JP2020066620A - Ester compound and use therefor - Google Patents
Ester compound and use therefor Download PDFInfo
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- JP2020066620A JP2020066620A JP2019117012A JP2019117012A JP2020066620A JP 2020066620 A JP2020066620 A JP 2020066620A JP 2019117012 A JP2019117012 A JP 2019117012A JP 2019117012 A JP2019117012 A JP 2019117012A JP 2020066620 A JP2020066620 A JP 2020066620A
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- 0 *OCc(c(F)c(c(CO)c1F)F)c1F Chemical compound *OCc(c(F)c(c(CO)c1F)F)c1F 0.000 description 1
Abstract
Description
本発明はエステル化合物及びそのマダニを防除するための用途に関する。 The present invention relates to ester compounds and their use for controlling ticks.
[4−(メトキシメチル)−2,3,5,6−テトラフルオロフェニル]メチル 2,2−ジメチル−3−((Z)−1−プロペニル)シクロプロパンカルボキシラート
が有害生物防除活性を有することが知られている。(特許文献1)
[4- (Methoxymethyl) -2,3,5,6-tetrafluorophenyl] methyl 2,2-dimethyl-3-((Z) -1-propenyl) cyclopropanecarboxylate
Is known to have pest control activity. (Patent Document 1)
また、[4−(メトキシメチル)−2,3,6−トリフルオロフェニル]メチル 2,2−ジメチル−3−(2−メチル−1−プロペニル)シクロプロパンカルボキシラート
Further, [4- (methoxymethyl) -2,3,6-trifluorophenyl] methyl 2,2-dimethyl-3- (2-methyl-1-propenyl) cyclopropanecarboxylate
が有害生物防除活性を有することが知られている。(特許文献2) Is known to have pest control activity. (Patent Document 2)
本発明は、マダニに対して優れた防除効力を有する化合物を提供することを課題とする。 An object of the present invention is to provide a compound having an excellent controlling effect against ticks.
本発明は[4−(メトキシメチル)−2,3,6−トリフルオロフェニル]メチル 2,2−ジメチル−3−((Z)−1−プロペニル)シクロプロパンカルボキシラート The present invention relates to [4- (methoxymethyl) -2,3,6-trifluorophenyl] methyl 2,2-dimethyl-3-((Z) -1-propenyl) cyclopropanecarboxylate.
及びそのマダニ防除のための用途を提供する。 And its use for controlling ticks.
本発明により、マダニを防除することができる。 According to the present invention, ticks can be controlled.
本発明化合物である[4−(メトキシメチル)−2,3,6−トリフルオロフェニル]メチル 2,2−ジメチル−3−((Z)−1−プロペニル)シクロプロパンカルボキシラートは、2,2−ジメチル−3−((Z)−1−プロペニル)シクロプロパンカルボン酸又はその誘導体と[4−(メトキシメチル)−2,3,6−トリフルオロフェニル]メタノールとのエステル化反応により製造することができる。より詳細には、1,4−ビス(ヒドロキシメチル)−2,3,5,6−テトラフルオロベンゼンとtert−ブチルジメチルクロロシランとの反応により得られる1−tert−ブチルジメチルシリルオキシメチル−4−ヒドロキシメチル−2,3,5,6−テトラフルオロベンゼンを水素化アルミニウムリチウムで還元することで1−tert−ブチルジメチルシリルオキシメチル−4−ヒドロキシメチル−2,3,6−トリフルオロベンゼンに導き、メチル化、tert−ブチルジメチルシリル基の脱保護を経て[4−(メトキシメチル)−2,3,6−トリフルオロフェニル]メタノールを調製した後、エステル化反応により製造することができる。必要により、後述の実施例を参照することができる。 The compound of the present invention, [4- (methoxymethyl) -2,3,6-trifluorophenyl] methyl 2,2-dimethyl-3-((Z) -1-propenyl) cyclopropanecarboxylate, is 2,2. -Preparation by esterification of dimethyl-3-((Z) -1-propenyl) cyclopropanecarboxylic acid or its derivative with [4- (methoxymethyl) -2,3,6-trifluorophenyl] methanol You can More specifically, 1-tert-butyldimethylsilyloxymethyl-4-obtained by the reaction of 1,4-bis (hydroxymethyl) -2,3,5,6-tetrafluorobenzene and tert-butyldimethylchlorosilane. Reduction of hydroxymethyl-2,3,5,6-tetrafluorobenzene with lithium aluminum hydride leads to 1-tert-butyldimethylsilyloxymethyl-4-hydroxymethyl-2,3,6-trifluorobenzene. , [4- (methoxymethyl) -2,3,6-trifluorophenyl] methanol via methylation and deprotection of the tert-butyldimethylsilyl group, and then can be produced by an esterification reaction. If necessary, the examples described below can be referred to.
本発明化合物をマダニ防除のために使用する場合、通常、該化合物と不活性担体とを含有する組成物であるマダニ防除用組成物の形態で使用する。 When the compound of the present invention is used for controlling ticks, it is usually used in the form of a composition for controlling ticks, which is a composition containing the compound and an inert carrier.
該組成物は、通常、本発明化合物と固体担体、液体担体等の不活性担体とを混合し、必要に応じて界面活性剤、その他の製剤用補助剤を添加して、エマルジョン、油剤、油性液剤、水性液剤、溶解液、シャンプー、サスペンジョン等の液剤、粉剤、クリーム剤、軟膏剤、エアゾール製剤、シート製剤等の製剤等に製剤化して得ることができる。 The composition is usually prepared by mixing the compound of the present invention with an inert carrier such as a solid carrier and a liquid carrier, and optionally adding a surfactant and other auxiliary agents for formulation to prepare an emulsion, an oil agent, an oily agent. It can be obtained by formulating into a liquid preparation such as a liquid preparation, an aqueous liquid preparation, a solution, a shampoo and a suspension, a powder preparation, a cream preparation, an ointment preparation, an aerosol preparation and a sheet preparation.
固体担体としては、例えば、粘土(カオリンクレー、珪藻土、ベントナイト、酸性白土等)、乾式シリカ、湿式シリカ、タルク、セラミック、その他の無機鉱物(セリサイト、石英、硫黄、活性炭、炭酸カルシウムなどの微粉末及び粒状物並びに合成樹脂(ポリプロピレン、ポリアクリロニトリル、ポリメタクリル酸メチル、ポリエチレンテレフタレート等のポリエステル樹脂、ナイロン−6、ナイロン−11、ナイロン−66等のポリアミド樹脂、ポリ塩化ビニル、ポリ塩化ビニリデン、塩化ビニル−プロピレン共重合体等)が挙げられる。 Examples of the solid carrier include clay (kaolin clay, diatomaceous earth, bentonite, acid clay, etc.), dry silica, wet silica, talc, ceramics, and other inorganic minerals (cericite, quartz, sulfur, activated carbon, calcium carbonate, etc.). Powders and granules and synthetic resins (polyester resins such as polypropylene, polyacrylonitrile, polymethylmethacrylate and polyethylene terephthalate, polyamide resins such as nylon-6, nylon-11 and nylon-66, polyvinyl chloride, polyvinylidene chloride, chloride Vinyl-propylene copolymers and the like).
液体担体としては、例えば、水、アルコール(メタノール、エタノール、プロパノール、イソプロピルアルコール、ブタノール、イソブチルアルコール、ヘキサノール、2−エチルヘキサノール、オクタノール等)、ケトン(アセトン、メチルエチルケトン等)、芳香族炭化水素(トルエン、キシレン等)、脂肪族炭化水素(ヘキサン、シクロヘキサン等)、エステル(酢酸エチル、酢酸ブチル、フタル酸ジエチル、アジピン酸ジイソブチル、安息香酸ベンジル等)、ニトリル(アセトニトリル等)、エーテル(ジイソプロピルエーテル、ジエチレングリコールジメチルエーテル等)、アミド(N,N−ジメチルホルムアミド等)、スルホキシド(ジメチルスルホキシド等)及び植物油(大豆油、綿実油等)が挙げられる。 Examples of liquid carriers include water, alcohols (methanol, ethanol, propanol, isopropyl alcohol, butanol, isobutyl alcohol, hexanol, 2-ethylhexanol, octanol, etc.), ketones (acetone, methyl ethyl ketone, etc.), aromatic hydrocarbons (toluene). , Xylene, etc.), aliphatic hydrocarbons (hexane, cyclohexane, etc.), esters (ethyl acetate, butyl acetate, diethyl phthalate, diisobutyl adipate, benzyl benzoate, etc.), nitriles (acetonitrile, etc.), ethers (diisopropyl ether, diethylene glycol) Dimethyl ether and the like), amide (N, N-dimethylformamide and the like), sulfoxide (dimethyl sulfoxide and the like) and vegetable oil (soybean oil, cottonseed oil and the like).
界面活性剤としては、例えば、ポリオキシエチレンアルキルエーテル、ポリオキシエチレンアルキルアリールエーテル、ポリエチレングリコール脂肪酸エステル等の非イオン界面活性剤、及びアルキルスルホン酸塩、アルキルベンゼンスルホン酸塩、アルキル硫酸塩等の陰イオン界面活性剤が挙げられる。 Examples of the surfactant include nonionic surfactants such as polyoxyethylene alkyl ether, polyoxyethylene alkylaryl ether, and polyethylene glycol fatty acid ester, and anionic surfactants such as alkyl sulfonate, alkylbenzene sulfonate, and alkyl sulfate. An ionic surfactant is mentioned.
その他の製剤用補助剤としては、固着剤、分散剤、着色剤及び安定剤等、具体例としてはカゼイン、ゼラチン、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、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、ポリアクリル酸類等)、酸性リン酸イソプロピル、2,6−ジ−tert−ブチル−4−メチルフェノール、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)、シリコーンオイル、トリグリセリドが挙げられる。 As other auxiliaries for formulation, fixing agents, dispersants, colorants, stabilizers, etc., specific examples include casein, gelatin, sugars (starch, gum arabic, cellulose derivatives, alginic acid, etc.), lignin derivatives, bentonite, synthetic Water-soluble polymer (polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acid, etc.), acidic isopropyl phosphate, 2,6-di-tert-butyl-4-methylphenol, BHA (2-tert-butyl-4-methoxyphenol) Mixtures with 3-tert-butyl-4-methoxyphenol), silicone oils, triglycerides.
本発明のマダニ防除用組成物は、ヒト以外の動物、例えば、ウシ、ヒツジ、ヤギ、ブタ、ウマ、ロバ、イヌ、ネコ、ウサギ、マウス、ラット、ハムスター、リス、サル等に対する獣医学的組成物として使用することができ、特にイヌ及びネコに対して使用すると効果的なマダニ防除が行える。 The tick control composition of the present invention is a veterinary composition for animals other than humans, for example, bovine, sheep, goat, pig, horse, donkey, dog, cat, rabbit, mouse, rat, hamster, squirrel, monkey and the like. When used for dogs and cats, it can effectively control ticks.
本発明のマダニ防除用組成物を用いる防除方法としては、浸漬、噴霧、塗布、入浴、洗浄、摩り込み又は散布等が挙げられる。好ましい投与方法としては、スポットオン処理及びポアオン処理が挙げられる。スポットオン処理とは一般に宿主動物の頭部や肩胛骨背部等の皮膚に液状の製剤を滴下又は塗布する方法であり、ポアオン処理とは一般に宿主動物体の背中線に沿って液状の製剤を注ぐ方法である。 Examples of the control method using the tick control composition of the present invention include dipping, spraying, coating, bathing, washing, rubbing or spraying. Preferred administration methods include spot-on treatment and pour-on treatment. Spot-on treatment is generally a method of dropping or applying a liquid preparation onto the skin of the host animal's head, scapula, etc., and pour-on treatment is generally a method of pouring a liquid preparation along the back line of the host animal body. Is.
本発明化合物の投与量は、通常0.01〜100mg/kgである。 The dose of the compound of the present invention is usually 0.01 to 100 mg / kg.
本発明化合物により防除されるマダニ(Ixodidae)としては、例えば、フタトゲチマダニ(Haemaphysalis longicornis)、ヤマトチマダニ(Haemaphysalis flava)、ツリガネチマダニ(Haemaphysalis campanulata)等のHaemaphysalis属、アメリカンドッグチック(Dermacentor variabilis)、タイワンカクマダニ(Dermacentor taiwanicus)、デルマセントル・アンデルソニ(Dermacentor andersoni)等の Dermacentor属、ヤマトマダニ(Ixodes ovatus)、シュルツマダニ(Ixodes persulcatus)、ブラックレッグドチック(Ixodes scapularis)、西部クロアシマダニ(Ixodes pacificus)、イキソデス・ホロシクラス(Ixodes holocyclus)等のIxodes属、ローンスターチック(Amblyomma americanum)、アンブリオンマ・マクラタム(Ambryomma maculatum)等のAmblyomma属、オウシマダニ(Rhipicephalus (Boophilus) microplus)、ブーフィラス・アンヌラタス(Boophilus annulatus)等のBoophilus属、クリイロコイタマダニ(Rhipicephalus sanguineus)、リピセファラス・アペンディキュレイタス(Rhipicephalus appendiculatus)等のRhipicephalus属が挙げられる。 Examples of the ticks (Ixodidae) controlled by the compound of the present invention include Haemaphysalis such as Haemaphysalis longicornis, Haemaphysalis flava, Haemaphysalis campanulata, American dog tick (Dermacentor wanabilis), Genus Dermacentor such as ticks (Dermacentor taiwanicus) and Dermacentor andersoni (Dermacentor andersoni), Ixodes ovatus (Ixodes persulcatus), Ixodes scapularis (Ixodes scapularis), western black-footed tick Ixodes genus such as Ixodes holocyclus, Amblyomma americanum, Amblyomma genus such as Ambryomma maculatum, Rhipicephalus (Boophilus) microplus, Boophilus ann Examples include Boophilus genus such as Nuratus (Boophilus annulatus), genus Rhipicephalus such as Rhipicephalus sanguineus, and Lipicephalus appendiculatus.
本発明化合物として、式(A)
The compound of the present invention has the formula (A)
で示される光学活性体又は該光学活性体を多く含む異性体混合物を使用するのが好ましい。 It is preferable to use the optically active substance represented by or an isomer mixture containing a large amount of the optically active substance.
まず、本発明化合物の製造例を示す。以下の製造例においてTBSはtert−ブチルジメチルシリル基を表す。 First, production examples of the compound of the present invention will be shown. In the production examples below, TBS represents a tert-butyldimethylsilyl group.
1,4−ビス(ヒドロキシメチル)−2,3,5,6−テトラフルオロベンゼン15.0g、イミダゾール4.86g及びN,N−ジメチルホルミアミド60mLの混合物に、tert−ブチルジメチルクロロシラン10.76gをゆっくり加え、室温で10時間撹拌した。得られた混合物に5%塩酸を加え、酢酸エチルで抽出した。得られた有機層を水及び飽和食塩水で順次洗浄し、無水硫酸マグネシウムで乾燥し、減圧下で濃縮した。得られた残渣をシリカゲルカラムクロマトグラフィーに付し、1−tert−ブチルジメチルシリルオキシメチル−4−ヒドロキシメチル−2,3,5,6−テトラフルオロベンゼン、即ち、式
A mixture of 15.0 g of 1,4-bis (hydroxymethyl) -2,3,5,6-tetrafluorobenzene, 4.86 g of imidazole and 60 mL of N, N-dimethylformamide was added to tert-butyldimethylchlorosilane 10. 76 g was slowly added, and the mixture was stirred at room temperature for 10 hours. 5% Hydrochloric acid was added to the obtained mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to give 1-tert-butyldimethylsilyloxymethyl-4-hydroxymethyl-2,3,5,6-tetrafluorobenzene, that is, the formula:
で示される化合物15.05gを得た。 There was obtained 15.05 g of the compound represented by.
窒素雰囲気下で、水素化アルミニウムリチウム1.25g及びテトラヒドロフラン75mLの混合物に、0℃で15.05gの1−tert−ブチルジメチルシリルオキシメチル−4−ヒドロキシメチル−2,3,5,6−テトラフルオロベンゼン及びテトラヒドロフラン75mLの溶液をゆっくり加えた。得られた混合物を還流下で6時間撹拌した。得られた混合物を10℃にし、これに10%硫酸水溶液を加え、得られた混合物をtert−ブチルメチルエーテルで抽出した。得られた有機層を水洗し、無水硫酸マグネシウムで乾燥し、減圧下で濃縮した。得られた残渣をシリカゲルカラムクロマトグラフィーに付し、1−tert−ブチルジメチルシリルオキシメチル−4−ヒドロキシメチル−2,3,6−トリフルオロベンゼン、即ち、式
Under a nitrogen atmosphere, a mixture of 1.25 g of lithium aluminum hydride and 75 mL of tetrahydrofuran was added to 15.05 g of 1-tert-butyldimethylsilyloxymethyl-4-hydroxymethyl-2,3,5,6-tetratetrahydrofuran at 0 ° C. A solution of 75 mL of fluorobenzene and tetrahydrofuran was added slowly. The resulting mixture was stirred under reflux for 6 hours. The obtained mixture was heated to 10 ° C., 10% aqueous sulfuric acid solution was added thereto, and the obtained mixture was extracted with tert-butyl methyl ether. The obtained organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to give 1-tert-butyldimethylsilyloxymethyl-4-hydroxymethyl-2,3,6-trifluorobenzene, that is, the formula:
で示される化合物9.93gを得た。 Thus, 9.93 g of the compound represented by
9.93gの1−tert−ブチルジメチルシリルオキシメチル−4−ヒドロキシメチル−2,3,6−トリフルオロベンゼン、ヨードメタン23g及びテトラヒドロフラン75mLの混合物に、5℃で水素化ナトリウム(60%油性)を少しずつ加え、5℃で12時間撹拌した。得られた混合物に水を加え、tert−ブチルメチルエーテルで抽出した。得られた有機層を水及び飽和食塩水で順次洗浄し、無水硫酸マグネシウムで乾燥し、減圧下で濃縮した。得られた残渣をシリカゲルカラムクロマトグラフィーに付し、1−tert−ブチルジメチルシリルオキシメチル−4−メトキシメチル−2,3,6−トリフルオロベンゼン、即ち、式
To a mixture of 9.93 g of 1-tert-butyldimethylsilyloxymethyl-4-hydroxymethyl-2,3,6-trifluorobenzene, 23 g of iodomethane and 75 mL of tetrahydrofuran was added sodium hydride (60% oily) at 5 ° C. It was added little by little and stirred at 5 ° C. for 12 hours. Water was added to the obtained mixture, and the mixture was extracted with tert-butyl methyl ether. The obtained organic layer was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to give 1-tert-butyldimethylsilyloxymethyl-4-methoxymethyl-2,3,6-trifluorobenzene, that is, the formula:
で示される化合物8.4gを得た
8.4gの1−tert−ブチルジメチルシリルオキシメチル−4−メトキシメチル−2,3,6−トリフルオロベンゼン及びテトラヒドロフラン17mLの混合物に、酢酸17mL及び10%塩酸17mLを順次加え、室温で5時間撹拌した。得られた混合物をtert−ブチルメチルエーテルで抽出した。得られた有機層を水及び飽和食塩水で順次洗浄し、無水硫酸マグネシウムで乾燥し、減圧下で濃縮した。得られた残渣をシリカゲルカラムクロマトグラフィーに付し、[4−(メトキシメチル)−2,3,6−トリフルオロフェニル]メタノール、即ち、式
8.4 g of the compound shown in 8.4 g was obtained. To a mixture of 8.4 g of 1-tert-butyldimethylsilyloxymethyl-4-methoxymethyl-2,3,6-trifluorobenzene and tetrahydrofuran 17 mL, acetic acid 17 mL and 10% 17 mL of hydrochloric acid was sequentially added, and the mixture was stirred at room temperature for 5 hours. The resulting mixture was extracted with tert-butyl methyl ether. The obtained organic layer was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to give [4- (methoxymethyl) -2,3,6-trifluorophenyl] methanol, that is, the formula
で示される化合物4.59gを得た。
1H-NMR (CDCl3) δ(ppm): 2.90 (1H, t), 3.40 (3H, s), 4.51 (2H, s), 4.72 (2H, d), 6.94 (1H, m).
4.59gの[4−(メトキシメチル)−2,3,6−トリフルオロフェニル]メタノール、ピリジン2.64g及びトルエン45mLの混合物に、US6562853に記載の方法で製造した(1R)−トランス−2,2−ジメチル−3−((Z)−1−プロペニル)シクロプロパンカルボン酸クロリド4.41gを氷冷下で加え、室温で2時間撹拌した。得られた混合物に4%硫酸水溶液を加え、トルエンで抽出した。得られた有機層を飽和食塩水で洗浄し、無水硫酸マグネシウムで乾燥し、減圧下で濃縮した。得られた残渣をシリカゲルカラムクロマトグラフィーに付し、式(A)で示される化合物7.21gを得た。
1H-NMR (CDCl3) δ(ppm): 1.13 (3H, s), 1.28 (3H, s), 1.45 (1H, d), 1.70 (3H, d), 2.17 (1H, dd), 3.44 (3H, s), 4.53 (2H, s), 5.10 (1H, m), 5.20 (2H, s), 5.59 (1H, m), 7.00 (1H, m).
次に、本発明化合物である式(A)で示される化合物
Thus, 4.59 g of a compound represented by
1 H-NMR (CDCl 3 ) δ (ppm): 2.90 (1H, t), 3.40 (3H, s), 4.51 (2H, s), 4.72 (2H, d), 6.94 (1H, m).
(1R) -trans-2 prepared by the method described in US6562853 in a mixture of 4.59 g [4- (methoxymethyl) -2,3,6-trifluorophenyl] methanol, 2.64 g pyridine and 45 mL toluene. , 2-Dimethyl-3-((Z) -1-propenyl) cyclopropanecarboxylic acid chloride (4.41 g) was added under ice cooling, and the mixture was stirred at room temperature for 2 hours. A 4% aqueous sulfuric acid solution was added to the obtained mixture, and the mixture was extracted with toluene. The obtained organic layer was washed with saturated saline, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 7.21 g of the compound represented by the formula (A).
1 H-NMR (CDCl 3 ) δ (ppm): 1.13 (3H, s), 1.28 (3H, s), 1.45 (1H, d), 1.70 (3H, d), 2.17 (1H, dd), 3.44 ( 3H, s), 4.53 (2H, s), 5.10 (1H, m), 5.20 (2H, s), 5.59 (1H, m), 7.00 (1H, m).
Next, the compound of the formula (A) which is a compound of the present invention
と比較するための式(B)
Expression (B) for comparison with
で示される[4−(メトキシメチル)−2,3,5,6−テトラフルオロフェニル]メチル (1R)−トランス−2,2−ジメチル−3−((Z)−1−プロペニル)シクロプロパンカルボキシラート(特許文献1参照)及び式(C)
[4- (methoxymethyl) -2,3,5,6-tetrafluorophenyl] methyl (1R) -trans-2,2-dimethyl-3-((Z) -1-propenyl) cyclopropanecarboxy represented by Rat (see Patent Document 1) and formula (C)
で示される[4−(メトキシメチル)−2,3,6−トリフルオロフェニル]メチル (1R)−トランス−2,2−ジメチル−3−(2−メチル−1−プロペニル)シクロプロパンカルボキシラート(特許文献2参照)
とを用いた試験例を示す。
試験例1
内容量20mLの容器に式(A)で示される化合物のアセトン溶液を注ぎ、化合物Aが0.032mg/m2となるように容器の内面に均一にコーティングし、その後乾燥させた。2時間後、該容器にフタトゲチマダニ若虫5頭を入れ、蓋を閉めた。48時間後、フタトゲチマダニの生死を調査し死虫率を求めた。死虫率は下式により計算した。
[4- (methoxymethyl) -2,3,6-trifluorophenyl] methyl (1R) -trans-2,2-dimethyl-3- (2-methyl-1-propenyl) cyclopropanecarboxylate ( (See Patent Document 2)
A test example using and is shown.
Test example 1
An acetone solution of the compound represented by the formula (A) was poured into a container having an inner volume of 20 mL, the inner surface of the container was uniformly coated with the compound A at 0.032 mg / m 2, and then dried. Two hours later, 5 nymphs of Haemaphysalis longicornis were placed in the container and the lid was closed. After 48 hours, the life and death of Haemaphysalis longicornis was investigated to determine the mortality rate. The mortality was calculated by the following formula.
死虫率(%)=(死虫数/供試虫数)×100
その結果、死虫率は80%であった。
Mortality rate (%) = (number of dead insects / number of test insects) x 100
As a result, the mortality rate was 80%.
式(A)で示される化合物に代えて式(B)で示される化合物を用いて同じ試験を行った結果、死虫率は20%であった。 As a result of conducting the same test using the compound represented by the formula (B) instead of the compound represented by the formula (A), the mortality rate was 20%.
式(A)で示される化合物に代えて式(C)で示される化合物を用いて同じ試験を行った結果、死虫率は10%であった。
As a result of conducting the same test using the compound represented by the formula (C) instead of the compound represented by the formula (A), the mortality rate was 10%.
試験例2
内容量20mLの容器に式(A)で示される化合物のアセトン溶液を注ぎ、式(A)で示される化合物が4mg/m2となるように容器の内面に均一にコーティングし、その後乾燥させた。24時間後、該容器にフタトゲチマダニ若虫5頭を入れ、蓋を閉めた。48時間後、フタトゲチマダニの生死を調査し死虫率を求めた。その結果、死虫率は60%であった。
Test example 2
An acetone solution of the compound represented by the formula (A) was poured into a container having an inner volume of 20 mL, the inner surface of the container was uniformly coated so that the compound represented by the formula (A) was 4 mg / m 2, and then dried. . After 24 hours, 5 nymphs of Haemaphysalis longicornis were placed in the container and the lid was closed. After 48 hours, the life and death of Haemaphysalis longicornis was investigated to determine the mortality rate. As a result, the mortality rate was 60%.
式(A)で示される化合物に代えて式(B)で示される化合物を用い同じ試験を行った結果、死虫率は0%であった。 As a result of conducting the same test using the compound represented by the formula (B) instead of the compound represented by the formula (A), the mortality rate was 0%.
式(A)で示される化合物に代えて式(C)で示される化合物を用い同じ試験を行った結果、死虫率は0%であった。
As a result of conducting the same test using the compound represented by the formula (C) instead of the compound represented by the formula (A), the mortality rate was 0%.
本発明化合物はマダニに対して優れた防除効果を示すことから、マダニ防除用組成物の有効成分として有用である。 Since the compound of the present invention has an excellent controlling effect on ticks, it is useful as an active ingredient of a composition for controlling ticks.
Claims (2)
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JP2000063329A (en) * | 1998-02-26 | 2000-02-29 | Sumitomo Chem Co Ltd | Ester compound |
JP2007145781A (en) * | 2005-11-30 | 2007-06-14 | Sumitomo Chemical Co Ltd | Ester compound and its use |
CN101792392A (en) * | 2010-04-08 | 2010-08-04 | 大连多相触媒有限公司 | Optically active synthetic pyrethroid compound and preparation method and application thereof |
WO2017208632A1 (en) * | 2016-05-31 | 2017-12-07 | 大日本除蟲菊株式会社 | Ester compound and use thereof |
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JP2000063329A (en) * | 1998-02-26 | 2000-02-29 | Sumitomo Chem Co Ltd | Ester compound |
JP2007145781A (en) * | 2005-11-30 | 2007-06-14 | Sumitomo Chemical Co Ltd | Ester compound and its use |
CN101792392A (en) * | 2010-04-08 | 2010-08-04 | 大连多相触媒有限公司 | Optically active synthetic pyrethroid compound and preparation method and application thereof |
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