Title of Invention	A NOVEL PYRIMIDINE COMPOUND
Abstract	ABSTRACT 295I/CHENP/2005 "A novel pyrimidine compound" The present invention relates to a pyrimidine compound of the formula (I): wherein R represents a hydrogen atom, halogen atom or C1-C4 alkyl; R represents C3-C7 alkynyloxy; R3 represents a hydrogen atom, halogen atom or C1-C3 alkyl; X represents C4-C7 polymethylene, in which a CH2-CH2 may be replaced with a CH=CH, optionally substituted with at least one substituent selected from the group consisting of halogen atoms, trifiuoromethyl and C1-C4 alkyls. The pyrimidine compound has an excellent activity of controlling pests.

Title of Invention

A NOVEL PYRIMIDINE COMPOUND

Abstract

ABSTRACT 295I/CHENP/2005 "A novel pyrimidine compound" The present invention relates to a pyrimidine compound of the formula (I): wherein R represents a hydrogen atom, halogen atom or C1-C4 alkyl; R represents C3-C7 alkynyloxy; R3 represents a hydrogen atom, halogen atom or C1-C3 alkyl; X represents C4-C7 polymethylene, in which a CH2-CH2 may be replaced with a CH=CH, optionally substituted with at least one substituent selected from the group consisting of halogen atoms, trifiuoromethyl and C1-C4 alkyls. The pyrimidine compound has an excellent activity of controlling pests.

Full Text	PYRIMIDINE COMPOUND AND PESTS CONTROLLING COMPOSITION CONTAINING THE SAME Technical Field The present invention relates to a pyrimidine compound and a pests controlling composition containing the same. Background Art Various compounds have been used in the past for the purpose of pest control. Compounds having' a pyrimidine ring are. known ta have an effect of controlling harmful pests (WO 02/024663), And also a compound having a pyrimidine ring substituted with piperldino is known. Disclosure of the Invention The object of the present invention is to provide a pyrimidine compound having an effect of controlling pests, an pests controlling composition having this pyrimidine compound as an effective ingredient, and a method of controlling pests. Namely the present invention provides a pyrimidine compound (hereinafter, referred to as the present compound) of the formula (I): wherein R1 represents a hydrogen atom, halogen atom or C1-C4 alkylj R2 represents C3-C7 alkynyloxy; R3 represents a hydrogen atom, halogen atom or C1-C3 alkyl; X represents C4-C7 polymethylene, in which a CH2-CH2 may be replaced with a CH=CH, 2 optionally substituted with at least one substituent selected from the group consisting of halogen atoms, trifluoromethyl and C1-C4 alkyls; an pests controlling, composition containing the present compound as an effective ingredient, and a method of controlling pests comprising applying an effective amount of the present compound to pests or the habitat of pests. Embodiments of the Invention In this specification, "sec" denotes secondary and "tert" denotes tertiary. The representation of "C3-C7", for example in the "C3-C7 alkynyloxy", means the number of the total carbon atoms in the substituent. "C3-C7 Alkynyloxy" means alkynyloxy in which the number of the- total carbon atoms is 3 to 7. In this specification; the halogen atom represented by R1 includes, for example, a fluorine atom and chlorine atom; the C1-C4 alkyl represented by R1 includes, for example, methyl, ethyl, propyl, lsopropyl, butyl and isobutyl; the C3-C7 alkynyloxy represented by Ra includes, for example, C3-C7 alkynyloxy wherein the triple bond is located between the carbons of 2 and 3-position in alkynyl (hereinafter, referred to as C3-C7 2-alkynyloxy), and the C3-C7 2-alkynyloxy include, for example, 2-propynyloxy, 2-butynyloxy, 1-methy1-2-butynyloxy, 2-pentynyloxy, 4,4-dimethyl-2-pentynyloxy, l-methyl-2-propynyloxy and 1,l-dimethyl-2-propynyloxy; the halogen atom represented by R3 includes, for example, a fluorine atom and chlorine atom; the C1-C3 alkyl represented by R3 includes, for example, methyl and ethyl. In the C4-C7 polymethylene, in which a CH2-CH2 may be 3 replaced with a CH=CH, optionally substituted with a halogen atom, trifluoromethyl and C1-C4 alkyl represented by X; the halogen atom includes fluorine atom, chlorine atom and bromine atom; the C1-C4 alkyl includes methyl, ethyl, propyl, lsopropyl, isobutyl, sec-butyl and tert-butyl. In the C4-C7 polymethylene, in which a CH2-CH2 may be replaced with a CH«CH, optionally substituted with at least one substituent selected from the group consisting of halogen atoms, trifluoromethyl and C1-C4 alkyls represented by X, the C4-C7 polymethylene, in which a CH2-CK2 may be replaced with a CH-CH, includes tetramethylene, pentamethylene, hexamethylene, heptamethylene and 2-penten-l,5-ylene. The C4-C7 polymethylene, in which a CH2-CHa may be replaced with a CH-CH, optionally substituted with at least one substituent selected from the group consisting of halogen atoms , trifluoromethyl and C1-C4 alkyls represented by X includes C4-C7 polymethylene optionally substituted with at least one substituent selected from the group consisting of halogen atoms , trifluoromethyl and C1-C4 alkylsr and C4-C7 linear alkenylene optionally substituted with at least one substituent selected from the group consisting of halogen atoms, trifluoromethyl and C1-C4 alkyls. The C4-C7 polymethylene optionally substituted with at least one substituent selected from the group consisting of halogen atoms, trifluoromethyl and C1-C4 alkyls includes, for example, C4-C7 polymethylene, C4-C7 polymethylene substituted with a halogen atom(s), C4-C7 polymethylene substituted with trifluoromethyl, C4-C7 polymethylene substituted with a C1-C4 alkyl(s); more specifically it Includes tetramethylene, 1-methyltetramethylene, 2-methyltetramethylene, 1-ethyltetramethylene, 1-propyltetramethylene, 1-isopropyltetramethylene, l-(tejrt-butyUtetrainethylene, 2-ethyltetramethylene, 1,4-dimethyltetramethylene, 2,3-dimethyItetramethylene, 2,2-dimethyltetramethylene, 4 2-fluorotetramathylene,. 2-(trifluoromethyl)tatramethylene, 3-(trIfluoromethyl)tetramethylene, pentamethylene, 1-methylpentamethylene, 2-methylpentamethylene, 3-methylpentamethylene, 1-ethylpentamethylene, 2-ethylpentamethylene, 1-propylpentamethylene, 2-propylpentamethylene, 3-propylpentamethylene, 1-isopropylpentamethylene, 2-isopropylpentamethylene, 3-isopropylpentamethylene, l-(tert-butyllpentamethylene, 2-(tert-butyl)pentamethylene, 3 -(tart-butyl)pentamethylene, 1-(sec-butyl)pentamethylene, 2-(sec-butyl)pentamethylene, 1, 5-dimethylpentamethylene, 1-, 3-dimethy lpentamethylene-, 1,4-dimethylpentamethylene, 2,4-dimethylpentamethylene, 1,1-dimethylpentamethylene, 2, 2-dimethylpentantefciiylene , 3,3-dimethylpentamethylene, 2~ethyl-5-methylpentamethylene, 2-ethyl- 4-methylpentamethylene, 2,4-diethylpentamethylene, 1,2-dimethylpentamethylene, 2,2,4-trimathylpentamethylene, 1,2,4,5-tetramethylpentamethylene, 2,2,4,4-tetramethylpentamethylene, 2-fluoropentamethylene, 2-chloropentamethylene, 2-bromopentamethylene, 3-fluoropentamethylene, 3-chloropentamethylene, 3-bromopentamethylene, 2,2-difluoropentamethylene, 3,3-difluoropentamethylene. 2-fluoro-2-methylpentamethylene, 1-(trifluoromethyllpentamethylene, 2 -(trifluoromethyllpentamethylene, 3-(trifluoromethyl)pentamethylene, hexamethylene, 1-methylhexamethylene, 2-methy lhexame thylene., 3-methylhexamethylene, 4-methylhexamethylene, 1-ethylhexamethylene, 2-ethylhexamethylene, 3-ethylhexamethylene, 1-propylhexamethylene, 2-propylhexamethylene, 3-propylhexamethylene, I-isopropylhexamethylene, 2-isopropylhexamethylene, 3-isopropylhexamethylene, 1-(tert-butyl)hexamethylene, 1-isobutylhexamethylene, 1-(trifluoromethyl)hexamethylene, 5 1, 4-dimfethylhexamethylene, 1, 5 -dimethylhexamethylene, 1, 6-dimethylhexa:raethylene, 2, 5-dimethylhexamethylene and heptamethylene. The C4-C7 linear alkenylene optionally substituted with at least one substituent selected from the group consisting of halogen atoms, trifluoromethyl and C1-C4 alkyls, for example, 2-buten-1,4-ylene, 2-methyl-2-buten-l,4-ylen, 2,3-dimethyl-2-buten-1,4-ylen, 2-penten-l,5-ylene, 1-ethyl-2-penten-l,5-ylene, 2-methyl-2-penten-l,5-ylene , 2-ethyi-2-penten-l,5-ylene, 4-methyl-2-penten-l,5-ylene, 5-methyl-2-penten-l,5-ylene, 5-ethyl-2-penten-l,5-ylene, 2,4-dimethyl-2-penten-l,5-ylene, 2-hexen-l,6-ylene, 1-methyl- 2-hexen-1,6-ylene, 1-ethyl-2-hexen-1,6-ylene, 2-methyl-2-hexen-l,6-ylene, 6-ethyl-2-hexen-1,6-ylene, 2,5-dimethyl-2-hexen-1,6-ylene, 3-hexen-l,6-ylene. 2-hepten-l,7-ylena and 3-hepten-l,7-ylen&. Embodiments of the present compound include, for example, the following compounds: the pyrimidine compound wherein R1 is a hydrogen atom or C1-C4 alkyl in the formula (I); the pyrimidine compound wherein R1 is a hydrogen atom In the formula (I); the pyrimidine compound wherein R2 is C3-C7 2-alkynyloxy in the formula (I); the pyrimidine compound wherein R2 is 2-butynyloxy or 2-pentynyloxy in the formula (I); the pyrimidine compound wherein R3 is a hydrogen atom in the formula (I); the pyrimidine compound wherein R2 is a halogen atom in the formula (I); the pyrimidine compound wherein R2 is a fluorine atom in the formula (I); 6 the pyrimidine compound wherein X is C4-C7 polymethylene optionally substituted with at least one substifcuent selected from the group consisting of halogen atoms, trifluoromethyl and C1-C4 alkyl in the formula (I); the pyrimidine compound wherein X is C4-C7 polymethylene optionally substituted with a halogen atom, trifluoromethyl or C1-C4 alkyl in the formula (I); the pyrimidine compound wherein X is C4-C7 polymethyleTie in the formula (I J; the pyrimidine compound wherein X is C4-C7 polymethylene substituted with a halogen atom Is) in the formula (I); the pyrimidine compound wherein X is C4-C7 polymethylene substituted with a trifluoromethyl in the formula (I); the pyrimidine compound wherein X is C4-C7 polymethylene substituted with a C1-C4 alkylts) in the formula (I) ; the pyrimidine compound wherein X is tetraethy] ene or pentamethylene, optionally substituted with at least one substituent selected from the group consisting of halogen atoms, trifluoromethyl and C1-C4 alkyls in the formula (I); the pyrimidine compound wherein X is C4-C7 linear alkenylene optionally substituted with at least one substituent selected from the group consisting of halogen atoms, trifluoromethyl and C1-C4 alkyls in the formula (I); the pyrimidine compound wherein X is tetramethylene optionally substituted with at least one substituent selected from the group consisting of halogen atoms, trifluoromethyl and C1-C4 alkyls in the formula {1}; the pyrimidine compound wherein X is pentamethylene optionally substituted with at least one substituent selected from the group consisting of halogen atoms, trifluoromethyl and C1-C4 7 alkyls in the formula the pyrimidine compound wherein X is hexamethylene optionally substituted with at least one substituent selected from the group consisting of halogen atoms, trifluoromethyl and C1-C4 alkyls in the formula (I); the pyrimidine compound wherein X is tQtramethylene optionally substituted with a halogen atom, trifluoromethyl or C1-C4 alkyl in the formula (1) ; the pyrimidine compound wherein X is pentamethylene optionally substituted with a halogen atom, trifluoromethyl or C1-C4 alfcyl in the formula (I) ; the pyrimidine compound wherein X is hexamethylene optionally substituted with a halogen atozn, trifluoromethyl or C1-C4 alkyl in the formula (1); the pyrimidine compound wherein x is tetramethylene in the f ormula (I), following described; 8 the pyrimidine compound wherein R1 is a hydrogen atom or C1-C4 alkyl, and X is C4-C7 polymethylena optionally substituted with at least one substltuent selected from the group consisting of halogen atoms, trifluoromethyl and C1-C4 alkyls in the formula CD; the pyrimidine compound wherein R1 is a hydrogen atom or C1-C4 alkyl, and X is C4-C7 polymethylene optionally substituted with a halogen atom, trifluoromethyl or C1-C4 alkyl in the formula (I); the pyrimidine compound wherein R1 is a hydrogen atom or C1-C4 alkyl, and X is -tetraethylen© or pentamethylene, optionally substituted with at least one substituent selected from the group consisting of halogen atoms, trifluoromethyl and C1-C4 alkyls in the formula (I); the pyrimidine compound wherein R1 is a hydrogen atom or C1-C4 alkyl, and X is C4-C7 linear alkenylene optionally substituted 9 with at least one substituent selected from the group consisting of halogen atoms, trlfluoromethyl and C1-C4 alkyls in the formula (I) ; the pyrimidine compound wherein Ra is 2-butynyloxy or 2-pentynyloxy, and X is C4-C7 polymethylene optionally substituted with at least one substituent selected from the group consisting of halogen atoms, trlfluoromethyl and C1-C4 alkyls in the formula (I); the pyrimidine compound wherein R2 is 2-butynyloxy or 2-pentynyloxy, and X is C4-C7 polymethylene optionally substituted with a halogen atom, trlfluoromethyl or C1-C4 alkyl in the formula (I); the pyrimidine compound wherein R2 is 2-butynyloxy or 2-pentynyloxy, and X is tetraethylene or pentamethylene, optionally substituted with at least one substituent selected from the group consisting of halogen atoms, trlfluoromethyl and C1-C4 alkyls in the formula (I); the pyrimidine compound wherein R2 is 2-butynyloxy or 2-pentynyloxy, and X is C4-C7 linear alkenylene optionally substituted with at least one substituent selected from the group consisting of halogen atoms, trlfluoromethyl and C1-C4 alkyls in the formula (I); the pyrimidine compound wherein R1 is a hydrogen atom or C1-C4 alkyl, R2 is 2-butynyloxy or 2-pentynyloxy, and X is C4-C7 polymethylene optionally substituted with at least one substituent selected from the group consisting of halogen atoms, trlfluoromethyl and C1-C4 alkyls in the formula (I); the p-yrimidine compound wherein-R?' is ..a hydrogen atom, or .C1-C4 alkyl, R2 is 2-butynyloxy or 2-pentynyloxy, and X is C4-C7 polymethylene optionally substituted with a halogen atom, trlfluoromethyl or C1-C4 alkyl in the formula (I); the pyrimidine compound wherein R1 is a hydrogen atom or C1-C4 alkyl, R2 is 2-butynyloxy or 2-pentynyloxy, and X is 10 tetraethylene or pentamethylene , optionally substituted with at least one substituent selected from the group consisting of halogen atoms, trifluoromethyl and C1-C4 alkyls in the formula (I); the pyrimldine compound wherein R1 is a hydrogen atom or C1-C4 alkyl, R2 is 2-butynyloxy or 2-pentynyloxy, and X is C4-C7 linear alkenylene optionally substituted with at least one substituent selected from the group consisting of halogen atoms, trifluoromethyl and C1-C4 alkyls in the formula (I); the pyrimidine compound wherein R1 is a hydrogen atom, and R3 is a hydrogen atom in the formula (I); the pyrimidine compound wherein R1 is a hydrogen atom, and R3 is a halogen atom in the formula (I); the'pyrimidine compound wherein R1 is a hydrogen atom, and R3 is a fluorine atom in the formula (I); the pyrimidine compound wherein R1 is a hydrogen atom, R2 is C3-C7 2-alkynyloxy, and R3 is a hydrogen atom in the formula (I); the pyrimidine compound wherein R1 is a hydrogen atom, Rz is C3-C7 2-alkynyloxy, and R3 is a halogen atom in the formula (I); the pyrimidine compound wherein Rl is a hydrogen atom, R2 is C3-C7 2-alkynyloxy, and R3 is a fluorine atom in the formula (I); the pyrimidine compound wherein R1 is a hydrogen atom, R2 is C3-C7 2-alkynyloxy, R3 is a hydrogen atom, and X is C3-C8 pentamethylene optionally substituted with at least one substituent selected from the group consisting of halogen atoms, trifluoromethyl and C1-C4 alkyls in the formula (I); the pyrimidine compound wherein R1 is a hydrogen atom, R3 is C3-C7 2 - alkynyloxy,-R3- is a halogen-atom, and X-is C3-C8 pentamethylene optionally substituted with at least one substituent selected from the group consisting of halogen atoms, trifluoromethyl and C1-C4 alkyls in the formula (I); the pyrimidine compound wherein R1 is a hydrogen atom, Rz is C3-C7 2-alkynyloxy, R3 is a fluorine atom, and X is C3-C8 11 pentamethylene optionally substituted with at least one substituent selected from the group consisting of halogen atoms, trifluoromethyl and C1-C4 alkyls in the formula (I); the pyrimidine compound wherein R1 is a hydrogen atom, R2 is C3-C7 2-alkynyloxy, R3 is a hydrogen atom, and X is C3-C8 hexamethylene optionally substituted with at least one substituent selected from the group consisting of halogen atoms, trif luoromethyl and C1-C4 alkyls in the formula (I); the pyrimidine compound wherein R1 is a hydrogen atom, R2 is C3-C7 2-alkynyloxy, R3 is a halogen atom, and X is C3-C8 hexamethylene optionally substituted with at least one substituent selected from the group consisting of halogen atoms, trif luoromethyl and C1-C4 alkyls in the formula (I); the pyrimidine compound wherein R1 is a hydrogen atom, Rz is C3-C7 2-alkynyloxy, R3 is a fluorine atom, and X is C3-C8 hexamethylene optionally substituted with at least one substituent selected from the group consisting of halogen atoms, trifluoromethyl and C1-C4 alkyls in the formula (I); the pyrimidine compound wherein R1 is a hydrogen atom, R2 is C3-C7 2-alkynyloxy, R3 is a hydrogen atom, and X is C3-C8 pentamethylene optionally substituted with a halogen atom, trifluoromethyl or C1-C4 alkyl in the formula (I); the pyrimidine compound wherein R1 is a hydrogen atom, Ra is C3-C7 2-alkynyloxy, R3 is a halogen atom, and X is C3-C8 pentamethylene optionally substituted with a halogen atom, trifluoromethyl or C1-C4 alkyl in the formula (I); the pyrimidine compound wherein R1 is a hydrogen atom, R2 is C3-C7 2 alkynylbxy, R"3 is' a fluorine atom, and X is C3-C8 pentamethylene optionally substituted with a halogen atom, trifluoromethyl or C1-C4 alkyl in the formula (I); the pyrimidine compound wherein R1 is a hydrogen atom, R2 is. C3-C7 2-alkynyloxy, R3 is a hydrogen atom, and X is C3-C8 hexamethylene optionally substituted with a halogen atom, trifluoromethyl or 12 C1-C4 alkyl in the formula {I); the pyrimidine compound wh&rein R1 is a hydrogen atom, R2 is C3-C7 2-alkynyloxy, R3 is a halogen atom, and X is C3-C8 hexamethylene optionally substituted with a halogen atom, trif luoromethyl or C1-C4 alkyl in the formula (I); the pyrimidine compound wherein R1 is a hydrogen atom, R2 Is C3-C7 2-alkynyloxy, £3 is a fluorine atom, and X is C3-C8 hexamethylene optionally substituted with a halogen atom, trlfluoromethyl or C1-C4 alkyl in the formula (I). The production method of the present invention will be illustrated below. The present compound can be produced, for example, by the production method 1 and 2 described below. Production method 1 This reaction is usually carried out in a solvent. As the solvent used in the reaction, there are listed, for example, ethers such as tetrahydrofuran, diethyl ether, tert-butyl methyl ether, ethylene glycol dimethyl ether and 1,4-dioxane, acid amides such as N,N-dimethyl formamide, nitriles such as acetonitrile, sulfoxides such as dimethyl sulfoxide, hydrocarbons such as hexane, aromatic hydrocarbons such as benzene and toluene, and the mixture thereof. As the base used in the reaction, there are listed, for 13 example, alkali metal hydride such as sodium hydride and. potassium hydride, carbonate such as potassium carbonate, alJcali metal alkoxide such as potassium tert-butoxide and sodium tert-butoxide. The amount of the compound of the formula (III) is usually 1 to 2 moles, and the amount of the base is usually 1 to 2 mole, based on one mol of the compound of the formula (II). The reaction temperature' of the reaction is usually in the range from o to 80"C, and the reaction time, is usually in the range from 0.5 to 12 hours. After completion of the reaction, the compound of the formula (I) can be isolated by the procedure such as extracting the reaction mixture into an organic solvent, drying, and concentrating. The isolated compound of the formula (I) can be further purified by chromatography, re-crystallization and the like. 14 tert-butyl methyl ether, ethylene glycol dimethyl ether and 1,4-dioxane, acid amides such as N,N-dimethyl formamide, nitriles such as acetonitrile, alcohols such as methanol and ethanol, hydrocarbons such as hexane, aromatic hydrocarbons such as benzene and toluene, and the mixture thereof. ■ As the base used in the reaction, there are listed, for example, alkali metal hydride such as sodium hydride and potassium hydride, carbonate such as potassium carbonate, tertiary amines such as trlethylamine and ethyldiisopropylamine. The amount of the compound of the formula (V) is usually 1 to 3 moles based on one mol of the compound of the formula (IV) . When the reaction is carried out in the presence of the base, the amount of base is usually 1 to 4 moles, based on one mol of the compound of the formula (IV). The reaction temperature of the reaction is usually in the range from 0 to ISO'C, and the reaction time is usually in the range from 0.1 to 48 hours. After completion of the reaction, the compound of the formula (I) can be isolated by the following procedure: (i) extracting the reaction mixture into an organic solvent, drying and concentrating; (li) concentrating the reaction mixture as it is. The isolated compound of the formula (I) can be further purified by chromatography, re-crystallization and the like. Next, the production methods of the intermediates of the present compound will be illustrated below. Reference production method 1 The'compound of the formula (II) can be produced by making a compound of the formula (VI) react with a compound of the formula (Vj or its salt such as a hydrochloride of the compound of the formula (V). 15 wherein R1, Rz, R3 and x are as defined above. This reaction is usually carried out in a solvent, and optionally carried out in the presence of a base. As the solvent used in the reaction, there are listed, for example, ethers such as tetrahydrofuran, diethyl ether, tert-butyl methyl ether, ethylene glycol dimethyl ether and 1,4-dioxane, acid amides such as N,N-dimethyl formamide, nitriles such as acetonitrile, alcohols such as methanol and ethanol, hydrocarbons such as hexane, aromatic hydrocarbons such as benzene and toluene, sulfoxide such as dimethyl sulfoxide, and the mixture thereof. As the base used in the reaction, there are listed, for example, alkali metal hydride such as sodium hydride and potassium hydride, carbonate such as potassium carbonate, alkali metal hydroxide such as potassium tert-butoxide and sodium tert-butoxide. The amount of the compound of the formula (VI) is usually 1 to 3 moles based on one mol of the compound of the formula (V) . When the reaction is carried out in the presence of the base, the amount of base is usually 1 to 4 moles based on one mol of the compound of the formula (V). The reaction temperature of the reaction is usually in the range from 0 to lSO'C, and the reaction time is usually in the range from 0.1 to 48 hours. After completion of the reaction, the compound of the formula (II) can be isolated by the following procedure: (i) extracting the reaction' mixture into an organic 16 solvent, drying and concentrating; (ii) concentrating the reaction mixture as it is. The isolated compound of the formula (II) can be further purified by chromatography, re-crystallization and the like. The compounds of the formula (II) includes, for example, the following compounds: the compound wherein X is C4-C7 polymethylene in the formula (ID; a compound of the formula (VI) react with a compound of the formula (III) in the presence of a base. wherein R1, R2, R3 and X are as defined above. This reaction is usually carried out in a solvent, and optionally carried out in the presence of a base. As the solvent used in the reaction, there are listed, for example, ethers such as tetrahydrofuran, diethyl ether, tert-butyl methyl ether, ethylene glycol dimethyl ether and 1,4-dioxane, acid amides such as N,N-dimethyl formamide, nitriles such as acetonitrile, hydrocarbons such as hexane, aromatic hydrocarbons such as benzene and toluene, sulfoxide such as dimethyl sulfoxide, and the mixture thereof. As the base used in the reaction, there are listed, for example, alkali metal hydride such as sodium hydride and potassium hydride, carbonate such as potassium carbonate, alkali metal hydroxide such as potassium tert-butoxide and sodium tert-butoxide. The amount of the compound of the formula (III) is usually 1 to 2 moles, and the amount of the base is usually 1 to 2 moles, based on one mol of the compound of the formula (IV). The reaction temperature of the reaction is usually in the range from -20 to SO^C, and the reaction time is usually in the range f-rom- 0 .-5- to 12 hours. After completion of the reaction, the compound of the formula (IV) can be isolated by the procedure such as extracting the reaction mixture into an organic solvent, drying and concentrating. The isolated compound of the formula (IV) can be further 18 purified by chromatography, re-crystallization and the like. The compounds of the formula (IV) includes, for example, the following compounds: the compound wherein R1 is a hydrogen atom or C1-C4 alkyl in the formula (IV); the compound wherein R1 is a hydrogen atom in the formula (II) ; the compound wherein R2 is 2-butynyloxy or 2-pentynyloxy in the formula (IV). Reference production method 3 The compound of the formula (V) can be produced, for example, from a compound of the formula (IX) by the following scheme. wherein X1 represents C3-C6 polymethylene optionally substituted with at least one substituent selected from the group consisting of halogen atoms, trifluoromethyl and C1-C4 alkyIs. Process 3-1 The compound of the formula (VII) can be produced by making a compound of the formula (VII) react with a hydroxy amine in a solvent. This reaction is usually carried out in a solvent, and optionally carried out in the presence, of a base. As the solvent used in the reaction, there are listed, for example, ethers such as tetrahydrofuran, diethyl ether, tert-butyl methyl ether, ethylene glycol dimethyl ether and 1,4-dioxane, acid amides such as N,N-dimethyl formaraide, alcohols such as methanol and ethanol, water, and the mixture 19 thereof. As the base used in the reaction, there are listed, for example, inorganic base such as sodium hydroxide and potassium hydroxide, tertiary amines such as triethylamine, and nitrogen containing aromatlcs such as pyridine. The amount of hydroxylamine or its salt is usually l to 3 mole, and the amount of the base is 1 to 5 moles, based on one mol of the compound of the formula (VII). The reaction temperature of the reaction is usually in the range from 0 to 80^, and the reaction time is usually in the range from 1 to 24 hours. After completion of the reaction, the compound of the formula (VIII) can be isolated by the procedure such as extracting the reaction mixture into an organic solvent, drying and concentrating. The isolated compound of the formula (VIII) can be further purified by chromatography, re-crystallization and the like. The compound of the formula (IX) is the compound disclosed, for example, in Synthesis, (1980), p.222-223, or J. Am. Chem. Soc, (1983), 105, p.2381-2843; or can be produced by the following process. Process 3-2 The compound of the formula (IX) can be produced by making a compound of the formula (VIII) react in the presence of the reagent for the rearrangement reaction. This reaction is usually carried out in a solvent. As the solvent-used i-n the reaction, there are listed, for example, acid amides such as N,N-dimethyl formamide, aromatic hydrocarbons such as toluene and benzen, and the mixture thereof. As the reagent for the rearrangement reaction, there are listed chlorides of phosphorous such as phosphorous oxychloride. 20 chlorides of sulfur such as thionyl chloride, and poly phosphoric acid. The amount of the reagent of the rearrangement reaction is usually 0.1 mole to excess amount based on one mole of the compound of the formula (VIII) . The reaction temperature of the reaction is usually in the range from 0 to 1500, and the reaction time is usually in the range from 0.1 to 48 hours. After completion of the reaction, the compound of the formula (VIII) can be isolated by the procedure such as extracting the reaction mixture into an organic solvent, drying and concentrating. The isolated compound of the formula (VIII) can be further purified by chromatography, re-crystallization and the like. The compound of the formula (V ) is the compound disclosed, for example, in J. Am. Chem. Soc, (1983), 105, p.2381-2843 or 3. Heterocyclic. Chem., {1980)17, p.603; or can be produced by the following process. Process 3-3 The compound of the formula (V ) can be produced by making a compound of the formula (IX) react with the reducing reagent. This reaction is usually carried out in a solvent. As the solvent used in the reaction, there are listed, for example, ethers such as tetrahydrofuran and diethyl ether. As the reducing reagent, there are listed hydrides of aluminum such as lithium aluminium hydride. The amount of the reducing reagent is usua-lly 0 . 5 to 6 moles based on one mole of the compound of the formula (IX). The reaction temperature of the reaction is usually in the range from 0 to 120^, and the reaction time is usually in the range from 1 to 2 4 hours. After completion of the reaction, the compound of the 21 formula (V) can be isolated by the following procedure: (i) poring successively water, aqueous solution of 15% sodium hydroxide, and water into the reaction mixture, extracting into an organic solvent, drying and concentrating; when necessary, distilling; (ii) poring successively water, aqueous solution of 15% sodium hydroxide, and water into the reaction mixture, extracting into an organic solvent, drying, and collecting the hydrochloric salts of the compound of the formula (V) by stirring in the presence of hydrogen chloride or hydrochloric acid. Reference production method 4 The compound of the formula (V) can be produced, for example, from a compound of the formula (IX) by the following scheme. wherein X2 represents C2-C5 polymethylene optionally substituted with at least one substituent selected from the group consisting of halogen atoms, trifluoromethyl and C1-C4 alkyls. Process 4-1 The compound of the formula (XI) can be produced by making a compound of the formula (X) react with urea. This reaction is usually carried out in absence of a solvent. The amount of urea is usually 10 moles to excess amount based one mole of the compound of the formula (X). The reaction temperature of the reaction is usually in the range from 50 to 1700, and the reaction time is usually in the 22 range from 1 to 24 hours. After completion of the reaction, the compound of the formula (XI) can be isolated by the procedure such as extracting the reaction mixture into an organic solvent, drying and concentrating. The isolated compound of the formula (XI) can be further purified by chromatography, re-crystallization and the like. Process 4-2 The compound of the formula (V" ) can be produced by making a compound of the formula (XI) react with the reducing reagent. This reaction is usually carried out in a solvent. As the solvent used in the reaction, there are listed, for example, ethers such as tetrahydrofuran and diethyl ether. As the reducing reagent, there are listed hydrides of aluminum such as lithium aluminium hydride. The amount of the reducing reagent is usually 1 to 6 moles based on one mole of the compound of the formula (XI). The reaction temperature of the reaction is usually in the range from 0 to 1200, and the reaction time is usually in the range from 1 to 24 hours. After completion of the reaction, the compound of the formula (V) can be isolated by the following procedure: (i) poring successively water, aqueous solution of 15% sodium hydroxide, and water into the reaction mixture, extracting into an organic solvent, drying and concentrating; when necessary, distilling; (ii) poring successively water, aqueous solution.of 15% sodium hydroxide, and water into the reaction mixture, extracting into an organic solvent, drying, and collecting the hydrochloric salts of the compound of the formula (V") by stirring in the presence of hydrogen chloride or hydrochloric acid. 23 Next, the specific examples of the present compounds are showing below. The pyrimidine compound wherein R1 is a hydrogen atom, R2 is 2-propynyloxy, R3 is a hydrogen atom, X is one selected from the group (A) below. Group (A): tetramethylene, 1-methyltetramethylene, 1-ethyltetramethylene, 1-propyltetramethylene, 1-isopropyltetramethylene, 1-(tert-butyl)tetramethylene, 1,4-dimethyltetramethylene, 2-(trifluoromethyl)tetramethylene, 3- (trif luoromethyl) tetramethylene, pent ante thyl en e, 1-methylpsntamethylene, 2-methylpentamethylene, 3-methylpentamethylene, 1-ethylpentaraethylene, 2-ethylpentamethylene, 1-propylpentamethylene, 2-propylpentamethylene, 3-propylpentamethylene, 3-isopropylpentamethylene, 1-(tert-butyl)pentamethylene, 3-(tert-butyl)pentamethylene, 1-(sec-butyl)pentamethylene, 1,5-dimethylpentamethylene, 1,3-dimethylpentamethylene, 1,4-dimethylpentamethylene, 2,2-dimethylpentamethylene, 3,3-dimethyIpentamethylene, 2 -ethyl-5-methylpentamethylene, 2-fluoropentamethylene.,. 3-fluoropentamethylene,, 2,2-difluoropentamethylene, 3,3-difluoropentamethylene, 1-(trifluoromethyl)pentamethylene, 2 -(trifluoromethyl)pentamethylene, 3-(trifLuoromethyl)pentamethylene, hexamethylene, 1-me thylhexamethylene, 2-methylhexamethylene, 3-methylhexamethylene, 1-ethylhexamethylene, 2 -ethylhexamethylene, 3-ethylhexamethylene, 1- propylhexamethylene, 1-isopropylhexamethylene, 1-(tert-butyl)hexamethylene, 1-isobutylhexamethylene, 1,4-dimethylhexamethylenegroup, 1,5-dimethylhexamethylene, 1,6-dimethylhexamethylene, 2,5-dimethylhexamethylene, 1-(trifluoromethyl)hexamethylene, heptamethylene, 2-penten-l,5-ylene and 2,4-dimethyl-2-penten-l,5-ylene. The pyrimidine compound wherein R1 is a hydrogen atom, R2 is 2-butynyloxy, R3 is methyl, X is one selected from the group (B) below. Group (B): tetramethylene, 1-methyltetramethylene, 1-ethyltetramethylene, 1,4-dimethyltetramethylene, 2-(trifluoromethyl)tetramethylene , 3-(trifluoromethyl)tetramethylene, pentamethylene, 1-methylpentamethylene, 2-methylpentamethylene, 3-methylpentamethylene, 1-ethylpentamethylene, 2-ethylpentamethylene, 1,5-dimethylpentamethyiene, 1,3-dimethylpentamethylene, 1,4-dimethylpentamethylene, 2,2-dimethylpentamethylene, 3,3-dimethylpentamethylene, 2-ethyl-5-methylpentamethylene, 1-{trifluoromethy1)pentamethylene, 2-(trifluoromethyl)pentamethylene, 3 -(trifluoromethyl)pentamethylene, hexamethylene, l-methyihexamethylerie-, 2-methylhexamethylene, 3-methylhexamethylene, 1-ethylhexamethylene, 2-ethylhexamethylene, 3-ethylhexamethylene, 1-(trifluoromethyl)hexaraethylene, heptamethylene, 2-penten-l, 5-ylene and 2 , 4-dimet,hyl-2-penten-l, 5-ylene. 25 The pyrimidine compound wherein Rl is a hydrogen atom, R2 is 2-propynyloxy, R3 is a fluorine atom, X is one selected from the group (A) above. The pyrimidine compound wherein Rx is a hydrogen atom, R2 is 2-propynyloxy, R3 is a chlorine atom, X is one selected from the group (B) above. The pyrimidine compound wherein R1 is a hydrogen atom, R1 is l-methyl-2-propynyloxy, R3 is a chlorine atom, X is one selected from the group (B) above. The pyrimidine compound wherein R1 is a hydrogen atom, R1 is 2-pentynyloxy, R3 is a hydrogen atom, X is one selected from the group (C) below. Group (C): tetramethylene, 1-methyltetramethylene, 2-methyltetramathylene, 1-ethyltetramethylene, 1-propyltetramethylene, 1-isopropyltetramethylene, 1-(tert-butyl)tetramethylene, 2-ethyltetramethylene, 1,4-dimethyltetramethylene, 2,3-dimethyltetramethylene, 2,2-dimethyltetramethylene, 2-fluorotetramethylene, 2-(trifluoromethyl)tetramethylene , 3-{trifluoromethyl}tetramethylene, pentamethylene, 1-methylpentamethylene, 2-methylpentamethylene, 3-methylpentamethylene, 1-ethylpentamethylene, 2-ethylpentamethylene, 1-propylpentamethylene, 2-propylpentamethylene, 3-propylpentamethylene, 1-isopropylpentamethylene, 2-isopropylpentamethylene, 3-isopropylpentamethylene, 1- (tert-butyl)pe'ntamethylene, 2-(tert-butyl)pentamethylene, 3-(tert-butyl)pentamethylene, 1-(sec-butyl)pentamethylene, 2-(sec-butyl)pentamethylene, 1,5-dimethylpentamethylene, 1,3-dimethylpentamethylene, 1,4-dimethylpentamethylene, 2,4-dimethylpentamethylene, 1,1-dimethylpentamethylene, 2,2-dimethylpentamethylene, 26 3, 3-dimethylpentamethylene, 2-ethyl-4-methylpentamethylene, 2-ethyl-5-methylpentamethylene, 2,4-diethylpentamethylene, 2-fluoropentamethylene, 2-chloropentamethylene, 2-brojnopentaroethylene, 3-fluoropentamethylene, 3-chloropentamethylene, 3-bromopentamethylene, 2,2-difluoropentamethylene, 3,3-difluoropentamethylene, 2-fluoro-2-methylpentamethylene, 1-(trlfluoromethyl)pentamethylene, 2-{trifluoromethyl)pentamethylene, 3-(trifluoromethyl)pentamethylene, hexamethylene, 1-methylhexamethylene, 2-methyIhexamethylene, 3-methylhexamethylene, 1-ethylhexamethylene, 2 -ethyIhexamethylene, 3-ethylhexamethylene, 1-propylhexamethylene, 2-propylhexamethylene, 3-propylhexamethylene, 1-isopropyIhexamethylene, 2-isopropylhexamethylene, 3-isopropylhexamethylene. 1-[tert-butyllhexamethylene, 1-isobutylhexamethylene, 1,4-dimethylhexamethylenegroup, 1,5-dimethyIhexamethylene, 1,6-dimethylhexamethylene, 2,5-dimethylhexamethylene, 1-(trifluoromethyl)hexamethylene, heptamethylene, 2-penten-l,5-ylene and 2,4-dimethyl-2-penten-l,5-ylene. The pyrlmidine compound wherein R1 is a hydrogen atom, RJ is 2-pentynyloxy, R3 is methyl, X is one selected from the group (B) above. The pyrlmidine compound wherein Rl is a hydrogen atom, R is 2-pentynyloxy, R3 is a fluorine atom, X is one selected from the group (C) above. The pyrlmidine compound wherein R1 is a hydrogen atom, R2 is 2-pentynyloxy, R3 is a chlorine atom, X is one selected from the group (A) above. The pyrlmidine compound wherein R1 is a hydrogen atom, K2 is 2-butynyloxy, R3 is ahydrogen atom, X is one selected from 27 the group (C) above. The pyrimidine compound wherein R1 is a hydrogen atom, R2 is 2-butynyloxy, R3 is a fluorine atom, X is one selected from the group (C) above. The pyrimidine compound wherein R1 is a hydrogen atom, R2 is 2-butynyloxy, R3 is a chlorine atom, X is one selected from the group (A) above. The pyrimidine compound wherein R1 is a hydrogen atom, R2 is l-methyl-2-propynyloxy, R3 is a hydrogen atom, X is one selected from the group (A) above. The pyrimidine compound wherein R1 is a hydrogen atom, Ra is l-methyl-2-propynyloxy, R3 is a fluorine atom, X is one selected from the group (A) above. The pyrimidine compound wherein R1 is a hydrogen atom, R2 is l-inethyl-2-butynyloxy, R3 is a hydrogen atom, X is one selected from the group (A) above. The pyrimidine compound wherein Rl is a hydrogen atom, R2 is l-methyl-2-butynyloxy, R3 is a fluorine atom, X is one selected from the group (A) above. The pyrimidine compound wherein Rl is a hydrogen atom, R2 is l-methyl-2-butynyloxy, R3 is a chlorine atom, X is one selected from the group (B) above. The pests against which the present compounds have an effect may include arthropods (e.g., insects, acarlnes) and nemathelminthes, specific examples of which are as follows: Hemiptera: Delphacidae such as Laodelphax striatellus,-Niiaparva.ta lugens, Sogatella furcifera and the like, Deltocephalidae such as Nephotettix cincticeps, Nephotettix virescens and the like, Aphididae such as Aphis gossypii, Myzus persicae and the like. 28 Pentatomidae such as Nezara antennata, Riptortus clavetus and the like, Aleyrodidae such as Trialeurodes vaporariorum, Bemisia argentlfolii and the like, Coccidae such as Aonidiella aurantii. Cornstockaspis perniciosa, Unaspis citri, Ceroplastes rubens, Icerya purchasi and the like, Tingidae, Psyllidae, and the like; kepidoptera: Pyralidae such as Chilo suppressalis, Cnaphalocrocis medinalis, Notarcha derogata, Plodia interpuncteila and the Like, Noctuidae such as Spodoptera litura, Pseudaletia separata, Thoricoplusia spp., Heliothis spp., Helicoverpa spp. and the like, Pieridae such as Pieris rapae and the like, Tortricidae such as Adoxophyes spp., Grapholita molesta, Cydia poraonella and the like, Carposinidae such as Carposina niponensis and the like, Lyonetiidae such as Lyonetia spp. and the like, Lymantriidae such as Lymantria spp., Euproctis spp., and the like, Yponomeutidae such as Plutella xylostella and the like, Gelechiidae such as Pectinophora gossypiella and the like, Arctiidae such as Hyphantria cunea and the like, Tineidae such-as -Tinea txanslucens, Tineola bisselliella. and the like? Diptera: Calicidae such as Culex pipiens pallens, Culex tritaeniorhynchus, Culex guinquefasciatus and the like, Aedes spp. such as Aedes aegypti, Aedes albopictus and the 29 i like, ' Anopheles such as Anopheles sinensis and the like, Chironomidae, Muscidae such as Musca domestica, Muscina stabulans and the like, Calliphoridae, Sarcophagidae, Fanniidae, Anthoroyiidae such as Delia platura, Delia antiqua and the like, Tephritidae, Drosophilidaa, Psychodidae, Tabanidae, Simuliidae, Stomoxyidae, Agromyzidae, and the like; Coleoptera: Diabrotica spp. such as Diabrotica virgifera virglfera, Diabrotica undecimpunctata howardi and the like, Scarabaeidae such as Anomala cuprea, Anomala rufocuprea and the like, Curculionidae such as Sitophilus zeaxnais, Lissorhoptrus orysophilus, Callosobruchuys chienensis and the like, Tenebrionidae such as Tenebrio molitor, Tribolium castaneum and the like, Chrysomelidae such as Oulema oryzae, Aulacophora femoralis, Phyllotreta strlolata, Leptinotarsa decemlineata and the like, Anobiidae, Epilachna spp. such as Epilachna vigintioctopunctata and the like, Lyctidae, 30 Bostrychidae, Cerambycidae, Paederus fuscipes; Blattodea: Blattella germanica, Perlplaneta fuliginosa, Periplaneta amerlcana, Peri'planeta brunnea, Blatta orientalis and the like; Thysanoptera: Thrips palmi, Thrlps tabacl, Frankllniella occidentalls and the like; Hymenoptera: Formlcidae such as Monomorium pharaonis, Vespidae, bethylid wasp, Tenthredinidae such as Athalia japonica, and the like; Orthoptera: Gryllotalpidae, Acrididae, and the like; Aphaniptera: Ctenocephalides felis, Ctenocephalides canis, Pulex irrltans, Xenopsylla cheopis, and the like; Anoplura: Pediculus humanus corporis, Phthirus pubis, Haematopirms eurysternus, Dalmalinia ovis, and the like; Isoptera: Reticulitermes speratus, Coptotermes formosanua, and the like; Acarina: Tetranychidae such as Tetranychus urticae, Panonychus citri, Oligonychus spp., and the like, Eriophyidae such as Aculops pelekassi and the like, Tarsonemidae such as Polyphagotarsonemus latus, and the like, Tenuipalpidae, Tuckerellidae, Ixodidae such as Haemaphysalis longicornis. 37 Haemaphysails flava, Dermacentor talwanicus, Ixodes ovatus, Ixodes persulcatus, Boophilus microplus, Rhipicephalus sanguineus, and the like, Acarldae such as Tyrophagus putrescentiae, and the like, Epidermoptidae such as Dermatophagoides farinae, Dermatophagoldes ptrenyssnus, and the like, Cheyletidae such as Cheyletus eruditus, Cheyletus malaccensis, Cheyletus moorei, and the like, Dermanyssidae, and the like. Nematodes: Pratylenchus coffeae, Pratylenchus fallax, Heterodera glycines, Globadera rostochiensis, Meloidogyne hapla, Meloidogyne incognita and the like. The pests controlling composition of the present invention contains the present compound and an inert carrier. Generally, it is a formulation obtained by mixing the present compound and a carrier such as a solid carrier, a liquid carrier, a gaseous carrier and/or bait for poison bait, and if necessary, adding a surfactant and other adjuvant for formulation. The formulation includes , for example, an oil solution, an emulsion, a flowable formulation, a wettable powder, a granule, a powder, a microcapsule, and the like. These formulations can be converted to use into a poison bait, a sheet. In the pests controlling composition of the present invention, the present compound is usually contained in an amount of 0.01% to 95% by weight. As the so-lid carrier used in formulation, there are listed, for example, fine powders or granules of clays (kaolin clay, diatomaceous earth, synthetic water-containing silicon oxide, bentonite, Fubasami clay, acid clay and the like), talcs, ceramics, other inorganic minerals {sericite, quartz, sulfur, activated carbon, calcium carbonate, hydrated silica and the 32 like), chemical fertilizers (ammonia sulfate, ammonia phosphate , ammonia nitrate, urea, ammonia chloride) and the like, and as the liquid carrier, there are listed, for example, water, alcohols (methanol, ethanoi and the like), ketones (acetone, methyl ethyl ketone and the like), aromatic hydrocarbons (benzene, toluene, xylene, ethylbenzene, methylnaphthalene and the like), aliphatic hydrocarbons (hexane, cyclohexane, kerosene, light oil and the like), esters (ethyl acetate, butyl acetate and the like) , nitriles (acetonitrile, isobutylonitrile and the like), ethers (diisopropyl ether, 1,4-dioxane and the like), acid amides (N,N-dimethylformamide, N,N-dimethylacetamide and the like), halogenated hydrocarbons (dichloromethane, trichloroethane, carbon tetrachloride and the like), dimethyl sulfoxide and vegetable oils (soy bean oil, cotton seed oil and the like). As the gaseous carrier, there are listed, for example, fluorocarbon, butane gas, LPG (liquefied petroleum gas), dimethyl ether and carbon dioxide. As the surfactant, there are listed, for example, alkylsulfate salts, alkyisulfonate salts, alkyl aryl sulfonic acid salts, alkyl aryl ethers and their polyoxyethylenated substances, polyethylene glycol ethers, polyhydric alcohol esters, and sugar alcohol derivatives. As the other formulation auxiliaries, there are listed, for example, fixing agents, dispersing agents, stabilizer and the like, specifically, casein, gelatin, polysaccharides (starch powder, gum Arabic, cellulose derivatives, alginic acid and the like), ■ lignin de-rivatives.-bentonite, saccharides, synthetic water-soluble polymers (polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acids and the like), PAP (acidic isopropyl phosphate), BHT (2,6-di-tert-butyl-4-methylphenol), BHA (mixture of 2 - ter-t -butyl- 4 -methoxyphenol. and 33 3-tert-butyl-4-methoxyphenol) , vegetable oils, mineral oils, fatty acids and fatty esters. As the poison bait base material, there are listed, for example, bait components such as crop powders, vegetable oils, saccharides, crystalline cellulose and the like. To the poison bait, antioxidants such as dibutylhydroxytoluene, nordihydroguaiaretic acid and the like, preservatives such as dehydroacetic acid and the like, accidental ingestion-preventing agents for child and pets such as a capsicum powder and the like, harmful insect-attracting aromatics such as cheese aromatics, onion aromatics, peanut oil, and the like, are added, if necessary. The pests controlling composition of the present invention is applied to pests directly and/or habitats of pests {nest, plant body, soil and the like). When pests parasitic on cultivated plants are controlled, for example, the pests controlling composition of the present invention is sprayed on the ground part of the cultivated plants, the pests controlling composition of the present invention is irrigated near to the stub, and the like. When the pests controlling composition of the present invention is used to control pests in the agriculture and forestry field, its application amount is usually from 0.1 to 10,000 g in terms of the amount of the present compound per 1000 ma. When the pests controlling composition of the present invention "is" the'formulation "Of an emulsion, flowable, wettable powders, microcapsule or the like, it is applied after dilution with water to have a concentration of the present compound of usually 10 to 10, 000 ppm. When the pests controlling composition of the present invention is the formulation of an oil solution, granule, powder and the like, it is usually applied as it is. 34 When the pests controlling composition of the present invention is used to control pests in indoor field, the amount of the present compound per m2 of the application area, if treating plane, is usually from 0.001 to 100 mg, and the amount of the present compound per m3 of the application space, if treating space, is usually from 0.001 to 10 mg. When the pests controlling composition of the present invention is the formulation of the an emulsion, flowable, wettable powder, microcapsule, and the like, it is applied after dilution with water to have a concentration of the present compound of usually from 0.01 to 100,000 ppm in application thereof. When the pests controlling composition of the present invention is the formulation of an oil solution, aerosol, smoking agent, poison bait and the like, it is usually applied as it is. The pests controlling composition of the present invention can be used to treat stems and leaves of plants such as crops and the like to be protected from pests, and can also be used to treat beds before planting of nursery plants and the planting hole and stub in planting. Further, for the purpose of controlling pests living in soil of cultivation ground, it may also be used to treat the soil. It is also possibly that a resin formulation processed into sheet, string and thfe like is wound on crops, put around crops and/or placed on the surface of the soil at the stub, and the like. The pests controlling composition of the present invention can be used together with other insecticides, nematicldes , ._a.caricides,. bactericides.,. phytoci.des, . plaint growth controlling compositions, synergists, fertilizers, soil improving agents, animal fodders and the like. Mentioned as such insecticides, acaricides and nematicides are, for example; organic phosphorus compounds such as fenitrothion, 35 fenthion, pyridaphenthion, diazinon, chlorpyrifos, chlorpyrifos-methyl, acephate, methidathion, disulfoton, DDVP , sulprofos, profenofos, cyanophos, dioxabenzofos, dimethoate, phenthoate, malathion, trichlorfon, azinphosmethyl, monocrotophos, dicrotophos, ethion, fosthiazate and the like; carbamate compounds such as BPMC, benfuracarb, propoxur, carbosulfan, carbaryl, methomyl, ethiofencarb, aldicarb, oxamyl, fenothiocarb, thiodicarb, alanycarb and the like; pyrethroid compounds such as etofenprox, fenvalerate, esfenvalerate, fenpropathrin, cypermethrin, a-cypermethrin, Z-cypermethrin, permethrin, cyhalothrin, A-cyhalothrln, cyfluthrin, 8-cyfluthrin, deltamethrin, cycloprothrin, r -fluvalinate, flueythrinate, bifenthrin, acrinathrin, tralomethrin, silafluofen, halfenprox and the like; neonlcotlnoid compounds such as thiamethoxam, dinotefuran, acetamiprid, clothianidin and the like; benzoylphenylurea compounds such as chlorfluazuron, teflubenzuron, flufenoxuron, lufenuron and the like; benzoylhydrazide compounds such as tebufenozide, halofenozide, methoxyfenozide, chxomafenozide and the like; thiadiazine derivatives such as buprof ezin and the like; nelicetoxin derivatives such as cartap, thiocyclam, bensultap and the like; chlorinated hydrocarbon compounds such as endosulfan, 7-BHC, 1,1-bis(chlorophenyl)-2,2,2-trichloroethanol and the like; formamidine derivatives such as amitraz, chlordimeform and the like; thiourea derivatives such as diafenthiuron and the like; phenylpyrazole compounds such as ethiprole, acetoprole and the like; chlorfeirapyr"~pym~e"trozine;"spinosa'd', indoxacarb, pyridalyl, pyriproxyfen, fenoxycarb, diofenolan, cyromazine, bromopropylate, tetradifon, quinomethlonate, propargite, fenbutatin oxide, hexythiazox, etoxazole, clofentezine, pyridaben, fenpyroximate, tebufenpyrad, pyriraidifen, fenazaquin, acequinocyl, bifenazate, fluacrypyrim. 36 spirodiclofen, spiremesifen, milbemectin, avsrmectin, emamectin benzoate, azadirachtin, polynactin complex [tetranactin, dinactin, trinactin] and the like. The present invention will be illustrated further in detail by the following formulation examples, test examples and the like, but the present invention is not limited to these examples. In production examples and reference production examples, regarding aH-NMR, data measured using tetramethylsilane as an internal standard in a deuterochloroform solvent are shown in terms of chemical shift ( 6 [ppmjvalue) unless otherwise stated. [Working Examples] Production Example 1 Into 3 ml of ethanol was resolved 0.3 g of 4-(2-butynyloxy)-6-chloro-5-fluoropyrimidine, 0.45 g of 2-methylpyperidine was added tnererin, and the mixture was stirred for 5 hours under reflux condition. The reaction mixture was cooled to near room temperature and concentrated. The residue was subjected to silica gel column chromatography to obtain 0.28 g of 4-{2-butynyloxy)-5-fluoro-6-(2-methylpiperidinojpyriniidine (hereinafter, referred to as Compound (1)). CH3 F OCH2C=CCH3 XH-NMR: 1.25 (d. 3H), 1.58-1.79 (m, 6H), 1.88 (t, 3H) , 3.14-3.18 (m, 1H), 4.21-4.24 (m, 1H), 4.65-4.78 (m, 1H) , 4.97 Production Example 2 37 Into 3 ml of ethanol was resolved 0.3 g of 4-{2-butynyloxy)-6-chloro-5-fluoropyrimidine, 0.38 g of piperidine was added thererin, and the mixture was stirred for 7 hours under reflux condition. The reaction mixture was cooled to near room temperature and concentrated. The residue was subjected to silica gel column chromatography to obtain 0.37 g of 4-(2-butynyloxy)-5-fluoro-6-piperidinopyr±midine (hereinafter, referred to as Compound (2)). 1.81-1.91 (m, 4H, involving a triplet at 1.87), 2.60-2.64 (m, 1H), 2.92-3.01 (m, 1H) . 4.26-4.38 (m, 2H), 4.97 (q, 2H), 8.04 (s, 1H) Production Example 4 Into 3 ml of ethanol was resolved 0.3 g of 4-(2-butynyloxy)-6-chloro-5-fluoropyrimidine, 0.51 g of 3,5-dimethylpiperidine {cis/trans = about 3/1) was added thererin, and the mixture was stirred for 8 hours under reflux condition. The reaction mixture was cooled to near room temperature, and concentrated. Into the residue was added a saturated ammonium chloride aqueous solution, and the mixture was extracted with tart-butyl methyl ether three times. The organic layers were washed with a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to obtain 0.40 g of 4-(2-butynyloxy)-5-fluoro-6-(3,5-dimethylpiperidlno)pyrimidlne (hereinafter, referred to as Compound [4)). Compound (4) had the cis/trans diastereomer originated two methyls on the piperidine ring. The ratio of the cis/trans diastereomer was about 3.3/1. Production Example 5 Into 3 ml of ethanol was resolved 0.3 g of 4-(2-butynyloxy)-6-chloro-5-fluoropyrimidine, 0.45 g of 39 hexarnethyleneimine was added thererin, and the mixture was stirred for 10 hours under reflux condition. The reaction mixture was cooled to near room temperature, and concentrated. The residue was subjected to silica gel column chromatography to obtain 0.29 g of l-{6-(2-butynyloxy)-5-fluoro-4-pyr±midinyl}hexahydro-lH-azepine (hereinafter, referred to as Into 3 ml of ethanol was resolved 0.3 g of 4-(2-butynyloxy)-6-chloropyrimidine, 0.55 g of 3,5-dimethylpiperidine (cis/trans = about 3/1) was added thererin, and the mixture was stirred for 10 hours under reflux condition. The reaction mixture was cooled to near room temperature, and concentrated. Into the residue was added a saturated ammonium chloride aqueous solution, and the mixture was extracted with tert-butyl methyl ether three times. The-organic layers were washed with a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica .gel column chromatography to obtain 0.44 g of 4-{2-butynyloxy)-6-(3,5-dlmethylpiperidino)pyrimidine (hereinafter, referred to as Compound (7) ) . Compound (7) had the cis/trans diastereomer originated two methyls on the piperidine ring. The ratio of the cis/trans diastereomer was about 3.1/1. Production Example 8 Into 3 ml of ethanol was resolved 0.3 g of 4-(2-butynyloxy)-5,6-dichloropyrimidine, 0.47 g of 3,5-dimethylpiperidine (cis/trans = about 3/1) was added thererin, and the mixture was stirred for 8 hours under reflux condition. The reaction mixture was cooled to near room temperature, and concentrated. Into the residue was added a saturated ammonium chloride aqueous solution, and the mixture 41 was extracted with tert-butyl methyl ether three times. The organic layers were washed with a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column, chromatography to obtain 0.36 g of 4~(2-butynyloxy)-5-chloro- 6 - (3,5-dimethylpiperidino)pyrimidine (hereinafter, referred to as Compound (8)). Compound (8) had the cis/trana diastereomer originated two methyls on the piperidine ring. The ratio of the cis/trans diastereomer was about 3.6/1. Production Example 9 Into 3 ml of ethanol was resolved 0.3 g of 4-(2-butynyloxy)-6-chloro-5-methylpyr±midine, 0.47 g of 3,5-dlmethylpiperidine (cis/trans = about 3/1) was added thererin, and the mixture was stirred for 16 hours under reflux condition. The reaction mixture was cooled to near room temperature, and concentrated. Into the residue was added a saturated ammonium chloride aqueous solution, and the mixture was extracted with tert-butyl methyl ether three times. The organic layers were washed with -a- saturated sodium-chloride aqueous solution, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to obtain 0.33 g of 4-{2-butynyloxy)-5-methyl-6-(3,5-dimethylpiperidino)pyrimidine (hereinafter, referred to as Compound (9)). Compound (9) had the cis/trans 42 Production .Example -11 0.2 g of 4-chloro-5-fluoro-6-(2-pentynyloxy)pyrimidine and 0.32 g of 3,5-dimethylpiperidine (cis/trans = about 3/1) were mixed and left for 3 hours at room temperature. The reaction mixture was subjected to silica gel column chromatography to obtain 0.23 g of 4-(3.5-dimethylpiperidino)-5-fluoro- 43 6-(2-pentynyloxy)pyriniidine (hereinafter, referred to as Compound (11)). Compound (11) had the cis/trans diastereomer originated two methyls on the piperidine ring. The ratio of the cis/trans diastereomer was about 3.8/1. 44 Production Example 15 0.07 g of sodium hydride (60% oil suspention) was suspended in 2 ml of tetrahydrofuran. 0.5 ml of tetrahydrofuran solution of 0.13 g of 2-pentyn-l-ol was added dropwise at 0 "C therein, and the mixture was stirred for 10 minutes. Into the mixture was added dropwise-0-.S ml of tetrahydrofuran solution of 0.3 g of 4-chloro-6-(3,5-dlmethylpiperidino)pyrimidine obtained the Reference Production Example 6, and stirred for 6 hours at room temperature. Into the reaction mixture was added a saturated ammonium chloride aqueous solution, and the mixture was extracted with tert-butyl methyl ether three times. The organic 45 layers were washed with a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to obtain 0.15 g of 4-(3,5-diroethylpiperidino) ~6-(2-pentynyloxy)pyriraid±ne (hereinafter, referred to as Compound (15)}. Compound (15) had the cis/trans diastereomer originated two methyls on the pyperidine ring. The ratio of the cis/trans diastereomer was about 8.2/1. 2H), 5.86 (s, 1H), 8.30 {s, 1H) Production Example 17 Into 2 ml of N,N-dimethylformamide was resolved 183 mg of 4-chloro-6-{2-butynyloxy}pyrimidine, 166 mg of pottasium carbonate and 71 mg of pyrrolidine was added thererin, and the mixture was stirred for 4 hours at 55-60^ . The reaction mixture was cooled to near room temperature, ethyl acetate was added therein, and the mixture was washed with a saturated sodium chloride aqueous solution three times. The organic layers were dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to obtain 170 mg of 4-(2-butynyloxy)-6-(l-pyrrolidinyl)pyrimidine (hereinafter, referred to as Compound (17)). Production Example IB Into 2 ml of N,N-dimethylformamide was resolved 183 mg of 4-chloro-6-(2-butynyloxy)pyrimidine, 166 mg of pottasium carbonate and 99 mg of 4-methylpiperidine was added thererin, and the mixture was stirred for 4 hours at BO'C. The reaction mixture was cooled to near room temperature, ethyl acetate was added therein, and the mixture was washed with a saturated sodium chloride aqueous solution three times. The organic layers were dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to obtain 206 mg of 4-(2-butynyloxy)-6-(4-methylpiperidino) pyrimidine (hereinafter, referred to as Compound (18)). 47 Production Example 20 Into-2 ml of N,N-dimethylf ormamide was resolved 183 mg of 4-chloro-6-(2-butynyloxyJpyrimidine, 166 mg of pottasium carbonate and 99 mg of 2-methylpiperidine was added thererin, and the mixture was stirred for 4 hours at SOt^ and 3 hours at 1200 . The reaction mixture was cooled to near room temperature, ethyl acetate was added therein, and the mixture was washed with 48 a saturated sodium chloride aqueous solution three times . The organic layers were dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to obtain 66 mg of 4-(2-butynyloxy)-6-(2-methylpiperidino)pyrimidine {hereinafter, referred to as Compound (20)) . 0.3 g of 4-chloro-6-(2-butynyloxy)pyrimidine and 0.56 g of 2-ethylpiperidine were mixed and left for 18 hours at 800 . The reaction mixture was cooled to near room temperature and subjected to silica gel column chromatography to obtain 0.14 g of 4-(2-butynyloxy)-6-(2-ethylpiperidino)pyrimidine (hereinafter, referred to as Compound (22)). 1H), 4.61 (brd, 1H), 4.95 (q, 2H) , 5.92 (s, 1H}, 8.33 (s, 1H) Production Example 26 Into 2 ml of N,N-dimethylformam±de was resolved 0.2 g of 4-(2-butynyloxy)-5-fluoro-6-chloropyrimidine, 0.28 g of pottasium carbonate and 0.15 g of 3-triflucromethylplperidine was added thererin, and the mixture was stirred for 5 hours at 70"C. The reaction mixture was cooled to near room temperature, ethyl acetate was added therein, and the mixture was washed with a saturated sodium chloride aqueous solution three times. The organic layers were dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to obtain 0.28 g of 4-(2-butynyloxy}-5-fluoro-6-(3-methylpiperidino)pyrimidine (hereinafter, referred to as Compound (26)}. Production Example 27 Into 4 ml of N,N-dimethylformamide was resolved 0.37 g of 4-(2-butynyloxy)-6-chloropyrimidine, 0.56 g of pottasium carbonate and 0.2 g of 3,3-dimethylpyrrolidine was added thererin, and the mixture was stirred for 6 hours at- SO'C. The reaction mixture was cooled to near room temperature, ethyl acetate was added therein, and the mixture was washed with a saturated sodium chloride aqueous solution three times. The organic layers were dried, over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column 52 Production Example 2 9 0.10 g of sodium hydride (6 0% oil suspention} was suspended in 3 ml of tetrahydrofuran. 1 ml of tetrahydrofuran solution 53 of 0.16 g of 2-butyn-l-ol was added dropwise therein, and the mixture was stirred for 10 minutes. Into the mixture was added dropwise 1 ml of tetrahydrofuran solution of 0.31 g of 4-chloro-6-(cis-3,5-dimethylpiperidino) -5-fluoropyrimidine and stirred for 6 hours at 60 T3. Into the reaction mixture was added a saturated ammonium chloride aqueous solution, and the mixture was extracted with tert-butyl methyl ether three times. The organic layers were washed with a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to obtain 0.32 g of 4-(2-butynyloxy}-5 -fluoro-6-(cis-3,5-dlmethylpiperidino}pyrimidine (hereinafter, referred to as Compound (29)), Production Example 30 0.16 g of sodium hydride (60% oil suspention) was suspended in 4 ml of tetrahydrofuran. 1 ml of tetrahydrofuran solution of 0.27 g of 2-butyn-l-ol was added dropwise therein, and the mixture was stirred for 10 minutes at room temperature. Into the mixture was added dropwise 1 ml of tetrahydrofuran solution of -0:64 g of A -chlorous- ( 3 , S-'di-e-thylpi-peridinolpyrim-idine , wherein the ratio of cis/trans diasteromer on the piperidino ring was 1:1, and stirred for 5 hours at eo'C. Into the reaction mixture was added a saturated ammonium chloride aqueous solution, and the mixture was extracted with tert-butyl methyl ether three times. The organic layers were washed with a saturated sodium 54 Production Example 31 Into 2 ml of acetnltrlle were added 0.20 g of 4-(2-butynyloxy)-6-chloropyrimidine, 0.45 g of pottasium carbonate and 0.20 g of 3,3-dimethylpiperidine hydrochloride, and the mixture was stirred for 2 hours at SO'C. The reaction mixture was cooled to near room temperature, a saturated ammonium chloride aqueous solution was added therein, and the mixture was extracted with tert-butyl methyl ether three times. The organic layers were washed with a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate and Concentrated. Th"e "residue was subjected to srlrca -g-ei eo-lumn-chromatography to obtain 0.27 g of 4-(2-butynyloxy)-6 -(3,3 -dimethylpiperidino)pyrimidine (hereinafter, referred to as Compound (31)). 55 pmsmierton Example -33 ■ 0 . 05 g of sodium hydride (60% oil suspention) was suspended in 2 ml of tetrahydrofuran. Ths 0.5 ml of tetrahydrofuran solution of 0.08 g of 2-butyn-l-ol was added dropwise at room temperature therein, and the mixture was stirred for 10 minutes. Into the mixture was added dropwise 0-5 ml of tetrahydrofuran 56 Production Example 34 0.08 g of sodium hydride ( 60% oil suspention) was suspended in 3 ml of tetrahydrofuran. 0.5 ml of tetrahydrofuran solution of 0.15 g of 2-butyn-l-ol was added dropwise at room temperature therein, and the mixture was stirred for 10 minutes. Into the mixture was added dropwise 0.5 ml of tetrahydrofuran solution of 0.33 g of l-(6-chloropyrimidin-4-yl)-2,5-dimethyl hexahydro-lH-azepine at room temperature, and stirred for 4 hours at"600. ffi'f ter 'the reaction" mixture was cooled--to-near room temperature, a saturated ammonium chloride aqueous solution was added therein, and the mixture was extracted with tert-butyl methyl ether three times. The organic layers were washed with a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate and concentrated. The residue 57 58 Production Example 37 Into 3 ml of acetnitrile were added 0.30 g of 4-(2-butynyloxy)-6-chloropyrimidine, 0.68 g of pottasium carbonate and 0.33 g of 3,4-dimethylpyrrolidine hydrochloride 59 (cis and trans diastereomer mixture), and the mixture was stirred for 4 hours at 70C. The reaction mixture was cooled to near room temperature, a saturated ammonium chloride aqueous solution was added therein, and the mixture was extracted with cert-butyl methyl ether three times. The organic layers were washed with a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to obtain 0.42 g of 4-(2-butynyloxy)-6-(3,4-dimethylpyrrolidin-1-yl) pyrimidine (hereinafter, referred to as Compound (37)). Production Example 38 Into 2 ml of acetnitrile were added 0.20 g of 4-(2-butynyloxy)-6-chloropyrimidine, 0.45 g of pottasium carbonate and 0.24 g of 3,3,5,5-tetramethylpiperidine hydrochloride, and the mixture was stirred for 4 hours at 6 0 t. The reaction mixture was cooled to near room temperature, a saturated ammonium chloride aqueous solution was added therein, and the mixture was extracted with tert-butyl methyl ether three ■times. -The organic layers were washed-wlt-h a saturated solium chloride aqueous solution, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to obtain 0.23 g of 4-(2-butynyloxy)-6-(3 , 3,5,5-tetramethylpiperidino)pyrimidine (hereinafter, referred to .as Compound (38)). 60 Production Example 40 0 . 07 g of sodium hydride { 60% oil suspention) was suspended in 3 ml of tetrahydrofuran. 0.5 ml of tetrahydrofuran solution of 0.11 g of 2-butyn-l-ol was added dropwise at room temperature 61 therein, and the mixture was stirred for 10 minutes. Into the mixture was added dropwise 0.5 ml of tetrahydrofuran solution of 0.30 g of l-(6-chloropyrimidih-4-yl)-cis-2,6-dimethyl-hexahydro-lH-azepine at room temperature, and stirred for 8 hours at 600. After the reaction mixture was cooled to near room temperature, the reaction mixture was poured into a saturated ammonium chloride aqueous solution, and the mixture was extracted with tert-butyl methyl ether three times. The organic layers were washed with a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to obtain 0.25 g of 1-{6-(2-butynyloxy) pyrimidin-4-yl)-cis- 2,6-dimethyl-hexahydro-1H-azepine (hereinafter, referred to as Compound (40)). Production Example 41 0.10 g of sodium hydride (60% oil suspention) was suspended in 3 ml of tetrahydrofuran. 0.5 ml of tetrahydrofuran solution of 0.15 g of 2-butyn-l-ol was added dropwise at room temperature therein, and the mixture was stirred for 10 minutes. Into the mixture was added dropwise 0.5 ml of tetrahydrofuran solution of 0.30 g of l-(6-chloro-5-fluoropyrimidin-4-yl)-cis~2-,6-dimethyl-hexahydro-lH-azep±ne at room temperature.;-and stirred for 8 hours at 700. After the reaction mixture was cooled to near room temperature, the reaction mixture was poured into a saturated ammonium chloride aqueous solution, and the mixture was extracted with tert-butyl methyl ether three times. The organic layers were washed with a saturated sodium chloride 62 Production Example 42 0 .10 g of sodium hydride (6 0% oil suspention) was suspended in 3 ml of tetrahydrofuran, 0.5 ml of tetrahydrofuran solution of 0.15 g of 2-butyn-l-ol was added dropwise at room temperature therein, and the mixture was stirred for 10 minutes. Into the mixture was added dropwise 0.5 ml of tetrahydrofuran solution of 0.31 g of 1-(6-chloro-5-fluoropyrimidin-4-yl)-trans-2,6-dimethyl-hexahydro-lH-azepine at room temperature, and stirred for 6 hours at SO'C. After the reaction mixture was cooled to near room temperature, the reaction mixture was poured into a saturated ammonium chloride aqueous solution, and the mixture was extracted with tert-butyl methyl ether three times. - The organic laye-r-s we-re-washed.-with.-a-saturated sodium, chloride aqueous solution, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to obtain 0.34 g of 1-(6-{2-butynyloxy)-5-fluoropyrimidin-4-yl)-trans-2,6-dimethyl-hexahydro-lH-azep ine (hereinafter, referred to as Compound (42)). 63 Production Example 43 0.10 g of sodium hydride (60% oil suspention) was suspended in 3 ml of tetrahydrofuran. 0.5 ml of tetrahydrofuran solution of 0.16 g of 2-butyn-l-ol was added dropwise at room temperature therein, and the mixture was stirred for 10 minutes. Into the mixture was added dropwise 0.5 ml of tetrahydrofuran solution of 0.30 g of 1-(6-chloropyrimidin-4-yl)-trans-2,6-dimethyl hexahydro-lH-azepine at room temperature, and stirred for 5 hours at 600. After the reaction mixture was cooled to near room temperature, the reaction mixture was poured into a saturated ammonium chloride aqueous solution, and the mixture was extracted with terr-butyl methyl ether three times. The organic layers were washed with a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to obtain 0.25 g of 1~(6-(2-butynyloxy) pyrimidin-4-yl}-trans-2,6-dimethyl-hexahydro-lH-azepina (hereinafter, referred to as Compound (43)). {q, 2H), 5.85 (s, 1H), 8.01 (s, IH) GC-MS: 273 (M+) Production Example 44 0.02 g" of sodium hydride (6 0% oil suspention) was suspended in 1 ml of tetrahydrofuran. 0.3 ml of tetrahydrofuran solution of 0.O2 g of 2-butyn-l-ol was added dropwise at room temperature therein, and the mixture was stirred for 10 minutes. Into the mixture was added dropwise 0.3 ml of tetrahydrofuran solution of 0.05 g of 6-chloro-4-(trans-3,5-dimethylpiperidine)-5-fluoropyrimidine at room temperature, and stirred for 7 hours at 60^. After the reaction mixture was cooled to near room temperature, the reaction mixture was poured into a saturated ammonium chloride aqueous solution, and the mixture was extracted with tert-butyl methyl ether three times. The organic layers were washed with a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to obtain 0.05 g of 4-{2-butynyloxy)-6- (trans-3 , 5-dimethylpiperidino)pyri[nidine (hereinafter, referred to as Compound (44)). Production Example 45 0.2 g of 4-chloro-6-{2-pentynyloxy)pyrimidine and 0.31 g of octahydroazocine were mixed and left for 2 hours at room temperature. The reaction mixture was subjected to silica gel column chromatography to obtain 0.30 g of l-(6-{2-butynyloxy) 65 Production Example 47 0 . 07 g of sodium hydride {60% oil suspention) was suspended in 2 ml of tetrahydrof uran. 0 . 5 ml of tetrahydrofuran solution of 0.10 g of 2-butyn-l-ol was added dropwise at room temperature therein, and the-mixture was stirred for 10 minutes. Into the., mixture was added dropwise 0.5 ml of tetrahydrofuran solution of 0.20 g of 1-(6-chloro-5-fluoropyrimldin-4-yl)-2-methyl-hexahydro-lH-azepine at room temperature, and stirred for 6 hours at 60tC. After the reaction mixture was cooled to near room temperature, the reaction mixture was poured into a 66 saturated ammonium chloride aqueous solution, and the mixture was extracted with tert-butyl methyl ether three times. The organic layers were washed with a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to obtain 0.27 g of 1-{6-{2-butynyloxy) -5-fluoropyrimidin-4-yl)-2-methyl-hexahydro-lH-azepine (hereinafter, referred to as Compound (47)). Production Example 48 0.06 g of sodium hydride (6 0% oil suspentlon) was suspended in 1. 5 ml of tetrahydrof uran. 0 . 3 ml of tetrahydrof uran solution of 0.08 g of 2-butyn-l-ol was added dropwise at room temperature therein, and the mixture was stirred for 10 minutes. Into the mixture was added dropwise 0.3 ml of tetrahydrofuran solution of 0.19 g of 6-chloro-4-(cis-2,6-dimethylpiperidino)pyrimldine at room temperature, and stirred for 6 hours at SO'C . After the reaction mixture was cooled to near room temperature, the reaction mixture was poured into a saturated ammonium chloride aqueous solution, and the mixture was extracted with tert-butyl methyl ether three times. The organic layers were washed with a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to obtain 0.20 g of 4- (2-butynyloxy) -6- (cis-2, 6-dimethylpiperidino)pyritaidine (hereinafter, referred to as Compound (48)). 67 Production Example 49 0 . 05 g of sodium hydride (60% oil suspention) was suspended in 2 ml of tetrahydrofuran. 0.3 ml of tetrahydrofuran solution of 0,09 g of 2-butyn-l-ol was added dropwise at room temperature therein, and the mixture was stirred for 10 minutes. Into the mixture was added dropwise 0.3 ml of tetrahydrofuran solution of 0.21 g of 6-chloro-4-(cis-2,6-dimethylpiperidino)-5-fluoropyrimidine at room temperature, and stirrea for 6 hours at 600. After the reaction mixture was cooled to near room temperature, the reaction mixture was poured into a saturated ammonium chloride aqueous solution, and the mixture was extracted with tert-butyl methyl ether three times. The organic layers were' washed with a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to obtain 0-21 g of 4-(2-butynyloxy)-G-(cis-2,6-dimethylpiperidino)-5-fluoropyrimldins (hereinafter, referred to as Compound (49)). 68 Production Example 50 0.07 g of sodium hydride (6 0% oil suspention) was suspended in 2 ml of tetrahydrofuran. 0.3 ml of tetrahydrofuran solution of 0.11 g of 2-butyn-l-ol was added dropwise at room temperature therein, and the mixture was stirred for 10 minutes. Into the mixture was added dropwise 0.3 ml of tetrahydrofuran solution of 0.30 g of 1-(6-chloro-5-fluoropyrimldin-4-yl)-2-ethyl-hexahydro-lH-azepine at room temperature, and stirred for 9 hours at 600. After the reaction mixture was cooled to near room temperature, the reaction, mixture was poured into a saturated ammonium chloride aqueous solution, and the mixture was extracted with tert-butyl methyl ether three times. The organic layers were washed with a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to obtain 0.31 g of 1-(6-{2-butynyloxy)-5-fluoropyrimidin-4-yl)-2-ethyl-hexahy&ro-lH-azepine (hereinafter, referred to as Compound (50)). ..Production Example 51 0.09 g of sodium hydride (6 0% oil suspention) was suspended in 3 ml of tetrahydrofuran. 0.3 ml of tetrahydrofuran solution of 0.15 g of 2-butyn-l-ol was added dropwise at room temperature therein, and the mixture was stirred for 10 minutes. Into the mixture was added dropwise 0.3 ml of tetrahydrofuran solution 69 of 0.40 gof 4,S-difluoro-6-(3, 5-dimethylpiperidino) pyrimidine {cis/trans diastereomer - about 5/l)at room temperature, and stirred for 20 minutes at 00. The reaction mixture was poursd into a saturated ammonium chloride aqueous solution, and the mixture was extracted with tert-butyl methyl ether three times. The organic layers were washed with a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to obtain 0.46 g of 4-(2-butynyloxy)-5-fluoro-6-(3,5-dimethylpiperidino)pyrimidine (hereinafter, referred to as Compound (51)). Compound (51) had the cis/trans diastereomer originated two methyls on the pyperidine ring. The ratio of the cis/trans diastereomer was about 5/1. Produntion Example 52 0. 09 g of sodium hydride (60% oil suspention) was suspended in 2 ml of tetrahydrofuran. 0.3 ml of tetrahydrofuran solution of 0.13 g of 2-butyn-l-ol was added dropwise at room temperature therein, and the mixture was stirred for 10 minutes. Ipto the mixture was added dropwise 0.3 ml of tetrahydrofuran solution of 0.4 g of 5-chloro-2,4-difluoro-6-(3,5-dimethylpiperidino) pyrimidine at 0"C, and stirred for 30 minutes at same temperature. The reaction mixture was poured into a saturated ammonium chloride aqueous solution, and the mixture was extracted with 70 text-butyl methyl ether three times. The organic layers were washed with a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to obtain 0.20 g of 5-chloro-4-(2-butynyloxy)-2-fluoro-6-(3,5-dimethyl piperidinojpyrimidine (hereinafter, referred to as Compound (52)}. Compound (52J had the cis/trans diastereomer originated two methyls on the pyperidine ring. The ratio of the cis/trans diastereomer was about 5/1., Formulation Example 3 Each 3 parts of the present compounds (1) to (51) were dissolved in a mixture of 5 parts of a synthetic water-containing silicon oxide fine powder, 5 parts of sodium dodecylbenzeneuslfonate, 30 parts of bentonite, and 57 parts of clay, and, they were mixed thoroughly, then, suitable amount of water was added to the mixture thereof, the resulted mixture was further stirred, granulated in a granulator, and dried under ventilation to obtain a formulation. Formulation Example 4 Each 4. 5 parts of the present compounds (1) to (51) , 1 part of a synthetic water-containing silicon oxide fine powder, 1 part of DRILESS B (manufactured by Sankyo Co. , Ltd. ) and 7 parts of clay were mixed thoroughly in a mortar, then, stirred to mix by a juice mixer. To the resulted mixture was added 86.5 parts of cut clay, they were sufficiently stirred to mix, to obtain a formulation. Formulation Example 5 Each 10 parts of the present compounds (1) to (51) , 35 parts of white carbon containing 50 parts of ammonium polyoxyethylene alkyl ether sulfate, and 55 parts of water were mixed and finely ground according to a wet grinding method, to obtain a formulation. Then, the effect of the present compound of controlling pests will be shown by test examples. Test Example 1 A formulation of a test compound obtained in Formulation Example 5 was diluted with water so that the active ingredient concentration came to 500 ppm to prepare a test spray liquid. The seeds of cucumber were planted in polyethylene cups and grown until their first foliage leaves developed, on which about 20 cotton aphids {Aphis gossypli) were made parasitic. 93 and grown until their first foliage leaves developed, and then a test spray liquid was applied at a ratio of 20 ml/cup to the plant. After the liquid 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 Western flower thxips (Frankllniella occidentalls) were set free on the first true leaf, which was covered with a polyethylene cup. After seven days, the number of surviving pests was examined. As a result, the number of surviving pests was 0 on the leaves treated with each of the present compounds (4), (8) to (11), (23), (24), (26), (29), (32), (33), (44), (46), (47), (51), (52) and (53) . Test Example 3 A formulation of each test compound obtained according to Formulation Example 5 was diluted with water to give the spray liquid for test wherein an effective ingredient concentration is 500 ppm. The seeds of cabbage were planted in polyethylene cups and grown until their first foliage leaves developed. The first foliage leaves were left and the other leaves were cut off. Some adults of silverleaf whiteflies [Bemisia argentlfolii) were set free on the cabbage plants and allowed to lay eggs for about 24 hours. The cabbage plants with about 80 to 100 eggs thus laid were left in a greenhouse for 8 days, and the above test spray liquid was sprayed at the rate of 20 ml/cup onto the cabbage plants with larvae being hatched from the laid eggs. On the 7th day after the application, the number of surviving larvae was counted. As a result, for the present compounds (1) to (53), the number of surviving larvae on the cabbage leaves treated with each of these compounds was not greater than 10. 95 Test Example 4 A formulation of a test compound obtained in Formulation Example 5 was diluted with water so that the active Ingredient concentration came to 500 ppm to prepare a test spray liquid. 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. The rice plants were grown until the second foliage leaves developed and then cut into the same height of 5 cm. The test spray liquid, which had been prepared as described above, was sprayed at the rate of 20 ml/cup onto these rice plants. After the test liquid sprayed onto the rice plants was dried, thirty first-instar larvae of brown planthoppers (Nllaparvata Xugens) were set free on the rice plants, which were then left in a greenhouse at 25" C. On the 6th day after the release of brown planthopper larvae, the number of brown planthoppers parasitic on the rice plants was examined. As a result, in the treatment with each of the present compounds (2), (3), (6), (10) to (12), (14), (15), (17), (18), (22) to (26), (30), (31), (33) to (35), (41) to (43), (45) to (49) and (51), the number of parasitic insects on the 6th day after the treatment was not greater than 3. INDUSTRIAL APPLICABILITY The present compound has an excellent ability of controlling pests, therefore, it is useful as an effective ingredient in a pests controlling composition. WE CLAIM: 1. A pyrimidine compound of the formula (I): wherein R1 represents a hydrogen atom, halogen atom or C1-C4 alkyl; R2 represents C3-C7 alkynyloxy; R3 represents a hydrogen atom, halogen atom or C1-C3 alkyl; X represents C4-C7 polymethylene, in which a CH2-CH2 may be replaced with a CH=CH, optionally substituted with at least one substituent selected from the group consisting of halogen atoms, trifluoromethyl and C1-C4 alkyls. 2. The pyrimidine compound as claimed in claim 1, wherein X is C4-C7 polymethylene optionally substituted with at least one substituent selected from the group consisting of halogen atoms, trifluoromethyl and C1-C4 alkyls. 3. The pyrimidine compound as claimed in claim 1, wherein X is C4-C7 polymethylene optionally substituted with a halogen atom, trifluoromethyl and C1-C4 alkyl. 4. The pyrimidine compound as claimed in claim 1, wherein X is C4-C7 polymethylene. 5. The pyrimidine compound as claimed in claim 1, wherein X is C4-C7 polymethylene substituted with a halogen atom(s). 6. The pyriraidine compound as claimed in claim 1, wherein X is C4-C7 polymethylene substituted with a trifluoromethyl. 7. The pyrimidine compound as claimed in claim 1, wherein X is C4-C7 polymethylene substituted with a C1-C4 alkyl(s). 8. The pyrimidine compound as claimed in claim 1, wherein X is C4-C7 linear alkenylene optionally substituted with a halogen atom, trifluoromethyl and C1-C4 alkyl. 9. The pyrimidine compound as claimed in any one of claim 1 to 8, wherein R1 is a hydrogen atom or C1-C4 alkyl. 10. The pyrimidine compound as claimed in any one of claim 1 to 8, wherein R is 2- butynyloxy or 2-pentynyloxy. U, A pests controlling composition comprising a pyrimidine compound as claimed in claim 1 as an effective ingredient. wherein R1 represents a hydrogen atom, halogen atom or C1-C4 alkyl; R3 represents a hydrogen atom, halogen atom or C1-C3 alkyl; X3 represents C4-C7 poiymethylene, in which a CH2-CH2 may be replaced with a CH=CH, substituted with at least one substituent selected from the group consisting of halogen atoms, trifluoromethyl and Cl-C4aikyls. 13. The pyrimidine compound as claimed in claim 12, wherein X is C4-C7 poiymethylene substituted with at least one substituent selected from the group consisting of halogen atoms, trifluoromethyl and C1-C4 alkyls. 14. The pyrimidine compound as claimed in claim 12, wherein X3 is C4-C7 poiymethylene substituted with a halogen atom(s). 15. The pyrimidine compound as claimed in claim 12, wherein X is C4-C7 poiymethylene substituted with a trifluoromethyl. 16. The pyrimidine compound as claimed in claim 12, wherein X3 is C4-C7 poiymethylene substituted with a C1-C4 alkyl(s).

Full Text

PYRIMIDINE COMPOUND AND PESTS CONTROLLING COMPOSITION
CONTAINING THE SAME
Technical Field
The present invention relates to a pyrimidine compound and a pests controlling composition containing the same.
Background Art
Various compounds have been used in the past for the purpose of pest control. Compounds having' a pyrimidine ring are. known ta have an effect of controlling harmful pests (WO 02/024663), And also a compound having a pyrimidine ring substituted with piperldino is known.
Disclosure of the Invention
The object of the present invention is to provide a pyrimidine compound having an effect of controlling pests, an pests controlling composition having this pyrimidine compound as an effective ingredient, and a method of controlling pests.
Namely the present invention provides a pyrimidine compound (hereinafter, referred to as the present compound) of the formula (I):

wherein R1 represents a hydrogen atom, halogen atom or C1-C4 alkylj R2 represents C3-C7 alkynyloxy; R3 represents a hydrogen atom, halogen atom or C1-C3 alkyl; X represents C4-C7 polymethylene, in which a CH2-CH2 may be replaced with a CH=CH,
2

optionally substituted with at least one substituent selected from the group consisting of halogen atoms, trifluoromethyl and C1-C4 alkyls;
an pests controlling, composition containing the present compound as an effective ingredient, and a method of controlling pests comprising applying an effective amount of the present compound to pests or the habitat of pests.
Embodiments of the Invention
In this specification, "sec" denotes secondary and "tert" denotes tertiary. The representation of "C3-C7", for example in the "C3-C7 alkynyloxy", means the number of the total carbon atoms in the substituent. "C3-C7 Alkynyloxy" means alkynyloxy in which the number of the- total carbon atoms is 3 to 7.
In this specification; the halogen atom represented by R1 includes, for example, a fluorine atom and chlorine atom;
the C1-C4 alkyl represented by R1 includes, for example, methyl, ethyl, propyl, lsopropyl, butyl and isobutyl; the C3-C7 alkynyloxy represented by Ra includes, for example, C3-C7 alkynyloxy wherein the triple bond is located between the carbons of 2 and 3-position in alkynyl (hereinafter, referred to as C3-C7 2-alkynyloxy), and the C3-C7 2-alkynyloxy include, for example, 2-propynyloxy, 2-butynyloxy, 1-methy1-2-butynyloxy, 2-pentynyloxy, 4,4-dimethyl-2-pentynyloxy, l-methyl-2-propynyloxy and 1,l-dimethyl-2-propynyloxy; the halogen atom represented by R3 includes, for example, a fluorine atom and chlorine atom;
the C1-C3 alkyl represented by R3 includes, for example, methyl and ethyl.
In the C4-C7 polymethylene, in which a CH2-CH2 may be
3

replaced with a CH=CH, optionally substituted with a halogen atom, trifluoromethyl and C1-C4 alkyl represented by X; the halogen atom includes fluorine atom, chlorine atom and bromine atom; the C1-C4 alkyl includes methyl, ethyl, propyl, lsopropyl, isobutyl, sec-butyl and tert-butyl.
In the C4-C7 polymethylene, in which a CH2-CH2 may be replaced with a CH«CH, optionally substituted with at least one substituent selected from the group consisting of halogen atoms, trifluoromethyl and C1-C4 alkyls represented by X, the C4-C7 polymethylene, in which a CH2-CK2 may be replaced with a CH-CH, includes tetramethylene, pentamethylene, hexamethylene, heptamethylene and 2-penten-l,5-ylene.
The C4-C7 polymethylene, in which a CH2-CHa may be replaced with a CH-CH, optionally substituted with at least one substituent selected from the group consisting of halogen atoms , trifluoromethyl and C1-C4 alkyls represented by X includes C4-C7 polymethylene optionally substituted with at least one substituent selected from the group consisting of halogen atoms , trifluoromethyl and C1-C4 alkylsr and C4-C7 linear alkenylene optionally substituted with at least one substituent selected from the group consisting of halogen atoms, trifluoromethyl and C1-C4 alkyls. The C4-C7 polymethylene optionally substituted with at least one substituent selected from the group consisting of halogen atoms, trifluoromethyl and C1-C4 alkyls includes, for example, C4-C7 polymethylene, C4-C7 polymethylene substituted with a halogen atom(s), C4-C7 polymethylene substituted with trifluoromethyl, C4-C7 polymethylene substituted with a C1-C4 alkyl(s); more specifically it Includes tetramethylene, 1-methyltetramethylene, 2-methyltetramethylene, 1-ethyltetramethylene, 1-propyltetramethylene, 1-isopropyltetramethylene, l-(tejrt-butyUtetrainethylene, 2-ethyltetramethylene, 1,4-dimethyltetramethylene, 2,3-dimethyItetramethylene, 2,2-dimethyltetramethylene,
4

2-fluorotetramathylene,. 2-(trifluoromethyl)tatramethylene,
3-(trIfluoromethyl)tetramethylene, pentamethylene,
1-methylpentamethylene, 2-methylpentamethylene,
3-methylpentamethylene, 1-ethylpentamethylene,
2-ethylpentamethylene, 1-propylpentamethylene,
2-propylpentamethylene, 3-propylpentamethylene,
1-isopropylpentamethylene, 2-isopropylpentamethylene,
3-isopropylpentamethylene, l-(tert-butyllpentamethylene,
2-(tert-butyl)pentamethylene, 3 -(tart-butyl)pentamethylene,
1-(sec-butyl)pentamethylene, 2-(sec-butyl)pentamethylene,
1, 5-dimethylpentamethylene, 1-, 3-dimethy lpentamethylene-,
1,4-dimethylpentamethylene, 2,4-dimethylpentamethylene,
1,1-dimethylpentamethylene, 2, 2-dimethylpentantefciiylene ,
3,3-dimethylpentamethylene, 2~ethyl-5-methylpentamethylene,
2-ethyl- 4-methylpentamethylene, 2,4-diethylpentamethylene,
1,2-dimethylpentamethylene, 2,2,4-trimathylpentamethylene,
1,2,4,5-tetramethylpentamethylene,
2,2,4,4-tetramethylpentamethylene, 2-fluoropentamethylene,
2-chloropentamethylene, 2-bromopentamethylene,
3-fluoropentamethylene, 3-chloropentamethylene,
3-bromopentamethylene, 2,2-difluoropentamethylene,
3,3-difluoropentamethylene. 2-fluoro-2-methylpentamethylene,
1-(trifluoromethyllpentamethylene,
2 -(trifluoromethyllpentamethylene,
3-(trifluoromethyl)pentamethylene, hexamethylene,
1-methylhexamethylene, 2-methy lhexame thylene.,
3-methylhexamethylene, 4-methylhexamethylene,
1-ethylhexamethylene, 2-ethylhexamethylene,
3-ethylhexamethylene, 1-propylhexamethylene,
2-propylhexamethylene, 3-propylhexamethylene,
I-isopropylhexamethylene, 2-isopropylhexamethylene,
3-isopropylhexamethylene, 1-(tert-butyl)hexamethylene,
1-isobutylhexamethylene, 1-(trifluoromethyl)hexamethylene,
5

1, 4-dimfethylhexamethylene, 1, 5 -dimethylhexamethylene,
1, 6-dimethylhexa:raethylene, 2, 5-dimethylhexamethylene and
heptamethylene.
The C4-C7 linear alkenylene optionally substituted with at least one substituent selected from the group consisting of halogen atoms, trifluoromethyl and C1-C4 alkyls, for example, 2-buten-1,4-ylene, 2-methyl-2-buten-l,4-ylen, 2,3-dimethyl-2-buten-1,4-ylen, 2-penten-l,5-ylene, 1-ethyl-2-penten-l,5-ylene, 2-methyl-2-penten-l,5-ylene , 2-ethyi-2-penten-l,5-ylene, 4-methyl-2-penten-l,5-ylene, 5-methyl-2-penten-l,5-ylene, 5-ethyl-2-penten-l,5-ylene, 2,4-dimethyl-2-penten-l,5-ylene, 2-hexen-l,6-ylene, 1-methyl- 2-hexen-1,6-ylene, 1-ethyl-2-hexen-1,6-ylene, 2-methyl-2-hexen-l,6-ylene, 6-ethyl-2-hexen-1,6-ylene, 2,5-dimethyl-2-hexen-1,6-ylene, 3-hexen-l,6-ylene. 2-hepten-l,7-ylena and 3-hepten-l,7-ylen&.
Embodiments of the present compound include, for example, the following compounds:
the pyrimidine compound wherein R1 is a hydrogen atom or C1-C4 alkyl in the formula (I);
the pyrimidine compound wherein R1 is a hydrogen atom In the formula (I);
the pyrimidine compound wherein R2 is C3-C7 2-alkynyloxy in the formula (I);
the pyrimidine compound wherein R2 is 2-butynyloxy or 2-pentynyloxy in the formula (I);
the pyrimidine compound wherein R3 is a hydrogen atom in the formula (I);
the pyrimidine compound wherein R2 is a halogen atom in the formula (I);
the pyrimidine compound wherein R2 is a fluorine atom in the formula (I);
6

the pyrimidine compound wherein X is C4-C7 polymethylene
optionally substituted with at least one substifcuent selected
from the group consisting of halogen atoms, trifluoromethyl and
C1-C4 alkyl in the formula (I);
the pyrimidine compound wherein X is C4-C7 polymethylene
optionally substituted with a halogen atom, trifluoromethyl or
C1-C4 alkyl in the formula (I);
the pyrimidine compound wherein X is C4-C7 polymethyleTie in the
formula (I J;
the pyrimidine compound wherein X is C4-C7 polymethylene
substituted with a halogen atom Is) in the formula (I);
the pyrimidine compound wherein X is C4-C7 polymethylene
substituted with a trifluoromethyl in the formula (I);
the pyrimidine compound wherein X is C4-C7 polymethylene
substituted with a C1-C4 alkylts) in the formula (I) ;
the pyrimidine compound wherein X is tetraethy] ene or
pentamethylene, optionally substituted with at least one
substituent selected from the group consisting of halogen atoms,
trifluoromethyl and C1-C4 alkyls in the formula (I);
the pyrimidine compound wherein X is C4-C7 linear alkenylene
optionally substituted with at least one substituent selected
from the group consisting of halogen atoms, trifluoromethyl and
C1-C4 alkyls in the formula (I);
the pyrimidine compound wherein X is tetramethylene optionally
substituted with at least one substituent selected from the
group consisting of halogen atoms, trifluoromethyl and C1-C4
alkyls in the formula {1};
the pyrimidine compound wherein X is pentamethylene optionally
substituted with at least one substituent selected from the
group consisting of halogen atoms, trifluoromethyl and C1-C4
7

alkyls in the formula the pyrimidine compound wherein X is hexamethylene optionally
substituted with at least one substituent selected from the
group consisting of halogen atoms, trifluoromethyl and C1-C4
alkyls in the formula (I);
the pyrimidine compound wherein X is tQtramethylene optionally
substituted with a halogen atom, trifluoromethyl or C1-C4 alkyl
in the formula (1) ;
the pyrimidine compound wherein X is pentamethylene optionally
substituted with a halogen atom, trifluoromethyl or C1-C4 alfcyl
in the formula (I) ;
the pyrimidine compound wherein X is hexamethylene optionally
substituted with a halogen atozn, trifluoromethyl or C1-C4 alkyl
in the formula (1);
the pyrimidine compound wherein x is tetramethylene in the f ormula (I), following described;

8

the pyrimidine compound wherein R1 is a hydrogen atom or C1-C4 alkyl, and X is C4-C7 polymethylena optionally substituted with at least one substltuent selected from the group consisting of halogen atoms, trifluoromethyl and C1-C4 alkyls in the formula
CD;
the pyrimidine compound wherein R1 is a hydrogen atom or C1-C4
alkyl, and X is C4-C7 polymethylene optionally substituted with
a halogen atom, trifluoromethyl or C1-C4 alkyl in the formula
(I);
the pyrimidine compound wherein R1 is a hydrogen atom or C1-C4
alkyl, and X is -tetraethylen© or pentamethylene, optionally
substituted with at least one substituent selected from the
group consisting of halogen atoms, trifluoromethyl and C1-C4
alkyls in the formula (I);
the pyrimidine compound wherein R1 is a hydrogen atom or C1-C4
alkyl, and X is C4-C7 linear alkenylene optionally substituted
9

with at least one substituent selected from the group consisting
of halogen atoms, trlfluoromethyl and C1-C4 alkyls in the
formula (I) ;
the pyrimidine compound wherein Ra is 2-butynyloxy or
2-pentynyloxy, and X is C4-C7 polymethylene optionally
substituted with at least one substituent selected from the
group consisting of halogen atoms, trlfluoromethyl and C1-C4
alkyls in the formula (I);
the pyrimidine compound wherein R2 is 2-butynyloxy or
2-pentynyloxy, and X is C4-C7 polymethylene optionally
substituted with a halogen atom, trlfluoromethyl or C1-C4 alkyl
in the formula (I);
the pyrimidine compound wherein R2 is 2-butynyloxy or
2-pentynyloxy, and X is tetraethylene or pentamethylene,
optionally substituted with at least one substituent selected
from the group consisting of halogen atoms, trlfluoromethyl and
C1-C4 alkyls in the formula (I);
the pyrimidine compound wherein R2 is 2-butynyloxy or
2-pentynyloxy, and X is C4-C7 linear alkenylene optionally
substituted with at least one substituent selected from the
group consisting of halogen atoms, trlfluoromethyl and C1-C4
alkyls in the formula (I);
the pyrimidine compound wherein R1 is a hydrogen atom or C1-C4
alkyl, R2 is 2-butynyloxy or 2-pentynyloxy, and X is C4-C7
polymethylene optionally substituted with at least one
substituent selected from the group consisting of halogen atoms,
trlfluoromethyl and C1-C4 alkyls in the formula (I);
the p-yrimidine compound wherein-R?' is ..a hydrogen atom, or .C1-C4
alkyl, R2 is 2-butynyloxy or 2-pentynyloxy, and X is C4-C7
polymethylene optionally substituted with a halogen atom,
trlfluoromethyl or C1-C4 alkyl in the formula (I);
the pyrimidine compound wherein R1 is a hydrogen atom or C1-C4
alkyl, R2 is 2-butynyloxy or 2-pentynyloxy, and X is
10

tetraethylene or pentamethylene , optionally substituted with at
least one substituent selected from the group consisting of
halogen atoms, trifluoromethyl and C1-C4 alkyls in the formula
(I);
the pyrimldine compound wherein R1 is a hydrogen atom or C1-C4
alkyl, R2 is 2-butynyloxy or 2-pentynyloxy, and X is C4-C7 linear
alkenylene optionally substituted with at least one substituent
selected from the group consisting of halogen atoms,
trifluoromethyl and C1-C4 alkyls in the formula (I);
the pyrimidine compound wherein R1 is a hydrogen atom, and R3
is a hydrogen atom in the formula (I);
the pyrimidine compound wherein R1 is a hydrogen atom, and R3
is a halogen atom in the formula (I);
the'pyrimidine compound wherein R1 is a hydrogen atom, and R3
is a fluorine atom in the formula (I);
the pyrimidine compound wherein R1 is a hydrogen atom, R2 is C3-C7
2-alkynyloxy, and R3 is a hydrogen atom in the formula (I);
the pyrimidine compound wherein R1 is a hydrogen atom, Rz is C3-C7
2-alkynyloxy, and R3 is a halogen atom in the formula (I);
the pyrimidine compound wherein Rl is a hydrogen atom, R2 is C3-C7
2-alkynyloxy, and R3 is a fluorine atom in the formula (I);
the pyrimidine compound wherein R1 is a hydrogen atom, R2 is C3-C7
2-alkynyloxy, R3 is a hydrogen atom, and X is C3-C8
pentamethylene optionally substituted with at least one
substituent selected from the group consisting of halogen atoms,
trifluoromethyl and C1-C4 alkyls in the formula (I);
the pyrimidine compound wherein R1 is a hydrogen atom, R3 is C3-C7
2 - alkynyloxy,-R3- is a halogen-atom, and X-is C3-C8 pentamethylene
optionally substituted with at least one substituent selected
from the group consisting of halogen atoms, trifluoromethyl and
C1-C4 alkyls in the formula (I);
the pyrimidine compound wherein R1 is a hydrogen atom, Rz is C3-C7
2-alkynyloxy, R3 is a fluorine atom, and X is C3-C8
11

pentamethylene optionally substituted with at least one
substituent selected from the group consisting of halogen atoms,
trifluoromethyl and C1-C4 alkyls in the formula (I);
the pyrimidine compound wherein R1 is a hydrogen atom, R2 is C3-C7
2-alkynyloxy, R3 is a hydrogen atom, and X is C3-C8 hexamethylene
optionally substituted with at least one substituent selected
from the group consisting of halogen atoms, trif luoromethyl and
C1-C4 alkyls in the formula (I);
the pyrimidine compound wherein R1 is a hydrogen atom, R2 is C3-C7
2-alkynyloxy, R3 is a halogen atom, and X is C3-C8 hexamethylene
optionally substituted with at least one substituent selected
from the group consisting of halogen atoms, trif luoromethyl and
C1-C4 alkyls in the formula (I);
the pyrimidine compound wherein R1 is a hydrogen atom, Rz is C3-C7
2-alkynyloxy, R3 is a fluorine atom, and X is C3-C8 hexamethylene
optionally substituted with at least one substituent selected
from the group consisting of halogen atoms, trifluoromethyl and
C1-C4 alkyls in the formula (I);
the pyrimidine compound wherein R1 is a hydrogen atom, R2 is C3-C7
2-alkynyloxy, R3 is a hydrogen atom, and X is C3-C8
pentamethylene optionally substituted with a halogen atom,
trifluoromethyl or C1-C4 alkyl in the formula (I);
the pyrimidine compound wherein R1 is a hydrogen atom, Ra is C3-C7
2-alkynyloxy, R3 is a halogen atom, and X is C3-C8 pentamethylene
optionally substituted with a halogen atom, trifluoromethyl or
C1-C4 alkyl in the formula (I);
the pyrimidine compound wherein R1 is a hydrogen atom, R2 is C3-C7
2 alkynylbxy, R"3 is' a fluorine atom, and X is C3-C8
pentamethylene optionally substituted with a halogen atom,
trifluoromethyl or C1-C4 alkyl in the formula (I);
the pyrimidine compound wherein R1 is a hydrogen atom, R2 is. C3-C7
2-alkynyloxy, R3 is a hydrogen atom, and X is C3-C8 hexamethylene
optionally substituted with a halogen atom, trifluoromethyl or
12

C1-C4 alkyl in the formula {I);
the pyrimidine compound wh&rein R1 is a hydrogen atom, R2 is C3-C7
2-alkynyloxy, R3 is a halogen atom, and X is C3-C8 hexamethylene
optionally substituted with a halogen atom, trif luoromethyl or
C1-C4 alkyl in the formula (I);
the pyrimidine compound wherein R1 is a hydrogen atom, R2 Is C3-C7
2-alkynyloxy, £3 is a fluorine atom, and X is C3-C8 hexamethylene
optionally substituted with a halogen atom, trlfluoromethyl or
C1-C4 alkyl in the formula (I).
The production method of the present invention will be illustrated below.
The present compound can be produced, for example, by the production method 1 and 2 described below. Production method 1

This reaction is usually carried out in a solvent.
As the solvent used in the reaction, there are listed, for example, ethers such as tetrahydrofuran, diethyl ether, tert-butyl methyl ether, ethylene glycol dimethyl ether and 1,4-dioxane, acid amides such as N,N-dimethyl formamide, nitriles such as acetonitrile, sulfoxides such as dimethyl sulfoxide, hydrocarbons such as hexane, aromatic hydrocarbons such as benzene and toluene, and the mixture thereof.
As the base used in the reaction, there are listed, for
13

example, alkali metal hydride such as sodium hydride and. potassium hydride, carbonate such as potassium carbonate, alJcali metal alkoxide such as potassium tert-butoxide and sodium tert-butoxide.
The amount of the compound of the formula (III) is usually 1 to 2 moles, and the amount of the base is usually 1 to 2 mole, based on one mol of the compound of the formula (II).
The reaction temperature' of the reaction is usually in the range from o to 80"C, and the reaction time, is usually in the range from 0.5 to 12 hours.
After completion of the reaction, the compound of the formula (I) can be isolated by the procedure such as extracting the reaction mixture into an organic solvent, drying, and concentrating. The isolated compound of the formula (I) can be further purified by chromatography, re-crystallization and the like.

14

tert-butyl methyl ether, ethylene glycol dimethyl ether and 1,4-dioxane, acid amides such as N,N-dimethyl formamide, nitriles such as acetonitrile, alcohols such as methanol and ethanol, hydrocarbons such as hexane, aromatic hydrocarbons such as benzene and toluene, and the mixture thereof.
■ As the base used in the reaction, there are listed, for example, alkali metal hydride such as sodium hydride and potassium hydride, carbonate such as potassium carbonate, tertiary amines such as trlethylamine and ethyldiisopropylamine.
The amount of the compound of the formula (V) is usually 1 to 3 moles based on one mol of the compound of the formula (IV) . When the reaction is carried out in the presence of the base, the amount of base is usually 1 to 4 moles, based on one mol of the compound of the formula (IV).
The reaction temperature of the reaction is usually in the range from 0 to ISO'C, and the reaction time is usually in the range from 0.1 to 48 hours.
After completion of the reaction, the compound of the formula (I) can be isolated by the following procedure:
(i) extracting the reaction mixture into an organic solvent, drying and concentrating;
(li) concentrating the reaction mixture as it is.
The isolated compound of the formula (I) can be further purified by chromatography, re-crystallization and the like.
Next, the production methods of the intermediates of the present compound will be illustrated below. Reference production method 1
The'compound of the formula (II) can be produced by making a compound of the formula (VI) react with a compound of the formula (Vj or its salt such as a hydrochloride of the compound of the formula (V).
15

wherein R1, Rz, R3 and x are as defined above.
This reaction is usually carried out in a solvent, and optionally carried out in the presence of a base.
As the solvent used in the reaction, there are listed, for example, ethers such as tetrahydrofuran, diethyl ether, tert-butyl methyl ether, ethylene glycol dimethyl ether and 1,4-dioxane, acid amides such as N,N-dimethyl formamide, nitriles such as acetonitrile, alcohols such as methanol and ethanol, hydrocarbons such as hexane, aromatic hydrocarbons such as benzene and toluene, sulfoxide such as dimethyl sulfoxide, and the mixture thereof.
As the base used in the reaction, there are listed, for example, alkali metal hydride such as sodium hydride and potassium hydride, carbonate such as potassium carbonate, alkali metal hydroxide such as potassium tert-butoxide and sodium tert-butoxide.
The amount of the compound of the formula (VI) is usually 1 to 3 moles based on one mol of the compound of the formula (V) . When the reaction is carried out in the presence of the base, the amount of base is usually 1 to 4 moles based on one mol of the compound of the formula (V).
The reaction temperature of the reaction is usually in the range from 0 to lSO'C, and the reaction time is usually in the range from 0.1 to 48 hours.
After completion of the reaction, the compound of the formula (II) can be isolated by the following procedure:
(i) extracting the reaction' mixture into an organic
16

solvent, drying and concentrating;
(ii) concentrating the reaction mixture as it is.
The isolated compound of the formula (II) can be further purified by chromatography, re-crystallization and the like.
The compounds of the formula (II) includes, for example, the following compounds:
the compound wherein X is C4-C7 polymethylene in the formula (ID;

a compound of the formula (VI) react with a compound of the formula (III) in the presence of a base.

wherein R1, R2, R3 and X are as defined above.
This reaction is usually carried out in a solvent, and optionally carried out in the presence of a base.
As the solvent used in the reaction, there are listed, for example, ethers such as tetrahydrofuran, diethyl ether, tert-butyl methyl ether, ethylene glycol dimethyl ether and 1,4-dioxane, acid amides such as N,N-dimethyl formamide, nitriles such as acetonitrile, hydrocarbons such as hexane, aromatic hydrocarbons such as benzene and toluene, sulfoxide such as dimethyl sulfoxide, and the mixture thereof.
As the base used in the reaction, there are listed, for example, alkali metal hydride such as sodium hydride and potassium hydride, carbonate such as potassium carbonate, alkali metal hydroxide such as potassium tert-butoxide and sodium tert-butoxide.
The amount of the compound of the formula (III) is usually 1 to 2 moles, and the amount of the base is usually 1 to 2 moles, based on one mol of the compound of the formula (IV).
The reaction temperature of the reaction is usually in the range from -20 to SO^C, and the reaction time is usually in the range f-rom- 0 .-5- to 12 hours.
After completion of the reaction, the compound of the formula (IV) can be isolated by the procedure such as extracting the reaction mixture into an organic solvent, drying and concentrating.
The isolated compound of the formula (IV) can be further
18

purified by chromatography, re-crystallization and the like.
The compounds of the formula (IV) includes, for example, the following compounds:
the compound wherein R1 is a hydrogen atom or C1-C4 alkyl in the formula (IV);
the compound wherein R1 is a hydrogen atom in the formula (II) ; the compound wherein R2 is 2-butynyloxy or 2-pentynyloxy in the formula (IV).
Reference production method 3
The compound of the formula (V) can be produced, for example, from a compound of the formula (IX) by the following scheme.

wherein X1 represents C3-C6 polymethylene optionally substituted with at least one substituent selected from the group consisting of halogen atoms, trifluoromethyl and C1-C4 alkyIs. Process 3-1
The compound of the formula (VII) can be produced by making a compound of the formula (VII) react with a hydroxy amine in a solvent.
This reaction is usually carried out in a solvent, and optionally carried out in the presence, of a base.
As the solvent used in the reaction, there are listed, for example, ethers such as tetrahydrofuran, diethyl ether, tert-butyl methyl ether, ethylene glycol dimethyl ether and 1,4-dioxane, acid amides such as N,N-dimethyl formaraide, alcohols such as methanol and ethanol, water, and the mixture
19

thereof.
As the base used in the reaction, there are listed, for example, inorganic base such as sodium hydroxide and potassium hydroxide, tertiary amines such as triethylamine, and nitrogen containing aromatlcs such as pyridine.
The amount of hydroxylamine or its salt is usually l to 3 mole, and the amount of the base is 1 to 5 moles, based on one mol of the compound of the formula (VII).
The reaction temperature of the reaction is usually in the range from 0 to 80^, and the reaction time is usually in the range from 1 to 24 hours.
After completion of the reaction, the compound of the formula (VIII) can be isolated by the procedure such as extracting the reaction mixture into an organic solvent, drying and concentrating.
The isolated compound of the formula (VIII) can be further purified by chromatography, re-crystallization and the like.
The compound of the formula (IX) is the compound disclosed, for example, in Synthesis, (1980), p.222-223, or J. Am. Chem. Soc, (1983), 105, p.2381-2843; or can be produced by the following process.
Process 3-2
The compound of the formula (IX) can be produced by making a compound of the formula (VIII) react in the presence of the reagent for the rearrangement reaction.
This reaction is usually carried out in a solvent.
As the solvent-used i-n the reaction, there are listed, for example, acid amides such as N,N-dimethyl formamide, aromatic hydrocarbons such as toluene and benzen, and the mixture thereof.
As the reagent for the rearrangement reaction, there are listed chlorides of phosphorous such as phosphorous oxychloride.
20

chlorides of sulfur such as thionyl chloride, and poly phosphoric acid.
The amount of the reagent of the rearrangement reaction is usually 0.1 mole to excess amount based on one mole of the compound of the formula (VIII) .
The reaction temperature of the reaction is usually in the range from 0 to 150*0, and the reaction time is usually in the range from 0.1 to 48 hours.
After completion of the reaction, the compound of the formula (VIII) can be isolated by the procedure such as extracting the reaction mixture into an organic solvent, drying and concentrating.
The isolated compound of the formula (VIII) can be further purified by chromatography, re-crystallization and the like.
The compound of the formula (V ) is the compound disclosed, for example, in J. Am. Chem. Soc, (1983), 105, p.2381-2843 or 3. Heterocyclic. Chem., {1980)17, p.603; or can be produced by the following process.
Process 3-3
The compound of the formula (V ) can be produced by making a compound of the formula (IX) react with the reducing reagent.
This reaction is usually carried out in a solvent.
As the solvent used in the reaction, there are listed, for example, ethers such as tetrahydrofuran and diethyl ether.
As the reducing reagent, there are listed hydrides of aluminum such as lithium aluminium hydride.
The amount of the reducing reagent is usua-lly 0 . 5 to 6 moles based on one mole of the compound of the formula (IX).
The reaction temperature of the reaction is usually in the range from 0 to 120^, and the reaction time is usually in the range from 1 to 2 4 hours.
After completion of the reaction, the compound of the
21

formula (V) can be isolated by the following procedure:
(i) poring successively water, aqueous solution of 15% sodium hydroxide, and water into the reaction mixture, extracting into an organic solvent, drying and concentrating; when necessary, distilling;
(ii) poring successively water, aqueous solution of 15% sodium hydroxide, and water into the reaction mixture, extracting into an organic solvent, drying, and collecting the hydrochloric salts of the compound of the formula (V) by stirring in the presence of hydrogen chloride or hydrochloric acid.
Reference production method 4
The compound of the formula (V) can be produced, for example, from a compound of the formula (IX) by the following scheme.

wherein X2 represents C2-C5 polymethylene optionally substituted with at least one substituent selected from the group consisting of halogen atoms, trifluoromethyl and C1-C4 alkyls. Process 4-1
The compound of the formula (XI) can be produced by making a compound of the formula (X) react with urea.
This reaction is usually carried out in absence of a solvent.
The amount of urea is usually 10 moles to excess amount based one mole of the compound of the formula (X).
The reaction temperature of the reaction is usually in the range from 50 to 170*0, and the reaction time is usually in the
22

range from 1 to 24 hours.
After completion of the reaction, the compound of the formula (XI) can be isolated by the procedure such as extracting the reaction mixture into an organic solvent, drying and concentrating.
The isolated compound of the formula (XI) can be further purified by chromatography, re-crystallization and the like.
Process 4-2
The compound of the formula (V" ) can be produced by making a compound of the formula (XI) react with the reducing reagent.
This reaction is usually carried out in a solvent.
As the solvent used in the reaction, there are listed, for example, ethers such as tetrahydrofuran and diethyl ether.
As the reducing reagent, there are listed hydrides of aluminum such as lithium aluminium hydride.
The amount of the reducing reagent is usually 1 to 6 moles based on one mole of the compound of the formula (XI).
The reaction temperature of the reaction is usually in the range from 0 to 120*0, and the reaction time is usually in the range from 1 to 24 hours.
After completion of the reaction, the compound of the formula (V) can be isolated by the following procedure:
(i) poring successively water, aqueous solution of 15% sodium hydroxide, and water into the reaction mixture, extracting into an organic solvent, drying and concentrating; when necessary, distilling;
(ii) poring successively water, aqueous solution.of 15% sodium hydroxide, and water into the reaction mixture, extracting into an organic solvent, drying, and collecting the hydrochloric salts of the compound of the formula (V") by stirring in the presence of hydrogen chloride or hydrochloric acid.
23

Next, the specific examples of the present compounds are showing below.

The pyrimidine compound wherein R1 is a hydrogen atom, R2 is 2-propynyloxy, R3 is a hydrogen atom, X is one selected from the group (A) below.
Group (A):
tetramethylene, 1-methyltetramethylene, 1-ethyltetramethylene,
1-propyltetramethylene, 1-isopropyltetramethylene,
1-(tert-butyl)tetramethylene, 1,4-dimethyltetramethylene,
2-(trifluoromethyl)tetramethylene,
3- (trif luoromethyl) tetramethylene, pent ante thyl en e,
1-methylpsntamethylene, 2-methylpentamethylene,
3-methylpentamethylene, 1-ethylpentaraethylene,
2-ethylpentamethylene, 1-propylpentamethylene,
2-propylpentamethylene, 3-propylpentamethylene,
3-isopropylpentamethylene, 1-(tert-butyl)pentamethylene,
3-(tert-butyl)pentamethylene, 1-(sec-butyl)pentamethylene,
1,5-dimethylpentamethylene, 1,3-dimethylpentamethylene,
1,4-dimethylpentamethylene, 2,2-dimethylpentamethylene,
3,3-dimethyIpentamethylene, 2 -ethyl-5-methylpentamethylene,
2-fluoropentamethylene.,. 3-fluoropentamethylene,,
2,2-difluoropentamethylene, 3,3-difluoropentamethylene,
1-(trifluoromethyl)pentamethylene,
2 -(trifluoromethyl)pentamethylene,
3-(trifLuoromethyl)pentamethylene, hexamethylene,
1-me thylhexamethylene, 2-methylhexamethylene,

3-methylhexamethylene, 1-ethylhexamethylene,
2 -ethylhexamethylene, 3-ethylhexamethylene, 1-
propylhexamethylene, 1-isopropylhexamethylene,
1-(tert-butyl)hexamethylene, 1-isobutylhexamethylene,
1,4-dimethylhexamethylenegroup, 1,5-dimethylhexamethylene,
1,6-dimethylhexamethylene, 2,5-dimethylhexamethylene,
1-(trifluoromethyl)hexamethylene, heptamethylene,
2-penten-l,5-ylene and 2,4-dimethyl-2-penten-l,5-ylene.
The pyrimidine compound wherein R1 is a hydrogen atom, R2 is 2-butynyloxy, R3 is methyl, X is one selected from the group (B) below.
Group (B):
tetramethylene, 1-methyltetramethylene, 1-ethyltetramethylene,
1,4-dimethyltetramethylene,
2-(trifluoromethyl)tetramethylene ,
3-(trifluoromethyl)tetramethylene, pentamethylene,
1-methylpentamethylene, 2-methylpentamethylene,
3-methylpentamethylene, 1-ethylpentamethylene,
2-ethylpentamethylene, 1,5-dimethylpentamethyiene,
1,3-dimethylpentamethylene, 1,4-dimethylpentamethylene,
2,2-dimethylpentamethylene, 3,3-dimethylpentamethylene,
2-ethyl-5-methylpentamethylene,
1-{trifluoromethy1)pentamethylene,
2-(trifluoromethyl)pentamethylene,
3 -(trifluoromethyl)pentamethylene, hexamethylene,
l-methyihexamethylerie-, 2-methylhexamethylene,
3-methylhexamethylene, 1-ethylhexamethylene, 2-ethylhexamethylene, 3-ethylhexamethylene, 1-(trifluoromethyl)hexaraethylene, heptamethylene, 2-penten-l, 5-ylene and 2 , 4-dimet,hyl-2-penten-l, 5-ylene.
25

The pyrimidine compound wherein Rl is a hydrogen atom, R2 is 2-propynyloxy, R3 is a fluorine atom, X is one selected from the group (A) above.
The pyrimidine compound wherein Rx is a hydrogen atom, R2 is 2-propynyloxy, R3 is a chlorine atom, X is one selected from the group (B) above.
The pyrimidine compound wherein R1 is a hydrogen atom, R1 is l-methyl-2-propynyloxy, R3 is a chlorine atom, X is one selected from the group (B) above.
The pyrimidine compound wherein R1 is a hydrogen atom, R1 is 2-pentynyloxy, R3 is a hydrogen atom, X is one selected from the group (C) below.
Group (C):
tetramethylene, 1-methyltetramethylene,
2-methyltetramathylene, 1-ethyltetramethylene,
1-propyltetramethylene, 1-isopropyltetramethylene,
1-(tert-butyl)tetramethylene, 2-ethyltetramethylene,
1,4-dimethyltetramethylene, 2,3-dimethyltetramethylene,
2,2-dimethyltetramethylene, 2-fluorotetramethylene,
2-(trifluoromethyl)tetramethylene ,
3-{trifluoromethyl}tetramethylene, pentamethylene,
1-methylpentamethylene, 2-methylpentamethylene,
3-methylpentamethylene, 1-ethylpentamethylene,
2-ethylpentamethylene, 1-propylpentamethylene,
2-propylpentamethylene, 3-propylpentamethylene,
1-isopropylpentamethylene, 2-isopropylpentamethylene,
3-isopropylpentamethylene, 1- (tert-butyl)pe'ntamethylene,
2-(tert-butyl)pentamethylene, 3-(tert-butyl)pentamethylene,
1-(sec-butyl)pentamethylene, 2-(sec-butyl)pentamethylene,
1,5-dimethylpentamethylene, 1,3-dimethylpentamethylene,
1,4-dimethylpentamethylene, 2,4-dimethylpentamethylene,
1,1-dimethylpentamethylene, 2,2-dimethylpentamethylene,
26

3, 3-dimethylpentamethylene, 2-ethyl-4-methylpentamethylene,
2-ethyl-5-methylpentamethylene, 2,4-diethylpentamethylene,
2-fluoropentamethylene, 2-chloropentamethylene,
2-brojnopentaroethylene, 3-fluoropentamethylene,
3-chloropentamethylene, 3-bromopentamethylene,
2,2-difluoropentamethylene, 3,3-difluoropentamethylene,
2-fluoro-2-methylpentamethylene,
1-(trlfluoromethyl)pentamethylene,
2-{trifluoromethyl)pentamethylene,
3-(trifluoromethyl)pentamethylene, hexamethylene,
1-methylhexamethylene, 2-methyIhexamethylene,
3-methylhexamethylene, 1-ethylhexamethylene,
2 -ethyIhexamethylene, 3-ethylhexamethylene,
1-propylhexamethylene, 2-propylhexamethylene,
3-propylhexamethylene, 1-isopropyIhexamethylene,
2-isopropylhexamethylene, 3-isopropylhexamethylene.
1-[tert-butyllhexamethylene, 1-isobutylhexamethylene,
1,4-dimethylhexamethylenegroup, 1,5-dimethyIhexamethylene,
1,6-dimethylhexamethylene, 2,5-dimethylhexamethylene,
1-(trifluoromethyl)hexamethylene, heptamethylene,
2-penten-l,5-ylene and 2,4-dimethyl-2-penten-l,5-ylene.
The pyrlmidine compound wherein R1 is a hydrogen atom, RJ is 2-pentynyloxy, R3 is methyl, X is one selected from the group (B) above.
The pyrlmidine compound wherein Rl is a hydrogen atom, R* is 2-pentynyloxy, R3 is a fluorine atom, X is one selected from the group (C) above.
The pyrlmidine compound wherein R1 is a hydrogen atom, R2 is 2-pentynyloxy, R3 is a chlorine atom, X is one selected from the group (A) above.
The pyrlmidine compound wherein R1 is a hydrogen atom, K2 is 2-butynyloxy, R3 is ahydrogen atom, X is one selected from
27

the group (C) above.
The pyrimidine compound wherein R1 is a hydrogen atom, R2 is 2-butynyloxy, R3 is a fluorine atom, X is one selected from the group (C) above.
The pyrimidine compound wherein R1 is a hydrogen atom, R2 is 2-butynyloxy, R3 is a chlorine atom, X is one selected from the group (A) above.
The pyrimidine compound wherein R1 is a hydrogen atom, R2 is l-methyl-2-propynyloxy, R3 is a hydrogen atom, X is one selected from the group (A) above.
The pyrimidine compound wherein R1 is a hydrogen atom, Ra is l-methyl-2-propynyloxy, R3 is a fluorine atom, X is one selected from the group (A) above.
The pyrimidine compound wherein R1 is a hydrogen atom, R2 is l-inethyl-2-butynyloxy, R3 is a hydrogen atom, X is one selected from the group (A) above.
The pyrimidine compound wherein Rl is a hydrogen atom, R2 is l-methyl-2-butynyloxy, R3 is a fluorine atom, X is one selected from the group (A) above.
The pyrimidine compound wherein Rl is a hydrogen atom, R2 is l-methyl-2-butynyloxy, R3 is a chlorine atom, X is one selected from the group (B) above.
The pests against which the present compounds have an effect may include arthropods (e.g., insects, acarlnes) and nemathelminthes, specific examples of which are as follows: Hemiptera:
Delphacidae such as Laodelphax striatellus,-Niiaparva.ta lugens, Sogatella furcifera and the like,
Deltocephalidae such as Nephotettix cincticeps, Nephotettix virescens and the like,
Aphididae such as Aphis gossypii, Myzus persicae and the like.
28

Pentatomidae such as Nezara antennata, Riptortus clavetus and the like,
Aleyrodidae such as Trialeurodes vaporariorum, Bemisia argentlfolii and the like,
Coccidae such as Aonidiella aurantii. Cornstockaspis perniciosa, Unaspis citri, Ceroplastes rubens, Icerya purchasi and the like,
Tingidae,
Psyllidae, and the like; kepidoptera:
Pyralidae such as Chilo suppressalis, Cnaphalocrocis medinalis, Notarcha derogata, Plodia interpuncteila and the Like,
Noctuidae such as Spodoptera litura, Pseudaletia separata, Thoricoplusia spp., Heliothis spp., Helicoverpa spp. and the like,
Pieridae such as Pieris rapae and the like,
Tortricidae such as Adoxophyes spp., Grapholita molesta, Cydia poraonella and the like,
Carposinidae such as Carposina niponensis and the like,
Lyonetiidae such as Lyonetia spp. and the like,
Lymantriidae such as Lymantria spp., Euproctis spp., and the like,
Yponomeutidae such as Plutella xylostella and the like,
Gelechiidae such as Pectinophora gossypiella and the like,
Arctiidae such as Hyphantria cunea and the like,
Tineidae such-as -Tinea txanslucens, Tineola bisselliella. and the like? Diptera:
Calicidae such as Culex pipiens pallens, Culex tritaeniorhynchus, Culex guinquefasciatus and the like,
Aedes spp. such as Aedes aegypti, Aedes albopictus and the
29

i
like, '
Anopheles such as Anopheles sinensis and the like,
Chironomidae,
Muscidae such as Musca domestica, Muscina stabulans and the like,
Calliphoridae,
Sarcophagidae,
Fanniidae,
Anthoroyiidae such as Delia platura, Delia antiqua and the like,
Tephritidae,
Drosophilidaa,
Psychodidae,
Tabanidae,
Simuliidae,
Stomoxyidae,
Agromyzidae, and the like; Coleoptera:
Diabrotica spp. such as Diabrotica virgifera virglfera, Diabrotica undecimpunctata howardi and the like,
Scarabaeidae such as Anomala cuprea, Anomala rufocuprea and the like,
Curculionidae such as Sitophilus zeaxnais, Lissorhoptrus orysophilus, Callosobruchuys chienensis and the like,
Tenebrionidae such as Tenebrio molitor, Tribolium castaneum and the like,
Chrysomelidae such as Oulema oryzae, Aulacophora femoralis, Phyllotreta strlolata, Leptinotarsa decemlineata and the like,
Anobiidae,
Epilachna spp. such as Epilachna vigintioctopunctata and the like,
Lyctidae,
30

Bostrychidae,
Cerambycidae,
Paederus fuscipes; Blattodea:
Blattella germanica, Perlplaneta fuliginosa, Periplaneta amerlcana, Peri'planeta brunnea, Blatta orientalis and the like; Thysanoptera:
Thrips palmi, Thrlps tabacl, Frankllniella occidentalls and the like; Hymenoptera:
Formlcidae such as Monomorium pharaonis, Vespidae, bethylid wasp, Tenthredinidae such as Athalia japonica, and the like; Orthoptera:
Gryllotalpidae, Acrididae, and the like; Aphaniptera:
Ctenocephalides felis, Ctenocephalides canis, Pulex irrltans, Xenopsylla cheopis, and the like; Anoplura:
Pediculus humanus corporis, Phthirus pubis, Haematopirms eurysternus, Dalmalinia ovis, and the like; Isoptera:
Reticulitermes speratus, Coptotermes formosanua, and the like; Acarina:
Tetranychidae such as Tetranychus urticae, Panonychus citri, Oligonychus spp., and the like,
Eriophyidae such as Aculops pelekassi and the like,
Tarsonemidae such as Polyphagotarsonemus latus, and the like,
Tenuipalpidae,
Tuckerellidae,
Ixodidae such as Haemaphysalis longicornis.
37

Haemaphysails flava, Dermacentor talwanicus, Ixodes ovatus, Ixodes persulcatus, Boophilus microplus, Rhipicephalus sanguineus, and the like,
Acarldae such as Tyrophagus putrescentiae, and the like,
Epidermoptidae such as Dermatophagoides farinae, Dermatophagoldes ptrenyssnus, and the like,
Cheyletidae such as Cheyletus eruditus, Cheyletus malaccensis, Cheyletus moorei, and the like,
Dermanyssidae, and the like. Nematodes:
Pratylenchus coffeae, Pratylenchus fallax, Heterodera glycines, Globadera rostochiensis, Meloidogyne hapla, Meloidogyne incognita and the like.
The pests controlling composition of the present invention contains the present compound and an inert carrier. Generally, it is a formulation obtained by mixing the present compound and a carrier such as a solid carrier, a liquid carrier, a gaseous carrier and/or bait for poison bait, and if necessary, adding a surfactant and other adjuvant for formulation. The formulation includes , for example, an oil solution, an emulsion, a flowable formulation, a wettable powder, a granule, a powder, a microcapsule, and the like. These formulations can be converted to use into a poison bait, a sheet. In the pests controlling composition of the present invention, the present compound is usually contained in an amount of 0.01% to 95% by weight.
As the so-lid carrier used in formulation, there are listed, for example, fine powders or granules of clays (kaolin clay, diatomaceous earth, synthetic water-containing silicon oxide, bentonite, Fubasami clay, acid clay and the like), talcs, ceramics, other inorganic minerals {sericite, quartz, sulfur, activated carbon, calcium carbonate, hydrated silica and the
32

like), chemical fertilizers (ammonia sulfate, ammonia phosphate , ammonia nitrate, urea, ammonia chloride) and the like, and as the liquid carrier, there are listed, for example, water, alcohols (methanol, ethanoi and the like), ketones (acetone, methyl ethyl ketone and the like), aromatic hydrocarbons (benzene, toluene, xylene, ethylbenzene, methylnaphthalene and the like), aliphatic hydrocarbons (hexane, cyclohexane, kerosene, light oil and the like), esters (ethyl acetate, butyl acetate and the like) , nitriles (acetonitrile, isobutylonitrile and the like), ethers (diisopropyl ether, 1,4-dioxane and the like), acid amides (N,N-dimethylformamide,
N,N-dimethylacetamide and the like), halogenated hydrocarbons (dichloromethane, trichloroethane, carbon tetrachloride and the like), dimethyl sulfoxide and vegetable oils (soy bean oil, cotton seed oil and the like).
As the gaseous carrier, there are listed, for example, fluorocarbon, butane gas, LPG (liquefied petroleum gas), dimethyl ether and carbon dioxide.
As the surfactant, there are listed, for example, alkylsulfate salts, alkyisulfonate salts, alkyl aryl sulfonic acid salts, alkyl aryl ethers and their polyoxyethylenated substances, polyethylene glycol ethers, polyhydric alcohol esters, and sugar alcohol derivatives.
As the other formulation auxiliaries, there are listed, for example, fixing agents, dispersing agents, stabilizer and the like, specifically, casein, gelatin, polysaccharides (starch powder, gum Arabic, cellulose derivatives, alginic acid and the like), ■ lignin de-rivatives.-bentonite, saccharides, synthetic water-soluble polymers (polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acids and the like), PAP (acidic isopropyl phosphate), BHT
(2,6-di-tert-butyl-4-methylphenol), BHA (mixture of 2 - ter-t -butyl- 4 -methoxyphenol. and
33

3-tert-butyl-4-methoxyphenol) , vegetable oils, mineral oils, fatty acids and fatty esters.
As the poison bait base material, there are listed, for example, bait components such as crop powders, vegetable oils, saccharides, crystalline cellulose and the like. To the poison bait, antioxidants such as dibutylhydroxytoluene, nordihydroguaiaretic acid and the like, preservatives such as dehydroacetic acid and the like, accidental ingestion-preventing agents for child and pets such as a capsicum powder and the like, harmful insect-attracting aromatics such as cheese aromatics, onion aromatics, peanut oil, and the like, are added, if necessary.
The pests controlling composition of the present invention is applied to pests directly and/or habitats of pests {nest, plant body, soil and the like). When pests parasitic on cultivated plants are controlled, for example, the pests controlling composition of the present invention is sprayed on the ground part of the cultivated plants, the pests controlling composition of the present invention is irrigated near to the stub, and the like.
When the pests controlling composition of the present invention is used to control pests in the agriculture and forestry field, its application amount is usually from 0.1 to 10,000 g in terms of the amount of the present compound per 1000 ma. When the pests controlling composition of the present invention "is" the'formulation "Of an emulsion, flowable, wettable powders, microcapsule or the like, it is applied after dilution with water to have a concentration of the present compound of usually 10 to 10, 000 ppm. When the pests controlling composition of the present invention is the formulation of an oil solution, granule, powder and the like, it is usually applied as it is.
34

When the pests controlling composition of the present invention is used to control pests in indoor field, the amount of the present compound per m2 of the application area, if treating plane, is usually from 0.001 to 100 mg, and the amount of the present compound per m3 of the application space, if treating space, is usually from 0.001 to 10 mg. When the pests controlling composition of the present invention is the formulation of the an emulsion, flowable, wettable powder, microcapsule, and the like, it is applied after dilution with water to have a concentration of the present compound of usually from 0.01 to 100,000 ppm in application thereof. When the pests controlling composition of the present invention is the formulation of an oil solution, aerosol, smoking agent, poison bait and the like, it is usually applied as it is.
The pests controlling composition of the present invention can be used to treat stems and leaves of plants such as crops and the like to be protected from pests, and can also be used to treat beds before planting of nursery plants and the planting hole and stub in planting. Further, for the purpose of controlling pests living in soil of cultivation ground, it may also be used to treat the soil. It is also possibly that a resin formulation processed into sheet, string and thfe like is wound on crops, put around crops and/or placed on the surface of the soil at the stub, and the like.
The pests controlling composition of the present invention can be used together with other insecticides, nematicldes , ._a.caricides,. bactericides.,. phytoci.des, . plaint growth controlling compositions, synergists, fertilizers, soil improving agents, animal fodders and the like.
Mentioned as such insecticides, acaricides and nematicides are, for example;
organic phosphorus compounds such as fenitrothion,
35

fenthion, pyridaphenthion, diazinon, chlorpyrifos, chlorpyrifos-methyl, acephate, methidathion, disulfoton, DDVP , sulprofos, profenofos, cyanophos, dioxabenzofos, dimethoate, phenthoate, malathion, trichlorfon, azinphosmethyl, monocrotophos, dicrotophos, ethion, fosthiazate and the like; carbamate compounds such as BPMC, benfuracarb, propoxur, carbosulfan, carbaryl, methomyl, ethiofencarb, aldicarb, oxamyl, fenothiocarb, thiodicarb, alanycarb and the like; pyrethroid compounds such as etofenprox, fenvalerate, esfenvalerate, fenpropathrin, cypermethrin, a-cypermethrin, Z-cypermethrin, permethrin, cyhalothrin, A-cyhalothrln, cyfluthrin, 8-cyfluthrin, deltamethrin, cycloprothrin, r -fluvalinate, flueythrinate, bifenthrin, acrinathrin, tralomethrin, silafluofen, halfenprox and the like; neonlcotlnoid compounds such as thiamethoxam, dinotefuran, acetamiprid, clothianidin and the like; benzoylphenylurea compounds such as chlorfluazuron, teflubenzuron, flufenoxuron, lufenuron and the like; benzoylhydrazide compounds such as tebufenozide, halofenozide, methoxyfenozide, chxomafenozide and the like; thiadiazine derivatives such as buprof ezin and the like; nelicetoxin derivatives such as cartap, thiocyclam, bensultap and the like; chlorinated hydrocarbon compounds such
as endosulfan, 7-BHC, 1,1-bis(chlorophenyl)-2,2,2-trichloroethanol and the like; formamidine derivatives such as amitraz, chlordimeform and the like; thiourea derivatives such as diafenthiuron and the like; phenylpyrazole compounds such as ethiprole, acetoprole and the like; chlorfeirapyr"~pym~e"trozine;"spinosa'd', indoxacarb, pyridalyl, pyriproxyfen, fenoxycarb, diofenolan, cyromazine, bromopropylate, tetradifon, quinomethlonate, propargite, fenbutatin oxide, hexythiazox, etoxazole, clofentezine, pyridaben, fenpyroximate, tebufenpyrad, pyriraidifen, fenazaquin, acequinocyl, bifenazate, fluacrypyrim.
36

spirodiclofen, spiremesifen, milbemectin, avsrmectin, emamectin benzoate, azadirachtin, polynactin complex [tetranactin, dinactin, trinactin] and the like.
The present invention will be illustrated further in detail by the following formulation examples, test examples and the like, but the present invention is not limited to these examples.
In production examples and reference production examples, regarding aH-NMR, data measured using tetramethylsilane as an internal standard in a deuterochloroform solvent are shown in terms of chemical shift ( 6 [ppmjvalue) unless otherwise stated.
[Working Examples] Production Example 1
Into 3 ml of ethanol was resolved 0.3 g of 4-(2-butynyloxy)-6-chloro-5-fluoropyrimidine, 0.45 g of 2-methylpyperidine was added tnererin, and the mixture was stirred for 5 hours under reflux condition. The reaction mixture was cooled to near room temperature and concentrated. The residue was subjected to silica gel column chromatography to obtain 0.28 g of 4-{2-butynyloxy)-5-fluoro-6-(2-methylpiperidinojpyriniidine (hereinafter, referred to as Compound (1)). CH3
F OCH2C=CCH3
XH-NMR: 1.25 (d. 3H), 1.58-1.79 (m, 6H), 1.88 (t, 3H) , 3.14-3.18 (m, 1H), 4.21-4.24 (m, 1H), 4.65-4.78 (m, 1H) , 4.97 Production Example 2
37

Into 3 ml of ethanol was resolved 0.3 g of 4-{2-butynyloxy)-6-chloro-5-fluoropyrimidine, 0.38 g of piperidine was added thererin, and the mixture was stirred for 7 hours under reflux condition. The reaction mixture was cooled to near room temperature and concentrated. The residue was subjected to silica gel column chromatography to obtain 0.37 g of 4-(2-butynyloxy)-5-fluoro-6-piperidinopyr±midine (hereinafter, referred to as Compound (2)).

1.81-1.91 (m, 4H, involving a triplet at 1.87), 2.60-2.64 (m, 1H), 2.92-3.01 (m, 1H) . 4.26-4.38 (m, 2H), 4.97 (q, 2H), 8.04 (s, 1H)
Production Example 4
Into 3 ml of ethanol was resolved 0.3 g of 4-(2-butynyloxy)-6-chloro-5-fluoropyrimidine, 0.51 g of 3,5-dimethylpiperidine {cis/trans = about 3/1) was added thererin, and the mixture was stirred for 8 hours under reflux condition. The reaction mixture was cooled to near room temperature, and concentrated. Into the residue was added a saturated ammonium chloride aqueous solution, and the mixture was extracted with tart-butyl methyl ether three times. The organic layers were washed with a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to obtain 0.40 g of 4-(2-butynyloxy)-5-fluoro-6-(3,5-dimethylpiperidlno)pyrimidlne (hereinafter, referred to as Compound [4)). Compound (4) had the cis/trans diastereomer originated two methyls on the piperidine ring. The ratio of the cis/trans diastereomer was about 3.3/1.

Production Example 5
Into 3 ml of ethanol was resolved 0.3 g of 4-(2-butynyloxy)-6-chloro-5-fluoropyrimidine, 0.45 g of
39

hexarnethyleneimine was added thererin, and the mixture was stirred for 10 hours under reflux condition. The reaction mixture was cooled to near room temperature, and concentrated. The residue was subjected to silica gel column chromatography to obtain 0.29 g of l-{6-(2-butynyloxy)-5-fluoro-4-pyr±midinyl}hexahydro-lH-azepine (hereinafter, referred to as

Into 3 ml of ethanol was resolved 0.3 g of 4-(2-butynyloxy)-6-chloropyrimidine, 0.55 g of 3,5-dimethylpiperidine (cis/trans = about 3/1) was added thererin, and the mixture was stirred for 10 hours under reflux condition. The reaction mixture was cooled to near room temperature, and concentrated. Into the residue was added a saturated ammonium chloride aqueous solution, and the mixture was extracted with tert-butyl methyl ether three times. The-organic layers were washed with a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica .gel column chromatography to obtain 0.44 g of 4-{2-butynyloxy)-6-(3,5-dlmethylpiperidino)pyrimidine (hereinafter, referred to as Compound (7) ) . Compound (7) had the cis/trans diastereomer originated two methyls on the piperidine ring. The ratio of the cis/trans diastereomer was about 3.1/1.

Production Example 8
Into 3 ml of ethanol was resolved 0.3 g of 4-(2-butynyloxy)-5,6-dichloropyrimidine, 0.47 g of 3,5-dimethylpiperidine (cis/trans = about 3/1) was added thererin, and the mixture was stirred for 8 hours under reflux condition. The reaction mixture was cooled to near room temperature, and concentrated. Into the residue was added a saturated ammonium chloride aqueous solution, and the mixture
41

was extracted with tert-butyl methyl ether three times. The organic layers were washed with a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column, chromatography to obtain 0.36 g of 4~(2-butynyloxy)-5-chloro- 6 - (3,5-dimethylpiperidino)pyrimidine (hereinafter, referred to as Compound (8)). Compound (8) had the cis/trana diastereomer originated two methyls on the piperidine ring. The ratio of the cis/trans diastereomer was about 3.6/1.

Production Example 9
Into 3 ml of ethanol was resolved 0.3 g of 4-(2-butynyloxy)-6-chloro-5-methylpyr±midine, 0.47 g of 3,5-dlmethylpiperidine (cis/trans = about 3/1) was added thererin, and the mixture was stirred for 16 hours under reflux condition. The reaction mixture was cooled to near room temperature, and concentrated. Into the residue was added a saturated ammonium chloride aqueous solution, and the mixture was extracted with tert-butyl methyl ether three times. The organic layers were washed with -a- saturated sodium-chloride aqueous solution, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to obtain 0.33 g of 4-{2-butynyloxy)-5-methyl-6-(3,5-dimethylpiperidino)pyrimidine (hereinafter, referred to as Compound (9)). Compound (9) had the cis/trans
42

Production .Example -11
0.2 g of 4-chloro-5-fluoro-6-(2-pentynyloxy)pyrimidine and 0.32 g of 3,5-dimethylpiperidine (cis/trans = about 3/1) were mixed and left for 3 hours at room temperature. The reaction mixture was subjected to silica gel column chromatography to obtain 0.23 g of 4-(3.5-dimethylpiperidino)-5-fluoro-
43

6-(2-pentynyloxy)pyriniidine (hereinafter, referred to as Compound (11)). Compound (11) had the cis/trans diastereomer originated two methyls on the piperidine ring. The ratio of the cis/trans diastereomer was about 3.8/1.

44

Production Example 15
0.07 g of sodium hydride (60% oil suspention) was suspended in 2 ml of tetrahydrofuran. 0.5 ml of tetrahydrofuran solution of 0.13 g of 2-pentyn-l-ol was added dropwise at 0 "C therein, and the mixture was stirred for 10 minutes. Into the mixture was added dropwise-0-.S ml of tetrahydrofuran solution of 0.3 g of 4-chloro-6-(3,5-dlmethylpiperidino)pyrimidine obtained the Reference Production Example 6, and stirred for 6 hours at room temperature. Into the reaction mixture was added a saturated ammonium chloride aqueous solution, and the mixture was extracted with tert-butyl methyl ether three times. The organic
45

layers were washed with a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to obtain 0.15 g of 4-(3,5-diroethylpiperidino) ~6-(2-pentynyloxy)pyriraid±ne (hereinafter, referred to as Compound (15)}. Compound (15) had the cis/trans diastereomer originated two methyls on the pyperidine ring. The ratio of the cis/trans diastereomer was about 8.2/1.

2H), 5.86 (s, 1H), 8.30 {s, 1H)
Production Example 17
Into 2 ml of N,N-dimethylformamide was resolved 183 mg of 4-chloro-6-{2-butynyloxy}pyrimidine, 166 mg of pottasium carbonate and 71 mg of pyrrolidine was added thererin, and the
mixture was stirred for 4 hours at 55-60^ . The reaction mixture was cooled to near room temperature, ethyl acetate was added therein, and the mixture was washed with a saturated sodium chloride aqueous solution three times. The organic layers were dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to obtain 170 mg of 4-(2-butynyloxy)-6-(l-pyrrolidinyl)pyrimidine (hereinafter, referred to as Compound (17)).

Production Example IB
Into 2 ml of N,N-dimethylformamide was resolved 183 mg of 4-chloro-6-(2-butynyloxy)pyrimidine, 166 mg of pottasium carbonate and 99 mg of 4-methylpiperidine was added thererin, and the mixture was stirred for 4 hours at BO'C. The reaction mixture was cooled to near room temperature, ethyl acetate was added therein, and the mixture was washed with a saturated sodium chloride aqueous solution three times. The organic layers were dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to obtain 206 mg of 4-(2-butynyloxy)-6-(4-methylpiperidino) pyrimidine (hereinafter, referred to as Compound (18)).
47

Production Example 20
Into-2 ml of N,N-dimethylf ormamide was resolved 183 mg of 4-chloro-6-(2-butynyloxyJpyrimidine, 166 mg of pottasium carbonate and 99 mg of 2-methylpiperidine was added thererin, and the mixture was stirred for 4 hours at SOt^ and 3 hours at 120*0 . The reaction mixture was cooled to near room temperature, ethyl acetate was added therein, and the mixture was washed with
48

a saturated sodium chloride aqueous solution three times . The organic layers were dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to obtain 66 mg of 4-(2-butynyloxy)-6-(2-methylpiperidino)pyrimidine {hereinafter, referred to as Compound (20)) .

0.3 g of 4-chloro-6-(2-butynyloxy)pyrimidine and 0.56 g of 2-ethylpiperidine were mixed and left for 18 hours at 80*0 . The reaction mixture was cooled to near room temperature and subjected to silica gel column chromatography to obtain 0.14 g of 4-(2-butynyloxy)-6-(2-ethylpiperidino)pyrimidine (hereinafter, referred to as Compound (22)).

1H), 4.61 (brd, 1H), 4.95 (q, 2H) , 5.92 (s, 1H}, 8.33 (s, 1H)
Production Example 26
Into 2 ml of N,N-dimethylformam±de was resolved 0.2 g of 4-(2-butynyloxy)-5-fluoro-6-chloropyrimidine, 0.28 g of pottasium carbonate and 0.15 g of 3-triflucromethylplperidine was added thererin, and the mixture was stirred for 5 hours at
70"C. The reaction mixture was cooled to near room temperature, ethyl acetate was added therein, and the mixture was washed with a saturated sodium chloride aqueous solution three times. The organic layers were dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to obtain 0.28 g of 4-(2-butynyloxy}-5-fluoro-6-(3-methylpiperidino)pyrimidine (hereinafter, referred to as Compound (26)}.

Production Example 27
Into 4 ml of N,N-dimethylformamide was resolved 0.37 g of 4-(2-butynyloxy)-6-chloropyrimidine, 0.56 g of pottasium carbonate and 0.2 g of 3,3-dimethylpyrrolidine was added
thererin, and the mixture was stirred for 6 hours at- SO'C. The reaction mixture was cooled to near room temperature, ethyl acetate was added therein, and the mixture was washed with a saturated sodium chloride aqueous solution three times. The organic layers were dried, over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column
52

Production Example 2 9
0.10 g of sodium hydride (6 0% oil suspention} was suspended in 3 ml of tetrahydrofuran. 1 ml of tetrahydrofuran solution
53

of 0.16 g of 2-butyn-l-ol was added dropwise therein, and the mixture was stirred for 10 minutes. Into the mixture was added dropwise 1 ml of tetrahydrofuran solution of 0.31 g of 4-chloro-6-(cis-3,5-dimethylpiperidino) -5-fluoropyrimidine and stirred for 6 hours at 60 T3. Into the reaction mixture was added a saturated ammonium chloride aqueous solution, and the mixture was extracted with tert-butyl methyl ether three times. The organic layers were washed with a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to obtain 0.32 g of 4-(2-butynyloxy}-5 -fluoro-6-(cis-3,5-dlmethylpiperidino}pyrimidine (hereinafter, referred to as Compound (29)),

Production Example 30
0.16 g of sodium hydride (60% oil suspention) was suspended in 4 ml of tetrahydrofuran. 1 ml of tetrahydrofuran solution of 0.27 g of 2-butyn-l-ol was added dropwise therein, and the mixture was stirred for 10 minutes at room temperature. Into the mixture was added dropwise 1 ml of tetrahydrofuran solution of -0:64 g of A -chlorous- ( 3 , S-'di-e-thylpi-peridinolpyrim-idine , wherein the ratio of cis/trans diasteromer on the piperidino
ring was 1:1, and stirred for 5 hours at eo'C. Into the reaction mixture was added a saturated ammonium chloride aqueous solution, and the mixture was extracted with tert-butyl methyl ether three times. The organic layers were washed with a saturated sodium
54

Production Example 31
Into 2 ml of acetnltrlle were added 0.20 g of 4-(2-butynyloxy)-6-chloropyrimidine, 0.45 g of pottasium carbonate and 0.20 g of 3,3-dimethylpiperidine hydrochloride,
and the mixture was stirred for 2 hours at SO'C. The reaction mixture was cooled to near room temperature, a saturated ammonium chloride aqueous solution was added therein, and the mixture was extracted with tert-butyl methyl ether three times. The organic layers were washed with a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate and Concentrated. Th"e "residue was subjected to srlrca -g-ei eo-lumn-chromatography to obtain 0.27 g of 4-(2-butynyloxy)-6 -(3,3 -dimethylpiperidino)pyrimidine (hereinafter, referred to as Compound (31)).
55

pmsmierton Example -33 ■
0 . 05 g of sodium hydride (60% oil suspention) was suspended in 2 ml of tetrahydrofuran. Ths 0.5 ml of tetrahydrofuran solution of 0.08 g of 2-butyn-l-ol was added dropwise at room temperature therein, and the mixture was stirred for 10 minutes. Into the mixture was added dropwise 0-5 ml of tetrahydrofuran
56

Production Example 34
0.08 g of sodium hydride ( 60% oil suspention) was suspended in 3 ml of tetrahydrofuran. 0.5 ml of tetrahydrofuran solution of 0.15 g of 2-butyn-l-ol was added dropwise at room temperature therein, and the mixture was stirred for 10 minutes. Into the mixture was added dropwise 0.5 ml of tetrahydrofuran solution of 0.33 g of l-(6-chloropyrimidin-4-yl)-2,5-dimethyl hexahydro-lH-azepine at room temperature, and stirred for 4 hours at"60*0. ffi'f ter 'the reaction" mixture was cooled--to-near room temperature, a saturated ammonium chloride aqueous solution was added therein, and the mixture was extracted with tert-butyl methyl ether three times. The organic layers were washed with a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate and concentrated. The residue
57

58

Production Example 37
Into 3 ml of acetnitrile were added 0.30 g of 4-(2-butynyloxy)-6-chloropyrimidine, 0.68 g of pottasium carbonate and 0.33 g of 3,4-dimethylpyrrolidine hydrochloride
59

(cis and trans diastereomer mixture), and the mixture was stirred for 4 hours at 70*C. The reaction mixture was cooled to near room temperature, a saturated ammonium chloride aqueous solution was added therein, and the mixture was extracted with cert-butyl methyl ether three times. The organic layers were washed with a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to obtain 0.42 g of 4-(2-butynyloxy)-6-(3,4-dimethylpyrrolidin-1-yl) pyrimidine (hereinafter, referred to as Compound (37)).

Production Example 38
Into 2 ml of acetnitrile were added 0.20 g of 4-(2-butynyloxy)-6-chloropyrimidine, 0.45 g of pottasium carbonate and 0.24 g of 3,3,5,5-tetramethylpiperidine hydrochloride, and the mixture was stirred for 4 hours at 6 0 t. The reaction mixture was cooled to near room temperature, a saturated ammonium chloride aqueous solution was added therein, and the mixture was extracted with tert-butyl methyl ether three ■times. -The organic layers were washed-wlt-h a saturated solium chloride aqueous solution, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to obtain 0.23 g of 4-(2-butynyloxy)-6-(3 , 3,5,5-tetramethylpiperidino)pyrimidine (hereinafter, referred to .as Compound (38)).
60

Production Example 40
0 . 07 g of sodium hydride { 60% oil suspention) was suspended in 3 ml of tetrahydrofuran. 0.5 ml of tetrahydrofuran solution of 0.11 g of 2-butyn-l-ol was added dropwise at room temperature
61

therein, and the mixture was stirred for 10 minutes. Into the mixture was added dropwise 0.5 ml of tetrahydrofuran solution of 0.30 g of l-(6-chloropyrimidih-4-yl)-cis-2,6-dimethyl-hexahydro-lH-azepine at room temperature, and stirred for 8 hours at 60*0. After the reaction mixture was cooled to near room temperature, the reaction mixture was poured into a saturated ammonium chloride aqueous solution, and the mixture was extracted with tert-butyl methyl ether three times. The organic layers were washed with a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to obtain 0.25 g of 1-{6-(2-butynyloxy) pyrimidin-4-yl)-cis- 2,6-dimethyl-hexahydro-1H-azepine (hereinafter, referred to as Compound (40)).

Production Example 41
0.10 g of sodium hydride (60% oil suspention) was suspended in 3 ml of tetrahydrofuran. 0.5 ml of tetrahydrofuran solution of 0.15 g of 2-butyn-l-ol was added dropwise at room temperature therein, and the mixture was stirred for 10 minutes. Into the mixture was added dropwise 0.5 ml of tetrahydrofuran solution of 0.30 g of l-(6-chloro-5-fluoropyrimidin-4-yl)-cis~2-,6-dimethyl-hexahydro-lH-azep±ne at room temperature.;-and
stirred for 8 hours at 70*0. After the reaction mixture was cooled to near room temperature, the reaction mixture was poured into a saturated ammonium chloride aqueous solution, and the mixture was extracted with tert-butyl methyl ether three times. The organic layers were washed with a saturated sodium chloride
62

Production Example 42
0 .10 g of sodium hydride (6 0% oil suspention) was suspended in 3 ml of tetrahydrofuran, 0.5 ml of tetrahydrofuran solution of 0.15 g of 2-butyn-l-ol was added dropwise at room temperature therein, and the mixture was stirred for 10 minutes. Into the mixture was added dropwise 0.5 ml of tetrahydrofuran solution of 0.31 g of 1-(6-chloro-5-fluoropyrimidin-4-yl)-trans-2,6-dimethyl-hexahydro-lH-azepine at room temperature, and
stirred for 6 hours at SO'C. After the reaction mixture was cooled to near room temperature, the reaction mixture was poured into a saturated ammonium chloride aqueous solution, and the mixture was extracted with tert-butyl methyl ether three times. - The organic laye-r-s we-re-washed.-with.-a-saturated sodium, chloride aqueous solution, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to obtain 0.34 g of 1-(6-{2-butynyloxy)-5-fluoropyrimidin-4-yl)-trans-2,6-dimethyl-hexahydro-lH-azep ine (hereinafter, referred to as Compound (42)).
63

Production Example 43
0.10 g of sodium hydride (60% oil suspention) was suspended in 3 ml of tetrahydrofuran. 0.5 ml of tetrahydrofuran solution of 0.16 g of 2-butyn-l-ol was added dropwise at room temperature therein, and the mixture was stirred for 10 minutes. Into the mixture was added dropwise 0.5 ml of tetrahydrofuran solution of 0.30 g of 1-(6-chloropyrimidin-4-yl)-trans-2,6-dimethyl hexahydro-lH-azepine at room temperature, and stirred for 5 hours at 60*0. After the reaction mixture was cooled to near room temperature, the reaction mixture was poured into a saturated ammonium chloride aqueous solution, and the mixture was extracted with terr-butyl methyl ether three times. The organic layers were washed with a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to obtain 0.25 g of 1~(6-(2-butynyloxy) pyrimidin-4-yl}-trans-2,6-dimethyl-hexahydro-lH-azepina (hereinafter, referred to as Compound (43)).

{q, 2H), 5.85 (s, 1H), 8.01 (s, IH) GC-MS: 273 (M+)
Production Example 44
0.02 g" of sodium hydride (6 0% oil suspention) was suspended in 1 ml of tetrahydrofuran. 0.3 ml of tetrahydrofuran solution of 0.O2 g of 2-butyn-l-ol was added dropwise at room temperature therein, and the mixture was stirred for 10 minutes. Into the mixture was added dropwise 0.3 ml of tetrahydrofuran solution of 0.05 g of 6-chloro-4-(trans-3,5-dimethylpiperidine)-5-fluoropyrimidine at room temperature, and stirred for 7 hours at 60^. After the reaction mixture was cooled to near room temperature, the reaction mixture was poured into a saturated ammonium chloride aqueous solution, and the mixture was extracted with tert-butyl methyl ether three times. The organic layers were washed with a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to obtain 0.05 g of 4-{2-butynyloxy)-6- (trans-3 , 5-dimethylpiperidino)pyri[nidine (hereinafter, referred to as Compound (44)).

Production Example 45
0.2 g of 4-chloro-6-{2-pentynyloxy)pyrimidine and 0.31 g of octahydroazocine were mixed and left for 2 hours at room temperature. The reaction mixture was subjected to silica gel column chromatography to obtain 0.30 g of l-(6-{2-butynyloxy)
65

Production Example 47
0 . 07 g of sodium hydride {60% oil suspention) was suspended in 2 ml of tetrahydrof uran. 0 . 5 ml of tetrahydrofuran solution of 0.10 g of 2-butyn-l-ol was added dropwise at room temperature therein, and the-mixture was stirred for 10 minutes. Into the., mixture was added dropwise 0.5 ml of tetrahydrofuran solution of 0.20 g of 1-(6-chloro-5-fluoropyrimldin-4-yl)-2-methyl-hexahydro-lH-azepine at room temperature, and stirred
for 6 hours at 60tC. After the reaction mixture was cooled to near room temperature, the reaction mixture was poured into a
66

saturated ammonium chloride aqueous solution, and the mixture was extracted with tert-butyl methyl ether three times. The organic layers were washed with a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to obtain 0.27 g of 1-{6-{2-butynyloxy) -5-fluoropyrimidin-4-yl)-2-methyl-hexahydro-lH-azepine (hereinafter, referred to as Compound (47)).

Production Example 48
0.06 g of sodium hydride (6 0% oil suspentlon) was suspended in 1. 5 ml of tetrahydrof uran. 0 . 3 ml of tetrahydrof uran solution of 0.08 g of 2-butyn-l-ol was added dropwise at room temperature therein, and the mixture was stirred for 10 minutes. Into the mixture was added dropwise 0.3 ml of tetrahydrofuran solution of 0.19 g of 6-chloro-4-(cis-2,6-dimethylpiperidino)pyrimldine
at room temperature, and stirred for 6 hours at SO'C . After the reaction mixture was cooled to near room temperature, the reaction mixture was poured into a saturated ammonium chloride aqueous solution, and the mixture was extracted with tert-butyl methyl ether three times. The organic layers were washed with a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to obtain 0.20 g of 4- (2-butynyloxy) -6- (cis-2, 6-dimethylpiperidino)pyritaidine (hereinafter, referred to as Compound (48)).
67

Production Example 49
0 . 05 g of sodium hydride (60% oil suspention) was suspended in 2 ml of tetrahydrofuran. 0.3 ml of tetrahydrofuran solution of 0,09 g of 2-butyn-l-ol was added dropwise at room temperature therein, and the mixture was stirred for 10 minutes. Into the mixture was added dropwise 0.3 ml of tetrahydrofuran solution of 0.21 g of 6-chloro-4-(cis-2,6-dimethylpiperidino)-5-fluoropyrimidine at room temperature, and stirrea for 6 hours at 60*0. After the reaction mixture was cooled to near room temperature, the reaction mixture was poured into a saturated ammonium chloride aqueous solution, and the mixture was extracted with tert-butyl methyl ether three times. The organic layers were' washed with a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to obtain 0-21 g of 4-(2-butynyloxy)-G-(cis-2,6-dimethylpiperidino)-5-fluoropyrimldins (hereinafter, referred to as Compound (49)).

68

Production Example 50
0.07 g of sodium hydride (6 0% oil suspention) was suspended in 2 ml of tetrahydrofuran. 0.3 ml of tetrahydrofuran solution of 0.11 g of 2-butyn-l-ol was added dropwise at room temperature therein, and the mixture was stirred for 10 minutes. Into the mixture was added dropwise 0.3 ml of tetrahydrofuran solution of 0.30 g of 1-(6-chloro-5-fluoropyrimldin-4-yl)-2-ethyl-hexahydro-lH-azepine at room temperature, and stirred for 9 hours at 60*0. After the reaction mixture was cooled to near room temperature, the reaction, mixture was poured into a saturated ammonium chloride aqueous solution, and the mixture was extracted with tert-butyl methyl ether three times. The organic layers were washed with a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to obtain 0.31 g of 1-(6-{2-butynyloxy)-5-fluoropyrimidin-4-yl)-2-ethyl-hexahy&ro-lH-azepine (hereinafter, referred to as Compound (50)).

..Production Example 51
0.09 g of sodium hydride (6 0% oil suspention) was suspended in 3 ml of tetrahydrofuran. 0.3 ml of tetrahydrofuran solution of 0.15 g of 2-butyn-l-ol was added dropwise at room temperature therein, and the mixture was stirred for 10 minutes. Into the mixture was added dropwise 0.3 ml of tetrahydrofuran solution
69

of 0.40 gof 4,S-difluoro-6-(3, 5-dimethylpiperidino) pyrimidine {cis/trans diastereomer - about 5/l)at room temperature, and
stirred for 20 minutes at 0*0. The reaction mixture was poursd into a saturated ammonium chloride aqueous solution, and the mixture was extracted with tert-butyl methyl ether three times. The organic layers were washed with a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to obtain 0.46 g of 4-(2-butynyloxy)-5-fluoro-6-(3,5-dimethylpiperidino)pyrimidine (hereinafter, referred to as Compound (51)). Compound (51) had the cis/trans diastereomer originated two methyls on the pyperidine ring. The ratio of the cis/trans diastereomer was about 5/1.

Produntion Example 52
0. 09 g of sodium hydride (60% oil suspention) was suspended in 2 ml of tetrahydrofuran. 0.3 ml of tetrahydrofuran solution of 0.13 g of 2-butyn-l-ol was added dropwise at room temperature therein, and the mixture was stirred for 10 minutes. Ipto the mixture was added dropwise 0.3 ml of tetrahydrofuran solution of 0.4 g of 5-chloro-2,4-difluoro-6-(3,5-dimethylpiperidino) pyrimidine at 0"C, and stirred for 30 minutes at same temperature. The reaction mixture was poured into a saturated ammonium chloride aqueous solution, and the mixture was extracted with
70

text-butyl methyl ether three times. The organic layers were washed with a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to obtain 0.20 g of 5-chloro-4-(2-butynyloxy)-2-fluoro-6-(3,5-dimethyl piperidinojpyrimidine (hereinafter, referred to as Compound (52)}. Compound (52J had the cis/trans diastereomer originated two methyls on the pyperidine ring. The ratio of the cis/trans diastereomer was about 5/1.,

Formulation Example 3
Each 3 parts of the present compounds (1) to (51) were dissolved in a mixture of 5 parts of a synthetic water-containing silicon oxide fine powder, 5 parts of sodium
dodecylbenzeneuslfonate, 30 parts of bentonite, and 57 parts of clay, and, they were mixed thoroughly, then, suitable amount of water was added to the mixture thereof, the resulted mixture was further stirred, granulated in a granulator, and dried under ventilation to obtain a formulation. Formulation Example 4
Each 4. 5 parts of the present compounds (1) to (51) , 1 part of a synthetic water-containing silicon oxide fine powder, 1 part of DRILESS B (manufactured by Sankyo Co. , Ltd. ) and 7 parts of clay were mixed thoroughly in a mortar, then, stirred to mix by a juice mixer. To the resulted mixture was added 86.5 parts of cut clay, they were sufficiently stirred to mix, to obtain a formulation. Formulation Example 5
Each 10 parts of the present compounds (1) to (51) , 35 parts of white carbon containing 50 parts of ammonium polyoxyethylene alkyl ether sulfate, and 55 parts of water were mixed and finely ground according to a wet grinding method, to obtain a formulation.
Then, the effect of the present compound of controlling pests will be shown by test examples. Test Example 1
A formulation of a test compound obtained in Formulation Example 5 was diluted with water so that the active ingredient concentration came to 500 ppm to prepare a test spray liquid.
The seeds of cucumber were planted in polyethylene cups and grown until their first foliage leaves developed, on which about 20 cotton aphids {Aphis gossypli) were made parasitic.
93

and grown until their first foliage leaves developed, and then a test spray liquid was applied at a ratio of 20 ml/cup to the plant. After the liquid 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 Western flower thxips (Frankllniella occidentalls) were set free on the first true leaf, which was covered with a polyethylene cup. After seven days, the number of surviving pests was examined.
As a result, the number of surviving pests was 0 on the leaves treated with each of the present compounds (4), (8) to (11), (23), (24), (26), (29), (32), (33), (44), (46), (47), (51), (52) and (53) .
Test Example 3
A formulation of each test compound obtained according to Formulation Example 5 was diluted with water to give the spray liquid for test wherein an effective ingredient concentration is 500 ppm.
The seeds of cabbage were planted in polyethylene cups and grown until their first foliage leaves developed. The first foliage leaves were left and the other leaves were cut off. Some adults of silverleaf whiteflies [Bemisia argentlfolii) were set free on the cabbage plants and allowed to lay eggs for about 24 hours. The cabbage plants with about 80 to 100 eggs thus laid were left in a greenhouse for 8 days, and the above test spray liquid was sprayed at the rate of 20 ml/cup onto the cabbage plants with larvae being hatched from the laid eggs. On the 7th day after the application, the number of surviving larvae was counted.
As a result, for the present compounds (1) to (53), the number of surviving larvae on the cabbage leaves treated with each of these compounds was not greater than 10.
95

Test Example 4
A formulation of a test compound obtained in Formulation Example 5 was diluted with water so that the active Ingredient concentration came to 500 ppm to prepare a test spray liquid.
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. The rice plants were grown until the second foliage leaves developed and then cut into the same height of 5 cm. The test spray liquid, which had been prepared as described above, was sprayed at the rate of 20 ml/cup onto these rice plants. After the test liquid sprayed onto the rice plants was dried, thirty first-instar larvae of brown planthoppers (Nllaparvata Xugens) were set free on the rice plants, which were then left in a greenhouse at 25" C. On the 6th day after the release of brown planthopper larvae, the number of brown planthoppers parasitic on the rice plants was examined.
As a result, in the treatment with each of the present compounds (2), (3), (6), (10) to (12), (14), (15), (17), (18), (22) to (26), (30), (31), (33) to (35), (41) to (43), (45) to (49) and (51), the number of parasitic insects on the 6th day after the treatment was not greater than 3.
INDUSTRIAL APPLICABILITY
The present compound has an excellent ability of controlling pests, therefore, it is useful as an effective ingredient in a pests controlling composition.

WE CLAIM:
1. A pyrimidine compound of the formula (I):

wherein R1 represents a hydrogen atom, halogen atom or C1-C4 alkyl; R2 represents C3-C7 alkynyloxy; R3 represents a hydrogen atom, halogen atom or C1-C3 alkyl; X represents C4-C7 polymethylene, in which a CH2-CH2 may be replaced with a CH=CH, optionally substituted with at least one substituent selected from the group consisting of halogen atoms, trifluoromethyl and C1-C4 alkyls.
2. The pyrimidine compound as claimed in claim 1, wherein X is C4-C7 polymethylene optionally substituted with at least one substituent selected from the group consisting of halogen atoms, trifluoromethyl and C1-C4 alkyls.
3. The pyrimidine compound as claimed in claim 1, wherein X is C4-C7 polymethylene optionally substituted with a halogen atom, trifluoromethyl and C1-C4 alkyl.
4. The pyrimidine compound as claimed in claim 1, wherein X is C4-C7 polymethylene.
5. The pyrimidine compound as claimed in claim 1, wherein X is C4-C7 polymethylene substituted with a halogen atom(s).

6. The pyriraidine compound as claimed in claim 1, wherein X is C4-C7 polymethylene substituted with a trifluoromethyl.
7. The pyrimidine compound as claimed in claim 1, wherein X is C4-C7 polymethylene substituted with a C1-C4 alkyl(s).
8. The pyrimidine compound as claimed in claim 1, wherein X is C4-C7 linear
alkenylene optionally substituted with a halogen atom, trifluoromethyl and C1-C4
alkyl.
9. The pyrimidine compound as claimed in any one of claim 1 to 8, wherein R1 is a
hydrogen atom or C1-C4 alkyl.
10. The pyrimidine compound as claimed in any one of claim 1 to 8, wherein R is 2-
butynyloxy or 2-pentynyloxy.
U, A pests controlling composition comprising a pyrimidine compound as claimed in claim 1 as an effective ingredient.

wherein R1 represents a hydrogen atom, halogen atom or C1-C4 alkyl; R3 represents a hydrogen atom, halogen atom or C1-C3 alkyl; X3 represents C4-C7 poiymethylene, in which a CH2-CH2 may be replaced with a CH=CH, substituted with at least one substituent selected from the group consisting of halogen atoms, trifluoromethyl and
Cl-C4aikyls.
13. The pyrimidine compound as claimed in claim 12, wherein X is C4-C7 poiymethylene substituted with at least one substituent selected from the group consisting of halogen atoms, trifluoromethyl and C1-C4 alkyls.
14. The pyrimidine compound as claimed in claim 12, wherein X3 is C4-C7 poiymethylene substituted with a halogen atom(s).
15. The pyrimidine compound as claimed in claim 12, wherein X is C4-C7 poiymethylene substituted with a trifluoromethyl.
16. The pyrimidine compound as claimed in claim 12, wherein X3 is C4-C7
poiymethylene substituted with a C1-C4 alkyl(s).

Documents:

2951-chenp-2005 abstract duplicate.pdf

2951-chenp-2005 abstract.pdf

2951-chenp-2005 claims duplicate.pdf

2951-chenp-2005 claims.pdf

2951-chenp-2005 correspondence-others.pdf

2951-chenp-2005 correspondence-po.pdf

2951-chenp-2005 description (complete) duplicate.pdf

2951-chenp-2005 description (complete).pdf

2951-chenp-2005 form-1.pdf

2951-chenp-2005 form-13.pdf

2951-chenp-2005 form-18.pdf

2951-chenp-2005 form-26.pdf

2951-chenp-2005 form-3.pdf

2951-chenp-2005 form-5.pdf

2951-chenp-2005 pct.pdf

2951-chenp-2005 petition.pdf

« Previous Patent

Next Patent »

Patent Number

230281

Indian Patent Application Number

2951/CHENP/2005

PG Journal Number

13/2009

Publication Date

27-Mar-2009

Grant Date

25-Feb-2009

Date of Filing

10-Nov-2005

Name of Patentee

SUMITOMO CHEMICAL COMPANY LIMITED

Applicant Address

27-1, Shinkawa 2-chome, Chuo-ku, Tokyo 104-8260,

Inventors:

#	Inventor's Name	Inventor's Address
1	MIZUNO, Hajime	2-10-3-312, Sonehigashino-cho, Toyonaka-shi, Osaka 561-0802,
2	MANABE, Akio	6-1-6-503, Yayoigaoka, Sanda-shi, Hyogo 669-1546,

PCT International Classification Number

C07D239/46

PCT International Application Number

PCT/JP2004/006586

PCT International Filing date

2004-05-10

PCT Conventions:

#	PCT Application Number	Date of Convention	Priority Country
1	2003-132663	2003-05-12	Japan
2	2003-404230	2003-12-03	Japan