CN103951655A - Nicosulfuron derivative, herbicide containing same, preparation methods of nicosulfuron derivative and herbicide and application of herbicide - Google Patents
Nicosulfuron derivative, herbicide containing same, preparation methods of nicosulfuron derivative and herbicide and application of herbicide Download PDFInfo
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- CN103951655A CN103951655A CN201410204086.XA CN201410204086A CN103951655A CN 103951655 A CN103951655 A CN 103951655A CN 201410204086 A CN201410204086 A CN 201410204086A CN 103951655 A CN103951655 A CN 103951655A
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- nicosulfuron
- derivative
- weedicide
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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
-
- 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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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
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- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
The invention discloses a nicosulfuron derivative, a herbicide containing the same, preparation methods of the nicosulfuron derivative and the herbicide and application of the herbicide, and relates to a herbicide containing an organic compound directly connected to an NCON group on at least one heterocycle. The invention aims at providing a nicosulfuron derivative with parent herbicidal activity and high water solubility and a preparation method for the same, as well as an environment-friendly herbicide containing the nicosulfuron derivative and easy to process, and a preparation method and an application for the same. The nicosulfuron derivative disclosed by the invention has the structure shown in the general formula (I) shown in the specification, wherein x is Na<+>, K<+>, NH4<+>, (CH3)2CHNH2<+>, (C2H5)3N<+> or (C2H5O)3N<+>. The preparation method disclosed by the invention comprises the following steps of: dissolving nicosulfuron and hydroxide or organic base of the corresponding salt of x in water; filtering; desolventizing; recrystallizing to obtain the nicosulfuron derivative. The derivative prepared by the preparation method disclosed by the invention has parent herbicidal activity, and high water solubility, and the herbicide which is environment-friendly and good in herbicidal effect is easily prepared. The nicosulfuron derivative, the herbicide containing the same, the preparation methods of the nicosulfuron derivative and the herbicide and application of the herbicide disclosed by the invention are used in the field of chemical plant protection.
Description
Technical field
The present invention relates to a kind of weedicide of the organic compound that contains the NCON base being directly connected at least 1 heterocycle, particularly relate to a kind of weedicide that contains nicosulfuron derivative.
Background technology
Nicosulfuron (Nicosulfuron)
Nicosulfuron is inner-adsorption conduction-type herbicide, can be by the cauline leaf of plant and root absorption conduction rapidly, by suppressing the activity of acetolactate synthestase in plant materials, stop branched-chain amino acid α-amino-isovaleric acid, leucine and Isoleucine to synthesize and then stop cell fission, sensitive plant is stopped growing.The weeds symptom of being injured is lobus cardiacus flavescence, chlorosis, albefaction, then other leaf flavescence successively from top to bottom.Generally within 3～4 days after dispenser, can see the weeds symptom of being injured, annual grassy weeds 1～3 week is dead, and the following perennial broadleaf weed of 6 leaf is suppressed, stops growing, and loses the competitive capacity of same corn; High dosage also can make perennial weeds death.Main nicosulfuron herbicide agent formulation kind has 4% suspension agent, 40g/L to dispersible oil, 10%WP, 75%WDG, 95%TC at present.
Due to nicosulfuron improper use, very easily, to doing deposits yields poisoning, cause production loss.Existing formulation is to be all suspended particle shape after adding water while using, sprays at crop or soil surface.Although grain graininess is very little, due to amount of water number, the factor such as uniformity coefficient while spraying more or less affect the degree of uniformity of particulate pharmaceutical agent in soil and crop surface, then affect the performance of drug effect, the collection of regional area medicament is deposited and is more easily produced poisoning.Thereby, develop a kind of result of use that improves nicosulfuron, the weedicide that reduces environmental pollution is significant.
Summary of the invention
The technical problem to be solved in the present invention is to provide a kind of the have weeding activity of parent, solubleness is high in water nicosulfuron derivative and preparation method thereof and weedicide, its preparation method and application containing nicosulfuron derivative environmentally friendly, that be easy to processing.
A kind of nicosulfuron derivative of the present invention, i.e. compound (I), i.e. 2-(4,6-dimethoxypyridin-2-base carbamyl aminosulfonyl)-N, the water-soluble salt of N-dimethyl nicotinamide, its structure is as follows:
Wherein x is Na
+, K
+, NH
4 +, (CH
3)
2cHNH
2 +, (C
2h
5)
3n
+, (C
2h
5o)
3n
+.
A kind of nicosulfuron derivative of the present invention, i.e. the preparation method of compound (I), comprises the following steps: the oxyhydroxide of equimolar nicosulfuron and corresponding salt or organic bases are stirred in the aqueous solution; After solid all dissolves, filter, filtrate precipitation is obtained to pale yellow powder; Then use recrystallizing methanol, obtain nicosulfuron derivative.
A kind of weedicide containing nicosulfuron derivative of the present invention, it comprises: effective active component cpd (I) and carrier; Described carrier is the upper acceptable carrier of agricultural, for solid or liquid, and be to well known to a person skilled in the art material, as mineral substance, organic solvent, solubilizing agent, tensio-active agent (emulsifying agent, dispersion agent, wetting agent), thickening material, tamanori, disintegrating agent, frostproofer natural or regeneration.
Further, a kind of weedicide containing nicosulfuron derivative of the present invention, the content of described compound (I) is 0.1～99%.
Further, a kind of weedicide containing nicosulfuron derivative of the present invention, the content of described compound (I) is 2～90%.
The preparation method of a kind of weedicide containing nicosulfuron derivative of the present invention, step is as follows: upper to compound (I) and agricultural acceptable carrier is mixed, make the weedicide containing nicosulfuron derivative.
Further, the preparation method of a kind of weedicide containing nicosulfuron derivative of the present invention, described in the weedicide that makes be further processed into various formulations, as wettable powder, aqua and soluble powder.
Further, the preparation method of a kind of weedicide containing nicosulfuron derivative of the present invention, described in the weedicide that makes add synergistic agent, stablizer or carry out compositely with other effective active composition, can greatly improve the practicality in drug effect and the agricultural of composition.
The application of a kind of weedicide containing nicosulfuron derivative of the present invention, method is as follows: the weedicide containing nicosulfuron derivative is imposed on to the crop Tanaka that will cut weeds, and these methods comprise soil and foliar treatment.
Further, the application of a kind of weedicide containing nicosulfuron derivative of the present invention, the application process of described weedicide is for broadcasting the spraying of the front soil table of rear seedling, or cauline leaf processing after seedling, can effectively prevent and kill off Gramineae class weeds.
Further, the application of a kind of weedicide containing nicosulfuron derivative of the present invention, the amount of described herbicide application is every mu of 0.5～6g compound (I).
Further, the application of a kind of weedicide containing nicosulfuron derivative of the present invention, the amount of described herbicide application is every mu of 2～4g compound (I).
The present invention has following beneficial effect:
Weedicide of the present invention has good weeding activity to gramineous weeds, can directly be used in the field weeding in land for growing field crops.Owing to corn being had to good selectivity, this compound in use and use is difficult afterwards causes the poisoning to above-mentioned crop because of moving of medicament, has also greatly reduced the injury of pedo relict to farm crop simultaneously.
Weedicide of the present invention, because compound (I) has well water-soluble at normal temperatures, make it more easily be processed into the various pesticide formulation, be processed into the various formulations such as environment amenable soluble powder or aqua to this medicine good condition is provided, can cut down finished cost, for industrialization and the marketing of this medicine have brought wide prospect.
Embodiment
By following examples, the present invention is further detailed, but only conduct explanation of these embodiment, instead of limit the invention.
Embodiment 1
The synthetic method of the present embodiment nicosulfuron (2-(4,6-dimethoxypyridin-2-base carbamyl aminosulfonyl)-N, N-dimethyl nicotinamide) sodium salt, step is as follows:
Taking respectively 4.1g nicosulfuron and 0.4g sodium hydroxide powder adds in 50mL water; Stirring at room temperature, after solid all dissolves, it is faint yellow that solution is; Filter, filtrate precipitation is obtained to pale yellow powder, obtain white needle-like crystals by recrystallizing methanol, be nicosulfuron sodium salt.
The solubleness of the nicosulfuron sodium salt making in water is greater than 150g/L.
Embodiment 2
The synthetic method of the present embodiment nicosulfuron (2-(4,6-dimethoxypyridin-2-base carbamyl aminosulfonyl)-N, N-dimethyl nicotinamide) sylvite, step is as follows:
Taking respectively 4.1g nicosulfuron and 0.56g potassium hydroxide adds in 50mL water; Stirring at room temperature, after solid all dissolves, it is faint yellow that solution is; Filter, filtrate precipitation is obtained to pale yellow powder, obtain white needle-like crystals by recrystallizing methanol, be nicosulfuron sylvite.
The solubleness of the nicosulfuron sylvite making in water is greater than 150g/L.
Embodiment 3
The synthetic method of the present embodiment nicosulfuron (2-(4,6-dimethoxypyridin-2-base carbamyl aminosulfonyl)-N, N-dimethyl nicotinamide) triethylamine salt, step is as follows:
Taking respectively 4.1g nicosulfuron and 1.01g triethylamine adds in 50mL water; Stirring at room temperature, after solid all dissolves, it is faint yellow that solution is; Filter, filtrate precipitation is obtained to pale yellow powder, obtain white needle-like crystals by recrystallizing methanol, be nicosulfuron triethylamine salt.
The solubleness of the nicosulfuron triethylamine salt making in water is greater than 150g/L.
Embodiment 4
The synthetic method of the present embodiment nicosulfuron (2-(4,6-dimethoxypyridin-2-base carbamyl aminosulfonyl)-N, N-dimethyl nicotinamide) triethanolamine salt, step is as follows:
Taking respectively 4.1g nicosulfuron and 1.49g trolamine adds in 50mL water; Stirring at room temperature, after solid all dissolves, it is faint yellow that solution is; Filter, filtrate precipitation is obtained to pale yellow powder, obtain white needle-like crystals by recrystallizing methanol, be nicosulfuron triethanolamine salt.
The solubleness of the nicosulfuron triethanolamine salt making in water is greater than 150g/L.
Embodiment 5
The synthetic method of the present embodiment nicosulfuron (2-(4,6-dimethoxypyridin-2-base carbamyl aminosulfonyl)-N, N-dimethyl nicotinamide) isopropyl amine salt, step is as follows:
Taking respectively 4.1g nicosulfuron and 0.59g Isopropylamine adds in 50mL water; Stirring at room temperature, after solid all dissolves, it is faint yellow that solution is; Filter, filtrate precipitation is obtained to pale yellow powder, obtain white needle-like crystals by recrystallizing methanol, be nicosulfuron isopropyl amine salt.
The solubleness of the nicosulfuron isopropyl amine salt making in water is greater than 150g/L.
Embodiment 6
The preparation method of the present embodiment 90% nicosulfuron sodium salt soluble powder, step is as follows:
By 900kg nicosulfuron sodium salt, 50kg sodium lignosulfonate, 10kg sodium lauryl sulphate, 40kg Sodium sulfate anhydrous.min(99) mixes; Pulverize by 200 mesh sieves, make 90% nicosulfuron sodium salt soluble powder.
Embodiment 7
The preparation method of the present embodiment 20% nicosulfuron sylvite soluble powder, step is as follows:
By 2kg nicosulfuron sylvite, 1.3kg calcium lignin sulphonate, 0.2kg sodium lauryl sulphate, 0.8kg sodium carbonate, 0.7kg sodium bicarbonate, 5kg urea mixes; Pulverize by 200 mesh sieves, make 20% nicosulfuron sylvite soluble powder.
Embodiment 8
The preparation method of the present embodiment 4% nicosulfuron isopropamide AS, step is as follows:
Take respectively 40g nicosulfuron isopropyl amine salt, 40g polyoxyethylenated alcohol sodium sulfate, 40g ammonium sulfate and 50g alkylphenol polyoxyethylene formaldehyde condensation products vitriol and add in 830g water, stirring and dissolving, makes 4% nicosulfuron isopropamide AS.
Embodiment 9
The preparation method of the present embodiment 10% nicosulfuron triethylamine salt aqua, step is as follows:
Take respectively 100g nicosulfuron triethylamine salt, 40g polyoxyethylenated alcohol sodium sulfate, 40g ammonium sulfate and 50g alkylphenol polyoxyethylene formaldehyde condensation products vitriol and add in 770g water, stirring and dissolving, makes 10% nicosulfuron triethylamine salt aqua.
Embodiment 10
The preparation method of the present embodiment 1% nicosulfuron tri ethanol ammonium salt aqua, step is as follows:
Take respectively 10g nicosulfuron triethanolamine salt, 40g polyoxyethylenated alcohol sodium sulfate, 40g fatty alcohol-polyoxyethylene ether and 50g sodium lauryl sulphate and add in 860g water, stirring and dissolving, makes 1% nicosulfuron tri ethanol ammonium salt aqua.
Proof test 1
Embodiment 6,7 prevents and kill off the test of corn field annual grassy weeds
Application method: adopt cauline leaf processing, water consumption is 600L/ha, tests after the strain preventive effect of 30 days and dispenser the fresh weight preventive effect (in table 1 and table 2) of 45 days.
Table 1 embodiment 6-7 to strain preventive effect-dispenser of weeds after 30 days
Note: lowercase represents 0.05 level, capitalization 0.01 level
Table 2 embodiment 6-7 to fresh weight preventive effect-dispenser of weeds after 45 days
Note: lowercase represents 0.05 level, capitalization 0.01 level
From table 1 and table 2, nicosulfuron sodium salt and sylvite have identical biological activity with nicosulfuron, and field weeding effect is suitable.
Proof test 2
Embodiment 8～10 prevents and kill off corn field and is mixed with the careless test of pesticide effectiveness
Application method: the corn field weed 2-5 leaf phase, the processing of weeds cauline leaf even spraying, can effectively prevent and kill off the weeds such as corn field lady's-grass, Herba Eleusines Indicae, anti-bitterroot, purslane, last dispenser the results are shown in Table 3.
Table 3 embodiment 8～10 prevents and kill off corn weeds in field test-results
As shown in Table 3, strain preventive effect to corn field weed of nicosulfuron isopropyl amine salt, triethylamine salt, trolamine ammonium salt aqua and fresh weight preventive effect are higher than nicosulfuron oil-suspending agent.The production technique of the present embodiment is simple, under equal preventive effect, can save production cost.
Although more than described the specific embodiment of the present invention, it will be understood by those of skill in the art that these only illustrate, protection scope of the present invention is limited by appended claims.Those skilled in the art is not deviating under the prerequisite of principle of the present invention and essence, can make various changes or modifications to these embodiments, but these changes and amendment all fall into protection scope of the present invention.
Claims (10)
1. a nicosulfuron derivative, i.e. compound (I), is characterized in that: have following structure:
Wherein x is Na
+, K
+, NH
4 +, (CH
3)
2cHNH
2 +, (C
2h
5)
3n
+or (C
2h
5o)
3n
+.
2. a preparation method for nicosulfuron derivative claimed in claim 1, is characterized in that comprising the following steps:
By equimolar nicosulfuron and Na
+, K
+, NH
4 +, (CH
3)
2cHNH
2 +, (C
2h
5)
3n
+or (C
2h
5o)
3n
+oxyhydroxide or the organic bases of corresponding salt stir in the aqueous solution; After solid all dissolves, filter, filtrate precipitation is obtained to pale yellow powder; Then use recrystallizing methanol, obtain nicosulfuron derivative.
3. a weedicide that contains nicosulfuron derivative claimed in claim 1, is characterized in that: comprise nicosulfuron derivative and carrier; Wherein, described carrier is the upper acceptable carrier of agricultural, for solid or liquid, described carrier is mineral substance, organic solvent, solubilizing agent, tensio-active agent (emulsifying agent, dispersion agent, wetting agent), thickening material, tamanori, disintegrating agent or frostproofer natural or regeneration.
4. the weedicide containing nicosulfuron derivative according to claim 3, is characterized in that: the mass percent concentration of described nicosulfuron derivative is 0.1～99%.
5. the weedicide containing nicosulfuron derivative according to claim 4, is characterized in that: the mass percent concentration of described nicosulfuron derivative is 2～90%.
6. a preparation method for the weedicide containing nicosulfuron derivative claimed in claim 3, is characterized in that comprising the following steps:
Upper to nicosulfuron derivative and agricultural acceptable carrier is mixed, make the weedicide containing nicosulfuron derivative.
7. the preparation method of the weedicide containing nicosulfuron derivative according to claim 6, is characterized in that: described in the weedicide that makes be further processed into various formulations, described formulation is wettable powder, aqua or soluble powder.
8. the preparation method of the weedicide containing nicosulfuron derivative according to claim 6, is characterized in that: described in the weedicide that makes add synergistic agent and stablizer, or carry out composite with other effective active composition.
9. an application for the weedicide containing nicosulfuron derivative claimed in claim 3, is characterized in that comprising the following steps: the weedicide containing nicosulfuron derivative is imposed on to the crop Tanaka that will cut weeds.
10. the application of the weedicide containing nicosulfuron derivative according to claim 9, is characterized in that: the application process of described weedicide is for broadcasting the spraying of the front soil table of rear seedling, or cauline leaf processing after seedling.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410204086.XA CN103951655B (en) | 2014-05-15 | 2014-05-15 | Nicosulfuron derivative and containing the herbicide of this derivative, and preparation method thereof with application |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410204086.XA CN103951655B (en) | 2014-05-15 | 2014-05-15 | Nicosulfuron derivative and containing the herbicide of this derivative, and preparation method thereof with application |
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| Publication Number | Publication Date |
|---|---|
| CN103951655A true CN103951655A (en) | 2014-07-30 |
| CN103951655B CN103951655B (en) | 2016-05-11 |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108947965A (en) * | 2018-07-03 | 2018-12-07 | 天津大学 | A kind of nicosulfuron N,N-dimethylformamide solvated compounds crystal and preparation method thereof |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN87100436A (en) * | 1986-01-30 | 1987-08-12 | 石原产业株式会社 | The pyridinsulfonamide compounds that replaces, the method that contains the weedicide of this compounds and prepare this compounds |
| CN101262770A (en) * | 2005-09-08 | 2008-09-10 | 拜尔作物科学股份公司 | Storage-stable sulphonamide formulations |
| GB2496643A (en) * | 2011-11-17 | 2013-05-22 | Rotam Agrochem Int Co Ltd | Herbicidal suspension concentrate |
-
2014
- 2014-05-15 CN CN201410204086.XA patent/CN103951655B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN87100436A (en) * | 1986-01-30 | 1987-08-12 | 石原产业株式会社 | The pyridinsulfonamide compounds that replaces, the method that contains the weedicide of this compounds and prepare this compounds |
| CN101262770A (en) * | 2005-09-08 | 2008-09-10 | 拜尔作物科学股份公司 | Storage-stable sulphonamide formulations |
| GB2496643A (en) * | 2011-11-17 | 2013-05-22 | Rotam Agrochem Int Co Ltd | Herbicidal suspension concentrate |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108947965A (en) * | 2018-07-03 | 2018-12-07 | 天津大学 | A kind of nicosulfuron N,N-dimethylformamide solvated compounds crystal and preparation method thereof |
| CN108947965B (en) * | 2018-07-03 | 2021-07-27 | 天津大学 | Nicosulfuron N, N-dimethylformamide solvent compound crystal and preparation method thereof |
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| CN103951655B (en) | 2016-05-11 |
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Inventor after: Yu Maoxiang Inventor after: Qiao Lidong Inventor after: Zhao Xiaocui Inventor after: Tian Haifeng Inventor after: Li Jihong Inventor after: Zhang Yichao Inventor after: Tian Jinsheng Inventor after: Jia Zhenmei Inventor after: Kou Junjie Inventor before: Qiao Lidong Inventor before: Zhao Xiaocui Inventor before: Tian Haifeng Inventor before: Li Jihong Inventor before: Zhang Yichao Inventor before: Tian Jinsheng Inventor before: Kou Junjie Inventor before: Jia Zhenmei |
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