CN105949125A - Method for catalytically synthesizing pyraclostrobin - Google Patents
Method for catalytically synthesizing pyraclostrobin Download PDFInfo
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- CN105949125A CN105949125A CN201610455713.6A CN201610455713A CN105949125A CN 105949125 A CN105949125 A CN 105949125A CN 201610455713 A CN201610455713 A CN 201610455713A CN 105949125 A CN105949125 A CN 105949125A
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- pyraclostrobin
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
- C07D231/18—One oxygen or sulfur atom
- C07D231/20—One oxygen atom attached in position 3 or 5
- C07D231/22—One oxygen atom attached in position 3 or 5 with aryl radicals attached to ring nitrogen atoms
Abstract
The invention discloses a method for catalytically synthesizing pyraclostrobin, relating to the technical fields of chemical industry and pesticide intermediate preparation. The method comprises the following steps: adding a compound II N-hydroxy-N-2-[(N-p-chlorphenyl)-3-pyrazolyloxymethyl]carbanilate into a two-phase solvent, adding a phase-transfer catalyst, and meanwhile, dropwisely adding an acid-binding agent water solution and dimethyl sulfate to carry out etherification reaction on the compound II N-hydroxy-N-2-[(N-p-chlorphenyl)-3-pyrazolyloxymethyl]carbanilate and dimethyl sulfate while keeping the pH value of the reaction system at 8-9, thereby obtaining the compound I pyraclostrobin. The method has the advantages of short reaction time and high product yield, lowers the production cost, and reduces the generated wastewater, thereby being beneficial to environment protection.
Description
Technical field
The present invention relates to the preparing technical field of pyraclostrobin.
Background technology
Pyraclostrobin (chemical name: N-methoxyl group-N-[(N-rubigan)-3-pyrazoles epoxide methyl] carbanilate, compounds I), it is that BASF Aktiengesellschaft is in a kind of novel wide spectrum Strobin series bactericidal agent containing pyrrazole structure of discovery in 1993.It is mainly used in stem and leaf spraying, can effectively prevent and treat the crop pest caused by Ascomycetes, Basidiomycetes, Oomycete fungal and Fungi Imperfecti, there is again the selective feature of low ecological risk, highly drug effect simultaneously.It is widely used in preventing and treating the disease on Semen Tritici aestivi, Semen arachidis hypogaeae, Oryza sativa L., vegetable fruit tree and field crop.It is classified as " Candidate Agents reducing risk " by Environmental Protection Agency.
The synthetic route of pyraclostrobin etherificate is mainly N-hydroxy-n-2-[(N-rubigan)-3-pyrazoles epoxide methyl] carbanilate (compound ii) in halogenated alkane solvents, with Carbon Dioxide sodium salt or potash salt as acid binding agent, dimethyl sulfate is dripped in reaction system, after having reacted, add sodium sulfate salt or potassium sulfate salt that water dissolution generates, divide and remove aqueous phase, organic facies concentrating under reduced pressure, recrystallisation solvent is added in concentrate, obtaining pyraclostrobin (compounds I), synthetic route is as follows:
Although this synthetic method can reach the purpose of synthesizing pyrazole kresoxim-methyl, but in preparation process in place of Shortcomings: (1) severe reaction conditions, reaction system requires that moisture is low, and compound ii reacts after needing to dry；(2), after dropping dimethyl sulfate, the response time is longer and reaction is the most thorough；(3) sodium carbonate used or potassium carbonate excess, last handling process needs to add the inorganic salt that a large amount of water dissolution generates, produces a large amount of high-salt wastewater.
Summary of the invention
The technical problem to be solved in the present invention is to provide a kind of method catalyzing and synthesizing pyraclostrobin, and the method response time is short, and product yield is high, reduces production cost, reduces waste water and produces, is conducive to protecting environment.
For solving above-mentioned technical problem, the technical solution used in the present invention is: a kind of method catalyzing and synthesizing pyraclostrobin, compound ii N-hydroxy-n-2-[(N-rubigan)-3-pyrazoles epoxide methyl] carbanilate is joined in two-phase solvent, add phase transfer catalyst, it is simultaneously added dropwise aqueous solution and the dimethyl sulfate of acid binding agent, keep reaction system pH=8-9, compound ii N-hydroxy-n-2-[(N-rubigan)-3-pyrazoles epoxide methyl] carbanilate and dimethyl sulfate is made to carry out etherification reaction, obtain compounds I pyraclostrobin, reaction equation is as follows:
。
PTC i.e. Phase Transfer Catalyst phase transfer catalyst.
Phase transfer catalyst is quaternary ammonium compound or polyether compound.
Preferably, quaternary ammonium compound is tetrabutylammonium chloride, tetrabutyl ammonium bromide, benzyltrimethylammonium chloride or benzyltrimethylammonium bromide；Polyether compound is PEG400, Macrogol 600 or polyethylene glycol-800.
Acid binding agent is the mixture of one or more in Lithium hydrate, potassium hydroxide, sodium hydroxide.
Preferably, acid binding agent is sodium hydroxide.
Two-phase solvent is made up of halogenated alkane and water, halogenated alkane be dichloromethane, 1,2-dichloroethanes, chloroform or carbon tetrachloride.
The mol ratio of raw material is: compound ii: dimethyl sulfate: acid binding agent=1: 1～2: 1～2, and phase transfer catalyst consumption is the 0.5%～10% of compound ii quality.
The grams of compound ii is 1: 5～15 with the milliliter number ratio of two-phase solvent, and two-phase solvent is halogenated alkane and water, and wherein the volume ratio of halogenated alkane and water is 1: 0.1～1.2.
Etherification reaction temperature is 20 DEG C～80 DEG C.
After etherification reaction completes, divide and remove aqueous phase, organic facies concentrating under reduced pressure, in concentrate, add recrystallisation solvent, obtain compounds I pyraclostrobin.
Using and have the beneficial effects that produced by technique scheme: the inventive method response time is short, product yield is high, and compound used therefor II, without drying, can react by band water, makes operating process simpler；Use low cost acid binding agent, effectively reduce production cost；Control process water consumption, decrease the generation of waste water, advantageously in protection environment.
Accompanying drawing explanation
The present invention is further detailed explanation below in conjunction with the accompanying drawings；
Fig. 1 is compounds I in the embodiment of the present invention 11H-NMR testing result spectrogram；
Fig. 2 is the MS testing result spectrogram of compounds I in the embodiment of the present invention 1.
Detailed description of the invention
Below in conjunction with instantiation, the present invention is described in detail.
Embodiment 1
By 373.8 g(1 mol) compound ii joins 2250 mL
In the two-phase solvent of chloroform and 350 mL water composition, add 11.2 g tetrabutyl ammonium bromide, be warming up to backflow, be simultaneously added dropwise 173 g
30%(1.3 mol) sodium hydrate aqueous solution and 164g(1.3 mol) dimethyl sulfate, keep reaction system pH=8-9,2 hours dropping complete, return stirring 2 hours, it is down to room temperature, divides and remove aqueous phase, organic facies concentrating under reduced pressure, recrystallisation solvent isopropanol is added in concentrate, being filtrated to get compounds I, pale yellow crystals 373 g, HPLC measure (external standard) content 98.8%, yield 96.2%, mp:63-65 DEG C.
1H-NMR(400MHz, CDCl3): δ=3.761 (3H, s ,-CH3), δ = 3.795(3H, s, -CH3), δ = 5.345(2H, s, -CH2), δ = 5.9215.927(1H, d, -CH), δ =
7.344～7.405 (5H, m, Phenyl-H ,-CH), δ=7.5147.551 (2H, d, Phenyl-H), δ=7.6537.693 (2H, m, Phenyl-H), as shown in Figure 1.
ESI (m/z): 389.9 (M+1), as shown in Figure 2.
Embodiment 2
By 373.8 g(1 mol) compound ii joins 1699 mL
In the two-phase solvent of dichloromethane and 170 mL water composition, add 22.4 g tetrabutylammonium chlorides, it is warming up to 39-42 DEG C, be simultaneously added dropwise 173 g 30%(1.3 mol) sodium hydrate aqueous solution and 164g(1.3 mol) dimethyl sulfate, keep reaction system pH=8-9, dropping in 2 hours is complete, 39-42 DEG C of insulated and stirred 2 hours, is down to room temperature, point removes aqueous phase, organic facies concentrating under reduced pressure, in concentrate, add recrystallisation solvent isopropanol, be filtrated to get compounds I, pale yellow crystals 370g, HPLC measures (external standard) content 98.3%, yield 95.4%.
Embodiment 3
By 373.8 g(1 mol) compound ii joins 2250 mL
1, in the two-phase solvent of 2-dichloroethanes and 350 mL water composition, add 11.2 g tetrabutyl ammonium bromide, it is warming up to 60 DEG C-65 DEG C, be simultaneously added dropwise 173 g 30%(1.3 mol) sodium hydrate aqueous solution and 164g(1.3 mol) dimethyl sulfate, keep reaction system pH=8-9, dropping in 2 hours is complete, 60 DEG C of-65 DEG C of insulated and stirred 2 hours, it is down to room temperature, divide and remove aqueous phase, organic facies concentrating under reduced pressure, recrystallisation solvent isopropanol is added in concentrate, it is filtrated to get compounds I, pale yellow crystals 370 g, HPLC measures (external standard) content 98.5%, yield 95.4%.
Embodiment 4
By 373.8 g(1 mol) compound ii joins 2549 mL
In the two-phase solvent of carbon tetrachloride and 3058 mL water composition, add 1.869 g benzyltrimethylammonium chlorides, it is warming up to 75 DEG C-80 DEG C, be simultaneously added dropwise 173 g 30%(1.3 mol) sodium hydrate aqueous solution and 164g(1.3 mol) dimethyl sulfate, keep reaction system pH=8-9, dropping in 2 hours is complete, 75 DEG C of-80 DEG C of insulated and stirred 3 hours, it is down to room temperature, divide and remove aqueous phase, organic facies concentrating under reduced pressure, recrystallisation solvent isopropanol is added in concentrate, it is filtrated to get compounds I, pale yellow crystals 368g, HPLC measures (external standard) content 98.7%, yield 94.9%.
Embodiment 5
By 373.8 g(1 mol) compound ii joins 2250 mL
In the two-phase solvent of chloroform and 350 mL water composition, add 11.2 g tetrabutyl ammonium bromide, at room temperature, be simultaneously added dropwise 243.5
G 30%(1.3 mol) potassium hydroxide aqueous solution and 164g(1.3 mol) dimethyl sulfate, keep reaction system pH=8-9, within 2 hours, drip complete, continue stirring and terminate to reaction, divide and remove aqueous phase, organic facies concentrating under reduced pressure, in concentrate, add recrystallisation solvent isopropanol, be filtrated to get compounds I, pale yellow crystals 371g, HPLC measures (external standard) content 98.6%, yield 95.8%.
Embodiment 6
By 373.8 g(1 mol) compound ii joins 2336 mL
1, in the two-phase solvent of 2-dichloroethanes and 1402 mL water composition, add 37.38 g PEG400s, it is warming up to 60 DEG C-65 DEG C, be simultaneously added dropwise 173 g 30%(1.3 mol) sodium hydrate aqueous solution and 164g(1.3 mol) dimethyl sulfate, keep reaction system pH=8-9, dropping in 2 hours is complete, 60 DEG C of-65 DEG C of insulated and stirred 2 hours, it is down to room temperature, divide and remove aqueous phase, organic facies concentrating under reduced pressure, recrystallisation solvent isopropanol is added in concentrate, it is filtrated to get compounds I, pale yellow crystals 374g, HPLC measures (external standard) content 98.1%, yield 96.4%.
Embodiment 7
By 373.8 g(1 mol) compound ii joins 2250 mL
In the two-phase solvent of chloroform and 350 mL water composition, add 11.2 g Macrogol 600s, be warming up to backflow, be simultaneously added dropwise 173 g 30%(1.3
Mol) sodium hydrate aqueous solution and 164g(1.3
Mol) dimethyl sulfate, keeping reaction system pH=8-9, dropping in 2 hours is complete, return stirring 2 hours, it is down to room temperature, divide and remove aqueous phase, organic facies concentrating under reduced pressure, in concentrate, add recrystallisation solvent isopropanol, it is filtrated to get compounds I, pale yellow crystals 375 g, HPLC measure (external standard) content 98.4%, yield 96.7%.
Embodiment 8
By 373.8 g(1 mol) compound ii joins 2250 mL
In the two-phase solvent of chloroform and 350 mL water composition, add 11.2 g benzyltrimethylammonium bromides, at 20 DEG C-25 DEG C, be simultaneously added dropwise 478.8 g 10%(2 mol) lithium hydroxide aqueous solution and 252.3g(2 mol) dimethyl sulfate, keep reaction system pH=8-9, dropping in 2 hours is complete, 20 DEG C-25 DEG C are continued stirring and terminate to reaction, divide and remove aqueous phase, organic facies concentrating under reduced pressure, in concentrate, add recrystallisation solvent isopropanol, it is filtrated to get compounds I, pale yellow crystals 375g, HPLC measure (external standard) content 98.5%, yield 96.7%.
Embodiment 9
By 373.8 g(1 mol) compound ii joins 2250 mL
In the two-phase solvent of 1,2-dichloroethanes and 350 mL water composition, add 11.2 g Macrogol 600s, be warming up to backflow, be simultaneously added dropwise 173 g 30%(1.3
Mol) sodium hydrate aqueous solution and 164g(1.3
Mol) dimethyl sulfate, keeping reaction system pH=8-9, dropping in 2 hours is complete, return stirring 2 hours, it is down to room temperature, divide and remove aqueous phase, organic facies concentrating under reduced pressure, in concentrate, add recrystallisation solvent isopropanol, it is filtrated to get compounds I, pale yellow crystals 372 g, HPLC measure (external standard) content 98.6%, yield 95.9%.
Embodiment 10
By 373.8 g(1 mol) compound ii joins 2250 mL
1, in the two-phase solvent of 2-dichloroethanes and 350 mL water composition, add 11.2 g polyethylene glycol-800, it is warming up to backflow, be simultaneously added dropwise 133 g 30%(1 mol) sodium hydrate aqueous solution and 126.1 g(1 mol) dimethyl sulfate, keeping reaction system pH=8-9, dropping in 2 hours is complete, return stirring 2 hours, it is down to room temperature, divide and remove aqueous phase, organic facies concentrating under reduced pressure, in concentrate, add recrystallisation solvent isopropanol, it is filtrated to get compounds I, pale yellow crystals 372g, HPLC measure (external standard) content 98.2%, yield 95.9%.
For those of ordinary skills, can be improved according to the above description or be converted, and all these modifications and variations all should be belonged to the protection domain of claims of the present invention.
Claims (10)
1. the method catalyzing and synthesizing pyraclostrobin, it is characterized in that: compound ii N-hydroxy-n-2-[(N-rubigan)-3-pyrazoles epoxide methyl] carbanilate is joined in two-phase solvent, add phase transfer catalyst, it is simultaneously added dropwise aqueous solution and the dimethyl sulfate of acid binding agent, keep reaction system pH=8-9, compound ii N-hydroxy-n-2-[(N-rubigan)-3-pyrazoles epoxide methyl] carbanilate and dimethyl sulfate is made to carry out etherification reaction, obtain compounds I pyraclostrobin, reaction equation is as follows:
。
A kind of method catalyzing and synthesizing pyraclostrobin the most according to claim 1, it is characterised in that described phase transfer catalyst is quaternary ammonium compound or polyether compound.
A kind of method catalyzing and synthesizing pyraclostrobin the most according to claim 2, it is characterised in that described quaternary ammonium compound is tetrabutylammonium chloride, tetrabutyl ammonium bromide, benzyltrimethylammonium chloride or benzyltrimethylammonium bromide；Polyether compound is PEG400, Macrogol 600 or polyethylene glycol-800.
A kind of method catalyzing and synthesizing pyraclostrobin the most according to claim 1, it is characterised in that described acid binding agent is the mixture of one or more in Lithium hydrate, potassium hydroxide, sodium hydroxide.
A kind of method catalyzing and synthesizing pyraclostrobin the most according to claim 4, it is characterised in that described acid binding agent is sodium hydroxide.
A kind of method catalyzing and synthesizing pyraclostrobin the most according to claim 1, it is characterised in that described two-phase solvent is made up of halogenated alkane and water, halogenated alkane be dichloromethane, 1,2-dichloroethanes, chloroform or carbon tetrachloride.
A kind of method catalyzing and synthesizing pyraclostrobin the most according to claim 1, it is characterized in that: the mol ratio of raw material is: compound ii: dimethyl sulfate: acid binding agent=1: 1～2: 1～2, phase transfer catalyst consumption is the 0.5%～10% of compound ii quality.
A kind of method catalyzing and synthesizing pyraclostrobin the most according to claim 1, it is characterized in that: the grams of compound ii is 1: 5～15 with the milliliter number ratio of two-phase solvent, two-phase solvent is halogenated alkane and water, and wherein the volume ratio of halogenated alkane and water is 1: 0.1～1.2.
A kind of method catalyzing and synthesizing pyraclostrobin the most according to claim 1, it is characterised in that: etherification reaction temperature is 20 DEG C～80 DEG C.
A kind of method catalyzing and synthesizing pyraclostrobin the most according to claim 1, it is characterised in that: after etherification reaction completes, divide and remove aqueous phase, organic facies concentrating under reduced pressure, in concentrate, add recrystallisation solvent, obtain compounds I
Pyraclostrobin.
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Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106243040A (en) * | 2016-07-28 | 2016-12-21 | 山东康乔生物科技有限公司 | A kind of pyraclostrobin novel crystal forms V and preparation method thereof |
| CN106543066A (en) * | 2016-11-11 | 2017-03-29 | 深圳市新阳唯康科技有限公司 | A kind of pyraclostrobin novel crystal forms and preparation method thereof |
| CN106631965A (en) * | 2016-12-21 | 2017-05-10 | 深圳市新阳唯康科技有限公司 | Novel pyraclostrobin crystal form and preparation method thereof |
| CN106749025A (en) * | 2016-11-14 | 2017-05-31 | 四川福思达生物技术开发有限责任公司 | A kind of method of succinct synthesizing pyrazole kresoxim-methyl |
| CN107021927A (en) * | 2017-03-28 | 2017-08-08 | 天津大学 | A kind of pyraclostrobin crystal formation and preparation method thereof |
| CN110092755A (en) * | 2018-01-31 | 2019-08-06 | 江苏优嘉植物保护有限公司 | A kind of production technology of pyraclostrobin safely cleaning |
| CN111655668A (en) * | 2018-01-17 | 2020-09-11 | Gsp作物科学有限公司 | Improved process for the preparation of pyraclostrobin |
| CN115304548A (en) * | 2022-09-05 | 2022-11-08 | 江苏七洲绿色科技研究院有限公司 | Preparation method of pyraclostrobin |
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Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106243040A (en) * | 2016-07-28 | 2016-12-21 | 山东康乔生物科技有限公司 | A kind of pyraclostrobin novel crystal forms V and preparation method thereof |
| CN106543066A (en) * | 2016-11-11 | 2017-03-29 | 深圳市新阳唯康科技有限公司 | A kind of pyraclostrobin novel crystal forms and preparation method thereof |
| CN106543066B (en) * | 2016-11-11 | 2018-12-21 | 深圳市新阳唯康科技有限公司 | A kind of pyraclostrobin crystal form and preparation method thereof |
| CN106749025A (en) * | 2016-11-14 | 2017-05-31 | 四川福思达生物技术开发有限责任公司 | A kind of method of succinct synthesizing pyrazole kresoxim-methyl |
| CN106749025B (en) * | 2016-11-14 | 2019-10-08 | 四川福思达生物技术开发有限责任公司 | A kind of method of succinct synthesizing pyrazole kresoxim-methyl |
| CN106631965A (en) * | 2016-12-21 | 2017-05-10 | 深圳市新阳唯康科技有限公司 | Novel pyraclostrobin crystal form and preparation method thereof |
| CN107021927A (en) * | 2017-03-28 | 2017-08-08 | 天津大学 | A kind of pyraclostrobin crystal formation and preparation method thereof |
| CN111655668A (en) * | 2018-01-17 | 2020-09-11 | Gsp作物科学有限公司 | Improved process for the preparation of pyraclostrobin |
| CN111655668B (en) * | 2018-01-17 | 2024-02-13 | Gsp作物科学有限公司 | Improved process for the preparation of pyraclostrobin |
| CN110092755A (en) * | 2018-01-31 | 2019-08-06 | 江苏优嘉植物保护有限公司 | A kind of production technology of pyraclostrobin safely cleaning |
| CN110092755B (en) * | 2018-01-31 | 2022-04-01 | 江苏优嘉植物保护有限公司 | Process for producing pyraclostrobin |
| CN115304548A (en) * | 2022-09-05 | 2022-11-08 | 江苏七洲绿色科技研究院有限公司 | Preparation method of pyraclostrobin |
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