JP6061759B2 - Transester compounds and uses thereof - Google Patents
Transester compounds and uses thereof Download PDFInfo
- Publication number
- JP6061759B2 JP6061759B2 JP2013077384A JP2013077384A JP6061759B2 JP 6061759 B2 JP6061759 B2 JP 6061759B2 JP 2013077384 A JP2013077384 A JP 2013077384A JP 2013077384 A JP2013077384 A JP 2013077384A JP 6061759 B2 JP6061759 B2 JP 6061759B2
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- Prior art keywords
- compound
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- transester
- general formula
- chemical formula
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Description
本発明は、トランスエステル化合物及びその用途に関する。 The present invention relates to a transester compound and use thereof.
従来、有害生物を防除するために種々の化合物が合成されている(非特許文献1参照)。また、特許文献1には、ある種のエステル化合物が記載されている。しかしながら、これらの有害生物防除効力は必ずしも満足のいくものではない。 Conventionally, various compounds have been synthesized in order to control pests (see Non-Patent Document 1). Patent Document 1 describes certain ester compounds. However, these pest control effects are not always satisfactory.
本発明らは、優れた有害生物防除効力を有する新規なエステル化合物を提供することを課題とする。 It is an object of the present invention to provide a novel ester compound having an excellent pest control effect.
本発明者は、鋭意検討を行った結果、下記一般式[化1]で示されるトランスエステル化合物が優れた有害生物防除効力を有することを見出し、本発明を完成するに至った。 As a result of intensive studies, the present inventor has found that the transester compound represented by the following general formula [Chemical Formula 1] has an excellent pest control effect, and has completed the present invention.
即ち、本発明は、以下の発明に係るものである。
(1)一般式[化1]
[化1]
〔式中、Xは酸素原子、または硫黄原子のいずれかを表し、Yはメチル基または塩素原子を表し、Yがメチル基の時、Zは水素原子またはメチル基を表し、Yが塩素原子の時、Zは塩素原子を表す。〕
で示されるトランスエステル化合物(以下、本発明化合物と記す。)。
(2)前記一般式[化1]において、Xが酸素原子である(1)に記載のトランスエステル化合物。
(3)前記一般式[化1]において、Xが硫黄原子である(1)に記載のトランスエステル化合物。
(4)前記一般式[化1]において、Xが酸素原子、YおよびZがメチル基である(1)に記載のトランスエステル化合物。
(5)前記一般式[化1]において、Xが酸素原子、YおよびZが塩素原子である(1)に記載のトランスエステル化合物。
(6)前記一般式[化1]において、Xが酸素原子、Yがメチル基、Zが水素原子である(1)に記載のトランスエステル化合物。
(7)(1)ないし(6)のいずれか1に記載のトランスエステル化合物を有効成分として含有する有害生物防除剤。
(8)(1)ないし(6)のいずれか1に記載のトランスエステル化合物の有効量を有害生物又は有害生物の生息場所に施用する有害生物の防除方法、ただし人体への使用は除く。
That is, the present invention relates to the following inventions.
(1) General formula [Formula 1]
[Chemical 1]
[In the formula, X represents either an oxygen atom or a sulfur atom, Y represents a methyl group or a chlorine atom, and when Y is a methyl group, Z represents a hydrogen atom or a methyl group, and Y represents a chlorine atom. When Z represents a chlorine atom. ]
A transester compound (hereinafter referred to as the present compound).
(2) The transester compound according to (1), wherein in the general formula [Chemical Formula 1], X is an oxygen atom.
(3) The transester compound according to (1), wherein, in the general formula [Chemical Formula 1], X is a sulfur atom.
(4) The transester compound according to (1), wherein in the general formula [Chemical Formula 1], X is an oxygen atom, and Y and Z are methyl groups.
(5) The transester compound according to (1), wherein, in the general formula [Chemical Formula 1], X is an oxygen atom, and Y and Z are chlorine atoms.
(6) The transester compound according to (1), wherein, in the general formula [Chemical Formula 1], X is an oxygen atom, Y is a methyl group, and Z is a hydrogen atom.
(7) A pest control agent comprising the transester compound according to any one of (1) to (6) as an active ingredient.
(8) A pest control method in which an effective amount of the transester compound according to any one of (1) to (6) is applied to a pest or a pest habitat , except for use on the human body .
本発明化合物は優れた有害生物防除効力を有することから、有害生物防除剤の有効成分として有用である。 Since the compound of the present invention has an excellent pesticidal activity, it is useful as an active ingredient of a pesticidal agent.
本発明化合物には、シクロプロパン環上の1位および3位に存在する2個の不斉炭素原子に由来する光学異性体、並びに、シクロプロパン環3位の置換基に存在する1’位の二重結合に由来する異性体が存在するが、本発明には有害生物防除活性を有する各異性体および任意の比率の異性体混合物が含まれる。 The compound of the present invention includes an optical isomer derived from two asymmetric carbon atoms present at the 1-position and the 3-position on the cyclopropane ring, and a 1'-position present on a substituent at the 3-position of the cyclopropane ring. Although there are isomers derived from double bonds, the present invention includes each isomer having pesticidal activity and a mixture of isomers in any ratio.
即ち、一般式[化2]
において、シクロプロパン環1位の置換基とシクロプロパン環3位の置換基との相対立体配置がトランス配置である化合物;
一般式[化2]において、シクロプロパン環1位の絶対立体配置がR配置であり、シクロプロパン環1位の置換基とシクロプロパン環3位の置換基との相対立体配置がトランス配置である化合物;
一般式[化2]において、Yがメチル基、Zが水素原子を表す時、シクロプロパン環1位の置換基とシクロプロパン環3位の置換基との相対立体配置がトランス配置であり、シクロプロパン環3位の置換基に存在する1’位の二重結合の相対配置がZ配置である化合物;
一般式[化2]において、Yがメチル基、Zが水素原子を表す時、シクロプロパン環1位の絶対立体配置がR配置であり、シクロプロパン環1位の置換基とシクロプロパン環3位の置換基との相対立体配置がトランス配置であり、シクロプロパン環3位の置換基に存在する1’位の二重結合の相対配置がE配置である化合物;
That is, the general formula [Chemical Formula 2]
Wherein the relative configuration of the substituent at the 1-position of the cyclopropane ring and the substituent at the 3-position of the cyclopropane ring is a trans configuration;
In the general formula [Chemical Formula 2], the absolute configuration at the 1-position of the cyclopropane ring is an R configuration, and the relative configuration between the substituent at the 1-position of the cyclopropane ring and the substituent at the 3-position of the cyclopropane ring is a trans configuration. Compound;
In the general formula [Chemical Formula 2], when Y represents a methyl group and Z represents a hydrogen atom, the relative configuration of the substituent at the 1-position of the cyclopropane ring and the substituent at the 3-position of the cyclopropane ring is a trans configuration. A compound in which the relative configuration of the 1′-position double bond in the substituent at the 3-position of the propane ring is the Z configuration;
In the general formula [Chemical Formula 2], when Y represents a methyl group and Z represents a hydrogen atom, the absolute configuration at the 1-position of the cyclopropane ring is the R-configuration, and the substituent at the 1-position of the cyclopropane ring and the 3-position of the cyclopropane ring A compound in which the relative configuration with respect to the substituent is a trans configuration, and the relative configuration of the 1′-position double bond present in the substituent at the 3-position of the cyclopropane ring is the E configuration;
一般式[化2]において、Xが酸素原子である化合物。
一般式[化2]において、Xが硫黄原子である化合物。
In the general formula [Chemical Formula 2], compounds wherein X is an oxygen atom.
In the general formula [Chemical Formula 2], compounds wherein X is a sulfur atom.
次に本発明化合物の製造法について説明する。
本発明化合物は、例えば以下に示す方法により製造することができる。
(製造法1)
一般式[化3]
〔式中、Xは前記と同じ意味を表す。〕で示されるアルコール化合物と、
一般式[化4]
〔式中、YおよびZは前記と同じ意味を表す。〕で示されるカルボン酸化合物又はその反応性誘導体とを反応させる方法。
Next, the manufacturing method of this invention compound is demonstrated.
The compound of the present invention can be produced, for example, by the method shown below.
(Production method 1)
[Formula 3]
[Wherein X represents the same meaning as described above. An alcohol compound represented by
[Formula 4]
[Wherein Y and Z represent the same meaning as described above. ] The carboxylic acid compound shown by this, or its reactive derivative is made to react.
該反応性誘導体としては、一般式[化4]で示されるカルボン酸化合物の酸ハロゲン化物、該カルボン酸化合物の酸無水物および該カルボン酸化合物のエステル等が挙げられる。該酸ハロゲン化物としては、酸クロライド化合物が挙げられ、エステルとしてはメチルエステル、エチルエステルなどが挙げられる。
該反応は、通常、縮合剤又は塩基の存在下、溶媒中で行なわれる。
縮合剤としては、例えば、ジシクロヘキシルカルボジイミド、1−エチル−3−(3−ジメチルアミノプロピル)カルボジイミド ハイドロクロライドが挙げられ、また、
塩基としては、トリエチルアミン、ピリジン、4−ジメチルアミノピリジン、ジイソプロピルエチルアミン等の有機塩基が挙げられる。
溶媒としては、例えばトルエン及びヘキサン等の炭化水素、テトラヒドロフラン等のエ−テル、エチルアセテートなどのエステル、並びに、クロロベンゼン等のハロゲン化炭化水素、及びこれらの混合溶媒等が挙げられる。
Examples of the reactive derivative include an acid halide of the carboxylic acid compound represented by the general formula [Chemical Formula 4], an acid anhydride of the carboxylic acid compound, and an ester of the carboxylic acid compound. Examples of the acid halide include acid chloride compounds, and examples of the ester include methyl ester and ethyl ester.
The reaction is usually performed in a solvent in the presence of a condensing agent or a base.
Examples of the condensing agent include dicyclohexylcarbodiimide, 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride,
Examples of the base include organic bases such as triethylamine, pyridine, 4-dimethylaminopyridine, diisopropylethylamine.
Examples of the solvent include hydrocarbons such as toluene and hexane, ethers such as tetrahydrofuran, esters such as ethyl acetate, halogenated hydrocarbons such as chlorobenzene, and mixed solvents thereof.
反応時間は、通常、5分間〜72時間の範囲である。
反応温度は、通常、−20℃〜100℃(但し、使用する溶媒の沸点が100℃未満の場合には、−20℃〜溶媒の沸点)の範囲である。
該反応において、一般式[化3]で示されるアルコ−ル化合物と、一般式[化4]で示されるカルボン酸化合物又はその反応性誘導体の使用モル比は任意に設定できるが、好ましくは、等モル又はそれに近い比である。
縮合剤又は塩基は、一般式[化3]で示されるアルコ−ル化合物1モルに対して、通常は0.25モルから過剰量まで任意の割合で使用することができ、好ましくは0.5モル〜2モルである。これらの縮合剤又は塩基は、一般式[化4]で示されるカルボン酸化合物又はその反応性誘導体の種類により適宜選択される。
反応終了後の反応混合物は、これを濾過して濾液を濃縮する、又は、これを水に注加した後に有機溶媒抽出、濃縮する等の通常の後処理操作を施すことにより、本発明化合物を得ることができる。得られた本発明化合物はクロマトグラフィ−、蒸留等の操作によって精製することができる。
The reaction time is usually in the range of 5 minutes to 72 hours.
The reaction temperature is usually in the range of −20 ° C. to 100 ° C. (however, when the boiling point of the solvent used is less than 100 ° C., it is −20 ° C. to the boiling point of the solvent).
In the reaction, the molar ratio of the alcohol compound represented by the general formula [Chemical Formula 3] and the carboxylic acid compound represented by the general formula [Chemical Formula 4] or a reactive derivative thereof can be arbitrarily set. Equimolar or close ratio.
The condensing agent or base can be used in an arbitrary ratio from 0.25 mol to an excess amount with respect to 1 mol of the alcohol compound represented by the general formula [Chem. 3], preferably 0.5 Mol to 2 mol. These condensing agents or bases are appropriately selected depending on the type of the carboxylic acid compound represented by the general formula [Chemical Formula 4] or a reactive derivative thereof.
The reaction mixture after completion of the reaction is filtered to concentrate the filtrate, or poured into water and then subjected to usual post-treatment operations such as organic solvent extraction and concentration, whereby the compound of the present invention is obtained. Can be obtained. The obtained compound of the present invention can be purified by operations such as chromatography and distillation.
一般式[化3]で示されるアルコール化合物(X=酸素原子)は、特開平6−25205号公報記載の公知化合物であり、該特許に記載の方法で製造することができる。また、一般式[化3]で示されるアルコール化合物(X=硫黄原子)は、新規化合物であり、下記に示した方法により市販の2,5−チオフェンジカルバルデヒドより2工程で合成することが出来る。
一方、一般式[化4]で示されるカルボン酸化合物又はその反応性誘導体は市販品またはSynthetic
Communications(2004) 34巻1001-10に記載の公知化合物であり、市販品を購入、または該文献に記載の方法で製造することができる。
The alcohol compound represented by the general formula [Chemical Formula 3] (X = oxygen atom) is a known compound described in JP-A-6-25205 and can be produced by the method described in the patent. In addition, the alcohol compound (X = sulfur atom) represented by the general formula [Chemical Formula 3] is a novel compound, and can be synthesized in two steps from commercially available 2,5-thiophenedicarbaldehyde by the method shown below. I can do it.
On the other hand, the carboxylic acid compound represented by the general formula [Chemical Formula 4] or a reactive derivative thereof is a commercially available product or a synthetic compound.
This is a known compound described in Communications (2004) 34, 1001-10, and can be purchased from the market or produced by the method described in the document.
本発明の有害生物防除剤は本発明化合物そのものでもよいが、通常は下記のような製剤として使用する。その製剤としては、例えば、蚊取線香、蚊取マットや蚊取リキッドのような加熱蒸散剤、ファン式蚊取、油剤、乳剤、エアゾール剤、炭酸ガス製剤、水和剤、フロアブル剤(水中懸濁剤、水中乳濁剤等)、マイクロカプセル剤、粉剤、粒剤、錠剤、ピエゾ式殺虫製剤、加熱燻煙剤(自己燃焼型燻煙剤、化学反応型燻煙剤、多孔セラミック板燻煙剤等)、非加熱蒸散剤(樹脂蒸散剤、紙蒸散剤、不織布蒸散剤、編織物蒸散剤、昇華性錠剤等)、煙霧剤(フォッギング等)、直接接触剤(シート状接触剤、テープ状接触剤、ネット状接触剤等)、ULV剤及び毒餌などが挙げられる。 The pest control agent of the present invention may be the compound of the present invention itself, but is usually used as the following preparation. Examples of the preparation include heat transpiration agents such as mosquito coils, mosquito mats and mosquito liquids, fan mosquito traps, oils, emulsions, aerosols, carbon dioxide preparations, wettable powders and flowables Suspensions, emulsions in water, etc.), microcapsules, powders, granules, tablets, piezo insecticides, heated smokes (self-burning smoke, chemical reaction smoke, porous ceramic smoke) Agent), non-heating transpiration agent (resin transpiration agent, paper transpiration agent, non-woven fabric transpiration agent, knitted fabric transpiration agent, sublimation tablet, etc.), fumes (fogging etc.), direct contact agent (sheet-like contact agent, tape form) Contact agents, net-like contact agents, etc.), ULV agents and poison baits.
製剤化の方法としては、例えば以下の方法を挙げることができる。
(1)本発明化合物を、固体担体、液体担体、ガス状担体、餌等と混合し、必要に応じて界面活性剤その他の製剤用補助剤を添加・加工する方法。
(2)本発明化合物を、有効成分を含有していない基材に含浸する方法。
(3)本発明化合物及び基材を混合した後に成形加工する方法。
これらの製剤には、製剤形態にもよるが、通常、本発明化合物を重量比で0.001〜98%含有する。
Examples of the formulation method include the following methods.
(1) A method in which the compound of the present invention is mixed with a solid carrier, liquid carrier, gaseous carrier, bait and the like, and a surfactant and other formulation adjuvants are added and processed as necessary.
(2) A method of impregnating a base material containing no active ingredient with the compound of the present invention.
(3) A method of molding after mixing the compound of the present invention and the substrate.
These preparations usually contain 0.001 to 98% by weight of the compound of the present invention, depending on the form of preparation.
製剤化の際に用いられる固体担体としては、例えば粘土類(カオリンクレー、珪藻土、ベントナイト、フバサミクレー、酸性白土等)、合成含水酸化珪素、タルク、セラミック、その他の無機鉱物(セリサイト、活性炭、炭酸カルシウム、シリカ等)等の微粉末及び粒状物、常温で固体の物質(2,4,6−トリイソプロピル−1,3,5−トリオキサン、ナフタリン、p−ジクロロベンゼン、樟脳、アダマンタン等)、並びに羊毛、絹、綿、麻、パルプ、合成樹脂(例えば、低密度ポリエチレン、直鎖状低密度ポリエチレン、高密度ポリエチレン等のポリエチレン系樹脂;エチレン−酢酸ビニル共重合体等のエチレン−ビニルエステル共重合体;エチレン−メタクリル酸メチル共重合体、エチレン−メタクリル酸エチル共重合体等のエチレン−メタクリル酸エステル共重合体;エチレン−アクリル酸メチル共重合体、エチレン−アクリル酸エチル共重合体等のエチレン−アクリル酸エステル共重合体;エチレン−アクリル酸共重合体等のエチレン−ビニルカルボン酸共重合体;ポリプロピレン、プロピレン−エチレン共重合体等のポリプロピレン系樹脂;ポリ−4−メチルペンテン−1、ポリブテン−1、ポリブタジエン、ポリスチレン;アクリロニトリル−スチレン樹脂;アクリロニトリル−ブタジエン−スチレン樹脂、スチレン−共役ジエンブロック共重合体、スチレン−共役ジエンブロック共重合体水素添加物等のスチレン系エラストマー;フッ素樹脂;ポリメタクリル酸メチル等のアクリル系樹脂;ナイロン6、ナイロン66等のポリアミド系樹脂;ポリエチレンテレフタレート、ポリエチレンナフタレート、ポリブチレンテレフタレエート等のポリエステル系樹脂;ポリカーボネート、ポリアセタール、ポリアリレート、ヒドロキシ安息香酸ポリエステル、ポリエーテルイミド、ポリエステルカーボネート、ポリフェニレンエーテル樹脂、ポリ塩化ビニル、ポリ塩化ビニリデン、ポリウレタン、発泡ポリウレタン、発泡ポリプロピレン、発泡エチレン等の多孔質樹脂)、ガラス、金属、セラミック等の1種または2種以上からなるフェルト、繊維、布、編物、シート、紙、糸、発泡体、多孔質体及びマルチフィラメントが挙げられる。 Examples of solid carriers used in the formulation include clays (kaolin clay, diatomaceous earth, bentonite, fusami clay, acidic clay), synthetic hydrous silicon oxide, talc, ceramic, and other inorganic minerals (sericite, activated carbon, carbonic acid). Fine powders and granules such as calcium, silica, etc., solid substances at room temperature (2,4,6-triisopropyl-1,3,5-trioxane, naphthalene, p-dichlorobenzene, camphor, adamantane, etc.), and Wool, silk, cotton, hemp, pulp, synthetic resin (eg, polyethylene resins such as low density polyethylene, linear low density polyethylene, and high density polyethylene; ethylene-vinyl ester copolymer such as ethylene-vinyl acetate copolymer) Polymer; Ethylene such as ethylene-methyl methacrylate copolymer, ethylene-ethyl methacrylate copolymer -Methacrylic acid ester copolymer; Ethylene-acrylic acid ester copolymer such as ethylene-methyl acrylate copolymer and ethylene-ethyl acrylate copolymer; Ethylene-vinyl carboxylic acid such as ethylene-acrylic acid copolymer Copolymers; Polypropylene resins such as polypropylene and propylene-ethylene copolymers; poly-4-methylpentene-1, polybutene-1, polybutadiene, polystyrene; acrylonitrile-styrene resins; acrylonitrile-butadiene-styrene resins, styrene-conjugates Styrene elastomers such as diene block copolymers and hydrogenated styrene-conjugated diene block copolymers; fluororesins; acrylic resins such as polymethyl methacrylate; polyamide resins such as nylon 6 and nylon 66; Polyester resins such as rate, polyethylene naphthalate, polybutylene terephthalate; polycarbonate, polyacetal, polyarylate, hydroxybenzoic acid polyester, polyetherimide, polyester carbonate, polyphenylene ether resin, polyvinyl chloride, polyvinylidene chloride, polyurethane, Felt, fiber, cloth, knitted fabric, sheet, paper, thread, foam, porous body composed of one or more of foamed polyurethane, foamed polypropylene, foamed ethylene, etc.), glass, metal, ceramic, etc. And multifilaments.
液体担体としては、例えば芳香族または脂肪族炭化水素類(キシレン、アルキルナフタレン、フェニルキシリルエタン、ケロシン、軽油、ヘキサン、シクロヘキサン等)、アルコール類(メタノール、エタノール、イソプロピルアルコール、ブタノール、ヘキサノール、ベンジルアルコール、エチレングリコール等)、エーテル類(ジエチルエーテル、エチレングリコールジメチルエーテル、ジエチレングリコールモノエチルエーテル、ジエチレングリコールモノブチルエーテル、プロピレングリコールモノメチルエーテル、テトラヒドロフラン等)、エステル類(酢酸エチル、酢酸ブチル等)、ケトン類(アセトン、メチルエチルケトン、メチルイソブチルケトン、シクロヘキサノン等)、ニトリル類(アセトニトリル、イソブチロニトリル等)、スルホキシド類(ジメチルスルホキシド等)、酸アミド類(N,N−ジメチルホルムアミド、N−メチル−ピロリドン等)、炭酸アルキリデン類(炭酸プロピレン等)、植物油(大豆油、綿実油等)、植物精油(オレンジ油、ヒソップ油、レモン油等)、及び水が挙げられる。 Examples of the liquid carrier include aromatic or aliphatic hydrocarbons (xylene, alkylnaphthalene, phenylxylylethane, kerosene, light oil, hexane, cyclohexane, etc.), alcohols (methanol, ethanol, isopropyl alcohol, butanol, hexanol, benzyl). Alcohol, ethylene glycol, etc.), ethers (diethyl ether, ethylene glycol dimethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether, tetrahydrofuran, etc.), esters (ethyl acetate, butyl acetate, etc.), ketones (acetone) , Methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, etc.), nitriles (acetonitrile, isobutyronitrile) ), Sulfoxides (dimethylsulfoxide, etc.), acid amides (N, N-dimethylformamide, N-methyl-pyrrolidone, etc.), alkylidene carbonates (propylene carbonate, etc.), vegetable oils (soybean oil, cottonseed oil, etc.), plant essential oils (Orange oil, hyssop oil, lemon oil, etc.) and water.
ガス状担体としては、例えばブタンガス、フロンガス、液化石油ガス(LPG)、ジメチルエーテル、及び炭酸ガス等の圧縮ガスが挙げられる。 Examples of the gaseous carrier include compressed gases such as butane gas, Freon gas, liquefied petroleum gas (LPG), dimethyl ether, and carbon dioxide gas.
界面活性剤としては、例えばアルキル硫酸エステル塩、アルキルスルホン酸塩、アルキルアリールスルホン酸塩、アルキルアリールエーテル類、アルキルアリールエーテル類のポリオキシエチレン化物、ポリエチレングリコールエーテル類、多価アルコールエステル類及び糖アルコール誘導体が挙げられる。 Surfactants include, for example, alkyl sulfate esters, alkyl sulfonates, alkyl aryl sulfonates, alkyl aryl ethers, polyarylethylenes of alkyl aryl ethers, polyethylene glycol ethers, polyhydric alcohol esters and sugars. Examples include alcohol derivatives.
その他の製剤用補助剤としては、固着剤、分散剤及び安定剤等、具体的には例えばカゼイン、ゼラチン、多糖類(でんぷん、アラビアガム、セルロース誘導体、アルギン酸等)、リグニン誘導体、ベントナイト、糖類、合成水溶性高分子(ポリビニルアルコール、ポリビニルピロリドン)、ポリアクリル酸等、BHT(2,6−ジ−tert−ブチル−4−メチルフェノール)、及びBHA(2−tert−ブチル−4−メトキシフェノールと3−tert−ブチル−4−メトキシフェノールとの混合物)が挙げられる。更に、必要に応じて着色剤や香料等が適宜配合されても構わない。 Other formulation adjuvants include fixing agents, dispersants and stabilizers, such as casein, gelatin, polysaccharides (starch, gum arabic, cellulose derivatives, alginic acid, etc.), lignin derivatives, bentonite, saccharides, Synthetic water-soluble polymers (polyvinyl alcohol, polyvinylpyrrolidone), polyacrylic acid, etc., BHT (2,6-di-tert-butyl-4-methylphenol), and BHA (2-tert-butyl-4-methoxyphenol) 3-tert-butyl-4-methoxyphenol). Furthermore, a coloring agent, a fragrance | flavor, etc. may be mix | blended suitably as needed.
蚊取線香の基材としては、例えば木粉、除虫菊抽出粕粉等の植物性粉末とタブ粉、澱粉、カルボキシメチルセルロース、グルテン等の結合剤との混合物が挙げられる。
蚊取マットの基材としては、例えばコットンリンターを板状に固めたもの、及びコットンリンターとパルプとの混合物のフィリブルを板状に固めたものが挙げられる。
自己燃焼型燻煙剤の基材としては、例えば、硝酸塩、亜硝酸塩、グアニジン塩、塩素酸カリウム、ニトロセルロース、エチルセルロース、木粉等の燃焼発熱剤、アルカリ金属塩、アルカリ土類金属塩の熱分解刺激剤、硝酸カリウム等の酸素供給剤、メラミン、小麦デンプン等の支燃剤、珪藻土等の増量剤及び合成糊料等の結合剤が挙げられる。
Examples of the base material of the mosquito coil include a mixture of a vegetable powder such as wood powder and pesticide extracted chrysanthemum powder and a binder such as tab powder, starch, carboxymethylcellulose, and gluten.
Examples of the base material of the mosquito trap include those obtained by solidifying a cotton linter into a plate shape and those obtained by solidifying a fillet of a mixture of cotton linter and pulp into a plate shape.
Examples of the base material of the self-burning smoke agent include nitrate, nitrite, guanidine salt, potassium chlorate, nitrocellulose, ethyl cellulose, wood powder and other combustion exothermic agents, alkali metal salts, alkaline earth metal salt heat Examples include decomposition stimulants, oxygen supply agents such as potassium nitrate, flame retardants such as melamine and wheat starch, bulking agents such as diatomaceous earth, and binders such as synthetic pastes.
化学反応型燻煙剤の基材としては、例えば、アルカリ金属の硫化物、多硫化物、水硫化物、酸化カルシウム等の発熱剤、炭化鉄、活性白土等の触媒剤、アゾジカルボンアミド、ベンゼンスルホニルヒドラジド、ジニトロペンタメチレンテトラミン、ポリスチレン、ポリウレタン等の有機発泡剤、及び、天然繊維片、合成繊維片等の充填剤が挙げられる。 Examples of the base material for the chemical reaction type smoke agent include exothermic agents such as alkali metal sulfides, polysulfides, hydrosulfides, and calcium oxide, catalyst agents such as iron carbide and activated clay, azodicarbonamide, and benzene. Examples thereof include organic foaming agents such as sulfonyl hydrazide, dinitropentamethylenetetramine, polystyrene, and polyurethane, and fillers such as natural fiber pieces and synthetic fiber pieces.
樹脂蒸散剤等の基材に用いられる樹脂としては、例えば、低密度ポリエチレン、直鎖状低密度ポリエチレン、高密度ポリエチレン等のポリエチレン系樹脂;エチレン−酢酸ビニル共重合体等のエチレン−ビニルエステル共重合体;エチレン−メタクリル酸メチル共重合体、エチレン−メタクリル酸エチル共重合体等のエチレン−メタクリル酸エステル共重合体;エチレン−アクリル酸メチル共重合体、エチレン−アクリル酸エチル共重合体等のエチレン−アクリル酸エステル共重合体;エチレン−アクリル酸共重合体等のエチレン−ビニルカルボン酸共重合体;ポリプロピレン、プロピレン−エチレン共重合体等のポリプロピレン系樹脂;ポリ−4−メチルペンテン−1、ポリブテン−1、ポリブタジエン、ポリスチレン、アクリロニトリル−スチレン樹脂;アクリロニトリル−ブタジエン−スチレン樹脂、スチレン−共役ジエンブロック共重合体、スチレン−共役ジエンブロック共重合体水素添加物等のスチレン系エラストマー;フッ素樹脂;ポリメタクリル酸メチル等のアクリル酸樹脂;ナイロン6、ナイロン66等のポリアミド系樹脂;ポリエチレンテレフタレート、ポリエチレンナフタレート、ポリブチレンフタレート等のポリエステル系樹脂;ポリカーボネート、ポリアセタール、ポリアリレート、ヒドロキシ安息香酸ポリエステル、ポリエーテルイミド、ポリエステルカーボネート、ポリフェニレンエーテル樹脂、ポリ塩化ビニル、ポリ塩化ビニリデン、ポリウレタン等が挙げられ、これらの基材は、単独で用いても2種以上の混合物として用いても良く、これらの基材には必要によりフタル酸エステル類(フタル酸ジメチル、フタル酸ジオクチル等)、アジピン酸エステル類、ステアリン酸等の可塑剤が添加されていてもよい。樹脂蒸散剤は、本発明化合物を上記基材中に混練した後、射出成型、押出成型、プレス成型等により成型することにより得ることができる。得られた樹脂製剤は、必要により更に成型、裁断等の工程を経て、板状、フィルム状、テープ状、網状、ひも状等の形状に加工することもできる。これらの樹脂製剤は、例えば、非加熱蒸散剤、動物用首輪、動物用イヤータッグ、シート製剤、誘引テープ、誘引紐、園芸用支柱として加工される。 Examples of the resin used for the substrate such as a resin transpiration agent include polyethylene resins such as low density polyethylene, linear low density polyethylene, and high density polyethylene; and ethylene-vinyl ester copolymers such as ethylene-vinyl acetate copolymer. Polymer; ethylene-methacrylic acid ester copolymer such as ethylene-methyl methacrylate copolymer, ethylene-ethyl methacrylate copolymer; ethylene-methyl acrylate copolymer, ethylene-ethyl acrylate copolymer, etc. Ethylene-acrylic acid ester copolymer; ethylene-vinyl carboxylic acid copolymer such as ethylene-acrylic acid copolymer; polypropylene resin such as polypropylene and propylene-ethylene copolymer; poly-4-methylpentene-1, Polybutene-1, polybutadiene, polystyrene, acrylonitrile Styrene resin; Styrenic elastomer such as acrylonitrile-butadiene-styrene resin, styrene-conjugated diene block copolymer, hydrogenated styrene-conjugated diene block copolymer; Fluororesin; Acrylic resin such as polymethyl methacrylate; Nylon 6, polyamide resins such as nylon 66; polyester resins such as polyethylene terephthalate, polyethylene naphthalate, polybutylene phthalate; polycarbonate, polyacetal, polyarylate, hydroxybenzoic acid polyester, polyetherimide, polyester carbonate, polyphenylene ether resin, poly Examples thereof include vinyl chloride, polyvinylidene chloride, polyurethane and the like. These substrates may be used alone or as a mixture of two or more. Phthalates necessary to (dimethyl phthalate, dioctyl phthalate, etc.), adipic acid esters, plasticizers such as stearic acid may be added. The resin transpiration agent can be obtained by kneading the compound of the present invention in the above-mentioned base material and then molding it by injection molding, extrusion molding, press molding or the like. The obtained resin preparation can be further processed into a plate shape, a film shape, a tape shape, a net shape, a string shape or the like through steps such as molding and cutting if necessary. These resin preparations are processed, for example, as a non-heated transpiration agent, an animal collar, an animal ear tag, a sheet preparation, an attracting tape, an attracting string, and a garden support.
毒餌の基材としては、例えば、穀物粉、植物油、糖、結晶セルロース等の餌成分、BHT、ノルジヒドログアイアレチン酸等の酸化防止剤、デヒドロ酢酸等の保存料、トウガラシ粉末等の子どもやペットによる誤食防止剤、及びチーズ香料、タマネギ香料、ピーナッツオイル等の害虫誘引性香料があげられる。 As a bait base, for example, bait ingredients such as cereal flour, vegetable oil, sugar, crystalline cellulose, antioxidants such as BHT and nordihydroguaiaretic acid, preservatives such as dehydroacetic acid, children such as pepper powder and Examples include anti-fouling agents for pets, and pest-attracting perfumes such as cheese flavor, onion flavor, and peanut oil.
本発明化合物は他の殺虫剤、殺ダニ剤、殺菌剤、除草剤、忌避剤、共力剤、肥料、土壌改良剤と混用または併用して用いることもできる。 The compound of the present invention can be used in combination with or in combination with other insecticides, acaricides, fungicides, herbicides, repellents, synergists, fertilizers, and soil conditioners.
かかる殺虫剤、殺ダニ剤の有効成分としては、例えば、
(1)合成ピレスロイド系化合物
ピレトリン(pyrethrins)、アレスリン(allethrin)、プラレトリン(prallethrin)、フラメトリン(furamethrin)、レスメトリン(resmethrin)、テトラメトリン(tetramethrin)、イミプロトリン(imiprothrin)、エンペントリン(empenthrin)、トランスフルトリン(transfluthrin)、メトフルトリン(metofluthrin)、プロフルトリン(profluthrin)、フェノトリン(phenothrin)、シフェノトリン(cyphenothrin)、ペルメトリン(permethrin)、シペルメトリン(cypermethrin)、シフルトリン(cyfluthrin)、ベータ−シフルトリン(beta−cyfluthrin)、フェンプロパトリン(fenpropathrin)、ビフェントリン(bifenthrin)、シクロプロトリン(cycloprothrin)、デルタメトリン(deltamethrin)、フルメトリン(flumethrin)、アクリナトリン(acrinathrin)、トラロメトリン(tralomethrin)、シハロトリン(cyhalothrin)、ラムダシハロトリン(lambda−cyhalothrin)、テフルトリン(tefluthrin)、フェンバレレート(fenvalerate)、フルバリネート(fluvalinate)、エトフェンプロックス(ethofenprox)、シラフルオフェン(silafluofen)、ジメフルトリン(dimefluthrin)、2,3,5,6−テトラフルオロ−4−(メトキシメチル)ベンジル=2,2,3,3−テトラメチルシクロプロパンカルボキシレート等;
(2)有機リン系化合物
アセフェート(acephate)、ブタチオホス(butathiofos)、ダイアジノン(diazinon)、ジクロルボス(dichlorvos:DDVP)、ジメトエート(dimethoate)、フェンチオン(fenthion:MPP)、フエニトロチオン(fenitrothion:MEP)、マラチオン(malathion)、ピリダフェンチオン(pyridafenthion)、プロパホス(propaphos)、トリクロルホン(trichlorphon:DEP)等;
(3)カーバメート系化合物
カルバリル(carbary1)、カルボフラン(carbofuran)、フェノブカルブ(fenobucarb)、イソプロカルブ(isoprocarb:MIPC)、メソミル(methomyl)、NAC、プロポクスル(propoxur:PHC)等;
(4)ネライストキシン系化合物
カルタップ(cartap)、ベンスルタップ(bensu1tap)等;
(5)ネオニコチノイド系化合物
イミダクロプリド(imidac1oprid)、ニテンピラム(nitenpyram)、アセタミプリド(acetamiprid)、チアメトキサム(thiamethoxam)、チアクロプリド(thiacloprid)、ジノテフラン(dinotefuran)、クロチアニジン(clothianidin)等;
(6)ベンゾイル尿素系化合物
クロルフルアズロン(chlorfluazuron)、ビストリフルロン(bistrifluron)、ジフルベンズロン(diflubenzuron)、フルフェノクスロン(flufenoxuron)、ヘキサフルムロン(hexaflumuron)、テフルベンズロン(teflubenzuron)、トリフルムロン(triflumuron)等;
(7)フェニルピラゾール系化合物
フィプロニル(fiproni1)、ピリプロール(pyriprole)、ピラフルプロール(pyrafluprole)等;
(8)ヒドラジン系化合物
クロマフェノジド(chromafenozide)、ハロフェノジド(halofenozide)、メトキシフェノジド(methoxyfenozide)等;
(9)天然系殺虫剤
マシン油(machine oil)、硫酸ニコチン(nicotine−sulfate);
(10)その他の殺虫剤
アベルメクチン(avermectin−B)、ブプロフェジン(buprofezin)、クロルフェナピル(chlorphenapyr)、ハイドロプレン(hydroprene)、メトプレン(methoprene)、インドキサカルブ(indoxacarb)、メトキサジアゾン(metoxadiazone)、ミルベマイシンA(milbemycin−A)、ピリダリル(pyridalyl)、ピリプロキシフェン(pyriproxyfen)、スピノサッド(spinosad)、スルフラミド(sulfluramid)、トルフェンピラド(tolfenpyrad)、トリアゼメイト(triazamate)、フルベンジアミド(flubendiamide)、臭化メチル(Methyl bromide)、オレイン酸カリウム(Potassium oleate)等が挙げられる。
As an active ingredient of such insecticides and acaricides, for example,
(1) Synthetic pyrethroid compounds pyrethrins, allethrin, praretrin, furamethrin, resmethrin, tetramethrin, imiprothrin, imiprothrin (Transfluthrin), methfluthrin, profluthrin, phenothrin, cyphenothrin, permethrin, cypermethrin, cypermethrin. uthrin), beta-cyfluthrin, fenpropathrin, bifenthrin, cycloprothrin, deltamethrin, flumethrin (flumethrin), flumethrin (flumethrin) , Cyhalothrin, lambda-cyhalothrin, tefluthrin, fenvalerate, fulvalinate, etofenprox, silaflufen Silafluofen), dimefluthrin (dimefluthrin), 2,3,5,6- tetrafluoro-4- (methoxymethyl) benzyl = 2,2,3,3-tetramethyl-cyclopropane carboxylate;
(2) Organophosphorus compounds Acephate, butathiofos, diazinon, dichlorvos (DDVP), dimethoate, fenthion (MPP), fenitrothion (MEP) malathion), pyridafenthion, propaphos, trichlorphone (DEP) and the like;
(3) Carbamate compounds Carbaryl (carbary1), carbofuran, fenobucarb, isoprocarb (MIPC), mesomyl, NAC, propoxur (PHC), etc .;
(4) Nereistoxin compounds, such as cartap and bensultap;
(5) Neonicotinoid compounds imidacloprid (imidac1oprid), nitenpyram (nitenpyram), acetamiprid (acetamipride), thiamethoxam (thiacloprid) (thiacloprid), dinotefur (din)
(6) Benzoylurea compounds Chlorfluazuron, bistrifluron, diflubenzuron, flufenoxuron, hexafluuron, fluflutriuron, fluflutriuron etc;
(7) Phenylpyrazole compound fipronil (pyproni1), pyriprole (pyriprole), pyrafluprole (pyrafluprole) and the like;
(8) Hydrazine-based compounds Chromafenozide, halofenozide, methoxyphenozide and the like;
(9) Natural insecticide machine oil, nicotine sulfate (nicotine-sulfate);
(10) Other insecticides avermectin (vermectin-B), buprofezin, chlorfenapyr, hydroprene, metoprene, toxacarbine, indoxacarb milbemycin-A), pyridalyl, pyriproxyfen, spinosad, sulfuramide, tolfenpyrad, triazemate dimethyl, fludeamamide, fludeamamide Examples thereof include methyl bromide and potassium oleate.
忌避剤の有効成分としては、例えばN,N−ジエチル−m−トルアミド、リモネン、リナロール、シトロネラール、メントール、メントン、ヒノキチオール、ゲラニオール、ユーカリプトール、カラン−3,4−ジオール、IR−3535、MGK−R−326、MGK−R−874及びBAY−KBR−3023が挙げられる。 As an active ingredient of the repellent, for example, N, N-diethyl-m-toluamide, limonene, linalool, citronellal, menthol, menthone, hinokitiol, geraniol, eucalyptol, caran-3,4-diol, IR-3535, MGK -R-326, MGK-R-874 and BAY-KBR-3023.
共力剤の有効成分としては、例えば5−〔2−(2−ブトキシエトキシ)エトキシメチル〕−6−プロピル−1,3−ベンゾジオキソール、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、オクタクロロジプロピルエーテル、チオシアノ酢酸イソボルニル、N−(2−エチルへキシル)−1−イソプロピル−4−メチルビシクロ[2.2.2]オクト−5−エン−2,3−ジカルボキシイミド等が挙げられる。 As an active ingredient of a synergist, for example, 5- [2- (2-butoxyethoxy) ethoxymethyl] -6-propyl-1,3-benzodioxole, N- (2-ethylhexyl) bicyclo [2.2 .1] Hept-5-ene-2,3-dicarboximide, octachlorodipropyl ether, isobornyl thiocyanoacetate, N- (2-ethylhexyl) -1-isopropyl-4-methylbicyclo [2.2. 2] Oct-5-ene-2,3-dicarboximide and the like.
本発明化合物が効力を有する有害生物としては、例えば有害昆虫や有害ダニ等の有害節足動物が挙げられ、具体的には以下のものが挙げられる。
双翅目害虫:アカイエカ、コガタアカイエカ等のイエカ類、ネッタイシマカ、ヒトスジシマカ等のヤブカ類、シナハマダラカ等のハマダラカ類、ユスリカ類、イエバエ、オオイエバエ、ヒメイエバエ等のイエバエ類、クロバエ類、ニクバエ類、タネバエ、タマネギバエ等のハナバエ類、ミバエ類、ハモグリバエ類、ショウジョウバエ類、チョウバエ類、ノミバエ類、アブ類、ブユ類、サシバエ類、ヌカカ類等;
網翅目害虫:チャバネゴキブリ、クロゴキブリ、ワモンゴキブリ、トビイロゴキブリ、コバネゴキブリ等;
膜翅目害虫:アリ類、スズメバチ類、アリガタバチ類、カブラハバチ等のハバチ類等;
隠翅目害虫:イヌノミ、ネコノミ、ヒトノミ等;
シラミ目害虫:ヒトジラミ、ケジラミ、アタマジラミ、コロモジラミ等;
等翅目害虫:ヤマトシロアリ、イエシロアリ等;
半翅目害虫:ヒメトビウンカ、トビイロウンカ等のウンカ類、ツマグロヨコバイ等のヨコバイ類、ワタアブラムシ等のアブラムシ類、カメムシ類、トコジラミ等のトコジラミ類等;
鱗翅目害虫:ニカメイガ、コブノメイガ等のメイガ類、ハスモンヨトウ、アワヨトウ、ヨトウガ等のヨトウ類、シンクイガ類、ハモグリガ類、ドクガ類、コナガ、イチモンジセセリ、イガ、コイガ等;
鞘翅目害虫:ヒメカツオブシムシ、ヒメマルカツオブシムシ、コクゾウムシ、アズキゾウムシ等のゾウムシ類、チャイロコメノゴミムシダマシ、コクヌストモドキ等のゴミムシダマシ類、シバンムシ類、ヒラタキクイムシ類等;
ダニ類:コナヒョウヒダニ、ヤケヒョウヒダニ等のヒョウヒダニ類、ケナガコナダニ、ムギコナダニ等のコナダニ類、チリニクダニ、イエニクダニ、サナアシニクダニ等のニクダニ類、クワガタツメダニ、フトツメダニ等のツメダニ類、ホコリダニ類、マルニクダニ類、イエササラダニ類、フタトゲチマダニ等のマダニ類、トリサシダニ、ワクモ等のワクモ類。
Examples of pests for which the compounds of the present invention are effective include harmful arthropods such as harmful insects and harmful mites, and specific examples thereof include the following.
Diptera: Culex mosquitoes, Culex mosquitoes, etc., Aedes aegypti, Aedes albopictus, etc. Mosquitoes, fruit flies, leafhoppers, fruit flies, butterflies, flea flies, fly flies, flyfish, sand flies, nucifers, etc .;
Reticulate pests: German cockroaches, black cockroaches, American cockroaches, flying cockroaches, cockroaches, etc .;
Hymenoptera: ants, wasps, scallops, wasps such as wasps, etc .;
Lepidoptera: Inu fleas, cat fleas, human fleas, etc .;
Lice eye pests: human lice, white lice, head lice, body lice etc .;
Isoptera pests: Yamato termites, termites, etc .;
Hemiptera: insects such as Japanese brown planthopper, leafhopper, leafhopper such as leafhopper, aphids such as cotton aphid, bed bugs such as stink bug, bed bug, etc .;
Lepidopterous pests: Japanese moths such as Japanese moth, Japanese corn borer, Japanese cypresses such as Spodoptera litura, Ayayotou, Satsuma moth, Sinigas, Hamamoga, Dokuga, Konaga, Ichimon disseri, iga, Koiga, etc .;
Coleopterous insects: weevil such as longhorn beetle, longhorn beetle, weevil, weevil, weevil such as white beetle, beetle such as white beetle, red beetle, hornet beetle, etc .;
Tick: Leopard mites, such as Scarlet mite, Yake leopard mite, Scarlet mites, such as Scarlet mite, Scarlet mite, Scarlet mites, Scarlet mites, Mite, Mite Spiders such as ticks, avian mites, and spiders.
本発明の有害生物の防除方法は、本発明化合物の有効量を、通常本発明の有害生物防除剤の形態にて、有害生物又は有害生物の生息場所に施用することにより行われる。
本発明の有害生物防除剤の施用方法としては、例えば以下の方法が挙げられ、本発明の有害生物防除剤の形態、使用場所等に応じて適宜選択できる。
(1)本発明の有害生物防除剤をそのまま有害生物又は有害生物の生息場所に処理する方法。
(2)本発明の有害生物防除剤を水等の溶媒で希釈した後に、有害生物又は有害生物の生息場所に散布処理する方法。
この場合には、通常、乳剤、水和剤、フロアブル剤、マイクロカプセル製剤等に製剤化された本発明の有害生物防除剤を本発明化合物の濃度が0.1〜10000ppmとなるように希釈する。
(3)本発明の有害生物防除剤を有害生物の生息場所で、加熱等の手段により有効成分を揮散させる方法。
この場合、本発明化合物の施用量、施用濃度はいずれも本発明の有害生物防除剤の形態、施用時期、施用場所、施用方法、有害生物の種類、被害状況等に応じて適宜定めることができる。
The pest control method of the present invention is carried out by applying an effective amount of the compound of the present invention to a pest or a pest habitat, usually in the form of the pest control agent of the present invention.
Examples of the application method of the pest control agent of the present invention include the following methods, which can be appropriately selected depending on the form, use place, etc. of the pest control agent of the present invention.
(1) A method of treating the pest control agent of the present invention as it is in a pest or a habitat of the pest.
(2) A method in which the pest control agent of the present invention is diluted with a solvent such as water and then sprayed to a pest or a habitat of the pest.
In this case, the pest control agent of the present invention formulated in an emulsion, wettable powder, flowable agent, microcapsule preparation or the like is usually diluted so that the concentration of the compound of the present invention becomes 0.1 to 10,000 ppm. .
(3) A method of volatilizing an active ingredient by means of heating or the like in a pest habitat where the pest control agent of the present invention is present.
In this case, both the application amount and the application concentration of the compound of the present invention can be appropriately determined according to the form of the pest control agent of the present invention, the application time, the application place, the application method, the type of the pest, the damage situation, etc. .
本発明化合物を害虫防除用として用いる場合は、その施用量は空間に適用するときは、本発明化合物の量として通常0.001〜100mg/m3であり、平面に適用するときは0.001〜100mg/m2である。蚊取線香、蚊取マット等はその製剤形態に応じて加熱により有効成分を揮散させて施用する。樹脂蒸散剤、紙蒸散剤、不織布蒸散剤、編織物蒸散剤、昇華性錠剤等は例えば施用する空間にそのまま放置する、および、該製剤に送風下に設置することにより使用できる。
本発明の有害生物防除組成物を害虫防除用として施用する空間としては、例えば、リビングルーム、食堂、寝室、クローゼット、押入れ、和ダンス、食器棚、トイレ、浴場、物置、倉庫、車内等が挙げられ、さらに野外の開放空間で施用することもできる。
When the compound of the present invention is used for pest control, the application amount is usually 0.001 to 100 mg / m 3 as the amount of the compound of the present invention when applied to a space, and 0.001 when applied to a plane. ˜100 mg / m 2 . Mosquito coils, mosquito coils, etc. are applied by volatilizing the active ingredient by heating according to the formulation form. Resin transpiration agents, paper transpiration agents, non-woven fabric transpiration agents, knitted fabric transpiration agents, sublimable tablets and the like can be used, for example, by leaving them in the space to be applied as they are and by placing them in the preparation under ventilation.
Examples of the space to which the pest control composition of the present invention is applied for pest control include living rooms, canteens, bedrooms, closets, closets, Japanese dance, cupboards, toilets, bathhouses, storerooms, warehouses, and the like. In addition, it can be applied in open spaces outside.
本発明の有害生物防除組成物をウシ、ウマ、ブタ、ヒツジ、ヤギ、ニワトリ等の家畜、イヌ、ネコ、ラット、マウス等の小動物の外部寄生虫防除に用いる場合は、獣医学的に公知の方法で動物に使用することができる。具体的な使用方法としては、全身抑制(systemic control)を目的にする場合には、例えば錠剤、飼料混入、坐薬、注射(筋肉内、皮下、静脈内、腹腔内等)により投与され、非全身的抑制(non-systemic
control)を目的とする場合には、例えば油剤若しくは水性液剤を噴霧する、ポアオン(pour-on)処理若しくはスポットオン(spot-on)処理する、シャンプー製剤で動物を洗う又は樹脂蒸散剤を首輪や耳札にして動物に付ける等の方法により用いられる。動物体に投与する場合の本発明化合物の量は、通常動物の体重1kgに対して、0.01〜100mgの範囲である。
When the pesticidal composition of the present invention is used for controlling ectoparasites of domestic animals such as cattle, horses, pigs, sheep, goats and chickens, and small animals such as dogs, cats, rats and mice, it is well known in veterinary medicine. Can be used on animals in any way. As a specific method of use, for the purpose of systemic control, for example, it is administered by tablet, feed mixing, suppository, injection (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.) Non-systemic
For the purpose of control), for example, spraying an oil or aqueous solution, pour-on treatment or spot-on treatment, washing an animal with a shampoo preparation, or using a resin transpiration agent on a collar or It can be used by attaching it to animals using ear tags. The amount of the compound of the present invention when administered to an animal body is usually in the range of 0.01 to 100 mg per 1 kg body weight of the animal.
以下、製造例、参考製造例、製剤例及び試験例等により本発明をさらに詳しく説明するが、本発明はこれらの例に限定されるものではない。 Hereinafter, the present invention will be described in more detail with reference to production examples, reference production examples, formulation examples, test examples, and the like, but the present invention is not limited to these examples.
まず、本発明化合物の製造例を示す。
製造例1
5−エチニル−2−フランメタノール(145mg,1.19mmol)及び(1R)−トランス−3−(2−メチル−1−プロペニル)−2,2−ジメチルシクロプロパンカルボン酸(202mg,1.20mmol)のクロロホルム溶液(4mL)に1−エチル−3−(3−ジメチルアミノプロピル)カルボジイミド ハイドロクロライド(306mg、1.6mmol)及び4−ジメチルアミノピリジン(20mg)を加えた。室温で12時間攪拌した後、反応液に水を注加し、これを酢酸エチルで抽出した。該有機層を硫酸マグネシウムで乾燥した後、減圧条件下に濃縮し、残渣をシリカゲルカラムクロマトグラフィーに付し、下記式[化6]
で示される5−エチニル−2−フリルメチル=(1R)−トランス−3−(2−メチル−1−プロペニル)−2,2−ジメチルシクロプロパンカルボキシレート(以下、本発明化合物(1)と記す。)247mgを得た。
First, the manufacture example of this invention compound is shown.
Production Example 1
5-Ethynyl-2-furanmethanol (145 mg, 1.19 mmol) and (1R) -trans-3- (2-methyl-1-propenyl) -2,2-dimethylcyclopropanecarboxylic acid (202 mg, 1.20 mmol) 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride (306 mg, 1.6 mmol) and 4-dimethylaminopyridine (20 mg) were added to a chloroform solution (4 mL). After stirring at room temperature for 12 hours, water was poured into the reaction solution, which was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography, and the following formula [Chem. 6]
5-ethynyl-2-furylmethyl = (1R) -trans-3- (2-methyl-1-propenyl) -2,2-dimethylcyclopropanecarboxylate (hereinafter referred to as the present compound (1)) ) 247 mg was obtained.
無色液体:1H−NMR(CDCl3,TMS)δ(ppm): 1.13(s,3H)、1.26(s,3H)、1.43(d,1H)、1.70(m、6H)、2.07(dd,1H)、3.40(s,1H)、4.86(dm,1H)、5.02(dd,2H)、6.37(d,1H)、6.60(d,1H) Colorless liquid: 1 H-NMR (CDCl 3 , TMS) δ (ppm): 1.13 (s, 3H), 1.26 (s, 3H), 1.43 (d, 1H), 1.70 (m 6H), 2.07 (dd, 1H), 3.40 (s, 1H), 4.86 (dm, 1H), 5.02 (dd, 2H), 6.37 (d, 1H), 6 .60 (d, 1H)
製造例2
5−エチニル−2−チオフェンメタノール(100mg,0.72mmol)をトルエン(3mL)に溶かし、ピリジン0.10mLを加えた。ここに氷冷下で、(1R)−トランス−3−(2−メチル−1−プロペニル)−2,2−ジメチルシクロプロパンカルボン酸クロリド(135mg,0.72mmol)のトルエン溶液(1mL)を加えた。室温で12時間攪拌した後、反応液に水を注加し、これを酢酸エチルで抽出した。該有機層を5%塩酸、飽和重曹水、飽和食塩水で順次洗浄後、硫酸マグネシウムで乾燥した。減圧条件下に濃縮し、残渣をシリカゲルカラムクロマトグラフィーに付し、下記式[化7]
で示される5−エチニル−2−テニルメチル=(1R)−トランス−3−(2−メチル−1−プロペニル)−2,2−ジメチルシクロプロパンカルボキシレート(以下、本発明化合物(2)と記す。)168mgを得た。
Production Example 2
5-Ethynyl-2-thiophenemethanol (100 mg, 0.72 mmol) was dissolved in toluene (3 mL), and 0.10 mL of pyridine was added. To this was added a toluene solution (1 mL) of (1R) -trans-3- (2-methyl-1-propenyl) -2,2-dimethylcyclopropanecarboxylic acid chloride (135 mg, 0.72 mmol) under ice cooling. It was. After stirring at room temperature for 12 hours, water was poured into the reaction solution, which was extracted with ethyl acetate. The organic layer was washed successively with 5% hydrochloric acid, saturated aqueous sodium hydrogen carbonate and saturated brine, and dried over magnesium sulfate. The mixture was concentrated under reduced pressure, and the residue was subjected to silica gel column chromatography.
5-ethynyl-2-enylmethyl = (1R) -trans-3- (2-methyl-1-propenyl) -2,2-dimethylcyclopropanecarboxylate (hereinafter referred to as the present compound (2)). ) 168 mg was obtained.
淡黄色液体:1H−NMR(CDCl3,TMS)δ(ppm):1.13(s,3H)、1.26(s,3H)、1.41(d,1H)、1.70(m、6H)、2.09(dd,1H)、3.35(s,1H)、4.87(d,1H)、5.20(s,2H)、6.93(d、1H)、7.14(d,1H) Pale yellow liquid: 1 H-NMR (CDCl 3 , TMS) δ (ppm): 1.13 (s, 3H), 1.26 (s, 3H), 1.41 (d, 1H), 1.70 ( m, 6H), 2.09 (dd, 1H), 3.35 (s, 1H), 4.87 (d, 1H), 5.20 (s, 2H), 6.93 (d, 1H), 7.14 (d, 1H)
製造例3
製造例1において、(1R)−トランス−3−(2−メチル−1−プロペニル)−2,2−ジメチルシクロプロパンカルボン酸の代わりに、(1R)−トランス−3−(2,2−ジクロロエテニル)−2,2−ジメチルシクロプロパンカルボン酸を用いて同様に操作を行い、下記式[化8]
で示される5−エチニル−2−フリルメチル=(1R)−トランス−3−(2,2−ジクロロエテニル)−2,2−ジメチルシクロプロパンカルボキシレート(以下、本発明化合物(3)と記す。)を得た。
Production Example 3
In Production Example 1, instead of (1R) -trans-3- (2-methyl-1-propenyl) -2,2-dimethylcyclopropanecarboxylic acid, (1R) -trans-3- (2,2-dichlorobenzene) was used. Tenyl) -2,2-dimethylcyclopropanecarboxylic acid was used in the same manner, and the following formula [Chemical Formula 8]
5-Ethynyl-2-furylmethyl = (1R) -trans-3- (2,2-dichloroethenyl) -2,2-dimethylcyclopropanecarboxylate (hereinafter referred to as the present compound (3)). )
無色液体:1H−NMR(CDCl3,TMS)δ(ppm):1.18(s,3H)、1.28(s,3H)、1.63(d,1H)、2.25(dd,1H)、3.40(s,1H)、5.04(dd,2H)、5.59(d、1H)、6.39(d,1H)、6.61(d,1H) Colorless liquid: 1 H-NMR (CDCl 3 , TMS) δ (ppm): 1.18 (s, 3H), 1.28 (s, 3H), 1.63 (d, 1H), 2.25 (dd , 1H), 3.40 (s, 1H), 5.04 (dd, 2H), 5.59 (d, 1H), 6.39 (d, 1H), 6.61 (d, 1H)
製造例4
製造例1において、(1R)−トランス−3−(2−メチル−1−プロペニル)−2,2−ジメチルシクロプロパンカルボン酸の代わりに、(1R)−トランス−3−[(1Z)−1−プロペニル]−2,2−ジメチルシクロプロパンカルボン酸を用いて、同様に操作を行って、下記式[化9]
で示される5−エチニル−2−フリルメチル=(1R)−トランス−3−[(1Z)−1−プロペニル]−2,2−ジメチルシクロプロパンカルボキシレート(以下、本発明化合物(4)と記す。)を得た。
Production Example 4
In Production Example 1, instead of (1R) -trans-3- (2-methyl-1-propenyl) -2,2-dimethylcyclopropanecarboxylic acid, (1R) -trans-3-[(1Z) -1 -Propenyl] -2,2-dimethylcyclopropanecarboxylic acid was used in the same manner, and the following formula [Chemical Formula 9]
5-Ethynyl-2-furylmethyl = (1R) -trans-3-[(1Z) -1-propenyl] -2,2-dimethylcyclopropanecarboxylate (hereinafter referred to as the present compound (4)) .)
無色液体:1H−NMR(CDCl3,TMS)δ(ppm):1.14(s,3H)、1.27(s,3H)、1.49(d,1H)、1.70(dm,3H)、2.17(dd,1H)、3.40(s,1H)、5.03(dd,2H)、5.11(m、1H)、5.57(m、1H)、6.38(d,1H)、6.61(d,1H) Colorless liquid: 1 H-NMR (CDCl 3 , TMS) δ (ppm): 1.14 (s, 3H), 1.27 (s, 3H), 1.49 (d, 1H), 1.70 (dm , 3H), 2.17 (dd, 1H), 3.40 (s, 1H), 5.03 (dd, 2H), 5.11 (m, 1H), 5.57 (m, 1H), 6 .38 (d, 1H), 6.61 (d, 1H)
次に、一般式[化3]で示されるアルコール化合物(X=硫黄原子)の参考製造例を示す。
参考製造例
2,5−チオフェンジカルバルデヒド(200mg,1.43mmol)及びジメチル(1−ジアゾ−2−オキソプロピル)フォスフォネート(250mg,1.30mmol)のメタノール溶液(5mL)に炭酸カリウム(200mg、1.45mmol)を氷冷下で加えた。室温で12時間攪拌した後、反応液に水を注加し、これを酢酸エチルで2回抽出した。該有機層を食塩水で洗浄後、硫酸マグネシウムで乾燥した後、減圧条件下に濃縮した。残渣をさらに精製することなく、2−プロパノール4mLを加えた後、氷冷下でテトラヒドロほう酸ナトリウム50mgを加え2時間室温で攪拌した。反応液を氷水(10mL)に注加し、これを酢酸エチルで2回抽出した。該有機層を食塩水で洗浄後、硫酸マグネシウムで乾燥した後、減圧条件下に濃縮し、残渣をシリカゲルカラムクロマトグラフィーに付し、下記式で示される5−エチニル−2−チオフェンメタノール102mgを得た。
Next, a reference production example of an alcohol compound (X = sulfur atom) represented by the general formula [Chemical Formula 3] is shown.
Reference Production Example 2,5-thiophene dicarbaldehyde (200 mg, 1.43 mmol) and dimethyl (1-diazo-2-oxopropyl) phosphonate (250 mg, 1.30 mmol) in methanol (5 mL) were added to potassium carbonate (5 mL). 200 mg, 1.45 mmol) was added under ice cooling. After stirring at room temperature for 12 hours, water was poured into the reaction solution, which was extracted twice with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate, and concentrated under reduced pressure. Without further purification of the residue, 4 mL of 2-propanol was added, 50 mg of sodium tetrahydroborate was added under ice cooling, and the mixture was stirred at room temperature for 2 hours. The reaction solution was poured into ice water (10 mL), and this was extracted twice with ethyl acetate. The organic layer is washed with brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue is subjected to silica gel column chromatography to obtain 102 mg of 5-ethynyl-2-thiophenemethanol represented by the following formula. It was.
淡黄色液体:1H−NMR(CDCl3,TMS)δ(ppm):3.34(s,1H)、4.80(s,2H)、6.87(d、1H)、7.15(d,1H) Pale yellow liquid: 1 H-NMR (CDCl 3 , TMS) δ (ppm): 3.34 (s, 1H), 4.80 (s, 2H), 6.87 (d, 1H), 7.15 ( d, 1H)
次に、製剤例を示す。なお、部は質量部を示す。 Next, formulation examples are shown. In addition, a part shows a mass part.
製剤例1
本発明化合物(1)〜(4)の各々0.1部をキシレン 10部に溶解し、これを脱臭灯油 89.9部に混合して、油剤を得る。
Formulation Example 1
0.1 parts of each of the compounds (1) to (4) of the present invention are dissolved in 10 parts of xylene and mixed with 89.9 parts of deodorized kerosene to obtain an oil agent.
製剤例2
本発明化合物(1)〜(4)の各々0.1部及び脱臭灯油 39.9部を混合溶解したものをエアゾール容器に充填し、バルブ部分を取付けた後、該バルブ部分を通じて噴射剤(液化石油ガス)
60部を加圧充填して、油性エアゾールを得る。
Formulation Example 2
A solution obtained by mixing and dissolving 0.1 part of each of the compounds (1) to (4) of the present invention and 39.9 parts of deodorized kerosene is filled in an aerosol container, and after attaching a valve part, a propellant (liquefaction is passed through the valve part. Oil and gas)
60 parts are pressure-filled to obtain an oily aerosol.
製剤例3
本発明化合物(1)〜(4)の各々0.6部、キシレン 5部、脱臭灯油 3.4部及びレオドールMO−60 (乳化剤、花王株式会社登録商標)
1部を混合溶解したものと、水 50部とをエアゾール容器に充填し、バルブ部分を通じて噴射剤(液化石油ガス) 40部を加圧充填して、水性エアゾールを得る。
Formulation Example 3
0.6 parts of each of the compounds (1) to (4) of the present invention, 5 parts of xylene, 3.4 parts of deodorized kerosene and Rheodor MO-60 (emulsifier, registered trademark of Kao Corporation)
An aerosol container is filled with 1 part mixed and dissolved and 50 parts of water, and 40 parts of propellant (liquefied petroleum gas) is pressurized and filled through a valve part to obtain an aqueous aerosol.
製剤例4
本発明化合物(1)〜(4)の各々0.3g及びBHT0.5gを、蚊取線香用基材(除虫菊抽出粕粉、木粉、タブ粉、及び澱粉を混合したもの)
99.2gに均一に攪拌混合した後、着色剤としてマラカイトグリーンを含む水 100mLを加え、十分混練したものを成型乾燥し、蚊取線香を得る。
Formulation Example 4
Each of the compounds (1) to (4) of the present invention (0.3 g) and BHT (0.5 g) are mixed with a mosquito coil incense base material (mixed with insecticide chrysanthemum extract powder, wood powder, tab powder, and starch)
After uniformly stirring and mixing to 99.2 g, 100 mL of water containing malachite green is added as a colorant, and the mixture is sufficiently kneaded and dried to obtain a mosquito coil.
製剤例5
本発明化合物(1)〜(4)の各々0.8g、ピペロニルブトキシド 0.4g、及び染料に脱臭灯油を加えて溶解し、全部で10mLとする。この溶液
0.5mLを22mm×35mm、厚さ2.8mmの蚊取マット用基材(コットンリンターとパルプの混合物のフィリブルを板状に固めたもの)に均一に含浸させて、蚊取マット剤を得る。
Formulation Example 5
Deodorized kerosene is added to and dissolved in 0.8 g of each of the compounds (1) to (4) of the present invention, 0.4 g of piperonyl butoxide, and the dye to make a total of 10 mL. This solution is uniformly impregnated with 0.5 mL of this solution on a mosquito mat substrate (22 mm x 35 mm, 2.8 mm thick) (a mixture of cotton linter and pulp mixed in a plate), Get.
製剤例6
本発明化合物(1)〜(4)の各々0.7部及びBHT0.3部を、界面活性剤(ジエチレングリコールモノブチルエーテル)50部と精製水49部に溶解して得られる液剤をポリエステル製容器に入れ、上部をヒーターで加熱できるようにした吸液芯(無機粉体を焼成したもの)を挿入することにより、加熱蒸散装置に用いる水性蚊取リキッド剤を得る。
Formulation Example 6
A solution obtained by dissolving 0.7 parts of each of the compounds (1) to (4) of the present invention and 0.3 part of BHT in 50 parts of a surfactant (diethylene glycol monobutyl ether) and 49 parts of purified water is placed in a polyester container. An aqueous mosquito repellent liquid agent used in a heat transpiration device is obtained by inserting a liquid absorption core (in which inorganic powder is baked) whose upper part can be heated with a heater.
製剤例7
本発明化合物(1)〜(4)の各々100mgを適量のアセトンに溶解し、4cm×4cm、厚さ1.2cmの多孔セラミック板に含浸させて、加熱燻煙剤を得る。
Formulation Example 7
100 mg of each of the compounds (1) to (4) of the present invention is dissolved in an appropriate amount of acetone and impregnated in a porous ceramic plate having a size of 4 cm × 4 cm and a thickness of 1.2 cm to obtain a heated smoke.
製剤例8
本発明化合物(1)〜(4)の各々10mgを適量のアセトンに溶解し、5cm×5cm、厚さ0.3mmの不織布に均一に塗布した後、アセトンを風乾して、常温揮散剤を得る。
Formulation Example 8
10 mg of each of the compounds (1) to (4) of the present invention is dissolved in an appropriate amount of acetone and uniformly applied to a nonwoven fabric having a size of 5 cm × 5 cm and a thickness of 0.3 mm, and then acetone is air-dried to obtain a room temperature volatilizer. .
製剤例9
本発明化合物(1)〜(4)の各々10部、ポリオキシエチレンアルキルエーテルサルフェートアンモニウム塩50部を含むホワイトカーボン35部、及び水55部を混合し、湿式粉砕法で微粉砕することにより、10%フロアブル剤を得る。
Formulation Example 9
By mixing 10 parts of each of the compounds (1) to (4) of the present invention, 35 parts of white carbon containing 50 parts of polyoxyethylene alkyl ether sulfate ammonium salt, and 55 parts of water, and finely pulverizing by a wet pulverization method, 10% flowable is obtained.
次に、本発明化合物が有害生物防除剤の有効成分として有効であることを試験例として示す。 Next, it shows as a test example that this invention compound is effective as an active ingredient of a pest control agent.
試験例1
供試化合物0.3gと蚊取線香用基材(除虫菊抽出粕粉、木粉、タブ粉、及び澱粉を混合したもの) 99.7gに均一に攪拌混合した後、水
100mLを加え、十分混練したものを成型乾燥し、蚊取線香を調製した。
アカイエカ成虫20頭(雌)を入れた密閉された円筒(直径20cm、高さ43cm)内の下部で、上記に従って調製した線香(本発明化合物、比較化合物およびアレスリン)を1分間燃やし15分間暴露させた。暴露から一定時間後(5分後)にノックダウンした虫数をカウントした(2反復平均)。
また、比較対照として下記式[化11]
で示される5−エチニル−2−フリルメチル=(1R)−シス−3− (2−クロル−3,3,3−トリフルオロ−1−プロペニル)−2,2−ジメチルシクロプロパンカルボキシレート(特開平6−25205号公報に記載の化合物。以下、比較化合物と記す。)およびアレスリン:(RS)−2−メチル−3−(2−プロペニル)−シクロペント−2−エン−4−オン−1−イル=(1RS)−トランス、シス−3−(2−メチル−1−プロペニル)−2,2−ジメチルシクロプロパンカルボキシレート
を用い、同様に試験を行った。
結果を表1に示す。
Test example 1
0.3 g of test compound and mosquito coil incense base material (mixed with pesticide chrysanthemum extract powder, wood powder, tab powder and starch) After stirring and mixing uniformly to 99.7 g, add 100 mL of water and knead well The product was molded and dried to prepare a mosquito coil.
In the lower part of a sealed cylinder (diameter 20 cm, height 43 cm) containing 20 adult mosquitoes (female), the incense sticks prepared according to the above (compound of the present invention, comparative compound and allethrin) were burned for 1 minute and exposed for 15 minutes. It was. The number of insects knocked down after a certain time (5 minutes) after exposure was counted (2 repeated averages).
Further, as a comparative control, the following formula [Chemical Formula 11]
5-ethynyl-2-furylmethyl = (1R) -cis-3- (2-chloro-3,3,3-trifluoro-1-propenyl) -2,2-dimethylcyclopropanecarboxylate Compounds described in Kaihei 6-25205, hereinafter referred to as comparative compounds) and allethrin: (RS) -2-methyl-3- (2-propenyl) -cyclopent-2-en-4-one-1- A similar test was conducted using yl = (1RS) -trans, cis-3- (2-methyl-1-propenyl) -2,2-dimethylcyclopropanecarboxylate.
The results are shown in Table 1.
試験例2
直径28mm、内高13mm、底面積6.15cm2であるシャーレに本発明化合物(1)、(3)、およびペルメトリン[3−フェノキシベンジル=(1RS)−トランス、シス−3−(2、2−ジクロルエテニル)−2,2−ジメチルシクロプロパンカルボキシレート]0.1mgを含む0.2%アセトン溶液0.05mLを滴下し、底面に均一になるよう拡げた後、2連球でアセトンを除去する。各試料が底面に保持されたシャーレに、アカイエカの雌3匹を入れ、穴あきフィルムで上側をカバーした後、5分毎にノックダウン数を記録し、KT50(50%ノックダウンする時間)と24時間後の致死率を測定しかつ記録する。ノックダウン率につき所定以上の数値を示す試料については、前記0.2%アセトン溶液に更にアセトンを加えて10倍に希釈し、0.02%アセトン溶液とし、前記の各器具(シャーレ)、試験方法を順次繰り返した。
以下、同様に処理し、各化合物として0.001mgまで希釈した試料の効力を表2に示す。
Test example 2
A petri dish having a diameter of 28 mm, an inner height of 13 mm, and a bottom area of 6.15 cm 2 was added to the compounds (1) and (3) of the present invention and permethrin [3-phenoxybenzyl = (1RS) -trans, cis-3- (2, 2 -Dichloroethenyl) -2,2-dimethylcyclopropanecarboxylate] 0.05 mL of 0.2% acetone solution containing 0.1 mg was added dropwise and spread evenly on the bottom, and then acetone was removed with double balls. . Place 3 female squids in a petri dish with each sample held on the bottom, cover the top with a perforated film, and record the number of knockdowns every 5 minutes. KT 50 (Time to knock down 50%) And measure and record the mortality after 24 hours. For samples showing a predetermined value or more with respect to the knockdown rate, acetone is further added to the 0.2% acetone solution to dilute it 10-fold to obtain a 0.02% acetone solution. The method was repeated sequentially.
Table 2 shows the efficacy of samples treated in the same manner and diluted to 0.001 mg as each compound.
本発明化合物は優れた有害生物防除効力を有することから、有害生物防除剤の有効成分として有用である。 Since the compound of the present invention has an excellent pesticidal activity, it is useful as an active ingredient of a pesticidal agent.
Claims (8)
で示されるトランスエステル化合物。 [Formula 1]
A transester compound represented by
A method for controlling pests, wherein an effective amount of the transester compound according to any one of claims 1 to 6 is applied to pests or habitats of pests , except for use on the human body .
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