KR100781191B1 - 2-phenyl-4h-chromen-4-one and their use as nematocides - Google Patents

2-phenyl-4h-chromen-4-one and their use as nematocides Download PDF

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KR100781191B1
KR100781191B1 KR1020070003555A KR20070003555A KR100781191B1 KR 100781191 B1 KR100781191 B1 KR 100781191B1 KR 1020070003555 A KR1020070003555 A KR 1020070003555A KR 20070003555 A KR20070003555 A KR 20070003555A KR 100781191 B1 KR100781191 B1 KR 100781191B1
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심용희
백융기
임융호
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건국대학교 산학협력단
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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/14—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings
    • A01N43/16—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings with oxygen as the ring hetero atom
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    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
    • C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
    • C07D311/28—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only

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Abstract

A composition comprising 2-phenyl-4H-chromen-4-one is provided to show the nematocidal activity on B. xylophilus by influencing on the growth of a germ and a larva of nematoda and gamete proliferation, thereby being usefully used as a nematocide. A nematocide having the activity of killing B. xylophilus comprises a compound represented by the formula(1) or a pharmaceutically acceptable salt thereof as an effective ingredient, wherein 100-150 ml of the compound having a concentration of 0.1mM as an effective amount is administered to nematoda.

Description

소나무 재선충에 대해 치사 효과를 나타내는 화합물 2-페닐-4에이치-크로멘-4-온 및 살선충제로서의 용도 {2-Phenyl-4H-chromen-4-one and their use as nematocides} Compound 2-Phenyl-4H-chromen-4-one and its use as nematocides with a lethal effect on pine re-nematodes {2-Phenyl-4H-chromen-4-one and their use as nematocides}

도 1 은 본 발명에 따른 2-페닐-4에이치-크로멘-4-온의 구조를 나타낸 것이다.1 shows the structure of 2-phenyl-4H-chromen-4-one according to the present invention.

도 2 는 본 발명에 따른 2-페닐-4에이치-크로멘-4-온의 농도별 선충 치사율을 나타낸 것이다.Figure 2 shows nematode mortality according to the concentration of 2-phenyl-4H-chromen-4-one according to the present invention.

본 발명은 하기 화학식 1을 갖는 화합물 또는 약학적으로 허용 가능한 그의 염을 유효 성분으로 하는 소나무 재선충(B. xylophilus)에 대한 살선충제 및 그의 살선충제로서의 용도에 관한 것이다.The present invention relates to nematicides against pine bar nematodes (B. xylophilus) and their use as nematicides, comprising as an active ingredient a compound having the formula (1) or a pharmaceutically acceptable salt thereof.

[화학식 1][Formula 1]

Figure 112007003089135-pat00002
Figure 112007003089135-pat00002

소나무재선충은 소나무 에이즈로 불릴 만큼 확산속도나 치료가 어려운 질병 중 하나로, 1988년 부산에서 시작되어 10여년 만에 경북지역까지 확산되었다. 재선충은 솔수염하늘소를 매개로 하여 감염 1년 만에 99.9%의 소나무가 말라죽게 한다.Pine reptiles are one of the diseases that are difficult to spread or cure enough to be called pine AIDS. It started in Busan in 1988 and spread to Gyeongbuk in 10 years. Re-nematodes, mediated by the beetles, kill 99.9% of pines after one year of infection.

20세기 초 일본과 미국에서 시작된 재선충은 국제교역의 증대로 세계로 확산되었고, 일단 재선충에 감염된 소나무는 강도가 떨어지기 때문에 목재로서의 활용도 어려운 실정이다.Re-nematodes, which originated in Japan and the United States in the early twentieth century, have spread to the world through increased international trade, and pine trees infected with re-nematodes are less likely to be used as timber.

재선충은 1 ㎜ 이하의 크기를 가지며, 약 3주 만에 20만 마리로 번식하는 엄청난 번식력을 갖고 있다. 소나무에서 재선충은 수관에 기생하기 때문에 수관을 통한 물과 양분의 이동이 어렵게 되어 소나무가 고사하게 되고, 소나무 속의 재선충은 솔수염하늘소의 유충을 통해 번데기를 거쳐 솔수염하늘소 몸속으로 이동하여 다른 소나무로 전염된다. Reptiles are less than 1 mm in size and have a tremendous breeding capacity of 200,000 in about three weeks. In the pine, re-nematodes are parasitic in the water pipes, which makes it difficult for the water and nutrients to move through the water pipes, and the pines die. It is transmitted.

현재 사용 중인 재선충 살충제인 메타소디움은 고가인 관계로 사용에 많은 어려움이 있으며, 소나무에 살선충제를 주사하는데도 문제가 있다. 따라서, 새로운 재선충 살선충제의 개발이 필요한 실정이다.Metasodium, which is currently being used as a nematode insecticide, is expensive and has a lot of difficulties in use, and there is also a problem of injecting an insecticide into pine trees. Therefore, the development of a new worm nematode nematode is required.

이에 본 발명자들은 소나무 재선충으로부터 소나무를 보호할 수 있는 살선충제를 개발하고자 예의 노력한 결과, 2-페닐-4에이치-크로멘-4-온이 소나무 재선충의 일생 중 배아 및 유충 성장과 생식세포 증식에 영향을 주어 선충을 효과적으로 치사시키는 것을 확인하고 본 발명을 완성하였다. Therefore, the present inventors have made efforts to develop a nematicide that can protect pine from pine re-nematode. As a result, 2-phenyl-4H-chromen-4-one is used for embryonic and larval growth and germ cell proliferation during the life of pine re-nematode. Influenced to confirm that effectively killing nematodes and completed the present invention.

따라서, 본 발명의 주된 목적은 소나무 재선충에 대해 치사 효과를 나타내는 화합물 2-페닐-4에이치-크로멘-4-온 (2-Phenyl-4H-chromen-4-one)을 제공하는데 있다.Therefore, the main object of the present invention is to provide a compound 2-phenyl-4H-chromen-4-one which has a lethal effect on pine re-nematode.

또한, 본 발명의 다른 목적은 상기 화합물을 유효 성분으로 포함하되, 소나무 재선충을 치사시키는 살선충제를 제공하는데 있다.In addition, another object of the present invention is to provide an nematicide that includes the compound as an active ingredient, killing pine re-nematode.

또한, 본 발명의 또 다른 목적은 상기 화학물을 유효 성분으로 포함하고, 소나무 재선충을 치사시키는 살선충제의 조성물을 제공하는데 있다.In addition, another object of the present invention is to provide a composition of the nematicidal agent containing the chemical as an active ingredient and killing pine re-nematode.

또한, 본 발명의 또 다른 목적은 본 발명에 따른 2-페닐-4에이치-크로멘-4-온의 소나무 재선충을 치사시키는 살선충제로서의 용도를 제공하는데 있다. Still another object of the present invention is to provide a use as an nematicide for killing pine re nematodes of 2-phenyl-4H-chromen-4-one according to the present invention.

이에 상기의 목적을 이루기 위해 본 발명은 소나무 재선충에 대해 치사 효과를 나타내는 화학식 1 을 갖는 화합물 2-페닐-4에이치-크로멘-4-온 (2-Phenyl-4H-chromen-4-one)을 제공한다.In order to achieve the above object, the present invention provides a compound 2-phenyl-4H-chromen-4-one (2-Phenyl-4H-chromen-4-one) having the formula 1 showing a lethal effect on pine re-nematode. to provide.

[화학식 1][Formula 1]

Figure 112007003089135-pat00003
Figure 112007003089135-pat00003

또한, 본 발명은 상기의 화학식 1 을 갖는 화합물 또는 약학적으로 허용 가능한 그의 염을 유효성분으로 포함하되, 소나무 재선충을 치사시키는 살선충제를 제공한다.In addition, the present invention includes a compound having the formula (1) or a pharmaceutically acceptable salt thereof as an active ingredient, and provides an nematicide to kill pine re-nematode.

상기 화합물의 약학적으로 허용 가능한 염의 예로는 염산, 황산, 인산 등의 무기염 및 수산, 푸마르산, 말레인산, 능금산, 구연산, 주석산, 글루탐산 등의 유기염 등 약학적으로 허용할 수 있는 산부가염을 들 수 있다.Examples of pharmaceutically acceptable salts of the compounds include pharmaceutically acceptable acid addition salts such as inorganic salts such as hydrochloric acid, sulfuric acid, phosphoric acid, and organic salts such as hydroxyl acid, fumaric acid, maleic acid, neumum acid, citric acid, tartaric acid, and glutamic acid. Can be.

본 발명은 또한, 상기 화학식 1 의 화합물 또는 약학적으로 허용 가능한 그 염을 유효 성분으로 포함하고, 소나무 재선충을 치사시키는 살선충제용 조성물을 제공한다.The present invention also provides a nematicide composition comprising the compound of Formula 1 or a pharmaceutically acceptable salt thereof as an active ingredient and killing pine re-nematodes.

상기 조성물은 선충에 대해서 0.1 mM 농도 100 ~ 150 ㎖ 범위의 유효량으로 포함하는 것이 바람직하며, 투여는 하루에 한번 투여할 수도 있고, 수회 나누어 투여할 수도 있다.The composition is preferably included in an effective amount in the range of 100 ~ 150 mL 0.1 mM concentration to the nematode, the administration may be administered once a day, may be administered several times divided.

또한, 본 발명은 상기 화학식 1 을 갖는 화합물을 사용하는 소나무 재선충을 치사시키는 살선충 방법을 제공한다.In addition, the present invention provides a nematicidal method for killing pine re-nematode using the compound having the formula (1).

이하, 본 발명을 하기 실시예에 의거하여 보다 구체적으로 설명한다. 이들 실시예는 오로지 본 발명을 예시하기 위한 것으로서, 본 발명의 범위가 이들 실시예에 의해 제한되는 것으로 해석되지는 않는 것은 당업계에서 통상의 지식을 가진 자에게 있어서 자명할 것이다.Hereinafter, the present invention will be described in more detail based on the following examples. These examples are only for illustrating the present invention, it will be apparent to those skilled in the art that the scope of the present invention is not to be construed as being limited by these examples.

실시예. 생존률에 미치는 효과 확인Example. Identify effects on survival

본 발명은 소나무 재선충에 대한 2-페닐-4에이치-크로멘-4-온이 배아 및 유충 성장과 생식세포 증식에 미치는 영향을 관찰하기 위하여, 소나무재선충에 스크리닝을 하였다. In order to observe the effect of 2-phenyl-4H-chromen-4-one on pineal worm nematode on embryonic and larval growth and germ cell proliferation, the pineal nematode was screened.

2-페닐-4에이치-크로멘-4-온을 디메틸설폭사이드(DMSO; dimethyl sulfoxide)에 녹여 1 M로 저장액을 만든 후 각 농도별로 희석하고, 소나무재선충과 2-페닐-4에이치-크로멘-4-온을 96 웰 플레이트에 분주를 하였다. 2-phenyl-4H-chromen-4-one was dissolved in dimethyl sulfoxide (DMSO) to make a stock solution at 1 M, and then diluted at each concentration. Men-4-one was dispensed into 96 well plates.

이때, 2-페닐-4에이치-크로멘-4-온의 최종 농도는 10, 2, 1, 0.1, 0.01, 0.001 mM가 되게 하였으며, 분주가 끝난 뒤, 6시간 동안 25℃에서 배양을 하였다. 6시간 후 샘플에서 20 ㎕씩 채취해 소나무 재선충 전체 수와 살아있는 수, 죽은 수를 각각 세었다. 이중 50% 이상 죽은 경우에는 50% 치사율(IC50)을 측정하였고, 그 결과를 도 2에 명시하였다.At this time, the final concentration of 2-phenyl-4H-chromen-4-one was 10, 2, 1, 0.1, 0.01, 0.001 mM, and after the dispensing, incubated at 25 ℃ for 6 hours. Six hours later, 20 μl were taken from the sample and the total number of pine re-nematodes, live and dead were counted, respectively. 50% mortality (IC50) was measured when more than 50% died, and the results are shown in FIG. 2.

도 2에서 보는 바와 같이, 2 mM의 2-페닐-4에이치-크로멘-4-온 농도에서 치사율(morality rate)이 100%에 달했으며, IC50(50% 치사율)은 0.0982 mM임을 확인 되었다(표 1 참조).As shown in FIG. 2, mortality rate reached 100% at a concentration of 2-phenyl-4H-chromen-4-one at 2 mM, and an IC50 (50% mortality rate) was 0.0982 mM (Table 1). 1).

따라서, 본 발명의 2-페닐-4에이치-크로멘-4-온을 소나무 재선충에 처리할 경우, 선충의 치사율이 100%에 이르러 살선충제로서의 효과가 매우 우수함을 확인하였다. Therefore, when the 2-phenyl-4H-chromen-4-one of the present invention was treated with pine re-nematode, it was confirmed that the nematode mortality reached 100%, which was very excellent as an nematicide.

[표 1]TABLE 1

선충의 IC50 치사 농도Nematode IC50 Lethal Concentration

IC50(mM)IC50 (mM) 2-페닐-4에이치-크로멘-4-온2-phenyl-4H-chromen-4-one 0.09820.0982

이상 설명한 바와 같이, 본 발명에 따른 2-페닐-4에이치-크로멘-4-온 (2-Phenyl-4H-chromen-4-one)은 소나무 재선충을 치사시키는 활성을 갖는 살선충 특성을 나타내므로 살선충제로서 유용하게 사용될 수 있다.As described above, 2-phenyl-4H-chromen-4-one according to the present invention exhibits nematicidal properties having the activity of killing pine re-nematodes. It can be usefully used as an nematicide.

Claims (3)

하기의 화학식 1 을 갖는 화합물 또는 약학적으로 허용 가능한 그의 염을 유효성분으로 포함하되, 소나무 재선충(B. xylophilus)을 치사시키는데 활성을 갖는 살선충제.An nematicide comprising a compound having the formula 1 or a pharmaceutically acceptable salt thereof as an active ingredient, and having an activity to kill B. xylophilus. [화학식 1][Formula 1]
Figure 112007003089135-pat00004
Figure 112007003089135-pat00004
 상기 화학식 1 을 갖는 화합물 또는 약학적으로 허용 가능한 그의 염을 유효성분으로 포함하는 소나무 재선충(B. xylophilus)의 살선충제 조성물.An nematicide composition of pine bar nematode (B. xylophilus) comprising the compound of Formula 1 or a pharmaceutically acceptable salt thereof as an active ingredient. 상기 화학식 1 을 갖는 화합물을 사용하는 소나무 재선충(B. xylophilus)의 살선충 방법.Nematode method of pine re-nematode (B. xylophilus) using the compound having the formula (1).
KR1020070003555A 2007-01-12 2007-01-12 2-phenyl-4h-chromen-4-one and their use as nematocides KR100781191B1 (en)

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JPH08225409A (en) * 1995-02-21 1996-09-03 Kobe Steel Ltd Agent and coating for controlling attachment of underwater organism
JPH11116564A (en) 1997-10-09 1999-04-27 Otsuka Chem Co Ltd Chromone derivative
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JP2006069906A (en) 2004-08-31 2006-03-16 Sumitomo Chemical Co Ltd Chromone compound and its use

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH08193078A (en) * 1995-01-12 1996-07-30 Hokko Chem Ind Co Ltd Chromone derivative and agricultural and horticultural germicide
JPH08225409A (en) * 1995-02-21 1996-09-03 Kobe Steel Ltd Agent and coating for controlling attachment of underwater organism
JPH11116564A (en) 1997-10-09 1999-04-27 Otsuka Chem Co Ltd Chromone derivative
KR20000018305A (en) * 1998-09-01 2000-04-06 성재갑 Chromene derivative useful for a cdk inhibitor
JP2006069906A (en) 2004-08-31 2006-03-16 Sumitomo Chemical Co Ltd Chromone compound and its use

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