KR100514977B1 - Composition having mosquito larvicidal activity - Google Patents

Abstract

The present invention relates to a mosquito larvae insecticidal composition, the composition is an extract of a plant selected from the group consisting of bay, bergamot, caraway, carot, cardamom, cumin, galbanum, marzoram, myrra, neroyl and niauli , Anthrabic acid, α-cadrene, 1,2-dimethylnaphthalene, emodine, 1-ethoxycarbonylpiperazine, 2-hydroxymethylanthraquinone, 8-hydroxyquinaldine, p -naphthohydro At least one compound selected from the group consisting of quinones, α-naphthoquinolines, α-naphthoquinones, and β-naphthoquinones and derivatives thereof, and at least one substance selected from the group consisting of active ingredients.

As described above, the plant extracts or compounds of the present invention have the effect of the invention of excellent mosquito larvae pesticides to remove mosquito larvae which are mediators of various diseases. In particular, natural plant extracts are environmentally friendly materials that are less toxic to humans as well as fish and lungs compared to synthetic chemicals used as pesticides.

Description

Mosquito larvae insecticidal composition {COMPOSITION HAVING MOSQUITO LARVICIDAL ACTIVITY}

[Industrial use]

The present invention relates to a mosquito larvae insecticidal composition, and more particularly, to a mosquito larvae insecticidal composition having excellent mosquito larvae insecticidal ability and low toxicity.

[Prior art]

Mosquitoes are a representative taxa of numerous sanitary pests from olden days to the present, and more than 2,500 species are distributed worldwide and live in the tropics as well as in the temperate and polar regions. In addition to underground tunnels, deep coal mines, or 4,000 meters above sea level, they also live in the basement of apartments recently, moving to homes by elevator in winter (Seasonal prevalence and composition rate of Culex pipiens group occurring in the basement of an apartment, Taegu , Korea.Korean journal of entomology Vol.26 (1) pp.21-27, 1996). Mosquitoes mediate globally important diseases such as malaria, filamentous fever, yellow fever, and encephalitis (Evolutionary studies of malaria vectors, Trends in Parasitology, Volume 18, Issue 2, 1 February 2002, Pages 75-80 Martin J. Donnelly, Frederic Simard and Tovi Lehmann) as well as vampire bites cause redness and swelling, severe itching, sleep disturbances and severe scratches, which are secondary to direct damage such as inflammation caused by germ infection.

In Korea, mosquito-borne diseases are mainly caused by malaria caused by Anopheles sinensis and encephalitis caused by Culex tritaeniorhynchus (Seasonal Prevalence of Mosquitoes). Collected from Light Trap in Korea (1993 ~ 1994) .Korean journal of entomology Vol.27 (1) pp.21-28, 1997).

As the global warming gradually slows the subtropics, mosquito damage is expected to increase. According to a report by the World Health Organization in 1992, 20 million people worldwide are infected with malaria each year. Of these, 14,000 to 26,000 people died, and the number of infections is expected to increase in the future.

And the most important means so far in controlling mosquitoes, which are the mediators of human health-threatening diseases, is to rely on insecticides. The biggest problem is the emergence of mosquitoes that are resistant to insecticides. the promoters for the esterase genes associated with insecticide resistance in the mosquito Culex quinquefasciatus , Biochimica et Biophysica Acta (BBA)-Gene Structure and Expression, In Press, Uncorrected Proof, Available online 4 December 2001, Nicola J. Hawkes and Janet Hemingway; Genetic changes associated with insecticide exposure in mosquitoes, Pathophysiology, Volume 5, Supplement 1, June 1998, A. Callaghan). Insecticide susceptibility of Culex pipiens pallens (Culicidae, Diptera) larvae in Seoul.Korean journal of entomology Vol.27 (1) pp.9-13, 1997). In addition, the problem that the existing pesticides are likely to be harmful to the human body is also seriously pointed out.

Control of mosquitoes includes adult control by chemical control and infertility male radiation, and larval control by biological control and chemical control methods. In particular, among insecticides for mosquito control, insecticides for larvae control include 10 organophosphorus compounds, 3 pyrethroid compounds, 4 insect growth regulators, and 2 microbial insecticides (Hygiene Insectology, pp221. Lee, Han-il. 2002). Among them, insect growth regulators, which are known to solve the problem of resistance to general insecticides because they do not harm the environment and mammals, and are considered to solve the problem of resistance to general insecticides. [1- (2, 6-di-phenyl-fluorenyl auto -3- p - chlorophenyl a treatment with urea ([1- (2,6-difluotophenyl) -3- p -chlorophenyl urea] 1,000 g / ha of the formulation) A 10-day control effect was obtained with a mortality rate of 70% or more.Bti- based microbial insecticides were reported to have a sustained effect for one month and insect growth regulators with a main component of metoprene for five months (Toxicology of insecticides.pp. 503. F. Mantsumura.Prenum Press. 1975).

Therefore, researches to replace the pesticides for mosquito larvae and adults have been conducted worldwide in natural materials (The use of Garlic ( Allium Sativa ) and Lemon Peel ( Citrus Limon ) Extracts as Culex Pipiens Larvacides: Persistence and Interaction with an Organophosphate Resistance Mechanism, Chemosphere, Volume 39, Issue 14, December 1999, Pages 2489-2496 Claire J. Thomas and Amanda Callaghan; Insecticidal Potentials of Ocimum basilicum Leaf-extract, Bioresource Technology, Volume 64, Issue 3, June 1998, Pages 237-239

SC Umerie, HU Anaso and LJC Anyasoro; Larvicidal Activity of Isobutylamides Identified in Piper nigrum Fruits against Three Mosquito Species, Journal of Agricultural and Food Chemistry; 2002; 50 (7); 1866-1870. Il-Kwon Park, Sang-Gil Lee, Sang-Chul Shin, Ji-Doo Park, and Young-Joon Ahn *), have not yet found satisfactory materials.

It is an object of the present invention to provide a mosquito larvae insecticidal composition which is harmless to humans and exhibits insecticidal properties against mosquito larvae.

In order to achieve the above object, the present invention is a bay ( Pimenta racemosa ), Bergamot ( Citrus bergamia ), Caraway ( Carum carvi ), Carot ( Daucus carot ), Cardamun ( Juniperis virginiana ), Cumin ( Cuminum cyminum ), Galbanum ( Ferula galbanifulua ), Marjoram ( Origanum majorana ), Mirra ( Commiphora myrrha ), Nerol ( Lavandula officinalis ) and Niauli ( Melaeuca viridiflora ) Extracts of plants selected from the group consisting of Provided is a larvae pesticidal composition comprising at least one substance selected from the group consisting of the above compounds and derivatives thereof as an active ingredient.

[Formula 1]

(In Formula 1,

R ₁ is —H, —OH, —CH ₃ ,

R ₂ is -H, -OH, -CH ₃ )

[Formula 2]

(In Formula 2,

R ₁ is —H, —OH, —CH ₃ ,

R ₂ is —H, —OH, —CH, —COOH,

R ₃ is —H, —OH, —CH ₃ ,

R ₄ is -H, -OH, -CH ₃ )

[Formula 3]

(In Chemical Formula 3,

R ₁ is -H, -OH, -CH ₃

R ₂ is —H, —OH, —CH ₃ , -COOH)

[Formula 4]

(In Formula 4,

R ₁ is —H, —OH, —CH ₃ ,

R ₂ is —H, —OH, —CH ₃ ,

R ₃ is —H, —OH, —CH ₃ , -COOH, -NH ₂ ,

R ₄ is —H, —OH, —CH ₃ , -COOH, -COCH ₃ )

[Formula 5]

(In Chemical Formula 5,

R ₁ is —H, —OH, —CH ₃ , —CONH ₂ ,

R ₂ is -H, -NH, -O, -CH ₂ )

[Formula 6]

(In Chemical Formula 6, R is -H, -OH, -CH ₃ , -COOH, -COCH ₂ CH ₃ )

[Formula 7]

(In Chemical Formula 7,

R ₁ is —H, —OH, —CH ₃ , —COOH, —CONH ₂ ,

R ₂ is -H, -OH, -CH ₃ , -COOH

[Formula 8]

(In Formula 8,

R ₁ is —OH, —CH ₃ ,

R ₂ is -OH, -CH ₃ )

[Formula 9]

[Formula 10]

[Formula 11]

Hereinafter, the present invention will be described in more detail.

The present invention relates to a mosquito larvae insecticidal composition using an extract obtained from a fragrant aromatic plant used as a medicament for folk medicine. In addition, the mosquito larvae pesticidal composition of the present invention may include a synthetic compound in addition to the plant extract, and may simultaneously include the plant extract and the synthetic compound.

The aromatic plant extract used in the present invention is to screen insecticidal properties against mosquito larvae among the plants used as drug treatments, and to select plant extracts having excellent effect.

These plant extracts include Pimenta racemosa , Citrus bergamia , Carum carvi , Daucus carot , Juniperis virginiana , Cuminum cyminum , Ferula galbanifulua , Extracts of at least one plant selected from the group consisting of marjoram ( Origanum majorana ), mirra ( Commiphora myrrha ), neroyl ( Lavandula officinalis ) and niauli ( Melaeuca viridiflora ) can be used. Preferably, at least one plant extract selected from the group consisting of bay ( Pimenta racemosa ), bergamot ( Citrus bergamia ), cardamom ( Juniperis virginiana ) and marjoram ( Origanum majorana ) is preferred because of its mosquito larvae insecticidal effect. .

Extracts of these plants may be essential oils or organic solvent extracts. Plant essential oils can be extracted or used commercially available essential oils. Plant essential oil extraction method can be carried out by a conventional method, and representative extraction methods include distillation using water or steam and compression.

The organic solvent extract can be prepared using an alcohol having 1 to 5 carbon atoms, ethyl acetate, hexane or chloroform organic solvent. Among the alcohols, methanol or ethanol is preferable.

The mosquito larvae pesticidal composition of the present invention also includes at least one compound selected from the group consisting of the compounds of Formulas 1 to 11 or at least one derivative thereof. The compounds selected from the group consisting of the following formulas (1), (3), (4), (6) to (11), or derivatives thereof are preferable, and the compounds of the following formulas (6), (10) or (11) are more preferable because they have the best insecticidal effect.

[Formula 1]

(In Formula 1,

R ₁ is H, OH, CH ₃ ,

R ₂ is H, OH, CH ₃ ,

Anthraflavic acid is preferred, wherein R ₁ and R ₂ are both OH)

[Formula 2]

(In Formula 2,

R ₁ is H, OH, CH ₃ ,

R ₂ is H, OH, CH, COOH,

R ₃ is H, OH, CH ₃ ,

R ₄ is H, OH, CH ₃ ,

Α-Cedrene is preferred, wherein both R ₁ and R ₃ are CH ₃ )

[Formula 3]

(In Chemical Formula 3,

R ₁ is H, OH, CH ₃

R ₂ is H, OH, CH ₃ , COOH,

Preferred is 1,2-dimethylnaphthalene, in which both R ₁ and R ₂ are CH ₃ )

[Formula 4]

(In Formula 4,

R ₁ is —H, —OH, —CH ₃ ,

R ₂ is —H, —OH, —CH ₃ ,

R ₃ is —H, —OH, —CH ₃ , -COOH, -NH ₂ ,

R ₄ is —H, —OH, —CH ₃ , -COOH, -COCH ₃ ),

R ₁ is CH ₃ and Emodine is preferred wherein R ₂ , R ₃ and R ₄ are all OH)

[Formula 5]

(In Chemical Formula 5,

R ₁ is —H, —OH, —CH ₃ , —CONH ₂ ,

R ₂ is —H, —NH, —O, —CH ₂ ,

Preference is given to 1-ethoxycarbonylpiperazine wherein R ₁ is CH ₃ and R ₂ is NH.)

[Formula 6]

(In Chemical Formula 6, R is -H, -OH, -CH ₃ , Preferred is 2-Hydroxymethyl anthraquinone wherein -COOH, -COCH ₂ CH ₃ and R is OH.

[Formula 7]

(In Chemical Formula 7,

R ₁ is —H, —OH, —CH ₃ , —COOH, —CONH ₂ ,

R ₂ is —H, —OH, —CH ₃ , —COOH,

Preferred is 8-Hydroxyquinaldine, wherein R ₁ is OH and R ₂ is CH _3. )

[Formula 8]

(In Formula 8,

R ₁ is —OH, —CH ₃ ,

R ₂ is —OH, —CH ₃ ,

Preferably naphthoquinone, hydroquinone (p -Naphthohydroquinone)) - R ₁ and R ₂ are both OH is p.

[Formula 9]

[Formula 10]

[Formula 11]

In the present invention, the derivative of the compound refers to a parent-nucleus compound, wherein the parent-nucleus compound is a conventionally known property by adding or removing hydroxyl groups or other chemical structures through chemical synthesis based on the structure of a known substance. As a new substance that has been removed or enhanced the effect, the parent-nucleus compound, that is, derivatives prepared based on the compounds of Formulas 1 to 11 of the present invention may exhibit pesticidal properties.

The mosquito larvae insecticidal composition of the present invention is Culex pipiens pallens , Culex tritaeniorhynchus , Coolex Select from the group consisting of Culex vishnui , Culex gelidus , Culex fuscocephala , A edes aegyti and Anopheles stephensi It has excellent pesticidal activity against mosquito larvae.

In the mosquito larvae pesticidal composition of the present invention, the content of the active ingredient may be appropriately adjusted according to the formulation of the pesticide and the spraying method, but 0.01 to 40% by weight is preferable. If the content of the active ingredient is less than 0.01% by weight mosquito larvae pesticidal effect is minimal, 40% by weight can obtain a sufficient pesticidal effect, it is no longer necessary to use an excess.

The mosquito larvae insecticidal composition of the present invention is a powder, granules, wettable powders, flowable formulations, emulsion concentrates, microcapsules, oily formulations according to the methods commonly used in the insecticide field by mixing excipients according to uses and purposes other than the active ingredient. It can be prepared to take the form of various preparations such as, aerosols, heated fumigants, clouding agents, unheated fumigants and the like.

The excipients may be those well known in the art, such as liquid or solid carriers (diluents), electrodeposition agents, emulsifiers, humectants, dispersants, pressure-sensitive adhesives, disintegrants and the like. Examples of the liquid carrier include aromatic hydrocarbons such as toluene and xylene, alcohols such as butanol, octanol and glycol, ketones such as acetone, amides such as dimethylformamide, sulfoxides such as dimethyl sulfoxide, methylnaphthylene and cyclohexane Petroleum fractions such as warm, animal oils, vegetable oils, fatty acids, fatty acid esters, kerosene and diesel oils or water.

Examples of the solid carrier include clay, kaolin, talc, diatomaceous earth, silica, calcium carbonate, montmillonite, bentonite, feldspar, quartz, alumina, sawdust and the like.

Examples of the electrodeposition agent include polyoxyethylene nonyl penny ether, polyoxyethylene lauryl ether, and the like, and examples of the emulsifier or dispersant include anionic surfactants, cationic surfactants, nonionic surfactants and amphoteric surfactants. For example, triton series, such as higher alcohol sodium sulfate, stearyl trimethylammonium chloride, polyoxyethylene alkyl phenyl ether, lauryl betaine, Triton-X-100, etc. are mentioned.

Examples of the moisturizing agent include polyoxyethylene nonyl phenyl ether dialkyl sulfosuccinate, and the like. Examples of the pressure-sensitive adhesive include carboxymethyl cellulose, polyvinyl alcohol, and the disintegrants include sodium lignin sulfonate, Sodium lauryl sulfate.

The mosquito larvae insecticidal composition of the present invention is used where the mosquitoes inhabit, the method of use is preferably a method such as spray treatment, sleep treatment, contact treatment, the application dose can be used as a dose to apply a conventional insecticide. In addition, when the insecticidal composition of the present invention is sprayed to the place where the mosquito larvae naturally inhabit, it may form a film on the contact poison or water surface to kill the mosquito larvae due to respiratory depression.

Hereinafter, preferred examples are provided to aid in understanding the present invention. However, the following examples are merely provided to more easily understand the present invention, and the present invention is not limited to the following examples.

[Examples 1 to 11] Sample Preparation and Insecticidal Plant Essential Oils and Compounds

Bay ( Pimenta racemosa ), Bergamot ( Citrus bergamiaum ), Caraway ( Carum carvi ), Carrot ( Daucus carot ), Cardamun ( Juniperis virginiana ), Cuminum cyminum , Galulanum ( Ferula galbaniflua ), Marjoram ( Origanum majorana) ), Myra ( Commiphora myrrha ), Nerol ( Lavandula officinalis ) and Nyauli ( Melaleuca viridiflora ) were collected and dried in the shade and finely chopped.

In 300 g of 11 kinds of finely divided plants, 2,000 ml of distilled water and 200 ml of hexane were put, and 100 ml of continuous steam distillation apparatus (SDE, Nickerson & Likens apparatus) was continuously extracted for 5-6 hours. The hexane extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure at 20 ° C. or lower to use as an active ingredient of the mosquito larvae insecticidal composition.

Experimental Example 1

Mosquitoes Used in Insecticidal Assays

Insecticidal activity was performed against two mosquito larvae. Culex pipiens pallens and Egyptian mosquitoes ( Aedes aegypti ) were bred in a breeding room maintained at a relative humidity of 70 ± 5% and a temperature of 28 ± 1 ° C. (Ebioze ^® ) 1: 1 mixed feed, distilled water and tap water 1: 1 mixed of 200 ml was poured into the breeding container and put in the breeding room. The mosquitoes were bred without exposure to pesticides.

Insecticidal test

The plant extracts of Examples 1 to 11 were dissolved in acetone so as to be in a concentration range of 1.25 to 200 ppm, as shown in Tables 1 and 2, and then diluted in stages. Triton-X-100 was added to the obtained diluent as an emulsifier in a ratio of 99: 1 (vol.%) And mixed well to prepare a mosquito larvae insecticidal composition.

Insecticidal experiments were conducted on Culex pipiens pallens and Aedes aegypti four instars using the composition. All experiments were conducted in a laboratory adjusted to maintain 28 ± 1 ° C. and relative humidity of 70 ± 5%.

250 ml of the composition was transferred to a beetle with 30 four insects. To compare the test results, untreated controls were prepared containing the same number of mosquito larvae in the test solution mixed with acetone, Triton X-100 and water. Five identical test solutions were prepared for each experiment. Mortality was measured 24 hours after treatment with the composition and control, and the results are shown in Dig Table 1 ( Culled mosquito: Culex pipiens pallens ) and Table 2 (Egyptian Mosquito: Aedes aegypti ). A comparison between the means for mortality was made using Scheffe's test (SAS Institute, 1996).

In Tables 1 and 2, a and b indicate that the mean is not statistically different ( P = 0.05, Sheffe's test), and the insecticidal rate is represented by transforming the square root of the arc sine.

Plant name Insecticidal rate (mean ± standard deviation,%) Treatment Concentration (ppm) 200 100 50 25 12.5 6.25 Example 1 Bay ( Pimenta racemosa ) 100a 100a 100a 100a 52.3 ± 2.3b 32.2 ± 1.5b Example 2 Citrus bergamia 100a 100a 100a 100a 32.5 ± 1.3 b 24.2 ± 3.1b Example 3 Carum carvi 100a 100a 100a 44.5 ± 1.6b 0b 0b Example 4 Daucus carot 100a 100a 100a 84.4 ± 2.2b 59.2 ± 1.8b 48.9 ± 2.4b Example 5 Cardamom ( Juniperis virginiana ) 100a 100a 52.2 ± 2.3b 40.5 ± 1.8b 0b 0b Example 6 Cuminum cuminum 100a 100a 100a 24.5 ± 2.6b 0b 0b Example 7 Galulanum ( Ferula galbaniflua ) 100a 100a 85.1 ± 2.3b 32.9 ± 1.5b 0b 0b Example 8 Marzoram ( Origanum majorana ) 100a 100a 100a 83.5 ± 2.3b 51.2 ± 1.7 b 10.4 ± 1.2b Example 9 Mirra ( Commiphora myrrha ) 100a 100a 100a 100a 11.5 ± 1.7 b 0b Example 10 Neroo ( Lavandula officinalis ) 100a 100a 74.6 ± 2.4b 28.7 ± 2.5b 0b 0b Example 11 Nyauli ( Melaleuca viridiflora ) 100a 100a 68.6 ± 1.5 b 31.1 ± 1.3 b 0b 0b

Jung, Yumyung  Insecticidal rate (mean ± standard deviation,%) Treatment Concentration (ppm) 200 100 50 25 12.5 6.25 Example 1 Bay ( Pimenta racemosa ) 100a 100a 100a 100a 38.5 ± 1.8b 0b Example 2 Citrus bergamia 100a 100a 100a 100a 14.5 ± 1.9b 0b Example 3 Carum carvi 100a 100a 100a 25.4 ± 1.9b 0b 0b Example 4 Daucus carot 100a 100a 100a 61.3 ± 1.6b 38.3 ± 1.6 b 23.1 ± 2.1b Example 5 Cardamom ( Juniperis virginiana ) 100a 100a 37.8 ± 2.5b 12.4 ± 2.1b 0b 0b Example 6 Cuminum cuminum 100a 100a 100a 0b 0b 0b Example 7 Galulanum ( Ferula galbaniflua ) 100a 100a 67.3 ± 1.7 b 11.4 ± 1.2b 0b 0b Example 8 Marzoram ( Origanum majorana ) 100a 100a 100a 72.3 ± 2.1b 32.4 ± 1.6 b 0b Example 9 Mirra ( Commiphora myrrha ) 100a 100a 100a 100a 0b 0b Example 10 Neroo ( Lavandula officinalis ) 100a 100a 64.1 ± 1.8b 0b 0b 0b Example 11 Nyauli ( Melaleuca viridiflora ) 100a 100a 54.3 ± 1.3b 15.8 ± 1.1 b 0b 0b

In the results shown in Table 1, when the plant extracts of Examples 1 to 11 were used at concentrations of 200ppm and 100ppm, all showed a 100% insecticidal rate against the red larvae larvae, even when treated with 25ppm Bay, Bergamot In the case of extracts extracted from and Myra, the insecticidal rate was 100%, and the carrot extract was about 85%. In addition, the 12.5 ppm treatment showed a pesticide rate of 50% or more in the essential oils of bay, carrot and marjoram.

In addition, in the Egyptian forest mosquito larva of Table 2, all of the plant extracts of Examples 1 to 11 at 200ppm, 100ppm treatment showed 100% insecticidal rate, even if the treatment of 25ppm 100 in the extract extracted from bay, bergamot and mirra Pesticide rate was shown in%, and the pesticide rate was over 50% in the carrot and marjoram extracts.

(Examples 12 to 22)

Anthraflavic acid, α-naphthoquinoline, α-naphthoquinone are Wako, α-cadrene, 1,2-dimethylnaphthalene, emodine, 1-ethoxycarbonylpiperazine, 2-hydroxy Methyl anthraquinone, 8-hydroxyquinaldine, Fluka, p -naphthohydroquinone, and p-naphthoquinone were purchased from Sigma and used as active ingredients in mosquito larvae insecticidal compositions.

Experimental Example 2

Insecticidal assay

The mosquito larvae insecticidal composition was prepared in the same manner as in Experimental Example 1 using the active ingredient, and the results were measured using the same method as in Table 3 (Red mosquito: Culex pipiens pallens ) and Table 4 (Egypt forest mosquito). : Aedes aegypti ).

compound Insecticidal rate (mean ± standard deviation,%) Treatment Concentration (ppm) 50 20 10.0 5.0 2.5 1.25 Example 12 Anthraflavic Acid 100a 100a 92.4 ± 1.9b 38.5 ± 1.1b 4.4 ± 0.9b 0b Example 13 α-cadren 100a 84.5 ± 2.1b 60.4 ± 2.5b 15.8 ± 1.9b 0b 0b Example 14 1,2-dimethylnaphthalene 100a 100a 87.3 ± 2.2b 28.6 ± 1.8 b 0b 0b Example 15 Emodin 100a 100a 100a 68.4 ± 1.6 b 23.5 ± 1.1 b 8.7 ± 1.0b Example 16 1-ethoxycarbonylpiperazine 100a 65.8 ± 2.2 b 50.3 ± 1.8b 10.6 ± 1.7 b 0b 0b Example 17 2- (hydroxymethyl) anthraquinone 100a 100a 100a 100a 56.3 ± 2.1b 42.9 ± 1.8b Example 18 8-hydroxyquinaldine 100a 100a 64.4 ± 1.5b 25.6 ± 2.3b 13.8 ± 2.1b 0b Example 19 p -naphthohydroquinone 100a 100a 100a 85.6 ± 2.7 b 35.7 ± 2.4b 12.2 ± 1.1 b Example 20 α-naphthoquinoline 100a 100a 76.5 ± 1.6 b 32.6 ± 1.5 b 18.2 ± 1.1 b 0b Example 21 α-naphthoquinone 100a 100a 100a 100a 73.5 ± 1.6b 48.1 ± 1.8b Example 22 β-naphthoquinone 100a 100a 86.5 ± 1.7 b 72.2 ± 2.4b 63.1 ± 1.7 b 46.9 ± 1.4 b Comparative Example 1 Benzyl benzoate 100a 41.2 ± 1.9b 15.3 ± 2.8b 0b 0b 0b

Table 3 shows the results of the insecticidal test for the larvae larvae, all 11 compounds showed a pesticidal rate of 100% at 50ppm treatment level. In addition, at 20ppm treatment level, anthrabic acid, 1,2-dimethylnaphthalene, emodine, 2-hydroxymethylanthraquinone, 8-hydroxyquinaldine, p -naphthohydroquinone, α-naphthoquinoline, α- Naphthoquinone and α-naphthoquinone showed 100% insecticidal rate, and at 2.5 ppm treatment level, 2-hydroxymethylanthraquinone, α-naphthoquinone and α-naphthoquinone showed more than 50% insecticide. It can be seen that the pesticide rate against mosquito larvae is excellent. The eleven compounds of Examples 12 to 22 showed superior activity to the red colony larvae compared to the benzyl benzoate of Comparative Example 1, which is a conventional mosquito larvae insecticide.

compound Insecticidal rate (mean ± standard deviation,%) Treatment Concentration (ppm) 50 20 10.0 5.0 2.5 1.25 Example 12 Anthraflavic Acid 100a 100a 85.2 ± 1.7 b 21.4 ± 1.5b 0b 0b Example 13 α-cadren 100a 72.5 ± 2.8 b 49.6 ± 2.2 b 8.5 ± 1.1 b 0b 0b Example 14 1,2-dimethylnaphthalene 100a 100a 76.5 ± 2.3b 14.6 ± 1.5b 0b 0b Example 15 Emodin 100a 100a 100a 55.3 ± 2.7b 13.9 ± 1.3 b 0b Example 16 1-ethoxycarbonylpiperazine 100a 53.1 ± 1.9b 48.4 ± 2.7 b 0b 0b 0b Example 17 2- (hydroxymethyl) anthraquinone 100a 100a 100a 100a 44.6 ± 2.4b 34.1 ± 2.9 b Example 18 8-hydroxyquinaldine 100a 100a 49.8 ± 1.4 b 20.5 ± 2.1b 0b 0b Example 19 p -naphthohydroquinone 100a 100a 100a 72.3 ± 2.1b 25.1 ± 2.5b 0b Example 20 α-naphthoquinoline 100a 100a 60.3 ± 1.5b 24.2 ± 2.5b 9.4 ± 1.0 b 0b Example 21 α-naphthoquinone 100a 100a 100a 100a 60.3 ± 2.6b 40.6 ± 2.3b Example 22 β-naphthoquinone 100a 100a 73.2 ± 2.5b 63.5 ± 2.1b 54.6 ± 1.5b 39.6 ± 1.5b Comparative Example 1 Benzyl benzoate 100a 35.3 ± 2.6b 10.1 ± 2.5b 0b 0b 0b

Table 4 shows the insecticidal rate for Egyptian forest mosquito larvae. All compounds of Examples 12-22 exhibited 100% pesticide at 50 ppm treatment level. In addition, at 20ppm treatment level, anthrabic acid, 1,2-dimethylnaphthalene, emodine, 2-hydroxymethylanthraquinone, 8-hydroxyquinaldine, p -naphthohydroquinone, α-naphthoquinoline, α- Naphthoquinone and β-naphthoquinone showed 100% insecticidal rate, 44.6% 2-hydroxymethylanthraquinone, 60.3% α-naphthoquinone and β-naphthoquinone at 2.5 ppm The insecticide rate of 54.6% indicates that the insecticide rate against mosquito larvae is excellent. The eleven compounds of Examples 12 to 22 showed superior activity to the Egyptian forest mosquito larvae compared to the benzyl benzoate of Comparative Example 1, which is a conventional mosquito larvae insecticide.

As described above, the plant extracts or compounds of the present invention have the effect of the invention of excellent mosquito larvae pesticides to remove mosquito larvae which are mediators of various diseases. In particular, natural plant extracts are environmentally friendly materials that are less toxic to humans as well as fish and lungs compared to synthetic chemicals used as pesticides.

Claims (7)

Bay ( Pimenta racemosa ), Bergamot ( Citrus bergamia ), Caraway ( Carum carvi ), Carrot ( Daucus carot ), Cardamun ( Juniperis virginiana ), Cuminum cyminum , Galulanum ( Ferula galbanifulua ), Marjoram ( Origanum majorana) ), An extract of a plant selected from the group consisting of Commiphora myrrha , Lavandula officinalis and Melaeuca viridiflora , at least one compound selected from Chemical Formulas 1 to 11, and derivatives thereof Mosquito larvae insecticidal composition comprising one or more substances selected from the active ingredient, the content of the active ingredient is 0.01 to 40% by weight. [Formula 1] (In Formula 1, R ₁ is —H, —OH, —CH ₃ , R ₂ is -H, -OH, -CH ₃ ) [Formula 2] (In Formula 2, R ₁ is —H, —OH, —CH ₃ , R ₂ is —H, —OH, —CH, —COOH, R ₃ is —H, —OH, —CH ₃ , R ₄ is -H, -OH, -CH ₃ ) [Formula 3] (In Chemical Formula 3, R ₁ is -H, -OH, -CH ₃ R ₂ is —H, —OH, —CH ₃ , -COOH) [Formula 4] (In Formula 4, R ₁ is —H, —OH, —CH ₃ , R ₂ is —H, —OH, —CH ₃ , R ₃ is —H, —OH, —CH ₃ , -COOH, -NH ₂ , R ₄ is —H, —OH, —CH ₃ , -COOH, -COCH ₃ ) [Formula 5] (In Chemical Formula 5, R ₁ is —H, —OH, —CH ₃ , —CONH ₂ , R ₂ is -H, -NH, -O, -CH ₂ ) [Formula 6] (In Chemical Formula 6, R is -H, -OH, -CH ₃ , -COOH, -COCH ₂ CH ₃ ) [Formula 7] (In Chemical Formula 7, R ₁ is —H, —OH, —CH ₃ , —COOH, —CONH ₂ , R ₂ is -H, -OH, -CH ₃ , -COOH [Formula 8] (In Formula 8, R ₁ is —OH, —CH ₃ , R ₂ is -OH, -CH ₃ ) [Formula 9] [Formula 10] [Formula 11] The mosquito larvae insecticidal composition according to claim 1, wherein the extract is an alcohol or organic solvent extract having 1 to 5 carbon atoms. The mosquito larvae insecticidal composition according to claim 1, wherein the extract is a plant essential oil. The method of claim 1, wherein the extract is a plant extract extracted from one plant selected from the group consisting of bay ( Pimenta racemosa ), bergamot ( Citrus bergamia ), cardamom ( Juniperis virginiana ) and marjoram ( Origanum majorana ) Mosquito larvae insecticidal composition. The mosquito larvae pesticidal composition according to claim 1, wherein the mosquito larvae pesticidal composition comprises one or more compounds selected from the group consisting of Formulas 1, 3, 4, 6 to 11, and derivatives thereof. [Formula 1] (In Formula 1, R ₁ is —H, —OH, —CH ₃ , R ₂ is -H, -OH, -CH ₃ ) [Formula 3] (In Chemical Formula 3, R ₁ is -H, -OH, -CH ₃ R ₂ is —H, —OH, —CH ₃ , -COOH) [Formula 4] (In Formula 4, R ₁ is —H, —OH, —CH ₃ , R ₂ is —H, —OH, —CH ₃ , R ₃ is —H, —OH, —CH ₃ , -COOH, -NH ₂ , R ₄ is —H, —OH, —CH ₃ , -COOH, -COCH ₃ ) [Formula 6] (In Chemical Formula 6, R is -H, -OH, -CH ₃ , -COOH, -COCH ₂ CH ₃ ) [Formula 11] The mosquito larvae insecticidal composition according to claim 5, wherein the mosquito larvae insecticidal composition comprises at least one compound selected from the group consisting of Chemical Formulas 6, 10, and 11 and derivatives thereof. [Formula 6] (In Chemical Formula 6, R is -H, -OH, -CH ₃ , -COOH, -COCH ₂ CH ₃ ) [Formula 10] [Formula 11] According to claim 1, wherein the mosquito larva is Culex pipiens pallens , Coolex Culex tritaeniorhynchus , Coolex Select from the group consisting of Culex vishnui , Culex gelidus , Culex fuscocephala , A edes aegyti and Anopheles stephensi Mosquito larvae insecticidal composition that is a larva.