Indian Patents. 251964:CYCLIC AMINE COMPOUNDS AND PESTICIDAL COMPOSITION COMPRISING THEM

Title of Invention	CYCLIC AMINE COMPOUNDS AND PESTICIDAL COMPOSITION COMPRISING THEM
Abstract	The invention discloses cyclic amine compounds represented by formula (1): wherein Cy1, Cy2, Rla, Rlb, R2a, R2b, R3a, R3b, R4a, R4b , R5 and X are as described in the specification. The invention is also for a pesticidal composition comprising the above cyclic amine compounds.

Full Text	SPECIFICATION [Title of the Invention] [Field of the Invention] The present invention relates to novel cyclic amine compounds and agents for pest control which contain these cyclic amine compounds or the like as active ingredients. Priority is claimed on Japanese Patent Application No. 2005-294126, filed October 6,2005, Japanese Patent Application No. 2005-294127, filed October 6,2005, Japanese Patent Application No. 2005-297803, filed October 12, 2005, Japanese Patent Application No. 2005-297804, filed October 12,2005, Japanese Patent Application No. 2006-016877, filed January 25,2006, and Japanese Patent Application No. 2006-182314, filed June 30,2006, the contents of which are incorporated herein by reference. [Description of the Related Art] Although many compounds which have insecticidal/acaricidal activities are conventionally known, there are problems such as insufficient effect thereof, limitation of use thereof because of drug resistance problems, occurrence of phytotoxicity or contamination in plant bodies, or strong toxicity against mammalians, fish, or the like. As compounds with backbones similar to those of the compounds of the present invention, compounds represented by the formula below are known. In the formula, X represents -O-, -N(R3)-, -S-, or the like and R1 represents a substituted saturated heterocyclic group or the like. As a representative of such compounds, the compound represented by the formula below is known (refer to Patent document 1). Moreover, the compounds represented by the formula below are known. In the formula, X represents -CH- or the like; Z represents a bonding or the like; R3 represents an optionally substituted aryl or an optionally substituted heteroaryl; and R7 and R8 represent -(CH2)s- or the like together. However, when R7 and R8 represent -(CH2)S- together, only the compounds where R is a substituted phenyl like the compound represented by the formula below are specifically shown as examples (refer to Patent document 2). Furthermore, the compounds known in Patent documents 1 and 2 are for medical purposes and their use in the agents for pest control is not described. [Patent document 1] WO 02/100833 [Patent document 2] WO 05/14578 [Problems to be Solved by the Invention] An object of the present invention is to provide agents for pest control, which can be synthesized industrially favorably, which have excellent bioactivities, and which are problem-free in terms of safety. [Means for Solving the Problem] As a result of intensive research in order to solve the above problems, the present inventors discovered that novel cyclic amine compounds with a specific structure have excellent insecticidal/acaricidal activities to complete the present invention. In other words, the present invention firstly provides cyclic amine compounds represented by the formula (1), salts thereof, or N-oxides thereof. In the formula, Cy1 represents an unsubstituted or substituted aromatic ring. X represents oxygen, sulfur, unsubstituted or substituted nitrogen, sulfinyl, or sulfonyl. R1a and R2a, R1a and R4a, R2a and R3 3, or R3a and R a form saturated rings together. R1a, Rlb, R2a, R2b, R3a, R3b, R4a, R4b, and R5 which do not form the aforementioned saturated rings each independently represents hydrogen, hydroxyl, halogen, unsubstituted or substituted amino, nitro, or an organic group. Cy2 represents an unsubstituted or substituted aromatic ring with a proviso that Cy2 is an unsubstituted or substituted heteroaromatic ring when R1a and R2a form a saturated ring together and Cy1 is an unsubstituted or substituted phenyl; and Cy2 is a substituted pyridin-2-yl having one or more cyano as a substituent when Cy1 is an unsubstituted or substituted phenyl and Cy2 is a pyridin-2-yl. Moreover, the present invention secondly provides cyclic amine compounds represented by the formula (2), salts thereof, or N-oxides thereof. In the formula, Cy1 represents an unsubstituted or substituted aromatic ring. X represents oxygen, sulfur, sulfinyl, or sulfonyl. R3a and R4a form a saturated ring together. R1a, R1b, R2a, R2b, R3b, R4b and R5 each independently represents hydrogen, hydroxyl, halogen, unsubstituted or substituted amino, nitro, or an organic group. R represents hydrogen, alkoxycarbonyl, alkylcarbonyl, or 1-alkoxyalkyl. Furthermore, the present invention thirdly provides agents for pest control, which contains at least one of cyclic amine compounds represented by the formula (3), salts thereof, or N-oxides thereof, as active ingredients. In the formula, Cy11 represents an unsubstituted or substituted aromatic ring. X11 represents oxygen, sulfur, unsubstituted or substituted nitrogen, sulfinyl, or sulfonyl. R11a and R21a, R11a and R41a, R21a and R31a, or R31a and R41a form saturated rings together. R11a, R11b, R21a, R21b, R31a, R31b, R41a, R41b, and R51 which do not form the aforementioned saturated rings each independently represents hydrogen, hydroxyl, halogen, unsubstituted or substituted amino, nitro, or an organic group. Cy21 represents an unsubstituted or substituted aromatic ring. [Effects of the Invention] According to the present invention, it is possible to provide cyclic amine compounds with a novel structure, salts thereof, N-oxides thereof, or intermediates thereof during the production, and especially agents for pest control with insecticidal/acaricidal activities for particularly crop-damaging insects and acarids whereby high safety can be provided. [Preferred Embodiments of the Invention] The present invention will be described in detail below. 1) Cyclic amine compounds represented by the formulae (1) and (2), salts thereof, or N-oxides thereof In the cyclic amine compounds represented by the formula (1), Cy1 represents an unsubstituted or substituted aromatic ring: Specific examples of the aromatic rings include aromatic hydrocarbons such as phenyl, naphthalen-1-yl, naphthalen-2-yl; and heteroaromatic rings such as furan-2-yl, furan-3-yl, thiophen-2-yl, thiophen-3-yl, pyrrol-2-yl, pyrrol-3-yl, oxazol-2-yl, oxazol-4-yl, oxazol-5-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, imidazol-2-yl, imidazol-4-yl, imidazol-5-yl, pyrazol-3-yl, pyrazol-4-yl, pyrazol-5-yl, l,3,4-oxadiazol-2-yl, l,3,4-thiadiazol-2-yl, l,2,3-triazol-4-yl, l,2,4-triazol-3-yl, l,2,4-triazol-5-yl, pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyridazin-3-yl, pyridazin-4-yl, pyrazin-2-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl, l,3,5-triazin-2-yl, and l,2,4-triazin-3-yl; and phenyl is preferable. Specific examples of the substituents of the aromatic rings include hydroxyl; thiol; halogen such as fluorine, chlorine, bromine, and iodine; cyano; nitro; formyl; unsubstituted or substituted amino such as amino, methylamino, benzylamino, anilino, dimethylamino, diethylamino, and phenylethylamino; alkyl (preferably C1-6 alkyl) such as methyl, ethyl, n-propyl, isopropyl, n-butyl, s-butyl, isobutyl, t-butyl, n-pentyl, and n-hexyl; alkenyl such as vinyl, allyl, and 2-methoxy-ethenyl; alkynyl such as ethynyl, 1-propynyl, 2-phenylethynyl, and propargyl; alkoxy (preferably C1-6 alkoxy) such as methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, s-butoxy, isobutoxy, and t-butoxy; alkenyloxy such as vinyloxy and allyloxy; alkynyloxy such as ethynyloxy and propargyloxy; aryloxy such as phenoxy and bezyloxy; heteroaryloxy such as 2- pyridyloxy; haloalkyl (preferably C1-6 haloalkyl) such as chloromethyl, fluoromethyl, bromomethyl, dichloromethyl, difluoromethyl, dibromomethyl, trichloromethyl, trifluoromethyl, bromodifluoromethyl, 1,1,1-trifluoroethyl, 1-chloroethyl, 2-chloroethyl, 1-bromoethyl, and pentafluoroethyl; haloalkoxy (preferably C1-6 haloalkoxy) such as fluoromethoxy, chloromethoxy, bromomethoxy, difluoromethoxy, dichloromethoxy, dibromomethoxy, trifluoromethoxy, trichloromethoxy, tribromomethoxy, 1,1,1-trifluoroethoxy, pentafluoroethoxy, and heptafluoron-propoxy; alkylthiocarbonyl (preferably C1-6 alkylthiocarbonyl) such as methylthiocarbonyl, ethylthiocarbonyl, n-propylthiocarbonyl, isopropylthiocarbonyl, n-butylthiocarbonyl, isobutylthiocarbonyl, s-butylthiocarbonyl, and t-butylthiocarbonyl; alkylsulfonylamino (preferably C1-6 alkylsulfonylamino) such as methylsulfonylamino, ethylsulfonylamino, n-propylsulfonylamino, isopropylsulfonylamino, n-butylsulfonylamino, and t-butylsulfonylamino; arylsulfonylamino (preferably C6-12 arylsulfonylamino) such as phenylsulfonylamino; heteroarylsulfonylamino (preferably C3-12 heteroarylsulfonylamino) such as piperazinylsulfonylamino; alkylcarbonylamino (preferably C1-6 alkylcarbonylamino) such as methylcarbonylamino, ethylcarbonylamino, n-propylcarbonylamino, and isopropylcarbonylamino; alkoxycarbonylamino (preferably C1-6 alkoxylcarbonylamino) such as methoxycarbonylamino, ethoxycarbonylamino, n-propoxycarbonylamino, and isopropoxycarbonylamino; haloalkylsulfonylamino (preferably C1-6 haloalkylsulfonylamino) such as fluoromethylsulfonylamino, chloromethylsulfonylamino, bromomethylsulfonylarnino, difluoromethylsulfonylamino, dichloromethylsulfonylamino, 1,1 -difluoroethylsulfonylamino,trifluoromethylsulfonylamino, 1,1,1-trifluoroethylsulfonylamino and pentafluoroethylsulfonylamino; bis(alkylsulfonyl)amino (preferably bis(C1-6 alkylsulfonylamino) such as bis(methylsulfonyl)amino, bis(ethylsulfonyl)amino, (ethylsulfonyl) (methylsulfonyl) amino, bis(n-propylsulfonyl)amino, bis(isopropylsulfonyl)amino, bis(n-butylsulfonyl)amino, and bis(t-butylsulfonyl)amino; bis(haloalkylsulfonyl)amino (preferably bis(C1-6 haloalkylsulfonylamino) such as bis(fluoromethylsulfonyl)amino, bis(chloromethylsulfonyl)amino, bis(bromomethylsulfonyl)amino, bis(difluoromethylsulfonyl)amino, bis(dichloromethylsulfonyl)amino, bis( 1,1 -difluoroethylsulfonyl)amino, bis(trifluoromethylsulfonyl)amino, bis(1, 1,1 -trifluoroethylsulfonyl)amino, and bis(pentafluoroethylsulfonyl)amino; unsubstituted or substituted hydrazino such as hydrazino, N'-phenylhydrazino, N'-methoxycarbonylhydrazino, N'-acetylhydrazino, and N'-methylhydrazino; alkoxycarbonyl (preferably C1-6 alkoxycarbonyl) such as methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl, n-butoxycarbonyl, and t-butoxycarbonyl; aryl (preferably C6-12 aryl) such as phenyl, 1-naphthyl, and 2-naphthyl; aralkyl (preferably C7-20 aralkyl) such as benzyl, and phenethyl; unsaturated 5-membered heterocycle such as furan-2-yl, furan-3-yl, thiophen-2-yl, thiophen-3-yl, pyrrol-2-yl, pyrrol-3-yl, oxazol-2-yl, oxazol-4-yl, oxazol-5-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, imidazol-2-yl, imidazol-4-yl, imidazol-5-yl, pyrazol-3-yl, pyrazol-4-yl, pyrazol-5-yl, l,3,4-oxadiazol-2-yl, l,3,4-thiadiazol-2-yl, l,2,3-triazol-4-yl, l,2,4-triazol-3-yl, and l,2,4-triazol-5-yl; unsaturated 5-membered heterocycle alkyl such as 5-phenyl-5-trifluoromethyl-isoxazolin-3-yl, 2-furfurylmethyl, 3-thienylmethyl, and l-methyl-3-pyrazolomethyl; unsaturated 6-membered heterocycle such as pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyridazin-3-yl, pyridazin-4-yl, pyrazin-2-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl, l,3,5-triazin-2-yl, and l,2,4-triazin-3-yl; unsaturated 6-membered heterocycle alkyl such as 2-pyridylmethyl, 3-pyridylmethyl, 6-chlor-3-pyridylmethyl, and 2-pyrimidylmethyl; sanitated heterocyclic group such as tetrahydrofuran-2-yi, tetrahydrapyran-4-yl, piperidin-3-yl, pyrrolidin-2-yl, morpholino, piperidino, and N-methylpiperazinyl; sanitated heterocyclic alkyl such as 2-tetrahydrafuranylmethyl, 3-piperazylmethyl, N-methyl-3-pyrrolidylmethyl, and morpholinomethyl; N-unsubstituted- or N-substituted iminoalkyl such as N-dimethylaminoiminomethyl, 1 -N-phenyliminoethyl, N-hydroxyiminomethyl, and N-methoxyiminomethyl; N-unsubstituted- or N-substituted hydrazinocarbonyl such as N'-methylhydrazinocarbonyl, N'-phenylhydrazinocarbonyl, and hydrazinocarbonyl; N-unsubstituted- or N-substituted aminocarbonyl such as aminocarbonyl, dimethylaminocarbonyl, and N-phenyl-N-methylaminocarbonyl; alkylthio such as methylthio, ethylthio, and t-butylthio; alkenylthio such as vinylthio and allylthio; alkynylthio such as ethynylthio and propargylthio; arylthio such as phenylthio, and 4-chlorophenylthio,; heteroarylthio such as 2- piperidylthio and 3-pyridazylthio; aralkylthio such as benzylthio and phenethylthio; alkylsulfonyl such as methylsulfonyl, ethylsulfonyl, and t-butylsulfonyl; alkenylsulfonyl such as allylsulfonyl; alkynylsulfonyl such as propargylsulfonyl; arylsulfonyl such as phenylsulfonyl,; heteroarylsulfonyl such as 2-pyridylsulfonyl and 3- pyridylsulfonyl; aralkylsulfonyl such as benzylsulfonyl and phenethylsulfonyl; groups represented by the formulae (a) to (c) below; [ In the formulae (a), (b), and (c), R6 and R7 each independently represents hydrogen, unsubstituted or substituted hydrocarbon, unsubstituted or substituted heterocyclic group, unsubstituted or substituted amino, hydrocarbonoxy, or hydrocarbonthio; R 8and R11 each independently represents hydrogen, unsubstituted or substituted hydrocarbon, unsubstituted or substituted heterocyclic group, or unsubstituted or substituted amino; R9 represents hydrogen or unsubstituted or substituted hydrocarbon; R10 represents hydrogen, unsubstituted or substituted hydrocarbon, or unsubstituted or substituted heterocyclic group; Y and Z each independently represents oxygen, or unsubstituted or substituted nitrogen; R6 and R7, R8 and R9, and R10 and R11 may bond to form rings and in that case, both two groups in the pair represent functional groups, which may integrate to form a ring. Specific examples of hydrocarbons commonly present in R6 to R11 include alkyl such as methyl, ethyl, isopropyl, n-propyl, n-hexyl, and n-octyl; alkenyl such as vinyl, allyl, 1-propenyl, and 2-phenylethenyl; alkynyl such as ethynyl and propargyl; and aromatic hydrocarbon such as phenyl, 1-naphthyl, and 9-anthracel. Specific examples of heterocyclic groups commonly present in R6 , R7 , R8 , R10 , and R11 include unsaturated 5-membered heterocycle such as furan-2-yl, furan-3-yl, thiophen-2-yl, thiophen-3-yl, pyrrol-2-yl, pyrrol-3-yl, oxazol-2-yl, oxazol-4-yl, oxazol-5-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, imidazol-2-yl, imidazol-4-yl, imidazol-5-yl, pyrazol-3-yl, pyrazol-4-yl, pyrazol-5-yl, l,3,4-oxadiazol-2-yl, l,3,4-thiadiazol-2-yl, l,2,3-triazol-4-yl, l,2,4-triazol-3-yl, and l,2,4-triazol-5-yl; unsaturated 5-membered heterocycle alkyl such as 5-phenyl-5-trifluoromethyl-isoxazolin-3-yl, 2-furfurylmethyl, 3-thienylmethyl, and l-methyl-3-pyrazolomethyl; unsaturated 6-membered heterocycle such as pyridn-2-yl, pyridin-3-yl, pyridin-4-yl, pyridazin-3-yl, pyridazin-4-yl, pyrazin-2-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl, l,3,5-triazin-2-yl, and 1,2,4-triazin-3-yl; unsaturated 6-membered heterocycle alkyl such as, 2-pyridylmethyl, 3-pyridylmethyl, 6-chlor-3-pyridylmethyl, and 2-pyrimidylmethyl; and saturated heterocycle such as tetrahydrofuran-2-yl, tetrahydrapyran-4-yl, piperidin-3-yl, pyrrolidin-2-yl, morpholino, piperidino, and N-methylpiperazinyl; sanitated heterocyclic alkyl group such as 2-tetrahydrofuranylmethyl, 3-piperazylmethyl, N-methyl-3-pyrrolidylmethyl, and morpholinomethyl. Specific examples of hydrocarbonoxy and hydrocarbonthio commonly present in R6 nad R7 include methoxy, ethoxy, isopropoxy, phenoxy, benzyloxy, methylthio, ethylthio, phenylthio, and benzylthio. Specific examples of substituents of functional groups present in R6 to R11 include the same as those shown as specific examples of the substituents of Cy1. Y and Z each independently represent oxygen, or unsubstituted or substituted nitrogen and specific examples of a substituent on nitrogen include the same as those shown as specific examples of the substituents of Cy1. Specific examples of the group represented by the formulae (a) to (c) include the group represented by the formula below. ]C1-6 haloalkyl is particularly preferable. By associating two or more substituents listed above by substituting one substituent onto another, the resulting substituent can be used in a similar manner as a new substituent. In formula (1), X represents oxygen; sulfur; unsubstituted or substituted nitrogen; sulfinyl; or sulfonyl and oxygen is preferable. It should be noted that when nitrogen is unsubstituted, hydrogen is bonded to nitrogen. When X is substituted nitrogen, specific examples of substituents on nitrogen include those similar to the specific examples of the substituents of Cy1. Moreover, in formula (1), R1a and R2a, R1a and R4a, R2a and R3a or R3a and R4a form saturated rings together and it is preferable that R1a and R a or R3a and R4a come together to form a ring and the number of atoms at the cross-linking site of the piperidine ring, which forms the saturated ring, is preferably 2 or 3. In addition, elements which constitute the cross-linking site of the piperidine ring of the saturated ring are not particularly limited as long as they are within a chemically acceptable range and specific examples thereof include carbon, oxygen, sulfur, nitrogen, or silicon and the saturated rings can be constituted by combining 2 or more of these elements within a chemically acceptable range. Moreover, each atom can have hydrogen or substituents within the chemically acceptable range thereon and R1a and R2a, R1a and R4a, R a and R3a, or R3a and R4a may bind oxygen, sulfur, or nitrogen via a double bond within a chemically acceptable range to form carbonyl, thiocarbonyl, imino, or the like. R1a, R1b, R2a, R2b, R3a, R3b, R4a, R4b, and R5 which do not form the aforementioned saturated rings together each independently represents hydrogen, halogen, unsubstituted or substituted amino, nitro, hydroxyl, or an organic group. The organic group represents functional groups generally which contain carbon and the specific examples thereof include cyano; formyl; alkyl; alkoxycarbonyl; alkoxy; haloalkyl; haloalkoxy; alkylthiocarbonyl; alkylsulfonylamino; haloalkylsulfonylamino; bis(alkylsulfonyl)amino; bis(haloalkylsulfonyl)amino; and aryl; or the like. As the organic groups, alkyl; alkoxycarbonyl; and alkoxy are preferable and C1-6 alkyl; C1-6 alkoxycarbonyl; and C1-6 alkoxy are more preferable. Specific examples thereof include the same as those shown as specific examples of the substituents of Cy1 . Specific examples of a piperidine ring, which is constituted in formula (1), include the structures represented by the formulae shown below. Although specific examples of an aromatic ring of Cy2 include those similar to the specific examples of Cy1, pyridazyl is preferable, and pyridazin-3-yl is more preferable with a proviso that R1 a and R2a come together to form a saturated ring and Cy2 is an unsubstituted or substituted heteroaromatic ring when Cy1 is unsubstituted or substituted phenyl. Moreover, Cy2 is a substituted pyridin-2-yl having one or more cyano as a substituent when Cy1 is an unsubstituted or substituted phenyl and Cy2 is a substituted pyridin-2-yl. Cy2 does not include unsubstituted pyridin-2-yl, when Cy1 is an unsubstituted or substituted phenyl. The substituted pyridin-2-yl having one or more cyano as a substituent means that the substituted pyridin-2-yl has only cyano as a substituent or cyano and another substituent; as substituents. Several pairs of isomers exist when R1a and R2a or R3a and R4a of the compound (1) of the present invention come together to form a saturated ring. These isomers are all included in the present invention. It should be noted that the same also applies when R1a and R4a or R2a and R3a come together to form a saturated ring. Moreover, the same applies to the compounds (2) of the present invention which will be described later. The following compounds can be shown as examples of N-oxides of the compounds represented by the formula (1); i.e. the compounds represented by the formula (1) where nitrogen represented by X or nitrogen in the cyclic amine parts of the tropane ring, isotropane ring, or the like is oxidized. Moreover, examples of salts of the compounds represented by the formula (1) include salts of inorganic acids such as hydrochloride salts, nitrate salts, sulfate salts, and phosphate salts; and salts of organic acids such as acetate salts, lactate salts, propionate salts, and benzoate salts. X0 in the formula (2) corresponds to X in the formula (1) except that X0 does not include nitrogen and R1a to R5 in the formula (2) are the same as R1a to R5 in the formula (1) except that only R3a and R4a form a saturated ring together. R represents hydrogen; alkoxycarbonyl such as 1- chloroethoxycarbonyl, methoxymethoxycarbonyl, 1-ethoxyethoxycarbonyl, 1,1,1-trichloroethoxycarbonyl, and others similar to those examples of the specific examples of the substituents of Cy1 such as alkoxycarbonyl (preferably C1-6 alkoxycarbonyl); alkylcarbonyl (preferably C1-6 alkylcarbonyl) such as methylcarbonyl, ethylcarbonyl, n-propylcarbonyl, isopropylcarbonyl, n-butylcarbonyl, isobutylcarbonyl, s-butylcarbonyl, and t-butylcarbonyl; or 1-alkoxyalkyl (preferably 1-C1-6 alkoxyalkyl) such as methoxymethyl, ethoxymethyl, and 1-ethoxyethyl. 2) Production method (1) When X is oxygen or optionally oxidized sulfur The compound (1) can be obtained by, for example, obtaining the compound represented by the formula (5) by eliminating protecting group such as methyl and benzyl from the compound represented by the formula (4) (hereinafter referred to as the "compound (4)) as shown below and coupling the compound (5) with the compound represented by the formula (6) by the general method. (In the formula, Cy1, Cy2, X, R1a, R1b, R2a, R2b, R3a, R3b, R4a, R4b, and R5 are the same as above. X' represents a leaving group such as halogen and R' represents a protecting group.) The compound (4), which is an intermediate during the production, can be produced by general reaction conditions as described next. (In the formula, Cy1, X, R1a, R1b, R2a, R2b, R3a, R3b, R4a, R4b, R5 and R' are the same as above. X1 and X2 each independently represents hydroxyl or mercapto and X3 represents a leaving group such as halogen.) Moreover, the compound (1) can also be produced by the general method shown below. (In the formula, Cy1, Cy2, X, R1a, R1b, R2a, R2b, R3a, R3b, R4a, R4b, and R5 are the same as above. X4 represents a leaving group such as halogen and X5 represents hydroxyl or mercapto.) The compound (11), which will be a raw material, can also be produced by the general method shown in the below reaction formula (IV). (In the formula, Cy2, X4, R1a, Rlb, R2a, R2b, R3a, R3b, R4a, R4b, and R5 are the same as abdve. X6 represents a leaving group such as halogen.) (2) When X is optionally substituted nitrogen The compounds represented by the formula (17) can be produced by reacting the compounds represented by the formula (15) with the compounds represented by the formula (16) by the general method as shown in the below reaction formula (V). (In the formula, Cy1, Cy2, R1a, R1b, R2a, R2b, R3a, R3b, R4a, and R4b are the same as above. R" represents a substituent on nitrogen such as hydrogen, trifluoroacetyl, or trifluoromethylsulfonyl.) The compound (17), which is a compound of the present invention, can also be produced by coupling the compound (15) and the compound represented by the formula (18) by the general method as shown in the below reaction formula (VI). (In the formula, Cy1, Cy2, R1a, Rlb, R2a, R2b, R3a, R3b, R4a, R4a, R5, and R" are the same as above. X7 represents a leaving group such as halogen and sulfonyloxy.) The compound (17), which is a compound of the present invention, can also be produced by coupling the compound (19) and the compound represented by the formula (20) by the general method as shown in the below reaction formula (VII). (In the formula, Cy1, Cy2, X7, R1a, R1b, R2a, R2b, R3a, R3b, R4a, R4b, R5, and R" are the same as above.) 3) Agents for pest control represented by formula (3) The agents for pest control of the present invention are characterized by having the compounds represented by the formula (3), salts thereof or N-oxides thereof, as active ingredient. The present invention relates to agents for pest control which contain the compounds represented by the formula (3), salts thereof or N-oxides thereof, as active ingredients. In the formula (3), Cy11, Cy21, X11, and R11a to R51 are the same as corresponding Cy1, Cy2, X, and R1a to R5 in the formula (1), respectively, except that there is no proviso regarding Cy11 and Cy21 . Since the compounds of the present invention (the compounds represented by the formula (1), salts thereof, or N-oxides thereof) have adulticidal, nymphicidal, larvicidal, or ovicidal activities, they can be used for controlling crop-damaging insect, acarid, sanitary insects, stored grain pest insects, clothes pests, household pests, or the like. Specific organisms to be the target of control include the following. Preferably, pests which belong to the order of Lepidoptera such as Spodoptera litura, Mamestra brassicae, Agrotis ipsilon, green caterpillars, Autographa nigrisigna, Plutella xylostella, Adoxophyes honmai, Homona magnanima, Carposina sasakii, Grapholita molesta, Phyllocnistis citrella, Caloptilia theivora, Phyllonorycter ringoniella, Lymantria dispar, Euproctis pseudoconspersa, Chilo suppressalis, Cnaphalocrocis medinalis, Ostrinia nubilasis, Hyphantria cunea, Cadra cautella, genus Heliothis, genus Helicoverpa, genus Agrothis, Tinea translucens, Cydia pomonella, and Pectinophora gossypiella; pests which belong to the order of Hemiptera such as Myzus persicae, Aphis gossypii, Lipaphis erysimi, Rhopalosiphum padi, Riptortus clavatus, Nezara antennata, Unaspis yanonensis, Pseudococcus comstocki, Trialeurodes vaporariorum, Bemisia tabaci, Bemisia argentifolii, Psylla pyrisuga, Stephanitis nashi, Nilaparuata lugens, Laodelphax stratella, Sogatellafurcifera, and Nephotettix cincticeps; pests which belong to the order of Coleoptera such as Phyllotreta striolata, Aulacophorafemoralis, Leptinotarsa decemlineata, Lissorhoptrus oryzophilus, Sitophilis zeamais, Callosobruchus chinensis, Popillia japonica, Anomala rufocuprea, genus Diabrotica, Lasioderma serricorne, Lyctus brunneus, Monochamus alternates, Anoplophora malasiaca, genus Agriotis, Epilachna vigintioctopunctata, Tenebroides mauritanicus, and Anthonomus grandis; pests which belong to the order of Diptera such as Musca domestica, Calliphora lata, Boettcherisca peregrine, Zeugodacus cucurbitae, Bactrocera dorsalis, Delia platura, Agromyza oryzae, Drosophila melanogaster, Stomoxys calcitrans, Culex tritaeniorhynchus, Aedes aegypti, and Anopheles sinensis; pests which belong to the order of Thysanoptera such as Thrips palmi and Scirtothrips dorsalis; pests which belong to the order of Hymenoptera such as Monomorium pharaonis, Vespa simillima xanthoptera, and Athalia rosae ruficornis; pests which belong to the order of Orthoptera such as Locusta migratoria, Blattella germanica, Periplaneta americana, and Periplanetafuliginosa; pests which belong to the order oflsoptera such as Coptotermes formosanus and Reticulitermes speratus speratus; pests which belong to the order of Siphonaptera such as Pulex irritans and Ctenocephalides felis felis; pests which belong to the order of Phthiraptera such as Pediculus humanus; Acarina such as Tetranychus urticae, Tetranychus cinnabarinus, Tetranychus kanzawai, Panonychus citri, Panonychus ulmi, Aculopspelekassi, Aculus schlechtendali, Polyphagotarsonemus latus, genus Brevipalpus, genus Eotetranichus, Rhizoglyphus robini, Tyrophagus putrescentiae, Dermatophagoides farinae, Boophilus microplus, and Haemaphysalis longicornis; and plant parasitic nematodes such as Meloidogyne incognita, Pratylenchus spp., Heterodera glycines, Aphelenchoides besseyi, and Bursaphelenchus xylophilus. Pests to which the present invention is preferably applied are pests which belong to the order of Lepidoptera, pests which belong to the order of Hemiptera, Acarina, pests which belong to the order of Thysanoptera, and pests which belong to the order of Coleoptera, and particularly preferably Acarina. Moreover, drugs which are also effective for pests or Acarnia that are of resistant lineage are desired because in recent years, resistance to organophosphorus pesticides, carbamate pesticides, or acaricides developed among many pests such as Plutella xylostella, Delphacidae, Deltocephalidae, and Aphididae has caused problems because of insufficient effects of these drugs. The compounds of the present invention are drugs having excellent insecticidal and acaricidal effects not only on those of sensitive lineages but also on pests of lineages resistant to organophosphorus pesticides, carbamate pesticides, and pyrethroid pesticides, and on Acarnia of lineages resistant to acaricides. Additionally, the compounds of the present invention are drugs that show less herbicide injuries, have lower toxicity to fish and warm-blooded animals, and higher safety. The compounds of the present invention can also be used as an antifoulant to prevent aquatic organisms attaching to objects which contact water such as ship bottoms (or hulls, alternatively) and fishing nets. Some of the compounds of the present invention exhibit germicidal activities, herbicidal activities, or plant-growth regulating activities. Moreover, some intermediates of the compounds of the present invention, which are represented by the formula (1) or (3), exhibit insecticidal/acaricidal activities. The agents for pest control of the present invention have the compounds of the present invention, which are represented by the formula (1) or (3), as active ingredients and the agents can be used either singularly or by mixing two or more thereof. The compounds of the present invention can be used as they are without adding any other components. However, when used practically, they are normally further mixed with solid, liquid, or gaseous carriers, or are impregnated in substrates such as porous ceramic plates and nonwoven fabrics, and by adding surfactants and/or other adjuvants where necessary, used as formulations in the form which general agrochemicals may adopt, that is, wettable powder, granule, dusting powder, emulsion, water-soluble powder, suspending agent, granulated wettable powder, floable, aerosol, transpiration agent by heating, fumigant, poison bait, microcapsule, or the like. As additives and carriers, vegetable powders such as soy flour and wheat flour; fine mineral powder such as diatomaceous earth, apatite, gypsum, talc, bentonite, pyrophyllite, and clay; and organic and inorganic compounds such as sodium benzoate, urea, and sodium sulfate are used when solid formulation is required. When liquid form of formulation is required, petroleum fractions such as kerosene, xylene, and solvent naphtha, and cyclohexane, cyclohexanone, dimethylformamide, dimethyl sulfoxide, alcohol, acetone, methyl isobutyl ketone, mineral oil, vegetable oil, water, or the like are used as a solvent. As gaseous carriers used in propellant, butane (gas), LPG, dimethyl ether, and carbon dioxide gas can be used. As a substrate of poison bait, bait components such as grain powder, vegetable oil, sugar, and crystalline cellulose; antioxidants such as dibutylhydroxytoluene and nordihydroguaiaretic acid; preservatives such as dehydroacetic acid; agents for preventing accidental ingestion by children or pets such as capsicum powder; and pest-insect attracting scents such as cheese scents and onion scents can be used. Additionally, in order to achieve homogenous and stable forms in these formulations, it is also possible to add surfactants if necessary. Although surfactants are not particularly limited, examples thereof include, for instance, nonionic surfactants such as alkyl ether where polyoxyethylene is added, higher fatty acid ester where polyoxyethylene is added, sorbitan higher fatty acid ester where polyoxyethylene is added, and tristyryl phenyl ether where polyoxyethylene is added; sulfate ester salt of alkyl phenyl ether where polyoxyethylene is added, alkyl naphthalene sulfonate salt, polycarboxylate salt, lignin sulfonate salt, formaldehyde condensate of alkyl naphthalene sulfonate, and isobutylene-maleic anhydride copolymer. When the compounds of the present invention are used as agents for pest control in agriculture, the amount of active ingredient in the formulation is 0.01 to 90 weight% and particularly preferably 0.05 to 85 weight% and wettable powder, emulsion, suspending agents, floable agents, water-soluble powder, granulated wettable powder which are diluted to predetermined concentrations with water, and dusting powder and granules as they are, can be applied onto plants or soil. In addition, when the compounds of the present invention are used as agents for pest control in quarantine purposes, emulsion, wettable powder, floable agents, and the like are applied by diluting to predetermined concentrations with water and oil solution, and aerosol, poison bait, anti-acarid sheet, and the like can be applied as they are. When the compounds of the present invention are used as agents for pest control in controlling ectoparasites of livestock such as cattle and pigs or of pets such as dogs and cats, formulations using the compounds of the present invention are used in known methods in the field of veterinary medicine. As such methods, examples thereof include a method for administering in forms such as tablets, capsules, immersion liquid, feedstuff mix, suppository, and injection (intramuscular, subcutaneous, intravenous, intraperitoneal, or the like) when systemic control is required and a method for administering by spraying, pouring-on, or spotting-on oily- or aqueous liquid formulations or a method for mounting objects, which are resin formulations shaped into collars, ear tags, or the like, when non-systemic control is required. In this case, the proportion can be normally used where 0.01 to 1000 mg of the compounds of the present invention are applied per 1 kg of host animal. It should be noted that although the compounds of the present invention are, needless to say, sufficiently effective even when used solely, they can also be used by mixing or combining with one or more of other agents for pest control, germicides, insecticides/acaricides, herbicides, plant growth regulators, synergists, fertilizers, soil conditioners, animal feed, or the like. Representative examples of active ingredients of germicides, acaricides, plant growth regulators, or the like which can be used by mixing or combining with the compounds of the present invention are shown below. Germicides: captan, folpet, thiuram, ziram, zineb, maneb, mancozeb, propineb, polycarbamate, chlorothalonin, quintozene, captafol, iprodione, procymidone, fluoroimide, mepronil, flutolanil, pencycuron, oxycarboxin, fosetyl-aluminum, propamocarb, triadimefon, triadimenol, propiconazole, diclobutrazol, bitertanol, hexaconazole, myclobutanil, flusilazole, etaconazole, fluotrimazole, fiutriafen, penconazole, diniconazole, cyproconazole, fenarimol, triflumizole, prochloraz, imazalil, pefurazoate, tridemorph, fenpropimorph, triforine, buthiobate, pyrifenox, anirazine, polyoxins, metalaxyl, oxadixyl, furalaxyl, isoprothiolane, probenazole, pyrrolnitrin, blasticidin S, kasugamycin, validamycin, dihydrostreptomycin sulfate, benomyl, carbendazim, thiophanate-methyl, hymexazol, basic copper chloride, basic copper sulfate, fentinacetate, triphenyltin hydroxide, diethofencarb, chinomethionat, binapacryl, lecithin, baking soda, dithianon, dinocap, fenaminosulf, diclomezine, guazatine, dodine, IBP, edifenphos, mepanipyrim, fermzone, trichlamide, methasulfocarb, fluazinam, ethoquinolac, dimethomorph, pyroquilon, tecloftalam, phthalide, phenazine oxide, thiabendazole, tricyclazole, vinclozolin, cymoxanil, cyclobutanil, guazatine, propamocarb hydrochloride, oxolinic acid, cyflufenamid, iminoctadine, kresoxim-methyl, triazine, fenhexamid, cyazofamid, cyprodinil, prothioconazole, fenbuconazole, trifloxystrobin, azoxystrobin, hexaconazole, imibenconazole, tebuconazole, difenoconazole, and carpropamid; Insecticides/acaricides: organophosphorus and carbamate pesticides: fenthion, fenitrothion, diazinon, chlorpyrifos, ESP, vamidothion, phenthoate, dimethoate, formothion, malathion, trichlorphon, thiometon, phosmet, dichlorvos, acephate, EPBP, methyl parathion, oxydemeton methyl, ethion, salithion, cyanophos, isoxathion, pyridafenthion, phosalone, methidathion, sulprofos, chlorfenvinphos, tetrachlorvinphos, dimethylvinphos, propaphos, isofenphos, ethylthiometon, profenofos, pyraclofos, monocrotophos, azinphos-methyl, aldicarb, methomyl, thiodicarb, carbofuran, carbosulfan, benfuracarb, furathiocarb, propoxur, BPMC, MTMC, MIPC, carbaryl, pirimicarb, ethiofencarb, fenoxycarb, cartap, thiocyclam, bensultap, and the like; pyrethroid pesticides: permethrin, cypermethrin, deltamethrin, fenvalerate, fenpropathrin, pyrethrin, allethrin, tetramethrin, resmethrin, dimethrin, propathrin, phenothrin, prothrin, fluvalinate, cyfluthrin, cyhalothrin, flucythrinate, etofenprox, cycloprothrin, tralomethrin, silafluofen, and acrinathrin; benzoylurea and other pesticides: diflubenzuron, chlorfluazuron, hexaflumuron, triflumuron, flufenoxuron, flucycloxuron, buprofezin, pyriproxyfen, methoprene, benzoepin, diafenthiuron, imidacloprid, fipronil, nicotine sulfate, rotenone, metaldehyde, acetamiprid, chlorfenapyr, nitenpyram, thiacloprid, clothianidin, thiamethoxam, dinotefuran, indoxacarb, pymetrozine, spinosad, emamectin, pyridalyl, tebufenozide, chromafenozide, methoxyfenozide, tolfenpyrad, machine oil, microbial pesticides such as BT and entomopathogenic viruses; nematicides: fenamiphos, fosthiazate, cadusafos, and the like; acaricides: chlorobenzilate, phenisobromolate, dicofol, amitraz, BPPS, benzomate, hexythiazox, fenbutatin oxide, polynactin, chinomethionat, CPCBS, tetradifon, avermectin, milbemectin, clofentezine, cyhexatin, pyridaben, fenpyroximate, tebufenpyrad, pyrimidifen, fenothiocarb, dienochlor, fluacrypyrim, acequinocyl, bifenazate, etoxazole, spirodiclofen, fenazaquin, and the like; plant growth regulators: gibberellins (for example, gibberellin A3, gibberellin A4, or gibberellin A7), IAA, NAA. [Example] Next, the present invention will be described in further detail by using Examples. However, the present invention is not limited to the Examples below in any aspects. Production Example 1 (Example 1) Production of 3a-(5-trifluoromethyl-2-pyridyloxy)-8-(5-trifluoromethyl-pyridin-2-yl)-8-azabicyclo[3.2. 1] octane 23.3 g of 2,2,2-trichloroethyl chloroformate ester was added to 150 ml of the benzene suspension containing 14.1 g of tropine and 1.4 g of potassium carbonate at room temperature and the entire mixture was refluxed for 3.5 hours. After being cooled to room temperature, the reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with saline and dried with anhydrous magnesium sulfate. 30.1 g of an oily carbonate (A) was obtained by evaporating the solvents under reduced pressure and this carbonate was used directly in the next reaction. Next, 65 g of zinc powder was added to 250 ml of the acetate solution of this carbonate (A). After being stirred for 5 minutes, the mixture was heated at 80°C for 1 hour. After being cooled to room temperature, the mixture was subjected to celite filtration. 15.5 g of a crude product of the compound (B) was obtained by vacuum-concentrating the filtrate. 150 ml of acetonitrile suspension containing 5.64 g of the crude product of the compound (B) obtained as above, 41.5 g of potassium carbonate, and 8.2 g of 2-chloro-5-trifluoromethylpyridine was refluxed for 3.5 hours. After being cooled to room temperature, the reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with saline and dried with anhydrous magnesium sulfate. 3.5 g of the compound (C) was obtained as crystals by evaporating the solvents under reduced pressure. 32 mg of 60% sodium hydride was added to 3 ml of dimethylformamide (DMF) solution containing 0.21 g of the compound (C) with ice-cooling and the entire mixture was stirred for 40 minutes. Subsequently, 0.17 g of 2-chloro-5-trifluoromethylpyridine was added to this mixture and the resulting mixture was heated to 100°C and was stirred overnight with heating. After cooling to room temperature, the reaction mixture was poured into ice-cold water and extracted with ethyl acetate. After being washed with water and dried with anhydrous magnesiunvsulfate, the organic layer was filtered and then vacuum-concentrated. The residue was purified by column chromatography (developing solution: mixed solvent of n-hexane and ethyl acetate) to obtain 0.06 g of the target compound. Melting temperature: 104-105°C 1H-NMRCCDCl3, δppm):1.25(s, 1H), 1.55(s, 1H), 1.95-2.33(m, 6H), 4.58(brs, 2H), 5.37(t, 1H), 6.55(d, 1H), 6.80(d, 1H), 7.61(dd, 1H), 7.78(dd, 1H), 8.41(s, 2H) (Example 2) Production of 3α- [2-n-propoxy-4-(trifluoromethyl)phenoxy] -8- [3-fluoro-4-(trifluoromethyl)phenyl] -8-a zabicyclo[3.2.1]octane 0.44 g of 60% sodium hydride was added to 15 ml of DMF solution containing 1.8 g of 4-fluoro-3-hydroxybenzotrifluoride and after stirring the entire mixture for 20 minutes, 3 ml of DMF solution containing 1.7 g of 1-iodopropane was added thereto and the resulting solution was further stirred for 4 hours at room temperature. 1.4 g of tropine and 0.43 g of 60% sodium hydride were added to the obtained mixture at room temperature and the resulting solution was heated to 100°C and was stirred overnight with heating. After cooling to room temperature, the reaction mixture was poured into ice-cold water and extracted with ethyl acetate. After being washed with water and dried with anhydrous magnesium sulfate, the organic layer was filtered and then vacuum-concentrated. The residue was purified by column chromatography to obtain 1.1 g of an oily compound (D). 4 ml of methylene chloride solution containing 0.83 g of 1-chloroethyl chloroformate ester was added to 6 ml of methylene chloride solution containing 1.0 g of the compound (D) at room temperature and the entire mixture was refluxed overnight. The reaction mixture was diluted with methylene chloride, washed with saturated sodium bicarbonate water and then with saline, and dried with anhydrous magnesium sulfate. A crude carbonate (E) was obtained by evaporating the solvents under reduced pressure and was used directly in the next reaction. 6 ml of methanol was added to the compound (E) and the mixture was refluxed for 2.5 hours. The resulting mixture was vacuum-concentrated to obtain a crude compound (F). The crude compound (F) was alkali-treated to obtain a free amine and this amine was used directly in the next reaction. 0.4 g of t-butoxysodium, 13.7 mg of Pd2(dba)3, and 17.7 mg of 2-(dicyclohexylphosphino)-2'-(N,N-dimethylamino)biphenyl were added to 11 ml of toluene solution containing 1 g of the free form of the compound (F) obtained above and 0.73 g of 4-bromo-2-fluorobenzotrifluoride and the entire mixture was refluxed overnight under nitrogen atmosphere. After cooling to room temperature, the reaction mixture was poured into water and extracted with ethyl acetate. After being washed with water and dried with anhydrous magnesium sulfate, the organic layer was filtered and then vacuum-concentrated. The residue was purified by column chromatography (developing solution: mixed solvent of n-hexane and ethyl acetate) to obtain 0.54 g of the target compound. Viscous oil 1H-NMR(CDCl3, δppm):1.08(t, 3H), 1.81-1.97(m, 4H), 2.04-2.23(m, 4H), 2.45(q,2H), 3.97(t, 2H), 4.19(brs, 2H), 4.57(brt, 1H), 6.44-6.51(m, 2H), 6.76(d, 1H), 7.13(s, 1H), 7.16(d, 1H),7.38(t, 1H) (Example 3) Production of 3a-[5-(trifluoromethyl)-2-pyridyloxy]-8-(2-formyl-4-(trifluoromethyl)phenyl)-8-azabicyc lo[3.2.1]octane A total of 5.8 g of 60% sodium hydride was added at multiple steps to 240 ml of DMF solution containing 17.6 g of tropine and 21.6 g of 2-chloro-5-trifluoromethylpyridine at 80°C and the entire mixture was stirred for 2 hours at the same temperature. After cooling to room temperature, the reaction mixture was poured into ice-cold water and extracted with ethyl acetate. After being washed with water and dried with anhydrous magnesium sulfate, the organic layer was filtered and then vacuum-concentrated. The residue was purified by column chromatography (NH-gel; DM-1020 was used; developing solution: mixed solvent of n-hexane and ethyl acetate) to obtain 25 g of the compound (G). 26 g of 2,2,2-trichloroethyl chloroformate ester was added to 150 ml of the benzene suspension containing 25 g of the compound (G) and 1.33 g of potassium carbonate at room temperature and the mixture was refluxed for 1 hour with heating. After being cooled to room temperature, the mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with saline and dried with anhydrous magnesium sulfate. A solid carbonate was obtained by evaporating the solvents under reduced pressure and this carbonate was used directly in the next reaction. 42 g of zinc powder was added to 300 ml of the acetate solution containing the carbonate obtained above and the entire mixture was stirred for 1 hour with heating at 100°C. After being cooled to room temperature, the mixture was subjected to celite filtration and after adding chloroform and water to the resulting filtrate, the organic layer was separated. The aqueous layer was made weakly alkaline, extracted with chloroform, and mixed with the separated organic layer. The mixture was washed with water, dried with anhydrous magnesium sulfate, and then the solvents thereof were evaporated under reduced pressure to obtain 14.4 g of a crude compound (H). 30 ml of acetonitrile suspension containing 2 g of the compound (H), 3.04 g of potassium carbonate, and 1.41 g of 2-fluoro-5-trifluoromethylbenzaldehyde was refluxed for 3.5 hours. After being cooled to room temperature, the reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with saline and dried with anhydrous magnesium sulfate. 2.77 g of the target compound was obtained by evaporating the solvents under reduced pressure and purifying the residue with silica gel column chromatography (developing solution: mixed solvent of n-hexane and ethyl acetate). Melting temperature: 122-123°C 1H-NMR(CDCl3, δppm):1.99-2.05(m, 2H), 2.12(s, 1H), 2.17(s, 1H), 2.21-2.28(m, 2H), 2.41(t, 1H), 2.45(t, 1H), 4.04(brs, 2H), 5.50(t, 1H), 6.79(d, 1H), 7.05(d, 1H), 7.61(d, 1H), 7.79(dd, 1H), 8.02(s, 1H), 8.44(s, 1H), 10.19(s, 1H) (Example 4) Production of 3α- [2-isopropoxy carbonyl-4-(trifluoromethyl)phenoxy] - 8 - [6-cyano -pyridazine-3 -yl] -8 -az abicyclo[3.2. l]octane Step 1 Production of 3a-[2-isopropoxycarbonyl-4-(trifluoromethyl)phenoxy]-8-azabicyclo[3.2.1]octane(J) 0.56 g of 60% sodium hydride was added to 20 ml of DMF solution containing 1.0 g of tropine. 1.76 g of 4-fluoro-3-isopropoxycarbonylbenzotrifluoride was added dropwise to this mixture. After being stirred overnight at room temperature, the mixture was poured into water and extracted with ethyl acetate. After being washed with water and dried with anhydrous magnesium sulfate, the organic layer was filtered and the resulting filtrate was evaporated under reduced pressure to obtain 1.15 g of a crude compound (I). The crude compound (I) was directly used in the next reaction. Note that 4-fluoro-3-isopropoxycarbonylbenzotrifluoride was obtained by isopropyl-esterifying the commercially available 2-fluoro-5-trifluoromethylbenzoate. 0.05 g of potassium carbonate and 0.52 g of 1-chloroethyl chloroformate ester were added to 20 ml of benzene solution containing 1.23 g of the crude compound (I) and the mixture was refluxed for 5 hours with heating. After being cooled to room temperature, the mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with saline and dried with anhydrous magnesium sulfate. The concentrate obtained by evaporating the solvents under reduced pressure was dissolved in 20 ml of methanol and the entire solution was stirred overnight at room temperature. 1.0 g of a crude compound (J) was obtained by evaporating the solvents under reduced pressure and this compound was used directly in the next reaction. Step 2 Production of 3a-[2-isopropoxycarbonyl-4-(trifluoromethyl)phenoxy]-8-[6-cyano-pyridazin-3-yl]-8-aza bicyclo[3.2.1 ]octane 30 ml of acetonitrile suspension containing 1.0 g of the crude compound (J), 1.16 g of potassium carbonate, and 0.39 g of 3-chloro-6-cyanopyridazine was refluxed for 3 hours with heating. After being cooled to room temperature, the mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with saline and dried with anhydrous magnesium sulfate. The concentrate obtained by evaporating the solvents under reduced pressure was purified with silica gel column chromatography (eluant: mixed solvent of n-hexane and ethyl acetate) to obtain 0.18 g of crystals. Furthermore, these crystals were washed with diethylether to obtain 0.04 g of the target compound. Melting temperature: 219-221 °C 1H-NMR(CDCl3, δppm):1.39(d, 6H), 2.03-2.37(m, 6H), 2.48-2.5 l(m, 2H), 4.69(brs, 3H), 5.22-5.30(m, 1H), 6.75(d, 1H), 6.85(d, 1H), 7.44(d, 1H), 7.68(d, 1H), 7.98(s, 1H) (Example 5) Production of 8β- [2-propoxy-4-(trifluoromethyl)phenoxy] -3 - [6-(trifluoromethyl)-pyridin-3 -yl]-3-azabic yclo[3.2.1]octane Step 1 Production of N-benzyl-8β- [2-propoxy-4-(trifluoromethyl)phenoxy]-3-azabicyclo[3.2.1]octane (L) 0.12 g of 60% sodium hydride was added to 4 ml of DMF solution containing 0.50 g of 4-fluoro-3-hydroxybenzotrifluoride with ice-cooling. After stirring the mixture at room temperature for 30 minutes, 0.51 g of 1 -iodopropane was added thereto. The mixture was heated to 90°C and the mixture was stirred for 30 minutes. 4 ml of DMF solution containing 0.41 g of the compound (K) and 0.09 g of 60% sodium hydride were added to the mixture at room temperature and after being stirred for 15 minutes, the resulting mixture was heated to 100°C and stirred for 2 hours. After being cooled to room temperature, the mixture was poured into water and extracted with ethyl acetate. After being washed with water and dried with anhydrous magnesium sulfate, the organic layer was filtered and then vacuum-concentrated. The concentrate was purified by silica gel column chromatography (eluant: mixed solvent of n-hexane and ethyl acetate) to obtain 0.75 g of the compound (L) as an oily matter. 1H-NMR(CDCl3, δppm):1.05(t, 3H), 1.75-1.91(m, 6H), 2.19(d, 2H), 2.34(brs, 2H), 2.74(d, 2H), 3.51(s, 2H), 3.96(t, 2H), 4.33(s, 1H), 6.94(d, 1H), 7.07(s, 1H), 7.13(d, 1H), 7.20-7.34(m, 5H) Step 2 Production of 8P-[2-propoxy-4-(trifluoromethyl)phenoxy]-3-[6-(trifluoromethyl)-pyridin-3-yl]-3-azabic yclo[3.2.1]octane 0.13 g of 10% palladium-carbon was added to 20 ml of the ethanol solution containing 0.66 g of the compound (L). The suspension was stirred overnight at room temperature under hydrogen atmosphere (1.01 x 105 Pa). The reaction solution was subjected to celite filtration and the resulting filtrate was evaporated under reduced pressure to obtain 0.55 g of a crude compound (M). 3-bromo-6-(trifluoromethyl)pyridine was derived from the commercially available 3-amino-6-(trifluoromethyl)pyridine by the usual Sandmeyer reaction. 0.16 g of 3-bromo-6-(trifluoromethyl)pyridine, 0.1 g of t-butoxy sodium, 6.47 mg of Pd2(dba)3, and 8.34 mg of 2-(dicyclohexylphosphino)-2'-(N,N-dimethylamino)biphenyl were added to 2 ml of the toluene solution containing 0.23 g of the crude compound (M) and the mixture was refluxed with heating overnight under nitrogen atmosphere. After cooling, the reaction mixture was poured into water and extracted with ethyl acetate. After being washed with water and dried with anhydrous magnesium sulfate, the organic layer was filtered and then vacuum-concentrated. The concentrate was purified by silica gel column chromatography (eluant: mixed solvent of n-hexane and ethyl acetate) to obtain 0.1 g of the target compound. Melting temperature: 79-80°C 1H-NMR(CDCl3, δppm):1.07(t, 3H), 1.67-1.71(m, 2H), 1.80-1.92 (m, 2H), 2.09-2.12 (m, 2H), 2.62(brs, 2H), 3.07(d, 2H), 3.69(dd, 2H), 3.98(t, 2H), 4.60(s, 1H), 7.01(d, 1H), 7.09-7.19(m, 3H), 7.50(d, 1H), 8.28(d, 1H) (Example 6) Production of 8P42-isopropylideneaminooxy-4-(trifluoromethyl)phenoxy]-3-(5-trifluoromethyl-l,3,4-t hiadiazol-2-yl)-3-azabicyclo[3.2.1]octane Stepl Production of 3-(5-trifluoromethyl-1,3,4-thiadiazol-2-yl)-3-azabicyclo[3.2.1]octan-8p-ol 2.6 g of 10% palladium-carbon was added to 100 ml of the ethanol solution containing 4.32 g of the compound (K). The suspension was heated to 50°C and stirred for 2 hours under hydrogen atmosphere and further stirred overnight at room temperature. The reaction solution was subjected to celite filtration and the resulting filtrate was evaporated under reduced pressure to obtain 2.5 g of the crude compound (N). 2-bromo-5-(trifluoromethyl)thiadiazole was derived from the commercially available 2-amino-5-(trifluoromethyl)thiadiazole by the usual Sandmeyer reaction. 0.37 g of 2-bromo-5-(trifluoromethyl)-l,3,4-thiadiazole, 0.65 g of potassium carbonate, and 10 mg of tetra-n-butylammoniumbromide were added to 6 ml of the acetonitrile solution containing 0.2 g of the crude compound (N) and the mixture was refluxed with heating overnight. After being cooled to room temperature, the mixture was poured into water and extracted with ethyl acetate. After being washed with water and dried with anhydrous magnesium sulfate, the organic layer was filtered and then vacuum-concentrated. The concentrate was purified by silica gel column chromatography (eluant: mixed solvent of n-hexane and ethyl acetate) to obtain 0.25 g of the target compound. Step 2 Production of 8 β- [2-hydroxy-4-(trifluoromethyl)phenoxy] -3 -(5-trifluoromethyl-1,3,4-thiadiazol-2-yl)-3 -azabicyclo[3.2.1]octane (Q) 1.6 g of 60% sodium hydride was added to 60 ml of the DMF solution containing 6.0 g of 4-fluoro-3-hydroxybenzotrifluoride with ice-cooling. After stirring the mixture for 30 minutes at room temperature, 3.2 g of chloromethyl ether was added dropwise with ice-cooling. After reaching room temperature, the resulting mixture was stirred for 30 minutes, poured into water, and extracted with ethyl acetate. After being washed with water and dried with anhydrous magnesium sulfate, the organic layer was filtered and then vacuum-concentrated. The concentrate was purified by silica gel column chromatography (eluant: mixed solvent of n-hexane and ethyl acetate) to obtain 6.88 g of a compound (O). 0.34 g of the compound (N) was added to 6 ml of the DMF solution containing 0.36 g of the compound (0). The mixture was heated to 80°C and 0.07 g of 60 % sodium hydride was added thereto and the resulting mixture was kept heated to 80°C for 2 hours. After being cooled to room temperature, the mixture was poured into water and extracted with ethyl acetate. After being washed with water and dried with anhydrous magnesium sulfate, the organic layer was filtered and then vacuum-concentrated. The concentrate was purified by silica gel column chromatography (eluant: mixed solvent of n-hexane and ethyl acetate) to obtain 0.28 g of a compound (P). 1H-NMR(CDCl3, δppm): 1.68-1.71 (m, 2H), 2.10-2.13(m, 2H), 2.62(brs,2H), 3.45(d 2H), 3.52(s, 3H), 3.84(d, 2H), 4.63(s, 1H), 5.20(s, 2H), 7.01(d, 1H), 7.25(d, 1H), 7. 37(s, 1H) 4 ml of 10% hydrochloric acid was added to 4 ml of tetrahydrofuran(THF) solution containing 0.28 g of the compound (P) at room temperature. The mixture was refluxed with heating for 1 hour and then poured into water and extracted with ethyl acetate. The organic layer was washed with saturated sodium bicarbonate water and then with saline, and dried with anhydrous magnesium sulfate. 0.25 g of the target compound (Q) was obtained by evaporating the solvents under reduced pressure. 1H-NMR(CDCl3, δppm): 1.68-1.79(m, 2H), 2.05-2.10(m, 2H), 2.69(brs, 2H), 3.50(d, 2H), 3.89(d, 2H), 4.67(s, 1H), 5.58(s, 1H), 6.97(d, 1H), 7.15(d, 1H), 7.21(s, 1H) Step 3 Production of 8β- [2-isopropylideneaminooxy-4-(trifluoromethyl)phenoxy] -3 -(5-trifluoromethyl-1,3,4-t hiadiazol-3 -yl)-3 -azabicyclo [3.2.1]octane 0.07 g of a compound (R) was synthesized by the method described in Japanese Patent Application Laid-Open No. 2001-81071 using 0.25 g of the compound (Q). 0.5 ml of acetone and 1 drop of concentrated hydrochloric acid were added to 1 ml of ethanol solution containing 0.07 g of the compound (R) and the entire mixture was stirred for 80 minutes at room temperature. The reaction mixture was poured into water and extracted with ethyl acetate. After being washed with water and dried with anhydrous magnesium sulfate, the organic layer was filtered and then vacuum-concentrated. The concentrate was purified by silica gel column chromatography (eluant: mixed solvent of n-hexane and ethyl acetate) to obtain 0.05 g of the target compound. Melting temperature: 113-115°C 1H-NMR(CDCl3, δppm): 51.64-1.70(m, 2H), 2.06(d, 6H), 2.03-2.13(m, 2H), 2.61(brs, 2H), 3.42(d, 2H), 3.82(dd, 2H), 4.64(s, 1H), 7.01(d, 1H), 7.21(d, 1H), 7.70(s, 1H) (Example 7) Production of 8p-[2-isopropylideneaminooxy-4-(trifluoromethyl)phenoxy]-3-(5-cyano-pyridin-2-yl)-3- azabicyclo[3.2.1]octane (e) Step 1 Production of 8β-hydroxy-3-(5-cyano-pyridin-2-yl)-3-azabicyclo[3.2.1 ]octane (S) 5 ml of acetonitrile suspension containing 0.15 g of 3-azabicyclo[3.2.1]octa-8-ol, 0.65 g of potassium carbonate, and 0.33 g of 2-chloro-5-cyanopyridine was refluxed with heating overnight. After being cooled to room temperature, the mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with saline and dried with anhydrous magnesium sulfate. 0.16 g of a crude compound (S) was obtained by evaporating solvents under reduced pressure and this compound was directly used in the next step. Step 2 Production of 8β-[2-methoxymethoxy-4-(trifluoromethyl)phenoxy]-3-(5-cyano-pyridin-2-yl)-3-azabicy clo[3.2.1] octane (T) 0.14 g of 60% sodium hydride was added to 10 ml of DMF solution containing 0.58 g of 4-fluoro-3-hydroxybenzotrifluoride with ice-cooling. After stirring the mixture for 30 minutes at room temperature, 0.28 g of chloromethyl ether was added dropwise thereto with ice-cooling. After completing the addition, the reaction solution was heated to room temperature and stirred for 30 minutes and then further heated to 80°C and stirred for 30 minutes. 0.49 g of the compound (S) and 0.13 g of 60% sodium hydride were added to the reaction mixture at 80°C and the resulting mixture was stirred for 30 minutes and then heated to 80°C and was further stirred for 2 hours. The reaction mixture was cooled to room temperature, poured into water, and extracted with ethyl acetate. After being washed with water and dried with'anhydrous magnesium sulfate, the organic layer was filtered and vaccum-concentrated. The concentrate was purified by silica gel column chromatography (eluant: mixed solvent of n-hexane and ethyl acetate) to obtain 0.82 g of the target compound (T). 1H-NMR(CDCl3, δppm):1.55-1.63(m, 2H), 2.02-2.05(m, 2H), 2.60(brs, 2H), 3.13(d,2H), 3.52(s, 3H), 4.22(d, 2H), 4.63(s, 1H), 5.20(s, 2H), 6.58(d, 1H), 7.03(d, 1H) 7.26(d, 1H), 7.37(s, 1H), 7.62(d, 1H), 8.41(s, 1H) Step 3 Production of 8β-[2-hydroxy-4-(trifluoromethyl)phenoxy]-3-(5-cyano-pyridin-2-yl)-3-azabicyclo[3.2.1] octane (U) 10 ml of 10% hydrochloric acid was added to 10 ml of THF solution containing 0.82 g of the compound (T) at room temperature. The mixture was refluxed with heating for 30 minutes, poured into water, and extracted with ethyl acetate. The organic layer was washed with saline and dried with anhydrous magnesium sulfate. 0.74 g of the target compound (U) was obtained by evaporating the solvents under reduced pressure. 1H-NMR(CDCl3, δppm):1.62-1.75(m, 2H), 1.91-1.98(m, 2H), 2.65(brs, 2H), 3.17(d, 2H), 4.26(d, 2H), 4.66(s, 1H), 5.63(s, 1H), 6.60(d, 1H), 6.98(d, 1H), 7.13(d, 1H) 7.16(s, 1H), 7.63(d, 1H), 8.42(s, 1H) This compound was directly used in the next step without purification. Step 4 Production of 8P-[2-isopropylideneaminooxy-4-(trifluoromethyl)phenoxy]-3-(5-cyano-pyridin-2-yl)-3- azabicyclo[3.2.1]octane (W) 0.76 g of a compound (V) was synthesized by the method described in Japanese Patent Application Laid-OpenNo. 2001-81071 using 0.74 g of the compound (U). 1H-NMR(CDCl3,δppm):1.55-1.68(m, 2H), 1.99-2.04(m, 2H), 2.59(brs, 2H), 3.13(d, 2H), 4.22(d, 2H), 4.60(s, 1H), 6.00(brs, 2H), 6.59(d, 1H), 6.98(d, 1H), 7.20(d, 1H), 7.60(d, 2H),8.01(s, 1H),8.41(s, 1H) 3 ml of acetone and 1 drop of concentrated hydrochloric acid were added to 3 ml of ethanol solution containing 0.76 g of the compound (V) and the entire mixture was stirred for 1 hour at room temperature. The mixture was poured into water and extracted with ethyl acetate. After being washed with water and dried with anhydrous magnesium sulfate, the organic layer was filtered and then vacuum-concentrated. The concentrate was purified by silica gel column chromatography (eluant: mixed solvent of n-hexane and ethyl acetate) to obtain 0.45 g of the target compound (W). The structure was confirmed by NMR. Melting temperature: 120-122°C (Example 8) Production of 9P-[2-cyclopropylmethoxy-4-(trifluoromethyl)phenoxy]-7-[6-(trifluoromethyl)-3-pyridaz yl] -3 -oxa-7-azabicyclo [3.3.1] nonane (AC) Step 1 Production of N-benzyl-3-oxa-7- azabicyclo[3.3.1]nonan-9-ol (Z) 1.2 g of acetic acid, 80 ml of methanol, and 5.33 g of 90% formalin were added to 2.2 g of benzylamine in this order. Furthermore, while gradually heating the mixture from 20°C to 45°C, 2.0 g of the compound (X) was added dropwise thereto and the resulting mixture was refluxed for 5.5 hours and stirred overnight at room temperature. The solvents were evaporated under reduced pressure from the reaction mixture and 100 ml of water and 2 ml of concentrated hydrochloric acid were added to the obtained residue and washed with diethylether. pH of the aqueous layer was adjusted to 7 or more by adding sodium hydroxide and extracted with chloroform. After drying the organic layer with anhydrous magnesium sulfate, the solvents were evaporated under reduced pressure and the residue was purified by silica gel column chromatography (chloroform: methanol = 10:1 (v/v)) to obtain 4.09 g of a compound (Y). Yield 88.5% Subsequently, 1.86 g of sodium borohydride was added to 30 ml of 2-propanol solution containing 2.24 g of the compound (Y) at 0°C and thereafter, 15 ml of water was added thereto and the resulting mixture was heated to room temperature and stirred for one day. After cooling the reaction mixture to 0°C, 75 ml of 10% hydrochloric acid was added thereto and thereafter, 45 ml of 10% sodium hydroxide was added thereto at the same temperature. The resulting mixture was extracted with chloroform and the organic layer was dried with anhydrous magnesium sulfate. The solvents were evaporated under reduced pressure to obtain 1.56 g of the compound (Z) as a viscous oil. Yield 83.8% Step 2 Production of the compound (AA) 0.40 g of 60%o sodium hydride was added to 20 ml of DMF solution containing 1.56 g of the compound (Z) obtained in Step 1 and the resulting mixture was stirred for 15 minutes at room temperature. 2.35 g of 4-fluoro-3-(cyclopropylmethoxy)benzotrifluoride was added to the mixture and the resultant mixture was stirred for 3 hours at 100°C. After cooling the reaction mixture to room temperature, water was poured thereto and extracted with ethyl acetate. After being washed with saturated saline and dried with anhydrous magnesium sulfate, the organic layer was filtered and vacuum-concentrated to obtain a crude compound (AA). The obtained crude compound (AA) was purified by silica gel column chromatography (eluant: n-hexane: ethyl acetate = 2:3 (v/v)) to obtain 0.98 g of a compound (AA-cis) as a viscous oil (yield 32.7%o) and 0.76 g of a compound (AA-trans) as a viscous oil (yield 25.4%>), respectively. NMR data of AA-cis: 1H-NMR(CDCl3, δppm):0.34-0.44(m, 2H), 0.60-0.67(m, 2H), 1.26-1.3 l(m, 2H), 1.94(brs, 2H), 2 .49(d, 2H), 3.17(d, 2H), 3.57(s, 2H), 3.79(d, 2H), 3.88(d, 2H), 4.27(d, 2H), 4.43(t, 1H), 6.94(d, 1H), 7.10(s, 1H), 7.17(d, 1H), 7.20-7.40(m, 5H) NMR data of AA-trans: 1H-NMR(CDCl3, δppm):0.39-0.44(m, 2H), 0.62-0.71(m, 2H), 1.25-1.35(m, 1H), 2.04(brs, 2H), 2.84(brs, 4H), 3.55(s, 2H), 3.82(d, 2H), 3.89(d, 2H), 4.13(d, 2H), 4.59(t, 1H), 6.95(d, 1H), 7.10(s, 1H), 7.14(d, 1H), 7.20-7.42(m, 5H) Step 3 0.20 g of 10% Pd/C was added to 20 ml of ethanol solution containing 0.98 g of the compound (AA-cis) obtained in Step 2 and the entire mixture was stirred for 6.5 hours at 60°C under hydrogen atmosphere (atmospheric pressure). The reaction mixture was filtered and the filtrate was evaporated under reduced pressure to obtain 0.75 g of a debenzylated product (AB) as an oily matter. Yield 95.9% 1H-NMR(CDCl3, δppm):0.35-0.40(m, 2H), 0.60-0.69(m, 2H), 1.23-1.34(m, 1H), 1.83(brs, 2H), 1.99(brs, 1H), 3.04(d, 2H), 3.38(d, 2H), 3.85-3.91(m, 4H), 4.35(d, 2H), 4.59(t, 1H), 6.95(d, 1H), 7.10(s, 1H), 7.12(d, 1H) 0.19 g of 3-chloro-6-(trifluoromethyl)pyridazine and 0.15 g of DBU were added to 3 ml of N-methylpyrrolidone solution containing the obtained compound (AB) and the resulting mixture was stirred for 3 hours at 120 to 130°C. After cooling the reaction mixture to room temperature, water was poured thereto and extracted with ethyl acetate. After being washed with saturated saline and dried with anhydrous magnesium sulfate, the organic layer was filtered and vacuum-concentrated. The obtained residue was purified by silica gel column chromatography (eluant: n-hexane: ethyl acetate =1:1 (v/v)) to obtain 0.24 g of the target compound (AC). Yield 57%, mp. 93 to 95°C Examples of the compounds of the present invention produced by the method according to the above Examples are shown in the Table below including the compounds produced in the above Examples. Note that in the Table below, R1 and R2 show substituents including substituents associated by two or more substituents so that the Table is simplified. Also, the description "vis" shows that the compound is a viscous oil and the description "amor" shows that the compound is amorphous. Moreover, nD21.8-1.5008 means that the refractive index at 21.8°C is 1.5008 (the same also applies to others). In addition, the description "cPr" means cyclopropyl, the description "cHex" means cyclohexyl (the same also applies to others), the description "Ac" means acetyl, the description "nPr" means normal propyl, the description "iPr" means isopropyl, the description "nBu" means normal butyl, the description "iBu" means isobutyl, and the description "tBu" means tertiary butyl, and the description "TMS" means trimethylsilyl and the description "THF" means tetrahydrofuranyl. Formulation Examples [Insecticides/acaricides] Although a few examples regarding compositions of the present invention are shown next, additives and proportions added are changeable over a wide range without being limited to these examples. Parts in Formulation Examples show parts by weight. Formulation Example 1 Wettable powder Compound of the present invention 40 parts Diatomaceous earth 53 parts Higher alcohol sulfate ester 4 parts Alkylnaphthalenesulfonate salt 3 parts The above components were mixed homogenously and ground finely to obtain a wettable powder with 40% of active ingredient. Formulation Example 2 Emulsion Compound of the present invention 3 0 parts Xylene 33 parts Dimethylformamide 30 parts Polyoxyethylene alkyl allyl ether 7 parts The above components were mixed and dissolved to obtain an emulsion with 30% of active ingredient. Formulation Example 3 Dusting powder Compound of the present invention 10 parts Talc 89 parts Polyoxyethylene alkyl allyl ether 1 part The above components were mixed homogenously and ground finely to obtain a dusting powder with 10% of active ingredient. Formulation Example 4 Granules Compound of the present invention 5 parts Clay 73 parts Bentonite 20 parts Sodium dioctylsulfosuccinate salt 1 part Sodium phosphate 1 part The above components were mixed and ground well and, after adding water thereto and kneading together, granulated and dried to obtain granules with 5% of active ingredient. Formulation Example 5 Suspending agent Compound of the present invention 10 parts Sodium lignin sulfonate 4 parts Sodium dodecylbenzenesulfonate 1 part Xanthan gum 0.2 parts Water 84.8 parts The above components were mixed and subjected to wet-grinding until the grain size of 1 µm or less was achieved to obtain a suspending agent with 10% of active ingredient. Test Example 1 Effectiveness against Tetranychus urticae 17 adult female Tetranychus urticae, which were resistant to organophosphorous pesticides, were inoculated on the first true leaf of a common bean, which was seeded in a pot with a diameter of 9 cm, where 7 to 10 days had passed after the germination. After the inoculation, the drug solution, which was prepared by following the method of the wettable powder shown in Example 1 of the drugs and by diluting with water to achieve the compound concentration of 125 ppm, was applied. The pot was placed in a temperature-controlled room where the temperature and humidity were set to 25°C and 65% respectively, and the adulticidal rate was examined 3 days after the application. The test was repeated twice. As a result, the compounds below showed the insecticidal rate of 100%. 1-1, 1-4 to 1-7,1-10,1-13, 1-17,1-18,1-21 to 1-29,1-31 to 1-36,1-39 to 1-47, 1-50, 1-51, 1-54, 2-3, 3-1,4-5, 4-7,4-9, 4-13, 4-16,4-18 to 4-20,4-53 to 4-55,4-58 to 4-61, 4-64, 4-70, 4-71, 5-1 to 5-8,10-1, 11-1, 13-2, 15-1,15-17,16-1 to 16-26, 16-61, 16-65, 16-69,16-73 to 16-75,16-78,16-82 to 16-91,17-2,17-3,17-7 to 17-10,19-1 to 19-3, 21-1, 21-3,21-5, 21-6,21-14 to 21-16 Test Example 2 Effectiveness against Panonychus citri 10 adult female Panonychus citri were inoculated on the leaf of a mandarin orange, which was placed in a petri dish. After the inoculation, the drug solution, which was prepared by following the method of the emulsion shown in Example 2 of the drugs and by diluting with water to achieve the compound concentration of 125 ppm, was applied using a rotary spreading tower. The dish was placed in a temperature-controlled room where the temperature and humidity were set to 25°C and 65% respectively, adults were removed 3 days after the application, and whether eggs laid during these 3 days could grow to become adults was examined on the 11th day. As a result, the compounds below showed the insecticidal rate of 100%. 1-1,1-5,1-7, 1-13,1-17,1-24,1-31,1-32,1-47,1-50, 3-1, 4-5, 4-53, 4-54, 4-58 to 4-61, 4-64, 4-70, 4-71, 5-1, 5-2, 5-4, 5-8,10-1, 12-4,16-1 to 16-13,16-15 to 16-20,16-22, 16-23,16-26, 16-61, 16-73, 16-83, 16-84, 16-89 to 16-91, 17-7,17-9,17-10,19-1 to 19-3,21-5,21-6,21-13 Test Example 3 Effectiveness test against Pseudaletia separata 0.2 ml of a commercially available artificial diet (Insecta LFS manufactured by Nihon Nosan-Kogyo Co., Ltd) was put into a plastic test tube with a volume of 1.4 ml and was used as a test diet. The compound was adjusted to prepare 1% solution using dimethylsulfoxide containing 0.5% tween 20 and this solution was applied by adding dropwise onto the surface of the diet in an amount equivalent to 10 µg of the compound. 2 second-instar larvae of Pseudaletia separate were inoculated to each test tube and the tubes were sealed with plastic lids. The tubes were left at 25°C and the insecticidal rate and amount of food ingested were examined after 5 days. The test was repeated twice. In the present test, the compounds below were effective by showing the insecticidal rate of 100%, or the amount of food ingested was 10% or less compared to the solvent control group. 4-3, 4-4,16-1,16-2,17-3, 17-7 to 17-9 Test Example 4 Effectiveness test against Culexpipiens molestus 10 larvae of Culex pipiens molestus, which were hatched 1 day before, and 0.225 ml of distilled water containing 0.5 mg of feed for aquarium fish (TetraMin® manufactured by Tetra Japan Co. Ltd) were put into a polystyrene test vessel with a volume of 0. 3 ml. The compound was adjusted to prepare 1% solution using dimethylsulfoxide containing 0.5% tween 20 and further diluted to 0.01% with distilled water. 0.025ml of this diluted drug solution was added to the test vessel with Culex pipiens molestus and was stirred (final compound concentration 0.001%). The vessels were left at 25 °C and the insecticidal rate was examined after 2 days. The test was repeated twice. In the present test, the compound below was effective by showing the insecticidal rate of 90% or more. 4-3 While preferred embodimentss or the invention nave been illustrated above, it should be understood that these are exemplary of the invention and are not to be considered as limiting. Additions, omissions, substitutions, and other modifications can be made without departing from the spirit or scope of the present invention. Accordingly, the invention is not to be considered as being limited by the foregoing description, and is only limited by the scope of the appended claims. [Industrial Applicability] According to the present invention, it is possible to provide cyclic amine compounds with a novel structure, salts thereof, N-oxides thereof, or intermediates thereof during the production and especially agents for pest control with excellent bioactivities in terms of insecticidal/acaricidal activities and high safety. WE CLAIM: 1. Cyclic amine compounds represented by formula (1) or salts thereof or N-oxides thereof, wherein Cy1 represents one selected from the group consisting of unsubstituted or substituted phenyl, unsubstituted or substituted naphthalen-1-yl, and unsubstituted or substituted heteroaromatic ring; X represents oxygen, sulfur, unsubstituted or substituted nitrogen, sulfinyl, or sulfonyl; R1a, and R2a, R1a and R4a, R2a and R3a, or R3a and R4a form saturated rings together; R1a, R1b, R2a, R2b, R3a, R3b, R4a, R4b, and R5 which do not form the saturated rings are each independently hydrogen, hydroxyl, halogen, unsubstituted or substituted amino, nitro, or an organic group; Cy2 represents one selected from the group consisting of unsubstituted or substituted aromatic hydrocarbon, unsubstituted or substituted furan-2-yl, unsubstituted or substituted furan-3-yl, unsubstituted or substituted thiophen-2-yl, unsubstituted or substituted thiophen-3-yl, unsubstituted or substituted pyrrol-2-yl, unsubstituted or substituted pyrrol-3-yl, unsubstituted or substituted oxazol-2-yl, unsubstituted or substituted oxazol-4-yl, unsubstituted or substituted oxazol-5-yl, unsubstituted or substituted thiazol-2-yl, unsubstituted or substituted thiazol-4-yl, unsubstituted or substituted thiazol-5-yl, unsubstituted or substituted isoxazol-3-yl, unsubstituted or substituted isoxazol-4-yl, unsubstituted or substituted isoxazol-5-yl, unsubstituted or substituted isothiazol-3-yl, unsubstituted or substituted isothiazol-4-yl, unsubstituted or substituted isothiazol- 5-yl, unsubstituted or substituted imidazol-4-yl, unsubstituted or substituted imidazol-5-yl, unsubstituted or substituted pyrazol-3-yl, unsubstituted or substituted pyrazol-4-yl, unsubstituted or substituted pyrazol-5-yl, unsubstituted or substituted 1,3,4-oxadiazol-2-yl, unsubstituted or substituted 1,3,4-thiadiazol-2-yl, unsubstituted or substituted 1,2,3-triazol-4-yl, unsubstituted or substituted 1,2,4-triazol-3-yl, unsubstituted or substituted 1,2,4-triazol-5-yl, unsubstituted or substituted pyridin-2-yl, unsubstituted or substituted pyridin-3-yl, unsubstituted or substituted pyridin-4-yl, unsubstituted or substituted pyridazin-3- yl, unsubstituted or substituted pyridazin-4-yl, unsubstituted or substituted pyrazin-2-yl, unsubstituted or substituted pyrimidin-2-yl, unsubstituted or substituted pyrimidin-4-yl, unsubstituted or substituted pyrimidin-5-yl, unsubstituted or substituted 1,3,5- triazin-2-yl, and unsubstituted or substituted 1,2,4- triazin-3-yl; with a proviso that Cy2 is an unsubstituted or substituted furan-2-yl, unsubstituted or substituted furan-3-yl, unsubstituted or substituted thiophen-2-yl, unsubstituted or substituted thiophen-3-yl, unsubstituted or substituted pyrrol-2-yl, unsubstituted or substituted pyrrol-3-yl, unsubstituted or substituted oxazol-2-yl, unsubstituted or substituted oxazol-4-yl, unsubstituted or substituted oxazol-5-yl, unsubstituted or substituted thiazol-2-yl, unsubstituted or substituted thiazol-4-yl, unsubstituted or substituted thiazol-5-yl, unsubstituted or substituted isoxazol-3-yl, unsubstituted or substituted isoxazol-4-yl, unsubstituted or substituted isoxazol-5-yl, unsubstituted or substituted isothiazol-3- yl, unsubstituted or substituted isothiazol-4-yl, unsubstituted or substituted isothiazol-5-yl, unsubstituted or substituted imidazol-4-yl, unsubstituted or substituted imidazol-5-yl, unsubstituted or substituted pyrazol-3-yl, unsubstituted or substituted pyrazol-4-yl, unsubstituted or substituted pyrazol-5-yl, unsubstituted or substituted 1,3,4-oxadiazol-2-yl, unsubstituted or substituted 1,3,4-thiadiazol-2-yl, unsubstituted or substituted 1,2,3-triazol-4-yl, unsubstituted or substituted 1,2,4-triazol-3-yl, unsubstituted or substituted 1,2,4-triazol-5-yl, unsubstituted or substituted pyridin-2-yl, unsubstituted or substituted pyridin-3-yl, unsubstituted or substituted pyridin-4-yl, unsubstituted or substituted pyridazin-3- yl, unsubstituted or substituted pyridazin-4-yl, unsubstituted or substituted pyrazin-2-yl, unsubstituted or substituted pyrimidin-2-yl, unsubstituted or substituted pyrimidin-4-yl, unsubstituted or substituted pyrimidin-5-yl, unsubstituted or substituted 1,3,5- triazin-2-yl, and unsubstituted or substituted 1,2,4- triazin-3-yl when R1a and R2a form a saturated ring together and Cy1 is an unsubstituted or substituted phenyl, and Cy2 is a substituted pyridin-2-yl having one or more cyano as a substituent when Cy1 is an unsubstituted or substituted phenyl and Cy2 is a pyridin- 2-yl. 2. Cyclic amine compounds, salts thereof, or N-oxides thereof as claimed in Claim 1, wherein the organic groups Rla, R1b, R2a, R2b, R3a, R3b, R4a, R4b, and R5 which do not form the saturated rings in the formula (1) are alkyl, alkoxycarbonyl, or alkoxy. 3. Cyclic amine compounds, salts thereof, or N-oxides thereof as claimed in Claim 1 or 2, wherein Rla and R2a, or R3a and R4a form the saturated ring together. 4. Cyclic amine compounds, salts thereof, or N-oxides thereof as claimed in Claim 1, wherein the number of atoms at a crosslink of a piperidine ring, which forms the saturated ring, is 2 or 3. 5. Cyclic amine compounds represented by a formula (2) or salts thereof or N-oxides thereof, wherein Cy1 represents an unsubstituted or substituted aromatic ring; X0 represents oxygen, sulfur, sulfinyl, or sulfonyl; R3a and R4a form a saturated ring together; R1a, R1b, R2a, R2b, R3b, R4b, and R5 each independently represents hydrogen, hydroxyl, halogen, unsubstituted or substituted amino, nitro, or an organic group; and R represents hydrogen, alkoxycarbonyl, alkylcarbonyl, or 1-alkoxyalkyl. 6. Cyclic amine compounds, salts thereof, or N-oxides thereof as claimed in Claim 5, wherein the organic groups R1a, R1b, R2a, R2b, R3b, R4b, and R5 in the formula (2) which do not form the saturated rings are alkyl, alkoxycarbonyl, or alkoxy. 7. Cyclic amine compounds, salts thereof, or N-oxides thereof as claimed in Claim 5, wherein R3a and R4a form the saturated ring together and the number of atoms at a cross-linking site of the piperidine ring, which forms the saturated ring, is 2 or 3. 8. A pesticidal composition comprising at least one of cyclic amine compounds represented by formula (3), salts thereof, or N-oxides thereof as an active ingredient, wherein Cy11 represents an unsubstituted or substituted aromatic ring; X11 represents oxygen, sulfur, unsubstituted or substituted nitrogen, sulfinyl, or sulfonyl; R11a and R21a, R11a and R41a, R21a and R31a, or R31a and R41a form saturated rings together; R11a, R11b, R21a, R21b, R31a, R31b, R41a, R41b, and R51 which do not form the saturated rings each independently represents hydrogen, hydroxyl, halogen, unsubstituted or substituted amino, nitro, or an organic group; and Cy21 represents an unsubstituted or substituted aromatic ring 9. A pesticidal composition as claimed in Claim 8, wherein the pest is a insect or an acarid. The invention discloses cyclic amine compounds represented by formula (1): wherein Cy1, Cy2, Rla, Rlb, R2a, R2b, R3a, R3b, R4a, R4b , R5 and X are as described in the specification. The invention is also for a pesticidal composition comprising the above cyclic amine compounds.

Full Text

SPECIFICATION
[Title of the Invention]
[Field of the Invention]
The present invention relates to novel cyclic amine compounds and agents for
pest control which contain these cyclic amine compounds or the like as active
ingredients.
Priority is claimed on Japanese Patent Application No. 2005-294126, filed
October 6,2005, Japanese Patent Application No. 2005-294127, filed October 6,2005,
Japanese Patent Application No. 2005-297803, filed October 12, 2005, Japanese Patent
Application No. 2005-297804, filed October 12,2005, Japanese Patent Application No.
2006-016877, filed January 25,2006, and Japanese Patent Application No. 2006-182314,
filed June 30,2006, the contents of which are incorporated herein by reference.
[Description of the Related Art]
Although many compounds which have insecticidal/acaricidal activities are
conventionally known, there are problems such as insufficient effect thereof, limitation of
use thereof because of drug resistance problems, occurrence of phytotoxicity or
contamination in plant bodies, or strong toxicity against mammalians, fish, or the like.
As compounds with backbones similar to those of the compounds of the present
invention, compounds represented by the formula below are known.

In the formula, X represents -O-, -N(R3)-, -S-, or the like and R1 represents a
substituted saturated heterocyclic group or the like. As a representative of such
compounds, the compound represented by the formula below is known (refer to Patent
document 1).

Moreover, the compounds represented by the formula below are known.

In the formula, X represents -CH- or the like; Z represents a bonding or the like;
R3 represents an optionally substituted aryl or an optionally substituted heteroaryl; and R7
and R8 represent -(CH2)s- or the like together. However, when R7 and R8 represent
-(CH2)S- together, only the compounds where R is a substituted phenyl like the
compound represented by the formula below are specifically shown as examples (refer to
Patent document 2).

Furthermore, the compounds known in Patent documents 1 and 2 are for
medical purposes and their use in the agents for pest control is not described.
[Patent document 1] WO 02/100833
[Patent document 2] WO 05/14578
[Problems to be Solved by the Invention]
An object of the present invention is to provide agents for pest control, which
can be synthesized industrially favorably, which have excellent bioactivities, and which
are problem-free in terms of safety.
[Means for Solving the Problem]
As a result of intensive research in order to solve the above problems, the
present inventors discovered that novel cyclic amine compounds with a specific structure
have excellent insecticidal/acaricidal activities to complete the present invention. In
other words, the present invention firstly provides cyclic amine compounds represented
by the formula (1), salts thereof, or N-oxides thereof.

In the formula, Cy1 represents an unsubstituted or substituted aromatic ring. X
represents oxygen, sulfur, unsubstituted or substituted nitrogen, sulfinyl, or sulfonyl.
R1a and R2a, R1a and R4a, R2a and R3 3, or R3a and R a form saturated rings together. R1a,
Rlb, R2a, R2b, R3a, R3b, R4a, R4b, and R5 which do not form the aforementioned saturated

rings each independently represents hydrogen, hydroxyl, halogen, unsubstituted or
substituted amino, nitro, or an organic group. Cy2 represents an unsubstituted or
substituted aromatic ring with a proviso that Cy2 is an unsubstituted or substituted
heteroaromatic ring when R1a and R2a form a saturated ring together and Cy1 is an
unsubstituted or substituted phenyl; and Cy2 is a substituted pyridin-2-yl having one or
more cyano as a substituent when Cy1 is an unsubstituted or substituted phenyl and Cy2
is a pyridin-2-yl.
Moreover, the present invention secondly provides cyclic amine compounds
represented by the formula (2), salts thereof, or N-oxides thereof.

In the formula, Cy1 represents an unsubstituted or substituted aromatic ring. X
represents oxygen, sulfur, sulfinyl, or sulfonyl. R3a and R4a form a saturated ring
together. R1a, R1b, R2a, R2b, R3b, R4b and R5 each independently represents hydrogen,
hydroxyl, halogen, unsubstituted or substituted amino, nitro, or an organic group. R
represents hydrogen, alkoxycarbonyl, alkylcarbonyl, or 1-alkoxyalkyl.
Furthermore, the present invention thirdly provides agents for pest control,
which contains at least one of cyclic amine compounds represented by the formula (3),
salts thereof, or N-oxides thereof, as active ingredients.

In the formula, Cy11 represents an unsubstituted or substituted aromatic ring. X11
represents oxygen, sulfur, unsubstituted or substituted nitrogen, sulfinyl, or sulfonyl.
R11a and R21a, R11a and R41a, R21a and R31a, or R31a and R41a form saturated rings together.
R11a, R11b, R21a, R21b, R31a, R31b, R41a, R41b, and R51 which do not form the aforementioned
saturated rings each independently represents hydrogen, hydroxyl, halogen, unsubstituted
or substituted amino, nitro, or an organic group. Cy21 represents an unsubstituted or
substituted aromatic ring.
[Effects of the Invention]
According to the present invention, it is possible to provide cyclic amine
compounds with a novel structure, salts thereof, N-oxides thereof, or intermediates
thereof during the production, and especially agents for pest control with
insecticidal/acaricidal activities for particularly crop-damaging insects and acarids
whereby high safety can be provided.
[Preferred Embodiments of the Invention]
The present invention will be described in detail below.
1) Cyclic amine compounds represented by the formulae (1) and (2), salts thereof, or
N-oxides thereof
In the cyclic amine compounds represented by the formula (1), Cy1 represents

an unsubstituted or substituted aromatic ring:
Specific examples of the aromatic rings include aromatic hydrocarbons such as
phenyl, naphthalen-1-yl, naphthalen-2-yl; and heteroaromatic rings such as furan-2-yl,
furan-3-yl, thiophen-2-yl, thiophen-3-yl, pyrrol-2-yl, pyrrol-3-yl, oxazol-2-yl,
oxazol-4-yl, oxazol-5-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl, isoxazol-3-yl,
isoxazol-4-yl, isoxazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl,
imidazol-2-yl, imidazol-4-yl, imidazol-5-yl, pyrazol-3-yl, pyrazol-4-yl, pyrazol-5-yl,
l,3,4-oxadiazol-2-yl, l,3,4-thiadiazol-2-yl, l,2,3-triazol-4-yl, l,2,4-triazol-3-yl,
l,2,4-triazol-5-yl, pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyridazin-3-yl, pyridazin-4-yl,
pyrazin-2-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl, l,3,5-triazin-2-yl, and
l,2,4-triazin-3-yl; and phenyl is preferable.
Specific examples of the substituents of the aromatic rings include hydroxyl;
thiol; halogen such as fluorine, chlorine, bromine, and iodine; cyano; nitro; formyl;
unsubstituted or substituted amino such as amino, methylamino, benzylamino, anilino,
dimethylamino, diethylamino, and phenylethylamino; alkyl (preferably C1-6 alkyl) such
as methyl, ethyl, n-propyl, isopropyl, n-butyl, s-butyl, isobutyl, t-butyl, n-pentyl, and
n-hexyl; alkenyl such as vinyl, allyl, and 2-methoxy-ethenyl; alkynyl such as ethynyl,
1-propynyl, 2-phenylethynyl, and propargyl; alkoxy (preferably C1-6 alkoxy) such as
methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, s-butoxy, isobutoxy, and t-butoxy;
alkenyloxy such as vinyloxy and allyloxy; alkynyloxy such as ethynyloxy and
propargyloxy; aryloxy such as phenoxy and bezyloxy; heteroaryloxy such as 2-
pyridyloxy; haloalkyl (preferably C1-6 haloalkyl) such as chloromethyl, fluoromethyl,
bromomethyl, dichloromethyl, difluoromethyl, dibromomethyl, trichloromethyl,
trifluoromethyl, bromodifluoromethyl, 1,1,1-trifluoroethyl, 1-chloroethyl, 2-chloroethyl,
1-bromoethyl, and pentafluoroethyl; haloalkoxy (preferably C1-6 haloalkoxy) such as

fluoromethoxy, chloromethoxy, bromomethoxy, difluoromethoxy, dichloromethoxy,
dibromomethoxy, trifluoromethoxy, trichloromethoxy, tribromomethoxy,
1,1,1-trifluoroethoxy, pentafluoroethoxy, and heptafluoron-propoxy; alkylthiocarbonyl
(preferably C1-6 alkylthiocarbonyl) such as methylthiocarbonyl, ethylthiocarbonyl,
n-propylthiocarbonyl, isopropylthiocarbonyl, n-butylthiocarbonyl, isobutylthiocarbonyl,
s-butylthiocarbonyl, and t-butylthiocarbonyl; alkylsulfonylamino (preferably C1-6
alkylsulfonylamino) such as methylsulfonylamino, ethylsulfonylamino,
n-propylsulfonylamino, isopropylsulfonylamino, n-butylsulfonylamino, and
t-butylsulfonylamino; arylsulfonylamino (preferably C6-12 arylsulfonylamino) such as
phenylsulfonylamino; heteroarylsulfonylamino (preferably C3-12
heteroarylsulfonylamino) such as piperazinylsulfonylamino; alkylcarbonylamino
(preferably C1-6 alkylcarbonylamino) such as methylcarbonylamino, ethylcarbonylamino,
n-propylcarbonylamino, and isopropylcarbonylamino; alkoxycarbonylamino (preferably
C1-6 alkoxylcarbonylamino) such as methoxycarbonylamino, ethoxycarbonylamino,
n-propoxycarbonylamino, and isopropoxycarbonylamino; haloalkylsulfonylamino
(preferably C1-6 haloalkylsulfonylamino) such as fluoromethylsulfonylamino,
chloromethylsulfonylamino, bromomethylsulfonylarnino, difluoromethylsulfonylamino,
dichloromethylsulfonylamino,
1,1 -difluoroethylsulfonylamino,trifluoromethylsulfonylamino,
1,1,1-trifluoroethylsulfonylamino and pentafluoroethylsulfonylamino;
bis(alkylsulfonyl)amino (preferably bis(C1-6 alkylsulfonylamino) such as
bis(methylsulfonyl)amino, bis(ethylsulfonyl)amino, (ethylsulfonyl) (methylsulfonyl)
amino, bis(n-propylsulfonyl)amino, bis(isopropylsulfonyl)amino,
bis(n-butylsulfonyl)amino, and bis(t-butylsulfonyl)amino; bis(haloalkylsulfonyl)amino
(preferably bis(C1-6 haloalkylsulfonylamino) such as bis(fluoromethylsulfonyl)amino,

bis(chloromethylsulfonyl)amino, bis(bromomethylsulfonyl)amino,
bis(difluoromethylsulfonyl)amino, bis(dichloromethylsulfonyl)amino,
bis( 1,1 -difluoroethylsulfonyl)amino, bis(trifluoromethylsulfonyl)amino,
bis(1, 1,1 -trifluoroethylsulfonyl)amino, and bis(pentafluoroethylsulfonyl)amino;
unsubstituted or substituted hydrazino such as hydrazino, N'-phenylhydrazino,
N'-methoxycarbonylhydrazino, N'-acetylhydrazino, and N'-methylhydrazino;
alkoxycarbonyl (preferably C1-6 alkoxycarbonyl) such as methoxycarbonyl,
ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl, n-butoxycarbonyl, and
t-butoxycarbonyl; aryl (preferably C6-12 aryl) such as phenyl, 1-naphthyl, and 2-naphthyl;
aralkyl (preferably C7-20 aralkyl) such as benzyl, and phenethyl; unsaturated 5-membered
heterocycle such as furan-2-yl, furan-3-yl, thiophen-2-yl, thiophen-3-yl, pyrrol-2-yl,
pyrrol-3-yl, oxazol-2-yl, oxazol-4-yl, oxazol-5-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl,
isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl,
imidazol-2-yl, imidazol-4-yl, imidazol-5-yl, pyrazol-3-yl, pyrazol-4-yl, pyrazol-5-yl,
l,3,4-oxadiazol-2-yl, l,3,4-thiadiazol-2-yl, l,2,3-triazol-4-yl, l,2,4-triazol-3-yl, and
l,2,4-triazol-5-yl; unsaturated 5-membered heterocycle alkyl such as
5-phenyl-5-trifluoromethyl-isoxazolin-3-yl, 2-furfurylmethyl, 3-thienylmethyl, and
l-methyl-3-pyrazolomethyl; unsaturated 6-membered heterocycle such as pyridin-2-yl,
pyridin-3-yl, pyridin-4-yl, pyridazin-3-yl, pyridazin-4-yl, pyrazin-2-yl, pyrimidin-2-yl,
pyrimidin-4-yl, pyrimidin-5-yl, l,3,5-triazin-2-yl, and l,2,4-triazin-3-yl; unsaturated
6-membered heterocycle alkyl such as 2-pyridylmethyl, 3-pyridylmethyl,
6-chlor-3-pyridylmethyl, and 2-pyrimidylmethyl; sanitated heterocyclic group such as
tetrahydrofuran-2-yi, tetrahydrapyran-4-yl, piperidin-3-yl, pyrrolidin-2-yl, morpholino,
piperidino, and N-methylpiperazinyl; sanitated heterocyclic alkyl such as
2-tetrahydrafuranylmethyl, 3-piperazylmethyl, N-methyl-3-pyrrolidylmethyl, and

morpholinomethyl; N-unsubstituted- or N-substituted iminoalkyl such as
N-dimethylaminoiminomethyl, 1 -N-phenyliminoethyl, N-hydroxyiminomethyl, and
N-methoxyiminomethyl; N-unsubstituted- or N-substituted hydrazinocarbonyl such as
N'-methylhydrazinocarbonyl, N'-phenylhydrazinocarbonyl, and hydrazinocarbonyl;
N-unsubstituted- or N-substituted aminocarbonyl such as aminocarbonyl,
dimethylaminocarbonyl, and N-phenyl-N-methylaminocarbonyl; alkylthio such as
methylthio, ethylthio, and t-butylthio; alkenylthio such as vinylthio and allylthio;
alkynylthio such as ethynylthio and propargylthio; arylthio such as phenylthio, and
4-chlorophenylthio,; heteroarylthio such as 2- piperidylthio and 3-pyridazylthio;
aralkylthio such as benzylthio and phenethylthio; alkylsulfonyl such as methylsulfonyl,
ethylsulfonyl, and t-butylsulfonyl; alkenylsulfonyl such as allylsulfonyl; alkynylsulfonyl
such as propargylsulfonyl; arylsulfonyl such as phenylsulfonyl,; heteroarylsulfonyl such
as 2-pyridylsulfonyl and 3- pyridylsulfonyl; aralkylsulfonyl such as benzylsulfonyl and
phenethylsulfonyl; groups represented by the formulae (a) to (c) below;

[ In the formulae (a), (b), and (c), R6 and R7 each independently represents
hydrogen, unsubstituted or substituted hydrocarbon, unsubstituted or substituted
heterocyclic group, unsubstituted or substituted amino, hydrocarbonoxy, or

hydrocarbonthio; R 8and R11 each independently represents hydrogen, unsubstituted or
substituted hydrocarbon, unsubstituted or substituted heterocyclic group, or unsubstituted
or substituted amino; R9 represents hydrogen or unsubstituted or substituted
hydrocarbon; R10 represents hydrogen, unsubstituted or substituted hydrocarbon, or

unsubstituted or substituted heterocyclic group; Y and Z each independently represents
oxygen, or unsubstituted or substituted nitrogen; R6 and R7, R8 and R9, and R10 and R11
may bond to form rings and in that case, both two groups in the pair represent functional
groups, which may integrate to form a ring. Specific examples of hydrocarbons
commonly present in R6 to R11 include alkyl such as methyl, ethyl, isopropyl, n-propyl,
n-hexyl, and n-octyl; alkenyl such as vinyl, allyl, 1-propenyl, and 2-phenylethenyl;
alkynyl such as ethynyl and propargyl; and aromatic hydrocarbon such as phenyl,
1-naphthyl, and 9-anthracel. Specific examples of heterocyclic groups commonly

present in R6 , R7 , R8 , R10 , and R11 include unsaturated 5-membered heterocycle such as
furan-2-yl, furan-3-yl, thiophen-2-yl, thiophen-3-yl, pyrrol-2-yl, pyrrol-3-yl, oxazol-2-yl,
oxazol-4-yl, oxazol-5-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl, isoxazol-3-yl,
isoxazol-4-yl, isoxazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl,
imidazol-2-yl, imidazol-4-yl, imidazol-5-yl, pyrazol-3-yl, pyrazol-4-yl, pyrazol-5-yl,
l,3,4-oxadiazol-2-yl, l,3,4-thiadiazol-2-yl, l,2,3-triazol-4-yl, l,2,4-triazol-3-yl, and
l,2,4-triazol-5-yl; unsaturated 5-membered heterocycle alkyl such as
5-phenyl-5-trifluoromethyl-isoxazolin-3-yl, 2-furfurylmethyl, 3-thienylmethyl, and
l-methyl-3-pyrazolomethyl; unsaturated 6-membered heterocycle such as pyridn-2-yl,
pyridin-3-yl, pyridin-4-yl, pyridazin-3-yl, pyridazin-4-yl, pyrazin-2-yl, pyrimidin-2-yl,
pyrimidin-4-yl, pyrimidin-5-yl, l,3,5-triazin-2-yl, and 1,2,4-triazin-3-yl; unsaturated
6-membered heterocycle alkyl such as, 2-pyridylmethyl, 3-pyridylmethyl,
6-chlor-3-pyridylmethyl, and 2-pyrimidylmethyl; and saturated heterocycle such as
tetrahydrofuran-2-yl, tetrahydrapyran-4-yl, piperidin-3-yl, pyrrolidin-2-yl, morpholino,
piperidino, and N-methylpiperazinyl; sanitated heterocyclic alkyl group such as
2-tetrahydrofuranylmethyl, 3-piperazylmethyl, N-methyl-3-pyrrolidylmethyl, and
morpholinomethyl. Specific examples of hydrocarbonoxy and hydrocarbonthio

commonly present in R6 nad R7 include methoxy, ethoxy, isopropoxy, phenoxy,
benzyloxy, methylthio, ethylthio, phenylthio, and benzylthio. Specific examples of
substituents of functional groups present in R6 to R11 include the same as those shown as
specific examples of the substituents of Cy1. Y and Z each independently represent
oxygen, or unsubstituted or substituted nitrogen and specific examples of a substituent on
nitrogen include the same as those shown as specific examples of the substituents of Cy1.
Specific examples of the group represented by the formulae (a) to (c) include the
group represented by the formula below.

]C1-6 haloalkyl is particularly preferable. By associating two or more
substituents listed above by substituting one substituent onto another, the resulting
substituent can be used in a similar manner as a new substituent.
In formula (1), X represents oxygen; sulfur; unsubstituted or substituted
nitrogen; sulfinyl; or sulfonyl and oxygen is preferable. It should be noted that when
nitrogen is unsubstituted, hydrogen is bonded to nitrogen.
When X is substituted nitrogen, specific examples of substituents on nitrogen
include those similar to the specific examples of the substituents of Cy1.
Moreover, in formula (1), R1a and R2a, R1a and R4a, R2a and R3a or R3a and R4a
form saturated rings together and it is preferable that R1a and R a or R3a and R4a come

together to form a ring and the number of atoms at the cross-linking site of the piperidine
ring, which forms the saturated ring, is preferably 2 or 3.
In addition, elements which constitute the cross-linking site of the piperidine
ring of the saturated ring are not particularly limited as long as they are within a
chemically acceptable range and specific examples thereof include carbon, oxygen, sulfur,
nitrogen, or silicon and the saturated rings can be constituted by combining 2 or more of
these elements within a chemically acceptable range. Moreover, each atom can have
hydrogen or substituents within the chemically acceptable range thereon and R1a and R2a,
R1a and R4a, R a and R3a, or R3a and R4a may bind oxygen, sulfur, or nitrogen via a double
bond within a chemically acceptable range to form carbonyl, thiocarbonyl, imino, or the
like.
R1a, R1b, R2a, R2b, R3a, R3b, R4a, R4b, and R5 which do not form the
aforementioned saturated rings together each independently represents hydrogen, halogen,
unsubstituted or substituted amino, nitro, hydroxyl, or an organic group. The organic
group represents functional groups generally which contain carbon and the specific
examples thereof include cyano; formyl; alkyl; alkoxycarbonyl; alkoxy; haloalkyl;
haloalkoxy; alkylthiocarbonyl; alkylsulfonylamino; haloalkylsulfonylamino;
bis(alkylsulfonyl)amino; bis(haloalkylsulfonyl)amino; and aryl; or the like. As the
organic groups, alkyl; alkoxycarbonyl; and alkoxy are preferable and C1-6 alkyl; C1-6
alkoxycarbonyl; and C1-6 alkoxy are more preferable. Specific examples thereof include
the same as those shown as specific examples of the substituents of Cy1 .
Specific examples of a piperidine ring, which is constituted in formula (1),
include the structures represented by the formulae shown below.

Although specific examples of an aromatic ring of Cy2 include those similar to

the specific examples of Cy1, pyridazyl is preferable, and pyridazin-3-yl is more
preferable with a proviso that R1 a and R2a come together to form a saturated ring and Cy2
is an unsubstituted or substituted heteroaromatic ring when Cy1 is unsubstituted or
substituted phenyl. Moreover, Cy2 is a substituted pyridin-2-yl having one or more
cyano as a substituent when Cy1 is an unsubstituted or substituted phenyl and Cy2 is a
substituted pyridin-2-yl. Cy2 does not include unsubstituted pyridin-2-yl, when Cy1 is
an unsubstituted or substituted phenyl. The substituted pyridin-2-yl having one or more
cyano as a substituent means that the substituted pyridin-2-yl has only cyano as a
substituent or cyano and another substituent; as substituents.
Several pairs of isomers exist when R1a and R2a or R3a and R4a of the compound
(1) of the present invention come together to form a saturated ring. These isomers are
all included in the present invention. It should be noted that the same also applies when
R1a and R4a or R2a and R3a come together to form a saturated ring. Moreover, the same
applies to the compounds (2) of the present invention which will be described later.

The following compounds can be shown as examples of N-oxides of the
compounds represented by the formula (1); i.e. the compounds represented by the
formula (1) where nitrogen represented by X or nitrogen in the cyclic amine parts of the
tropane ring, isotropane ring, or the like is oxidized.
Moreover, examples of salts of the compounds represented by the formula (1)
include salts of inorganic acids such as hydrochloride salts, nitrate salts, sulfate salts, and
phosphate salts; and salts of organic acids such as acetate salts, lactate salts, propionate
salts, and benzoate salts.
X0 in the formula (2) corresponds to X in the formula (1) except that X0 does not
include nitrogen and R1a to R5 in the formula (2) are the same as R1a to R5 in the formula
(1) except that only R3a and R4a form a saturated ring together.

R represents hydrogen; alkoxycarbonyl such as 1- chloroethoxycarbonyl,
methoxymethoxycarbonyl, 1-ethoxyethoxycarbonyl, 1,1,1-trichloroethoxycarbonyl, and
others similar to those examples of the specific examples of the substituents of Cy1 such
as alkoxycarbonyl (preferably C1-6 alkoxycarbonyl); alkylcarbonyl (preferably C1-6
alkylcarbonyl) such as methylcarbonyl, ethylcarbonyl, n-propylcarbonyl,
isopropylcarbonyl, n-butylcarbonyl, isobutylcarbonyl, s-butylcarbonyl, and
t-butylcarbonyl; or 1-alkoxyalkyl (preferably 1-C1-6 alkoxyalkyl) such as methoxymethyl,
ethoxymethyl, and 1-ethoxyethyl.
2) Production method
(1) When X is oxygen or optionally oxidized sulfur
The compound (1) can be obtained by, for example, obtaining the compound represented
by the formula (5) by eliminating protecting group such as methyl and benzyl from the
compound represented by the formula (4) (hereinafter referred to as the "compound (4))
as shown below and coupling the compound (5) with the compound represented by the
formula (6) by the general method.

(In the formula, Cy1, Cy2, X, R1a, R1b, R2a, R2b, R3a, R3b, R4a, R4b, and R5 are the same as
above. X' represents a leaving group such as halogen and R' represents a protecting
group.)
The compound (4), which is an intermediate during the production, can be
produced by general reaction conditions as described next.

(In the formula, Cy1, X, R1a, R1b, R2a, R2b, R3a, R3b, R4a, R4b, R5 and R' are the same as
above. X1 and X2 each independently represents hydroxyl or mercapto and X3
represents a leaving group such as halogen.)
Moreover, the compound (1) can also be produced by the general method shown
below.

(In the formula, Cy1, Cy2, X, R1a, R1b, R2a, R2b, R3a, R3b, R4a, R4b, and R5 are the same as

above. X4 represents a leaving group such as halogen and X5 represents hydroxyl or
mercapto.)
The compound (11), which will be a raw material, can also be produced by the
general method shown in the below reaction formula (IV).

(In the formula, Cy2, X4, R1a, Rlb, R2a, R2b, R3a, R3b, R4a, R4b, and R5 are the same as
abdve. X6 represents a leaving group such as halogen.)
(2) When X is optionally substituted nitrogen
The compounds represented by the formula (17) can be produced by reacting the
compounds represented by the formula (15) with the compounds represented by the
formula (16) by the general method as shown in the below reaction formula (V).

(In the formula, Cy1, Cy2, R1a, R1b, R2a, R2b, R3a, R3b, R4a, and R4b are the same as above.
R" represents a substituent on nitrogen such as hydrogen, trifluoroacetyl, or
trifluoromethylsulfonyl.)
The compound (17), which is a compound of the present invention, can also be
produced by coupling the compound (15) and the compound represented by the formula

(18) by the general method as shown in the below reaction formula (VI).

(In the formula, Cy1, Cy2, R1a, Rlb, R2a, R2b, R3a, R3b, R4a, R4a, R5, and R" are the same as
above. X7 represents a leaving group such as halogen and sulfonyloxy.)
The compound (17), which is a compound of the present invention, can also be
produced by coupling the compound (19) and the compound represented by the formula
(20) by the general method as shown in the below reaction formula (VII).

(In the formula, Cy1, Cy2, X7, R1a, R1b, R2a, R2b, R3a, R3b, R4a, R4b, R5, and R" are the
same as above.)
3) Agents for pest control represented by formula (3)
The agents for pest control of the present invention are characterized by having
the compounds represented by the formula (3), salts thereof or N-oxides thereof, as active
ingredient.
The present invention relates to agents for pest control which contain the
compounds represented by the formula (3), salts thereof or N-oxides thereof, as active

ingredients.
In the formula (3), Cy11, Cy21, X11, and R11a to R51 are the same as corresponding
Cy1, Cy2, X, and R1a to R5 in the formula (1), respectively, except that there is no proviso
regarding Cy11 and Cy21 .
Since the compounds of the present invention (the compounds represented by
the formula (1), salts thereof, or N-oxides thereof) have adulticidal, nymphicidal,
larvicidal, or ovicidal activities, they can be used for controlling crop-damaging insect,
acarid, sanitary insects, stored grain pest insects, clothes pests, household pests, or the
like. Specific organisms to be the target of control include the following.
Preferably, pests which belong to the order of Lepidoptera such as Spodoptera
litura, Mamestra brassicae, Agrotis ipsilon, green caterpillars, Autographa nigrisigna,
Plutella xylostella, Adoxophyes honmai, Homona magnanima, Carposina sasakii,
Grapholita molesta, Phyllocnistis citrella, Caloptilia theivora, Phyllonorycter
ringoniella, Lymantria dispar, Euproctis pseudoconspersa, Chilo suppressalis,
Cnaphalocrocis medinalis, Ostrinia nubilasis, Hyphantria cunea, Cadra cautella, genus
Heliothis, genus Helicoverpa, genus Agrothis, Tinea translucens, Cydia pomonella, and
Pectinophora gossypiella;
pests which belong to the order of Hemiptera such as Myzus persicae, Aphis
gossypii, Lipaphis erysimi, Rhopalosiphum padi, Riptortus clavatus, Nezara antennata,
Unaspis yanonensis, Pseudococcus comstocki, Trialeurodes vaporariorum, Bemisia
tabaci, Bemisia argentifolii, Psylla pyrisuga, Stephanitis nashi, Nilaparuata lugens,
Laodelphax stratella, Sogatellafurcifera, and Nephotettix cincticeps;
pests which belong to the order of Coleoptera such as Phyllotreta striolata,
Aulacophorafemoralis, Leptinotarsa decemlineata, Lissorhoptrus oryzophilus, Sitophilis
zeamais, Callosobruchus chinensis, Popillia japonica, Anomala rufocuprea, genus

Diabrotica, Lasioderma serricorne, Lyctus brunneus, Monochamus alternates,
Anoplophora malasiaca, genus Agriotis, Epilachna vigintioctopunctata, Tenebroides
mauritanicus, and Anthonomus grandis;
pests which belong to the order of Diptera such as Musca domestica, Calliphora
lata, Boettcherisca peregrine, Zeugodacus cucurbitae, Bactrocera dorsalis, Delia platura,
Agromyza oryzae, Drosophila melanogaster, Stomoxys calcitrans, Culex
tritaeniorhynchus, Aedes aegypti, and Anopheles sinensis;
pests which belong to the order of Thysanoptera such as Thrips palmi and
Scirtothrips dorsalis;
pests which belong to the order of Hymenoptera such as Monomorium
pharaonis, Vespa simillima xanthoptera, and Athalia rosae ruficornis;
pests which belong to the order of Orthoptera such as Locusta migratoria,
Blattella germanica, Periplaneta americana, and Periplanetafuliginosa;
pests which belong to the order oflsoptera such as Coptotermes formosanus and
Reticulitermes speratus speratus;
pests which belong to the order of Siphonaptera such as Pulex irritans and
Ctenocephalides felis felis;
pests which belong to the order of Phthiraptera such as Pediculus humanus;
Acarina such as Tetranychus urticae, Tetranychus cinnabarinus, Tetranychus kanzawai,
Panonychus citri, Panonychus ulmi, Aculopspelekassi, Aculus schlechtendali,
Polyphagotarsonemus latus, genus Brevipalpus, genus Eotetranichus, Rhizoglyphus
robini, Tyrophagus putrescentiae, Dermatophagoides farinae, Boophilus microplus, and
Haemaphysalis longicornis; and
plant parasitic nematodes such as Meloidogyne incognita, Pratylenchus spp.,
Heterodera glycines, Aphelenchoides besseyi, and Bursaphelenchus xylophilus.

Pests to which the present invention is preferably applied are pests which belong
to the order of Lepidoptera, pests which belong to the order of Hemiptera, Acarina, pests
which belong to the order of Thysanoptera, and pests which belong to the order of
Coleoptera, and particularly preferably Acarina.
Moreover, drugs which are also effective for pests or Acarnia that are of
resistant lineage are desired because in recent years, resistance to organophosphorus
pesticides, carbamate pesticides, or acaricides developed among many pests such as
Plutella xylostella, Delphacidae, Deltocephalidae, and Aphididae has caused problems
because of insufficient effects of these drugs. The compounds of the present invention
are drugs having excellent insecticidal and acaricidal effects not only on those of
sensitive lineages but also on pests of lineages resistant to organophosphorus pesticides,
carbamate pesticides, and pyrethroid pesticides, and on Acarnia of lineages resistant to
acaricides.
Additionally, the compounds of the present invention are drugs that show less
herbicide injuries, have lower toxicity to fish and warm-blooded animals, and higher
safety.
The compounds of the present invention can also be used as an antifoulant to
prevent aquatic organisms attaching to objects which contact water such as ship bottoms
(or hulls, alternatively) and fishing nets.
Some of the compounds of the present invention exhibit germicidal activities,
herbicidal activities, or plant-growth regulating activities. Moreover, some
intermediates of the compounds of the present invention, which are represented by the
formula (1) or (3), exhibit insecticidal/acaricidal activities.
The agents for pest control of the present invention have the compounds of the
present invention, which are represented by the formula (1) or (3), as active ingredients

and the agents can be used either singularly or by mixing two or more thereof. The
compounds of the present invention can be used as they are without adding any other
components. However, when used practically, they are normally further mixed with
solid, liquid, or gaseous carriers, or are impregnated in substrates such as porous ceramic
plates and nonwoven fabrics, and by adding surfactants and/or other adjuvants where
necessary, used as formulations in the form which general agrochemicals may adopt, that
is, wettable powder, granule, dusting powder, emulsion, water-soluble powder,
suspending agent, granulated wettable powder, floable, aerosol, transpiration agent by
heating, fumigant, poison bait, microcapsule, or the like.
As additives and carriers, vegetable powders such as soy flour and wheat flour;
fine mineral powder such as diatomaceous earth, apatite, gypsum, talc, bentonite,
pyrophyllite, and clay; and organic and inorganic compounds such as sodium benzoate,
urea, and sodium sulfate are used when solid formulation is required. When liquid form
of formulation is required, petroleum fractions such as kerosene, xylene, and solvent
naphtha, and cyclohexane, cyclohexanone, dimethylformamide, dimethyl sulfoxide,
alcohol, acetone, methyl isobutyl ketone, mineral oil, vegetable oil, water, or the like are
used as a solvent. As gaseous carriers used in propellant, butane (gas), LPG, dimethyl
ether, and carbon dioxide gas can be used.
As a substrate of poison bait, bait components such as grain powder, vegetable
oil, sugar, and crystalline cellulose; antioxidants such as dibutylhydroxytoluene and
nordihydroguaiaretic acid; preservatives such as dehydroacetic acid; agents for
preventing accidental ingestion by children or pets such as capsicum powder; and
pest-insect attracting scents such as cheese scents and onion scents can be used.
Additionally, in order to achieve homogenous and stable forms in these
formulations, it is also possible to add surfactants if necessary. Although surfactants are

not particularly limited, examples thereof include, for instance, nonionic surfactants such
as alkyl ether where polyoxyethylene is added, higher fatty acid ester where
polyoxyethylene is added, sorbitan higher fatty acid ester where polyoxyethylene is
added, and tristyryl phenyl ether where polyoxyethylene is added; sulfate ester salt of
alkyl phenyl ether where polyoxyethylene is added, alkyl naphthalene sulfonate salt,
polycarboxylate salt, lignin sulfonate salt, formaldehyde condensate of alkyl naphthalene
sulfonate, and isobutylene-maleic anhydride copolymer.
When the compounds of the present invention are used as agents for pest control
in agriculture, the amount of active ingredient in the formulation is 0.01 to 90 weight%
and particularly preferably 0.05 to 85 weight% and wettable powder, emulsion,
suspending agents, floable agents, water-soluble powder, granulated wettable powder
which are diluted to predetermined concentrations with water, and dusting powder and
granules as they are, can be applied onto plants or soil.
In addition, when the compounds of the present invention are used as agents for
pest control in quarantine purposes, emulsion, wettable powder, floable agents, and the
like are applied by diluting to predetermined concentrations with water and oil solution,
and aerosol, poison bait, anti-acarid sheet, and the like can be applied as they are.
When the compounds of the present invention are used as agents for pest control
in controlling ectoparasites of livestock such as cattle and pigs or of pets such as dogs
and cats, formulations using the compounds of the present invention are used in known
methods in the field of veterinary medicine. As such methods, examples thereof
include a method for administering in forms such as tablets, capsules, immersion liquid,
feedstuff mix, suppository, and injection (intramuscular, subcutaneous, intravenous,
intraperitoneal, or the like) when systemic control is required and a method for
administering by spraying, pouring-on, or spotting-on oily- or aqueous liquid

formulations or a method for mounting objects, which are resin formulations shaped into
collars, ear tags, or the like, when non-systemic control is required. In this case, the
proportion can be normally used where 0.01 to 1000 mg of the compounds of the present
invention are applied per 1 kg of host animal.
It should be noted that although the compounds of the present invention are,
needless to say, sufficiently effective even when used solely, they can also be used by
mixing or combining with one or more of other agents for pest control, germicides,
insecticides/acaricides, herbicides, plant growth regulators, synergists, fertilizers, soil
conditioners, animal feed, or the like.
Representative examples of active ingredients of germicides, acaricides, plant
growth regulators, or the like which can be used by mixing or combining with the
compounds of the present invention are shown below.
Germicides:
captan, folpet, thiuram, ziram, zineb, maneb, mancozeb, propineb,
polycarbamate, chlorothalonin, quintozene, captafol, iprodione, procymidone,
fluoroimide, mepronil, flutolanil, pencycuron, oxycarboxin, fosetyl-aluminum,
propamocarb, triadimefon, triadimenol, propiconazole, diclobutrazol, bitertanol,
hexaconazole, myclobutanil, flusilazole, etaconazole, fluotrimazole, fiutriafen,
penconazole, diniconazole, cyproconazole, fenarimol, triflumizole, prochloraz, imazalil,
pefurazoate, tridemorph, fenpropimorph, triforine, buthiobate, pyrifenox, anirazine,
polyoxins, metalaxyl, oxadixyl, furalaxyl, isoprothiolane, probenazole, pyrrolnitrin,
blasticidin S, kasugamycin, validamycin, dihydrostreptomycin sulfate, benomyl,
carbendazim, thiophanate-methyl, hymexazol, basic copper chloride, basic copper sulfate,
fentinacetate, triphenyltin hydroxide, diethofencarb, chinomethionat, binapacryl, lecithin,
baking soda, dithianon, dinocap, fenaminosulf, diclomezine, guazatine, dodine, IBP,

edifenphos, mepanipyrim, fermzone, trichlamide, methasulfocarb, fluazinam,
ethoquinolac, dimethomorph, pyroquilon, tecloftalam, phthalide, phenazine oxide,
thiabendazole, tricyclazole, vinclozolin, cymoxanil, cyclobutanil, guazatine,
propamocarb hydrochloride, oxolinic acid, cyflufenamid, iminoctadine, kresoxim-methyl,
triazine, fenhexamid, cyazofamid, cyprodinil, prothioconazole, fenbuconazole,
trifloxystrobin, azoxystrobin, hexaconazole, imibenconazole, tebuconazole,
difenoconazole, and carpropamid;
Insecticides/acaricides:
organophosphorus and carbamate pesticides:
fenthion, fenitrothion, diazinon, chlorpyrifos, ESP, vamidothion, phenthoate,
dimethoate, formothion, malathion, trichlorphon, thiometon, phosmet, dichlorvos,
acephate, EPBP, methyl parathion, oxydemeton methyl, ethion, salithion, cyanophos,
isoxathion, pyridafenthion, phosalone, methidathion, sulprofos, chlorfenvinphos,
tetrachlorvinphos, dimethylvinphos, propaphos, isofenphos, ethylthiometon, profenofos,
pyraclofos, monocrotophos, azinphos-methyl, aldicarb, methomyl, thiodicarb, carbofuran,
carbosulfan, benfuracarb, furathiocarb, propoxur, BPMC, MTMC, MIPC, carbaryl,
pirimicarb, ethiofencarb, fenoxycarb, cartap, thiocyclam, bensultap, and the like;
pyrethroid pesticides:
permethrin, cypermethrin, deltamethrin, fenvalerate, fenpropathrin, pyrethrin,
allethrin, tetramethrin, resmethrin, dimethrin, propathrin, phenothrin, prothrin, fluvalinate,
cyfluthrin, cyhalothrin, flucythrinate, etofenprox, cycloprothrin, tralomethrin, silafluofen,
and acrinathrin;
benzoylurea and other pesticides:
diflubenzuron, chlorfluazuron, hexaflumuron, triflumuron, flufenoxuron,
flucycloxuron, buprofezin, pyriproxyfen, methoprene, benzoepin, diafenthiuron,

imidacloprid, fipronil, nicotine sulfate, rotenone, metaldehyde, acetamiprid, chlorfenapyr,
nitenpyram, thiacloprid, clothianidin, thiamethoxam, dinotefuran, indoxacarb,
pymetrozine, spinosad, emamectin, pyridalyl, tebufenozide, chromafenozide,
methoxyfenozide, tolfenpyrad, machine oil, microbial pesticides such as BT and
entomopathogenic viruses;
nematicides:
fenamiphos, fosthiazate, cadusafos, and the like;
acaricides:
chlorobenzilate, phenisobromolate, dicofol, amitraz, BPPS, benzomate,
hexythiazox, fenbutatin oxide, polynactin, chinomethionat, CPCBS, tetradifon,
avermectin, milbemectin, clofentezine, cyhexatin, pyridaben, fenpyroximate,
tebufenpyrad, pyrimidifen, fenothiocarb, dienochlor, fluacrypyrim, acequinocyl,
bifenazate, etoxazole, spirodiclofen, fenazaquin, and the like;
plant growth regulators:
gibberellins (for example, gibberellin A3, gibberellin A4, or gibberellin A7),
IAA, NAA.
[Example]
Next, the present invention will be described in further detail by using Examples.
However, the present invention is not limited to the Examples below in any aspects.
Production Example 1
(Example 1)
Production of
3a-(5-trifluoromethyl-2-pyridyloxy)-8-(5-trifluoromethyl-pyridin-2-yl)-8-azabicyclo[3.2.
1] octane

23.3 g of 2,2,2-trichloroethyl chloroformate ester was added to 150 ml of the
benzene suspension containing 14.1 g of tropine and 1.4 g of potassium carbonate at
room temperature and the entire mixture was refluxed for 3.5 hours. After being cooled
to room temperature, the reaction mixture was poured into water and extracted with ethyl
acetate. The organic layer was washed with saline and dried with anhydrous
magnesium sulfate. 30.1 g of an oily carbonate (A) was obtained by evaporating the
solvents under reduced pressure and this carbonate was used directly in the next reaction.
Next, 65 g of zinc powder was added to 250 ml of the acetate solution of this
carbonate (A). After being stirred for 5 minutes, the mixture was heated at 80°C for 1
hour. After being cooled to room temperature, the mixture was subjected to celite
filtration. 15.5 g of a crude product of the compound (B) was obtained by
vacuum-concentrating the filtrate.
150 ml of acetonitrile suspension containing 5.64 g of the crude product of the
compound (B) obtained as above, 41.5 g of potassium carbonate, and 8.2 g of
2-chloro-5-trifluoromethylpyridine was refluxed for 3.5 hours. After being cooled to
room temperature, the reaction mixture was poured into water and extracted with ethyl
acetate. The organic layer was washed with saline and dried with anhydrous

magnesium sulfate. 3.5 g of the compound (C) was obtained as crystals by evaporating
the solvents under reduced pressure.
32 mg of 60% sodium hydride was added to 3 ml of dimethylformamide (DMF)
solution containing 0.21 g of the compound (C) with ice-cooling and the entire mixture
was stirred for 40 minutes. Subsequently, 0.17 g of 2-chloro-5-trifluoromethylpyridine
was added to this mixture and the resulting mixture was heated to 100°C and was stirred
overnight with heating. After cooling to room temperature, the reaction mixture was
poured into ice-cold water and extracted with ethyl acetate. After being washed with
water and dried with anhydrous magnesiunvsulfate, the organic layer was filtered and
then vacuum-concentrated. The residue was purified by column chromatography
(developing solution: mixed solvent of n-hexane and ethyl acetate) to obtain 0.06 g of the
target compound. Melting temperature: 104-105°C
1H-NMRCCDCl3, δppm):1.25(s, 1H), 1.55(s, 1H), 1.95-2.33(m, 6H), 4.58(brs, 2H), 5.37(t,
1H), 6.55(d, 1H), 6.80(d, 1H), 7.61(dd, 1H), 7.78(dd, 1H), 8.41(s, 2H)
(Example 2)
Production of
3α- [2-n-propoxy-4-(trifluoromethyl)phenoxy] -8- [3-fluoro-4-(trifluoromethyl)phenyl] -8-a
zabicyclo[3.2.1]octane

0.44 g of 60% sodium hydride was added to 15 ml of DMF solution containing
1.8 g of 4-fluoro-3-hydroxybenzotrifluoride and after stirring the entire mixture for 20
minutes, 3 ml of DMF solution containing 1.7 g of 1-iodopropane was added thereto and
the resulting solution was further stirred for 4 hours at room temperature. 1.4 g of
tropine and 0.43 g of 60% sodium hydride were added to the obtained mixture at room
temperature and the resulting solution was heated to 100°C and was stirred overnight
with heating. After cooling to room temperature, the reaction mixture was poured into
ice-cold water and extracted with ethyl acetate. After being washed with water and
dried with anhydrous magnesium sulfate, the organic layer was filtered and then
vacuum-concentrated. The residue was purified by column chromatography to obtain
1.1 g of an oily compound (D).
4 ml of methylene chloride solution containing 0.83 g of 1-chloroethyl
chloroformate ester was added to 6 ml of methylene chloride solution containing 1.0 g of
the compound (D) at room temperature and the entire mixture was refluxed overnight.

The reaction mixture was diluted with methylene chloride, washed with saturated sodium
bicarbonate water and then with saline, and dried with anhydrous magnesium sulfate. A
crude carbonate (E) was obtained by evaporating the solvents under reduced pressure and
was used directly in the next reaction.
6 ml of methanol was added to the compound (E) and the mixture was refluxed
for 2.5 hours. The resulting mixture was vacuum-concentrated to obtain a crude
compound (F). The crude compound (F) was alkali-treated to obtain a free amine and
this amine was used directly in the next reaction.
0.4 g of t-butoxysodium, 13.7 mg of Pd2(dba)3, and 17.7 mg of
2-(dicyclohexylphosphino)-2'-(N,N-dimethylamino)biphenyl were added to 11 ml of
toluene solution containing 1 g of the free form of the compound (F) obtained above and
0.73 g of 4-bromo-2-fluorobenzotrifluoride and the entire mixture was refluxed overnight
under nitrogen atmosphere. After cooling to room temperature, the reaction mixture
was poured into water and extracted with ethyl acetate. After being washed with water
and dried with anhydrous magnesium sulfate, the organic layer was filtered and then
vacuum-concentrated. The residue was purified by column chromatography
(developing solution: mixed solvent of n-hexane and ethyl acetate) to obtain 0.54 g of the
target compound. Viscous oil
1H-NMR(CDCl3, δppm):1.08(t, 3H), 1.81-1.97(m, 4H), 2.04-2.23(m, 4H), 2.45(q,2H),
3.97(t, 2H), 4.19(brs, 2H), 4.57(brt, 1H), 6.44-6.51(m, 2H), 6.76(d, 1H), 7.13(s, 1H),
7.16(d, 1H),7.38(t, 1H)
(Example 3)
Production of
3a-[5-(trifluoromethyl)-2-pyridyloxy]-8-(2-formyl-4-(trifluoromethyl)phenyl)-8-azabicyc
lo[3.2.1]octane

A total of 5.8 g of 60% sodium hydride was added at multiple steps to 240 ml of DMF
solution containing 17.6 g of tropine and 21.6 g of 2-chloro-5-trifluoromethylpyridine at
80°C and the entire mixture was stirred for 2 hours at the same temperature. After
cooling to room temperature, the reaction mixture was poured into ice-cold water and
extracted with ethyl acetate. After being washed with water and dried with anhydrous
magnesium sulfate, the organic layer was filtered and then vacuum-concentrated. The
residue was purified by column chromatography (NH-gel; DM-1020 was used;
developing solution: mixed solvent of n-hexane and ethyl acetate) to obtain 25 g of the
compound (G).
26 g of 2,2,2-trichloroethyl chloroformate ester was added to 150 ml of the
benzene suspension containing 25 g of the compound (G) and 1.33 g of potassium
carbonate at room temperature and the mixture was refluxed for 1 hour with heating.
After being cooled to room temperature, the mixture was poured into water and extracted
with ethyl acetate. The organic layer was washed with saline and dried with anhydrous
magnesium sulfate. A solid carbonate was obtained by evaporating the solvents under
reduced pressure and this carbonate was used directly in the next reaction.
42 g of zinc powder was added to 300 ml of the acetate solution containing the
carbonate obtained above and the entire mixture was stirred for 1 hour with heating at

100°C. After being cooled to room temperature, the mixture was subjected to celite
filtration and after adding chloroform and water to the resulting filtrate, the organic layer
was separated. The aqueous layer was made weakly alkaline, extracted with chloroform,
and mixed with the separated organic layer. The mixture was washed with water, dried
with anhydrous magnesium sulfate, and then the solvents thereof were evaporated under
reduced pressure to obtain 14.4 g of a crude compound (H).
30 ml of acetonitrile suspension containing 2 g of the compound (H), 3.04 g of
potassium carbonate, and 1.41 g of 2-fluoro-5-trifluoromethylbenzaldehyde was refluxed
for 3.5 hours. After being cooled to room temperature, the reaction mixture was poured
into water and extracted with ethyl acetate. The organic layer was washed with saline
and dried with anhydrous magnesium sulfate. 2.77 g of the target compound was
obtained by evaporating the solvents under reduced pressure and purifying the residue
with silica gel column chromatography (developing solution: mixed solvent of n-hexane
and ethyl acetate). Melting temperature: 122-123°C
1H-NMR(CDCl3, δppm):1.99-2.05(m, 2H), 2.12(s, 1H), 2.17(s, 1H), 2.21-2.28(m, 2H),
2.41(t, 1H), 2.45(t, 1H), 4.04(brs, 2H), 5.50(t, 1H), 6.79(d, 1H), 7.05(d, 1H), 7.61(d, 1H),
7.79(dd, 1H), 8.02(s, 1H), 8.44(s, 1H), 10.19(s, 1H)
(Example 4)
Production of
3α- [2-isopropoxy carbonyl-4-(trifluoromethyl)phenoxy] - 8 - [6-cyano -pyridazine-3 -yl] -8 -az
abicyclo[3.2. l]octane
Step 1
Production of
3a-[2-isopropoxycarbonyl-4-(trifluoromethyl)phenoxy]-8-azabicyclo[3.2.1]octane(J)

0.56 g of 60% sodium hydride was added to 20 ml of DMF solution containing
1.0 g of tropine. 1.76 g of 4-fluoro-3-isopropoxycarbonylbenzotrifluoride was added
dropwise to this mixture. After being stirred overnight at room temperature, the
mixture was poured into water and extracted with ethyl acetate. After being washed
with water and dried with anhydrous magnesium sulfate, the organic layer was filtered
and the resulting filtrate was evaporated under reduced pressure to obtain 1.15 g of a
crude compound (I). The crude compound (I) was directly used in the next reaction.
Note that 4-fluoro-3-isopropoxycarbonylbenzotrifluoride was obtained by
isopropyl-esterifying the commercially available 2-fluoro-5-trifluoromethylbenzoate.
0.05 g of potassium carbonate and 0.52 g of 1-chloroethyl chloroformate ester
were added to 20 ml of benzene solution containing 1.23 g of the crude compound (I)
and the mixture was refluxed for 5 hours with heating. After being cooled to room
temperature, the mixture was poured into water and extracted with ethyl acetate. The
organic layer was washed with saline and dried with anhydrous magnesium sulfate.
The concentrate obtained by evaporating the solvents under reduced pressure was
dissolved in 20 ml of methanol and the entire solution was stirred overnight at room
temperature. 1.0 g of a crude compound (J) was obtained by evaporating the solvents
under reduced pressure and this compound was used directly in the next reaction.

Step 2
Production of
3a-[2-isopropoxycarbonyl-4-(trifluoromethyl)phenoxy]-8-[6-cyano-pyridazin-3-yl]-8-aza
bicyclo[3.2.1 ]octane

30 ml of acetonitrile suspension containing 1.0 g of the crude compound (J),
1.16 g of potassium carbonate, and 0.39 g of 3-chloro-6-cyanopyridazine was refluxed
for 3 hours with heating. After being cooled to room temperature, the mixture was
poured into water and extracted with ethyl acetate. The organic layer was washed with
saline and dried with anhydrous magnesium sulfate. The concentrate obtained by
evaporating the solvents under reduced pressure was purified with silica gel column
chromatography (eluant: mixed solvent of n-hexane and ethyl acetate) to obtain 0.18 g of
crystals. Furthermore, these crystals were washed with diethylether to obtain 0.04 g of
the target compound. Melting temperature: 219-221 °C
1H-NMR(CDCl3, δppm):1.39(d, 6H), 2.03-2.37(m, 6H), 2.48-2.5 l(m, 2H), 4.69(brs, 3H),
5.22-5.30(m, 1H), 6.75(d, 1H), 6.85(d, 1H), 7.44(d, 1H), 7.68(d, 1H), 7.98(s, 1H)
(Example 5)
Production of
8β- [2-propoxy-4-(trifluoromethyl)phenoxy] -3 - [6-(trifluoromethyl)-pyridin-3 -yl]-3-azabic
yclo[3.2.1]octane
Step 1
Production of

N-benzyl-8β- [2-propoxy-4-(trifluoromethyl)phenoxy]-3-azabicyclo[3.2.1]octane (L)

0.12 g of 60% sodium hydride was added to 4 ml of DMF solution containing
0.50 g of 4-fluoro-3-hydroxybenzotrifluoride with ice-cooling. After stirring the
mixture at room temperature for 30 minutes, 0.51 g of 1 -iodopropane was added thereto.
The mixture was heated to 90°C and the mixture was stirred for 30 minutes. 4 ml of
DMF solution containing 0.41 g of the compound (K) and 0.09 g of 60% sodium hydride
were added to the mixture at room temperature and after being stirred for 15 minutes, the
resulting mixture was heated to 100°C and stirred for 2 hours. After being cooled to
room temperature, the mixture was poured into water and extracted with ethyl acetate.
After being washed with water and dried with anhydrous magnesium sulfate, the organic
layer was filtered and then vacuum-concentrated. The concentrate was purified by
silica gel column chromatography (eluant: mixed solvent of n-hexane and ethyl acetate)
to obtain 0.75 g of the compound (L) as an oily matter.
1H-NMR(CDCl3, δppm):1.05(t, 3H), 1.75-1.91(m, 6H), 2.19(d, 2H), 2.34(brs, 2H),
2.74(d, 2H), 3.51(s, 2H), 3.96(t, 2H), 4.33(s, 1H), 6.94(d, 1H), 7.07(s, 1H), 7.13(d, 1H),
7.20-7.34(m, 5H)
Step 2
Production of
8P-[2-propoxy-4-(trifluoromethyl)phenoxy]-3-[6-(trifluoromethyl)-pyridin-3-yl]-3-azabic
yclo[3.2.1]octane

0.13 g of 10% palladium-carbon was added to 20 ml of the ethanol solution
containing 0.66 g of the compound (L). The suspension was stirred overnight at room
temperature under hydrogen atmosphere (1.01 x 105 Pa). The reaction solution was
subjected to celite filtration and the resulting filtrate was evaporated under reduced
pressure to obtain 0.55 g of a crude compound (M).
3-bromo-6-(trifluoromethyl)pyridine was derived from the commercially
available 3-amino-6-(trifluoromethyl)pyridine by the usual Sandmeyer reaction.
0.16 g of 3-bromo-6-(trifluoromethyl)pyridine, 0.1 g of t-butoxy sodium, 6.47
mg of Pd2(dba)3, and 8.34 mg of
2-(dicyclohexylphosphino)-2'-(N,N-dimethylamino)biphenyl were added to 2 ml of the
toluene solution containing 0.23 g of the crude compound (M) and the mixture was
refluxed with heating overnight under nitrogen atmosphere. After cooling, the reaction
mixture was poured into water and extracted with ethyl acetate. After being washed
with water and dried with anhydrous magnesium sulfate, the organic layer was filtered
and then vacuum-concentrated. The concentrate was purified by silica gel column
chromatography (eluant: mixed solvent of n-hexane and ethyl acetate) to obtain 0.1 g of
the target compound. Melting temperature: 79-80°C
1H-NMR(CDCl3, δppm):1.07(t, 3H), 1.67-1.71(m, 2H), 1.80-1.92 (m, 2H), 2.09-2.12 (m,

2H), 2.62(brs, 2H), 3.07(d, 2H), 3.69(dd, 2H), 3.98(t, 2H), 4.60(s, 1H), 7.01(d, 1H),
7.09-7.19(m, 3H), 7.50(d, 1H), 8.28(d, 1H)
(Example 6)
Production of
8P42-isopropylideneaminooxy-4-(trifluoromethyl)phenoxy]-3-(5-trifluoromethyl-l,3,4-t
hiadiazol-2-yl)-3-azabicyclo[3.2.1]octane
Stepl
Production of
3-(5-trifluoromethyl-1,3,4-thiadiazol-2-yl)-3-azabicyclo[3.2.1]octan-8p-ol

2.6 g of 10% palladium-carbon was added to 100 ml of the ethanol solution
containing 4.32 g of the compound (K). The suspension was heated to 50°C and stirred
for 2 hours under hydrogen atmosphere and further stirred overnight at room temperature.
The reaction solution was subjected to celite filtration and the resulting filtrate was
evaporated under reduced pressure to obtain 2.5 g of the crude compound (N).
2-bromo-5-(trifluoromethyl)thiadiazole was derived from the commercially
available 2-amino-5-(trifluoromethyl)thiadiazole by the usual Sandmeyer reaction.
0.37 g of 2-bromo-5-(trifluoromethyl)-l,3,4-thiadiazole, 0.65 g of potassium
carbonate, and 10 mg of tetra-n-butylammoniumbromide were added to 6 ml of the
acetonitrile solution containing 0.2 g of the crude compound (N) and the mixture was
refluxed with heating overnight. After being cooled to room temperature, the mixture
was poured into water and extracted with ethyl acetate. After being washed with water

and dried with anhydrous magnesium sulfate, the organic layer was filtered and then
vacuum-concentrated. The concentrate was purified by silica gel column
chromatography (eluant: mixed solvent of n-hexane and ethyl acetate) to obtain 0.25 g of
the target compound.
Step 2
Production of
8 β- [2-hydroxy-4-(trifluoromethyl)phenoxy] -3 -(5-trifluoromethyl-1,3,4-thiadiazol-2-yl)-3
-azabicyclo[3.2.1]octane (Q)

1.6 g of 60% sodium hydride was added to 60 ml of the DMF solution
containing 6.0 g of 4-fluoro-3-hydroxybenzotrifluoride with ice-cooling. After stirring
the mixture for 30 minutes at room temperature, 3.2 g of chloromethyl ether was added
dropwise with ice-cooling. After reaching room temperature, the resulting mixture was
stirred for 30 minutes, poured into water, and extracted with ethyl acetate. After being
washed with water and dried with anhydrous magnesium sulfate, the organic layer was
filtered and then vacuum-concentrated. The concentrate was purified by silica gel
column chromatography (eluant: mixed solvent of n-hexane and ethyl acetate) to obtain
6.88 g of a compound (O).
0.34 g of the compound (N) was added to 6 ml of the DMF solution containing

0.36 g of the compound (0). The mixture was heated to 80°C and 0.07 g of 60 %
sodium hydride was added thereto and the resulting mixture was kept heated to 80°C for
2 hours. After being cooled to room temperature, the mixture was poured into water
and extracted with ethyl acetate. After being washed with water and dried with
anhydrous magnesium sulfate, the organic layer was filtered and then
vacuum-concentrated. The concentrate was purified by silica gel column
chromatography (eluant: mixed solvent of n-hexane and ethyl acetate) to obtain 0.28 g of
a compound (P).
1H-NMR(CDCl3, δppm): 1.68-1.71 (m, 2H), 2.10-2.13(m, 2H), 2.62(brs,2H), 3.45(d
2H), 3.52(s, 3H), 3.84(d, 2H), 4.63(s, 1H), 5.20(s, 2H), 7.01(d, 1H), 7.25(d, 1H), 7. 37(s,
1H)
4 ml of 10% hydrochloric acid was added to 4 ml of tetrahydrofuran(THF)
solution containing 0.28 g of the compound (P) at room temperature. The mixture was
refluxed with heating for 1 hour and then poured into water and extracted with ethyl
acetate. The organic layer was washed with saturated sodium bicarbonate water and
then with saline, and dried with anhydrous magnesium sulfate. 0.25 g of the target
compound (Q) was obtained by evaporating the solvents under reduced pressure.
1H-NMR(CDCl3, δppm): 1.68-1.79(m, 2H), 2.05-2.10(m, 2H), 2.69(brs, 2H), 3.50(d,
2H), 3.89(d, 2H), 4.67(s, 1H), 5.58(s, 1H), 6.97(d, 1H), 7.15(d, 1H), 7.21(s, 1H)
Step 3
Production of
8β- [2-isopropylideneaminooxy-4-(trifluoromethyl)phenoxy] -3 -(5-trifluoromethyl-1,3,4-t
hiadiazol-3 -yl)-3 -azabicyclo [3.2.1]octane

0.07 g of a compound (R) was synthesized by the method described in Japanese
Patent Application Laid-Open No. 2001-81071 using 0.25 g of the compound (Q).
0.5 ml of acetone and 1 drop of concentrated hydrochloric acid were added to 1
ml of ethanol solution containing 0.07 g of the compound (R) and the entire mixture was
stirred for 80 minutes at room temperature. The reaction mixture was poured into water
and extracted with ethyl acetate. After being washed with water and dried with
anhydrous magnesium sulfate, the organic layer was filtered and then
vacuum-concentrated. The concentrate was purified by silica gel column
chromatography (eluant: mixed solvent of n-hexane and ethyl acetate) to obtain 0.05 g of
the target compound. Melting temperature: 113-115°C
1H-NMR(CDCl3, δppm): 51.64-1.70(m, 2H), 2.06(d, 6H), 2.03-2.13(m, 2H), 2.61(brs,
2H), 3.42(d, 2H), 3.82(dd, 2H), 4.64(s, 1H), 7.01(d, 1H), 7.21(d, 1H), 7.70(s, 1H)
(Example 7)
Production of
8p-[2-isopropylideneaminooxy-4-(trifluoromethyl)phenoxy]-3-(5-cyano-pyridin-2-yl)-3-
azabicyclo[3.2.1]octane (e)
Step 1
Production of 8β-hydroxy-3-(5-cyano-pyridin-2-yl)-3-azabicyclo[3.2.1 ]octane
(S)

5 ml of acetonitrile suspension containing 0.15 g of 3-azabicyclo[3.2.1]octa-8-ol,
0.65 g of potassium carbonate, and 0.33 g of 2-chloro-5-cyanopyridine was refluxed with
heating overnight. After being cooled to room temperature, the mixture was poured
into water and extracted with ethyl acetate. The organic layer was washed with saline
and dried with anhydrous magnesium sulfate. 0.16 g of a crude compound (S) was
obtained by evaporating solvents under reduced pressure and this compound was directly
used in the next step.
Step 2
Production of
8β-[2-methoxymethoxy-4-(trifluoromethyl)phenoxy]-3-(5-cyano-pyridin-2-yl)-3-azabicy
clo[3.2.1] octane (T)

0.14 g of 60% sodium hydride was added to 10 ml of DMF solution containing
0.58 g of 4-fluoro-3-hydroxybenzotrifluoride with ice-cooling. After stirring the
mixture for 30 minutes at room temperature, 0.28 g of chloromethyl ether was added
dropwise thereto with ice-cooling. After completing the addition, the reaction solution
was heated to room temperature and stirred for 30 minutes and then further heated to
80°C and stirred for 30 minutes. 0.49 g of the compound (S) and 0.13 g of 60% sodium
hydride were added to the reaction mixture at 80°C and the resulting mixture was stirred

for 30 minutes and then heated to 80°C and was further stirred for 2 hours. The reaction
mixture was cooled to room temperature, poured into water, and extracted with ethyl
acetate. After being washed with water and dried with'anhydrous magnesium sulfate,
the organic layer was filtered and vaccum-concentrated. The concentrate was purified
by silica gel column chromatography (eluant: mixed solvent of n-hexane and ethyl
acetate) to obtain 0.82 g of the target compound (T).
1H-NMR(CDCl3, δppm):1.55-1.63(m, 2H), 2.02-2.05(m, 2H), 2.60(brs, 2H), 3.13(d,2H),
3.52(s, 3H), 4.22(d, 2H), 4.63(s, 1H), 5.20(s, 2H), 6.58(d, 1H), 7.03(d, 1H) 7.26(d, 1H),
7.37(s, 1H), 7.62(d, 1H), 8.41(s, 1H)
Step 3
Production of
8β-[2-hydroxy-4-(trifluoromethyl)phenoxy]-3-(5-cyano-pyridin-2-yl)-3-azabicyclo[3.2.1]
octane (U)

10 ml of 10% hydrochloric acid was added to 10 ml of THF solution containing
0.82 g of the compound (T) at room temperature. The mixture was refluxed with
heating for 30 minutes, poured into water, and extracted with ethyl acetate. The organic
layer was washed with saline and dried with anhydrous magnesium sulfate. 0.74 g of
the target compound (U) was obtained by evaporating the solvents under reduced
pressure.
1H-NMR(CDCl3, δppm):1.62-1.75(m, 2H), 1.91-1.98(m, 2H), 2.65(brs, 2H), 3.17(d,
2H), 4.26(d, 2H), 4.66(s, 1H), 5.63(s, 1H), 6.60(d, 1H), 6.98(d, 1H), 7.13(d, 1H) 7.16(s,
1H), 7.63(d, 1H), 8.42(s, 1H)

This compound was directly used in the next step without purification.
Step 4
Production of
8P-[2-isopropylideneaminooxy-4-(trifluoromethyl)phenoxy]-3-(5-cyano-pyridin-2-yl)-3-
azabicyclo[3.2.1]octane (W)

0.76 g of a compound (V) was synthesized by the method described in Japanese
Patent Application Laid-OpenNo. 2001-81071 using 0.74 g of the compound (U).
1H-NMR(CDCl3,δppm):1.55-1.68(m, 2H), 1.99-2.04(m, 2H), 2.59(brs, 2H), 3.13(d, 2H),
4.22(d, 2H), 4.60(s, 1H), 6.00(brs, 2H), 6.59(d, 1H), 6.98(d, 1H), 7.20(d, 1H), 7.60(d,
2H),8.01(s, 1H),8.41(s, 1H)
3 ml of acetone and 1 drop of concentrated hydrochloric acid were added to 3 ml of
ethanol solution containing 0.76 g of the compound (V) and the entire mixture was
stirred for 1 hour at room temperature. The mixture was poured into water and
extracted with ethyl acetate. After being washed with water and dried with anhydrous
magnesium sulfate, the organic layer was filtered and then vacuum-concentrated. The
concentrate was purified by silica gel column chromatography (eluant: mixed solvent of
n-hexane and ethyl acetate) to obtain 0.45 g of the target compound (W). The structure
was confirmed by NMR. Melting temperature: 120-122°C

(Example 8)
Production of
9P-[2-cyclopropylmethoxy-4-(trifluoromethyl)phenoxy]-7-[6-(trifluoromethyl)-3-pyridaz
yl] -3 -oxa-7-azabicyclo [3.3.1] nonane (AC)
Step 1
Production of N-benzyl-3-oxa-7- azabicyclo[3.3.1]nonan-9-ol (Z)

1.2 g of acetic acid, 80 ml of methanol, and 5.33 g of 90% formalin were added
to 2.2 g of benzylamine in this order. Furthermore, while gradually heating the mixture
from 20°C to 45°C, 2.0 g of the compound (X) was added dropwise thereto and the
resulting mixture was refluxed for 5.5 hours and stirred overnight at room temperature.
The solvents were evaporated under reduced pressure from the reaction mixture
and 100 ml of water and 2 ml of concentrated hydrochloric acid were added to the
obtained residue and washed with diethylether. pH of the aqueous layer was adjusted to
7 or more by adding sodium hydroxide and extracted with chloroform. After drying the
organic layer with anhydrous magnesium sulfate, the solvents were evaporated under
reduced pressure and the residue was purified by silica gel column chromatography
(chloroform: methanol = 10:1 (v/v)) to obtain 4.09 g of a compound (Y). Yield 88.5%
Subsequently, 1.86 g of sodium borohydride was added to 30 ml of 2-propanol
solution containing 2.24 g of the compound (Y) at 0°C and thereafter, 15 ml of water was
added thereto and the resulting mixture was heated to room temperature and stirred for
one day. After cooling the reaction mixture to 0°C, 75 ml of 10% hydrochloric acid was

added thereto and thereafter, 45 ml of 10% sodium hydroxide was added thereto at the
same temperature. The resulting mixture was extracted with chloroform and the organic
layer was dried with anhydrous magnesium sulfate. The solvents were evaporated
under reduced pressure to obtain 1.56 g of the compound (Z) as a viscous oil. Yield
83.8%
Step 2
Production of the compound (AA)

0.40 g of 60%o sodium hydride was added to 20 ml of DMF solution containing
1.56 g of the compound (Z) obtained in Step 1 and the resulting mixture was stirred for
15 minutes at room temperature. 2.35 g of
4-fluoro-3-(cyclopropylmethoxy)benzotrifluoride was added to the mixture and the
resultant mixture was stirred for 3 hours at 100°C. After cooling the reaction mixture to
room temperature, water was poured thereto and extracted with ethyl acetate. After
being washed with saturated saline and dried with anhydrous magnesium sulfate, the
organic layer was filtered and vacuum-concentrated to obtain a crude compound (AA).
The obtained crude compound (AA) was purified by silica gel column
chromatography (eluant: n-hexane: ethyl acetate = 2:3 (v/v)) to obtain 0.98 g of a
compound (AA-cis) as a viscous oil (yield 32.7%o) and 0.76 g of a compound (AA-trans)
as a viscous oil (yield 25.4%>), respectively.

NMR data of AA-cis:
1H-NMR(CDCl3, δppm):0.34-0.44(m, 2H), 0.60-0.67(m, 2H), 1.26-1.3 l(m, 2H),
1.94(brs, 2H), 2 .49(d, 2H), 3.17(d, 2H), 3.57(s, 2H), 3.79(d, 2H), 3.88(d, 2H), 4.27(d,
2H), 4.43(t, 1H), 6.94(d, 1H), 7.10(s, 1H), 7.17(d, 1H), 7.20-7.40(m, 5H)
NMR data of AA-trans:
1H-NMR(CDCl3, δppm):0.39-0.44(m, 2H), 0.62-0.71(m, 2H), 1.25-1.35(m, 1H),
2.04(brs, 2H), 2.84(brs, 4H), 3.55(s, 2H), 3.82(d, 2H), 3.89(d, 2H), 4.13(d, 2H), 4.59(t,
1H), 6.95(d, 1H), 7.10(s, 1H), 7.14(d, 1H), 7.20-7.42(m, 5H)
Step 3

0.20 g of 10% Pd/C was added to 20 ml of ethanol solution containing 0.98 g of
the compound (AA-cis) obtained in Step 2 and the entire mixture was stirred for 6.5
hours at 60°C under hydrogen atmosphere (atmospheric pressure). The reaction
mixture was filtered and the filtrate was evaporated under reduced pressure to obtain 0.75
g of a debenzylated product (AB) as an oily matter. Yield 95.9%
1H-NMR(CDCl3, δppm):0.35-0.40(m, 2H), 0.60-0.69(m, 2H), 1.23-1.34(m, 1H),

1.83(brs, 2H), 1.99(brs, 1H), 3.04(d, 2H), 3.38(d, 2H), 3.85-3.91(m, 4H), 4.35(d, 2H),
4.59(t, 1H), 6.95(d, 1H), 7.10(s, 1H), 7.12(d, 1H)
0.19 g of 3-chloro-6-(trifluoromethyl)pyridazine and 0.15 g of DBU were added
to 3 ml of N-methylpyrrolidone solution containing the obtained compound (AB) and the
resulting mixture was stirred for 3 hours at 120 to 130°C. After cooling the reaction
mixture to room temperature, water was poured thereto and extracted with ethyl acetate.
After being washed with saturated saline and dried with anhydrous magnesium sulfate,
the organic layer was filtered and vacuum-concentrated. The obtained residue was
purified by silica gel column chromatography (eluant: n-hexane: ethyl acetate =1:1
(v/v)) to obtain 0.24 g of the target compound (AC). Yield 57%, mp. 93 to 95°C
Examples of the compounds of the present invention produced by the method
according to the above Examples are shown in the Table below including the compounds
produced in the above Examples. Note that in the Table below, R1 and R2 show
substituents including substituents associated by two or more substituents so that the
Table is simplified. Also, the description "vis" shows that the compound is a viscous oil
and the description "amor" shows that the compound is amorphous. Moreover,
nD21.8-1.5008 means that the refractive index at 21.8°C is 1.5008 (the same also applies
to others). In addition, the description "cPr" means cyclopropyl, the description "cHex"
means cyclohexyl (the same also applies to others), the description "Ac" means acetyl,
the description "nPr" means normal propyl, the description "iPr" means isopropyl, the
description "nBu" means normal butyl, the description "iBu" means isobutyl, and the
description "tBu" means tertiary butyl, and the description "TMS" means trimethylsilyl
and the description "THF" means tetrahydrofuranyl.

Formulation Examples
[Insecticides/acaricides]
Although a few examples regarding compositions of the present invention are shown
next, additives and proportions added are changeable over a wide range without being
limited to these examples. Parts in Formulation Examples show parts by weight.
Formulation Example 1 Wettable powder
Compound of the present invention 40 parts
Diatomaceous earth 53 parts
Higher alcohol sulfate ester 4 parts
Alkylnaphthalenesulfonate salt 3 parts
The above components were mixed homogenously and ground finely to obtain a wettable
powder with 40% of active ingredient.
Formulation Example 2 Emulsion
Compound of the present invention 3 0 parts
Xylene 33 parts
Dimethylformamide 30 parts
Polyoxyethylene alkyl allyl ether 7 parts
The above components were mixed and dissolved to obtain an emulsion with 30% of
active ingredient.
Formulation Example 3 Dusting powder
Compound of the present invention 10 parts
Talc 89 parts
Polyoxyethylene alkyl allyl ether 1 part
The above components were mixed homogenously and ground finely to obtain a dusting
powder with 10% of active ingredient.

Formulation Example 4 Granules
Compound of the present invention 5 parts
Clay 73 parts
Bentonite 20 parts
Sodium dioctylsulfosuccinate salt 1 part
Sodium phosphate 1 part
The above components were mixed and ground well and, after adding water thereto and
kneading together, granulated and dried to obtain granules with 5% of active ingredient.
Formulation Example 5 Suspending agent
Compound of the present invention 10 parts
Sodium lignin sulfonate 4 parts
Sodium dodecylbenzenesulfonate 1 part
Xanthan gum 0.2 parts
Water 84.8 parts
The above components were mixed and subjected to wet-grinding until the grain size of 1
µm or less was achieved to obtain a suspending agent with 10% of active ingredient.
Test Example 1 Effectiveness against Tetranychus urticae
17 adult female Tetranychus urticae, which were resistant to organophosphorous
pesticides, were inoculated on the first true leaf of a common bean, which was seeded in
a pot with a diameter of 9 cm, where 7 to 10 days had passed after the germination.
After the inoculation, the drug solution, which was prepared by following the method of
the wettable powder shown in Example 1 of the drugs and by diluting with water to
achieve the compound concentration of 125 ppm, was applied. The pot was placed in a
temperature-controlled room where the temperature and humidity were set to 25°C and

65% respectively, and the adulticidal rate was examined 3 days after the application.
The test was repeated twice.
As a result, the compounds below showed the insecticidal rate of 100%.
1-1, 1-4 to 1-7,1-10,1-13, 1-17,1-18,1-21 to 1-29,1-31 to 1-36,1-39 to 1-47, 1-50,
1-51, 1-54, 2-3, 3-1,4-5, 4-7,4-9, 4-13, 4-16,4-18 to 4-20,4-53 to 4-55,4-58 to 4-61,
4-64, 4-70, 4-71, 5-1 to 5-8,10-1, 11-1, 13-2, 15-1,15-17,16-1 to 16-26, 16-61, 16-65,
16-69,16-73 to 16-75,16-78,16-82 to 16-91,17-2,17-3,17-7 to 17-10,19-1 to 19-3,
21-1, 21-3,21-5, 21-6,21-14 to 21-16
Test Example 2 Effectiveness against Panonychus citri
10 adult female Panonychus citri were inoculated on the leaf of a mandarin
orange, which was placed in a petri dish. After the inoculation, the drug solution, which
was prepared by following the method of the emulsion shown in Example 2 of the drugs
and by diluting with water to achieve the compound concentration of 125 ppm, was
applied using a rotary spreading tower. The dish was placed in a temperature-controlled
room where the temperature and humidity were set to 25°C and 65% respectively, adults
were removed 3 days after the application, and whether eggs laid during these 3 days
could grow to become adults was examined on the 11th day.
As a result, the compounds below showed the insecticidal rate of 100%.
1-1,1-5,1-7, 1-13,1-17,1-24,1-31,1-32,1-47,1-50, 3-1, 4-5, 4-53, 4-54, 4-58 to 4-61,
4-64, 4-70, 4-71, 5-1, 5-2, 5-4, 5-8,10-1, 12-4,16-1 to 16-13,16-15 to 16-20,16-22,
16-23,16-26, 16-61, 16-73, 16-83, 16-84, 16-89 to 16-91, 17-7,17-9,17-10,19-1 to
19-3,21-5,21-6,21-13
Test Example 3 Effectiveness test against Pseudaletia separata

0.2 ml of a commercially available artificial diet (Insecta LFS manufactured by
Nihon Nosan-Kogyo Co., Ltd) was put into a plastic test tube with a volume of 1.4 ml
and was used as a test diet. The compound was adjusted to prepare 1% solution using
dimethylsulfoxide containing 0.5% tween 20 and this solution was applied by adding
dropwise onto the surface of the diet in an amount equivalent to 10 µg of the compound.
2 second-instar larvae of Pseudaletia separate were inoculated to each test tube and the
tubes were sealed with plastic lids. The tubes were left at 25°C and the insecticidal rate
and amount of food ingested were examined after 5 days. The test was repeated twice.
In the present test, the compounds below were effective by showing the
insecticidal rate of 100%, or the amount of food ingested was 10% or less compared to
the solvent control group.
4-3, 4-4,16-1,16-2,17-3, 17-7 to 17-9
Test Example 4 Effectiveness test against Culexpipiens molestus
10 larvae of Culex pipiens molestus, which were hatched 1 day before, and
0.225 ml of distilled water containing 0.5 mg of feed for aquarium fish (TetraMin®
manufactured by Tetra Japan Co. Ltd) were put into a polystyrene test vessel with a
volume of 0. 3 ml. The compound was adjusted to prepare 1% solution using
dimethylsulfoxide containing 0.5% tween 20 and further diluted to 0.01% with distilled
water. 0.025ml of this diluted drug solution was added to the test vessel with Culex
pipiens molestus and was stirred (final compound concentration 0.001%). The vessels
were left at 25 °C and the insecticidal rate was examined after 2 days. The test was
repeated twice.
In the present test, the compound below was effective by showing the
insecticidal rate of 90% or more.

4-3
While preferred embodimentss or the invention nave been
illustrated above, it should be understood that these are exemplary of the invention and
are not to be considered as limiting. Additions, omissions, substitutions, and other
modifications can be made without departing from the spirit or scope of the present
invention. Accordingly, the invention is not to be considered as being limited by the
foregoing description, and is only limited by the scope of the appended claims.
[Industrial Applicability]
According to the present invention, it is possible to provide cyclic amine
compounds with a novel structure, salts thereof, N-oxides thereof, or intermediates
thereof during the production and especially agents for pest control with excellent
bioactivities in terms of insecticidal/acaricidal activities and high safety.

WE CLAIM:
1. Cyclic amine compounds represented by formula (1)

or salts thereof or N-oxides thereof, wherein
Cy1 represents one selected from the group
consisting of unsubstituted or substituted phenyl,
unsubstituted or substituted naphthalen-1-yl, and
unsubstituted or substituted heteroaromatic ring;
X represents oxygen, sulfur, unsubstituted or
substituted nitrogen, sulfinyl, or sulfonyl;
R1a, and R2a, R1a and R4a, R2a and R3a, or R3a and R4a form
saturated rings together;
R1a, R1b, R2a, R2b, R3a, R3b, R4a, R4b, and R5 which do
not form the saturated rings are each independently
hydrogen, hydroxyl, halogen, unsubstituted or substituted
amino, nitro, or an organic group;
Cy2 represents one selected from the group
consisting of unsubstituted or substituted aromatic

hydrocarbon, unsubstituted or substituted furan-2-yl,
unsubstituted or substituted furan-3-yl, unsubstituted or
substituted thiophen-2-yl, unsubstituted or substituted
thiophen-3-yl, unsubstituted or substituted pyrrol-2-yl,
unsubstituted or substituted pyrrol-3-yl, unsubstituted
or substituted oxazol-2-yl, unsubstituted or substituted
oxazol-4-yl, unsubstituted or substituted oxazol-5-yl,
unsubstituted or substituted thiazol-2-yl, unsubstituted
or substituted thiazol-4-yl, unsubstituted or substituted
thiazol-5-yl, unsubstituted or substituted isoxazol-3-yl,
unsubstituted or substituted isoxazol-4-yl, unsubstituted
or substituted isoxazol-5-yl, unsubstituted or
substituted isothiazol-3-yl, unsubstituted or substituted
isothiazol-4-yl, unsubstituted or substituted isothiazol-
5-yl, unsubstituted or substituted imidazol-4-yl,
unsubstituted or substituted imidazol-5-yl, unsubstituted
or substituted pyrazol-3-yl, unsubstituted or substituted
pyrazol-4-yl, unsubstituted or substituted pyrazol-5-yl,
unsubstituted or substituted 1,3,4-oxadiazol-2-yl,
unsubstituted or substituted 1,3,4-thiadiazol-2-yl,
unsubstituted or substituted 1,2,3-triazol-4-yl,

unsubstituted or substituted 1,2,4-triazol-3-yl,
unsubstituted or substituted 1,2,4-triazol-5-yl,
unsubstituted or substituted pyridin-2-yl, unsubstituted
or substituted pyridin-3-yl, unsubstituted or substituted
pyridin-4-yl, unsubstituted or substituted pyridazin-3-
yl, unsubstituted or substituted pyridazin-4-yl,
unsubstituted or substituted pyrazin-2-yl, unsubstituted
or substituted pyrimidin-2-yl, unsubstituted or
substituted pyrimidin-4-yl, unsubstituted or substituted
pyrimidin-5-yl, unsubstituted or substituted 1,3,5-
triazin-2-yl, and unsubstituted or substituted 1,2,4-
triazin-3-yl; with a proviso that Cy2 is an unsubstituted
or substituted furan-2-yl, unsubstituted or substituted
furan-3-yl, unsubstituted or substituted thiophen-2-yl,
unsubstituted or substituted thiophen-3-yl, unsubstituted
or substituted pyrrol-2-yl, unsubstituted or substituted
pyrrol-3-yl, unsubstituted or substituted oxazol-2-yl,
unsubstituted or substituted oxazol-4-yl, unsubstituted
or substituted oxazol-5-yl, unsubstituted or substituted
thiazol-2-yl, unsubstituted or substituted thiazol-4-yl,
unsubstituted or substituted thiazol-5-yl, unsubstituted

or substituted isoxazol-3-yl, unsubstituted or
substituted isoxazol-4-yl, unsubstituted or substituted
isoxazol-5-yl, unsubstituted or substituted isothiazol-3-
yl, unsubstituted or substituted isothiazol-4-yl,
unsubstituted or substituted isothiazol-5-yl,
unsubstituted or substituted imidazol-4-yl, unsubstituted
or substituted imidazol-5-yl, unsubstituted or
substituted pyrazol-3-yl, unsubstituted or substituted
pyrazol-4-yl, unsubstituted or substituted pyrazol-5-yl,
unsubstituted or substituted 1,3,4-oxadiazol-2-yl,
unsubstituted or substituted 1,3,4-thiadiazol-2-yl,
unsubstituted or substituted 1,2,3-triazol-4-yl,
unsubstituted or substituted 1,2,4-triazol-3-yl,
unsubstituted or substituted 1,2,4-triazol-5-yl,
unsubstituted or substituted pyridin-2-yl, unsubstituted
or substituted pyridin-3-yl, unsubstituted or substituted
pyridin-4-yl, unsubstituted or substituted pyridazin-3-
yl, unsubstituted or substituted pyridazin-4-yl,
unsubstituted or substituted pyrazin-2-yl, unsubstituted
or substituted pyrimidin-2-yl, unsubstituted or
substituted pyrimidin-4-yl, unsubstituted or substituted

pyrimidin-5-yl, unsubstituted or substituted 1,3,5-
triazin-2-yl, and unsubstituted or substituted 1,2,4-
triazin-3-yl when R1a and R2a form a saturated ring
together and Cy1 is an unsubstituted or substituted
phenyl, and Cy2 is a substituted pyridin-2-yl having one
or more cyano as a substituent when Cy1 is an
unsubstituted or substituted phenyl and Cy2 is a pyridin-
2-yl.
2. Cyclic amine compounds, salts thereof, or N-oxides
thereof as claimed in Claim 1, wherein the organic groups
Rla, R1b, R2a, R2b, R3a, R3b, R4a, R4b, and R5 which do not form
the saturated rings in the formula (1) are alkyl,
alkoxycarbonyl, or alkoxy.
3. Cyclic amine compounds, salts thereof, or N-oxides
thereof as claimed in Claim 1 or 2, wherein Rla and R2a,
or R3a and R4a form the saturated ring together.
4. Cyclic amine compounds, salts thereof, or N-oxides
thereof as claimed in Claim 1, wherein the number of
atoms at a crosslink of a piperidine ring, which forms

the saturated ring, is 2 or 3.
5. Cyclic amine compounds represented by a formula (2)

or salts thereof or N-oxides thereof, wherein
Cy1 represents an unsubstituted or substituted
aromatic ring;
X0 represents oxygen, sulfur, sulfinyl, or
sulfonyl;
R3a and R4a form a saturated ring together;
R1a, R1b, R2a, R2b, R3b, R4b, and R5 each independently
represents hydrogen, hydroxyl, halogen, unsubstituted or
substituted amino, nitro, or an organic group; and
R represents hydrogen, alkoxycarbonyl,
alkylcarbonyl, or 1-alkoxyalkyl.
6. Cyclic amine compounds, salts thereof, or N-oxides
thereof as claimed in Claim 5, wherein the organic groups

R1a, R1b, R2a, R2b, R3b, R4b, and R5 in the formula (2) which
do not form the saturated rings are alkyl,
alkoxycarbonyl, or alkoxy.
7. Cyclic amine compounds, salts thereof, or N-oxides
thereof as claimed in Claim 5, wherein R3a and R4a form
the saturated ring together and the number of atoms at a
cross-linking site of the piperidine ring, which forms
the saturated ring, is 2 or 3.
8. A pesticidal composition comprising at least one of
cyclic amine compounds represented by formula (3),

salts thereof, or N-oxides thereof as an active
ingredient, wherein
Cy11 represents an unsubstituted or substituted
aromatic ring;
X11 represents oxygen, sulfur, unsubstituted or
substituted nitrogen, sulfinyl, or sulfonyl;

R11a and R21a, R11a and R41a, R21a and R31a, or R31a and R41a
form saturated rings together;
R11a, R11b, R21a, R21b, R31a, R31b, R41a, R41b, and R51 which
do not form the saturated rings each independently
represents hydrogen, hydroxyl, halogen, unsubstituted or
substituted amino, nitro, or an organic group; and
Cy21 represents an unsubstituted or substituted
aromatic ring
9. A pesticidal composition as claimed in Claim 8,
wherein the pest is a insect or an acarid.

The invention discloses cyclic amine compounds
represented by formula (1):

wherein Cy1, Cy2, Rla, Rlb, R2a, R2b, R3a, R3b, R4a, R4b , R5 and
X are as described in the specification.
The invention is also for a pesticidal composition
comprising the above cyclic amine compounds.

Documents:

01308-kolnp-2008-abstract.pdf

01308-kolnp-2008-claims.pdf

01308-kolnp-2008-correspondence others.pdf

01308-kolnp-2008-description complete.pdf

01308-kolnp-2008-form 1.pdf

01308-kolnp-2008-form 3.pdf

01308-kolnp-2008-form 5.pdf

01308-kolnp-2008-gpa.pdf

01308-kolnp-2008-international publication.pdf

01308-kolnp-2008-international search report.pdf

01308-kolnp-2008-others.pdf

1308-KOLNP-2008-(09-04-2012)-CORRESPONDENCE.pdf

1308-KOLNP-2008-(17-02-2012)-CORRESPONDENCE.pdf

1308-kolnp-2008-abstract.pdf

1308-kolnp-2008-amanded claims.pdf

1308-KOLNP-2008-ASSIGNMENT.pdf

1308-KOLNP-2008-CORRESPONDENCE 1.1.pdf

1308-KOLNP-2008-CORRESPONDENCE 1.3.pdf

1308-KOLNP-2008-CORRESPONDENCE-1.2.pdf

1308-KOLNP-2008-CORRESPONDENCE.pdf

1308-kolnp-2008-description (complete).pdf

1308-kolnp-2008-english translation.pdf

1308-KOLNP-2008-EXAMINATION REPORT.pdf

1308-kolnp-2008-form 1.pdf

1308-KOLNP-2008-FORM 18.pdf

1308-kolnp-2008-form 2.pdf

1308-KOLNP-2008-FORM 3.pdf

1308-KOLNP-2008-FORM 5.pdf

1308-KOLNP-2008-GPA.pdf

1308-KOLNP-2008-GRANTED-ABSTRACT.pdf

1308-KOLNP-2008-GRANTED-CLAIMS.pdf

1308-KOLNP-2008-GRANTED-DESCRIPTION (COMPLETE).pdf

1308-KOLNP-2008-GRANTED-FORM 1.pdf

1308-KOLNP-2008-GRANTED-FORM 2.pdf

1308-KOLNP-2008-GRANTED-SPECIFICATION.pdf

1308-kolnp-2008-others-1.1.pdf

1308-KOLNP-2008-OTHERS.pdf

1308-KOLNP-2008-PETITION UNDER RULE 137.pdf

1308-kolnp-2008-reply to examination report.pdf

1308-KOLNP-2008-REPLY TO EXAMINATION REPORT1.1.pdf

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Patent Number

251964

Indian Patent Application Number

1308/KOLNP/2008

PG Journal Number

16/2012

Publication Date

20-Apr-2012

Grant Date

18-Apr-2012

Date of Filing

01-Apr-2008

Name of Patentee

NIPPON SODA CO., LTD.

Applicant Address

2-1, OHTEMACHI 2-CHOME, CHIYODA-KU, TOKYO

Inventors:

#	Inventor's Name	Inventor's Address
1	HAMAMOTO, ISAMI	C/O NIPPON SODA CO., LTD., ODAWARA RESEARCH CENTER, 345, TAKADA, ODAWARA-SHI, KANAGAWA-KEN
2	HANAI, DAISUKE	C/O NIPPON SODA CO., LTD., ODAWARA RESEARCH CENTER, 3967, AZA BIKUNIYAMA, OAZA SARASHINA, BANDAI-MACHI, YAMA-GUN, FUKUSHIMA-KEN
3	IWASA, TAKAO	C/O NIPPON SODA CO., LTD., ODAWARA RESEARCH CENTER, 345, TAKADA, ODAWARA-SHI, KANAGAWA-KEN
4	YANO, MAKIO	C/O NIPPON SODA CO., LTD., ODAWARA RESEARCH CENTER, 345, TAKADA, ODAWARA-SHI, KANAGAWA-KEN
5	KAWAGUCHI, MASAHIRO	C/O NIPPON SODA CO., LTD., ODAWARA RESEARCH CENTER, 345, TAKADA, ODAWARA-SHI, KANAGAWA-KEN
6	TAKAHASHI, JUN	C/O NIPPON SODA CO., LTD., ODAWARA RESEARCH CENTER, 345, TAKADA, ODAWARA-SHI, KANAGAWA-KEN

PCT International Classification Number

C07D 451/14

PCT International Application Number

PCT/JP2006/320133

PCT International Filing date

2006-10-06

PCT Conventions:

#	PCT Application Number	Date of Convention	Priority Country
1	2006-182314	2006-06-30	Japan
2	2005-297803	2005-10-12	Japan
3	2005-294127	2005-10-06	Japan
4	2006-016877	2006-01-25	Japan
5	2005-294126	2005-10-06	Japan