JP2022140500A - Curable composition for crawling pest control, sealing material, and crawling pest control method - Google Patents
Curable composition for crawling pest control, sealing material, and crawling pest control method Download PDFInfo
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- JP2022140500A JP2022140500A JP2022112978A JP2022112978A JP2022140500A JP 2022140500 A JP2022140500 A JP 2022140500A JP 2022112978 A JP2022112978 A JP 2022112978A JP 2022112978 A JP2022112978 A JP 2022112978A JP 2022140500 A JP2022140500 A JP 2022140500A
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- pest control
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- 239000000203 mixture Substances 0.000 title claims abstract description 102
- 241000607479 Yersinia pestis Species 0.000 title claims abstract description 87
- 238000000034 method Methods 0.000 title claims abstract description 23
- 230000009193 crawling Effects 0.000 title claims abstract description 21
- 239000003566 sealing material Substances 0.000 title claims abstract description 12
- -1 carboxylic acid diester Chemical class 0.000 claims abstract description 72
- 229920000642 polymer Polymers 0.000 claims abstract description 70
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 47
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims abstract description 34
- 229920001451 polypropylene glycol Polymers 0.000 claims abstract description 29
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- OMFRMAHOUUJSGP-IRHGGOMRSA-N bifenthrin Chemical compound C1=CC=C(C=2C=CC=CC=2)C(C)=C1COC(=O)[C@@H]1[C@H](\C=C(/Cl)C(F)(F)F)C1(C)C OMFRMAHOUUJSGP-IRHGGOMRSA-N 0.000 claims abstract description 17
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- VQXSOUPNOZTNAI-UHFFFAOYSA-N Pyrethrin I Natural products CC(=CC1CC1C(=O)OC2CC(=O)C(=C2C)CC=C/C=C)C VQXSOUPNOZTNAI-UHFFFAOYSA-N 0.000 claims abstract description 7
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- VJFUPGQZSXIULQ-XIGJTORUSA-N pyrethrin II Chemical group CC1(C)[C@H](/C=C(\C)C(=O)OC)[C@H]1C(=O)O[C@@H]1C(C)=C(C\C=C/C=C)C(=O)C1 VJFUPGQZSXIULQ-XIGJTORUSA-N 0.000 claims abstract description 7
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- 239000004480 active ingredient Substances 0.000 description 3
- 229960005286 carbaryl Drugs 0.000 description 3
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- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- HPYNBECUCCGGPA-UHFFFAOYSA-N silafluofen Chemical compound C1=CC(OCC)=CC=C1[Si](C)(C)CCCC1=CC=C(F)C(OC=2C=CC=CC=2)=C1 HPYNBECUCCGGPA-UHFFFAOYSA-N 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229920002379 silicone rubber Polymers 0.000 description 1
- 239000004945 silicone rubber Substances 0.000 description 1
- 239000004590 silicone sealant Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- XIUROWKZWPIAIB-UHFFFAOYSA-N sulfotep Chemical compound CCOP(=S)(OCC)OP(=S)(OCC)OCC XIUROWKZWPIAIB-UHFFFAOYSA-N 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000005936 tau-Fluvalinate Substances 0.000 description 1
- INISTDXBRIBGOC-XMMISQBUSA-N tau-fluvalinate Chemical compound N([C@H](C(C)C)C(=O)OC(C#N)C=1C=C(OC=2C=CC=CC=2)C=CC=1)C1=CC=C(C(F)(F)F)C=C1Cl INISTDXBRIBGOC-XMMISQBUSA-N 0.000 description 1
- CJDWRQLODFKPEL-UHFFFAOYSA-N teflubenzuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC1=CC(Cl)=C(F)C(Cl)=C1F CJDWRQLODFKPEL-UHFFFAOYSA-N 0.000 description 1
- 229950004921 temefos Drugs 0.000 description 1
- WWJZWCUNLNYYAU-UHFFFAOYSA-N temephos Chemical compound C1=CC(OP(=S)(OC)OC)=CC=C1SC1=CC=C(OP(=S)(OC)OC)C=C1 WWJZWCUNLNYYAU-UHFFFAOYSA-N 0.000 description 1
- 229960005199 tetramethrin Drugs 0.000 description 1
- 239000004308 thiabendazole Substances 0.000 description 1
- WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 description 1
- 229960004546 thiabendazole Drugs 0.000 description 1
- 235000010296 thiabendazole Nutrition 0.000 description 1
- BAKXBZPQTXCKRR-UHFFFAOYSA-N thiodicarb Chemical compound CSC(C)=NOC(=O)NSNC(=O)ON=C(C)SC BAKXBZPQTXCKRR-UHFFFAOYSA-N 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 150000003609 titanium compounds Chemical class 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- YWSCPYYRJXKUDB-KAKFPZCNSA-N tralomethrin Chemical compound CC1(C)[C@@H](C(Br)C(Br)(Br)Br)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 YWSCPYYRJXKUDB-KAKFPZCNSA-N 0.000 description 1
- AMFGTOFWMRQMEM-UHFFFAOYSA-N triazophos Chemical compound N1=C(OP(=S)(OCC)OCC)N=CN1C1=CC=CC=C1 AMFGTOFWMRQMEM-UHFFFAOYSA-N 0.000 description 1
- NFACJZMKEDPNKN-UHFFFAOYSA-N trichlorfon Chemical compound COP(=O)(OC)C(O)C(Cl)(Cl)Cl NFACJZMKEDPNKN-UHFFFAOYSA-N 0.000 description 1
- XAIPTRIXGHTTNT-UHFFFAOYSA-N triflumuron Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)NC(=O)C1=CC=CC=C1Cl XAIPTRIXGHTTNT-UHFFFAOYSA-N 0.000 description 1
- AZJYLVAUMGUUBL-UHFFFAOYSA-A u1qj22mc8e Chemical compound [F-].[F-].[F-].[F-].[F-].[F-].[F-].[F-].[F-].[F-].[F-].[F-].[F-].[F-].[F-].[F-].[F-].[F-].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].O=[Si]=O.O=[Si]=O.O=[Si]=O.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3 AZJYLVAUMGUUBL-UHFFFAOYSA-A 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- WCJYTPVNMWIZCG-UHFFFAOYSA-N xylylcarb Chemical compound CNC(=O)OC1=CC=C(C)C(C)=C1 WCJYTPVNMWIZCG-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 229940043810 zinc pyrithione Drugs 0.000 description 1
- PICXIOQBANWBIZ-UHFFFAOYSA-N zinc;1-oxidopyridine-2-thione Chemical compound [Zn+2].[O-]N1C=CC=CC1=S.[O-]N1C=CC=CC1=S PICXIOQBANWBIZ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION 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
- A01N25/00—Biocides, 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
- A01N25/02—Biocides, 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
- A01N25/04—Dispersions, emulsions, suspoemulsions, suspension concentrates or gels
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/22—O-Aryl or S-Aryl esters thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/09—Carboxylic acids; Metal salts thereof; Anhydrides thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/10—Esters; Ether-esters
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/35—Heterocyclic compounds having nitrogen in the ring having also oxygen in the ring
- C08K5/353—Five-membered rings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
- C08L71/02—Polyalkylene oxides
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K3/00—Materials not provided for elsewhere
- C09K3/10—Materials in mouldable or extrudable form for sealing or packing joints or covers
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
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- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
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Abstract
Description
本発明は、匍匐害虫防除用硬化性組成物、シーリング材、並びに、匍匐害虫の防除方法に関する。本発明は、チャタテムシ等の匍匐害虫の防除に有用なものである。 TECHNICAL FIELD The present invention relates to a curable composition for controlling creeping pests, a sealing material, and a method for controlling creeping pests. INDUSTRIAL APPLICABILITY The present invention is useful for controlling crawling pests such as bookworms.
チャタテムシは体長１～２ｍｍ程度の微小昆虫であり、主にカビ類を餌としている。チャタテムシは人に直接被害を与えるものではないが、いわゆる不快害虫と認識されている。近年、一般家屋や工場、貯蔵食物、古い書物などにチャタテムシが大量発生する事例が増えており、大きな問題となっている。特に食品工場や医薬品工場では、虫体の製品への混入リスクが高まり、その対策が求められている。 Bookworms are microscopic insects with a body length of about 1 to 2 mm, and mainly feed on fungi. Bookworms do not directly harm humans, but are recognized as so-called nuisance pests. In recent years, there have been an increasing number of cases of bookworms infesting general houses, factories, stored food, old books, etc., and this has become a serious problem. Especially in food factories and pharmaceutical factories, the risk of contamination of products with insect bodies is increasing, and countermeasures are required.
チャタテムシが生息する場所は間仕切壁裏面や天井裏が主であり、餌を求めて、シーリング材や幅木の亀裂、隙間から、室内に出現する。チャタテムシの防除方法としては、殺虫液剤や殺虫エアゾール剤を直接噴霧することや、燻蒸剤で部屋全体や工場内全体を燻蒸することが挙げられる。しかしこれらの方法では、一般家屋の場合には殺虫剤の人体への暴露の問題があり、工場の場合には生産物への殺虫剤混入のリスクがある。 Bookworms live mainly on the back of partition walls and ceilings, and appear indoors through cracks and crevices in sealing materials and baseboards in search of food. Methods for controlling bookworms include direct spraying of insecticide liquids and insecticide aerosols, and fumigation of entire rooms and factories with fumigants. However, with these methods, there is a problem of exposure of the human body to insecticides in the case of ordinary houses, and there is a risk of contamination of products with insecticides in the case of factories.
室内への害虫の侵入を防ぐために、殺虫剤や害虫忌避剤を含有するシーリング材が開発されている。例えば特許文献１には、殺虫剤及び／又は害虫忌避剤としてピレスロイド系化合物を含有するシーリング材について記載されている。特許文献２には、ピレスロイド系化合物の１つであるアクリナトリンを配合したシリコーンゴム組成物について記載されている。 Sealing materials containing insecticides and pest repellents have been developed to prevent pests from entering indoor spaces. For example, Patent Document 1 describes a sealing material containing a pyrethroid compound as an insecticide and/or insect repellent. Patent Document 2 describes a silicone rubber composition containing acrinathrin, which is one of the pyrethroid compounds.
チャタテムシに対する殺虫剤の効果を調べた報告として、以下の非特許文献１、２がある。 The following Non-Patent Documents 1 and 2 are reports examining the effect of insecticides on bookworms.
近年の住宅は気密性が高く湿気がこもるためカビが繁殖しやすく、チャタテムシが発生しやすい。また工場においては虫体の異物混入のリスクをできる限り排除する必要がある。そのため、チャタテムシ等の害虫の発生と屋内への侵入を防止するための更なる技術開発が望まれる。
そこで本発明は、チャタテムシ等の匍匐害虫の防除に有用な技術を提供することを目的とする。
Houses in recent years are highly airtight and tend to be filled with moisture, making it easier for mold to grow and more likely for bookbugs to grow. In factories, it is necessary to eliminate the risk of contamination by insect bodies as much as possible. Therefore, further technical development is desired to prevent pests such as bookworms from occurring and from entering indoors.
Accordingly, an object of the present invention is to provide a technique useful for controlling crawling pests such as bookworms.
本発明者らは、チャタテムシ等の害虫の屋内への侵入を防止するための、室温硬化性樹脂を用いた殺虫組成物を検討し、その中で変性シリコーン系シーリング材用の硬化性樹脂に着目し、害虫防除能を付与するべく種々検討を行った。 The present inventors have investigated an insecticidal composition using a room temperature curable resin for preventing insect pests such as bookworms from entering indoors. Various investigations were carried out in order to impart pest control ability.
本発明の１つの様相は、（Ａ）下記一般式（１）：
－Ｓｉ（Ｒ１）３－ａＸａ （１）
（式中、Ｒ１は１価炭化水素基又はハロゲン化１価炭化水素基を表し、Ｘは水素原子、ハロゲン原子、又はアルコキシ基を表し、ａは０～３の整数を表す。）
で表される反応性ケイ素基を１分子中に少なくとも１個含有するポリオキシアルキレン系重合体を主成分とする基材、
（Ｂ）炭素数４～１２アルコールの２価カルボン酸ジエステル及び／又はポリプロピレングリコール、並びに、
（Ｃ）害虫防除剤、
を含む、匍匐害虫防除用硬化性組成物である。
One aspect of the present invention is (A) the following general formula (1):
—Si(R 1 ) 3-a X a (1)
(Wherein, R 1 represents a monovalent hydrocarbon group or a halogenated monovalent hydrocarbon group, X represents a hydrogen atom, a halogen atom, or an alkoxy group, and a represents an integer of 0 to 3.)
A substrate mainly composed of a polyoxyalkylene-based polymer containing at least one reactive silicon group per molecule represented by
(B) C4-C12 alcohol divalent carboxylic acid diester and/or polypropylene glycol, and
(C) a pest control agent;
A curable composition for controlling crawling pests, comprising
好ましくは、前記害虫防除剤が、ピレスロイド系化合物、カーバメート系化合物及び有機リン系化合物からなる群から選ばれる少なくとも１種である。 Preferably, the pest control agent is at least one selected from the group consisting of pyrethroid compounds, carbamate compounds and organophosphorus compounds.
好ましくは、前記害虫防除剤がピレスロイド系化合物である。 Preferably, the pest control agent is a pyrethroid compound.
好ましくは、前記ピレスロイド系化合物が、ピレトリン、トランスフルトリン、又はビフェントリンである。 Preferably, the pyrethroid compound is pyrethrin, transfluthrin, or bifenthrin.
好ましくは、さらに共力剤を含む。 Preferably, it further contains a synergist.
好ましくは、前記共力剤が、Ｎ－（２－エチルヘキシル）ビシクロ[２．２．１]ヘプト－５－エン－２，３－ジカルボキシイミド又はピペロニルブトキシドである。 Preferably, said synergist is N-(2-ethylhexyl)bicyclo[2.2.1]hept-5-ene-2,3-dicarboximide or piperonyl butoxide.
好ましくは、前記ピレスロイド系化合物が、ピレトリン、トランスフルトリン、又はビフェントリンであり、前記共力剤が、Ｎ－（２－エチルヘキシル）ビシクロ[２．２．１]ヘプト－５－エン－２，３－ジカルボキシイミド又はピペロニルブトキシドである。 Preferably, the pyrethroid compound is pyrethrin, transfluthrin, or bifenthrin, and the synergist is N-(2-ethylhexyl)bicyclo[2.2.1]hept-5-ene-2,3 - dicarboximide or piperonyl butoxide.
好ましくは、前記ピレスロイド系化合物がビフェントリンであり、前記共力剤がＮ－（２－エチルヘキシル）ビシクロ[２．２．１]ヘプト－５－エン－２，３－ジカルボキシイミドである。 Preferably, the pyrethroid compound is bifenthrin and the synergist is N-(2-ethylhexyl)bicyclo[2.2.1]hept-5-ene-2,3-dicarboximide.
好ましくは、前記ピレスロイド系化合物がビフェントリンであり、前記共力剤がピペロニルブトキシドである。 Preferably, the pyrethroid compound is bifenthrin and the synergist is piperonyl butoxide.
好ましくは、前記ピレスロイド系化合物がトランスフルトリンであり、前記共力剤がＮ－（２－エチルヘキシル）ビシクロ[２．２．１]ヘプト－５－エン－２，３－ジカルボキシイミドである。 Preferably, the pyrethroid compound is transfluthrin and the synergist is N-(2-ethylhexyl)bicyclo[2.2.1]hept-5-ene-2,3-dicarboximide.
好ましくは、前記ピレスロイド系化合物１重量部に対して、前記共力剤を１重量部～２０重量部含む。 Preferably, the synergist is contained in an amount of 1 to 20 parts by weight with respect to 1 part by weight of the pyrethroid compound.
好ましくは、前記害虫防除剤がカーバメート系化合物である。 Preferably, the pest control agent is a carbamate-based compound.
好ましくは、前記カーバメート系化合物が、メトキサジアゾン、カルバリル、フェノブカルブ、又はプロポキスルである。 Preferably, the carbamate compound is methoxadiazone, carbaryl, fenocarb, or propoxur.
好ましくは、（Ａ）１００重量部に対し、（Ｂ）を１０重量部～８０重量部、（Ｃ）を０．１重量部～１０重量部含む。 Preferably, 10 to 80 parts by weight of (B) and 0.1 to 10 parts by weight of (C) are included with respect to 100 parts by weight of (A).
好ましくは、前記反応性ケイ素基が、トリメトキシシリル基、メチルジメトキシシリル基、ジメチルメトキシシリル基、トリエトキシシリル基、メチルジエトキシシリル基、及びメチルジメトキシエトキシシリル基からなる群から選ばれる少なくとも１つである。 Preferably, the reactive silicon group is at least one selected from the group consisting of a trimethoxysilyl group, a methyldimethoxysilyl group, a dimethylmethoxysilyl group, a triethoxysilyl group, a methyldiethoxysilyl group, and a methyldimethoxyethoxysilyl group. is one.
好ましくは、前記ポリオキシアルキレン系重合体が、ポリオキシエチレン、ポリオキシプロピレン、又はポリオキシブチレンである。 Preferably, the polyoxyalkylene polymer is polyoxyethylene, polyoxypropylene, or polyoxybutylene.
好ましくは、前記基材が、さらに反応性ケイ素基を有する（メタ）アクリル酸エステル系重合体を含む。 Preferably, the substrate further contains a (meth)acrylate polymer having a reactive silicon group.
好ましくは、さらに昆虫成長制御剤、防黴剤、硬化剤、充填剤、垂れ防止剤、脱水剤、光安定剤、紫外線吸収剤、及び酸化防止剤からなる群から選ばれる少なくとも１つの成分を含む。 Preferably, it further contains at least one component selected from the group consisting of insect growth regulators, antifungal agents, curing agents, fillers, anti-sagging agents, dehydrating agents, light stabilizers, UV absorbers, and antioxidants. .
好ましくは、前記匍匐害虫がチャタテムシ類である。 Preferably, the creeping pests are bookworms.
本発明の他の様相は、上記の匍匐害虫防除用硬化性組成物を含む、シーリング材である。 Another aspect of the present invention is a sealant containing the curable composition for controlling creeping pests.
本発明の他の様相は、上記の匍匐害虫防除用硬化性組成物又は上記のシーリング材を用いて匍匐害虫を防除する、匍匐害虫の防除方法である。 Another aspect of the present invention is a method for controlling creeping pests, wherein the curable composition for controlling creeping pests or the sealing material is used to control creeping pests.
本発明によれば、チャタテムシ等の匍匐害虫を効率的に防除することができる。 According to the present invention, crawling pests such as bookworms can be efficiently controlled.
本発明の匍匐害虫防除用硬化性組成物は、（Ａ）下記一般式（１）：
－Ｓｉ（Ｒ１）３－ａＸａ （１）
（式中、Ｒ１は１価炭化水素基又はハロゲン化１価炭化水素基を表し、Ｘは水素原子、ハロゲン原子、又はアルコキシ基を表し、ａは０～３の整数を表す。）
で表される反応性ケイ素基を１分子中に少なくとも１個含有するポリオキシアルキレン系重合体を主成分とする基材、
（Ｂ）炭素数４～１２アルコールの２価カルボン酸ジエステル及び／又はポリプロピレングリコール、並びに、
（Ｃ）害虫防除剤、
を含むものである。
The curable composition for controlling crawling pests of the present invention has (A) the following general formula (1):
—Si(R 1 ) 3-a X a (1)
(Wherein, R 1 represents a monovalent hydrocarbon group or a halogenated monovalent hydrocarbon group, X represents a hydrogen atom, a halogen atom, or an alkoxy group, and a represents an integer of 0 to 3.)
A substrate mainly composed of a polyoxyalkylene polymer containing at least one reactive silicon group in one molecule represented by
(B) C4-C12 alcohol divalent carboxylic acid diester and/or polypropylene glycol, and
(C) a pest control agent;
includes.
上記ポリオキシアルキレン系重合体は、いわゆる変性シリコーン系シーリング材を構成する重合体である。一般に、変性シリコーン系シーリング材とは、末端に反応性シリル基（反応性ケイ素基）を導入したシリル化ポリエーテルを主成分とし、湿気硬化でシロキサン結合を形成するものを指す（日本シーリング材工業会「建築用シーリング材－基礎と正しい使い方－」第３版（平成２４年１０月１日発行）ｐ１８２）。反応性ケイ素基は、加水分解性ケイ素基、架橋性ケイ素基、とも称される。 The above polyoxyalkylene polymer is a polymer that constitutes a so-called modified silicone sealant. In general, modified silicone-based sealants are those whose main component is silylated polyether with reactive silyl groups (reactive silicon groups) introduced at the ends, and which form siloxane bonds when cured with moisture (Nippon Sealant Industry Co., Ltd. ``Building Sealing Materials - Basics and Correct Usage-'' 3rd Edition (published October 1, 2012) p182). Reactive silicon groups are also referred to as hydrolyzable silicon groups or crosslinkable silicon groups.
本発明の匍匐害虫防除用硬化性組成物の（Ａ）成分である基材は、上記ポリオキシアルキレン系重合体を主成分とするものである。ここで「主成分」とは、基材中における含有量が５０重量％以上であることを指し、好ましくは６０重量％以上、より好ましくは６６重量％以上である。副成分を含めず、上記ポリオキシアルキレン系重合体のみで（Ａ）成分を構成してもよい。 The base material, which is the component (A) of the curable composition for controlling creeping pests of the present invention, contains the polyoxyalkylene polymer as a main component. Here, the "main component" means that the content in the substrate is 50% by weight or more, preferably 60% by weight or more, and more preferably 66% by weight or more. The component (A) may be composed only of the above polyoxyalkylene-based polymer without containing any subcomponents.
上記ポリオキシアルキレン系重合体としては、例えば、下記のオキシアルキレン単位が複数個連なったポリオキシアルキレン骨格を含むものが挙げられる。
－（ＣＨ２）ｎ－Ｏ－（ｎは１～４の整数）
－ＣＨ２ＣＨ（ＣＨ３）－Ｏ－
－ＣＨ２ＣＨ（Ｃ２Ｈ５）－Ｏ－
－ＣＨ２Ｃ（ＣＨ３）２－Ｏ－
－ＣＨ２ＣＨ（ＣＨ＝ＣＨ２）－Ｏ－
これらの中で、ポリオキシエチレン（－ＣＨ２－ＣＨ２－Ｏ－）、ポリオキシプロピレン（－ＣＨ２ＣＨ（ＣＨ３）－Ｏ－）、ポリオキシブチレン（－ＣＨ２ＣＨ（Ｃ２Ｈ５）－Ｏ－）が好ましく、作業性に優れる点でポリオキシプロピレンが特に好ましい。
上記ポリオキシアルキレン系重合体には、上記の繰り返し単位が１種又は２種以上含まれていてもよい。
Examples of the polyoxyalkylene-based polymer include those containing a polyoxyalkylene skeleton in which a plurality of the following oxyalkylene units are linked.
—(CH 2 ) n —O— (n is an integer of 1 to 4)
-CH2CH ( CH3 )-O-
-CH2CH ( C2H5 )-O-
-CH2C( CH3 ) 2 - O-
-CH2CH(CH = CH2 )-O-
Among these are polyoxyethylene (--CH 2 --CH 2 --O--), polyoxypropylene (--CH 2 CH(CH 3 )--O--), polyoxybutylene (--CH 2 CH(C 2 H 5 )—O—) is preferable, and polyoxypropylene is particularly preferable in terms of excellent workability.
The above polyoxyalkylene polymer may contain one or more of the above repeating units.
上記ポリオキシアルキレン系重合体は直鎖状でもよく、分鎖を有するものでもよい。上記ポリオキシアルキレン系重合体の数平均分子量は、４０００～３００００であることが好ましい。このような反応性ケイ素基を有するポリオキシアルキレン系重合体の具体例としては、株式会社カネカ製の商品名「ＭＳポリマーＳ２０３」、「ＭＳポリマーＳ３０３」、「ＭＳポリマーＳ２０３Ｈ」、及び「ＭＳポリマーＳ３０３Ｈ」、旭硝子株式会社製 の商品名「エクセスターＥＳ２４１０」、等が例示される。なお、リビングラジカル重合法を用いることによって、デッドポリマーが少なく分子量分布が狭いポリオキシアルキレン系重合体を得ることができる。 The polyoxyalkylene polymer may be linear or branched. The polyoxyalkylene polymer preferably has a number average molecular weight of 4,000 to 30,000. Specific examples of polyoxyalkylene-based polymers having such reactive silicon groups include trade names "MS Polymer S203", "MS Polymer S303", "MS Polymer S203H" and "MS Polymer" manufactured by Kaneka Corporation. S303H", Asahi Glass Co., Ltd. trade name "Excester ES2410", and the like. By using the living radical polymerization method, it is possible to obtain a polyoxyalkylene-based polymer having a small amount of dead polymer and a narrow molecular weight distribution.
上記一般式（１）で表される反応性ケイ素基としては、トリアルコキシシリル基、アルキルジアルコキシシリル基、ジアルキルアルコキシシリル基、等が挙げられる。ここでアルコキシ基、アルキル基の炭素数は１０以下が好ましく、メトキシ基、エトキシ基、メチル基、エチル基がさらに好ましい。
トリアルコキシシリル基としては、トリメトキシシリル基、トリエトキシシリル基、等が挙げられる。アルキルジアルコキシシリル基としては、メチルジメトキシシリル基、メチルジエトキシシリル基、メチルジメトキシエトキシシリル基、等が挙げられる。ジアルキルアルコキシシリル基としては、ジメチルメトキシシリル基等が挙げられる。
これらの中で、トリメトキシシリル基とメチルジメトキシシリル基が特に好ましい。
Examples of the reactive silicon group represented by the general formula (1) include a trialkoxysilyl group, an alkyldialkoxysilyl group, a dialkylalkoxysilyl group, and the like. Here, the number of carbon atoms in the alkoxy group and alkyl group is preferably 10 or less, more preferably methoxy group, ethoxy group, methyl group and ethyl group.
The trialkoxysilyl group includes a trimethoxysilyl group, a triethoxysilyl group, and the like. The alkyldialkoxysilyl group includes a methyldimethoxysilyl group, a methyldiethoxysilyl group, a methyldimethoxyethoxysilyl group, and the like. A dimethylmethoxysilyl group etc. are mentioned as a dialkylalkoxysilyl group.
Among these, a trimethoxysilyl group and a methyldimethoxysilyl group are particularly preferred.
反応性ケイ素基の数としては、上記ポリオキシアルキレン系重合体１分子中に少なくとも１個あればよい。反応性ケイ素基は、上記ポリオキシアルキレン系重合体の主鎖と側鎖のいずれに導入されていてもよく、分子鎖末端に導入されていることが好ましい。 The number of reactive silicon groups should be at least one per molecule of the polyoxyalkylene polymer. The reactive silicon group may be introduced into either the main chain or the side chain of the polyoxyalkylene polymer, and is preferably introduced into the terminal of the molecular chain.
上記ポリオキシアルキレン系重合体の分子鎖末端に対する反応性ケイ素基の導入率は特に限定されるものではないが、５０％以上であることが好ましい。なお、反応性ケイ素基の導入率について、分子鎖末端の官能基が水酸基の場合は、例えば、反応性ケイ素基導入後の未反応の水酸基を水酸基価分析法にて定量および算出することができる。分子鎖末端の官能基が水酸基以外の場合は、例えば、赤外分光法や核磁気共鳴法などを用いて、反応性ケイ素基導入後の未反応の官能基を定量および算出することができる。 Although the introduction ratio of reactive silicon groups to the molecular chain ends of the polyoxyalkylene polymer is not particularly limited, it is preferably 50% or more. Regarding the introduction rate of reactive silicon groups, when the functional group at the end of the molecular chain is a hydroxyl group, for example, unreacted hydroxyl groups after the introduction of reactive silicon groups can be quantified and calculated by hydroxyl value analysis. . If the functional group at the end of the molecular chain is other than a hydroxyl group, the unreacted functional group after the introduction of the reactive silicon group can be quantified and calculated using, for example, infrared spectroscopy or nuclear magnetic resonance.
反応性ケイ素基を有するポリオキシアルキレン系重合体は、公知の方法で製造することができる。例えば、上記した「建築用シーリング材－基礎と正しい使い方－（第３版）」のｐ１８２－１８３に記載の方法が挙げられる。具体的には、分子量３０００程度のポリプロピレングリコール（ＰＰＧ）の末端ヒドロキシル基をアルコキシド基に転換させた後、多価ハロゲン化合物を反応させることによって分子量を増大させ、分子量延長反応により高分子量化する。次に、ＣＨ２＝ＣＨＲＸで示される有機ハロゲン化合物を反応させることによって末端にオレフィン基を導入する。その後、脱塩精製工程を経てヒドロキシル化反応によって末端に反応性のシリコーン官能基（反応性ケイ素基）を導入する。 A polyoxyalkylene polymer having a reactive silicon group can be produced by a known method. For example, the method described on pp. 182-183 of the above-mentioned "Sealant for construction -Foundation and correct usage- (3rd edition)" can be mentioned. Specifically, after converting the terminal hydroxyl group of polypropylene glycol (PPG) having a molecular weight of about 3000 to an alkoxide group, the molecular weight is increased by reacting with a polyvalent halogen compound, and the molecular weight elongation reaction is performed to increase the molecular weight. Next, an olefinic group is introduced at the end by reacting an organic halogen compound represented by CH 2 =CHRX. After that, a reactive silicone functional group (reactive silicon group) is introduced to the end by a hydroxylation reaction through a desalting purification step.
下記（イ）又は（ロ）の方法によっても、反応性ケイ素基をポリオキシアルキレン系重合体に導入することができる（特許第３９１３８５９号公報）。
（イ）分子中に水酸基等の官能基を有するオキシアルキレン系重合体に、この官能基に対して反応性を示す活性基及び不飽和基を有する有機化合物を反応させ、不飽和基を含有するオキシアルキレン系重合体を得るか、又は、不飽和基含有エポキシ化合物との共重合により不飽和基を含有するオキシアルキレン系重合体を得る。次いで、得られた不飽和基を含有するオキシアルキレン系重合体に反応性ケイ素基を有するヒドロシランを作用させてヒドロシリル化する。
A reactive silicon group can also be introduced into a polyoxyalkylene polymer by the following method (a) or (b) (Japanese Patent No. 3913859).
(b) An oxyalkylene polymer having a functional group such as a hydroxyl group in the molecule is reacted with an organic compound having an active group and an unsaturated group that exhibit reactivity with the functional group to obtain an unsaturated group. An oxyalkylene polymer is obtained, or an oxyalkylene polymer containing an unsaturated group is obtained by copolymerization with an epoxy compound containing an unsaturated group. Then, the resulting oxyalkylene polymer containing an unsaturated group is hydrosilylated by reacting it with a hydrosilane having a reactive silicon group.
（ロ）分子中に水酸基、エポキシ基やイソシアネート基等の官能基を有するオキシアルキレン系重合体に、この官能基に対して反応性を示す官能基及び反応性ケイ素基を有する化合物を反応させる。 (b) An oxyalkylene polymer having a functional group such as a hydroxyl group, an epoxy group or an isocyanate group in its molecule is reacted with a compound having a reactive silicon group and a functional group showing reactivity to the functional group.
その他、反応性ケイ素基を有するポリオキシアルキレン系重合体の製造方法は、特開昭５０－１５６５９９号公報、特開昭５２－７３９９８号公報、特開昭６０－６７４７号公報、等の文献に記載されている。 In addition, the method for producing a polyoxyalkylene polymer having a reactive silicon group is described in documents such as JP-A-50-156599, JP-A-52-73998, and JP-A-60-6747. Have been described.
（Ａ）の主成分である上記ポリオキシアルキレン系重合体以外の成分（副成分）としては、反応性ケイ素基を有する（メタ）アクリル酸エステル系重合体が挙げられる。すなわち本発明の匍匐害虫防除用硬化性組成物においては、上記ポリオキシアルキレン系重合体（以下、重合体（ａ－１）と称することがある。）と反応性ケイ素基を有する（メタ）アクリル酸エステル系重合体（以下、重合体（ａ－２）と称することがある。）とを併用することができる。これにより、硬化したシーリング材の耐候性や接着性が向上する。重合体（ａ－２）としては、例えば、上記一般式（１）で表される反応性ケイ素基を１分子中に少なくとも１個含有する（メタ）アクリル酸エステル系重合体が挙げられる。重合体（ａ－１）と重合体（ａ－２）とを併用した重合体の具体例としては、株式会社カネカ製の商品名「ＭＳポリマーＳ９０３」、「ＭＳポリマーＳ９４３」が例示される。 Components (subcomponents) other than the polyoxyalkylene-based polymer, which is the main component of (A), include (meth)acrylic acid ester-based polymers having reactive silicon groups. That is, in the curable composition for controlling crawling pests of the present invention, the above polyoxyalkylene polymer (hereinafter sometimes referred to as polymer (a-1)) and a (meth)acryl having a reactive silicon group An acid ester polymer (hereinafter sometimes referred to as polymer (a-2)) can be used in combination. This improves the weather resistance and adhesiveness of the cured sealant. Examples of the polymer (a-2) include a (meth)acrylic acid ester polymer containing at least one reactive silicon group represented by the general formula (1) per molecule. Specific examples of polymers in which polymer (a-1) and polymer (a-2) are used in combination include trade names “MS Polymer S903” and “MS Polymer S943” manufactured by Kaneka Corporation.
重合体（ａ－１）に対する重合体（ａ－２）の配合量としては、重合体（ａ－１）１００重量部に対して１重量部～１００重量部が好ましく、より好ましくは１０重量部～１００重量部、さらに好ましくは１０重量部～８０重量部である。 The blending amount of the polymer (a-2) relative to the polymer (a-1) is preferably 1 to 100 parts by weight, more preferably 10 parts by weight, per 100 parts by weight of the polymer (a-1). 100 parts by weight, more preferably 10 parts to 80 parts by weight.
（メタ）アクリル酸エステル系重合体は、公知の方法で製造することができる。例えば、アリル基を有する（メタ）アクリル酸エステル系重合体を、VIII族金属の存在下でヒドロシリコン化合物と反応させる方法（特開昭５４－３６３９５号公報）、アルキル（メタ）アクリレートを、アルコキシシリル基を含有するアルキル（メタ）アクリレート、及びメルカプト基を含有する連鎖移動剤の存在下で共重合させる方法（特開昭５７－１７９２１０号公報）、アルキル（メタ）アクリレートを、２官能ラジカル重合性化合物及び連鎖移動剤としてアルコキシシリル基を含有するメルカプタンの存在下で共重合させる方法（特開昭５９－７８２２２号公報）、アルキル（メタ）アクリレートを、重合開始剤としてアルコキシシリル基を含有するアゾビスニトリル化合物を使用して重合する方法（特開昭６０－２３４０５号公報）、等を用いて製造することができる（特開２００２－２０１３５０号公報）。 A (meth)acrylic ester-based polymer can be produced by a known method. For example, a method of reacting a (meth)acrylic acid ester polymer having an allyl group with a hydrosilicon compound in the presence of a group VIII metal (JP-A-54-36395), an alkyl (meth)acrylate, an alkoxy A method of copolymerizing in the presence of an alkyl (meth) acrylate containing a silyl group and a chain transfer agent containing a mercapto group (JP-A-57-179210), an alkyl (meth) acrylate is subjected to bifunctional radical polymerization. A method of copolymerizing in the presence of a mercaptan containing an alkoxysilyl group as a chemical compound and a chain transfer agent (JP-A-59-78222), an alkyl (meth)acrylate containing an alkoxysilyl group as a polymerization initiator. It can be produced by a method of polymerization using an azobisnitrile compound (JP-A-60-23405), etc. (JP-A-2002-201350).
本発明の匍匐害虫防除用硬化性組成物は、（Ｂ）炭素数４～１２アルコールの２価カルボン酸ジエステル及び／又はポリプロピレングリコール、を含有する。
炭素数４～１２アルコールの２価カルボン酸ジエステルとしては、フタル酸ジエステルやアジピン酸ジエステルが挙げられ、特にフタル酸ジエステルが好ましく、その中でもフタル酸ジエチルヘキシル、フタル酸ジイソノニルが害虫防除剤の溶解性が良好なことから特に好ましい。
ポリプロピレングリコールとしては、分子量１０００～５０００のものが低粘度であることから取扱い易く好ましい。ポリプロピレングリコールはジオール型、トリオール型のいずれを使用してもよい。
The curable composition for controlling crawling pests of the present invention contains (B) a dihydric carboxylic acid diester of 4 to 12 carbon atoms alcohol and/or polypropylene glycol.
Dihydric carboxylic acid diesters of 4 to 12 carbon atoms include phthalic acid diesters and adipic acid diesters, and phthalic acid diesters are particularly preferable, and among them, diethylhexyl phthalate and diisononyl phthalate are soluble in pest control agents. is particularly preferred because of good
Polypropylene glycol having a molecular weight of 1,000 to 5,000 is preferable because of its low viscosity and ease of handling. Either diol type or triol type polypropylene glycol may be used.
本発明の匍匐害虫防除用硬化性組成物における（Ｂ）成分の含有量は、（Ａ）成分１００重量部に対して、好ましくは１０重量部～８０重量部、より好ましくは２０重量部～８０重量部、さらに好ましくは４０重量部～６０重量部である。（Ａ）成分１００重量部に対して（Ｂ）成分の含有量が８０重量部より多い場合、硬化剤を加えた場合組成物の硬度が低くなる傾向があり好ましくない。一方、（Ａ）成分１００重量部に対して（Ｂ）成分の含有量が１０重量部未満であると、殺虫効果が低くなる場合があり好ましくない。 The content of component (B) in the curable composition for controlling crawling pests of the present invention is preferably 10 parts by weight to 80 parts by weight, more preferably 20 parts by weight to 80 parts by weight, per 100 parts by weight of component (A). parts by weight, more preferably 40 to 60 parts by weight. When the content of component (B) is more than 80 parts by weight per 100 parts by weight of component (A), the hardness of the composition tends to be lowered when a curing agent is added, which is not preferred. On the other hand, if the content of component (B) is less than 10 parts by weight per 100 parts by weight of component (A), the insecticidal effect may be lowered, which is undesirable.
本発明の匍匐害虫防除用硬化性組成物は、（Ｃ）害虫防除剤、を含有する。害虫防除剤としては、匍匐害虫に対する防除効果を有するものであれば特に限定はない。好ましくは、ピレスロイド系化合物、カーバメート系化合物及び有機リン系化合物からなる群から選ばれる少なくとも１種である。 The curable composition for controlling creeping pests of the present invention contains (C) a pest control agent. The pest control agent is not particularly limited as long as it has an effect of controlling creeping pests. Preferably, it is at least one selected from the group consisting of pyrethroid compounds, carbamate compounds and organophosphorus compounds.
ピレスロイド系化合物としては、アクリナトリン、アレスリン、ベータ－シフルトリン、ビフェントリン、シクロプロトリン、シフルトリン、シハロトリン、シペルメトリン、エンペントリン、デルタメトリン、エスフェンバレレート、エトフェンプロックス、フェンプロパトリン、フェンバレレート、フルシトリネート、フルフェンプロックス、フルメトリン、フルバリネート、ハルフェンプロックス、イミプロトリン、ペルメトリン、プラレトリン、ピレトリン、レスメトリン、シグマ－サイパーメトリン、シラフルオフェン、テフルトリン、トラロメトリン、トランスフルトリン、メトフルトリン、プロフルトリン、テトラメトリン、フェノトリン、シフェノトリン、アルファシペルメトリン、フラメトリン、タウフルバリネート、等が挙げられる。この中で、ピレトリン、トランスフルトリン、及びビフェントリンが好ましく、トランスフルトリンとビフェントリンが特に好ましい。本発明において用いられるピレスロイド系化合物には各種異性体が含まれる。 Pyrethroid compounds include acrinathrin, allethrin, beta-cyfluthrin, bifenthrin, cycloprothrin, cyfluthrin, cyhalothrin, cypermethrin, empentrin, deltamethrin, esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate, Flufenprox, flumethrin, fluvalinate, halffenprox, imiprothrin, permethrin, prallethrin, pyrethrin, resmethrin, sigma-cypermethrin, silafluofen, tefluthrin, tralomethrin, transfluthrin, metofruthrin, profluthrin, tetramethrin, phenothrin, cyphenothrin, alfax permethrin, flamethrin, taufluvalinate, and the like. Among these, pyrethrin, transfluthrin and bifenthrin are preferred, and transfluthrin and bifenthrin are particularly preferred. Various isomers are included in the pyrethroid compounds used in the present invention.
カーバメート系化合物としては、メトキサジアゾン、アラニカルブ、ベンダイオカルブ、ベンフラカルブ、カルバリル、カルボフラン、カルボスルファン、クロエトカルブ、エチオフェンカルブ、フェノブカルブ、フェノチオカルブ、フラチオカルブ、イソプロカルブ、メトルカルブ、メソミル、メチオカルブ、オキサミル、ピリミカーブ、プロポキスル、ＸＭＣ、チオジカルブ、キシリルカルブ、アルジカルブ、等が挙げられる。この中で、メトキサジアゾン、カルバリル、フェノブカルブ、及びプロポキスルが、殺虫活性が高いことから特に好ましい。本発明において用いられるカーバメート系化合物には各種異性体が含まれる。 Carbamate compounds include methoxadiazone, alanicarb, bendiocarb, benfuracarb, carbaryl, carbofuran, carbosulphan, cloetocarb, ethiophenecarb, fenocarb, phenothiocarb, furatiocarb, isoprocarb, metolcarb, methomyl, methiocarb, oxamyl, pirimicarb, propoxur, XMC, thiodicarb, xylylcarb, aldicarb, and the like. Among these, methoxadiazone, carbaryl, fenocarb and propoxur are particularly preferred due to their high insecticidal activity. Carbamate compounds used in the present invention include various isomers.
有機リン系化合物としては、アセフェート、アザメチホス、アジンホスエチル、アジンホスメチル、カズサホス、クロレトキシホス、クロルフェンビンホス、クロルメホス、クロルピリホス、クロルピリホスメチル、クマホス、シアノホス、デメトン－Ｓ－メチル、ダイアジノン、ジクロルボス、ジクロトホス、ジメトエート、ジメチルビンホス、ジスルホトン、ＥＰＮ、エチオン、エトプロホス、ファンフル、フェミナホス）、フェニトロチオン、フェンチオン、ヘプテノホス、イソフェンホス、イソプロピル＝Ｏ－（メトキシアミノチオホスホリル）サリチラートまたはイソカルボホス、イソキサチオン、マラチオン、メカルバム、メタミドホス、メチダチオン、メビンホス、モノクロトホス、ナレッド、オメトエート、オキシジメトンメチル、パラチオン、パラチオンメチルまたはメチルパラチオン、フェントエート、ホレート、ホサロン、ホスメット、ホスファミドン、ホキシム、ピリミホスメチル、プロフェノホス、プロペタムホス、プロチオホス、ピラクロホス、ピリダフェンチオン、キナルホス、スルホテップ、テブピリムホス、テメホス、テルブホス、テトラクロルビンホス、チオメトン、トリアゾホス、トリクロルホン、バミドチオン等が挙げられる。本発明において用いられる有機リン系化合物には各種異性体が含まれる。 Organic phosphorus compounds include acephate, azamethyphos, azinphos-ethyl, azinphos-methyl, cassaphos, chlorethoxyphos, chlorfenbinphos, chlormephos, chlorpyrifos, chlorpyrifos-methyl, coumaphos, cyanophos, demeton-S-methyl, diazinon, dichlorvos, dicrotophos, dimethoate, dimethyl vinphos, disulfotone, EPN, ethione, ethprophos, fanfur, feminophos), fenitrothion, fenchion, heptenophos, isofenphos, isopropyl O-(methoxyaminothiophosphoryl) salicylate or isocarbophos, isoxathion, malathion, mecarbam, methamidophos, methidathion, mevinphos , monocrotophos, naled, omethoate, oxydimethone methyl, parathion, parathion methyl or methyl parathion, phenthate, folate, fosarone, phosmet, phosphamidone, phoxime, pirimiphos methyl, propenofos, propetamphos, prothiophos, pyraclophos, pyridafenthion, quinarphos, sulfotep, tebupyrimphos, temefos , terbufos, tetrachlorbinphos, thiometone, triazophos, trichlorfon, vamidothione and the like. Various isomers are included in the organophosphorus compounds used in the present invention.
これらの害虫防除成分については、１種のみを用いてもよいし、複数種を組み合わせて用いてもよい。例えば、２種以上のピレスロイド系化合物、２種以上のカーバメート系化合物、又は２種以上の有機リン系化合物を組み合わせて用いてもよいし、ピレスロイド系化合物、カーバメート系化合物及び有機リン系化合物からなる群から選ばれる２種以上の化合物を組み合わせて用いてもよい。 These insect pest control components may be used singly or in combination. For example, two or more pyrethroid compounds, two or more carbamate compounds, or two or more organophosphorus compounds may be used in combination, or pyrethroid compounds, carbamate compounds and organophosphorus compounds. Two or more compounds selected from the group may be used in combination.
本発明の匍匐害虫防除用硬化性組成物における（Ｃ）成分の含有量は、（Ａ）成分１００重量部に対して、好ましくは０．１重量部～５０重量部、より好ましくは０．３重量部～１５重量部、さらに好ましくは０．３重量部～５重量部である。（Ａ）成分１００重量部に対して（Ｃ）成分の含有量が５０重量部より多い場合、硬化剤を加えたときの硬度が低くなる傾向があり好ましくない。一方、（Ａ）成分１００重量部に対して（Ｃ）成分の含有量が０．１重量部未満であると、殺虫効果の持続期間が短くなることから好ましくない。 The content of component (C) in the curable composition for controlling crawling pests of the present invention is preferably 0.1 to 50 parts by weight, more preferably 0.3 parts by weight, per 100 parts by weight of component (A). It is from 0.3 to 5 parts by weight, more preferably from 0.3 to 5 parts by weight. If the content of component (C) is more than 50 parts by weight with respect to 100 parts by weight of component (A), the hardness tends to be low when a curing agent is added, which is undesirable. On the other hand, if the content of component (C) is less than 0.1 parts by weight per 100 parts by weight of component (A), the duration of the insecticidal effect will be shortened, which is undesirable.
（Ｃ）成分としてピレスロイド系化合物を用いる場合は、（Ｃ）成分の含有量は、（Ａ）成分１００重量部に対して、好ましくは０．１重量部～１０重量部、より好ましくは、０．３重量部～５重量部、さらに好ましくは０．３重量部～３重量部である。なお、（Ｃ）成分としてピレスロイド系化合物を用い、かつ後述する共力剤と組み合わせると、（Ｃ）成分の殺虫効果が高くなり、（Ｃ）成分であるピレスロイド系化合物の含有量を低く抑えることが可能である。 When a pyrethroid compound is used as component (C), the content of component (C) is preferably 0.1 to 10 parts by weight, more preferably 0, per 100 parts by weight of component (A). .3 to 5 parts by weight, more preferably 0.3 to 3 parts by weight. When a pyrethroid compound is used as the component (C) and combined with a synergist to be described later, the insecticidal effect of the component (C) is enhanced, and the content of the pyrethroid compound as the component (C) can be kept low. is possible.
（Ｃ）成分としてカーバメート系化合物を用いる場合は、（Ｃ）成分の含有量は、（Ａ）成分１００重量部に対して、好ましくは０．１重量部～１０重量部、より好ましくは、０．３重量部～５重量部、さらに好ましくは０．９重量部～３重量部である。なお、（Ｃ）成分としてカーバメート系化合物を用いる場合は、（Ａ）成分と（Ｃ）成分との組み合わせによって（Ｃ）成分の殺虫効果、害虫忌避効果が高くなり、（Ｃ）成分であるカーバメート系化合物の含有量を低く抑えることが可能である。 When a carbamate compound is used as component (C), the content of component (C) is preferably 0.1 to 10 parts by weight, more preferably 0, per 100 parts by weight of component (A). .3 to 5 parts by weight, more preferably 0.9 to 3 parts by weight. When a carbamate-based compound is used as component (C), the combination of component (A) and component (C) enhances the insecticidal and pest-repellent effects of component (C). It is possible to keep the content of the system compound low.
本発明の匍匐害虫防除用硬化性組成物は、反応性ケイ素基の反応を促進する目的でシラノール縮合触媒（硬化剤、硬化触媒）を含んでもよい。シラノール縮合触媒としては、例えば、カルボン酸のアルキルスズ塩、アルキルスズアルコキシド、アルキルスズキレート化合物、アルキルスズオキサイド及びその反応生成物、アルキルスズ塩とシリケート化合物との反応生成物、カルボン酸スズ塩、等が挙げられる。この中で、１,１,３,３－テトラブチル－１,３－ジラウリルオキシカルボニル－ジスタノキサン、ジブチル錫塩と正ケイ酸エチルとの反応生成物、ジブチル錫ジアセチルアセトナートが好ましい。また他にも、アルコキシ基およびキレート基を有するチタン化合物、ジルコニウムオキシド化合物、バナジウムオキシド化合物を用いてもよい。シラノール縮合触媒の含有量は、（Ａ）成分１００重量部に対して０．０１重量部～２０重量部が好ましく、０．１重量部～１０重量部がより好ましい。
なお、本発明の匍匐害虫防除用硬化性組成物にシラノール縮合触媒を含めない場合は、匍匐害虫防除用硬化性組成物の使用時にシラノール縮合触媒を添加し、硬化させることができる。
The curable composition for controlling crawling pests of the present invention may contain a silanol condensation catalyst (curing agent, curing catalyst) for the purpose of promoting the reaction of the reactive silicon groups. Examples of silanol condensation catalysts include alkyltin salts of carboxylic acids, alkyltin alkoxides, alkyl suzukilate compounds, alkyltin oxides and their reaction products, reaction products of alkyltin salts and silicate compounds, tin carboxylates, and the like. mentioned. Among these, 1,1,3,3-tetrabutyl-1,3-dilauryloxycarbonyl-distannoxane, the reaction product of dibutyltin salt and orthoethyl silicate, and dibutyltin diacetylacetonate are preferred. In addition, titanium compounds having alkoxy groups and chelate groups, zirconium oxide compounds, and vanadium oxide compounds may also be used. The content of the silanol condensation catalyst is preferably 0.01 to 20 parts by weight, more preferably 0.1 to 10 parts by weight, per 100 parts by weight of component (A).
When the curable composition for controlling creeping pests of the present invention does not contain a silanol condensation catalyst, the curable composition for controlling creeping pests can be cured by adding a silanol condensation catalyst at the time of use.
本発明の匍匐害虫防除用硬化性組成物は、その性能を損なわない限りにおいて、他の成分をさらに含んでもよい。例えば、共力剤をさらに含んでもよい。その他、昆虫成長制御剤、防黴剤、充填剤、垂れ防止剤、脱水剤、光安定剤、紫外線吸収剤、及び酸化防止剤からなる群から選ばれる少なくとも１つの成分をさらに含んでもよい。 The curable composition for controlling creeping pests of the present invention may further contain other components as long as the composition does not impair its performance. For example, a synergist may be further included. In addition, it may further contain at least one component selected from the group consisting of insect growth regulators, antifungal agents, fillers, anti-sagging agents, dehydrating agents, light stabilizers, UV absorbers, and antioxidants.
共力剤は、殺虫剤と混合することで殺虫効果を著しく高める化合物である。共力剤の例としては、ビス－（２，３，３，３－テトラクロロプロピル）エーテル（別名：Ｓ－４２１）、Ｎ－（２－エチルヘキシル）ビシクロ[２．２．１]ヘプト－５－エン－２，３－ジカルボキシイミド（別名：ＭＧＫ２６４）、５－プロピル－６－[２－（２－ブトキシエトキシ）エトキシメチル]－１，３－ベンゾジオキソール（別名：ピペロニルブトキシド、ＰＢＯ）、等が挙げられる。これらの共力剤については１種類のみを用いてもよいし、複数種を組み合わせて用いてもよい。共力剤の含有量は、（Ｃ）成分１重量部に対して、１重量部～２０重量部が好ましく、３重量部～1０重量部がより好ましい。 Synergists are compounds that, when mixed with insecticides, significantly enhance their insecticidal efficacy. Examples of synergists include bis-(2,3,3,3-tetrachloropropyl) ether (also known as S-421), N-(2-ethylhexyl)bicyclo[2.2.1]hept-5 -ene-2,3-dicarboximide (alias: MGK264), 5-propyl-6-[2-(2-butoxyethoxy)ethoxymethyl]-1,3-benzodioxole (alias: piperonyl butoxide, PBO) , etc. Only one type of these synergists may be used, or a plurality of types may be used in combination. The content of synergist is preferably 1 to 20 parts by weight, more preferably 3 to 10 parts by weight, per 1 part by weight of component (C).
なお、共力剤と組み合わせる害虫防除剤としては特に限定はないが、ピレスロイド系化合物と組み合わせることが特に好ましい。すなわち、共力剤を組み合わせることにより、ピレスロイド系化合物の害虫防除効果がより高く発揮される。例えば、ピレトリンとＭＧＫ２６４、トランスフルトリンとＭＧＫ２６４、ビフェントリンとＭＧＫ２６４、ビフェントリンとＰＢＯ、ペルメトリンとＭＧＫ２６４、レスメトリンとＭＧＫ２６４、シフェノトリンとＭＧＫ２６４、ペルメトリンとＰＢＯ、等の組み合わせが推奨される。このうち、トランスフルトリンとＭＧＫ２６４、ビフェントリンとＭＧＫ２６４、ビフェントリンとＰＢＯ、の組み合わせが特に推奨される。 Although there are no particular restrictions on the pest control agent to be combined with the synergist, combination with a pyrethroid compound is particularly preferred. That is, by combining a synergist, the pyrethroid compound exhibits a higher pest control effect. For example, combinations of pyrethrin and MGK264, transfluthrin and MGK264, bifenthrin and MGK264, bifenthrin and PBO, permethrin and MGK264, resmethrin and MGK264, cyphenothrin and MGK264, permethrin and PBO, and the like are recommended. Among these, combinations of transfluthrin and MGK264, bifenthrin and MGK264, and bifenthrin and PBO are particularly recommended.
昆虫成長制御剤は、昆虫の成長や休眠、産卵等の昆虫特有の機能を阻害する化合物である。昆虫成長制御剤の例としては、ピリプロキシフェン、メソプレン、ハイドロピレン、フェノキシカルブ、ルフェヌロン、フルフェノクスロン、ノバルロン、ヘキサフルムロン、テフルベンズロン、ジフルベンズロン、トリフルムロン、ブプロフェジン、シロマジン、等が挙げられる。これらの昆虫成長制御剤については１種類のみを用いてもよいし、複数種を組み合わせて用いてもよい。昆虫成長制御剤の含有量は、（Ａ）成分１００重量部に対して０．０１重量部～３０重量部が好ましく、０．１重量部～1０重量部がより好ましい。 Insect growth regulators are compounds that inhibit insect-specific functions such as insect growth, dormancy, and egg-laying. Examples of insect growth regulators include pyriproxyfen, mesoprene, hydropyrene, fenoxycarb, lufenuron, flufenoxuron, novaluron, hexaflumuron, teflubenzuron, diflubenzuron, triflumuron, buprofezin, cyromazine, and the like. Only one type of these insect growth regulators may be used, or a plurality of types may be used in combination. The content of the insect growth regulator is preferably 0.01 to 30 parts by weight, more preferably 0.1 to 10 parts by weight, per 100 parts by weight of component (A).
防黴剤としては、２－ｎ－オクチル－４－イソチアゾリン－３－オン、４，５－ジクロロ－２－オクチル－４－イソチアゾリン－３－オン、Ｎ－ｎ－ブチル－１，２－ベンズイソチアゾリン－３－オン、２－メチル－４－イソチアゾリン－３－オン、５－クロロ－２－メチル－４－イソチアゾリン－３－オン、１，２－ベンゾイソチアゾリン－３－オン等のイソチアゾリノン系化合物；チアベンダゾール、カルベンダジム等のベンズイミダゾール系化合物；テトラクロロメチルスルホニルピリジン；ジヨードメチル－ｐ－トリルスルホン、３－ヨード－２－プロピニルブチルカーバメート等の有機ヨウ素系化合物；２，２－ジブロモ－３－ニトリルプロピオンアミド；ジンクピリチオン、等が挙げられる。防黴剤の含有量は、（Ａ）成分１００重量部に対して０．０１重量部～１０重量部が好ましく、０．１重量部～６重量部がより好ましい。 Antifungal agents include 2-n-octyl-4-isothiazolin-3-one, 4,5-dichloro-2-octyl-4-isothiazolin-3-one, Nn-butyl-1,2-benzisothiazoline -3-one, 2-methyl-4-isothiazolin-3-one, 5-chloro-2-methyl-4-isothiazolin-3-one, 1,2-benzisothiazolin-3-one and other isothiazolinone compounds; thiabendazole , benzimidazole compounds such as carbendazim; tetrachloromethylsulfonylpyridine; diiodomethyl-p-tolylsulfone, 3-iodo-2-propynylbutylcarbamate and other organic iodine compounds; 2,2-dibromo-3-nitrilepropionamide zinc pyrithione, and the like. The content of the antifungal agent is preferably 0.01 to 10 parts by weight, more preferably 0.1 to 6 parts by weight, per 100 parts by weight of component (A).
充填剤としては、無水ケイ酸、炭酸カルシウム、炭酸マグネシウム、ケイソウ土タルク、酸化チタン、ベントナイト、酸化亜鉛、ガラス繊維、等が挙げられる。これらの充填剤については１種類のみを用いてもよいし、複数種を組み合わせて用いてもよい。充填剤の含有量は、（Ａ）成分１００重量部に対して１０重量部～２００重量部が好ましく、５０重量部～１２０重量部がより好ましい。 Fillers include anhydrous silicic acid, calcium carbonate, magnesium carbonate, diatomaceous earth talc, titanium oxide, bentonite, zinc oxide, glass fiber, and the like. Only one type of these fillers may be used, or a plurality of types may be used in combination. The content of the filler is preferably 10 to 200 parts by weight, more preferably 50 to 120 parts by weight, per 100 parts by weight of component (A).
垂れ防止剤としては、高分散シリカ、有機変性ベントナイト、合成ヘクトライト、有機ワックス類、反応性有機シリコン化合物、等が挙げられる。これらの垂れ防止剤については１種類のみを用いてもよいし、複数種を組み合わせて用いてもよい。 Anti-sagging agents include highly dispersed silica, organically modified bentonite, synthetic hectorite, organic waxes, reactive organic silicon compounds, and the like. Only one type of these anti-sagging agents may be used, or a plurality of types may be used in combination.
脱水剤としては、酸化カルシウム、ビニルトリメトキシシラン等の反応性有機シリコン化合物、オルトギ酸メチル、オルト酢酸エチル等のオルトギ酸アルキル、などが挙げられる。脱水剤の含有量は、（Ａ）成分１００重量部に対して０．１重量部～１０重量部が好ましく、０．２重量部～５重量部がより好ましい。 Examples of dehydrating agents include calcium oxide, reactive organic silicon compounds such as vinyltrimethoxysilane, and alkyl orthoformates such as methyl orthoformate and ethyl orthoacetate. The content of the dehydrating agent is preferably 0.1 to 10 parts by weight, more preferably 0.2 to 5 parts by weight, per 100 parts by weight of component (A).
光安定剤としては、ベンゾトリアゾール系化合物、ヒンダードアミン系化合物、ベンゾエート系化合物、等が挙げられる。この中でも、ヒンダードアミン系化合物が好ましい。光安定剤の含有量は、（Ａ）成分１００重量部に対して０．１重量部～１０重量部が好ましく、０．２重量部～５重量部がより好ましい。 Light stabilizers include benzotriazole-based compounds, hindered amine-based compounds, benzoate-based compounds, and the like. Among these, hindered amine compounds are preferred. The content of the light stabilizer is preferably 0.1 to 10 parts by weight, more preferably 0.2 to 5 parts by weight, per 100 parts by weight of component (A).
紫外線吸収剤としては、ベンゾフェノン系化合物、ベンゾトリアゾール系化合物、サリシレート系化合物、置換トリル系化合物、金属キレート系化合物、等が挙げられる。この中でもベンゾトリアゾール系化合物が好ましい。紫外線吸収剤の含有量は、（Ａ）成分１００重量部に対して０．１重量部～１０重量部が好ましく、０．２重量部～５重量部がより好ましい。 Examples of ultraviolet absorbers include benzophenone-based compounds, benzotriazole-based compounds, salicylate-based compounds, substituted tolyl-based compounds, metal chelate-based compounds, and the like. Among these, benzotriazole compounds are preferred. The content of the ultraviolet absorber is preferably 0.1 to 10 parts by weight, more preferably 0.2 to 5 parts by weight, per 100 parts by weight of component (A).
酸化防止剤としては、ヒンダードフェノール系酸化防止剤、モノフェノール系酸化防止剤、ビスフェノール系酸化防止剤、ポリフェノール系酸化防止剤、等が挙げられる。この中でもヒンダードフェノール系酸化防止剤が好ましい。酸化防止剤の含有量は、（Ａ）成分１００重量部に対して０．１重量部～１０重量部が好ましく、０．２重量部～５重量部がより好ましい。 Antioxidants include hindered phenol antioxidants, monophenol antioxidants, bisphenol antioxidants, polyphenol antioxidants, and the like. Among these, hindered phenol-based antioxidants are preferred. The content of the antioxidant is preferably 0.1 to 10 parts by weight, more preferably 0.2 to 5 parts by weight, per 100 parts by weight of component (A).
本発明の匍匐害虫防除用硬化性組成物は、例えば、反応性ケイ素基を有するポリオキシアルキレン系重合体からなる（Ａ）成分に、（Ｂ）成分及び（Ｃ）成分、必要に応じて他の成分を添加し、加熱・攪拌等の条件を適宜調節し、均一に分散及び溶解させることにより製造することができる。（Ａ）成分として反応性ケイ素基を有する（メタ）アクリル酸エステル系重合体を併用する場合には、反応性ケイ素基を有するポリオキシアルキレン系重合体（重合体（ａ－１））と反応性ケイ素基を有する（メタ）アクリル酸エステル系重合体（重合体（ａ－２））との混合物に、（Ｂ）成分及び（Ｃ）成分、必要に応じて他の成分を添加すればよい。 The curable composition for controlling crawling pests of the present invention comprises, for example, component (A) comprising a polyoxyalkylene polymer having a reactive silicon group, component (B) and component (C), and optionally other components. It can be produced by adding the components of (1), appropriately adjusting conditions such as heating and stirring, and uniformly dispersing and dissolving. (A) When a (meth)acrylic acid ester polymer having a reactive silicon group is used in combination as the component (A), the reaction with the polyoxyalkylene polymer having a reactive silicon group (polymer (a-1)) Components (B) and (C), and if necessary, other components may be added to a mixture with a (meth)acrylic acid ester polymer having a silicon group (polymer (a-2)). .
本発明における硬化性組成物は、室温硬化性組成物、湿分硬化性組成物、等と言い換えることができる。 The curable composition in the present invention can be called a room temperature curable composition, a moisture curable composition, and the like.
本発明のシーリング材は、上記の匍匐害虫防除用硬化性組成物を含むものである。本発明の匍匐害虫の防除方法は、上記の匍匐害虫防除用硬化性組成物又はシーリング材を用いて匍匐害虫を防除するものである。 The sealing material of the present invention contains the above curable composition for controlling creeping pests. The method for controlling creeping pests of the present invention uses the above curable composition for controlling creeping pests or sealing material to control creeping pests.
本発明のシーリング材を施用することによって、チャタテムシ等の匍匐害虫を防除することができる。本発明のシーリング材は、従来の変性シリコーン系シーリング材と同様に、建築用シーリング材として用いることができる。 By applying the sealant of the present invention, crawling pests such as bookworms can be controlled. The sealant of the present invention can be used as a building sealant in the same manner as conventional modified silicone-based sealants.
本発明の対象となる匍匐害虫としては、チャタテムシ類、トビムシ類、キクイムシ類、シバンムシ類、ヒメマキムシ類、ハネカクシ類、ケシキスイ類、カツオブシムシ類、アリ類、ダンゴムシ類、シロアリ類、ゴキブリ類、などが挙げられる。 Crawling insect pests to be targeted by the present invention include bookworms, springtails, bark beetles, beetles, horse beetles, sting beetles, poplars, deer beetles, ants, pill bugs, termites, cockroaches, and the like. be done.
チャタテムシ類としては、コチャタテ等のコチャタテ科；ヒラタチャタテ、カツブシチャタテ、ソウメンチャタテ等のコナチャタテ科；ヒメチャタテ等のヒメチャタテ科、などに属する微小昆虫が挙げられる。 Examples of the chatatemushi include microscopic insects belonging to the family Pelargonium, such as Peppermint; Pelargonium, such as Hiratatatate, Katsubushichatate, and Soumenchatate;
以下に、実施例をもって本発明をさらに具体的に説明するが、本発明はこの実施例に限定されるものではない。 EXAMPLES The present invention will be described in more detail with reference to examples below, but the present invention is not limited to these examples.
〔実施例１〕
メチルジメトキシシリル基末端ポリプロピレンオキシド系重合体（商品名「ＭＳポリマーＳ３０３Ｈ」、株式会社カネカ）１００重量部に、乾燥器により水分を除去した炭酸カルシウム（関東化学株式会社）１２０重量部およびルチル型酸化チタン（関東化学株式会社）２０重量部を混合して充分混練した。メトキサジアゾン（住友化学株式会社）０．３重量部をフタル酸ジエチルヘキシル（ＤＥＨＰ）（関東化学株式会社）５７．７重量部に溶解した溶液を混練物に滴下し、撹拌した。硬化触媒として１，１，３，３－テトラブチル－１，３－ジラウリルオキシカルボニル－ジスタノキサン（商品名「ネオスタンＵ－１３０」、日東化成株式会社）２重量部を加えて混練し、本発明硬化性組成物１を得た。
[Example 1]
To 100 parts by weight of a methyldimethoxysilyl group-terminated polypropylene oxide polymer (trade name "MS Polymer S303H", Kaneka Co., Ltd.), 120 parts by weight of calcium carbonate (Kanto Kagaku Co., Ltd.) from which water was removed by a dryer and rutile type oxidation 20 parts by weight of titanium (Kanto Kagaku Co., Ltd.) was mixed and sufficiently kneaded. A solution prepared by dissolving 0.3 parts by weight of methoxadiazon (Sumitomo Chemical Co., Ltd.) in 57.7 parts by weight of diethylhexyl phthalate (DEHP) (Kanto Chemical Co., Ltd.) was added dropwise to the kneaded product and stirred. 2 parts by weight of 1,1,3,3-tetrabutyl-1,3-dilauryloxycarbonyl-distannoxane (trade name “Neostan U-130”, Nitto Kasei Co., Ltd.) as a curing catalyst was added and kneaded to cure the present invention. A sexual composition 1 was obtained.
〔実施例２〕
実施例１におけるフタル酸ジエチルヘキシル５７．７重量部をポリプロピレングリコール１０００（ＰＰＧ１０００）（関東化学株式会社）５７．７重量部に代え、後は同様の操作をして、本発明硬化性組成物２を得た。
[Example 2]
The 57.7 parts by weight of diethylhexyl phthalate in Example 1 was replaced with 57.7 parts by weight of polypropylene glycol 1000 (PPG1000) (Kanto Kagaku Co., Ltd.), and the rest was repeated in the same manner to obtain the curable composition 2 of the present invention. got
〔実施例３〕
実施例１におけるフタル酸ジエチルヘキシル５７．７重量部をポリプロピレングリコール３０００（ＰＰＧ３０００）（ジオール型、関東化学株式会社）５７．７重量部に代え、後は同様の操作をして、本発明硬化性組成物３を得た。
[Example 3]
The 57.7 parts by weight of diethylhexyl phthalate in Example 1 was replaced with 57.7 parts by weight of polypropylene glycol 3000 (PPG3000) (diol type, Kanto Kagaku Co., Ltd.), and then the same operation was performed to obtain the curability of the present invention. Composition 3 was obtained.
〔実施例４〕
実施例１におけるフタル酸ジエチルヘキシル５７．７重量部をポリプロピレングリコール４０００（ＰＰＧ４０００）（トリオール型、関東化学株式会社）５７．７重量部に代え、後は同様の操作をして、本発明硬化性組成物４を得た。
[Example 4]
The 57.7 parts by weight of diethylhexyl phthalate in Example 1 was replaced with 57.7 parts by weight of polypropylene glycol 4000 (PPG4000) (triol type, Kanto Kagaku Co., Ltd.), and then the same operation was performed to obtain the curability of the present invention. Composition 4 was obtained.
〔実施例５〕
実施例１におけるメチルジメトキシシリル基末端ポリプロピレンオキシド系重合体１００重量部をメチルジメトキシシリル基末端ポリプロピレンオキシド系重合体（商品名「ＭＳポリマーＳ２０３Ｈ」、株式会社カネカ）１００重量部に代え、後は同様の操作をして、本発明硬化性組成物５を得た。
[Example 5]
Replace 100 parts by weight of the methyldimethoxysilyl group-terminated polypropylene oxide polymer in Example 1 with 100 parts by weight of the methyldimethoxysilyl group-terminated polypropylene oxide polymer (trade name "MS Polymer S203H", Kaneka Corporation), and the rest is the same. to obtain a curable composition 5 of the present invention.
〔実施例６〕
実施例５におけるフタル酸ジエチルヘキシル５７．７重量部をポリプロピレングリコール３０００（ＰＰＧ３０００）（ジオール型、関東化学株式会社）５７．７重量部に代え、後は同様の操作をして、本発明硬化性組成物６を得た。
[Example 6]
57.7 parts by weight of diethylhexyl phthalate in Example 5 was replaced with 57.7 parts by weight of polypropylene glycol 3000 (PPG3000) (diol type, Kanto Kagaku Co., Ltd.), and then the same operation was performed to obtain the curability of the present invention. Composition 6 was obtained.
〔実施例７〕
主鎖骨格にアクリル変性されたセグメントを一部導入したメチルジメトキシシリル基末端ポリプロピレンオキシド系重合体（商品名「ＭＳポリマーＳ９４３」、株式会社カネカ）１００重量部に、乾燥器により水分を除去した炭酸カルシウム（関東化学株式会社）１２０重量部およびルチル型酸化チタン（関東化学株式会社）２０重量部を混合して充分混練した。メトキサジアゾン（住友化学株式会社）０．３重量部をポリプロピレングリコール４０００（トリオール型、関東化学株式会社）５．７７重量部に溶解した溶液を混練物に滴下し、撹拌した。硬化触媒として１，１，３，３－テトラブチル－１，３－ジラウリルオキシカルボニル－ジスタノキサン（商品名「ネオスタンＵ－１３０」、日東化成株式会社）２重量部を加えて混練し、本発明硬化性組成物７を得た。
[Example 7]
100 parts by weight of a methyldimethoxysilyl group-terminated polypropylene oxide polymer (trade name “MS Polymer S943”, Kaneka Co., Ltd.) in which an acryl-modified segment is partially introduced into the main chain skeleton, and carbonic acid from which moisture has been removed using a dryer. 120 parts by weight of calcium (Kanto Chemical Co., Ltd.) and 20 parts by weight of rutile type titanium oxide (Kanto Chemical Co., Ltd.) were mixed and sufficiently kneaded. A solution prepared by dissolving 0.3 parts by weight of methoxadiazon (Sumitomo Chemical Co., Ltd.) in 5.77 parts by weight of polypropylene glycol 4000 (triol type, Kanto Kagaku Co., Ltd.) was added dropwise to the kneaded product and stirred. 2 parts by weight of 1,1,3,3-tetrabutyl-1,3-dilauryloxycarbonyl-distannoxane (trade name “Neostan U-130”, Nitto Kasei Co., Ltd.) as a curing catalyst was added and kneaded to cure the present invention. A sexual composition 7 was obtained.
〔実施例８〕
実施例１における炭酸カルシウム（関東化学株式会社）１２０重量部を脂肪酸表面処理が施された軽質炭酸カルシウム（商品名「白艶華ＣＣＲ」、白石工業株式会社）１２０重量部に代え、ルチル型酸化チタン（関東化学株式会社）２０重量部をルチル型酸化チタン（商品名「タイペークＣＲ－８２０」、石原産業株式会社）２０重量部に代え、後は同様の操作をして、本発明硬化性組成物８を得た。
[Example 8]
Instead of 120 parts by weight of calcium carbonate (Kanto Kagaku Co., Ltd.) in Example 1, 120 parts by weight of light calcium carbonate (trade name “Hakuenka CCR”, Shiraishi Kogyo Co., Ltd.) subjected to fatty acid surface treatment, rutile titanium oxide ( Kanto Kagaku Co., Ltd.) was replaced with 20 parts by weight of rutile-type titanium oxide (trade name “Tipaque CR-820”, Ishihara Sangyo Co., Ltd.), and the same operation was performed thereafter to obtain the curable composition 8 of the present invention. got
〔実施例９〕
実施例８におけるフタル酸ジエチルヘキシル５７．７重量部をポリプロピレングリコール３０００（関東化学株式会社）５．７７重量部に代え、後は同様の操作をして、本発明硬化性組成物９を得た。
[Example 9]
The curable composition 9 of the present invention was obtained by replacing 57.7 parts by weight of diethylhexyl phthalate in Example 8 with 5.77 parts by weight of polypropylene glycol 3000 (Kanto Kagaku Co., Ltd.). .
〔実施例１０〕
実施例１におけるメトキサジアゾン０．３重量部をペルメトリン（住友化学株式会社）５０重量部に代え、フタル酸ジエチルヘキシル５７．７重量部を１０重量部に代え、また炭酸カルシウム１２０重量部、酸化チタン２０重量部をそれぞれ１１９重量部、１９重量部に代え、同様の操作をして本発明硬化性組成物１０を得た。
[Example 10]
0.3 parts by weight of methoxadiazone in Example 1 was replaced with 50 parts by weight of permethrin (Sumitomo Chemical Co., Ltd.), 57.7 parts by weight of diethylhexyl phthalate was replaced with 10 parts by weight, and 120 parts by weight of calcium carbonate and 20 parts by weight of titanium oxide were used. The curable composition 10 of the present invention was obtained in the same manner except that the weight parts were changed to 119 weight parts and 19 weight parts, respectively.
〔実施例１１〕
実施例１におけるメトキサジアゾン０．３重量部をｄ－Ｔ８０－レスメトリン（住友化学株式会社）１５重量部に代え、フタル酸ジエチルヘキシル５７．７重量部を５０重量部に代え、また炭酸カルシウム１２０重量部、酸化チタン２０重量部をそれぞれ１１４重量部、１９重量部に代え、同様の操作をして本発明硬化性組成物１１を得た。
[Example 11]
0.3 parts by weight of methoxadiazone in Example 1 was replaced with 15 parts by weight of d-T80-resmethrin (Sumitomo Chemical Co., Ltd.), 57.7 parts by weight of diethylhexyl phthalate was replaced with 50 parts by weight, and 120 parts by weight of calcium carbonate. , and 20 parts by weight of titanium oxide were replaced with 114 parts by weight and 19 parts by weight, respectively, to obtain a curable composition 11 of the present invention.
〔実施例１２〕
実施例１におけるメトキサジアゾン０．３重量部をｄ－Ｔ８０－レスメトリン１５重量部に代え、フタル酸ジエチルヘキシル５７．７重量部をポリプロピレングリコール３０００（ジオール型）５０重量部に代え、また炭酸カルシウム１２０重量部、酸化チタン２０重量部をそれぞれ１１４重量部、１９重量部に代え、同様の操作をして本発明硬化性組成物１２を得た。
[Example 12]
0.3 parts by weight of methoxadiazone in Example 1 was replaced with 15 parts by weight of d-T80-resmethrin, 57.7 parts by weight of diethylhexyl phthalate was replaced with 50 parts by weight of polypropylene glycol 3000 (diol type), and 120 parts by weight of calcium carbonate. and 20 parts by weight of titanium oxide were replaced with 114 parts by weight and 19 parts by weight, respectively, to obtain a curable composition 12 of the present invention.
〔実施例１３〕
実施例１におけるメトキサジアゾン０．３重量部をｄ－Ｔ８０－レスメトリン２２．５重量部に代え、フタル酸ジエチルヘキシル５７．７重量部を５０重量部に代え、また炭酸カルシウム１２０重量部、酸化チタン２０重量部をそれぞれ１０７．５重量部、１８重量部に代え、同様の操作をして本発明硬化性組成物１３を得た。
[Example 13]
0.3 parts by weight of methoxadiazone in Example 1 was replaced with 22.5 parts by weight of d-T80-resmethrin, 57.7 parts by weight of diethylhexyl phthalate was replaced with 50 parts by weight, 120 parts by weight of calcium carbonate, and 20 parts by weight of titanium oxide. The curable composition 13 of the present invention was obtained in the same manner except that the weight parts were changed to 107.5 parts by weight and 18 parts by weight, respectively.
本発明硬化性組成物１～１３の組成を表１にまとめた。すなわち、実施例１～９（本発明硬化性組成物１～９）では害虫防除剤としてメトキサジアゾンを用いている。実施例１０（本発明硬化性組成物１０）では害虫防除剤としてペルメトリンを用いており、害虫防除剤の使用量が実施例１～９の１６７倍である。実施例１１、１２（本発明硬化性組成物１１、１２）では害虫防除剤としてｄ－Ｔ８０－レスメトリンを用いており、害虫防除剤の使用量が実施例１～９の５０倍である。実施例１３（本発明硬化性組成物１３）では害虫防除剤としてｄ－Ｔ８０－レスメトリンを用いており、害虫防除剤の使用量が実施例１～９の７５倍である。 The compositions of the curable compositions 1 to 13 of the present invention are summarized in Table 1. That is, in Examples 1 to 9 (curable compositions 1 to 9 of the present invention), methoxadiazon is used as an insect control agent. In Example 10 (curable composition 10 of the present invention), permethrin is used as the pest control agent, and the amount of the pest control agent used is 167 times that of Examples 1-9. In Examples 11 and 12 (curable compositions 11 and 12 of the present invention), d-T80-resmethrin was used as the pest control agent, and the amount of pest control agent used was 50 times that of Examples 1-9. In Example 13 (curable composition 13 of the present invention), d-T80-resmethrin was used as the pest control agent, and the amount of the pest control agent used was 75 times that of Examples 1-9.
〔試験例１〕
各硬化性組成物を４．０～４．２ｇを、底面の直径８０ｍｍ、高さ４５ｍｍの円柱型ポリカップの円底面に厚さ１．０～１．５ｍｍ、直径６０ｍｍの円状になるようになるように広げ、４８時間以上室温で放置することにより硬化させた。硬化組成物の円の中心付近に、飼育用餌粉末約１００ｍｇを置き、ヒラタチャタテ約５０匹を放し、２５℃の温度環境下に置いた。４８時間後に、ポリカップ内のヒラタチャタテの生存成虫数と生存幼虫数および致死成虫数と致死幼虫数を調査した。致死成虫数と致死幼虫数の合計を、試験開始時に放した虫数で除し、致死率（％）を算出した。この試験を２回行い（Ｎ＝２）、致死率の平均値（平均致死率）を算出した。結果を表２に示す。
[Test Example 1]
4.0 to 4.2 g of each curable composition is placed on the circular bottom of a cylindrical plastic cup with a bottom diameter of 80 mm and a height of 45 mm so that it becomes a circle with a thickness of 1.0 to 1.5 mm and a diameter of 60 mm. It was spread out so as to be even and hardened by standing at room temperature for 48 hours or more. About 100 mg of feeding powder for breeding was placed near the center of the circle of the cured composition, and about 50 flatfish were released and placed in a temperature environment of 25°C. After 48 hours, the number of surviving adult larvae, the number of surviving larvae, and the number of dead adult larvae and larvae of flatfish in the plastic cup were investigated. The total number of dead adults and dead larvae was divided by the number of insects released at the start of the test to calculate the mortality rate (%). This test was performed twice (N=2), and the average mortality rate (mean mortality rate) was calculated. Table 2 shows the results.
すなわち、実施例１～９の硬化性組成物（本発明硬化性組成物１～９）では全て１００％の致死率であった。一方、実施例１０～１３の硬化性組成物（本発明硬化性組成物１０～１３）の致死率は７０～８６％であった。害虫防除剤の使用量に着目すると、実施例１０（ペルメトリン使用）では実施例１～９（メトキサジアゾン使用）の１６７倍量の害虫防除剤を用いて７０％の致死率が得られた。実施例１１、１２（ｄ－Ｔ８０－レスメトリン使用）では実施例１～９の５０倍量の害虫防除剤を用いて７５～８２％の致死率が得られた。実施例１３（ｄ－Ｔ８０－レスメトリン使用）では実施例１～９の７５倍量の害虫防除剤を用いて８４％の致死率が得られた。 That is, all the curable compositions of Examples 1 to 9 (curable compositions 1 to 9 of the present invention) had a mortality rate of 100%. On the other hand, the fatality rate of the curable compositions of Examples 10 to 13 (curable compositions 10 to 13 of the present invention) was 70 to 86%. Focusing on the amount of pest control agent used, in Example 10 (using permethrin), a mortality rate of 70% was obtained using 167 times the amount of pest control agent as in Examples 1 to 9 (using methoxadiazon). In Examples 11 and 12 (using d-T80-resmethrin), 75-82% lethality was obtained using 50 times the amount of insect control agent as in Examples 1-9. Example 13 (using d-T80-resmethrin) gave 84% mortality with 75 times the amount of pest control agent as Examples 1-9.
試験例１の結果についてさらに考察する。まず、上記非特許文献１には、ヒラタチャタテに対するペルメトリンとｄ－Ｔ８０－レスメトリンの効果について記載されている。本報告によれば、ペルメトリンのＬＤ５０（ｇ／ｍ２）が０．２４３、ｄ－Ｔ８０－レスメトリンのＬＤ５０（ｇ／ｍ２）が０．０４６であり、ｄ－Ｔ８０－レスメトリンの方がペルメトリンより殺虫効果が約５倍高いことが示されている。
また、上記非特許文献２には、ヒラタチャタテに対するカーバメート剤（プロポキスル）とピレスロイド剤（ペルメトリン、ｄ－Ｔ８０－レスメトリン）の効果について記載されている。本報告によれば、継続接触試験における２４時間後の致死率が、
・プロポキスル：有効成分量１０（ｍｇ／ｍ２）で９８．７％、
・ペルメトリン：有効成分量２５０（ｍｇ／ｍ２）で３２．５％、
・ｄ－Ｔ８０－レスメトリン：有効成分量２５０（ｍｇ／ｍ２）で９９．２％、
であり、プロポキスルはｄ－Ｔ８０－レスメトリンの１／２５量で９８％以上の致死率を示している。
The results of Test Example 1 are further considered. First, Non-Patent Document 1 mentioned above describes the effect of permethrin and d-T80-resmethrin on flounder. According to this report, the LD 50 (g/m 2 ) of permethrin is 0.243 and the LD 50 (g/m 2 ) of d-T80-resmethrin is 0.046. It has been shown to be approximately five times more insecticidal than permethrin.
In addition, Non-Patent Document 2 mentioned above describes the effects of a carbamate agent (propoxur) and a pyrethroid agent (permethrin, d-T80-resmethrin) on flounder. According to this report, the fatality rate after 24 hours in the continuous contact test was
- Propoxur: 98.7% at an active ingredient amount of 10 (mg/m 2 ),
・Permethrin: 32.5% at an active ingredient amount of 250 (mg/m 2 ),
・d-T80-resmethrin: 99.2% at an active ingredient amount of 250 (mg/m 2 ),
, and propoxur shows a mortality rate of 98% or more at 1/25 dose of d-T80-resmethrin.
一方、試験例１の結果では、ペルメトリンとｄ－Ｔ８０－レスメトリンの場合、メトキサジアゾンの５０～１６７倍重量の量を使用しても致死率が１００％に届かなかった。この結果は、非特許文献１、２の記載から予想されるカーバメート系化合物とピレスロイド系化合物との効果の差（２５倍程度）を大きく超えるものであった。これは、変性シリコーン系シーリング材とカーバメート系化合物との組み合わせにより得られる効果といえる。 On the other hand, according to the results of Test Example 1, in the case of permethrin and d-T80-resmethrin, the fatality rate did not reach 100% even when 50 to 167 times the weight of methoxadiazon was used. This result greatly exceeded the difference (about 25 times) in the effect between the carbamate compound and the pyrethroid compound expected from the descriptions in Non-Patent Documents 1 and 2. This can be said to be an effect obtained by the combination of the modified silicone-based sealant and the carbamate-based compound.
〔実施例１４〕
実施例８におけるメトキサジアゾン０．３重量部を０．９重量部に代え、フタル酸ジエチルヘキシル５７．７重量部を５７．１重量部に代え、後は同様の操作をして、本発明硬化性組成物１４を得た。
[Example 14]
The 0.3 parts by weight of methoxadiazone in Example 8 was replaced with 0.9 parts by weight, and the 57.7 parts by weight of diethylhexyl phthalate was replaced with 57.1 parts by weight. Composition 14 was obtained.
〔実施例１５〕
実施例９におけるメトキサジアゾン０．３重量部を０．９重量部に代え、ポリプロピレングリコール３０００（ＰＰＧ３０００）５７．７重量部を５７．１重量部に代え、同様の操作をして本発明硬化性組成物１５を得た。
[Example 15]
The curable composition of the present invention was prepared in the same manner by replacing 0.3 parts by weight of methoxadiazone in Example 9 with 0.9 parts by weight and replacing 57.7 parts by weight of polypropylene glycol 3000 (PPG3000) with 57.1 parts by weight. I got item 15.
〔実施例１６〕
実施例１５におけるメチルジメトキシシリル基末端ポリプロピレンオキシド系重合体１００重量部をメチルジメトキシシリル基末端ポリプロピレンオキシド系重合体（商品名「ＭＳポリマーＳ２０３Ｈ」、株式会社カネカ）１００重量部に代え、メトキサジアゾン０．９重量部をフェノブカルブ０．９重量部に代え、後は同様の操作をして、本発明硬化性組成物１６を得た。
[Example 16]
100 parts by weight of the methyldimethoxysilyl group-terminated polypropylene oxide polymer in Example 15 was replaced with 100 parts by weight of a methyldimethoxysilyl group-terminated polypropylene oxide polymer (trade name: "MS Polymer S203H", Kaneka Corporation), and 0.5 parts by weight of methoxadiazone was added. The curable composition 16 of the present invention was obtained by replacing 9 parts by weight with 0.9 parts by weight of fenocarb and performing the same operation.
〔実施例１７〕
実施例１４におけるメチルジメトキシシリル基末端ポリプロピレンオキシド系重合体１００重量部をメチルジメトキシシリル基末端ポリプロピレンオキシド系重合体（商品名「ＭＳポリマーＳ２０３Ｈ」、株式会社カネカ）１００重量部に代え、メトキサジアゾン０．９重量部をプロポキスル０．９重量部に代え、後は同様の操作をして、本発明硬化性組成物１７を得た。
[Example 17]
100 parts by weight of the methyldimethoxysilyl group-terminated polypropylene oxide polymer in Example 14 was replaced with 100 parts by weight of a methyldimethoxysilyl group-terminated polypropylene oxide polymer (trade name: "MS Polymer S203H", Kaneka Corporation), and 0.5 parts of methoxadiazone was added. A curable composition 17 of the present invention was obtained by replacing 9 parts by weight with 0.9 parts by weight of propoxur and performing the same operation thereafter.
〔実施例１８〕
実施例１におけるメトキサジアゾン０．３重量部をｄ・ｄ－Ｔ－シフェノトリン１重量部および「ＭＧＫ２６４」５重量部に、フタル酸ジエチルヘキシル５７．７重量部をフタル酸ジイソノニル（ＤＩＮＰ）（和光純薬株式会社）５２重量部に代え、後は同様の操作をして、本発明硬化性組成物１８を得た。
[Example 18]
0.3 parts by weight of methoxadiazone in Example 1 was added to 1 part by weight of d·dT-cyphenothrin and 5 parts by weight of "MGK264", and 57.7 parts by weight of diethylhexyl phthalate was added to diisononyl phthalate (DINP) (Wako Jun Yaku Co., Ltd.) was replaced with 52 parts by weight, and the same procedure was followed to obtain curable composition 18 of the present invention.
〔実施例１９〕
実施例１におけるメトキサジアゾン０．３重量部をメトキサジアゾン０．１５重量部およびピペロニルブトキシド（ＰＢＯ）１．５重量部に、フタル酸ジエチルヘキシル５７．７重量部をフタル酸ジイソノニル（ＤＩＮＰ）（和光純薬株式会社）５６．３５重量部に代え、後は同様の操作をして、本発明硬化性組成物１９を得た。
[Example 19]
0.3 parts by weight of methoxadiazone in Example 1 was added to 0.15 parts by weight of methoxadiazon and 1.5 parts by weight of piperonyl butoxide (PBO), and 57.7 parts by weight of diethylhexyl phthalate was added to diisononyl phthalate (DINP) (Wako Pure Chemical Industries, Ltd.). Company) was replaced with 56.35 parts by weight, but the same procedure was followed to obtain curable composition 19 of the present invention.
〔実施例２０〕
実施例１９におけるピペロニルブトキシド（ＰＢＯ）１．５重量部をピリプロキシフェン０．０１重量部に代え、フタル酸ジイソノニル（ＤＩＮＰ）（和光純薬株式会社）５６．４重量部を５７．８４重量部に代え、後は同様の操作をして、本発明硬化性組成物２０を得た。
[Example 20]
1.5 parts by weight of piperonyl butoxide (PBO) in Example 19 was replaced with 0.01 parts by weight of pyriproxyfen, and 56.4 parts by weight of diisononyl phthalate (DINP) (Wako Pure Chemical Industries, Ltd.) was changed to 57.84 parts by weight. A curable composition 20 of the present invention was obtained by performing the same operation instead.
〔比較例１〕
実施例１８におけるｄ・ｄ－Ｔ－シフェノトリン１重量を０重量部に代え（不使用）、フタル酸ジイソノニル５２重量部を５３重量部に代え、後は同様の操作をして、比較硬化性組成物１を得た。
[Comparative Example 1]
Replace 1 part by weight of d·dT-cyphenothrin in Example 18 with 0 parts by weight (not used), replace 52 parts by weight of diisononyl phthalate with 53 parts by weight, and then perform the same operation to obtain comparative curability. Composition 1 was obtained.
本発明硬化性組成物１４～２０と比較硬化性組成物１の組成を表３にまとめた。すなわち、実施例１４～１７、１９、２０では害虫防除剤としてカーバメート系化合物を用いている。実施例１８では害虫防除剤としてピレスロイド系化合物を用いている。また実施例１８、１９では共力剤を、実施例２０では昆虫成長制御剤を併用している。比較例１では害虫防除剤を使用せず共力剤のみを使用している。 The compositions of curable compositions 14 to 20 of the present invention and comparative curable composition 1 are summarized in Table 3. That is, in Examples 14 to 17, 19 and 20, a carbamate compound is used as an insect control agent. In Example 18, a pyrethroid compound is used as an insect control agent. In Examples 18 and 19, a synergist is used, and in Example 20, an insect growth regulator is used. In Comparative Example 1, only a synergist was used without using an insect control agent.
〔試験例２〕
試験例１と同様の方法で試験を行い、ヒラタチャタテの致死率の平均値（平均致死率）を算出した。結果を表４に示す。
[Test Example 2]
A test was conducted in the same manner as in Test Example 1, and the average mortality rate (average mortality rate) of flatfish was calculated. Table 4 shows the results.
すなわち、実施例１４、１５、１７、１９、２０の硬化性組成物（本発明硬化性組成物１４、１５、１７、１９、２０）では１００％の致死率であった。実施例１６、１８の硬化性組成物（本発明硬化性組成物１６、１８）でも９０％以上の高い致死率が得られた。特に、実施例１８において、ピレスロイド系化合物を用いる場合でも共力剤と組み合わせることによって、カーバメート系化合物と同程度の使用量で高い致死率が得られた。なお、共力剤のみ用いた比較例１では致死率が非常に低かった。 That is, the curable compositions of Examples 14, 15, 17, 19 and 20 (curable compositions 14, 15, 17, 19 and 20 of the present invention) had a mortality rate of 100%. The curable compositions of Examples 16 and 18 (Inventive Curable Compositions 16 and 18) also gave a high mortality rate of 90% or more. In particular, in Example 18, even when a pyrethroid compound was used in combination with a synergist, a high lethality rate was obtained at the same dosage as the carbamate compound. In Comparative Example 1, in which only a synergist was used, the fatality rate was very low.
以下の実施例２１～２７では、ピレスロイド系化合物と共力剤との組み合わせについてさらに検討した。 In Examples 21 to 27 below, combinations of pyrethroid compounds and synergists were further investigated.
〔実施例２１〕
実施例１におけるメトキサジアゾン０．３重量部をペルメトリン３重量部および「ＭＧＫ２６４」１５重量部に代え、フタル酸ジエチルヘキシル５７．７重量部をフタル酸ジイソノニル（ＤＩＮＰ）４０重量部に代え、後は同様の操作をして本発明硬化性組成物２１を得た。
[Example 21]
Replace 0.3 parts by weight of methoxadiazone in Example 1 with 3 parts by weight of permethrin and 15 parts by weight of "MGK264", replace 57.7 parts by weight of diethylhexyl phthalate with 40 parts by weight of diisononyl phthalate (DINP), and the rest is the same. to obtain a curable composition 21 of the present invention.
〔実施例２２〕
実施例２１におけるペルメトリン３重量部を４．５重量部に代え、「ＭＧＫ２６４」１５重量部を１８重量部に代え、フタル酸ジイソノニル４０重量部を３５．５重量部に代え、後は同様の操作をして本発明硬化性組成物２２を得た。
[Example 22]
Replace 3 parts by weight of permethrin in Example 21 with 4.5 parts by weight, replace 15 parts by weight of "MGK264" with 18 parts by weight, replace 40 parts by weight of diisononyl phthalate with 35.5 parts by weight, and then repeat the procedure. to obtain a curable composition 22 of the present invention.
〔実施例２３〕
実施例２１におけるペルメトリン３重量部をｄ－Ｔ８０－レスメトリン３重量部に代え、後は同様の操作をして本発明硬化性組成物２３を得た。
[Example 23]
A curable composition 23 of the present invention was obtained in the same manner as in Example 21 except that 3 parts by weight of permethrin in Example 21 was replaced with 3 parts by weight of d-T80-resmethrin.
〔実施例２４〕
実施例２１におけるペルメトリン３重量部をトランスフルトリン１．５重量部に代え、フタル酸ジイソノニル４０重量部を４１．５重量部に代え、後は同様の操作をして本発明硬化性組成物２４を得た。
[Example 24]
The 3 parts by weight of permethrin in Example 21 was replaced with 1.5 parts by weight of transfluthrin, and the 40 parts by weight of diisononyl phthalate was replaced with 41.5 parts by weight. got
〔実施例２５〕
実施例２４におけるトランスフルトリン１．５重量部を０．９重量部に代え、「ＭＧＫ２６４」１５重量部を９重量部に代え、フタル酸ジイソノニル４１．５重量部を４８．１重量部に代え、後は同様の操作をして本発明硬化性組成物２５を得た。
[Example 25]
Replace 1.5 parts by weight of transfluthrin in Example 24 with 0.9 parts by weight, replace 15 parts by weight of "MGK264" with 9 parts by weight, and replace 41.5 parts by weight of diisononyl phthalate with 48.1 parts by weight. , and then the same operation was performed to obtain a curable composition 25 of the present invention.
〔実施例２６〕
実施例２４における「ＭＧＫ２６４」１５重量部を０重量部に代え（不使用）、フタル酸ジイソノニル４１．５重量部を５６．５重量部に代え、後は同様の操作をして本発明硬化性組成物２６を得た。
[Example 26]
15 parts by weight of "MGK264" in Example 24 was replaced with 0 parts by weight (not used), 41.5 parts by weight of diisononyl phthalate was replaced with 56.5 parts by weight, and then the same operation was performed to obtain the curability of the present invention. Composition 26 was obtained.
〔実施例２７〕
実施例２１におけるペルメトリン３重量部を４．５重量部に代え、「ＭＧＫ２６４」１５重量部をピペロニルブトキシド（ＰＢＯ）１８重量部に代え、フタル酸ジイソノニル４０重量部を３５．５重量部に代え、後は同様の操作をして本発明硬化性組成物２７を得た。
[Example 27]
Replace 3 parts by weight of permethrin in Example 21 with 4.5 parts by weight, replace 15 parts by weight of "MGK264" with 18 parts by weight of piperonyl butoxide (PBO), replace 40 parts by weight of diisononyl phthalate with 35.5 parts by weight, and obtained the curable composition 27 of the present invention by performing the same operation.
本発明硬化性組成物２１～２７の組成を表５にまとめた。すなわち、実施例２１と２２では、ペルメトリンとＭＧＫ２６４を併用している。実施例２３では、ｄ－Ｔ８０－レスメトリンとＭＧＫ２６４を併用している。実施例２４と２５では、トランスフルトリンとＭＧＫ２６４を併用している。実施例２６では、トランスフルトリンのみを使用している。実施例２７では、ペルメトリンとＰＢＯを併用している。 The compositions of curable compositions 21 to 27 of the present invention are summarized in Table 5. That is, in Examples 21 and 22, permethrin and MGK264 are used together. Example 23 uses a combination of d-T80-resmethrin and MGK264. Examples 24 and 25 use a combination of transfluthrin and MGK264. Example 26 uses only transfluthrin. In Example 27, permethrin and PBO are used together.
〔試験例３〕
試験例１と同様の方法で試験を行い、ヒラタチャタテの致死率の平均値（平均致死率）を算出した。ただし、致死率は放虫後２４時間後と４８時間後の２点で観察した。結果を表６に示す。
[Test Example 3]
A test was conducted in the same manner as in Test Example 1, and the average mortality rate (average mortality rate) of flatfish was calculated. However, the mortality rate was observed at two points, 24 hours and 48 hours after release. Table 6 shows the results.
すなわち、ピレスロイド系化合物と共力剤を併用した実施例２１～２５、２７の硬化性組成物（本発明硬化性組成物２１～２５、２７）では、組成物中におけるピレスロイド系化合物の含有率が０．３％（実施例２５）～１．５％（実施例２２、２７）程度でも、６６％以上の致死率（４８時間後）が得られた。特に、トランスフルトリンとＭＧＫ２６４を併用した実施例２４と実施例２５では、ほぼ１００％の致死率（２４時間、４８時間）が得られ、効果が特に顕著であった。 That is, in the curable compositions of Examples 21 to 25 and 27 (curable compositions 21 to 25 and 27 of the present invention) in which a pyrethroid compound and a synergist were used in combination, the content of the pyrethroid compound in the composition was A fatality rate of 66% or more (after 48 hours) was obtained even at about 0.3% (Example 25) to 1.5% (Examples 22 and 27). In particular, in Examples 24 and 25, in which transfluthrin and MGK264 were used in combination, almost 100% lethality (24 hours, 48 hours) was obtained, and the effect was particularly remarkable.
上記実施例と同様の手順にて、表７、表８に示す組成の本発明硬化性組成物２８～４１と比較硬化性組成物２、３を得た（実施例２８～４１、比較例２、比較例３）。上記試験例３と同様の手順にて、各組成物についてヒラタチャタテの致死率の平均値（平均致死率）を算出した（表９）。 The curable compositions 28 to 41 of the present invention and comparative curable compositions 2 and 3 having the compositions shown in Tables 7 and 8 were obtained in the same procedure as in the above Examples (Examples 28 to 41, Comparative Example 2 , Comparative Example 3). In the same manner as in Test Example 3, the average mortality rate (average mortality rate) of flounder flounder was calculated for each composition (Table 9).
ビフェントリンとＭＧＫ２６４を併用した実施例３２、３３（本発明硬化性組成物３２、３３）と、ビフェントリンとＰＢＯを併用した実施例３４（本発明硬化性組成物３４）において、ほぼ１００％の致死率（２４時間、４８時間）が得られ、特に効果が顕著であった。 Nearly 100% fatality rate in Examples 32 and 33 (inventive curable compositions 32 and 33) in which bifenthrin was used in combination with MGK264, and in Example 34 (inventive curable composition 34) in which bifenthrin and PBO were used in combination. (24 hours, 48 hours) were obtained, and the effect was particularly remarkable.
Claims (13)
－Ｓｉ（Ｒ１）３－ａＸａ （１）
（式中、Ｒ１は１価炭化水素基又はハロゲン化１価炭化水素基を表し、Ｘは水素原子、ハロゲン原子、又はアルコキシ基を表し、ａは０～３の整数を表す。）
で表される反応性ケイ素基を１分子中に少なくとも１個含有するポリオキシアルキレン系重合体を主成分とする基材、
（Ｂ）炭素数４～１２アルコールの２価カルボン酸ジエステル及び／又はポリプロピレングリコール、並びに、
（Ｃ）害虫防除剤、
を含む匍匐害虫防除用硬化性組成物であって、
前記害虫防除剤が、ピレトリン、トランスフルトリン、シフェノトリン、又はビフェントリンであり、
さらに共力剤を含み、
前記匍匐害虫がチャタテムシ類である、匍匐害虫防除用硬化性組成物。 (A) the following general formula (1):
—Si(R 1 ) 3-a X a (1)
(Wherein, R 1 represents a monovalent hydrocarbon group or a halogenated monovalent hydrocarbon group, X represents a hydrogen atom, a halogen atom, or an alkoxy group, and a represents an integer of 0 to 3.)
A substrate mainly composed of a polyoxyalkylene polymer containing at least one reactive silicon group in one molecule represented by
(B) C4-C12 alcohol divalent carboxylic acid diester and/or polypropylene glycol, and
(C) a pest control agent;
A curable composition for controlling crawling pests comprising
the pest control agent is pyrethrin, transfluthrin, cyphenothrin, or bifenthrin;
further containing a synergist,
A curable composition for controlling creeping pests, wherein the creeping pests are bookworms.
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| PCT/JP2017/039164 WO2018079780A1 (en) | 2016-10-31 | 2017-10-30 | Curable composition for crawling pest control, sealing material, and crawling pest control method |
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| JP2006117595A (en) * | 2004-10-22 | 2006-05-11 | Earth Chem Corp Ltd | Psocid-controlling agent and psocid-controlling material |
| JP2011088859A (en) * | 2009-10-23 | 2011-05-06 | Sharp Kagaku Kogyo Kk | Moisture curing resin composition for repelling insect pest, article for repelling insect pest, and insect pest repelling method |
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| JP2011088859A (en) * | 2009-10-23 | 2011-05-06 | Sharp Kagaku Kogyo Kk | Moisture curing resin composition for repelling insect pest, article for repelling insect pest, and insect pest repelling method |
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| PEST MANAG SCI, vol. 66, JPN6017050616, 2010, pages 295 - 300, ISSN: 0005219576 * |
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