BACKGROUND ART W003/84927, W004/52872 and EP432861 disclose haloalkene compounds having certain specific chemical structures, respectively. However, they do not disclose or suggest haloalkene compounds of the after-mentioned formula (I).

DISCLOSURE OF THE INVENTION For many years, many pesticides have been used, but many of them have various problems such that the effects are inadequate, their use is restricted as pests have acquired resistance, etc. Accordingly, it is desired to develop a novel pesticide substantially free from such problems,'for example, a pesticide capable of controlling various pests which create problems in agricultural and horticultural fields or a pesticide which is capable of controlling pests parasitic on animals.

The present inventors have conducted various studies on haloalkene compounds in an effort to find a superior

pesticide. As a result, they have found that a novel haloalkene compound has an extremely high pesticidal effect against pests at a low dose and at the same time has safety to crop plants, the natural enemy to pests, or mammals, and have accomplished the present invention.

Namely, the present invention relates to a haloalkene compound represented by the formula (I) or its salt: wherein each of X1 and X2 is halogen; Y is alkyl, haloalkyl or phenyl; n is from 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, - (D) C (=B) B'Q,-N (D) S02Q,-N=CHQ,-N=C (Q) 2,-S02Q, - S02N (D) Q or alkyl substituted by J (the alkyl may further be substituted by other substituents); J is-C (=B) B'Q, -C (=B) N (D) Q,-S02Q or-SO2N (D) Q; each of G and D 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, -S02Q,-SN (G') Q, -SN (G') C (=B) B'Q or-son (G') Q; G'is alkyl, haloalkyl, phenylalkyl, alkenyl, haloalkenyl, phenylalkenyl, alkynyl, haloalkynyl or phenylalkynyl; each of A, B and B'is an oxygen atom or a sulfur atom ; Q is alkyl which may be substituted, alkenyl which may be substituted, alkynyl which may be substituted, a cyclic

hydrocarbon group which may be substituted, or a 5-to 12-membered heterocyclic group (the heterocyclic group may be substituted) containing an optional hetero atom selected from an oxygen atom, a sulfur atom and a nitrogen atom; a process for its production; and a pesticide containing it.

The pesticide containing, as an active ingredient, the novel haloalkene compound of the formula (I), has an extremely high pesticidal effect against pests at a low dose and at the same time has safety to crop plants, the natural enemy to pests, or mammals.

BEST MODE FOR CARRYING OUT THE INVENTION In-N=C (Q) 2 in L, two Q may be the same or different.

In a case where the alkyl substituted by J (the alkyl may further be substituted by other substituents) for L has other substituents, such substituents may, for example, be W.

The respective substituents for the alkyl which may be substituted, the alkenyl which may be substituted, the alkynyl which may be substituted, the cyclic hydrocarbon group which may be substituted, or the 5-to 12-membered heterocyclic group (the heterocyclic group may be substituted) containing an optional hetero atom selected from an oxygen atom, a sulfur atom and a nitrogen atom, for Q, may, for example, be W.

W may, for example, be halogen, nitro, cyano, alkyl which may be substituted by K, alkenyl which may be substituted by K, alkynyl which may be substituted by K, a cyclic hydrocarbon group which may be substituted by M1, a 5-to 12-membered heterocyclic group (the heterocyclic group may be substituted by M1) containing an optional hetero atom selected from an oxygen atom, a sulfur atom and a nitrogen atom, -OR1, -SR1, -NR1R2, -COR1, -CO2R1, - COSR1, -CSOR1, -CS2R1, -SO2NR1R2, -CONR1R2, -CSNR1R2, - C (=NOV) Ri,-N (Rl) CORON (R1) C02R3,-N (Rl) COSR3, -N(R1)CSOR3, -N(R1)CS2R3, -N(R1)SO2R3, -SOR3, -SO2R3, -CSR3, - OCOR3,-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.

K may, for example, be halogen, nitro, cyano, a cyclic hydrocarbon group which may be substituted by M1, a 5-to 12-membered heterocyclic group (the heterocyclic group may be substituted by M1) containing an optional hetero atom selected from an oxygen atom, a sulfur atom and a nitrogen atom, -OM2, -SM2, -NM2M3, -COM2, -CO2M2, - COSM2, -CSOM2, -CS2M2, -SO2NM2M3, -CONM2M3, -CSNM2M3, - C (=NOV) M2, -N(M2)COM4, -N(M2)CO2M4, -N(M2)COSM4, -N(M2)CSOM4, -N(M2)CS2M4, -N(M2)SO2M4, -SOM4, -SO2M4, -CSM4, - OCOM4,-OCSM4,-SCOM4 or-SCSM4. The number of substituents K may be one or more, and if more, they may be the same or different. mi may, for example, be halogen, nitro, cyano, alkyl,

haloalkyl, cycloalkyl, halocycloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl,-oR4,-SR4,-NR4R5, - COR4,-C02R4,-COSR4,-CSOR4,-CS2R4,-S02NR4R5,-CONR4R5, CSNR4R5-C (=NOV) R4-N (R4) COR6,-N (R4) CO2R6,-N (R) COSR -N(R4)CSOR6, -N(R4)CS2R6, -N9R4)SO2R6, -SOR6, -SO2R6, -CSR6, -OCOR6, -OCSR6, -SCOR6, -SCSR6. The number of substituents M 1 may be one or more, and if more, they may be the same or different.

Each of M2 and M3 may, for example, be a hydrogen atom, alkyl which may be substituted by M5, alkenyl which may be substituted by M5, alkynyl which may be substituted by M5, a cyclic hydrocarbon group which may be substituted by M1, a 5-to 12-membered heterocyclic group (the heterocyclic group may be substituted by Ml) containing an optional hetero atom selected from an oxygen atom, a sulfur atom and a nitrogen atom. Ml is as defined above.

M4 may, for example, be alkyl which may be substituted by M5, alkenyl which may be substituted by M5, alkynyl which may be substituted by M5, a cyclic hydrocarbon group which may be substituted by M1, or a 5- to 12-membered heterocyclic group (the heterocyclic group may be substituted by Ml) containing an optional hetero atom selected from an oxygen atom, a sulfur atom and a nitrogen atom. Ml is as defined above.

M5 may, for example, be halogen, alkoxy which may be substituted by M1, alkylthio which may be substituted by

Ml, alkylsulfinyl which may be substituted by M1, alkylsulfonyl which may be substituted by M1, -M6, -OM6 or -SM6. The number of substituents M5 may be one or more, and if more, they may be the same or different. Ml is as defined above.

M6 may, for example, be a cyclic hydrocarbon group which may be substituted by M1, or a 5-to 12-membered heterocyclic group (the heterocyclic group may be substituted by M1) containing an optional hetero atom selected from an oxygen atom, a sulfur atom and a nitrogen atom. M1 is as defined above.

Each of R1 and R2 may, for example, be a hydrogen atom, alkyl which may be substituted by M7, alkenyl which may be substituted by M7, alkynyl which may be substituted by k7, a cyclic hydrocarbon group which may be substituted by M1, or a 5-to 12-membered heterocyclic group (the heterocyclic group may be substituted by M1) containing an optional hetero atom selected from an oxygen atom, a sulfur atom and a nitrogen atom. Ml is as defined above.

R3 may, for example, be alkyl which may be substituted by M7, alkenyl which may be substituted by M7, alkynyl which may be substituted by M7, a cyclic hydrocarbon group which may be substituted by M1, or a 5- to 12-membered heterocyclic group (the heterocyclic group may be substituted by M1) containing an optional hetero atom selected from an oxygen atom, a sulfur atom and a

nitrogen atom. Ml is as defined above.-.. ; M7 may, for example, be halogen, a cyclic hydrocarbon group which may be substituted by M3-, a 5-to 12-membered heterocyclic group (the heterocyclic group may be substituted by Ml) containing an optional hetero atom selected from an oxygen atom, a sulfur atom and a nitrogen atom, -OM8, -SM8, -NM8M9, -COM8, -CO2M8, -COSM8, -CSOM8, -CS2M8, -SO2NM8M9, -CONM8M9, -CSNM8M9, -C (=NOV) M8, -N(M8)COM10, -N(M8)CO2M10, -N(M8)COSM10, -N(M8)CSOM10, -N(M8)CS2M10, -N(M8)SO2M10, -SOM10, -SO2M10, -CSM10, -OCOM10, -OCSM10, -SCOM10 or -SCSM10. The number of substituents M7 may be one or more, and if more, they may be the same or different. Ml is as defined above.

Each of M8 and M9 may, for example, be a hydrogen atom, alkyl which may be substituted by M1, alkenyl which may be substituted by M1, alkynyl which may be substituted by M1, a cyclic hydrocarbon group which may be substituted by M1, or a 5-to 12-membered heterocyclic group (the heterocyclic group may be substituted by M1) containing an optional hetero atom selected from an oxygen atom, a sulfur atom and a nitrogen atom. M1 is as defined above. mio may, for example, be alkyl which may be substituted by M1, alkenyl which may be substituted by M1, alkynyl which may be substituted by M1, a cyclic hydrocarbon group which may be substituted by M1, or a 5- to 12-membered heterocyclic group (the heterocyclic group

may be substituted by M1) containing an optional hetero atom selected from an oxygen atom, a sulfur atom and a nitrogen atom. M1 is as defined above.

V may, for example, be a hydrogen atom, alkyl which may be substituted by M alkenyl which may be substituted by M1, alkynyl which may be substituted by M1, a cyclic hydrocarbon group which may be substituted by M1, or a 5-to 12-membered heterocyclic group (the heterocyclic group may be substituted by M1) containing an optional hetero atom selected from an oxygen atom, a sulfur atom and a nitrogen atom. M1 is as defined above.

Each of R4 and R5 may, for example, be a hydrogen atom, alkyl, haloalkyl, arylalkyl, heteroarylalkyl, cycloalkyl, halocycloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, aryl or heteroaryl.

R6 may, for example, be alkyl, haloalkyl, arylalkyl, heteroarylalkyl, cycloalkyl, halocycloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, aryl or heteroaryl.

As the halogen or halogen as a substituent, each atom of fluorine, chlorine, bromine or iodine may be mentioned. The number of halogens as substituents may be 1 or more, and if more, the respective halogens may be the same-or different. Further, the positions for substitution of halogens may be any positions.

The alkyl or alkyl moiety may be linear or branched, and as its specific example, Cl-12 alkyl such as methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, pentyl,

hexyl, heptyl, octyl, nonyl, decyl, undecyl or dodecyl may be mentioned.

The alkenyl or alkenyl moiety may be linear or branched, and as its specific example, C2-12 alkenyl such as vinyl, 1-propenyl, allyl, isopropenyl, 1-butenyl, 1,3- butadienyl, 1-hexenyl, 1-heptenyl, 4-octenyl, 2-decenyl or 2-dodecenyl may be mentioned.

The alkynyl or alkynyl moiety may be linear or branched, and as its specific example, C212 alkynyl such as ethynyl, 2-butynyl, 2-pentynyl, 3-hexynyl, 4,4- dimethyl-2-pentynyl, 4-octynyl, 2-decynyl or 2-dodecynyl may be mentioned.

The cyclic hydrocarbon group may be either a monocyclic type or a condensed polycyclic type and may be saturated or may have an unsaturated moiety. A specific Example of the monocyclic hydrocarbon group may, for example, be cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclooctyl, cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cyclooctenyl, cyclohexadienyl,. cyclooctadienyl, cyclooctynyl or phenyl.

A specific example of the condensed polycyclic hydrocarbon group may, for example, be naphthyl, anthryl, phenanthryl, indenyl or indanyl.

As the 5-to 12-membered heterocyclic group containing an optional hetero atom selected from an oxygen atom, a sulfur atom and a nitrogen atom, a monocyclic or condensed ring type heterocyclic group

containing from 1 to 4 hetero atoms, may, for example, be mentioned. Such a heterocyclic group may be saturated or may have an unsaturated moiety, or its methylene moiety may be converted to oxo or thioxo, or may be an N-oxide such as N-oxypyridyl. Preferably, it may, for example, be 1) a heterocyclic group selected from the group consisting of thienyl, furyl, pyrrolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, imidazolyl, pyrazolyl, thiadiazolyl, oxadiazolyl, triazolyl, tetrazolyl, dithiazolyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, oxazinyl, thiazinyl, pyranyl, benzothienyl, benzofuranyl, indolyl, isoindolyl, benzothiazolyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, benzimidazolyl, indazolyl, cyclopentapyrazolyl, benzothiadiazolyl, benzotriazolyl, quinolyl, isoquinolyl, phthalazinyl, cinnolinyl, quinazolinyl, quinoxalinyl, benzotriazinyl, naphthyridinyl, thiazolopyridyl, benzodioxolyl, benzodioxynyl, pyrazolopyrimidinyl, triazolopyrimidinyl and purinyl, 2) a partially saturated heterocyclic group having a part of such a heterocyclic group hydrogenated, 3) a saturated heterocyclic group having such a heterocyclic group completely hydrogenated, or 4) an oxo or thioxo heterocyclic group having a methylene moiety in the above-mentioned dithiazolyl, oxadinyl, thiadinyl, pyranyl, cyclopentapyrazolyl, benzodioxolyl, partially saturated heterocyclic group or saturated heterocyclic group, converted to oxo or thioxo.

The above-mentioned heterocyclic group may have several combinations due to the differences in the positions of hetero atoms or the differences of the condensed moieties, and the present invention includes all of them. For example, the thiadiazolyl includes 1,2, 3-thiadiazolyl and 1,3, 4-thiadiazolyl; the triazolyl includes 1,2, 3-triazolyl and 1,2, 4-triazolyl; the triazinyl includes, 1,2, 4-triazinyl and 1,3, 5-triazinyl; the benzothienyl includes benzo [b] thienyl and benzo [c] thienyl ; the benzofuranyl includes benzo [b] furanyl and benzo [c] furanyl ; the benzisothiazolyl includes 1, 2-benzisothiazolyl and 2, 1-benzisothiazolyl ; the benzisoxazolyl includes 1, 2-benzisoxazolyl and 2,1- benzisoxazolyl ; and the benzothiadiazolyl includes 1,2, 3- benzothiadiazolyl and 2,1, 3-benzothiadiazolyl. Further, the same applies to the partially saturated heterocyclic group, the saturated heterocyclic group or the oxo or thioxo heterocyclic group.

The above-mentioned partially saturated heterocyclic group may be one having a part of the above heterocyclic group hydrogenated. It may, for example, be 4,5- dihydrothiazolyl, 4,5-dihydrooxazolyl, 4,5- dihydroisoxazolyl, 4, 5-dihydro-lH-imidazolyl, 4,5- dihydro-lH-pyrazolyl, 3,4, 5,6-tetrahydropyridinyl, 1,4, 5,6-tetrahydropyrimidinyl, 2,3-dihydrobenzofuranyl or 4a, 5,6, 7,8, 8a-hexahydroquinoxalinyl.

The above-mentioned saturated heterocyclic group may

be one having the above heterocyclic group completely hydrogenated. It may, for example, be tetrahydrofuranyl, tetrahydropyranyl, pyrrolidinyl, piperidinyl, piperazinyl or morpholinyl.

The above-mentioned oxo or thioxo heterocyclic group may be one having a methylene moiety in the above- mentioned dithiazolyl, oxadinyl, thiadinyl, pyranyl, cyclopentapyrazolyl, benzodioxolyl, partially saturated heterocyclic group or saturated heterocyclic group, converted to oxo or thioxo. It may, for example, be 2- oxotetrahydrothienyl, 2-thioxotetrahydrothienyl, 2- oxotetrahydrofuranyl, 2-thioxotetrahydrofuranyl, 2- oxopyrrolidinyl, 2,5-dioxopyrrolidinyl, 2,4- dioxothiazolidinyl, 4-oxo-4,5-dihydrooxazolyl, 4-oxo-4,5- dihydro-lH-imidazol-2-yl, 5-oxo-4, 5-dihydro-lH-pyrazolyl, 3-oxo-2, 3-dihydro-lH-pyrazolyl, 5-thioxo-5H- [1, 2, 43dithiazolyl, 6-oxo-1, 6-dihydropyridinyl, 6-oxo- 1,6-dihydropyridazinyl, 2, 6-dioxo-1, 2,3, 6- tetrahydropyrimidinyl, 3-oxo-3H- [1, 2,4] triazinyl, 2-oxo- 1,2-dihydroquinolinyl, or 1, 3-dioxo-1, 3-dihydroisoindol- 2-yl.

As the cycloalkyl or cycloalkyl moiety, C3-8 cycloalkyl such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or cyclooctyl may be mentioned.

As the aryl or aryl moiety, phenyl, naphthyl, anthryl, phenanthryl, indenyl or indanyl may be mentioned.

As the heteroaryl or heteroaryl moiety, the same one

as the above-mentioned heterocyclic group may be mentioned.

The salt of the haloalkene compound of the above formula (I) includes all kinds so long as they are agriculturally acceptable. For example, an alkali metal salt such as a sodium salt or a potassium salt; an alkaline earth metal salt such as a magnesium salt or a calcium salt; an ammonium salt such as a dimethylamine salt or a triethylamine salt; an inorganic acid salt such as a hydrochloride, a perchlorate, a sulfate or a nitrate; or an organic acid salt such as an acetate or a methanesulfonate, may be mentioned.

The haloalkene compound of the formula (I) may have geometrical isomers, optical isomers or tautomeric isomers, and such isomers and mixtures thereof are both included in the present invention. Further, in the present invention, various isomers other than those mentioned above, may be included within the scope of the common knowledge in this technical field. Further, depending upon the type of such an isomer, the chemical structure may be different from the above-mentioned formula (I), but. it is obvious to one skilled in the art that such a structure is in isomeric relation and thus falls within the scope of the present invention.

The haloalkene compound of the formula (I) or its salt (hereinafter referred to simply as the compound of the present invention) can be produced by the following reactions (A) to (H) and in accordance with a usual method for producing a salt. [A] xi A G X1\C=CY HN-L (III). or its salt X2/CH2t.. 2CH2) Il-C_CI (II) , Y A G , C C X2 (CH2CHz) nCN-L 0

In the reaction (A), X x I Y, n, L, G and A are as defined above. Further, as the salt of the compound of the formula (III), a salt with an organic or inorganic acid, such as a hydrochloride, a sulfate, an oxalate or a methanesulfonate, may be mentioned.

The reaction (A) can be carried out in the presence of a base, as the case requires. As the base, one or more types may suitably be selected for use from, for example, a tertiary amine such as trimethylamine, triethylamine, triisopropylamine, diisopropylethylamine, pyridine, 4-dimethylaminopyridine, 2,6-dimethylpyridine, 4-pyrrolidinopyridine, N-methylmorpholine, N, N- dimethylaniline, N, N-diethylaniline, N-ethyl-N- methylaniline, 1, 8-diazabicyclo [5. 4. 0]-7-undecene or 1,4- diazabicyclo [2. 2. 2] octane; an alkali metal such as sodium or potassium; an alkali metal carbonate such as sodium carbonate or potassium carbonate ; an alkali metal hydroxide such as sodium hydroxide or potassium

hydroxide; an alkali metal hydride such as sodium hydride or potassium hydride; an alkali metal bicarbonate such as- sodium bicarbonate or potassium bicarbonate; and an alkyl lithium such as butyl lithium. The base may be used in an amount of from 1 to 5 times by mol, preferably from 1 to 2.5 times by. mol, to the compound of the formula (II).

The reaction (A) can be carried out in the presence of a solvent, as the case requires. The solvent may be any solvent so long as it is a solvent inert to the reaction, and one or more types may suitably be selected for use from, for example, an aliphatic hydrocarbon such as pentane, hexane, heptane, octane or cyclohexane ; an aromatic hydrocarbon such as benzene, toluene, xylene or pyridine ; a halogenated hydrocarbon such as chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane or trichloroethane; an ether such as diethyl ether, butyl ethyl ether, tetrahydrofuran, dioxane, dimethoxyethane or anisole; an ester such as methyl acetate, ethyl acetate or propyl acetate; a ketone such as acetone, diethyl ketone, methyl ethyl ketone or methyl isobutyl ketone; and a polar aprotic solvent such as acetonitrile, propionitrile, N, N- dimethylformamide, dimethylsulfoxide, hexamethylphosphoric triamide, sulfolane, dimethylacetamide or N-methylpyrrolidone.

The reaction (A) can be carried out in an atmosphere of an inert gas, as the case requires. As such an inert

gas, each gas such as nitrogen, helium or argon may be mentioned.

The reaction (A) can be carried out usually at a temperature of from-78 to +250°C, preferably from-78 to +150°C, and the reaction'time is usually from 0.1 to 72 hours, preferably from 0.1 to 24 hours. [B] xi A G X\ Y A) A . C--C. jj HN--L () H) or its salt x2 CH2 (CH2CH2) n-C-T-H (IV) x2z", Y A G , C C X CH2 (CH2CH2) nCN L 0 In the reaction (B), X1, X, Y, n, L, G and A are as defined above, T is an oxygen atom or a sulfur atom.

Further, as the salt of the compound represented by the formula (III), the same one as exemplified in the above- mentioned reaction (A) may be mentioned.

The reaction (B) can be carried out by azeotropic dehydration in the presence of a solvent or in the presence of a condensing agent.

The solvent to be used for the azeotropic dehydration may be any solvent so long as it is a solvent inert to the reaction, and for example, one or more types may suitably be selected for use from those exemplified in the above-mentioned reaction (A). Further, in a case

where the reaction is carried out in the presence of a condensing agent, a solvent may be used as the case requires. The solvent to be used here may be any solvent so long as it is a solvent inert to the reaction, and for example, one or more types may suitably be selected for use from those exemplified in the above reaction (A).

As the condensing agent to be used in the reaction (B), a carbodiimide such as 1,3-dicyclohexylcarbodiimide, 1,3-diisopropylcarbodiimide or 1-ethyl-3- (3- dimethylaminopropyl) carbodiimide hydrochloride; or others such as phenyl dichlorophosphate, diethyl cyanophosphonate, 1, 3, 5-triaza-2,4, 6-triphosphorin- 2,2, 4,4, 6, 6-hexachloride, cyanuric chloride, isobutyl chloroformate, chlorosulfonyl isocyanate, N, N'-carbonyl diimidazole, or trifluoroacetic anhydride, may be mentioned. The condensing agent may be used in an amount of from 1 to 5 times by mol, preferably from 1 to 2 times by mol, to the compound of the formula (IV).

The reaction (B) can be carried out in the presence of a base, as the case requires. As the base, one or more types may suitably be selected for use from, for example, tertiary amines such as trimethylamine, triethylamine, triisopropylamine, diisopropylethylamine, pyridine, 4-dimethylaminopyridine, 2,6-dimethylpyridine, 4-pyrrolidinopyridine, N-methylmorpholine, N, N- dimethylaniline, N, N-diethylaniline, and N-ethyl-N- methylaniline. The base may be used in an amount of from

0.1 to 5 times by mol, preferably from 0.1 to 2.5 times by mol, to the compound of the formula (IV).

The reaction (B) can be carried out in an atmosphere of an inert gas, as the case requires. As such an inert gas, one such as nitrogen, helium or argon may be mentioned.

The reaction (B) can be carried out usually at a temperature of 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 0.1 to 24 hours. fol 1 x1*-,-ZY A I or its salt x2/CH2 (CH2CH2) nCTZ (V) X1 jY A G 2/C C x2 CH2CH2) n-C-N-L ( !) In the reaction (C), X1, X2, Y, n, L, G, A and T are f as defined above, and Z is 1-4 alkyl. Further, as the salt of the compound represented by the formula (III), the same one as exemplified in the above reaction (A) may, for example, be mentioned.

The reaction (C) can be carried out in the presence of a base, as the case requires. As the base, one or more types may suitably be selected for use from, for example, those exemplified in the above reaction (A), and alkali metal alkoxides such as sodium methoxide, sodium

ethoxide and potassium butoxide; and tertiary amines such as trimethylamine, triethylamine, triisopropylamine, diisopropylethylamine, pyridine, 4-dimethylaminopyridine, 2,6-dimethylpyridine, 4-pyrrolidinopyridine, N- methylmorpholine, N, N-dimethylaniline, N, N-diethylaniline, and N-ethyl-N-methylaniline. The base may be used in an amount of from 0.01 to 5 times. by mol, preferably from 0.01 to 2.5 times by mol, to the compound of the formula (V).

The reaction (C) can be carried out in the presence of a solvent, as the case requires. The solvent may be any solvent so long as it is a solvent inert to the reaction, and for example, one or more types may suitably be selected for use from, for example, those exemplified in the above reaction (A).

The reaction (C) can be carried out in an atmosphere of an inert gas, as the case requires. As the inert gas, each gas such as nitrogen, helium or argon may be mentioned.

The reaction (C) can be carried out usually at a temperature of 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 0.1 to 24 hours.

In the reaction (D), G1 is 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 - S02N (G') Q, and X3 is halogen, and Xl, X2, Y, n, L, G', A, B and Q are as defined above.

The reaction (D) can be carried out in the presence of a base, as the case requires. As the base, one or more types may suitably be selected for use from, for example, those exemplified in the above reaction (A).

The base may be used in an amount of from 0.01 to 10 times by mol, preferably from 0.01 to 5 times by mol, to the compound of the formula (I-1).

The reaction (D) can be carried out in the presence of an N-trialkylsilyl-alkylcarbamate, as the case requires. As such an N-trialkylsilyl-alkylcarbamate, one or more types may suitably be selected for use from, for example, N-trimethylsilyl-ethylcarbamate and N- triethylsilyl-methylcarbamate. The N-trialkylsilyl- alkylcarbamate may be used in an amount of from 0.01 to

10 times by mol, preferably from 0.01 to 5 times by mol, to the compound of the formula (I-1).

The reaction (D) can be carried out in the presence of a solvent, as the case requires. The solvent may be any solvent so long as it is a solvent inert to the reaction, and for example, one or more types may suitably be selected for use from, for example, those exemplified in the above-mentioned reaction (A).

The reaction (D) can be carried out in an atmosphere of an inert gas, as the case requires. As such an inert gas, one such as nitrogen, helium or argon may be mentioned.

The reaction (D) can be carried out usually at a temperature of 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 0.1 to 24 hours.

In the reaction (E), X1, X2, Y, n, L and A are as defined above, G2 is alkyl, and U is alkyl, haloalkyl, alkoxy, phenyl, phenyl substituted by halogen, or phenyl substituted by alkyl.

The reaction (E) can be carried out in the presence of a base, as the case requires. As the base, one or more types may suitably be selected for use from, for example, those exemplified in the above reaction (A).

The base may be used in an amount of from 0.01 to 10 times by mol, preferably from 0.01 to 5 times by mol, to the compound of the formula (I-1).

The reaction (E) can be carried out in the presence of a solvent, as the case requires. The solvent may be any solvent so long as it is a solvent inert to the reaction, and for example, one or more types may suitably be selected for use from, for example, those exemplified in the above-mentioned reaction (A).

The reaction (E) can be carried out in an atmosphere of an inert gas, as the case requires. As such an inert gas, each gas such as nitrogen, helium or argon may be mentioned.

The reaction (E) can be carried out usually at a temperature of 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 0.1 to 24 hours. [F] X1s wY O G Thionizing agent x2/CH2 (CH2CH2) n-C-N L S G X1 C/Y (1-4) 2 CH2 (CH2CH2) n-C-N-L 0-5)

In the reaction (F), XI, X2, Y, n, L and G are as defined above. By the reaction (F), in a case where a carbonyl moiety is present in L, such a carbonyl moiety can be thionized.

As the thionizing agent to be used in the reaction (F), phosphorus pentasulfide or Lawesson's reagent may, for example, be mentioned. The thionizing agent may be used in an amount of from 1 to 10 times by mol, preferably from 1 to 4 times by mol, to the compound of the formula (1-4). Further, in a case where a carbonyl group in L is to be thionized, the corresponding amount of the thionizing agent may be added.

The reaction (F) can be carried out in the presence of a solvent, as the case requires. The solvent may be any solvent so long as it is a solvent inert to the reaction, and for example, one or more types may suitably be selected for use from, for example, 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, dichloroethane and trichloroethane; ethers such as diethyl ether, butyl ethyl ether, tetrahydrofuran, dioxane, dimethoxyethane and anisole; esters such as methyl acetate, ethyl acetate and propyl acetate; and polar aprotic solvents such as acetonitrile, propionitrile, dimethylsulfoxide and sulfolane.

The reaction (F) can be carried out in an atmosphere of an inert gas, as the case requires. As such an inert gas, each gas such as nitrogen, helium or argon may be mentioned.

The reaction (F) can be carried out usually at a temperature of 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 0.1 to 24 hours.

Among the compounds of the present invention, a compound wherein L is-C (=B) Q, -C (=B) B'Q, - C (=B) N (D) Q,-S02Q or-SO2N (D) Q, can also be produced in accordance with the reaction (G). [G] X Y A G X X/Y | G (Vlil) or its salt X CH2 (CH2CH2) n-C-N-H xi N.-I y A G CI-E 1\ Y A G C X CH2 (CH2CH2) n-C-N-E (1-6)

In the reaction (G), E is-C (=B) Q, -C (=B) B'Q, - C (=B) N (D) Q,-SO2Q or-S02N (D) Q, and X1, X2, Y, n, G, D, A, B, B'and Q are as defined above. Further, as the salt of the compound of the formula (VIII), the same one as the salt of the compound of the above formula (III) may, for example, be mentioned.

The reaction (G) can be carried out in the same manner as the above reaction (A).

Among the compounds of the present invention, a compound wherein L is-C (=B) NHQ, may also be produced in accordance with the reaction (H).

[H] X Y A G zC :-Cs l l l (Vlil) or its salt X2 CH2 (CH2CH2) n-C-N-H B=C=N-Q X1s wY A G B II I II x2 CH2 (CH2CH2) nCN C NH Q (1-7) In the reaction (H), X1, X2, Y, n, G, A, B and Q are

as defined above. Further, as the salt of the compound of the formula (VIII), the same one as the salt of the compound of the above formula (III) may, for example, be mentioned.

The reaction (H) can be carried out in the same manner as the above reaction (A).

Each starting materials of the formula (II), (IV) or (V) in the above reaction (A) to (C) is (1) a known compound, or (2) can be produced by or in accordance with the Preparation Examples given hereinafter, or (3) can be produced by or in accordance with the method disclosed in W092/15555, EP661289 or EP432861. The above (3) will be described in more detail. a) The method disclosed from p. 15, line 16 to p. 16, line 3 in W092/15555, a method of optionally carrying out usual chlorination or esterification, following such a method, the method disclosed in Preparation Example 16, 22,28 or 42 in the same publication or a method in accordance therewith. b) The method disclosed from p. 13, line 25 to p. 14, line 37 in EP661289, the method disclosed in Preparation Example Z1, Z2 or Z3 in the same publication or a method in accordance therewith. c) The method disclosed from p. 4, line 22 to p. 8, line 45 in EP432861, the method disclosed in Preparation Example 3,4, 8,9, 10 or 16 in the same publication or a method in accordance therewith.

The compound of the formula (VIII) or its salt in the above reaction (G) or (H) can be produced by the following reaction (I) to (K) and a usual method for producing a salt. [1 11 or its salt G-NH2 (IX) x2/CH2 (CH2CH2) n-C-CI (") X1s wY A G (II) X1\ iY A G 2, C C (Vll I) (Vill)

In the reaction (I), Xl, X2, Y, n, G and A are as defined above. Further, as the salt of the compound of the formula (IX), the same one as the salt of the compound of the above formula (III) may, for example, be mentioned.

The reaction (I) can be carried out in the same manner as the above reaction (A). [J] G-NH2 (IX) or its salt x2 CH2 (CH2CH2) n-C-T-H (IV) , C C x2/\CH2 (CH2CH2) n-C-N-H (VIII) In the reaction (J), X X2, Y, n, G, A and T are as defined above. Further, as the salt of the compound of

the formula (IX), the same one as the salt of the compound of the above formula (III) may, for example, be mentioned.

The reaction (J) can be carried out in the same manner as the above reaction (B). [K] G-NH2 (IX) or its salt 2, C=C _ X CH2 (CH2CH2) n-C-T-Z (V) f I i X2 1-11 11 1 x2/\CH2 (CH2CH2) n-C-N-H (Vlil) In the reaction (K), Xi, X2, Y, n, G, A, T and Z are as defined above. Further, as the salt of the compound of the formula (IX), the same one as the salt of the compound of the above formula (III) may, for example, be mentioned.

The reaction (K) can be carried out in the same manner as the above reaction (C).

Preferred embodiments of pesticides containing the compounds of the present invention will be described below. The pesticides containing the compounds of the present invention are particularly useful, for example, as agents for controlling various pests which become problematic in the agricultural and horticultural fields, i. e. agricultural and horticultural pesticides, or as agents for controlling pests which are parasitic on

animals i. e. pesticides against parasites on animals.

The agricultural and horticultural pesticides containing the compounds of the present invention are useful as an insecticide, a miticide, a nematicide and a soil pesticide, and they are effective for controlling plant parasitic mites such as two-spotted spider mite (Tetranychus urticae), carmine spider mite (Tetranychus cinnabarinus), kanzawa spider mite (Tetranychus kanzawai), citrus red mite (Panonychus citri), European red mite (Panonychus ulmi), broad mite (Polyphagotarsonemus latus), pink citrus rust mite (Aculops pelekassi) and bulb mite (Rhizoglyphus echinopus) ; aphids such as green peach aphid (Myzus persicae) and cotton aphid (Aphis gossypii); agricultural insect pests such as diamondback moth (Plutella xylostella), cabbage armyworm (Mamestra brassicae), common cutworm (Spodoptera litura), codling moth (Laspeyresia pomonella), bollworm (Heliothis zea), tobacco budworm (Heliothis virescens), gypsy moth (Lymantria dispar), rice leafroller (Cnaphalocrocis medinalis), Adoxophyes sp., colorado potato beetle (Leptinotarsa decemlineata), cucurbit leaf beetle (Aulacophora femoralis), boll weevil (Anthonomus grandis), planthoppers, leafhoppers, scales, bugs, whiteflies, thrips, grasshoppers, anthomyiid flies, scarabs, black cutworm (Agrotis ipsilon), cutworm (Agrotis segetum) and ants; plant parasitic nematodes such as root-knot nematodes, cyst nematodes, root-lesion nematodes, rice white-tip nematode (Aphelenchoides besseyi), strawberry bud nematode (Nothotylenchus acris), pine wood nematode (Bursaphelenchus lignicolus); gastropods such as slugs and snails ; soil pests such as isopods such as pillbugs (Armadilidium vulgare) and pillbugs (Porcellio scaber); hygienic insect pests such as tropical rat mite (Ornithonyssus bacoti), cockroachs, housefly (Musca domestic) and house mosquito (Culex pipiens); stored grain insect pests such as angoumois grai moth (Sitotroga cerealella), adzuki bean weevil (Callosobruchus chinensis), red flour beetle (Tribolium castaneum) and mealworms; household goods insect pests such as casemaking clothes moth (Tinea pellionella), black carpet beetle (Anthrenus scrophularidae) and subterranean termites; domestic mites such as mold mite (Tyrophagus putrescentiae), Dermatophagoides farinae and Chelacaropsis moorei. Among them, the agricultural and horticultural pesticides containing the compounds of the present invention are particularly effective for controlling plant parasitic mites, agricultural insect pests, plant parasitic nematodes or the like. Further, they are effective against insect pests having acquired resistance to organophosphorus, carbamate and/or synthetic pyrethroid insecticides. Moreover, the compounds of the present invention have excellent systemic properties, and by the application of the compounds of the present invention to soil treatment, not

only noxious insects, noxious mites, noxious nematodes, noxious gastropods and noxious isopods in soil but also foliage pests can be controlled.

Another preferred embodiments of the pesticides containing compounds of the present invention may be agricultural and horticultural pesticides which collectively control the above-mentioned plant parasitic mites, agricultural insect pests, plant parasitic nematodes, gastropods and soil pests.

The agricultural and horticultural pesticide containing the compound of the present invention, is usually formulated by mixing the compound with various agricultural adjuvants and used in the form of a formulation such as a dust, granules, water-dispersible granules, a wettable powder, a water-based suspension concentrate, an oil-based suspension concentrate, water soluble granules, an emulsifiable concentrate, a soluble concentrate, a paste, an aerosol or an ultra low-volume formulation. However, so long as it is suitable'for the purpose of the present invention, it may be formulated into any type of formulation which is commonly used in this field. Such agricultural adjuvants include solid carriers such as diatomaceous earth, slaked lime, calcium carbonate, talc, white carbon, kaoline, bentonite, a mixture of kaolinite and sericite, clay, sodium carbonate, sodium bicarbonate, mirabilite, zeolite and starch; solvents such as water, toluene, xylene, solvent naphtha,

dioxane, acetone, isophorone, methyl isobutyl ketone, chlorobenzene, cyclohexane, dimethylsulfoxide, N, N- dimethylformamide, dimethylacetamide, N-methyl-2- pyrrolidone, and alcohol ; anionic surfactants and spreaders such as a salt of fatty acid, a benzoate, an alkylsulfosuccinate, a dialkylsulfosuccinate, a polycarboxylate, a salt of alkylsulfuric acid ester, an alkyl sulfate, an alkylaryl sulfate, an alkyl diglycol ether sulfate, a salt of alcohol sulfuric acid ester, an alkyl sulfonate, an alkylaryl sulfonate, an aryl sulfonate, a lignin sulfonate, an alkyldiphenyl ether disulfonate, a polystyrene sulfonate, a salt of alkylphosphoric acid ester, an alkylaryl phosphate, a styrylaryl phosphate, a salt of polyoxyethylene alkyl ether sulfuric acid ester, a polyoxyethylene alkylaryl ether sulfate, a salt of polyoxyethylene alkylaryl ether sulfuric acid ester, a polyoxyethylene alkyl ether phosphate, a salt of polyoxyethylene alkylaryl phosphoric acid ester, and a salt of a condensate of naphthalene sulfonate with formalin; nonionic surfactants and spreaders such as a sorbitan fatty acid ester, a glycerin fatty acid ester, a fatty acid polyglyceride, a fatty acid alcohol polyglycol ether, acetylene glycol, acetylene alcohol, an oxyalkylene block polymer, a polyoxyethylene alkyl ether, a polyoxyethylene alkylaryl ether, a polyoxyethylene styrylaryl ether, a polyoxyethylene glycol alkyl ether, a polyethylene glycol,

a polyoxyethylene fatty acid ester, a polyoxyethylene sorbitan fatty acid ester, a polyoxyethylene glycerin fatty acid ester, a polyoxyethylene hydrogenated castor oil, and a polyoxypropylene fatty acid ester; 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, cottonseed oil, soybean oil, rapeseed oil, linseed oil, tung oil, and liquid paraffins. Each of the components as such adjuvants may be one or more suitably selected for use, so long as the purpose of the present invention can thereby be accomplished. Further, various additives which are commonly used, such as a filler, a thickener, an anti-settling agent, an anti-freezing agent, a dispersion stabilizer, a phytotoxicity reducing agent, and an anti-mold agent, may also be employed.

The weight ratio of the compound of the present invention to the various agricultural adjuvants is usually from 0.001 : 99.999 to 95: 5, preferably from 0.005 : 99.995 to 90: 10.

In the actual application of such a formulation, it may be used as it is, or may be diluted to a predetermined concentration with a diluent such as water, and various spreaders e. g. surfactants, vegetable oils or mineral oils may be added thereto, as the case requires.

The application of the agricultural and horticultural pesticide containing the compound of the

present invention can not generally be defined, as it varies depending upon the weather conditions, the type of the formulation, the application season, the application site or the types or degree of outbreak of the pest insects. However, it is usually applied in a concentration of the active ingredient being from 0.05 to 800,000 ppm, preferably from 0.5 to 500,000 ppm, and the dose per unit area is such that the compound of the present invention is from 0.05 to 50,000 g, preferably from 1 to 30,000 g, per hectare. Further, agricultural and horticultural pesticides as another preferred embodiment of pesticides containing the compounds of the present invention may be applied in accordance with the above-described application of pesticides. The present invention includes such a method for controlling pests, particularly for controlling plant parasitic mites, agricultural insect pests or plant parasitic nematodes by such applications.

Various formulations of agricultural and horticultural pesticides containing the compounds of the present invention or their diluted compositions may be applied by conventional methods for application which are commonly employed, such as spraying (e. g. spraying, jetting, misting, atomizing, powder or grain scattering or dispersing in water), soil application (e. g. mixing or drenching), surface application (e. g. coating, powdering or covering) or impregnation to obtain poisonous feed.

Further, it is possible to feed domestic animals with a food containing the above active ingredient and to control the outbreak or growth of pests, particularly insect pests, with their excrements. Furthermore, the active ingredient may also be applied by a so-called ultra low-volume application method. In this method, the composition may be composed of 100% of the active ingredient.

Further, the agricultural and horticultural pesticides containing compounds of the present invention may be mixed with or may be used in combination with other agricultural chemicals, fertilizers or phytotoxicity-reducing agents, whereby synergistic effects or activities may sometimes be obtained. Such other agricultural chemicals include, for example, a herbicide, an insecticide, a miticide, a nematicide, a soil pesticide, a fungicide, an antivirus agent, an attractant, an antibiotic, a plant hormone and a plant growth regulating agent. Especially, with a mixed pesticide having a compound of the present invention mixed with or used in combination with one or more active compounds of other agricultural chemicals, the application range, the application time, the pesticidal activities, etc. may be improved to preferred directions.

The compound of the present invention and the active compounds of other agricultural chemicals may separately be formulated so that they may be mixed for use at the

time of application, or they may be formulated together.

The present invention includes such a mixed pesticidal composition.

The mixing ratio of the compound of the present invention to the active compounds of other agricultural chemicals can not generally be defined, since it varies depending upon the weather conditions, the types of formulations, the application time, the application site, the types or degree of outbreak of insect pests, etc., but it is usually within a range of from 1: 300 to 300: 1, preferably from 1 : 100 to 100: 1, by weight. Further, the dose for the application is such that the total amount of the active compounds is from 0.1 to 50,000 g, preferably from 1 to 30,000 g, per hectare. The present invention includes a method for controlling pests by an application of such a mixed pesticide composition.

The active compounds of insect pest control agents such as insecticides, miticides, nematicides or soil pesticides in the above-mentioned other agricultural chemicals, include, for example, (by common names, some of them are still in an application stage) organic phosphate compounds such as Profenofos, Dichlorvos, Fenamiphos, Fenitrothion, EPN, Diazinon, Chlorpyrifos- methyl, Acephate, Prothiofos, Fosthiazate, Phosphocarb, Cadusafos, Disulfoton, Chlorpyrifos, Demeton-S-methyl, Dimethoate, and Methamidophos; carbamate compounds such as Carbaryl, Propoxur, Aldicarb, Carbofuran, Thiodicarb,

Methomyl, Oxamyl, Ethiofencarb, Pirimicarb, Fenobucarb, Carbosulfan, and Benfuracarb; nereistoxin derivatives such as Cartap, Thiocyclam, and Bensultap; organic chlorine compounds such as Dicofol, and Tetradifon; organometallic compounds such as Fenbutatin Oxide; pyrethroid compounds such as Fenvalerate, Permethrin, Cypermethrin, Deltamethrin, Cyhalothrin, Tefluthrin, Ethofenprox, Fenpropathrin and Bifenthrin; benzoylurea compounds such as Diflubenzuron, Chlorfluazuron, Teflubenzuron, Flufenoxuron, Lufenuron, and Novaluron; juvenile hormone-like compounds such as Methoprene, Pyriproxyfen, and Fenoxycarb; pyridazinone compounds such as Pyridaben; pyrazole compounds such as Fenpyroximate, Fipronil, Tebufenpyrad, Ethiprole, Tolfenpyrad, and Acetoprole ; neonicotinoids such as Imidacloprid, Nitenpyram, Acetamiprid, Thiacloprid, Thiamethoxam, Clothianidin, and Dinotefuran; hydrazine compounds such as Tebufenozide, Methoxyfenozide, and Chromafenozide; dinitro compounds; organic sulfur compounds; urea compounds; triazine compounds; hydrazone compounds; and other compounds, such as Flonicamid, Buprofezin, Hexythiazox, Amitraz, Chlordimeform, Silafluofen, Triazamate, Pymetrozine, Pyrimidifen, Chlorfenapyr, Indoxacarb, Acequinocyl, Etoxazole, Cyromazine, 1,3- dichloropropene, Diafenthiuron, Benclothiaz, Flufenerim, Pyridalyl, Spirodiclofen, Bifenazate, Spiromesifen, Propargite, Clofentezine, and Fluacrypyrim. Further, BT

agents, microbial agricultural chemicals such as insect viruses, entomopathogenic fungi, and nematophagous fungi, or antibiotics such as Avermectin, Emamectin-Benzoate, Milbemectin, Spinosad, and Ivermectin, may be used in admixture or in combination.

The active compounds of fungicides among the above- mentioned other agricultural chemicals include, for example, (by common names, some of which are still in an application stage) pyrimidinamine compounds such as Mepanipyrim, Pyrimethanil, and Cyprodinil; azole compounds such as Triad'imefon, Bitertanol, Triflumizole, Etaconazole, Propiconazole, Penconazole, Flusilazole, Myclobutanil, Cyproconazole, Terbuconazole, Hexaconazole, Furconazole-cis, Prochloraz, Metconazole, Epoxiconazole, Tetraconazole, Oxpoconazole, and Sipconazole; quinoxaline compounds such as Quinomethionate ; dithiocarbamate compounds such as Maneb, Zineb, Mancozeb, Polycarbamate, Propineb; organic chlorine compounds such as Fthalide, Chlorothalonil, and Quintozene; imidazole compounds such as Benomyl, Thiophanate-Methyl, Carbendazim, and Cyazofamid; pyridinamine compounds such as Fluazinam; cyanoacetamide compounds such as Cymoxanil ; phenylamide compounds such as Metalaxyl, Oxadixyl, Ofurace, Benalaxyl, Furalaxyl, and Cyprofuram; sulfenic acid compounds such as Dichlofluanid; copper compounds such as cupric hydroxide, and Oxine Copper; isoxazole compounds such as Hydroxyisoxazole ; organophosphorus compounds such as

Fosetyl-Al,. Tolclofos-Methyl, S-benzyl 0, 0- diisopropylphosphorothioate, O-ethyl S, S- diphenylphosphorodithioate, and aluminumethylhydrogen phosphonate ; N-halogenothioalkyl compounds such as Captan, Captafol, and Folpet; dicarboximide compounds such as Procymidone, Iprodione, and Vinclozolin; benzanilide compounds such as Flutolanil, Mepronil, and Zoxamide; piperazine compounds such as Triforine; pyrizine compounds such as Pyrifenox; carbinol compounds such as Fenarimol, and Flutriafol; piperidine compounds such as Fenpropidine; morpholine compounds such as Fenpropimorph; organotin compounds such as Fentin Hydroxide, and Fentin Acetate; urea compounds such as Pencycuron; cinnamic acid compounds such as Dimethomorph; phenylcarbamate compounds such as Diethofencarb ; cyanopyrrole compounds such as Fludioxonil, and Fenpiclonil; Strobilurin compounds such as Azoxystrobin, Kresoxim-Methyl, Metominofen, Trifloxystrobin, Picoxystrobin, and Pyraclostrobin; oxazolidinone compounds such as Famoxadone; thiazole carboxamide compounds such as Ethaboxam; silyl amide compounds such as Silthiopham; aminoacid amidecarbamate compounds such as Iprovalicarb; imidazolidine compound such as Fenamidone; hydroxyanilide compounds such as Fenhexamid; benzene sulfonamide compounds such as Flusulfamide; anthraquinone compounds; crotonic acid compounds; antibiotics; and other compounds, such as Isoprothiolane, Tricyclazole, Pyroquilon, Diclomezine,

Probenazole, Quinoxyfen, Propamocarb Hydrochloride, Spiroxamine, Chloropicrin, Dazomet, and Metam-Sodium.

Further, agricultural chemicals which may be used in admixture with or in combination with the compounds of the present invention, may, for example, be the active ingredient compounds in the herbicides as disclosed in Farm Chemicals Handbook (2000 edition), particularly those of soil treatment type.

The pesticides against parasites on animals are effective for controlling e. g. external parasites which are parasitic on the body surface of host animals (such as the back, the axilla, the lower abdomen or inside of the thigh) or internal parasites which are parasitic in the body of host animals (such as the stomach, the intestinal tract, the lung, the heart, the liver, the blood vessels, the subcutis or lymphatic tissues), but they are particularly effective for controlling the external parasites.

The external parasites may, for example, be animal parasitic acarus or fleas. Their species are so many that it is difficult to list all of them, and therefore, their typical examples will be given.

The animal parasitic acarus may, for example, be ticks such as Boophilus microplus, Rhipicephalus sanguineus, Haemaphysalis longicornis, Haemaphysalis flava, Haemaphysalis campanulata, Haemaphysalis concinna, Haemaphysalis japonica, Haemaphysalis kitaokai,

Haemaphysalis ias, Ixodes ovatus, Ixodes nipponensis, Ixodes persulcatus, Amblyomma testudinarium, Haemaphysalis megaspinosa, Dermacentor reticulatus, and Dermacentor taiwanesis; common red mite (Dermanyssus gallinae); northern fowl mites such as Ornithonyssus sylviarum, and Ornithonyssus bursa; trombidioids such as Eutrombicula wichmanni, Leptotrombidium akamushi, Leptotrombidium pallidum, Leptotrombidium fuji, Leptotrombidium tosa, Neotrombicula autumnalis, Eutrombicula alfreddugesi, and Helenicula miyagawai; cheyletidae such as Cheyletiella yasguri, Cheyletiella parasitivorax, and Cheyletiella blakei; sarcoptic mange mites such as Psoroptes cuniculi, Chorioptes bovis, Otodectes cynotis, Sarcoptes scabiei, and Notoedres cati; and Demodicidae such as Demodex canis. The pesticides against parasites on animals, containing the compounds of the present invention, are particularly effective for the control of ticks among them.

The fleas may, for example, be externally parasitic wingless insects belonging to Siphonaptera, more specifically, fleas belonging to Pulicidae, Ceratephyllus, etc. Fleas belonging to Pulicidae may for example, be Ctenocephalides canis, Ctenocephalides felis, Pulex irritans, Echidnophaga gallinacea, Xenopsylla cheopis, Leptopsylla segnis, Nosopsyllus fasciatus, and Monopsyllus anisus. The pesticides against parasites on animals, containing the compounds of the present

invention, are particularly effective for the control of fleas belonging to Pulicidae, particularly Ctenocephalides canis and Ctenocephalides felis, among them.

Other external parasites may, for example, be sucking lice (Anoplura) such as shortnosed cattle louse (Haematopinus eurysternus), horse sucking louse (Haematopinus asini), sheep louse, longnosed cattle louse (Linognathus vituli), and head louse (Pediculus capitis); biting lice such as dog biting louse (Trichodectes canis); and blood-sucking dipterous insects such as horsefly (Tabanus trigonus), biting midges (Culicoides schultzei), and blackfly (Simulium ornatum). Further, the internal parasites may, for example, be nematodes such as lung worms, whipworms (Trichuris), tuberous worms, gastric parasites, ascaris, and filarioidea; tapeworms; flukes; and protozoa such as coccidia, malaria parasites (Plasmodium malariae), intestinal sarcocyst, toxoplasma, and cryptosporidium.

The host animals may, for example, be pet animals such as dogs, cats, mice, rats, hamsters, guinea pigs, squirrels, rabbits, ferrets, birds (such as pigeons, parrots, hill mynas, Java sparrows, honey parrots, lovebirds and canaries); domestic animals such as cows, horses, pigs and sheep; and poultry such as ducks and chickens. The pesticides against parasites on animals, containing the compounds of the present invention, are

particularly effective for the control of pests parasitic on pet animals or domestic animals, especially for the control of external parasites, among them. Among pet animals, they are effective particularly for dogs and cats, and among domestic animals, they are particularly effective for cows and horses.

When the compound of the present invention is used as a pesticide against parasites on animals, it may be used as it is or may be used together with suitable adjuvants, as formulated into various formulations such as a dust, granules, tablets, a powder, capsules, a soluble concentrate, an emulsifiable concentrate, a water-based suspension concentrate and an oil-based suspension concentrate. In addition to such formulations, it may be formulated into any type of formulation which is commonly used in this field, so long as it is suitable for the purpose of the present invention. The adjuvants to be used for formulations may, for example, be anionic surfactants or nonionic surfactants exemplified above as adjuvants for formulation of agricultural and horticultural pesticides; a cationic surfactant such as cetyl trimethylammonium bromide; a solvent such as water, acetone, acetonitrile, monomethylacetamide, dimethylacetamide, dimethylformamide, 2-pyrrolidone, N- methyl-2-pyrrolidone, kerosene, triacetin, methanol, ethanol, isopropanol, benzyl alcohol, ethylene glycol, propylene glycol, polyethylene glycol, liquid

polyoxyethylene glycol, butyl diglycol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monoethyl ether, diethylene glycol n- butyl ether, dipropylene glycol monomethyl ether, or dipropylene glycol n-butyl ether; an antioxidant such as butylhydroxyanisole, butylhydroxytoluene, ascorbic acid, sodium hydrogenmetasulfite, propyl gallate or sodium thiosulfate; a coating film-forming agent such as polyvinylpyrrolidone, polyvinyl alcohol, or a copolymer of vinyl acetate and vinyl pyrrolidone ; the vegetable oils and mineral oils as exemplified above as adjuvants for formulation of agricultural and horticultural pesticides ; and a carrier such as lactose, sucrose, glucose, starch, wheat flour, corn powder, soybean cake and meal, defatted rice bran, calcium carbonate or other commercially available feed materials. One or more of the respective components of these adjuvants may be suitably selected for use, so long as such will not depart from the purpose of the present invention.

Further, other than the above-mentioned adjuvants, some among those known in this field may suitably be selected for use, and still further, some among the above- mentioned various adjuvants to be used in the agricultural and horticultural field may suitably be selected for use.

The blend ratio of the compound of the present invention to various adjuvants is usually from 0.1 : 99.9

to 90 : 10. In the actual use of such a formulation, it may be used as it is, or may be diluted to a predetermined concentration with a diluent such as water, and various spreaders (e. g. surfactants, vegetable oils or mineral oils) may be added thereto, as the case requires.

Administration of the compound of the present invention to a host animal is carried out orally. or parenterally. As an oral administration method, a method of administering-a tablet, a liquid agent, a capsule, a wafer, a biscuit, a minced meat or other feed, containing the compound of the present invention, may be mentioned.

As a parenteral administration method, there may, for example, be mentioned a method wherein the compound of the present invention is formulated into a suitable formulation and then taken into the body by e. g. intravenous administration, intramuscular administration, intradermal administration, hypodermic administration, etc.; a method wherein it is administered on the body surface by spot-on treatment, pour-on treatment or spray treatment ; or a method of embedding a resin fragment or the like containing the compound of the present invention under the skin of the host animal.

The dose of the compound of the present invention to a host animal varies depending upon the administration method, the purpose of administration, the deceased symptom, etc., but it is usually administered in a

proportion of from 0.01 mg to 100 g, preferably from 0.1 mg to 10 g, per 1 kg of the body weight of the host animal.

The present invention also includes a method for controlling a pest by the above-mentioned administration method or by the above-mentioned dose, particularly a method for controlling external parasites or internal parasites.

When the compound of the present invention is used as a pesticide against parasites on animals, various vitamins, minerals, amino acids, nutrients, enzymes, antipyretics, sedatives, antiphlogistics, fungicides, colorants, aromatic substances, preservatives, etc. , may be used in admixture with or in combination with the adjuvants. Further, as the case requires, other animal drugs or agricultural chemicals, such as vermicides, anti-coccidium agents, insecticides, miticides, pulicides, nematocides, bactericides or antibacterial agents, may be mixed or combined for use, whereby improved effects may sometimes be obtained. The present invention includes such a mixed pesticidal composition having the above- mentioned various components mixed or combined for use, and further a method for controlling a pest by using it, particularly a method for controlling external parasites or internal parasites.

Now, some of preferred embodiments of the compounds of the present invention will be shown. However, the

present invention is by no means thereby restricted.

(1) The above compound wherein 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) S02Q,-N=CHQ, -N=C (Q) 2,-SO2Q or-S02N (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 alkyl which may be substituted by W, alkenyl which may be substituted by W, alkynyl which may be substituted by W, a cyclic hydrocarbon group which may be substituted by W, or a 5-to 12-membered heterocyclic group (the heterocyclic group may be substituted by W) containing an optional hetero atom selected from an oxygen atom, a sulfur atom and a nitrogen atom; W is halogen, nitro, cyano, alkyl which may be substituted by K, alkenyl which may be substituted by K, alkynyl which may be substituted by K, a cyclic hydrocarbon group which may be substituted by M1, a 5-to 12-membered heterocyclic group (the heterocyclic group may be substituted by M1) containing an optional hetero atom selected from an oxygen atom, a sulfur atom and a nitrogen atom,-OR1,-SR1,-NR1R2,-COR1,-CO2R1,-COSR1, -CSOR1,-CS2R1,-SO2NR1R2,-CONR1R2,-CSNR1R2,-C (=NOV) R -N(R1)COR3, -N(R1)CO2R3, -N(R1)COSR3, -N(R1)CSOR3, -N(R1)CS2R3, -N(R1)SO2R3, -SOR3, -SO2R3, -CSR3, -OCOR3, - OCSR3,-SCOR3,-SCSR3, trialkylsilyl or trialkylsilyloxy;

K is halogen, nitro, cyano, a cyclic hydrocarbon group which may be substituted by M1, a 5-to 12-membered heterocyclic group (the heterocyclic group may be substituted by M1) containing an optional hetero atom selected from an oxygen atom, sulfur atom and a nitrogen atom-oM2,-SM2,-NM2M3,-COM2,-CO2M2,-COSM2,-CSOM2, -CS2M2, -SO2NM2M3, -CONM2M3, -CSNM2M3, -C (=NOV) M2,-N (M2) CoM4, -N (M) CO2M,-N (M) COSM,-N (M) CSOM,-N (M) CS2M, -N(M2)SO2M4, -SOM4, -SO2M4, -CSM4, -OCOM4, -OCSM4, -SCOM4 or-SCSM4 M1 is halogen, nitro, cyano, alkyl, haloalkyl, cycloalkyl, halocycloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, -OR4, -SR4, -NR4R5, -COR4, -CO2R4, -COSR4, -CSOR4, -CS2R4, -SO2NR4R5, -CONR4R5, -CSNR4R5, -C (=NOV) R4, <BR> <BR> <BR> <BR> -N (R4) COR6-N (R4) C02R6-N (R4) COSR6,-N (R4) CSOR6,<BR> <BR> <BR> <BR> <BR> <BR> -N (R4) CS2R6,-N (R4) S02R6,-SOR6,-SO2R6,-CSR6,-OCOR6, -OCSR6, -SCOR6 or -SCSR6; each of M2 and M3 is a hydrogen atom, alkyl which may be substituted by M5, alkenyl which may be substituted by M5, alkynyl which may be substituted by M5, a cyclic hydrocarbon group which may be substituted by M1, or a 5- to 12-membered heterocyclic group (the heterocyclic group may be substituted by M1) containing an optional hetero atom selected from an oxygen atom, a sulfur atom and a nitrogen atom; M4 is alkyl which may be substituted by M5, alkenyl which may be substituted by M5, alkynyl which may be

substituted by M5, a cyclic hydrocarbon group which may be substituted by M1, or a 5-to 12-membered heterocyclic group (the heterocyclic group may be substituted by M1) containing an optional hetero atom selected from an oxygen atom, a sulfur atom and a nitrogen atom; M5 is halogen, alkoxy which may be substituted by Ml, alkylthio which may be substituted by M1, alkylsulfinyl which may be substituted by M1, alkylsulfonyl which may be substituted by M1, -M6, -OM6 or-SM6 ; M5 is a cyclic hydrocarbon group which may be substituted by M1, or a 5-to 12-membered heterocyclic group (the heterocyclic group may be substituted by M1) containing an optional hetero atom selected from an oxygen atom, a sulfur atom and a nitrogen atom; each of R1 and R2 is a hydrogen atom, alkyl which may be substituted by M7, alkenyl which may be substituted by M7, alkynyl which may be substituted by M7, a cyclic hydrocarbon group which may be substituted by M1, or a 5- to 12-membered heterocyclic group (the heterocyclic group may be substituted by M1) containing an optional hetero atom selected from an oxygen atom, a sulfur atom and a nitrogen atom; R3 is alkyl which may be substituted by M7, alkenyl which may be substituted by M7, alkynyl which may be substituted by M7, a cyclic hydrocarbon group which may be substituted by M1, or a 5-to 12-membered heterocyclic group (the heterocyclic group may be substituted by M1)

containing an optional hetero atom selected from an oxygen atom, a sulfur atom and a nitrogen atom; M7 is halogen, a cyclic hydrocarbon group which may be substituted by M1, a 5-to 12-membered heterocyclic group (the heterocyclic group may be substituted by M1) containing an optional hetero atom selected from an oxygen atom, a sulfur atom and a nitrogen atom,-OMB,-SMB,-NM8M9,-COMB,-CO2MB,-COSM8,-CSOMB, -CS2M8, -SO2NM8M9, -CONM8M9, -CSNM8M9, -C(=NOV)M8, -N(M8)COM10, -N(M8)CO2M10, -N(M8)COSM10, -N(M8)CSOM10, -N(M8)CS2M10, -N(M8)SO2M10, -SOM10, -SO2M10, -CSM10, -OCOM10, -OCSM10, -SCOM10 or -SCSM10; each of M8 and M9 is a hydrogen atom, alkyl which may be substituted by M1, alkenyl which may be substituted by Mi, alkynyl which may be substituted by M1, a cyclic hydrocarbon group which may be substituted by M1, or a 5- to 12-membered heterocyclic group (the heterocyclic group may be substituted by M1) containing an optional hetero atom selected from an oxygen atom, a sulfur atom and a nitrogen atom; M1° is alkyl which may be substituted by M1, alkenyl which may be substituted by M1, alkynyl which may be substituted by M1, a cyclic hydrocarbon group which may be substituted by M1, or a 5-to 12-membered heterocyclic group (the heterocyclic group may be substituted by M1) containing an optional hetero atom selected from an oxygen atom, a sulfur atom and a nitrogen atom;

V is a hydrogen atom, alkyl which may be substituted by M1, alkenyl which may be substituted by M1, alkynyl which may be substituted by M1, a cyclic hydrocarbon group which may be substituted by M1, or a 5-to 12-membered heterocyclic group (the heterocyclic group may be substituted by M1) containing an optional hetero atom selected from an oxygen atom, a sulfur atom and a nitrogen atom; each of R4 and R5 is a hydrogen atom, alkyl, haloalkyl, arylalkyl, heteroarylalkyl, cycloalkyl, halocycloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, aryl or heteroaryl; R6 is alkyl, haloalkyl, arylalkyl, heteroarylalkyl, cycloalkyl, halocycloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, aryl or heteroaryl.

(4) The above compound wherein Q is a cyclic hydrocarbon group which may be substituted by W, or a 5- to 12-membered heterocyclic group (the heterocyclic group may be substituted by W) containing an optional hetero atom selected from an oxygen atom, a sulfur atom and a nitrogen atom.

(5) The above compound wherein Q is a cyclic hydrocarbon group which may be substituted by W.

(6) The above compound wherein Q is a 5-to 12- membered heterocyclic group (the heterocyclic group may be substituted by W) containing an optional hetero atom selected from an oxygen atom, a sulfur atom and a

nitrogen atom.

(7) The above compound wherein W is halogen, nitro, cyano, alkyl, haloalkyl, alkoxyalkyl, phenylalkyl (the phenyl moiety may be substituted by M1), phenoxyalkyl (the phenyl moiety may be substituted by M), alkenyl, haloalkenyl, alkynyl, haloalkynyl, a cyclic hydrocarbon group which may be substituted by M1, a 5-to 12-membered heterocyclic'group (the heterocyclic group may be substituted by M1) containing an optional hetero atom selected from an oxygen atom, a sulfur atom and a nitrogen'atom, hydroxy, alkoxy, haloalkoxy, alkoxyalkoxy, phenylalkoxy (the phenyl moiety may be substituted by M1), phenoxyalkoxy (the phenyl moiety may be substituted by Ml), phenoxy which may be substituted by M, alkylthio, haloalkylthio, phenylthio which may be substituted by M1, amino, monoalkylamino, dialkylamino, monophenylamino (the phenyl moiety may be substituted by M1), diphenylamino (the phenyl moiety may be substituted by M1), amino substituted by alkyl and phenyl (the phenyl moiety may be substituted by M1), alkoxycarbonyl, dialkylaminocarbonyl, aminocarbonyl substituted by alkyl and phenyl (the phenyl moiety may be substituted by M1), alkylsulfinyl, haloalkylsulfinyl, benzenesulfinyl which may be substituted by M1, alkylsulfonyl, haloalkylsulfonyl, benzenesulfonyl which may be substituted by M1, acyl, acyloxy, trialkylsilyl or trialkylsilyloxy.

(8) The above compound wherein W is halogen, nitro,

cyano, alkyl, haloalkyl, phenyl which may be substituted by M1, hydroxy, alkoxy, haloalkoxy, phenoxy which may be substituted by M1, alkylthio, haloalkylthio, phenylthio which may be substituted by M1, alkoxycarbonyl, benzenesulfinyl which may be substituted by M1, or benzenesulfonyl which may be substituted by M1.

(9) The above compound wherein G is a hydrogen atom, alkyl, haloalkyl, phenylalkyl, alkenyl, haloalkenyl, phenylalkenyl, alkynyl, haloalkynyl, phenylalkynyl or-C (=B) Q.

(10) The above compound wherein X1 and X2 are both fluorine atoms.

(11) The above compound wherein Y is alkyl.

(12) The above compound wherein Y is methyl or ethyl.

(13) 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 the formula (I) is represented by the formula (Ia) : wherein each of X1 and X2 is halogen; Y is alkyl, haloalkyl or phenyl; n is from 0 to 5; each of A and B is an oxygen atom or a sulfur atom; G is a hydrogen atom, alkyl, haloalkyl, phenylalkyl, alkenyl, haloalkenyl, phenylalkenyl, alkynyl, haloalkynyl or phenylalkynyl; Q is a 5-to 12-membered heterocyclic group (the

heterocyclic group may be substituted) containing an optional hetero atom selected from an oxygen atom, a sulfur atom and a nitrogen atom, alkyl which may be substituted by W, alkenyl which may be substituted by W, alkynyl which may be substituted by W, or a cyclic hydrocarbon group which may be substituted by W; W is halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, hydroxy, alkoxycarbonyl, cyano, nitro, phenyl which may be substituted, phenoxy which may be substituted, phenylthio which may be substituted, benzenesulfinyl which may be substituted, or benzenensulfonyl which may be substituted.

(16) The above compound wherein in the compound of the above (14) the substituent of the heterocyclic group for Q, or the substituent in the phenyl which may be substituted, the phenoxy which may be substituted, the phenylthio which may be substituted, the benzenesulfinyl which may be substituted or the benzenesulfonyl which may be substituted, for W, is halogen, nitro, cyano, (Cl8) alkyl, halo (Ci-8) alkyl, aryl (Cl8) alkyl wherein the aryl moiety may be substituted, heteroaryl (C1-8) alkyl wherein the heteroaryl moiety may be substituted, (C3-8) cycloalkyl, halo (C3-8) cycloalkyl, (C2-8) alkenyl, halo (C28) alkenyl, (C28) alkynyl, halo (C2-8) alkynyl, aryl which may be substituted, heteroaryl which may be substituted,-NR1R2,-OR1,-SR1,-SOR1,-SO2R1,-SO2NR1R2, - COR1,-C02R1,-COSR1,-CSOR1,-OCOR3 or-CH2CN ;

each of Ri and R2 is a hydrogen atom, (Cl8) alkyl, halo (Cl8) alkyl, aryl (C1-8) alkyl wherein the aryl moiety may be substituted, heteroaryl (Cl-8) alkyl wherein the heteroaryl moiety may be substituted, (C3-8) cycloalkyl, halo (C3-8) cycloalkyl, (C2-8) alkenyl, halo (C28) alkenyl, (C2-8) alkynyl, halo (C2-8) alkynyl, aryl which may be substituted or heteroaryl which may be substituted; R3 is (C1-8) alkyl, halo (C1-8) alkyl, aryl (C1-8) alkyl wherein the aryl moiety may be substituted, heteroaryl (C1-8) alkyl wherein the heteroaryl moiety may be substituted, (C3-8) cycloalkyl, halo (C3_8) cycloalkyl, (C2-8) alkenyl, halo (C2-8) alkenyl, (C2-8) alkynyl, halo (C2-8) alkynyl, aryl which may substituted, or heteroaryl which may be substituted; the substituent for the aryl which may be substituted or for the heteroaryl which may be substituted, is halogen, nitro, cyano, (C1-8) alkyl, halo (Cl8) alkyl, (C3-8) cycloalkyl, halo (C3-8) cycloalkyl, (C2-8) alkenyl, halo (C2-8) alkenyl, (C2-8) alkynyl, halo (C28) alkynyl, -NR4R5, -OR4, -SR4, -SOR4, - S02R4,-S02NR4R5,-COR4,-C02R. 4,-COSR4,-CSOR4 or-OCOR6 ; each of R4 and R5 is a hydrogen atom, (C1-8) alkyl, halo (C1-8) alkyl, (C38) cycloalkyl, halo (C3-8) cycloalkyl, (C2-8) alkenyl, halo (C2-8) alkenyl, (C28) alkynyl or halo (C2-8) alkynyl ; R6 is (C1-8) alkyl, halo (C1-8) alkyl, aryl (C1-8) alkyl, heteroaryl (Cl8) alkyl, (C3-8) cycloalkyl, halo (C3-8) cycloalkyl, (C2-8) alkenyl, halo (C2-8) alkenyl,

(C2-8) alkynyl, halo (C2-8) alkynyl, aryl or heteroaryl.

Now, Examples of the present invention will be given, but the present invention is by no means thereby restricted. Firstly, Preparation Examples of the compounds of the present invention will be described.

PREPARATION EXAMPLE 1 Preparation of. N- (7-ethyl-8, 8-difluoro-7- octenoylAbenzamide (after-mentioned Compound No. 1-45) (1) To a mixed solution comprising 33 g of sodium and 1,340 ml of ethanol, 186.72 g of methyl 3-keto-n-valerate and then 300 g of ethyl 5-bromovalerate were added, and the mixture was reacted for 7 hours and 30 minutes under reflux.

After completion of the reaction, the reaction mixture was left to stand at room temperature for 13 hours, and ethanol was distilled off under reduced pressure. Then, 164 ml of water, 150 ml of a saturated sodium chloride aqueous solution and 150 ml of ethyl acetate were added, followed by extraction. The aqueous layer was further extracted twice with 150 ml of ethyl acetate, and the obtained all organic layers were dried over anhydrous sodium sulfate, and ethyl acetate was distilled off under reduced pressure to obtain 374.5 g of oily crude diethyl 2-propionylpimelate.

(2) A mixed solution comprising 180 g of 85% potassium hydroxide and 1,770 ml of water, was added to 374.5 g of the crude diethyl 2-propionylpimelate, and the mixture

was reacted at room temperature for 6 days. The reaction mixture was washed with 500 ml of hexane, and 235 ml of concentrated sulfuric acid was added to the aqueous layer, and the mixture was further reacted for 1 hour under reflux.

After completion of the reaction, the reaction mixture was cooled and saturated by an addition of sodium chloride. Thereafter, it was extracted four times with 300 ml of ethyl ether. The organic layer was dried over anhydrous sodium sulfate, and ethyl ether was distilled off under reduced pressure to obtain 232.84 g of crude 7- oxononanoic acid as white crystals.

(3) A mixed solution comprising 227.97 g of the crude 7- oxononanoic acid, 2,000 ml of ethanol and 30 ml of concentrated sulfuric acid, were reacted for 21 hours and 30 minutes under reflux.

After completion of the reaction, ethanol was distilled off under reduced pressure from the reaction mixture, and 150 g of ice and 500 ml of ethyl ether were added, then separated. Thereafter, the organic layer was washed with 100 ml of water and washed three times with 50 ml of a saturated sodium chloride aqueous solution.

The aqueous layer was extracted with 200 ml of ethyl ether, followed by washing five times with 50 ml of a saturated sodium chloride aqueous solution. The obtained all organic layers were dried over anhydrous sodium sulfate, and ethyl ether was distilled off under reduced

pressure to obtain 243.82 g of oily crude ethyl 7- oxononanoate.

(4) Under a nitrogen atmosphere, 550 ml of tris (dimethylamino) phosphine was dropwise added at 2 to 15°C to a mixture comprising 2,000 ml of anhydrous 2- methoxyethyl ether and 138. 5 ml of dibromodifluoromethane.

After completion of the dropwise addition, 151.5 g of the crude ethyl 7-oxononanoate was added at 25°C, and the mixture was reacted at 50°C for 15 hours. Thereafter, it was further reacted at 100°C for 4 hours.

After completion of the reaction, the reaction mixture was put into 930 ml of water and extracted with 930 ml of hexane. The organic layer was washed once with 930 ml of water and five times with 400 ml of water and thereafter washed once with 100 ml of a saturated sodium chloride aqueous solution, to obtain 149.6 g of oily crude ethyl 7-ethyl-8,8-difluoro-7-octenoate.

(5) A mixed solution comprising 50. 64 g of 85% potassium hydroxide and 550 ml of methanol, was added to 149.6 g of the crude ethyl 7-ethyl-8,8-difluoro-7-octenoate, and the mixture was reacted at room temperature for 3 days.

After completion of the reaction, methanol was distilled off under reduced pressure from the reaction mixture, and the rest was dissolved in 430 ml of water and then washed three times with 60 ml of dichloromethane.

The aqueous layer was acidified with concentrated hydrochloric acid and extracted three times with 40 ml of

dichloromethane. The organic layer was dried over anhydrous sodium sulfate, and ethyl ether was distilled off under reduced pressure to obtain 118.94 g of oily crude 7-ethyl-8,8-difluoro-7-octenoic acid. The NMR spectrum data of this product were as follows.

1H-NMR ppm (solvent: CDCl3/400 MHz) 2.34 (2H, t, J=7.6Hz), 1. 92-1. 99 (4H, m), 1.63 (2H, quintet, J=7. 5Hz), 1.28-1. 42 (4H, m), 0.97 (3H, t, J=7.4Hz) (6) 12 ml of oxalyl chloride was dropwise added to 5.95 g of the crude 7-ethyl-8, 8-difluoro-7-octenoic acid under cooling with ice. 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 7- ethyl-8, 8-difluoro-7-octenoyl chloride.

19.2 ml of 1.58 M butyl lithium (hexane solution) was dropwise added at-78°C under a nitrogen atmosphere to a mixed solution comprising 3.50 g of benzamide and 40 ml of tetrahydrofuran. After stirring for 40 minutes, a mixed solution comprising the above crude 7-ethyl-8, 8- difluoro-7-octenoyl chloride and 10 ml of tetrahydrofuran, was dropwise added thereto, and the mixture was reacted for 20 minutes. Then, the mixture was returned to room temperature and further reacted for 5 hours and 30 minutes.

After completion of the reaction, the reaction

mixture was put into a small amount of water and then into a saturated sodium chloride aqueous 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 (developing solvent: hexane/ethyl acetate=8/2) and then crystallized from a mixed solvent of ethyl ether and hexane. Crystals were collected by filtration and washed with hexane to obtain 1.995 g of the desired product having a melting point of from 63 to 64°C.

PREPARATION EXAMPLE 2 Preparation of N- (7-ethyl-8, 8-difluoro-7-octenoyl) 2- thiophenecarboxamide (after-mentioned Compound No. 1-67) 1. 3 ml of oxalyl chloride and 0.5 g of crude 7- ethyl-8,8-difluoro-7-octenoic 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-octenoyl chloride.

1.68 ml of 1.59 M butyl lithium (hexane solution) was dropwise added at-78°C under a nitrogen atmosphere to a mixed solution comprising 0.309 g of 2- thiophenecarboxamide, 10 ml of tetrahydrofuran and 1 ml of hexamethylphosphoric triamide. After stirring for 35 minutes, a mixed solution comprising the above crude 7- ethyl-8,8-difluoro-7-octenoyl chloride and 2 ml of tetrahydrofuran, was dropwise added, and the mixture was

reacted for 40 minutes. The mixture was then returned to room temperature and further reacted overnight.

After completion of the reaction, the reaction mixture was put 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 (developing solvent: hexane/ethyl acetate=8/2) and then washed with hexane to obtain 0.055 g of the desired product having a melting point of from 75 to 78°C.

PREPARATION EXAMPLE 3 Preparation of N- (7-ethyl-8, 8-difluoro-7-octenoyl) 2- phenoxyacetamide (after-mentioned Compound No. 1-90) 16 ml of oxalyl chloride was dropwise added under cooling with ice to 6. 0 g of crude 7-ethyl-8, 8-difluoro- 7-octenoic acid. 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-octenoyl chloride.

20 ml of 1.59 M butyl lithium (hexane solution) was dropwise added at-78°C under a nitrogen atmosphere to a mixed solution comprising 4.4 g of phenoxyacetamide and 150 ml of tetrahydrofuran. After stirring for 40 minutes, a mixed solution comprising the above crude 7-ethyl-8,8- difluoro-7-octenoyl chloride and 10 ml of tetrahydrofuran,

was dropwise. added, and the mixture was reacted for 35 minutes. Thereafter, the mixture was returned to room temperature and further reacted overnight.

After completion of the reaction, the reaction mixture was put 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 (developing solvent: hexane/ethyl acetate=7.5/2. 5), and then crystallized from a mixed solvent of ethyl ether and hexane. Crystals were collected by filtration and washed with hexane to obtain 2.22 g of the desired product having a melting point of from 64 to 65°C.

PREPARATION EXAMPLE 4 Preparation of phenyl N- (7-ethyl-8, 8-difluoro-7- octenoyl) carbamate (after-mentioned Compound No. 2-3) 0.8 ml of oxalyl chloride was dropwise added to 0.4 g of crude 7-ethyl-8, 8-difluoro-7-octenoic acid. After completion of the dropwise addition, the mixture was reacted at room temperature for 1 hour and 20 minutes, and the reaction mixture was concentrated under reduced pressure to obtain crude 7-ethyl-8,8-difluoro-7-octenoyl chloride.

1.3 ml of 1.58 M butyl lithium (hexane solution) was dropwise added at-78°C under a nitrogen atmosphere to a mixed solution comprising 0.266 g of phenyl carbamate and

3 ml of tetrahydrofuran. After stirring for 40 minutes, a mixed solution comprising the above crude 7-ethyl-8,8- difluoro-7-octenoyl chloride and 2 ml of tetrahydrofuran, was dropwise added, and the mixture was reacted for 15 minutes. Thereafter, the mixture was returned to room temperature and further reacted overnight.

After completion of the reaction, the reaction mixture was put 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 (developing solvent: hexane/ethyl acetate=8/2), to obtain 0.34 g of the desired product as an oily substance.

PREPARATION EXAMPLE 5 Preparation of 1-(7-ethyl-8, 8-difluoro-7-octenoyl) -3- phenylurea (after-mentioned Compound No. 2-4) (1) 5.3 ml of oxalyl chloride was dropwise added to 2.0 g of 7-ethyl-8, 8-difluoro-7-octenoic acid. After completion of the dropwise addition, the mixture was reacted at room temperature for 2 hours, and the reaction mixture was concentrated under reduced pressure to obtain crude 7-ethyl-8,8-difluoro-7-octenoyl chloride.

Ammonia gas was blown under cooling with ice into 50 ml of tetrahydrofuran to saturation, and a mixed solution comprising the above crude 7-ethyl-8,8-difluoro-7- octenoyl chloride and 5 ml of tetrahydrofuran, was

dropwise added thereto. The mixture was reacted at room temperature for 16 hours and 30 minutes.

After completion of the reaction, a small amount of water was added to the reaction mixture to dissolve the solid product, and a saturated sodium chloride aqueous solution was further added. The mixture was 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 (developing solvent: hexane/ethyl acetate=3/7), to obtain 1.70 g of 7-ethyl- 8,8-difluoro-7-octenamide having a melting point of from 68 to 71°C. The NMR spectrum data of this product were as follows.

1H-NMR bppm (solvent: Cd 13/400 MHz) 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), 1.26-1. 42 (4H, m), 0.96 (3H, t, J=7.6Hz) (2) 0.116 g of phenyl isocyanate was added to a mixed solution comprising 0.2 g of the 7-ethyl-8, 8-difluoro-7- octenamide obtained in the above step and 2 ml of dioxane, and the mixture was reacted at room temperature for 2 hours. Thereafter, it was further reacted for 17 hours and 30 minutes under reflux.

After completion of the reaction, dioxane was distilled off under reduced pressure from the reaction mixture, and the residue was purified by silica gel

column chromatography (developing solvent: hexane/ethyl acetate=8/2) to obtain 0.14 g of the desired product having a melting point of from 76 to 78°C.

PREPARATION EXAMPLE 6 Preparation of 2'-benzhydrylidene 7-ethyl-8,8-difluoro-7- octenohydrazide (after-mentioned Compound No. 2-8) A mixture comprising 0.206 g of crude 7-ethyl-8,8- difluoro-7-octenoic acid, 0.196 g of benzophenone hydrazone, 0.2 g of 1-ethyl-3- (3- dimethylaminopropyl) carbodiimide hydrochloride and 3 ml of dichloromethane, was reacted at room temperature for 17 hours. Thereafter, it was further reacted at 40°C for 5 hours.

After completion of the reaction, the reaction mixture was washed with water and then with a saturated sodium chloride aqueous solution. The organic layer was dried over anhydrous sodium sulfate, and dichloromethane was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate=17/3) to obtain 0.15 g of the desired product having a melting point of from 70 to 74°C.

Now, typical examples of the compounds of the present invention represented by the above formula (I) will be given in Tables 1 and 2, and the NMR spectrum data thereof will be given in Table 3. These compounds can be prepared by the above-described Preparation

Examples or by the above-mentioned various processes for the production of the compounds of the present invention.

In Tables 1 to 3, No. represents Compound Number.

Further, in Tables 1 and 2, Me represents a methyl group, Et an ethyl group, n-Pr a n-propyl group, i-Pr an isopropyl group, t-Bu a tert-butyl group, n-Oct a n-octyl group, n-Dode a n-dodecyl group, and Ph a phenyl group.

Further, in Tables 1 and 2, Ph (2-Cl) represents a phenyl group having a chlorine atom substituted at the 2- position, Ph (4-Ph (4-CF3) ) a phenyl group having a phenyl group (this phenyl group has a CF3 group substituted at the 4-position) substituted at the 4-position, and Ph (4- 0-2-pyridyl (5-CF3) ) a phenyl group having a 2-pyridyloxy group (this pyridyl group has a CF3 group substituted at the 5-position) substituted at the 4-position. The same applies to other similar descriptions.

Table 1 Physical No. X1 x2 Y n A G B Q property (mp : °C) 1-1 F F Me O O H O Ph 1-2 F F Me 0 O H O Ph (2-Cl) 1-3 F F Et 0 O H O Ph 1-4 F F Et 0 O H O Ph (2-Cl) 1-5 F F Me 1 O H O Ph 1-6 F F Me 1 O H 0 Ph (2-Cl) 1-7 F F Me 1 O H 0 Ph (2-Me) 1-8 F F Me 1 O H 0 Ph (4-Cl) 1-9 F F Me 1 O H O CH20Ph 1-10 F F Me 1 O H O CH20Ph (4-Cl) 1-11 F F Me 1 O H 0 CH2SPh 1-12 F F Me 1 O H 0 CH2SPh (4-Cl) 1-13 F F Me 1 O H O CH2SO2Ph 1-14 F F Et 1 O H O Ph Non- crystalline 1-15 F F Et 1 O H O Ph (2-Cl) 81-87 1-16 F F Et 1. 0 H O Ph (2-Me) 83-84 1-17 F F Et 1 O H O Ph (4-Cl) 93-95 1-18 F F Et 1 O H O Ph (2, 6-C12) 1-19 F F Et 1 O H O Ph (2, 4-Cl2) 1-20 F F Et 1 O H O Ph (2, 4, 6-Cl3) 1-21 F F Et 1 O H O CH20Ph oi ly 1-22 F F Et 1 O H O CH2OPh (4-Cl) 1-23 F F Et 1 O H O CH2SPh 1-24 F F Et 1 O H O CH2SPh (4-Cl) 1-25 F F Et 1 O H O CH2S02Ph 1-26 F F Me 2 O H O Ph 78-79 1-27 F F Me 2 O H O Ph (2-Cl) 94-95 1-28 F F Me 2 O H O Ph (2-Me) 80-81 1-29 F F Me 2 O H O Ph (4-Cl) 113-114. 5 1-30 F F Me 2 O H O Ph (2, 6-C12) 1-31 F F Me 2 O H O Ph (2, 4-Cl2) 1-32 F F Me 2 O H O Ph (2, 4, 6-Cl3) 1-33 F F Me 2 O CH2Ph O Ph 1-34 F F Me 2 O CH2Ph 0Ph (2-Cl) 1-35 F F Me 2 O CH2Ph O Ph (2-Me) Table 1 (continued) Physical No. X1 x2 Y n A G B Q property (mp : °C) 1-36 F F Me 2 O CH2Ph O Ph (4-Cl) 1-37 F F Me 2 0 CH2Ph O Ph (2, 6-Cl2) 1-38 F F Me 2 O CH2Ph O Ph (2, 4-Cl2) 1-39 F F Me 2 O CH2Ph O Ph (2, 4, 6-Cl3) 1-40 F F Me 2 O H O CH2OPh 1-41 F F Me 2 O H 0 CH20Ph (4-Cl) 1-42 F F Me 2 O H 0 CH2SPh 1-43 F F Me 2 O H O CH2SPh (4-Cl) 1-44 F F Me 2 O H O CH2S02Ph 1-45 F F Et 2 O H O Ph 63-64 1-46 F F Et 2 O H O Ph (2-C1) 68-87 1-47 F F Et 2 O H O Ph (3-C1) 75-82 1-48 F F Et 2 O H0 Ph (4-Cl) 65-84 1-49 F F Et 2 O H O Ph (2-Me) 30-70 1-50 F F Et 2 O H O Ph (3-Me) 53-56 1-51 F F Et 2 O H O Ph (4-Me) 63-67 1-52 F F Et 2 O H O Ph (4-OMe) 46-75 1-53 F F Et 2 O H O Ph (4-Et) 30-47 1-54 F F Et 2 O H O Ph (4-t-Bu) 36-66 1-55 F F Et 2 O H O Ph (2-CF3) Non- crystalline 1-56 F F Et 2 O H O Ph (2-CO2Et) 1-57 F F Et 2 O H O Ph (4-SMe) 1-58 F F Et 2 O H O Ph (2-N02) Oily 1-59 F F Et 2 O H O Ph (2-CN) 1-60 F F Et 2 O H O Ph (2, 6-Cl2) 99-101 1-61 F F Et 2 O H O Ph (2, 4-Cl2) 37-45 1-62 F F Et 2 O H O Ph (3, 5-C12) 1-63 F F Et 2 0 H O Ph (2, 4, 6-C13) 1-64 F F Et 2 O H O 2-Pyridyl Oily 1-65 F F Et 2 O H O 3-Pyridyl Oily 1-66 F F Et 2 O H O 4-Pyridyl 40-45 1-67 F F Et 2 O H O 2-Thienyl 75-78 1-68 F F Et 2 O H O 3-Isoxazolyl 1-69 F F Et 2 O H O 5-Isoxazolyl 1-70 F F Et 2 O H O 2-Thiazolyl 1-71 F F Et 2 O H 0 1, 3- (Me) 2-5- pyrazolyl 1-72 F F Et 2 O H O 2-Pyrimidinyl Table 1 (continued) Physical No. xi Z2 Y n A G B Q property (mp : °C) 1-73 F F Et 2 O H O 2-Pyrazinyl Oily 1-74 F F Et 2 O H O 2-Quinolyl 1-75 F F Et 2 10 H 0 Me 1-76 F F Et 2 O H O Et 1-77 F F Et 2 O H O n-Pr 1-78 F F Et 2 O H O i-Pr 1-79 F F Et 2 O H O t-Bu 1-80 F F Et 2 H0CH2CH2CH20Et 1-81 F F Et 2 O H 0 CH2CH=CH2 1-82 F F Et 2 O H 0 CH=CH2 1-83 F F Et 2 O H O CH2C-CH 1-84 F F Et 2 O H O Cyclopropyl 1-85 F F Et 2 O H O Cyclohexyl 1-86 F F Et 2 O H O 1-Naphthyl 119-126 1-87 F F Et 2 O H O Ph (4-OPh) Ph (4-Ph (4- 1-88 F F Et 2 O H O Ph (4-Ph (4- 1-89 F F Et 2 O H O Ph (4-Ph) 1-90 F F Et 2 O H O CH2OPh 64-65 1-91 F F Et 2 O H O CH2SPh 69-72 1-92 F F Et 2 O H O CH2SOPh 1-93 F F Et 2 O H O CH2So2Ph 1-94 F F Et 2 O H O CHMeOPh 73-74 1-95 F F Et 2 0 H 0 CMe20Ph 1-96 F F Et 2 O H O CH2CH2OPh 1-97 F F Et 2 O H O CH20Ph (2-Cl) Oily 1-98 F F Et 2 O H O CH20Ph (3-Cl) Oily 1-99 F F Et 2 O H O CH20Ph (4-Cl) 38-53. 5 1-100 F F Et 2 O H O CHOPh (2-Me) Oily 1-101 F F Et 2 O H 0 CH20Ph (3-Me) 58-59 1-102 F F Et 2 O H O CH2OPh (4-Me) 53-54 1-103 F F Et 2 O H 0 CH2SPh (2-Cl) 1-104 F F Et 2 O H O CH2SPh (4-Cl) 1-105 F F Me 3 O H O Ph 1-106 F F Me 3 0 H 0 Ph (2-Cl) 1-107 F F Me 3 O H O Ph (2-Me) 1-108 F F Me 3 O H O Ph (4-Cl) 1-109 F F Me 3 O H O CH2OPh 1-110 F F Me 3 O H O CH20Ph (4-Cl) Table 1 (continued) Physical No. X1 x2 Y n A G B Q property (mp : °C) 1-111 F F Me 3 O H O CH2SPh 1-112 F F Me 3 0 H O CH2SPh (4-Cl) 1-113 F F Me 3 0 H O CH2SO2Ph 1-114 F F Et 3 O H O Ph Oily 1-115 F F Et 3 O H O Ph (2-Cl) <73 1-116 F F Et 3 0 H O Ph (2-Me) None- crystalline 1-117 F F Et 3 O H O Ph (4-Cl) <98 1-118 F F Et 3 O H O CH2OPh 1-119 F F Et 3 O H. O CH20Ph (4-C1) 1-120 F F Et 3 O H 0 CH2SPh 1-121 F F Et 3 O H O CH2SPh (4-C1) 1-122 F F Et 3 O H 0 CH2SO2Ph 1-123 F F Me 4 O H O Ph 1-124 F F Me 4 O H O Ph (2-Cl) 1-125 F F Me 4 O H O Ph (2-Me) 1-126 F F Me 4 O H O Ph (4-C1) 1-127 F F Me 4 O H O CH2OPh 1-128 F F Me 4 O H0CH2SPh (4-C1) 1-129 F F Et 4 O H O Ph 1-130 F F Et 4 O H O Ph (2-Cl) 1-131 F F Et 4 O H O Ph (2-Me) 1-132 F F Et 4 O H O Ph (4-C1) 1-133 F F Et 4 O H O CH20Ph 1-134 F F Et 4 O H O CH2SPh (4-Cl) 1-135 F F Me 5 O H O Ph 1-136 F F Me 5 O H O Ph (2-Cl) 1-137 F F Me 5 O H O Ph (2-Me) 1-138 F F Me 5 O H O Ph (4-C1) 1-139 F F Me 5 O H O CH2OPh 1-140 F F Me 5 O H O CH2SPh (4-Cl) 1-141 F F Et 5 O H0 Ph 1-142 F F Et 5 O H O Ph (2-C1) 1-143 F F Et 5 O H O Ph (2-Me) 1-144 F F Et 5 O H O Ph (4-C1) 1-145 F F Et 5 O H O CH2OPh 1-146 F F Et 5 0 H O CH2SPh (4-Cl) 1-147 F F Et 2 0 Me O Ph Oily 1-148 F F Et 2 0 CH2CH2Cl O Ph Table 1 (continued) Physical No. xi x2 Y n A G B Q property (mp : C) 1-149 F F Et 2 0 CH=CH2 0 Ph 1-150 F F Et 2 O CH=CHPh O Ph 1-151 F F Et 2 O CH-CCl2 O Ph 1-152 FFEt 2 0 CH2C==CH 0 Ph 1-153 FF Et 2 0 CH : 2C==CI 0 Ph 1-154 FFEt 2 0 CH2C=CPh 0 Ph 1-152 F F Et 2 O CH2C-CH O Ph 1-153 F F Et 2 O CH2C=CI O Ph 1-154 F Cl Et 2 O H0Ph I-IS5 F Cl Et 2 0 H 0 Ph 1-156 Cl Cl Et 2 O H O Ph 1-156 Cl C1 Et 2 O H O Ph 1-157 Br Br Et 2 O H 0 Ph 1-158 F F Et 2 S H S Ph 1-159 F F Et 2 S H S Ph (2-Cl) 1-160 F F Et 2 O H s Ph 1-161 F F Et 2 O H S Ph (2-Cl) 1-162 F F Et 2 S H O Ph 1-163 F F Et 2 S H O Ph (2-C1) 1-164 F F CH2C1 2 O H O Ph 1-165 F F CF3 2 O H0 Ph 1-166 F F Ph 2 O H O Ph 1-167 F F Et 2 O H 0 Pyridazinyl Pyridazinyl 1-168 F F Et 1 O H O Ph (4-Me) 75-77 1-169 F F Et 2 O H0Ph (2, 4-F2) 92-94 in- 1-170 F F Et 2 O H O Ph (4-Br) 105- 106. 5 Non- 1-171 F F Et 2 O H O Ph (2-I) crystal- line 1-172 F F Et 2 O H 0 Ph (4-I) 75-114 1-173 F F Et 2 O H0 Ph (2-SMe) 78-82 1-174 F F Et 2 O H0 Ph (4-OPh) 84-86 1-175 F F Et 2 O H0 Ph (2-F) Oily 1-176 F F Et 2 O H 0 Ph (2-Br) 83-88 1-177 F F Et 3 O H 0 Ph (4-Me) 37-58. 5 1-178 F F Et 2 O H 0 CH20Ph (2-F) Oily QQ E 1-179 F F Et 2 O H 0 CH2N (Me) Ph go8. 55~ 90. 5 Table 1 (continued) Physical No. Xl x2 Y n A G B Q property (mp : °C) 1-180 F F Et 2 0 CO (CH2) 5C (Et) = O Ph Oily Cru TTT"p Y'o"ph LFz 1-181 F F Et 2 O CO (CH2) 5C (Et) = O Ph CF2 1-182 F F Et 2 O CO (CH2) 5C (Et) = O Ph (2-Cl) L-Fg 2 1-183 F F Et 2 O CF O Ph (2-Me) CO (CH2) SC (Et) _ ' (Et) = I CF2 CO (CH) 5C (Et) _ 1-185 F F Et 2 O CF O CHOPh CF2 phf4- 1-186 F F Et 2 O H 0 Ph (4- Sites) Phf4- 1-187 F F Et 2 O H. 0 Ph (4- C02Me) Ph (4-COZ- 1-188 F F Et 2 O H 0 Ph (4-CO2- t-Bu) 1-189 F F Et 2 O H O ph't 2 CONMez) 1-190 F F Et 2 O H O Ph (4-Ph) Phf4- 1-191 F F Et 2 O H 0 Ph (4- Oh (4- Phf4- 1-192 F F Et 2 0 O CF (CF3) 2) 1-193 F F Et 2 O H O Ph (4- I I CH=CH2) 1-194 F F Et 2 O H 0 Ph (4-C CH) 1-195 F F Et 2 O H O Ph (2-i-Pr) 1-196 F F Et 2 0 H 0 pht4- CHZOPh) 1-197 F F Et 2 O H O Ph (4- OCH Ph) Ph (4- 1-198 F F Et 2 0 H O OSi (t- Bu) Me2) 1-199 F F Et 2 0 H O Ph (4-OH) 1-200 F F Et 2 0 H O Ph (4-NMe2) 65-94 1-201 F F Et 2 0 H O Ph (4-SCF3) 1-202 F F Et 2 0 H O Ph (2-COMe) Table 1 (continued) Physical No. Xz X2 Y n A G B Q property (mp : °C) 1-203 F F Et 2 O H O Ph (4-CO-t-Bu) 1-204 F F Et 2 O H O CH2-cyclopropyl 1-205 F F Et 2 O H p CHtMe)- cyclopropyl 1-206 F F Me 2 O H O Ph (4-Br) 1-207 F F Me 2 O H O Ph (4-Me) 93-94 1-208 F F Me 2 O H O Ph (2-Br) 1-209 F F Et 2 O H O Ph (4-Br) 1-210 F F Et 2 O H O Ph (2-Br) Ph (4-O- 1-211 F F Et 2 O H 0 'O' _ _ cyclopropyl) 1-212 F F Et 2 O H O Ph (4-SCH2CH2Cl) 1-213 F F Et 2 O H O Ph (4-SOCH2CH2OPh) 1-214 F F Et 2 O H 0Ph (4- S02CH2CH2OPh) 1-215 F F Et 2 O H O Ph (4-OCH2CH2OPh) 1-216 F F Et 2 O H 0Ph ph4- I IOCH2CH2OPh (2-F) 1-217 F F Et 2 O H O Ph (4-OCH2C=CMe) 1-218 F F Et 2 O H O Ph (4-OCH2CH2OEt) 1-219 F F Et 2 O H O CH2CH2OMe 1-220 F F Et 2 O H O CH2CH2COMe Ph (4-0-2- 1-221 F F Et 2 O H oPh (4-0-2- pyridyl) 1-222 F F Et 2 O H O Ph (4-COPh) 1-223 F F Et 2 O H O Ph (4-COSMe) 1-224 F F Et 2 O H O Ph (4-coMMe2) 1-225 F F Et 2 O H O Ph (4-C (=NOMe) Me) CHZCHZCOCH2- I cyclohexyl cyclohexyl 1-227 F F Et 2 0 H O CH2CH2COCH2Ph 1-228 F F Et 2 O H O Ph (4-CH2CH2OEt) Phf4- 1-229 F F Et 2 O 10 Ph (4- CH2CH20CH2Ph) 1-230 F F Et 2 0 H O CH2CH2NMe2 1-231 F F Et 2 O H O CH2CH2N (Me) CH2CH2 _ SHe 1-232 F F Et 2 O H O CH2CH2COMMe2 1-233 F F Et 2 0 H O Ph (4-CH2SMe) 1-234 F F Et 2 0 H O Ph (4-CH2SH) 1-235 F F Et 2 0 H O Ph (4-CH2NMe2) Table 1 (continued) Physical No. X1 x2 Y n A G B Q property (mp : °C) 1-236 F F Et 2 0 H O Ph (4-CH2COEt) 1-237 F F Et 2 O H O Ph (4-CH2CO2Me) 1-238 F F Et 2 O H O Ph (4-CH2COS-i-Pr) 1-239 F F Et 2 O H O Ph (4-CH2CSOMe) 1-240 F F Et 2 O H O Ph (4-CH2CS2Ph) 1-241 FFEt 20H0 Ph (4-CH2SO2NMe2) 1-242 FFEt 20H0 Ph (4-CH2CONMe2) 1-243 FFEt 20H0 Ph (4-CH2CSNMe2) 1-244 F F Et 2 O H O Ph (4- CHEZ C (=NOMe) Me) 1-245 F F Et 2 O H O Ph (4-CH2NHCOMe) Ph (4- 1-246 F F Et 2 O H 0ph (4- CHAN (Me) Camez 1-247 F F Et 2 O H O Ph (4-CH2NHSO2Me) 1-248 F F Et 2 O H O Ph (4-CH2SOMe) 1-249 F F Et 2 O H O Ph (4-CH2SO2Me) 1-250 F F Et 2 O H O Ph (2-CH2CSMe) 1-251 F F Et 2 O H O Ph (4-OCOMe) 1-252 F F Et 2 O H O Ph (4-OCSMe) 1-253 F F Et 2 O H O Ph (4-SCOCH2CCH) 1-254 F F Et 2 O H O Ph (4-CH20-n-Dode) 1-255 F F Et 2. O H 0 Ph (4- . Ph (4- Ph (4- 1-256 F F Et 2 0 H O CH2SCH2CH2SPh (4- Cl)) 1-257 F F Et 2 O H 0 Ph (4-CH20-2- pyridyl) 1-258 F F Et 2 O H O Ph (4-CSOMe) 1-259 F F Et 2 O H O Ph (4-CS2Ph) 1-260 F F Et 2 O H O Ph (4-SO2NMe2) 1-2 61 F F Et 2 O H O Ph. (4-CSNMe2) 1-262 F F Et 2 O H O Ph (4-OCH2CH2NMe2) Ph (4-. OCHZCHZCOZCH2CHN0z) Ph (4- 1-264 F F Et 2 O H 0 Phi4- OCHCHZCONHCHZCN) 1-265 F F Et 2 O H O Ph (4-N (Me) COMe) 1-266 F F Et 2 O H O Ph (4-N (Me) CO2Me) 1-267 FFEt 20H0 Ph (4-N (Me) COSMe) 1-268 F F Et 2 O H O Ph (4-N (Me) CSOMe) Table 1 (continued) Physical No. X1 x2 Y n A G B Q property (mp : °C) Ph (4- 1-269 F F Et 2 0 H O N (Me) CS2Me) I I I N (Me) CS2Me) 1-270 F F Et 2 O H O Ph (4-CSMe) 1-271 F F Et 2 0 H O Ph (4-OCOMe) 1-272 F F Et 2 0 IH 0 Ph (4-OCSMe) 1-273 F F Et 2 O H O Ph (4-SCO-n-Oct) 1-274 F F Et 2 O H O Ph (4-SCSPh) Ph (4-O-2- 1-275 F F Et 2 O H 0 Ph (4-0-2- pyndyl (5-CF3)) . Ph (4-O-2- 1-276 F F Et 2 O H O pyridyl (3-Cl-5- CF3)) 1-277 F F Et 2 O CONMe2 O Ph 1-278 F F Et 2 O H H 0 Ph (4-CH2Ph (4- N (Me) COMe) ? 1-279 F F Et 2 0 H O Ph (4-OMe) Oily 1-280 F F Et 2 O H O Ph (4-OCF3) Oily Table 2 Physical No. Xi xi Y n A G L property (mp : °C) 2-1 F F Et 2 O H CH2CO2Et oily 2-2 F F Et 2 O H SO2Ph oily 2-3 F F Et 2 O H CO2Ph oily 2-4 F F Et 2 O H CONHPh 76-78 2-5 F F Et 2 O H NHPh 74-78 2-6 F F Et 2 O H NH-2-pyrimidinyl 83-85 2-7 F F Et 2 O H NHCOPh 77-80 2-8 F F Et 2 O H N=CPh2 70-74 2-9 F F Et 3 O H NHCO2Me oily 2-10 F F Et 3 0. H NHSO2Ph 78-80 2-11 F F Et 2 O H CO2CH2OPh 2-12 F F Et 2 O H COSPh 2-13 F F Et 2 O H CSOPh 2-14 F F Et 2 S H CONHPh 2-15 F F Et 2 O H NHPh (2-Cl) 2-16 F F Et 2 O H NHPh (4-Cl) 2-17 F F Et 2 O H NHPh (2-Me) 2-18 F F Et 2 0 H NHPh (4-Me) 2-19 F F Et 2 O H NHCOPh (2-Cl) 2-20 F F Et 2 O H NHCOPh (4-Cl) 2-21 F F Et 2 O H NHCOPh (2-Me) 2-22 F F Et 2 S H NHCOPh (4-Me) 2-23 F F Et 2 O H N=C (Me) Ph 2-24 F F Et 2 O H NHCO2Ph 2-25 F F Et 2 O H NHCO2Ph (2-Cl) 2-26 F F Et 2 O H NHCO2Ph (4-Cl) 2-27 F F Et 2 S H NHCO2Ph (2-Me) 2-28 F F Et 2 O H NHCO2Ph (4-Me) 2-29 F F Et 2 O H CSNHPh 2-30 F F Et 2 O H CO2-t-Bu 2-31 F F Et 2 0 H CH2CO2-t-Bu 2-32 F F Et 2 O H CO2Ph (4-Cl) 2-33 F F Et 2 O H CO2Ph (4-Me) Table 2 (continued) Physical No. xI X2 Y n A G L property (mp : °C) 2-34 F F Et 2 O H CO2Ph (2-Cl) 2-35 F F Et 2 O H CO2Ph (2-Me) 2-36 F F Et 2 O H N=CHPh (4-Cl) 2-37 F F Et 2 O H S02NMe2 2-38 F F Et 2 O H CH2CH2CON (Me) Ph 2-39 F F Et 2 O H CH2CH2CONMe2 2-40 F F Et 2 O H CH2CH2SO2Ph 2-41 F F Et 2 O H CH2CH2SO2N (Me) Ph 2-42 F F Et 2 O H CH2CH2SO2NMe2 2-43 F F Et 2 O Me CON (Me) Ph CH2CH2CON (Me) CH2 2-44 F F Et 2 O H CN 2-45 F F Et 2 O S02Me CHzC02Et 2-46 F F Et 2 0 S02NMe2 CHXEt 2-46 F F Et 2 O SO2NMe2 CH2CO2Et 2-47 F F Et 2 O SO2CH2Ph CH2CO2Et 2-48 F F Et 2 O S02PhCH2C02Et 2-49 F F Et 2 0 CH) Ph CH2CO2Et CH) Ph 2-50 F F Et 2 0 S02N (CH2C= CH2co2Et CC 12) Me 2-51 F F Et 2 O CO2Ph CH2CO2Et 2-52 F F Et 2 O. SPh CO2Ph 2-53 F F Et 2 O SN (Me) Ph CO2Ph _ SN (Me) CO- 2-54 F F Et 2 O i_pr COPh 2-55 F F Et 2 0 SN (i- CO2Ph. lPr) C02Me I Table 3 No. 1H-NMR 8ppm (Solvent : CDC13/40OMHz) 1-14 8.68 (lH, brs), 7.83 (2H, d, J=7.6Hz), 7.59 (lH, t, J=7. 2Hz), 7.4 9 (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 (1H, brs), 7. 60 (1H, d, J=8. OHz), 7. 33- 7.44 (3H, m), 2.90 (2H, t, J=7. 4Hz), 1.94- 2.10 (4H, m), 1. 80 (2H, quintet, J=7. 5Hz), 0. 99 (3H, t, J=7.6Hz) 1-16 8.11 (1H, 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, quintet, J=7. 5Hz), 1. 00 (3H, t, J=7.4Hz) 1-17 8. 49 (1H, brs), 7. 76 (2H, td, J=2. 2, 8. 8Hz), 7. 47 (2H, td, J=2.2, 8.8Hz), 2. 96 (2H, t, J=7. 2Hz), 1. 97- 2.10 (4H, m), 1. 80 (2H, quintet, J=7.5Hz), 0. 99 (3H, t, J=7.2Hz) 1-21 8. 78 (1H, brs), 7. 32 (2H, t, J=7. 6Hz), 7. 04 (lH, t, J=7. 2Hz), 6.9 2 (2H, d, J=7.6Hz), 4. 58 (2H, s), 2. 82 (2H, t, J=7.4Hz), 1. 95- 2. 07 (4H, m), 1. 77 (2H, quintet, J=7. 5Hz), 0. 99 (3H, t, J=7.2Hz) 1-26 8. 52 (1H, brs), 7. 82 (2H, d, J=8. 0Hz), 7. 59 (1H, t, J=7.6Hz), 7.4 9 (2H, t, J=7.6Hz), 2. 99 (2H, t, J=7.2Hz), 1. 93- 1. 98 (2H, m), 1. 71 (2H, quintet, J=7. 6Hz), 1. 53 (3H, t, J=3. 2Hz) , 1.33-1. 47 (4H, m) 1-27 8. 37 (1H, brs), 7. 61 (1H, d, J=7.6Hz), 7. 34- 7. 44 (3H, m), 2. 90 (2H, t, J=7.6Hz), 1. 93- 1.98 (2H, m), 1. 71 (2H, quintet, J=7. 3Hz), 1. 53 (3H, t, J=2.8Hz), 1. 32-1.47 (4H, m) 1-28 8.10 (lH, brs), 7.. 36-7.43 (2H, m), 7.23- 7.27 (2H, m), 2. 95 (2H, t, J=7.6Hz), 2.47 (3H, s), 1. 94- 1.98 (2H, m), 1. 71 (2H, quintet, J=7.6Hz), 1. 53 (3H, t, J=3.2Hz), 1.35-1. 47 (4H, m) 1-29 8.55 (lH, brs), 7.77 (2H, td, J=2.4, 8.8Hz), 7.46 (2H, td, J=2.3, 8. 4Hz), 2.97 (2H, t, J=7. 6Hz), 1.93- 1.98 (2H, m), 1. 70 (2H, quintet, J=7.6Hz), 1.53 (3H, t, J=3. OHz), 1.32-1. 47 (4H, m) 1-45 8.77 (lH, brs), 7.84 (2H, d, J=7. 2Hz), 7.58 (1H, t, J=7. 2Hz), 7.4 3 (2H, t, J=7.2Hz), 2.99 (2H, t, J=7.4Hz), 1.93- 1.99 (4H, m), 1. 71 (2H, quintet, J=7. 3Hz), 1.34- 1.46 (4H, m), 0.97 (3H, t, J=7.6Hz) 1-46 8.53 (lH, brs), 7.60 (1H, d, J=7.2Hz), 7.43 (2H, d, J=4. 0Hz), 7.3 3-7. 38 (lH, m), 2.89 (2H, t, J=7. 4Hz), 1.92- 1.99 (4H, m), 1.70 (2H, quintet, J=7. 3Hz), 1.32- 1.45 (4H, m), 0.97 (3H, t, J=7.6Hz) 1-47 9.16 (1H, brs), 7.90 (1H, t, J=2. 0Hz), 7. 76 (lH, d, J=8. 0Hz), 7.5 6 (lH, d, J=8. 0Hz), 7.42 (1H, t, J=8. 0Hz), 2.98 (2H, t, J=7.6Hz), 1.93-1. 98 (4H, m), 1.71 (2H, quintet, J=7. 3Hz), 1.32- 1.45 (4H, m), 0.97 (3H, t, J=7. 6Hz) Table 3 (continued) No. 1H-NMR # ppm (Solvent : CDCl3 / 400MHz) 1-48 9.18 (lH, brs), 7.84 (2H, d, J=8. 8Hz), 7.45 (2H, d, J=8.4Hz), 2.9 7 (2H, t, J=7.4Hz), 1. 93- 1.99 (4H, m), 1. 69 (2H, quintet, J=7. 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 (lH, brs), 7.64 (lH, s), 7.61 (lH, d, J=7.6Hz), 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=7.2Hz) 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, m), 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), 2.9 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), 1.29- 1. 40 (4H, m), 1.19 (3H, t, J=7. 6Hz), 0.92 (3H, t, J=7.6Hz) 1-54 8.86 (lH, brs), 7.79 (2H, d, J=8. 4Hz), 7.48 (2H, d, J=8. 4Hz), 2. 9 8 (2H, 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 (lH, brs), 8.19 (lH, dd, J=8.2, 1. (0Hz), 7.72 (lH, td, J=7. 6, 1. 4Hz), 7.62 (lH, td, J=7. 8,1. 6Hz), 7.43 (lH, dd, J=7.6, 1.2Hz) , 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, t, J=7. 2Hz) 1-60 8.68 (lH, brs), 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 (3H, t, J=7.4Hz) 1-61 8.59 (lH, brs), 7.54 (lH, d, J=8. 4Hz), 7.45 (lH, d, J=2. 0Hz), 7.3 4 (lH, dd, J=8.4, 2. 0Hz), 2.85 (2H, t, J=7. 6Hz), 1.92- 1.99 (4H, m), 1.68 (2H, quintet, J=7. 3Hz), 1.32- 1.45 (4H, m), 0.97 (3H, t, J=7.6Hz) Table 3 (continued) No. 1H-NMR # ppm (Solvent : CDCl3 / 400MHz) 1-64 10.45 (lH, brs), 8. 59 (lH, d, J=4. 0Hz), 8.23 (1H, d, J=7.6Hz), 7. 90 (lH, td, J=7.7, 1. 6Hz), 7.50- 7.53 (lH, m), 2.95 (2H, t, J=7.6Hz), 1.92- 1.99 (4H, m), 1. 72 (2H, quintet, J=7.5Hz), 1.33- 1.45 (4H, m), 0. 96 (3H, t, J=7.2Hz) 1-65 9.71 (1H, brs), 9.13 (lH, s), 8.78 (lH, d, J=4. 0Hz), 8.24 (1H, td, J=2.0, 8. 0Hz), 7.43 (1H, dd, J=8.0, 4.8Hz), 2.96 (2H, t, J=8. OHz ), 1.91-1. 96 (4H, m), 1.68 (2H, quintet, J=7.3Hz), 1. 31- 1.43 (4H, m), 0. 95 (3H, t, J=7.6Hz) 1-66 9.13 (lH, brs), 8.82 (2H, d, J=4. 4Hz), 7.74 (2H, d, J=6. OHz), 2.9 6 (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 (lH, dd, J=4.8, 0.8Hz), 7.62 (lH, dd, J=3.8, 0.8Hz), 7.13 (1H, dd, J=4.8, 3.8Hz), 2.96 (2H, t, J=7.6Hz), 1.93 - 1. 99 (4H, m), 1. 70 (2H, quintet, J=7. 4Hz), 1. 32- 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 (1H, dd, J=2.4, 1. 6Hz), 2. 95 (2H, t, J=7. 4Hz), 1.92- 1. 98 (4H, m), 1. 71 (2H, quintet, 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. OHz), 8. 00 (lH, d, J=8. 0Hz), 7.9 0 (1H, d, J=8. 0Hz), 7. 70 (1H, d, J=7. 6Hz), 7. 53- 7.60 (2H, m), 7.49 (1H, t, J=7.8Hz), 3.04 (2H, t, J=7.4Hz), 1.95- 2.01 (4H, m, 1. 76 (2H, quintet, J=7. 3Hz), 1.38- 1.47 (4H, m), 0.98 (3H, 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, J=7.6Hz), 4.59 (2H, s), 2.82 (2H, t, J=7. 2Hz), 1.92- 1.99 (4H, m), 1.67 (2H, quintet, J=7. 5Hz), 1.30- 1.44 (4H, m), 0.97 (3H, t, J=7. 6Hz) 1-91 8.89 (1H, 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 (1H, brs), 7. 30 (2H, t, J=8. 0Hz), 7.03 (1H, t, J=7.6Hz), 6.8 8 (2H, d, J=7. 6Hz), 4.72 (1H, q, J=6. 9Hz), 2.82 (2H, t, J=7.6Hz), 1.92-1. 98 (4H, m), 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 (lH, dd, J=8.0, 1. 6Hz), 7.22 (lH, td, J=8.4, 1. 2Hz), 6.99 (lH, td, J=7.8, 1. OHz), 6.87 (lH, dd, J=8. 2,1. OHz) , 4.64 (2H, s), 2.77 (2H, t, J=7. 6Hz) 1.92- 1. 98 (4H, m), 1.67 (2H, quintet, J=7. 5Hz), 1. 30- 1.44 (4H, m), 0.96 (3H, t, J=7.6Hz) Table 3 (continued) No. 1H-NMR 6ppm (Solvent : CDC13/400MHz) 1-98 8.76 (lH, brs), 7.23 (lH, t, J=8.2Hz), 7.02 (lH, td, J=0.8, 8. OHz ), 6.93 (lH, t, J=2.2Hz), 6.81 (lH, dd, J=8.0, 2. 2Hz), 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=7.6Hz) 1-99 8.70 (lH, brs), 7.27 (2H, d, J=8.8Hz), 6. 85 (2H, d, J=8.8Hz), 4.6 0 (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), 7.19 (1H, t, J=7. 8Hz), 6.85 (lH, d, J=7.6Hz), 6.7 2 (2H, t, J=7.6Hz), 4. 56 (2H, s), 2.82 (2H, t, 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- 1.99 (4H, m), 1.66 (2H, quintet, J=7.5Hz), 1.30- 1. 44 (4H, m), 0.97 (3H, t, J=7.4Hz) 1-114 8.78 (lH, brs), 7.84 (2H, d, J=7.2Hz), 7.58 (lH, t, J=7.4Hz), 7.4 8 (2H, t, J=7. 6Hz), 2.98 (2H, t, J=7. 2Hz), 1. 91- 1.99 (4H, m), 1. 69 (2H, quintet, J=7.3H), 1.23- 1. 42 (8H, m), 0.96 (3H, t, J=7. 2Hz) 1-115 8.42 (lH, brs), 7.60 (lH, d, J=7.6Hz), 7.42-7. 44 (2H, m), 7.34- 7. 38 (lH, m), 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), 2.9 6 (2H, t, J=7.4Hz), 1.90- 1. 98 (4H, m), 1. 68 (2H, quintet, J=7. 1Hz), 1. 24- 1.41 (8H, m), 0. 96 (3H, t, J=7.4Hz) 1-147 7. 58 (2H, d, J=7.2Hz), 7. 53 (1H, t, J=8. 4Hz), 7.44 (2H, t, J=7.2H z), 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) Table 3 (continued) No. 1H-NMR 5ppm (Solvent : CDCl3/400MHz) 1-168 8.49 (lH, brs), 7.71 (2H, d, J=8. 4Hz), 7.28 (2H, d, J=7.6Hz), 2.9 8 (2H, t, J=7.4Hz), 2.39 (3H, s), 1.97- 2.10 (4H, m), 1.80 (2H, quintet, J=7.5Hz), 0.99 (3H, t, J=7.6Hz) 1-169 8.39 (lH, brs), 7.40- 7.47 (lH, m), 6.98 (2H, t, J=8.2Hz), 2.83 (2H, t, J=7. 6Hz), 1.92- 1.99 (4H, m), 1. 68 (2H, quintet, J=7.3Hz), 1.32- 1. 45 (4H, m), 0.97 (3H, t, J=7.6Hz) 1-170 8.80 (lH, brs), 7.73 (2H, d, J=8.8Hz), 7.62 (2H, d, J=8.8Hz), 2.9 7 (2H, t, J=7.4Hz), 1. 92- 1.99 (4H, m), 1.70 (2H, quintet, J=7.5Hz), 1.33- 1. 45 (4H, m), 0.97 (3H, t, J=7.4Hz) 1-171 8.22 (lH, brs), 7.89 (lH, d, J=8. 0Hz), 7.39-7. 42 (2H, m), 7. 13- 7. 18 (lH, m), 2.89 (2H, t, J=7.4Hz), 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), 2.9 6 (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 (lH, brs), 7.57 (lH, dd, J=7.6, 1.6Hz), 7.46 (lH, td, J=8.0, 1. 6Hz), 7.34 (lH, d, J=7.2Hz), 7.22 (lH, t, J=8. OHz), 2.95 (2H, t , J=7.4Hz), 2.47 (3H, s), 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 (lH, brs), 7. 80 (2H, d, J=8.8Hz), 7.39 (2H, t, J=8. 0Hz), 7.2 0 (lH, t, J=7.6Hz), 7. 00- 7.07 (4H, m), 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) 1-175 8.87 (lH, brd, J=13.2Hz), 8.03 (lH, td, J=7.7, 2. 0Hz), 7.53- 7.59 (lH, m), 7.30 (lH, td, J=7.4, 0. 8Hz), 7.17 (lH, dd, J=12.0, 8 . 4Hz), 2.94 (2H, t, J=7. 8Hz), 1.93- 1.99 (4H, m), 1.71 (2H, quintet, J=7.5Hz), 1.34- 1.46 (4H, m), 0.97 (3H, t, J=7.6Hz) 1-176 8.33 (lH, brs), 7.62 (lH, dd, J=8. 0, 0.8Hz), 7.50 (lH, 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), 1.34- 1. 45 (4H, m), 0.97 (3H, t, J=7. 4Hz) 1-177 8.58 (lH, brs), 7.72 (2H, d, J=8. OHz), 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) Table 3 (continued) No. 1H-NMR §ppm (Solvent : CDC13/400MHz) 1-178 8.82 (lH, brs), 6.93- 7.15 (4H, m), 4.65 (2H, s), 2.79 (2H, t, J=7.2Hz), 1.92- 1.99 (4H, m), 1. 67 (2H, quintet, J=7.4Hz), 1.31- 1.43 (4H, m), 0.97 (3H, t, J=7. 4Hz) 1-179 9.00 (lH, brs), 7.29 (2H, t, J=7. 6Hz), 6.93 (lH, t, J=7.4Hz), 6.8 3 (2H, d, J=8. 0Hz), 4.02 (2H, s), 3.04 (3H, s), 2.78 (2H, t, J=8. OH z), 1.93-1. 99 (4H, m), 1.63 (2H, quintet, J=7. 4Hz), 1.28- 1. 43 (4H, m), 0.97 (3H, t, J=7. 6Hz) 1-180 7.86 (lH, td, J=7.8, 2. 0Hz), 7.53- 7.59 (lH, m), 7.27 (lH, td, J=7.6, 1.2Hz), 7.09 (lH, dd, J=11. 2,8 . 4Hz), 2. 65 (4H, t, J=7. 2Hz), 1.92- 1.97 (8H, m), 1, 65 (4H, 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, quintet, J=7.4Hz), 1.34- 1. 45 (4H, m), 0.96 (3H, t, J=7.6Hz) 1-207 8.51 (lH, brs), 7. 71 (2H, d, J=8. 4Hz), 7.28 (2H, d, J=8. 0Hz), 2.9 8 (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) 1-279 10.17 (lH, brs), 8. 13 (lH, dd, J=8.0, 2. OHz), 7.51 (lH, td, J=8.0 , 2. 0Hz), 7.08 (1H, td, 8.0, 0.8Hz), 6. 99 (lH, 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 8.66 (1H, brs), 7.88 (1H, dd, J=7.6, 2. 0Hz), 7.58 (lH, td, J=7.8, 2. 0Hz), 7.43 (lH, t, J=7.8Hz), 7.33 (lH, d, J=8. 0Hz), 2.89 (2H, t , J=7.4Hz), 1.93- 1.99 (4H, m), 1. 70 (2H, quintet, J=7.3Hz), 1.34- 1.45 (4H, m), 0.97 (3H, t, J=7.4Hz) 2-1 5.93 (lH, brs), 4.20 (2H, q, J=7. lHz), 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 (lH, brs), 8.05 (2H, d, J=6. 8Hz), 7.64 (lH, t, J=7.2Hz), 7.5 4 (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, m), 0.92 (3H, t, J=7.6Hz) 2-3 7.36 (2H, t, J=7.8Hz), 7.21 (lH, t, J=7.2Hz), 7.06 (2H, d, J=7.6H z), 2.54 (2H, t, J=7.2Hz), 1.94- 2.01 (4H, m), 1.75 (2H, quintet, J=7.5Hz), 1.35- 1.48 (4H, m), 0.98 (3H, t, J=7.6Hz) Table 3 (continued) No. 1H-NMR 6ppm (Solvent : CDC13/400MHz) 2-4 10. 68 (lH, s), 10.03 (lH, brs), 7.51 (2H, d, J=8. 0Hz), 7.31 (2H, t , J=8. 0Hz), 7. 11 (1FI, t, J=7. 6Hz), 2.43 (2H, t, J=7. 4Hz), 1. 92- 1.98 (4H, m), 1.72 (2H, quintet, J=7. 6Hz), 1.32- 1.44 (4H, m), 0.95 (3H, t, J=7. 6Hz) 2-5 8.08 (lH, brs), 7.09 (2H, t, J=7.2Hz), 6.81 (lH, t, J=7.2Hz), 6. 6 5 (2H, d, J=8. OHz), 6.19 (lH, brs), 2.05 (2H, t, J=7.6Hz), 1.84-1. 89 (4H, m), 1.47-1. 55 (2H, m), 1.17- 1. 27 (4H, m), 0.90 (3H, t, J=7.6Hz) 2-6 8.37 (2H, d, J=4. 8Hz), 7.62 (lH, brs), 7.14 (1H, brs), 6. 75 (lH, t, J=4.8Hz), 2.29 (2H, t, J=7.6Hz), 1. 91- 1.99 (4H, m), 1.66-1. 73 (2H, m), 1. 31- 1.42 (4H, m), 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 , J=7.2Hz), 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 (4H, d, J=7. 2Hz), 7. 32-7. 36 (4H, m), 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 (1H, 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 Test on southern root-knot nematode (Meloidogyne incognita) To 200 ml of the soil contaminated by southern root- knot nematode, 10 ml of a chemical solution having the concentration of the compound of the present invention adjusted to be 800 ppm, was poured, followed by mixing so that the compound was uniformly dispersed. The treated

soil was put into a pot (diameter: 8 cm, height: 9 cm), and then a tomato seedling in 2-leaf stage was transplanted and placed in a greenhouse. After six weeks from the transplantation of the tomato, the root knot index was determined based on the following standards of Table 4. Such determination was made with respect to the above-mentioned Compound Nos. 1-51,2-1, 2-3,2-4, 2-6 and 2-9, whereby all compounds showed high controlling effects at a level of a root knot index of not more than 1.

Table 4 Degree of formation of root Root knot index knots 0 No knot was formed Knots were formed to a slight degree Knots were formed to a moderate degree Knots were formed to a heavy degree Knots were formed to the heaviest degree TEST EXAMPLE 2 Miticidal test against two-spotted spider mite (Tetranychus urticae) A miticidal solution was prepared to bring the concentration of a compound of the present invention to 200 ppm. Kidney bean (Phaseolus vulgaris) seedling with only one primary leaf left, was transplanted in a pot (diameter: 8 cm, height: 7 cm) and 20 adults of two-

spotted spider mite (Tetranychus urticae) were inoculated thereto. The adult mites were immersed together with the kidney bean leaf in the above miticidal solution, then dried in air. and left in a constant temperature chamber at 25°C with lightening. On the second or third day after the treatment, dead adult mites were counted, and the mortality was calculated by the following equation.

The adult mites dropped off the leaf were counted as dead adult mites. The mortality was obtained with respect to the above-mentioned Compound Nos. 1-14 to 1-17, 1-21, 1- 26 to 1-29,1-45 to 1-55, 1-58, 1-60, 1-61, 1-64 to 1-67, 1-73,1-86, 1-90,1-91, 1-94,1-97 to 1-102, 1-114 to 1- 117,1-168 to 1-180,1-200, 1-207,1-279, 1-280 and 2-1 to 2-10, whereby all compounds showed high controlling effects with a mortality of at least 80%.

Number of dead adult mites Mortality (%) = x 100 Number of treated adult mites TEST EXAMPLE 3 Insecticidal test against small brown planthopper (Laodelphax striatellus) Rice seedling was dipped in an insecticidal solution prepared to bring the concentration of a compound of the present invention to 200 ppm and then dried in air. Then, the seedling with its root wrapped with a wet absorbent cotton, was put into a test tube. Then, 10 larvae of

small brown planthopper (Laodelphax striatellus) were released therein, and the test tube was covered with a gauze and left in a constant temperature chamber at 25°C with lightening. On the 5th day after the release, dead larvae were counted, and the mortality was calculated by the following equation.

The mortality was obtained with respect to the above-mentioned Compound Nos. 1-14 to 1-17, 1-21, 1-26 to 1-29,1-45 to 1-51,1-53, 1-55, 1-58, 1-60, 1-61, 1-64 to 1-67,1-73, 1-90,1-91, 1-94,1-98 to 1-102, 1-114,1-116, 1-168,1-169, 1-171,1-173, 1-175,1-177, 1-178,1-200, 1-207,1-280 and 2-9, whereby all compounds showed high controlling effects with a mortality of at least 80%.

Number of dead insects Mortality (%) = x 100 Number of released insects TEST EXAMPLE 4 Pesticidal test against New Zealand cattle mite (Haemaphysalis longicornis) In a Petri dish having a diameter of 9 cm, 1 ml of an acetone solution of the compound of the present invention (concentration: 10 ug/ml) is dropped by a micropipette. After the internal surface of the Petri dish dries up, from 60 to 180 infant mites are put, and the Petri dish is covered with a polyethylene sheet and sealed by an elastic band. The number of knocked down mites after contact with the pesticide is observed,

whereby the compound of the present invention knocks down the majority of New Zealand cattle mite.

TEST EXAMPLE 5 Pesticidal test against New Zealand cattle mite (Haemaphysalis longicornis), employing a dog 50 Young mites of New Zealand cattle mite are released on the auricle of a dog (beagle, 8 months old) and artificially parasitized. Upon expiration of two days from parasitizing, the number of parasitized mites is counted, and then the compound of the present invention formulated is spotted on at a dose of 10 mg/kg at the dorsal cervical region. Up to five days after administration of the pesticide, observation is carried out to insect the parasitic number, the fallen number and the mortality of the fallen New Zealand cattle mite.

Here, the dog is individually raised in a cage and permitted to drink tap water freely, and a predetermined amount of a dog food is given once a day. As a result, the compound of the present invention is effective to have the parasitized New Zealand cattle mite fallen or dead.

TEST EXAMPLE 6 Pesticidal test against cat flea, employing a dog 100 non-bloodsucked adults of cat flea (Ctenocephalides felis) within three days after adult emergence are released on the dorsal fur of a dog (beagle, 8 months old) and artificially parasitized, and the

compound of the present invention formulated is spotted on at a dose of 10 mg/kg on the dorsal cervical region.

On the third day after administration of the pesticide, the cat flea. is recovered by means of a flea catching comb, and the parasitized number is counted. Here, the dog is individually raised in a cage and permitted to drink tap water freely, and a predetermined amount of a dog food is given once a day. As a result, the compound of the present invention is effective to control the parasitizing of cat flea.

FORMULATION EXAMPLE 1 (1) Compound of the present invention 20 parts by weight (2) Clay 72 parts by weight (3) Sodium lignin sulfonate 8 parts by weight The above components are uniformly mixed to. obtain a wettable powder.

FORMULATION EXAMPLE 2 (1) Compound of the present invention 5 parts by weight (2) Talc 95 parts by weight The above components are uniformly mixed to obtain a dust.

FORMULATION EXAMPLE 3 (1) Compound of the present invention 20 parts by weight (2) N, N'-dimethylacetamide 20 parts by weight

(3) Polyoxyethylenealkylphenyl ether 10 parts by weight (4) Xylene 50 parts by weight The above components are uniformly mixed and dissolved to obtain an emulsifiable concentrate.

FORMULATION EXAMPLE 4 (1) Clay 68 parts by weight (2) Sodium lignin sulfonate 2 parts by weight (3) Polyoxyethylenealkylaryl sulfate 5 parts by weight (4) Fine silica powder 25 parts by weight A mixture of the above components is mixed with compound of the present invention in a weight ratio of 4: 1 to obtain a wettable powder.

FORMULATION EXAMPLE 5 (1) Compound of the present invention 50 parts by weight (2) Oxylated polyalkylphenyl phosphate-triethanolamine 2 parts by weight (3) Silicone 0.2 part by weight (4) Water 47.8 parts by weight The above components are uniformly mixed and pulverized to obtain a base liquid, and (5) Sodium polycarboxylate 5 parts by weight (6) Anhydrous sodium sulfate 42.8 parts by weight are added, and the mixture is uniformly mixed and dried to obtain water-dispersible granules.

FORMULATION EXAMPLE 6 (1) Compound of the present invention 5 parts by weight (2) Polyoxyethyleneoctylphenyl ether 1 part by weight (3) polyoxyethylene phosphoric acid ester 0.1 part by weight (4) Granular calcium carbonate 93.9 parts by weight The above components (1) to (3) are preliminarily uniformly mixed and diluted with a proper amount of acetone, and then the mixture is sprayed onto the component (4), and acetone is removed to obtain granules.

FORMULATION EXAMPLE 7 (1) Compound of the present invention 2.5 parts by weight (2) N-methyl-2-pyrrolidone 2.5 parts by weight (3) Soybean oil 95.0 parts by weight The above components are uniformly mixed and dissolved to obtain an ultra low volume formulation.

FORMULATION EXAMPLE 8 (1) Compound of the present invention 40 parts by weight (2) Oxylated polyalkylphenylphosphate- triethanolamine 2 parts by weight (3) Silicone 0.2 part by weight (4) Xanthan gum 0.1 part by weight (5) Ethylene glycol 5 parts by weight

(6) Water 52.7 parts by weight The above components are uniformly mixed and pulverized to obtain a water-based suspension concentrate.

FORMULATION EXAMPLE 9 (1) Compound of the present invention 10 parts by weight (2) Diethylene glycol monoethyl ether 90 parts by weight The above components are uniformly mixed to obtain a soluble concentrate.