CN108218766A - A kind of preparation method of the compound containing paraquat or diquat - Google Patents
A kind of preparation method of the compound containing paraquat or diquat Download PDFInfo
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- CN108218766A CN108218766A CN201711305006.XA CN201711305006A CN108218766A CN 108218766 A CN108218766 A CN 108218766A CN 201711305006 A CN201711305006 A CN 201711305006A CN 108218766 A CN108218766 A CN 108218766A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D213/06—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 containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D213/22—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 containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing two or more pyridine rings directly linked together, e.g. bipyridyl
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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
- A01N39/00—Biocides, pest repellants or attractants, or plant growth regulators containing aryloxy- or arylthio-aliphatic or cycloaliphatic compounds, containing the group or, e.g. phenoxyethylamine, phenylthio-acetonitrile, phenoxyacetone
- A01N39/02—Aryloxy-carboxylic acids; Derivatives thereof
- A01N39/04—Aryloxy-acetic acids; Derivatives thereof
-
- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
-
- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D213/72—Nitrogen atoms
- C07D213/73—Unsubstituted amino or imino radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
- C07D471/14—Ortho-condensed systems
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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)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The invention discloses a kind of preparation methods of the compound containing paraquat or diquat.First, paraquat or diquat dibromide aqueous solution by strong basic anion-exchange resin, three-level exchanges to obtain 98.5% paraquat of purity or diquat dibromide strong base solution；Secondly, inorganic acid or organic acid herbicidal are added in, is stirred at room temperature, vacuum distillation removes moisture, can obtain the compound containing paraquat or diquat, yield 95%, purity 97.5%；Finally, reaction terminates, and adds in the regeneration of 1%~4%NaOH solions exchanger resin, can reuse, service efficiency is high.The method of the present invention, easy to operate, organic solvent-free; it is all carried out in water phase, pollution-free, ion exchange resin may be reused; the difunctional herbicide containing anionic pesticide and paraquat cation can be obtained, there is higher economic benefit and environmental protection meaning.
Description
Technical field
The present invention relates to a kind of the compound containing paraquat or diquat is synthesized using anion exchange resin
Preparation method, belong to technical field of chemistry.
Background technology
Paraquat, chemical name are 1-1'- dimethyl -4-4'- bipyridine cation salt, are a kind of quick total weed controls
Agent has action of contace poison and certain systemic action, can be absorbed by plant green tissues rapidly, make its withered.The structure of paraquat
Formula is as follows：
Diquat dibromide, chemical name are 1,1'- ethylidene -2,2'- bipyridyl dibromo salts, and non-selective contact killing type herbicide inhibits
Photosynthetic electron transmission, the Bipyridine compound of the reducing condition object cell membrane disruption under photoinduction are withered and yellow by medicine position.
The structural formula of diquat dibromide is as follows：
It is its cationic moiety that herbicide effect is played in paraquat diquat dibromide, unrelated with chlorion bromide ion.Meanwhile paraquat enemy's grass
Fast or other herbicides if long-term be used alone, all easily make weeds generate certain drug resistance, dosage can be caused to increase,
The problem of preventive effect reduces, the duration shortens.Using single variety herbicide, weeding range is relatively narrow, and user is caused to repeat dispenser, increases
Add labour cost, be unfavorable for energy conservation and environmental protection.
Invention content
Technical problem：The object of the present invention is to provide a kind of preparations of the compound containing paraquat or diquat
Method, the preparation method is simple, environmental-friendly, and yield is high, can not only obtain with synergistic function, expand herbicide controlling spectrum,
The Herbicidal combinations that use cost is low, drug effect is outstanding have higher application value.
Technical solution：A kind of preparation method of the compound containing paraquat or diquat of the present invention, the system
Preparation Method includes the following steps：
A. paraquat aqueous solution or diquat dibromide aqueous solution are slowly added to anion-exchange resin column, can obtain strong base solution；
B. inorganic acid or organic acid herbicidal are added in above-mentioned strong base solution, stirring is completely dissolved, solution clarification；
C. it is evaporated under reduced pressure, removes moisture, obtain the compound containing paraquat or diquat.
The synthetic route of above-mentioned paraquat cation salt and diquat salt is as follows：
HB：Inorganic acid described in patent or organic acid herbicidal shorthand notation.
Further, step a. is slowly added to paraquat aqueous solution or diquat dibromide aqueous solution by three anion exchange trees
The three-level exchange column that fat column is connected in series, three-level exchange can obtain strong base solution.
Further, step a. is slowly added to paraquat aqueous solution or diquat dibromide aqueous solution by three anion exchange trees
The three-level exchange column that fat column is connected in series, three-level obtain the strong base solution that purity reaches more than 98.5% after exchanging.
The inorganic acid is hydrochloric acid, sulfuric acid, phosphoric acid, hydroiodic acid, hydrobromic acid, perchloric acid, periodic acid, hyperbromic acid, chloric acid, iodine
Acid, bromic acid, nitric acid, nitrous acid or carbonic acid；Organic acid herbicidal is contains carboxylic acid group, thiocarbonic acid group, sulfonic acid group, Asia
The herbicide of sulfonic acid group, thiosulfonic acid group or phosphorous acid.
The herbicide containing carboxylic acid group includes aromatics acid herbicide, phenoxy carboxylic acid class herbicide or includes carboxylic acid
Organophosphor (organophosphorous) herbicide, other herbicides comprising carboxylic acid group of group.
The aromatics acid herbicide is selected from：Benzoic acid herbicides, such as difluoro pyrrole grand (diflufenzopyr), alanap
(naptalam), Amiben (chloramben), Mediben, 2,3,6- trichlorobenzoic acids (2,3,6-TBA), tricamba
(tricamba)；Pyrimidine oxy-benzoic acid herbicide, such as double phonetic benzoic acid (bispyribac), oxime pyridine are careless (pyriminobac)；
Pyrimadinylthio benzoic acid herbicides, such as phonetic sulphur benzoic acid (pyrithiobac)；O-phthalic acid herbicide, such as chlorthal
(chlorthal)；Pyridine carboxylic acid herbicide, such as Dorema ammoniacum pyridine (aminopyralid), morpholine acid dichloride picoline (clopyralid), poison
Green bristlegrass is fixed (picloram)；Quinoline carboxylic acid's herbicide, such as dichloro quinolinic acid (quinclorac), quinmerac (quinmerac)；Or its
His aromatics acid herbicide, such as the third pyrimidine acid of ring (aminocyclopyrachlor).It is preferred that benzoic acid herbicides, especially wheat straw
Fear.
The phenoxy carboxylic acid herbicide is selected from：Phenoxy acetic acids herbicide, such as 4- tomatotone (Tomatotones
(4-CPA)), (2,4 dichloro benzene oxygroup) acetic acid (2,4- drops (2,4-D)), (3,4- dichlorophenoxies) acetic acid (3,4- drops amine (3,
4-DA)), 2 first, 4 chlorine (MCPA) (4- (4- chlorine oxy-o-cresyl) butyric acid), 2- first -4- chloroethenes thioesters (MCPA-thioethyl),
(2,4,5- Trichlorophenoxies) acetic acid (2,4,5- tears (2,4,5-T))；Phenoxybutyhc class herbicide, such as chlorobenzene oxy butyrate (4-
CPB), 4- (2,4 dichloro benzene oxygroup) butyric acid (2,4- Embutoxs (2,4-DB)), 4- (3,4- dichlorophenoxies) butyric acid (3,4- drops
Butyric acid (3,4-DB)), 4- (4- chlorine oxy-o-cresyl) butyric acid (Thistrol (MCPB)), 4- (2,4,5- Trichlorophenoxies) fourth
Sour (2,4,5- tears butyric acid (2,4,5-TB))；Phenoxypropionic acid herbicide, such as Fruitone CPA (cloprop), 2- (4- chlorophenoxies)
Propionic acid (chlorine phenoxy propionic acid (4-CPP)), 2,4- drops propionic acid (dichlorprop), high 2,4- drops propionic acid (dichlorprop-P),
4- (3,4- dichlorophenoxies) butyric acid (3,4- drops propionic acid (3,4-DP)), 2,4,5- tears propionic acid (fenoprop), 2- first -4- chlorine third
Sour (mecoprop), high -2 first -4- chloropropionic acids (mecoprop-P)；Aryloxyphenoxypropionic herbicide, such as chloroazifoppropynyl
(chlorazifop), clodinafop-propargyl (clodinafop), neoprene careless (clofop), cyhalofop-butyl (cyhalofop), chloroformate grass
(diclofop), oxazoles diclofop-methyl (fenoxaprop), Gao oxazoles diclofop-methyls (fenoxaprop-P), diclofop-methyl thiazole
(fenthiaprop), fluazifop (fluazifop), efficient fluazifop (fluazifop-P), haloxyfop
(haloxyfop), the careless ether (isoxapyrifop) of haloxyfop-P-methyl (haloxyfop-P), evil, metamifop
(metamifop), propaquizafop (propaquizafop), quizalofop-ethyl (quizalofop), Quizalotop-ethyl (quizalofop-P),
Trifluoromethoxy phenoxy propionic acid (trifop).It is preferred that phenoxyacetic acid herbicide, especially 2- first -4- chlorine (MCPA).
The organophosphorus herbicide comprising carboxylic acid group is selected from：Bilanafos (bialafos), glufosinate-ammonium
(glufosinate), glufosinate-ammonium (glufosinate-P), glyphosate (glyphosate).It is preferred that glyphosate.
Described other herbicides comprising carboxylic acid group are selected from：Wrap pyridine Herbicides carboxylic-containing acid, such as fluroxypramide
(fluroxypyr), Triclopyr (triclopyr)；Triazolo pyrimidine herbicide carboxylic-containing acid is wrapped, such as the phonetic sulfanilic acid of azoles
(cloransulam)；Pyrimidine radicals sulfonylurea herbicide carboxylic-containing acid is wrapped, such as benzyl ethyl methyl (bensulfuron), chlorimuron
(chlorimuron), amide sulphur grand (foramsulfuron), pyrrole chlorsulfuron (halosulfuron), mesosulfuronmethyl
(mesosulfuron), Fluoropyrimidinesulfuron (primisulfuron), ethyl methyl (sulfometuron)；Imidazolidinone weedicide, such as
Miaow grass ester (imazamethabenz), imazamox (imazamox), imazapic (imazapic), Arsenal
(imazapyr), Scepter (imazaquin) and Imazethapyr (imazethapyr).
The strong basic anion-exchange resin, containing strong basicity group, such as quaternary amine base (also known as level Four amido)-NR3OH(R
For hydrocarbon group), OH can be dissociated in water - , 0.1~1.2mm of diameter of particle.
The anion exchange resin, before the reaction 1%~4%NaOH of use quality concentration solution pretreatment.
The mass concentration of the paraquat or diquat dibromide aqueous solution is 10%~20%.
The paraquat or diquat dibromide sun water soluble alkali and the molar ratio of inorganic acid or organic acid herbicidal are 1：1~2.
The inorganic acid or organic acid herbicidal and the molar ratio of paraquat or diquat salt are 1~2：1.
The solvent is water.
The temperature is room temperature, preferably 20 DEG C~30 DEG C.
Advantageous effect：Technical solution of the present invention preparation method is simple, and production technology is environmentally protective, not using any other
Reagent, solvent is also water, pollution-free, and resin can reuse, and can be used as long as the more than ten years, suitable for industrial metaplasia
There is synergistic function, the prevention significantly improved compared with single dose exclusive use to weeds to imitate for production, obtained Herbicidal combinations
Fruit.
Specific embodiment
In order to ensure paraquat or diquat dibromide salt is fully converted into paraquat diquat dibromide highly basic, anion in following embodiments
Use quality 1%~4%NaOH of concentration solution pretreatment before exchanger resin reaction.Solvent used in following embodiments is
Water, the temperature of experiment are room temperature, preferably 20 DEG C~30 DEG C.
Embodiment 1
Weigh 192.75 grams of the paraquat solution of mass concentration 10%（0.075mol paraquats）, three-level exchange column is slowly added to, it should
Three-level exchange column is connected in series by three ion exchange columns, and about 67 milliliters of strong alkali anions are filled in each ion exchange column and are exchanged
Resin, three-level collects filtrate after exchanging, then adds 50 milliliters of distilled water flushing anion-exchange resin columns, and merging filtrate slowly drips
Add 7.5 grams of 98% sulfuric acid of mass concentration（0.075mol sulfuric acid）, stir, vacuum distillation removes moisture, obtains 20.1 grams of whites and consolidates
Body is identified by cation chromatography qualitative detection and ion chromatography anion, determines it is paraquat sulfate, yield 95% is pure
Degree 98.5%.
Embodiment 2
Weigh 192.75 grams of the paraquat solution of mass concentration 10%（0.075mol paraquats）, three-level exchange column is slowly added to, it should
Three-level exchange column is connected in series by three ion exchange columns, and about 67 milliliters of strong alkali anions are filled in each ion exchange column and are exchanged
Resin, three-level collects filtrate after exchanging, then adds 50 milliliters of distilled water flushing anion-exchange resin columns, and merging filtrate slowly adds
Enter 27.9 grams of the chloro- phenoxyacetic acids of 4-（The chloro- phenoxyacetic acids of 0.15mol4-）, stir 30 minutes, solution clarification, vacuum distillation
Moisture is removed, obtains 39.3 grams of white solids, is identified by cation chromatography qualitative detection and ion chromatography anion, is determined
It is the chloro- phenoxyacetic acid salt of paraquat 4-, yield 94%, purity 97.6%.
Embodiment 3
Weigh 192.75 grams of the paraquat solution of mass concentration 10%（0.075mol paraquats）, three-level exchange column is slowly added to, it should
Three-level exchange column is connected in series by three ion exchange columns, and about 67 milliliters of strong alkali anions are filled in each ion exchange column and are exchanged
Resin, three-level collects filtrate after exchanging, then adds 50 milliliters of distilled water flushing anion-exchange resin columns, and merging filtrate slowly adds
Enter 38.4 grams of fluroxypramide（0.15mol fluroxypramides）, stir 30 minutes, solution clarification, vacuum distillation removes moisture, obtains 50.1 grams
White solid is identified by cation chromatography qualitative detection and ion chromatography anion, determines it is paraquat fluroxypramide salt, receives
Rate 96%, purity 97.3%.
Embodiment 4
Weigh 258.03 grams of the diquat dibromide solution of mass concentration 10%（0.075mol diquat dibromide）, three-level exchange column is slowly added to, it should
Three-level exchange column is connected in series by three ion exchange columns, and about 67 milliliters of strong alkali anions are filled in each ion exchange column and are exchanged
Resin, three-level collects filtrate after exchanging, then adds 50 milliliters of distilled water flushing anion-exchange resin columns, and merging filtrate slowly drips
Add 7.3 grams of 85% phosphatase 11（0.15mol phosphoric acid）, stir, vacuum distillation removes moisture, obtains 26.9 grams of white solids, passes through sun
Ion chromatography qualitative detection and the identification of ion chromatography anion, determine it is diquat dibromide dihydric phosphate, yield 95%, purity
98.1%.
Embodiment 5
258.03 grams of the diquat dibromide solution of mass concentration 10% is weighed, is slowly added to three-level exchange column, the three-level exchange column is by three
Ion exchange column is connected in series, and about 67 milliliters of strong basic anion-exchange resins is filled in each ion exchange column, after three-level exchanges
Filtrate is collected, then adds 50 milliliters of distilled water flushing anion-exchange resin columns, merging filtrate is slowly added to the chloro- phenoxy group second of 4-
27.9 grams of acid（The chloro- phenoxyacetic acids of 0.15mol4-）, stir 30 minutes, solution clarification, vacuum distillation removes moisture, obtains
39.9 grams of white solids by cation chromatography qualitative detection and the identification of ion chromatography anion, determine it is that diquat dibromide 4- is chloro-
Phenoxyacetic acid salt, yield 96%, purity 97.3%.
Embodiment 6
258.03 grams of the diquat dibromide solution of mass concentration 10% is weighed, is slowly added to three-level exchange column, the three-level exchange column is by three
Ion exchange column is connected in series, and about 67 milliliters of strong basic anion-exchange resins is filled in each ion exchange column, after three-level exchanges
Filtrate is collected, then adds 50 milliliters of distilled water flushing anion-exchange resin columns, merging filtrate is slowly added to 38.4 grams of fluroxypramide
（0.15mol fluroxypramides）, stir 30 minutes, solution clarification, vacuum distillation removes moisture, obtains 49.3 grams of white solids, pass through
Cation chromatography qualitative detection and the identification of ion chromatography anion, determine it is paraquat fluroxypramide salt, yield 95%, purity
98.3%.
Claims (10)
- A kind of 1. preparation method of the compound containing paraquat or diquat, which is characterized in that the preparation method Include the following steps：A. paraquat aqueous solution or diquat dibromide aqueous solution are slowly added to anion-exchange resin column, can obtain strong base solution；B. inorganic acid or organic acid herbicidal are added in above-mentioned strong base solution, stirring is completely dissolved, solution clarification；C. it is evaporated under reduced pressure, removes moisture, obtain the compound containing paraquat or diquat.
- 2. a kind of preparation method of compound containing paraquat or diquat according to claim 1, special Sign is：The inorganic acid is hydrochloric acid, sulfuric acid, phosphoric acid, hydroiodic acid, hydrobromic acid, perchloric acid, periodic acid, hyperbromic acid, chloric acid, iodine One kind in acid, bromic acid, nitric acid, nitrous acid and carbonic acid；The organic acid herbicidal is contains carboxylic acid group, thiocarbonic group Group, sulfonic acid group, sulfinate, thiosulfonic acid group or phosphorous acid herbicide.
- 3. a kind of preparation method of compound containing paraquat or diquat according to claim 1, special Sign is：Step a. is slowly added to paraquat aqueous solution or diquat dibromide aqueous solution to be connected by three anion-exchange resin columns The three-level exchange column formed, three-level exchange can obtain strong base solution.
- 4. a kind of preparation method of compound containing paraquat or diquat according to claim 1, special Sign is：Step a. is slowly added to paraquat aqueous solution or diquat dibromide aqueous solution to be connected by three anion-exchange resin columns The three-level exchange column formed, three-level obtain the strong base solution that purity reaches more than 98.5% after exchanging.
- 5. a kind of preparation method of compound containing paraquat or diquat according to claim 1, special Sign is：Exchanger resin in the anion-exchange resin column is strong basic anion-exchange resin, contains strong basicity on resin Group can dissociate OH in water - , 0.1~1.2mm of diameter of resin particle, use quality concentration 1%~4% before ion exchange NaOH solution pre-processes anion-exchange resin column.
- 6. a kind of preparation method of compound containing paraquat or diquat according to claim 1, special Sign is：The mass concentration of the paraquat aqueous solution or diquat dibromide aqueous solution is 10%~20%.
- 7. a kind of preparation method of compound containing paraquat or diquat according to claim 1, special Sign is：Paraquat or diquat dibromide highly basic and the molar ratio of inorganic acid or organic acid herbicidal are 1 in the strong base solution：1~ 2。
- 8. a kind of preparation method of compound containing paraquat or diquat according to claim 1, special Sign is：The inorganic acid or organic acid herbicidal and the molar ratio of paraquat or diquat salt are 1~2：1.
- 9. a kind of preparation method of compound containing paraquat or diquat according to claim 1, special Sign is：Solvent used in the reaction process is water.
- 10. a kind of preparation method of compound containing paraquat or diquat according to claim 1, special Sign is：The temperature of the reaction is room temperature.
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|---|---|---|---|---|
| GB1244179A (en) * | 1968-03-15 | 1971-08-25 | Ici Ltd | Synthesis of n,n'-disubstituted bipyridylium salts |
| GB1358124A (en) * | 1972-04-21 | 1974-06-26 | Ici Ltd | Manufacture of 1,1,-dimethyl-4,4,- bipyridylium salts |
| GB1577317A (en) * | 1976-04-12 | 1980-10-22 | Ici Ltd | Herbicidal compositions |
| CA1096191A (en) * | 1976-04-15 | 1981-02-24 | George E. Davies | Herbicidal compositions |
| JPS5490180A (en) * | 1977-12-27 | 1979-07-17 | Asahi Chem Ind Co Ltd | Purification and recovery of n,n'-disubstituted bipyridium |
| JPS62135474A (en) * | 1985-12-09 | 1987-06-18 | Tokuyama Soda Co Ltd | Viologen compound |
| CN101874487A (en) * | 2009-12-22 | 2010-11-03 | 安徽丰乐农化有限责任公司 | Paraquat methoxone composite weedicide |
| CN107439555A (en) * | 2017-09-11 | 2017-12-08 | 东南大学 | The method that anionic pesticide and paraquat cation salt are prepared into compound pesticide |
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