CN109293565A - A kind of preparation method of fluopyram - Google Patents
A kind of preparation method of fluopyram Download PDFInfo
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- CN109293565A CN109293565A CN201811255959.4A CN201811255959A CN109293565A CN 109293565 A CN109293565 A CN 109293565A CN 201811255959 A CN201811255959 A CN 201811255959A CN 109293565 A CN109293565 A CN 109293565A
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- 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
- C07D213/61—Halogen atoms or nitro radicals
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Abstract
The present invention relates to a kind of preparation methods of fluopyram, including the following steps successively carried out: (1) by 2, bis- chloro-5-trifluoromethylpyridine of 3- and ethyl cyanoacetate or methyl cyanoacetate are in the presence of alkali and solvent, substitution reaction is carried out under conditions of 30~160 DEG C, after reaction, reaction solution is adjusted to acidity, carries out decarboxylic reaction under conditions of 80~160 DEG C, obtains 3- chloro- 5- (trifluoromethyl) -2- acetonitrile yl pyridines；(2) 3- chloro- 5- (the trifluoromethyl) -2- acetonitrile yl pyridines and o-trifluoromethyl chlorobenzoyl chloride step (1) being prepared are in the presence of catalyst, hydrogen, alkali and solvent, concatenated hydrogenation and condensation reaction are carried out under conditions of 20~100 DEG C, obtains the fluopyram.Step of the present invention is brief, avoids unnecessary upper protection-deprotection steps, and more economical environmental protection is suitable for industrialized production.
Description
Technical field
Present invention relates particularly to a kind of preparation methods of fluopyram.
Background technique
Fluopyram is a kind of new benzamides class fungicide of high-efficiency low-toxicity, by hindering succinic acid in respiratory chain
The electronics transfer of dehydrogenase and inhibit mitochondrial respiratory.Its fungicidal spectrum wide spectrum, is applicable to the multiple diseases of 70 multiple kinds of crops,
It is either applied alone or compounding all shows preferable control efficiency, be mainly used for prevention and treatment by the microbial grey mold of fungal pathogen
Disease, powdery mildew, late blight, downy mildew, rice blast etc. have very big development potentiality on pesticide market.
Route is mainly the following about the preparation of fluopyram at present:
Route one:
The route is starting with 2,3-, bis- chloro-5-trifluoromethylpyridine, diethyl malonate and o-trifluoromethyl benzoic acid
Raw material obtains final product fluopyram by 7 steps.The routine synthetic steps are more, and reaction condition is violent, and intermediate product
It is not easily separate purification, by-product is more, is not suitable for the large-scale production of industrialization.
Route two:
The route is with 2,3-, bis- chloro-5-trifluoromethylpyridine, ethyl cyanoacetate (or methyl cyanoacetate) and o-trifluoromethyl
Benzoic acid is raw material, and by deprotection and condensation are protected, restored in substitution, decarboxylation, reduction, totally 6 steps (include 1 step neighbour's trifluoromethyl benzonitrile
The synthesis of acyl chlorides) synthesis final product fluopyram.The route reduces one-step synthesis step, mesh compared with route one
This synthetic route is all selected as previous.
The patent of invention of Publication No. CN1674784A discloses Novel 2-pyridylethylbenzamidderivative derivative, public
The reaction route opened are as follows:
The route synthesizes final product by 5 steps (synthesis comprising 1 step neighbour's trifluorobenzoyl chloride), and reduction is anti-in the technique
Product yield is lower, and the three wastes are more.
Summary of the invention
The object of the present invention is to provide a kind of preparation methods of fluopyram that reaction step is few.
In order to solve the above technical problems, the present invention adopts the following technical scheme:
A kind of preparation method of fluopyram, including the following steps successively carried out:
(1) by bis- chloro-5-trifluoromethylpyridine of 2,3- (formula I) and ethyl cyanoacetate or methyl cyanoacetate (formula II) in alkali
In the presence of solvent, substitution reaction is carried out under conditions of 30~160 DEG C, after reaction, reaction solution is adjusted to acidity,
Decarboxylic reaction is carried out under conditions of 80~160 DEG C, obtains 3- chloro- 5- (trifluoromethyl) -2- acetonitrile yl pyridines (formula III)；
(2) 3- chloro- 5- (the trifluoromethyl) -2- acetonitrile yl pyridines (formula III) and adjacent fluoroform step (1) being prepared
Base chlorobenzoyl chloride (formula IV) carries out concatenated in the presence of catalyst, hydrogen, alkali and solvent under conditions of 20~100 DEG C
Hydrogenation and condensation reaction obtain the fluopyram (formula V).
Reaction equation of the invention are as follows:
Preferably, in step (1), the alkali be potassium hydroxide, potassium carbonate, sodium carbonate, sodium hydroxide, potassium tert-butoxide,
Sodium tert-butoxide, Sodamide, triethylamine, N, N- diisopropyl ethyl amine, N, one or more of N- dimethyl cyclohexyl amine.
Preferably, in step (1), the solvent is dimethyl sulfoxide, n,N-Dimethylformamide, N, N- dimethylacetamide
One of amine, N-Methyl pyrrolidone, tetrahydrofuran, acetonitrile, methylene chloride, 1,2- dichloroethanes, the tert-butyl alcohol, benzene, toluene
Or it is several.
Preferably, it in step (1), adopts and is adjusted with acid reaction solution to acidity, the acid is hydrochloric acid, hydrobromic acid or sulphur
Acid.
Preferably, in step (1), the acid pH is 2~3.
Preferably, in step (1), 2,3-, bis- chloro-5-trifluoromethylpyridine, the ethyl cyanoacetate or cyanogen
Methyl acetate, the alkali molar ratio be 1:1.0~2.0:1.0~4.0, further preferably 1:1~1.5:1~2.
Preferably, the specific embodiment of step (1) are as follows: by 2,3-, bis- chloro-5-trifluoromethylpyridine, described
Alkali is added in the solvent, and the ethyl cyanoacetate or methyl cyanoacetate is then added dropwise, after being added dropwise, 30~
It reacts 1~16 hour at 160 DEG C, after completion of the reaction, is cooled down, reaction solution is then adjusted into pH to 2~3 with acid, then 80
It reacts 1~16 hour at~160 DEG C, after reaction, is cooled down, the pH to 8~9 of reaction solution is then adjusted, with acetic acid second
Ester extraction, organic phase are concentrated, are evaporated under reduced pressure to obtain described 3- chloro- 5- (the trifluoromethyl) -2- acetonitrile yl pyridines.
Preferably, in step (2), the catalyst is palladium carbon, platinum carbon or Raney Ni.
Preferably, in step (2), the alkali is triethylamine, N, N- diisopropyl ethyl amine, N, N- dimethyleyelohexane
One or more of amine, potassium hydroxide, potassium carbonate, sodium hydroxide, sodium carbonate.
Preferably, in step (2), the solvent is dimethyl sulfoxide, n,N-Dimethylformamide, N, N- dimethylacetamide
Amine, N-Methyl pyrrolidone, tetrahydrofuran, acetonitrile, methylene chloride, 1,2- dichloroethanes, the tert-butyl alcohol, ethyl acetate, acetic acid fourth
One or more of ester, benzene, toluene.
Preferably, in step (2), the 3- chloro- 5- (trifluoromethyl) -2- acetonitrile yl pyridines, the adjacent fluoroform
The molar ratio of base chlorobenzoyl chloride and the alkali is 1:1.0~2.0:1.0~3.0, further preferably 1:1~1.5:1
~2.
Preferably, in step (2), the quality that feeds intake of the catalyst is described 3- chloro- 5- (the trifluoromethyl) -2- second
The 0.1~10% of itrile group pyridine quality, further preferably 1~10%.
Preferably, in step (2), being passed through the hydrogen to pressure is 0.1~10MPa.
Preferably, the specific embodiment of step (2) are as follows: by described 3- chloro- 5- (the trifluoromethyl) -2- acetonitrile-base pyrrole
Pyridine, the o-trifluoromethyl chlorobenzoyl chloride, the alkali are dissolved in the solvent, after leading to nitrogen displaced air, are added
The catalyst, then it is passed through the hydrogen, it is reacted 1~18 hour at 20~100 DEG C, after reaction, by reaction solution
Filtering is concentrated to get crude product after filtrate water washing, the crude product is carried out to be recrystallized to give the fluorine pyrrole bacterium acyl
Amine.
Due to the implementation of above technical scheme, the present invention has the advantage that compared with prior art
Step of the present invention is brief, avoids unnecessary upper protection-deprotection steps, and more economical environmental protection is suitable for industry
Metaplasia produces.
Specific embodiment
The present invention is described in further details below in conjunction with specific embodiment.It should be understood that these embodiments are for saying
The bright basic principles, principal features and advantages of the present invention, and the present invention is not limited by the following examples.It is used in the examples
Implementation condition can do further adjustment according to specific requirement, and the implementation condition being not specified is usually the condition in routine experiment.
The content is mass content below.
Embodiment one
The preparation method of the fluopyram of the present embodiment has follow steps:
By 2,3-, bis- chloro-5-trifluoromethylpyridine (10.0g, 46.5mmol), potassium carbonate (7.7g, 55.8mmol) is added to
In N,N-dimethylformamide (50mL).At room temperature, into said mixture instill cyan-acetic ester (6.3g,
55.8mmol).After being added dropwise, reaction is reacted 3 hours at 70 DEG C.After completion of the reaction, it is cooled to room temperature.With hydrochloric acid by pH tune
To 2~3, reaction solution stirs 16 hours at 140 DEG C.Reaction solution is cooled to room temperature, with 30% potassium hydroxide solution by pH
It is extracted with ethyl acetate after being adjusted to 8~9.It is evaporated under reduced pressure after organic phase concentration, obtains 3- chloro- 5- (trifluoromethyl) -2- acetonitrile-base pyrrole
Pyridine (8.63g), yellow oily liquid, yield 81%, purity 96%.
Be added into reaction flask obtained by step (1) 3- chloro- 5- (trifluoromethyl) -2- acetonitrile yl pyridines (8.63g,
37.7mmol), o-trifluoromethyl chlorobenzoyl chloride (9.4g, 45.2mmol), potassium carbonate (6.24g, 45.2mmol) and ethyl acetate
(100mL) is added Raney Ni (0.8g) after leading to nitrogen displaced air 3 times, then is passed through hydrogen displacement nitrogen 2 times, is flushed with hydrogen gas extremely
1.0MPa is gradually heated to 60 DEG C, reacts 10 hours, until stopping reaction when pressure no longer changes.Reaction solution is filtered, filtrate is used
It is concentrated after water washing.Crude product is recrystallized to obtain fluopyram (12.2g), white solid, yield 80%, purity 98%.
Embodiment two
The preparation method of the fluopyram of the present embodiment has follow steps:
By 2,3-, bis- chloro-5-trifluoromethylpyridine (10.0g, 46.5mmol), potassium hydroxide (2.6g, 46.5mmol) is added
To in dimethyl sulfoxide (50mL).At room temperature, cyan-acetic ester (5.25g, 46.5mmol) is instilled into said mixture.Drop
After adding, reaction is reacted 3 hours at 70 DEG C.After completion of the reaction, it is cooled to room temperature.PH is adjusted to 2~3 with hydrochloric acid, reaction
Liquid stirs 13 hours at 160 DEG C.Reaction solution is cooled to room temperature, is used after pH is adjusted to 8~9 with 30% potassium hydroxide solution
Ethyl acetate extraction.It is evaporated under reduced pressure after organic phase concentration, obtains 3- chloro- 5- (trifluoromethyl) -2- acetonitrile yl pyridines (8.5g), yellow
Oily liquids, yield 79%, purity 95%.
Be added into reaction flask obtained by step (1) 3- chloro- 5- (trifluoromethyl) -2- acetonitrile yl pyridines (8.5g,
36.7mmol), o-trifluoromethyl chlorobenzoyl chloride (8.4g, 40.4mmol), potassium carbonate (5.57g, 40.4mmol) and toluene
(100mL) is added Raney Ni (0.8g) after leading to nitrogen displaced air 3 times, then is passed through hydrogen displacement nitrogen 2 times, is flushed with hydrogen gas extremely
3.0MPa is gradually heated to 40 DEG C, reacts 6 hours, until stopping reaction when pressure no longer changes.Reaction solution is filtered, filtrate is used
It is concentrated after water washing.Crude product is recrystallized to obtain fluopyram (11.7g), white solid, yield 78%, purity 97%.
Embodiment three
The preparation method of the fluopyram of the present embodiment has follow steps:
By 2,3-, bis- chloro-5-trifluoromethylpyridine (10.0g, 46.5mmol), potassium carbonate (9.6g, 70.0mmol) is added to
In dimethyl sulfoxide (70mL).At room temperature, malonic methyl ester nitrile (6.93g, 70.0mmol) is instilled into said mixture.It is added dropwise
After, reaction is reacted 2 hours at 80 DEG C.After completion of the reaction, it is cooled to room temperature.PH is adjusted to 2~3 with hydrochloric acid, reaction solution
It is stirred 14 hours at 160 DEG C.Reaction solution is cooled to room temperature, uses second after pH is adjusted to 8~9 with 30% potassium hydroxide solution
Acetoacetic ester extraction.It is evaporated under reduced pressure after organic phase concentration, obtains 3- chloro- 5- (trifluoromethyl) -2- acetonitrile yl pyridines (8.84g), yellow
Oily liquids, yield 83%, purity 96%.
Be added into reaction flask obtained by step (1) 3- chloro- 5- (trifluoromethyl) -2- acetonitrile yl pyridines (8.84g,
38.6mmol), o-trifluoromethyl chlorobenzoyl chloride (12g, 57.9mmol), sodium carbonate (6.14g, 57.9mmol) and ethyl acetate
(100mL) is added palladium carbon (0.5g) after leading to nitrogen displaced air 3 times, then is passed through hydrogen displacement nitrogen 2 times, is flushed with hydrogen gas extremely
2.0MPa is gradually heated to 60 DEG C, reacts 8 hours, until stopping reaction when pressure no longer changes.Reaction solution is filtered, filtrate is used
It is concentrated after water washing.Crude product is recrystallized to obtain fluopyram (13g), white solid, yield 82%, purity 96%.
Example IV
The preparation method of the fluopyram of the present embodiment has follow steps:
By 2,3-, bis- chloro-5-trifluoromethylpyridine (10.0g, 46.5mmol), sodium carbonate (5.9g, 55.8mmol) is added to
In N,N-dimethylformamide (50mL).At room temperature, into said mixture instill cyan-acetic ester (6.3g,
55.8mmol).After being added dropwise, reaction is reacted 3 hours at 70 DEG C.After completion of the reaction, it is cooled to room temperature.With hydrochloric acid by pH tune
To 2~3, reaction solution stirs 16 hours at 140 DEG C.Reaction solution is cooled to room temperature, with 30% potassium hydroxide solution by pH
It is extracted with ethyl acetate after being adjusted to 8~9.It is evaporated under reduced pressure after organic phase concentration, obtains 3- chloro- 5- (trifluoromethyl) -2- acetonitrile-base pyrrole
Pyridine (7.65g), yellow oily liquid, yield 70%, purity 94%.
Be added into reaction flask obtained by step (1) 3- chloro- 5- (trifluoromethyl) -2- acetonitrile yl pyridines (7.65g,
32.6mmol), o-trifluoromethyl chlorobenzoyl chloride (8.2g, 39.1mmol), potassium carbonate (5.4g, 39.1mmol) and ethyl acetate
(100mL) is added Raney Ni (0.8g) after leading to nitrogen displaced air 3 times, then is passed through hydrogen displacement nitrogen 2 times, is flushed with hydrogen gas extremely
1.0MPa is gradually heated to 60 DEG C, reacts 10 hours, until stopping reaction when pressure no longer changes.Reaction solution is filtered, filtrate is used
It is concentrated after water washing.Crude product is recrystallized to obtain fluopyram (10.65g), white solid, yield 79%, purity 96%.
Embodiment five
By 2,3-, bis- chloro-5-trifluoromethylpyridine (10.0g, 46.5mmol), potassium carbonate (7.7g, 55.8mmol) is added to
In N,N-dimethylformamide (50mL).At room temperature, into said mixture instill cyan-acetic ester (6.3g,
55.8mmol).After being added dropwise, reaction is reacted 3 hours at 70 DEG C.After completion of the reaction, it is cooled to room temperature.With hydrochloric acid by pH tune
To 2~3, reaction solution stirs 16 hours at 140 DEG C.Reaction solution is cooled to room temperature, with 30% potassium hydroxide solution by pH
It is extracted with ethyl acetate after being adjusted to 8~9.It is evaporated under reduced pressure after organic phase concentration, obtains 3- chloro- 5- (trifluoromethyl) -2- acetonitrile-base pyrrole
Pyridine (8.63g), yellow oily liquid, yield 81%, purity 96%.
Be added into reaction flask obtained by step (1) 3- chloro- 5- (trifluoromethyl) -2- acetonitrile yl pyridines (8.63g,
37.7mmol), o-trifluoromethyl chlorobenzoyl chloride (9.4g, 45.2mmol), potassium carbonate (6.24g, 45.2mmol) and ethyl acetate
(100mL) is added Raney Ni (0.5g) after leading to nitrogen displaced air 3 times, then is passed through hydrogen displacement nitrogen 2 times, is flushed with hydrogen gas extremely
1.0MPa is gradually heated to 30 DEG C, reacts 10 hours, until stopping reaction when pressure no longer changes.Reaction solution is filtered, filtrate is used
It is concentrated after water washing.Crude product is recrystallized to obtain fluopyram (8.13g), white solid, yield 50%, purity 92%.
The above embodiments merely illustrate the technical concept and features of the present invention, and its object is to allow person skilled in the art
Scholar cans understand the content of the present invention and implement it accordingly, and it is not intended to limit the scope of the present invention, it is all according to the present invention
Equivalent change or modification made by Spirit Essence, should be covered by the protection scope of the present invention.
Claims (11)
1. a kind of preparation method of fluopyram, it is characterised in that: including the following steps successively carried out:
(1) by 2,3-, bis- chloro-5-trifluoromethylpyridine and ethyl cyanoacetate or methyl cyanoacetate in the presence of alkali and solvent,
Substitution reaction is carried out under conditions of 30~160 DEG C, after reaction, reaction solution is adjusted to acidity, in 80~160 DEG C of condition
Lower carry out decarboxylic reaction obtains 3- chloro- 5- (trifluoromethyl) -2- acetonitrile yl pyridines；
(2) 3- chloro- 5- (the trifluoromethyl) -2- acetonitrile yl pyridines and o-trifluoromethyl chlorobenzoyl chloride step (1) being prepared
In the presence of catalyst, hydrogen, alkali and solvent, concatenated hydrogenation and condensation reaction are carried out under conditions of 20~100 DEG C, is obtained
To the fluopyram.
2. the preparation method of fluopyram according to claim 1, it is characterised in that: in step (1), the alkali is
Potassium hydroxide, potassium carbonate, sodium carbonate, sodium hydroxide, potassium tert-butoxide, sodium tert-butoxide, Sodamide, triethylamine, N, N- diisopropyl
Ethylamine, N, one or more of N- dimethyl cyclohexyl amine；The solvent be dimethyl sulfoxide, N,N-dimethylformamide,
DMAC N,N' dimethyl acetamide, N-Methyl pyrrolidone, tetrahydrofuran, acetonitrile, methylene chloride, 1,2- dichloroethanes, the tert-butyl alcohol,
One or more of benzene, toluene.
3. the preparation method of fluopyram according to claim 1, it is characterised in that: in step (1), adopt and be adjusted with acid
For reaction solution to acidity, the acid is hydrochloric acid, hydrobromic acid or sulfuric acid.
4. the preparation method of fluopyram according to claim 1, it is characterised in that: in step (1), the acidity
PH be 2~3.
5. the preparation method of fluopyram according to claim 1, it is characterised in that: in step (1), described 2,3-
Two chloro-5-trifluoromethylpyridines, the ethyl cyanoacetate or methyl cyanoacetate, the alkali molar ratio be 1:
1.0~2.0:1.0~4.0.
6. the preparation method of fluopyram according to any one of claim 1 to 5, it is characterised in that: step (1)
Specific embodiment are as follows: be added to 2,3-, bis- chloro-5-trifluoromethylpyridine, the alkali in the solvent, so
The ethyl cyanoacetate or methyl cyanoacetate are added dropwise afterwards, after being added dropwise, reacts 1~16 hour at 30~160 DEG C, instead
It after answering, is cooled down, reaction solution is then adjusted into pH to 2~3 with acid, then react 1~16 hour at 80~160 DEG C,
After reaction, it is cooled down, then adjusts the pH to 8~9 of reaction solution, be extracted with ethyl acetate, organic phase is concentrated, is subtracted
Pressure distillation obtains described 3- chloro- 5- (the trifluoromethyl) -2- acetonitrile yl pyridines.
7. the preparation method of fluopyram according to claim 1, it is characterised in that: in step (2), the catalysis
Agent is palladium carbon, platinum carbon or Raney Ni；The alkali is triethylamine, N, N- diisopropyl ethyl amine, N, N- dimethyl cyclohexyl amine, hydrogen
One or more of potassium oxide, potassium carbonate, sodium hydroxide, sodium carbonate；The solvent is dimethyl sulfoxide, N, N- dimethyl methyl
Amide, DMAC N,N' dimethyl acetamide, N-Methyl pyrrolidone, tetrahydrofuran, acetonitrile, methylene chloride, 1,2- dichloroethanes, tertiary fourth
One or more of alcohol, ethyl acetate, butyl acetate, benzene, toluene.
8. the preparation method of fluopyram according to claim 1, it is characterised in that: in step (2), the 3-
The molar ratio of chloro- 5- (trifluoromethyl) -2- acetonitrile yl pyridines, the o-trifluoromethyl chlorobenzoyl chloride and the alkali is
1:1.0~2.0:1.0~3.0.
9. the preparation method of fluopyram according to claim 1, it is characterised in that: in step (2), the catalysis
The quality that feeds intake of agent is the 0.1~10% of described 3- chloro- 5- (the trifluoromethyl) -2- acetonitrile yl pyridines quality.
10. the preparation method of fluopyram according to claim 1, it is characterised in that: in step (2), be passed through described
Hydrogen to pressure be 0.1~10MPa.
11. the preparation method of fluopyram according to any one of claims 7 to 10, it is characterised in that: step (2)
Specific embodiment are as follows: by 3- chloro- 5- (the trifluoromethyl) -2- acetonitrile yl pyridines, the o-trifluoromethyl benzene first
Acyl chlorides, the alkali are dissolved in the solvent, and after leading to nitrogen displaced air, the catalyst is added, then are passed through described
Hydrogen, react 1~18 hour at 20~100 DEG C, after reaction, reaction solution filtered, filtrate water washing after be concentrated
Crude product is obtained, the crude product is carried out to be recrystallized to give the fluopyram.
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| CN110437139A (en) * | 2019-08-12 | 2019-11-12 | 大连九信精细化工有限公司 | A kind of synthetic method of fluopyram |
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| CN114031551A (en) * | 2021-12-27 | 2022-02-11 | 利民化学有限责任公司 | Fluopyram and synthesis method thereof |
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| CN110437138A (en) * | 2019-08-12 | 2019-11-12 | 大连九信精细化工有限公司 | A kind of improvement synthesis technology of fluopyram |
| CN110437139A (en) * | 2019-08-12 | 2019-11-12 | 大连九信精细化工有限公司 | A kind of synthetic method of fluopyram |
| CN111056997A (en) * | 2019-12-09 | 2020-04-24 | 西安近代化学研究所 | Synthetic method of benzamide compound |
| CN113429338A (en) * | 2021-05-20 | 2021-09-24 | 陕西泰合利华工业有限公司 | Method for synthesizing fluopyram |
| CN114031551A (en) * | 2021-12-27 | 2022-02-11 | 利民化学有限责任公司 | Fluopyram and synthesis method thereof |
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