CN103951655B - Nicosulfuron derivative and containing the herbicide of this derivative, and preparation method thereof with application - Google Patents
Nicosulfuron derivative and containing the herbicide of this derivative, and preparation method thereof with application Download PDFInfo
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- CN103951655B CN103951655B CN201410204086.XA CN201410204086A CN103951655B CN 103951655 B CN103951655 B CN 103951655B CN 201410204086 A CN201410204086 A CN 201410204086A CN 103951655 B CN103951655 B CN 103951655B
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- 0 CN(C)C(c(cccn1)c1S(NC(Nc1nc(OC)cc(*)n1)=O)(=O)=O)=O Chemical compound CN(C)C(c(cccn1)c1S(NC(Nc1nc(OC)cc(*)n1)=O)(=O)=O)=O 0.000 description 1
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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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- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Nicosulfuron derivative of the present invention and containing the herbicide of this derivative, and preparation method thereof relate to a kind of herbicide of the organic compound that contains the NCON base being directly connected at least 1 heterocycle with application. Its objective is for a kind of the have activity of weeding of parent, solubility is high in water nicosulfuron derivative and preparation method thereof and herbicide, its preparation method and application containing nicosulfuron derivative environmentally friendly, that be easy to processing are provided. Nicosulfuron derivative of the present invention has the structure of following general formula (I), and wherein x is NH4 +，(CH3)2CHNH2 +Or (C2H5O)3N+. Preparation method of the present invention, comprises the following steps: by soluble in water to hydroxide or the organic base of nicosulfuron and the corresponding salt of described x; Filter; Precipitation; Recrystallization, obtains nicosulfuron derivative. The derivative that the present invention makes has the activity of weeding of parent, and in water, solubility is high, be easy to prepare environmentally friendly, the herbicide that herbicidal effect is good. The present invention is for chemical plant protection field.
Description
Technical field
The present invention relates to a kind of herbicide of the organic compound that contains the NCON base being directly connected at least 1 heterocycle, specialRelate to a kind of herbicide 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 plantThe activity of acetolactate synthestase in body, stops branched-chain amino acid valine, leucine and isoleucine to synthesize and then stops cellDivision, stops growing sensitive plant. The weeds symptom of being injured is lobus cardiacus flavescence, chlorosis, albefaction, and then other leaf from top to bottomFlavescence successively. Generally within 3～4 days after dispenser, can see the weeds symptom of being injured, annual grassy weeds 1～3 week is dead, 6 leaves withLower perennial broadleaf weed is suppressed, stops growing, and loses the competitiveness of same corn; High dose also can make perennial weeds deadDie. At present main nicosulfuron herbicide agent formulation kind have 4% suspending agent, 40g/L dispersible oil, 10%WP, 75%WDG,95％TC。
Due to nicosulfuron improper use, very easily, to doing deposits yields poisoning, cause production loss. Existing formulation is all while usingAfter adding water, be suspended particulate shape, spray at crop or soil surface. Although grain graininess is very little, due to the number of amount of water,The factors such as uniformity when sprinkling more or less affect the uniformity coefficient of particulate pharmaceutical agent in soil and crop surface, then affect medicineThe performance of effect, the collection of regional area medicament is deposited and is more easily produced poisoning. Thereby, develop a kind of use effect that improves nicosulfuronReally, the herbicide of minimizing environmental pollution is significant.
Summary of the invention
The technical problem to be solved in the present invention be to provide a kind ofly there is the activity of weeding of parent, the high nicosulfuron of solubility in waterDerivative and preparation method thereof with environmentally friendly, be easy to processing containing the herbicide of nicosulfuron derivative, its preparation method andApplication.
A kind of nicosulfuron derivative of the present invention, i.e. compound (I), i.e. 2-(4,6-dimethoxypyridin-2-base carbamyl aminoSulphonyl)-N, the water-soluble salt of N-dimethyl nicotinamide, its structure is as follows:
Wherein x is NH4 +，(CH3)2CHNH2 +，(C2H5O)3N+。
A kind of nicosulfuron derivative of the present invention, i.e. the preparation method of compound (I), comprises the following steps: by equimolar cigaretteHydroxide or the organic base of Sulfometuron Methyl and corresponding salt stir in the aqueous solution; After all dissolving, filters solid, by filtrate precipitationObtain pale yellow powder; Then use recrystallizing methanol, obtain nicosulfuron derivative.
A kind of herbicide containing nicosulfuron derivative of the present invention, it comprises: effective active component cpd (I) and carrier; InstituteThe carrier of stating is the upper acceptable carrier of agricultural, is solid or liquid, and is to well known to a person skilled in the art material, asThe mineral matter, organic solvent, solubilizer, surfactant (emulsifying agent, dispersant, wetting agent), thickener of natural or regeneration,Binder, disintegrant, antifreezing agent.
Further, a kind of herbicide containing nicosulfuron derivative of the present invention, the content of described compound (I) is 0.1～99%.
Further, a kind of herbicide containing nicosulfuron derivative of the present invention, the content of described compound (I) is 2～90%.
The preparation method of a kind of herbicide containing nicosulfuron derivative of the present invention, step is as follows: by compound (I) and agriculturalAcceptable carrier mixes, and makes the herbicide containing nicosulfuron derivative.
Further, the preparation method of a kind of herbicide containing nicosulfuron derivative of the present invention, described in the herbicide that makes furtherBe processed into various formulations, as wettable powder, aqua and soluble powder.
Further, the preparation method of a kind of herbicide containing nicosulfuron derivative of the present invention, described in the herbicide that makes add increasingEffect agent, stabilizing agent or carry out compositely with other effective active composition, can improve the practicality in drug effect and the agricultural of composition greatlyProperty.
The application of a kind of herbicide containing nicosulfuron derivative of the present invention, method is as follows: by the weeding containing nicosulfuron derivativeAgent imposes on the crop Tanaka that will cut weeds, and these methods comprise soil and foliar treatment.
Further, the application of a kind of herbicide containing nicosulfuron derivative of the present invention, the application process of described herbicide is for after broadcastingSoil table spraying before seedling, or cauline leaf processing after seedling, can effectively prevent and kill off grass family class weeds.
Further, the application of a kind of herbicide containing nicosulfuron derivative of the present invention, the amount of described herbicide application is 0.5～6gEvery mu of compound (I).
Further, the application of a kind of herbicide containing nicosulfuron derivative of the present invention, the amount of described herbicide application is 2～4gizationEvery mu of compound (I).
The present invention has following beneficial effect:
Herbicide of the present invention has good activity of weeding to grassy weed, can directly be used in the field weeding in land for growing field crops. ByPreferably selective in corn is had, this compound in use and after using, be difficult for causing above-mentioned because of moving of medicamentThe poisoning of crop, has also greatly reduced the injury of pedo relict to crops simultaneously.
Herbicide of the present invention, because compound (I) has well water-solublely at normal temperatures, is more easily processed into it variousThe formulations of pesticide, are processed into the various formulations such as environment amenable soluble powder or aqua to this medicine good condition are provided, canTo cut down finished cost, for industrialization and the marketing of this medicine have brought wide prospect.
Detailed description of the invention
By following examples, the present invention is further detailed, but only conduct explanation of these embodiment, instead of to thisBright restriction.
Embodiment 1
The present embodiment nicosulfuron (2-(4,6-dimethoxypyridin-2-base carbamyl aminosulfonyl)-N, N-dimethyl nicotinamide) sodiumThe synthetic method of salt, step is as follows:
Taking respectively 4.1g nicosulfuron and 0.4g sodium hydroxide powder adds in 50mL water; Stirring at room temperature, treats that solid is wholeAfter dissolving, it is faint yellow that solution is; Filter, filtrate precipitation obtained to pale yellow powder, obtain white needle-like crystals by recrystallizing methanol,Be nicosulfuron sodium salt.
The solubility of the nicosulfuron sodium salt making in water is greater than 150g/L.
Embodiment 2
The present embodiment nicosulfuron (2-(4,6-dimethoxypyridin-2-base carbamyl aminosulfonyl)-N, N-dimethyl nicotinamide) potassiumThe synthetic method of salt, step is as follows:
Taking respectively 4.1g nicosulfuron and 0.56g potassium hydroxide adds in 50mL water; Stirring at room temperature, treats that solid all dissolvesAfter, it is faint yellow that solution is; Filter, filtrate precipitation is obtained to pale yellow powder, obtain white needle-like crystals by recrystallizing methanol,For nicosulfuron sylvite.
The solubility of the nicosulfuron sylvite making in water is greater than 150g/L.
Embodiment 3
The present embodiment nicosulfuron (2-(4,6-dimethoxypyridin-2-base carbamyl aminosulfonyl)-N, N-dimethyl nicotinamide) threeThe synthetic method of ethylamine 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 cigaretteSulfometuron Methyl triethylamine salt.
The solubility of the nicosulfuron triethylamine salt making in water is greater than 150g/L.
Embodiment 4
The present embodiment nicosulfuron (2-(4,6-dimethoxypyridin-2-base carbamyl aminosulfonyl)-N, N-dimethyl nicotinamide) threeThe synthetic method of ethanolamine salt, step is as follows:
Taking respectively 4.1g nicosulfuron and 1.49g triethanolamine adds in 50mL water; Stirring at room temperature, treats that solid all dissolvesAfter, it is faint yellow that solution is; Filter, filtrate precipitation is obtained to pale yellow powder, obtain white needle-like crystals by recrystallizing methanol,For nicosulfuron triethanolamine salt.
The solubility of the nicosulfuron triethanolamine salt making in water is greater than 150g/L.
Embodiment 5
The present embodiment nicosulfuron (2-(4,6-dimethoxypyridin-2-base carbamyl aminosulfonyl)-N, N-dimethyl nicotinamide) is differentThe synthetic method of propylamine 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 cigaretteSulfometuron Methyl isopropyl amine salt.
The solubility 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 lignin sulfonate, 10kg lauryl sodium sulfate, 40kg glauber salt is mixedClose evenly; 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 lignosulfonate, 0.2kg lauryl sodium sulfate, 0.8kg sodium carbonate, 0.7Kg sodium acid carbonate, 5kg urea mixes; Pulverize by 200 mesh sieves, make 20% nicosulfuron sylvite soluble powderAgent.
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 sodium sulfate of polyethenoxy ether of fatty alcohol, 40g ammonium sulfate and 50g alkaneBase phenol polyethenoxy ether formaldehyde condensation products sulfate adds in 830g water, and stirring and dissolving makes 4% nicosulfuron isopropyl amine saltAqua.
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 sodium sulfate of polyethenoxy ether of fatty alcohol, 40g ammonium sulfate and 50gAPES formaldehyde condensation products sulfate adds in 770g water, and stirring and dissolving makes 10% nicosulfuron three secondAmine 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 sodium sulfate of polyethenoxy ether of fatty alcohol, 40g fatty alcohol polyoxy secondAlkene ether and 50g lauryl sodium sulfate add in 860g water, and stirring and dissolving makes 1% nicosulfuron tri ethanol ammonium salt aqua.
Demonstration 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 of 45 daysPreventive effect (in table 1 and table 2).
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 biologically active with nicosulfuron, field weeding effectQuite.
Demonstration 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 corn field lady's-grass, oxThe weeds such as muscle grass, 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 result of the test
As shown in Table 3, nicosulfuron isopropyl amine salt, triethylamine salt, the strain preventive effect of triethanolamine ammonium salt aqua to corn field weedWith fresh weight preventive effect higher than nicosulfuron oil-suspending agent. The production technology of the present embodiment is simple, under equal preventive effect, can save and be produced intoThis.
Although more than described the specific embodiment of the present invention, it will be understood by those of skill in the art that these are only to liftExample explanation, protection scope of the present invention is limited by appended claims. Those skilled in the art is not deviating from the present inventionPrinciple and the prerequisite of essence under, can make various changes or modifications to these embodiments, but these changes and amendment all fallEnter 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 NH4 +、(CH3)2CHNH2 +Or (C2H5O)3N+。
2. a preparation method for nicosulfuron derivative claimed in claim 1, is characterized in that comprising the following steps:
By equimolar nicosulfuron and NH4 +、(CH3)2CHNH2 +Or (C2H5O)3N+The hydroxide of corresponding salt or organic baseIn the aqueous solution, stir; After solid all dissolves, filter, filtrate precipitation is obtained to pale yellow powder; Then use recrystallizing methanol,Obtain nicosulfuron derivative.
3. a herbicide that contains nicosulfuron derivative claimed in claim 1, is characterized in that: comprise that nicosulfuron spreads outBiology and carrier; Wherein, described carrier is the upper acceptable carrier of agricultural, is solid or liquid, and described carrier is naturalOr mineral matter, organic solvent, solubilizer, surfactant, thickener, binder, disintegrant or the antifreezing agent of regeneration.
4. the herbicide containing nicosulfuron derivative according to claim 3, is characterized in that: described nicosulfuron is derivativeThe mass percent concentration of thing is 0.1～99%.
5. the herbicide containing nicosulfuron derivative according to claim 4, is characterized in that: described nicosulfuron is derivativeThe mass percent concentration of thing is 2～90%.
6. a preparation method for the herbicide containing nicosulfuron derivative claimed in claim 3, is characterized in that comprising followingStep:
Upper to nicosulfuron derivative and agricultural acceptable carrier is mixed, make the weeding containing nicosulfuron derivativeAgent.
7. the preparation method of the herbicide containing nicosulfuron derivative according to claim 6, is characterized in that: described systemThe herbicide obtaining is further processed into various formulations, and described formulation is wettable powder, aqua or soluble powder.
8. the preparation method of the herbicide containing nicosulfuron derivative according to claim 6, is characterized in that: described systemThe herbicide obtaining adds synergist and stabilizing agent, or carries out composite with other effective active composition.
9. an application for the herbicide containing nicosulfuron derivative claimed in claim 3, is characterized in that comprising the following steps:Herbicide containing nicosulfuron derivative is imposed on to the crop Tanaka that will cut weeds.
10. the application of the herbicide containing nicosulfuron derivative according to claim 9, is characterized in that: described weedingThe application process of agent 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 |
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| 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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| 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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| CN108947965B (en) * | 2018-07-03 | 2021-07-27 | 天津大学 | Nicosulfuron N, N-dimethylformamide solvent compound 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 |
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- 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 |
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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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