CN110330480A - A kind of nicosulfuron crystalline hydrate and its preparation method and application - Google Patents
A kind of nicosulfuron crystalline hydrate and its preparation method and application Download PDFInfo
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- CN110330480A CN110330480A CN201910693435.1A CN201910693435A CN110330480A CN 110330480 A CN110330480 A CN 110330480A CN 201910693435 A CN201910693435 A CN 201910693435A CN 110330480 A CN110330480 A CN 110330480A
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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Abstract
The present invention provides a kind of nicosulfuron crystalline hydrates and its preparation method and application, belong to organic synthesis field.The present invention provides a kind of nicosulfuron crystalline hydrates with good crystal form, the no longer moisture absorption moisture absorption in air, stability is good, it is easily dried and following process, and the product chemical purity is very high, even particle size distribution, good dispersion, the better stability of preparation of following process, disintegration rate is fast, bioactivity is high, with apparent quality-advantage, it is dry in workshop, it crushes, in packaging and Downstream processing production process, there is no the tacky phenomenons of the material moisture absorption, be conducive to clean manufacturing and preparation ingredients, and have production process simple, high income, the advantages that at low cost.
Description
Technical field
The present invention relates to technical field of organic synthesis more particularly to a kind of nicosulfuron crystalline hydrate and preparation method thereof
And application.
Background technique
Nicosulfuron product currently on the market be it is anhydrous unformed powdered, it is special with the stronger moisture absorption moisture absorption
Point, thus in workshop drying, crushing, packaging and Downstream processing production process, the generally existing material moisture absorption is tacky, produces
Scene pollution, preparation ingredient is uneven, even generates the disadvantages of phytotoxicity.
Summary of the invention
In view of this, the purpose of the present invention is to provide a kind of nicosulfuron crystalline hydrate and preparation method thereof and answering
With.The nicosulfuron crystalline hydrate provided by the invention no longer moisture absorption moisture absorption in air, stability is good, is easily dried and subsequent
Processing.
In order to achieve the above-mentioned object of the invention, the present invention the following technical schemes are provided:
The present invention provides a kind of nicosulfuron crystalline hydrate, structure is shown in formula I:
The present invention also provides the preparation method of the nicosulfuron crystalline hydrate described in above-mentioned technical proposal, including it is following
Step:
By pyrilamine, [3- (N, N- Dimethylaminocarbonyl -2- pyridyl group) sulfonyl amido] phenyl formate and dichloromethane
Alkane mixing, carries out amidation process, obtains amidated products；
It is layered after the amidated products are mixed with sodium carbonate liquor, obtains water layer；
Water layer acid is neutralized, neutralized reaction product is obtained；
The neutralized reaction product is successively carried out to cooling filtering and drying, obtains the nicosulfuron crystalline hydrate.
Preferably, the pyrilamine and [3- (N, N- Dimethylaminocarbonyl -2- pyridyl group) sulfonyl amido] formic acid benzene
The molar ratio of ester is 1.1~1.3:1.
Preferably, the temperature of the amidation process is 38~60 DEG C.
Preferably, the heating rate for being warming up to the amidation process is 5~12 DEG C/h.
Preferably, the outlet temperature of the cooling filtering is 15~20 DEG C.
Preferably, the rate of temperature fall of the cooling filtering is 10~18 DEG C/h.
Preferably, the temperature of the drying is 50~70 DEG C, and the time is 4~6h.
Preferably, the acid is sulfuric acid, acetic acid, phosphoric acid, formic acid or hydrochloric acid.
The present invention also provides described in above-mentioned technical proposal nicosulfuron crystalline hydrate or above-mentioned technical proposal described in
Application of the nicosulfuron crystalline hydrate in pesticide field made from preparation method.
The present invention provides a kind of nicosulfuron crystalline hydrate, structure is shown in formula I:
The present invention provides a kind of nicosulfuron crystalline hydrates with good crystal form, and no longer moisture absorption is inhaled in air
Tide, stability is good, is easily dried and following process, and the product chemical purity is very high, even particle size distribution, good dispersion, after
The better stability of preparation of continuous processing, disintegration rate is fast, and disintegration time was less than 40 seconds, and the preparation of anhydrous nicosulfuron disintegration speed
It spends and is greater than 55 seconds, bioactivity is high, has apparent quality-advantage, in workshop drying, crushing, packaging and Downstream processing system
During agent, the tacky phenomenon of the material moisture absorption is not present, is conducive to clean manufacturing and preparation ingredients, and there is production process letter
Easily, high income, it is at low cost the advantages that.
Detailed description of the invention
Fig. 1 is the DSC curve of nicosulfuron crystalline hydrate made from embodiment 1；
Fig. 2 is the thermogravimetric curve of nicosulfuron crystalline hydrate made from embodiment 1；
Fig. 3 is the infrared spectrum of nicosulfuron crystalline hydrate made from embodiment 1.
Specific embodiment
The present invention provides a kind of nicosulfuron crystalline hydrate, structure is shown in formula I:
Heretofore described nicosulfuron crystalline hydrate is colorless and odorless powder, and fusing point is 138~140 DEG C, is not dissolved in
Toluene and chloroform, are slightly soluble in ethyl alcohol, can be used as the use of high-efficiency low-toxicity broad-spectrum herbicide.
The present invention also provides the preparation method of the nicosulfuron crystalline hydrate described in above-mentioned technical proposal, including it is following
Step:
By pyrilamine, [3- (N, N- Dimethylaminocarbonyl -2- pyridyl group) sulfonyl amido] phenyl formate and dichloromethane
Alkane mixing, carries out amidation process, obtains amidated products；
It is layered after the amidated products are mixed with sodium carbonate liquor, obtains water layer；
Water layer acid is neutralized, neutralized reaction product is obtained；
The neutralized reaction product is successively carried out to cooling filtering and drying, obtains the nicosulfuron crystalline hydrate.
The present invention by pyrilamine, [3- (N, N- Dimethylaminocarbonyl -2- pyridyl group) sulfonyl amido] phenyl formate and
Methylene chloride mixing, carries out amidation process, obtains amidated products.
In the present invention, the pyrilamine and [3- (N, N- Dimethylaminocarbonyl -2- pyridyl group) sulfonyl amido] first
The molar ratio of acid phenenyl ester is preferably 1.1~1.3:1.The present invention does not have special restriction to the dosage of the methylene chloride, can
Guarantee that raw material is uniformly mixed.The present invention is to the pyrilamine and [3- (N, N- Dimethylaminocarbonyl -2- pyridyl group) sulphonyl
Base amido] source of phenyl formate do not have special restriction, it is made using preparation method well known to those skilled in the art or city
Sell commodity.
In the present invention, the structure of the pyrilamine is as shown in Formula II:
In the present invention, described [3- (N, the N- Dimethylaminocarbonyl -2- pyridyl group) sulfonyl amido] phenyl formate
Structure is as shown in formula III:
In the present invention, the temperature of the amidation process is preferably 38~60 DEG C, and more preferably 40~45 DEG C.The present invention
There is no special restriction to the time of the amidation process, is when the mass concentration of unreacted pyrilamine is less than 2%
Fully reacting.In the present invention, it is preferred to detect pyrilamine using thin-layered chromatography, the solvent of the thin-layered chromatography is preferably
The volume ratio of the mixed solvent of chloroform and methanol, the in the mixed solvent chloroform and methanol is preferably 2:1.
In the present invention, the heating rate for being warming up to the temperature of the amidation process is preferably 5~12 DEG C/h, more preferably
For 8~10 DEG C/h.
After obtaining amidated products, the present invention is layered after mixing the amidated products with sodium carbonate liquor, obtains water
Layer.In the present invention, the sodium carbonate liquor is preferably prepared by 150 kilograms of sodium carbonate with 400 kg of water.
After obtaining water layer, the present invention neutralizes water layer acid, obtains neutralized reaction product.In the present invention, the acid is excellent
It is selected as sulfuric acid, acetic acid, phosphoric acid, formic acid or hydrochloric acid.The present invention does not have special restriction to the dosage of the acid, can obtain neutrality
Product.In the present invention, the concentration of the hydrochloric acid is preferably 30%.
After obtaining neutralized reaction product, the neutralized reaction product is successively carried out cooling filtering and drying by the present invention, obtains the cigarette
Sulfometuron Methyl crystalline hydrate.
In the present invention, the outlet temperature of the cooling filtering is preferably 15~20 DEG C.
In the present invention, the rate of temperature fall of the cooling filtering is preferably 10~18 DEG C/h, more preferably 13~15 DEG C/h.
In the present invention, the temperature of the drying is preferably 50~70 DEG C, and the time is preferably 4~6h.In the present invention, exist
Drying removing is carried out at a temperature of this is free water.
The present invention also provides described in above-mentioned technical proposal nicosulfuron crystalline hydrate or above-mentioned technical proposal described in
Application of the nicosulfuron crystalline hydrate in pesticide field made from preparation method.
In order to further illustrate the present invention, below with reference to example to nicosulfuron crystalline hydrate provided by the invention and its
Preparation method and application are described in detail, but they cannot be interpreted as limiting the scope of the present invention.
Embodiment 1
2000 kilograms of methylene chloride measured are added in 3000 liters of glassed steel reaction vessels, are separately added into 580 kilograms of [3-
(N, N- Dimethylaminocarbonyl -2- pyridyl group) sulfonyl amido] phenyl formate and 215 kilograms of pyrilamines, it is heated to 40 DEG C and (adds
Hot rate is 5 DEG C/h), it is stirred to react, pyrilamine is detected using thin-layered chromatography after 5 hours, terminal is unreacted pyrilamine
Mass concentration less than 2%, the solvent of thin-layered chromatography is the mixed solvent (volume ratio 2:1) of chloroform and methanol, until
Reaction terminates, and the solution of 150 kilograms of sodium carbonate and 400 kg of water is added, and stirring, stratification separates water layer and enters neutralization kettle,
It is neutralized with hydrochloric acid (30%), nicosulfuron crystalline hydrate is precipitated, filtering (reduction rate is 10 DEG C/h), filter after being cooled to 15 DEG C
Cake is measured by sampling after drying 4 hours in 50 DEG C, until terminating drying when material constant weight, obtains finished product nicosulfuron crystalline hydrate
543 kilograms, yield 95.47%, external standard method detection level is 98.11%.
XRD test is carried out to nicosulfuron crystalline hydrate made from embodiment 1, obtains that the results are shown in Table 1, by table
1 it is found that nicosulfuron crystalline hydrate has been made in the present invention.
1 nicosulfuron crystalline hydrate XRD test data of table
Peak List
Dsc analysis is carried out to nicosulfuron crystalline hydrate made from embodiment 1, obtained spectrogram is as shown in Figure 1, to reality
It applies nicosulfuron crystalline hydrate made from example 1 and carries out thermogravimetric analysis, obtained spectrogram is as shown in Fig. 2, to made from embodiment 1
Nicosulfuron crystalline hydrate carries out infrared spectrum analysis, and obtained spectrogram is as shown in figure 3, by Fig. 1~3 it is found that system of the present invention
The nicosulfuron crystalline hydrate molecular weight 410.41+18 obtained, wherein nicosulfuron molecular weight is 410.41, and moisture is calculated
Accounting 4.2%, it is known that contain a crystallization water in nicosulfuron crystalline hydrate obtained.
The disintegration rate and stability of nicosulfuron crystalline hydrate made from the present embodiment are measured, disintegration speed
Degree measuring method indicates that general provision is not more than 3min to measure disintegration time length, the method is as follows: Xiang Hanyou 90mL distillation
In 100mL tool plug graduated cylinder (interior high 22.5cm, internal diameter 28mm) of water, sample particle (0.5g, the diameter of particle are added at 25 DEG C
It is 250~1410 μm), the middle part of graduated cylinder is clamped later, clogs nozzle, is rotated with the speed of 8r/min around center, until sample
Disintegration completely in water, records time, as disintegration rate.The results are shown in Table 2, and as can be seen from Table 2, the present embodiment is made
Nicosulfuron crystalline hydrate disintegration rate it is fast, thermodynamic stability is high.
2 nicosulfuron crystalline hydrate of table and commercially available nicosulfuron performance comparison
| Number | Sample source | Content % | Crystal form | Disintegration rate | Thermodynamic stability | Remarks |
| 1 | Commercially available JB | 92.3 | Ib | 185 seconds | Decompose 7% | Anhydride |
| 2 | Commercially available JY | 90.1 | Ib | 92 seconds | Decompose 9% | Anhydride |
| 3 | Commercially available ZZ | 97.6 | Ib | 195 seconds | Decompose 6% | Anhydride |
| 4 | Commercially available Xin Nongji | 97.8 | Ib | 55 seconds | Decompose 1.3% | Anhydride |
| 5 | Embodiment 1 | 95.4 | II | 36 seconds | Decompose 0.6% | One crystallization water |
The moisture absorption weight gain performance of nicosulfuron crystalline hydrate made from the present embodiment is measured, porosity test operation
Process: each 5 grams of nicosulfuron crystalline hydrate sample made from commercially available nicosulfuron and the present embodiment are weighed respectively, are put into cleaning
Glass culture dish in shakeout, open room temperature be stored in humidity be 50~60% air in, timing sampling measures its moisture and contains
Amount the results are shown in Table 3, as can be seen from Table 3, nicosulfuron crystalline hydrate made from the present embodiment with the extension of time,
Its contained humidity content is constant, and appearance particle is comfortable not to be changed；And commercially available nicosulfuron sample is with the extension of time, appearance is micro-
Grain is more and more viscous, and contained humidity content gradually increases, but (the exactly anhydrous nicosulfuron molecular weight when increasing to 4.2%
410, increase the incrementss of a hydrone molecular weight 18), crystal form tends to completely, not continue to the moisture absorption.
3 nicosulfuron crystalline hydrate of table and commercially available nicosulfuron moisture absorption weight gain performance result
Embodiment 2
2000 kilograms of methylene chloride measured are added in 3000 liters of glassed steel reaction vessels, are separately added into 580 kilograms of [3-
(N, N- Dimethylaminocarbonyl -2- pyridyl group) sulfonyl amido] phenyl formate and 220 kilograms of pyrilamines, it is heated to 41 DEG C and (rises
Warm rate is 7 DEG C/h), it is stirred to react, pyrilamine is detected using thin-layered chromatography after 5 hours, terminal is unreacted pyrilamine
Mass concentration less than 2%, the solvent of thin-layered chromatography is the mixed solvent (volume ratio 2:1) of chloroform and methanol, until
Reaction terminates, and the solution of 150 sodium carbonate and 400 kg of water, stirring is added, and stratification separates water layer and enters neutralization kettle, uses
30% hydrochloric acid neutralizes, and nicosulfuron crystalline hydrate is precipitated, filtering (reduction rate is 10 DEG C/h), filter cake after being cooled to 17 DEG C
Drying to constant weight in 60 DEG C, obtains 538 kilograms of finished product nicosulfuron crystalline hydrate, yield 94.59%, external standard method detection level
It is 98.21%.
Embodiment 3
2000 kilograms of methylene chloride measured are added in 3000 liters of glassed steel reaction vessels, are separately added into 580 kilograms of [3-
(N, N- Dimethylaminocarbonyl -2- pyridyl group) sulfonyl amido] phenyl formate and 225 kilograms of pyrilamines, it is heated to 38 DEG C and (adds
Hot rate is 10 DEG C/h), it is stirred to react, pyrilamine is detected using thin-layered chromatography after 6 hours, terminal is unreacted pyrilamine
Mass concentration less than 2%, the solvent of thin-layered chromatography is the mixed solvent (volume ratio 2:1) of chloroform and methanol, until
Reaction terminates, and the solution of 150 sodium carbonate and 400 kg of water, stirring is added, and stratification separates water layer and enters neutralization kettle, uses
30% hydrochloric acid neutralizes, and nicosulfuron crystalline hydrate is precipitated, filtering (reduction rate is 18 DEG C/h), filter cake after being cooled to 20 DEG C
It is dried 5 hours in 70 DEG C, obtains 535 kilograms of finished product nicosulfuron crystalline hydrate, yield 94.06%, external standard method detection level
It is 98.23%.
Embodiment 4
2000 kilograms of methylene chloride measured are added in 3000 liters of glassed steel reaction vessels, are separately added into 580 kilograms of [3-
(N, N- Dimethylaminocarbonyl -2- pyridyl group) sulfonyl amido] phenyl formate and 234 kilograms of pyrilamines, it is heated to 38 DEG C and (adds
Hot rate is 10 DEG C/h), it is stirred to react, pyrilamine is detected using thin-layered chromatography after 6 hours, terminal is unreacted pyrilamine
Mass concentration less than 2%, the solvent of thin-layered chromatography is the mixed solvent (volume ratio 2:1) of chloroform and methanol, until
Reaction terminates, and the solution of 150 sodium carbonate and 400 kg of water, stirring is added, and stratification separates water layer and enters neutralization kettle, uses
30% hydrochloric acid neutralizes, and nicosulfuron crystalline hydrate is precipitated, filtering (reduction rate is 15 DEG C/h), filter cake after being cooled to 18 DEG C
It is dried 5 hours in 70 DEG C, obtains 540 kilograms of finished product nicosulfuron crystalline hydrate, yield 94.94%, external standard method detection level
It is 98.19%.
The performance of nicosulfuron crystalline hydrate made from embodiment 2~4 is measured, the results are shown in Table 4, by table
4 as can be seen that nicosulfuron crystalline hydrate chemical purity produced by the present invention is high, and the preparation of good dispersion, following process is steady
Qualitative good, disintegration rate is fast, and thermodynamic stability is good, is not easy moisture absorption weight gain.
The performance measurement result of nicosulfuron crystalline hydrate made from 4 embodiment 2~4 of table
| Sample source | Content % | Disintegration rate | Thermodynamic stability | The moisture absorption increases weight 24 hours |
| Embodiment 2 | 95.5 | 35 seconds | Decompose 0.7% | 0 |
| Embodiment 3 | 95.4 | 34 seconds | Decompose 0.6% | 0 |
| Embodiment 4 | 95.3 | 35 seconds | Decompose 0.6% | 0 |
The above is only a preferred embodiment of the present invention, it is not intended to limit the present invention in any form.It should
It points out, for those skilled in the art, without departing from the principle of the present invention, if can also make
Dry improvements and modifications, these modifications and embellishments should also be considered as the scope of protection of the present invention.
Claims (10)
1. a kind of nicosulfuron crystalline hydrate, which is characterized in that structure is shown in formula I:
2. the preparation method of nicosulfuron crystalline hydrate described in claim 1, which comprises the following steps:
Pyrilamine, [3- (N, N- Dimethylaminocarbonyl -2- pyridyl group) sulfonyl amido] phenyl formate and methylene chloride is mixed
It closes, carries out amidation process, obtain amidated products；
It is layered after the amidated products are mixed with sodium carbonate liquor, obtains water layer；
Water layer acid is neutralized, neutralized reaction product is obtained；
The neutralized reaction product is successively carried out to cooling filtering and drying, obtains the nicosulfuron crystalline hydrate.
3. preparation method according to claim 2, which is characterized in that the pyrilamine and [3- (N, N- dimethylamino carbonyl
Base -2- pyridyl group) sulfonyl amido] phenyl formate molar ratio be 1.1~1.3:1.
4. preparation method according to claim 2, which is characterized in that the temperature of the amidation process is 38~60 DEG C.
5. preparation method according to claim 2 or 4, which is characterized in that be warming up to the heating speed of the amidation process
Rate is 5~12 DEG C/h.
6. preparation method according to claim 2, which is characterized in that the outlet temperature of the cooling filtering is 15~20
℃。
7. the preparation method according to claim 2 or 6, which is characterized in that it is described cooling filtering rate of temperature fall be 10~
18℃/h。
8. preparation method according to claim 2, which is characterized in that the temperature of the drying is 50~70 DEG C, the time 4
~6h.
9. preparation method according to claim 2, which is characterized in that the acid is sulfuric acid, acetic acid, phosphoric acid, formic acid or salt
Acid.
10. any one of nicosulfuron crystalline hydrate described in claim 1 or claim 2~9 preparation method are made
Application of the nicosulfuron crystalline hydrate in pesticide field.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111978293A (en) * | 2020-08-24 | 2020-11-24 | 天津大学 | Nicosulfuron-urea eutectic and preparation method thereof |
| CN113387928A (en) * | 2021-06-15 | 2021-09-14 | 淄博新农基作物科学有限公司 | Method for circularly producing nicosulfuron technical by using byproduct phenol |
| RU2827153C1 (en) * | 2024-03-11 | 2024-09-23 | Акционерное общество "Щелково Агрохим" | Method of producing herbicide nicosulfuron |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0237292A2 (en) * | 1986-03-07 | 1987-09-16 | E.I. Du Pont De Nemours And Company | Herbicidal pyridine sulfonamides |
| EP0298752A2 (en) * | 1987-07-10 | 1989-01-11 | Ishihara Sangyo Kaisha, Ltd. | Mercapto-substituted pyridine compounds and process for preparing the same |
| WO1990005728A1 (en) * | 1988-11-21 | 1990-05-31 | E.I. Du Pont De Nemours And Company | Process for the interconversion of two separate crystal forms of a herbicidal pyridine sulfonamide |
-
2019
- 2019-07-30 CN CN201910693435.1A patent/CN110330480A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0237292A2 (en) * | 1986-03-07 | 1987-09-16 | E.I. Du Pont De Nemours And Company | Herbicidal pyridine sulfonamides |
| EP0298752A2 (en) * | 1987-07-10 | 1989-01-11 | Ishihara Sangyo Kaisha, Ltd. | Mercapto-substituted pyridine compounds and process for preparing the same |
| WO1990005728A1 (en) * | 1988-11-21 | 1990-05-31 | E.I. Du Pont De Nemours And Company | Process for the interconversion of two separate crystal forms of a herbicidal pyridine sulfonamide |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111978293A (en) * | 2020-08-24 | 2020-11-24 | 天津大学 | Nicosulfuron-urea eutectic and preparation method thereof |
| CN111978293B (en) * | 2020-08-24 | 2023-10-27 | 天津大学 | Nicosulfuron-urea eutectic and preparation method thereof |
| CN113387928A (en) * | 2021-06-15 | 2021-09-14 | 淄博新农基作物科学有限公司 | Method for circularly producing nicosulfuron technical by using byproduct phenol |
| CN113387928B (en) * | 2021-06-15 | 2022-06-24 | 淄博新农基作物科学有限公司 | Method for circularly producing nicosulfuron original drug by using byproduct phenol |
| RU2827153C1 (en) * | 2024-03-11 | 2024-09-23 | Акционерное общество "Щелково Агрохим" | Method of producing herbicide nicosulfuron |
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Application publication date: 20191015 |