KR20120039882A - Pesticide composition of insecticidal activity for paddy rice insects - Google Patents

Abstract

PURPOSE: An insecticidal composition against paddy rice insects is provided to ensure excellent insecticidal activity to small brown plant hopper, blown plant hopper, and Sogatella furcifera. CONSTITUTION: An insecticidal composition against paddy rice insets contains Sebastiania corniculata organic solvent extract, 8-hydroxyquinolinie, or 8-hydroxyquinoline derivatives. The organic solvent extract is methanol extract, ethanol extract, hexane extract, or ethyl acetate extract of Sebastiania corniculata. A method for preparing 8-hydroxyquinoline comprises: a step of dipping Sebastiania corniculata in methanol at 20-30°C for 24-72 hours; a step of filtering and concentrating at 40-50°C under a vacuum condition for 6-8 hours to prepare methanol extract; a step of dissolving the methanol extract in 800-1500ml of distilled water and adding 800-1500ml of hexane to separate an aqueous layer and a hexane layer; and a step of adding 800-1500ml of chloroform to the aqueous layer and mixing the aqueous layer and chloroform.

Description

Pesticide composition of insecticidal activity for paddy rice insects}

The present invention relates to an insecticide composition having excellent insecticidal activity against water pests, and more particularly, to Sebastiania corniculata organic solvent extract, 8-Hydroxyquinoline and 8-. The present invention relates to an insecticide composition having excellent pesticidal activity against a water pest including at least one selected from hydroxyquinoline derivatives.

Aemyeolgu (Laodelphax striatellus) belonging to myeolgugwa (Delphacidae), Brown Planthopper (Nilaparvata lugens) and huindeung myeolgu (Sogatella furcifera) is rice, while widely distributed in tropical and subtropical, rice-growing regions, including Korea, as well as damage caused by direct heupjeup Rice It is a major insect pest that causes huge economic losses to rice grain production, as a mediator of rice rot virus such as streaked leaf blight and black streaks (Bae, SH and Pathak, MD 1966. International Rice Research Institute Newsl, 15: 33 Dyck, VA and Thomas, B. 1979. International Rice Research Institute, 3-17; Kim, YK, Lee, JJ, and Choi, MY 2008. Korean Journal of Applied Entomology , 47 (1): 65-74 ).

The emergence of organic synthetic insecticides after World War II marked a major turning point in two aspects: increased crops by agricultural pest control and improved human health by sanitary pest control.

Insecticides used for pest control in Korea are increasing every year, of which organophosphorus and carbamate account for about 90% of total consumption. However, decades of abuse and abuse of these existing organic synthetic pesticides have caused a number of side effects such as the emergence of resistant pests, toxic toxicity, disturbance of biological control by natural enemies, residual poisoning and environmental pollution. Therefore, as interest in the side effects and environmental effects of such synthetic insecticides increases, the use of synthetic insecticides is gradually limited (Brown, A. W. A. and Pal, R. 1971. Insecticide resistance in arthropods. World Health Organization, Geneva).

Recently, with increasing interest in food safety and the natural environment, the use of pesticides in food production is recognized as an act of destroying human health and the environment. Recently, researches on alternative pesticides that have a wide range of pesticidal effects and are harmless to humans and do not have a significant environmental impact have been actively conducted (Schrmutterer, H. 1980. Procedure 1st International Neem Conference. 33-59; Kim, YK). , Lee, JJ, and Choi, MY 2008. Korean Journal of Applied Entomology , 47 (1): 65-74).

In this respect the plant can be used as a very useful pest control agent. It can be used more safely than chemical control methods because various secondary metabolites contained in plants selectively act only on restricted species and are easily decomposed into non-toxic compounds and can be used as an integrated pest control (IPM) source. Therefore, many researches have been made on plant-derived materials having excellent value as pest control agents. In addition, many studies have shown that terpene and alkaloid compounds have insecticidal properties. Especially, ricninine, an alkaloid present in the leaves of Ricinus communis , has strong insecticidal activity against rice plant. Harborne, JB 1993. Introduction to ecological biochemistry (4th edition) .Academic Press, London; Thornber, CW 1970. Phytochemistry , 9: 157-187.

Korean Patent Publication No. 10-0034853 (Pesticide Insecticide Composition) has a pesticidal effect on aquatic pests comprising ginkgo biloba A, B, C, bilobalide and derivatives thereof derived from ginkgo biloba leaves. It is disclosed about pesticides having.

Also, Kwon (1993) [Kwon Min. 1993. Isolation and Identification of Insecticides from the Leaves of Ginkgo biloba L. According to the master's thesis of Seoul National University], mutagenicity test was performed on bilobalide, a ginkgo leaf-derived terpene compound, which has been reported to exhibit strong insecticidal activity against rice plant. .

Therefore, many researches have been made to develop new eco-friendly insecticides that can replace the existing insecticides without harming the environment, harming the human body, while killing water pests that damage water crops.

An object of the present invention is to provide a pesticide composition having pesticidal activity against such insect pests by studying a compound that is harmless to the human body and has a selective pesticidal activity against a water pest in order to solve the problems of the synthetic insecticide.

In another aspect, the present invention is any one selected from plant extracts having insecticidal activity against aquatic pests such as anchovy, rice plant and white locust, quinoline compound and derivatives of the quinoline compound obtained from the plant extract having the insecticidal activity It is intended to provide pesticide compositions comprising at least one species.

The present invention is an organic solvent extract of Sebastiania corniculata as a plant extract having insecticidal activity against aquatic pests such as anchovy, rice locust and white locust, the Sebastiania corniculata organic It is possible to provide a pesticide composition having excellent insecticidal activity against aquatic pests including any one or more selected from 8-hydroxyquinolline and 8-hydroxyquinolline derivatives obtained from a solvent extract. .

Sebastiania corniculata organic solvent extract of the present invention, 8-hydroxyquinoline (8-Hydroxyquinoline) obtained from the Sebastiania corniculata organic solvent extract and Insecticide compositions having excellent insecticidal activity against aquatic pests including any one or more selected from 8-hydroxyquinoline derivatives exhibit excellent pesticidal activity against aquatic pests such as larvae, rice larvae and white larvae. In particular, plant-derived 8-hydroxyquinolones, as well as derivatives thereof, isoquinolones, 4-methylquinololines, 6-methylquinololines, 8-hydroxy-2-methylquinololines and 6- Methoxyquinolane can also be used as a pesticide for insect pests that exhibit the most excellent activity against water pests such as larvae, rice larvae and white larvae, and can compensate for the disadvantages of existing synthetic insecticides.

Meanwhile, in the present invention, 8-hydroxyquinolin, isoquinolin, 4-methylquinolin, 6-methylquinolin, and 8-hydroxy-2-methylquinola having high insecticidal activity against aquatic pests. Phosphorus and 6-methoxyquinololine can be used as lead compounds to develop new compounds with higher pesticidal activity and effects on various layers by modifying the chemical structure based on the structure of each component. Therefore, pesticides using these parent nucleus compounds can be applied to various kinds of pest control.

FIG. 1 is an EI-MS graph showing that the chloroform fraction of the Sebastianic Corniculata methanol extract obtained in Example (2) is 8-Hydroxyquinoline of Formula (1).
FIG. 2 is a ¹ H-NMR graph showing that the chloroform fraction of the Sebastianic Corniculata methanol extract obtained in Example (2) is 8-Hydroxyquinoline of Formula (1) .
FIG. 3 is a ¹³ C-NMR graph showing that the chloroform fraction of the Sebastianic Corniculata methanol extract obtained in Example (2) is 8-Hydroxyquinoline of Formula (1) .

The present invention shows a pesticide composition having excellent pesticidal activity against water pests.

The present invention is directed to a sesame pest comprising at least one selected from Sebastiania corniculata organic solvent extract, 8-Hydroxyquinoline and 8-Hydroxyquinoline derivatives. An insecticide composition having good pesticidal activity is shown.

The sebastian corniculata organic solvent extract refers to the sebastian corniculata methanol extract obtained by extracting sebastian corniculata with a methanol solvent.

The sebastian corniculata organic solvent extract refers to the sebastian corniculata ethanol extract obtained by extracting sebastian corniculata with an ethanol solvent.

The sebastian corniculata organic solvent extract refers to the sebastian corniculata hexane extract obtained by extracting sebastian corniculata with a hexane solvent.

The sebastian corniculata organic solvent extract refers to the sebastian corniculata ethyl acetate extract obtained by extracting sebastian corniculata with an ethyl acetate solvent.

In the above 8-hydroxyquinoline can be used that obtained by fractionating the sebastian corniculata methanol extract with chloroform (chloroform).

The 8-hydroxyquinolin is the step of obtaining a methanol extract by extracting Sebastiania corniculata with methanol; The Sebastian corniculata methanol extract may be obtained by fractionation with chloroform.

In the above 8-hydroxyquinololine, sebastian coniculata is added to 2-5 times the amount of methanol relative to the weight of sebastian conniculata, soaked at 20-30 DEG C for 24 to 72 hours, and then filtered. Filtrating to obtain a filtrate and concentrating the filtrate under reduced pressure for 6-8 hours at 40-50 ° C. and vacuum to obtain a methanol extract; After dissolving the Sebastian cornicula methanol extract in 800-1500 ml of distilled water, pour 800-1500 ml of hexane and mixing it to mix well with the distilled water and hexane of the Sebastian corniculata methanol extract. Separating the water layer and the hexane layer; The chloroform 800 ~ 1500ml is poured into the water layer and mixed to mix the water layer and chloroform well, and the water layer and the chloroform layer can be obtained as a chloroform layer fraction obtained by separating the water layer and the chloroform layer.

In the above 8-hydroxyquinololine, sebastian coniculata is added to 2-5 times the amount of methanol relative to the weight of sebastian conniculata, soaked at 20-30 DEG C for 24 to 72 hours, and then filtered. Filtrating to obtain a filtrate and concentrating the filtrate under reduced pressure for 6-8 hours at 40-50 ° C. and vacuum to obtain a methanol extract; Methanol extract of Sebastian corniculata was dissolved in 800-1500 ml of distilled water and placed in a 2,000-10,000 ml aliquot, followed by 800-1500 ml of hexane. Mixing to mix well with distilled water and hexane and separating into a water layer and a hexane layer to obtain a hexane layer fraction; The remaining water layer may be poured into chloroform 800-1500ml, mixed to mix the water layer and chloroform well, and then separated from the water layer and the chloroform layer to obtain a chloroform layer fraction.

In the step of obtaining the methanol extract of Sebastian cornicula sebastian cornicula may be used to dry for 24 to 48 hours in the shade and then pulverized to 10-100 mesh (mesh).

As the 8-hydroxyquinoline derivatives, derivatives of 8-hydroxyquinolane represented by the following general formula (1) may be used, and isoquinolane represented by the following general formulas (2) to (6) ( Isoquinoline] [See Formula (2)], 4-Methylquinoline [See Formula (3)], 6-Methylquinoline [See Formula (4)], 8- Any one selected from 8-Hydroxy-2-methylquinoline (see formula (5)) and 6-methoxyquinoline (see formula (6)) Can be used.

...화학식(1)

... Formula (1)

...화학식(2)

... Formula (2)

...화학식(3)

... Formula (3)

...화학식(4)

... Formula (4)

...화학식(5)

... Formula (5)

...화학식(6)

... Formula (6)

Isoquinoline (see Formula (2)), 4-Methylquinoline (see Formula (3)), 6-methylquine, which is a derivative of 8-hydroxyquinololine. 6-Methylquinoline [see Formula (4)], 8-Hydroxy-2-methylquinoline [See Formula (5)] and 6-methoxyquinoline (6-Methoxyquinoline) [Refer Formula (6)] can be used commercially available.

Insect pests represent Laodelphax striatellus .

Insect pests refer to Nilaparvata lugens .

Water pests represent Sogatella furcifera .

In the pest may represent any combination of two or more selected from aemyeolgu (Laodelphax striatellus), Brown Planthopper (Nilaparvata lugens) and huindeung myeolgu (Sogatella furcifera).

Insecticide composition of the present invention is in accordance with the application method, the application site, the hydrating agent, liquid, emulsion, liquid hydrating agent, granules, powders, granules, capsules, fine powder, suspending agent, coating agent, smoke screening agent according to the application method, the application site for insect pests It can be formulated and used in any one or more of the selected forms.

Insecticide composition of the present invention can be used to apply the contact method, the fumigation method and / or digestive poisoning method for water pests, preferably can be used to insect pests using the contact method.

In the above method of contacting the pesticide composition, the insecticide composition may be sprayed directly onto the water pests by spraying to spray the insecticide composition on the water pests to kill the water pests.

In the above method of contacting the pesticide composition, the insecticide composition is formulated with a hydrating agent, a liquid agent, an emulsion and / or a liquid hydrating agent, and then sprayed directly onto the pest with a spray to contact the pesticide composition with the pest, thereby killing the pest. Can be.

According to the pesticide composition having excellent insecticidal activity against the water pest of the present invention under various conditions, in order to achieve the object of the present invention, it is desirable to provide an insecticide composition having excellent insecticidal activity to the insect pest under the above-mentioned conditions. desirable.

The present invention includes a pesticidal pesticide containing the pesticide composition mentioned above.

The present invention includes a pesticide insecticide in which the pesticide composition mentioned above contains 1 to 10% by weight based on the total weight of the pesticide.

In the present invention, the above-described insecticide composition may contain 1 to 10% by weight of the total pesticide, and 90 to 99% by weight of any one or more excipients selected from neutralization, carrier, and synergist. Include pest pesticides. At this time, the excipient is usually used as a component used in the preparation of the pesticide, so if those skilled in the art can be used properly selected, detailed description thereof will be omitted below.

Hereinafter, the present invention will be described in detail with reference to Examples and Test Examples. However, these are for the purpose of illustrating the present invention in more detail, and the scope of the present invention is not limited thereto.

Example 1 Insecticidal Compounds of the Sebastianic Corniculata Methanol Extract

Preparation of Sebastian Corniculata Methanol Extract

Sebastiania corniculata was dried in the shade for 24 hours and then ground to 50 mesh.

6 kg of the crushed Sebastian corniculata was added to 15 kg of methanol, immersed at 25 ± 2 ° C. for 48 hours, and then filtered through a filter paper (Toyofilter paper No. 2, Toyo Roshi, Japan) to obtain a filtrate. The filtrate was concentrated under reduced pressure at 45 ° C. and vacuum for 6 to 8 hours to obtain a sebastian corniculata methanol extract.

Example 2 Preparation of Solvent Fraction of Sebastian Corniculata Methanol Extract

(1) Preparation of Hexane Fraction of Sebastian Corniculata Methanol Extract

Dissolve 20 g of Sebastian corniculata methanol extract obtained in Example 1 in 800 mL of distilled water, and place it in a 3,000 mL aliquot, and then pour 800 mL of hexane (SEC) in order to dissolve the Sebastian extract and the solvent distilled water. And the mixture was mixed well with hexane and then separated into a water layer and a hexane layer to obtain a hexane fraction (hexane fraction).

(2) Preparation of Chloroform Fraction of Methanol Extract of Sebastian Corniculata

Dissolve 20 g of the sebastian corniculata methanol extract obtained in Example 1 in 800 ml of distilled water and place it in a 3,000 ml aliquot, and then pour 800 ml of hexane to extract methanol and the solvent, distilled water. And the mixture was mixed well with hexane and then separated into a water layer and a hexane layer to obtain a hexane layer fraction. 800 ml of chloroform was poured into the remaining water layer, the water layer and chloroform were mixed well, and the water layer and the chloroform layer were separated to obtain a chloroform fraction.

The chloroform fraction of the sebastian corniculata methanol extract obtained above was examined by EI-MS, ¹ H-NMR and ¹³ C-NMR to obtain the following results (see FIGS. 1, 2 and 3). The chloroform fraction of the Sebastian corniculata methanol extract was found to be 8-Hydroxyquinoline of formula (1).

EI-MS (70 eV) m / z (% relative intensity): M ⁺ 145 (100), 144 (2), 117 (85), 116 (14), 90 (7), 89 (6);

¹ H-NMR (CD ₃ OD, 400 MHz): 8.75-8.76 (1H, m, J = 5.84 Hz, H-2), 8.20-8.22 (1H, m, J = 10 Hz, H-4), 7.42- 7.46 (1H, m, J = 17.8 Hz, H-5), 7.38-7.40 (1H, d, J = 7.6 Hz, H-3), 7.32-7.34 (1H, m, J = 9.52 Hz, H-6 ), 7.07-7.10 (1H, m, J = 8.8 Hz, H-7), 5.42 (OH, s, H-8)

¹³ C-NMR (CD ₃ OD, 100MHz): 152.7 (C-8), 150.3 (C-2), 138.8 (C-9), 135.3 (C-4), 129.0 (C-10), 126.2 (C -6), 121.3 (C-3), 120.3 (C-5), 112.0 (C-7)

...화학식(1)

... Formula (1)

(3) Preparation of Ethyl Acetate Fraction of Methanol Extract of Sebastian Corniculata

Dissolve 20 g of Sebastian corniculata methanol extract obtained in Example 1 in 800 mL of distilled water, and place it in a 3,000 mL aliquot, and then pour 800 mL of hexane (SEC) in order to dissolve the Sebastian extract and the solvent distilled water. And the mixture was mixed well with hexane and then separated into a water layer and a hexane layer to obtain a hexane layer fraction. 800 ml of chloroform was poured into the remaining water layer and mixed to mix the water layer and chloroform well, and then the water layer and the chloroform layer were separated to obtain a chloroform layer fraction. 800 ml of ethyl acetate was poured into the remaining water layer, and the mixture was mixed with the water layer and ethyl acetate. Then, the water layer and the ethyl acetate layer were separated to obtain an ethyl acetate layer fraction.

(4) Preparation of Butanol Fraction of Sebastian Corniculata Methanol Extract

Dissolve 20 g of Sebastian corniculata methanol extract obtained in Example 1 in 800 mL of distilled water, and place it in a 3,000 mL aliquot, and then pour 800 mL of hexane (SEC) in order to dissolve the Sebastian extract and the solvent distilled water. And the mixture was mixed well with hexane and then separated into a water layer and a hexane layer to obtain a hexane layer fraction. 800 ml of chloroform was poured into the remaining water layer, the water layer and chloroform were mixed well, and the water layer and the chloroform layer were separated to obtain a chloroform layer fraction. 800 ml of ethyl acetate was poured into the remaining water layer, and the mixture was mixed with the water layer and ethyl acetate. Then, the water layer and the ethyl acetate layer were separated to obtain an ethyl acetate layer fraction. 800 mL of butanol was poured into the remaining water layer, followed by mixing the water layer and the butanol layer to obtain a butanol fraction.

(5) Preparation of Water Fraction of Sebastian Corniculata Methanol Extract

20 g of the sebastian corniculata methanol extract obtained in Example 1 was dissolved in 800 ml of distilled water and placed in a 3,000 ml aliquot, followed by 800 ml of hexane (hexane). The mixture was mixed well with distilled water and hexane and then separated into a water layer and a hexane layer to obtain a hexane layer fraction. 800 ml of chloroform was poured into the remaining water layer, the water layer and chloroform were mixed well, and the water layer and the chloroform layer were separated to obtain a chloroform layer fraction. 800 ml of ethyl acetate was poured into the remaining water layer, and the mixture was mixed with the water layer and ethyl acetate. Then, the water layer and the ethyl acetate layer were separated to obtain an ethyl acetate layer fraction. 800 mL of butanol was poured into the remaining water layer, followed by mixing the water layer and the butanol layer to obtain a butanol fraction. The remaining water layer was concentrated under reduced pressure at 55 ° C. for 6-8 hours, preferably 7 hours, using a rotary vacuum concentrator to obtain a water fraction.

Test Example 1 Pesticide Insecticidal Activity Assay for Methanol Extracts and Fractions of Sebastian Corniculata

(1) water pests used in insecticidal activity assays

The three kinds may pests of aemyeolgu (Laodelphax striatellus), Brown Planthopper (Nilaparvata lugens) and huindeung myeolgu (Sogatella furcifera) used in the present invention was used to breed successive generations without selection with any pesticide, it is primarily the chucheongbyeo (Oryza sativa L.), and seedling seedlings 14 days or more after sowing were planted in small pots, and then inoculated with three kinds of water pests, and then placed in plastic breeding boxes filled with water. At this time, the breeding conditions of the breeding room were bred under the conditions of a temperature of 27 ° C., a humidity of 65%, and a light condition of 16: 8 (day: night).

(2) Insecticidal activity test of aquatic pests

Insecticidal activity assay for rice hoppers was performed by anesthetizing 20 adult females (7 days after allegory) with carbon dioxide for 20 seconds, and then using a Burkard hand microapplicator (UK) on the thoracic ventricle with an initial concentration of 100 ㎍ in acetone. Diluted and used, all samples were treated with 0.2 μl per water pest. Only 0.2 μl acetone was grafted without treatment.

Insecticidal assays of larvae and white larvae were also treated with 0.1 μl of the sample diluted at each concentration in the same way as above, and the treated worms were placed in a plastic cage 6.5 cm in diameter and 30 cm high. A lid was put on to prevent each pest from escaping. Larvae were examined after 24 hours, 48 hours or 72 hours, and all experiments were conducted in three replicates for each sample. Pesticide results were compared by analysis of variance and Duncan's multiple test (SAS Institute, 1998).

In Table 1 below, the 95% confidence zone represents a 95% probability that the results can be relied upon, and the adult extracts of the plants using the microlocalization method and for the adult females of the rice larvae, larvae and whites larvae for each fraction. Insecticidal activity was expressed as LD ₅₀ (half dose).

Insecticidal Activity against Methanol Extracts and Fractions of Sebastian Corniculata sample Notification LD ₅₀ (μg / female adult) 95% confidence Methanol extract Annihilation 11.15 10.94-11.32 A light bulb 15.64 14.95-16.86 White Lantern 13.89 13.24-14.36 Hexane fraction Annihilation - - A light bulb - - White Lantern - - Chloroform fraction Annihilation 1.09 0.86-1.43 A light bulb 4.46 4.07-4.89 White Lantern 2.32 1.89-2.67 Ethyl acetate fraction Annihilation 59.89 58.26-61.33 A light bulb 78.23 77.29-80.13 White Lantern 75.57 73.19-77.86 Buntanol fraction Annihilation - - A light bulb - - White Lantern - - Water fraction Annihilation - - A light bulb - - White Lantern - -

* In Table 1, "-" indicates that the insecticidal activity was not shown.

* The methanol extract in the sample of Table 1 refers to the sebastian corniculata methanol extract obtained in Example 1, and the hexane fraction to the water fraction refer to the respective solvents in (1) to (5) of Example 2. Each solvent fraction for the Sebastian corniculata methanol extract obtained.

In Table 1, the semi-lethal concentration of the Sebastian extract of Corniculta methanol was 11.15 µg for adult adult larvae after 48 hours of treatment, 15.64 µg per adult adult larvae, and 13.89 µg for white larvae female adult. From the above results, it can be seen that the methanol extract of Sebastian corniculata exhibits high insecticidal activity against three types of water pests of anchovy, rice locust and white locust.

Therefore, the hexane fraction, chloroform fraction, ethyl acetate fraction, butanol fraction and water fraction of methanol extracts of sebastian corniculata showed excellent insecticidal properties. As a result, the chloroform fraction showed 1.09 ug of female larvae, 4.46 ug of female larvae and 2.32 ug of white larvae females. In addition, ethyl acetate fraction showed 59.89 µg, 78.23 µg, and 75.57 µg activity against three types of water pests, respectively. From the above results, it can be seen that the chloroform fraction of the sebastian corniculata methanol extract exhibits excellent insecticidal activity against three kinds of water pests of anchovy, rice locust and white locust.

However, hexane, butanol and water fractions did not show any pesticidal activity against the three types of water pests.

Test Example 2 Pesticide Insecticidal Activity Assay for 8-hydroxyquinolin and Its Derivatives

8-Hydroxyquinoline obtained from the chloroform fraction of the Sebastian extract of Sebastian corniculata methanol obtained in Example 2, (2) and five 8-hydroxyquinolones (8- Each of the hydroxyquinoline derivatives was treated with the micro-treatment using the method mentioned in (2) of Test Example 1 for each of three types of pests such as larvae, rice larvae, and rare larvae at an initial treatment concentration of 0.5 µg. Insecticidal activity against water pests was investigated and the results are shown in Table 2 below.

The 8-hydroxyquinoline derivatives in the above isoisoquinoline (Isoquinoline) [Formula (2)], 4-Methylquinoline (4-Methylquinoline) [ [Formula (3)]], 6-Methylquinoline (See Formula (4)], 8-Hydroxy-2-methylquinoline (8-Hydroxy-2-methylquinoline) ) And 6-Methoxyquinoline (see Formula (6)), which were purchased from Aldrich, Fluka and Waco.

...화학식(2)

...화학식(3)

... Formula (2)

... Formula (3)

...화학식(4)

...화학식(5)

... Formula (4)

... Formula (5)

...화학식(6)

... Formula (6)

Pesticide Insecticidal Activity against 8-hydroxyquinolin and Its Derivatives compound LD ₅₀ value (µg / Female adult)
(95% confidence)
(Tilt ± standard deviation) Annihilation A light bulb White Lantern 8-hydroxyquinololine 0.0546
(0.0515? 0.0578)
(0.72 ± 0.23) 0.2684
(0.2327? 0.2887)
(1.3 ± 0.23) 0.2159
(0.2032? 0.2243)
(1.4 ± 0.25) Isoquinolane 0.0352
(0.0323? 0.0369)
(0.47 ± 0.22) 0.0862
(0.0835? 0.0896)
(1.6 ± 0.25) 0.0694
(0.0661? 0.0732)
(1.1 ± 0.23) 4-methylquinololine 0.0827
(0.0795? 0.0854)
(1.2 ± 0.25) 0.1628
(0.1585? 0.1659)
(1.2 ± 0.24) 0.1482
(0.1426? 0.1529)
(1.3 ± 0.21) 6-methylquinololine 0.0547
(0.0513? 0.0579)
(1.0 ± 0.23) 0.1209
(0.1183? 0.1246)
(1.5 ± 0.25) 0.1143
(0.1117? 0.1186)
(1.3 ± 0.26) 8-hydroxy-2-methylquinololine 0.1586
(0.1357? 0.1761)
(1.6 ± 0.24) 0.1316
(0.1266? 0.1351)
(1.7 ± 0.27) 0.1256
(0.1219? 0.1286)
(1.2 ± 0.22) 6-methoxyquinololine 0.0462
(0.0415? 0.0488)
(1.1 ± 0.23) 0.0945
(0.0911? 0.0972)
(1.5 ± 0.25) 0.0757
(0.0721? 0.0793)
(1.4 ± 0.26)

In Table 2, 8-hydroxyquinolin, which is a chloroform fraction of the Sebastian extract of Sebastian corniculata, has an LD ₅₀ value of water pests, anchovy, rice locust, and white locust, respectively, at 0.0546 µg, 0.2684 µg per adult adult, and The insecticidal activity of 0.2159 µg was shown.

Derivatives of 8-hydroxyquinoline having a chemical structure similar to that of 8-hydroxyquinololine, which have five quinololine compounds and obtained LD ₅₀ values for larvae in the same manner, isoquinoline The highest activity was 0.0352 [mu] g per female adult, and the sequential order was 0.0462 [mu] g of 6-methoxyquinolline, 0.0547 [mu] g of 6-methylquinolline, 0.0827 [mu] g of 4-methylquinoline, and 8-hydr. Roxy-2-methylquinoline was found in the order of 0.1586 μg. The LD ₅₀ values for the rice hoppers showed the highest activity of isoquinoline at 0.0862 μg per adult, followed by 0.0945 μg of 6-methoxyquinoline and 0.1209 μg of 6-methylquinoline, 8- Insecticidal activity was observed in the order of 0.1316 µg of hydroxy-2-methylquinoline and 0.1628 µg of 4-methylquinoline. In addition, the LD ₅₀ value of the white larvae showed the highest activity of 0.0694 µg per adult adult in isoquinoline, followed by 0.0757 µg of 6-methoxyquinolin and 0.1143 µg of 6-methylquinoline. Hydroxy-2-methylquinololine was 0.1256 µg, and 4-methylquinolinline was 0.1482 µg in order.

<Test Example 3> Stability Data

According to the Hodge and Sterner (1949) classification of acute toxicity, half a lethal dose of 500 to 5,000 mg / kg body weight is a weak toxic substance and 5,000 to 15,000 mg is a substantial non-toxic substance. US Environmental Protection Agency, 1998 In the case of half dose of oral administration, it is classified as weak toxic substance if 500 ~ 5,000mg per kg body weight (Class III) and harmless substance if more than 5,000mg (Class IV).

Insecticidal activity against water pests and 8-hydroxyquinolin, which is the chloroform fraction of the sebastian corniculata methanol extract in Example 2 (2), and the 8-hydroxyquine mentioned in Test Example 2 above Based on material safety data sheets (MSDS) and international papers provided by Sigma & Aldrich to consider the stability of five outstanding quinoline compounds as surprise derivatives It was prepared as, and the half lethal dose (LD ₅₀ ) through the oral toxicity test of the mouse (mouse) is indicated and the results are shown in Table 3 below.

Determination of stability for 8-hydroxyquinolin and its derivatives compound Oral administration Half lethal dose (LD ₅₀ : mg / kg) 8-hydroxyquinololine mouse 1,200 Isoquinolane 615 4-methylquinololine - 6-methylquinololine 800 8-hydroxy-2-methylquinololine 2125-2250 6-methoxyquinololine -

In Table 3, 8-Hydroxyquinoline (8-Hydroxyquinoline), Isoquinoline (Isoquinoline), 6-Methylquinoline (6-Methylquinoline) and 8-hydroxy-2-methylquinoline (8 -Hydroxy-2-methylquinoline) was found to be mildly toxic (low toxicity) with a half lethal dose (LD ₅₀ ) in oral toxicity experiments of mice. 4-Methylquinoline and 4-Methylquinoline (6-Methoxyquinoline) has not yet been reported or confirmed toxicity to a semi-numerical dose, it is indicated as "-" in Table 3.

From the results in Table 3, 8-hydroxyquinolin and its derivatives were able to secure stability in the control of the pests of the rice crops.

While the present invention has been particularly shown and described with reference to exemplary embodiments thereof, it is evident that many alternatives, modifications and variations will be apparent to those skilled in the art without departing from the spirit and scope of the invention as defined by the following claims. It will be understood that the invention may be modified and varied without departing from the scope of the invention.

Sebastiania corniculata organic solvent extract of the present invention, 8-hydroxyquinoline (8-Hydroxyquinoline) obtained from the Sebastiania corniculata organic solvent extract and Insecticide composition having excellent insecticidal activity against aquatic pests including any one or more selected from 8-hydroxyquinoline derivatives exhibits excellent insecticidal activity against aquatic pests such as anthococcus, rice plant and white locust. It can be used as a pesticide for water pests that can be supplemented, so there is industrial applicability.

Claims (8)

Excellent pesticidal activity against water pests including any one or more selected from Sebastiania corniculata organic solvent extract, 8-Hydroxyquinoline and 8-Hydroxyquinoline derivatives Insecticide composition. The method of claim 1,
The sebastian corniculata organic solvent extracts include sebastian corniculata methanol extract, sebastian corniculata ethanol extract, sebastian corniculata hexane extract, sebastian corniculata ethyl acetate Insecticide composition having excellent insecticidal activity, characterized in that any one selected from the extract. The method of claim 1,
8-Hydroxyquinololine was placed in 2 to 5 times methanol by weight of sebastian corniculata and immersed at 20-30 ° C for 24 to 72 hours, followed by filtration. Obtaining a filtrate and concentrating the filtrate under reduced pressure for 6-8 hours at 40-50 ° C. and vacuum to obtain a methanol extract;
After dissolving the Sebastian cornicula methanol extract in 800-1500 ml of distilled water, pour 800-1500 ml of hexane and mixing it to mix well with the distilled water and hexane of the Sebastian corniculata methanol extract. Separating the water layer and the hexane layer;
Insecticide composition having excellent insecticidal activity against water pests, characterized in that the chloroform (800 ~ 1500ml) is poured into the water layer and mixed so that the water layer and chloroform are mixed well, and the water layer and the chloroform layer are separated. . The method of claim 1,
8-hydroxyquinoline derivatives include isoquinoline, 4-methylquinoline, 6-methylquinoline, 8-hydroxy-2-methylqui Insecticide composition having excellent insecticidal activity against water pests, characterized in that any one selected from (8-Hydroxy-2-methylquinoline) and 6-methoxyquinoline (6-Methoxyquinoline). The method of claim 1,
Water insect pests ( Laodelphax striatellus ), rice larvae ( Nilaparvata lugens ) and white larvae ( Sogatella furcifera ) is a pesticide composition having excellent pesticidal activity to the water pest, characterized in that at least one selected from. The method of claim 1,
Pesticide composition is excellent for water pests, characterized in that formulated in any one form selected from hydrating, liquid, emulsion, liquid hydrating, granules, powder, granules, capsules, fine powders, powders, coatings, smokescreens Insecticide composition having insecticidal activity. Claim 1 to 6, pesticide pesticide comprising a pesticide composition of any one selected from claims. 8. The insecticide pesticide of claim 7, wherein the insecticide composition comprises 1 to 10% by weight based on the total weight of the insecticide.

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