| Title of Invention | PYRIMIDINE COMPOUNDS AND THEIR USE AS PESTICIDES |
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| Abstract | ABSTRACT 1993/CHENP/2004 "Pyrimidine compounds and their use as pesticides" The present invention relates to a pyrimidine compound of formula (1): wherein R<sup>1</sup> is C3-C7 alkynyl; R<sup>2</sup> is hydrogen, halogen, or C1-C3 alkyl; and R<sup>3</sup> is C1-C8 alkyl that may be substituted with halogen or C1-C3, alkoxy or C3-C8 cycloalkyl (that may be substituted with halogen or C1-C3 alkyl) C1-C3 alkyl; a pesticidal composition comprising the pyrimidine compound as an active ingredient; and a method for controlling pests comprising applying the pyri¬midine compound to pests or habitats of pests. |
| Full Text | DESCRIPTION PYRIMIDINE COMPOUNDS AND THEIR USE Technical Field The present invention relates to pyrimidine compounds and their use. Background Art Various compounds have been developed so far to control pests and they have been put into practice. Some of these compounds cannot always exhibit satisfactory activity. It is an objective of the present invention to provide novel compounds having pesticidal activity. Disclosure of Invention The present inventors have intensively studied to find compounds having excellent pesticidal activity, and as a result, they have found that the compounds of formula (1) as depicted below have excellent pesticidal activity, thereby completing the present invention. Thus the present invention provides a pyrimidine compound of for¬mula (1): (hereinafter referred to as the present compound{s)) wherein R1 is C3-C, alkynyl; R- is hydrogen, halogen, or C1-C3 alkyl; and R2 is C1-C8alkyl that may be substituted with halogen or C1-C3 alkoxy, or C3-C3 cycloalkyl- (that may be substituted with halogen or C1-C3 alkyl) C1-C8 alkyl; a pesticidal composition comprising the present compound as an active ingredient; and a method for controlling pests comprising applying the present compound to pests or habitats of pests. Mode for Carrying Out the Invention In the definition of substituents as used herein, each group has the following meaning: The C3-C7 alkynyl represented by R1 may include, for example, C3-C7 alkynyl in which the bond between the carbon atoms at positions 2 and 3 is a triple bond. Specific examples are 2-propynyl, 2-butynyl, l-methyl-2-butynyl. 2-pentynyl, l-methyi-2-pentynyl, 4,4-dimethyl-2-pentynyl, 1-methyl-2-propynyl, and l,l-dimethyl-2-propynyi. The C1-C3 alkyl represented by R2 may include, for example, methy! and ethyl. The halogen may include, for example, fluorine and chlorine. In the C1-C3 alkyl that may be substituted with halogen or C1-C3 alkoxy represented by R2 the halogen may include, for example, fluorine, chlorine, and bromine, and the C1-C3 alkoxy may include, for example, methoxy, ethoxy, propoxy, and isopropoxy The C1-C3 alkyl that may be substituted with halogen or C1-C3 alkoxy, represented by R2 may include, for example, C3-C3 branched alkyl that may be substituted with halogen or C1-C3 alkoxy. Specific examples are as follows: isopropyl, isobutyl, sec-butyl, 1,2-dimethylpropyl, isopentyl, neopen-tyl, 1-methylbutyl, 2-methylbutyl, 1-ethylpropyl, 1,2,2-trimethylpropyi, 1,2-dimethylbutyl, l-ethyt-2-methyIpropyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, isohexyl, 2-ethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, l-ethyl-2,2-dimethylpropyl, 1,3,3-trimeth- ylbutyl, 2,3,3-trimethylbutyl, l-isopropyi-2-methylpropyl, l-ethyl-3,3-di-methylbutyl, 1,2,3,3-tetramethylbutyl, l-methyl-2,2-dimethoxyethyl, 1-methyl-2,2,2-trichloroethyl. l-methyl-2,2,2-trifluoroethyl, l-methyl-2,2-di-chloroethyl, l-methyl-2,2-difluoroethyl, 2-methyl-2-methyloxypropyl, 1-methyl-2-chioroethyl, 1-methyl-2-fluoroethy 1, l-methyl-2-i8opropyloxyethyl, l-methyl-2-chloropropyl, l-methyl-2-fiuoropropyl, l-methyl-2,2-dichloropro-pyl, l-methyl-2,2-difluoropropyl, 2-chloro-2-methylpropyl, 2-fluoro-2-methyl-propyl, 2-bromo-2-methylpropyl. 3-fluoro-2-methylpropyl, 3-chloro-2-methyl-propyl. 2,3-dichloro-2-methylpropyl, l,2-dimethyl-2-methyloxypropyi, 3-bro-mo-2,2-dimethylpropyl, 3-chloro-2.2-dimethylpropyl, 2,2-dichloro-2-£luoro-l-methylethyi, 3-fluoro-2,2-dimethylpropyl, 2,3-dichioro-l,2-dimethylpropyl, l,2-dimethyl-2-fluoropropyl, l,2-dimethyl-2-chloropropyl, l,2-dimethyl-2-bromopropyl, 3-fluoro-l,2-dimethylpropyl, 3-chloro-l,2-dimethylpropyl, 3,3-difluoro-l,2-dimethylpropyl, 3,3,3-trifluoro-2-trifluoromethyl-2-methylpropyl, 2,2-dichloro-l-isopropylethyl, 2,2,2-trifluoro-l-isopropylethyl, 2,2-difluoro-l-isopropylethyl, 2,2,2-trichloro-l-(t-butyl)ethyl, 2,2-dichloro-l-(t-butyI)ethyl, 3-£luoro-l,3-dimethylbutyl, 3-chloro-l,3-dimethylbutyl, 3-bromo-l,3-dimeth-ylbutyl, 3-fluoro-2,3-dimethylbutyl, 3-chloro-2,3-dimethyibutyl, 3-bromo-2,3-dimethylbutyl, 3-fluoro-l,2,2-trimethylpropyl, 3-chloro-l,2.2-trimethylpropyl, 3-bromo-l,2,2-trimethylpropyl, 2-fluoro-l-ethyl-2-methylpropyl, 2-bromo-l-ethyl-2-methylpropyl. 2-chloro-l-ethyl-2-methylpropyl, l-trichloromethyl-2-methylpropyl, 2,2,2-trichloro-l-chIoromethylethyi, 2,2-dichloro-l.dichloro-methylethyl, 1-trichloromethylpropyl, 2,2-dichloro-l-ethylpropyl, 2,2-dichlo-ro-2-fluoroethyl, 2,2-dichloro-l-trifluoromethylethyl, 3,3,3-trichloroethyl, and 3,3,3 -trifluor op ropyl. In the C3-C3 cycloalkyl- (that may be substituted with halogen or C1-Cg alkyl) C3-C3 alkyl. represented by R2, the halogen may include, for example, fluorine, chlorine, and bromine, and the C-C8alkyl may include, for example. methyl and ethyl. The C3-C3 cycloalkyl- (that may be substituted with halogen or C1-C3 alkyl) C1-C3 alkyl represented by R2 may include, for example, cyclo- propylmethyl, l-(cyclopropyl)ethyl. 2-(cyciopropyl)ethyl, l-(l-methylcyclo- propyl)ethyl, 2-(l-methylcyclopropyl)ethyl, l-(2-ethyicyclopropyl)ethyl, 2-(2- ethylcyclopropyl)ethyl. l-(2-flubrocyclopropyl)ethyl,* 2-(2-fluorocyclopropyl)- ethyl, l-(2-chlorocyclopropyl)ethyl, 2-(2-chlorocyclopropyl)ethyl, l-(l,2-di- methylcyclopropyl)ethyl, 2-(l,2-dimethylcyclopropyl)ethyl, l-(2.2-dimethyl- cyclopropyl)ethyl, 2-(2.2-dimethylcyclopropyl)ethyl, l-(2,2-dichloro-l-methyl- cyclopropyl)ethyl, 2-(2,2-dichloro-l-methylcyclopropyl)ethyi, l-(2,2-dichloro- 3,3-dimethylcyclopropyl)ethyl, 2-(2,2-dichloro-3,3-dimethylcyclopropyl)ethyL l-(cyclobutyl)ethyl, 2-(cyclobutyl)ethyl, l-(l-methylcyclobutyl)ethyl. 2-(l- methyicyclobutyl)ethyl, l-(2-methylcyclobutyl)ethyl, 2-(2-methylcyclobutyl)- ethyl, l-(l-chlorocyclobutyl)ethyI, 2-(l-chlorocyclobutyl) ethyl, l-(2-cliioro- cyclobutyl)ethyl, 2-(2-chlorocyclobutyl)ethyl, l-(2,2-difluorocyciobutyi)ethyl, 2-(2,2-di£luorocyciobutyl)ethyl, l-(cyIoropentyl)ethyl, 2-(cyloropentyI)ethyI, I- (l-methylcyloropentyl)ethyl, 2-(l-methylcyloropentyl)ethyl, l-(2-methyl- cyloropentyl)ethyl, 2-(2-methylcyloropentyl)ethyl, l-(2-ethyicyloropentyl)- ethyl, 2-(2-ethylcyloropentyl)ethyl, l-(2-£luorocyloropentyl)ethyi, 2-(2-£luoro- cyloropentyl)ethyl, l-(2-chlorocyloropentyl)ethyl, 2-(2-chlorocyclopentyi)ethyl, l-(2-bromocyclopentyl)ethyl, 2-(2-bromocyclopentyl)ethyl, l-(l,2-di- methylcyclopentyl)ethyl, 2-(l,2-dimethylcyclopentyl)ethyl, l-(3-methylcyclo-pentyl)ethyl, 2-(3-methylcyclopentyl)ethyl, l-(3-fluorocyclopentyl)ethyl, 2-(3-fluorocyclopentyl)ethyl, l-(3-chlorocyclopentyl)ethyl, 2-(3-chlorocyclopentyl)-ethyl, l-(cylcohexyl)ethyl, and 2-(cylcohexyl)ethyL The embodiments of the present compounds may include, for example, the following compounds: the compounds of formula (1) wherein R2 is C3-C7 altynyl in which the bond between the carbon atoms at positions 2 and 3 is a triple bond; the compounds of formula (1) wherein R1 is 2-propynyl. 2-butynyl, 1-methyl-2-butynyl, or 2-pGntynyl; the compounds of formula (1) wherein R2 is hydrogen: the compounds of formula (1) wherein R1' is Co-C3 alkyl that may be substituted with halogen; the compounds of formula (1) wherein R2 is C3-C8branched alkyl that may be substituted with halogen or C1-C3 alkoxy;the compounds of formula (1) wherein R2 is C3-C3 cycloalkyl- (that may be substituted with halogen or C,-C3 alkyl) C.-C3 alkyl; the compounds of formula (1) wherein R1 is C3-C7 alkynyl in which the bond between the carbon atoms at positions 2 and 3 is a triple bond; R2 is hydrogen; and R1' is 0,-08 alkyl that may be substituted with halogen; the compounds of formula (1) wherein R1 is C3-C7 alkynyl in which the bond between the carbon atoms at positions 2 and 3 is a triple bond; R2 is hydrogen; and R2 is Ca-C3 branched alkyl that may be substituted with halogen; the compounds of formula (1) wherein R1 is C3-C7 alkynyl in which the bond between carbon atoms at positions 2 and 3 is a triple bond; R2 is hydrogen; R2 is C3-C3 cycloalkyl- {that may be substituted with halogen or C.-C3 alkyl) C1-C3 alkyl; the compounds of formula (1) wherein R1 is C3-C7 alkynyl in which the bond between carbon atoms at positions 2 and 3 is a triple bond; R" is hydrogen; R2 is methyl substituted with C3-Ce cycloalkyl that may be substituted with halogen or C1-C3 alkyl; the compounds of formula (1) wherein R1 is C3-C- alkynyl in which the bond between carbon atoms at positions 2 and 3 is a triple bond; R2 is hydrogen; R2 is ethyl substituted on the carbon atom at position 1 with C3-Cs cycloalkyl that may be substituted with halogen or C1-C3 alkyl; the compounds of formula {1) wherein R1 is C3-C7 alkynyl in which the bond between carbon atoms at positions 2 and 3 is a triple bond; R2 is hydrogen; R2 is ethyl substituted on the carbon atom at position 2 with C3-C3 cycloaikyi that may be substituted with halogen or C1-C3 alkyl; the compounds of formula (1) wherein R1 is C3-C alkynyl in which the-bond between carbon atoms at positions 2 and 3 is a triple bond; R- is hydrogen; R2 is propyl substituted on the carbon atom at position 1 with C3-C cycloalkyl that may be substituted with halogen or C1-C3 alkyl; and the compounds of formula (1) wherein R1 is C3-C. alkynyl in which the bond between carbon atoms at positions 2 and 3 is a triple bond; R" is hydrogen; R2 is propyl substituted on the carbon atom at position 2 with C3-Ce cycloalkyl that may be substituted with halogen or C1-C3 alkyl. The following will describe a production process for the present com¬pound. (Production Process) The present compound of formula (1) can be produced from a 4,6-di-chloropyrimidine compound of formula (2) via the following steps: The compound of formula (3) can be produced by reacting a 4,6-di-chloropyrimidine compound of formula (2) with an alcohol compound of for- mula (4): R1OH (4) wherein R1' is as defined'above. The reaction is usually carried out in a solvent in the presence of a base. The solvent that can be used in the reaction may include, for example, ethers such as tetrahydrofuran. diethyl ether, and methyl t-butyl ether; acid amides such as N,N-dimethylformamide; sulfoxides such as dime thy Isulfox-ide; and mixtures thereof. The base that can be used in the reaction may include, for example, inorganic bases such as sodium hydride; alkah metal carbonates such as potassium carbonate and sodium carbonate; and organic lithium compounds such as n-buty! lithium. The amount of the base that can be used in the reaction is usually in the ratio of 1 to 2.5 moles per mole of the 4,6-dichloro-pyrimidine compound of formula (2). The amount of the alcohol compound of the formula (4) that can be used in the reaction is usually in the ratio of 1 to 1.5 moles per mole of the 4,6-dichloropyrimidine compound of formula (2). The reaction temperature is usually in the range of 0'C to 80°C, and the reaction time is usually in the range of 0.1 to 12 hours. After completion of the reaction, the reaction mixture is subjected to ordinary post-treatment procedures such as extraction with an organic sol¬vent, drying the organic layer, and subsequent concentration, to isolate the compound of formula (3). The compound of formula (3) thus isolated can be purified by a technique such as chromatography. Step (1-2) The present compound of formula (1) can be produced by reacting the compound of formula (3) with an alcohol compound of formula (5): R1OH (5) wherein R1 is as defined above. The reaction is usually in a solvent in the presence of a base. The solvent that can be used in the reaction may include, for example, ethers such as tetrahydrofuran, diethyl ether, and methyl t-butyl ether; acid amides such as N,N-dimethylformamide; sulfoxides such as dimethylsulfox-ide; and mixtures thereof. The base that can be used in the reaction may include, for example, inorganic bases such as sodium hydride. The amount of the base that can be used in the reaction is usually in the ratio of 1 to 2.5 moles per mole of the compound of formula {3). The amount of the alcohol compound of the formula (5) that can be used in the reaction is usually in the ratio of 1 to 1.5 moles per mole of the compound of formula (3). The reaction temperature is usually in the range of 0°C to 80°C, and the reaction time is usually in the range of 0.1 to 12 hours. After completion of the reaction, the reaction mixture is subjected to ordinary post-treatment procedures such as extraction with an organic sol¬vent, drying the organic layer, and subsequent concentration, to isolate the present compound of formula (1). The present compound of formula (1) thus isolated can be purified by a technique such as chromatography. Specific examples of the present compound are Usted below; The compounds of formula (1) wherein R1 is 2-propynyl; R- is hydrogen: and R2 is any of the following suhstituents: isobutyl. 1.2-dimethylpropyl. isopentyl. neopentyl. 1.2,2-trimethyl" propyl, l-ethyl-2-methylpropyl. 3.3-dimethylbutyl, 1.3-dimethylbutyl. 1-ethyi-2.2-dimethylpropyl. l-methyl-2.2.2-trichloroethyl, l-methyl-2,2-dichlo-roethyl, l-methyl-2,2-difluoroethyl. l-methyl-2-chloropropyl, l-methyl-2.2-dichloropropyl, l-methyl-2,2-difluoropropyl. 2-chloro-2-methylpropyl. 2-fluo-ro-2-methylpropyl, 2-bromo-2-methylpropyl, 3-fluoro-2-methylpropyl, 3-chlo-ro-2-methylpropyl, 2.3-dichloro-2-methylpropyl, 3-bromo-2.2-dimethylpropyl, 3-chloro-2.2-dimethylpropyl, 3-fluoro-2.2-dimethylpropyl. 2.3-dichloro-l,2-dimethylpropyl, l,2-dimethyl-2-fluoroethyL 1.2-dimethyl-2-chloroethyi, 1,2-dimethyl-2-bromoethyl, 3-fluoro-l,2-dimethylpropyl, 3-chloro-l,2-dimethyi-propyl, 3.3-difl.uoro-1.2-dimethyipropyi, l-dichloromethyl-2-methylpropyl, 1-dichioromethyl-2-methylpropyl. 2.2-dimethyl-l-trichloromethyl, 2,2-dimeth-yl-l-dichloromethylpropyl, 3-fluoro-1.2.2-trimethylpropyl, 3-chloro-l,2.2-tri-methylpropyl, 2-fluoro-l-ethyl-2-inethylpropyl. 2-bromo-l-ethyl-2-methyi-propyi, 2-chloro-l-ethyl-2-methylpropyl, 2-methyl-2-methyloxypropyl, 1,2-dimethyl-2-methyloxypropyl, 2,2-dichloro-2-fluoro-l-methyiethyl, or 2-meth-yl-l-trichloromethyipropyl. The compounds of formula (1) wherein R1 is 2-butynyl; R2 is hydro¬gen; and R2 is any of the following suhstituents: isopropyl, isobutyl, sec-butyl, 1,2-dimethylpropyl, isopentyl, neopen¬tyl, isohexyl, 1,2.2-trimethylpropyl, 1,2-dimethylbutyi, l-ethyl-2-iiiethylpro-pyl, 2,3-dimethylbutyl, 2,2-dimethylbutyl, 3,3-dimethylbutyl, l,3-.dimethyl- butyl, l-ethyl-2,2-dimethylpropyl, 2.3,3-trimethylbutyl, 1,3,3-trimethylbutyl. l-ethyl-3,3-diinethylbutyl, 1,2.3,3-tetramethylbutyl, 1-methyl-2,2-dime-thoxyethyl, l-methyl-2,2,2-trichloroethyl, l-methyl-2,2.2-trifluoromethyl, 1-methyl-2,2-dichloroethyl. l-methyi-2,2-difluoroethyl, l-methyl-2-chloroethyi. l-methyl-2-fluoroethyl, 1-methyl-2-isopropoxyethy 1, l-metbyl-2-chloropropyL l-methyl-2-fluoropropyl, l-methyl-2,2-dichloropropyl, l-methyi-2.2-diiluoro-propyl. 2-chloro-2-methylpropyl, 2-fluoro-2-methylpropyl, 2-bromo-2-methyl-propyl, 3-fluoro-2-methylpropyl, 3-chloro-2-methylpropyL 2,3-dichioro-2-methylpropyl, 3-bromo-2,2-dimethylpropyl, 3-chloro-2,2-dimethylpropyI, 3-fluoro-2,2-dimethylpropyl, 2.3-dichloro-l,2-dimethylpropyi, 1.2-dimethyi-2-fluoroethyl, l,2-dimethyi-2-chloroethyl, l,2-dimethyl-2-bromoethyl, 3-fluoro-1,2-dimethylpropyl, 3-chloro-l,2-dimethylpropyl 3,3-difluoro-1.2-dimethyl-propyl, 3.3,3-trifluoro-2-trifluoromethyl-2-methylpropyl, l-dichloromethyi-2-methylpropyl, l-trifluoromethyl-2-methylpropyl, l-dichioromethyl-2-methyl-propyl. 2.2-dimethyl-l-trichloromethylpropyl, 2.2-dimethyl-l-dichlorometh-ylpropyl, 3-fluoro-l,3-dimeChyibuty!, 3-chloro-l,3-dimethyIbutyI, 3-bromo-1,3-dimethylbutyl, 3-fluoro-2.3-dimethylbutyl, 3-chloro-2,3-dimethylbutyl, 3-bromo-2,3-dimethylbutyl, 3-fluoro-l,2,2-trimethylpropyl, 3-chloro-l,2,2-tri-methyipropyl, 3-bromo-l,2,2-trimethylpropyl, 2-fluoro-l-ethyl-2-m.ethylpro-pyl, 2-bromo-l-ethyl-2-methylpropyl, 2-chloro-l-ethyl-2-methylpropyI, 2-methyl-2-methoxypropyl, l,2-dimethyl-2-methoxypropyl, 2,2-dichloro-2-fIuo-ro-1-methylethyl, or 2-methyl-l-trichloromethylpropyl. The compounds of formula (1) wherein R1 is 2-butynyi; R2 is methyl; and R2 is any of the following substituents: isobutyl, 1,2-dimethylpropyl, isopentyl, neopentyl, 1,2,2-trimethyl-propyl, l-ethyl-2-methylpropyl, 3,3-dimethylbutyi, 1,3-dimethylbutyl, 1-ethyl-2,2-dimethylpropyl, l-methyi-2,2,2-trichloroethyl. 1-methy 1-2,2-dichlo-roethyl, l-methyl-2,2-difluoroethyl, l-methyl-2-chloropropyl, l-iuethyi-2.2- dichloropropyl, l-methyl-2,2-difluoropropyl, 2-cliloro-2-methylpropyi, 2-fIuo-ro-2-methylpropyl, 2-broiuo-2-methylpropyi, 3-fluoro-2-methylpropyl, 3-chlo-ro-2-metliylpropyl, 2,3-dichioro-2-methylpropyl, 3-bromo-2,2-dimethylpropyl. 3-chloro-2,2-dimethylpropyl, 3-fluoro-2,2-dimethylpropyl, 2,3-dichloro-l,2-di-methylpropyl, 1.2-dimethyl-2-fluoroethyl, 1.2-dimethyl-2-Ghloroethyl,'1,2-di-inethy]-2-bromoethy]. 3-i3uoro-l,2-dimethylpropyl. 3-ciiJoro-i;2-diinethylpro-pyl, 3,3-difluoro-1.2-dim6thylpropyl, l-dichloromethyl-2-methylpropyl, 1-di-chioromethyi-2-methylpropyl. 2,2-dimethyl-l-trichloroniethyl, 2,2-dimethy 1-1-dichloromethylpropyl, 3-fluoro-1.2.2-trimethyipropyl, 3-chloro-l,2.2-tri-methylpropyl, 2-fluoro-l-ethyl-2-methylpropyl. 2-bromo-l-ethyl-2-methyl-propyl, 2-chloro-l-ethyl-2-methylpropyi, 2-methyl-2-methyloxypropyL 1,2-di-methyl-2-methyloxypropyl, 2,2-dichloro-2-fluoro-l-methylethyl, or 2-methyi-1 - trichlor 0 me thy Ip rop y 1. The compounds of formula {1} wherein R1 is 2-butynyl; R2 is chlorine; and R2 is any of the following substituents: isobutyl, 1.2-dimethylpropyl, isopentyl, neopentyl, 1,2,2-trimethyi-propyl, l-ethyl-2-methylpropyl, 3,3-dimethylbutyl, 1,3-dimethylbutyl, 1-ethyl-2.2-dimethylpropyl, l-methyl-2.2,2-trichloroetliyl. l-methyl-2,2-dichlo-roethyl, l-methyl-2,2-difluoroethyi, l-methyl-2-chloropropyl, l-methyl-2,2-dichloropropyl, l-methyl-2,2-difluoropropyl, 2-chloro-2-methylpropyl, 2-fluo-ro-2-methylpropyl, 2-bromo-2-methylpropyl, 3-fluoro-2-methylpropyl, 3-chlo-ro-2-methylpropyl, 2,3-dichloro-2-methyipropyl, 3-bromo-2,2-dimethyipropyl, 3-chloro-2,2-dimethylpropyl, 3-fluoro-2,2-dimethylpropyl, 2,3-dichloro-l,2-di-methylpropyl, l,2-dimethyl-2-fluoroethyl, l,2-dimethyl-2-Ghloroethyl, 1,2-di-methyl-2-bromoethyl, 3-fluoro-l,2-dimethyipropyl, 3-chloro-1,2-dimethylpro-pyl, 3,3-difluoro-l,2-dimethyIpropyI, l-dichloromethy]-2-methylpropyl, 1-di-chloromethyl-2-methylpropyl, 2,2-dimethyl-l-trichloromethyl, 2,2-dimethyl-1-dichloromethylpropyl, 3-fluoro-l,2,2-trimethylpropyl, 3-cliloro-l,2,2-tri- metiiylpropyl, 2-nuoro-l-etiiyi-2-metbylpropyl, 2-bromo-l-etiiyl-2-methyl-propyl, 2-chloro-l-ethyl-2-methylpropyl, 2-methyl-2-inethyloxypropy 1, 1,2-di-methyl-2-methyloxypropyl, 2,2-dichloro-2-fluoro-l-methyiethyl, or 2-methyl-1-trichloromethylpropyl. The compounds of formula (1) wherein R1 is 2-pentynyl; R" is hydro¬gen; and R2 is any of the following substituents: isopropyl, isobutyl. sec-butyl. 1.2-dimethyIpropyl. isopentyi, neopen-tyl. isohexyl. 1,2,2-trimethylpropyl, 1.2-dimethylbutyi, l-ethyl-2-methyl-propyl. 2.3-dimethylbutyl, 2.2-dimethylbutyl. 3.3-dimethylbutyL 1.3-dimeth-ylbutyl. l-ethyl-2,2-dimethy Ipropyl, 2.3,3-triinethylbutyl. 1,3,3-trimethyl-butyl, l-ethyl-3,3-dimethylbutyl, 1.2.3.3-tetramethylbutyl. l-methyl-2.2-di-methoxyethyl, l-methyl-2.2,2-trichloroethyl, l-methyi-2.2.2-trifluoromethyl, l-methyl-2,2-dichloroethyl, l-methyl-2,2-difluoroethyl, l-methyl.2-chloro-ethyl, l-methyi-2-fluoroethyl, l-methyl-2-isopropoxyethyl. l-methyl-2-chlo-ropropyi, l-methyl-2-fiuoropropyl, l-methyl-2,2-dichloropropyl, l-methyl-2,2-difluoropropyl, 2-ch]oro-2-iaethylpropyl, 2-fluoro-2-methyipropyl, 2-bromo-2-methyipropyl, 3-fluoro-2-methyipropyl, 3-chloro-2-methy Ipropyl, 2,3-dichloro-2-methylpropyl, 3-bromo-2,2-dimethylpropyl, 3-chloro-2,2-dimethyi-propyl, 3-fluoro-2,2-dimethylpropyl, 2.3-dichioro-l,2-dimethylpropyl, 1.2-di-methyl-2-fluoroethyl. l,2-dimethyl-2-chloroethyl, l,2-dimethyl-2-bromoethyl. 3-fluoro-l,2-dimethylpropyl, 3-chloro-l,2-dimethylpropyl, 3,3-difluoro-l,2-di-methylpropyl, 3,3,3-trifluoro-2-trifluoromethyl-2-methylpropyl, l-dichloro-methyi-2-methyipropyl, l-trifluoromethyl-2-methylpropyl, 1-dichloromethyl-2-methy]propyl, 2,2-dimethyl-1-trichloromethylpropyI, 2,2-diineth3'l-l-di-chlorome thy Ipropyl, 3-fluoro-i,3-dimethylbutyi, 3-chloro-l,3-dimethyibutyl, 3-bromo-1.3-dimethyibutyl, 3-£luoro-2,3-dimethylbutyl, 3-chloro-2.3-dimeth-ylbutyl, 3-bromo-2,3-dimethylbutyl, 3-fluoro-l,2.2-trimethylpropyl, 3-chloro-1,2,2-trimethylpropyl. 3-bromo-1,2,2-trimethylpropyl, 2-fluoro-l-ethyl-2- meth3'lpropyi, 2-bromo-l-ethy]-2-methylpropyl, 2-chloro-l-ethyJ-2-me£hy]-propyl, 2-methyl-2-methoxypropyl. 1.2-dimethyl-2-methoxypropyl, 2.2-di-chioro-2-£luoro-l-methylethyl, or 2-methyi-l-trichloroinethylpropyl. The compounds of formula (1) wherein R1 is l-methyl-2-butynyl; R" is hydrogen: and R1 is any of the following substituents: isobutyl, 1,2-dimethylpropyl, isopentyl. neopentyL 1.2.2-trimetb.yl-propyl, l-ethyl-2-niethyipropyL 3.3-dimethylbutyl, 1,3-dimethylbutyl. 1-ethyi-2,2-dimethylpropyl. l-methyl-2.2.2-trichloroethyl, l-methyl-2.2-dichlo-roethyl, l-methyl-2.2-difluoroethyl. l-methyl-2-chloropropyl, l-methyl-2.2-dichloropropvL l-methyl-2.2-difluoropropyl, 2-chloro-2-methylpropyl, 2-fluo-ro-2-methyIpropyl. 2-bromo-2-methylpropyl. 3-fluoro-2-methyipropyI, 3-chlo-ro-2-methylpropyl, 2,3-dichloro-2-methylpropyl, 3-bromo-2.2-dimethylpropyl. 3-chloro-2,2-dimethylpropyl. 3-fluoro-2.2-dimethylpropyl, 2,3-dichloro-l,2-di-methylpropyl, l,2-dimethyl-2-fluoroethyl, l,2-dimethyl-2-chloroethyl, 1,2-di-methyl-2-bromoethyl, 3-fluoro-1.2-dimethyipropyl, 3-chloro-l,2-dimethylpro-pyL 3,3-difluoro-l,2-dimethylpropyL l-dichloromethyl-2-methylpropyl, 1-di-chloromethyl-2-methylpropyl. 2,2-dimethyl-l-trichloromethyl. 2.2-dimethyl-1-dichloromethylpropyl, 3-fluoro-1.2,2-trimethylpropyL 3-chloro-l,2.2-tri-methylpropyl, 2-fluoro-l-ethyl-2-methylpropyl, 2-bromo-l-ethyl-2-methyl-propyl, 2-chloro-l-ethyi-2-methylpropyl, 2-methyl-2-methyloxypropyL 1,2-di-metfayI-2-methyloxypropyi, 2.2-dichIoro-2-fIuoro-l-methylethyI, or 2-methyI-l-trichioromethylpropyl. The compounds of formula (6) wherein R1 is 2-propynyl; R2 is hydro¬gen; and R1* is any of the following substituents: cyclopropyi, l-methylcyclopropyl, 2-methylcyclopropyl, 2-fluorocyclo- propyl, 2-chlorocyclopropyi, 1,2-dimethylcyclopropyl, 2,2-diniethyicydopropyl. 2,2-dichloro-l-methylcyclopropyl, 2,2-(iichloro-3,3-dimethylcyclopropyi. cyclobutyl, 1-methylcyclobutyl. 2-methylcyclobutyl, l-chlorocyclobutyl. 2-chlorocyciobutyl, cyclopentyl, ■1-methylcyclopentyl, 2-methylcyclope'ntyl, 2-chlorocyelopentyl, cyclohexyl. 2.2-d.ifluorocyclobutyl or 1.2-dimethylcyclo-pentyl. The compounds of formula (6) wherein R1 is 2-butynyl: R2 is hydrogen: and R1 is any of the following substituents: cyclopropyi, l-methylcyclopropyl, 2-methylcyciopropyl. 2-fluorocyclo- propyl, 2-chlorocyclopropyl. 1.2-dimethylcyclopropyl, 2,2-dimethylcyclopropyl, 2.2-dichloro-l-methylcyclopropyl. 2,2-dichloro-3,3-dimethylcyclopropyl, cyclobutyl, 1-methylcyclobutyl, 2-methylcyclobutyl, 1-chiorocyclobutyl, 2-chlorocyclobutyl, cyclopentyl, 1-me thy icy elope ntyl, 2-methylcyclopentyl. 2-chiorocyclopentyl, cyclohexyl, 2,2-difluorocyclobutyl, or l,2-dim6thylcyclo-pentyl. The compounds of formula (7) wherein R1 is 2-propynyl: R" is hydro¬gen; and R* is any of the following substituents: cyclopropyi, l-methylcyclopropyl, 2-methyicyclopropyl, 2-fluorocyclo- propyl, 2-chlorocyclopropyl, 1,2-dimethylcyclopropyl, 2,2-dimethylcyclopropyl, 2,2-dichloro-1-methy ley clop ropyl, 2.2-dichloro-3,3-dimethylcyclopropyl, cyclobutyl, 1-methylcyclobutyl, 2-methylcyclobutyl, l-chlorocyclobutyl, 2-chlorocyclobutyi, cyclopentyl, 1-methylcyciopentyl, 2-methylcyclopentyl, 2-chlorocyclopentyl, cyclohexyl, 2,2-difluorocyclobutyl, or 1,2-dimethylcyclo- pentyl. The compounds of formula (7) wherein R1 is 2-butynyl; R2 is hydro¬gen; and R1' is any of the following substituents: ■ cyclopropyl. 1-methylcyclopropyl, 2-methylcyclopropyl, 2-fluorocycio- propyl, 2-chiorocycJopropyi. 1.2-dimethylcyclopropyl, 2,2-dimethyIcyclopropyl. 2.2-dichloro-l-methylcyciopropyl, 2,2-dichloro-3,;-dimethylcyclopropyl, cyclobutyl, 1-methyicyclobutyl. 2-methylcyclobutyl. 1-chlorocyclobutyl, 2-chlorocyclobutyl. cyclopentyl, 1-methylcyclopentyl. 2-methylcyciopentyl. 2-chlorocyclopentyl, cyclohexyl. 2,2-difluorocyclobutyl, or 1.2-dimethylcycio-pentyl. The compounds of formula (7) wherein R1is 2-pentynyl; R1 is hydro¬gen: and R"* is any of the following substituents: cyclopropyl, 1-methylcyclopropyl, 2-methylcyclopropyl, 2-fluorocycio- propyl, 2-chlorocyclopropyl. 1,2-dimethylcyclopropyl, 2,2-dimethylcyclopropyl, 2.2-dichloro-l-methylcyelopropyl, 2,2-dichloro-3.3-dimethylcyclopropyl. cyclobutyl, 1-metbyicyclobutyl, 2-methyIcyciabutyl, 1-chlorocyclobutyl. 2-chlorocyclobutyl, cyclopentyl, 1-methylcyclopentyl, 2-methylcyclopentyl, 2-chlorocyclopentyl, cyclohexyl, 2,2-difluorocyclohutyl, or 1,2-dimethylcyclo-pentyl. The compounds of formula (7) wherein R1 is l-methyl-2-butynyl; R2 is hydrogen; and R* is any of the following substituents: cyclopropyl. 1-methylcyclopropyi, 2-methylcyclopropyL 2-fl,uorocyclo- propyl, 2-chlorocyclopropyl, 1.2-dimethylcyclopropyl, 2.2-dimethyicyclopropyi, 2.2-dichloro-l-methylcyclopropyl, 2.2-dichloro-3,3-dimethylcyclopropyl. cyclobutyl, 1-methylcyclobutyl, 2-methylcyclobutyl, 1-chlorocyclobutyl, 2-chlorocyclobutyi, cyclopentyl, 1-methylcyclopentyl, 2-methylcyclopentyl, 2-chlorocyciopentyl, cyclohexyl, 2,2-difluorocyclobutyl, or 1,2-dimethyIcyclo-pentyl. The compounds of formula (8) wherein R1 is 2-propynyl: R1 is- hydro¬gen: and R* is any of fhe following substituents: cyclopropyl, l-methylcyclopropyl, 2-methylcyclopropyL 2-fluorocyGlo- propyl, 2-chIorocyclopropyl, 1.2-dimethylcyclopropyl, 2,2-dimethylcyclopropyL 2.2-dichloro-l-methylcyclopropyl, 2.2-dichloro-3,3-dimethylcyciopropyl. cyclobutyl, 1-methylcyclobutyL 2-methylcyclobutyl, 1-chlorocyclobutyl. 2-chiorocyclobutyl. cyclopentyl, 1-methylcyclopentyl, 2-methylcyciopentyi. 2-chlorocyclopentyl, cyclohexyl, 2,2-difluorocyclobutyl, 1,2-dimethylcyclopentyl. The compounds of formula (8) wherein R1 is 2-butynyl; R" is hydrogen: and R"* is any of the following substituents: cyclopropyl, l-methylcyclopropyl, 2-methylcyciopropyl, 2-fluorocyclo- propyl, 2-chlorocyclopropyl, 1.2-dimethylcyclopropyl, 2,2-dimethylcyclopropyl, 2.2-dichlot-o-l-methylcyclopropyl, 2.2-dichloro-3.3-dime thy Icyclopropvl. cyclobutyl, 1-methylcyclobutyl, 2-methylcyclobutyl, l-chlorocyclobutyl 2-chlorocyclobutyl, cyclopentyl. 1-methylcyclopentyl, 2-methylcyclopentyL 2-chlorocyclopentyl, cyclohexyl, 2,2-difluorocyclobutyl, or 1,2-dimethylcyclo¬pentyl. The compounds of formula (8) wherein R1 is 2-pentynyl; R2 is hydro¬gen; and }i* is any of the following substituents: cyclopropyl, l-methylcyclopropyl, 2-methylcyclopropyl, 2-fluorocyclo- propyl, 2-chlorocyclopropyl. 1,2-dimethylcyclopropyl, 2,2-dimethylcyciopropyl, 2.2-dichloro-l-methylcyclopropyl, 2,2-dichlorQ-3,3-dimethylcycloprapyl, cyclobutyl, 1-methylcyclobutyl, 2-methylcyclobutyl, 1-chlorocyclobutyl. 2-chlorocyclobutyi, cyclopentyl, 1-methylcyclopentyl. 2-methylcyclQpentyl, 2- chiorocyclopentyl, cyclohexyL 2,2-difIuorocyclobutyl, or 1,2-dimethylcyclo-pentyl. The compounds of formula (8) wherein R1 is l-methyl-2-butynyl: R- is hydrogen: and R1* is any of the following substituents: cyclopropyl, 1-methyicyciopropyl. 2-methylcyclopropyl. 2-£luorocyclo- propyL 2-chlorocyclopropyl. 1.2-dimethylcyclopropyl, 2,2-dimethylcyciopropyl. 2.2-dichloro-l-methylcyclopropyl. 2,2-dichloro-3,3-dimethyicyclopropvl, cyclobutyl, 1-methylcyclobutyl, 2-methylcyclobutyl, l-chlorocyclobutyl. 2-chlorocyclobutyl. cyclopentyl, 1-methylcyclopentyl, 2-methylcyclopentyl. 2-chlorocyclopentyl. cyclohexyl, 2.2-difluorocyclobutyi. or 1.2-dimethylcycio-pentyl. The pests against which the present compound has activity mav include, for example, arthropods such as insects and acarines; and nema-thelminthes such as nematodes. Specific examples are listed below: Hemiptera: Delphacidae such as LaodeJphax striateBus, NiJaparvata lugens. and Sogatella furcifera; Deltocephalidae such as Nephotettix cincticeps and Empoasca onukii: Aphididae such as Aphis gossypii and Myzus persicaePentatomidae: Aieyrodidae such as TriaJeurodes vaporariorum, Bewisia tubaci, and Bemisia argentifohi; Coccidae; Tingidae; Psyllidae; Lepidoptera: Pyralidae such as Chilo suppressahs, Cnaphalocrocis tnedinalis, Ostrinia nubilalis. and Parapediasia tererreUa; Noctuidae such as Spodoptera Jitura, Spodoptera exigua, Pseudaletia separata, Mamestra brassicae, Agrotis ipsilon. Thoricoplusia spp., Heliothis spp., IleJicoverpa sp-p., and Eariasspp.: Pieridae such as Pieris rapae crucivora; Tortricidae such as Adoxophves orana fasciata, Grapholita molesta. and Cydia pomonelJa; Carposinidae such as Carposina niponensis; Lyonetiidae such as Lyonetia clerkelia: Gracillariidae such as Phyllonorycter ringoniella; Phyllocnistidae such as Phylhcnistis citrella; Yponomeutidae such as Plutela xylosteila; Gelechiidae such as Pectinophora gossypiella: Arctiidae: Tineidae; Diptera: Calicidae such as Culex pipiens paJIens, Culex tntaeniorhynchus. and Culex quinquefasciatus; Aedes spp. such as Aedes aegyptiand Aedes albopictus: Anopheles spp. such as Anopheles sinensis; Chironomidae; Muscidae such as Musca domestica and Muscina stabulans. Calliphoridae: Sarcophagidae; Fanniidae; Anthomyiidae such as Delia platura and Delia antiqua; Tephritidae; Drosophilidae; Psychodidae; Tabanidae; Simuhidae; Stomoxyidae; Agromyzidae; Coleoptera: Diabrotica spp. such as Diabrotica virgifera virgifera and Diabrotica undecimpunctata howardi: Scarabaeidae such as Anomala cuprea and Anomala rufocuprea: Curcuhonidae such as Sitophilus zeamais, Lissorhoptrus oryzophilus, and Callosobruchuys chienensis; Tenebrionidae such as Tenebrio molitor and Tribolium castaneum: Chr>'somehdae- such as Oulema oryzae, Aulacopbora femoralis, Phyl-lotreta striolata. and Leptinotarsa decemlineata; Anobiidae; Epilachna spp. such as Epilachna vigintioctopunctata; Lyctidae; Bostrychidae; Cerambycidae; Paederus fuscipes; Thysanoptera: Thripidae spp. including Thrips spp. such as Thrips paJmi, Frank¬liniella spp. such as Frankliniella occidentalis, and Sciltothrips spp. such as Sciltothrips dorsalis; Phlaeothripidae spp.; Hymenoptera: Tenthredinidae; Formicidae; Vespidae; Dictyoptera: Periplaneta spp.; Blatta spp.; Orthoptera; Acrididae; Gryllotalpidae: ,. Aphaniptera: Pulex irritans: Anoplura: Pediculus humanus: Isoptera: Termitidae; Acarina: Tetranychidae such as Tetranvchus urticae, Tetranvchus kanzawai. Panonychus citri, Panonychus ulmi. and Ohgonychus spp.: Eriophyidae such as AcuJops peJekassi and AcuJus schJechtendaJi; Tarsonemidae such as Polyphagotarsonernus latus: Tenuipalpidae; Tuckerellidae; Ixodidae such as Haemaphysalis longicornis. Haemaphysalis Uava. Dermacentor taiwanjcus, Ixodes ovatus, Ixodes persulcatus. and Boophilus micropius; Acaridae such as Tyrophagusputrescentiae, Epidermoptidae such as Dermatophagoides farinae and Dermato-phagoides ptrenyssnus; Cheyletidae such as Cheyletus eruditus, Cheyletus maJaccensis, and Cheyletus rnoorei; Dermanvssidae; Nematoda: Pratylenchus coffeae, Pratylenchus fallax, Heterodera glycines. GJo-bodera rostochiensis, Meloidogyne hapla. Meloidogyne incognita. The pesticidal composition of the present invention is comprising the ptesent compound as an active ingredient, and an additive. The pesticidal composition bf the present invention may be prepared by mixing the present compound with a solid carrier, a Uquid carrier, a gaseous carrier and/or a bait, and if necessary, adding a surfactant and other adjuvants, and then formulating the mixture into an oil solution, an emulsifiable concentrate, a flowable, a granule, a dust, a poison bait, a microcapsule formulation, or the like. In each of these formulations, the present compound is usually contained in an amount of 0.1% to 95% by weight. The solid carrier which can be used in the formulation may include, for example, the following materials in iine powder or granular form: clays (e.g., kaolin clay, diatomaceous earth, synthetic hydrated silicon oxide, ben-tonite, Fubasami clay, acid clay); talc, ceramic, and other inorganic minerals {e.g., sericite, quartz, sulfur, activated carbon, calcium carbonate, hydrated silica); and chemical fertilizers {e.g., ammonium sulfate, ammonium phos¬phate, ammonium nitrate, urea, ammonium chloride). The liquid carrier may include, for example, water: alcohols (e.g.. methanol, ethanol); ketones (e.g., acetone, methyl ethyl ketone); aromatic hydrocarbons {e.g., benzene, toluene, xylene, ethylbenzene, methylnaphtha-lene); aliphatic hydrocarbons (e.g., hexane, cyclohexane, kerosine, hght oil); esters (e.g., ethyl acetate, butyl acetate); nitriles (acetonitrile, isobutyro-nitrile); ethers {e.g., dusopropyl ether, dioxane); acid amides (e.., N,N-di-methylformamide, N,N-dimethylacetamide); halogenated hydrocarbons {e.g., dichloromethane, trichloroethane, carbon tetrachloride); dimethyisulfoxide; and vegetable oils (e.g., soy bean oil and cotton seed oil). The gaseous carrier may include, for example, fluorocarbon, butane gas, hquefied petroleum gas (LPG), dimethyl ether, and carbon dioxide. The surfactant may include, for example, alkyl sulfate salts; alkyl- sulfonic acid salts; aikylarylsulfonic acid salts; alkyl aryl ethers and their poiyoxyethylene derivatives; polyethylene glycol ethers: polyhydric alcohol esters; and sugar alcohol derivatives. ■ ' The other adjuvants may include binders, dispersants, and stabilizers, specific examples of which are casein, gelatin, polysaccharides {e.g., starch, gum arable, cellulose derivatives, alginic acid), iignin derivatives, bentonite, sugars, synthetic water-soluble polymers {e.g., polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acid), PAP (isopropyl acid phosphate), BHT (2,6-di-t-butyl-4-methylphenol), BHA (mixtures of 2-t-butyl-4-methoxyphenol and 3-t-butyl-4-methoxyphenol), vegetable oils, mineral oils, fatty acids, and fatty acid esters. The base material for poison baits may include, for example, bait ingredients such as grain powders, vegetable oils, sugars, and crystalline cellulose: antioxidants such as dibutylhydroxytoluene and nordihydroguai-aretic acid; preservatives such as dehydroacetic acid; agents for preventing children and pets from erroneously eating, such as hot pepper powder; and pest-attractive flavors such as cheese flavor, onion flavor, and peanut oil. The method for controlling pests according to the present invention is carried out by applying the pesticidal composition of the present invention to pests or habitats of pests. When the pesticidal composition of the present invention is used for the control of pests in agriculture and forestry, the application amount is usually 1 to 10,000 g as the amount of the present compound per 1,000 m". Formulations such as emulsifiable concentrates, wettable powders, flowables, and microcapsule formulations are usually used after dilution with water to have an active ingredient concentration of 10 to 10,000 ppm, while formula¬tions such as granules and dusts are usually used as such. The pesticidal composition of the present invention can be used by foliar treatment to plants such as crop plants to be protected from pests or can also be used by treatment to seedbeds prior to tjie planting of crop plant seedlings or to planting holes or plant bottoms in the planting. Further, for the purpose of controlling pests inhabiting the soil of a cultivated land, the pesticidal composition of the present invention may also be used by treat¬ment to the soil. The pesticidal composition of the present invention can also be used by winding a resin formulation processed into a sheet, string, or cord form around crop plants, or by stretching it in the vicinity of crop plants and/or laying it on the soil surface at the plant bottom. The pesticidal composition of the present invention can also be used in admixture or combination with other insecticides, nematocides, acaricides, bactericides, fungicides, herbicides, plant growth regulators, synergists, fer¬tilizers, soil conditioners, animal feeds, and the like. The insecticide and/or acaricide and/or nematocide which can be used may include, for example, organophosphorus compounds such as Fenitro-thion. Fenthion, Pyridaphenthion, Diazinon, Chlorpyriphos, Chlorpyriphos-methyl. Acephate. Metliidathion, Disulfoton, DDVP, Sulprofos, Profenofos, Cyanophos, Dioxabenzofos, Dimethoate, Phenthoate. Malathion, Trichlorfon. Azinphos-methyl, Monocrotophos. Dicrotophos, Ethion, and Fosthiazate: carbamate compounds such as BPMC, Benfuracarb, Propoxur, Carbosulfan, Carbaril, Methomyl. Ethiofencarb, Aldicarb, Oxamyl, Fenothiocarb, Thio-dicarb, and Alanycarb; pyrethroid compounds such as Etofenprox, Fenvaler-ate, Esfenvalerate, Fenpropathrin, Cypermethrin, a-Cypermethrin, Z-Cy-permethrin, Permethrin, Cyhalothrin, X-Cyhalothrin, Cyfluthrin, p-Cyflu-thrin. Deltamethrin, Cycloprothrin, x-Fluvalinate, Flucythrinate, Bifenthrin, Acrinathrin. Traromethrin. Silafluofen. and Halfenprox; neonicotinoid com¬pounds such as Thiamethoxiam and Acetamiprid; benzoylphenylurea com¬pounds such as Chlorfluazuron, Teflubenzuron, Fulphenoxron, and Lufenu-ron; benzoylhydrazide compounds such as Tebufenozide, Halofenozide, Me-thoxyfenozide, and Chromafenozide; thiadiazine derivatives such as Bupro-fezin; Nereistoxin derivatives such as Cartap, Thiocyclam, and Bensultap; chlorinated hydrocarbon compounds such as Endosulfan, y-BHC, and 1,1-bis(chlorophenyl)-2,2.2-trichloroethanol; formamidine derivatives such as Amitraz and Chlordimeform; thiourea derivatives such as Diafenthiuron; phenylpyrazol compounds; Chlorfenapyr; Pymetrozine,' Spinosad; Indoxa-carb; Pyridalyl; Pyriproxyfen; Fenoxycarb; Diofenolan: Cyromazine; Bromo-propylate; Tetradifon; Chmomethionat; Propargite; Fenbutatin oxide; Hexa-thiazox; Etoxazole; Clofentezine; Pyridaben; Fenpyroximate; Tebufenpyrad; Pyrimidifen; Fenazaquin; Acequinocyl; Bifenazate; Fluacrypyrim; Milbemec-tin: Avermectm; Emamectin benzoate; Azadiiactin [AZAD]; and polynactin complexes [e.g., tetranactin, dinactin, trinactin]. Examples The present invention will be further illustrated by the following production examples, formulation examples, and test examples; however, the present invention is not hmited to these examples. In the production examples and reference production examples, all 'H-NMR data were measured in deuterated chloroform using tetramethyl-silane as the internal standard, unless otherwise indicated. The following will describe production examples for the present com¬pounds. The present compound numbers used in the production examples are those shown below in Tables 1 and 2. Production Example 1 In 0.5 ml of tetrahydrofuran was suspended 0.02 g of sodium hydride {60% in oil), to which 0.1 ml of a solution containing 0.02 g of 2-butyn-l-ol in tetrahvdrofuran was added dropwise at room temperature. After stirring at room temperature for 20 minutes, 0,1 ml of a solution containing 0.05 g of 4-chloro-6-(isopropyloxy)pyrimidine in tetrahydrofuran was added dropwise at room temperature, followed by stirring for 2 hours. The mixture was then poured into a saturated aqueous ammonium chloride solution, which was extracted three times with t-butyl methyl ether. The combined organic layers were washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated. The residue was subjected to silica gel column chromatography to give 0.05 g of 4-{2-butynyloxy}-6-isopropoxypyrimidine (the present compound (1)). 'H-NMR: 1.34 (d. 6H), 1.87 (t, 3H), 4.94 (q, 2H). 5.25-5.34 (m. IH), 6.05 (s, IH). 8.42 (s, IH). Production Example 2 In 4 ml of tetrahydrofuran was suspended 0.11 g of sodium hydride (60% in oil), to which 0.5 ra! of a solution containing 0.19 g of 1-cycIopropyI-ethanol in tetrahydrofuran was added dropwise at room temperature. After stirring at room temperature for 10 minutes. 0.5 ml of a solution containing 0.3 g of 4,6-dichloropyrimidine m tetrahydrofuran was added dropwise at 0°C, followed by stirring at the same temperature for 4 hours. The reaction mixture was then poured into a saturated aqueous ammonium chloride solu¬tion, which was extracted three times with t-butyl methyl ether. The com¬bined organic layers were washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated to give a crude product of 4-chloro-6-(l-cyclopropylethoxy)pyrimidine. In 4 ml of tetrahydrofuran was suspended 0.11 g of sodium hydride (60% in oil), to which 0.5 ml of a solution containing 0.15 g of 2-butyn-l-ol in tetrahydrofuran was added dropwise at room temperature, followed by stir- ring for 10 minutes. To this was slowly added dropwise 0.5 ml of a solution containing the above 4-chloro-6-{l-cyclopropylethoxy)pyrimidine in tetra-hydrofuran, followed by stirring at room temperatiure for 1 hour. The reac¬tion mixture was then poured into a saturated aqueous ammonium chloride solution, which was extracted three times with t-butyl methyl ether. The combined organic layers were washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then con¬centrated. The resulting residue was subjected to sihca gel column chro¬matography to give 0.22 g of 4-(2-butynyloxy)-6-(l-cyclopropylethoxy)pyrimi-dine (the present compound (2)). 'H-NMR; 0.28-0.33 (m. IH), 0.39-0.58 (m, 3H). 1.08-1,14 (m, iHj, 1.38 {d. 3H), 1.87 (t, 3H). 4.65-4.74 (m, IH), 4.94 (q, 2H), 6.08 (s, IH), 8.39 (s, IH). Production Example 3 In 2 ml of tetrahydrofuran was suspended 0.06 g of sodium hydride (60% in oil), to which 0.3 ml of a solution containing 0.09 g of 2-butyn-l-ol in tetrahydrofuran was added dropwise at room temperature, followed by stir¬ring for 10 minutes. To this was added dropwise 0.3 ml of a solution con¬taining 0.24 g of 4-chloro-G-(l,2.2-trimethylpropyloxy)pyrimidine in tetra¬hydrofuran at room temperature, followed by stirring for 3 hours. The reaction mixture was then poured into a saturated aqueous ammonium chloride solution, which was extracted three times with t-butyl methyl ether. The combined organic layers were washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then con¬centrated. The residue was subjected to silica gel column chromatography to give 0.25 g of 4-(2-butynyloxy)-6-(l,2,2-trimethylpropyloxy)pyrimidine (the present compound (3)). 'H-NMR: 0.96 (s, 9H), 1.22 (d, 3H), 1.87 (t, 3H), 4.93-5.01 (m, 3H, involving two quartet at 4.95 and 4.98), 6.06 (s, IH), 8.42 (s, IH). Production Example 4 In 3 ml of tetrahydrofuran was suspended 0.08 g of sodium hydride (60% in oil), to which 0.3 ml of a solution containing 0.12 g of 2-butyn-l-ol in tetrahydrofuran was added dropwise at room temperature, followed by stir¬ring for 10 minutes. To this was added dropwise 0.3 ml of a solution con¬taining 0.35 g of 4-Chl Production Example 5 In 4 ml of tetrahydrofuran was suspended 0.11 g of sodium hydride (60% in oil), to which 0.5 ml of a solution containing 0.23 g of 4-methyl-2-pentanol in tetrahydrofuran was added dropwise at room temperature, followed by stirring for 10 minutes. To this was added dropwise 0.5 ml of a solution containing 0.3 g of 4,6-dichioropyrimidine in tetrahydrofuran at 0°C. followed by stirring at the same temperature for 2 hours and further stirring at room temperature for 4 hours. The reaction mixture was then poured into a saturated aqueous ammonium chloride solution, which was extracted three times with t-butyl methyl ether. The combined organic layers were washed with a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate to give a crude product of 4-chloro-6-(1.3-di- methylbutoxy)pyrimidine. In 3.5 ml of tetrahydrofuran was suspended 0.1 g of sodium hydride (60% in oil), to which 0.3 ml of a solution containing 0.16 g of 2-butyn-l-ol in tetrahydrofuran was added dropwise at room temperature, followed by stir¬ring for 10 minutes. To this wasadded drppwise'O.'S'ml of a solution con¬taining the above 4-chIoro-6-(1.3-dimethylbutoxy)pyrimidirie in tetrahydro¬furan, followed by stirring at room temperature for 4 hour. The reaction mixture was then poured into a saturated aqueous ammonium chloride solution, which was extracted three times with t-butyl methyl ether. The combined organic layers were washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then con¬centrated. The resulting residue was subjected to silica gel column chro¬matography to give 0.30 g of 4-(2-butynyloxy)-6-(l,3-dimethylbutyloxy)pyri-midine (the present compound (5)). 'H-NMR: 0.89-0.94 (m, 6H), 1.29 (d, 3H), 1.32-1.41 (m, IH), 1.65-1.83 (m. 2H), 1.87 (t, 3H), 4.94 (q, 2H), 5.26-5.35 (m, IH), 6.05 (s, IH), 8.42 (s, IH). Production Example 6 In 1.6 ml of tetrahydrofuran was suspended 0.04 g of sodium hydride (60% in oil), to which 0.2 ml of a solution containing 0.06 g of 2-butyn-l-ol in tetrahydrofuran was added dropwise at room temperature, followed by stir¬ring for 10 minutes. To this was added dropwise 0.2 ml of a solution con¬taining 0.16 g of 4-chloro-6-(2,2-dimethylpropyloxy)pyrimidine in tetrahy¬drofuran at room temperature, followed by stirring for 2 hours. The reaction mixture was then poured into a saturated aqueous ammonium chloride solution, which was extracted three times with t-butyl methyl ether. The combined organic layers were washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then con¬centrated. The residue was subjected to silica gel column chromatography to give 0.15 g of 4-(2-butynyioxy)-6-(2,2-dimethylpropyloxy)pyrimidine (the present compound (6)). 'H-NMR: 1.01 (s, 9H), 1.87 (t, 3H), 3.98 {s, 2H), 4.95 (q, 2H), 6.11 {s, IH), 8.43 (s, IH). Production Example 7 In 4 ml of tetrahydrofuran was suspended 0.11 g of sodium hydride (60% in oil), to which 0.5 ml of a solution containing 0.24 g of 4,4-dimethyl-2-pentanol in tetrahydrofuran was added dropwise at room temperature, fol¬lowed by stirring for 10 minutes. To this was added dropwise 0.5 ml of a solution containing 0.3 g of 4,6-dichloropyrimidine in tetrahydrofuran at 0°C, followed by stirring at the same temperature for 2 hours and further stirring at room temperature for 4 hours. The reaction mixture was then poured into a saturated aqueous ammonium chloride solution, which was extracted three times with t-butyl methyl ether. The combined organic layers were washed with a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate to give a crude product of 4-chloro-6-(l,3.3-trimethy lb utoxy )pyrimidine. In 2 ml of tetrahydrofuran was suspended 0.03 g of sodium hydride (60% in oil), to which 0.5 ml of a solution containing 0.05 g of 2-butyn-l-ol in tetrahydrofuran was added dropwise at room temperature, followed by stir¬ring for 10 minutes. To this was added dropwise 0.5 ml of a solution con¬taining the above 4-Ghloro-6-(l,3,3-trimethylbutoxy)pyrimidine in tetrahy¬drofuran, followed by stirring at room temperature for 4 hour. The reaction mixture was then poured into a saturated aqueous ammonium chloride solu¬tion, which was extracted three times with t-butyl methyl ether. The com¬bined organic layers were washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated. The residue was subjected to sihca gel column chromatography to give 0.14 g of 4-(2-butynyloxy)-6-(l,3,3-triniethylbutyioxy)pyrimidine (the present com¬pound (7)). 'H-NMR: 0.91 (s, 9H), 1.29 (d, 3H), 1.40 (dd, IH), 1.78 {dd, IH), 1.87 {t, 3H). 4.94 (q, 2H), 5.34-5.39 (m. IH), 6.03 (s, IH), 8.44 (s. IH). Production Example 8 In 2 ml of tetrahydrofuran was suspended 0.03 g of sodium hydride (60% in oil), to which 0.3 ml of a solution containing 0.05 g of 2-butyn-l-ol in tetrahydrofuran was added dropwise at room temperature, followed bv stir¬ring for 10 minutes. To this was added dropwise 0.3 ml of a solution con¬taining 0.10 g of 4-chloro-6-[l-(l-methylcyclopropyl)ethyloxy]pyriinidine in tetrahydrofuran, followed by stirring at room temperature for 3 hours. The reaction mixture was then poured into a saturated aqueous ammonium chloride solution, which was extracted three times with t-butyl methyl ether. The combined organic layers were washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then con¬centrated. The residue was subjected to silica gel column chromatography to give 0.09 g of 4-(2-butynyloxy)-6-[l-(l-methylcyclopropyl)ethyloy]pyrimi-dine (the present compound (8)). 'H-NMR: 0.29-0.37 (m, 2H), 0.43-0.46 (m, IH), 0.55-0.61 (m, IH), 1.14 (s, 3H), 1.33 (d, 3H), 1.87 (t, 3H), 4.71 (q, IH), 4.94 (q, 2H), 6.07 (s, IH), 8.39 (s, IH). Production Example 9 In 4 ml of tetrahydrofuran was suspended 0.11 g of sodium hydride (60% in oil), to which 0.5 ml of a solution containing 0.44 g of 2,2-bis(trifluo-romethyl)propanol in tetrahydrofuran was added dropwise at room tempera¬ture, followed by stirring for 10 minutes. To this was added dropwise 0.5 ml of a solution containing 0.3 g of 4,6-dichloropyrimidine in tetrahydrofuran at 0°C, followed by stirring at the same temperature for 1.5 hours. The reac- tion mixture was then poured into a saturated aqueous ammonium chloride solution, which was extracted three times with t-butyl methyl ether. The combined organic layers were washed with a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate to give a crude 3roduct of 4-chloro-6-[2.2-bis(trifluoromethyl)propoxy]pyrimidine. In 4 ml of tetrahydrofuran was suspended 0.11 g of sodium hydride ;60% in oil), to which 0.5 ml of a solution containing 0.16 g of 2-butyn-l-ol in tetrahydrofuran was added dropwise at room temperature, followed by stir¬ring for 10 minutes. To this was added dropwise 0.5 ml of a solution con¬taining the above 4-chloro-6-[2.2-bis(trifluoromethyl)propoxy]pyrimidine in tetrahydrofuran. followed by stirring at room temperature for 6 hour. The reaction mixture was then poured into a saturated aqueous ammonium chloride solution, which was extracted three times with t-butyl methyl ether. The combined organic layers were washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then con¬centrated. The residue was subjected to silica gel column chromatography to give 0.30 g of 4-(2-butynyloxy)-6-[2,2-bis(trifluoromethyl)propyloxy]pyri-midine (the present compound (9)). 'H-NMR: 1.49 {s, 3H), 1.87 (t, 3H), 4.69 (s, 2H), 4.97 (q, 2H), 6.17 (s, IH), 8.45 (s, IH). Production Example 10 In 5 ml of tetrahydrofuran was suspended 0.14 g of sodium hydride (60% in oil), to which 0.5 ml of a solution containing 0.22 g of 2-butyn-l-ol in tetrahydrofuran was added dropwise at room temperature, followed by stir¬ring for 10 minutes. To this was added dropwise 0.5 ml of a solution con¬taining 0.62 g of 4-chloro-6-(3-chloro-2,2-dimethylpropyloxy)pyrimidine in tetrahydrofuran at Q°C, followed by stirring at the same temperature for 4 hours. The reaction mixture was then poured into a saturated aqueous ammonium chloride solution, which was extracted three times with t-butyl methyl ether. The combined organic layers were washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated. The residue was subjected to sihca gel column chromatography to give 0.62 g of 4-(2-butynyloxy)-6-(3-chloro-2,2-dimethyi-propyloxy}pyrimidine (the present compound (10)). 'H-NMR: 1.11 (s, 6H), 1.87 (t, 3H), 3.52 (s. 2H), 4.16 (s. 2H), 4.96 (q. 2H), 6.11 (s, IH), 8,44(s, IH). Production Example 11 In 4 ml of tetrahydrofuran was suspended 0.10 g of sodium hydride (60% in oil), to which 0.5 ml of a solution containing 0.15 g of 2-butyn-l-ol in tetrahydrofuran was added dropwise at room temperature, followed by stir¬ring for 10 minutes. To this was added dropwise 0.5 ml of a solution con¬taining 0.41 g of 4-chloro-6-(3,3-dimethylbutyloxy)pyrimidine in tetrahydrofuran at CC, followed by stirring at the same temperature for 5 hours. The reaction mixture was then poured into a saturated aqueous ammonium chloride solution, which was extracted three times with t-butyl methyl ether. The combined organic layers were washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated. The residue was subjected to siUca gel column chromatography to give 0.40 g of 4-(2-butynyloxy)-6-(3,3-dimethylbutyloxy)-pyrimidine (the present compound (11)). 'H-NMR: 0.98 (s, 9H), 1.70 (t, 2H), 1.87 (t, 3H), 4.37 (t, 2H), 4.95 (q, 2H), 6.08 (s, IH), 8.44 (s, IH). Production Example 12 In 3.5 ml of tetrahydrofuran was suspended 0.09 g of sodium hydride (60% in oil), to which 0.5 ml of a solution containing 0.13 g of 2-butyn-l-ol in tetrahydrofuran was added dropwise at room temperature, followed by stir- .ng for 10 minutes. To this was added dropwise 0.5 ml of a solution con-iining 0.35 g of 4-chloro-6-(l,2-dimethylpropyloxy)pyrimidine in tetra-ydrofuran at 0°C, followed by stirring at the same temperature for 4 hours, 'he reaction mixture was then poured into a saturated aqueous ammonium bloride solution, which was extracted three times with t-butyl methyl ether, 'he combined organic layers were washed with a saturated aqueous sodium hloride solution, dried over anhydrous magnesium sulfate, and then con-entrated. The residue was subjected to silica gel column chromatography 3 give 0,41 g of 4-(2-butynyloxy)-6-(I,2-dimethylpropyloxy)pyrimidine (the resent compound (12)). 'H-NMR: 0.94 (d, 3H), 0.96 (d. 3H), 1.25 (d, 3H), 1.87-1.98 (m, 4H, nvolving a triplet at 1.87), 4.94-5.06 (m, 3H, involving a quartet at 4.95), 6.06 s, IH), 8.42 (s, IH). Production Example 13 In 4 ml of tetrahydrofuran was suspended 0.11 g of sodium hydride 60% in oil), to which 0.5 ml of a solution containing 0.16 g of 2-butyn-l-oi in -etrahydrofuran was added dropwise at room temperature, followed by stir¬ring for 10 minutes. To this was added dropwise 0.5 ml of a solution con¬taining 0.56 g of 4-chloro-6-(3-bromo-2.2-dimethylpropyloxy)pyrimidine in tetrahydrofuran at 0°C, followed by stirring at the same temperature for 4 [lours. The reaction mixture was then poured into a saturated aqueous immonium chloride solution, which was extracted three times with t-butyl methyl ether. The combined organic layers were washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated. The residue was subjected to silica gel column chromatography to give 0.54 g of 4-{2-butynyloxy)-6-(3-bromo-2,2-dimethyl-propyloxy)pyrimidine (the present compound (13)). 'H-NMR: 1.14 (s, 6H), 1.87 (t, 3H), 3.45 (s, 2H), 4.16 (s, 2H), 4.96 (q, 2H), 6.11(s, IH), 8.44(s, IH). Production Example 14 First, 0.41 g of 4-(2-butynyloxy)-6-(2-hydroxy-l,2-dimethylpropyi-oxy)pyrimidine was dissolved in 3 ml of chloroform, to which 0.5 ml of a solution' containing 0.31 g of dimethylaminosulfate trifluoride (hereinafter referred to as DAST) in chloroform was added dropwise at CC, followed by stirring for 20 minutes. The reaction mixture was then poured into water, which was extracted three times with chloroform. The combined organic layers were washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate , and then concentrated. The residue was subjected to silica gel column chromatography to give 0.20 g of 4-{2-butynyloxy)-6-(2-fluoro-l,2-dimethylpropyloxy)pyrimidine (the present com¬pound (14)), 'H-NMR: 1.32 (d. 3H), 1.37 (d. 3H), 1.43 (d, 3H), 1.87 (t. 3H), 4.95 (q, 2H), 5.33 (dq, IH), 6.12 (s, IH), 8.43 (s, IH). Production Example 15 In 4 ml of tetrahydrofuran was suspended 0.11 g of sodium hydride (60% in oil), to which 0.4 ml of a solution containing 0.15 g of 2-methyl-l-propanol in tetrahydrofuran was added dropwise at 0°C, followed by stirring for 10 minutes. To this was added dropwise 0.4 ml of a solution containing 0.30 g of 4,6-dichloropyrimidine in tetrahydrofuran, followed by stirring at the same temperature for 2 hours. To this was added dropwise 0.4 ml of a solution containing 0.14 g of 2-butyn-l-ol at 0°C and further added 0.11 g of sodium hydride (60% in oil), followed by further stirring at room temperature for 4 hours. The reaction mixture was then poured into a saturated aqueous ammonium chloride solution, which was extracted three times with t-butyl methyl ether. The combined organic layers were washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate. and then concentrated. The residue was subjected to silica gel column chromatography to give 0.35 g of 4-(2-butynyloxy)-6-isobutyloxjT3yriniidine (the present compound (15)). 'H-NMR: 1.00 (d, 6H), 1.87 (t, 3H), 2.01-2.12 (m, IH), 4.07 (d, 2H), 4.95 {q, 2H), 6.10 (s, IH), 8.43 (s, IH). Production Example 16 , In 4 ml of tetrahydrofuran was suspended 0.10 g of sodium hydride (60% in oil), to which 0.4 ml of a solution containing 0.21 g of 3-methyl-2-pentanol in tetrahydrofuran was added dropwise at 0°C, followed by stirring for 10 minutes. To this was slowly added dropwise 0.4 ml of a solution containing 0.30 g of 4.6-dichioropyrimidin6 in tetrahydrofuran, followed by stirring at the same temperature for 3 hours. To this was added dropwise 0.4 ml of a solution containing 0,14 g of 2-butyn-l-ol at 0°C and further added 0.10 g of sodium hydride (60% in oil), followed by further stirring at room temperature for 4 hours. The reaction mixture was then poured into a saturated aqueous ammonium chloride solution, which was extracted three times with t-butyl methyl ether. The combined organic layers were washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated. The residue was subjected to silica gel column chromatography to give 0.29 g of 4-(2-butynyloxy)-6-(l,2-dimethylbutyloxy)pyrimidine (the present compound (16)), 'H-NMR: 0.86-0.97 (m, 6H), 1.14-1.27 (m, 4H), 1.47-1.82 (m, 2H), 1.87 (t, 3H), 4.95 (q, 2H), 5.08-5.17 (m, IH), 6.05 (s, IH), 8.42 (s. IH). Production Example 17 First, 0.31 g of 4-(2-pentynyloxy)-6-(2-hydroxy-l,2-dimethylpropyl-oxy)pyrimidine was dissolved in 3 ml of chloroform, to which 0.5 ml of a solution containing 0.24 g of DAST in chloroform was added dropwise at 0°C, followed by stirring for 10 minutes. The reaction mixture was then poured into water, which was extracted three times with chloroform. The combined organic layers were washed with a saturated aqueous sodium chloride solu¬tion, dried over anhydrous magnesium sulfate , and then concentrated. The residue was subjected to silica gel column chromatography to give 0.16 g of 4-{2-fluoro-l,2-dimethylpropyloxy)-6-(2-pentynyloxy)pyrimidine (the present' compound (17)). ' H-NMR: 1.14 (t, 3H), 1.33 (d. 3H), 1.37 (d, 3H), 1.44 (d, 3H), 2.22 (qt, 2H), 4.97 (t, 2H), 5.27-5.38 (m. IH), 6.12 (s, IH), 8.42 (s, IH). Production Example 18 In 1.5 ml of tetrahydrofuran was suspended 0.04 g of sodium hydride (60% in oil), to which 0.3 ml of a solution containing 0.05 g of 2-buryn-l-ol in tetrahydrofuran was added dropwise at room temperature, followed by stir¬ring for 10 minutes. To this was added dropwise 0.3 ml of a solution con¬taining 0.16 g of 4-chloro-6-(2.2-dimethoxy-l-methylethoxy)pyrimidine in tetrahydrofuran at 0°C, followed by stirring at the same temperature for 1 hour and further stirring at room temperature for 3 hours. The reaction mixture was then poured into a saturated aqueous ammonium chloride solu¬tion, which was extracted three times with t-butyi methyl ether. The com¬bined organic layers were washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated. The residue was subjected to sihca gel column chromatography to give 0.11 g of 4-(2-butynyloxy)-6-(2,2-dimethoxy-l-methylethoxy)pyrimidine (the present compound (18)). ' H-NMR: 1.32 (d, 3H), 1.87 (t, 3H), 3.42 (s, 3H), 3.45 (s, 3H), 4.40 (d, IH), 4.94 (q, 2H), 5.36 (dt, IH), 6.12 (s, IH), 8.43 (s, IH). Production Example 19 In 4 ml of tetrahydrofuran was suspended 0.10 g of sodium hydride (60% in oil), to which 0.4 ml of a solution containing 0.33 g of 1,1,1-trichloro- 2-propanol in tetrahydrofuran was added dropwise at 0°C, followed by stir¬ring for 10 minutes. To this was added dropwise 0.4 ml of a solution con¬taining' 0.30 g of 4,6-dichloropyrimidine in tetrahydrofuran, followed by stir¬ring at the same temperature for 35 minutes. To this was added dropwise 0.4 ml of a solution containing 0.16 g of 2-butyn-l-ol in tetrahydrofuran and further added 0.10 g of sodium hydride (60% in oil), followed by stirring at room temperature for 35 minutes. The reaction mixture was then poured into a saturated aqueous ammonium chloride solution, which was extracted three times with t-butyl methyl ether. The combined organic layers were washed with a saturated aqueous sodium chloride solution, dried over an¬hydrous magnesium sulfate, and then concentrated. The residue was sub¬jected to silica gel column chromatography to give 0.44 g of 4-(2-butynyloxy)-6-(2.2,2-trichloo-l-methyiethoxy)pyrimidine (the present compound {19)). 'H-NMR: 1.66 (d, 3H), 1.87 (t, 3H), 4.97 (q, 2H), 6.02 (q, IH), 6.22 (s, IH), 8.46 (s, IH). Production Example 20 In 1.2 ml of carbon tetrachloride were dissolved 0.15 g of 4-(2-buty-nyloxy)-6-(2-methylallyloxy)pyrimidine and 0.01 g of trioctylmethylammo-nium chloride, to which 1 ml of concentrated hydrochloric acid was added dropwise at 0°C, followed by stirring at 0°C for 30 minutes and at room tem¬perature for 50 minutes. The reaction mixture was then poured into water, which was extracted three times with t-butyl methyl ether. The combined organic layer was washed with a saturated aqueous sodium hydrogencar-bonate solution, a saturated aqueous sodium chloride solution, dried over anhydrous magnesium, and then concentrated. The residue was subjected to silica gel column chromatography to give 0.08 g of 4-(2-butynyioxy)-6-(2-chloro-2-methylpropyloxy)pyrimidine (the present compound (20)). 'H-NMR: 1.66 (s, 6H), 1.87 (t, 3H), 4.42 (s, 2H), 4.96 (q, 2H), 6.18 (s. IH), 8.44 (s, IH). Production Example 21 In 3 ml of tetrahydrofuran was suspended 0.18 g of sodium hydride (60% in oil), to which 8.43 ml of a 0.4 M solution {tetrahydrofuran solution) of 1-cyclobutylethanol was added dropwise at 0°C, followed by stirring for 10 minutes. To this was added dropwise 0.3 ml of a solution containing 0.50 g of 4,6-dichloropyrimidine in tetrahydrofuran, followed by stirring at the same temperature for 3 hours. To this was added dropwise 0.3 ml of a solution containing 0.35 g of 2-butyn-l-ol in tetrahydrofuran and further added 0.24 g of sodium hydride (60% in oil), followed by stirring at room temperature for 7 hours. The reaction mixture was then poured into a saturated aqueous ammonium chloride solution, which was extracted three times with t-butyl methyl ether. The combined organic layers were washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated. The residue was subjected to silica gel column chromatograpliy to give 0.45 g of 4-(2-butynyloxy)-6-(l-cylclobutyl-ethyloxy)pyrimidine (the present compound (21)). 'H-NMR; 0.94 (d, 3H), 0.96 (d, 3H), 1.15 {t, 3H), 1.25 (d, 3H), 1.86-1.97 (m. IH), 2.45 (qt, 2H), 4.96-5.07 {m, 3H, involving a quartet at 4.97), 6.07 (s, IH), 8.41 (s,lH). Production Example 22 In 4 ml of tetrahydrofuran was suspended 0.13 g of sodium hydride (60% in oil), to which 0.5 ml of a solution containing 0.24 g of 3-inethyl-2-butanol was added dropwise at 0°C, followed by stirring for 10 minutes. To this was added dropwise 0.5 ml of a solution containing 0.40 g of 4,6-dichlo-ropyrimidine in tetrahydrofuran, followed by stirring at 0°C for 3 hours. To this was added dropwise 0.5 ml of a solution containing 0.29 g of 2-pentyn-l-ol in tetrahydrofuran and further added 0.15 g of sodium hydride {60% in oil), followed by stirring at room temperature for 4 hours. The reaction mixture was then poured into a saturated aqueous ammonium chloride solution, which was extracted three times with t-butyl methyl ether. The combined organic layers were washed with a saturated aqueous sodium chloride solu¬tion, dried over anhydrous magnesium sulfate, and then concentrated. The residue was subjected to silica gel column chromaT;ography to give 0.44 g of 4-(1.2-dimethylpropyloxy)-6-(2-pentynyloxy)pyrimidine (the present com¬pound (22)). 'H-NMR: 0.94 (d, 3H), 0.96 (d. 3H), 1.15 (t, 3H), 1.25 (d, 3H), 1.86-1.97 (m, IH). 2.45 (qt, 2H), 4.96-5.07 (m. 3H, involving a quartet at 4.97). 6.07 (s, IH), 8,41 (s. IH). Production Example 23 In 4 ml of tetrahydrofuran was suspended 0.10 g of sodium hydride (60% in oil), to which 0.4 ml of a solution containing 0.17 g of 2-butanol was added dropwise at 0°C, followed by stirring for 10 minutes. To this was added dropwise 0.4 ml of a solution containing 0.30 g of 4,6-dichioropyrimi-dine in tetrahydrofuran, followed by stirring at the same temperature for 3 hours. To this was added dropwise 0.4 ml of a solution containing 0.18 g of 2-butyn-l-ol in tetrahydrofuran and further added 0.10 g of sodium hydride (60% in oil), followed by stirring at room temperature for 7 hours. The reaction mixture was then poured into a saturated aqueous ammonium chloride solution, which was extracted three times with t-butyl methyl ether. The combined organic layers were washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then con¬centrated. The residue was subjected to silica gel column chromatography to give 0.31 g of 4-(sec-butyloxy)-6-(2-butynyloxy)pyrimidine (the present compound (23)). 'H-NMR: 0.94 (t, 3H), 1.30 (d, 3H), 1.59-1.78 (m, 2H), 1.87 (t, 3H), 4.95 (q, 2H), 5.10-5.15 (m, IH), 6.06 (s, IH). 8.42 (s, IH). Production Example 24 In 2 ml of tetrahydrofuran was suspended 0.05 g of sodium hydride "0% in oil), to which 0.3 ml of a solution containing 0.10 g of 3-methyl-2-atanol was added dropwise at 0°C, followed by stirring for 10 minutes. To lis was added dropwise 0.3 ral of a solution containing 0.20 g of 4,5,6-tri-iloropyrimidine in tetrahydrofuran, followed by stirring at the same tern-erature for 6 hours. To this was added dropwise 0.3 ml of a solution con-lining 0.08 g of 2-butyn-l-ol in tetrahydrofuran and further added 0.05 g of Ddium hydride (60% in oil), followed by stirring at room temperature for 3 ours. The reaction mixture was then poured into a saturated aqueous mmonium chloride solution, which was extracted three times with t-butyl aethyl ether. The combined organic layers were washed with a saturated .queous sodium chloride solution, dried over anhydrous magnesium sulfate, md then concentrated. The residue was subjected to silica gel column :hromatography to give 0.15 g of 4-(2-butynyloxy)-5-chloro-6-(l,2-dimethyl-)ropyloxy)pyrimidine (the present compound (24)). 'H-NMR: 0.97-1.00 (m, 6E), 1.30 (d, 3H), 1.87 (t, 3H), 1.93-2.01 (m, LH), 5.02-5.14 (m. 3H, involving a quartet at 5.03), 8.28 (s, iH). Production Example 25 In 2 ml of tetrahydrofuran was suspended 0.06 g of sodium hydride (60% in oil), to which 0.3 ml of a solution containing 0.11 g of 3-methyl-2-butanol was added dropwise at 0°C, followed by stirring for 10 minutes. To this was added dropwise 0.3 ml of a solution containing 0.20 g of 4,6-di-chloro-5-methylpyrimidine in tetrahydrofuran, followed by stirring at the same temperature for 5 hours. To this was added dropwise 0.3 ml of a solu¬tion containing 0.10 g of 2-butyn-l-ol in tetrahydrofuran and further added 0.06 g of sodium hydride (60% in oil), followed by stirring at room tempera- ture for 3 hours. The reaction mixture was then poured into a saturated aqueous ammonium chloride solution, which was extracted three times with t-butyl methyl ether. The combined organic layers were washed with a saturated aqueous sodium chloride solution, dried over anhydrous magne¬sium sulfate, and then concentrated. The residue was subjected- to silica gel column chromatography to give 0.20 g of 4-(2-butynyloxy)-6-{l,2-dimethyl-propyloxy)-5-methylpyrimidine {the present compound (25)). 'H-NMR: 0.95-0.98 (m. GH), 1.26 (d. 3H), 1.86-1.96 (m, 4H, involving a triplet at 1.87), 2.02 (s, 3H), 4.97 (q, 2H), 5.02-5.09 (m, IH), 8.29 (s, IH). Production Example 26 In 4 ml of tetrahydrofuran was suspended 0.10 g of sodium hydride (60% in oil), to which 0.4 ml of a solution containing 0.23 g of l-cyclopentyl-ethanol was added dropwise at 0°C, followed by stirring for 10 minutes. To this was added dropwise 0.4 ml of a solution containing 0.30 g of 4,6-di-chloropyrimidine in tetrahydrofuran, followed by stirring at the same tem¬perature for 4 hours. To this was added dropwise 0.4 ml of a solution con¬taining 0.16 g of 2-butyn-l-ol in tetrahydrofuran and further added 0.10 g of sodium hydride (60% in oil), followed by stirring for 3 hours. The reaction mixture was then poured into a saturated aqueous ammonium chloride solu¬tion, which was extracted three times with t-butyl methyl ether. The com¬bined organic layers were washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated. The residue was subjected to silica gel column chromatography to give 0.25 g of 4-(2-butynyloxy)-6-(l-cyclopentylethyloxy)pyrimidine (the present com¬pound (26)). 'H-NMR: 1.23-1.36 (m, 5H), 1.55-1.87 (m, 8H, involving a triplet at 1.87), 2.02-2.14 (m, IH), 4.95 (q, 2H), 5.03-5.10 (m, IH), 6.05 (s, IH), 8.42 (s, IH). Production Example 27 In 4 ml of tetrahydrofuran was suspended 0.10 g of sodium hydride (60% in oil), to which 0.4 ml of a solution containing 0.26 g of 1-cyclohexyl-ethanol was added dropwise at 0°C, followed by stirring for 10 minutes. To this was added dropwise 0,4 ml of a solution containing 0.30 g of 4,6-di-chloropyrimidine in tetrahydrofuran, followed by stirring at the same tem¬perature for 4 hours. To this was added dropwise 0.4 ml of a solution con¬taining 0.16 g of 2-butyn-l-ol in tetrahydrofuran and further added 0.10 g of sodium hydride (60% in oil), followed by stirring for 4 hours. The reaction mixture was then poured into a saturated aqueous ammonium chloride solu¬tion, which was extracted three times with t-butyl methyl ether. The com¬bined organic layers were washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated. The residue was subjected to sihca gel column chromatography to give 0.44 g of 4-(2-butynyloxy)-6-(l-cyclohexylethyloxy)pyrimidine (the present com¬pound (27)). 'H-NMR: 0.88-1.27 (m, 8H, involving a doublet at 1.24), 1.57-1.88 (m, 9H, involving a triplet at 1.87), 4.94 (q, 2H), 4.97-5.06 (m, IH), 6.05 (s, IH), 8.41 (s, IH). Production Example 28 First, 0.33 g of 4-(2-butynyloxy)-6-(2-hydroxy-2-methylpropyloxy)-pyrimidine was dissolved in 3 ml of chloroform, to which 0.5 ml of a solution containing 0.25 g of DAST in chloroform was added dropwise at OC, followed by stirring for 30 minutes. The reaction mixture was then poured into water, ) which was extracted three times with chloroform. The combined organic layers were washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate , and then concentrated. The residue was subjected to silica gel column chromatography to give 0.21 g of 4-(2- butynyloxy)-6-(2-fluoro-2-methylpropyloxy)pyrimidine (the present com¬pound (28)). H-NMR: 1.45 (d, 6H), 1.87 (t, 3H), 4.37 (d, 2H), 4.96 (q, 2H), 6.18 (s, IH), 8.43 (s, IH). Production Example 29 First, 0.38 g oi 4,6-dichioropyrimidine was" dissolved in 5 inl'of tetra-hydrofuran, to which 0.12 g of sodium hydride (60% in oil) was added and 0.4 ml of a solution containing 0.33 g of l.l-dichloro-2-propanol in tetrahydro-furan was added dropwise at 0°C, followed by stirring at 0°C for 2 hours. To this was added dropwise 0,4 ml of a solution containing 0.16 g of 2-butyu-l-ol in tetrahydrofuran at room temperature and further added 0.10 g of sodium hydride (60% in oU), followed by stirring at room temperature for 3 hours. The reaction mixture was then poured into a saturated aqueous ammonium chloride solution, which was extracted three times with t-butyl methyl ether. The combined organic layers were washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then con¬centrated. The residue was subjected to silica gel column chromatography to give 0.32 g of 4-(2-butynyloxy)-6-(2,2-dichloro-l-methylethyloxy)pyrimi-dine (the present compound (29)). 'H-NMR: 1.55 (d, 3H), 1.87 (t, 3H), 4.95 (q, 2H), 5.54-5.62 (m, IH), 6.05 (m, IH), 6.16 (s, IH), 8.43 (s, IH). Production Example 30 In 4 ml of tetrahydrofuran was suspended 0.11 g of sodium hydride (60% in oil), to which 0.4 ml of a solution containing 0.23 g of 2,4-dimethyl-3-pentanol was added dropwise at 0°C, followed by stirring for 10 minutes. To this was added dropwise 0.4 ml of a solution containing 0.30 g of 4,6-di-chloropyrimidine in tetrahydrofuran, followed by stirring at the same tem¬perature for 3 hours. To this was added dropwise 0.4 ml of a solution con- taining 0.17 g of 2-butyn-l-ol in tetrahydrofuran at room temperature and further added 0.11 g of sodium hydride (60% in oil), followed by stirring for 4 hours. The reaction mixture was then poured into a saturated aqueous ammonium chloride solution, which was extracted three times with t-butyl methyl ether. The combined organic layers were washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated. The residue was subjected to silica gel column chromatography to give 0.44 g of 4-(2-butynyloxy)-6-(l-isopropyl-2-methyl-propyloxy)pyrimidine (the present compound (30)). 'H-NMR: 0.91 (d, 12H), 1.88 (t, 3H), 1.96-2.04 (m. 2H), 4.95 (q, 2H), 5.05-5.08 (m. IH), 6.07 (s, IH). 8.39 (s, IH). Production Example 31 In 2 ml of tetrahydrofuran was suspended 0.03 g of sodium hydride (60% in oil), to which 0.3 ml of a solution containing 0.26 g of 4-chioro-6-(2-hydroxy-l,2-dimethylpropyloxy)pyrimidine was added dropwise at room temperature, followed by stirring for 10 minutes. To this was added drop-wise 0.3 ml of a solution containing 0.11 g of iodomethane in tetrahydrofuran, followed by further stirring at the same temperature for 4 hours. To this was added dropwise 0.3 ml of a solution containing 0.06 g of 2-butyn-l-ol in tetrahydrofuran at room temperature and further added 0.03 g of sodium hydride (60% in oil), followed by stirring for 5 hours. The reaction mixture was then poured into a saturated aqueous ammonium chloride solution, which was extracted three times with t-butyl methyl ether. The combined organic layers were washed with a saturated aqueous sodium chloride solu¬tion-, dried over anhydrous magnesium sulfate, and then concentrated. The residue was subjected to silica gel column chromatography to give 0.04 g of 4-(2-butynyloxy)-6-(2-methoxy-l,2-dimethylpropyloxy)pyrimidine (the pre¬sent compound (31)). 'H-NMR: 1.21 (s, 3H), 1.22 (s, 3H), 1.28 (d, 3H), 1.87 (t, 3H), 3.26 (s, 3H), 4.94 (q, 2H), 5.28 (q, IH), 6.10 (s, IH), 8.42 (s. IH). Production Example 32 In 1.5 ml of tetrahydrofuran was suspended 0.04 g of sodium hydride (60% in oil), to which 0.3 ml of a solution containing 0.07 gof 2-butyn-l-ol was added dropwise at room temperatute, foUoweti by stirring for 10,minutes. To this was added dropwise 0.3 ml of a solution containing 0.23 g of 4-chio-ro-6-(2,2-dichloro-l-methylcyclopropylmethyloxy)pyrimidine in tetrahydro¬furan at Q°C, followed by stirring at room temperature for 7 hours. The reaction mixture was then poured into a saturated aqueous ammonium chloride solution, which was extracted three times with t-butyl methyl ether. The combined organic layers were washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then con¬centrated. The residue was subjected to silica gel column chromatography to give 0.22 g of 4-(2-butynyloxy)-6-{2,2-dichloro-l-methylcyclopropyl)me-thoxypyrimidine (the present compound (32)). 'H-NMR: 1.36 (d, IH), 1.50 (s, 3H), 1.56 (d, IH), 1.88 {t, 3H), 4.34 (d, IH), 4.58 (d, IH), 4.96 (q, 2H), 6.18 (s, IH), 8.43 {s, IH). Production Example 33 In 7 ml of tetrahydrofuran was suspended 0.24 g of sodium hydride (60% in oil), to which 1 ml of a solution containing 0.28 g of propargyl alcohol was added dropwise at room temperature, followed by stirring for 10 minutes. To this was added dropwise 1 ml of a solution containing 1 g of 4-chloro-6-(l,2-dimethylpropyloxy)pyriniidine in tetrahydrofuran at the same tempera¬ture, followed by stirring at room temperature for 5 hours. The reaction mixture was then poured into a saturated aqueous ammonium chloride solu¬tion, which was extracted three times with t-butyl methyl ether. The com¬bined organic layers were washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated. The residue was subjected to sihca gel column chromatography to give 1.24 g of 4-(l,2-dimethylpropyloxy)-6-(2-propynloxy)pyrimidine (the present com¬pound (33)). 'H-NMR: 0.95 (d, 3H), 0.98 (d, 3H), 1.26 (d, 3H), 1.88-1.96 (m, IH). 2.50 (t, IH), 4.98-5.05 {m, 3H), 6.07 (s, IH),' 8.44 (s,lH). Production Example 34 In 3 ml of carbon tetrachloride were dissolved 0.23 g of 4-(2-butynyl-oxy)-6-(l,2-dimethylallyloxy)pyrimidine and 0.01 g of trioctylmethylammo-nium chloride, to which 1 ml of concentrated hydrochloric acid was added dropwise at 0°C, followed by stirring at 0°C for 30 minutes and at room tem¬perature for 3 hours. The reaction mixture was then poured into water, which was extracted three times with t-butyl methyl ether. The combined organic layer was washed with a saturated aqueous sodium hydrogencar-bonate solution, a saturated aqueous sodium chloride solution, dried over anhydrous magnesium, and then concentrated. The residue was subjected to silica gel column chromatography to give 0.05 g of 4-{2-butynyloxy)-6-(2-chloro-l,2-dimethylpropyloxy)pyrimidine (the present compound (34)). 'H-NMR: 1.41 (d, 3H), 1.60 (s, 6H), 1.87 (t, 3H), 4.95 (q, 2H), 5.41 (q, IH), 6.12 (s, IH), 8.43 (s, IH). Production Example 35 In 4 ml of tetrahydrofuran was suspended 0.11 g of sodium hydride (60% in oil), to which 0.4 ml of a solution containing 0.30 g of 2,2,2-trichloro-ethanol was added dropwise at 0°C, followed by stirring for 10 minutes. To this was added dropwise 0.4 ml of a solution containing 0.30 g of 4,6-di-chloropyrimidine in tetrahydrofuran, followed by stirring at the same tem¬perature for 2 hours. To this was added dropwise 0.4 ml of a solution con¬taining 0.17 g of 2-butyn-l-ol at room temperature and further added 0.11 g of sodium hydride (60% in oil), followed by stirring for 3 hours. The reaction ■ mixture was then poured into a saturated aqueous ammonium chloride solu¬tion, which was extracted three times with t-butyl methyl ether. The com¬bined organic layers were washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated. The'reiduewas sabjected to silica gercolumn chromatography to give 0.20 g of 4-(2-butynyloxy)-6-(2,2.2-trichloroethyloxy)pyrimidine (the present com¬pound (35)). 'H-NMR: 1.88 (t, 3H), 4.98 (q, 2H), 5.08 (s, 2H), 6.29 (s, IH), 8.46 (s, IH). Production Example 36 In 6 ml of tetrahydrofuran was suspended 0.15 g of sodium hydride (60% in oil), to which 0.4 ml of a solution containing 0.45 g of 3,3-dichloro-2-butanol was added dropwise at 0°C, followed by stirring for 10 minutes. To this was added dropwise 0.4 ml of a solution containing 0.47 g of 4,6-di-chloropyrimidine in tetrahydrofuran, followed by stirring at the same tem¬perature for 4 hours. To this was added dropwise 0.4 ml of a solution con¬taining 0.17 g of 2-butyn-l-ol at room temperature and further added 0.19 g of sodium hydride (60% in oil), followed by stirring for 2 hours. The reaction mixture was then poured into a saturated aqueous ammonium chloride solu¬tion, which was extracted three times with t-butyl methyl ether. The com¬bined organic layers were washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated. The residue was subjected to sihca gel column chromatography to give 0.39 g of 4-(2-butynyloxy)-6-(2,2-dichloro-l-methylpropyloxy)pyrimidine (the pre¬sent compound (36)). H-NMR: 1.57 (d, 3H), 1.88 (t, 3H), 2.16 (s, 3H), 4.96 (q, 2H), 5.72 (q, 12H), 6.17(s, IH), 8.45(s, IH). Production Example 37 In 1.5 ml of tetrahydrofuran was suspended 0.04 g of sodium hydride {60% in oil), to which 0.5 ml of a solution containing 0.07 gof 2-butyn-l-ol was added dropwise at room temperature, followed by stirring for 10 minutes. To this was added dropwise 0.5 ml of a solution containing 0.18 g of 4-chlo-ro-6-(2,2-dichloropropyloxy)pyrimidine in tetrahydrofuran, followed by stir¬ring for 2 hours. The reaction mixture was then poured into a saturated aqueous ammonium chloride solution, which was extracted three times with t-butyl methyl ether. The combined organic layers were washed with a saturated aqueous sodium chloride solution, dried over anhydrous magne¬sium sulfate, and then concentrated. The residue was subjected to silica gel column chromatography to give 0.08 g of 4-(2-butynyloxy)-6-(2,2-dichloro-propyloxy)pyrimidine (the present compound (37)). 'H-NMR: 1.87 (t, 3H), 2.19 (s, 3H), 4.78 (s, 2H), 4.98 (q, 2H), 6.22 (s, IH), 8.45 (s, IH). Production Example 38 In 3 ml of tetrahydrofuran was suspended 0.10 g of sodium hydride (60% in oil), to which 0.4 ml of a solution containing 0.33 g of 3,3,3-trichIoro-2-propanol was added dropwise at room temperature, followed by stirring for 10 minutes. To this was added dropwise 0.4 ml of a solution containing 0.3 g of 4,6-dichloropyrimidine in tetrahydrofuran at 0°C, followed by stirring at the same temperature for 30 minutes. To this was added dropwise 0.4 ml of a solution containing 0.20 g of 2-pentyn-l-ol at room temperature and further added 0.10 g of sodium hydride (60% in oil), followed by stirring for 2 hours. The reaction mixture was then poured into a saturated aqueous ammonium chloride solution, which was extracted three times with t-butyl methyl ether. The combined organic layers were washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated. The residue was subjected to silica gel column chromatography to give 0.47 g of 4-(2-pentynyloxy)-6-(2,2,2-trichloro-l-methylethoxy)pyrimidine (the present compound (38)). 'H-NMR: 1.15 (t, 3H), 1.67 (d, 3H), 2.25 (qt, 2H), 4.99 (t, 2H), 6.02 (q, IH), 6.22 (s, IH), 8.45 (s, IH). Production Example 39 In 3 ml of tetrahydrofuran was suspended 0.09 g of sodium hydride (60% in oil), to which 0.4 ml of a solution containing 0.31 g of 1,1-dichloro-3,3-dimethyl-2-butanol was added dropwise at room temperature, followed by stirring for 10 minutes. To this was added dropwise 0.4 ml of a solution containing 0.27 g of 4,6-dichloropyrimidine in tetrahydrofuran at 0°C, fol¬lowed by stirring at the same temperature for 2.5 hours. To this was added dropwise 0.4 ml of a solution containing 0.15 g of 2-butyn-l-ol in tetrahydro¬furan at room temperature and further added 0.09 g of sodium hydride (60% in oil), followed by stirring for 4 hours. The reaction mixture was then poured into a saturated aqueous ammonium chloride solution, which was extracted three times with t-butyl methyl ether. The combined organic layers were washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated. The residue was subjected to silica gel column chromatography to give 0.45 g of 4-(2-butynyloxy)-6-(l-(dichloromethyl)-2,2-dimethylpropyloxy)pyrimidine (the present compound (39)). 'H-NMR: 1.08 (s, 9H), 1.88 (t, 3H), 4.97 (q, 2H), 5.79 (d, IH), 6.06 (d, IH), 6.24 (s, IH), 8.44 (s, IH). Production Example 40 In 5 ml of chloroform were dissolved 0.64 g of 4-(2-pentynyloxy)-6-(2-methyI-2-propenyloxy)pyrimidine and 0.06 g of trioctylmethylammonium chloride, to which 3 ml of concentrated hydrochloric acid was added dropwise at OC, followed by stirring at 0°C for 30 minutes and at room temperature for 7 hours. The reaction mixture was then poured into water, which was extracted three times with t-butyl methyl ether. The combined organic layer was washed with a saturated aqueous sodium hydrogencarbonate solution, a saturated aqueous sodium chloride solution, dried over anhydrous magnesium, and then concentrated. The' residue was subjected to silica gel column chromatography to give 0.12 g of 4-(2-pentynyloxy)-6-(2-chloro-2-methylpropyloxy)pyrimidine (the present compound (40)). 'H-NMR: 1.15 (t, 3H), 1.66 (s, 6H), 2.24 (qt. 2H), 4.42 (s, 2H), 4.97 (t, 2H), 6.18 (s, IH), 8.43 (s, IH). Production Example 41 To a solution containing 0.3 g of 4-(2-pentynyloxy)-6-(l,2-dimethyl-2-propenyloxy)pyrimidine in 3 ml of tetrahydrofuran was added dropwise 3.66 ml of a 1 mol/1 solution of hydrogen chloride in diethyl ether, followed by stirring at room temperature for 9 hours. The reaction mixture was then poured into a saturated aqueous sodium hydrogencarbonate solution, which was extracted three times with t-butyl methyl ether. The combined organic layers were washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium chloride, and then concentrated. The residue was subjected to silica gel column chromatography to give 0.07 g of 4-(2-pen-tynyloxy)-6-(2-chloro-l,2-dimethylpropyloxy)pyrimidine (the present com¬pound (41)), 'H-NMR: 1.15 (t, 3H), 1.31 (d, 3H), 1.64 (s, 6H), 2.25 (qt, 2H), 4.96 (t, 2H), 5.39 (q, IH). 6.13 (s, IH), 8.42 (s, IH). The present compounds described in the above production examples are listed together with their compound numbers in Tables 1 and 2. The compounds of formula (1): The following will reference production examples for the production of intermediates in the production of the present compounds. Reference Production Example 1 In 3.5 ml of tetrahydrofuran was suspended 0.11 g of sodium hydride (60% in oil), to which 0.5 mFof tetrahydrofuran containing 0.12 g of isopropyl alcohol dissolved therein was added dropwise at 0°C, followed'Uy stirring for 10 minutes. To this was added dropwise 0.5 ml of tetrahydrofuran contain¬ing 0.3 g of 4,6-dichloropyrimidine dissolved therein, followed by stirring at 0°C for 2 hours. The reaction mixture was then poured into a saturated aqueous ammonium chloride solution, which was extracted three times with t-butyl methyl ether. The combined organic layers were washed with a saturated aqueous sodium chloride solution, dried over anhydrous magne¬sium sulfate, and then concentrated. The residue was subjected to silica gel column chromatography to give 0.26 g of 4-chloro-6-isopropyloxypyrimidine. 'H-NMR: 1.36 (d. 6H), 5.33-5.43 (m, IH), 6.70 (s, IH), 8.55 (s, IH). Reference Production Example 2 In 4 ml of tetrahydrofuran was suspended 0.11 g of sodium hydride (60% in oU), to which 0.5 ml of tetrahydrofuran containing 0.23 g of 3,3-di-methyl-2-butanol dissolved therein was added dropwise at room temperature, followed by stirring for 10 minutes. To this was added dropwise 0.5 ml of tetrahydrofuran containing 0.3 g of 4,6-dichloropyrimidine dissolved therein, followed by stirring at the same temperature for 6 hours. The reaction mixture was then poured into a saturated aqueous ammonium chloride solu¬tion, which was extracted three times with t-butyl methyl ether. The com¬bined organic layers were washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated. The residue was subjected to sihca gei column chromatography to give 0.24 g of 4-chloro-6-(l,2,2-trimethylpropyloxy)pyrimidine. Reference Production Example 3 In 4 ml of tetrahydrofuran was suspended 0.11 g of sodiunJ hydride (60% in oil), to which 0.5 ml of tetrahydrofuran containing 0.26 g of 2.2-di-methyl-3-pentanol dissolved therein was added dropwise at room tempera¬ture, followed by stirring for 10 minutes. To this was added dropwise 0.5 ml of tetrahydrofuran containing 0.3 g of 4,6-dichloropyrimidine dissolved therein at 0°C, followed by stirring at the same temperature for 1 hour and at room temperature for 4 hours. The reaction mixture was then poured into a saturated aqueous ammonium chloride solution, which was extracted three times with t-butyl methyl ether. The combined organic layers were washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated. The residue was subjected to silica gel column chromatography to give 0.35 g of 4-chloro-6-(l-ethyl-2,2-dime thy Ip ropy loxy)pyrimi dine. 6.75 (s, IH), 8.52 (s, IH). Reference Production Example 4 In 4 ml of tetrahydrofuran was suspended 0.10 g of sodium hydride (60% in oil), to which 0.5 ml of tetrahydrofuran containing 0.14 g of 2,2-di-methyl-l-propanol dissolved therein was added dropwise at room tempera¬ture, followed by stirrfn'for 10 minutes. To this was added dropwise 0.5 ml of tetrahydrofuran containing 0.3 g of 4,6-dichloropyrimidine dissolved therein at QC, followed by stirring at the same temperature for 4 hours. The reaction mixture was then poured into a saturated aqueous ammonium chloride solution, which was extracted three times with t-butyl methyl ether. The combined organic layers were washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then con¬centrated. The residue was subjected to siUca gel column chromatography to give 0.16 g of 4-chloro-6-{2,2-dimethylpropyloxy)pyrimidine. 4-Chloro-6-(2,2-dimethylpropyloxy)pyrimidine Reference Production Example 5 In 4 ml of tetrahydrofuran was suspended 0.13 g of sodium hydride (60% in oil), to which 5.4 ml of a 0.5 molTl solution containing l-(l-methyl-:yloropropyl)ethanol was added dropwise at 0°C, followed by stirring for 10 minutes. To this was added dropwise 0.5 ml of tetrahydrofuran containing 3.4 g of 4,6-dichloropyrimidine dissolved therein at 0°C, followed by stirring at the same temperature for 4 hours. The reaction mixture was then poured into a saturated aqueous ammonium chloride solution, which was extracted three times with t-butyl methyl ether. The combined organic layers were washed with a saturated aqueous sodium chloride solution, dried over i anhydrous magnesium sulfate, and then concentrated. The residue was subjected to silica gel column chromatography to give 0.18 g of 4-chloro-6-[l-(l-methylcyclopropyl)ethyloxy]pyrimidine. 4-Chloro-6-[l-(l-methyicyclopropyl)ethyloxy]pyrimidine Reference Production Example 6 In 5 ml of tetrahydrofuran was suspended 0.14 g of sodium hydride {60% in oil), to which 0.5 ml of a solution containing 0.36 g of 3-chloro-2,2-dimethyl-1-propanol was added dropwise at 0°C, followed by stirring for 10 minutes. To this was added dropwise 0.5 ml of tetrahydrofuran containing 0.4 g of 4,6-dichloropyrimidine dissolved therein, followed by stirring at the same temperature for 2 hours. The reaction mixture was then poured into a saturated aqueous ammonium chloride solution, which was extracted three times with t-butyl methyl ether. The combined organic layers were washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated. The residue was subjected to silica gel column chromatography to give 0.62 g of 4-chloro-6-{3-chloro-2,2-dimethylpropyloxy)pyrimidine. In 4 ml of tetrahydrofuran was suspended 0.11 g of sodium hydride (60% in oil), to which 0.5 ml of a solution containing 0.23 g of 3,3-diinethyl-l-butanol was added dropwise at 0°C, followed by stirring for 10 minutes.. To this was added dropwise 0.5 ml of tetrahydrofuran containing 0.3 g of 4,6-dichloropyrimidine dissolved therein, followed by stirring at the same temperature for 4 hours. The reaction mixture was then poured into a saturated aqueous ammonium chloride solution, which was extracted three times with t-butyl methyl ether. The combined organic layers were washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated. The residue was subjected to silica gel column chromatography to give 0.41 g of 4-chloro-6-(3,3-dimethyl-b uty loxy)py r imidine. Reference Production Example 8 In 4 ml of tetrahydrofuran was suspended 0.10 g of sodium Hydride (60% in oU), to which 0.5 ml of a solution containing 0.18 g of 3-methyl-2-butanol was added dropwise at 0°C, followed by stirring for 10 minutes. To this was added dropwise 0.5 ml of tetrahydrofuran containing 0.3 g of 4.6-di-chioropyrimidine dissolved therein, followed by stirring at the'same temper-' ature for 4 hours. The reaction mixture was then poured into a saturated aqueous ammonium chloride solution, which was extracted three times with t-butyi methyl ether. The combined organic layers were washed with a saturated aqueous sodium chloride solution, dried over anhydrous magne¬sium sulfate, and then concentrated. The residue was subjected to silica gel column chromatography to give 0.35 g of 4-chloro-6-{l,2-dimethylpropyl-oxy)pyrimidine, 'H-NMR: 0.95 (d, 3H), 0.97 (d, 3H), 1.27 (d, 3H). 1.78-2.14 (m, IH), 5.10-5.16 (m, IH), 6.73 (s. IH), 8.54 (s, IH). Reference Production Example 9 In 4 ml of tetrahydrofuran was suspended 0.10 g of sodium hydride (60% in oil), to which 0.5 ml of a solution containing 0.34 g of 3-bromo-2.2-dimethyl-1-propanoI was added dropwise at 0°C, followed by stirring for 10 minutes. To this was added dropwise 0.5 ml of tetrahydrofuran containing 0.3 g of 4,6-dichloropyrimidine dissolved therein, followed by stirring at the same temperature for 4 hours. The reaction mixture was then poured into a saturated aqueous ammonium chioride solution, which was extracted three times with t-butyl methyl ether. The combined organic layers were washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated. The residue was subjected to silica'gel column chromatography to give 0.56 g of 4-chloro-6K3-bromo-2,2-dimethylpropyloxy)pyrimidine. Reference Production Example 10 In 8 ml of tetrahydrofuran was suspended 0.41 g of sodium hydride (60% in oil), to which 0.6 ml of a solution containing 0.49 g of 2-methyl-butane-2,3-diol was added dropwise at 0°C, followed by stirring for 10 min¬utes. To this was added dropwise 0.6 ml of tetrahydrofuran containing 0.69 g of 4,6-dichloropyrimidine dissolved therein, followed by stirring at the same temperature for 4.5 hours. The reaction mixture was then poured into a saturated aqueous ammonium chloride solution, which was extracted three times with t-butyl methyl ether. The combined organic layers were washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated. The residue was subjected to silica gel column chromatography to give 0.74 g of 4-chloro-6-(2-hydroxy-l,2-dimethylpropyloxy)pyrimidine. 4-Chloro-6-(2-hydroxy-l,2-dimethylpropyloxy)pyrimidine In 3 ml of tetrahydrofuran was suspended 0.17 g of sodium hydride (60% in oil), to which 0.4 ml of a solution containing 0.17 g of 2-pentyn-l-ol was added dropwise at 0°C, followed by stirring for 10 minutes. To this was added dropwise 0.4 ml of tetrahydrofuran coGtaining 0.37 g of 3-(G-chloro-4-pyrimidyloxy)-2-methyl-2-butanol dissolved therein, followed by stirring at the same temperature for 1 hour and at room temperature for 4 hours. The reaction mixture was then poured into a saturated aqueous amm.onium chloride solution, which was extracted three times with t-butyi methyl ether The combined organic layers were washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then con¬centrated. The residue was subjected to siUca gel column chromatography to ve 0.33 g of 4-{2-pentynyioxy)-6-(2-hydroxy-l,2-dimethylpropyloxy)pyri-midine. Reference Production Example 12 In 5 ml of tetrahydroftoran was suspended 0.13 g of sodium hydride (60% in oil), to which 5.4 ml of a 0.5 mol/l solution containing 1,1-diinethoxy-2-propanoI in tetrahydrofuran was added dropwise at OC, followed by stir¬ring for 10 minutes. To this was added dropwise 0.5 ml of tetrahydrofuran containing 0.4 g of 4,6-dichloropyrimidine dissolved therein, followed by stir¬ring at 0°C for 4 hours. The reaction mixture was then poured into a saturated aqueous ammonium chloride solution, which was extracted three times with t-butyi methyl ether. The combined organic layers were washed yiith a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated. The residue was subjected to silica gel column chromatography to give 0.16 g of 4-chioro-6-(2,2-dimethoxy-1 - me thyiethoxy )pyrim idine. In 4 ml of tetrahydrofuran was suspended 0.11 g of sodium hydride (60% in oil), to which 0.5 ml of a solution containing 0.16 g of 2-methyl-2-propenol in tetrahydrofuran was added dropwise at 0°C, followed by stirring for 10 minutes. To this was added dropwise 0.5 ml of a solution containing 0.4 g of 4-{2-butynyloxy)-6-chloropyrimidine in tetrahydrofuran, followed by stirring at the same temperature for 2 hours. The reaction mixture was then poured into a saturated aqueous ammonium chloride solution, which was extracted three times with t-butyl methyl ether. The combined organic layers were washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated. The residue was subjected to siHca gel column chromatography to give 0.15 g of 4-(2-butynyloxy)-6-(2-methyla!lyloxy)pyrimidine. In 20 ml of tetrahydrofuran was dissolved 1 g of l-hydroxy-2-propanone, to which 26 ml of a 1.14 mol/1 solution (diethyl ether solution) of methyl lithium was added dropwise at -78°C. The mixture was stirred at the same temperature for 1 hour. After gradually increasing the tempera¬ture up to 0°C, 4 ml of a solution containing 2 g of 4,6-dichloropyrimidine in tetrahydrofuran was added dropwise, followed by further stirring 2 hours. The reaction mixture was then poured into a saturated aqueous ammonium chloride solution, which was extracted three times with ethyl acetate. The combined organic layers were washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then con¬centrated. The residue was subjected to silica gel column chromatography to give 0.66 g of 4-chloro-6-(2-hydroxy-2-methylpropyloxy)pyrimidine. 4-Chloro-6-(2-hydroxy-2-methylpropyioxy)pyrimidiiie In 6 ml of tetrahydrofuran was suspended 0.29 g of sodium hydride (60% in oil), to which 0.4 ml of a solution containing 0.25 g of 2-butyn-l-ol in tetrahydrofuran was added dropwise at room temperature, followed hy stir¬ring for 10 minutes. To this was added dropwise 0.4 ml of a solution con¬taining 0.66g of l-(6-chloropyrimidin-4-yloxy)-2-methyi-2-propanol" in tetrahydrofuran at 0°C, followed by increasing the temperature up to room temperature and stirring for 5 hours. The reaction mixture was then poured into a saturated aqueous ammonium chloride solution, which was extracted three times with ethyl acetate. The combined organic layers were washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated. The residue was subjected to silica gel column chromatography to give 0.33 g of 4-(2-butynyloxy)-6-(2-hydroxy-2-methylpropyloxy)pyrimidine. Ueference Production Example 16 In 5 ml of tetrahydrofuran was suspended 0.24 g of sodium hydride {60% in oil), to which 0.4 ml of a solution containing 0.26 g of 2-methylbutan-2,3-diol in tetrahydrofuran was added dropwise at 0°C, followed by stirring for 10 minutes. To this was added dropwise 0.4 ml of a solution containing 0.38 g of 4,6-dichloropyrimidin in tetrahydrofuran.'followed by stirring at 0°C for 4 hours. To this was added dropwise 0.4 ml of a solution containing 0.20 g of 2-butyn-l-ol and further added 0.12 g of sodium hydride (60% m oil), followed by stirring at room temperature for 3.5 hours. The reaction mix¬ture was then poured into a saturated aqueous ammonium chloride solution, which was extracted three times with t-butyl methyl ether. The combined organic layers were washed with a saturated aqueous sodium chloride solu¬tion, dried over anhydrous magnesium sulfate, and then concentrated. The residue was subjected to silica gel column chromatography to give 0.41 g of 4-(2-butynyloxy)-6-(2-hydroxy-l,2-dimethylpropyloxy)pyrimidine. 4-{2-Butynyloxy)-6-(2-hydroxy-l,2-dimethylpropyloxy)pyrimidine Reference Production Example 17 In 10 mlof tetrahydrofuran was suspended 0.322 g of sodium hydride (60% in oil), to which 0.5 ml of a solution containing 0.16 g of 2-methyI-2-propenol in tetrahydrofuran was added dropwise at 0°C, followed by stirring for 10 minutes. To this was added dropwise 0.5 ml of a solution containing I g of 4,6-dichloropyrimidine in tetrahydrofuran, followed by stirring at the same temperature for 2 hours. The reaction mixture was then poured into a saturated aqueous ammonium chloride solution, which was extracted three times with t-butyl methyl ether. The combined organic layers were washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated. The residue was subjected to silica gel column chromatography to give 1.27 g of 4-chloro-6-{2-methylaIlyl- In 6.5 ml of chloroform was dissolved 0.6 g of 4-chloro-6-(2-methyl-allyloxy)pyrimidine, to which 0.02 g of benzyItriethy 1 ammonium chloride was added at 0°C and 3.25 ml of a 50% sodium hydroxide solution was further added dropwise at the same temperature, followed by stirring at room temperature for 14 hours. The reaction mixture was then poured into water, which was extracted three times with t-butyl methyl ether. The combined organic layers were washed with a saturated aqueous sodium chloride solu¬tion, dried over anhydrous magnesium sulfate, and then concentrated. The residue was subjected to sihca gel column chromatography to give 0.23 g of 4-chloro-6-[(2,2-dichloro-l-methylcyclopropyl)methoxy]pyrimidine. 4-Chloro-6-[(2,2-dichloro-l-methylcyclopropyl)methoxy]pyrimidine inidin-4-yIoxy]-2-methyl-2-butanol, to which 0.2 g of pyridine was added and 0.15 ml of thionyl chioride was added dropwise at -13°C, followed by stirring 2 hours. The reaction mixture was then poured into water, which was extracted three times with chloroform. The combined organic layers were washed with a saturated aqueous sodium hydrogencarbonate, a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated. The residue was subjected to silica gel column chromatography to give 0.23 g of 4-(2-butynyloxy)-6-(l,2-dimethyialIyloxy)- First, 0.23 g of 4,6-dichloropyrimidine and 0.2 g of 2,2-dichloro-l- propanol were dissolved in 2 ml of tetrahydrofuran, to which 0.07 g of sodium hydride (60% in oil) was added at 0°C, followed by stirring at the same tem¬perature for 2 hours. The reaction mixture was then poured into a satu¬rated aqueous ammonium chloride solution, which was extracted three times with t-butyl methyl ether. The combined organic layers were washed with a saturated aqueous sodium chloride solution, dried over anhydrous magne¬sium sulfate, and then concentrated. The residue was subjected to silica gel chromatography to give 0.18 g of 4-chloro-6-(2,2-dichlDropropyloxy)pyrimi- In 10 ml of tetrahydrofuran was suspended 0.19 g of sodium hydride (60% in oil), to which 0.5 ml of a solution containing 0.57 g of 2-pentyn-l-ol in tetrahydrofuran was added dropwise at room temperature, followed by stir¬ring for 10 minutes. To this was added dropwise 0.4 ml of a solution con¬taining 0.3 g of 4,6-dichloropyrimidin in tetrahydrofuran at 0°C, followed by stirring for 1 hour. To this was added dropwise 0.5 ml of a solution con¬taining 0.48 g of 2-methyl-2-propen-l-ol in tetrahydrofuran at the same temperature and further added 0.19 g of sodium hydride (60% in oil), followed by stirring at 2 hours. The reaction mixture was then poured into a saturated aqueous ammonium chloride solution, which was extracted three times with t-butyl methyl ether. The combined organic layers were washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated. The residue was subjected to silica gel column chromatography to give 0.64 g of 4-(2-methyl-2-propenyl-)xy)-6-(2-pentynyloxy)pyrimidine. In 3 ml of chloroform was dissolved 0.5 g of 4-{2-pentynyioxy)-6-(2-iydroxy-l,2-dimethylpropyloxy)pyrimidine, to which 0.18 g of pyridine was idded and 0.27 g of thionyl chloride was added dropwise at -13°C, followed yy stirring for 1.5 hours. The reaction mixture was then poured into water, vhich was extracted three times with chloroform. The combined organic ayers were washed with a saturated aqueous sodium hydrogencarbonate iolution, a saturated aqueous sodium chloride solution, dried over anhydrous nagnesium sulfate, and then concentrated. The residue was subjected to iihca gel column chromatography to give 0.3 g of 4-(2-pentynyloxy)-6-{l,2-limethyl- 2 -prop enyloxy)pyrimidine. ' H-NMR: 1.15 (t, 3H), 1.43 (d, 3H), 1.78 (s, 3H), 2.24 (qt, 2H), 4.87 (s, IH), 4.97 (t, 2H), 5.00 (s, IH), 5.54 (q, IH), 6.13 (s, IH), 8.42 (s, IH). The following will describe some formulation examples wherein parts represent parts by weight. The present compounds are designated by their compound numbers shown in Tables 1 and 2. Formulation Example 1 Emulsifiable concentrate Nine parts of each of the present compounds (1) to (40) is dissolved in 37.5 parts of xylene and 37.5 parts of dirDethylformamide, and 10 parts of polyoxyethylene styryl phenyl ether and 6 parts of calcium dodecylbenzene-sulfonate are added thereto, followed by well stirring and mixing, to give an Bmulsifiable concentrate for each compound. Formulation Example 2 Wettable powder Nine parts of each of the present compounds (1) to (40) is added to a mixture containing 4 parts of sodium lauryisulfate. 2 parts of calcium hgnin sulfonate, 20 parts of synthetic hydrated silicone oxide fine powder, and 65 parts of diatomaceous earth, followed by well stirring and mixing, to give a ivettable powder for each compound. Formulation Example 3 Granule To 3 parts of each of the present compounds (1) to (40) are added 5 jarts of synthetic hydrated silicon oxide fine powder, 5 parts of sodium iodecylbenzenesulfonate, 30 parts of bentonite, and 57 parts of clay, followed jy well stirring and mixing, and an appropriate amount of water is added to :his mixture, followed by further stirring, granulation with a granulator, and lir drying, to give a granule for each compound. Formulation Example 4 Dust First, 4.5 parts of each of the present compounds (1) to (40), 1 part of !ynthetic hydrated silicon oxide fine powder, 1 part of Doriresu B (Sankyo Co., jtd.) as a flocculant, and 7 parts of clay are well mixed with a mortar, followed by stirring and mixing with a mixer. To the resulting mixture is added 86.5 parts of cut clay, followed by well stirring and mixing, to give a dust for each compound. Formulation Example 5 Ten parts of each of the present compounds (1) to (40), 35 parts of white carbon containing 50 parts of polyoxyethylene alkyl ether sulfate am¬monium salt, and 55 parts of water are mixed and pulverized by the wet grinding method to give a formulation for each compound. The following test example will demonstrate that the present com¬pounds have excellent pesticidal activity. Test Example 1 Ten parts of each of the present compounds (1) to (6), (8) to (23), (30), (31), and (34) to (40); white carbon containing 50 parts of polyoxyethylene alkyl ether sulfate ammonium salt: and 55 parts of water were mixed and pulverized by the wet grinding method to give a formulation for each compound. The formulation of each present compound was diluted with water so that the active ingredient concentration came to 500 ppm to prepare a spray solution. A polyethylene cup was seeded with cucumber and a plant was grown until the first true leaf was developed, on which about twenty Aphis gossypii (cotton aphid) are allowed to be parasitic. On the next day, the above spray solution was applied at a ratio of 20 ml/cup to the cucumber plant. On the sixth day after the application, the number of Aphis gossypii was examined and the preventive value was determined by the following equation: Preventive value (%) = {1 - (Cb x Tai) / (Cai x Tb)} x 100 where the variables in the equation have the following meanings: Cb: the number of pests before treatment in an untreated area Cai: the number of pests when observed in the untreated area Tb: the number of pests before treatment in a treated area Tai: the number of pests when observed in the treated area. As a result, all the present compounds (1) to (6), (8) to (23), (30), (31), and (34) to (40) exhibited the preventive value of 90% or higher. Test Example 2 Ten parts of each of the present compounds (2), (4), (6). (7). (8), (11), (12), (14), (16). (17), (19) to (24), (26), (28), (29), (34), (36) to (38), and (40); white carbon containing 50 parts of polyoxyethylene alkyl ether sulfate am¬monium salt; and 55 parts of water were mixed and pulverized by the wet grinding method to give a formulation for each compound. The formulation of each present compound was diluted with water so that the active ingredient concentration came to 500 ppm to prepare a spray solution. A polyethylene cup was seeded with cucumber and a plant was grown until the first true leaf was developed, to which the above spray solution was applied at a ratio of 20 m.l/cup. After the chemical solution sprayed to the cucumber were dried, the first true leaf was cut off and placed on a filter paper (70 mm in diameter) impregnated with water in a polyethylene cup (110 mm in diameter). Thirty larvae of Frankliniella occidentahs (Western flower thrips) were set free on the iirst true leaf, which was covered with a polyethylene cup. After seven days, the number of surviving pests was ex¬amined. As a result, the number of siuiving pests was 0 on the leaves treated with each of the present compounds (2), (4), (6), (7), (8), (11), (12), (14), (16), (17), (19) to (24), (26), (28), (29), (34), (36) to (38), and (40). Test Example 3 Ten parts of each of the present compounds (2) to (8), (10) to (32) and (34) to (40); white carbon containing 50 parts of polyoxyethylene alkyl ether sulfate ammonium salt; and 55 parts of water were mixed and pulverized by the wet grinding method to give a formulation for each compound. formulation of each present compound was diluted with water so that the active ingredient concentration came to 500 ppm to prepare a spray solution. A polyethylene cup was seeded with cabbage and a plant was grown until the first true leaf was developed. The first true leaf was left, while the other leaves were cut off. Adults of Bemisia argentifolii (silverleaf whitefly) were set free on the first true leaf and allowed to lay eggs for about 24 hours. The cabbage leaf with about 80 to 100 eggs thus laid thereon was kept in a greenhouse. On eighth day after, when greater part of the larvae were hatching from the laid eggs, the above spray solution was applied at a ratio of 20 ml/cup to the cabbage plant. On the seventh day after the application, the number of surviving larvae was counted. As a result, the number of surviving larvae was not greater than 10 on the cabbage leaves treated with each of the present compounds (2) to (8), (10) to (32) and (34) to (40). Test Example 4 Ten parts of each of the present compounds (1) to (23) and (25) to (40); white carbon containing 50 parts of polyoxyethylene alkyl ether sulfate am¬monium salt; and 55 parts of water were mixed and pulverized by the wet grinding method to give a formulation for each compound. The formulation of each present compound obtained according to Formulation Example 5 was diluted so that the active ingredient concentration came to 500 ppm to prepare a spray solution-Fifty grams of molding Bonsoru 2 (available from Sumitomo Chemical Co., Ltd.) was put into a polyethylene cup, and 10 to 15 seeds of rice were planted in the polyethylene cup. Then rice plants were grown until the second foliage leaves developed and then cut into the same height of 5 cm. The above spray solution was applied at the rate of 20 ml/cup to these rice plants. After the chemical solution sprayed onto the rice plants were dried, thirty first-instar larvae of Nilaparvata lugens (brown planthopper) were set free on the rice plants, which was then left in a greenhouse at 25°C. On the sixth Say after the release of larvae of Nilaparvata lugens, the number of parasitic Nilaparvata lugens on the rice plants was examined. As a result, in the treatment with each of the present compounds (1) to (23) and (25) to (40), the number of parasitic Nilaparvata lugens on the sixth day after the treatment was not greater than 3. Industrial Applicability The present compounds have excellent pesticidal activity, and there¬fore, they are useful as the active ingredients of pesticidal compositions. WE CLAIM: 1. Apyrimidine compound of formula (1): wherein R1 is C3-C7 alkynyl; R2 is hydrogen, halogen, or C1-C3 alkyl; and R3 is C1-C8 alkyl that may be substituted with halogen or C1-C3 alkoxy, or C3-C6 cydoalkyl- (that may be substituted with halogen or C1-C3 alkyl) C1-C3 alkyl. 2. The pyrimidine compound as claimed in claim 1, wherein R1 is C3-C7 alkyuyl in which the bond between the carbon atoms at positions 2 and 3 is a triple bond. 3. The pyrimidine compound as claimed in claim 1, wherein R1 is 2-butyny1, 2-pentynyl, 3-methyl-2-bytynyl or l-methy]-2-pentynyl. 4. The pyrimidine compound as claimed in any one of claims 1 to 3, wherein R2 is hydrogen. 5. A pesticidal composition comprising a pyrimidine compound as claimed in claim 1 as an active ingredient. 6. Amethod for controlling pests comprising applying a pyrimi¬ dine compound as claimed in claim 1 to pests or habitats of pests. |
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1993-chenp-2004 abstract duplicate.pdf
1993-chenp-2004 claims duplicate.pdf
1993-chenp-2004 correspondence others.pdf
1993-chenp-2004 correspondence po.pdf
1993-chenp-2004 description (complete) duplicate.pdf
1993-chenp-2004 description (complete).pdf
1993-chenp-2004 pct search report.pdf
| Patent Number | 226373 | |||||||||
|---|---|---|---|---|---|---|---|---|---|---|
| Indian Patent Application Number | 1993/CHENP/2004 | |||||||||
| PG Journal Number | 02/2009 | |||||||||
| Publication Date | 09-Jan-2009 | |||||||||
| Grant Date | 17-Dec-2008 | |||||||||
| Date of Filing | 06-Sep-2004 | |||||||||
| Name of Patentee | SUMITOMO CHEMICAL COMPANY, LIMITED | |||||||||
| Applicant Address | 5-33, KITAHAMA 4-CHOME, CHUO-KU, OSAKA 541-8550, | |||||||||
Inventors:
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| PCT International Classification Number | C07D239/52 | |||||||||
| PCT International Application Number | PCT/JP03/02464 | |||||||||
| PCT International Filing date | 2003-03-04 | |||||||||
PCT Conventions:
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