, eluent is petroleum ether: ethyl acetate, volume ratio are
2:1；Target liquid is separated, solvent is distilled off, obtains colorless and transparent oily object 208mg, as haptens IV, yield: 36.9%.
It above are only part specific embodiment of the invention, but design concept of the invention is not limited to this, all utilizations
This design makes a non-material change to the present invention, and should all belong to behavior that violates the scope of protection of the present invention.As long as without departing from
The content of technical solution of the present invention, it is to the above embodiments according to the technical essence of the invention any type of simply to repair
Change, equivalent variations and remodeling, still falls within the protection scope of technical solution of the present invention.
Claims (9)
1. a kind of propargite haptens, which is characterized in that its structure is as follows:
2. the synthetic method of propargite haptens described in claim 1, which comprises the steps of:
1) 4-TBP and 1 are taken, the mixing of 2- epoxy -4- vinyl cyclohexane is added alkali and solvent reaction after stirring, obtains
To intermediate product I；
2) it takes toluene and thionyl chloride to mix, is cooled to 0 DEG C and starts to stir, intermediate product I is added, reacts, obtains under condition of ice bath
Intermediate product II, refrigeration；
3) toluene, triethylamine and propilolic alcohol mixing are taken, leads to nitrogen, stirs under condition of ice bath, a dropping step 2) made from intermediate produce
Object II, first ice bath reaction is rear to react at room temperature, and ethyl acetate is added later and pure water extracts organic layer repeatedly, obtains intermediate product
III；
4) intermediate product III, 3- mercaptopropionic acid made from step 3), benzoin dimethylether and methylene chloride mixing are taken, stirring is purple
Outer illumination obtains haptens IV after reaction；
The synthetic route of all of above reaction is as follows:
3. by the synthetic method of propargite haptens as claimed in claim 2, which is characterized in that 4- tert-butyl described in step 1)
Phenol and 1, the dosage molar ratio of 2- epoxy -4- vinyl cyclohexane are 1.0:(1.0-1.2)；The alkali include sodium hydroxide or
Person's potassium hydroxide；The solvent includes toluene or purified water.
4. by the synthetic method of propargite haptens as claimed in claim 2, which is characterized in that intermediate product described in step 2)
The dosage molar ratio of I and thionyl chloride is 1.0:(1.0-1.5)；The mass volume ratio of intermediate product I and toluene is 1.0g:
(1.0ml-5.0ml)。
5. the synthetic method of propargite haptens as described in Claims 2 or 3 or 4, which is characterized in that in described in step 3)
Between product I, propilolic alcohol and triethylamine dosage molar ratio be 1.0:(1.5-2.0): (1.5-2.0).
6. the synthetic method of propargite haptens as described in claim 5, which is characterized in that be added dropwise described in step 3) intermediate
Temperature is controlled when product II at 0~5 DEG C, the room temperature reaction time is 2~3h.
7. the synthetic method of propargite haptens as described in Claims 2 or 3 or 4, which is characterized in that in described in step 4)
Between the dosage molar ratio of product III, 3- mercaptopropionic acid and styrax monomethyl ether be 1.0:(1.5-3.0): 0.1；The ultraviolet waves
A length of 254~365nm.
8. the application of propargite haptens described in claim 1, which is characterized in that the propargite haptens is used to prepare alkynes
Mite spy's artificial immunity antigen.
9. the application of propargite haptens described in claim 1, which is characterized in that the propargite haptens is in food
The immunoassay of propargite residue detection.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115806512A (en) * | 2021-09-15 | 2023-03-17 | 张建勋 | Fluorine-containing acaricide and preparation method thereof |
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| CN1830253A (en) * | 2006-03-31 | 2006-09-13 | 青岛瀚生生物科技股份有限公司 | Manufacturing method of high content propargite |
| CN103073634A (en) * | 2011-10-25 | 2013-05-01 | 天津科技大学 | Specific antibody against herbicide anilofos |
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| CN1830253A (en) * | 2006-03-31 | 2006-09-13 | 青岛瀚生生物科技股份有限公司 | Manufacturing method of high content propargite |
| CN103073634A (en) * | 2011-10-25 | 2013-05-01 | 天津科技大学 | Specific antibody against herbicide anilofos |
| CN105924549A (en) * | 2016-05-05 | 2016-09-07 | 中山大学 | New method for functional modification of poly(beta-pinene) resin |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115806512A (en) * | 2021-09-15 | 2023-03-17 | 张建勋 | Fluorine-containing acaricide and preparation method thereof |
| CN115806512B (en) * | 2021-09-15 | 2024-07-19 | 张建勋 | Fluorine-containing acaricide and preparation method thereof |
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