JP2007055964A - Sulfonyl compound and harmful arthropod control use - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a new sulfonyl compound having excellent control efficacy against harmful arthropods. <P>SOLUTION: This sulfonyl compound represented by formula (I) (R<SP>1</SP>is 3-6C fluoroalkyl; R<SP>2</SP>is 1-5C fluoroalkyl; Q is O or NR<SP>3</SP>; R<SP>3</SP>is H or 1-4C alkyl). The sulfonyl compound has excellent control efficacy against harmful arthropods. <P>COPYRIGHT: (C)2007,JPO&INPIT

Description

  The present invention relates to a sulfonyl compound and its use for controlling harmful arthropods.

  Conventionally, many harmful arthropod control agents have been developed and put into practical use for controlling harmful arthropods.

  An object of the present invention is to provide a novel compound having an excellent control effect on harmful arthropods.

〔式中、
Ｒ¹はＣ３−Ｃ６フルオロアルキル基を表し、Ｒ²はＣ１−Ｃ５フルオロアルキル基を表し、Ｑは酸素原子又はＮＲ³を表し、Ｒ³は水素原子又はＣ１−Ｃ４アルキル基を表す。〕で示されるスルホニル化合物（以下、本発明化合物と記す。）、本発明化合物を有効成分として含有する有害節足動物防除剤、並びに本発明化合物の有効量を有害節足動物又は有害節足動物の生息場所に施用することを特徴とする有害節足動物の防除方法を提供する。 As a result of intensive studies to find a compound having an excellent controlling effect on harmful arthropods, the present inventor has found that the sulfonyl compound represented by the following formula (I) is harmful to harmful arthropods such as harmful insects and mites. The present invention has been found to have excellent control efficacy.
That is, the present invention relates to the formula (I)

[Where,
R ¹ represents a C3-C6 fluoroalkyl group, R ² represents a C1-C5 fluoroalkyl group, Q represents an oxygen atom or NR ³ , and R ³ represents a hydrogen atom or a C1-C4 alkyl group. ], A harmful arthropod control agent containing the compound of the present invention as an active ingredient, and an effective amount of the compound of the present invention is determined to be a harmful arthropod or a harmful arthropod. Provided is a method for controlling harmful arthropods, characterized by being applied to the habitat of

  Since the compound of the present invention has an excellent controlling effect on harmful arthropods, it is useful for controlling harmful arthropods.

  In the present invention, the description such as C1-C5 represents the total number of carbon atoms constituting each substituent. In the present invention, the term “fluoroalkyl group” represents an alkyl group substituted with one or more fluorine atoms.

Examples of the C3-C6 fluoroalkyl group represented by R ¹ in the formula (I) include a 2-fluoropropyl group, a 2,2-difluoropropyl group, a 3-fluoropropyl group, a 3,3-difluoropropyl group, 3, 3,3-trifluoropropyl group, 2,2,3,3,3-pentafluoropropyl group, 2,2,2-trifluoro- (1-trifluoromethyl) ethyl group, 1,2,2,2 -C3 fluoroalkyl groups such as tetrafluoro- (1-trifluoromethyl) ethyl group and 2,2,3,3-tetrafluoropropyl group;
2-fluorobutyl group, 2,2-difluorobutyl group, 3-fluorobutyl group, 3,3-difluorobutyl group, 4-fluorobutyl group, 4,4-difluorobutyl group, 4,4,4-trifluoro Butyl group, 3,3,4,4,4-pentafluorobutyl group, 2,2,3,4,4-pentafluorobutyl group and 2,2,3,3,4,4,4-heptafluorobutyl A C4 fluoroalkyl group such as a group;
2-fluoropentyl group, 2,2-difluoropentyl group, 3-fluoropentyl group, 3,3-difluoropentyl group, 4-fluoropentyl group, 4,4-difluoropentyl group, 5-fluoropentyl group, 5, 5-difluoropentyl group, 5,5,5-trifluoropentyl group, 4,4,5,5,5-pentafluoropentyl group, 3,3,4,4,5,5,5-heptafluoropentyl group , 2,2,3,3,4,4,5,5-octafluoropentyl group and 2,2,3,3,4,4,5,5,5-nonafluoropentyl group ;
2-fluorohexyl group, 2,2-difluorohexyl group, 3-fluorohexyl group, 3,3-difluorohexyl group, 4-fluorohexyl group, 4,4-difluorohexyl group, 5-fluorohexyl group, 5, 5-difluorohexyl group, 6-fluorohexyl group, 6,6-difluorohexyl group, 6,6,6-trifluorohexyl group, 5,5,6,6,6-pentafluorohexyl group, 4,4,4 5,5,6,6,6-heptafluorohexyl group, 3,3,4,4,5,5,6,6,6-nonafluorohexyl group and 2,2,3,3,4,4, C6 fluoroalkyl group such as 5,5,6,6,6-undecafluorohexyl group,
Examples of the C1-C5 fluoroalkyl group represented by R ² include a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a 1-fluoroethyl group, a 2-fluoroethyl group, a 1,1-difluoroethyl group, 2, A C1-C2 fluoroalkyl group such as a 2-difluoroethyl group, a 2,2,2-trifluoroethyl group and a 1,1,2,2,2-pentafluoroethyl group;
1-fluoropropyl group, 1,1-difluoropropyl group, 2-fluoropropyl group, 2,2-difluoropropyl group, 3-fluoropropyl group, 3,3-difluoropropyl group, 3,3,3-trifluoro Propyl group, 1,1,2,2,3,3,3-heptafluoropropyl group, 2,2,3,3,3-pentafluoropropyl group, 2,2,2-trifluoro- (1-tri Fluoromethyl) ethyl groups, 1,2,2,2-tetrafluoro- (1-trifluoromethyl) ethyl groups and C3 fluoroalkyl groups such as 2,2,3,3-tetrafluoropropyl groups;
1-fluorobutyl group, 1,1-difluorobutyl group, 2-fluorobutyl group, 2,2-difluorobutyl group, 3-fluorobutyl group, 3,3-difluorobutyl group, 4-fluorobutyl group, 4, 4-difluorobutyl group, 4,4,4-trifluorobutyl group, 3,3,4,4,4-pentafluorobutyl group, 2,2,3,4,4-pentafluorobutyl group, 2,2 , 3,3,4,4,4-heptafluorobutyl group and a C4 fluoroalkyl group such as 1,1,2,2,3,3,4,4,4-nonafluorobutyl group;
1-fluoropentyl group, 1,1-difluoropentyl group, 2-fluoropentyl group, 2,2-difluoropentyl group, 3-fluoropentyl group, 3,3-difluoropentyl group, 4-fluoropentyl group, 4, 4-difluoropentyl group, 5-fluoropentyl group, 5,5-difluoropentyl group, 5,5,5-trifluoropentyl group, 4,4,5,5,5-pentafluoropentyl group, 3,3, 4,4,5,5,5-heptafluoropentyl group, 2,2,3,3,4,4,5,5-octafluoropentyl group, 2,2,3,3,4,4,5, And C5-fluoroalkyl groups such as 5,5-nonafluoropentyl group and 1,1,2,2,3,3,4,4,5,5,5-undecafluoropentyl,
Examples of the C1-C4 alkyl group represented by R ³ include a methyl group, an ethyl group, a propyl group, a butyl group, a 1-methylethyl group, and a 1,1-dimethylethyl group.

As an aspect of this invention compound, the following are mentioned, for example.
A sulfonyl compound represented by formula (I), wherein R ¹ is a 3,3,3-trifluoropropyl group;
A sulfonyl compound represented by formula (I), wherein R ¹ is a 2,2,3,3,3-pentafluoropropyl group;
A sulfonyl compound represented by formula (I), wherein R ¹ is a 3,3,4,4,4-pentafluorobutyl group;
A sulfonyl compound represented by formula (I), wherein R ¹ is a 2,2,3,3,4,4,4-heptafluorobutyl group;
A sulfonyl compound represented by formula (I), wherein R ² is a C1-C3 fluoroalkyl group;
A sulfonyl compound represented by formula (I), wherein R ² is a trifluoromethyl group;
A sulfonyl compound represented by the formula (I), wherein R ² is a 2,2,2-trifluoroethyl group;
A sulfonyl compound represented by the formula (I), wherein R ² is a 1,1,2,2,2-pentafluoroethyl group;
A sulfonyl compound represented by formula (I), wherein R ² is a 1,1,2,2,3,3,3-heptafluoropropyl group;
A sulfonyl compound represented by formula (I), wherein Q is an oxygen atom;
A sulfonyl compound represented by the formula (I), wherein Q is NR ³ and R ³ is a hydrogen atom;
A sulfonyl compound represented by formula (I), wherein Q is NR ³ and R ³ is a methyl group.

〔式中、Ｒ¹、Ｒ²及びＱは前記と同じ意味を表し、Ｘはフッ素原子、塩素原子、臭素原子又はヨウ素原子を表す。〕
該反応は、通常溶媒及び塩基の存在下で行われる。
反応に用いられる溶媒としては、例えばジエチルエーテル、テトラヒドロフラン、ジメトキシエタン等のエーテル、Ｎ，Ｎ−ジメチルホルムアミド等の酸アミド、ジメチルスルホキシド、スルホラン等の有機硫黄、ヘキサン、ヘプタン等の脂肪族炭化水素、トルエン、キシレン等の芳香族炭化水素、クロロホルム、クロロベンゼン等のハロゲン化炭化水素、水及びこれらの混合物が挙げられる。
反応に用いられる塩基としては、例えばトリエチルアミン、１，４−ジアザビシクロ［２．２．２］オクタン、１，８−ジアザビシクロ［５．４．０］−７−ウンデセン等の有機塩基、炭酸カリウム、水素化ナトリウム、水酸化ナトリウム、水酸化カリウム等の無機塩基が挙げられる。
反応に用いられる塩基の量は、化合物（ａ）１モルに対して通常１〜１０モルの割合である。
反応に用いられる化合物（ｂ）の量は、化合物（ａ）１モルに対して通常０．１〜１モルの割合である。
該反応の反応温度は通常−５０〜１００℃の範囲であり、反応時間は通常１〜４８時間の範囲である。
反応終了後は、反応混合物を水に注加し、有機溶媒抽出してから濃縮する等の操作を行うことにより、本発明化合物を単離することができる。単離された本発明化合物は必要に応じてクロマトグラフィー、再結晶等によりさらに精製することもできる。 Next, the manufacturing method of this invention compound is demonstrated.
The compound of the present invention can be produced, for example, by reacting compound (a) with compound (b).

[Wherein R ¹ , R ² and Q represent the same meaning as described above, and X represents a fluorine atom, a chlorine atom, a bromine atom or an iodine atom. ]
The reaction is usually performed in the presence of a solvent and a base.
Examples of the solvent used in the reaction include ethers such as diethyl ether, tetrahydrofuran and dimethoxyethane, acid amides such as N, N-dimethylformamide, organic sulfur such as dimethyl sulfoxide and sulfolane, aliphatic hydrocarbons such as hexane and heptane, Aromatic hydrocarbons such as toluene and xylene, halogenated hydrocarbons such as chloroform and chlorobenzene, water, and mixtures thereof.
Examples of the base used in the reaction include organic bases such as triethylamine, 1,4-diazabicyclo [2.2.2] octane, 1,8-diazabicyclo [5.4.0] -7-undecene, potassium carbonate, hydrogen Inorganic bases such as sodium hydroxide, sodium hydroxide, potassium hydroxide and the like can be mentioned.
The amount of the base used for the reaction is usually 1 to 10 moles relative to 1 mole of the compound (a).
The amount of the compound (b) used in the reaction is usually 0.1 to 1 mol with respect to 1 mol of the compound (a).
The reaction temperature is usually in the range of −50 to 100 ° C., and the reaction time is usually in the range of 1 to 48 hours.
After completion of the reaction, the compound of the present invention can be isolated by performing an operation such as pouring the reaction mixture into water, extracting with an organic solvent and then concentrating. The isolated compound of the present invention can be further purified by chromatography, recrystallization or the like, if necessary.

〔式中、Ｒ²及びＸは前記と同じ意味を表し、Ｒ⁴は１，１−ジメチルエチル基又はベンジル基を表す。〕
該反応は、通常溶媒の存在下で行われる。
反応に用いられる溶媒としては、例えばクロロホルム、クロロベンゼン等のハロゲン化炭化水素、水及びこれらの混合物が挙げられる。
反応に用いられる塩素の量は、化合物（ｃ）１モルに対して通常１モルの割合〜反応系内での飽和量までの範囲である。
該反応の反応温度は通常−５０〜５０℃の範囲であり、反応時間は通常１〜４８時間の範囲である。
反応終了後は、反応混合物を必要に応じて水に注加した後、有機溶媒抽出してから濃縮する等の操作を行うことにより、化合物（ｂ）を単離することができる。単離された化合物（ｂ）は必要に応じて蒸留等によりさらに精製することもできる。 Compound (b) can be produced by the following method according to the method described in, for example, The Journal of Organic Chemistry, 46 (16), p.3335-36 (1981).

[Wherein, R ² and X represent the same meaning as described above, and R ⁴ represents a 1,1-dimethylethyl group or a benzyl group. ]
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include halogenated hydrocarbons such as chloroform and chlorobenzene, water, and mixtures thereof.
The amount of chlorine used in the reaction ranges from a ratio of usually 1 mol to 1 mol of compound (c) to a saturation amount in the reaction system.
The reaction temperature is usually in the range of −50 to 50 ° C., and the reaction time is usually in the range of 1 to 48 hours.
After completion of the reaction, the compound (b) can be isolated by performing an operation such as pouring the reaction mixture into water as necessary, extraction with an organic solvent, and concentration. The isolated compound (b) can be further purified by distillation or the like, if necessary.

  Examples of harmful arthropods for which the compounds of the present invention are effective include harmful insects and harmful mites. More specifically, the following are mentioned.

Hemiptera: Laodelphax striatellus, Japanese green planthopper (Nilaparvata lugens), Japanese green planthoppers (Sogatella furcifera) and other leafhoppers (Nephotettix cincticeps), Nephotettixvis , Aphids such as Myzus persicae, Nezara antennata, Riptortus clavetus, Eysarcoris lewisi, Eysarcoris parvus (Eysarcoris parvus) Plautia stali), Halyomorpha mista, Stenotus rubrovittatus, Trichonotylus ruficornis, etc., Trialeurodes vaporariorum, Silver leaf whitefly Whiteflies such as Bemisia argentifolii, Aonidiella aurantii, Sanho scale insect (Comstockaspis perniciosa), Citrus snow scale (Unaspis citri), Ruby beetle (Ceroplastes rubens), Icerya purchasi and Icerya purchasi , Bed bugs such as bed bugs (Cimex lectularius), whales etc .;

Lepidopterous insects: Chilo suppressalis, Cnaphalocrocis medinalis, Notarcha derogata, Plodia interpunctella, etc., Spodoptera litura, Psedia, Psedia, Heliotis genus, Helicobelpa genus moths, white butterflies (Pieris rapae), white butterflies, Adoxofies genus, Nashihime shinshin oyster (Grapholita molesta), codling moth (Cydia pomonella) scallop moth, Carposina niponensis, etc Anemone such as genus and other genus, Limantria and Euproctinis, etc., Suga such as Plutella xylostella, Pterinophora gossypiella and other species, Hyphantria cunea and other humans Common moths such as moths, moths (Tinea translucens), moths (Tineola bisselliella), etc .;

Diptera: Culex pipiens pallens, Culex tritaeniorhynchus, Culex quinquefasciatus, etc., Aedes aegypti, Aedes albopics, etc. Anopheles, chironomids, Musca domestica, Muscina stabulans and other house flies, black flies, sphagnum flies, fly flies, fly flies (Delia antiqua), flies, etc. Leafhoppers such as Liriomyza trifolii), fruit flies, fruit flies, fruit flies such as fruit flies (Megaselia spiracularis), butterflies such as Drosophila (Clogmia albipunctata), flyfish, aphids, sand flies, etc .;

Coleoptera: Western corn root worm (Diabrotica virgifera virgifera), corn root worms such as Southern corn root worm (Diabrotica undecimpunctata howardi); Weevil such as Sitophilus zeamais, rice weevil (Lissorhoptrus oryzophilus), weevil (Callosobruchuys chienensis), weevil (A), euphorus oleum (Tribo) femoralis, Phyllotreta striolata, Colorado potato beetle (Leptinotarsa decemlineata) and other horn beetles, Dermestes maculates, etc. Epilacunas such as Epilachna vigintioctopunctata, slat beetles, moth beetles, leopard beetles, beetles, Paederus fuscipes, etc .;

Cockroach insects: German cockroach (Blattella germanica), Black cockroach (Periplaneta fuliginosa), American cockroach (Periplaneta americana), Great cockroach (Periplaneta brunnea), Great cockroach (Blatta orientalis), etc .;

Thrips eye pests: Thrips palmi, Thrips tabaci, Frankliniella occidentalis, Frankliniella intonsa, etc .;
Hymenoptera: Monomorium pharaosis, Black ants (Formica fusca japonica), Luriari (Ochetellus glaber), Primustomy pexens, Pheidole noda, etc. japonica), etc .;

Straight-eyed pests: keratoids, grasshoppers, crickets, etc .;
Lepidoptera: Cat fleas (Ctenocephalides felis), Fleas (Ctenocephalides canis), Fleas (Pulex irritans), Xenopsylla cheopis, etc.
Lice insect pests: white lice (Pediculus humanus corporis), white lice (Phthirus pubis), cattle lice (Haematopinus eurysternus), sheep lice (Dalmalinia ovis), pig lice (Haematopinus suis), etc .;
Termite pests: Yamato termite (Reticulitermes speratus), Japanese termite (Coptotermes formosanus), Eastern subterranian termite (Reticulitermes flavipes), Western subterranian termite (Reticulitermes hesperus), Dark southern subterranian termite (Reticulitermes virginite territhite) (Reticulitermes tibialis), Subteranian termites such as Desert Subteranian termite (Heterotermes aureus), Drywood termites such as American termite minor (Incisitermes minor), Dumpwood termites such as Nevada Dumpwood Termite (Zootermopsis nevadensis);

Acarina: Tetranychus urticae, Kanzawa spider mite (Tetranychus kanzawai), Citrus spider mite (Panonychus citri), apple spider mite (Panonychus ulmi), spider mites (Aculops lycopers), citrus spider mite (Aculops lycopers) Mites (Aculus schlechtendali), mites (Polyphagotarsonemus latus), mites, mites, mites (Haemaphysalis longicornis), mites (Haemaphysalis flava), mites centor ), Dermacentor taiwanicus, Ixodes ovatus, Ixodes persulcatus, Black-legged tick (Ixodes scapularis), Boophilus microplus, Lone starch Ticks (Amblyomma americanum), ticks such as Rhipicephalus sanguineus, acarids such as Tyrophagus putrescentiae, Dermatophagoides farinae, Dermatophagoss tick , Tsutsu mites (Cheyletus malaccensis), tsume mites (Cheyletus moorei), etc. Etc .;
Spiders: Chiracanthium japonicum, Latrodectus hasseltii, etc .;

Lips and legs: Gezi (Thereuonema hilgendorfi), Tobismadede (Scolopendra subspinipes), etc .;
Double-legged class: Japanese red millipede (Oxidus gracilis), Japanese red millipede (Nedyopus tambanus), etc .;
Isopods: Armadillidium vulgare, etc .;
Gastropods: Limax marginatus, Limax flavus, etc.

The harmful arthropod control agent of the present invention may be the compound of the present invention itself, but it is usually mixed with a solid carrier, a liquid carrier and / or a gaseous carrier, and a surfactant or other formulation adjuvant is added if necessary. Into emulsions, oils, shampoos, flowables, powders, wettable powders, granules, pastes, microcapsules, foams, aerosols, carbon dioxide, tablets, resin formulations, etc. It has been done. These preparations may be used after being processed into poison baits, mosquito coils, electric mosquito mats, fumigants, fumigants, and sheets.
These preparations usually contain 0.1 to 95% by weight of the compound of the present invention.

  Examples of solid carriers used for formulation include clays (kaolin clay, diatomaceous earth, bentonite, fusami clay, acidic clay), synthetic hydrous silicon oxide, talc, ceramics, and other inorganic minerals (sericite, quartz, sulfur). , Activated carbon, calcium carbonate, hydrated silica, etc.), fine powders and granular materials such as chemical fertilizers (ammonium sulfate, phosphorous acid, ammonium nitrate, ammonium chloride, urea, etc.).

  Examples of the liquid carrier include aromatic or aliphatic hydrocarbons (xylene, toluene, alkylnaphthalene, phenylxylylethane, kerosene, light oil, hexane, cyclohexane, etc.), halogenated hydrocarbons (chlorobenzene, dichloromethane, dichloroethane, trichloroethane). Etc.), alcohols (methanol, ethanol, isopropyl alcohol, butanol, hexanol, ethylene glycol, etc.), ethers (diethyl ether, ethylene glycol dimethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, propylene glycol monomethyl ether, tetrahydrofuran, dioxane, etc.) ), Esters (ethyl acetate, butyl acetate, etc.), ketones (acetone, methyl ethyl keto) , Methyl isobutyl ketone, cyclohexanone, etc.), nitriles (acetonitrile, isobutyronitrile, etc.), sulfoxides (dimethyl sulfoxide, etc.), acid amides (N, N-dimethylformamide, N, N-dimethylacetamide, etc.), vegetable oil (Soybean oil, cottonseed oil, etc.), vegetable essential oils (orange oil, hyssop oil, lemon oil, etc.) and water.

  Examples of the gaseous carrier include butane gas, Freon gas, liquefied petroleum gas (LPG), dimethyl ether, carbon dioxide gas and the like.

  Examples of the surfactant include alkyl sulfate ester salts, alkyl sulfonate salts, alkyl aryl sulfonate salts, alkyl aryl ethers and polyoxyethylenated products thereof, polyethylene glycol ethers, polyhydric alcohol esters, and sugar alcohol derivatives. It is done.

  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 acids, etc.), PAP (isopropyl acid phosphate), BHT (2,6-di-t-butyl-4-methylphenol), BHA (2-t- Butyl-4-methoxyphenol and 3-t-butyl-4-methoxyphenol), vegetable oils, mineral oils, fatty acids and fatty acid esters.

Examples of the base material of the resin preparation include vinyl chloride polymers, polyurethanes, etc., and these base materials include phthalic acid esters (dimethyl phthalate, dioctyl phthalate, etc.) and adipic acid esters as necessary. Further, a plasticizer such as stearic acid may be added. The resin formulation is obtained by kneading the compound in the base material using a normal kneading apparatus, and then molding by injection molding, extrusion molding, press molding, etc., and if necessary, through steps such as molding, cutting, It can be processed into resin preparations such as plate, film, tape, net, and string. These resin preparations are processed, for example, as animal collars, animal ear tags, sheet preparations, attracting strings, or gardening supports.
Examples of the bait base include cereal flour, vegetable oil, sugar, crystalline cellulose and the like, and if necessary, antioxidants such as dibutylhydroxytoluene and nordihydroguaiaretic acid, and preservatives such as dehydroacetic acid. Additives for preventing accidental eating by children and pets such as pepper powder, pests such as cheese flavor, onion flavor and peanut oil are added.

  The harmful arthropod control agent of the present invention is used, for example, by being applied directly to harmful arthropods and / or by applying to harmful arthropod habitats (plants, animals, soil, etc.).

  When the harmful arthropod control agent of the present invention is used for controlling agricultural and forestry pests, the application amount is usually 1 to 10,000 g / ha, preferably 10 to 500 g / ha as the amount of active ingredient. Emulsions, wettable powders, flowables, microcapsule preparations, etc. are usually diluted with water so that the active ingredient concentration is 1-1000 ppm, and powders, granules, etc. are usually used as they are. These formulations may be applied directly to plants that are to be protected from harmful arthropods. By treating these preparations in the soil, harmful arthropods that inhabit the soil can be controlled, and these preparations can be treated on the nursery before planting, It can also be processed. Furthermore, the sheet preparation of the harmful arthropod control agent of the present invention can be applied by a method such as wrapping around a plant, installing in the vicinity of the plant, or laying on the soil surface of the plant origin.

When the harmful arthropod control agent of the present invention is used for prevention of epidemics, the application amount is usually 0.001 to 10 mg / m ³ as an active ingredient amount when applied to a space, and 0 when applied to a plane. 0.001 to 100 mg / m ² . Emulsions, wettable powders, flowables and the like are usually diluted with water so that the active ingredient concentration is 0.01 to 10000 ppm, and oils, aerosols, smoke agents, poison baits and the like are usually applied as they are.

  When the harmful arthropod control agent of the present invention is used for controlling ectoparasites of cattle, horses, pigs, sheep, goats, chickens, small animals such as dogs, cats, rats, mice, etc., it is well known in veterinary medicine. Can be used on animals. Specifically, for the purpose of systemic suppression, for example, tablets, feed mixing, suppositories, injections (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.) are intended for non-systemic suppression. In such a case, for example, an oil agent or an aqueous liquid agent is sprayed, a pour-on treatment or a spot-on treatment is performed, the animal is washed with a shampoo preparation, or a resin preparation is attached to the animal with a collar or ear tag. The amount of the compound of the present invention when administered to an animal body is usually in the range of 0.1 to 1000 mg per 1 kg body weight of the animal.

  The harmful arthropod control agent of the present invention includes other insecticides, nematicides, acaricides, fungicides, herbicides, plant growth regulators, synergists, fertilizers, soil improvers, animal feeds and the like. They can be mixed or used together.

  Examples of such other insecticides and acaricides are allethrin, tetramethrin, praretrin, phenothrin, resmethrin, ciphenothrin, permethrin, cypermethrin, alpha cypermethrin, zetacypermethrin, deltamethrin, tralomethrin, cyfluthrin, betacyfluthrin, cyhalothrin. , Lambda halothrin, framethrin, imiprotorin, etofenprox, fenvalerate, esfenvalerate, fenpropatoline, silafluophene, bifenthrin, transfluthrin, flucitrinate, taufulvalinate, acrinatrin, teflutrin, cycloprotorin, empensrin 2,3,5,6-tetrafluoro-4-methoxymethylbenzyl 3- (2-methyl-1-propenyl) -2 , 2-dimethylcyclopropanecarboxylate, 2,3,5,6-tetrafluoro-4-methoxymethylbenzyl 3- (1-propenyl) -2,2-dimethylcyclopropanecarboxylate, 2,3,5,6 -Pyrethroid compounds such as tetrafluoro-4-methylbenzyl 3- (1-propenyl) -2,2-dimethylcyclopropanecarboxylate, dichlorvos, fenitrothion, cyanophos, propenophos, sulfophos, phentoate, isoxathione, tetrachlorobinphos, fenthion , Organophosphorus compounds such as chlorpyrifos, diazinon, acephate, terbufos, folate, chlorethoxyphos, phosthiazate, etoprophos, kazusafos, methidathion, propoxer, carbaryl, methoxadiazone Carbamate compounds such as fenobucarb, mesomil, thiodicarb, alanicarb, benfuracarb, oxamyl, aldicarb, methiocarb, etc. Juvenile hormone-like substances such as urea compounds, pyriproxyfen, metoprene, hydroprene, phenoxycarb, N-phenyl such as acetamiprid, nitenpyram, thiacloprid, neonicotinoid compounds such as thiamethoxam, dinotefuran, clothianidin, and acetoprolol, ethiprole Pyrazole compounds, tebufenozide, chromafenozide, methoxyphenozide, halofenodi Benzoylhydrazine compounds such as diafenthiuron, pymetrozine, flonicamid, triazamate, buprofezin, spinosad, emamectin benzoate, chlorfenapyr, indoxacarb, pyridalyl, cyromazine, fenpyroximate, bifenazate, tefenfenpyrad, fenfenpyrim, pyridaben Examples include etoxazole, phenazaquin, acequinosyl, hexothiazox, clofentezine, fenbutane oxide, dicophor, propargite, evermectin, milbemectin, amitraz, cartap, bensultap, thiocyclam, endosulfan, spirodiclofen, spiromesifen, fulvendiamide and azadirachtin.

  Other fungicides include, for example, strobilurin compounds such as azoxystrobin, organophosphorus compounds such as triclofosmethyl, azole compounds such as triflumizole, pefrazoate, difenoconazole, fusalide, flutolanil, validamycin, probenazole, dicloromedin , Pencyclon, dazomet, kasugamycin, IBP, pyroxylone, oxolinic acid, tricyclazole, ferimzone, mepronil, EDDP, isoprothiolane, carpropamide, diclocimet, furametopir, fludioxonil, prosimidone and dietofencarb.

  Hereinafter, although this invention is demonstrated in more detail by a manufacture example, a formulation example, a test example, etc., this invention is not limited to these examples.

  First, the manufacture example of this invention compound is shown.

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）４．６３（ｔ，２Ｈ）、３．４２−３．４８（ｍ，２Ｈ）、２．６５−２．７８（ｍ，２Ｈ） Production Example 1
Benzyl = 3,3,3-trifluoropropyl = sulfide (1.5 g) and water (20 ml) were mixed, stirred under ice cooling, and blown until chlorine gas was saturated while maintaining the temperature of the mixture at 10 ° C. or lower. Then, it stirred at 10 degrees C or less for 2 hours. The reaction mixture was extracted with chloroform, and the organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give a residue.
The residue obtained by the above operation and 1.1 g of 2,2,3,3,3-pentafluoropropanol were added to 30 ml of tetrahydrofuran, and then 0.9 ml of triethylamine was added and stirred for 10 hours. 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to 2,3,3,3-trifluoropropanesulfonic acid 2,2,3,3,3-pentafluoropropyl (hereinafter referred to as the present compound (1)). .44 g was obtained.
Compound (1) of the present invention

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 4.63 (t, 2H), 3.42-3.48 (m, 2H), 2.65-2.78 (m, 2H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）４．６７（ｔ，２Ｈ）、３．４２−３．５０（ｍ，２Ｈ）、２．６６−２．７９（ｍ，２Ｈ） Production Example 2
According to the method described in Production Example 1, except that 1.4 g of 2,2,3,3,4,4,4-heptafluorobutanol was used instead of 2,2,3,3,3-pentafluoropropanol. 3,3,3-trifluoropropanesulfonic acid 2,2,3,3,4,4,4-heptafluorobutyl (hereinafter referred to as the present compound (2)) 1.50 g was obtained.
Compound (2) of the present invention

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 4.67 (t, 2H), 3.42-3.50 (m, 2H), 2.66-2.79 (m, 2H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）４．５４（ｔ，２Ｈ）、３．３４−３．４３（ｍ，２Ｈ）、２．５１−２．７８（ｍ，４Ｈ） Production Example 3
Benzyl = 3,3,3-trifluoropropyl = sulfide 0.8 g, triethylamine 0.5 ml, 3,3,4,4,4-pentafluoro instead of 2,2,3,3,3-pentafluoropropanol Except that 0.6 g of butanol was used, 3,3,4-trifluoropropanesulfonic acid 3,3,4,4,4-pentafluorobutyl (hereinafter referred to as the present compound ( 3) 0.52 g was obtained.
Compound (3) of the present invention

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 4.54 (t, 2H), 3.34-3.43 (m, 2H), 2.51-2.78 (m, 4H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）５．１７−５．２８（ｍ，１Ｈ）、３．４６−３．５３（ｍ，２Ｈ）、２．６３−２．７８（ｍ，２Ｈ）、１．６６（ｄ，３Ｈ） Production Example 4
Benzyl = 3,3,3-trifluoropropyl = sulfide 0.8 g, triethylamine 0.5 ml, 3,3,4,4,5,5 instead of 2,2,3,3,3-pentafluoropropanol According to the method described in Production Example 1 except that 0.8 g of 5-heptafluoropentan-2-ol was used, 3,3,3-trifluoropropanesulfonic acid 3,3,4,4,5,5,5 0.68 g of 5-heptafluoropentan-2-yl (hereinafter referred to as the present compound (4)) was obtained.
The present compound (4)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 5.17-5.28 (m, 1H), 3.46-3.53 (m, 2H), 2.63-2.78 (m , 2H), 1.66 (d, 3H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）４．６８（ｔ，２Ｈ）、３．４２−３．５０（ｍ，２Ｈ）、２．６３−２．７８（ｍ，２Ｈ） Production Example 5
Benzyl = 3,3,3-trifluoropropyl = sulfide 0.8 g, triethylamine 0.5 ml, 2,2,3,3,4,4 instead of 2,2,3,3,3-pentafluoropropanol 3,3,3-trifluoropropanesulfonic acid 2,2,3,3,4,4 according to the method described in Production Example 1 except that 0.9 g of 5,5,5-nonafluoropentanol was used , 5,5,5-Nonafluoropentyl (hereinafter referred to as the present compound (5)) 0.90 g was obtained.

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 4.68 (t, 2H), 3.42-3.50 (m, 2H), 2.62-2.78 (m, 2H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）４．６８（ｔ，２Ｈ）、３．４２−３．５０（ｍ，２Ｈ）、２．６６−２．８０（ｍ，２Ｈ） Production Example 6
Benzyl = 3,3,3-trifluoropropyl = sulfide 0.8 g, triethylamine 0.5 ml, 2,2,3,3,4,4 instead of 2,2,3,3,3-pentafluoropropanol 3,3,3-trifluoropropanesulfonic acid 2,2,3,3 according to the method described in Production Example 1 except that 1.1 g of 5,5,6,6,6-undecafluorohexanol was used , 4, 4, 5, 5, 6, 6, 6-undecafluorohexyl (hereinafter referred to as the present compound (6)) 1.10 g was obtained.

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 4.68 (t, 2H), 3.42-3.50 (m, 2H), 2.66-2.80 (m, 2H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）４．８２（ｂｓ，１Ｈ）、３．８６（ｄｔ，２Ｈ）、３．２９−３．３８（ｍ，２Ｈ）、２．５８−２．７２（ｍ，２Ｈ） Production Example 7
Benzyl = 3,3,3-trifluoropropyl = sulfide (1.5 g) and water (20 ml) were mixed, stirred under ice cooling, and blown until chlorine gas was saturated while maintaining the temperature of the mixture at 10 ° C. or lower. Then, it stirred at 10 degrees C or less for 2 hours. The reaction mixture was extracted with chloroform, and the organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give a residue.
The residue obtained by the above operation and 1.0 g of 2,2,3,3,3-pentafluoropropylamine were added to 30 ml of tetrahydrofuran, and then 0.9 ml of triethylamine was added and stirred for 10 hours. 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, and 3,3,3-trifluoropropanesulfonic acid 2,2,3,3,3-pentafluoropropylamide (hereinafter referred to as the present compound (7)). 1.35 g was obtained.
Compound (7) of the present invention

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 4.82 (bs, 1H), 3.86 (dt, 2H), 3.29-3.38 (m, 2H), 2.58- 2.72 (m, 2H)

本発明化合物８
¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）４．７７（ｂｓ，１Ｈ）、３．９１（ｄｔ，２Ｈ）、３．２９−３．３８（ｍ，２Ｈ）、２．５９−２．７１（ｍ，２Ｈ） Production Example 8
According to the method described in Production Example 7, except that 1.4 g of 2,2,3,3,4,4,4-heptafluorobutylamine was used instead of 2,2,3,3,3-pentafluoropropylamine. Thus, 1.81 g of 3,3,3-trifluoropropanesulfonic acid 2,2,3,3,4,4,4-heptafluorobutyramide (hereinafter referred to as the present compound (8)) was obtained. .

Compound 8 of the present invention
¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 4.77 (bs, 1H), 3.91 (dt, 2H), 3.29-3.38 (m, 2H), 2.59- 2.71 (m, 2H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）３．９８（ｔ，２Ｈ）、３．２２−３．２９（ｍ，２Ｈ）、３．１１（ｓ，３Ｈ）、２．５９−２．７１（ｍ，２Ｈ） Production Example 9
Production Example except that 1.5 g of N- (2,2,3,3,4,4,4-heptafluorobutyl) methylamine was used instead of 2,2,3,3,3-pentafluoropropylamine 7, 3,3,3-trifluoropropanesulfonic acid N- (2,2,3,3,4,4,4-heptafluorobutyl) methylamide (hereinafter referred to as the present compound (9)) 1.27 g was obtained.

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 3.98 (t, 2H), 3.22-3.29 (m, 2H), 3.11 (s, 3H), 2.59- 2.71 (m, 2H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）４．６４（ｔ，２Ｈ）、３．４６−３．５３（ｍ，２Ｈ）、２．５８−２．７４（ｍ，２Ｈ） Production Example 10
Mix 2.5 g of benzyl = 3,3,4,4,4-pentafluorobutyl = sulfide and 20 ml of water and stir under ice cooling to saturate chlorine gas while maintaining the temperature of the mixture at 10 ° C. or lower. Then, the mixture was stirred for 1 hour at 10 ° C. or lower and 2 hours at room temperature. The reaction mixture was extracted with chloroform, and the organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give a residue.
The residue obtained by the above operation and 1.4 g of 2,2,3,3,3-pentafluoropropanol were added to 30 ml of tetrahydrofuran, and then 1.3 ml of triethylamine was added and stirred for 16 hours. 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 2,3,4,4,4-pentafluorobutanesulfonic acid 2,2,3,3,3-pentafluoropropyl (hereinafter referred to as the present compound (10)). 2.0 g was obtained.
Compound (10) of the present invention

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 4.64 (t, 2H), 3.46-3.53 (m, 2H), 2.58-2.74 (m, 2H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）４．６８（ｔ，２Ｈ）、３．４５−３．５２（ｍ，２Ｈ）、２．５８−２．７３（ｍ，２Ｈ） Production Example 11
According to the method described in Preparation Example 10, except that 1.9 g of 2,2,3,3,4,4,4-heptafluorobutanol was used instead of 2,2,3,3,3-pentafluoropropanol. 3,3,4,4,4-pentafluorobutanesulfonic acid 2,2,3,3,4,4,4-heptafluorobutyl (hereinafter referred to as the present compound (11)) 2.58 g Obtained.

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 4.68 (t, 2H), 3.45-3.52 (m, 2H), 2.58-2.73 (m, 2H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）４．９０（ｂｓ，１Ｈ）、３．８７（ｄｔ，２Ｈ）、３．３２−３．３９（ｍ，２Ｈ）、２．５３−２．６８（ｍ，２Ｈ） Production Example 12
Mix 2.5 g of benzyl = 3,3,4,4,4-pentafluorobutyl = sulfide and 20 ml of water and stir under ice cooling to saturate chlorine gas while maintaining the temperature of the mixture at 10 ° C. or lower. Then, the mixture was stirred for 1 hour at 10 ° C. or lower and 2 hours at room temperature. The reaction mixture was extracted with chloroform, and the organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give a residue.
The residue obtained by the above operation and 1.4 g of 2,2,3,3,3-pentafluoropropylamine were added to 30 ml of tetrahydrofuran, and then 1.3 ml of triethylamine was added and stirred for 16 hours. 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 3,3,4,4,4-pentafluorobutanesulfonic acid 2,2,3,3,3-pentafluoropropylamide (hereinafter referred to as the present compound (12)). 2.03 g was obtained.

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 4.90 (bs, 1H), 3.87 (dt, 2H), 3.32-3.39 (m, 2H), 2.53- 2.68 (m, 2H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）４．７４（ｂｓ，１Ｈ）、３．９２（ｄｔ，２Ｈ）、３．３２−３．４０（ｍ，２Ｈ）、２．５２−２．６８（ｍ，２Ｈ） Production Example 13
According to the method described in Production Example 12, except that 1.8 g of 2,2,3,3,4,4,4-heptafluorobutylamine was used instead of 2,2,3,3,3-pentafluoropropylamine. 3,3,4,4,4-pentafluorobutanesulfonic acid 2,2,3,3,4,4,4-heptafluorobutyramide (hereinafter referred to as the present compound (13)) 73 g was obtained.

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 4.74 (bs, 1H), 3.92 (dt, 2H), 3.32-3.40 (m, 2H), 2.52- 2.68 (m, 2H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）４．６５（ｔ，２Ｈ）、３．４６−３．５２（ｍ，２Ｈ）、２．６０−２．７６（ｍ，２Ｈ） Production Example 14
Benzyl = 3,3,4,4,5,5,5-heptafluoropentyl = sulfide 1.3 g and water 30 ml were mixed and stirred under ice-cooling while maintaining the temperature of the mixture at 10 ° C. or lower. Chlorine gas was blown until saturated, and then stirred at 10 ° C. or lower for 2 hours. The reaction mixture was extracted with chloroform, and the organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give a residue.
The residue obtained by the above operation and 0.6 g of 2,2,3,3,3-pentafluoropropanol were added to 30 ml of tetrahydrofuran, and then 0.6 ml of triethylamine was added and stirred for 48 hours. 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 3,3,4,4,5,5,5-heptafluoropentanesulfonic acid 2,2,3,3,3-pentafluoropropyl (hereinafter referred to as the compound of the present invention). (14).) 0.9 g was obtained.
The present compound (14)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 4.65 (t, 2H), 3.46-3.52 (m, 2H), 2.60-2.76 (m, 2H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）４．６９（ｔ，２Ｈ）、３．４３−３．５２（ｍ，２Ｈ）、２．５９−２．７６（ｍ，２Ｈ） Production Example 15
According to the method described in Production Example 14, except that 0.8 g of 2,2,3,3,4,4,4-heptafluorobutanol was used instead of 2,2,3,3,3-pentafluoropropanol. 3,3,4,4,5,5,5-heptafluoropentanesulfonic acid 2,2,3,3,4,4,4-heptafluorobutyl (hereinafter referred to as the present compound (15)) 1.21 g was obtained.
The present compound (15)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 4.69 (t, 2H), 3.43-3.52 (m, 2H), 2.59-2.76 (m, 2H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）４．８５（ｂｓ，１Ｈ）、３．８８（ｄｔ，２Ｈ）、３．３２−３．４０（ｍ，２Ｈ）、２．５６−２．７２（ｍ，２Ｈ） Production Example 16
Benzyl = 3,3,4,4,5,5,5-heptafluoropentyl = sulfide 1.3 g and water 30 ml were mixed and stirred under ice-cooling while maintaining the temperature of the mixture at 10 ° C. or lower. Chlorine gas was blown until saturated, and then stirred at 10 ° C. or lower for 2 hours. The reaction mixture was extracted with chloroform, and the organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give a residue.
The residue obtained by the above operation and 0.6 g of 2,2,3,3,3-pentafluoropropylamine were added to 30 ml of tetrahydrofuran, and then 0.6 ml of triethylamine was added and stirred for 48 hours. 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 3,3,4,4,5,5,5-heptafluoropentanesulfonic acid 2,2,3,3,3-pentafluoropropylamide (hereinafter referred to as the present invention). It describes as a compound (16).) 1.11g was obtained.
The present compound (16)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 4.85 (bs, 1H), 3.88 (dt, 2H), 3.32-3.40 (m, 2H), 2.56- 2.72 (m, 2H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）４．７９（ｂｓ，１Ｈ）、３．９２（ｄｔ，２Ｈ）、３．３３−３．４０（ｍ，２Ｈ）、２．５６−２．７１（ｍ，２Ｈ） Production Example 17
According to the method described in Production Example 16, except that 0.8 g of 2,2,3,3,4,4,4-heptafluorobutylamine was used instead of 2,2,3,3,3-pentafluoropropylamine. 3,3,4,4,5,5,5-heptafluoropentanesulfonic acid 2,2,3,3,4,4,4-heptafluorobutyramide (hereinafter referred to as the present compound (17)) .) 1.31 g was obtained.
The present compound (17)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 4.79 (bs, 1H), 3.92 (dt, 2H), 3.33-3.40 (m, 2H), 2.56- 2.71 (m, 2H)

  Specific examples of the compound of the present invention are shown in (Table 1) to (Table 4).

  Next, production examples of intermediates of the compound of the present invention are shown as reference production examples.

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）７．２３−７．３８（ｍ，５Ｈ）、３．７６（ｓ，２Ｈ）、２．５９−２．６５（ｍ，２Ｈ）、２．１５−２．３０（ｍ，２Ｈ） Reference production example 1
18.0 g of 1-iodo-3,3,3-trifluoropropane and 10.0 g of benzyl mercaptan were dissolved in 100 ml of N, N-dimethylformamide, 11.1 g of potassium carbonate was added, and the mixture was stirred at room temperature for 8 hours. 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with 10% hydrochloric acid and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 16.2 g of benzyl = 3,3,3-trifluoropropyl sulfide.
Benzyl = 3,3,3-trifluoropropyl = sulfide

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 7.2-3.38 (m, 5H), 3.76 (s, 2H), 2.59-2.65 (m, 2H), 2.15-2.30 (m, 2H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）７．２３−７．３８（ｍ，５Ｈ）、３．７６（ｓ，２Ｈ）、２．５９−２．６５（ｍ，２Ｈ）、２．１５−２．３０（ｍ，２Ｈ） Reference production example 2
Except that 12.1-iodo-3,3,4,4,4-pentafluorobutyl sulfide was used instead of 1-iodo-3,3,3-trifluoropropane and the reaction time was 16 hours. In accordance with the method of Reference Production Example 1, 19.1 g of benzyl = 3,3,4,4,4-tetrafluorobutyl = sulfide was obtained.
Benzyl = 3,3,4,4,4-tetrafluorobutyl = sulfide

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 7.2-3.38 (m, 5H), 3.76 (s, 2H), 2.59-2.65 (m, 2H), 2.15-2.30 (m, 2H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）７．２３−７．３８（ｍ，５Ｈ）、３．７６（ｓ，２Ｈ）、２．５９−２．６５（ｍ，２Ｈ）、２．１５−２．３０（ｍ，２Ｈ） Reference production example 3
1-iodo-3,3,4,4,5,5,5-heptafluoropentane 12.0 g, benzyl mercaptan 4.6 g, potassium carbonate 5 instead of 1-iodo-3,3,3-trifluoropropane According to the method described in Reference Production Example 1 except that 1 g and 50 ml of N, N-dimethylformamide were used and the reaction time was 20 hours, benzyl = 3,3,4,4,5,5,5-hepta 10.7 g of fluoropentyl sulfide was obtained.

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 7.2-3.38 (m, 5H), 3.76 (s, 2H), 2.59-2.65 (m, 2H), 2.15-2.30 (m, 2H)

  Next, formulation examples are shown. In addition, a part shows a weight part.

Formulation Example 1
9 parts of the compounds (1) to (17) of the present invention are dissolved in 37.5 parts of xylene and 37.5 parts of N, N-dimethylformamide, and 10 parts of polyoxyethylene styrylphenyl ether and calcium dodecylbenzenesulfonate are dissolved therein. Add 6 parts and mix well with stirring to obtain an emulsion.

Formulation Example 2
To 40 parts of the present compounds (1) to (17), 5 parts of Solpol 5060 (registered trademark of Toho Chemical) is added and mixed well to prepare Carplex # 80 (registered trademark of Shionogi & Co., synthetic silicon hydroxide fine powder). ) Add 32 parts, 23 parts of 300 mesh diatomaceous earth and mix with a juice mixer to obtain a wettable powder.

Formulation Example 3
Add 3 parts of the compounds (1) to (17) of the present invention, 5 parts of fine powder of hydrous silicon oxide, 5 parts of sodium dodecylbenzenesulfonate, 30 parts of bentonite and 57 parts of clay, and stir and mix well. An appropriate amount of water is added, further stirred, granulated with a granulator, and dried by ventilation to obtain granules.

Formulation Example 4
After thoroughly mixing 4.5 parts of the present compounds (1) to (17), 1 part of a synthetic silicon hydroxide fine powder, 1 part of Doreles B (Sankyo Co., Ltd.) as a flocculant and 7 parts of clay in a mortar, Stir and mix. 86.5 parts of cut clay is added to the resulting mixture and mixed thoroughly with stirring to obtain a powder.

Formulation Example 5
The compound of the present invention (1) to (17): 10 parts; 35 parts of white carbon containing 50 parts of polyoxyethylene alkyl ether sulfate ammonium salt; and 55 parts of water are mixed and finely pulverized by a wet pulverization method. obtain.

Formulation Example 6
0.5 parts of the compounds (1) to (17) of the present invention are dissolved in 10 parts of dichloromethane and mixed with 89.5 parts of Isopar M (isoparaffin: Exxon Chemical Registration) to obtain an oil.

Formulation Example 7
This invention compound (1)-(17) 0.1 part and neothiozole (Chuo Kasei Co., Ltd.) 49.9 part are put into an aerosol can, and after mounting an aerosol valve, it is filled with 25 parts dimethyl ether and 25 parts LPG. Then, an oily aerosol is obtained by mounting the actuator.

Formulation Example 8
0.6 parts of the present compounds (1) to (17), 0.01 part of BHT, 5 parts of xylene, 3.39 parts of deodorized kerosene and 1 part of emulsifier {Atmos 300 (registered trademark name of Atmos Chemical)} were mixed and dissolved. One and 50 parts of distilled water are filled in an aerosol container, a valve part is attached, and 40 parts of propellant (LPG) is pressurized and filled through the valve to obtain an aqueous aerosol.

  Next, test examples show that the compounds of the present invention are effective as active ingredients for harmful arthropod control agents.

Test example 1
The active compound concentration of the preparations of the present compounds (2), (8), (9), (11), (12), (13), (16) and (17) obtained in Formulation Example 5 is 55. The test drug solution was prepared by diluting to 6 ppm.
On the other hand, 50 g of soil soil bonsol 2 (manufactured by Sumitomo Chemical Co., Ltd.) is put in a polyethylene cup having 5 holes with a diameter of 5 mm in the bottom, seeded with 10 to 15 seeds, and grown until the second true leaf develops. Rice was treated by absorbing 45 ml of the test chemical prepared as described above from the bottom of the cup. Then, after leaving still in the greenhouse <25 degreeC> for 6 days, the height of the rice was cut into 5 cm, 30 first-instar larvae of the brown planthopper were released, and left still in the greenhouse <25 degreeC>. Six days after releasing the green planthopper larvae, the number of the green planthopper parasitic on the rice was investigated.
As a result, in the treatments of the compounds (2), (8), (9), (11), (12), (13), (16) and (17) of the present invention, the number of insects parasitized 6 days after the treatment. Was 3 or less.

Test example 2
The compound of the present invention (2), (8), (9), (11), (14), (15), (16), and (17) obtained by Formulation Example 5 was prepared with an active ingredient concentration of 500 ppm. A test chemical solution was prepared by diluting with water. A filter paper of the same size was laid on the bottom of a polyethylene cup having a diameter of 5.5 cm, 0.7 ml of the test chemical solution was dropped on the filter paper, and 30 mg of sucrose was uniformly added as food. 10 female Musca domestica females were released into the polyethylene cup and capped. After 24 hours, the life-and-death of the house fly was investigated to determine the death rate.
As a result, in the treatments of the present compounds (2), (8), (9), (11), (14), (15), (16) and (17), a death rate of 70% or more was shown. .

Test example 3
The preparations of the present compounds (2), (8), (9), (11), (14) and (15) obtained in Formulation Example 5 were diluted with water so that the active ingredient concentration was 500 ppm, A test chemical solution was prepared. A filter paper of the same size was laid on the bottom of a polyethylene cup having a diameter of 5.5 cm, 0.7 ml of the test chemical solution was dropped on the filter paper, and 30 mg of sucrose was uniformly added as food. Two adult male cockroaches (Blattalla germanica) were released into the polyethylene cup and covered. Six days later, the death and death of German cockroaches were investigated to determine the death rate.
As a result, in the treatments of the compounds (2), (8), (9), (11), (14) and (15) of the present invention, a mortality rate of 100% was shown.

Test example 4
The preparations of the present compound (2), (8), (10), (11), (13), (14), (15), (16) and (17) obtained in Formulation Example 5 are used as active ingredients. It diluted with water so that a density | concentration might be 500 ppm, and prepared the chemical | medical solution for a test. 0.7 ml of the test chemical solution was added to 100 ml of ion-exchanged water (active ingredient concentration: 3.5 ppm). Twenty dead larvae of Culex pipiens pallens were released into the solution, and after 1 day, the viability was investigated to determine the mortality rate.
As a result, the death rate was 90% in the treatment of the compounds (2), (8), (10), (11), (13), (14), (15), (16) and (17) of the present invention. The above is shown.

Claims (4)

Formula (I)

[Where,
R ¹ represents a C3-C6 fluoroalkyl group,
R ² represents a C1-C5 fluoroalkyl group,
Q represents an oxygen atom or NR ³ ;
R ³ represents a hydrogen atom or a C1-C4 alkyl group. ]
A sulfonyl compound represented by: The sulfonyl compound according to claim 1, wherein R ² is a C1-C3 fluoroalkyl group.   A harmful arthropod control agent comprising the sulfonyl compound according to claim 1 as an active ingredient. A method for controlling harmful arthropods, which comprises applying an effective amount of the sulfonyl compound according to claim 1 or 2 to harmful arthropods or habitats of harmful arthropods.