CN118165293A - Isoeugenol methyl ether lignocellulose nanofiber emulsion and preparation method and application thereof - Google Patents
Isoeugenol methyl ether lignocellulose nanofiber emulsion and preparation method and application thereof Download PDFInfo
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- CN118165293A CN118165293A CN202410325591.3A CN202410325591A CN118165293A CN 118165293 A CN118165293 A CN 118165293A CN 202410325591 A CN202410325591 A CN 202410325591A CN 118165293 A CN118165293 A CN 118165293A
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- methyl ether
- isoeugenol methyl
- lignocellulose
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- nanofiber emulsion
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- NNWHUJCUHAELCL-UHFFFAOYSA-N cis-Methyl isoeugenol Natural products COC1=CC=C(C=CC)C=C1OC NNWHUJCUHAELCL-UHFFFAOYSA-N 0.000 title claims abstract description 44
- NNWHUJCUHAELCL-PLNGDYQASA-N cis-isomethyleugenol Chemical compound COC1=CC=C(\C=C/C)C=C1OC NNWHUJCUHAELCL-PLNGDYQASA-N 0.000 title claims abstract description 44
- SBENKNZHVXGNTP-UHFFFAOYSA-N methylconiferyl ether Natural products COCC=CC1=CC=C(O)C(OC)=C1 SBENKNZHVXGNTP-UHFFFAOYSA-N 0.000 title claims abstract description 44
- 239000000839 emulsion Substances 0.000 title claims abstract description 38
- 239000002121 nanofiber Substances 0.000 title claims abstract description 27
- 238000002360 preparation method Methods 0.000 title claims abstract description 17
- 238000004945 emulsification Methods 0.000 title description 2
- 241000736128 Solenopsis invicta Species 0.000 claims abstract description 23
- 239000002253 acid Substances 0.000 claims abstract description 18
- 238000000034 method Methods 0.000 claims abstract description 10
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 27
- 238000003756 stirring Methods 0.000 claims description 20
- 239000000843 powder Substances 0.000 claims description 16
- 239000007787 solid Substances 0.000 claims description 16
- 241000219000 Populus Species 0.000 claims description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- 239000008367 deionised water Substances 0.000 claims description 10
- 229910021641 deionized water Inorganic materials 0.000 claims description 10
- 238000010438 heat treatment Methods 0.000 claims description 8
- 239000000725 suspension Substances 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 5
- BJIOGJUNALELMI-ONEGZZNKSA-N Isoeugenol Natural products COC1=CC(\C=C\C)=CC=C1O BJIOGJUNALELMI-ONEGZZNKSA-N 0.000 claims description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 4
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 4
- 239000011976 maleic acid Substances 0.000 claims description 4
- 230000001846 repelling effect Effects 0.000 claims description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 4
- BJIOGJUNALELMI-UHFFFAOYSA-N trans-isoeugenol Natural products COC1=CC(C=CC)=CC=C1O BJIOGJUNALELMI-UHFFFAOYSA-N 0.000 claims description 4
- 238000001291 vacuum drying Methods 0.000 claims description 4
- 238000000265 homogenisation Methods 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- 238000001035 drying Methods 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 238000000967 suction filtration Methods 0.000 claims description 2
- 238000004140 cleaning Methods 0.000 claims 1
- 230000003647 oxidation Effects 0.000 abstract description 4
- 238000007254 oxidation reaction Methods 0.000 abstract description 4
- 238000001782 photodegradation Methods 0.000 abstract description 4
- 230000007613 environmental effect Effects 0.000 abstract description 3
- 241000607479 Yersinia pestis Species 0.000 abstract description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract description 2
- 150000002894 organic compounds Chemical class 0.000 abstract description 2
- 229910052760 oxygen Inorganic materials 0.000 abstract description 2
- 239000001301 oxygen Substances 0.000 abstract description 2
- 238000007781 pre-processing Methods 0.000 abstract 1
- 238000012360 testing method Methods 0.000 description 28
- 239000000123 paper Substances 0.000 description 22
- 239000005871 repellent Substances 0.000 description 11
- 230000002940 repellent Effects 0.000 description 11
- 239000000575 pesticide Substances 0.000 description 10
- 241000257303 Hymenoptera Species 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- 239000000835 fiber Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000003814 drug Substances 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 229940079593 drug Drugs 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 230000002265 prevention Effects 0.000 description 4
- 239000000341 volatile oil Substances 0.000 description 4
- PXRKCOCTEMYUEG-UHFFFAOYSA-N 5-aminoisoindole-1,3-dione Chemical compound NC1=CC=C2C(=O)NC(=O)C2=C1 PXRKCOCTEMYUEG-UHFFFAOYSA-N 0.000 description 3
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 3
- 241000238631 Hexapoda Species 0.000 description 3
- 230000009286 beneficial effect Effects 0.000 description 3
- 235000013305 food Nutrition 0.000 description 3
- 230000019637 foraging behavior Effects 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 229920001046 Nanocellulose Polymers 0.000 description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- 240000007594 Oryza sativa Species 0.000 description 2
- 235000007164 Oryza sativa Nutrition 0.000 description 2
- 231100000460 acute oral toxicity Toxicity 0.000 description 2
- 231100000403 acute toxicity Toxicity 0.000 description 2
- 230000007059 acute toxicity Effects 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 235000012907 honey Nutrition 0.000 description 2
- 239000000077 insect repellent Substances 0.000 description 2
- 238000012827 research and development Methods 0.000 description 2
- 235000009566 rice Nutrition 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- ZOCSXAVNDGMNBV-UHFFFAOYSA-N 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl)sulfinyl]-1H-pyrazole-3-carbonitrile Chemical compound NC1=C(S(=O)C(F)(F)F)C(C#N)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl ZOCSXAVNDGMNBV-UHFFFAOYSA-N 0.000 description 1
- IBSREHMXUMOFBB-JFUDTMANSA-N 5u8924t11h Chemical compound O1[C@@H](C)[C@H](O)[C@@H](OC)C[C@@H]1O[C@@H]1[C@@H](OC)C[C@H](O[C@@H]2C(=C/C[C@@H]3C[C@@H](C[C@@]4(O3)C=C[C@H](C)[C@@H](C(C)C)O4)OC(=O)[C@@H]3C=C(C)[C@@H](O)[C@H]4OC\C([C@@]34O)=C/C=C/[C@@H]2C)/C)O[C@H]1C.C1=C[C@H](C)[C@@H]([C@@H](C)CC)O[C@]11O[C@H](C\C=C(C)\[C@@H](O[C@@H]2O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](OC)C3)[C@@H](OC)C2)[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 IBSREHMXUMOFBB-JFUDTMANSA-N 0.000 description 1
- 239000005660 Abamectin Substances 0.000 description 1
- 240000006891 Artemisia vulgaris Species 0.000 description 1
- 235000003261 Artemisia vulgaris Nutrition 0.000 description 1
- 241000238421 Arthropoda Species 0.000 description 1
- 235000002566 Capsicum Nutrition 0.000 description 1
- 240000008574 Capsicum frutescens Species 0.000 description 1
- TWLLPUMZVVGILS-UHFFFAOYSA-N Ethyl 2-aminobenzoate Chemical compound CCOC(=O)C1=CC=CC=C1N TWLLPUMZVVGILS-UHFFFAOYSA-N 0.000 description 1
- 244000166124 Eucalyptus globulus Species 0.000 description 1
- 239000005899 Fipronil Substances 0.000 description 1
- 239000005906 Imidacloprid Substances 0.000 description 1
- 239000005907 Indoxacarb Substances 0.000 description 1
- 238000012313 Kruskal-Wallis test Methods 0.000 description 1
- MMOXZBCLCQITDF-UHFFFAOYSA-N N,N-diethyl-m-toluamide Chemical compound CCN(CC)C(=O)C1=CC=CC(C)=C1 MMOXZBCLCQITDF-UHFFFAOYSA-N 0.000 description 1
- 241000382353 Pupa Species 0.000 description 1
- 238000011869 Shapiro-Wilk test Methods 0.000 description 1
- 241000517830 Solenopsis geminata Species 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- 229950008167 abamectin Drugs 0.000 description 1
- 210000001015 abdomen Anatomy 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 238000000540 analysis of variance Methods 0.000 description 1
- VEMKTZHHVJILDY-UXHICEINSA-N bioresmethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-UXHICEINSA-N 0.000 description 1
- 239000001390 capsicum minimum Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007405 data analysis Methods 0.000 description 1
- 229960001673 diethyltoluamide Drugs 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229940013764 fipronil Drugs 0.000 description 1
- 235000013373 food additive Nutrition 0.000 description 1
- 239000002778 food additive Substances 0.000 description 1
- 238000003197 gene knockdown Methods 0.000 description 1
- 239000010440 gypsum Substances 0.000 description 1
- 229910052602 gypsum Inorganic materials 0.000 description 1
- 231100000086 high toxicity Toxicity 0.000 description 1
- YWTYJOPNNQFBPC-UHFFFAOYSA-N imidacloprid Chemical compound [O-][N+](=O)\N=C1/NCCN1CC1=CC=C(Cl)N=C1 YWTYJOPNNQFBPC-UHFFFAOYSA-N 0.000 description 1
- 229940056881 imidacloprid Drugs 0.000 description 1
- VBCVPMMZEGZULK-NRFANRHFSA-N indoxacarb Chemical compound C([C@@]1(OC2)C(=O)OC)C3=CC(Cl)=CC=C3C1=NN2C(=O)N(C(=O)OC)C1=CC=C(OC(F)(F)F)C=C1 VBCVPMMZEGZULK-NRFANRHFSA-N 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000011229 interlayer Substances 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000000419 plant extract Substances 0.000 description 1
- 231100000572 poisoning Toxicity 0.000 description 1
- 230000000607 poisoning effect Effects 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 235000013580 sausages Nutrition 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- 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
- A01N25/02—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 liquids as carriers, diluents or solvents
- A01N25/04—Dispersions, emulsions, suspoemulsions, suspension concentrates or gels
-
- 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
- A01N25/22—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 stabilising the active ingredients
-
- 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
- A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
- A01N31/08—Oxygen or sulfur directly attached to an aromatic ring system
- A01N31/16—Oxygen or sulfur directly attached to an aromatic ring system with two or more oxygen or sulfur atoms directly attached to the same aromatic ring system
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
- A01P17/00—Pest repellants
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/02—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
- C08J3/03—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in aqueous media
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2301/00—Characterised by the use of cellulose, modified cellulose or cellulose derivatives
- C08J2301/04—Oxycellulose; Hydrocellulose
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/06—Ethers; Acetals; Ketals; Ortho-esters
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Environmental Sciences (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- Agronomy & Crop Science (AREA)
- Dentistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Dispersion Chemistry (AREA)
- Toxicology (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The invention discloses isoeugenol methyl ether lignocellulose nanofiber emulsion and a preparation method and application thereof, relates to the technical field of pest (solenopsis invicta) control, and solves the problems that isoeugenol methyl ether pure products are easily influenced by environmental factors such as light, heat and oxygen in the use process, and the duration time is greatly shortened. The preparation method comprises the following steps: preparing and preprocessing the organic compound acid, and preparing isoeugenol methyl ether lignocellulose nanofiber emulsion by mechanical nanofibrillating treatment. The invention effectively improves the slow release, oxidation resistance, photodegradation resistance and heat resistance of isoeugenol methyl ether.
Description
Technical Field
The invention relates to the technical field of pest (solenopsis invicta) control, in particular to the field of research and development and application of solenopsis invicta repellent, and more particularly relates to isoeugenol methyl ether lignocellulose nanofiber emulsion and a preparation method and application thereof.
Background
Currently, tens of pesticides are applied to the prevention and treatment of solenopsis invicta worldwide, common medicaments comprise various pyrethroids, indoxacarb, imidacloprid, fipronil, abamectin and the like (Chen,J.,&Oi,D.H.(2020).Naturally Occurring Compounds/Materials as Alternatives to Synthetic Chemical Insecticides for Use in Fire Ant Management.Insects,11(11),Article 11.)., and the use of a slow stomach poisoning pesticide to prepare baits for large-area prevention and treatment, and the use of a high-toxicity contact pesticide to remove nest at fixed points is the most main prevention and treatment method at present. However, although considerable research progress and effort has been made in the current development of chemical control based on various pesticides, they have some drawbacks. For example, 1) cannot be immediately protected: although some quick-acting pesticides can quickly knock down (kill) the solenopsis invicta, the solenopsis invicta does not lose mobility immediately after contacting the pesticides, and can still initiate strong attack in a short time, and even cause greater harm; 2) The cost is higher: the cost of using pesticides to prevent and treat solenopsis invicta in a large area is quite high, the single prevention and treatment cost of the solenopsis invicta is about 50-100 yuan/mu currently, compared with rice planting, in the rice planting, the cost of each mu of chemical fertilizer, seeds and pesticide is 76.51 yuan, 50.02 yuan and 24.48 yuan respectively; 3) Environmental pollution: the impact of applying pesticides over a large area on other arthropods and aquatic organisms in the environment is also quite enormous.
Based on the above problems, a great deal of effort has been made in recent years to find targeted pesticide substitutes. Among them, repellents are one of the currently accepted solutions. Repellents generally refer to volatile chemical substances produced by plants or synthesized by humans that have the effect of repelling insects. After the repellent is applied, the volatile repellent can escape by stimulating the smell of the solenopsis invicta, so that the probability of contacting the solenopsis invicta with a protected target is reduced, and the instant protection effect is achieved.
Currently, there is no marketed red fire ant repellent product on the global scale, and the research and development of red fire ant repellent is in the stage of screening active ingredients. These studies have involved various insect repellent products, plant essential oils, skin care products, food additives, and the like, such as capsicum essential oil (Wang et al, 2014, doi:97 (2): 454-60), eucalyptus essential oil (Kun et al, 2014, doi:67 (2): 207-11), mugwort essential oil (Kun et al, 2014, doi:67 (2): 207-11), essential wind oil (Wen et al, 2016, doi:109 (4): 1827-33), ethyl anthranilate (Chen et al, 2019, doi:75 (3): 821-27), isoeugenol methyl ether (He et al, 2022, doi:96 (1): 327-344), and the like.
The isoeugenol methyl ether is a substance which is recently discovered to be capable of efficiently repelling solenopsis invicta, and has long lasting time, and the lasting time under laboratory conditions can be as long as 24 hours. Meanwhile, isoeugenol methyl ether is used as a natural plant extract, and has the characteristic of environmental protection. In terms of safety, isoeugenol methyl ether is slightly less toxic than the most mainstream insect repellent, DEET, of the world today. The oral acute toxicity LD50 is 2500mg/kg (mouse), the skin contact acute toxicity LD50 is >5000mg/kg (rabbit), the oral acute toxicity LD50 of the deet is 1950mg/kg (mouse), and the skin contact acute toxicity LD50 is 3180mg/kg (rabbit).
Therefore, the isoeugenol methyl ether is considered to have extremely strong application value and development potential. However, in the actual testing process of the pure isoeugenol methyl ether product, the pure isoeugenol methyl ether product is easy to be influenced by environmental factors such as light, heat and oxygen, and the duration of the pure isoeugenol methyl ether product can be greatly shortened to be within 4 hours especially under high-temperature and clear weather conditions.
Therefore, how to effectively improve the slow release, oxidation resistance, photodegradation resistance and heat resistance of isoeugenol methyl ether is a problem to be solved by those skilled in the art.
Disclosure of Invention
In view of the above, the invention provides an isoeugenol methyl ether lignocellulose nanofiber emulsion, a preparation method and application thereof, and the emulsion combines isoeugenol methyl ether and lignocellulose through a nanotechnology, so that the slow release, oxidation resistance, photodegradation resistance and heat resistance of the isoeugenol methyl ether are effectively improved.
In order to achieve the above purpose, the invention provides a preparation method of isoeugenol methyl ether lignocellulose nanofiber emulsion, which comprises the following specific steps:
1) Configuration and pretreatment of organic complex acid:
11 Adding deionized water into citric acid and maleic acid to prepare a mixed acid solution, and heating and stirring until the mixed acid solution is completely dissolved into a transparent solution;
12 Continuously heating the mixed acid solution to a certain temperature, adding poplar powder, and stirring for reaction;
13 After the reaction is finished, pumping filtration is carried out, absolute ethyl alcohol is continuously added to clean the solid residue until the dripped filtrate becomes transparent solution, the solid residue is centrifugally washed, and the solid residue is collected and placed in a dryer after vacuum drying;
The pretreatment of the organic compound acid has the beneficial effects that: the poplar powder can be effectively hydrolyzed, the interlayer binding force between fibers is weakened, and the polymerization degree and the diameter of the fibers are reduced; carboxyl is introduced to the surface of the fiber, so that electrostatic repulsive force among the fibers is increased, and the dispersion stability of the fibers in water can be improved.
2) Mechanical nanofibrillation treatment:
21 Adding deionized water into the dried solid residue to prepare suspension, stirring, and homogenizing for multiple times by adopting stepped boosting to obtain Lignocellulose (LCNF);
22 Mixing isoeugenol methyl ether and lignocellulose according to a certain proportion, and stirring to obtain isoeugenol methyl ether-lignocellulose nanofiber emulsion (LCNF-MiE).
The beneficial effects obtained by adopting the step boosting and the repeated homogenization are as follows: preventing large diameter fibers from clogging the machine.
Preferably, in the step 11), the mass ratio of the citric acid to the maleic acid is 3:7-7:3; the concentration of the mixed acid solution was 80wt%.
Preferably, in the step 12), the solid-liquid mass ratio of the poplar powder to the mixed acid solution is 1:10; the poplar powder is 60-80 meshes; the poplar powder is dried poplar powder which is dried for 24 hours at 105 ℃; and continuously heating to 120 ℃, and stirring for 180min.
Preferably, the speed of the heating agitation in step 11) and the agitation in step 12) are both 1000rpm.
Preferably, the centrifugal washing in the step 13) is performed under the centrifugal condition of 1000rpm/min and 5min.
Preferably, the vacuum drying condition in step 13) is 60 ℃, and the drying is carried out for 24 hours.
Preferably, step 21) the step-up multiple homogenization specific operation: homogenizing under 3.5MPa for 2 times, homogenizing under 30MPa for 3 times, and homogenizing under 100MPa for 12 times.
Preferably, the solid residue content of the suspension of step 21) is between 0.1% and 0.5% by weight; the stirring speed was 500rpm for 12 hours.
Preferably, in the step 22), the mass ratio of the isoeugenol methyl ether to the lignocellulose is 1:9-9:1; the stirring speed was 7000rpm for 1h.
In order to achieve the above purpose, the invention provides an application of isoeugenol methyl ether lignocellulose nanofiber emulsion, in particular to an application in repelling solenopsis invicta.
Compared with the prior art, the invention has the beneficial effects that at least:
The emulsion prepared by the invention combines isoeugenol methyl ether and lignocellulose through a nano technology, and effectively improves the slow release, oxidation resistance, photodegradation resistance and heat resistance of the isoeugenol methyl ether.
The environment-friendly fire ant repellent can be sprayed on the surfaces of clothes, objects and even skin, can kill the fire ants immediately and can continuously repel the fire ants within a certain time, has great protection significance for workers in field camping and agriculture and forestry industries, and greatly reduces the risk of injury of the fire ants.
Drawings
In order to more clearly illustrate the embodiments of the present invention or the technical solutions in the prior art, the drawings that are required to be used in the embodiments or the description of the prior art will be briefly described below, and it is obvious that the drawings in the following description are only embodiments of the present invention, and that other drawings can be obtained according to the provided drawings without inventive effort for a person skilled in the art.
Fig. 1 is a flowchart of the preparation of isoeugenol methyl ether lignocellulose nanofiber emulsion according to example 7 of the present invention.
Fig. 2 is a drawing showing an isoeugenol methyl ether lignocellulose nanofiber emulsion provided in example 7 of the present invention.
Fig. 3 is a diagram showing a solenopsis invicta repellency test apparatus according to example 8 of the present invention.
Fig. 4 is a diagram showing the result of the repellency test provided in embodiment 8 of the present invention.
Detailed Description
The following description of the embodiments of the present invention will be made clearly and completely with reference to the accompanying drawings, in which it is apparent that the embodiments described are only some embodiments of the present invention, but not all embodiments. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to be within the scope of the invention.
Example 1
The embodiment discloses a preparation method of lignocellulose, which specifically comprises the following steps:
pretreatment of organic complex acid:
(1) And (3) respectively weighing Citric Acid (CA) and Maleic Acid (MA) according to a mass ratio of 3:7, adding deionized water to prepare a mixed acid solution with the concentration of 80wt%, and heating and stirring at a stirring speed of 1000rpm.
(2) The mixed acid solution is completely dissolved into transparent solution, the temperature is continuously increased to 120 ℃, poplar powder is rapidly added, and the mixture is stirred at the speed of 1000rpm and reacts for 180min;
the solid-liquid mass ratio of the poplar powder to the mixed acid solution is 1:10;
The poplar powder is 60-80 meshes; the poplar powder is dried poplar powder dried at 105 deg.c for 24 hr.
(3) Immediately carrying out suction filtration after the reaction is finished, and continuously adding absolute ethyl alcohol to clean the solid residue until the dropped filtrate becomes transparent solution; adding deionized water into the obtained solid residue, stirring uniformly, centrifuging at 1000rpm/min for 5min, pouring out supernatant, adding deionized water, stirring uniformly, and repeatedly centrifuging and washing for 5 times; the solid residue was dried in vacuo at 60 ℃ for 24h; finally, collecting the mixture in a sealed bag and placing the sealed bag in a dryer.
Mechanical nanofibrillation treatment:
Adding deionized water into the dried solid residue to prepare a suspension with the weight percent of 0.1 percent, stirring for 12 hours, homogenizing for 2 times under the pressure of 3.5MPa by using a high-pressure homogenizer, homogenizing for 3 times under the pressure of 30MPa, and homogenizing for 12 times under the pressure of 100MPa to obtain the lignocellulose.
Example 2
The embodiment discloses a preparation method of lignocellulose, which comprises the following steps:
Citric Acid (CA) and Maleic Acid (MA) were weighed out in a mass ratio of 5:5, respectively, and the other conditions were the same as in comparative example 1.
Example 3
The embodiment discloses a preparation method of lignocellulose, which comprises the following steps:
citric Acid (CA) and Maleic Acid (MA) were weighed out respectively in a mass ratio of 7:3, and the other conditions were the same as in comparative example 1.
Example 4
The embodiment discloses a preparation method of lignocellulose, which comprises the following steps:
the dried solid residue was added to deionized water to prepare a 0.5wt% suspension, with the remainder being the same as in example 1.
Example 5
The embodiment discloses a preparation method of lignocellulose, which comprises the following steps:
the dried solid residue was added to deionized water to prepare a 0.5wt% suspension, with the remainder being the same as in example 2.
Example 6
The embodiment discloses a preparation method of lignocellulose, which comprises the following steps:
the dried solid residue was added to deionized water to prepare a 0.5wt% suspension, with the remainder being the same as in example 3.
Example 7
The embodiment discloses a preparation method of isoeugenol methyl ether lignocellulose nanofiber emulsion, which specifically comprises the following steps:
Isoeugenol methyl ether and lignocellulose of examples 1-6 are mixed according to the mass ratio of 1:9, 5:5 and 9:1 respectively, and stirred for 1h to prepare isoeugenol methyl ether-lignocellulose nanofiber emulsion, and the specific results are shown in Table 1:
Wherein LCNF is a lignocellulosic nanofiber, i.e., LCNF 1/2/3-1 represents 0.1wt% of the lignocellulosic nanocellulose prepared in examples 1-3, LCNF 1/2/3-2 represents 0.5wt% of the lignocellulosic nanocellulose prepared in examples 4-6; miE is isoeugenol methyl ether.
TABLE 1 isoeugenol methyl ether-lignocellulose nanofiber emulsion
| Numbering device | Dosage form name | Formulation of |
| 1 | LCNF1-1MiE(9:1) | 180g0.1％LCNF1+20gMiE |
| 2 | LCNF1-1MiE(5:5) | 20g0.1％LCNF1+20gMiE |
| 3 | LCNF1-1MiE(1:9) | 2g0.1％LCNF1+18gMiE |
| 4 | LCNF1-2MiE(9:1) | 180g0.5％LCNF1+20gMiE |
| 5 | LCNF1-2MiE(5:5) | 20g0.5％LCNF1+20gMiE |
| 6 | LCNF1-2MiE(1:9) | 2g0.5％LCNF1+18gMiE |
| 7 | LCNF2-1MiE(9:1) | 180g0.1％LCNF2+20gMiE |
| 8 | LCNF2-1MiE(5:5) | 20g0.1％LCNF2+20gMiE |
| 9 | LCNF2-1MiE(1:9) | 2g0.1％LCNF2+18gMiE |
| 10 | LCNF2-2MiE(9:1) | 180g0.5％LCNF2+20gMiE |
| 11 | LCNF2-2MiE(5:5) | 20g0.5％LCNF2+20gMiE |
| 12 | LCNF2-2MiE(1:9) | 2g0.5％LCNF2+18gMiE |
| 13 | LCNF3-1MiE(9:1) | 180g0.1％LCNF3+20gMiE |
| 14 | LCNF3-1MiE(5:5) | 20g0.1％LCNF3+20gMiE |
| 15 | LCNF3-1MiE(1:9) | 2g0.1％LCNF3+18gMiE |
| 16 | LCNF3 -2MiE(9:1) | 180g0.5％LCNF3+20gMiE |
| 17 | LCNF3-2MiE(5:5) | 20g0.5％LCNF3+20gMiE |
| 18 | LCNF3-2MiE(1:9) | 2g0.5％LCNF3+18gMiE |
Example 8
Testing the repellent performance of the emulsion on solenopsis invicta:
in the embodiment, the foraging behavior of solenopsis invicta workers is utilized to evaluate the repellent effect time of isoeugenol methyl ether emulsion (LCNF-MiE) on solenopsis invicta workers.
This example compares the foraging behavior of solenopsis invicta workers on square superplastic coated paper (5 x 5 cm) treated (blank, CK) with emulsion (LCNF-MiE), stock (MiE), lignocellulose (LCNF). The test was carried out in a plastic box (52X 35X 15 cm) with talc on the inner wall. The plastic box is provided with 1 artificial darkroom (made of 90mm petri dish, dental gypsum powder and black plastic coated cardboard) which is used as an inhabited place of the ant colony; 2 distilled water and 1 20% honey water (each in a 10-ml centrifuge tube) were used as food sources. Before the test, 1 ant, 5+/-0.1 g worker ant and 0.5+/-0.01 g egg/pupa/larva are randomly selected from the random ant colony raised in the insect raising chamber, and the selected ants are placed in an artificial darkroom of a test device for adaptation for 72 hours. The test was performed with a total of 10 test units, each of which had an ant colony from 10 different ant colonies in the feeding chamber, as 10 replicates. The test device is placed in a laboratory neatly, the temperature of the laboratory is 27-30 ℃, the humidity is 40-60% RH, and the photoperiod is 14D:10N. During the test, distilled water and honey water are replaced every 72 hours to ensure the supply and freshness of the food until the test is finished.
The target concentration of MiE on the surface of the coordinate paper was set to 1mg/cm 2 according to the pre-test results. The specific operation is as follows: first, 25mg MiE and corresponding amounts of LCNF-MiE containing 25mg MiE were uniformly applied to 2 sheets of the surface of the coordinate paper to give a concentration of 1mg/cm 2 on the surface MiE of the coordinate paper. Corresponding amounts of LCNF were then applied uniformly to the surface of 1 other sheet of co-ordinate paper (specific amounts of LCNF-MiE and LCNF are shown in Table 2) according to the formulation and amounts of LCNF-MiE, with MiE and LCNF-MiE treated co-ordinate papers being the treatment group and LCNF treated and untreated co-ordinate papers being the control group. After the treatment of the coordinate paper, the coordinate paper is put in a constant temperature and humidity box according to random sequence for preservation (the temperature is set to be 30+/-0.5 ℃ and the humidity is set to be 60+/-3% RH).
Tables 2LCNF-MiE and LCNF dosage form
The test comprises several tests, specifically, before each test is started, the coordinate paper required by the current test is taken out from a constant temperature and humidity box, and a square ham sausage sheet (10 multiplied by 1 mm) prepared in advance is put into the central square of the coordinate paper to serve as a food source for attracting the solenopsis invicta to eat. And then placing the coordinate paper into a test device according to a random sequence, wherein the vertical distance between the edge of the coordinate paper and an artificial darkroom is more than 10cm, the distance between the edges of adjacent coordinate paper is more than 1cm, and the distance between the edges of the coordinate paper and the wall of the box is more than 3cm (as shown in figure 1). After the coordinate paper is placed in the test apparatus, the test is started. The test was continued for 1h, and a photograph recording was made every 15 min. After each test, all the paper coordinates and the ham slices in the test apparatus were removed. During the test, 1 test was performed every 24 hours, and each LCNF-MiE test was performed 4 times, i.e., 0, 24, 48, and 72 hours of coordinate paper treatment.
For statistics, the number of ants on the coordinate paper in the photo was punctuated using Photoshop software, and these principles were followed:
(1) Clear independent individuals were counted as 1;
(2) At the edge of the coordinate paper, the ants with the body (head, chest and abdomen) entering the coordinate paper >50% are counted as 1, otherwise, are counted as 0;
(3) In the ant dense area, only the tail number is counted.
After statistics are completed, data analysis is performed using SAS 9.4 software.
First, the normal distribution of each data was checked using Shapiro-Wilk test, and the data of the non-normal distribution was checked again after square root or logarithmic transformation. Then, for data meeting normal distribution, analysis and multiple comparisons were performed using ANOVA and Tukey HSD; for data that do not fit the normal distribution, then Kruskal-WALLIS TESTS and Dwass-Steel-Critchlow-FLIGNERTEST (DSCF) were used for analysis and multiple comparisons. The significance level was α=0.05.
Test results
The test results show that at 0 hour, the number of ants on the coordinate paper of the emulsion (LCNF-MiE) and the original drug (MiE) of the 18 formulas is not significantly different, and the number of ants is significantly less than that of Lignocellulose (LCNF) and a blank control, and the complete inhibition effect on the foraging behavior of solenopsis invicta is shown. At 24 hours, half of the formulation emulsion remained significantly lower than the drug or control, with most of the drug not significantly different from the control. At 48 hours, the No. 02, 04, 13, 16 and 17 formulated emulsions were still significantly lower than the drug or control, all without significant difference from the control. At 72 hours, only emulsion number 16 was significantly lower than the blank.
Conclusion: among the 18 emulsion formulations, the No. 16 emulsion has the longest effective repellent time on solenopsis invicta, and is the optimal emulsion formulation.
The previous description of the disclosed embodiments is provided to enable any person skilled in the art to make or use the present invention. Various modifications to these embodiments will be readily apparent to those skilled in the art, and the generic principles defined herein may be applied to other embodiments without departing from the spirit or scope of the invention. Thus, the present invention is not intended to be limited to the embodiments shown herein but is to be accorded the widest scope consistent with the principles and novel features disclosed herein.
Claims (10)
1. The preparation method of the isoeugenol methyl ether lignocellulose nanofiber emulsion is characterized by comprising the following specific steps of:
1) Configuration and pretreatment of organic complex acid:
11 Preparing a mixed acid solution from citric acid and maleic acid, heating and stirring until the mixed acid solution is completely dissolved;
12 Continuously heating the mixed acid solution to a certain temperature, adding poplar powder, and stirring for reaction;
13 After the reaction is finished, carrying out suction filtration, cleaning a solid residue, and collecting and placing the solid residue in a dryer after vacuum drying;
2) Mechanical nanofibrillation treatment:
21 Adding deionized water into the dried solid residue to prepare suspension, stirring, and homogenizing for multiple times by adopting stepped boosting to obtain lignocellulose;
22 Mixing isoeugenol methyl ether and lignocellulose according to a certain proportion, and stirring to obtain the isoeugenol methyl ether-lignocellulose nanofiber emulsion.
2. The method for preparing isoeugenol methyl ether lignocellulose nanofiber emulsion according to claim 1, wherein the mass ratio of citric acid to maleic acid in the step 11) is 3:7-7:3;
The concentration of the mixed acid solution was 80wt%.
3. The method for preparing isoeugenol methyl ether lignocellulose nanofiber emulsion according to claim 1, wherein the solid-liquid mass ratio of the poplar powder to the mixed acid solution in step 12) is 1:10;
the poplar powder is 60-80 meshes and is dried poplar powder dried for 24 hours at 105 ℃;
and continuously heating to 120 ℃, and stirring and reacting for 180min.
4. The method of preparing isoeugenol methyl ether lignocellulose nanofiber emulsion according to claim 1, wherein the stirring speed in steps 11) and 12) is 1000rpm.
5. The method for preparing isoeugenol methyl ether lignocellulose nanofiber emulsion according to claim 1, wherein the vacuum drying condition in the step 13) is 60 ℃, and the drying is carried out for 24 hours.
6. The method for preparing isoeugenol methyl ether lignocellulose nanofiber emulsion according to claim 1, wherein the step-up multiple homogenization specific operation is carried out in the step 21): homogenizing under 3.5MPa for 2 times, homogenizing under 30MPa for 3 times, and homogenizing under 100MPa for 12 times.
7. The method for preparing isoeugenol methyl ether lignocellulose nanofiber emulsion according to claim 1, wherein the content of solid residues in the suspension in the step 21) is 0.1-0.5 wt%;
the stirring speed was 500rpm for 12 hours.
8. The method for preparing isoeugenol methyl ether lignocellulose nanofiber emulsion according to claim 1, wherein the mass ratio of isoeugenol methyl ether to lignocellulose in the step 22) is 1:9-9:1;
the stirring speed was 7000rpm for 1h.
9. An isoeugenol methyl ether lignocellulose nanofiber emulsion, which is characterized by comprising the isoeugenol methyl ether lignocellulose nanofiber emulsion prepared by the preparation method of claims 1-8.
10. The use of isoeugenol methyl ether lignocellulose nanofiber emulsion according to claim 9 for repelling solenopsis invicta.
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| WO2017073626A1 (en) * | 2015-10-30 | 2017-05-04 | 東レ株式会社 | Cellulose ether derivative fine particles |
| JP2020183499A (en) * | 2019-05-09 | 2020-11-12 | 凸版印刷株式会社 | Sustained release compound particle, molded body, method of manufacturing sustained release compound particle |
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