CN115108973A - Electrically neutral ionic liquid and preparation method thereof - Google Patents
Electrically neutral ionic liquid and preparation method thereof Download PDFInfo
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- CN115108973A CN115108973A CN202210927335.2A CN202210927335A CN115108973A CN 115108973 A CN115108973 A CN 115108973A CN 202210927335 A CN202210927335 A CN 202210927335A CN 115108973 A CN115108973 A CN 115108973A
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- compound
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- stereoisomer
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- 238000002360 preparation method Methods 0.000 title claims abstract description 13
- 239000011828 neutral ionic liquid Substances 0.000 title abstract description 9
- 150000001875 compounds Chemical class 0.000 claims abstract description 41
- 239000000575 pesticide Substances 0.000 claims abstract description 28
- 150000003839 salts Chemical class 0.000 claims abstract description 10
- -1 propylene, butylene, pentylene Chemical group 0.000 claims description 31
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 9
- ZMSRCMWBEGLBAI-UHFFFAOYSA-N 3,3,4,4-tetrafluorooxathietane 2,2-dioxide Chemical compound FC1(F)OS(=O)(=O)C1(F)F ZMSRCMWBEGLBAI-UHFFFAOYSA-N 0.000 claims description 8
- 125000002947 alkylene group Chemical group 0.000 claims description 8
- GCNTZFIIOFTKIY-UHFFFAOYSA-N 4-hydroxypyridine Chemical compound OC1=CC=NC=C1 GCNTZFIIOFTKIY-UHFFFAOYSA-N 0.000 claims description 7
- 239000002671 adjuvant Substances 0.000 claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- 230000000361 pesticidal effect Effects 0.000 claims 1
- 230000000052 comparative effect Effects 0.000 abstract description 5
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 abstract description 3
- 229910052731 fluorine Inorganic materials 0.000 abstract description 3
- 239000011737 fluorine Substances 0.000 abstract description 3
- QICUPOFVENZWSC-UHFFFAOYSA-N 5-bromopentylbenzene Chemical compound BrCCCCCC1=CC=CC=C1 QICUPOFVENZWSC-UHFFFAOYSA-N 0.000 description 5
- 239000002608 ionic liquid Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 241000196324 Embryophyta Species 0.000 description 3
- 241000208125 Nicotiana Species 0.000 description 3
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 3
- 150000001450 anions Chemical class 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000012752 auxiliary agent Substances 0.000 description 3
- 150000001768 cations Chemical class 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 125000004376 1,2-dimethylbutylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- FSSPGSAQUIYDCN-UHFFFAOYSA-N 1,3-Propane sultone Chemical group O=S1(=O)CCCO1 FSSPGSAQUIYDCN-UHFFFAOYSA-N 0.000 description 1
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- JMMZCWZIJXAGKW-UHFFFAOYSA-N 2-methylpent-2-ene Chemical group CCC=C(C)C JMMZCWZIJXAGKW-UHFFFAOYSA-N 0.000 description 1
- XPBQQAHIVODAIC-UHFFFAOYSA-N 4-bromobutylbenzene Chemical group BrCCCCC1=CC=CC=C1 XPBQQAHIVODAIC-UHFFFAOYSA-N 0.000 description 1
- RAOLIGFNQJMMKW-UHFFFAOYSA-N 6-bromohexylbenzene Chemical group BrCCCCCCC1=CC=CC=C1 RAOLIGFNQJMMKW-UHFFFAOYSA-N 0.000 description 1
- ASLQYSAHLPRDAY-UHFFFAOYSA-N 7-bromoheptylbenzene Chemical group BrCCCCCCCC1=CC=CC=C1 ASLQYSAHLPRDAY-UHFFFAOYSA-N 0.000 description 1
- XGBMCFCZEKCCDJ-UHFFFAOYSA-N 8-bromooctylbenzene Chemical group BrCCCCCCCCC1=CC=CC=C1 XGBMCFCZEKCCDJ-UHFFFAOYSA-N 0.000 description 1
- 150000007960 acetonitrile Chemical class 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001449 anionic compounds Chemical class 0.000 description 1
- WFDXOXNFNRHQEC-GHRIWEEISA-N azoxystrobin Chemical compound CO\C=C(\C(=O)OC)C1=CC=CC=C1OC1=CC(OC=2C(=CC=CC=2)C#N)=NC=N1 WFDXOXNFNRHQEC-GHRIWEEISA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000007385 chemical modification Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 150000002891 organic anions Chemical class 0.000 description 1
- 150000002892 organic cations Chemical class 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Classifications
-
- 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/68—One oxygen atom attached in position 4
-
- 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
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/24—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing ingredients to enhance the sticking of the active ingredients
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Toxicology (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The invention relates to a charge neutral ionic liquid and a preparation method thereof, in particular to a compound shown as a formula (I), or a salt or a stereoisomer thereof. Compared with the comparative example, the fluorine-containing neutral ionic liquid can effectively improve the attachment amount and the attachment firmness of pesticide droplets on the surface of plants, and can be used in the field of pesticides.
Description
Technical Field
The invention belongs to the technical field of chemistry, and particularly relates to a charge neutral ionic liquid and a preparation method thereof.
Background
Ionic liquids are low melting salts, typically consisting of organic cations and inorganic/organic anions. The physicochemical property of the ionic liquid can be adjusted and controlled by changing the anions and cations or modifying the anions and cations. Ionic liquids have many excellent physicochemical properties: (1) the vapor pressure is extremely low; (2) high heat resistance, wide liquid temperature range (up to 300 ℃); (3) flame retardancy; (4) the chemical stability is high, and the solubility to other polar substances is excellent; (5) the electrochemical window is wide, and the decomposition voltage is high (up to 6V); (6) the physicochemical properties can be adjusted by design through chemical modification of the cation or by changing the anion. These unique properties of ionic liquids have led to their gradual and widespread use.
To date, a variety of ionic liquids have been developed in the field of pesticides. However, there are few reports on electrically neutral ionic liquids for improving the adhesion amount and the adhesion firmness of pesticide droplets on plant surfaces, and there is still a great research space for developing novel electrically neutral ionic liquids for improving the adhesion amount and the adhesion firmness of pesticide droplets on plant surfaces through molecular structure design.
Disclosure of Invention
The invention aims to solve the defects in the prior art and provides a charge neutral ionic liquid and a preparation method thereof.
Aiming at the above purpose, the invention provides the following technical scheme:
in a first aspect, the present invention provides a compound of formula (I), or a salt, or stereoisomer thereof:
wherein:
x is selected from alkylene.
In some preferred embodiments, the compounds of the present invention are of formula (I), or a salt, or stereoisomer thereof, wherein:
x is selected from C 3-12 An alkylene group;
further preferably, X is selected from propylene, butylene, pentylene, n-hexylene, n-heptylene, n-octylene and n-nonylene.
In some embodiments, the compound of formula (I) is the following compound:
in a second aspect, the present invention provides a process for the preparation of a compound of formula (I) as defined above, comprising the reaction steps of:
1) dissolving a compound of formula (a) and 4-pyridone in an organic solvent to produce a compound of formula (b);
2) reacting the compound of the formula (b) with tetrafluoroethane-beta-sultone to prepare the compound of the formula (I).
In some preferred embodiments, the molar weight ratio of the compound of formula (a) to 4-pyridone is from 1:1 to 1: 2; more preferably, the molar ratio of the compound of formula (a) to 4-pyridone is from 1:1.4 to 1: 1.6; more preferably, the molar weight ratio of the compound of formula (a) to 4-pyridone is about 1: 1.5.
In some preferred embodiments, the molar amount ratio of the compound of formula (b) to tetrafluoroethane-beta-sultone is from 1:1 to 1: 2; more preferably, the molar ratio of the compound of formula (b) to tetrafluoroethane-beta-sultone is from 1:1 to 1: 1.5; more preferably, the molar ratio of the compound of formula (b) to tetrafluoroethane-beta-sultone is from 1:1.1 to 1: 1.2.
In some preferred embodiments, the method for preparing a compound of formula (I) is performed in step 1), wherein the organic solvent is one or more selected from tetrahydrofuran, acetonitrile, ethanol, and ethyl acetate.
The third aspect of the present invention provides a use of the compound represented by the above formula (I), or a salt thereof, or a stereoisomer thereof for producing an adjuvant for agricultural chemicals.
In some specific embodiments, the pesticide adjuvant of the present invention is used by adding the pesticide adjuvant to an aqueous pesticide solution. Preferably, the mass ratio of the pesticide auxiliary agent to the pesticide aqueous solution is 1:500-1: 4000; further preferably, the mass ratio of the pesticide adjuvant to the pesticide aqueous solution is 1: 2000.
Definition of terms
In order to clearly understand the technical contents of the present invention, the following terms will be further described.
"alkylene" refers to straight and branched chain saturated aliphatic hydrocarbon groups. "C 6-12 Alkylene "means an alkylene having 6 to 12 carbon atoms; non-limiting examples of alkylene groups include: propylene, butylene, pentylene, n-hexylene, 1-ethyl-2-methylpropylene, 1, 2-trimethylpropylene, 1-dimethylbutylene, 1, 2-dimethylbutylene, 2-dimethylbutylene, 1, 3-dimethylbutyleneene, 2-ethylbutyl, 2-methylpentylene, 3-methylpentylene, 4-methylpentylene, 2, 3-dimethylbutylene, n-heptylene2-methylhexylene, 3-methylhexylene, 4-methylhexylene, 5-methylhexylene, 2, 3-dimethylpentylene, 2, 4-dimethylpentylene, 2-dimethylpentylene, 3-dimethylpentylene, 2-ethylpentylene, 3-ethylpentylene, n-octylene, 2, 3-dimethylhexyl, 2, 4-dimethylhexyl, 2, 5-dimethylhexyl, 2-dimethylhexyl, 3-dimethylhexyl, 4-dimethylhexyl, 2-ethylhexyl, 3-ethylhexyl, 4-ethylhexyl, 2-methyl-2-ethylpentylene, 2-methyl-3-ethylpentylene, 2, 4-dimethylhexyl, 2-ethylhexyl, 4-dimethylhexyl, 2-methyl-3-ethylpentylene, 2-methyl-2-ethyl-pentyl, 2-ethyl-2, 2-ethyl-pentyl, 2-ethyl, 2-pentyl, 2-ethyl, 2-pentyl, 2-ethyl, 2-pentyl, 2, and so, N-nonylene, 2-methyl-2-ethylhexyl, 2-methyl-3-ethylhexyl, 2-diethylpentyl, n-decyl, 3-diethylhexyl, 2-diethylhexyl, and various branched isomers thereof.
Compared with the prior art, the invention has the beneficial effects that:
compared with the analog without fluorine, the fluorine-containing neutral ionic liquid can effectively improve the attachment amount and the attachment firmness of pesticide droplets on the surface of plants, and can be used in the field of pesticides.
Detailed Description
The following representative examples are intended to better illustrate the present invention and are not intended to limit the scope of the present invention. The materials used in the following examples are all commercially available unless otherwise specified.
Example 1
Step Synthesis of 11- (5-phenylpentyl) 4-pyridone
(5-bromo-n-pentyl) benzene (22.7g,0.1mol), 4-pyridone (14.27g,0.15mol) were dissolved in acetonitrile (200mL), stirred in an ice bath under nitrogen for 1 hour, stirred at room temperature for 1 hour, at 35 ℃ for 1 day, and at 45 ℃ for 2 days. The reaction solution was dried under reduced pressure, and the obtained solid was dissolved in chloroform. The mixture was separated with saturated aqueous sodium bicarbonate (3 times), and the chloroform layer was dried over magnesium sulfate, and the dried solution was evaporated. The crude product was recrystallized from ethanol-ether to give the title compound.
Step 2
10g of the product from step 1 was dissolved in 100mL of dehydrated acetonitrile and tetrafluoroethane-beta-sultone (55mmol, 9.90g) was added slowly while stirring. It was stirred under nitrogen atmosphere at 50 ℃ for 12 hours. The precipitated crystals were filtered off by standing at room temperature. The crude product was recrystallized from ethanol-ether to give the compound of example 1. MS M/z (ESI) 422.1[ M + H ]] + 。
Example 2
Preparation method the same as that of example 1 except that (5-bromo-n-pentyl) benzene was replaced with 4-phenyl-1-butyl bromide, was used to prepare the compound of example 2. MS M/z (ESI) 408.1[ M + H] + 。
Example 3
Preparation method the same as that of example 1 except that (5-bromo-n-pentyl) benzene was replaced with 1-bromo-6-phenylhexane, the compound of example 3 was prepared. MS M/z (ESI) 436.1[ M + H] + 。
Example 4
Preparation the same as that of example 1 except that (5-bromo-n-pentyl) benzene was replaced with 1-bromo-7-phenylheptane, to give the compound of example 4. MS M/z (ESI) 450.1[ M + H] + 。
Example 5
Preparation method the same as that of example 1 except that (5-bromo-n-pentyl) benzene was replaced with 1-bromo-8-phenyloctane was used to prepare the compound of example 5. MS M/z (ESI) 464.1[ M + H ]] + 。
Comparative example 1
Preparation method the same as that of example 1 except that tetrafluoroethane-beta-sultone was replaced with 1, 3-propane sultone was used to prepare the compound of comparative example 1. MS M/z (ESI) 364.2[ M + H] + 。
Examples of the experiments
Adding the compounds prepared in examples 1-5 and comparative example 1 into 2000 times of water solution of the first-positive-resistance Amistar according to the mass ratio of 1:2000, respectively, measuring pesticide droplets with the volume of 5 mu L on tobacco leaves, and measuring the contact angle of the pesticide droplets on the tobacco leaves; after drying, the mixture is soaked for 12h, and the pesticide retention is detected, and the result is shown in table 1.
TABLE 1
As can be seen from the above table, the pesticide adjuvant prepared in the embodiments 1 to 5 of the present invention is added to the pesticide aqueous solution according to the mass ratio of 1:2000, and the contact angle of the pesticide droplets on the tobacco leaves is between 30-50 ℃; after being dried, the pesticide is soaked in water for 12 hours, and the pesticide retention amount reaches 60 to 88 percent, which is far better than that of the pesticide auxiliary agent in the comparative example 1. Therefore, the pesticide auxiliary agent obtained by the invention can obviously improve the blade surface adhesion amount and the adhesion firmness of the pesticide liquid, and has wide application prospect in the field of pesticide reduction and use.
Although the present invention has been described in detail above, those skilled in the art will appreciate that various modifications and changes can be made to the present invention without departing from the spirit and scope of the invention. The scope of the invention is not to be limited by the above detailed description but is only limited by the claims.
Claims (10)
1. A compound of formula (I), or a salt, or stereoisomer thereof:
wherein:
x is selected from alkylene.
2. The compound of formula (I), or a salt or stereoisomer thereof, according to claim 1, wherein X is selected from C 3-12 An alkylene group.
3. The compound of formula (I), or a salt or stereoisomer thereof, according to claim 1, wherein X is selected from the group consisting of propylene, butylene, pentylene, n-hexylene, n-heptylene, n-octylene, and n-nonylene.
4. The compound of formula (I), or a salt or stereoisomer thereof, according to claim 1, wherein the compound of formula (I) is:
5. a process for the preparation of a compound of formula (I) according to claim 1, comprising the following reaction steps:
1) dissolving a compound of formula (a) and 4-pyridone in an organic solvent to produce a compound of formula (b);
2) reacting the compound of the formula (b) with tetrafluoroethane-beta-sultone to prepare the compound of the formula (I).
6. The process according to claim 5, wherein the molar ratio of the compound of formula (a) to the 4-pyridone is 1:1 to 1: 2.
7. The method for preparing the compound shown in the formula (I) according to claim 5, wherein the molar ratio of the compound shown in the formula (b) to the tetrafluoroethane-beta-sultone is 1:1-1: 2.
8. The method for preparing the compound represented by the formula (I) according to claim 5, wherein the organic solvent is one or more selected from tetrahydrofuran, acetonitrile, ethanol and ethyl acetate.
9. Use of a compound of formula (I), or a salt thereof, or a stereoisomer thereof, according to any one of claims 1 to 4, in the preparation of a pesticidal adjuvant.
10. Use according to claim 9, characterized in that the pesticide adjuvant is added to an aqueous pesticide solution.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210927335.2A CN115108973B (en) | 2022-08-03 | 2022-08-03 | Electrically neutral ionic liquid and preparation method thereof |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210927335.2A CN115108973B (en) | 2022-08-03 | 2022-08-03 | Electrically neutral ionic liquid and preparation method thereof |
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| Publication Number | Publication Date |
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| CN115108973A true CN115108973A (en) | 2022-09-27 |
| CN115108973B CN115108973B (en) | 2023-11-14 |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115304531A (en) * | 2022-08-03 | 2022-11-08 | 苏州旭珀禾科技有限公司 | Zwitterionic liquid and preparation method thereof |
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|---|---|---|---|---|
| SU134691A1 (en) * | 1960-04-09 | 1960-11-30 | нц И.Л. Кнун | Method for acylation of alcohols |
| US5414117A (en) * | 1992-02-21 | 1995-05-09 | Centre National De La Recherche Scientifique | Monomers derived from perhalogenated sultones and polymers obtained from these monomers |
| RU2503659C1 (en) * | 2012-12-20 | 2014-01-10 | Закрытое акционерное общество научно-производственное Объединение "ПиМ-Инвест" (ЗАО НПО "Пим-Инвест") | Method of producing oxaperfluoroalkane sulphonic acids and salts thereof |
| CN115304531A (en) * | 2022-08-03 | 2022-11-08 | 苏州旭珀禾科技有限公司 | Zwitterionic liquid and preparation method thereof |
| CN115304518A (en) * | 2022-08-03 | 2022-11-08 | 苏州旭珀禾科技有限公司 | Biocompatible zwitterionic compound and preparation method thereof |
-
2022
- 2022-08-03 CN CN202210927335.2A patent/CN115108973B/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU134691A1 (en) * | 1960-04-09 | 1960-11-30 | нц И.Л. Кнун | Method for acylation of alcohols |
| US5414117A (en) * | 1992-02-21 | 1995-05-09 | Centre National De La Recherche Scientifique | Monomers derived from perhalogenated sultones and polymers obtained from these monomers |
| RU2503659C1 (en) * | 2012-12-20 | 2014-01-10 | Закрытое акционерное общество научно-производственное Объединение "ПиМ-Инвест" (ЗАО НПО "Пим-Инвест") | Method of producing oxaperfluoroalkane sulphonic acids and salts thereof |
| CN115304531A (en) * | 2022-08-03 | 2022-11-08 | 苏州旭珀禾科技有限公司 | Zwitterionic liquid and preparation method thereof |
| CN115304518A (en) * | 2022-08-03 | 2022-11-08 | 苏州旭珀禾科技有限公司 | Biocompatible zwitterionic compound and preparation method thereof |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115304531A (en) * | 2022-08-03 | 2022-11-08 | 苏州旭珀禾科技有限公司 | Zwitterionic liquid and preparation method thereof |
| CN115304531B (en) * | 2022-08-03 | 2023-11-14 | 苏州旭珀禾科技有限公司 | Zwitterionic liquid and preparation method thereof |
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| Publication number | Publication date |
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| CN115108973B (en) | 2023-11-14 |
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