CN102090397B - High-purity imidazolone weedicide ammonium salt raw powder and production process thereof - Google Patents
High-purity imidazolone weedicide ammonium salt raw powder and production process thereof Download PDFInfo
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- CN102090397B CN102090397B CN 201010610830 CN201010610830A CN102090397B CN 102090397 B CN102090397 B CN 102090397B CN 201010610830 CN201010610830 CN 201010610830 CN 201010610830 A CN201010610830 A CN 201010610830A CN 102090397 B CN102090397 B CN 102090397B
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- imidazolinone herbicide
- ammonium salt
- ammonia
- purity
- amine
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- CAAMSDWKXXPUJR-UHFFFAOYSA-N 3,5-dihydro-4H-imidazol-4-one Chemical compound O=C1CNC=N1 CAAMSDWKXXPUJR-UHFFFAOYSA-N 0.000 title claims abstract description 28
- 239000000843 powder Substances 0.000 title claims abstract description 26
- 150000003863 ammonium salts Chemical class 0.000 title claims abstract description 18
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 14
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 34
- 239000003814 drug Substances 0.000 claims abstract description 18
- 229910021529 ammonia Inorganic materials 0.000 claims abstract description 17
- 239000002904 solvent Substances 0.000 claims abstract description 17
- 150000001412 amines Chemical class 0.000 claims abstract description 13
- 238000001035 drying Methods 0.000 claims abstract description 11
- 238000001914 filtration Methods 0.000 claims abstract description 4
- 239000004009 herbicide Substances 0.000 claims description 27
- 230000002363 herbicidal effect Effects 0.000 claims description 26
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
- -1 methoxyl methyl Chemical group 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 9
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 claims description 9
- 238000005516 engineering process Methods 0.000 claims description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 6
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 5
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 5
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 238000005469 granulation Methods 0.000 claims description 3
- 230000003179 granulation Effects 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 239000000463 material Substances 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 238000000034 method Methods 0.000 abstract description 6
- 150000001875 compounds Chemical class 0.000 abstract 1
- 238000001704 evaporation Methods 0.000 abstract 1
- 238000005453 pelletization Methods 0.000 abstract 1
- 241000196324 Embryophyta Species 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 8
- 230000008029 eradication Effects 0.000 description 8
- 239000007787 solid Substances 0.000 description 7
- 230000006837 decompression Effects 0.000 description 5
- QRSHQJLLXXEYPS-UHFFFAOYSA-N azane;5-ethyl-2-(4-methyl-5-oxo-4-propan-2-yl-1h-imidazol-2-yl)pyridine-3-carboxylic acid Chemical compound [NH4+].[O-]C(=O)C1=CC(CC)=CN=C1C1=NC(C)(C(C)C)C(=O)N1 QRSHQJLLXXEYPS-UHFFFAOYSA-N 0.000 description 4
- 235000019504 cigarettes Nutrition 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 210000003298 dental enamel Anatomy 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- XVOKUMIPKHGGTN-UHFFFAOYSA-N Imazethapyr Chemical compound OC(=O)C1=CC(CC)=CN=C1C1=NC(C)(C(C)C)C(=O)N1 XVOKUMIPKHGGTN-UHFFFAOYSA-N 0.000 description 3
- JACTTWVLMNPJQA-UHFFFAOYSA-N azane;quinoline Chemical compound N.N1=CC=CC2=CC=CC=C21 JACTTWVLMNPJQA-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 230000000442 meristematic effect Effects 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- CABMTIJINOIHOD-UHFFFAOYSA-N 2-[4-methyl-5-oxo-4-(propan-2-yl)-4,5-dihydro-1H-imidazol-2-yl]quinoline-3-carboxylic acid Chemical compound N1C(=O)C(C(C)C)(C)N=C1C1=NC2=CC=CC=C2C=C1C(O)=O CABMTIJINOIHOD-UHFFFAOYSA-N 0.000 description 1
- PVSGXWMWNRGTKE-UHFFFAOYSA-N 5-methyl-2-[4-methyl-5-oxo-4-(propan-2-yl)-4,5-dihydro-1H-imidazol-2-yl]pyridine-3-carboxylic acid Chemical compound N1C(=O)C(C(C)C)(C)N=C1C1=NC=C(C)C=C1C(O)=O PVSGXWMWNRGTKE-UHFFFAOYSA-N 0.000 description 1
- 239000005981 Imazaquin Substances 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000857 drug effect Effects 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 230000017074 necrotic cell death Effects 0.000 description 1
- 229960003512 nicotinic acid Drugs 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- YZHUMGUJCQRKBT-UHFFFAOYSA-M sodium chlorate Chemical compound [Na+].[O-]Cl(=O)=O YZHUMGUJCQRKBT-UHFFFAOYSA-M 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
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- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
The invention particularly discloses high-purity imidazolone weedicide ammonium salt raw powder and a production process thereof, which belong to the field of application of weedicides. The process comprises the following steps of: mixing an imidazolone weedicide active compound, amine (ammonia) and double solvents; completely salifying; evaporating a low-boiling-point solvent for pelletizing; filtering; and drying under the reduced pressure to obtain a product. By adopting the method, the product has the advantages of high content, good medicament effect, high mixing performance, short production period, simple production process, wide application range and broad market prospect.
Description
(1) technical field
The invention belongs to the weed killer herbicide application, particularly a kind of high-purity imidazolinone herbicide ammonium salt raw powder and production technology thereof.
(2) background technology
Imidazolinone herbicide is to absorb by plant roots and cauline leaf, in xylem and phloem conduction, accumulates in meristematic tissue.After cauline leaf was handled, susceptible weeds stopped growing immediately, and after the soil treatment, root absorption upwards conducts to the meristematic tissue on weeds top, it was stopped growing and necrosis.That at present, drops into that commercialization produces has imidazoles nicotinic acid.Miaow oxalate, imazaquin, imazethapyr etc.The former liquid medicine dissolubility of imidazolinone herbicide is poor, and the universal method of dealing with problems is salify, and the formulation of common usefulness is to be the theme with isopropyl amine salt and ammonium salt on the market now, and that uses for many years facts have proved that ammonium salt is generally accepted for users at home and abroad.
At present, the main technique of synthetic imidazolinone herbicide ammonium salt raw powder is single solvent method, and synthetic ammonium salt is vitreum, need leave standstill for a long time to become solid, could beat powder after thoroughly pulverizing, and the production cycle is long, complex manufacturing.
(3) summary of the invention
The present invention provides a kind of drug effect is remarkable, the performance that is mixed is good high-purity imidazolinone herbicide ammonium salt raw powder and production technology thereof in order to remedy the deficiencies in the prior art.
The present invention is achieved through the following technical solutions:
A kind of high-purity imidazolinone herbicide ammonium salt raw powder is characterized in that: the parts by weight that contain the imidazolinone herbicide ammonium salt in the former powder are 95～99%, and loss on drying≤0.1% during its high level, can reach 98～99%.
The former medicine of imidazolinone herbicide, amine (ammonia) and solvent pairs are mixed, behind the salify, steam low boiling point solvent and carry out granulation fully, the oven dry of reducing pressure after filtering more namely obtains product; Wherein, the former medicine of imidazolinone herbicide is
R is hydrogen, methyl, ethyl, methoxyl methyl or phenyl; The mol ratio of the former medicine of imidazolinone herbicide and amine (ammonia) is 1: 1～3, with the weight proportion of solvent pairs be 1: 1～6.
Described amine (ammonia) is organic amine or liquefied ammonia such as methylamine, n-propylamine, isopropylamine.
Described solvent pairs is the organic solvent that two kinds of materials in methyl alcohol, ethanol, acetone, ethyl acetate, carrene, dichloroethane, n-hexane, cyclohexane, ether, benzinum and the dioxane are formed by 1: 1 weight proportion.
The mol ratio of the former medicine of described imidazolinone herbicide and amine (ammonia) is 1: 1.5, with the weight proportion of solvent pairs be 1: 4.
Because the too high meeting of bake out temperature causes the product ammonium salt partly to decompose, and causes product water-soluble bad, therefore oven dry needs the decompression oven dry.
Product purity of the present invention adopts efficient liquid phase chromatographic analysis, and analyzing and testing result shows that the product purity of the inventive method can reach more than 98%.
Product content height of the present invention, good drug efficacy, the performance that is mixed is good, and is with short production cycle, and production technology is simple, is widely used, and market prospects are wide.
(4) embodiment
Embodiment 1;
The former medicine 500kg of the Imazethapyr of purity 98% (1.70kmol), 43.2kg (2.54kmol) liquefied ammonia, 1000kg acetone, 1000kg cyclohexane are reacted in the enamel reaction still of 3000L, after stirring reaction is transparent, steam acetone, cooling is filtered, solid can obtain high-purity Imazethapyr ammonium salt raw powder 482kg (1.56kmol) thus with the decompression oven for drying.In the resulting Imazethapyr ammonium salt raw powder, contain the Imazethapyr ammonium salt more than 98%, loss on drying≤1.0%.
State high-purity Imazethapyr ammonium salt raw powder product, be solid powdery, can be used as a kind of good composite female powder, mix with solid, or mix with liquid, all do not have bad physical phenomenons such as precipitation, layering, muddiness, the industrialization that very easy realization is mixed.Can be widely used.The present invention not only can directly use and be configurable, and female powder of holding concurrently, preparation are to use in the present Imazethapyr and the level that disposes in the preparation is the highest, product the most easily.
Embodiment 2:
The former medicine 500kg of the weed eradication cigarette of purity 98% (1.88kmol), 166kg (2.82kmol) isopropylamine, 1000kg carrene, 1000kg benzinum are reacted in the enamel reaction still of 3000L, after stirring reaction is transparent, steam carrene, cooling is filtered, solid can obtain the high-purity weed eradication cigarette former powder 558kg of isopropyl amine salt (1.73kmol) thus with the decompression oven for drying.In the former powder of resulting weed eradication cigarette isopropyl amine salt, contain weed eradication cigarette isopropyl amine salt more than 98%, loss on drying≤1.0%.。
Embodiment 3:
The former medicine 500kg of the imazapic of purity 98% (1.78kmol), 158kg (2.67kmol) isopropylamine, 1000kg methyl alcohol, 1000kg cyclohexane are reacted in the enamel reaction still of 3000L, after stirring reaction is transparent, steam methyl alcohol, cooling is filtered, solid can obtain the former powder 553kg of high-purity methyl Imazethapyr isopropyl amine salt (1.64kmol) thus with the decompression oven for drying.In the former powder of resulting imazapic isopropyl amine salt, contain the imazapic isopropyl amine salt more than 98%, loss on drying≤1.0%.
Embodiment 4:
The former medicine 500kg of the weed eradication quinoline of purity 98% (1.58kmol), 40.2kg (2.36kmol) liquefied ammonia, 1000kg acetone, 1000kg benzinum are reacted in the enamel reaction still of 3000L, after stirring reaction is transparent, steam acetone, cooling is filtered, solid can obtain high-purity weed eradication quinoline ammonium salt raw powder 480kg (1.45kmol) thus with the decompression oven for drying.In the resulting weed eradication quinoline ammonium salt raw powder, contain weed eradication quinoline ammonium salt salt more than 98%, loss on drying≤1.0%.
Claims (4)
1. high-purity imidazolinone herbicide ammonium salt raw powder, it is characterized in that: the parts by weight that contain the imidazolinone herbicide ammonium salt in the former powder are 95 ~ 99%, loss on drying≤0.1%, its production craft step is, the former medicine of imidazolinone herbicide, amine (ammonia) and solvent pairs are mixed, behind the salify, steam low boiling point solvent and carry out granulation fully, the oven dry of reducing pressure after filtering more namely obtains product; Wherein, the former medicine of imidazolinone herbicide is
, R is hydrogen, methyl, ethyl, methoxyl methyl or phenyl; The mol ratio of the former medicine of imidazolinone herbicide and amine (ammonia) is 1:1 ~ 3, with the weight proportion of solvent pairs be 1:1 ~ 6; Described amine (ammonia) is methylamine, n-propylamine, isopropylamine or liquefied ammonia; Described solvent pairs is the organic solvent that two kinds of materials in methyl alcohol, ethanol, acetone, ethyl acetate, carrene, dichloroethane, n-hexane, cyclohexane, ether, benzinum and the dioxane are formed by the weight proportion of 1:1.
2. high-purity imidazolinone herbicide ammonium salt raw powder according to claim 1, it is characterized in that: the parts by weight that contain the imidazolinone herbicide ammonium salt in the described former powder are 98 ~ 99%.
3. the production technology of high-purity imidazolinone herbicide ammonium salt raw powder according to claim 1, it is characterized in that: the former medicine of imidazolinone herbicide, amine (ammonia) and solvent pairs are mixed, fully behind the salify, steam low boiling point solvent and carry out granulation, the oven dry of reducing pressure after filtering more namely obtains product; Wherein, the former medicine of imidazolinone herbicide is
, R is hydrogen, methyl, ethyl, methoxyl methyl or phenyl; The mol ratio of the former medicine of imidazolinone herbicide and amine (ammonia) is 1:1 ~ 3, with the weight proportion of solvent pairs be 1:1 ~ 6; Described amine (ammonia) is methylamine, n-propylamine, isopropylamine or liquefied ammonia; Described solvent pairs is the organic solvent that two kinds of materials in methyl alcohol, ethanol, acetone, ethyl acetate, carrene, dichloroethane, n-hexane, cyclohexane, ether, benzinum and the dioxane are formed by the weight proportion of 1:1.
4. according to the production technology of the described high-purity imidazolinone herbicide of claim 3 ammonium salt raw powder, it is characterized in that: the mol ratio of the former medicine of described imidazolinone herbicide and amine (ammonia) is 1:1.5, with the weight proportion of solvent pairs be 1:4.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 201010610830 CN102090397B (en) | 2010-12-29 | 2010-12-29 | High-purity imidazolone weedicide ammonium salt raw powder and production process thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 201010610830 CN102090397B (en) | 2010-12-29 | 2010-12-29 | High-purity imidazolone weedicide ammonium salt raw powder and production process thereof |
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| Publication Number | Publication Date |
|---|---|
| CN102090397A CN102090397A (en) | 2011-06-15 |
| CN102090397B true CN102090397B (en) | 2013-08-07 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN 201010610830 Active CN102090397B (en) | 2010-12-29 | 2010-12-29 | High-purity imidazolone weedicide ammonium salt raw powder and production process thereof |
Country Status (1)
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101636084A (en) * | 2007-03-16 | 2010-01-27 | 组合化学工业株式会社 | herbicide composition |
| CN101671076A (en) * | 2009-09-01 | 2010-03-17 | 山东先达化工有限公司 | Oxidative degradation process for imidazolinone herbicide wastewater |
| TW201018399A (en) * | 2008-09-26 | 2010-05-16 | Basf Se | Liquid, water-emulsifiable active ingredient concentrates |
| CN101856036A (en) * | 2010-06-13 | 2010-10-13 | 南京农业大学 | Biological herbicide compound and preparation method thereof |
-
2010
- 2010-12-29 CN CN 201010610830 patent/CN102090397B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101636084A (en) * | 2007-03-16 | 2010-01-27 | 组合化学工业株式会社 | herbicide composition |
| TW201018399A (en) * | 2008-09-26 | 2010-05-16 | Basf Se | Liquid, water-emulsifiable active ingredient concentrates |
| CN101671076A (en) * | 2009-09-01 | 2010-03-17 | 山东先达化工有限公司 | Oxidative degradation process for imidazolinone herbicide wastewater |
| CN101856036A (en) * | 2010-06-13 | 2010-10-13 | 南京农业大学 | Biological herbicide compound and preparation method thereof |
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| CN102090397A (en) | 2011-06-15 |
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Effective date of registration: 20211130 Address after: 261000 East 2nd house, Lingang chemical park, Binhai Economic Development Zone, Weifang City, Shandong Province Patentee after: WEIFANG CYNDA CHEMICAL Co.,Ltd. Patentee after: Shandong Xianda agrochemical Co., Ltd Address before: 261000 Lingang Chemical Park, Weifang Binhai Economic Development Zone, Shandong Province Patentee before: WEIFANG CYNDA CHEMICAL Co.,Ltd. |
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