CN115304531B - Zwitterionic liquid and preparation method thereof - Google Patents
Zwitterionic liquid and preparation method thereof Download PDFInfo
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- CN115304531B CN115304531B CN202210926296.4A CN202210926296A CN115304531B CN 115304531 B CN115304531 B CN 115304531B CN 202210926296 A CN202210926296 A CN 202210926296A CN 115304531 B CN115304531 B CN 115304531B
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- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- 239000007788 liquid Substances 0.000 title abstract description 9
- 150000001875 compounds Chemical class 0.000 claims abstract description 39
- 239000000575 pesticide Substances 0.000 claims abstract description 29
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 9
- 238000000034 method Methods 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
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 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
- 239000002671 adjuvant Substances 0.000 claims description 5
- 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
- 238000004519 manufacturing process Methods 0.000 claims 1
- 230000000361 pesticidal effect Effects 0.000 claims 1
- 239000012752 auxiliary agent Substances 0.000 abstract description 6
- 230000000052 comparative effect Effects 0.000 abstract description 6
- 150000003839 salts Chemical class 0.000 abstract description 5
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 abstract description 4
- 229910052731 fluorine Inorganic materials 0.000 abstract description 4
- 239000011737 fluorine Substances 0.000 abstract description 4
- -1 propylene, butylene, pentylene Chemical group 0.000 description 24
- 125000002947 alkylene group Chemical group 0.000 description 6
- 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
- 239000007864 aqueous solution Substances 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
- 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
- 239000012043 crude product Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 2
- 239000011828 neutral ionic liquid Substances 0.000 description 2
- 239000000447 pesticide residue Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- FSSPGSAQUIYDCN-UHFFFAOYSA-N 1,3-Propane sultone Chemical group O=S1(=O)CCCO1 FSSPGSAQUIYDCN-UHFFFAOYSA-N 0.000 description 1
- XPBQQAHIVODAIC-UHFFFAOYSA-N 4-bromobutylbenzene Chemical group BrCCCCC1=CC=CC=C1 XPBQQAHIVODAIC-UHFFFAOYSA-N 0.000 description 1
- MVASPUFCXFNIKU-UHFFFAOYSA-N 5-ethylnon-2-ene Chemical group CCCCC(CC)CC=CC MVASPUFCXFNIKU-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
- 125000001931 aliphatic group Chemical group 0.000 description 1
- LKCWBDHBTVXHDL-RMDFUYIESA-N amikacin Chemical compound O([C@@H]1[C@@H](N)C[C@H]([C@@H]([C@H]1O)O[C@@H]1[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O1)O)NC(=O)[C@@H](O)CCN)[C@H]1O[C@H](CN)[C@@H](O)[C@H](O)[C@H]1O LKCWBDHBTVXHDL-RMDFUYIESA-N 0.000 description 1
- 229960004821 amikacin Drugs 0.000 description 1
- 150000001449 anionic compounds Chemical class 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
- 238000013461 design Methods 0.000 description 1
- 238000011161 development 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
- 239000000203 mixture Substances 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
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000011160 research Methods 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
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/04—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
-
- 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
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Plant Pathology (AREA)
- Toxicology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The invention relates toAnd a zwitterionic liquid and a preparation method thereof, in particular to a compound shown in a formula (I), or a salt or a stereoisomer thereof. Compared with the comparative example, the fluorine-containing pesticide auxiliary agent can effectively improve the adhesion quantity and the adhesion firmness of pesticide microdroplets on the plant surface, and can be used in the pesticide field.
Description
Technical Field
The invention belongs to the technical field of chemistry, and particularly relates to a zwitterionic liquid and a preparation method thereof.
Background
Ionic liquids are low melting salts, typically consisting of organic cations and inorganic/organic anions. The physicochemical properties of the ionic liquid can be modified and regulated by changing anions and cations or modifying anions and cations. Ionic liquids have many excellent physicochemical properties: (1) extremely low vapor pressure; (2) High heat resistance and wide liquid temperature range (up to 300 ℃); (3) flame retardancy; (4) The chemical stability is high, and the solubility of other polar substances is excellent; (5) The electrochemical window is wide, and the decomposition voltage is high (can reach 6V); (6) The physicochemical properties can be engineered by 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, although various ionic liquids have been developed in the pesticide field. However, there are few reports on zwitterionic liquids for improving the adhesion amount and the adhesion firmness of pesticide droplets on plant surfaces, and through molecular structure design, development of novel zwitterionic liquids for improving the adhesion amount and the adhesion firmness of pesticide droplets on plant surfaces still has a large research space.
Disclosure of Invention
The invention aims to solve the defects in the prior art and provides a zwitterionic liquid and a preparation method thereof.
In order to achieve the above object, the present invention provides the following technical solutions:
in a first aspect, the present invention provides a compound of formula (I), or a salt thereof, or a stereoisomer thereof:
wherein:
x is selected from alkylene groups.
In some preferred embodiments, the compounds of the present invention are compounds of formula (I), or salts thereof, or stereoisomers thereof, wherein:
x is selected from C 3-12 An alkylene group;
further preferably, X is selected from the group consisting of propylene, butylene, pentylene, n-hexylene, n-heptylene, n-octylene and n-nonylene.
In some embodiments, the compound of formula (I) is the following:
the second aspect of the present invention provides a method for preparing a compound represented by the above formula (I), which comprises the following reaction steps:
1) Dissolving a compound of formula (a) and azetidine in an organic solvent to produce a compound of formula (b);
2) Reacting the compound of formula (b) with tetrafluoroethane-beta-sultone to produce the compound of formula (I).
In some preferred embodiments, the molar amount ratio of the compound of formula (a) to azetidine is from 1:1 to 1:2; more preferably, the molar amount ratio of the compound of formula (a) to the azetidine is from 1:1.4 to 1:1.6; more preferably, the molar amount ratio of the compound of formula (a) to the azetidine is about 1:1.5.
In some preferred embodiments, the ratio of the compound of formula (b) to the tetrafluoroethane-beta-sultone molar amount is 1:1 to 1:2; more preferably, the ratio of the molar amount of the compound of formula (b) to tetrafluoroethane-beta-sultone is from 1:1 to 1:1.5; more preferably, the ratio of the molar amount 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 according to formula (I), wherein the organic solvent in step 1) is selected from one or more of tetrahydrofuran, acetonitrile, ethanol and ethyl acetate.
In a third aspect, the invention provides an application of a compound shown in the formula (I) or a salt or a stereoisomer thereof in preparing a pesticide adjuvant.
In some specific embodiments, the use of the pesticide adjuvant of the present invention is specifically the addition of 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 auxiliary agent to the pesticide aqueous solution is 1:2000.
Definition of terms
In order that the technical content of the present invention can be more clearly understood, the following terms of the present invention will be further described.
"alkylene" refers to straight and branched chain saturated aliphatic hydrocarbon groups. "C 6-12 Alkylene "refers to an alkylene group having 6 to 12 carbon atoms; non-limiting examples of alkylene groups include: 2-ethylpentylene, 3-ethylpentylene, n-octylylene, 2, 3-dimethylhexylylene, 2, 4-dimethylhexyl ylene, 2, 5-dimethylhexyl ylene 2, 2-dimethylhexylene, 3-dimethylhexyl ene, 4-dimethylhexyl ene, 2-ethylhexyl ene, 3-ethylhexyl ene 2-ethylpentylene, 3-ethylpentylene, n-octylylene, 2, 3-dimethylhexylylene, 2, 4-dimethylhexyl ylene, 2, 5-dimethylhexyl ylene, 2-dimethylhexyl ylene, 3-dimethylhexyl ylene, 4-dimethylhexyl ylene, 2-ethylhexyl ylene, 3-ethylhexyl ylene, 2, 5-dimethylhexyl ylene, 2-ethylhexyl ylene, 3-ethylhexyl ylene, 2-ethylhexyl propylene, 2-n-ethylhexyl propylene, 3-ethylhexyl propylene, 2-ethylhexyl propylene, 3-propylene, n-propylene, butylene, propylene, etc 4-ethylhexyl idene, 2-methyl-2-ethylpentyl idene, 2-methyl-3-ethylpentyl idene, n-nonyl idene, 2-methyl-2-ethylhexyl idene, 2-methyl-3-ethylhexyl idene, 2-diethylpentyl idene, n-decyl idene, 3-diethylhexyl idene, 2-diethylhexyl idene, and various branched isomers thereof.
Compared with the prior art, the invention has the beneficial effects that:
the fluorine-containing neutral ionic liquid has the advantages that compared with analogues without fluorine, the fluorine-containing neutral ionic liquid can effectively improve the adhesion quantity and the adhesion firmness of pesticide microdroplets on the surfaces of plants, and can be used in the field of pesticides.
Detailed Description
The following representative examples are intended to better illustrate the invention and are not intended to limit the scope of the invention. The materials used in the examples below are commercially available unless otherwise specified.
Example 1
Step 1 1 Synthesis of- (5-phenylpentyl) azetidine
(5-bromo-n-pentyl) benzene (22.7 g,0.1 mol), azetidine (8.56 g,0.15 mol) were dissolved in acetonitrile (200 mL), stirred under nitrogen in an ice bath for 1 hour, 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 chloroform layer was dried over magnesium sulfate and the solution was evaporated. The crude product was recrystallized from ethanol-ether to give the title compound.
Step 2
10g of the product obtained in step 1 was dissolved in 100mL of dehydrated acetonitrile, and tetrafluoroethane-beta-sultone (55 mmol,9.90 g) was slowly added 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) 384.3[ M+H ]] + 。
Example 2
The preparation method is the same as that of example 1The compound of example 2 was prepared by the preparation method except that (5-bromo-n-pentyl) benzene was replaced with 4-phenyl-1-butylbromide. MS m/z (ESI) 370.1[ M+H ]] + 。
Example 3
The procedure was followed, except that (5-bromo-n-pentyl) benzene was replaced with 1-bromo-6-phenylhexane, to give the compound of example 3. MS m/z (ESI): 398.1[ M+H ]] + 。
Example 4
The procedure was followed, 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): 412.1[ M+H ]] + 。
Example 5
The procedure was followed, except that (5-bromo-n-pentyl) benzene was replaced with 1-bromo-8-phenyloctane, to give the compound of example 5. MS m/z (ESI): 426.2[ M+H ]] + 。
Comparative example 1
The preparation method was the same as in example 1, except that tetrafluoroethane-beta-sultone was replaced with 1, 3-propane sultone, to prepare a compound of comparative example 1. MS m/z (ESI) 326.2[ M+H ]] + 。
Experimental example
The compounds prepared in examples 1-5 and comparative example 1 are respectively added into aqueous solution of first-day amikacin 2000 times according to the mass ratio of 1:2000, pesticide droplets with the volume of 5 mu L are respectively measured on tobacco leaves, and the contact angle of the pesticide droplets on the tobacco leaves is measured; after drying, the mixture was immersed for 12 hours, and the pesticide residue was measured, and the results are shown in Table 1.
TABLE 1
| Contact angle | Pesticide storage amount (%) | |
| Example 1 | 35° | 84.0 |
| Example 2 | 31° | 80.3 |
| Example 3 | 35° | 65.9 |
| Example 4 | 39° | 67.0 |
| Example 5 | 40° | 61.6 |
| Comparative example 1 | 71° | 14.7 |
From the table, the pesticide auxiliary agents prepared in the embodiments 1 to 5 are added into the pesticide aqueous solution according to the mass ratio of 1:2000, and the contact angle of pesticide microdroplets on tobacco leaves is between 30 degrees and 50 degrees; the pesticide is soaked for 12 hours after drying, and the pesticide residue reaches 60% -85%, which is far superior to the pesticide auxiliary agent of comparative example 1. Therefore, the pesticide auxiliary agent obtained by the invention can obviously improve the adhesion quantity and the adhesion firmness of the surface of the blade of the pesticide liquid, and has wide application prospect in the pesticide decrement application field.
Although the invention has been described in detail hereinabove, those skilled in the art will appreciate that various modifications and changes can be made thereto without departing from the spirit and scope of the invention. The scope of the invention is not limited by the detailed description set forth above, but rather is to be attributed to the claims.
Claims (7)
1. A compound of formula (I):
the method is characterized in that:
the compounds of formula (I) are:
2. a process for the preparation of a compound of formula (I) according to claim 1, comprising the reaction steps of:
1) Dissolving a compound of formula (a) and azetidine in an organic solvent to produce a compound of formula (b);
2) Reacting the compound of formula (b) with tetrafluoroethane-beta-sultone to produce the compound of formula (I).
3. The process for the preparation of a compound of formula (I) according to claim 2, wherein the molar amount ratio of the compound of formula (a) to the azetidine is from 1:1 to 1:2.
4. The method for producing a compound represented by formula (I) according to claim 2, wherein the molar ratio of the compound of formula (b) to tetrafluoroethane-beta-sultone is 1:1 to 1:2.
5. The method for preparing a compound represented by formula (I) according to claim 2, wherein the organic solvent is one or more selected from tetrahydrofuran, acetonitrile, ethanol and ethyl acetate.
6. Use of a compound of formula (I) according to claim 1 for the preparation of a pesticidal adjuvant.
7. The use according to claim 6, characterized in that the pesticide adjuvant is added to an aqueous pesticide solution.
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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 |
| CN115108973A (en) * | 2022-08-03 | 2022-09-27 | 苏州旭珀禾科技有限公司 | Electrically neutral ionic 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 CN202210926296.4A patent/CN115304531B/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 |
| CN115108973A (en) * | 2022-08-03 | 2022-09-27 | 苏州旭珀禾科技有限公司 | Electrically neutral ionic 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 |
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