KR20060110655A - Chemical compound having acaricidal activity - Google Patents

Chemical compound having acaricidal activity Download PDF

Info

Publication number
KR20060110655A
KR20060110655A KR1020050033127A KR20050033127A KR20060110655A KR 20060110655 A KR20060110655 A KR 20060110655A KR 1020050033127 A KR1020050033127 A KR 1020050033127A KR 20050033127 A KR20050033127 A KR 20050033127A KR 20060110655 A KR20060110655 A KR 20060110655A
Authority
KR
South Korea
Prior art keywords
formula
acaricide
mites
represented
phthalaldehyde
Prior art date
Application number
KR1020050033127A
Other languages
Korean (ko)
Inventor
이회선
Original Assignee
이회선
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 이회선 filed Critical 이회선
Priority to KR1020050033127A priority Critical patent/KR20060110655A/en
Publication of KR20060110655A publication Critical patent/KR20060110655A/en

Links

Classifications

    • 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
    • A01N35/00Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
    • A01N35/02Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical containing aliphatically bound aldehyde or keto groups, or thio analogues thereof; Derivatives thereof, e.g. acetals
    • 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
    • A01N25/00Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/02Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
    • 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
    • A01N25/00Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/02Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
    • A01N25/04Dispersions, emulsions, suspoemulsions, suspension concentrates or gels
    • 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
    • A01N25/00Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/12Powders or granules
    • 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
    • A01N25/00Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/18Vapour or smoke emitting compositions with delayed or sustained release
    • 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
    • A01N25/00Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/20Combustible or heat-generating compositions
    • 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
    • A01N27/00Biocides, pest repellants or attractants, or plant growth regulators containing hydrocarbons
    • 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
    • A01N35/00Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
    • A01N35/04Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical containing aldehyde or keto groups, or thio analogues thereof, directly attached to an aromatic ring system, e.g. acetophenone; Derivatives thereof, e.g. acetals
    • 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
    • A01N35/00Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
    • A01N35/06Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical containing keto or thioketo groups as part of a ring, e.g. cyclohexanone, quinone; Derivatives thereof, e.g. ketals

Abstract

Chemical compounds having acaricidal activity are provided to inhibit growth of Pyroglyphids including Dermatophagoides pteronyssinus and Dermatophagoides farinae Trouessart and Tyrophagus putrescentiae, and improve acaricidal activity and use safety. The acaricidal agent comprises caprylaldehyde represented by the formula(1), 1-naphtaldehydr represented by the formula(2), 2-naphtaldehyde represented by the formula(3), 5,8-dihydroxy-1,4-naphthoquinone represented by the formula(4), naphthalene represented by the formula(5) and phthalaldehyde represented by the formula(6), wherein the acaricidal agent is formulated as liquid, emulsion, ointment, smoking generator, fumigant, particles and solid.

Description

살비성을 나타내는 화합물{CHEMICAL COMPOUND HAVING ACARICIDAL ACTIVITY}Compound which shows acaricide {CHEMICAL COMPOUND HAVING ACARICIDAL ACTIVITY}

본 발명은 살비성 화합물 조성물에 관한 것으로서, 구체적으로 집먼지 진드기와 저장식품 진드기 양쪽에 우수한 살비 활성을 가지는 살비성 화합물에 관한 것이다.The present invention relates to a composition for the acaricidal compound, and more particularly to an acaricidal compound having excellent acaricide activity in both house dust mite and stored food mite.

집먼지 진드기과(pyroglyphid)에 속하는 종중 가장 중요한 종은 세로무늬 먼지진드기(Dermatophagoides pteronyssinus Hughus)와 큰다리 먼지진드기(Dermatophagoides farinae Trouessart)이다. 상기 두 종은 전세계적인 서식 분포를 나타내고, 가정 내 먼지에서 빈번히 관찰되는 주요한 알레르기원으로(Anonymous, 1989, 83,416-427; Anonymous, 1992, Report of a second International Workshop. Journal of Allergy Clinincal Immunology 89: 1046-1060), 특히 천식환자나 노약자가 거주하는 가정 내에서 이들 개체군이 번성하게 되면 질환을 더욱 악화시킬 수 있다.The most important species belonging to the family of pyroglyphids are the Dermatophagoides pteronyssinus Hughus and the Dermatophagoides farinae Trouessart. Both species show a global distribution of habitats and are the major allergens frequently observed in household dust (Anonymous, 1989, 83,416-427; Anonymous, 1992, Report of a second International Workshop.Journal of Allergy Clinincal Immunology 89 : 1046). -1060), especially if these populations thrive in families with asthmatics or the elderly, can make the disease worse.

저장식품 진드기(Tyrophagus putrescentiae)는 식품 저장소나 헛간, 곡물 저장소나 이동소, 건초 및 곡물 가루에 분포하고 있는 저장 곡류해충으로 알려져 있다. 또한 우리나라 가옥 내 집먼지 서식 진드기류 중 제 3의 우점종으로 밝혀짐에 따라 진드기에 오염된 식품을 먹음으로써 발생할 수 있는 질병들, 즉 심한 장염이나 과민증(anaphylaxis) 뿐만 아니라(Hughes, A.M. 1976. The mites of stores food and houses. Technical Bulletin of the ministry of Agriculture, Fisheries and Food 9: 1-400), 천식 및 비염, 결막염, 아토피 피부염 등 각종 알레르기성 질환을 야기하는 원인 항원으로 작용할 가능성이 높아져 연구의 대상이 되고 있다(Woodcock, A.A. and Cunnington, A.M. 1980. The allergenic importance of house dust and storage mites in asthmatics in Brunnei, S.E.Asia.Clin Allergy, 10: 609).Stored Food Mite ( Tyrophagus) putrescentiae ) are known as storage cereal pests found in food storage or barns, grain storage or mobile stations, and hay and grain flour. In addition, as a third dominant species among house dust mites in Korean houses, not only diseases caused by eating food contaminated with ticks, ie severe enteritis or anaphylaxis (Hughes, AM 1976. Technical Bulletin of the Ministry of Agriculture, Fisheries and Food 9 : 1-400), the subject of the study is more likely to act as a causative antigen causing various allergic diseases such as asthma and rhinitis, conjunctivitis, atopic dermatitis (Woodcock, AA and Cunnington, AM 1980. The allergenic importance of house dust and storage mites in asthmatics in Brunnei, SEAsia. Clin Allergy , 10 : 609).

최근에는 중앙난방식 관리 방식을 채용한 아파트 세대가 증가하고 있고, 다양한 형태의 보조 난방 장치가 개발, 사용되고 있으며, 가정 및 사무실 내에서 카펫 이용량이 증가하는 등 주거환경이 변화되면서 진드기 생육에 최적조건을 부여하게 되었다. 이로 인하여 집먼지 진드기는 빠른 증식과 4계절 실내조건 하에서 생존할 수 있게 되었다(Susan M.P. and Ward G.W. Jr, 1987, Immunol. Allergy North Amer 7, 447-461; Pollart S.M., Ward G.W. Jr and Platts-Mills A.E., 1989, Immunol. Allergy Clinics of North America 7: 447-461). In recent years, the number of apartments adopting central heating method is increasing, various types of auxiliary heating systems are being developed and used, and the living conditions are changing, such as the increase of carpet usage in homes and offices. Was given. This allows house dust mites to grow rapidly and survive under four seasons (Susan MP and Ward GW Jr, 1987, Immunol.Allergy North Amer 7, 447-461; Pollart SM, Ward GW Jr and Platts-Mills AE , 1989, Immunol.Allergy Clinics of North America 7 : 447-461).

집먼지 진드기들의 개체군을 감소시키기 위해 현재까지 주로 철저한 청결유지, 건조, 공기 중 상대습도 조절과 같은 물리적 방제와 저장식품 진드기 방제를 위하여 식품변질을 일으키지 않는 메티하이렌 브로마이드(metyhylene bromide)를 이용한 훈연법에 의존하고 있다. In order to reduce the population of dust mites, to date, mainly fume-based methods using methyylene bromide, which do not cause food deterioration, are mainly used for physical control such as thorough cleanliness, drying and control of relative humidity in the air and control of stored food mites. Depends.

현재 상기 집먼지 진드기 및 저장식품 진드기에 대한 화학적 방제를 위한 화 합물로는 γ-BHC, 피리미포스-메틸(pirimiphos-methyl), 벤질 벤조에이트(benzyl benzoate), 디에틸-메타-톨류아마이드(diethyl-m-toluamide; DEET) 및 디부틸 프탈레이트(dibutyl phthalate)가 사용되고 있다(Heller-Haupt A. and Busvine J.R., 1974, Journal of Medical Entomology 11: 551-558).Currently, the compounds for chemical control of house dust mite and stored food mites include γ-BHC, pyrimiphos-methyl, benzyl benzoate, diethyl-meth-tololeamide (diethyl). -m-toluamide (DEET) and dibutyl phthalate are used (Heller-Haupt A. and Busvine JR, 1974, Journal of Medical Entomology 11 : 551-558).

그 중 피리미포스 메틸(pirimiphos-methyl)은 포유 독성이 낮아 저장식품 진드기들을 억제하는 수단으로 실용화되었다. 이에 미첼 등은 피리미포스 메틸이 카페트에 서식하는 진드기 60 %를, 의자에 서식하는 진드기 50 %를 방제할 수 있다고 보고하였다(Mitchell, E.B., Wilkins, S., McCallum Deighton, J. and Platts-Mills, T.A.E. 1985. Reduction of house dust mite allergen levels in the home: use of the acaricide, pirimiphos methyl. Clin . Allergy 15: 234-240).Among them, pirimiphos-methyl has been used as a means of suppressing stored food mites due to its low mammalian toxicity. Mitchell et al. Reported that pyrimifos methyl could control 60% of ticks in carpets and 50% of ticks in chairs (Mitchell, EB, Wilkins, S., McCallum Deighton, J. and Platts-). Mills, TAE 1985. Reduction of house dust mite allergen levels in the home: use of the acaricide, pirimiphos methyl Clin Allergy 15:.. 234-240).

상기한 집먼지 진드기 및 저장식품 진드기를 방제하기 위한 다양한 방제법이 존재함에도 불구하고 물리적 방제법의 어려움과 천연물 방제제의 낮은 살비성으로 인해 기존에 알려진 화합물 중에서 새로운 기능성을 지닌 강력하고 안전한 화합물들을 찾고자 하는 각국의 연구가 활발히 진행되고 있다(Pollart S.M., Ward G.W. Jr and Platts-Mills A.E., 1987, Immunol Allergy Clinics of North America 7: 447-461). Despite the various control methods for controlling the house dust mite and stored food mite, the difficulty of physical control method and low fertilization of natural product control agent in each country to find strong and safe compounds with new functionality among known compounds Research is being actively conducted (Pollart SM, Ward GW Jr and Platts-Mills AE, 1987, Immunol Allergy Clinics of North America 7 : 447- 461).

이러한 측면에서 기존에 알려진 화합물의 집먼지 진드기 및 저장식품 진드기 방제원으로서 새로운 기능을 규명하는 것이 최선책이 될 수 있다. 왜냐하면 기존의 화합물은 다양한 생물활성 물질들이 존재하고 있으며, 이들 화합물 대다수는 안정성이 검증되어 있을 뿐만 아니라 쉽게 생분해할 수 있는 방법이 알려져 있으며, 특정한 목적 충만을 선택적으로 치사시킬 수 있을 뿐만 아니라 집먼지 진드기 및 저장식품 진드기의 종합적방제원으로 이용될 수 있기 때문이다(Namba T., 1993, Hoikusha, Osaka, Japan) 따라서 많은 연구 노력이 상업적인 집먼지 진드기 및 저장식품 진드기 방제원이나 그 선도화합물(lead compound)로서 기존의 알려진 화합물의 새로운 기능을 규명하는데 이용하는데 집중되고 있다. In this respect, it may be best to identify new functions as house dust mite and preserved food mite control of known compounds. Because the existing compounds exist in a variety of bioactive materials, most of these compounds have been proven to be stable and easy to biodegradable, can not only selectively kill the specific purpose filling, but also house dust mites and This is because it can be used as a comprehensive control agent for stored food mites (Namba T., 1993, Hoikusha, Osaka, Japan). Therefore, many research efforts have been carried out as commercial house dust mites and stored food mite control agents or their lead compounds. The focus is on identifying new functions of existing known compounds.

따라서 본 발명은 집먼지 진드기 및 저장식품 진드기에 대하여 살비성을 가지는 화합물을 포함하는 살비제를 제공하는 것을 목적으로 한다.Accordingly, an object of the present invention is to provide an acaricide comprising a compound having acaricide property against house dust mites and stored food mites.

상기한 목적을 달성하기 위하여, 본 발명은 카프릴알데히드(Caprylaldehyde), 1-나프트알데히드(1-Naphtaldehyde), 2-나프트알데히드(2-Naphtaldehyde), 5,8-디하이드록시-1,4-나프토퀴논(5,8-Dihydroxy-1,4-naphthoquinone), 나프탈렌(Naphthalene), 프탈알데히드(Phthalaldehyde)로 이루어진 군으로부터 1종 이상 선택된 화합물을 포함하는 살비제를 제공한다.In order to achieve the above object, the present invention is caprylaldehyde (Caprylaldehyde), 1-naphthaldehyde (1-Naphtaldehyde), 2-naphthaldehyde (2-Naphtaldehyde), 5,8-dihydroxy-1, Provided are acaricides comprising at least one compound selected from the group consisting of 4-naphthoquinone (5,8-Dihydroxy-1,4-naphthoquinone), naphthalene, and phthalaldehyde.

바람직하기로, 상기한 살비제는 집먼지 진드기 및 저장식품 진드기에 대하여 살비 효과를 나타낸다.Preferably, the acaricides have an acaricide effect against house dust mites and stored food mites.

이하 본 발명을 더욱 상세히 설명한다.Hereinafter, the present invention will be described in more detail.

본 발명자는 기존의 화합물 중 집먼지 진드기 및 저장식품 진드기 모두에 대하여 살비성을 나타내는 화합물을 스크리닝하였고, 이때의 살비 효과를 확인하였다. The present inventors screened compounds showing acaricidal property against both house dust mites and stored food mites among the existing compounds, and confirmed the killing effect at this time.

상기 화합물은 하기 화학식 1의 카프릴알데히드, 화학식 2의 1-나프트알데히드, 화학식 3의 2-나프트알데히드, 화학식 4의 5,8-디하이드록시-1,4-나프토퀴논, 화학식 5의 나프탈렌, 및 화학식 6의 프탈알데히드이다. The compound is caprylaldehyde of Formula 1, 1-naphthaldehyde of Formula 2, 2-naphthaldehyde of Formula 3, 5,8-dihydroxy-1,4-naphthoquinone of Formula 4, Formula 5 Naphthalene and phthalaldehyde of the formula (6).

Figure 112005020774087-PAT00001
Figure 112005020774087-PAT00001

Figure 112005020774087-PAT00002
Figure 112005020774087-PAT00002

Figure 112005020774087-PAT00003
Figure 112005020774087-PAT00003

Figure 112005020774087-PAT00004
Figure 112005020774087-PAT00004

Figure 112005020774087-PAT00005
Figure 112005020774087-PAT00005

Figure 112005020774087-PAT00006
Figure 112005020774087-PAT00006

상기 화학식 1 내지 6으로 표시되는 화합물은 집먼지 진드기(House Dust Mite) 및 저장식품 진드기(Tyrophagus putrescentiae)에 대하여 살비효과를 가지며, 상기 화학식 1 내지 6의 화합물 단독 또는 2종 이상 혼합하여 사용할 수 있다. 이때 상기 집먼지 진드기는 큰다리 먼지진드기(American house dust mite, Dermatophagoides farinae)및 세로무늬 먼지진드기(European house dust mite, Dermatophagoide pteronyssinus)이다. Compounds represented by Formulas 1 to 6 are house dust mite and stored food mite ( Tyrophagus) putrescentiae ) has an acaricidal effect, and may be used alone or in combination of two or more compounds of the formula (1). At this time, the house dust mite (American house dust mite, Dermatophagoides farinae ) and vertical house dust mite (European house dust mite, Dermatophagoide pteronyssinus ).

특히 집먼지 진드기와 저장식품 진드기는 서로 다른 생리작용 및 메카니즘을 지녀 현재 개발되어 있는 큰다리 먼지 진드기 및 세로무늬 먼지 진드기와 같은 집먼지 진드기를 방제하기 위한 살비제로서는 저장식품 진드기를 방제하기 못하여, 각각의 진드기에 대해 서로 다른 물질로 살비 제제를 제조하고 있다. 그러나 상기한 화학식 1 내지 6의 화합물은 집먼지 진드기에 대하여 살비 효과를 가지고, 특히 화학식 1의 카프릴알데히드, 화학식 5의 나프탈렌, 및 화학식 6의 프탈알데히드는 저장식품 진드기에 대해서도 우수한 살비 효과를 나타낸다.In particular, house dust mites and stored food mites have different physiological functions and mechanisms, and as acaricides for controlling house dust mites such as large-legged dust mites and vertically-patterned dust mites, which are currently developed, they cannot control stored food mites. For the preparation of acaricides with different materials for the preparation. However, the compounds of Formulas 1 to 6 have an acaricidal effect on house dust mites, in particular caprylaldehyde of formula (1), naphthalene of formula (5), and phthalaldehyde of formula (6) also exhibit excellent acaricide effects on stored food mites.

바람직한 실시예에 따르면, 상기 화학식 1 내지 6으로 표시되는 화합물을 이용하여 큰다리 먼지진드기, 세로무늬 먼지진드기 및 저장식품 진드기에 대한 살비 효과를 알아본 결과(표 1 내지 2 참조), 상기 3종류의 진드기 모두에 대하여 살비 효능을 나타내었을 뿐만 아니라 기존의 합성 살비제인 벤질 벤조에이트 및 디부틸 프탈레이트에 비해 우수한 활성을 나타내었다.According to a preferred embodiment, using the compound represented by the formula 1 to 6 as a result of examining the acaricide effect on the large leg dust mites, vertical pattern dust mites and stored food mites (see Tables 1 to 2), the three types In addition to showing the acaricidal effect on all the ticks of the showed excellent activity compared to the existing synthetic acaricides benzyl benzoate and dibutyl phthalate.

특히, 화학식 2의 1-나프트알데히드, 화학식 3의 2-나프트알데히드 및 화학식 4의 5,8-디하이드록시-1,4-나프토퀴논을 제외한 화합물은 저장식품 진드기에 매우 효과적으로 살비 효과를 지님을 확인하였다. In particular, compounds except 1-naphthaldehyde of formula (2), 2-naphthaldehyde of formula (3) and 5,8-dihydroxy-1,4-naphthoquinone of formula (4) have a very effective fertilizing effect on the stored food tick Confirmed to have.

본 발명에 따른 살비제는 화학식 1 내지 6으로 표시되는 화합물을 단독 또는 혼합물 형태로 0.01 내지 40 중량% 포함하여 진드기, 집먼지 진드기 및 저장식품 진드기가 서식하는 곳에 적용한다.The acaricide according to the present invention is applied to a place where mites, dust mites and stored food mites inhabit, including 0.01 to 40% by weight of the compound represented by Formulas 1 to 6 alone or in a mixture.

이때 상기 살비제에 사용되는 화합물의 함량은 살충제의 제형, 살포방법에 따라 달리 적용될 수 있으며, 이때 살비제 중의 활성 성분의 농도는 집먼지 진드기 및 저장식품 진드기를 구제하는 데 효과적인 양이 사용되며, 이때의 특정 농도는 제제의 형태 및 적용 방법에 따라 달라진다. At this time, the content of the compound used in the acaricide may be applied differently depending on the formulation of the pesticide, the spraying method, the concentration of the active ingredient in the acaricide is used to control the dust mites and stored food mites, and at this time The concentration depends on the form of the preparation and the method of application.

본 발명의 살비제는 진드기가 서식하는 곳에 사용하며, 사용방법은 도포처리, 침지처리, 훈증처리 등의 방법이 바람직하고, 더욱 바람직하게는 휘발성독 또는 접촉독으로 적용하여 진드기를 사멸시키는 것이고, 가장 바람직하게는 휘발성독 또는 훈증독으로 사용하는 것이다. 더욱이 상기 살비제는 진드기 이외의 해충에 대한 방제목적으로 사용될 수도 있으며, 이때 적용량은 통상적인 살충제를 적용시키는 양으로 사용할 수 있다. The acaricide of the present invention is used where a mite is inhabited, and the use method is preferably a coating treatment, dipping treatment, fumigation treatment, or the like, and more preferably, a volatile poison or a contact poison is used to kill the tick. Preferably it is used as a volatile poison or a fumigated poison. Moreover, the acaricide may be used for the control of pests other than mites, and the application amount may be used in an amount to apply a conventional pesticide.

본 발명에 따른 살비제는 다양한 형태로 제조 및 적용될 수 있으며, 도포 및 침지 처리를 위해 하나 이상의 용매에 용해 또는 분산시켜 액제, 유제, 도포제 또 는 입제의 형태로 제조될 수 있으며, 훈증 처리를 위해 임의로 계면활성제를 사용하여 증량제, 예를 들어 액체 용매, 가압 액화 가스 및/또는 고체 담체와 배합되어 훈연제, 훈증제, 도포제, 입제 및 고형제의 형태로 바람직하게 사용된다. Acaricides according to the invention can be prepared and applied in various forms, can be prepared in the form of solutions, emulsions, coatings or granules by dissolving or dispersing in one or more solvents for the application and dipping treatment, optionally for fumigation treatment Surfactants are used in combination with extenders such as liquid solvents, pressurized liquefied gases and / or solid carriers and are preferably used in the form of smokers, fumigants, coatings, granules and solids.

이와 같은 다양한 형태의 제제로 제조하기 위해, 상기 화합물에 더하여 이 분야에서 통상적으로 사용되고 있는 용매 및 첨가제가 사용될 수 있다. 일예로, 인체에 무해한 에탄올 또는 물을 분산액으로 사용하여 액상 형태로 제조할 수 있고, 통상의 부형제 등을 사용하여 고상 형태로 제조될 수 있다. In addition to the above compounds, solvents and additives conventionally used in the art can be used to prepare these various forms of preparations. For example, ethanol or water, which is harmless to the human body, may be prepared in a liquid form using a dispersion, and may be prepared in a solid form using a conventional excipient or the like.

또한 상기 살비제는 사용방법에 따라 부형제를 더욱 포함할 수 있다. 상기 부형제는 조성물의 용도 및 적용방법에 따라 적절한 물질을 사용하는 것이 바람직하며, 통상적인 살충제 제형에 포함되는 물질이 더욱 바람직하다. In addition, the acaricide may further include an excipient according to the method of use. The excipient preferably uses an appropriate material according to the use and application method of the composition, more preferably a material included in a conventional pesticide formulation.

또한 본 발명의 카프릴알데히드, 1-나프트알데히드, 2-나프트알데히드, 5,8-디하이드록시-1,4-나프토퀴논, 나프탈렌 및 프탈알데히드는 살비활성을 가지며 다양한 충에 효과를 가지는 신규 화합물을 위한 모핵 화합물의 기질로 이용할 수 있다. 예를 들어 모핵 화합물은 기존에 활성이 알려진 물질의 구조를 기반으로 화학 합성을 통해 수산화기(-OH), 알데히드기(-COH), 알콜기(-OH), 아미드기(-CONH) 또는 아릴기(-C6H5)와 같은 다양한 관능기를 알킬화, 에테르화 또는 에스테르화 반응과 같이 당업계에 통상적인 합성방법을 이용하여 치환된 유도체들을 제조할 수 있다.In addition, the caprylaldehyde, 1-naphthaldehyde, 2-naphthaldehyde, 5,8-dihydroxy-1,4-naphthoquinone, naphthalene and phthalaldehyde of the present invention have acaricide activity and effect on various insects Eggplants can be used as substrates for parent compound for novel compounds. For example, the parent compound may be a hydroxyl group (-OH), an aldehyde group (-COH), an alcohol group (-OH), an amide group (-CONH) or an aryl group through a chemical synthesis based on the structure of a known substance Substituted derivatives can be prepared using synthetic methods customary in the art, such as alkylation, etherification or esterification reactions, such as -C 6 H 5 ).

이하, 본 발명의 이해를 돕기 위하여 바람직한 실시예를 제시한다. 그러나 하기의 실시예는 본 발명을 보다 쉽게 이해하기 위하여 제공되는 것일 뿐 본 발명이 하기의 실시예에 한정되는 것은 아니다. Hereinafter, preferred examples are provided to aid in understanding the present invention. However, the following examples are provided only to more easily understand the present invention, and the present invention is not limited to the following examples.

실시예Example 1:  One: 살비성Acaricide 화합물 compound

카프릴알데히드, 1-나프트알데히드, 2-나프트알데히드, 5,8-디하이드록시-1,4-나프토퀴논, 나프탈렌은 알드리치(Aldrich), 프탈알데히드는 플루카(Fluka)사에서 구입하였다.Caprylaldehyde, 1-naphthaldehyde, 2-naphthaldehyde, 5,8-dihydroxy-1,4-naphthoquinone and naphthalene are purchased from Aldrich and phthalaldehyde from Fluka. It was.

실험예Experimental Example 1 One

(1) 진드기 사육(1) mite breeding

세로무늬 먼지진드기를 상대습도 75 ± 5 %, 온도 25 ±1 ℃를 유지한 사육실에 사육하였으며, 12.5×10.5 ×5 ㎝ 용기에 치어사료와 복합비타민제(에비오제)를 1:1로 혼합한 사료 및 17.5×17.5 ×17.5 ㎝ 부피의 용기 바닥에 식염수를 적당량 부어 사육실에 넣어 주었다. 상기 진드기는 살비제에 노출 없이 사육하였다. Vertical dust mites were bred in a breeding room maintained at a relative humidity of 75 ± 5% and a temperature of 25 ± 1 ° C. The mixture was mixed in a 12.5 × 10.5 × 5 cm container with a feed of mixed vitamins (Ebije ) in a 1: 1 ratio. Saline water was poured into the feed room and the bottom of the container with a volume of 17.5 x 17.5 x 17.5 cm. The mites were bred without exposure to acaricide.

(2) 세로무늬 먼지진드기(European house dust mite, (2) European house dust mite, DermatophagoideDermatophagoide pteronyssinus pteronyssinus )에 대한 For) 살비성Acaricide 검정 black

생물활성물질 탐색의 가장 중요한 점이 초기 출발농도의 설정이다. 본 발명에서는 진드기의 형태적인 특징이 현미경학적 구조를 갖고 있기 때문에 수차의 예비실험을 통해 2 ㎖ 마이크로튜브 당 시료 1 mg을 설정하였다. 실시예 1의 화합물들을 농도(80. 40. 20. 10. 5. 4. 2. 1. 0.5. 0.1. 0.05 ㎍/㎠)별로 40 ㎕의 메탄올에 녹이고, 무색의 마이크로튜브(2 ㎖)에 처리하여 튜브의 벽면과 뚜껑에 물질이 골고루 분산하여 묻을 수 있도록 수회 상하로 흔들어 준 후, 동결 건조기에서 1시간 동안 용매를 휘발시켰다. 각각의 튜브에 25개체의 진드기를 넣어 준 후, 25 ± 1 ℃의 조건하에서 검정을 하였다. The most important point in the search for bioactive substances is the setting of the initial starting concentration. In the present invention, since the morphological characteristics of the tick have a microscopic structure, 1 mg of the sample per 2 ml microtube was set through several preliminary experiments. The compounds of Example 1 were dissolved in 40 μl of methanol at a concentration (80. 40. 20. 10. 5. 4. 2. 1. 0.5. 0.1. 0.05 μg / cm 2) and in colorless microtubes (2 mL). After the treatment was shaken up and down several times so that the material was evenly dispersed and buried on the wall and the lid of the tube, the solvent was evaporated for 1 hour in a freeze dryer. 25 mites were put in each tube, and the assay was carried out under the conditions of 25 ± 1 ° C.

진드기들은 현미경에서 관찰하여 활동력이 우수한 개체들만을 미세한 붓을 이용해 선별하였다. 검정결과는 처리 24시간 후에 광학현미경(20배)하에서 조사하였는데, 미세한 붓을 이용해 부속지 및 몸통을 자극하여 전혀 움직임이 없는 개체는 사망한 것으로 간주하였다. 모든 검정은 5회 이상 반복하였으며, 살비율에 대한 평균간의 비교는 쉐페(Scheffe's test, SAS Institute, 1996)를 이용하였다. The ticks were observed under a microscope to select only those with high activity using a fine brush. Assay results were examined under an optical microscope (20 times) after 24 hours of treatment, the subject was considered to have died without any movement by stimulating the appendage and torso with a fine brush. All assays were repeated 5 or more times and a comparison between the means for the rate of fertilization was made using Scheffe's test (SAS Institute, 1996).

본 발명에 따른 6종 화합물들의 살비능은 하기 표 1(세로무늬 먼지진드기)에 나타내었다. 이때 비교예로서 종래 살비제로 사용되고 있는 벤질 벤조에이트와 디부틸 프탈레이트를 사용하였다. 하기 표 1 내지 3의 동일한 문자(a, b)는 평균이 통계상(P=0.05, Sheffe 검정) 별다른 차이가 없음을 나타내며, 살충율은 아크사인 제곱근으로 변형시켜 나타내었다. The a potency of the six compounds according to the present invention is shown in Table 1 (vertical pattern dust mites). At this time, benzyl benzoate and dibutyl phthalate, which are conventionally used as acaricides, were used as comparative examples. The same letters (a, b) in the following Tables 1 to 3 indicate that the mean is not statistically different ( P = 0.05, Sheffe test), and the insecticidal rate is represented by transforming the square of the arc sine.

화합물compound 세로무늬 먼지진드기 살 비 율(평균±표준편차, %)Vertical pattern dust mite rate (mean ± standard deviation,%) 처 리 농 도(㎍/㎠)Treatment concentration (㎍ / ㎠) 8080 4040 2020 1010 5.05.0 4.04.0 2.02.0 1.01.0 0.50.5 0.10.1 0.050.05 카프릴알데히드Caprylaldehyde 100a 100 a 100a 100 a 100a 100 a 100a 100 a 100a 100 a 85±4.385 ± 4.3 47±2.9c 47 ± 2.9 c 15±1.1c 15 ± 1.1 c 0d 0 d 0d 0 d 0d 0 d 1-나프트알데히드1-naphthaldehyde 100a 100 a 100a 100 a 100a 100 a 100a 100 a 100a 100 a 100a 100 a 81±2.2b 81 ± 2.2 b 43±3.5c 43 ± 3.5 c 17±1.3c 17 ± 1.3 c 0d 0 d 0d 0 d 2-나프트알데히드2-naphthaldehyde 100a 100 a 100a 100 a 100a 100 a 100a 100 a 100a 100 a 62± 2.362 ± 2.3 37±4.4c 37 ± 4.4 c 12±1.7c 12 ± 1.7 c 0d 0 d 0d 0 d 0d 0 d 5,8-디하이드록시-1,4-나프토퀴논5,8-dihydroxy-1,4-naphthoquinone 100a 100 a 100a 100 a 100a 100 a 100a 100 a 100a 100 a 100a 100 a 100a 100 a 100a 100 a 95.9±4.4b 95.9 ± 4.4 b 49.6±5.0c 49.6 ± 5.0 c 18.5±1.7c 18.5 ± 1.7 c 나프탈렌naphthalene 100a 100 a 100a 100 a 100a 100 a 100a 100 a 89.4±6.0b 89.4 ± 6.0 b 78.6±2.9b 78.6 ± 2.9 b 57.4±2.2b 57.4 ± 2.2 b 49.5±4.3c 49.5 ± 4.3 c 27.4±3.3c 27.4 ± 3.3 c 0d 0 d 0d 0 d 프탈알데히드Phthalaldehyde 100a 100 a 100a 100 a 94±2.9b 94 ± 2.9 b 76±1.7b 76 ± 1.7 b 62±4.4b 62 ± 4.4 b 51±2.2b 51 ± 2.2 b 28±2.7c 28 ± 2.7 c 10c 10 c 0d 0 d 0d 0 d 0d 0 d 벤질 벤조에이트Benzyl benzoate 100a 100 a 100a 100 a 100a 100 a 32.0±2.9b 32.0 ± 2.9 b 0d 0 d 0d 0 d 0c 0 c 0d 0 d 0d 0 d 0d 0 d 0d 0 d 디부틸 프탈레이트Dibutyl phthalate 100a 100 a 100a 100 a 92.0±3.8b 92.0 ± 3.8 b 62.2 ±1.9c 62.2 ± 1.9 c 29.9 ±1.7d 29.9 ± 1.7 d 0d 0 d 0d 0 d 0d 0 d 0d 0 d 0d 0 d 0d 0 d

상기 표 1은 세로무늬 먼지진드기에 대한 살비검정 결과를 나타낸 것으로, 6종의 화합물 중 가장 살비율이 우수한 화합물은 5,8-디하이드록시-1,4-나프토퀴논으로 최저 농도 1 ㎍/㎠까지의 모든 처리농도에서 100 %의 우수한 살비율을 보였다. 다음으로 1-나프트알데히드, 카프릴알데히드 순으로 우수한 살비율을 확인하였다.Table 1 shows the results of the astringent test for the vertical pattern dust mite, the compound having the best ratio of the six compounds is 5,8-dihydroxy-1,4-naphthoquinone with a minimum concentration of 1 ㎍ / At all treatment concentrations up to 2 cm 2, excellent agicide rate was shown. Next, 1-naphthaldehyde and caprylaldehyde were found to have excellent abundance.

실시예 1의 6종 화합물은 80, 40 ㎍/㎠로 농도 처리하였을 때 모두 100 %의 살비율을 나타내었고 20, 10 ㎍/㎠을 처리한 경우 프탈알데히드만 94 %, 76 %의 살비율을 보이고 나머지 5종 화합물 모두 100 %의 살비율을 나타내었다. 이 때 10 ㎍/㎠을 처리한 대조구의 벤질 벤조에이트 및 디부틸 프탈레이트는 32 % 와 62 %로 낮은 살비율을 보였다.The six compounds of Example 1 exhibited a 100% agicide rate when treated at 80, 40 ㎍ / ㎠ and 20, 10 ㎍ / ㎠ treated phthalaldehyde only 94%, 76% The remaining five compounds showed 100% agicide rate. At this time, the benzyl benzoate and dibutyl phthalate of the control group treated with 10 ㎍ / ㎠ showed a low agicide rate of 32% and 62%.

또한 5 ㎍/㎠을 처리한 경우, 카프릴알데히드, 1-나프트알데히드, 2-나프트알데히드, 5,8-디하이드록시-1,4-나프토퀴논은 100 %의 살비율을 보이고, 나프탈렌과 프탈알데히드는 각각 89 %와 62 %의 살비율을 나타내었다.In addition, when treated with 5 μg / cm 2, caprylaldehyde, 1-naphthaldehyde, 2-naphthaldehyde, 5,8-dihydroxy-1,4-naphthoquinone showed a 100% abundance ratio, Naphthalene and phthalaldehyde showed 89% and 62% application rates, respectively.

이 보다 낮은 농도인 4 ㎍/㎠ 농도 처리 시, 1-나프트알데히드, 5,8-디하이드록시-1,4-나프토퀴논은 여전히 100 %의 높은 살비율을 보였으며, 나머지 화합물들은 50 % 이상의 살비율을 나타내었다. 반면 대조구인 벤질 벤조에이트 및 디부틸 프탈레이트는 모두 0 %로 살비율을 전혀 확인할 수 없었다. At lower concentrations of 4 μg / cm 2, 1-naphthaldehyde, 5,8-dihydroxy-1,4-naphthoquinone still showed a high abundance of 100% and the remaining compounds were 50 A ratio of more than% was shown. On the other hand, the control group benzyl benzoate and dibutyl phthalate were all 0% could not be confirmed at all.

또한, 2 ㎍/㎠ 농도 처리 시, 5,8-디하이드록시-1,4-나프토퀴논은 100 %, 1-나프트알데히드와 나프탈렌은 50 % 이상의 살비율, 나머지 화합물은 50 % 이하의 살비율을 보였다. In addition, at the concentration of 2 μg / cm 2, 5,8-dihydroxy-1,4-naphthoquinone was 100%, 1-naphthaldehyde and naphthalene was 50% or more, and the remaining compounds were 50% or less. The rate of fat was shown.

1 ㎍/㎠ 농도에서 5,8-디하이드록시-1,4-나프토퀴논은 여전히 100 %의 높은 살비율을 보였고 나머지 5종 화합물은 50 % 이하의 살비율을 나타내었다. At a concentration of 1 μg / cm 2, 5,8-dihydroxy-1,4-naphthoquinone still showed a high agitation rate of 100% and the remaining five compounds showed a affinity rate of 50% or less.

더욱이 0.5 ㎍/㎠ 및 0.1 ㎍/㎠의 농도에서도 5,8-디하이드록시-1,4-나프토퀴논은 95 %와 49 %의 살비율을 나타내어 대조군인 벤질 벤조에이트 및 디부틸 프탈레이트에 비해 살비율이 훨씬 우수함을 확인할 수 있었다.Furthermore, even at concentrations of 0.5 μg / cm 2 and 0.1 μg / cm 2, 5,8-dihydroxy-1,4-naphthoquinone showed 95% and 49% abundance, compared to benzyl benzoate and dibutyl phthalate, the control. It was confirmed that the rate of fat was much better.

(3) (3) 큰다리Big leg 먼지진드기(American house dust mite,  American house dust mite, DermatophagoidesDermatophagoides farinae farinae )에 대한 For) 살비성Acaricide 검정 black

큰다리 먼지진드기에 대한 살비 활성을 알아보기 위해 상기 실험예 1과 동일하게 수행하여, 하기 표 2에 나타내었다. 이때 비교예로서 종래 살비제로 사용되고 있는 벤질 벤조에이트와 디부틸 프탈레이트를 사용하였다. 하기 표 2의 동일한 문자(a, b)는 평균이 통계상(P=0.05, Sheffe 검정) 별다른 차이가 없음을 나타내며, 살충율은 아크사인 제곱근으로 변형시켜 나타내었다. In order to determine the acaricide activity for the large leg dust mite was carried out in the same manner as in Experimental Example 1, it is shown in Table 2. At this time, benzyl benzoate and dibutyl phthalate, which are conventionally used as acaricides, were used as comparative examples. The same letters (a, b) in Table 2 indicate that the mean is not statistically different ( P = 0.05, Sheffe test), and the insecticidal rate is represented by modifying the square root of arc sine.

화합물compound 큰다리 먼지진드기에 대한 살 비 율(평균±표준편차, %)Percentage of application for large dust mites (mean ± standard deviation,%) 처 리 농 도(㎍/㎠)Treatment concentration (㎍ / ㎠) 8080 4040 2020 1010 5.05.0 4.04.0 2.02.0 1.01.0 0.50.5 0.10.1 0.050.05 카프릴알데히드Caprylaldehyde 100a 100 a 100a 100 a 100a 100 a 100a 100 a 100a 100 a 72±2.972 ± 2.9 35±3.3c 35 ± 3.3 c 0d 0 d 0d 0 d 0d 0 d 0d 0 d 1-나프트알데히드1-naphthaldehyde 100a 100 a 100a 100 a 100a 100 a 100a 100 a 100a 100 a 100a 100 a 70±2.4b 70 ± 2.4 b 26±1.3c 26 ± 1.3 c 0d 0 d 0d 0 d 0d 0 d 2-나프트알데히드2-naphthaldehyde 100a 100 a 100a 100 a 100a 100 a 100a 100 a 95±4.2b 95 ± 4.2 b 50±2.450 ± 2.4 25±2.9c 25 ± 2.9 c 0d 0 d 0d 0 d 0d 0 d 0d 0 d 5,8-디하이드록시 -1,4-나프토퀴논5,8-dihydroxy-1,4-naphthoquinone 100a 100 a 100a 100 a 100a 100 a 100a 100 a 100a 100 a 100a 100 a 100a 100 a 100a 100 a 82.5±4.3b 82.5 ± 4.3 b 32.5±2.2c 32.5 ± 2.2 c 0d 0 d 나프탈렌naphthalene 100a 100 a 100a 100 a 100a 100 a 100a 100 a 83.2±3.7b 83.2 ± 3.7 b 72.2±1.2b 72.2 ± 1.2 b 50.3±2.9b 50.3 ± 2.9 b 39.4 ±3.3c 39.4 ± 3.3 c 15.3±1.7c 15.3 ± 1.7 c 0d 0 d 0d 0 d 프탈알데히드Phthalaldehyde 100a 100 a 100a 100 a 85±4.2b 85 ± 4.2 b 65±9.2b 65 ± 9.2 b 55±1.2b 55 ± 1.2 b 41±2.2c 41 ± 2.2 c 18±1.7c 18 ± 1.7 c 0d 0 d 0d 0 d 0d 0 d 0d 0 d 벤질 벤조에이트Benzyl benzoate 100a 100 a 100a 100 a 100a 100 a 32.0± 2.9c 32.0 ± 2.9 c 0d 0 d 0d 0 d 0d 0 d 0d 0 d 0d 0 d 0d 0 d 0d 0 d 디부틸 프탈레이트Dibutyl phthalate 100a 100 a 100a 100 a 92.0±3.8b 92.0 ± 3.8 b 62.2± 1.9b 62.2 ± 1.9 b 29.9±1.7c 29.9 ± 1.7 c 0d 0 d 0d 0 d 0d 0 d 0d 0 d 0d 0 d 0d 0 d

상기 표 2를 참조하면, 본 발명에 따른 6종 화합물은 상기 세로무늬 진드기와 비슷한 양상의 살비율을 나타냄을 알 수 있으며, 특히 5,8-디하이드록시-1,4-나프토퀴논에서 강한 살비율을 확인하였다. Referring to Table 2, it can be seen that the six compounds according to the present invention show a similar ratio of the vertical pattern tick, particularly strong in 5,8-dihydroxy-1,4-naphthoquinone. The agitation rate was confirmed.

구체적으로 처리 농도 80, 40, 20, 및 10 ㎍/㎠ 에서 5종 화합물 모두 100 %의 살비율을 보였고, 프탈알데히드만 20 및 10 ㎍/㎠ 농도에서 85 %와 65 %의 살비율을 보였다. Specifically, all of the five compounds showed a 100% abundance at treatment concentrations of 80, 40, 20, and 10 μg / cm 2, and 85% and 65% at a concentration of 20 and 10 μg / cm 2 of phthalaldehyde alone.

5 ㎍/㎠ 농도에서는 2-나프트알데히드 95 %, 나프탈렌 83 %, 프탈알데히드 55 %의 살비율을 보이고 나머지 화합물은 100 %의 살비율을 나타내었다. 반면에 대조구인 벤질 벤조에이트 0 %, 디부틸 프탈레이트 29 %의 낮은 살비율을 확인하였다. 4 ㎍/㎠ 농도에서는 1-나프트알데히드, 5,8-디하이드록시-1,4-나프토퀴논은 여전히 100 %의 살비율을 나타내었고, 카프릴알데히드 72 %, 2-나프트알데히드 50 %, 나프탈렌 72 %, 프탈알데히드 41 %의 살비율을 나타내었다. At a concentration of 5 μg / cm 2, 95% of 2-naphthaldehyde, 83% of naphthalene, and 55% of phthalaldehyde were shown, while the remaining compounds showed a ratio of 100%. On the other hand, low control ratios of 0% benzyl benzoate and 29% dibutyl phthalate were observed. At a concentration of 4 μg / cm 2, 1-naphthaldehyde, 5,8-dihydroxy-1,4-naphthoquinone still showed 100% abundance, caprylaldehyde 72%, 2-naphthaldehyde 50 The ratio of naphthalene 72%, phthalaldehyde 41%.

5,8-디하이드록시-1,4-나프토퀴논은 2.0 및 1.0 ㎍/㎠의 낮은 농도에서도 100 %의 살비율을 보였으며, 특히 최저 농도인 0.1, 0.05 ㎍/㎠에서도 살비성을 나타내어 대조구인 벤질 벤조에이트와 디부틸 프탈레이트에 비하여 월등한 살비효과가 있음을 확인할 수 있었다. 5,8-dihydroxy-1,4-naphthoquinone showed 100% agicide at low concentrations of 2.0 and 1.0 ㎍ / ㎠, especially at the lowest concentrations of 0.1 and 0.05 ㎍ / ㎠ Compared with the control group benzyl benzoate and dibutyl phthalate it was confirmed that there is an excellent acaricide effect.

(4) 저장식품 진드기((4) stored food mites ( TyrophagusTyrophagus putrescentiaeputrescentiae )에 대한 For) 살비성Acaricide 검정 black

저장식품 진드기에 대한 살비 활성을 알아보기 위해 상기 실험예 1과 동일하게 수행하여, 하기 표 3에 나타내었다. 이때 비교예로서 종래 살비제로 사용되고 있는 벤질 벤조에이트와 디부틸 프탈레이트를 사용하였다. 하기 표 3의 동일한 문자(a, b)는 평균이 통계상(P=0.05, Sheffe 검정) 별다른 차이가 없음을 나타내며, 살충율은 아크사인 제곱근으로 변형시켜 나타내었다. In order to determine the acaricide activity for the stored food mite was carried out in the same manner as in Experiment 1, it is shown in Table 3. At this time, benzyl benzoate and dibutyl phthalate, which are conventionally used as acaricides, were used as comparative examples. The same letters (a, b) in Table 3 indicate that the mean is not statistically different ( P = 0.05, Sheffe test), and the insecticidal rate is represented by modifying the square root of arc sine.

화합물compound 저장식품 진드기에 대한 살 비 율(평균±표준편차, %)Percentage of application for stored food ticks (mean ± standard deviation,%) 처 리 농 도(㎍/㎠)Treatment concentration (㎍ / ㎠) 8080 4040 2020 1010 5.05.0 4.04.0 2.02.0 1.01.0 0.50.5 0.10.1 0.050.05 카프릴알데히드Caprylaldehyde 100a 100 a 100a 100 a 100a 100 a 100a 100 a 100a 100 a 75±1.7b 75 ± 1.7 b 47±3.5c 47 ± 3.5 c 15±1.7c 15 ± 1.7 c 0d 0 d 0d 0 d 0d 0 d 1-나프트알데히드1-naphthaldehyde 0d 0 d 0d 0 d 0d 0 d 0d 0 d 0d 0 d 0d 0 d 0d 0 d 0d 0 d 0d 0 d 0d 0 d 0d 0 d 2-나프트알데히드2-naphthaldehyde 0d 0 d 0d 0 d 0d 0 d 0d 0 d 0d 0 d 0d 0 d 0d 0 d 0d 0 d 0d 0 d 0d 0 d 0d 0 d 5,8-디하이드록시-1,4-나프토퀴논5,8-dihydroxy-1,4-naphthoquinone 0d 0 d 0d 0 d 0d 0 d 0d 0 d 0d 0 d 0d 0 d 0d 0 d 0d 0 d 0d 0 d 0d 0 d 0d 0 d 나프탈렌naphthalene 100a 100 a 100a 100 a 100a 100 a 89.7±4.4b 89.7 ± 4.4 b 37.8±2.3c 37.8 ± 2.3 c 15±1.1c 15 ± 1.1 c 0d 0 d 0d 0 d 0d 0 d 0d 0 d 0d 0 d 프탈알데히드Phthalaldehyde 100a 100 a 100a 100 a 100a 100 a 100a 100 a 87.5±4.3b 87.5 ± 4.3 b 72.4±2.9b 72.4 ± 2.9 b 51.2±1.7b 51.2 ± 1.7 b 30.6±2.2c 30.6 ± 2.2 c 11.5±1.3c 11.5 ± 1.3 c 0d 0 d 0d 0 d 벤질 벤조에이트Benzyl benzoate 100a 100 a 100a 100 a 100a 100 a 32.0±2.9c 32.0 ± 2.9 c 0d 0 d 0d 0 d 0d 0 d 0d 0 d 0d 0 d 0d 0 d 0d 0 d 디부틸 프탈레이트Dibutyl phthalate 100a 100 a 100a 100 a 92.0±3.8b 92.0 ± 3.8 b 62.2±1.9b 62.2 ± 1.9 b 29.9±1.7c 29.9 ± 1.7 c 0d 0 d 0d 0 d 0d 0 d 0d 0 d 0d 0 d 0d 0 d

상기 표 3을 참조하면, 본 발명의 카프릴알데히드, 나프탈렌, 프탈알데히드는 80, 40, 20 ㎍/㎠ 농도 처리 시 100 %의 살비율을 확인하였지만, 1-나프트알데히드, 2-나프트알데히드, 5,8-디하이드록시-1,4-나프토퀴논은 초기 농도부터 살비성을 전혀 확인할 수 없었다. Referring to Table 3, the caprylaldehyde, naphthalene, phthalaldehyde of the present invention was confirmed to be 100% of the abundance ratio of 80, 40, 20 ㎍ / ㎠ concentration treatment, 1-naphthaldehyde, 2-naphthaldehyde , 5,8-dihydroxy-1,4-naphthoquinone could not be confirmed at all at the initial concentration.

10 ㎍/㎠ 농도 처리 시는 나프탈렌의 89 %를 제외한 2종의 화합물에서 여전히 100 %의 강한 살비효과를 가지고 있음을 알 수 있었다. In the case of 10 ㎍ / ㎠ concentration, two compounds except 89% of naphthalene was still found to have a strong killing effect of 100%.

또한 5, 4 ㎍/㎠ 농도 처리 시, 카프릴알데히드, 나프탈렌, 프탈알데히드는 살비율이 감소하는 것을 확인하였다. 대조구로 이용된 벤질 벤조에이트, 디부틸 프탈레이트는 이미 10 ㎍/㎠ 농도에서부터 살비율이 감소하기 시작하여 4 ㎍/㎠에서는 살비율을 전혀 확인할 수 없었다. 그러나 프탈알데히드는 최소 농도의 1과 0.5 ㎍/㎠ 농도에서도 살비율을 보임으로써 대조구인 벤질 벤조에이트와 디부틸 프탈레이트에 비하여 월등한 살비효과가 있음을 확인할 수 있었다. In addition, it was confirmed that caprylaldehyde, naphthalene, and phthalaldehyde decreased the abundance ratio when the 5, 4 ㎍ / ㎠ concentration treatment. Benzyl benzoate and dibutyl phthalate, used as controls, had already started to reduce the agitation rate from a concentration of 10 μg / cm 2 and could not confirm the agitation rate at 4 μg / cm 2. However, phthalaldehyde was shown to have a superior acaricide effect compared to the control group benzyl benzoate and dibutyl phthalate by showing the rate of fertilization at the minimum concentration of 1 and 0.5 ㎍ / ㎠.

이와 같이, 본 발명에 의해 카프릴알데히드, 1-나프트알데히드, 화학식 3의 2-나프트알데히드, 5,8-디하이드록시-1,4-나프토퀴논, 나프탈렌 및 프탈알데히드이 집먼지 진드기 및 저장식품 진드기에 대한 우수한 살비 활성을 나타내었을 뿐만 아니라, 기존의 합성 살비제에 비해 우수한 살비율을 가진다.As such, caprylaldehyde, 1-naphthaldehyde, 2-naphthaldehyde of formula 3, 5,8-dihydroxy-1,4-naphthoquinone, naphthalene and phthalaldehyde are house dust mites and storage according to the present invention. Not only showed good acaricide activity against food mites, but also has a good acaricide rate compared to conventional synthetic acaricides.

Claims (4)

하기 화학식 1의 카프릴알데히드(Caprylaldehyde), 화학식 2의 1-나프트알데히드(1-Naphtaldehyde), 화학식 3의 2-나프트알데히드(2-Naphtaldehyde), 화학식 4의 5,8-디하이드록시-1,4-나프토퀴논(5,8-Dihydroxy-1,4-naphthoquinone), 화학식 5의 나프탈렌(Naphthalene), 및 화학식 6의 프탈알데히드(Phthalaldehyde)로 이루어진 군으로부터 1종 이상 선택된 화합물을 유효성분으로 포함하는 살비제:Caprylaldehyde of Formula 1, 1-naphtaldehyde of Formula 2, 2-naphtaldehyde of Formula 3, 5,8-dihydroxy- of Formula 4 1,4-naphthoquinone (5,8-Dihydroxy-1,4-naphthoquinone), Naphthalene of the formula (5), and phthalaldehyde (Phthalaldehyde) of the compound consisting of at least one compound selected from the group consisting of Contains acaricides: [화학식 1][Formula 1]
Figure 112005020774087-PAT00007
Figure 112005020774087-PAT00007
[화학식 2][Formula 2]
Figure 112005020774087-PAT00008
Figure 112005020774087-PAT00008
[화학식 3][Formula 3]
Figure 112005020774087-PAT00009
Figure 112005020774087-PAT00009
[화학식 4][Formula 4]
Figure 112005020774087-PAT00010
Figure 112005020774087-PAT00010
[화학식 5][Formula 5]
Figure 112005020774087-PAT00011
Figure 112005020774087-PAT00011
[화학식 6][Formula 6]
Figure 112005020774087-PAT00012
Figure 112005020774087-PAT00012
제 1항에 있어서, 상기 화학식 1 내지 6의 화합물은 세로무늬 먼지진드기(Dermatophagoides pteronyssinus) 및 큰다리 먼지진드기(Dermatophagoides farinae) 에 대하여 살비효과를 가지는 것을 특징으로 하는 살비제.The acaricide according to claim 1, wherein the compound of Chemical Formulas 1 to 6 has an acaricide effect against vertical pattern mites ( Dermatophagoides pteronyssinus ) and large leg mites ( Dermatophagoides farinae ). 제 1항에 있어서, 상기 화학식 1의 카프릴알데히드, 화학식 5의 나프탈렌, 및 화학식 6의 프탈알데히드는 저장식품 진드기(Tyrophagus putrescentiae)에 대하여 살비효과를 가지는 것을 특징으로 하는 살비제.The method of claim 1, wherein the caprylaldehyde of formula (1), naphthalene of formula (5), and phthalaldehyde of formula (6) are stored food ticks ( Tyrophagus) putrescentiae ) has an acaricide effect, characterized in that the acaricide. 제 1항에 있어서, 상기 살비제는 액제, 유제, 도포제, 훈연제, 훈증제, 입제 및 고형제로 이루어진 군에서 선택된 1종 이상의 제형 형태로 사용되는 것을 특징으로 하는 살비제.The acaricide according to claim 1, wherein the acaricide is used in the form of one or more formulations selected from the group consisting of liquids, emulsions, coatings, fumigants, fumigants, granules and solid agents.
KR1020050033127A 2005-04-21 2005-04-21 Chemical compound having acaricidal activity KR20060110655A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
KR1020050033127A KR20060110655A (en) 2005-04-21 2005-04-21 Chemical compound having acaricidal activity

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
KR1020050033127A KR20060110655A (en) 2005-04-21 2005-04-21 Chemical compound having acaricidal activity

Publications (1)

Publication Number Publication Date
KR20060110655A true KR20060110655A (en) 2006-10-25

Family

ID=37616419

Family Applications (1)

Application Number Title Priority Date Filing Date
KR1020050033127A KR20060110655A (en) 2005-04-21 2005-04-21 Chemical compound having acaricidal activity

Country Status (1)

Country Link
KR (1) KR20060110655A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100769708B1 (en) * 2006-09-21 2007-10-23 한국생명공학연구원 Chemical synthetic method for sulfonyl naphthoquinone compounds having pesticide and comprising their compounds
KR20160044927A (en) 2014-10-16 2016-04-26 전북대학교산학협력단 Natural acaricide for mite, Visual indicator for mite and Preparing method thereof
CN107072198A (en) * 2014-10-16 2017-08-18 全北大学校产学协力团 Natural acaricides for acarid, the identification for acarid are marked and preparation method thereof

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0152852A2 (en) * 1984-02-03 1985-08-28 Josef Dr. PÜHRINGER Antimicrobial agent for treating buildings, building materials, textiles, leather, agricultural products and foodstuffs
EP0292301A2 (en) * 1987-05-21 1988-11-23 JOHNSON & JOHNSON MEDICAL, INC. Odorless aromatic dialdehyde disinfecting and sterilizing composition
JPH1121262A (en) * 1997-07-01 1999-01-26 Tsumura & Co Naphthoquinone derivative and its use
EP1051909A1 (en) * 1999-05-11 2000-11-15 Sorex Limited The treatment of pests using substituted naphthoquinones
KR20030070222A (en) * 2002-02-21 2003-08-29 이회선 Chemical compound having acaricidal activity and indicator

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0152852A2 (en) * 1984-02-03 1985-08-28 Josef Dr. PÜHRINGER Antimicrobial agent for treating buildings, building materials, textiles, leather, agricultural products and foodstuffs
EP0292301A2 (en) * 1987-05-21 1988-11-23 JOHNSON & JOHNSON MEDICAL, INC. Odorless aromatic dialdehyde disinfecting and sterilizing composition
JPH1121262A (en) * 1997-07-01 1999-01-26 Tsumura & Co Naphthoquinone derivative and its use
EP1051909A1 (en) * 1999-05-11 2000-11-15 Sorex Limited The treatment of pests using substituted naphthoquinones
KR20030070222A (en) * 2002-02-21 2003-08-29 이회선 Chemical compound having acaricidal activity and indicator

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100769708B1 (en) * 2006-09-21 2007-10-23 한국생명공학연구원 Chemical synthetic method for sulfonyl naphthoquinone compounds having pesticide and comprising their compounds
KR20160044927A (en) 2014-10-16 2016-04-26 전북대학교산학협력단 Natural acaricide for mite, Visual indicator for mite and Preparing method thereof
CN107072198A (en) * 2014-10-16 2017-08-18 全北大学校产学协力团 Natural acaricides for acarid, the identification for acarid are marked and preparation method thereof

Similar Documents

Publication Publication Date Title
US6395789B1 (en) Non-hazardous pest control
JP3597479B2 (en) Sacrifice composition extracted from plants
CN111066808B (en) Ceramic tile cockroach-preventing agent, preparation method thereof, ceramic tile cockroach-preventing method and cockroach-preventing ceramic tile
KR20060110655A (en) Chemical compound having acaricidal activity
JPH0459703A (en) Miticide
JPH0461842B2 (en)
KR100472643B1 (en) Composition comprising plant oil and chemical compound having acaricidal activity
KR100624103B1 (en) Plant oil and chemical compound having acaricidal activity
KR101893125B1 (en) Composition for anti-insect coating
KR100654902B1 (en) Chemical compound having acaricidal activity
KR101288541B1 (en) Composition of acaricidal components containing Acetophenone's derivatives and acaricide using the same
JP7078314B2 (en) In-building pest control method and in-building pest control composition
KR20030000680A (en) Composition of acaricidal components
JP2993729B2 (en) Acaricide or mitic repellent
JPH01163104A (en) Extermination agent for household mite
KR100415622B1 (en) Chemical compound having acaricidal activity and indicator
WO2023095882A1 (en) Method for reducing allergens and allergen-reducing agent
RU2214093C2 (en) Preparation for protection against keratophages
JP3024765B2 (en) Granular insecticidal composition
JPH0578216A (en) Miticide for indoor use
JP2011153108A (en) Method for enhancing controlling efficacy for house dust mite, smoking agent composition for controlling house dust mite, and method for controlling house dust mite
JPH07138112A (en) Indoor dusty acaricide
JPH08225417A (en) Aerosol agent for controlling house tick
JPH08208413A (en) Aerosolagent for controlling interior mite
JPH05170601A (en) Insect-proofing agent

Legal Events

Date Code Title Description
A201 Request for examination
E902 Notification of reason for refusal
E601 Decision to refuse application