CN101503403A - Preparation of sulfonylurea herbicide nicosulfuron - Google Patents
Preparation of sulfonylurea herbicide nicosulfuron Download PDFInfo
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- CN101503403A CN101503403A CNA2009100680841A CN200910068084A CN101503403A CN 101503403 A CN101503403 A CN 101503403A CN A2009100680841 A CNA2009100680841 A CN A2009100680841A CN 200910068084 A CN200910068084 A CN 200910068084A CN 101503403 A CN101503403 A CN 101503403A
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- organic solvent
- binding agent
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- sulfonylurea herbicide
- dimethoxypyridin
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Abstract
The invention provides apreparation method for preparing sulfonylurea herbicide nicosulfuron. The method comprises the following step: 2-sulfonyl chloro-N,N-dimethyl-nicotinamide, 2-uramido-4,6-dimethoxypyrimidine and acid-binding agent are chosen to undergo reaction in the present of an organic solvent or an organic solvent-water mixture system so as to obtain the sulfonylurea herbicide nicosulfuron product. The mol ratio of the 2-uramido-4,6-dimethoxypyrimidine, the 2-uramido-4,6-dimethoxypyrimidine and the acid-binding agent is 1 : 1-2 : 1-2; the reaction temperature is 50-150 DEG C; the reaction time is 0.5-10 h; the mass ratio of the reactant, which is obtained by following the mol ratio of the 2-uramido-4,6-dimethoxypyrimidine, the 2-uramido-4,6-dimethoxypyrimidine and the acid-binding agent, and the organic solvent is 1 : 2-5. The invention has the advantages of cheap and easily-obtained raw materials, high yield rate, simple and convenient operation and less environment pollution during the production.
Description
Technical field
The present invention relates to a kind of by 2-sulfuryl chlorio-N, N-dimethyl nicotinamide and 2-urea groups-4, the preparation method of 6-dimethoxypyridin synthesizing nicosulfuron agricultural chemicals.
Background technology
Nicosulfuron is that Japanese Ishihara Sangyo Kaisha, Ltd. finds, the sulfonylurea systemic herbicide that late 1980s and du pont company are developed jointly.Nicosulfuron toxicity is very low, rat male and female acute oral LD
505000mg/kg, acute through skin LD
502000mg/kg; Suck LC
505.47mg/L, carp LC
50(96h)〉10mg/L has minimal irritation to lagophthalmos, and no carcinogenic, teratogenesis, mutagenesis belong to low-toxin farm chemicals.Nicosulfuron is active high, and the field usage quantity is low, uses 40-60g/hm behind the bud
2Can effectively prevent and treat annual or perennial gramineous weeds and some broadleaf weeds.Because it to corn growth safety, makes it become the corn herbicides special.Nicosulfuron has become the first brand of sulfonylurea herbicide according to statistics, the equal rank sulfonylurea herbicide of turnout and sales volume the first in the world.Nicosulfuron has good market outlook and considerable economic as new product development.
The synthetic method of nicosulfuron is a lot, and integrating roughly has following five routes:
In many synthetic routes, do not find with 2-sulfuryl chlorio-N as yet, N-dimethyl nicotinamide and 2-urea groups-4, the reaction of 6-dimethoxypyridin generates the synthetic method of nicosulfuron, and this is a new synthetic route.
Summary of the invention
The preparation method who the purpose of this invention is to provide a kind of sulfonylurea herbicide nicosulfuron is beneficial to reach and reduces cost, and is pollution-free, realizes cleaner production, satisfies the needs in market.
For achieving the above object, the technical solution used in the present invention provides a kind of preparation method of sulfonylurea herbicide nicosulfuron, and this method includes following steps:
Choose 2-sulfuryl chlorio-N, N-dimethyl nicotinamide, 2-urea groups-4,6-dimethoxypyridin and acid binding agent react and obtain the sulfonylurea herbicide nicosulfuron product in the presence of organic solvent or organic solvent-water mixed system;
Described 2-urea groups-4,6-dimethoxypyridin: 2-sulfuryl chlorio-N, the N-dimethyl nicotinamide: the mol ratio of acid binding agent is 1:1-2:1-2, temperature of reaction is 50-150 ℃, reaction times is 0.5-10 hours, described 2-urea groups-4, the 6-dimethoxypyridin: 2-sulfuryl chlorio-N, the N-dimethyl nicotinamide: the reactant that acid binding agent forms and the mass ratio of organic solvent are 1:2-5.
Described acid binding agent is a kind of of organic bases, salt of wormwood, yellow soda ash, potassium hydroxide, sodium hydroxide.
The mass ratio of organic solvent and water is 1:0.05-0.5 in described organic solvent-water mixed system.
Described organic solvent is a kind of of benzene, toluene, ethylene dichloride, ethyl acetate, acetonitrile, methyl-sulphoxide, dioxane, dimethyl formamide.
Effect of the present invention is to use the preparation method of this sulfonylurea herbicide nicosulfuron: 1) raw material is easy to get, low price; 2) yield is than higher; 3) operate fairly simple convenience; 4) environmental pollution is less in the production.
Embodiment
Below the preparation method of sulfonylurea herbicide nicosulfuron of the present invention is described further.
The preparation method of sulfonylurea herbicide nicosulfuron of the present invention is 2-sulfuryl chlorio-N, sulfuryl chlorio in the N-dimethyl nicotinamide and 2-urea groups-4, urea groups reaction in the 6-dimethoxypyridin is sloughed a hydrogenchloride molecule and is generated in the presence of acid binding agent.This is a synthetic method that nicosulfuron is brand-new.
The preparation method of sulfonylurea herbicide nicosulfuron of the present invention includes following steps:
Choose 2-sulfuryl chlorio-N, N-dimethyl nicotinamide, 2-urea groups-4,6-dimethoxypyridin and acid binding agent react and obtain the sulfonylurea herbicide nicosulfuron product in the presence of organic solvent or organic solvent-water mixed system;
Described 2-urea groups-4,6-dimethoxypyridin: 2-sulfuryl chlorio-N, the N-dimethyl nicotinamide: the mol ratio of acid binding agent is 1:1-2:1-2, temperature of reaction is 50-150 ℃, reaction times is 0.5-10 hours, described 2-urea groups-4, the 6-dimethoxypyridin: 2-sulfuryl chlorio-N, the N-dimethyl nicotinamide: the reactant that acid binding agent forms and the mass ratio of organic solvent are 1:2-5.
Described acid binding agent is a kind of of organic bases, salt of wormwood, yellow soda ash, potassium hydroxide, sodium hydroxide.
The mass ratio of organic solvent and water is 1:0.05-0.5 in described organic solvent-water mixed system.
Described organic solvent is a kind of of benzene, toluene, ethylene dichloride, ethyl acetate, acetonitrile, methyl-sulphoxide, dioxane, dimethyl formamide.
The preparation method of sulfonylurea herbicide nicosulfuron of the present invention is with 2-sulfuryl chlorio-N, N-dimethyl nicotinamide and 2-urea groups-4, and the synthetic route of 6-dimethoxypyridin prepared in reaction nicosulfuron is:
The preparation process of sulfonylurea herbicide nicosulfuron of the present invention is described by embodiment:
Embodiment 1: bottled with the 250ml four-hole with agitator, and thermometer, reflux condensing tube.Add 24.9g (0.1mol) 2-sulfuryl chlorio-N in it, the N-dimethyl nicotinamide, the 150ml methyl-sulphoxide, salt of wormwood 15.2g (0.11mol), and 2-urea groups-4,6-dimethoxypyridin 19.8g (0.1mol) reacts 3h down at 120-125 ℃.Cooling, solids removed by filtration salt washs with methyl-sulphoxide.Filtrate, decompression steams methyl-sulphoxide, obtains product 39.9g, product purity: 97%, yield: 94.3%.
Embodiment 2: bottled with the 250ml four-hole with agitator, and thermometer, reflux condensing tube.Add 24.9g (0.1mol) 2-sulfuryl chlorio-N in it, the N-dimethyl nicotinamide, 170ml toluene, salt of wormwood 15.2g (0.11mol), and 2-urea groups-4,6-dimethoxypyridin 21.8g (0.11mol) reacts 2.5h down at 95-110 ℃.Cooling, solids removed by filtration salt is used toluene wash.Filtrate, decompression steams toluene, obtains product 40.2g, product purity: 97.5%, yield: 95.5%.
Embodiment 3: bottled with the 500ml four-hole with agitator, and thermometer, reflux condensing tube.Add 49.8g (0.2mol) 2-sulfuryl chlorio-N in it, the N-dimethyl nicotinamide, 350ml toluene, yellow soda ash 24.4g (0.23mol), and 2-urea groups-4,6-dimethoxypyridin 41.6g (0.21mol) reacts 2.5h down at 95-110 ℃.Cooling, solids removed by filtration salt is used toluene wash.Filtrate, decompression steams toluene, obtains product 80g, product purity: 97.7%, yield 95.2%.
Embodiment 4: bottled with the 500ml four-hole with agitator, and thermometer, reflux condensing tube.Add 49.8g (0.2mol) 2-sulfuryl chlorio-N in it, the N-dimethyl nicotinamide, 350ml reclaims toluene, yellow soda ash 24.4g (0.23mol), and 2-urea groups-4,6-dimethoxypyridin 41.6g (0.21mol) reacts 2.5h down at 95-110 ℃.Cooling, solids removed by filtration salt is with reclaiming toluene wash.Filtrate, decompression steams toluene, obtains product 81g, product purity: 97.1%, yield 95.8%.
Embodiment 5: bottled with the 500ml four-hole with agitator, and thermometer, reflux condensing tube.Add 49.8g (0.2mol) 2-sulfuryl chlorio-N in it, the N-dimethyl nicotinamide, 320ml toluene, 30ml water, yellow soda ash 24.4g (0.23mol), and 2-urea groups-4,6-dimethoxypyridin 41.6g (0.21mol) reacts 3h down at 95-100 ℃.Cooling, layering removes and anhydrates and salt, the oil reservoir washing, decompression steams toluene, obtains product 80g, product purity: 97.1%, yield 94.6%.
Claims (4)
1, a kind of preparation method of sulfonylurea herbicide nicosulfuron, this method includes following steps:
Choose 2-sulfuryl chlorio-N, N-dimethyl nicotinamide, 2-urea groups-4,6-dimethoxypyridin and acid binding agent react and obtain the sulfonylurea herbicide nicosulfuron product in the presence of organic solvent or organic solvent-water mixed system;
Described 2-urea groups-4,6-dimethoxypyridin: 2-sulfuryl chlorio-N, the N-dimethyl nicotinamide: the mol ratio of acid binding agent is 1:1-2:1-2, temperature of reaction is 50-150 ℃, reaction times is 0.5-10 hours, described 2-urea groups-4, the 6-dimethoxypyridin: 2-sulfuryl chlorio-N, the N-dimethyl nicotinamide: the reactant that acid binding agent forms and the mass ratio of organic solvent are 1:2-5.
2, preparation method according to claim 1 is characterized in that: described acid binding agent is a kind of of organic bases, salt of wormwood, yellow soda ash, potassium hydroxide, sodium hydroxide.
3, preparation method according to claim 1 is characterized in that: the mass ratio of organic solvent and water is 1:0.05-0.5 in described organic solvent-water mixed system.
4, preparation method according to claim 1 is characterized in that: described organic solvent is a kind of of benzene, toluene, ethylene dichloride, ethyl acetate, acetonitrile, methyl-sulphoxide, dioxane, dimethyl formamide.
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| Application Number | Priority Date | Filing Date | Title |
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| CNA2009100680841A CN101503403A (en) | 2009-03-10 | 2009-03-10 | Preparation of sulfonylurea herbicide nicosulfuron |
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| CNA2009100680841A CN101503403A (en) | 2009-03-10 | 2009-03-10 | Preparation of sulfonylurea herbicide nicosulfuron |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101671327B (en) * | 2009-09-28 | 2011-04-06 | 南京第一农药集团有限公司 | Method for synthesizing nicosulfuron |
| CN107079919A (en) * | 2017-06-08 | 2017-08-22 | 合肥龙滨化工科技有限公司 | A kind of composition pesticide containing nicosulfuron and Prochloraz |
| CN109400581A (en) * | 2018-09-20 | 2019-03-01 | 安徽华星化工有限公司 | A method of improving nicosulfuron content |
-
2009
- 2009-03-10 CN CNA2009100680841A patent/CN101503403A/en active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101671327B (en) * | 2009-09-28 | 2011-04-06 | 南京第一农药集团有限公司 | Method for synthesizing nicosulfuron |
| CN107079919A (en) * | 2017-06-08 | 2017-08-22 | 合肥龙滨化工科技有限公司 | A kind of composition pesticide containing nicosulfuron and Prochloraz |
| CN109400581A (en) * | 2018-09-20 | 2019-03-01 | 安徽华星化工有限公司 | A method of improving nicosulfuron content |
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Application publication date: 20090812 |