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CN116649347A - Compound, solenopsis invicta repellent prepared from compound and combination of compound and solenopsis invicta repellent and application of solenopsis invicta repellent - Google Patents

Compound, solenopsis invicta repellent prepared from compound and combination of compound and solenopsis invicta repellent and application of solenopsis invicta repellent Download PDF

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CN116649347A
CN116649347A CN202310415244.5A CN202310415244A CN116649347A CN 116649347 A CN116649347 A CN 116649347A CN 202310415244 A CN202310415244 A CN 202310415244A CN 116649347 A CN116649347 A CN 116649347A
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compound
repellent
solenopsis invicta
anthranilate
application
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俞世冲
许益镌
毛孟飞
俞媛
丁一波
谭晓
曹广文
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Second Military Medical University SMMU
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    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N37/00Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/44Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01PBIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P17/00Pest repellants
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C229/00Compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C229/52Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
    • C07C229/54Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton with amino and carboxyl groups bound to carbon atoms of the same non-condensed six-membered aromatic ring
    • C07C229/56Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton with amino and carboxyl groups bound to carbon atoms of the same non-condensed six-membered aromatic ring with amino and carboxyl groups bound in ortho-position
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02ATECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
    • Y02A50/00TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
    • Y02A50/30Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

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  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Zoology (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Engineering & Computer Science (AREA)
  • Environmental Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Dentistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

The application relates to a compound, a solenopsis invicta repellent combined by the compound and application of the compound and the solenopsis invicta repellent combined by the compound. According to the application, the butyl anthranilate is found to have good repellent effect on solenopsis invicta in the derivatives and part of the compositions of the anthranilate, the selection behavior of the solenopsis invicta can be effectively interfered, the preventive effect can be further obtained, meanwhile, the combination of the butyl anthranilate, methyl anthranilate and ethyl aminobenzoate respectively can obviously increase the repellent effect, and meanwhile, the selected compound is easy to obtain and is an edible or essence raw material, is harmless to human bodies, and has very wide application prospects in the aspects of agricultural technical fields such as quarantine and prevention and control of the solenopsis invicta.

Description

一种化合物及其组合的红火蚁驱避剂及其应用A kind of red fire ant repellant of compound and its combination and application thereof

技术领域technical field

本发明涉及杀虫剂技术领域,具体地说,是关于一种化合物及其组合的红火蚁驱避剂及其应用。The invention relates to the technical field of insecticides, in particular to a compound and a red fire ants repellent combined with it and its application.

背景技术Background technique

红火蚁原产于南美洲的巴西和阿根廷巴拉纳河流域,是世界上最重要的100种入侵生物之一,对农业生态环境和公共安全造成严重威胁。岛礁的绿化建设过程中,红火蚁也频繁随着草皮和树木的移栽被转移到各岛礁。红火蚁一般随着苗木、草皮、农肥等带土植物材料进行远距离扩散,利用驱避剂对苗木、草皮等红火蚁的传播介质进行处理可有效的切断红火蚁传播途径的作用。另外,驱避剂也能阻止红火蚁对人体叮咬,起到预防保护的效果。The red imported fire ant is native to the Parana River Basin of Brazil and Argentina in South America. It is one of the 100 most important invasive organisms in the world and poses a serious threat to the agricultural ecological environment and public safety. During the greening construction of islands and reefs, RIFAs are also frequently transferred to various islands and reefs along with the transplanting of turf and trees. RIFA generally spreads long-distance with soil-bearing plant materials such as seedlings, turf, and agricultural fertilizers. Using repellents to treat seedlings, turf and other RIFA transmission media can effectively cut off the transmission route of RIFA. In addition, the repellent can also prevent the RIFA from biting the human body and play a preventive and protective effect.

邻氨基苯甲酸酯类化合物应用比较广泛,主要用于在香料领域,邻氨基苯甲酸甲酯具有葡萄样特殊性气味,可用于调制葡萄酒、橘子、橙花等香型香精应用于食品与化妆品领域;在染料领域,邻氨基苯甲酸甲酯是偶氮染料、蒽醌染料、靛族染料的重要中间体;在医药领域,邻氨基苯甲酸甲酯主要应用于抗心律失常药物、非甾体类抗炎镇痛药物、非巴比妥类催眠药物制造场景。Anthranilate compounds are widely used, mainly in the field of fragrances. Methyl anthranilate has a grape-like specific smell and can be used to prepare wine, orange, orange blossom and other flavors for food and cosmetics ; In the field of dyes, methyl anthranilate is an important intermediate of azo dyes, anthraquinone dyes, and indigo dyes; in the field of medicine, methyl anthranilate is mainly used in antiarrhythmic drugs, non-steroidal Anti-inflammatory analgesic drugs, non-barbiturate hypnotic drugs manufacturing scene.

中文专利CN113016797A,公开日2021.06.25,公开了一种用于灭杀或驱避红火蚁的药剂,所述药剂以异丁香酚甲醚作为活性成分。所述红火蚁为膜翅目蚁科切叶蚁亚科红火蚁,该发明实施例试验证明:异丁香酚甲醚对红火蚁具有强烈的驱避作用,异丁香酚甲醚常作为香料食用,对人畜无毒,可以作为环境友好型驱避剂使用。绿色环保,成分简单,挥发性弱,持续时间长,成本低,能够批量生产,有助于大面积驱避红火蚁。另一中文专利CN113476363A,公开日2021.10.08,还公开了一种驱避红火蚁的组合物及其应用。所述组合物包括除虫菊素和印楝素;所述除虫菊素和印楝素的质量比为(0.1~2.0):(0.1~3.0);除虫菊素和印楝素在组合物中的总浓度为0.2~5.0wt%;此外还包括乳化剂;所述乳化剂为聚醚胺和长链脂肪酸,该发明组合物能够针对红火蚁形成非常有效的驱避;进行试验符合安全标准,正常使用对人体无毒无害;红火蚁短期驱避效果达到99%以上。而由于红火蚁的泛滥,研究出更低高效无害的驱避也有十分重要的意义。Chinese patent CN113016797A, published on June 25, 2021, discloses a medicament for killing or repelling red fire ants. The medicament uses isoeugenol methyl ether as an active ingredient. The RIFA is the RIFA of the Hymenoptera Formicidae Leafcutter Subfamily. The test of the embodiment of the invention proves that isoeugenol methyl ether has a strong repelling effect on the RIFA, and isoeugenol methyl ether is often eaten as a spice. It is non-toxic to humans and animals and can be used as an environmentally friendly repellent. It is green and environmentally friendly, has simple ingredients, weak volatility, long duration, low cost, and can be mass-produced, which helps to repel red imported fire ants in large areas. Another Chinese patent CN113476363A, published on 2021.10.08, also discloses a composition for repelling red fire ants and its application. The composition includes pyrethrins and azadirachtin; the mass ratio of pyrethrins and azadirachtin is (0.1~2.0):(0.1~3.0); the total concentration of pyrethrins and azadirachtin in the composition is 0.2 to 5.0 wt%; in addition, it also includes an emulsifier; the emulsifier is polyetheramine and long-chain fatty acid, and the composition of the invention can form a very effective repellent against red fire ants; the test meets the safety standards, and normal use is harmful to the human body Non-toxic and harmless; the short-term repelling effect of red fire ants is over 99%. Due to the flooding of red imported fire ants, it is also of great significance to develop a lower, more efficient and harmless repellent.

而目前关于本发明的一种化合物及其组合的红火蚁驱避剂及其应用还未见报道。However, there is no report about a compound of the present invention and the red imported imported fire ant repellent of its combination and its application.

发明内容Contents of the invention

本发明的目的是,针对现有技术中的不足,提供一种化合物及其组合的红火蚁驱避剂及其应用。The object of the present invention is to provide a compound and its combined red imported fire ants repellent and its application.

一方面,提供了一种趋避红火蚁的化合物,所述的化合物为邻氨基苯甲酸丁酯。In one aspect, a compound for avoiding red fire ants is provided, and the compound is butyl anthranilate.

第二方面,提供了一种趋避红火蚁的组合物,所述的组合物的活性成分由A和B组成;所述的活性成分A为邻氨基苯甲酸丁酯;所述的活性成分B为邻氨基苯甲酸甲酯或氨基苯甲酸乙酯。In the second aspect, a composition for avoiding red fire ants is provided, the active ingredient of the composition is composed of A and B; the active ingredient A is butyl anthranilate; the active ingredient B is Methyl anthranilate or ethyl anthranilate.

第三方面,提供了一种红火蚁驱避剂,其特征在于,所述的趋避剂包含权利要求2所述的组合物和溶剂。In the third aspect, a repellant of red imported imported fire ants is provided, which is characterized in that said repellent comprises the composition as claimed in claim 2 and a solvent.

作为一个优选例,所述的溶剂为正己烷。As a preferred example, the solvent is n-hexane.

更优选地,所述的组合物的有效浓度为8ppm。More preferably, the effective concentration of the composition is 8ppm.

第三方面,提供了上述化合物、组合物以及趋避剂的两种用途,一是在制备趋避红火蚁药剂中的应用,二是在红火蚁的检疫和防治中的应用。The third aspect provides two uses of the above-mentioned compound, composition and repellant, one is the application in the preparation of RIFA repellent, and the other is the application in the quarantine and control of RIFA.

本发明优点在于:The present invention has the advantage that:

1、本发明选取邻氨基苯甲酸酯类的衍生物以及部分组合物中筛选得到对红火蚁具有良好驱避作用的种类,能有效干扰红火蚁的选择行为进而获得预防的效果。1. In the present invention, the derivatives of anthranilate esters and some of the compositions are screened to obtain species with good repelling effect on RIFA, which can effectively interfere with the selection behavior of RIFA and obtain the preventive effect.

2、本发明所述化合物容易获得且是食用或香精原材料,对人体无害,本发明在红火蚁的检疫和防治等农业技术领域方面有着非常广阔的应用前景。2. The compounds of the present invention are easy to obtain and are edible or flavor raw materials, and are harmless to the human body. The present invention has very broad application prospects in the field of agricultural technology such as the quarantine and control of red fire ants.

附图说明Description of drawings

附图1为本发明试验用培养皿。Accompanying drawing 1 is the petri dish for experiment of the present invention.

附图2为几种化合物及其组合对红火蚁驱避效果。图中的数字代表不同的化合物,分别为:1:邻氨基苯甲酸甲酯;2:间氨基苯甲酸甲酯;3:对氨基苯甲酸甲酯;4:邻氨基苯甲酸乙酯;5:间氨基苯甲酸乙酯;6:对氨基苯甲酸乙酯;7:对氨基苯甲酸异丙酯;8:对氨基苯甲酸丙酯;9:邻氨基苯甲酸丁酯;10:邻甲基苯甲酸甲酯;11:间甲基苯甲酸甲酯;12:对甲基苯甲酸甲酯;13:3-氨基-2-甲基苯甲酸乙酯;14:对二甲氨基苯甲酸乙酯。Accompanying drawing 2 is the repelling effect of several compounds and combinations thereof on red imported fire ants. The numbers in the figure represent different compounds, respectively: 1: methyl anthranilate; 2: methyl m-aminobenzoate; 3: methyl p-aminobenzoate; 4: ethyl anthranilate; 5: Ethyl m-aminobenzoate; 6: ethyl p-aminobenzoate; 7: isopropyl p-aminobenzoate; 8: propyl p-aminobenzoate; 9: butyl anthranilate; 10: o-methylbenzene Methyl formate; 11: methyl m-toluate; 12: methyl p-toluate; 13: ethyl 3-amino-2-methylbenzoate; 14: ethyl p-dimethylaminobenzoate.

具体实施方式Detailed ways

下面结合具体实施方式,进一步阐述本发明。应理解,这些实施例仅用于说明本发明而不用于限制本发明的范围。此外应理解,在阅读了本发明记载的内容之后,本领域技术人员可以对本发明作各种改动或修改,这些等价形式同样落于本申请所附权利要求书所限定的范围。The present invention will be further described below in combination with specific embodiments. It should be understood that these examples are only used to illustrate the present invention and are not intended to limit the scope of the present invention. In addition, it should be understood that after reading the contents of the present invention, those skilled in the art can make various changes or modifications to the present invention, and these equivalent forms also fall within the scope defined by the appended claims of the present application.

实施例1趋避效果的验证The verification of embodiment 1 avoidance effect

1材料1 material

红火蚁蚁群采自广州市市郊,通过水滴法分离后在实验室饲养供试。化合物1-6,10-12购于上海麦克林生化科技股份有限公司,化合物7-9购于上海阿拉丁生化科技股份有限公司,化合物13-14购于上海泰坦科技股份有限公司。The RIFA colonies were collected from the suburbs of Guangzhou City, separated by the water drop method and reared in the laboratory for testing. Compounds 1-6, 10-12 were purchased from Shanghai Macklin Biochemical Technology Co., Ltd., compounds 7-9 were purchased from Shanghai Aladdin Biochemical Technology Co., Ltd., and compounds 13-14 were purchased from Shanghai Titan Technology Co., Ltd.

2测试方法2 test method

将直径14.5cm,深度1.5cm的培养皿平放在试验台,在距离培养皿(图1)边缘2cm的地方用3mm规格钻头的电钻钻4个直径3mm的孔,4个孔以培养皿中心为圆心90度相隔开。将3ml规格指头瓶的瓶盖取下,用电钻在瓶盖的正中心钻一个直径3mm的孔;将热熔棒棒胶溶化后涂在钻好的指头瓶瓶盖平面,迅速粘在培养皿底部,保证两个孔对齐,用这样的方法将培养皿底部4个孔都粘上指头瓶的瓶盖;用小刷子蘸取氟隆均匀涂在培养皿壁上后晾干防止红火蚁爬出培养皿。Place a petri dish with a diameter of 14.5 cm and a depth of 1.5 cm on the test bench, and drill four holes with a diameter of 3 mm at a distance of 2 cm from the edge of the petri dish (Fig. 90 degrees apart from the center of the circle. Remove the bottle cap of the 3ml finger bottle, and drill a hole with a diameter of 3mm in the center of the bottle cap with an electric drill; melt the hot-melt glue and apply it on the surface of the drilled finger bottle cap, and quickly stick it to the petri dish At the bottom, make sure that the two holes are aligned. Use this method to stick the caps of the finger bottles on the four holes at the bottom of the petri dish; use a small brush to dip in Flon and apply it evenly on the wall of the petri dish, then dry it to prevent the red fire ants from crawling out petri dish.

取足量的沙子,洗净,80℃烘24h后备用。将各种化合物和化合物组合溶于正己烷配成浓度为8ppm,溶液为5ml,每巢红火蚁平行测试5次。试验前测得一个指头瓶大约可以装3-5g沙。取50g干沙,加入一个化合物的正己烷溶液5ml。在通风橱下用玻璃棒拌匀并不停搅拌5min,待正己烷完全挥发后沙子变干,再加入3ml蒸馏水并用玻璃棒不停搅拌5min以保证沙子湿润。先称指头瓶重量,用小勺将湿润的沙子装进指头瓶,保证填满并压实后称重,得出湿润沙子重量,之后拧在之前准备的培养皿底部瓶盖上。将50头红火蚁工蚁放入培养皿后再将培养皿置于26℃黑暗环境24h。将培养皿中的红火蚁全部诱出并移出培养皿,将所有指头瓶取下,80℃烘12h,将干沙倒出称重,记录数据,红火蚁搬运沙子重量=实验前干沙重量-实验后干沙重量,实验前干沙重量=湿沙重量-湿沙中水的质量,湿沙中水的质量=(3g水/50g干沙)*湿沙重量;驱避率(%)=(对照组平均搬沙量-处理组平均搬沙量/(对照组平均搬沙量)*100%。Take a sufficient amount of sand, wash it, and dry it at 80°C for 24 hours before use. Various compounds and compound combinations were dissolved in n-hexane to make a concentration of 8ppm, the solution was 5ml, and each nest of red fire ants was tested 5 times in parallel. Before the test, it was measured that a finger bottle could hold about 3-5g of sand. Take 50g of dry sand and add 5ml of a compound in n-hexane. Mix well with a glass rod under a fume hood and keep stirring for 5 minutes. After the n-hexane is completely volatilized, the sand becomes dry, then add 3ml of distilled water and keep stirring with a glass rod for 5 minutes to ensure that the sand is moist. Weigh the finger bottle first, put the wet sand into the finger bottle with a small spoon, make sure it is filled and compacted, weigh it, get the weight of the wet sand, and then screw it on the bottle cap at the bottom of the previously prepared Petri dish. Put 50 RIFA workers into the petri dish, and then place the petri dish in a dark environment at 26°C for 24 hours. All the RIFAs in the petri dish were lured out and removed from the petri dish, all finger bottles were removed, baked at 80°C for 12 hours, the dry sand was poured out and weighed, and the data was recorded. The weight of the sand carried by the RIFA = the weight of the dry sand before the experiment - Dry sand weight after experiment, dry sand weight before experiment=wet sand weight-the quality of water in wet sand, the quality of water in wet sand=(3g water/50g dry sand)*wet sand weight; Repellent rate (%)= (Average sand removal amount of the control group-average sand removal amount of the treatment group/(average sand removal amount of the control group)*100%.

3实验结果3 Experimental results

结果如附图2所示,供试的几种化合物及化合物组合除了对氨基苯甲酸乙酯、对氨基苯甲酸丙酯和邻甲基苯甲酸甲酯以外均有良好的驱避效果,有些化合物的驱避率都在55%以上,单个使用邻氨基苯甲酸丁酯的驱避效果在87%,联合使用的效果有些达到98%,以化合物邻氨基苯甲酸甲酯+邻氨基苯甲酸丁酯和化合物邻氨基苯甲酸乙酯+邻氨基苯甲酸丁酯的组合效果驱避明显,故可以被选为红火蚁的驱避剂。The results are shown in accompanying drawing 2, several compounds and compound combination for testing all have good repellent effect except ethyl p-aminobenzoate, propyl p-aminobenzoate and methyl o-toluate, some compounds The repelling rate of all drugs is above 55%, the repelling effect of single use of butyl anthranilate is 87%, and the effect of combined use can reach 98%. The compound methyl anthranilate + butyl anthranilate The combination of compound ethyl anthranilate + butyl anthranilate has obvious repelling effect, so it can be selected as the repellent of red imported fire ants.

以上所述仅是本发明的优选实施方式,应当指出,对于本技术领域的普通技术人员,在不脱离本发明方法的前提下,还可以做出若干改进和补充,这些改进和补充也应视为本发明的保护范围。The above is only a preferred embodiment of the present invention, it should be pointed out that for those of ordinary skill in the art, without departing from the method of the present invention, some improvements and supplements can also be made, and these improvements and supplements should also be considered Be the protection scope of the present invention.

Claims (7)

1. A compound for repelling solenopsis invicta is characterized in that the compound is butyl anthranilate.
2. A composition for repelling solenopsis invicta, which is characterized in that the active ingredients of the composition consist of A and B; the active ingredient A is butyl anthranilate; the active component B is methyl anthranilate or ethyl aminobenzoate.
3. A solenopsis invicta repellent comprising the composition of claim 2 and a solvent.
4. A repellent according to claim 3, wherein the solvent is n-hexane.
5. A repellent according to claim 3, wherein the effective concentration of the composition is 8ppm.
6. Use of a compound according to claim 1, a composition according to claim 2, or a repellent according to any one of claims 3 to 5 in the manufacture of a medicament for repelling solenopsis invicta.
7. Use of a compound according to claim 1, a composition according to claim 2, or a repellent according to any one of claims 3 to 5 for quarantine and control of solenopsis invicta.
CN202310415244.5A 2023-04-18 2023-04-18 Compound, solenopsis invicta repellent prepared from compound and combination of compound and solenopsis invicta repellent and application of solenopsis invicta repellent Pending CN116649347A (en)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN118165293A (en) * 2024-03-21 2024-06-11 华南农业大学 Isoeugenol methyl ether lignocellulose nanofiber emulsion and preparation method and application thereof

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN118165293A (en) * 2024-03-21 2024-06-11 华南农业大学 Isoeugenol methyl ether lignocellulose nanofiber emulsion and preparation method and application thereof
CN118165293B (en) * 2024-03-21 2024-09-10 华南农业大学 Isoeugenol methyl ether lignocellulose nanofiber emulsion and preparation method and application thereof

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