TW200526552A - Haloalkene compounds, process for their production and pesticides containing them - Google Patents

Abstract

Present invention relates to a haloalkene compound of the formula (I) or its salt, wherein each of X1 and X2 is halogen; Y is alkyl, haloalkyl or phenyl; n is 0 to 5; L is -C(=B)Q, -C(=B)B'Q, -C(=B)N(D)Q, -N(D)Q, -N(D)C(=B)Q, -N(D)C(=B)B'Q, -N(D)SO2Q, -N=CHQ, -N=C(Q)2, -SO2Q, -SO2N(D)Q or alkyl substituted by J, G is a hydrogen atom, alkyl, haloalkyl, phenylalkyl, alkenyl, haloalkenyl, phenylalkenyl, alkynyl, haloalkynyl, phenylalkynyl, -C(=B)Q, -C(=B)B'Q, -C(=B)N(G')Q, -SQ, -SO2Q, -SN(G')Q, -SN(G')C(=B)B'Q or -SO2N(G')Q; A is an oxygen atom or a sulfur atom.

Description

200526552 (1) IX. Description of the invention [Technical field to which the invention belongs] The present invention relates to a novel haloene compound which acts as an active ingredient of a pesticide. [Prior art] WO0 3/84927, WO04 / 528 7 2 and EP432861 respectively disclose haloene compounds having a certain chemical structure. However, none of them has disclosed or suggested a haloene compound of the following formula (I). [Summary of the Invention] Description of the invention Over the years, 'many insecticides have been used', but many of them have various problems, resulting in insufficient effects, and their use is limited because the pests have become resistant to drugs. Accordingly, it is desired to develop novel insecticides which are substantially free of such problems, for example, insecticides capable of controlling various pests which cause many problems in agriculture and horticulture, or insecticides capable of controlling parasitic pests on animals. The present inventors have worked hard to investigate haloene compounds to find excellent insecticides. As a result, they have found a novel haloene compound having a very high insecticidal effect at a low dose 'and being simultaneously safe to crops, pest natural predators or mammals, and completed the present invention. That is, the present invention relates to a haloene compound represented by formula (I) or a salt thereof: 200526552 (2)

χ2 CH2 (CH2〇H2) dC—N—L () where X1 and X2 are each halogen; Y is alkyl, haloalkyl, or phenyl; 11 is from 0 to 5, L is -C (= B) Q , A c (= B) B, Q, -C (= B) N (D) Q, -N (D) Q, -N (D) C (= B) Q, -N (D) C (= B) BQ, -N (D) S02Q, -n = CHQ, -N = C (Q) 2, -S〇2Q, -S〇2N (D) Q or J-substituted alkyl (alkyl May be further substituted by other substituents); J is -C (= B) B, Q, -C (= B) N (D) Q, -S02Q or -S〇2N (D) Q; G and D Each is a hydrogen atom, an alkyl group, an alkyl group, a phenylalkyl group, an alkenyl group, a haloalkenyl group, a phenylalkenyl group, an alkynyl group, a haloalkynyl group, a phenylalkynyl group, C (-B) Q, -C (= B) B 'Q,-c (= b) N (G,) Q,-SQ, • S02Q, -SN (G') Q, -SN (G ') C (= B) B'Q or -S02N (G ') Q; G' is k, haloalkyl, phenylalkyl, alkenyl, haloalkenyl, phenylalkenylalkynyl, haloalkynyl, or phenylalkynyl; a, b & B, each is an oxygen atom or a sulfur atom, Q is a substituted alkyl group, a substituted alkenyl group, a substituted alkynyl group, a substituted cycloalkyl group, or a group selected from an oxygen atom and a sulfur atom Random nitrogen atoms 5 - to 12-membered heterocyclic group (the heterocyclic group may be substituted); he system of law; He and containing the pesticides. Insecticides containing the novel haloene compounds of formula (1) serving as an active ingredient have a very good insecticidal effect in the low-lying sun, and at the same time are safe for crops, natural enemies of pests or mammals. -6- 200526552 (3) Best Mode for Implementing the Invention -N = C (Q) 2 in L, two Qs may be the same or different. In one case, in the definition of L ·, an alkyl group substituted by: r (the alkyl group may be further substituted with other substituents) has another substituent, and the substituent may be, for example, W. In the definition of Q, an alkyl group which may be substituted, an alkenyl group which may be substituted, an alkynyl group which may be substituted, a cycloalkyl group which may be substituted, or an arbitrary heteroatom containing an arbitrary hetero atom selected from an oxygen atom, a sulfur atom, and a nitrogen atom. The respective substituents in the 5-to-membered heterocyclyl (the heterocyclyl may be substituted) may be, for example, w. w may be, for example, halogen, nitro, cyano, an alkyl group which may be substituted by K, an alkenyl group which may be substituted by K, an alkynyl group which may be substituted by K, a cycloalkyl group which may be substituted by MJ, or a group selected from the group consisting of 5- to 1 2-membered heterocyclic groups of arbitrary heteroatoms of oxygen, sulfur and nitrogen atoms (heterocyclyl may be substituted by M1), -OR], -SR], -NR ^ R2, -COR], -C02R], -COSR1, -CSOR1, -CS2R], -SC ^ NR ^ R2, -CONR] R2, -CSNR] R2, -C (= N0V) Ri, _n (R)) COR3, _n (r) ) C2r3, -N (RJ) COSR3 ^ -NCR ^ CSOR3 > -N (R1) CS2R3 '-N (R)) S02R3, _s〇R3, -S02R3, -CSR3, _〇COR3, -OCSR3, -SCOR3, -SCSR3, trialkylsilyl or trialkylsilyloxy. The number of substituents W may be 1 or more, and if more, they may be the same or different. κ may be, for example, a halogen, a nitro group, a cyano group, a cyclonicino group which may be substituted by M], or a 5- to] 2-membered heterocyclic ring containing an arbitrary heteroatom selected from an oxygen atom, a sulfur atom, and a nitrogen atom. (Heterocyclyl may be substituted by μ1), -0M2, -7-200526552 (4) -SM2, _NM2M3, -COM2, _C〇2M2, _c〇SM2, -CS〇M2 -CS2M2, -S〇2NM2M3,- CONM2M3, -CSNM2M3, -C (= NOV) M2, -N (M2) COM4, -N (M2) C02M4, -N (M2) COSM4, -N (M2) CSOM4 ... n (m2) cs2m4,- N (M2) S02M4, -SOM4, -S02M4, -CSM4, -OCOM4, • CSM4, -SCOM4, or -SCSM4. The number of substituents K may be 1 or more, and if more, they may be the same or different. M1 may be, for example, halogen, nitro, cyano, alkyl, haloyl, cycloalkyl, halocycloalkyl, alkenyl, haloalkenyl, alkynyl, haloyl, ... OR4, -SR4,- NR4R5, -COR4 ... C〇2R4 ... coSr4, -CSOR4, -CS2R4, -S02NR4R5, -CONR4R5, -CSNR4R5, -C (= NOV) R4 ... N (R4) COR6, -N (H4) c 〇2r6, _N (R4) COSR6 > -N (R4) CSOR6 ^ -N (R4) CS2R6 > -n (r4) so2r6, SOR6, 's〇2R6, csr6, _〇c〇r6, -〇csr6 , -Sc〇r6 or _scsr6. The number of substituents M] may be [more] and if more, it may be the same or different. M and M may each be, for example, a hydrogen atom, a group that may be substituted, an alkenyl group that may be substituted by M, an alkynyl group that may be substituted with M5, a cycloalkyl group that may be substituted, or a group selected from an oxygen atom and a sulfur atom. And the nitrogen atom means a heteroatom to a 12-membered heterocyclic group (the heterocyclic group may be substituted by M). Is as defined above. ° 'M4 may be' e.g., a radical that may be substituted by M5, an alkenyl group that may be substituted by M ', an alkynyl group that may be substituted by M5, a cyclic hydrocarbon that may be substituted by M, "or it may be selected from the group consisting of an oxygen atom, a sulfur atom, and Arbitrary heteroatom work of nitrogen atom: 200526552 (5) to 12-membered heterocyclyl (heterocyclyl may be substituted by M1). μ1 is defined as μ ^ — as defined above. It may be, for example, a halogen, an alkoxy group which may be substituted by M], an alkylthio group which may be substituted by M1, an alkylsulfinyl group which may be substituted by M1, a fluorenyl group which may be substituted by μ], —M6, -OM6 or -SM6. The number of the substituents M5 may be 1 or more 'and if more, they may be the same or different. Think of it as defined above. M6 may be, for example, a cyclic hydrocarbon group which may be substituted by M] or a 5-membered heterocyclic group containing an arbitrary hetero atom selected from an oxygen atom, a sulfur atom, and a nitrogen atom (the heterocyclic group may be substituted by M1). M1 is as defined above. Each of R and R may be, for example, a hydrogen atom, an alkyl group which may be substituted by M7, an alkenyl group which may be substituted by M7, an alkynyl group which may be substituted by M7, a cycloalkyl group which may be substituted by μ], or a group selected from oxygen A 5- to 12-membered heterocyclic group of random heteroatoms of atoms, sulfur atoms and nitrogen atoms (the heterocyclic group may be substituted by M). " is as defined above. It may be, for example, an alkyl group which may be substituted by M7, an alkenyl group which may be substituted, an alkynyl group which may be substituted by M7, a cyclic hydrocarbon group which may be substituted by M], or a group selected from an oxygen atom, a sulfur atom, and a nitrogen atom 5_ to 12-membered heterocyclyl (heterocyclyl may be substituted by M) of random heteroatoms. M] is as defined above. M7 may be, for example, 'halogen, a cycloalkyl group which may be substituted by μ 1,% to a random heteroatom selected from an oxygen atom, a sulfur atom, and a nitrogen atom] to a 2-membered heterocyclic group (the heterocyclic group may be substituted by M1 ), -0M8,-SM8, _NM8M9, -COMs, -C02] V18, -COSM8, -CSOM8 '-CS2M8, 200526552 (6)

-n (m8) com] 0, -N (m8) C02M so2nm8m9, -conm8m9 C (= NOV) M8, N'N (M8) COSM10 -n (m8) so2m] -n (m8) csom] 0,- N (M8) CS2M] 〇,

-SOM

-S02M】 0… CSM

'OCOM

-OCSM 10 may be the same or not. The number of substituents M7 may be 1 or more, -SCOM] 0 or -SCSM and if more, 0M1 is as defined above and each M may be 'For example, a hydrogen atom, an alkyl group that may be substituted by M1, an alkyl group that may be substituted by W, an alkynyl group that may be substituted by W, a cycloalkyl group that may be substituted by W, or a group selected from an oxygen atom, a sulfur atom, and nitrogen 5 · to 12-membered heterocyclic group of an arbitrary heteroatom of the atom (The heterocyclic group may be as defined above.) M may be, for example, an alkyl group which may be substituted by M1, and an alkyl group which may be substituted by w ' Substituted alkynyl, cycloalkyl which may be substituted by M], or a 5 · all 12-membered heterocyclic group containing arbitrary heteroatoms selected from oxygen, sulfur, and nitrogen atoms (heterocyclyl may be substituted by M) Instead). ... is defined as above. "1 is, for example, a hydrogen atom, an alkyl group which may be substituted with M1, an alkenyl group which may be substituted with M <, an alkynyl group which may be substituted with M1, a cyclic hydrocarbon group which may be substituted with M1, or a group selected from an oxygen atom and a sulfur atom And 5 to 12 2 member heterocyclic groups of random heteroatoms of nitrogen atoms (heterocyclic groups may be substituted by Μ ί). μ] is the one defined above. R4 and R5 may each be, for example, a hydrogen atom, an alkyl group, a haloalkyl group, an aralkyl group, a heteroaralkyl group, a cycloalkyl group, a halocycloalkyl group, an alkenyl group, a haloalkenyl group, an alkyne-10-200526552 ( 7) radical, haloalkynyl, aryl or heteroaryl. 1 is, for example, a radical, a halogenated radical, an aromatic radical, a heteroaryl radical, an alkyl radical, a halocycloalkyl group, an alkenyl group, a haloalkenyl group, an alkynyl group, a haloalkynyl group, an aryl group, or a heteroaryl group . Halogen or a halogen acting as a substituent may include a parent atom of fluorine, chlorine, bromine or iodine. The number of halogens as a substituent may be 1 or more, and if more, the respective halogens may be the same or different. In addition, the substitution position of the halogen may be at any position. The radical or alkyl group may be linear or branched, and it may include a C]-] 2 alkyl group, for example, methyl, ethyl, propyl, isopropyl, butyl, butyl, As specific examples, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, or dodecyl. An alkynyl or alkynyl group may be straight or branched, and it may include c 2-] 2 alkenyl, for example, vinyl, 1-propenyl, allyl, isopropyl, 1-but Anthracene, 1,3-butanediyl, 1-hexyl, 1-heptyl, 4-octenyl, butdecenyl, or 2-dodecenyl are taken as specific examples. An alkynyl or alkynyl group may be straight or branched, and it may include a C 2 · 1 2 alkynyl ', for example, ethynyl, 2-butynyl, 2.pentynyl, 3.hexynyl , 4,4-dimethyl-2-pentynyl, 4-octynyl, 2-decynyl or dodecynyl as specific examples. The cyclic hydrocarbon group may be a monocyclic type or a condensed polycyclic type, and may be gastric saturated or have an unsaturated portion. Specific examples of the monocyclic hydrocarbon group may be, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclooctyl, cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cyclo Octenyl, cyclohexanedi-11-200526552 alkenyl, cyclooctadienyl, cyclooctynyl or phenyl. Specific examples of the condensed polycyclic hydrocarbon group may be, for example, naphthyl, anthracenyl, phenanthryl, dihydroindenyl, indenyl. The 5- to 12-membered heterocyclic group containing an arbitrary heteroatom selected from an oxygen atom, a sulfur atom, and a nitrogen atom may include a monocyclic or condensed ring type heterocyclic group containing 1 to 4 heteroatoms. This heterocyclic group may be saturated, or may have an unsaturated moiety, or its methylene moiety may be converted to a pendant oxo or thio (th 1 ο X 〇) ′ or may be N-oxidized Substance, for example, N_oxypyridyl. Preferably, it may be, for example, 1) a heterocyclic group, which is selected from the group consisting of thienyl, furanyl, allyl, thiazyl, isothio D, π, and iso , Imidazolyl, oxalyl, thiadiazolyl, Df diazolyl, triazolyl, tetrazolyl, dithiazolyl, pyridyl ', dacrotyl, pyrimidinyl, pyridyl, tricrotyl, Orthoxybenzyl, thiagenyl, piperanyl, benzothienyl, benzofuranyl, indolyl, isoindolyl, benzothiazolyl, benzoisothiazolyl, benzodoxazole

The methylene moiety is converted to a pendant oxygen group or a pendant sulfur group, a piperanyl group, a cyclopentylpyridyl group, or a saturated heterocyclic group containing a pendant oxygen group or a pendant sulfur group. 200526552 (9) group Ring base. The heterocyclic group described above may have several combinations through different positions of the hetero atom or different condensed portions, and the present invention includes all of them. For example, thiadiazolyl includes 1,2,3-thiadiazolyl and 1,3,4-thiadiazolyl; triazolyl includes 1,2,3-triazolyl and 152,4-triazolyl ; Trigenyl includes 1,2,4-trioxyl and 1,3,5-trigenyl; benzothienyl includes benzo [b] thienyl and benzo [c] thienyl; benzofuranyl Including benzo [b] furanyl and benzo [c] furanyl; benzoisothiazolyl includes 1,2-benzoisothiazolyl and 2,1-benzoisothiazolyl; benzoisoDfazolyl includes ; [, 2-benzoisodazolyl and 2 5 1-benzoisoxazolyl; and benzothiadiazolyl includes 1,2,3-benzothiadiazolyl and 2,1 5 3 -Benzothiadiazolyl. In addition, it applies to a partially saturated heterocyclic group, a saturated heterocyclic group, or a heterocyclic group containing a pendant oxygen group or a pendant sulfur group. The above-mentioned partially saturated heterocyclic group may be one having a part of the above-mentioned hydrogenated heterocyclic group. It may be, for example, 4 5 5 -dihydrothiazolyl, 4,5-dihydro Dfazolyl, 4,5-dihydroiso1] §azolyl, 455-dihydro-111-imidazolyl, 4, 5-dihydro-] fluorene-pyrazolyl, 3 5 4; 5,6-tetrahydropyridyl, 1,4; 5,6-tetrahydropyrimidinyl, 2; 3-dihydrobenzofuranyl or 4 a, 5 · 6,7,8,8 a _hexahydro D quinolinyl. The saturated heterocyclic group may be one having the fully hydrogenated heterocyclic group. It may be, for example, tetrahydrofuranyl, tetrahydropiperanyl, pyrrolidinyl, piperidinyl, oxanyl, or molyl. The heterocyclic group containing a pendant oxygen group or a pendant sulfur group may be partially saturated with the above-mentioned dithiazyl group, oxygen atom, sulfur atom, piperanyl group, cyclopentazopyrazolyl group, and benzodioxolium group. The methylene part of the heterocyclic group or the saturated heterocyclic group is converted into a pendant oxygen group or a pendant sulfur group. It may be, for example, 2- pendant oxytetrahydro-13- 200526552 (10) thienyl, 2- pendant thiotetrahydrothienyl, 2- pendant oxytetrahydrofuranyl, 2- pendant thiotetrahydrofuranyl, 2 -Pendantoxy pyrrolidinyl, 2 5 5 -dioxedyl pyrrolidinyl, 2,4-dioxedyl thiazolidinyl, heart pendant oxy-4,5-dihydrohumidyl, 4-side Oxy-4,5-dihydro-1H-imidazol-2-yl, 5-sideoxy-4,5-dihydro-1,1-Dttazolyl, 3-sideoxy-2,3-dihydro- 1H-pyrazolyl, 5-sidethio-5 '-[1,2,4] -dithiazolyl, 6-sideoxy-1,6-dihydropyridyl, 6-sideoxy-1,6 -Dihydrotapiryl, 2,6-dioxo-1,2,3,6-tetrahydropyrimidinyl, 3-oxo-3H- [1,2,4] trigenyl, 2- Pendant oxygen-1,2-dihydroquinolinyl, or 1,3-didoxy-1,3-dihydroisoindolyl. A cycloalkyl or cycloalkyl group may include a C3-8 cycloalkyl, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, or cyclooctyl. Aryl or aryl groups may include phenyl, naphthyl, anthracenyl, phenanthryl, dihydroindenyl or indenyl. Heteroaryl or heteroaryl groups may include those as described above. The salts of the haloene compounds of the above formula (I) include all kinds as long as the salts are acceptable in agriculture. For example, alkali metal salts, such as sodium or potassium salts; alkaline earth metal salts, such as magnesium or calcium salts; ammonium salts, such as dimethyl beta female salts or diethyl female salts, inorganic acid salts such as, Chlorochlorate, perchlorate, sulfate or nitrate; or organic acid salts, such as acetate or mesylate, may be included. The haloene compounds of formula (I) may have geometric isomers, optical isomers or tautomers, and both the isomers and mixtures thereof are included in the present invention. In addition, in the present invention, various strange objects' other than those described above may be included in the scope of general knowledge in the technical field. In addition, depending on the type of this isomer, the chemical structure of this isomer may be different from the formula (I) described above, but for those skilled in the art, this structure is an isomer relationship and therefore falls on It is obvious within the scope of the present invention. The haloene compound of the formula (I) or a salt thereof (hereinafter referred to as the compound of the present invention) can be prepared by the following reactions (A) to (H) and according to a general method for preparing a salt. G or its salt [A]

A II

XV X. , CH2 (CH2CH2) n-C-Cl (Μ)

XV / Y a G

II I

X〆 CH2 (CH2CH2) n-C-N-L (I) In the reaction (in), 乂 1, 2,2, y,]], [, 0, and eight are as defined above. In addition, the salts of the compound of the formula (? I) may include organic acid salts or inorganic acid salts, for example, hydrochloride, sulfate, oxalate or mesylate. Reaction (A) can be carried out in the presence of a base, if required by the case. One or more types of bases may be appropriately selected and used from the following groups: for example, tertiary amines, for example, trimethylamine, triethylamine, triisopropylamine, diisopropylethylamine, pyridine , 4-dimethylaminopyridine, 2,6-dimethylpyridine, 4-pyrrolidinopyridine, N-methylmorpholine, N, N-dimethylaniline, N5N-diethylaniline , N-ethyl, .methylaniline, 丨, 8-diazabicyclo [5 · 4.0] -7-undecene or 1,4-diazabicyclo [2 · 2.2] octane; alkali metals, For example, sodium or potassium; alkali metal carbonates, such as sodium carbonate or potassium carbonate; -15-200526552 (12) alkali metal hydroxides, such as sodium hydroxide or potassium hydroxide; alkali metal hydrides, such as hydrogenation Sodium or potassium hydride; alkali metal bicarbonates, such as sodium or potassium bicarbonate; and alkyl lithiums, such as butyl lithium. The base can be used in an amount of from 1 to 5 mol times, preferably from 1 to 2.5 mol times per mol of the compound of formula (II). Reaction (A) can be carried out in the presence of a solvent, if required by the case. The solvent may be any solvent as long as it is a solvent that is inert to the reaction, and one or more types of solvents may be appropriately selected from the following groups and used: for example, aliphatic hydrocarbons such as pentane, hexane, heptane , Octane or cyclohexane; aromatic hydrocarbons, such as benzene, toluene, xylene or pyridine; halogenated hydrocarbons, such as chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloride Ethane, or trichloroethane; ethers, such as diethyl ether, butylethyl ether, tetrahydrofuran, dioxane, dimethoxyethane, or anisole; esters, such as methyl acetate, ethyl acetate , Or propyl acetate; ketones, such as acetone, diethyl ketone, methyl ethyl ketone, or methyl isobutyl ketone; and polar aprotic acids, such as acetonitrile'propionitrile, N5N-dimethylformamide Pyridoxine, dimethylimide, hexamethylphosphortrioxamine, cyclobutane, dimethylacetamide, or N-methylpyrrolidone. The reaction (A) can be carried out in an inert gas atmosphere, 'if required by the case ^ in the case of inert gas', which may include each gas 'such as' nitrogen, helium or rapid gas. The reaction (A) can usually be carried out at a temperature from · 78 to +2 50 ° C ', preferably from · 78 to +50]. It is carried out in C, and the reaction time is usually from 0 ·] to 72 hours, preferably from 0 ·] to 24 hours. -16- 200526552 (13)

G HfV-UIII 丨 or its salts

CH2 (CH2CH2) n-C-N-L In the reaction (B), X ^ xlY'n'L, G, and a are as defined above, and T is an oxygen atom or a sulfur atom. The salts of the compound represented by the formula (III) may include the same as those exemplified in the above reaction (A). Reaction (B) can be carried out by azeotropic dehydration as a cycle in the presence of a solvent or a condensing agent '. The solvent to be used for the azeotropic dehydration may be any solvent as long as it is a solvent which is inert to the reaction, and, for example, one or more types of solvents may be appropriately selected from those exemplified in the above reaction (A) and used. In addition, in one case, the reaction was performed in the presence of a condensing agent, and a solvent could be used, if the case requires it. The solvent to be used in this case may be any solvent as long as it is inert to the reaction, and, for example, one or more types of solvents may be appropriately selected from those exemplified in the above reaction (A) and used. The condensing agent used in the reaction (B) may include carbodiimide; for example, 1: 3-dicyclohexylcarbonyldiimide, -diisopropylcarbonyldiimide, or ethyl 3- (3 -Dimethylaminopropyl) carbodiimide hydrochloride; or others, for example, phenyldichlorophosphate, diethylcyanophosphonate, 1,3; 5-triaza- 2; 4 5 6 -triphosphorus-2 5 2; 4,4,6; 6-hexachloride, cyanuric chloride, -17-200526552 (14) isobutylchloroformate, chlorosulfonyl Isocyanate, N, N'-carbonyl ditaste # group, or trifluoroacetic anhydride. The amount of the condensing agent used may be from 1 to 5 mol times, preferably from 1 to 2 mol times per mole of the compound of formula (IV).

Reaction (B) can be carried out in the presence of a base when the case requires it. _ Or more types of bases may be suitably selected and used from the following groups: for example, tertiary amines such as trimethylamine, triethylamine, triisopropylamine, diisopropylethylamine, D [t Didine, 4-dimethylaminopyridine, 2,6-dimethylpyridine, pyrrolidinopyridine, N-methylmorpholine, IN-dimethylaniline, N, N-diethyl Aniline, and N-ethyl-methylaniline. The amount of the base to be used may be from 0.1 to 5 mol times per mole (IV) of the compound, and preferably from 0.1 to 2.5 mol times. Reaction (B) can be carried out in an inert gas atmosphere when the case requires. In the case of an inert gas, it may include, for example, nitrogen, helium, or argon. The reaction (B) can usually be carried out at a temperature from -78 to +250 ° C, preferably from 0 to 150 ° C, and the reaction time is usually from 0.1 to 72 hours, preferably from 0 to · 1 to 24 hours. [C] P ^ C ====: < fi H (i_L (m) · or its salts X CH2 (CH2CH2) n ~ C-T-2--3 (V)

X1 \ Y A G

Y) c === z < II I

X CH2 (CH2CH2) n—C—N—L Ο) ~ 18- 200526552 (15) In reaction (C), X1, x2, Y, n, L, G, eight, and T are as defined above, and Z is a Cy alkyl group. The salts of the compound represented by the formula (111) may include the same as those exemplified in the above reaction (A). Reaction (C) can be carried out in the presence of a base when the case requires it. -One or more types of bases may be suitably selected from the following groups and used: for example, those exemplified in the above reaction (A), and alkali metal alkoxides, for example, β sodium methoxide, ethyl sodium, and potassium butoxide; And secondary amines, for example, trimethyl * amine, triethylamine, triisopropylamine, diisopropylethylamine, pyridine, 4-phi dimethylamino group D ratio, 2, 6 -Dimethyl 0 to 0, and D to slightly {] and D [: td, N_methylmorpholine, N, N-dimethylaniline, N, N-diethylaniline, and & Ethyl N-methylaniline. The amount used in the test may be from 0.001 to 5 mol times, preferably from 0.001 to: 2.5 mol times per mole of the compound (v). Reaction (C) can be carried out in the presence of a solvent when the case requires it. The solvent may be any solvent as long as it is inert to the reaction, and, for example, one or more types of solvents may be appropriately selected from those exemplified in the above reaction (A) and used. The Φ reaction (C) can be carried out in an inert gas atmosphere when the case requires it. The inert gas may include each gas, for example, nitrogen, helium, or gas. The reaction (C) is usually available at temperatures from -78 to +2.50. C, preferably from 0 to _] 50 ° C, and the reaction time is usually from 0.] to 72 hours, preferably from 0.1 to 24 hours. • 19- 200526552 (16) [D] XV X2 ‘; c— (M) CH2 (CH2CH2) n— 丨

NH-L G1-x3 (VI) X1 \ x2 * c = c. 、 CH2 (CH2CH2) n · (Bu 2)

G1I • N—L In reaction (D), G] is alkyl, haloalkyl, phenylalkyl, alkenyl, haloenyl, phenylalkenyl, alkynyl, haloalkynyl, phenylalkynyl, -C (= B) Q, -C (= B) B'Q, -C (= B) N (G,) Q, -SQ, -S02Q, -SN (G ') Q, -SN (G' ) C (= B) B'Q or-S02N (G ') Q, and χ3 is the tooth element, and 乂], and 2, ya'11,] ^, (}, 6, 6, and (5 are the above) As defined. Reaction (D) may be carried out in the presence of a base, when the case requires. One or more types of base may be appropriately selected from, for example, those exemplified in the above reaction (A), and used. The amount used may be from 0.01 to 10 mol times per mole of the compound of formula (1-1), and preferably from 0.001 to 5 mol times. The reaction (D) may be at N- Implemented in the presence of trialkylsilyl-alkylaminoformate 'when the case requires. In the case of N-trialkylsilyl-alkylaminoformates, one or more types of N-triane Silyl-alkylcarbamate may be appropriately selected from, for example, N-trimethylsilyl-ethylcarbamate and N-triethylsilane -Methylcarbamate, and used. N-trialkylsilyl-alkylcarbamate may be used in an amount of from 0.01 to 1 per mole (I-]) compound. To 10 mol times, preferably from -20- (17) (17) 200526552 〇1 to 5 mol times. Reaction (D) can be carried out in the presence of a solvent when the case requires. Solvents can Any solvent as long as it is inert to the reaction, and, for example, one or more types of solvents may be appropriately selected from those exemplified in the above reaction (A) and used. The reaction (D) may be in an inert gas atmosphere. It is implemented when the case requires. As far as the inert gas is concerned, it may include, for example, nitrogen, ammonia, or argon. The reaction (D) may be usually at a temperature from -78 to +25 0CC, preferably from 0. It is carried out to 150 ° C, and the reaction time is usually from 0 :: [to π hours, preferably from 0.1 to 24 hours. [E]

χΐ \ Y A / C — C \ II G2-〇s〇2-u (νιι) X CH2 (CH2CHj2) n—C-NH-L 1 ~ (1-1) 1 Λ 2

Xnv—〆 γ Γ G / C C \ j

X2 CH2 (CH2CH2) n-C ~ N-L (Bu 3) In the reaction (£), 乂], 乂 2, y, 11, 1 ^, and eight are as defined above, G2 is alkyl, and u It is alkyl, haloalkyl, alkoxy, phenyl, halogen-substituted phenyl, or phenyl. Reaction (E) can be carried out in the presence of a base when the case requires it. One or more types of bases may be appropriately selected from, for example, those exemplified by the above reaction (A) and used. The amount of base used may be from 0.001 to 10 mol times, preferably from 0.001 to 5 mols, per mole of the compound (I-1) compound -21-200526552 (18). Times. Reaction (E) can be carried out in the presence of a solvent when the case requires it. The solvent may be any solvent as long as it is a solvent inert to the reaction, and, for example, one or more types of solvents may be appropriately selected from those exemplified in the above reaction (A) and used. Reaction (E) can be carried out in an inert gas atmosphere when the case requires it. In the case of an inert gas, it may include each gas, for example, nitrogen, helium, or argon. Reaction (E) is usually available at temperatures from -78 to +250. (3, preferably from 0 to 150 ° C, and the reaction time is usually from 0 to 72 hours, preferably from 0.1 to 24 hours. [F] xV X2 y gc = < II I CH2 (CH2〇H2) n-C-N " (b. 4) Thiochemical reagent

-L x1 \ X2

S G C = C,

CH2 (CH2CH2) n-C-N-L (Bu 5) In reaction (F), X1, X2, γ'n, L and G are as defined above. In the reaction (F), in the case where a carbonyl group is present in L, this mineral group can be sulfated. The thiolation reagent used in the reaction (F) may include, for example, phosphorus pentasulfide or La wesson's reagent. The amount of the thiolation reagent may be from 1 to mol, preferably from 1 to 4 mol, per -22-200526552 (19) mol (1-4). In addition, in the case where the carbonyl group in L is to be thiolated, a corresponding amount of thiolating reagent can be added. Reaction (F) can be carried out in the presence of a solvent when the case requires it. The solvent may be any solvent as long as it is inert to the reaction, and, for example, one or more types of solvents may be appropriately selected from the following groups and used: aliphatic hydrocarbons such as pentane, hexane, heptane , Octane, and cyclohexane; aromatic hydrocarbons, such as benzene, toluene, xylene, and pyridine; halogenated hydrocarbons, such as chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloride Ethane, and trichloroethane; ethers, such as diethyl ether, butyl ethyl ether, tetrahydrofuran, dihumane, dimethoxyethane, and anisole; esters, such as methyl acetate , Ethyl acetate, and propyl acetate; and polar aprotic solvents, such as acetonitrile, propionitrile, dimethylasoterol, and cyclobutane. Reaction (F) can be carried out in an inert gas atmosphere when the case requires it. As far as the inert gas is concerned, it may include each gas, for example, nitrogen, helium, or M gas. The reaction (F) may generally be at a temperature from -78 to + 2 5 0 ° C, preferably from 0 to 5] It is carried out within 0 ° C, and the reaction time is usually from 0.1 to 72 hours, preferably from 0.1 to 24 hours. In the compounds of the present invention, compounds where L is -C (= B) Q, -C (= B) B'Q, -C (= B) N (D) Q, -S02Q or -S02N (D) Q are also It can be prepared according to the reaction (G). -23- 200526552 (20) [G] x > X〆

y ag < M CH2 (CH2CH2) n-C-N-H (VIII) or its salts

Ci—E X1, .Y AGX ii i X2 CH2 (CH2CH2) n—CN—E (I-6) In reaction (G), E is -C (= B) Q, -C (= B) B ' Q, -C (= B) N (D) Q, -S02Q or -S02N (D) Q, and X], X2, Y, n, G, D, A, B, B ^ Q are as defined above . In addition, the salts of the compound of the formula (VIII) may include, for example, the same as the salts of the compound of the formula (III). Reaction (G) can be carried out in the same manner as in the above reaction (A). Among the compounds of the present invention, compounds in which L is -C (= B) NHQ can be prepared according to reaction (i). [Η] χ1χ X〆

A G c = c. CH2 (CH2〇H2) n-C-N-Η (v " i) or its salts B = C = N_〇

Χ2 > = < Υ Η? I

X2 CH2 (CH2CH2) n-CN-C-ΝΗ-Q (Ι-7) In the reaction (Η), X], X2 'Υ, η, G, A, B, and Q are as defined in the above-mentioned 200526552 (21) By. In addition, the salt of the compound of the formula (V111) may include, for example, the same salt as the compound of the formula (III). Reaction (H) can be carried out in the same manner as in the above reaction (A).

Each of the starting materials of formulas (II), (IV) or (V) in the above reactions (A) to (C) is (1) a known one, or (2) can be prepared by or in accordance with the preparation examples below, Or (3) can be prepared by or according to the method disclosed in W092 / 1 5 5 5 5, EP661 2 8 9 or EP 4 3 2 8 61. The above (3) will be described in more detail. a) The method disclosed in W092 / 15555, page 15, line 16 to page 16, line 3, optionally implements the general chlorination or esterification method, followed by this method, in the WO Preparation Examples 16, 22 , 28, or 42. b) The method disclosed in EP 66 1 289, page 13, line 25 to page 14, page 37, method disclosed in or based on EP Preparation Example Zl, Z2 or Z3. c) EP4 3 2 8 6 1 The method disclosed on page 4 line 22 to page 8 line 45, the method or basis disclosed in EP Preparation Example 3, 4, 8, 9, 10 or 16 Method. The compound of formula (VIII) or its salt in the above reaction (G) or (H) can be prepared by the following general reactions (I) to (K) and general methods for preparing salts. -25- (22) (22) 200526552 χ1 \ Γ: == η / γ f | G-NΗ2 (IX) or its salts χ2〆 \ cH2 (CH2CH2) n-C-Cl

XV / Ah A G

2 > = < II I

X2 CH2 (CH2CH2) n-C-N ~ H (VIII) In reaction VII, f'f'Y'n'G and A are as defined above. In addition, the salts of the compound of the formula (IX) may include, for example, those which are the same as the salts of the compound of the formula (III). Reaction (I) can be carried out in the same manner as in the above reaction (A). [J] xVr; —p / Y A g—νη2 (π) or its salt 乂 2 ^ CH2 (CH2CH2) n—C-T-H " — (IV)

X1 \ / V A G

2 / C = < III

X2 CH2 (CH2CH2) n-C-N-H (VIII) In the reaction (J), X], X2, Y, n, G, and A are as defined above. In addition, the salts of the compound of the formula (IX) may include, for example, the same salts as those of the compound of the formula (III). The reaction (υ can be carried out in the same manner as the above reaction (B). -26- 200526552 (23) [K]

Xl \ c = icf Ah f) G-NH2 (IX) or its salt

2 > = < I I

X CH2 (CH2〇H2jn-C-N-H (VIII) In the reaction (K), 1, 2, 2, Ya, 11, 0, 8, D, and 2 are as defined above. In addition, the formula ( IX) The salt of the compound may include, for example, the same salt as the compound of the above formula (II). The reaction (K) can be carried out in the same manner as the above reaction (C). Preferable specific examples will be described below. Insecticide systems containing the compounds of the present invention are particularly useful, for example, for controlling various pests and reagents which have become a problem in the fields of agriculture and horticulture, that is, agricultural and horticultural killing. Insecticides, or agents that control parasitic pests on animals, that is, insecticides that resist parasitic pests on animals. Agricultural and horticultural insecticides containing the compounds of the present invention are useful insecticides, insecticides, nematicides Agents and soil insecticides, which effectively control plant parasitic contact, for example, Tetranychusurticae, T etranchusci η nabarinus, Tetranychus kanzawai 'Panonychus citri, Panonychus ulmi, Polyphagotarsonemus atus, A ci} 1 opspe ekassi, and Rhizoglyphus echinopus Polar insects, such as peach aphid (jyfyzus persicae) and cotton aphids (A phisg 〇ssypii); agricultural insect pests, such as -27-200526552 (24) Plutella xylostella, Mamestra brassicae , Spodoptera litura, Laspeyresia pomonella, Heliothis zea, He 1 iothisvirescens, Lymantriadispa ·, Rice leaf curler (Cnaphalocrocis medinalis), Chaji leaf roller moth (Adoxophyes s p.), potato beetle (Leptinotarsa decemlineata), yellow melons (Aulacophora fem oralis), cotton weevil (Anthonomus grandis), planthoppers, brown leafhopper, scale insect, insect , Whiteflies, thrips, locusts, black flies, scarabs, Agrotis ipsilon, night Agrotis segetum and ants; plant parasitic nematodes, such as rhizobial nematodes, cyst nematodes, root rot nematodes, A phe 1 ench 〇idesbesseyi, strawberry bud nematodes (Nothotylenchus acris), Pine wood nematodes (B u 1 · saphe 1 enchus 1 ignic ο 1 us); gastropods, for example, including snails and snails; soil pests, for example, isopoda, for example, pi 1] bugs (A rmadi 1 idi υ mv υ 1 gare) and pillbugs (Porcellio scaber); insect pests such as Ornithonyssus bacoti, cockroaches, Musca doniestica and Culex pipiens; collected grain insect pests such as, Sistotraga cerealella (Callosobruchus chinensis), Tribolium castaneum and bread worms; household goods insect pests, such as Tinea pellionel (a), black carpet beetle (A nthrenusscr 〇phu) aridae ) And subterranean termites; homes, for example, saprophytic shade (T y) · 〇phagusput · E s c e n t i a e) 'Americas dust -28 - 200526552 (25) (Dermatophagoides farinae) and South pawl lice (Chelacaropsis m ο ο ι · e i). Among them, agricultural and horticultural insecticides containing the compound of the present invention are particularly effective for controlling plant parasitic mites, agricultural insect pests, plant-derived nematodes or the like. In addition, it is effective against insect pests that have been resistant to organophosphorus, carbamate, and / or synthetic pyrethroid insecticides. Furthermore, the compounds of the present invention have outstanding systemic properties, and by applying the compounds of the present invention to soil treatment, not only can they control harmful insects, harmful mites, harmful nematodes, harmful gastropods, and other harmful substances in the soil. Foot animals can also control leaf pests. Another preferred specific example of the insecticide containing the compound of the present invention may be agricultural and horticultural insecticides, which collectively control the above-mentioned plant parasitic mites, agricultural insect pests, plant parasitic nematodes, gastropods, and soil pests.

Agricultural and horticultural pesticides containing the compounds of the present invention are usually prepared by mixing the compound with various agricultural adjuvants and used in the following dosage forms: powder, granules, water-dispersible granules, miscible with water Powder, suspension concentrate with water as substrate, suspension concentrate with oil as substrate, water-soluble particles, milky concentrate, soluble concentrate, paste, aerosol or ultra-small volume preparation. However, as long as it is suitable for the purpose of the present invention, it can be formulated into any type of preparation commonly used in the field. This agricultural adjuvant includes solid carriers such as diatomaceous earth, slaked lime, calcium carbonate, talc, white carbon, kaolin, bentonite, a mixture of kaolin and sericite, clay, sodium carbonate, sodium bicarbonate, thenardite, zeolite, and Starch; solvents, for example, water, toluene, xylene, solvent naphtha 'dioxane, acetone, isophorone, methyl isobutyl ketone, chlorobenzene, chlorohexane, dimethylmethylene, H- 29- 200526552 (26) Dimethylformamide, dimethylacetamide, N-methyl-2-pyrrolidone, and alcohol; anionic surfactants and dispersants, such as fatty acid salts, benzene Formates, alkylthiosuccinates, dialkylthiosuccinates, polycarboxylates, alkyl sulfate salts, alkyl sulfates, alkylaryl sulfates, alkyl diethylene glycol Ether sulfates, alcohol sulfate salts, alkane sulfonates, alkylaryl sulfonates, aryl sulfonates, lignin sulfonates, alkyl diphenyl ether disulfonates, polystyrene Sulfonates, salts of alkyl phosphates' alkylaryl phosphates, styryl aryl phosphates, polyoxyethylene alkyls Salts of sulfates, polyoxyethylene alkylaryl ether sulfates, polyoxyethylene alkylaryl ether sulfates, polyoxyethylene alkyl ether phosphates, polyoxyethylene alkylaryl phosphates Salts and salts of condensates of naphthalene sulfonates and aqueous formaldehyde; non-ionic surfactants and dispersants, such as sorbitan fatty acid esters, glyceryl fatty acid esters, fatty acid polyglyceryl esters, fatty acid alcohols Polyethylene diether, acetylene glycol, acetylenic alcohol, oxyalkenyl fluorene polymer, polyoxyethylene alkyl ether, polyoxyethylene alkylaryl ether, polyoxyethylene styrylaryl ether, polyoxyethylene Glycol alkyl ether, polyethylene glycol, polyoxyethylene fatty acid ester, polyoxyethylene sorbitan fatty acid ester, polyoxyethylene glycerol fatty acid ester, polyoxyethylene hydrogenated castor oil, and polyoxypropylene Fatty acid esters; and vegetable and mineral oils, such as olive oil, kapok oil, castor oil, 'palm oil', camellia oil, coconut oil, sesame oil, corn oil, rice bran oil, peanut oil, cotton seed oil, soybean oil, rapeseed rice oil, Linseed oil, tung oil, and liquid paraffin. In the case of an adjuvant, one or more of each ingredient may be appropriately selected for use, as long as the purpose of the present invention can be accomplished by this. In addition, various additives that are often used, such as --30- 200526552 (27) fillers, thickeners, anti-settling agents, anti-freezing agents, dispersion stabilizers, phytotoxicity reducing agents, and anti-mildew agents can also be used. used. The weight ratio of the compound of the present invention to various agricultural adjuvants is usually from 0.00 1: 99.999 to 95: 5, preferably from 0.005: 99.995 to 90: 10 °. In the real application of this preparation, it can be used when When the case requires, it can be diluted to a predetermined concentration with diluents, such as water and various dispersants, such as surfactants, vegetable oils or mineral oils. The application of agricultural and horticultural pesticides containing the compounds of the present invention may generally not be defined because it varies depending on weather conditions, the type of preparation, the season of application, the location of application, or the type or degree of attack of insect pests. However, it is generally applied in the form of an active ingredient concentration ranging from 0.5 to 8,000,000 ppm, preferably from 0.5 to 50,000 ppm, and the dosage per unit area is such that the compound of the present invention is from 0.05 to 50,000 g / ha , Preferably from] to 30,000 g / ha. In addition, an agricultural and horticultural insecticide 'containing the compound of the present invention as another preferable specific example of the insecticide can be applied according to the application of the above-mentioned insecticide. The present invention includes a method for controlling pests by the application, particularly for controlling plant parasites, agricultural insect pests or plant parasitic nematodes'. Various formulations of agricultural and horticultural pesticides containing a compound of the present invention or a diluted composition thereof may be applied by conventional application methods, such as spraying (ie, spraying, spraying, spraying, atomizing, powdering, or Particles scattered or dispersed in water), soil application (ie, mixing or soaking), surface coating (ie, coating, powder, or covering) or impregnation to obtain a toxic feed. 200526552 (28) In addition, it is possible to feed domestic animals with food containing the above-mentioned active ingredients, and to control the infestation and growth of pests, especially insect pests, with animal excrement. Furthermore, the active ingredient can also be applied by a so-called ultra-small volume application method. In this method, the composition can be composed of 100% active ingredient. In addition, agricultural and horticultural insecticides containing the compound of the present invention can be mixed with other agricultural chemicals, fertilizers, or phytotoxicity reducing agents or used in combination to obtain synergistic effects or activities. Other agrochemicals include, for example, herbicides, insecticides, herbicides, nematicides, soil insecticides, fungicides, antivirals, attractants, antibacterials, plant hormones and plant growth regulators Agent. More specifically, for a mixed insecticide having a compound of the present invention mixed with or combined with one or more active ingredients of other agricultural chemicals, the preferred improvement policy may be the application range, application time, and insecticidal activity. and many more. The compounds of the present invention and the active compounds of other agrochemicals can be prepared separately so that they can be mixed at the time of application 'or they can be prepared together. The present invention includes such a mixed insecticidal composition. The mixing ratio of the compound of the present invention to the active compounds of other agrochemicals may generally not be defined because it varies depending on weather conditions, the type of preparation, the application time, the application location, or the type or degree of insect pests, but it is usually From 1: 3 00 to 3 0 0: 1, preferably from! : 100 to 100: 1 in a weight ratio range. In addition, the application dose is such that the total amount of the active compound is from 0 ·] to 50; 000 g / ha, preferably from] to 3,000,000 g / ha. The present invention includes a method for controlling pests by applying the mixed insecticidal composition to -32-200526552 (29). Active compounds of insect pest control agents, such as insecticides, insecticides, nematicides, or soil insecticides among the other agrochemicals mentioned above, including, for example (common names, some of which are still in use) organophosphate compounds , For example, plus pine, dichloroson, fenfluxon, fenfluxon, one bite

PP pine, big pine, dosson-methyl, ethoxymone, thiophene pine, forsythia, phosphocarb, clendane, dithizone, dossone, mirazepine, damirson, and damascene; aminomethyl Acid salt compounds, for example, Gaboli, Andan, Temex, Gabof, Thiodix, Nanaide, Eurocide, Alfink, Bigap, Butyl Piraceta, Butyl Gabo Fu, and Fu Fu Ke; nereis toxin derivatives, such as Pedan, thiosulfan, and Mo Su Da; organic chlorides such as Da grams of mite, and de-mite; organometallic compounds, such as Fenbuci; Pyrethrin compounds, such as, for example, fenvaleride, fenpronil, cyphenidin, diphenirin, cylonin, tefluthrin, ifenin, fenpronin, and bifennine; phenazinamide compounds, for example, difuku Long, Cefron, Teflon, Flufenon, Lufenlon, and Nova 1 ur ο η; Barrenoid compounds, for example, Mithrin, Periperfin, and Fenock; Da Ketone compounds', for example, Bidamu; pyrazole compounds, for example, fenprox, fenproni, pyraclostrobin, acetaminophen, Tol fenpyrad, and Acetoprole; neonicotinoids, for example, itamide, nitenpyram, imifenpyr, thiamethoxam, celestine, cotinine, and dartnan; hydrazine compounds, such as Defeno, Meth ο X yfe η 〇zide, and Chr 〇in afe η ozide; dinitro compounds; organic sulfur compounds; urea compounds; trio compounds; hydrazone compounds, and other compounds, such as F 1 ο nicamid, bufenazole, Hesedor, Sanya, -33-200526552 (30) Insecticides, siloxafen, pyracloscarb, Piracetam, Bizifen, Kefanpai, Intec, Asia Quinone mite, ecdysticid, cyphenidine, 1,3-dichloropropene, Teflon, Benclothiaz, Flufenerim, Pyrida 1 y 1,

Spirodiclofen, Bifen azate 'Spiromesifen, Euclid, Kefen, and F 1 u a c r y p y r i m. In addition, BT reagents, microbial agrochemicals, such as' insect viruses, Entoniopathogenic fungi, and nem atop hagous fungi, or antibiotics, such as A vermecti η, It can be blended or combined for use with fendi, mirex, dioxin, and love insects. The active compounds of fungicides in the above-mentioned other agricultural chemicals include, for example (common names, some of which are still in use), pyrimidine compounds, for example, metronid, pameni, and cyproxazole; azole compounds, For example, Tritefen, Bidnon, Safeford, Etaconazole, Pukeley, Pinker, Huxide, Minick, Cyclops, Terbuconazole, Fikeli, Furconazole-cis, Poker, Metco n azole , Epox, Sicli, O X ρ 〇c ο na ζ 〇 e, and Sipconazole; mouth quinololine compounds, for example, qui η 〇methi ο nate; dithiocarbamate compounds, for example, manganese Naipu, Zinc Naipu, Zinc Manganese Naipu, Polycarbamate, Methylzine Naipu; Organic chloride compounds such as Rebis, Tetrachloroisobenzonitrile, and Pentachloronitrobenzene; Imidazole compounds , For example, radide, methyl doproxil, befentin, and thiophene; pyridine amine compounds, such as fugulimide; cyanoacetamide compounds, for example, chloracetamide; phenylamidamine compounds, For example, Mundal, Orgas, Ofu race, Bendale, Furalaxyl, and Cyprofuram; sulfenic acid compounds, such as Yifaling; copper compounds, such as, hydroxides, 200526552 (31) copper, and clodyne; isoDfazole compounds, such as hydroxyisoDfazole Organophosphorus compounds such as, for example, Foseid, Texon, S-benzyl 0,0-diisopropylthiophosphoric acid ester, 0-ethyl S 5 S-diphenyldithiophosphate, And aluminum methylphosphonic acid salts; N-halosulfanyl compounds, such as, for example, Gaptan, Tetrachlorodane, and Folke; dicarboxamide compounds, such as, for example, metronid, iptop, and exempt Knin; benzamidine benzene compounds, such as fordonine, metronidine, and Zoxamide; piperazine compounds, for example, safonine; pyrizine compounds, for example, bifenox; methanol compounds, for example, fenestram, And Hufenfen; _ B compounds, such as Fenpr oopidine; morpholine compounds, such as Fempf; organotin compounds, such as triphenyltin hydroxide, and triphenyl vinegar Tin; Urea compounds, such as Penclone; Cinnamate compounds, for example, Da Fen; phenylcarbamate compounds, such as Diethofencarb; cyanopyrrole compounds, such as Hutongning, and Fenpiclonil; Strobilurin compounds, such as attomin, ketoxin, Metominofen, trifluoromin, Picoxystrobin, and Bacromin; Oroxazolidine dione compounds, for example, Vanoxazine; Thiazole carboxamide compounds, for example, Et ha box am; Ethyl pyramine compounds, for example,

Silthiopham; aminoamine aminocarbamate compounds, for example, I pr vava 1 icarb; midazolide compounds, for example, F enamid ο ne; hydroxyanilide compounds, for example, Fenhexamid Benzsulfuronamide compounds, such as fluoxan; anthraquinone compounds; crotonic acid compounds; antibiotics; and other compounds, such as Yaciba, trisazole, Pyroquilon, dalimone, chlorpyrifol, fast norfen, general Pak, Sp i i ο X amine, bitter chloride, Myron, and Metam-S od] .um. -35-200526552 (32) In addition, the agricultural chemical that can be blended or combined with the compound of the present invention may be, for example, uncovered in F arm C hemica 1 s H andb οk (2 0 0 0 version) Active ingredient compounds in herbicides, especially those of soil treatment type. Insecticides that are effective against parasites in animals are effectively controlled, for example, external parasites that are parasitic on the surface of the host animal's body (for example, the back, underarms, lower abdomen, or the inside of the thigh), or in the host animal (for example, , Internal parasites of the stomach, intestines, lungs, heart, liver, blood vessels, subcutaneous or lymphoid tissues), but it is particularly effective in controlling external parasites. External parasites can be, for example, animal parasitic roundworms or fleas. Many types make it difficult to list all of them, so typical examples are as follows. Animal parasitic fleas can be, for example, ticks, such as boickus microplus, Rhipicephalus sanguineous, long-horned blood Haemaphysa] is longicornis, Haem aphysalis flave, Haem aphysalis campanu ata), Haem aphysalis concinna, Haem aphysalis japonica, blood Haemaphysalis kitaokai, Haem aphysalis ias, Ixodes ovatus, Ixodes nipponensis, Ixodes persulcatus (Amblyomma testudinarium), Haemaphysalis megaspinosa, Dermacentor reticulates, and Dermacentortaiwanwsis; Dermanyssusga Π inae; 1¾, -36- 200526552 ( 33) m such as: 〇rnith ο nyssussy 1 viar um and Ornithonyssus bursa; tromb idioids, for example, Eutrombicu] awichma η ni, Leptotrombidium akamushi, Leptotrombidium pallidum, Leptotrombidium fuji, Leptotrombidium tosa, Neotrombidium autumnalis, Eutrombicula alfredicula mica ; Ticks, for example, ascites (C hey 1 etie 11 ayasgul · i), ascites (Cheyletiella parasitivorax), and ascites (Cheyletiella blakei); tinea mites, for example, Psoroptes cuniculi, Horse sucking allows psoriasis bovis, Otodectes cynotis, Sarcoptes scabiei, and Notoedres cati; and hair follicles, for example, Demodexcanis . Insecticides against parasites on animals containing the compounds of the present invention are particularly effective in controlling ticks in parasites. Fleas can be, for example, external parasitic wingless insects belonging to the order Siphonaptera, and more specifically, fleas belong to the family Pulicidae, Ceratephyllns, and the like. The flea belonging to the family Flea family can be, for example, Ctenocephalides canis, Ctenocephalides felis, Pulex irritans, chicken flea (E chid η ophaga gallinacea), Indian rat flea (X e η opsy 1 la cheopis), blind eggs (Leptopsyl) a segnis) 'European rat flea (Nosopsyllus fasciatus) and monopsylus flea (Monopsyllus anisus). Insecticides against parasites on animals containing the compound of the present invention are particularly effective in controlling fleas belonging to the family Flea, in particular, dog flea and cat in the family Flea -37-200526552 (34) Fleas. Other external parasites can be, for example, sucking lice (A n oplura), for example, short nosed cattle louse (Haematopinus eury stern us), horse 1¾ (haematopinus asini), sheep 1¾, Long nosed cattle louse (Linognathus vituli) and head 1¾ (Pediculus capitis) i biting lice, for example, dog bites | ^ (Trichodectes canis); and blood-sucking dipterous insects, for example, Horse fly (T abanustrig ο nus), pupae (Culicoides schultzei), and pupae (Simuliinn ornatum). In addition, internal parasites can be, for example, nematodes, such as lung worms, Trichuris ^ tuberous worms, gastric parasites, roundworms, and filariasis; stripworms; trematodes; and protozoa, such as coccidia , Malaria parasite (Plasmodium malariae), intestinal sarcocyst, toxoplasma, and Cryptosporidium. The host animal may be, for example, a pet animal. , For example, dogs, cats, mice, rats, hamsters, guinea pigs, squirrels, rabbits, blood marten, birds (for example, pigeons, parrots, myna, pheasants, honey suckers, acacias and canaries); domestic animals, such as , Cattle, horses, pigs, and sheep; and poultry, such as ducks and chickens. Animal parasite-resistant insecticides containing the compounds of the present invention are particularly effective in controlling pests that are parasitic to pet animals or domestic animals, and particularly, to control external parasites therein. Among pet animals, it is particularly effective for dogs and cats, and among domestic animals, it is especially effective for cattle and horses. -38- 200526552 (35) When the compound of the present invention is used as a pesticide against animal parasites, it can be used 'or can be used with appropriate adjuvants, it can be formulated into various dosage forms', for example, powder, granules , Tablets 'powders, capsules, soluble concentrates' emulsifiable concentrates, water-based suspension concentrates and oil-based suspension concentrates. In addition to this dosage form, it can be formulated into any dosage form customarily used in the field as long as it is suitable for the purpose of the present invention. The adjuvant to be used in the dosage form may be, for example, an anionic surfactant or a non-ionic boundary φ surfactant as an adjuvant for agricultural and horticultural pesticide formulations exemplified above; a cationic surfactant, for example, Acetyltrimethyl bromide bromide; solvents such as water, acetone, acetonitrile, monomethylacetamidamine, dimethylacetamide, dimethylformamide, 2-pyrrolidone, N-formyl -2-Pyrrolidone, kerosene, triacetin, methanol, ethanol, isopropanol 'benzyl alcohol, ethylene glycol' propylene glycol, polyethylene glycol, liquid polyethylene oxide glycol, butylene glycol Ether, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monoethyl ether, diethylene glycol n-butyl ether, dipropylene glycol monomethyl ether, or monopropylene glycol n-butyl ether; Antioxidants, such as butyl hydroxyanisole, butylhydroxytoluene, ascorbic acid, sodium hydroxy metabisulfite, propyl gallate, or sodium thiosulfate; coating film forming agents, such as polyvinylpyrrolidine Copolymerization of ketones, polyvinyl alcohol, or vinyl acetate and vinyl pyrrolidone The above examples do not include vegetable and mineral oils and carriers that act as adjuvants for agricultural and artisan pesticide formulations, and carriers, such as lactose, sucrose, glucose, source flour, wheat flour, corn flour, soy cakes, and Coarse flour, degreased rice bran, coriander carbonate, or other commercially available feed materials. One or more ingredients of various compositions of these adjuvants can be appropriately selected for use as long as they are not far from the purpose of the present invention. In addition, some of the other adjuvants other than the above-mentioned known in the field may be appropriately selected for use, and further, some of the above-mentioned various adjuvants to be used in the fields of agriculture and horticulture may be appropriately selected. Was selected for use. The compounding ratio of the compound of the present invention with respect to various adjuvants is usually from 0.1: 99.9 to 90:10. In the actual use of the preparation, it can be used directly, or it can be diluted to a predetermined concentration by adding diluents such as water and various dispersants (for example, surfactants, vegetable oils or mineral oils). need. The compounds of the invention are administered to a host animal orally or parenterally. Oral administration methods may include methods of administering tablets, liquids, capsules, rice paper, soft cakes, minced meat, and other feeds containing the compound of the present invention. Parenteral administration methods may include, for example, a method in which a compound of the present invention is formulated into an appropriate dosage form and administered to the body, for example, via intravenous administration, intramuscular administration, transdermal administration, subcutaneous administration, and the like A method of administering to a body surface via spot treatment (s ρ 〇 t-ο η treatment), perfusion treatment (p0ur_ 〇n treatment) or spray treatment; or a resin fragment containing the compound of the present invention or Wait for the method to get into the skin of the host animal. The dosage of the compound of the present invention to the host animal varies depending on the method of administration, the purpose of administration, the symptoms that appear, etc., but it is usually in a ratio of from 0.01 to 100 g. ·] Mg to 10 g, administered per kg of body weight of the host animal. The present invention also includes a method for controlling pests by the above-mentioned administration method or the above-mentioned dosage, and in particular, a method for controlling external parasites or internal parasites -40-200526552 (37) method. When the compounds of the present invention are used as insecticides against animal parasites, various vitamins' minerals, amino acids, nutrients, enzymes, antipyretics, tranquilizers, anti-inflammatory agents, fungicides, colorants, fragrances Group substances, preservatives and the like can be used in admixture or combination with adjuvants. In addition, if required by the case, other animal or agricultural chemicals, such as helminths, anticoccidials, insecticides, insecticides, flea killers, nematicides, fungicides or antibacterials, can be used It can be used in combination or in combination, which can sometimes improve the efficacy. The present invention includes the mixed insecticidal composition having the above-mentioned various ingredients mixed or used in combination, and in addition, a method for controlling pests by using them, in particular, a method for controlling external parasites or internal parasites. Now, preferred specifics of the compounds of the present invention; examples will be shown. However, the present invention is by no means limited thereto. (1) The above compound, where L is-C (= B) Q, -c (= B) B'Q, "C (= B) N (D) Q, -N (D) Q, -N (D ) C (= B) Q, 'N (D) C (= B) B, Q, -N (D) S〇2Q, -N = CHQ, -N = C (Q) 2, -so2q, or -so2n (d) q. (2) The above compound, wherein L is -C (= B) Q, -c (= B) B, Q, -C (= b) n (D) Q, -N (D) Q Or -N = C (Q) 2. (3) The above compound, wherein: Q is an alkyl group which may be substituted by w, a carbonyl group which may be substituted by w, an alkynyl group which may be substituted by W, and a ring which may be substituted by W A hydrocarbon group, or a 5 to 12-membered heterocyclic group containing an arbitrary heteroatom selected from an oxygen atom, a sulfur atom, and a nitrogen atom (the heterocyclic group may be substituted by W); -41-200526552 (38) W is halogen, nitrate A cyano group, an alkyl group which may be substituted by κ, an alkenyl group which may be substituted by κ, an alkynyl group which may be substituted by K, a cycloalkyl group which may be substituted by M], or a group containing an atom selected from an oxygen atom, a sulfur atom, and a nitrogen atom 5- to 12-membered heterocyclic group of hetero atom (heterocyclic group may be substituted), _〇rI, _sr], -NR] R2, _C0R], < 〇 戍], -C〇SR], cs 〇Rl, _CS2R1 -S02NR] R2, -CONRiR2, CSNR〗 r2 ', -NiR ^ COR3 ^ -N (R1) C02R3 > -NCR ^ COSR3 ^ ^ (I ^ CSOR3 … N (R)) CS2R3, -N (R1) s〇2R3, _s〇r3, -S〇2R3, -CSR3, -OCOR3, -OCSR3, -SCOR3, -SCSR3, trialkylsilyl or trialkyl Silyloxy; K is a halogen, nitro, cyano, cyclic hydrocarbon group which may be substituted by M1, or a 5- to 12-membered heterocyclic group containing a hetero atom selected from an oxygen atom, a sulfur atom, and a nitrogen atom (hetero The ring group may be substituted), -0M2, -SM2, -N Μ2 Μ3 '-C 〇2,-C Ο 2 Μ2, -COS Μ2, -CS Ο Μ2, -cs2m2, -S02NM2M3, -CONM2M3,- CSNM2M3, -C (= NOV) M2, -N (M2) COM4, -N (M2) C02M4, -N (M2) COSM4, -N (M2) CSOM4 ... N (M2) CS2M4, -N (M2) S02M4 , -SOM4, -S02M4, -CSM4, -OCOM4, -OCSM4, -SCOM4, or -SCSM4; M1 is halogen, nitro, cyano, alkyl, haloalkyl, cycloalkyl 'halocycloalkyl, alkenyl , Haloalkenyl, alkynyl, haloalkynyl, -OR4, -SR4, · ΝΙΙΙΙ5, -COR4 ... C02R4, -COSR4, -CSOR4, -CS2R4, _so2nr4r5, -CONR4R5 > -CSNR4R5 ^ -C (= No. V) R4, -N (R4) COR6, -N (R4) C0R2, 200526552 (39) -N (R4) COSR6, -N (R4) CSOR6, -N (R4) CS2R6, -N (R4) S02R6, -SOR6, -S02R6, -C SR6, -0C0R6, -OCSR6, -SCOR6, or-SCSR6; M2 and M3 are each a hydrogen atom, an alkyl group which may be substituted by m 5, an alkenyl group which may be substituted by M 5, an alkynyl group which may be substituted by M 5, and M which may be substituted by M ] A substituted cyclic hydrocarbon group, or a 5- to 12-membered heterocyclic group containing an arbitrary heteroatom selected from an oxygen atom, a sulfur atom, and a nitrogen atom (the heterocyclic group may be substituted by M]); M4 is substituted by M5 Alkyl, alkenyl that may be substituted by M5, alkynyl that may be substituted by M5, cyclic hydrocarbon groups that may be substituted by M1, or 5 to 12-members containing arbitrary heteroatoms selected from oxygen, sulfur, and nitrogen atoms Heterocyclic ring (heterocyclic group may be substituted by M]); M 5 is halogen, alkoxy group which may be substituted by M], cardiothio group which may be substituted by M1, alkylsulfinyl group which may be substituted by MI, may M] substituted alkane group, -M6, -OM6 or -SM6; M6 is a cyclic hydrocarbon group which can be substituted by M1 or contains 5 to 5 of arbitrary heteroatoms selected from oxygen, sulfur and nitrogen atoms. ] 2-membered heterocyclyl (heterocyclyl may be substituted by M 1); R and R2 are each a hydrogen atom, an alkyl group that may be substituted by M7, an alkenyl group that may be substituted by M ?, an alkynyl group that may be substituted by M7 , Can be M, take A cyclic hydrocarbon or an arbitrary heteroatom containing an oxygen atom, a sulfur atom, and a nitrogen atom, a 窆] -membered heterocyclic group (the heterocyclic group may be substituted by M); 'V is an alkyl group which may be substituted by M7, Alkenyl substituted with M7, alkynyl substituted with jM, cyclic hydrocarbon substituted with M], or 5_ to 2_ membered heterocyclic rings containing arbitrary heteroatoms selected from the group consisting of 'atoms, atoms, and nitrogen atoms' 43 ^ 200526552 (40) group (heterocyclic group may be substituted by M]); M7 is halogen, cyclic hydrocarbon group which may be substituted by M1, and contains 5-to-] of arbitrary heteroatoms selected from oxygen, sulfur and nitrogen atoms 2-membered heterocyclyl (heterocyclyl may be substituted by M), -OM8, -SM8, -NM8M9, -COM8, -C02M8, -COSM8, -CSOM8, -CS2M8, -S02NM8M9, -CONM8M9, -CSNM8M9, -C (= NOV) M8, -n (m8) com10, -n (m8) co2m10, -n (m8) cosm] 0, -n (m8) csom10, -n (m8) cs2m] 0, -n ( m8) so2m10, -S Ο M] 0, -S Ο 2 M 1 0, -CSM 1 0, -0 C 〇 M 1 0,-〇c SM 1 0, -SCOM10 or -SCSM10; M8 and M9 are each Hydrogen atom, alkyl group which may be substituted by M 1, alkenyl group which may be substituted by M 1, alkynyl group which may be substituted by M 1, may be substituted by M] A substituted cyclic hydrocarbon group, or a 5- to 12-membered heterocyclic group containing an arbitrary heteroatom selected from an oxygen atom, a sulfur atom, and a nitrogen atom (the heterocyclic group may be substituted by μ 1); Μ 1 G is capable of being Μ ] Substituted alkyl groups, alkenyl groups that may be substituted by μ], alkynyl groups that may be substituted by M], cycloalkyl groups that may be substituted by M], or those containing arbitrary heteroatoms selected from oxygen, sulfur, and nitrogen atoms To 12-membered heterocyclyl (heterocyclyl may be substituted by M 1); V is a hydrogen atom, an alkyl group that may be substituted by M 1, an alkenyl group that may be substituted by M], an alkynyl group that may be substituted by M], A cycloalkyl group which may be substituted by M], or a 5 -g] 2-membered heterocyclic group containing an arbitrary heteroatom selected from an oxygen atom, a sulfur atom, and a nitrogen atom (the heterocyclic group may be substituted by Mm); R and R. Each is a hydrogen atom, alkyl, haloalkyl, aralkyl, heteroaralkyl, cycloalkyl, halocycloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkyn-44-200526552 (41) group , Aryl or heteroaryl; R6 is alkyl, haloalkyl, aralkyl, heteroaralkyl, halocycloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, aryl. (4) The above-mentioned compound, wherein Q is a ring which may be substituted by W, and contains a heterocyclic di 12-membered heterocyclic group selected from an oxygen atom, a sulfur atom, and a nitrogen atom (the heterocyclic group may be substituted by w). (5) The above-mentioned compound, wherein q is a ring fire which may be substituted by W. (6) The above-mentioned compound, wherein Q is a 5- to 12-membered heterocyclic group containing a hetero atom selected from an oxygen atom and a nitrogen atom (heteroW Instead). (7) The above-mentioned compound, wherein W is halogen, nitro, radical, haloalkyl, alkoxyalkyl, phenylalkyl (phenyl group may be substituted), phenoxyalkyl (phenyl group may be Substituted by M1), alkenyl, alkynyl, haloalkynyl, cyclic hydrocarbon group which may be substituted by M1, 5-to 1 2-(heterocyclic group may be substituted by M1) ), Hydroxyl, alkoxy, haloalkoxyalkoxy, phenylalkoxy (the phenyl group may be substituted by M]) oxo (the phenyl group may be substituted by M 1), may be substituted by M ] Substituted sulfanyl group, haloalkylthio group, phenylthio group which can be substituted by M1, amine-amino group, dialkylamino group, monophenylamino group (substitutable phenyl group), diphenylamine (Phenyl group may be substituted by M 1), amine group substituted by alkane (phenyl group may be substituted by M 1), alkoxycarbonylamino group, amino group substituted by alkyl group and phenyl group Carbonyl (benzenecycloalkyl, aryl or heteroaromatic, or 5- to fluorenyl of F., sulfur atom cyclic group can be cyano, alkane 'by M1, halogen may be selected from oxygen member heterocyclyl , Oxygen, phenoxyphenoxy , Alkoxy, and monoalkane are M] radicals and phenyl radicals, monoradical radicals may be -45 ► 200526552 (42) substituted by M1), alkylsulfinyl sulfonyl, haloalkylsulfinyl sulfonyl, may be M1 substituted phenylsulfenyl, alkanesulfonyl, halosulfanyl, benzenesulfonyl which may be substituted by M1, fluorenyl, fluorenyloxy, trialkylsilyl or trialkylsilyloxy. (8) The above compound, wherein W is halogen, nitro, cyano, alkyl, haloalkyl, phenyl which may be substituted by M1, hydroxyl, alkoxy, haloalkoxy, and phenoxy which may be substituted by M1 Group, alkylthio group, haloalkylthio group, phenylthio group which may be substituted by M 1, alkoxycarbonyl group, phenylsulfinyl group which may be substituted by M 1 or benzenesulfonyl group which may be substituted by M 1. (9) The above compound, wherein G is a hydrogen atom, an alkyl group, a haloalkyl group, a phenalkyl group, an alkenyl group, a haloalkenyl group, a phenylalkenyl group, an alkynyl group, a haloalkynyl group, a phenylalkynyl group, or -C ( = B) Q. (10) The above-mentioned compound, wherein both X1 and X2 are fluorine atoms. (1 1) The above compound, wherein Y is an alkyl group. (] 2) The above compound, wherein Y is methyl or ethyl. (1 3) The above compound, wherein A is an oxygen atom. (14) The above compound, wherein G is a hydrogen atom. (15) The above compound, wherein the compound of formula (I) is represented by formula (U):

X2 'CH2 (CH2CH2) n-C-N-C-Q where X] and X2 are each halogen; Y is alkyl, haloalkyl or phenyl; n is from 0 to 5; A and B are each oxygen atom Or sulfur atom; g is hydrogen atom -46-200526552 (43) sub, alkyl, haloalkyl, phenylalkyl, alkenyl, haloalkenyl, phenylalkenyl, alkynyl, haloalkynyl, or phenyl Alkynyl; Q is a 5- to 12-membered heterocyclic group containing a heterocyclic ring selected from an oxygen atom, a sulfur atom, and an Ml atom (a heterocyclic ring which may be substituted), a radical which may be substituted by W, Alkenyl substituted by w, alkynyl substituted by W, cyclic hydrocarbon substituted by w; w is halogen, alkyl, halogen alkyl, alkoxy, haloalkoxy, alkylthio, halothio Phenyl, triphenyl, alkoxycarbonyl, cyano, nitro, phenyl which may be substituted, phenoxy which may be substituted, phenylthio which may be substituted, phenylsulfinyl which may be substituted, or Can be substituted benzylsulfonyl. (16) The above-mentioned compound, wherein in the above (4) compound, the substituent of the heterocyclic group of q or the phenyl group that can be substituted, the phenoxy group that can be substituted, and the phenylthio group that can be substituted The phenylsulfinyl group which can be substituted or the substituent in this sulfofluorenyl group which can be substituted are halogen, nitro, cyano, (c 卜 8) alkyl, halo (C! -8) alkyl , Aryl (C) -8) alkyl, in which the aryl group can be substituted, heteroaryl (C 1 .8) alkyl, in which the heteroaryl group can be substituted, (C3.8) cycloalkyl , Halo (c3.8) cycloalkyl, (C2_8) alkenyl, halo ((: 2 8) alkenyl, (c 2 -8) alkynyl, halo (C 2 · 8) alkynyl, aryl which may be substituted , Optionally substituted heteroaryl, -NR] R2… 〇R], _SR1, _S0R], .s〇2R1, -S02NR1R2 '-COR1 ^ -C02ri n -COSR1 ^ -CSOR1 > -OCOR3 or -ch2cn ;

R1 and R2 are each a hydrogen atom, a (C) .8) alkyl group, a halogen (Cm) alkyl group, or an aryl (Cm) alkyl group, in which an aryl group may be substituted and a heteroaryl (Ci.g) alkane Group, wherein the heteroaryl group may be substituted, (0. 8) cycloalkyl, — (C3 8) cycloalkyl, (C.2.8) alkenyl, halo (C2.8) alkenyl, (C2. s) alkynyl, halo (C2 8) alkyn-47- 200526552 (44), aryl which may be substituted, or heteroaryl which may be substituted; R3 is (Cu) alkyl, halo (c) .8 ) Alkyl, aryl (C 丨 · 8) alkyl, in which the aryl group can be substituted, heteroaryl (C ^ 8) alkyl, in which the heteroaryl group can be substituted '(^ 3.8) ring Yuan Ji, _ (C3-8) ring Yuan Ji, (C2.8) cannyl, halo (C 2-8) alkenyl, (C 2 _ 8) alkynyl, halo (C 2. 8) alkynyl, Substitutable aryl, or substitutable heteroaryl; Substituents in substitutable aryl or substitutable heteroaryl are halogen, nitro, cyano, (Cu) alkyl, halogen (Cu) alkyl, (C3-8) cycloalkane φ, halogen (C3-8) cycloalkyl, (C2-8) alkenyl, halogen (c2.8) alkenyl, (C2.8) alkynyl , Halo (C2_8) alkynyl, -NR4R5, -OR4, -SR4, -SOR4, -S 2R4, -S〇2NR4R5, -COR4, -C02R4, -COSR4, -CSOR4 or _〇C〇R 6; R4 and R5 are each a hydrogen atom, (C) -8) alkyl, halo (C) _8) (C3.8) cycloalkyl, halo (C3.8) cycloalkyl, (C2_8) alkenyl, halo (C2-8) alkenyl, (C2_8) alkynyl or halo (C2_8) alkynyl; (C] .8) alkyl, halo (C) -8) alkyl, aryl (c] .8) alkyl, heteroβaryl (C ^ s) alkyl, (C3.8) cycloalkane Group, halo (C3.8) cycloalkyl, (<: 2.8) alkenyl, halo (C2-8) alkenyl, (C2.s) alkynyl, halo (C2.8) alkynyl, aryl or Heteroaryl. [Embodiment] Now, an example of the present invention will be shown, but the present invention is by no means limited thereto. First, preparation examples of the compound of the present invention will be described. -48-200526552 (45) Preparation Example 1 Preparation of N- (7-ethyl-8,8-difluoro-7-octenylfluorenyl) benzamide (Compound Nos. 1 to 4 5 below) (1 ) A mixed solution containing 33 g of sodium and 3,40 ml of ethanol was added with 1 8 6.72 g of 3-p-oxyl-n-valeric acid methyl ester, and then 3,000 g of ethyl 5-bromovalerate was added. The mixture The reaction was refluxed for 7 hours and 30 minutes. After the reaction was completed, the reaction mixture was left at room temperature for 13 hours, and ethanol was distilled off under reduced pressure. After that, 164 m 1 of water, 150 m 1 of a saturated sodium chloride aqueous solution, and 150 m 1 of ethyl acetate were added for extraction. The aqueous layer was further extracted twice with 150 m of ethyl acetate, and all the organic layers obtained were dried over anhydrous sodium sulfate, and the ethyl acetate was distilled off under reduced pressure to obtain 3 7 4 · 5 g of oily crude 2- Diethyl propionyl pimelate. (2) A mixed solution containing 180 g of 85% potassium hydroxide and 1577 ml of water was added to 37.4 · 5 g of crude diethylpropanylpimelate, and the mixture was reacted at room temperature for 6 days. The reaction mixture was washed with 500 m 1 of hexane, and 235 m of concentrated sulfuric acid was added to the aqueous layer, and the mixture was further reacted under reflux for 1 hour. After the reaction was completed, the reaction mixture was cooled and saturated with sodium chloride. After that, the mixture was extracted 4 times with 300 ml of ether. The organic layer was dried over anhydrous sodium sulfate, and the ether was distilled off under reduced pressure to obtain 2 3 2.84 g of crude 7-oxonanoic acid as white crystals. (3) A mixed solution containing 2 2 7.9 7 g of crude 7-oxonanoic acid, 2,000 ml of ethanol, and 30 m] concentrated sulfuric acid was reacted under reflux for 21 hours and 30 minutes. After the reaction was completed, ethanol was distilled off from the reaction mixture under reduced pressure. -49-200526552 (46) 150 g of ice and 500 ml of ether were added and then separated. The organic layer was washed with 100 ml of water and three times with 50 ml of saturated sodium chloride. The aqueous layer was extracted with 200 ml of diethyl ether, followed by washing with 50 ml of saturated sodium water for 5 times. All the obtained organic layers were dried over anhydrous sodium sulfate and distilled under reduced pressure to obtain 24.82 g of crude ethyl 7, nonanoate as an oil. (4) Under nitrogen, 550 ml of tris (dimethylamino) phosphine was added dropwise at 2 to a mixture containing 2,000 ml of anhydrous 2-methoxyethyl ether and 13 dibromodifluoromethane. After the dropwise addition was completed, at 1550 g of crude 7-oxo nonanoate was added and mixed at 50 ° C for 15 hours. After that, the mixture was further at 100 ° · for 4 hours. After the reaction was completed, the reaction mixture was poured into 930 ml of water, and 930 ml of hexane was extracted. The organic layer was washed once with 930 ml water, 5 times with 400 m water, and then once with 100 m 1 of a saturated sodium chloride aqueous solution to obtain 1 4 9.6 g of crude 7-B as an oil. Ethyl-8,8-difluoro-7-acid ethyl ester. (5) A solution containing 5 0.6 4 g of 85% potassium hydroxide and 5 50 m 1 of methanol was added to M9.6 g of a crude 7-ethyl-8,8-difluoro-7-octene acetate 'mixture The reaction was continued at room temperature for 3 days. After the reaction was completed, methanol was removed from the reaction mixture under reduced pressure, and the residue was dissolved in 430 ml of water, followed by 3 times with 60 ml of dichloromethane. The aqueous layer was acidified with concentrated hydrochloric acid and extracted twice with 40 ml of dichloromethane. The organic layer was dried over anhydrous sodium sulfate. After diethyl ether was evaporated under reduced pressure, the solution was chlorinated and dried. The side oxygen was 15 ° C and 8.5 ml at 25 ° C. The reaction mixture was washed with octene and mixed with ethyl acetate. Distilled and washed 3 off, -50- 200526552 (47) to obtain 18.94 g of crude 7-ethyl-8,8-difluoro-7-octenenoic acid as an oil. The NMR spectrum data of this product are as follows. ] H — NMR 5 ppm (Solution | J: CDCI3MOOMHZ) 2.34 (2H, t, J = 7.7Hz), 1.92—1.99 (4H'm), 1.63 (2H, quintet, J = 7.5Hz) '1.2 8 — 1.4. 2 (4 Η, m), 0.97 (3H, t, J = 7.4 Hz) 0 (6) 12 ml of grass chloride was added dropwise to 5.95 g of crude 7-ethyl-8 under ice cooling , 8-difluoro-7-octanoic acid. After completion of the dropwise addition, the mixture was reacted at room temperature for 1 hour and 10 minutes, and the reaction mixture was concentrated under reduced pressure to obtain crude ethyl-8,8-difluoro-7-octenyl chloride. 19.2 m] of 1.58 M butyl lithium (hexane solution) at -78. Under nitrogen, the solution was added dropwise to a mixed solution containing 3.50 g of benzamidine and 40 m 1 of tetrahydro Dfran. After stirring for 40 minutes, a mixed solution containing the above crude 7-ethyl-8,8-difluoro-7-octenyl chloride and 10 m 1 of tetrahydrofuran was added dropwise, and the reaction of the mixture was continued for 20 minutes. After that, the mixture was returned to room temperature, and further reaction was continued for 5 hours and 30 minutes. After completion of the reaction, the reaction mixture was poured into a small amount of water, and then poured into a saturated aqueous sodium chloride solution, and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and ethyl acetate was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (extraction solvent: hexane / ethyl acetate = 8/2), and then crystallized from a mixed solvent of ether and hexane. The crystals were collected by filtration and washed with hexane to obtain 1.995 g of the desired product, the melting point of which was from 63 to 200526552 (48) 64 0 C. Preparation Example 2 Preparation example of N- (7-ethyl-8,8-difluoro-7-octenylfluorenyl) 2-thiophenecarboxamide (Compound No. 1-67 below)

1.3 ml of chloramphenicol and 0.5 g of crude 7-ethyl-8,8-difluoro-7-octenic acid were reacted at room temperature for 1 hour, and the reaction mixture was concentrated under reduced pressure to obtain crude 7-ethyl- 8,8-difluoro-7-octenyl chloride. 1.68 ml of 1.59 M butyl lithium (hexane solution) was added dropwise to a mixed solution containing 0.3 09 g of 2-thiophenecarboxamide, 10 ml of tetrahydrofuran, and 1 ml of trimethylamine hexamethyl phosphate under -78 ° C nitrogen. After stirring for 35 minutes, a mixed solution containing the above crude 7-ethyl-858-difluoro-7-octenyl chloride and 2m] tetrahydrofuran was added dropwise, and the reaction of the mixture was continued for 40 minutes. The mixture was then returned to room temperature and further reacted overnight.

After the reaction was completed, the reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and ethyl acetate was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (extraction solvent: hexane / ethyl acetate = 8/2), and then washed with hexane, to obtain 0.05 g of the desired product, the melting point of which was from 75 To 78 ° C. Preparation Example 3 Preparation Example 16m of N- (7-ethyl-8,8-difluoro-7-octenylfluorenyl) 2-phenoxyacetamidamine (Compound No. 1-90 below) Under ice cooling, 6.0 g of crude 7-ethyl-52-200526552 (49) 8 5 8-difluoro-7-octenic acid was added dropwise. After completion of the dropwise addition, the mixture was reacted at room temperature for 1 hour and 15 minutes, and the reaction mixture was concentrated under reduced pressure to obtain crude 7-ethyl-8,8-difluoro-7-octenyl chloride. 20 ml of 1.59M butyllithium (hexane solution) was added dropwise to a mixed solution containing 4.4 g of phenoxyacetamide and 150 ml of tetrahydrofuran under a nitrogen atmosphere of -7 ° C. After stirring for a minute, a mixed solution containing the above crude 7 • ethyl-8,8-difluoro-7-octenyl chloride and 10 m 1 of tetrahydrofuran was added dropwise, and the reaction of the mixture was continued for 3 5 minutes. After that, the mixture was returned to room temperature, and further reaction was performed overnight. After the reaction was completed, the reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and ethyl acetate was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: hexane / ethyl acetate = 7.5 / 2.5), and then crystallized from a mixed solvent of ether and hexane. The crystals were collected by filtration and washed with hexane to obtain 2.2 g of the desired product with a melting point of 64 to 65 ° C. Preparation Example 4 Preparation Example of N- (7-ethyl-8, 8-difluoro-7-octenylfluorenyl) carbamate (Compound No. 2 to 3 below) 0.8 ml Chlorochlor To 0.4 g of crude 7-ethyl8,8-difluoro-7-octanoic acid. After the dropwise addition was completed, the mixture was allowed to react at room temperature for 20 hours and 20 minutes, and the reaction mixture was concentrated under reduced pressure to obtain crude 7-ethyl-8,8-difluoro-7-octenyl chloride. ] · 3 m 1] · 5 8 M Butyllithium (hexane solution) at -78. Under nitrogen, -53- (50) (50) 200526552 was added dropwise to a mixed solution containing 0.266 g of phenylcarbamate and 3 ml of tetrahydrofuran. After stirring for 40 minutes, a mixed solution containing the above crude 7-ethyl-8,8-difluoro-7-octenyl chloride and 2 ml of tetrahydrofuran was added dropwise, and the reaction of the mixture was continued for 15 minutes. After that, the mixture was returned to room temperature and further reacted overnight. After the reaction was completed, the reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and ethyl acetate was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (extraction solvent: hexane / ethyl acetate = 8/2) to obtain 0.34 g of the desired product as an oily substance. Production Example 5 Production Example (1) of 1- (7-ethyl-8,8-dihui-7-octenyl) 3-phenylurea (Compound No. 2 to 4 below) Add dropwise to 2. (^ 7-ethyl-8,8-difluoro-7-octenenoic acid. After the dropwise addition is complete, the mixture is allowed to react at room temperature for 2 hours, and the reaction mixture is concentrated under reduced pressure. To obtain crude 7-ethyl-8 5 8 -difluoro-7-octenyl chloride. Ammonia gas was blown into 50 ml of tetrahydrofuran under ice cooling to saturate, and the crude 7-ethyl-8 containing the above was added dropwise. , 8-difluoro-7-octenyl chloride and a mixed solution of 5 m 1 of tetrahydrofuran. The mixture was reacted at room temperature for 16 hours and 30 minutes. After the reaction was completed, a small amount of water was added to the reaction mixture to The solid product was dissolved and a saturated aqueous sodium chloride solution was further added. The mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and the ethyl acetate was distilled off under reduced pressure at -54-200526552 (51). Residual The product was purified by silica gel column chromatography (eluent: Kojin / Ethyl Acetate = 3/7) to obtain 1.7 g of 7 · ethyl_8,8_difluoro-7-octyl alcohol. Amine, its melting point From 6 8 to 7 1. C. The NMR data of this product are as follows: Η-NMR ppm (solvent: CDC13 / 400MHz) 5.59 (2H, brd, J = 59.6Hz),

2.20 (2H, t, J = 7.8Hz), 1.92 — 1.98 (4H, m), 1.62 (2H 'quintet »J = 7.6Hz) 5 1.26 — 1.42 (4H, m), 0.96 (3H, t, J = 7.6 Hz) 〇 (2) 0 · 1] 6 g of phenyl isocyanate was added to 0.2 g of 7-ethyl-8; 8-difluoro-7-octenylamine and 2 ml of diisocyanate obtained in the above step. In the mixed solution of naphthene, the mixture was reacted at room temperature for 2 hours. After that, the mixture was further reacted at reflux for 17 minutes and 30 minutes. After the reaction was completed, dioxane was distilled off from the reaction mixture under reduced pressure, and the residue was purified by silica gel column chromatography (extraction solvent: hexane / ethyl acetate = 8/2) to obtain 0.14 g of The desired product has a melting point from 76 to 78 ° C. Preparation Example 6 Preparation Example of 2'-Diphenylmethylene 7-ethyl-8, 8-difluoro-7-octenylhydrazine (the following compound -55- 200526552 (52) Article No. 2-8) contains 0.26 g of crude 7-ethyl-8,8-difluoro-7-octenic acid, 0.196 g of diphenyl ketone hydrazone, 0.2 g of ethyl-3- (3-dimethylaminopropylcarbonyl The mixture of diimine hydrochloride and 3 ml of dichloromethane continued to react at room temperature! After 7 hours, the mixture was further reacted at 40 ° C for 5 hours. After the reaction was completed, the reaction mixture was washed with water and then The organic layer was dried over anhydrous sodium sulfate, and the dichloromethane was evaporated under reduced pressure. The residue was subjected to silica gel column chromatography (extraction solvent: hexane / ethyl acetate = 1). 7/3) is purified to obtain 0.15 g of the desired product, the melting point of which is from 70 to 74 ° C. Now, typical examples of the compound of the present invention represented by the above formula (I) are shown in Tables 1 and 2 As shown, the NMR spectrum data are shown in Table 3. These compounds can be prepared by the above-mentioned Preparation Examples or the above-mentioned various methods for preparing the compounds of the present invention. In Tables 1 to 3, the numbers indicate the compounds In addition, in Tables 1 and 2, Me represents a methyl group, represents an ethyl group, and pr represents an n-propyl group, and: iP] represents isopropyl group, t_Bu represents t-butyl group, and n_oct represents n-octyl. NDode represents n-dodecyl, and ph represents phenyl. In Tables i and 2, Ph (2-C1) represents a base having a chlorine atom substituent at the 2-position, and PhH-PhM-CD ) Represents a phenyl group having a phenyl substituent (the phenyl group has a CF3 substituent at the 4-position) at the t position, and ph (4-◦J-pyridyKtcF3)) represents a 2-pyridyloxy group (the pyridyl group has The C F3 substituent is at the 5-position) and the phenyl is substituted at the 4-position. It applies to other similar descriptions. -56-200526552 (53) X 丨 c = c X2 Table 1

Λ o B, 丨 丨 丨 IICH2 (CH2CH2) n—C—N——C——Q number X1 X2 Y n AGBQ Physical properties (mp: 0C) 1-1 FF Me 0 〇H 〇Ph 1-2 FF Me 0 〇H 〇Ph (2-Cl) 1-3 FF Et 0 〇H 〇Ph 1-4 FF Et 0 〇H 〇Ph (2-Cl) 1-5 FF Me 1 〇H 〇Ph 1-6 FF Me 1 〇H 〇Ph (2-Cl) 1-7 FF Me 1 〇H 〇Ph (2-Me) 1-8 FF Me 1 〇H 〇Ph (4-Cl) 1-9 FF Me 1 〇H 〇CH2 〇Ph 1-10 FF Me 1 〇H 〇CH2〇Ph (4-Cl) 1-11 FF Me 1 〇H 〇CH2SPh 1-12 FF Me 1 〇H 〇CH2SPh (4 ~ Cl) 1-13 FF Me 1 〇H 〇CH2S〇2Ph 1-14 FF Et 1 〇H 〇Ph Amorphous 1-15 FF Et 1 〇H 〇Ph (2-C1) 81-87 1-16 FF Et 1 〇H 〇Ph (2- Me) 83-84 1 -17 FF Et 1 〇H 〇Ph (4-Cl) 93-95 1-18 FF Et 1 〇H 〇Ph (2,6-Cl2) 1-19 FF Et 1 〇H 〇Ph (2,4-Cl2) 1-20 FF Et 1 〇H 〇Ph (2,4,6-Cl3) 1-21 FF Et 1 〇K 〇.CH2〇Ph Oily 1-22 FF Et 1 〇H 〇 CH2〇Ph (4-Cl) 1-23 FF Et 1 〇H 〇CH2SPh 1-24 FF Et 1 〇H 〇CH2SPh (4-Cl) 1-25 FF Et 1 〇H 〇 C H2S02Ph 1-26 FF Me 2 〇H 〇Ph 78-79 1-27 FF Me 2 〇H 〇Ph (2-Cl) 94-95 1-28 F. F Me 2 〇H 〇Ph (2-Me) 80 -81 1-29 FF Me 2 〇H 〇Ph (4-Cl) 113-114.5 1-30 FF Me 2 〇H 〇Ph (2,6-Cl2) 1-31 FF Me 2 〇H 〇Ph (2, 4-Cl2) 1-32 FF Me 2 〇H 〇Ph (2,4, 6-Cl3) 1-33 FF Me 2 〇CH2Ph 〇Ph 1-34 FF Me 2 〇CH2Ph 〇Ph (2-Cl) 1- 35 FF Me 2 〇CH2Ph 〇Ph (2-Me) -57-200526552 (54) Table 1 (continued) No. X1 X2 Y n AGBQ Physical properties (mp: ° C) 1-36 FF Me 2 〇CH2Ph 〇Ph ( 4-Cl) 1 -3 7 FF Me 2 〇CH2Ph 〇Ph (2, 6-Cl2) 1-38 FF Me 2 〇CH2Ph 〇Ph (2 / 4-Ci2) 1-39 FF Me 2 〇CH2Ph 〇Ph ( 2/4 / 6-Cl3) 1-40 FF Me 2 〇H 〇CH2〇Ph 1-41 FF Me 2 〇H 〇CH2〇Ph (4-Cl) 1-42 FF Me 2 〇H 〇CH2SPh 1-43 FF Me 2 〇H 〇CH2SPh (4-Cl) 1-44 FF Me 2 〇H 〇CH2S〇2Ph 1-45 FF Et 2 〇H 〇Ph 63-64 1-46 FF Et 2 〇H 〇Ph (2- Cl) 68-87 1-47 fl F Et 2 〇H 〇Ph (3-Cl) 75-32 1-48 FF Et 2 〇H 〇Ph (4-Cl) 65-84 1-49 FF Et 2 〇H 〇Ph (2-Me) 30-70 1-50 FF Et 2 〇H 〇Ph (3-Me) 53-56 1-51 FF Et 2 〇H 〇Ph (4-Me) 63- 67 1-52 FF Et 2 〇H 〇Ph (4-OMe) 46-75 1-53 FF Et 2 〇H 〇Ph (4-Et) 30-47 1-54 FF Et 2 〇H 〇Ph (4- t-Bu) 36-66 1-55 FF Et 2 〇H 〇Ph (2-CF3) Amorphous 1-56 FF Et 2 〇H 〇Ph (2 — C〇2Et) 1-57 FF Et 2 〇H 〇Ph (4-SMe) 1-58 FF Et 2 〇H 〇Ph (2-N02) 'Oil 1-59 FF Et 2 〇H 〇Ph (2-CN) 1-60 FF Et 2 〇H 〇Ph (2, 6-Cl2) 99-101 1-61 FF Et 2 〇H 〇Ph (2,4-Cl2) 37-45 1-62 FF Et 2 〇H 〇Ph (3,5-Cl2) 1-63 FF Et 2 〇H 〇Ph (2,4,6-Cl3) 1-64 FF Et 2 〇H 〇2-pyridinyl oily 1-65 FF Et 2. 〇3 〇3-pyrimidinyl oily 1- 66 FF Et 2 〇H 〇f pyridyl 40-45 1-67 FF Et 2 〇H 〇2-thienyl 7 5_78 1-6 8 FF Et 2 〇H 〇3-isooxazolyl 1-69 FF Et 2 〇H 〇5-Isoxazolyl 1-70 FF Et 2 〇H 〇2-thiazolyl 1-71 FF Et 2 〇H 〇1,3- (Me) 2-5-pyrazolyl 1-72 FF Et 2 〇H 〇2-pyrimidine

-58-200526552 (55) Table 1 (continued) No. X1 X2 Y n AGBQ Physical properties (mp: ° C) 1-73 FF Et 2 〇H 〇2 -Pyrazine-based oily '1-7 4 FF Et 2 〇H 〇2 -quinolinyl 1-7 5 FF Et 2 〇H 〇Me 1-7 6 FF Et 2 〇H 〇Et 1-77 FF Et 2 〇H 〇n-Pr 1 -7 8 FF Et 2 〇H 〇 i-Pr 1-79 FF Et 2 〇H 〇t-Bu 1-80 FF Et 2 〇H. 〇CH2CH2CH2〇Et 1-81 FF Et 2 〇H 〇CH2CH = CH2 1-82 FF Et 2 〇H 〇ch = ch2 1-83 FF Et 2 〇H 〇ch2c. = ch 1-84 FF Et 2 〇H 〇 cyclopropyl 1-85 FF Et 2 〇H 〇 cyclohexyl 1-86 FF Et 2 〇H 〇1-naphthalene 119-126 1-87 FF Et 2 〇H 〇Ph (4-〇Ph) 1-88 FF Et 2 〇H 〇Ph (4-Ph (4-cf3)) 1-89 FF Et 2 〇H 〇Ph (4-Ph) 1-90 FF Et 2 〇H 〇CH2〇Ph 64-65 1-91 FF Et 2 〇H 〇CH2SPh 69-72 1-92 FF Et 2 〇H 〇CH2SOPh 1-93 FF Et 2 〇 H 〇CH2S02Ph 1-94 FF Et 2 〇H 〇CHMeOPh 73_74 1-95 FF Et 2 〇H 0 CMe2〇Ph 1-96 FF Et 2 〇H 〇CH2CH2OPh. 1-97 FF Et 2 〇H 〇CH2〇Ph ( 2- Cl) Oily 1-98 FF Et 2 〇H 〇CH2〇Ph (3-Ci) Oily 1 1-99 FF Et 2 〇H 〇CH2〇Ph (4-C1) 38-53.5 1-100 FF Et 2 〇H 〇CH2〇Ph (2-Me) Oily 1-101 FF Et 2 〇H 〇CH2〇Ph (3-Me) 58-59 1-102 FF Et 2 〇H 〇CH2〇Ph (4-Me) 53-54 1-103 FF Et 2 〇H 〇CH2SPh (2-C1) 1-104 FF Et 2 〇H 〇CH2SPh (4-Cl) 1-105 FF Me 3 〇H 〇Ph 1-106 FF Me 3 〇 H 〇Ph (2-Cl) 1-107 FF Me 3 〇H 〇Ph (2-Me) 1-108 FF Me 3 〇H 〇Ph (4-Cl) 1-109 FF Me 3 〇H 〇CH2〇Ph 1-110 FF Me 3 〇H 〇CH2〇Ph (4-Cl)

-59-200526552 (56) Table 1 (continued) No. X1 X2 Y n AGBQ Physical properties (rnp: ° C) 1-111 FF Me 3 〇H 〇CH2SPh 1-112 FF Me 3 〇H 〇CH2SPh (4-Cl ) 1-113 FF Me 3 〇H 〇CH2S〇2Ph 1-114 FF Et 3 〇H 〇Ph Oily 1-115 FF Et 3 〇H 〇Ph (2-Cl) < 73 1-116 FF Et 3 〇 H 〇Ph (2-Me) Amorphous 1-117 FF Et 3 '〇K 〇Ph (4-Cl) < 98 1-118 FF Et 3 〇H 〇CH2〇Ph 1-119 FF Et 3 〇H 〇CH2〇Ph (4-Cl) 1-120 FF Et 3 〇H 〇CH2SPh 1-121 FF Et 3 〇H 〇CH2SPh (4-Cl) 1-122 FF Et 3 〇H 〇CH2S02Ph 1-123 FF Me 4 〇H 〇Ph 1-124 FF Me 4 〇H 〇Ph (2-Cl) 1-125 FF Me 4 〇H 〇Ph (2-Me) 1-126 FF Me 4 〇K 〇Ph (4-Cl) 1 -12 7 FF Me 4 〇H 〇CH2〇Ph 1-128 FF Me 4 〇H 〇CH2SPh (4-Cl) 1-129 FF Et 4 〇H 〇Ph 1-130 FF Et 4 〇H 〇Ph (2 -Cl) 1-131 FF Et 4 〇H 〇Ph (2-Me) 1-132 FF Et 4 〇H 〇Ph (4-Cl) 1-133 FF Et 4 〇H 〇CH2 〇Ph 1-134 FF Et 4 〇H. 〇CH2SPh (4-Cl) 1-135 FF Me 5 H 〇Ph 1-136 FF Me 5 〇H 〇Ph (2-Cl) 1-13 7 FF Me 5 〇H 〇Ph C2-Me) 1-138 FF Me 5 〇H 〇Ph (4-Cl) 1 -139 FF Me 5 〇H 〇CH2〇Ph 1-140 FF Me 5 〇H 〇CH2SPh (4-Cl) 1-141 FF Et 5 〇H 〇Ph 1-142 FF Et 5 〇H 〇Ph (2-Cl ) 1-143 FF Et 5 〇H 〇Ph (2-Me) 1-144 FF Et 5 〇H 〇Ph (4-Cl) 1-145 FF Et 5 〇H 〇CH2〇Ph 1-146 FF Et 5 〇 H 〇CH2SPh (4-Cl) 1-147 FF Et 2 〇Me 〇Ph Oily 1-148 FF Et 2 〇CH2CH2C1 〇Ph

-60- (57) 200526552 Table 1 (continued) No. X1 X2 Y n AGBQ Physical properties (mp: ° C) 1-149 FF Et 2 〇ch = ch2 〇Ph 1-150 FF Et 2 〇CH = CHPh 〇Ph 1-151 FF Et 2 〇CH 2 CC12 〇Ph 1-152 FF Et 2 〇ch2c = ch 〇Ph 1-153 FF Et 2 〇ch2c Tri Cl 〇Ph 1-154 FF Et 2 〇CH2C = CPh 〇Ph 1- 155 F Cl Et 2 〇H 〇Ph 1-156 C1 Cl Et 2 〇H 〇Ph 1-157 Br Br Et 2 〇H 〇Ph 1-158 FF Et 2 SHS Ph 1-159 FF Et 2 SHS Ph (2- Cl) 1-160 FF Et 2 〇HS Ph 1-161 FF Et 2 〇H s Ph (2-Cl) 1-162 FF Et 2 s H 〇Ph 1-163 FF Et. 2 s H 〇Ph (2- (Cl) 1-164 FF CH2C1 2 〇H 〇Ph 1-165 FF cf3 2 〇H 〇Ph 1-166 FF Ph 2 〇H 〇Ph 1-167 FF Et 2 〇H 〇3- oxalyl 1-168 FF Et 1 〇H 〇Ph (4-Me) 75-77 1-169 FF Et 2 〇H 〇Ph (2,4-F2) 92-94 1-17 0 FF Et 2 〇H 〇Ph (4-Br) 105-106.5 1-171 FF Et 2 〇H 〇Ph (2-work) amorphous 1-172 FF Et 2 0 H 〇Ph (4-work) 75-114. 1-173 FF Et 2 〇H 〇Ph (2-SMe) 7 8-82 1-174 FF Et 2 〇H 〇Ph (4-OPh) 84 — 86 1-175 FF Et 2 〇H 〇Ph (2-F) Oily 1-17 6 FF Et 2 〇H 〇Ph (2-Br) 83-88 1 177 FF Et 3 〇H ό Ph (4-Me) 37-58.5 1-17 8 FF Et 2 〇H 〇CH2〇Ph (2-F) oily 1-179 FF Et 2 〇H 〇CH2N (Me ) Ph 88.5-90.5 -61-200526552 (58) Table 1 (continued) No. X1 X2 Y n AGBQ Physical properties (nap: 0C) 1-180 FF Et 2 〇CO (CH2) 5C (Et) = cf2 〇Ph ( 2-F) Oily 1-181 FF Et 2 〇C〇 (CH2) 5C (Et) = cf2 〇Ph 1-182 FF Et 2 〇C〇 (CH2) 5C (Et) = cf2 〇Ph (2-Cl ) 1-183 FF Et 2 〇C〇 (CH2) 5C (Et) = cf2 〇Ph (2-Me) 1-184 FF Et 2 〇C〇 (CH2) 5C (Et) = cf2 〇Ph (4-Me ) 1-185 FF Et 2 〇C〇 (CH2) 5C (Et) = cf2 〇CH2〇Ph 1-186 FF Et 2 〇H 〇Ph (4-SiMe3) 1-187 FF Et 2 〇H 〇Ph (4 -C02Me) 1-188 FF Et 2 〇H 〇Ph (4-C02-t-Bu) 1-189 FF Et 2 〇H 〇Ph (2-CONMe2) 1-190 FF Et 2 〇H 〇Ph (4- Ph) 1-191 FF Et 2 〇H 〇Ph (4-CON (Me) Ph) 1-192 FF Et 2 〇H 〇Ph (4-CF (CF3) 2) 1-193 FF Et 2 〇H 〇Ph (4- ch = ch2) 1-194 FF Et 2 〇H 〇Ph (4-C = CH) 1-195 FF Et 2 〇H 〇Ph (2-i-Pr) 1-196 FF Et 2 〇 H 〇Ph (4 ~ CH2〇Ph) 1 -197 FF Et 2 〇H 〇Ph (4- 〇CH2Ph) 1-198 FF Et 2 〇H 〇Ph (4-〇Si (t-Bu) Me2) 1- 199 FF Et 2 〇H 〇Ph (4-OH) 1-200 FF Et 2 〇H 〇Ph (4-NMe2) 65-94 1-201 FF Et 2 〇H 〇Ph (4-SCF3) 1-202 FF Et 2 〇H 〇Ph (2-C〇Me) -62-200526552 (59) Table 1 (continued) No. X1 X2 Y n AGBQ Physical properties (mp: ° C) 1-203 FF Et 2 〇H 〇Ph ( 4-CO-t-Bu) 1-204 FF Et 2 〇H 〇ch 2-cyclopropyl 1-205 FF Et 2 〇H 〇CH (Me) -cyclopropyl 1-206 FF Me 2 〇H 〇Ph ( 4-Br) 1-207 FF Me 2 〇H 〇Ph (4-Me) 93-94 1-208 FF Me 2 〇H 0 Ph (2-Br) 1-209 FF Et 2 〇H 〇Ph (4- Br) 1-210 FF Et 2 〇H 〇Ph (2-Br) 1-211 FF Et 2 〇H 〇Ph (4-0-cyclopropyl) 1-212 FF Et 2 〇H 〇Ph (4-SCH2CH2C1 ) 1-213 FF Et 2 〇H 〇Ph (4-SOCH2CH2〇Ph) 1-214 FF Et 2 〇H 〇Ph (4- S02CK2CH20Ph) 1-215 FF Et 2 〇H 〇Ph (4- 〇CH2CH2〇Ph) 1-216 FF Et 2 〇H 〇Ph (4- 0CH2CH20Ph (2-F)) 1-217 FF Et 2 〇H 〇Ph (4-OCH2C = CMe) 1-218 FF Et 2 〇H 〇Ph (4-0CH2CH20Et) 1-219 FF Et 2 〇H 〇CH2CH2OMe 1-220 FF Et 2 〇H 〇CH2CH2COMe 1-221 FF Et 2 〇H 〇Ph (4-0 ~ 2-pyridyl) 1-222 · FF Et 2 〇H 〇Ph (4-C〇Ph) 1-223 FF Et 2 〇H 〇Ph (4-COSMe) 1-224 'FF Et 2 〇H 〇Ph (4-CONMe2) 1-225 FF Et 2 〇H 〇Ph (4-C (= NOMe) Me) 1-226 FF Et 2 〇H 〇CH2CH2C〇CH2-cyclohexyl 1-22 7 FF Et 2 〇H 〇CH2CH2C〇CH2Ph 1-228 FF Et 2 〇H 〇Ph (4-CH2CH2〇Et) 1-229 FF Et 2 〇H 〇Ph (4- CH2CH2〇CH2Ph) 1-230 FF Et 2 〇H 〇CH2CH2NMe2 1-231 F. F Et 2 〇H 〇CH2CH2N (Me ) CH2CH2 SMe 1-232 FF Et 2 〇H 〇CH2CH2CONMe2 1-233 FF Et 2 〇H 〇Ph (4-CH2SMe) 1-234 FF Et 2 〇H 〇Ph (4-CH2SH) 1-235 FF Et 2 〇 H 〇Ph (4-CH2NMe2)

-63- 200526552 (60) Table 1 (continued) No. X1 X2 Y n AGBQ Physical properties (mp: ° C) 1-236 FF Et 2 〇H 〇Ph (4-CH2COEt) 1-23 7 FF Et 2 〇, H 〇Ph (4-CH2C02Me) 1-238 FF Et 2 〇H 〇Ph (4-CH2COS-i-Pr) 1-239 FF Et 2 〇H 〇Ph (4-CH2CSOMe) 1-240 FF Et 2 〇H 〇Ph (4-CH2CS2Ph) 1-241 FF Et 2 〇H 〇Ph (4-CH2S〇2NMe2) 1-242 FF Et 2 〇H 〇Ph (4-CH2CONMe2) 1-243 FF Et 2 〇H 〇Ph ( 4-CH2CSNMe2) 1-244 FF Et 2 〇H 〇Ph (4-CH2C (= NOMe) Me) 1-245 FF Et 2 〇H 〇Ph (4-CH2NHCOMe) 1-246 FF Et 2 〇H 〇Ph ( 4- CH2N (Me) C02Me) 1-247 FF Et 2 〇H 〇Ph (4-CH2NHS02Me) 1-248 FF Et 2 〇H 〇Ph (4-CH2SOMe) 1-249 FF Et 2 〇H 〇Ph (4 -CH2S〇2Me) 1-250 FF Et 2 〇H 〇Ph (2-CH2CSMe) 1-251 FF Et 2 〇H 〇Ph (4-OCOMe) 1-252 FF Et 2 〇H 〇Ph (4-OCSMe) 1-253 FF Et 2 〇H 〇Ph (4-SC〇CH2C tri-CH) 1-254 FF Et 2 〇H 〇Ph (4-CH20-n-Dode) 1-255 FF Et 2 〇H 〇Ph (4 -CH2S〇2CH2CH2S〇2Me) 1-256 FF Et 2 〇 H 〇Ph (4-CH2SCH2CH2SPh (4-Cl)) 1-257 FF Et 2 〇H 〇Ph (4-CH2〇-2 -pyridinyl) 1-258 FF Et 2 〇H 〇Ph (4-CSOMe) 1-259 FF Et 2 〇H 〇Ph (4-CS2Ph) 1-260 FF Et 2 〇H. 〇Ph (4-S02NMe2) 1-261 FF Et 2 〇H 〇Ph (4-CSNMe2) 1-262 FF Et 2 〇H 〇Ph (4-OCH2CK2NMe2) 1-263 FF Et 2 〇H 〇Ph (4- 〇CH2CH2C〇2CH2CH2N〇2) 1-264 FF Et 2 〇H 〇Ph (4- OCH2CH2CONHCH2CN) 1-265 FF Et 2 〇H 〇Ph (4-N (Me) COMe) 1-266 FF Et 2 〇H 〇Ph (4-N (Me) C02Me) 1-267 FF Et 2 〇H 〇Ph (4-N (Me ) COSMe) 1-268 FF Et 2 〇H 〇Ph (4-N (Me) CSOMe) -64- 200526552 (61) Table 1 (continued) No. X1 X2 Y n A. GBQ Physical properties (mp: 0C) 1 -269 FF Et 2 〇H 〇Ph (4-N (Me) CS2Me) 1-2 7 0 FF Et 2 〇H 〇Ph (4-CSMe) 1-271 FF Et 2 〇H 〇Ph (4-OCOMe) 1-2 7 2 FF Et 2 〇H 〇Ph (4_〇CSMe) 1-273 FF Et 2 〇H 〇Ph (4-SCO-n-Oct) 1-2 7 4 FF Et 2 〇H 〇Ph ( 4-SCSPh) 1-275 FF Et 2 〇H 〇Ph (4-0-2-pyridyl (5-CF3)) 1-2 7 6 FF Et 2 〇 H 〇Ph (4-0-2-Hydroxyl (3-Cl -5-cf3)) 1-277 FF Et 2 〇CONMe2 〇Ph 1 -2 7 8 FF Et 2 〇H 〇Ph (4-CH2Ph ( 4 ~ N (Me) C02Me)) 1-279 FF Et 2 〇H 〇Ph (4-OMe) Oily 1-280 FF Et 2 〇H 〇Ph (4-〇CF3) Oily-65- 200526552 (62 )

y1 Y

/ ° \ ii I

X2 CH2 (CH2CH2) n—C—N——L Table 2 No. X1 X2 Y n AGL Physical properties (mp: ° C) 2-1 FF Et 2 〇H CK2C〇2Et Oily 2-2 FF Et 2 〇H S02Ph Oily 2-3 FF Et 2 〇H C02Ph Oily 2-4 FF Et 2 〇H CONHPh 7 6 — 7 8 · 2-5 FF Et 2 〇H NHPh 74-7 8 2-6 FF Et 2 〇H NH_2-pyrimidinyl 83-85 2-7 FF Et 2 〇H NHCOPh 7 7-80 2-8 FF Et 2 〇HN = CPh2 70-74 2-9 FF Et 3 〇H NHC〇2Me oily 2-10 FF Et 3 〇H NHS02Ph 78-80 2-11 FF Et 2 • 0 H C02CH2〇Ph 2 -12 FF Et 2 〇H COSPh 2-13 FF Et 2 〇H CSOPh 2-14 FF Et 2 SH CONHPh 2-15 FF Et 2 〇H NHPh (2-Cl) 2-16 FF Et 2 〇H NHPh (4-Cl) 2-17 FF Et 2 〇H NHPh (2-Me) 2-18 FF Et 2 〇H NHPh (4- Me) 2-19 FF Et 2 〇H NHCOPh (2-Cl) 2-20 FF Et 2 〇H NHCOPh (4-Cl) 2-21 FF Et 2 〇H NHCOPh (2-Me) 2-22 FF Et 2 SH NHCOPh (4-Me) 2-23 FF Et 2 〇HN = C (Me) Ph 2-24 FF Et 2 〇H NHC〇2Ph 2-25 FF Et 2 〇H NHC02Ph (2-C1) 2-26 FF Et 2 〇H NHC〇2Ph (4-Cl) 2-27 · F · F Et 2 S H NHC02Ph (2-Me) 2-28 FF Et 2 〇H NHC02Ph (4-Me) 2-29 FF Et 2 〇H CSNHPh 2-30 FF Et 2 〇HC〇2 -1 -Bu 2-31 F: F Et 2 〇H CH2CO2 -1 -Bu 2-32 F: F Et 2 〇H CC2Ph (4-Cl) 2-33 FF Et 2 〇H C02Ph (4-Me) -66- (63) 200526552 Table 2 (continued ) No. X1 X2 Y n AGL Physical properties (mp: ° C) 2-34 FF Et 2 〇HC〇2Ph (2-Cl) 2-35 FF Et 2 〇HC〇2Ph (2-Me) 2-36 FF Et 2 〇HN = CHPh (4-Cl) 2-3 7 FF Et 2 〇H S02NMe2 • 2-38 FF Et 2 〇H CH2CH2C〇N (Me) Ph 2-39 FF Et 2 〇H CH2CH2C〇NMe2 2-40 FF Et 2 〇H CH2CH2S02Ph 2-41 FF Et 2 〇H CH2CH2S02N (Me) Ph 2-42 FF Et 2 〇H CH2CH2S〇2NMe2 2-43 FF Et 2 0 Me CON (Me) Ph 2-44 FF Et 2 〇 H CH2CH2CON (Me) CK2 CN 2-45 FF Et 2 〇S02Me CH2C02Et 2-46 FF Et 2 〇S〇2NMe2 CH2C〇2Et 2-47 FF Et 2 〇S02CH2Ph CH2C〇2Et 2-48 FF Et 2 〇S〇2Ph CH2C02Et 2-49 FF Et 2 〇S02N (CH2C = CH) Ph CH2C〇2Et 2-50 FF Et 2 〇S02N (CH2C = CCl2) Me CH2C02Et 2-51 FF Et 2 〇C〇2Ph CH2C〇2Et 2-52 FF Et 2 〇SPh C〇2Ph 2-53 FF Et 2 〇SN (Me) Ph C〇2Ph 2-54 FF Et 2 〇SN (Me) C02- i-Pr C02Ph. 2-55 FF Et 2 〇SN (i-Pr) C02Me C〇2Ph i -67- 200526552 (64) Table 3 No. ^-NMR δ ppm (solvent: CDC13 / 400MHz) 1-14 8.68 (lH / ors), 7.83 (2H / d / J = 7.6Hz), 7.59 (1H, t, J = 7.2Hz), 7.49 (2H, t, J = 7.0Hz), 2.99 (2H, t, J = 7.4Hz), 1.94_ 2.10 (4H, m ), 1.81 (2H, quintet, J = 7.6Hz); 1.00 (3H, t, J = 7.6Hz) 1-15 8 · 45 (lH'brs), 7.60 (1H, d, J = 8.0Hz) , 7.33-7.44 (31110,2.90 (2 ^ 1 = 7.4112), 1.94- 2.10 (4H, ιτ〇, 1.80 (2H, quintet, J = 7.5Hz), 0.99 (3H, t, J = 7.6Hz) 1-16 8.11 (lH, brs), 7.36-7.42 (2H, m), 7.23- 7..27 (2H, m), 2.95 (2H, t, J = 7.4Hz), 2.47 (3H , s), 1.98- 2.10 (4H, m), 1.81 (2H, guintet, .5Hz), 1.00 (3H, t, J = 7.4Hz) 1 -17 8.49 (IH'brs), 7.76 (2H, td, J = 2.2, 8.8Hz), 7.47 (2H, td, J = 2.2, 8.8Hz), 2.96 (2H, U = 7.2Hz), 1.97- 2.10 (4H, m), 1.80 (2H, quintet , J = 7 · 5Ήζ), 0.99 (3H, 1,: 7 = 7.2Hz) 1-21 8 · 78 (lH, brs), 7.32 (2H, t, J = 7.6Hz), 7.04 (1H, t, .2Hz), 6.9 2 < 2Ι1, ά ,: 7 = 7.6Ηζ), 4.58 (2Η, 5), 2.82 (2Η, 1:, νΤ = 7.4Ηζ), 1.95 2.07 (4H / m); 1.77 (2H, quintet; J = 7.5Hz), 0.99 (3H, t, J = 7.2Hz) 1-26 8.52 (lH, brs), 7.82 (2H, d, J = 8.0Hz ), 7.59 (lH, t, J = 7.6Hz), 7.49 (2H, t, .6Hz), 2.99 (2H, t, J: = 7.2Hz), 1.93 — 1.98 (2Η, π〇, 1.71 (2H, guintet, J = 7.6Hz), 1.53 (3H, t, J = 3.2Hz), 1.33-1.47 (4H / m) 1-2 7 8.37 (lH, brs), 7.61 (1H , d, .6Hz), 7.34—7.44 (3H, m), 2.90 (2H, t, J = 7.6Hz), 1.93-1.98 (2Η, π), 1.71 (2H, quintet, J = 7.3Hz), 1.53 (3H, t, J = 2.8Hz), 1.32-1.47 (4H, in) 1-28 8.10 (Hbrs), 7.36-7-43 (2Η, ιη), 7.23 — 7.27 (21 ^ 111), 2.95 (2H, t, J = 7 · 6Hz), 2 · 47 (3H, s), 1.94-1 · 98 (2H, m), 1 · 71 (2H, quint: et, J = 7 · 6Hz), 1.53 (3H, t ·, J = 3.2Hz), 1.35-1.47 (4H; in) 1-2.9 8 · 55 (lH, brs), 7.77 (2H, td, J: 2.4,8.8Hz), 7.46 (2H, td, J = 2.3, 8.4.1Ι3ζ), 2.97 (2Η, υ = 7.6Ηζ), 1.93-1.S8 (2Η, ιτ〇, 1.70 (2H, guintet, J = 7.6Hz) , 1.53 (3H, t, J = 3.0Hz), 1.32-1.47 (4H; m) 1-45 8.77 (lH, brs), 7.84 (2H, d, J = 7.2Hz), 7.58 (lH, t, J = 7.2H; 2), 7.4 3 (2H, t, J = 7.2Hz), 2.99 (2H, t, J = 7.4Hz), 1.93-1.99 (4H, m), 1.71 (2H, guintet, J = 7.3 Hz), 1.34-1.46 (4H, m), 0.97 (3H, t, J = 7 · 6Ηζ) 1-46 8.53 (Hbrs), 7.60 (1ϋ, υ = 7.2Ηζ), 7.43 (2ϋ: 7 = 4.0 × ζ), 7.3 3-7.38 (ΙΗ, ιη); 2.89 (2H, t, J = 7.4Hz); 1.92-1.99 (4H, ir〇, 1.70 (2H, guintet, J = 7.3Hz), 1.32- 1.45 (4H, in), 0.97 (3H # t, J = 7.6Hz) 1 -47 9.16 (lH, brs), 7.90 (1H, t; J = 2.0Hz); 7.76 (1H, dyJ = 8.0Hz), 7.5 6 (1 ^, 0, J = 8.0Hz) i7.42 (lH; t, J = 8.0Hz), 2.S8 (2H, t, J = 7.6Hz), 1.93-1.98 (4H, m), 1.71 (2H; quintet, J = 7.3Hz), 1.32-1.45 (4H, m) 7 0.97 (3H, t, J = 7.6Hz)

-68- 200526552 (65) Table 3 (continued) Number ^ -NMR δ ppm (solvent: CDC13 / 400MHz) 1-48 9.18 (lH ^ brs), 7.84 (2H, d; J = 8.8Hz), 7.45 (2H , d, J = 8.4Hz), 2.97 (2H, t, J = 7.4Hz); 1.93-1.99 (4H, m), 1.69 (2H, quintet, .5Hz), 1.33-1.45 (4H, m), 0.96 (3H, t, J = 7.4Hz) 1-49 8.32 (lH, brs), 7.21- 7.43 (4H, m), 2.93 (2H, t, J = 7.4Hz) , 2.46 (3H, s), 1.93-2.00 (4H / m), 1.69 (2H, quintet, J = 7.2Hz); 1.34-1 · 45 (4H, m), 0.97 (3H, t, J = 7.6Hz ) 1-50 8.60 (1Η, ϊ): Γ5), 7.64 (1Η, 5), 7.61 (1ϋ〇Γ = 7 · 6Η: ζ), 7.34-7 · 40 (2H, m), 2.98 (2H, t, J = 7.6Hz), 2.40 (3H, s), 1.94-2.00 (4H, m), 1.71 (2H, quintet, J = 7.4Hz); 1.33-1.46 (4H, m), 0 · 97 (3H, t, J = 7.6Hz) 1-51 8.57 (lH, brs), 7.72 (2H, d, J = 8.4Hz), 7.28 (2H, d, J = 7.6Hz), 2.9 8 (2H , t, J = 7.4Hz), 2.41 (3H, s), 1.93-1.99 (4H, m), 1.70 (2H, quintet, J = 7.3Hz), 1.33-1.46 (4H, m), 0 97 (3H, t, J = 7.2 Hz) 1-52 8.95 (lH, brs), 7.84 (2H, d, J = 8 0Hz), 6.95 (2H, d, J = 8.4Hz), 3 · 8 5 (3H, s) /2.98(2H/t/J=7.2Hz) /1.91-1.97(4H/iti),1.70-1.74(2H,m),1.31-1.46(4H / m), 0.96 (3H, t, J = 7.2Hz) 1-53 8.54 (lH, brs), 7.70 (2H, d, J = 7.6Hz), 7.25 (2H, d, J = 8.4Hz) r2. 9 3 (2H, t, J = 7.2Hz), 2.65 (2H, q, J = 7.7Hz), 1.86-1.94 (4H, m), 1.66 (2H, quintet, J = 7.5Hz), 1 μ-ΐ. 40 (4H, m), 1.19 (3H, t, J = 7.6 Hz), 0.92 (3H, t, '6Hz) 1-54 8 · 86 (1H, brs), 7.79 (2H, d, J = 8 · 4Hz), 7 · 48 (2H, d, J = 8.4Hz :), 2.9 8 (2H7 t, J = 7.4Hz), 1.93-1.99 (4H, m), 1.70 (2H , quintet, J = 7.5Hz), 1.35-1.43 (4H, m), 1.32 (9H, s), 0.96 (3H, t, J = 7.6Hz) 1-55 8.24 (lH, brs), 7.49-7.74 (4H, m), 2,84 (2H, t, J = 7.2Hz), 1.92-1.99 (4H, m), 1.67 (2H, quintet, J = 7.5Hz), 1.32--1.44 (4H / m), 0.97 (3H, t, J = 7.6Hz) 1-58 8.65 (IH'brs), 8.19 (1H, dd, J = 8.2, 1.0Hz), 7.72 (1H, td , J = 7.6, 1.4 Hz), 7.62 (1H, td, J = 7 · 8, 1.6 Hz), 7.43 (1H, dd, J = 7 · 6, 1.2 Hz), 2 · 58 (2H, t, J = 7.4Hz), 1.91- 1.98 (4H, m), 1.62 (2H, quintet, J = 7.5Hz), 1.25-1.41 (4H / m) /0.96 (3H, t7J = 7.2Hz ) 1-60 8.68 (IH ^ rs); 7.27-7.33 (3H, m), 2.71 (2H; brs), 1.92-1.99 (4H; m), 1.66 (2H; quintet, J = 7.3Hz), 1.29- 1.43 (4H / m), 0.96 (3Hft; J = 7.4Hz) 1-61 8.59 (lH, brs), 7.54 (ΙΗ, ά, J = 8 · 4Hz), 7.45 (1H, d, J = 2.0Hz), 7.3 4 (1H; dd; J = 8.4,2.0Hz), 2.85 (2H, t, J = 7.6Hz), 1.92-1.99 (4H, m), 1.68 (2H, quint et, J = 7.3 Hz), 1.32-1.45 (4H / m), 0.97 (3Hf t; J = 7.6Hz)

-69- 200526552 (66) Table 3 (continued) No. ^-NMR δ ppm (solvent: CDC13 / 400MHz) 1-64 10.45 (lH ^ rs), 8.59 (ΙΗ, ά, J = 4.0Hz), 8.23 (1H ; d, J = 7.6Hz), 7.90 (1H, td; J = 7.7,1.6Hz), 7.50-7.53 (lH, m), 2.95 (2H, t, J = 7.6Hz), 1.92- 1.99 ( 41 ^, 111), 1.72 (2?!, 21: 1: 111, 61:61, Ting = 7.5! '12), 1.-3 3- 1.45 (4H, m), 0.96 (3H, t, J = 7 · 2Hz) 1-65 9 · 71 (lH, brs), 9.13 (111,5), 8.78 (lH, d, J = 4.0Hz), 8.24 (lH, td, J = 2.0, .8 · 0Hz), 7.43 (1H, dd, J = 8 · 0,4 · 8Hz), 2 · 96 (2H, t, J = 8.0Hz), 1.91-1.96 (4H, m), 1.68 (2H, quintet, J = 7.3Hz), Ul-US (4H, m), 0.95 (3H, t, J = 7.6Hz) 1-66 9'13 (lH, brs), 8.82 (2H, d7J = 4.4Hz>, 7.74 (2H, 0Hz), 2.96 (2H, t, J = 7.4Hz), 1.92- 1.99 (4H, m), 1.70 (2H, quintet, J = 7.3Hz), 1.33-1.45 (4H / m) / 0.97 (3H / t, J = 7.6Hz) 1-67 8.44 (lH, brs), 7.64 (1H, dd, J = 4.8,0.8Hz), 7.62 (lH, dd, J = 3.8, 0.8 Hz), 7.13 (lH, dd, J = 4.8, 3.8Ηζ), 2.96 (2H, t, J = 7.6Hz), 1.93 1.45 (4H, m), 0.97 (3H, t, J = 7.4Hz) 1-73 10.06 (lH, brs), 9.43 (1H, d, J = 1.6Hz), 8.83 (lH, d, J = 2.4Hz), 8.58 (lH, dd, J = 2.4,1.6Hz ), 2.95 (2H, t, J = 7.4Hz), 1.92-1.98 (4H, m), 1.71 (2H, quint: et, J = 7.4Hz), 1.33-1.45 (4H / m), 0.95 (3H, t, J = 7.4Hz) 1-86 8.35 (lH, brs), 8.31 (lH, d, J = 8.0Hz), 8.00 ( lH, d, J = 8.0Hz), 7.90 (1Η, ζϊ, σ = 8.0Ηζ), 7.70 (ΐΗ, υ = 7.6Ηζ), 7.53 — 7.6 0 (211,111), 7.49 (111,1 :, ^ 7 = 7.8112), 3.04 (211, ^ = 7,41 ^), 1.95-2.01 (4H, m), 1.76 (2H, quintet, J = 7.3Hz), 1.38-1 · 47 (4Η, πι), 0 · 98 (3Η, t, J = 7 · 4Hz) 1-90 8.79 (lH, brs), 7.32 (2H, t, J = 8 · 0Hz), 7.04 (1H, t, J = 7 · 4Hz ), 6.9 2 (2H, d, vJ = 7.6Hz), 4.59 (2H, s), 2.82 (2H, t, J = 7.2Hz), 1.92-1. S9 (4H, in), 1.67 (2H , quintet, J = 7.5Hz), 1.30-1.44 (4H, m), 0.97 (3H, t, J = 7.6Hz) 1-91 8.89 (lH; brs), 7.16- 7.31 (5H, m), 3.78 (2H, s), 2,55 (2H, t, J = 7.4Hz), 1.86-1.93 (4H, m>, 1.55 (2H, quintet, J = 7.5Hz), 1.21-1.35 (4H, m), 0.91 (3H, t, J = 7.6Hz) 1-94 8.69 (lH, brs), 7.30 (2H, t, J = 8.0Hz), 7.03 (1H, t, J = 7.6Hz), 6.88 (2H, d, J = 7.6Hz), 4.72 (1H, q, J = 6.9Hz >, 2.82 (2H, t, J = 7.6Hz), 1.92-1 · 98 (4Η, ιπ), 1 61-1.67 (2H, m), 1.58 (3H, d, J = 6.8Hz), 1.28-1.42 (4H, m), 0.96 (3H, t, J = 7.4Hz) 1-97 9.05 (lH , brs), 7.39 (1H, dd, J = 8.0, 1.6Hz), 7.22 (1H, td, J = 8.4, 1.2Hz), 6.99 (1H, td, J = 7 · 8 , 1.OHz), 6.87 (1H, dd, J = 8.2, 1.0Hz), 4.64 (2 H, s), 2.77 (2H, t, J = 7.6Hz), 1.2-1.98 (4H, m), 1.67 (2H, quintet, J = 7.5Hz), 1.3 〇-Ο .44 (4H, m ), 0 .96 (3H, t, J = 7.6 Hz)

-70- 200526552 (67) Table 3 (continued) No. ^ H-NMR δ ppm (solvent: CDC13 / 400MHz) 1-98 8.76 (lH, brs), 7.23 (1H, t, J = 8 · 2Ηζ) , 7 · 02 (1H, td, J = 0 · 8,8 · 0Hz), 6.93 (1H, t, J = 2 · 2Ηζ), 6.81 (lH, dd, J = 8 · 0,2 2Ηζ), 4.63 (2H, s), 2.77 (2H, t, J = 7.2Hz), 1.92- 1.99 (4H / m), 1.65 (2H, quintet, J = 7.5Hz), 1.27-1.44 ( 4H, m), 0.97 (3H, t, J = 7.6 Hz) 1-99 8.70 (lH, brs), 7.27 (2H, d, J = 8.8 Hz), 6.85 (2H, d, J = 8.8Hz), 4.60 (2H, s), 2.78 (2H, t, J = 7.2Hz), 1.92-1.99 (4H, m); 1.66 (2H, quintet, J = 7.1Hz ), 1.31-1.44 (4H, m), 0.97 (3H, .t, J 7.4Hz) 1-100 8.74 (lH, brs), 7.13-7.24 (2H, m), 6.94 (1H, t, J = 7.6Hz), 6.74 (1H, d, J = 7.6Hz), 4.59 (2H, s), 2.82 (2H, t, J = 7.0Hz), 2.29 (3H, s), 1.92- 1.99 (4H, m), 1.67 (2H, quintet, J = 7.1Hz), 1.31-1 · 44 (4H, m), 0.97 (3H, t, J = 7.4Hz) 1-101 8.74 (lH, brs) , 7.198Hz), 6.85 (lH, d, J = 7.6Hz), 6.72 (2H, t, .6Hz), 4.56 (2H, s), 2.82 (2H, J = 7.4Hz), 2.33 (3H, s ), 1.92-1.99 (4H / m), 1.66 (2H, quintet, J = 7.4Hz), 1.30-1.44 (4H, m), 0.97 (3H, t, J = 7.4Hz) 1-102 8 · 76 (lH, brs), 7.10 (2H, d, J = 8.8Hz); 6.80 (2H, d, J = 8.8Hz), 4.5 4 (2H, s), 2.82 (2H, t , J = 7.6Hz), 2.28 (3H, s), 1.92-1.9 9 (4H, m), 1.66 (2H, quintet, J: = 7.5Hz), 1.3 0-1.44 (4¾ ^), 0.97 (3H, t, J = 7.4Hz) 1-114 8 · 78 (lH, brs ), 7.84 (2H, d, · 2Ηζ), 7.58 (1H, t, J = 7.4Hz), 7.48 (211,1 ^ = 7.6 ^), 2.98 (211,1:, ^ = 7.21 ^), 1.91-1 · 99 (4H, in), 1 · 69 (2H, quintet, J = 7 · 3H), 1.23-1.42 (8H, m), 0.96 (3H, t, J = 7.2Hz) 1-115 8.42 (IH'brs), 7.60 (lH, d, J = 7.6Hz), 7.42-7.44 (2H, m), 7.34-7.38, 2.89 (2H, t, J = 7.2Hz ), 1.91-1.99 (4H / m); 1.69 (2H # quintet, J = 7.5Hz), 1.23-.1.40 (8H, m), 0 · 97 (3H, t, J = 7.6Hz) 1-116 8.37 (lH, brs), 7.22- 7.43 (4H, m), 2.93 (2H, t, J = 7.6Hz), 2.46 (3H, s), 1.91-1.99 (4H, m), 1.69 (2H, quintet, J = 7.4Hz), 1.23-1.41 (8H, m), 0.97 (3H, t, J = 7.6Hz) 1-117 8.70 (lH, brs), 7.79 (2H, d, J = 8.4Hz), 7.46 (2H , d, J = 8.4Hz), 2.96 (2H, t, J = 7.4Hz), 1.90- 1.98 (4H / m), 1.68 (2H7 quintet, J = 7.1Hz), 1.24-1 · 41 (8H, m), 0.96 (3H, t, J = 7.4 Hz) 1-147 7.58 (2H, d, J = 7.2 Hz), 7.53 (1H, t, J = 8.4 Hz), 7.44 (2H , t, J = 7.2Hz), 3.17 (3H, s), 2.59 (2H, t, J = 7.4Hz), 1.89-1.96 (4H # m); 1.64 (2H, quintet, J = 7.5Hz) , 1.21-1.40 (4H / m), 0.94 (3H; t, J = 7.4Hz) -71-(68) 200526552 Table 3 (continued) No. ^-NMR δ ppm (solvent: CDC1 3 / 400MHz) 1-168 8.49 (1Η, 33ΐ ^), 7.71 (2Η, ά ,: Γ = 8.4Ηζ), 7.28 (2Η, υ = 7 · 6Ηζ), 2.9 8 (2H, t, J = 7.4Hz ), 2.39 (3H, s), 1.97-2.10 (4Η, ιη), 1.80 (2Η, quintet, J = 7.5Hz), 0.99 (3H, t, J = 7.6Hz) 1-169 8.39 ( lH'brs), 7.40- 1.99 (4H, m), 1.68 (2H, quintet, J = 7.3Hz), 1.32-1.45 (4H / m), 0.97 (3H; t; J = 7.6Hz) 1-17 0 8.80 (1Η,) 3Γ · 5), 7.73 (2H, d, J = 8.8Hz), 7.62 (2Η, υ = 8 · 8Ηζ), 2. 7 (2H, t, J = 7.4Hz), 1.92- 1.99 (4H, m), 1.70 (2H, quintet, J = 7.5Hz), 1.33-1.45 (4Η, ιπ), 0.97 (3H, t, J = 7.4Hz) 1-171 8.22 (IH ^ rs), 7.89 (1H, d, J = 8.0Hz); 7.39-7.42 (2H, m), 7.13-7.18 (ΙΗ, ιη), 2.89 (2H, t, · 4Hz), 1.93 — 1.99 (4H, m), 1.70 (2H, quintet, J = 7.5Hz), 1.34 -1.45 (4H, m), 0.97 (3H, t, J = 7.6Hz) 1-172 8.49 (lH, brs), 7.85 (2H, d, J = 8.8Hz), 7.54 (2H, d, J = 8.8Hz), 2.96 (2H, t, J = 7.4Hz), 1.93-1.99 (4H, m), 1-70 (2H, quintet, J = 7.4Hz), 1.33 -1.45 (4H, m), 0.97 (3H, t, J = 7.6Hz) 1-173 8.62 (1H, brs), 7.57 (lH, dd, J = 7.6, 1.6Hz), 7.46 (1H, td, J = 8.0, 1.6Hz), 7.34 (lH, d, J = 7.2Hz), 7.22 (lH, t, vJ = 8.0Hz), 2.95 (2H , t,: 3Γ = 7.4Ηζ), 2.47 (3Η, 5), 1.94 * 1.99 (4H / m), 1.71 (2H, quintet, J = 7.3Hz), 1.33-1.46 (4H / m) /0.97 (3H / t, J = 7.6Hz) 1-174 8.52 (1H, brs), 7.80 (2H, d, J = 8.8Hz), 7.39 (2H, t, J = 8.0Hz), 7.20 (1H # t, J = 7.6Hz), 7.00-7.07 (4¾ ^), 2.97 (2H; t , J = 7.6Hz), 1.93-1.99 (4H, m), 1.71 (2H, quintet, J = 7.3Hz), 1.33-1.45 (4H, m), 0.97 (3H, t, J = 7,6Hz ) 1-17 5 7.59 (lH, m), 7.30 (1H, td, J = 7.4,0.8Hz), 7.17 (1H, dd, J = 12.〇, 8.4Hz), 2.94 (2H, t , J = 7.8Hz), 1.93-1.99 (4¾ ^), 1.71 (2H, quintet, J = 7.5Hz), 1.34-1.46 (4H / m), 0.97 (3H, t, J = 7.6Hz) 1-17 6 8.33 (1H, brs), 7.62 (1H, dd, J = 8.0.0, 0.8Hz), 7.50 (1H, dd, J = 7.6, 1.6Hz), 7.31-7.41 (2H, m) , 2.89 (2H, t, J = 7.6Hz), 1.92-2 · 00 (4H, m), 1.70 (2H, quintet, J = 7.5Hz) 丄 34-1 · 45 (4H, m), 0 97 (3H, t, J = 7.4Hz) 1-177 8.58 (lH, brs), 7.72 (2H, d, J = 8.0Hz), 7.27 (2H, d, J = 8.0Hz), 2 9 7 (2H, t, J = 7.4Hz), 2.41 (3H, s), 1.91-1.98 (4H, m), 1.69 (2H, quintet, J = 7.3Hz), 1.24-1.41 (8H, m) , 0.96 (3H, t, J = 7.6Hz)

-72- 200526552 (69) Table 3 (continued) No. ^-NMR δ ppm (solvent: CDC13 / 400MHz) 1-178 8.82 (1H, brs), 6.93-7.15 (4H, no, 4.65 (2H, s) , 2.79 (2H, t, J = 7.2Hz), 1.92-1.99 (4H, m), 1.67 (2H, quintet, .4Hz), 1.31-1.43 (4H / m), 0.97 (3H, t, J = 7.4 Hz) 1-179 9.00 (lH, brs), 7.29 (2H, t, .6Hz), 6.93 (1H, t, J = 7.4Hz), 6.8 3 (2H, d, J = 8.0Hz), 4.02 (2H, s), 3.04 (3H; s), 2.78 (2H, tr J = 8.OH z), 1.93-1.99 (4H, m), 1.63 (2H, guintet, J = 7.4H2 :), 1.28- 1.43 (4H, m), 0.97 (3H, t, J = 7.6Hz) 1-180 7_ 86 (1H, td, J = 7.8, 2.0 Hz), 7.53- 7.59 (ΙΗ, ιη) , 7.27 (1Η; td, J = 7,6t 1.2Hz), 7.09 (1H, dd, J = li. 2,8 .4Hz), 2.65 (4H, t, J = 7.2Hz), 1.92-1.97 (8H ; m), 1.65 (4 ^ 1, quintet; J = 7.5Hz), 1.26-1.42 (8H, m), 0.95 (6H, t, J = 7.4Hz) 1-200 8.61 (lH, brs) , 7.74 (2H, d, J = 8.8Hz), 6.70 (2H, d, J = 8.8Hz), 3.0 5 (6H, s), 2.98 (2H, t, J = 7.4Hz), 1.93-1.98 (4H , m), 1.70 (2H, guintet:, J = 7.4Hz), 1.34-1.45 (4H / m) 7 0.9 6 (3H, t; J = 7.6Hz) 1-207 8.51 (lH, brs), 7.71 (2H, d, J = 8.4Hz), 7.28 (2H, d, J = 0.8Hz), 2.98 (2H, t, J = 7.4Hz), 2.41 (3H, s), 1.93- 1.98 ( 2H, m), 1.71 (2H, quintet, J = 7.4Hz), 1.53 (3H, t, J = 3.2Hz), 1.32-1.46 (4H; m) 1 -27 9 10.17 (lH, brs), 8.13 (1H, dd, J = 8.0, 2.0 Hz), 7.51 (1H, td, J = 8.0, 2.0 Hz), 7.08 (1H, td, 8.0, 0.8Hz), 6.99 (1H, d, J = 8.OHz), 3.98 (3H, s), 2.93 (2H; t, J = 7.6Hz), 1.92-1.98 (4H, m) , 1.69 (2H, quintet, J = 7.4Hz), 1.33-1.44 (4H, m), 0.95 (3H, t, J = 7.6Hz) 1-280 8.6 6 (1H, brs), 7.8 8 (1H, dd , J = 7.6,2.OHz), 7.58 (1H, td, J = 7.8 7 2.OHz), 7.43 (1H, t, J = 7.8Hz>, 7.33 (1H, d, J = 8.OHz), 2.89 (2H, t, J = 7.4Hz), 1.93- 1.99 (4H, m), 1.70 (2H, quintet, J = 7.3Hz), l .; 34-1 · 45 (4H, m), 0 97 (3H, t, J = 7.4Hz) 2-1 5.93 (lH'brs), 4.20 (2H, q, · 1Hz), 4.01 (2H, d, J = 5.2Hz) , 2.2 2 (2H, t, J = 7.6Hz), 1.92- 1.98 (4H, m), 1.64 (2H, quintet, J = 7.5Hz), 1.23-1.42 (7H, m), 0.96 (3H, t, J: 7.6Hz) 2-2 8.83 (IH'brs), 8.05 (2H, d, J = 6.8Hz), 7.64 (1H, t, .2Hz), 7.54 (2H, t, J = 7.2Hz), 2.24 (2H, t, J = 7.6Hz), 1.84—1.92 (4H / m), 1.54 (2H, quintet, J = 7.6Hz), 1.13-1 · 32 (4H, in), 0 · 92 (3H, t, J = 7 · 6Hz) 2-3 7 · 36 (2H, t, J = 7.8Hz), 7.21 (1H, t, J = 7.2Hz), 7.06 (2H, d, J = 7.6Hz); 2.54 (2H, t, J = 1.2Hz), 1.94-2.01 (4H, m), 1.75 (2H, quintet, J = 7.55Ηζ), 1.35-1.48 (4H , m), 0.98 (3H, t, J = 7.6 Hz) -73- 200526552 (70) Table 3 (continued ) No. ^-NMR δ ppm (solvent: CDC13 / 400MHz) 2-4 10 · 68 (lH, s), 10.03 (lH, brs), 7.51 (2H, d, J = 8.0Hz), 7.31 (2H, t ,: Γ = 8.0Ηζ), 7.11 (1Η, Ι :, ν7 = 7.6Ηζ), 2.43 (2Η, υ = 7 · 4Ηζ), 1.92-1.98 (4H, m), 1.72 (2Η, quintet , J = 7.6 Hz), 1.32 -1.44 (4H, m), 0.95 (3H, t, J = 7.6Hz) 2-5 8.08 (1H, brs), 7.09 (2 ^^ = 7.21 ^ ), 6.81 (2Hz), 6.65 (2H, d, J = 8.0Hz) J.lWlH'brs), 2.05 (2H, t, J = 7.6Hz), 1.84_1.89 (4Η, ιη), 1 47-1 · 55 (2Η, Γη), 1.17-1 · 27 (4H, m), 0.90 (3H, t, J = 7.6 Hz) 2-6 8.37 (2H, d, J = 4.8Hz), 7.62 (lH, brs), 7.14 (lH, brs), 6.75 (1H, t, J = 4.8Hz), 2.29 (2H, t, .6Hz), 1.91-1.99 (4H / m), 1.66-1.73 (2H, m), 1.31-1 · 42 ΜΗ, ιτι), 0.96 (3H, t, J = 7.6Hz) 2-7 9.03 (lH, brs), 8.70 (lH, brs) , 7.80 (2H, d, J = 7.2Hz), 7.53 (lH, t, vJ = 7.2H :?), 7.43 (2H, t, J = 7.2Hz), 2.31 (2H, t, J = 7.2Hz) , 1.93-1.97 (4H, m), 1.57-1.78 (2H, m), 1.28-1.43 (4H / m), 0.96 (3H # t # J = 7.2Hz) 2-8 8.40 (lH, brs), 7.53 (4Η, (^ νΙ = 7.2Η2), 7.32-7.3, 7.22 (2H / dd / J = 7.2, 1.6Hz), 2.83 (2H, t, J = 8Hz), 1.94-1.98 (4H, m), 1.71 -1.76 (2H, m), 1.39-1.45 (4H / m), 0.97 (3H, t, J = 7.6Hz) 2-9 7.33 (lH, brs), 6.73 (lH, brs), 3.74 (3H, s ),2. 21 (2H, t, J = 7.6Hz), 1.90-1.99 (4H, m) # 1.58-1.69 (2H / m), 1.21- 1.38 (8H, m), 0.96 (3H, t, J = 7.6Hz) 2-10 7.87-7.91 (2H, m), 7.58-7.66 (2H / m), 7.47- 7.52 (2H, m), 7.30 (lH, d, J = 5.6Hz), 2.01 (2H, t, J = 7.6Hz), 1.89-1.99 (4H, m), 1.29-1 · 41 (4H, m), 1.14-1.22 (4H, m), 1.05--1.11 (2H / m), 0.96 (3H, t, J = 7.6Hz) Now, test examples will be described. Test Example 1 Southern Rhizobial Nematode (M e 1 〇id 〇gyneinc 〇gnita) Test 200 ml of soil contaminated by Southern Rhizobial Nematode was poured into 10 ml of a chemical solution having a concentration of the compound of the present invention adjusted to 800 ppm, and then mixed to cause the compound Disperse evenly. The test soil was poured into pots (diameter: 8 cm, height: 9 cm), after which the tomato seedlings in the 2-leaf stage were replanted and placed in the greenhouse. Six weeks after transplanting from tomatoes, the nodule index was determined according to the criteria in Table 4 below. The above compound numbers 1-51, 2-1, 2-3, 2-4 '2-6 and 2-9 were determined, whereby all the compounds showed a small nodule index -74-200526552 (71) at a scale of 1. Control effect. Table 4 Degree of nodule formation Nodule formation 0 No nodulation formation 1 Nodulation formation to mild degree 2 Nodulation formation to moderate degree 3 Nodulation formation to severe degree 4 Nodulation formation to the most severe test example 2 Resistance to two-point lobe infusion (T etranychusurticae) Pesticide test Pesticide solution was prepared to bring the compound of the present invention to a concentration of 200 ppm. Phaseolus vulgaris seedlings with only one main leaf remaining were transplanted. In the pot (diameter: 8 cm, height: 7 cm), 20 mature Tetranychus imicae were budded. The mature mites are immersed in the upper killing solution together with kidney bean leaves, then dried in the air, and placed in an ordinary greenhouse with lighting at 25 ° C. On the second or third day after treatment, the dead adult mites were counted, and the mortality was calculated by the following formula. Adult mites falling from the leaves are counted as dead adult mites. Get about the above compound numbers 1 -1 4 to bu 17, 1-21, 1-26 to 1-29, 1-45 to bu 55, 1-58, bu 60, bu 61, 1-64 to 1-67, 1-73, 1-86, Bu 90, Bu 91, 1-94, Bu 97 to 1-102, Bu 114 to Bu]] 7, U68 to Bu 180, Bu 200, Bu 2 0 7, Bu 2 7 9 'Bu 2 8 0 and 2-] to 2-10 death rates, whereby all of the -75- 200526552 (72) compound deaths showed a highly controlled effect of at least 80% mortality, rate (%) = The number of adult mites killed "100 treated cotton sclerotia sclerophylla scoring cotton cotton spot test trial calculation. To] -1-64 1-1 \ ΊΊ, this test example 3 resistance to spot fly 1¾ ( L a 0 de 1 pha X striate 11 us) Insecticide test Rice seedlings are immersed in an insect solution containing a compound of the present invention at a concentration of 200 PPm, and then dried in the air. After that, the seedlings have their roots wrapped with moist flowers It was placed in a test tube. After that, 10 larvae (Laodelphax striatellus) were put into it, and the test tube was covered with gauze and placed in a greenhouse at 25 ° C with illumination. On the 5th day after the release, count Dead baby The death rate is calculated by the following formula for the above compound numbers 1-1 4 to 1-1 7, 1-2 1, Bu 2 6 • 29, 1-4 5 to Bu 5 1, 1-53 ^]-5 5,1-58,1-60,]-6], to Bu 67, Bu 73, Bu 90, Bu 91, 1-94, 1-98 to 1-102 > 4, 1-116, 1-168 , 1-169, 1-171, 1-173, 1-175, 1-1-178 > Bu 200, 1.207, Bu 280 and 2-9, with compounds showing a mortality rate of at least 80 % Height control effect.

Mortality Number of dead insects Number of insects put in X Test Example 4 Insecticide-76-200526552 (73) resistant to New Zealand cattle _ (Haemaphysa 1 is I ngic 〇rnis) Test 1 ml of the compound of the present invention ( The acetone solution (concentration: 10 pg / ml) was dropped into a 9 cm diameter petri dish with a micropipette. After the inner surface of the petri dish was dried, 60 to 180 young mites were placed, and the petri dish was covered with a polyethylene plate and sealed with a rubber band. The number of mites shot down after contact with the pesticide was observed, whereby the compound of the present invention shot down most New Zealand cattle mites. Test Example 5 Insecticide test using dogs to resist New Zealand cattle mites (Haemaphysalis longicornis) 50 young New Zealand cattle mites were placed in the ears of dogs (beagles, 8 months old) to be artificially parasitic. . From the expiration of 2 days of parasitism, the number of parasitic mites was counted, and the compound of the present invention prepared after that was dispersed at a dose of 10 mg / kg over the back and neck area. Five days after the pesticide was administered, the number of insect parasites, the number of drops, and the mortality of New Zealand cattle mites were observed. Here, dogs are individually housed in cages and allowed unlimited drinking water, given a predetermined amount of dog food once a day. As a result, the compounds of the present invention effectively cause parasitic New Zealand cattle mites to fall or die. Test Example 6 Insecticide test using dogs against cat flea 100 non-sucking mature cat flea (Ctenocephalides felis) were artificially placed in the fur of the back of a dog (beagle, 8 months old) within 3 days after maturation Parasitic, the compound of the present invention is prepared at a dose of 10 mg / kg -77- 200526552 (74) and is dispersed in the back and neck area. Three days after the pesticide was administered, cat flea was obtained by a flea capture comb, and the number of parasites was counted. Here, the dogs are individually housed in cages, and unlimited drinking is allowed. A predetermined amount of dog food is given once a day. As a result, the compounds of the present invention effectively control the parasite of cat flea. Formulation Example 1 (1) 20 parts by weight of the compound of the present invention (2) clay 72 parts by weight φ (3) 8 parts by weight of sodium lignosulfonate The above ingredients are uniformly mixed to obtain a powder that can be mixed with water. Formulation Example 2 (1) 5 parts by weight of the compound of the present invention (2) 95 parts by weight of talc The above ingredients were uniformly mixed to obtain a powder. Formulation Example 3 U) 20 parts by weight of the compound of the present invention (2) N; N '_- methylacetamide 20 parts by weight (3) polyoxyethylene alkyl phenyl ether 10 parts by weight (4) -formaldehyde 50 parts by weight of the above ingredients are uniformly mixed and dissolved to obtain an emulsifiable concentrate-78-200526552 (75) Formulation Example 4 (1) 68 parts by weight of clay (2) 2 parts by weight of sodium lignosulfonate (3 ) 5 parts by weight of polyoxyethylene alkylaryl sulfate (4) fine silica powder 2 5 parts by weight of the mixture of the above ingredients and the compound of the present invention are mixed at a weight ratio of 4: 1 to obtain a powder that can be mixed with water. Formulation Example 5 (1) 50 parts by weight of the compound of the present invention (2) oxyUted polyalkylphenyl phosphate-triethanolamine 2 parts by weight (3) polysiloxane 0.2 parts by weight (4) water 47.8 parts by weight of the above ingredients are uniformly mixed and honed to obtain a base liquid, and (5) 5 parts by weight of a sodium polycarboxylate · (6) anhydrous sodium sulfate 4 8.2 parts by weight, μ * 5T divided by 夂 is added The mixture is uniformly mixed and dried to obtain water particles. Formulation Example 6 (1) 5 parts by weight of the compound of the present invention (2) Polyoxyethylene octylphenyl ether 1 part by weight (3) Polyoxyethylene phosphate phosphate 0 ·] parts by weight -79- 200526552 (76) (4) granules After 93.9 parts by weight of calcium carbonate, the above components (1) to (3) were uniformly mixed and diluted with an appropriate amount of acetone, and then the mixture was sprayed onto the component (4), and the acetone was removed to obtain pine nuts. Formulation Example 7 (1) 2.5 parts by weight of the compound of the present invention (2) 72 parts by weight of N-methyl-2-pyrrolidone Φ (3) 95.0 parts by weight of soybean oil The above ingredients are uniformly mixed and dissolved to obtain an ultra-small volume Of preparations. Formulation Example 8 (1) 40 parts by weight of the compound of the present invention (2) oxidized polyalkylphenyl phosphate-triethanolamine 2 parts by weight (3) polysiloxane 0.2 parts by weight (4) Sansen Glue, weight, f, (5) ethylene glycol, 5 parts by weight, (6) water, 5 2.7 parts by weight, the above ingredients were uniformly mixed and honed to obtain a suspension concentrate based on water. Formulation Example 9 (1) 10 parts by weight of the compound of the present invention (2) 90 parts by weight of diethylene glycol monoethyl ether The above ingredients were uniformly mixed to obtain a soluble concentrated solution ° -80-

Claims (1)

200526552 (1) X. Application for patent scope 1. A haloene compound or a salt thereof represented by formula (I): χ1 \ / X2, A ΟIICH2 (CH2CH2) n—C-1 \ | L (I) where X1 and X2 are each halogen; Y is alkyl, haloalkyl, or benzene n is from 0 to 5, L is -C (= B) Q, = -C (= B) N (D) Q, -N ( D) Q, -N (D) c (= B) Q, -N (D) C (= B) B'Q, -N (D) S02Q, 'n = CHq, · ν = (: ((5 ) 2, -SO 2 Q, -S 0 2 N (D) Q or an alkyl group substituted with J (the alkyl group may be further substituted with another substituent), J is -C (= B) B, Q, -C ( = B) N (D) Q, _ or-S〇2N (D) Q; G and D are each a hydrogen atom, an alkyl group, a haloalkyl group, an alkyl group, an alkenyl group, a haloalkenyl group, a phenylalkenyl group, Alkynyl, haloalkynyl, phenyl, -C (= B) Q '-C (= B) B'Q, -c (= B) N (G,) Q, -SQ, -S02Q, -SN ( G ') Q, -SN (G') C (= B) B, Q or -S02N (G,) Q is a radical, halogen radical, phenyl radical, halogen radical, halogen radical, phenyl radical Alkynyl, haloalkynyl, or phenylalkynyl; A, B, and "each is an oxygen atom or a daughter; Q is an alkyl group that may be substituted, an alkenyl group that may be substituted, an alkynyl group that may be substituted, or a substituted one Cyclic hydrocarbon group, or 5- to 12-membered heterocyclic group (heterocyclyl can be substituted) selected from oxygen atom, thiogen nitrogen atom and random hetero atom. 2. The haloene compound or the salt thereof according to the scope of the patent application] wherein L Is -C (= B) Q… C (= B) B, Q… C (= B) N (D) Q, radical; its so2q phenylalkyne; G? Radical, sulfur primary proton and quilt Take the class, -81-200526552 (2) -N (D) Q, -N ^ COWq, n (d) c (= b) b, q, _n (d) s〇2q, -N = CHQ, -N = C (Q) 2, s〇2q, or · δ〇2Ν (] 〇) ρ. 3 · As for the haloene compounds or their salts in the second item of the patent application, where L is -C (= B) Q, -C (= b) b, q ,, · N (Ε)) (^ or -N = C (Q) 2. 4. If the haloene compound or the salt thereof is the first item in the scope of patent application, Where Q is an alkyl group which may be substituted by w, an alkenyl group which may be substituted by w, an alkynyl group which may be substituted by W, a cyclic hydrocarbon group which may be substituted by w, or an arbitrary heterocyclic group containing an atom selected from an oxygen atom, a sulfur atom, and a nitrogen atom. Atomic 12-membered heterocyclyl (heterocyclyl may be substituted by W); W is halogen, nitro, cyano, & substituted alkyl, K substituted alkenyl, K substituted Alkynyl, A cycloalkyl group substituted with μ1, or a 5- to 12-membered heterocyclic group containing an arbitrary heteroatom selected from an oxygen atom, a sulfur atom, and a nitrogen atom (the heterocyclic group may be substituted), _〇R〗, -SR] , -NR] R2, -COR], _C02R], -C〇SR], -csorI, _Cs2R] '-SC ^ NWR2, -CONR] R2, -CSNR ^ R2, _c (= n〇V) R], -NiR ^ COR3, -N (R)) C02R3, -N (Ri) c〇SR3, -N (R)) CSOR3 ... N (R)) CS2R3, -N (R)) s2R3, -SOR3, _S02R3, _CSR3, -OCOR3, -〇CSR3, _SCOR3, -SCSR3, Sanyuanjishayuan or Sanyuanjiyuanoxy; K is halogen, nitro, cyano, cyclic hydrocarbon group which may be substituted by M], Or a 5- to 12-membered heterocyclic group (heterocyclic group may be substituted) containing an arbitrary heteroatom selected from an oxygen atom, a sulfur atom, and a nitrogen atom, -0M2 ... sm2, -NM2M3, -COM2, C02M2, 'C0SM2, csOM2, -82 »200526552 (3) -CS2M2, -S02NM2M3, -CONM2M3, -CSNM2M3, -C (= NOV) M2, -N (M2) COM4, -N (M2) C02M4, -N (M2) COSM4, -N (M2) CSOM4, -n (m2) cs2m4, -N (M2) S02M4, -SOM4, -S02M4, -CSM4, -OCOM4, -OCSM4, -SC〇M4 or -SCSM4 ; M] is halogen Nitro, cyano, alkyl, haloalkyl, cycloalkyl, halocycloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, -OR4, -SR4, -NR4R5, -COR4, -C02R4 , -COSR4, -CSOR4, -CS2R4, -S〇2NR4R5, -CONR4R5, -CSNR4R5, -C (= NOV) R4, -N (R4) COR6, -N (R4) C02R6, -n (r4) cosr6, -N (R4) CSOR6, -N (R4) CS2R6, -N (R4) S02R6 > -SOR6 > -S02R6 '_CSR6, -OCOR6, OCSR6, _SC〇R6 or -SCSR6; M2 and M3 are each a hydrogen atom, Alkyl which may be substituted by M5, alkenyl which may be substituted by M5, alkynyl which may be substituted by M5, cyclic hydrocarbon group which may be substituted by M], or one containing an arbitrary heteroatom selected from an oxygen atom, a sulfur atom, and a nitrogen atom 5- to 12-membered heterocyclyl (heterocyclyl may be substituted by μ); M4 is an alkyl group which may be substituted by M5, an alkenyl group which may be substituted by M5, an alkynyl group which may be substituted by M5, and may be substituted by Mι Cyclic hydrocarbon group, or 1-membered heterocyclic group containing random heteroatoms selected from oxygen atom, sulfur atom and nitrogen atom (heterocyclic group may be substituted by M]); M5 is halogen, and alkyl substituted by M] Oxy group, alkylthio group which may be substituted by μ], Sulfinyl sulfenyl group, alkane luteinyl group which may be substituted by M, -M 6,-0 M6 or -S M 6; -83- 200526552 (4) M is a cyclic hydrocarbon group which may be substituted by M1 or contains a group selected from oxygen atoms 5_ to 12_ member heterocyclic groups of random heteroatoms of sulfur, nitrogen and nitrogen (heterocyclyl may be substituted by M 1), R1 and R2 are each a hydrogen atom, an alkyl group which may be substituted by M7, and may be substituted by M7 Diluted group substituted by M7, alkynyl group substituted by M7, cyclic hydrocarbon group substituted by μ 1, or a 5- to 12-membered heterocyclic group having a random heteroatom derived from oxygen atom, sulfur atom, and nitrogen atom (Heterocyclic group may be substituted by Mm); R3 is an alkyl group which may be substituted by M7, an alkenyl group which may be substituted by M7, an alkynyl group which may be substituted by M, a cycloalkyl group which may be substituted by M1, or a group selected from oxygen 5-membered heterocyclic groups of random heteroatoms of atoms, sulfur atoms and nitrogen atoms (heterocyclic groups may be substituted by M1); M7 is a halogen, a cycloalkyl group which may be substituted by M], containing a group selected from oxygen atoms, sulfur Atoms and nitrogen atoms of random heteroatoms to 12-membered heterocyclic groups (heterocyclic groups may be substituted by M1), -OM8, -SM8, -NM8M9, -COM8 > -C02M8 ^ -COSM8 > -CSOM8 ^ -CS2M8 ^ -S02NMsM9 ,, CONM8M9, -CSNM8M9, -C (= N〇V) M8, -n (ms) com] 0, -n (m8) co2m] 0, -n (m8) cosm10, -n (m8) csom] 0, -n (m8) cs2m10, -n (ms) so2m] 0, -s Ο μ] 0, -S 0 2 M] 0, -CSM] 0, -〇C 〇 M] 0,-〇c SM] 0, -SCOM10 or -SCSM10; M8 and M9 are each a hydrogen atom, an alkyl group which may be substituted by M 1, an alkenyl group which may be substituted by M 1, and an M group which may be substituted by M] An alkynyl group, a cycloalkyl group which may be substituted by M], or a 5-membered to 2-membered heterocyclic group containing an arbitrary heteroatom selected from an oxygen atom, a sulfur atom, and a nitrogen atom (the heterocyclic group may be substituted by M 1); -84-200526552 (5) M1 G is an alkyl group which may be substituted by Mi, an alkenyl group which may be substituted by M], an alkynyl group which may be substituted by M], a cycloalkyl group which may be substituted by M], and 8 a From 5 to King of random heteroatoms of oxygen atom, sulfur atom and nitrogen atom 1 2 · Λ 雑 ring group (heterocyclic group may be substituted by M]); V is hydrogen atom, alkyl group which may be substituted by M], Can be substituted by μ] 'canyl' may be substituted by M] alkynyl, cycloalkyl which may be substituted by M1, selected from oxygen atom, sulfur 5- to 12-membered heterocyclic group of random heteroatoms of nitrogen and nitrogen atom (heterocyclic group may be substituted by M1); R4 and R1 are each a hydrogen atom, an alkyl group, a haloalkyl group, an aralkyl group, and a heteroaralkyl group , Cycloalkyl, halocycloalkyl, alkenyl, haloalkenyl, alkynyl, dendritic N aryl or heteroaryl; R2 is academic, _ academic, aromatic, academic, heterogeneous academic, Ring j; Endyl, halogenated, halogenated, halogenated, halogenated, fast, aryl, or heteroaryl-85- 1 · As for halogenated compounds or their salts in the scope of patent application No. 4 Type, 2 where w is halogen, nitro, cyano, courtyard, halogen, radical, oxygen, radical, phenylalkyl (phenyl group may be substituted), phenoxyalkyl (phenyl group The group may be substituted by M1), an alkenyl group, a haloalkenyl group, an alkynyl group, a alkynyl group, a cycloalkyl group which may be substituted by M1, 5- to 12- containing an arbitrary hetero atom selected from an oxygen atom, a sulfur atom, and a nitrogen atom Membered heterocyclyl (heterocyclyl may be substituted by M1), hydroxyl, alkoxy, haloalkoxy, alkoxyalkoxy, phenylalkoxy (phenyl group may be substituted by M), benzene Oxyalkoxy (phenyl group can be ] Substitution), phenoxy, alkylthio, haloalkylthio which can be substituted by M1, phenylthio, amine, monoalkylamino, dialkylamine which can be substituted by M1 200526552 (6) group , Monophenylamino (phenyl group may be substituted by M]), diphenylamino (phenyl group may be substituted by M1), amino group substituted by alkyl and phenyl (phenyl group may be Substituted by M1), oxofluorenyl, diaminoaminofluorenyl, aminocarbonyl substituted with radical and phenyl (phenyl group may be substituted by M1), alkylsulfinylfluorenyl, halogen Alkylsulfinyl, benzenesulfinyl, which can be substituted by M1, alkanesulfinyl, halosulfonyl, benzenesulfinyl, fluorenyl, fluorenyl, trialkylsilane, which can be substituted by M1 Or trialkylsilyloxy. 6 · If a haloene compound or a salt thereof as claimed in item 5 of the scope of patent application, 0 where W is halogen, nitro, cyano, alkyl, haloalkyl, phenyl, hydroxyl, alkoxy which may be substituted by μ1 Methyl, haloalkoxy, phenoxy substituted by M1, alkylthio, haloalkylthio, phenylthio substituted by M], alkoxycarbonyl, phenylsulfinyl substituted by M] Or phenylsulfonyl which may be substituted by M 1. 7. The flammable compounds or salts thereof as described in item 1 of the patent application E1 of the patent application, wherein 0 is a hydrogen atom, a radical, a halogenated radical, a benzene radical, a halogenated radical, a halogenated radical, a phenylene Alkynyl, haloalkynyl, phenylalkynyl or -C (= B) q. Thai 8. If the halogen-flammable compound or its salt of item 1 of the scope of patent application, wherein: γ is (C) _12) courtyard, halogen (c!. ^) Courtyard or phenyl; L is -C ( = B) Q, -C (= b) B, Q, -C (= B) N (D) Q, -N (D) Q ^ .N (D) C (= B) Q > -N ( D) C (= B) B? Q > -N (D) s〇2Q ^ _N = CHQ, -N = C (Q) 2, -S02Q, _S02N (D) Q or J substituted (C) "2) Academic group (the alkyl group may be further substituted by other substituents); G and D are each a hydrogen atom, (c).] 2) Academic group, halogen (c). 12) Academic group, benzene-86- 200526552 (7) group (CI-I2); I: carbyl, (c2_) 2) alkenyl, halo (c2_12) alkenyl, benzene ^ fc. \ 2-] 2) alkenyl, (C2q2) alkynyl, halogen (C2_) 2) alkynyl, phenyl (C212) alkynyl, -C (= B) Q ... C (= B) B, Q ... C (= B) N (G,) Q, SQ s〇2Q- SN (G ') Q, -SN (G,) C (= B) B, Q or -so2n (g,) q ·, G' is (ι ·) 2) alkyl, halogen (c) _] 2 ) Alkyl, phenyl (C11y alkyl, (c2-12) alkenyl, halo (C212) alkenyl, phenyl (c2_ (.2 · 1 2) alkynyl, halo (C2_) 2) alkynyl, or benzene (C212) alkynyl; 〇 Q is (c ^ 2) alkyl which may be substituted by w, c ^ 2) Alkenyl group, (Cm 2) alkynyl group which may be substituted by W, cyclic hydrocarbon group which may be substituted by w, or 5_ to 1 2-membered heteroatom containing arbitrary heteroatoms selected from oxygen atom, sulfur atom and nitrogen atom Cyclic group (heterocyclic group may be substituted by W); W is halogen, nitro, cyano, (c)] 2) alkyl which may be substituted by κ, (c: 2-] 2) olefin which may be substituted by K (C212) alkynyl group which may be substituted by κ, cycloalkyl group which may be substituted, or 5-to 1 2 -membered heterocyclic group containing hetero atom selected from oxygen atom, sulfur atom and nitrogen atom Group may be substituted by M 1), 'OR], -SR1, -NR] R2… COR], -C〇2R1, c〇SR], -csor], -cs2r], -so2nr] r2, -conr] R2 , _Csnr] r2 -C (= NOV) Ri, -N (R)) COR3, -N (R)) C02r3, -N (R)) COSR3… N (R)) CSOR3, -N (R)) CS2R3 , -N (r)) so2r3, _sor3, _so2r3, _csR3, -〇c〇r3, -OCSR3, -SCOR3, -SCSR3, three (ChO alkyl sand base or three (C 1 _ I 2) base sand I is complete oxygen; K is _ prime, nitro, gas group, ring which may be substituted by M], which contains an arbitrary heteroatom selected from oxygen, sulfur and nitrogen atoms 2 to] 2_ -87- 200526552 (8) Member heterocyclic group (heterocyclyl may be substituted by M1), -〇M2, jM2, -NM2M3, -COM2, -CO2M2, -COSM2, -CSOM2, -CS2M2, -S〇2NM2M3 , -CONM2M3, -CSNM2M3, -C (NOV) M2, -N (M2) COM4 ... N (M2) c02M4, -N (M2) COSM4 ^ -N (M2) CSOM4 > -N (M2) CS2M4 ^ -N (M 2) SO 2 M4, -S Ο M 4 ,, -S 0 2 M4, -CS M4, -OC Ο M4, -〇CSM4, -SCOM4 or -SCSM4; M] is halogen , Nitro, cyano, (Cii2) alkyl, halo (Cii2) alkanoyl, (C3 · 8) cycloalkyl, halo (C3.8) cycloalkyl, (C2 i2) alkenyl, halo (c2_12 ) Alkenyl, (c2_) 2) alkynyl, halogen ((: 2 "2) alkynyl, -〇R4, -sr4, -NR4R5 ... COR4, -C02R4 ... C〇sr4, _cs〇r4, _CS2r4, -S 〇2NR4R5, -C〇NR4R5, -Csnr4r5, ... c (== n〇v) r4, -N (R4) COR6, -N (R4) C02R6, _N (R4) c〇SR6, -N (R4) CSOR6 , -N (R4) CS2R6, -N (R4) S02R6, -SOR6, -S02R6 ^ -CSR6 > »OC〇R6 > -OCSR6 '-SC0R6 ^-S CSR6; M2 and each is a hydrogen atom and can be M5 substituted (Ci ...) alkyl, Lu substituted by M (C2 ·! 2) alkenyl, substituted by M5 (C ^ 2) alkynyl, a bad hydrocarbon group which may be substituted by M, or a 5- to 12-membered heterocyclic group containing an arbitrary heteroatom selected from an oxygen atom, a sulfur atom, and a nitrogen atom (a heterocyclic group may be μ ]]); M4 is (Ci i2) alkyl which can be substituted by M5, (C2 ·! 2) green group which can be substituted by M5, (C2_) 2) alkynyl group which can be substituted by M5, and M1 Wang Aijingji, or a 5- to -2] -membered ring group containing an arbitrary heteroatom selected from the group consisting of oxygen, sulfur, and nitrogen atoms (heterocyclic group may be substituted by M 1), -88- 200526552 (9 ) M is a halogen, which may be substituted by M1 ^ ^ (Free,…) alkoxy, (C 丨 ·) 2) which may be substituted by M1, an alkylthio group, and (C) which may be substituted by glycan 1 Λ 1 2) Alkyl sulfinyl OM6 or-group, which can be substituted by M (Cl_ sulfonyl benzene group, M6 SM6; M6 is a ring furnace which can be substituted by M1, its heart group, or contains a group selected from oxygen atoms, standard &Amp; member heterocyclic groups of random heteroatoms of atoms and gas atoms (heterocycle 3 may be substituted by M 1); R1 and R2 are each a hydrogen atom, a (Ci_i2) alkyl group which can be substituted by "M", a (c ^ 2) alkenyl group substituted by M7, a (C2.12) alkynyl group substituted by 7 imitation M, Cycloalkyl group substituted by M], or 5- to 12-Chang containing random heteroatoms derived from oxygen, sulfur, and nitrogen atoms; ^ 1 benzyl (heterocyclyl may be substituted by M) : Generation); R3 is a (C ^ 2) alkyl group which may be substituted by M7, a (匸 2 ·) 2) alkenyl group which may be substituted by M7, a (c ^ 2) alkynyl group which may be substituted by M7, a cycloalkyl group which may be substituted by ... Or a 5- to 12-membered heterocyclic group (optionally substituted by μ) containing a heterocyclic ring selected from an oxygen atom, a sulfur atom, and a nitrogen atom; M7 is a halogen and a substituted cycloalkyl group , 5- to 12-membered heterocyclic groups containing random heteroatoms selected from the group consisting of oxygen, thiogen, and nitrogen, (heterocyclyl may be substituted by M 1), -0 μ 8, s M8,-N M 8 M 9, -COM8, -C02M8, -COSM8, -CSOM8, -CS2M8, -SO2NM M, -CONM M9, -CSNM8M9, -C (= NOV) M8, -N (M8) COM]. , -N (M8) C02M]. , -N (M8) COSM] 0, -N (M8) CSOM10 '-N (M8) CS2M10' -N (M8) S02M10 '-S 〇M 10… S 〇2 M] 0,-CSM】 0… 〇 c Ο M] 0 '-OCS 0, -89- 200526552 (10) -SCOM] ° or, ScsM] 〇; M / M9 are each a hydrogen atom, (C) _] 2) alkyl group which can be substituted by M1, (C ^ 2) alkenyl which may be substituted, (c2_) 2) alkynyl which may be substituted by M1, cyclonicotinyl which may be substituted by M, or a group containing an atom selected from an oxygen atom, a sulfur atom, and a nitrogen atom. The heteroatoms up to 12-membered heterocyclyl ring groups can be substituted); M] G is (Ci) 2) alkyl which can be substituted by M], (Cu2) alkyl which can be substituted by μ], (C2_i2) alkynyl substituted with M], O-ring hydrocarbon group which may be substituted by Mm, or 5-to 12-betheterocyclyl (heterocyclic ring) containing a random heterocycle selected from oxygen atom, sulfur atom and nitrogen atom Group may be substituted by M]); v is a hydrogen atom, (Ci i2) alkyl group which may be substituted by M], (Cm) alkenyl group which may be substituted by, (C2 i2) alkynyl group which may be substituted by M], Cycloalkyl groups which may be substituted by M !, or members containing arbitrary heteroatoms selected from oxygen, sulfur and nitrogen atoms up to 12 > members Cyclic group (heterocyclic group may be substituted by M]); ^ / and each is a hydrogen atom ~ ^^ alkyl ~ halo ^: ^ alkyl, aryl (Cm2) alkyl, heteroaryl (C). ^) Alkyl, (c3 8) cycloalkyl, halo (c3.8) #fluorenyl, (C 2 · 1 2) alkenyl, halo (c 2 ·] 2) alkenyl, (C 2 ·] 2) Alkynyl, halo (C2 · 12) quick, square or heteroside; R6 is (CH2) alkyl, halo (c) .12) alkyl, aryl (c).] 2) alkyl, heteroaryl (CH2) alkyl, (C3-8) cycloalkyl, halo ((: 3.8) cycloalkyl, (c2_) 2) alkene, (C2-) 2), cloth base, (C2-) 2) Bulk group, halogen (C2-12) fast group, square group or heteroaryl group. 9 · A method for preparing a haloene compound represented by formula (I) or a salt thereof -90- (I) (11) 200526552 Y c A GII CH2 (CH2〇H2) n-C-N where X1 and X2 are each halogen; Y is alkyl, haloalkyl or phenyl; η is from 0 to 5; L is -C (= B) Q, = C (= B) N (D) Q, -N (D) Q, -N (D) C (= B) Q, -N (D) C (= B) B, Q, -N ( D) S02Q, -N = CHQ ... n = c (q) 2, -S〇2Q, -S〇2N (D) Q or J substituted alkyl (alkyl may be further substituted by other substituents); J -C (= B) B, Q, -C (= B) N (D) Q, -S02Q, or -SO2N (D) Q ·, G and D are each a hydrogen atom, an alkyl group, and a haloalkyl group , Phenylalkyl, alkenyl, haloalkenyl, phenylalkenyl, alkynyl, haloalkynyl, phenylalkynyl, -C (= B) Q, -C (= B) B'Q, -C (= B) N (G,) Q, -SQ, -S02Q, -SN (G ') Q, -SN (G,) C (= B) B, Q or -S02N (G,) Q; G, Alkyl, haloalkyl, phenylalkyl'alkenyl, haloalkenyl, phenylalkenyl, alkynyl, haloalkynyl, or phenylalkynyl; A, B, and B, each of which is an oxygen atom or a sulfur atom ; Q is a substituted alkyl group, a substituted alkenyl group, a substituted alkynyl group, a substituted cycloalkyl group, or 5- containing an arbitrary heteroatom selected from an oxygen atom, a sulfur atom, and a nitrogen atom. To 12-members Ring group (heterocyclic group may be substituted) 'which includes (1) the compound represented by formula (11): χ1 \ _ / γ / C == C \ π ⑼ X CHpfCh ^ CHyn-C—CI -91- 200526552 (12) where X], X2, Υ, η and A are as defined above, and react with the compound represented by formula (III) or a salt thereof: GI HN-L (III) where L and G are as Or as defined above; or reaction; or (2) the compound represented by formula (IV): x1 \ / X2 c = c A, ll CH2 (CH2CH2) n_C-T—Η (IV) where X1, X2, Υ , Η and A are as defined above, and T is an oxygen atom or a sulfur atom, React with a compound represented by formula (III) or a salt thereof: GI ΗN-L (丨 丨 1) wherein L and G are as defined above; or (3) using a compound represented by formula (V):- 92- (V) 200526552 (13) X1 \ Υ 0 = 0 X2 CH2 (CH2CH2) n_C ~ Τ-Z where X], X2, Υ, η, A, and T are as defined above, and Z is Cb4 alkane Group, which reacts with a compound represented by formula (III) or a salt thereof: GI HN-L (III) where L and G are as defined above; or (4) a compound represented by formula (1-1) : X \ / X2 CH2 (CH2CH2) n-C-NΗ-L (1-1) where X], X2, Y, η, L, and A are as defined above, and react with a compound represented by formula (VI) or a salt thereof : G1-X3 (VI) where G1 is alkyl, haloalkyl, phenylalkyl, alkenyl, haloalkenyl, phenylalkyl, halo, halo, phenyl, and C (= B ) Q, -C (two B) B, Q, -C (= B) N (G "Q, -SQ, -S02Q, -SN (G,) Q, -SN (G ') C (= B) B: Q or-S〇2N (G〇Q, X3 is halogen, and B, Q and -93- 200526552 (14) G5 is as defined above, (5) make the formula (I-1) as Compound CH2 (CH2CH2) nC—NH-L (1-1) where X], X2, Y, n, L, and A are as defined above, and react with the compound represented by formula (VII) or a salt thereof: G2 -〇S〇2-U (VII) where G2 is a radical, U is a radical, a halogen radical, a fluorenyl radical, a phenyl radical, a halogen-substituted phenyl radical, or an alkyl-substituted phenyl radical; or, (6) Make the compound represented by formula (Bu 4): χ1ν X2〆.V 〇G, cc \ II I CH2 (CH2〇H2) n_C_N_L (1-4) where X1, X2, Y, n, L and G are as defined above, and Thio-nizing agent reaction; or (7) the compound represented by formula (VIII): -94- 200526552 (15) Y ft G II I CH2 (CH2CH2) n—0—N—H (vm) where X], X2, Y, n, A, and G are as defined above, and react with a compound represented by the formula Cl-E, Where e is _C (= B) Q, • C (= B) B'Q, -C (= B) N (D) Q, -S02Q or -S02N (D) Q, and D,, B, B5 And Q is as defined above, or 1 is reacted with a compound represented by the formula B = C = NQ (where b and Q are as defined above). 1 0 · —A kind of insecticide, which includes the haloene compound or the salt thereof as the active ingredient as in item 1 of the scope of patent application. 1 1 · An agricultural or garden insecticide, which includes a haloene compound or a salt thereof as an active ingredient as in the scope of patent application item 1. 1 2-An insecticide, insecticide or nematicide, which includes the halogenated alkenes a " of active ingredients such as those in the scope of patent application No. 1. ] 3. A method for controlling pests, which comprises applying an effective amount of a haloene compound or a salt thereof according to item 1 of the patent application. -95- 200526552 VII. (1), the designated representative picture in this case is ... (No), the component representative symbols of this representative picture are simply explained: 8. If there is a chemical formula in this case, please disclose the chemical formula that can best show the characteristics of the invention: X, C— / ft G / C ~ C \ II I X2 ΟΗ2 (ΟΗ2〇Η2) π—C—N—L