Title of Invention	2-(3-METHANESULFONYLOXYPROPYLOXY)-5- TRIFLUOROMETHYLPYRIDINE
Abstract	The present invention relates to 2-(3-methanesulfonyloxypropyloxy)-5-trifluoromethylpyridine.

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i I I 1 DESCRIPTION DIHALOPROPENE COMPOUNDS, INSECTICIDAL/ACARICIDAL AGENTS CONTAINING SAME, AND INTERMEDUTES FOR THEIR PRODUCTION Technical Held The present invention relates to dihalopropene compounds, iijsecticidal/acari-cidal agents containing these compounds as acti\"e ingredients, and intermediates for their production. Background Art As disclosed in JP-A 4g-86835/I973 and JP-A 49-1526/"I974, for example, it is well known that some kinds of propene compounds can be used as an active ingredient of insecticides. In view of their insecticidal/acaricidal activity, it cannot always be said that these compounds are satisfactorily effective for the control of noxious insects, mites and ticks. Disclosure of Invention The present inventors have intensively studied to find a compound having excellent insecticidal/acaricidal activity. Asa result, they have found that particular dihalo¬propene compounds have satisfactory insecticidal/acaricidal activity for the control of noxious insects, mites and ticks, thereby completing the present invention. That is, the present invention provides a dihalopropene compound (herein¬after referred to as the present compound) of the general formula: Examples of the halogen atom represented by R or R are fluorine, chlorine, bromine and iodine. Examples of the heterocyclic ring in the optionally substituted heterocyclic ring group represented by A are isoxazole, isothiazole, thiazole, 1,3,4-thiadiazoie, pyrrole, furan, thiophene, pyrazole, imidazole, l,2,3-tria2ole, l,2.4-tria2ole, 1,2,3,4-tetrazole, pyridine, pyridazine, pyrimidine, pyrazine, 1,2,4-triazine, 1,3,5-triazine, indole, benzofuran, thianaphthalene, indazole, benzimidazole, benzotriazole, benzisoxa-zole, benzoxazole, benzothiazole, quinoline, isoquinoline, quinoxaline, quinazole, piperidine, piperazine, tetrahydrofuran, tetrahydropyran, pyrazoline, phthalimide, dioxane, dioxolane and benzodioxolane. Examples of the substituent on the optionally substituted heterocyclic ring group represented by A are those of the general formula: (R ),. (wherein R^ is halogen, nitro, cyano, C]-C4 alkyl, CyC^ haloalkyl, C1-C4 alkoxy, C1-C3 haloalkoxy, CyCj alkylthio, C1-C3 haloalkylthio, C1-C2 aikylsulfmyl, C1-C2 alkylsulfonyl, C^-Cj halo-alkylsulfmyl, C1-C2 haloalkylsulfonyl, C2-C4 alkenyl, C2-C4 haloalkenyl, C2-C4 alkynyl, C2-C4 haloalkynyl, amino, dimethylamino, acetamido, acetyl, haloacetyl, formyl, caiboxyl, methoxycarbonyl, CyC^ cycloalkyi, (CpCj alkyI)aminocarbonyI or [di(Ci-C2 alkyl)amino]carbonyl, or R is phenyl, benzyl, phenoxy, benzyloxy or pyridyl-oxy, each of which is optionally substituted with halogen, C1-C4 alkyl, CyC^ haloalkyl, C1-C4 alkoxy or C1-C3 haloalkoxy; and r is an integer of 0 to 7. Examples of the halogen atom represented by R or present in R are fluorine, chlorine, bromine and iodine. Examples of the C1-C4 aJky] group represented by R or present in R are methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl and tert-butyl. Examples of the C1-C3 haloalkyl group represented by R or present in R° are trifluoromethyi, difluoromethyl, bromodifluoromethyl, 2,2,2-trifIuoroethyi, 2-fluoro-ethyl, 2-chloroethyl, 2-bromoethyl, 1-fluoroethyl, 1-chloroethyi, 1-bromoethyl, 2,2,3,3, 3-pentafIuoropropyl, 3.3,3-trifluoropropyl. l-fluoropropyl, 2-chloropropyI and 3-bromo-propyl. Examples of the Ci-C^ alkoxy group represented by R^ or present in R^ are methoxy, ethoxy, ti-propoxy, isopropoxy, n-butoxy, sec-butoxy. isobutoxy and ten-butoxy. Examples of the C1-C3 haloalkoxy group represented by R^ or present in R^ aie trifluoroniethoxy, difluoromethoxy, bromofluoromethoxy, 2-fluoioetfaoxy, 2,2.2-tri-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-dil(Wo-l,I,2-trifluoroethoxy, 2-bromo-1,1,2-trifluoroethoxy, 1,1,2,2-tetrafluoroethoxy. 1,2^33,3-hexafluoropropoxy, 3-fluo-ropropoxy, 3-chloropropoxy, 3-bromopropoxy, 2,23.3>3-pentafluoropropoxy, 3,3,3-tri-fluoropropoxy and 1,1,2,2,2-pentafluoroethoxy. Examples of the C1-C3 alkylthio group represented by R^ are methylthio, ethylthlo, n-propylthio and isopropylthio. Examples of the Cj-Cs haloalkylthio group represented by R^ aie triOuoro-methyhhio, difluoromethylthio, bromodifluoromethyltiiio, 2.2,2-trifluoroethyIthio, 2-chloro-l, 1,2-trifluoroethylthio, 2-bromo-1,1 ^-trifluoroethylthio, 1,1,2,2-tetrafluoro-ethylthio, 2-chloroethylthio, 2-fiuoroethylthio, 2-bromoethylthio, 3-fliioropropyIthio, 3-chloropropylthio. (3-bromopropyl)thio, 2.23.3.3-peiitafiQoropropylthto and 3,3.3-tri-fluoropropylthio. Examples of the C1-C2 alkylsulfinyl group represented by R^ are methyl-sulfinyl and ethylsulfuiyl. Examples of the CpCj alkyisulfonyl group represented by R^ are methyl-sulfonyl and ethylsulfonyl. Examples of the C1-C2 haloalkylsulfinyl group represented by R^ are trifluoromethylsulfinyl, 2^,2-tnfluoroethylsulfinyI and perfluoroethylsulfmyl. Examples of the C1-C2 haloalkylsulfonyl group represented by R^ are trifluoromethylsulfonyl, 2,2.2-tiifluoroethylsulfonyl and perfluoroethylsulfonyl. Examples of the C2-C4 alkenyl group represented by R are vinyl, isopro-penyl, l-propenyl, 2-^thyl-]-propenyl, ]-methyl-l-propenyl, aHy!, 2-meihy]propenyI and 2-butenyl. Examples of the C2-C4 haloalkenyl group represented by R* are 2,2-di-chloroethenyl, 2,2-d)bron:ioethenyl, 3,3-dichloroallyl, 3,3-dibromoaIlyl, 2,3-dichloro-allyl, 2,3-cIitiromoalIyI, 2-chtoro-2-propenyI, 3-chloro-2-propenyI, 2-broino-2-propenyI and 3-chloro-2-butenyl. Examples of the C2-C4 alkynyl group represented by R are ethynyl, ]-pro-pynyl, 2-propynyl and l-methy!-2-propyny]. Examples of the C2-C4 haloalkynyl group represented by R are chloro-echynyl, bromoethynyl, iodoethynyl, 3-chIoro-2-propynyI, 3-bromo-2-propynyt, 3-iodo-2-propynyl, l-methyl-3-ch!oro-2-propynyl, l-methyl-3-bromo-2-propyny! and 1-methyl-3-iodo-2-propynyl. Examples of the haloacetyl group represented by R are trifluoromethylacety] and trichloroacetyl. Examples of the CyC^ cycloaJk^"] group represented by R° are cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl. Examples of the C5-C6 cycloalkenyl are l-cyclopentenyl, 2-cydopentenyl, 3-cyclopenienyl, 1-cyclohexenyl, 2-cyclohexenyl and 3-cyclohexenyl. Examples of the (C1-C2 aIkyi)aminocarbonyI group represented by R are methyl aminocaibonyi and ethylamino cart)onyl. Examples of the [di(Ci-C2 alkyl)amino]carbonyl group represented by R are dimethyiaminocarbonyl, N-methyl-N-ethylaminocarbonyi and diethylaminocarbonyl. The following are preferred examples of the present compound: dihalopropene compounds wherein A is a 5- or 6-membered heterocyclic ring group containing at least one oxygen, sulfur or nitrogen and optionally substituted by {R \ (wherein R is halogen, nitro, cyano, C]-C4 alkyl, C1-C3 haloalkyl, CJ-C4 alkoxy, C1-C3 haloalkoxy, C1-C3 alkylthio, CyC^ haloalkylthio, C1-C2 alkylsulfmyl, C1-C2 alkyhulfonyl Cj-C? haloaikylsulfmy], Ci-Cj haioalkylsulfonyl. C2-C4 aJkenyl, C2-C4 haloalkenyl, C2-C4 alkynyl, C2-C4 haloalkynyl, amino, dimethylamino, acetamido, acetyl, haloacetyl, formyl, carboxyl, methoxycarbonyl. CyC^ cycloalkyl, {C1-C2 alkyl)-aminocaibonyl or [d\{CyC2 alkyl)amino]carbonyl, or R is phenyl, benzyl, phenoxy, benzyloxy or pyridyloxy, each of which is optionally substituted with halogen, CJ-C4 alkyl, C1-C3 haloalkj"l, C1-C4 alkoxy or Cj-Cj haloalkoxy; and r is an integer of 0 to 7); dihalopropene compounds wherein A is 2-pyridyl, 3-pyridyl, 4-pyridyl, 2-thienyl, 3-thienyl, 2-furanyl, 3-furanyl, 5-(l,3-thiazolyl), N-f 1,2-dihydro-2-oxo)pyri-dino, 1,3-dioxolanyl, 1,4-benzodioxanyl, 2-pyrazy!, 2-ben20thiazolyl, 2-ben20xa2olyl, 2-benzimidazoIyI. 2-quinoxaIyny!, N-benzimidazoIyl, 2-quinoIyl, 3-quinoIyl or N-phthaJ-imido, each of which is optionally substituted with (R ),. (wherein R^ and r are each as defined above); dihalopropene compounds wherein R and R are independently halogen or Ci-C3alky!,andtisO; dihaJopropene compounds wherein R and R are independently chlorine, bromine, methyl, ethyl or isopropyl, and t is 0; dihalopropene compounds wherein R and R-* are both chlorine, and t is 0; dihalopropene compounds wherein R is chlorine, R^ is methyl, and t is 0; dihalopropene compounds wherein R^ is ethyl, R is methyl, and t is 0; dihalopropene compounds wherein R and R are both bromine, and t is 0; dihalopropene compounds wherein R^ and R-^ are both ethyl, and t is 0; dihalopropene compounds wherein R and R are independently halogen or C]-C3 alkyl, t is 1 or 2. and R"° is halogen or €,-€3 alkyl; dihalopropene compounds wherein R- and R^ are independently halogen or C]-C3 alkyl, t is 1 or 2, and R"° is halogen; dihalopropene compounds wherein Y and Z are both oxygen; dihalopropene compounds wherein R is Qj, p is I to 6, and A is 2-pyridyI, 3-pyridy], 4-pyridy!, 2-thieny], 3-thienyJ, 2-furanyl, 3-fi)ranyl, 5-(],3-thia2oiy]X N-(),2-dihydro-2-oxo)pyridino, !3-dioxolany] or N-phthaliinido, each of which is optionally substituted with {K\ (wherein R^ and r are each as defined above); dihalopropene compounds wherein R" is Qj, p is 1 to 6, R^, R^ and R^ are all hydrogen, and A is 1,3-dioxolanyl optionally substituted with (R^)j. (wherein R^ and r are each as defined above); dihalopropene compounds wherein R^ is Qj, p is 1 to 4, R^, R^ and R^ are all hydrogen, and A is 1,3-diDxolanyl optionally substituted with {R% (wherein R^ and r are each as defined above); dihalopropene compounds wherein R is Q^. p is 0, and A is 2-pyridy!, 4-pyridyl, 2-thienyl, 3-thienyl, 2-furanyl, 3-furanyl, 5-(l,3-thia2olyl), 1,3-dioxolanyl or 1,4-benzodioxolanyl, each of which is optionally substituted with (R )j (wherein R^ and r are each as defined above); dihalopropene compounds wherein R is Q2; dihalopropene compounds wherein R" is Qj, and A is 2-pyridyI, 3-pyridyl, 4-pyridyi, 2-thienyl, 3-thienyI. 2-furany), 3-furanyl, 5-(l,3-ihiazolyl), 2-pyradyI, 2-benzothiazoly], 2-ben2oxazo]yl, 2-benzimida2o]y!, 2-quinoxalynyl, N-benzimidazo]yl, 2-quinolynyl or 3-quinQlyl, each of which is optionally substituted with {R \ {wherein R° and r are each as defined above); dihalopropene compounds wherein R is Q2, p is 1 to 4, and A is 2-pyridyl optionally substituted with (R )r (wherein R^ and r are each as defined above); dihalopropene compounds wherein R is Q2, p is 1 to 4, R^, R° and R are all hydrogen, and A is 2-pyridyl optionally substituted with {R \ (wherein R and r are each as defined above); dihalopropene compounds wherein R* is Q2, p is 1 to 4, R , R and R are all hydrogen, A is 2-pyridyl optionally substituted with (R )j (wherein R is halogen or C5-C3 haloalkyt and r is as defined above); The molar ratio of the starting materials and bases to be used in the reaction can be freely determined, but it is favorable to effect the reaction at an equimolar ratio or a ratio closer thereto. After completion of the reaction, the reaction mixture is subjeaed to ordinary post-treatments such as organic solvent extraction and concentration, and the desired compound of the present invention can be isolated. Further, purification can be carried out, if necessary, by an ordinary technique such as chromatography, distillation or recrystallization. (Production Process B for the present compounds wherein Y is oxygen) In this process, a compound of the general formuJa [III] is reacted with an alcohol compound of the general formula: HO-CH2CH=CX2 [V] wherein X is as defined above. The reaction is preferably effected in an inert solvent, if necessary, in the presence of a suitable dehydrating agent. Examples of the dehydrating agent which can be used are dicyclohexyl-carbodiimide, and dialkyl (e.g., CJ-C4) azodicarboxylates (e.g., diethylazodicaiboxylate, diisopropyla2odicarboxyiate)-trialkyl (e.g., CpC2o) phosphineor triaiylphosphine (e.g., triphenylphosphine, trioctylphosphine, tributylphosphine). Examples of the solvent which can be used are hydrocarbons such as benzene, xylene and toluene; ethers such as diethyl ether, diisopropyl ether, tetrahydro-furan and dioxane; and balogenated hydrocarbons such as carbon tetrachloride, dichloro-methane, chlorobenzene and dichJorobenzene. The reaction temperature is usually set within the range of -20"C to 200°C or the boiling point of a solvent used in the reaction. The molar ratio of the starting materials and dehydrating agents to be used in the reaction can be freely determined, but it is favorable to effect the reaction at an equjmolar ratio or a ratio closer thereto. After completion of the reaction, the reaction mixture is subjected to ordinary post-treatments such as organic solvent extraction and concentration, and the desired compound of the present invention can be isolated. Further, purification can be carried out by an ordinary technique such as chromatography, distillation or recrystallizaiion. (Production Process C for the present compounds wherein Y is oxygen) In this process, an aldehyde compound of the general formula: The molar ratio of the starting materials and reagents to be used in the reaction can be freely determined, but the ratio is preferably such that caibon tetrabromide or tetra¬chloride, trialkylphosphine or triarylphosphine, and zinc are 2 moles, 2 or 4 moles (2 moles when zinc is used), and 2 moles, respectively, per mole of the aldehyde compound of the general formula [VI], or it is favorable to effect the reaction at a ratio closer thereto. After completion of the reaction, the reaction mixture is subjected to ordinary post-treatments such as organic solvent extraction and concentration, and the desired compound of the present invention can be isolated. Further, purification can be carried out by an ordinary technique such as chromatography, distillation or recrystallization. (E^roduction Process D for the present compounds wherein Y and Z are both oxygen) suitable base. Examples of the solvent which can be used are ketones such as acetone, methyl ethyl ketone and cyclohexanone; ethers such as 1,2-dimethoxyethane, tetrahydro-furan, dioxane and dialkyl (e.g., C)-C4) ethers (e.g., diethyl ether, diisopropyl ether); N,N-dimethylformamide, dimethylsulfoxide, hexamethylphosphoric triamide. sulforane, acetonitrile, nitromethane; halogenated hydrocarbons such as dichloromethane, chloro¬form, 1,2-dichloroethane and chlorobenzene; hydrocarbons such as toluene, benzene and xylene; and water. If necessary, a mixture of these solvents can be used. Examples of the base which can be used are hydroxides of alkali meiais or alkaline earth metals, such as lithium hydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide; carbonates of alkali metals or alkaline earth metals, such as lithium carbonate, potassium carbonate, sodium carbonate and calcium carbonate; hydrides of alkali metals or alkaline earth metals, such as lithium hydride, sodium hydride, potassium hydride and calcium hydride; alkali metal alkoxides (e.g., C^-Cn) such as sodium methoxide, sodium ethoxide and potassium tert-butoxide; organic bases such as triethylamine and pyridine. If necessary, catalysts such as ammonium salts (e.g., triethylbenzylammonium chloride) may be added to the reaction system at a ratio of 0.01 to 1 mole per mole of the compound of the general formula [VII]. The reaction temperature is usually set within the range of -20°C to 1 SO"C or the boiling point of a solvent used in the reaction, preferably -5°C to 100°C or the boiling point of a solvent used in the reaction. The molar ratio of the starting materials and dehydrating agents to be used in the reaction can be freely determined, but it is favorable to effect the reaction at an equimolar ratio or a ratio closer thereto. After completion of the reaction, the reaction mixture is subjected to ordinary post-treatments such as organic solvent extraction and concentration, and the desired compound of the present invention can be isolated. Further, purification can be carried out by an ordinary technique such as chromatography, distillation or recrystallization. (Production Process E for the present compounds wherein Y and Z are both oxygen) In this process, a compound of the general formula [VII] is reacted with an alcohol compound of the general formula: R"-OH [IX] wherein R is as defined above. The reaction is preferably effected in an inert solvent, if necessary, in the presence of a suitable dehydrating agent. Examples of the dehydrating agent which can be used are dicyclohexyl-carbodiiraide, and dialkyl (e.g., CyC^) azodicarboxyiates (e.g., diethylazodicarboxylate, diisopropy]a2odicart>ox}"la£e>tria]lcyl (e.g., CI-CJQ) phosphine or triarylpbosphine (e.g., triphenylphosphine, trioctylphosphine, tributylphosphine). Examples of the solvent which can be used are hydrocarbons such as benzene, xylene and toluene; ethers such as diethyl ether, diisopropyl ether, tetrahydro-furan and dioxane; and halogenated hydrocarbons such as carbon tetrachloride, dichloro-methane, chlorobenzene and dichlorobenzene. The reaction temperature is usually set within the range of -20""C to 200°C or the boiling point of a solvent used in the reaction. The molar ratio of the materials and dehydrating agents to be used in the reaction can be freely determined, but it is favorable to effect the reaction at an equimoiar ratio or a ratio closer thereto. After completion of the reaction, the reaction mixture is subjected to ordinary post-treatments such as organic solvent extraction and concentration, and the desired compound of the present invention can be isolated. Further, purification can be carried out by an ordinary technique such as chromatography, distillation or recrystallizaiion. (Produaion Process F for the present compounds wherein Y and Z are both oxygen, R is Q2 or Q3, and B is B" (wherein B is oxygen, sulfur or NR [wherein R is as defined above]}) In this process, a compound of the general formula: The reaction is preferably effected in an inert solvent in the presence of a suitable base. Examples of the solvent which can be used are ketones such as acetone, methyl ethyl ketone and cyclohexanone; ethers such as 1,2-dimethoxyethane, tetrahydro-furan, dioxane and dialkyl (e.g., Ci-C^) ethers (e.g., diethyl ether, diisopropyl ether); N.N-dimethylformainide, dimethylsulfoxide, hexamethylphosphoric triamide, sulforane, acetonitrile, nitromethane; halogenated hydrocarbons such as dichloromethane, chloro¬form, 1,2-dichloroethane and chlorobenzene; hydrocarbons such as toluene, benzene and xylene; and water. If necessary, a mixture of these solvents can be used. Examples of the base which can be used are hydroxides of alkali metals or alkaline earth metals, such as lithium hydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide; carbonates of alkali metals or alkaline earth metals, such as lithium carbonate, potassium carbonate, sodium carbonate and calcium carbonate; hydrides of alkali metals or alkaline earth metals, such as lithium hydride, sodium hydride, potassium hydride and calcium hydride; alkali metal alkoxides (e.g., C1-C4) such as sodium methoxide, sodium ethoxide and potassium tert-butoxide; organic bases such as trielhylaniine and pyridine. If necessary, catalysts such as ammonium salts {e.g., triethylbenzylammonium chloride) may be added to the reaction system at a ratio of O.OJ to ] mole per moJe of the compound of the genera) fonnuJa [X], The reaction temperature is usually set within the range of -lO"C to 150°C or the boiling point of a solvent used in the reaction, preferably -S"C to 100°C or the boiling point of a solvent used in the reaction. The molar ratio of the starting materials and dehydrating agents to be used in the reaction can be freely determined, but it is favorable to effect the reaction at an equimolar ratio or a ratio closer thereto. After completion of the reaction, the reaction mixture is subjected to ordinary post-treatments such as organic solvent extraction and concentraijon, and the desired compound of the present invention can be isolated. Further, purification can be carried out by an ordinary technique such as chromatography, distillation or rccrystaHization. {Production Process G for the present compounds wherein Y, Z and B are all oxygen and R" is Q2, Q3, Qe or Q7) In this process, an alcohol compound of the general formula: The reaction is preferably effected in an inert solvent, if necessary, in the presence of a suitable dehydrating agent. Examples of the dehydrating agent which can be used are dicyclohexyl-carbodiimide, and dialkyl (e.g., C1-C4) azodicarboxylates (e.g., diethylazodicarboxylate, diisopropylazodicarboxylate)-trialkyl (e.g., C5-C20) phosphineor triarylphosphine (e.g., triphenyJphosphine, trioctyJphosphine, tribulylphosphine). Examples of the solvent which can be used are hydrocarbons such as benzene, xylene and toluene; ethers such as diethyl ether, diisopropyl ether, tetrahydro-furan and dioxane; and haiogenated hydrocarbons such as carbon tetrachloride, dichloro-methane, chlcrobenzene and dichlorobenzene. The reaaion temperature is usually set within the range of -SO"C to 2CX)°C or the boiling point of a solvent used in the reaction. The molar ratio of the materials and dehydrating agents to be used in the reaction can be freely determined, but it is favorable to effect the reaction at an equimolar ratio or a ratio closer thereto. After completion of the reaction, the reaction mixture is subjected to ordinary post-treatments such as organic solvent extraction and concentration, and the desired compound of the present invention can be isolated. Further, purification can be carried out by an ordinary technique such as chromatography, distillation or recrystallization. (Production Process H for the present compounds wherein Y and Zare both Examples of the solvent which can be used are ketones such as acetone, methyl ethyl ketone and cyclohexanone; ethers such as 1,2-dimethoxyethane, tetrahydro-furan, dioxane and dialkyi (e.g., C1-C4) ethers (e.g., diethyl ether, diisopropyl ether); N,N-dimethylformamide, dimethylsulfoxide, hexamethylphosphoric triamide, sulforane, acetonitrile, nitromethane; halogenated hydrocarbons such as dichloromethane, chloro¬form, i ,2-dichloroethane and chlorobenzene; hydrocarbons such as toluene, benzene and xylene; and water. If necessary, a mixture of these solvents can be used. Examples of the base which can be used are hydroxides of alkali metals or alkaline earth metals, such as lithium hydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide; carbonates of alkali metals or alkaline earth metals, such as lithium carbonate, potassium carbonate, sodium carbonate and calcium carbonate; hydrides of alkali metals or alkaline earth metals, such as lithium hydride, sodium hydride, potassium hydride and calcium hydride; alkali metal alkoxides (e.g., C^-C^ such as sodium methoxide, sodium ethoxide and potassium tert-butoxide; organic bases such as triethylamine and pyridine. If necessary, catalysts such as ammonium salts (e.g., triethylbenzylammonium chloride) may be added to the reaction system at a ratio of 0.01 to 1 mole per mole of the compound of the general fonnula [XIV]. The reaction temperature is usually set within the range of -20°C to !50°C or the boiling point of a solvent used in the reaction, preferably -5"Cto 100°C or the boiling point of a solvent used in the reaction. The molar ratio of the starting materials and dehydrating agents to be used in the reaction can be freely determined, but it is favorable to effect the reaction at an equimolar ratio or a ratio closer thereto. After completion of the reaction, the reaction mixture is subjected to ordinary post-treatments such as organic solvent extraction and concentration, and the desired compound of the present invention can be isolated. Further, purification can be earned out by an ordinary technique such as chromatography, distillation or recrystallization. When the present compound has an asymmetry cari)on atom, it is to be construed to include its optically acrive isomers (C+)-form and (-)-fonn) having biological activity and their mixtures at any ratio. When the present compound exhibits geometrical isomerism, it is to be construed to include its geometrical isomers (cis-form and trans¬form) and their mixtures at any ratio. The following are typical examples of the present compound (wherein R is as shown in Tables 1 to 46), which are not to be construed to limit the scope of the present invention. WE CLAIM : 1. 2-(3-methanesuIfonyloxyproplyloxy)-5-trifluoromethylpyridine, of the formulae

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