CN109476604A - The method for being used to prepare Boscalid - Google Patents
The method for being used to prepare Boscalid Download PDFInfo
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- CN109476604A CN109476604A CN201780045903.3A CN201780045903A CN109476604A CN 109476604 A CN109476604 A CN 109476604A CN 201780045903 A CN201780045903 A CN 201780045903A CN 109476604 A CN109476604 A CN 109476604A
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- boscalid
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
- C07D213/82—Amides; Imides in position 3
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- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Provide the method for crystal modification II for preparing Boscalid anhydride a kind of, this method includes that (i) reacts the chloro- nicotinoyl chlorine of 2- in dicyandiamide solution with 4 '-chloro- xenyl -2- base amine, while the hydrogen chloride formed during reaction is removed from reaction mixture；And (ii) recycles the crystal modification II of Boscalid anhydride from step (i) in the reaction mixture of generation.
Description
Cross reference to related applications
This application claims " be used to prepare Boscalid to the entitled of Department of Intellectual Property, Britain submission on August 4th, 2016
The priority of No. 1613458.7 UK Patent Application of method ", entire contents are incorporated herein by reference.
Technical field
The present invention relates to the methods for being used to prepare Boscalid, more particularly to the knot for being used to prepare Boscalid anhydride
The method of brilliant variant II.
Background technique
Adopted name is the chloro- N- of compound 2- (4 ' chlorine [1,1 ' xenyl] -2- base)-Niacinamide of Boscalid
With structural formula I:
Boscalid is carboxyl acylamide fungicide, and serve as succinate dehydrogenase inhibitors (SDHI), i.e. mitochondria
Respiration inhibitor.The carboxylic imide compound of this classification and the activity of these compounds are for the first time in US 4,001,416 and US
It is described in 5,330,995.
Boscalid has an activity as fungicide, and its now with it is a series of be used to handle fungal infection and its
The preparation of generated disease is commercially available.
US 7,087,239 is related to the crystalline hydrate of niacin aniline and/or Benzanilide derivatives.US7,087,239
In specifically illustrate Boscalid hydrate synthesis and recycling.The hydrate is described as by preparing Boscalid first
Anhydride obtains, which obtains at the end of synthesis process as the solution in hot dimethylbenzene.After cooling,
Boscalid is crystallized out from the solution and it is allowed to be dried in vacuo in an oven.The anhydride is noted special with following physics
Property:
US 7,087,239 disclose the hydrate can by 40 DEG C, in a solvent the anhydride is dissolved into tetrahydro
In furans (THF) and acquired solution is added in water and is formed.Sediment is isolated simultaneously in the mixture obtained by as filtering
It makes it dry, with the monohydrate of output Boscalid.The crystallization of Boscalid anhydride disclosed in US 7,087,239 becomes
Body is herein referred to as the crystal modification I of Boscalid.
US 7,241,896 is related to for generating 2- halogen-pyridine-2-carboxamide method.Disclose and illustrate Boscalid
Preparation.In this example, Boscalid be by the chloro- 3- cigarette acyl chloride II of 2- and 2- (4- chlorphenyl) aniline in water and
It is reacted to synthesize in the presence of dimethylbenzene.After completion of the reaction, water phase is removed.It then must be water-soluble with the sodium carbonate of heat
Liquid extracts remaining solution.After being extracted with sodium carbonate liquor, Boscalid is crystallized out by cooling down organic solution steadily.
We have found that grinding the crystal modification of Boscalid anhydride disclosed in US 7,087,239 in water is
Difficult.Therefore, directly the crystal modification of Boscalid is configured to need to grind and/or the expectation preparation of fine grinding process is not
One simple task.These preparations are, such as granula, microcapsulated granule, tablet, water-dispersible granules, water dispersed tablet, water
Dispersible powders or water-dispersible powder, powder preparation and reactive compound for seed treatment exist in a dispersed form
Preparation, such as suspending agent, oil-based suspension, suspoemulsion or the suspending agent for seed treatment.Before being configured to suspending agent,
It needs the crystal modification aquation of Boscalid.
US 7,501,384 discloses the new crystal modification claimed as Boscalid anhydride.It is disclosed in US 7,501,384
Crystal modification be herein referred to as the crystal modification II of Boscalid.It is proposed in US 7,501,384, Boscalid
Crystal modification II is more suitable for manufacturing various preparations, and otherwise these preparations need prolonged grinding/fine grinding process.
The crystal modification II that US 7,501,384 describes the Boscalid anhydride can be by the inclusion of following steps
Method preparation:
A) anhydride of the crystal modification I of Boscalid is dissolved in polar organic solvent or aromatic hydrocarbon；And
B) anhydride of the crystal modification II of Boscalid is precipitated by the cooling solvent.
The alternative that the crystal modification II of Boscalid anhydride is prepared disclosed in US 7,501,384 includes:
A) the crystal modification I of Boscalid is heated to 150 DEG C or more until fusing；And
B) the thawing object of the crystal seed of the cooling crystal modification II for being added to Boscalid.
The crystal modification II of Boscalid is described as having the property that by US 7,501,384
It is obtained from the Crystallographic Study of the crystal modification II of Boscalid using the single crystal diffractometer of Siemens (Siemens)
The key parameter and unit cell obtained provides as follows in US 7,501,384:
Parameter illustrated above has following meanings:
The rib of a, b, c=structure cell is long；
α, beta, gamma=corresponding angle；And
Molecular number in Z=structure cell.
If the improvement preparation method of the crystal modification II of Boscalid anhydride can be provided, it is particularly suitable in quotient
It is applied in industry scale, the method for variant II product with reproducible yield, will have significant advantage.Preferably, the party
Method is easy to operate and easily controllable.
Therefore, it is necessary to be used to prepare the improved method of Boscalid.Particularly, if being used to prepare changing for Boscalid
Into method can with high yield generate anhydride crystal modification II will be advantageous.If this method is easy to operate, that will
It is a further advantage that.Advantageously, which will use least component, the component preferably readily handled.
Summary of the invention
It has now been discovered that a kind of improvement for preparing Boscalid (the especially crystal modification II of Boscalid anhydride)
Method.Particularly, it has been found that one kind is related to the chloro- nicotinoyl chlorine of 2- and reacts in dicyandiamide solution with 4 '-chloro- xenyl -2- base amine
New method.
According to the present invention, the method for crystal modification II for preparing Boscalid anhydride a kind of is provided, this method includes:
(i) react the chloro- nicotinoyl chlorine of 2- in dicyandiamide solution with 4 '-chloro- xenyl -2- base amine, while from reaction mixture
Remove the hydrogen chloride formed during the reaction；And
(ii) the crystal modification II of Boscalid anhydride is recycled in the reaction mixture generated from step (i).
It has been found that method of the invention generates the crystal modification II of Boscalid anhydride with yield.This method has
It sharp ground can be using the component of minimal number and easy to operate, especially on extensive or commercial size.
In the method for the invention, the chloro- nicotinoyl chlorine of 2- is reacted with 4 '-chloro- xenyl -2- base amine.According to following logical
The reaction is carried out with reaction scheme:
The chloro- nicotinoyl chlorine of 2- and 4 '-chloro- xenyl -2- base amine are all known compounds and are commercially available.
The chloro- nicotinoyl chlorine of 2- and 4 '-chloro- xenyl -2- base amine can be present in reaction mixture with any suitable amount.
In a preferred embodiment, exist to 4 '-chloro- xenyl -2- base amine molar excess, to ensure the complete of the chloro- nicotinoyl chlorine of 2-
Full response.In this embodiment, 4 '-chloro- xenyl -2- base amine are preferably at least 10%, more preferably at least 20% mole
It is present in excess.Can use at most 50% molar excess, preferably up to 30%.The chloro- biphenyl in the 4 '-of 25% molar excess
Base -2- base amine is especially suitable for many embodiments.
The chloro- nicotinoyl chlorine of 2- occurs in the presence of dicyandiamide solution with 4 '-chloro- reacting for xenyl -2- base amine.Dicyandiamide solution
Most preferably single-phase solvent system, especially one-phase organic solvent system.Ability using single-phase solvent system is present invention side
Another advantage of method.
The dicyandiamide solution may include one or more of suitable solvents.Suitable solvent is organic solvent, including pole
Property organic solvent and aromatic hydrocarbon.Preferred organic solvent include alcohol (including polyalcohol, such as dihydric alcohol), nitrile, aromatic solvent,
Halogenated alkane and its mixture.
The example of suitable alcohol is C1To C8Alcohol, preferably C1To C5Alcohol.The alcohol can be linear chain or branched chain fatty alcohol, more excellent
Selection of land is ethyl alcohol, propyl alcohol and butanol.The alcohol can be alicyclic alcohol, such as cyclohexanol.The solvent may include polyalcohol, such as
Dihydric alcohol.The example of suitable dihydric alcohol is monoethylene glycol and polyethylene glycol, preferably ethylene glycol and diethylene glycol (DEG).It is a kind of preferred molten
Agent is isopropanol.
The example of suitable nitrile is C3To C8Nitrile, preferably C3To C6Nitrile.Acetonitrile is a kind of preferred nitrile.
Suitable aromatic solvent is benzene, toluene and dimethylbenzene.Benzene and toluene are two kinds of preferred aromatic solvents.
The example of suitable halogenated alkane is C1To C8Halogenated alkane, preferably C1To C5Halogenated alkane, more preferable C1To C3Halogen
For alkane.The alkane can be linear chain or branched chain fat alkane, more preferable halothane, propane or butane.The alkane can be
Alicyclic alkanes, such as cyclohexane halide.Suitable halogen moiety includes fluorine, chlorine and bromine, preferably chlorine.Alkane may include individually
Halogen moiety or two or more halogen moieties.The example of suitable halogenated alkane includes methylene chloride.
Solvent illustrated above is known in the art and is commercially available.
The method of the invention the step of in (i), the chloro- nicotinoyl chlorine of 2- is reacted with 4 '-chloro- xenyl -2- base amine, with
Generate Boscalid.The chloro- nicotinoyl chlorine of 2- reacts the hydrogen chloride generated as by-product with 4 '-chloro- xenyl -2- base amine.?
In method of the invention, while the chloro- nicotinoyl chlorine of 2- and 4 '-chloro- xenyl -2- base amine react from reaction mixture
Except de-chlorine hydride.In this way, it avoids and takes other step (such as by adding a large amount of alkali) Lai Zhonghe hydrogen chloride
It needs.
Hydrogen chloride generates in gaseous form and is present in reaction mixture, and can be in step (i) with any
Suitable mode is removed from reaction mixture.In a preferred embodiment, it is removed from reaction mixture by adsorbing
Hydrogen chloride.Suitable adsorbent is known in the art.A kind of preferred adsorbent includes aluminium oxide, especially active oxidation
Aluminium.Adsorbent can further include promotor, such as alkali metal.A kind of suitable adsorbent is disclosed in US 5,316,998
In.
Reaction in the step of this method (i) can carry out at any suitable temperature.Step (i) is liquid in dicyandiamide solution
It is carried out at a temperature of body.
The chloro- nicotinoyl chlorine of 2- is preferably working as solid Boscalid shape in the reaction with reacting for 4 '-chloro- xenyl -2- base amine
Achievement can be carried out from being crystallized at a temperature of solid in dicyandiamide solution.In this way, chloro- by the chloro- nicotinoyl chlorine of 2- and 4 '-
The Boscalid that the reaction of phenyl -2- base amine generates is obtained directly as solid in the reactive mixture.
React completion when the chloro- nicotinoyl chlorine of 2- and 4 '-chloro- xenyl -2- base amine, so that it may cooling reaction mixture with into
One-step crystallization remains in any Boscalid in the solution in dicyandiamide solution.For example, reaction mixture can be cooled to room temperature
Or the temperature of about room temperature, such as 10 DEG C to 20 DEG C.
In many embodiments, the chloro- nicotinoyl chlorine of 2- in step (i) is reacted with 4 '-chloro- xenyl -2- base amine
It is carried out at a temperature of greater than 10 DEG C, more preferably at least 15 DEG C, still more preferably at least 20 DEG C.In some preferred embodiments,
Reaction in step (i) at least 30 DEG C, more preferably at least 40 DEG C, still more preferably at least 50 DEG C at a temperature of carry out, and temperature
Degree is higher than 60 DEG C and is suitable for many embodiments.Reaction temperature in step (i) is lower than the boiling point of reaction mixture.Preferably,
Temperature is lower than 80 DEG C, still more preferably below 75 DEG C, is more preferably still below 70 DEG C.It has been found that 65 DEG C of reaction temperature is suitable for being permitted
More embodiments.
The chloro- nicotinoyl chlorine of 2- when this method the step of in (i) reacts completion with 4 '-chloro- xenyl -2- base amine, just from
Boscalid product is recycled in reaction mixture.For example, Boscalid can be recycled from reaction mixture by crystallization.From
Before or after crystallizing Boscalid in solution, the solid Boscalid generated in step (i) can be recovered by filtration.It can be with
Boscalid is crystallized out in the reaction mixture generated from step (i) using any suitable technology.It is preferred real at one
It applies in scheme, by sufficiently reducing the temperature of reaction mixture so that the crystallization of solid Boscalid is crystallized from reaction mixture
Boscalid out.The temperature that Boscalid is crystallized out from reaction mixture will depend on used dicyandiamide solution.Make pyridine acyl
The representative temperature of bacterium amine crystallization is 5 DEG C to 20 DEG C.The substitute technology that Boscalid is recycled from the solution in reaction mixture exists
This field is known, and including removing solvent from reaction mixture, such as by using vacuum or compressed air, and/
Or by the way that crystal seed is introduced into reaction mixture.If they are preferably the crystalline substance of the crystal modification II of Boscalid using crystal seed
Body.
When in the reactive mixture obtain solid Boscalid product, so that it may recycle the solid Boscalid product.It returns
The solid of receipts is the crystal modification II of Boscalid.Any suitable skill can be used in the crystal modification II of Boscalid anhydride
Art recycling, such as by removing one of solvent and filtering or their combination.The crystal modification II of the Boscalid of recycling
It is preferred that dry after being recycled in reaction mixture.
As described above, the method for the present invention particular advantage is hydrogen chloride when generating from the step (i) i.e. by from reaction
It is removed in mixture.As also described above, this avoids need using a large amount of other components (such as alkali) Lai Zhonghe hydrogen chloride.It is logical
The step of operating this method with excessive 4 '-chloro- xenyl -2- base amine (i) is spent, remaining micro chlorine in the reactive mixture
Change hydrogen by being removed with 4 '-chloro- reacting for xenyl -2- base amine, This further improves the efficiency of the method for the present invention and excellent
Point.
Detailed description of the invention
FTIR spectrum method record IR spectrum can be used.
Fig. 1 is the IR spectrum of the crystal modification II of Boscalid anhydride；
Fig. 2 is the IR spectrum of the crystal modification I of Boscalid anhydride.
Specific embodiment
It will only be now that the purpose illustrated describes embodiment of the present invention by the following example.
In the examples below, indicated percentage is weight percent, unless otherwise stated.
Embodiment
Embodiment 1
Boscalid is prepared using following general reaction sequence:
At 20 DEG C, the chloro- nicotinoyl chlorine of 3.5g 2- is added drop-wise to chloro- containing the 5.0g 4 '-in 30ml methylene chloride
In the reaction flask of the solution of phenyl -2- base amine.Reaction flask is connect with outside HCL absorber, which, which contains, includes
The adsorbent of activated alumina and alkali metal promoter.Mixture in reaction flask is maintained 20 DEG C 2 hours under stiring.
Then gained mixture is cooled to 10 DEG C under stiring, and Boscalid solid is made to crystallize out from solution.
Based on the chloro- nicotinoyl chlorine of 2- used, Boscalid solid is recycled to be equivalent to 90% amount of yield.
Obtained solid is confirmed by melting point analysis (DSC), infrared ray (IR) spectrometry and X-ray diffraction (XRD)
The form of Boscalid is the crystal modification II of Boscalid anhydride in material.
Embodiment 2
Boscalid is prepared according to general reaction sequence identical with above-described embodiment 1.
At room temperature, the chloro- nicotinoyl chlorine of 3.5g 2- is added drop-wise to containing the chloro- xenyl -2- of 5.0g 4 '-in 30ml benzene
In the reaction flask of the solution of base amine.Reaction flask is connect with outside HCL absorber, which contains comprising active oxidation
The adsorbent of aluminium and alkali metal promoter.Then 40 DEG C are heated the mixture to and maintains the temperature under stiring 2 hours.
Then gained mixture is cooled to room temperature under stiring, and Boscalid solid is made to crystallize out from solution.
Based on the chloro- nicotinoyl chlorine of 2- used, Boscalid solid is recycled from reaction mixture to be equivalent to 92% amount of yield.
Obtained solid is confirmed by melting point analysis (DSC), infrared ray (IR) spectrometry and X-ray diffraction (XRD)
The form of Boscalid is the crystal modification II of Boscalid anhydride in material.
Embodiment 3
Boscalid is prepared according to general reaction sequence identical with above-described embodiment 1.
At 40 DEG C, the chloro- nicotinoyl chlorine of 3.5g 2- is added drop-wise to equipped with the chloro- biphenyl of 5.0g 4 '-in 30ml isopropanol
In the reaction flask of the solution of base -2- base amine.Reaction flask is connect with outside HCL absorber, which contains comprising living
The adsorbent of property aluminium oxide and alkali metal promoter.Then 65 DEG C are heated the mixture to and maintains the temperature 2 small under stiring
When.
Then gained mixture is cooled to room temperature under stiring, and Boscalid solid is made to crystallize out from solution.
Based on the chloro- nicotinoyl chlorine of 2- used, Boscalid solid is recycled to be equivalent to 95% amount of yield.
Obtained solid is confirmed by melting point analysis (DSC), infrared ray (IR) spectrometry and X-ray diffraction (XRD)
The form of Boscalid is the crystal modification II of Boscalid anhydride in material.
Embodiment 4
Boscalid is prepared according to general reaction sequence identical with above-described embodiment 1.
At 40 DEG C, the chloro- nicotinoyl chlorine of 3.5g 2- is added drop-wise to equipped with the chloro- xenyl -2- of 5.0g 4 '-in 30ml acetonitrile
In the reaction flask of the solution of base amine.Reaction flask is connect with outside HCL absorber, which contains comprising active oxidation
The adsorbent of aluminium and alkali metal promoter.Then 65 DEG C are heated the mixture to and maintains the temperature under stiring 2 hours.
Then gained mixture is cooled to room temperature under stiring, and Boscalid solid is made to crystallize out from solution.
Based on the chloro- nicotinoyl chlorine of 2- used, Boscalid solid is recycled to be equivalent to 95% amount of yield.
Obtained solid is confirmed by melting point analysis (DSC), infrared ray (IR) spectrometry and X-ray diffraction (XRD)
The form of Boscalid is the crystal modification II of Boscalid anhydride in material.
Embodiment 5
Boscalid is prepared according to general reaction sequence identical with above-described embodiment 1.
At room temperature, the chloro- xenyl -2- base amine of the 5.0g 4 '-chloro- nicotinoyl chlorine of 3.5g 2- being added drop-wise in 30ml toluene
Solution in.Reaction flask is connect with outside HCL absorber, which contains comprising activated alumina and alkali metal promotion
The adsorbent of agent.Then 65 DEG C are heated the mixture to and maintains the temperature under stiring 2 hours.
Then gained mixture is cooled to room temperature under stiring, and Boscalid solid is made to crystallize out from solution.
Based on the chloro- nicotinoyl chlorine of 2- used, Boscalid solid is recycled to be equivalent to 92% amount of yield.
Obtained solid is confirmed by melting point analysis (DSC), infrared ray (IR) spectrometry and X-ray diffraction (XRD)
The form of Boscalid is the crystal modification II of Boscalid anhydride in material.
Claims (18)
1. a kind of method for the crystal modification II for preparing Boscalid anhydride, the method includes:
(i) it reacts the chloro- nicotinoyl chlorine of 2- in dicyandiamide solution with 4 '-chloro- xenyl -2- base amine, while being mixed from reaction
The hydrogen chloride formed during reaction is removed in object；And
(ii) the crystal modification II of Boscalid anhydride is recycled in the reaction mixture generated from step (i).
2. according to the method described in claim 1, wherein 4 '-chloro- xenyl -2- base amine are excessively present in the institute of step (i)
It states in reaction mixture.
3. according to the method described in claim 2, wherein 4 '-chloro- xenyl -2- base amine are deposited at least 10% molar excess
?.
4. according to the method described in claim 3, wherein 4 '-chloro- xenyl -2- base amine are deposited at least 20% molar excess
?.
5. according to the method described in claim 4, wherein 4 '-chloro- xenyl -2- base amine exist with about 25% molar excess.
6. method according to any preceding claims, wherein the dicyandiamide solution is one-phase organic solvent system.
7. method according to any preceding claims, wherein the dicyandiamide solution includes polar organic solvent and/or virtue
Fragrant race's solvent.
8. according to the method described in claim 7, wherein the dicyandiamide solution include alcohol, nitrile, aromatic solvent, halogenated alkane,
Or mixtures thereof.
9. according to the method described in claim 8, wherein the dicyandiamide solution includes isopropanol, acetonitrile, benzene, toluene, dichloromethane
Or mixtures thereof alkane,.
10. method according to any preceding claims, the hydrogen chloride wherein generated in step (i) is by using adsorbent
Absorption is carried out to be removed.
11. according to the method described in claim 10, wherein the adsorbent includes activated alumina.
12. method described in 0 or 11 according to claim 1, wherein the adsorbent includes alkali metal promoter.
13. method according to any preceding claims, wherein step (i) can be mixed in solid Boscalid from the reaction
It closes and is carried out at a temperature of being crystallized in object.
14. method according to any preceding claims, wherein step (i) at least 20 DEG C at a temperature of carry out.
15. method according to any preceding claims, wherein step (i) at most 80 DEG C at a temperature of carry out.
16. method according to any preceding claims, wherein step (ii) includes described anti-by what is generated in step (i)
Mixture is answered to be cooled down, so that Boscalid is crystallized from the reaction mixture.
17. according to the method for claim 16, wherein the reaction mixture to be cooled to 5 DEG C to 20 DEG C of temperature.
18. the method that one kind is used to prepare the crystal modification II of Boscalid anhydride substantially as described above.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1613458.7A GB2552697B (en) | 2016-08-04 | 2016-08-04 | Process for the preparation of boscalid |
| GB1613458.7 | 2016-08-04 | ||
| PCT/CN2017/094628 WO2018024146A1 (en) | 2016-08-04 | 2017-07-27 | Process for preparation of boscalid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN109476604A true CN109476604A (en) | 2019-03-15 |
Family
ID=60940411
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201780045903.3A Pending CN109476604A (en) | 2016-08-04 | 2017-07-27 | The method for being used to prepare Boscalid |
Country Status (3)
| Country | Link |
|---|---|
| CN (1) | CN109476604A (en) |
| GB (1) | GB2552697B (en) |
| WO (1) | WO2018024146A1 (en) |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1081936A (en) * | 1992-05-05 | 1994-02-16 | 发现化学品有限公司 | A kind of adsorbent that removes de-chlorine hydride |
| CN1558901A (en) * | 2001-09-25 | 2004-12-29 | �����ɷ� | Crystalline hydrates of nicotinic acid anilide and benzoyl anilide derivatives |
| CN1751026A (en) * | 2003-02-14 | 2006-03-22 | 巴斯夫股份有限公司 | Novel crystalline modification of the anhydrate of boscalid |
| CN103073489A (en) * | 2013-02-06 | 2013-05-01 | 利民化工股份有限公司 | Preparation method of Boscalid |
| CN103980192A (en) * | 2014-01-20 | 2014-08-13 | 泰州百力化学股份有限公司 | Selective synthesis method of cyprosulfamide with different crystal forms |
| WO2015106443A1 (en) * | 2014-01-17 | 2015-07-23 | 迈克斯(如东)化工有限公司 | Preparation and application of biphenyl compound |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE316959T1 (en) * | 2001-11-02 | 2006-02-15 | METHOD FOR PRODUCING 2-HALOPYRIDINCARBONIC ACID AMIDES | |
| WO2014174397A2 (en) * | 2013-04-25 | 2014-10-30 | Mandal Dr Swadhin K | Method of synthesis molecules using catalyst and composites thereof |
-
2016
- 2016-08-04 GB GB1613458.7A patent/GB2552697B/en not_active Expired - Fee Related
-
2017
- 2017-07-27 WO PCT/CN2017/094628 patent/WO2018024146A1/en active Application Filing
- 2017-07-27 CN CN201780045903.3A patent/CN109476604A/en active Pending
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1081936A (en) * | 1992-05-05 | 1994-02-16 | 发现化学品有限公司 | A kind of adsorbent that removes de-chlorine hydride |
| CN1558901A (en) * | 2001-09-25 | 2004-12-29 | �����ɷ� | Crystalline hydrates of nicotinic acid anilide and benzoyl anilide derivatives |
| CN1751026A (en) * | 2003-02-14 | 2006-03-22 | 巴斯夫股份有限公司 | Novel crystalline modification of the anhydrate of boscalid |
| CN103073489A (en) * | 2013-02-06 | 2013-05-01 | 利民化工股份有限公司 | Preparation method of Boscalid |
| WO2015106443A1 (en) * | 2014-01-17 | 2015-07-23 | 迈克斯(如东)化工有限公司 | Preparation and application of biphenyl compound |
| CN103980192A (en) * | 2014-01-20 | 2014-08-13 | 泰州百力化学股份有限公司 | Selective synthesis method of cyprosulfamide with different crystal forms |
Also Published As
| Publication number | Publication date |
|---|---|
| GB2552697B (en) | 2021-03-10 |
| WO2018024146A1 (en) | 2018-02-08 |
| GB2552697A (en) | 2018-02-07 |
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