Background Art Against pests such as insect pests, acarine pests, and nematode pests, various pesticide compositions have been used so far for their control. The conditions of pesticide compositions required have drastically been changed, including the care of their effects on the environment and the acquisition of drug resistance by pests to be controlled. Under such circumstances, there have been great demands for the development of new pesticide compositions.

Disclosure of Invention The present inventors have extensively studied to find compounds having excellent pest controlling activity. As a result, they have found that the malononitrile compounds of formula (X) as depicted below have excellent controlling activity against pests such as insect pests, acarine pests, and nematode pests, thereby reaching the present invention.

That is, the present invention provides a pesticide composition comprising malononitrile compounds of formula (X) :

(hereinafter referred to as compound (s) (X)) wherein R'and R'are the same or different and independently C1-C5 (halo)- alkyl, C1-C5 (halo) alkyloxy, C2-C5 (halo) alkenyl, C2-C5 (halo) alkynyl, hydrogen, or cyano; R3 and R4 are the same or different and independently C1-C10 alkyl, C2-C10 alkenyl, C2-C10 alkynyl, or hydrogen, or R3 and R4 are taken together to form C2-C6 (halo) alkylene or C4-C6 (halo) alkenylene; R5 is halogen, cyano, nitro, C1-C4 (halo) alkyl, C2-C4 (halo) alkenyl, C2- 4 (halo) alkynyl, C1-C4 (halo)alkyloxy, C1-C4 (halo) alkylthio, C,-C, (halo)- alkylsulfinyl, C1-C4 (halo) alkylsulfonyl, C1-C4 (halo) alkylcarbonyl, C1-C4 (halo) alkyloxycarbonyl, C1-C4 (halo) alkylcarbonyloxy, phenyloxy, or phenyl- thio, in which the phenyloxy and phenylthio groups may optionally be sub- stituted with halogen or C1-C3 alkyl ; n is an integer of 0 to 4; R6 is hydrogen, halogen, cyano, nitro, C1-C4 (halo) alkyl, C2-C4 (halo)- alkenyl, C2-C4 (halo) alkynyl, C1-C4 (halo) alkyloxy, C1-C4 (halo) alkylthio, C1-C4 (halo) alkylsulfinyl, C1-C4 (halo) alkylsulfonyl, C1-C4 (halo) alkylcarbonyl, C1-C4 (halo) alkyloxycarbonyl, C1-C4 (halo) alkylcarbonyloxy, phenyloxy, or phenyl- thio, in which the phenyloxy and phenylthio groups may optionally be sub- stituted with halogen or C1-C3 alkyl ; or R'and R'are taken together to form methylenedioxy; with the provisos that when R6 is hydrogen, then n is an integer of 1 to 4 and that when n is 2 or more, then Razzs are the same or different from each other; as an active ingredient.

The present invention also provides use of compounds (X) as active ingredients and pest controlling methods by applying compounds (X) to pests or habitats of pests.

Mode for Carrying Out the Invention In the definition of substituents as used herein, each group has the followingmeaning: The (halo) alkyl group refers to alkyl optionally substituted with halogen for one or more than one hydrogen atoms.

The (halo) alkyloxy group refers to alkyloxy optionally substituted with halogen for one or more than one hydrogen atoms.

The (halo) alkenyl group refers to alkenyl optionally substituted with halogen for one or more than one hydrogen atoms.

The (halo) alkynyl group refers to alkynyl optionally substituted with halogen for one or more than one hydrogen atoms.

The (halo) alkylene group refers to alkylene optionally substituted with halogen for one or more than one hydrogen atoms.

The (halo) alkenylene group refers to alkenylene optionally substi- tuted with halogen for one or more than one hydrogen atoms.

The (halo) alkylthio group refers to alkylthio optionally substituted with halogen for one or more than one hydrogen atoms.

The (halo) alkylsulfinyl group refers to alkylsulfinyl optionally sub- stituted with halogen for one or more than one hydrogen atoms.

The (halo) alkylsulfonyl group refers to alkylsulfonyl optionally sub- stituted with halogen for one or more than one hydrogen atoms.

The (halo) alkylcarbonyl group refers to alkylcarbonyl optionally sub- stituted with halogen for one or more than one hydrogen atoms.

The (halo) alkyloxycarbonyl group refers to alkyloxycarbonyl option-

ally substituted with halogen for one or more than one hydrogen atoms.

The (halo) alkylcarbonyloxy group refers to alkylcarbonyloxy option- ally substituted with halogen for one or more than one hydrogen atoms.

The term"C1-Clo"or the like refers to the number of carbon atoms constituting the alkyl, alkenyl, or alkynyl group in each substituent. For example, C1-C4 (halo) alkylcarbonyl means alkylcarbonyl optionally substi- tuted with halogen for one or more hydrogen atoms wherein the alkyl part is constituted by C1-C4 carbon atoms.

In compounds (X), each group includes specific ones as listed below: The Ci-Cg (halo) alkyl group represented by R'or R'may include methyl, ethyl, propyl, 1-methylethyl, 1, 1-dimethylethyl, 2,2-dimethylpropyl, chloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, 2,2,2-trifluoro- ethyl, and 1,1,2,2-tetrafluoroethyl.

The C1-C5 (halo) alkyloxy group represented by R'or R'may include methoxy, ethoxy, 1-methylethoxy, trifluoromethoxy, difluoromethoxy, 2,2,2- trifluoroethoxy, and 1, 1,2,2-tetrafluoroethoxy.

The C2-C5 (halo) alkenyl group represented by R'or R 2 may include vinyl, 1-propenyl, 2-propenyl, 2,2-difluorovinyl, and 1,2,2-trifluorovinyl.

The C2-C5 (halo) alkynyl group represented by R1 or R2 may include ethynyl, 1-propynyl, 2-propynyl and 3,3,3-trifluoro-1-propynyl.

The C1-C10 alkyl group represented by R3 or R4 may include methyl, ethyl, 1-methylethyl, propyl, 2-methylpropyl, 2,2-dimethylpropyl, butyl, 3- methylbutyl, and 3,3-dimethylbutyl.

The C2-Clo alkenyl group represented by R3 or R'may include vinyl, allyl, 1-propenyl, 3-butenyl, 2-methyl-1-propenyl, 3-methyl-2-butenyl, 3-pen- tenyl, 4-pentenyl, 3-methyl-3-butenyl, and 4-methyl-3-pentenyl.

The C2-Clo alkynyl group represented by R3 or R4 may include ethy- nyl, 1-propynyl, 2-propynyl, 1-butynyl, 3-methyl-1-butynyl, and 3,3-di-

methyl-1-butynyl.

The C2-C6 (halo) alkylene group represented by R3 and R4 taken to- gether may include ethylene, propylene, trimethylene, tetramethylene, and 3,3-dimethyltrimethylene.

The C4-C6 (halo) alkenylene group represented by R3 and R4 taken to- gether may include 2-butenylene and 2-pentenylene.

The halogen atom represented by R'or R'may include fluorine, chlorine, bromine, and iodine.

The C1-C4 (halo) alkyl group represented by R5 or R6 may include methyl, ethyl, propyl, 1-methylethyl, 1,1-dimethylethyl, trifluoromethyl, pentafluoroethyl, 3,3,3-trifluoroethyl, and 1,1,2,2-tetrafluoroethyl.

The C,-C, (halo) alkenyl group represented by R5 or R6 may include vinyl, 1-propenyl, 2-propenyl and 2,2-difluorovinyl.

The C2-Cq (halo) alkynyl group represented by R5 or R6 may include ethynyl, 1-propynyl, 2-propynyl and 3, 3,3-trifluoro-1-propynyl.

The C1-C4 (halo) alkyloxy group represented by R5 or R6 may include methoxy, ethoxy, propoxy, trifluoromethoxy, bromodifluoromethoxy, difluoro- methoxy, chlorodifluoromethoxy, pentafluoroethoxy, 2,2,2-trifluoroethoxy, and 1,1,2,2-tetrafluoroethoxy.

The C1-C4 (halo) alkylthio group represented by R5 or R6 may include methylthio, trifluoromethylthio, 2,2,2-trifluoroethylthio, and 1,1,2,2-tetra- fluoroethylthio.

The C1-C4 (halo) alkylsulfinyl group represented by R'or R'may include methylsulfinyl and trifluoromethylsulfinyl.

The C1-C4 (halo) alkylsulfonyl group represented by R5 or R6 may include methylsulfonyl and trifluoromethylsulfonyl.

The C1-C4 (halo) alkylcarbonyl group represented by R5 or R6 may include acetyl, propionyl, and trifluoroacetyl.

The C1-C4 (halo) alkyloxycarbonyl group represented by R5 or R6 may include methoxycarbonyl and 2,2,2-trifluoroethoxycarbonyl.

The C1-C4 (halo) alkylcarbonyloxy group represented by R5 or R6 may include acetyloxy, propionyloxy, and trifluoroacetyloxy.

The phenyloxy optionally substituted with halogen or Cl-C, alkyl, which is represented by R5 or R6, may include phenoxy, p-methylphenoxy, m- methylphenoxy, and p-chlorophenoxy.

The phenylthio group optionally substituted with halogen or C1-C3 alkyl, which is represented by R5 or R6, may include phenylthio, p-methyl- phenylthio, m-methylphenylthio, and p-chlorophenylthio.

The embodiments of compounds (X) may include the following com- pounds: The malononitrile compounds of formula (X) wherein R1 is hydrogen, and R2 is C1-C5 (halo) alkyl, C2-C5 (halo) alkenyl, or hydrogen; The malononitrile compounds of formula (X) wherein R'and R'are both hydrogen; The malononitrile compounds of formula (X) wherein R3 is C1-C10 alkyl, C2-C10 alkenyl, C2-Clo alkynyl, or hydrogen; R4 is C1-C10 alkyl, C2-C10 alkenyl, or C2-C10 alkynyl; The malononitrile compounds of formula (X) wherein R3 is hydrogen and R4 is C1-Clo alkyl, C2-Clo alkenyl, or C2-C10 alkynyl ; The malononitrile compounds of formula (X) wherein R3 is hydrogen and R4 is C1-Clo alkyl or C2-Clo alkenyl; The malononitrile compounds of formula (X) wherein R3 is hydrogen and R4 is C1-C10 alkyl ; The malononitrile compounds of formula (X) wherein R5 is halogen, n is an integer of 0 to 2; The malononitrile compounds of formula (X) wherein R6 is halogen,

cyano, nitro, C1-C4 haloalkyl, C1-C4 haloalkyloxy, or C1-C4 haloalkylthio ; The malononitrile compounds of formula (X) wherein Rois halogen, n is an integer of 0 to 2, and R6 is halogen, cyano, nitro, C1-C4 (halo) alkyl, C1-C4 (halo) alkyloxy, or C1-C4 (halo) alkylthio; The malononitrile compounds of formula (X) wherein R3 is hydrogen; R4 is C1-C10 alkyl, C2-C10 alkenyl, or C2-C10 alkynyl, R5 is halogen, n is an integer of 0 to 2, and R6 is halogen, cyano, nitro, C1-C4 (halo) alkyl, C1-C4 (halo) alkyloxy, or C1-C4 (halo) alkylthio; The malononitrile compounds of formula (X) wherein R1 is hydrogen, R2 is C1-C5 (halo) alkyl, C2-C5 (halo) alkenyl, or hydrogen, R3 is hydrogen; R4 is Cl-calo alkyl, C2-C10 alkenyl, or C2-C1O alkynyl, R5 is halogen, n is an integer of 0 to 2, and R6 is halogen, cyano, nitro, C1-C4 (halo) alkyl, C1-C4 (halo) alkyloxy, or C1-C4 (halo) alkylthio; The malononitrile compounds of formula (X) wherein R4 is vinyl and R6 is trifluoromethyl ; The malononitrile compounds of formula (X) wherein R4 is vinyl and R6 is difluoromethoxy; The malononitrile compounds of formula (X) wherein R4 is vinyl and R6 is trifluoromethoxy; The malononitrile compounds of formula (X) wherein R4 is vinyl and R6 is trifluoromethylthio ; The malononitrile compounds of formula (X) wherein R4 is vinyl and R6is 1,1,2,2-tetrafluoroethoxy; The malononitrile compounds of formula (X) wherein R4 is vinyl and R6 is chlorine; The malononitrile compounds of formula (X) wherein R4 is vinyl and R6 is bromine ; The malononitrile compounds of formula (X) wherein R4 is vinyl and

R6 is fluorine ; The malononitrile compounds of formula (X) wherein R4 is vinyl and R6 is cyano ; The malononitrile compounds of formula (X) wherein R4 is vinyl and R6 is nitro; The malononitrile compounds of formula (X) wherein R4 is allyl and R6 is trifluoromethyl; The malononitrile compounds of formula (X) wherein R4 is allyl and R6 is difluoromethoxy; The malononitrile compounds of formula (X) wherein R4 is allyl and R6 is trifluoromethoxy; The malononitrile compounds of formula (X) wherein R4 is allyl and R6 is trifluoromethylthio ; The malononitrile compounds of formula (X) wherein R4 is allyl and R6 is1,1,2,2-tetrafluoroethoxy; The malononitrile compounds of formula (X) wherein R4 is allyl and R6 is chlorine; The malononitrile compounds of formula (X) wherein R4 is allyl and R6 is bromine; The malononitrile compounds of formula (X) wherein R4 is allyl and R6 is fluorine ; The malononitrile compounds of formula (X) wherein R4 is allyl and R6 is cyano; The malononitrile compounds of formula (X) wherein R4 is allyl and R6 is nitro; The malononitrile compounds of formula (X) wherein R4 is ethyl and R6 is trifluoromethyl; The malononitrile compounds of formula (X) wherein R4 is ethyl and

R6 is trifluoromethoxy; The malononitrile compounds of formula (X) wherein R4 is ethyl and R6 is trifluoromethylthio ; The malononitrile compounds of formula (X) wherein R4 is ethyl and R6 is chlorine; The malononitrile compounds of formula (X) wherein R4 is ethyl and R6 is cyano ; The malononitrile compounds of formula (X) wherein R4 is 3-butenyl and R6 is trifluoromethyl; The malononitrile compounds of formula (X) wherein R4 is 3-butenyl and R6 is trifluoromethoxy; The malononitrile compounds of formula (X) wherein R4 is 3-butenyl and R6 is trifluoromethylthio ; The malononitrile compounds of formula (X) wherein R4 is 3-butenyl and R6 is chlorine; The malononitrile compounds of formula (X) wherein R4 is 3-butenyl and R3 is cyano; The malononitrile compounds of formula (X) wherein R4 is 2-methyl- 1-propenyl and R6 is trifluoromethyl ; The malononitrile compounds of formula (X) wherein R4 is 2-methyl- 1-propenyl and R6 is trifluoromethoxy ; The malononitrile compounds of formula (X) wherein R4 is 2-methyl- 1-propenyl and R6 is trifluoromethylthio ; The malononitrile compounds of formula (X) wherein R4 is 2-methyl- 1-propenyl and R6 is chlorine; The malononitrile compounds of formula (X) wherein R4 is 2-methyl- 1-propenyl and R6 is cyano; The malononitrile compounds of formula (X) wherein R4 is 1-propenyl

and R6 is trifluoromethyl ; The malononitrile compounds of formula (X) wherein R4 is 1-propenyl and R6 is trifluoromethoxy ; The malononitrile compounds of formula (X) wherein R4 is 1-propenyl and R6 is trifluoromethylthio ; The malononitrile compounds of formula (X) wherein R4 is 1-propenyl and R6 is chlorine; The malononitrile compounds of formula (X) wherein R4 is 1-propenyl and R6 is cyano; The malononitrile compounds of formula (X) wherein R4 is 2-methyl- propyl and R6 is trifluoromethyl; The malononitrile compounds of formula (X) wherein R4 is 2-methyl- propyl and R6 is difluoromethoxy; The malononitrile compounds of formula (X) wherein R4 is 2-methyl- propyl and R6 is trifluoromethoxy ; The malononitrile compounds of formula (X) wherein R4 is 2-methyl- propyl and R6 is trifluoromethylthio ; The malononitrile compounds of formula (X) wherein R4 is 2-methyl- propyl and R6 is 1,1,2,2-tetrafluoroethoxy; The malononitrile compounds of formula (X) wherein R4 is 2-methyl- propyl and R6 is chlorine; The malononitrile compounds of formula (X) wherein R4 is 2-methyl- propyl and R6 is bromine; The malononitrile compounds of formula (X) wherein R4 is 2-methyl- propyl and R6 is fluorine ; The malononitrile compounds of formula (X) wherein R4 is 2-methyl- propyl and R6 is cyano; The malononitrile compounds of formula (X) wherein R4 is 2-methyl-

propyl and R6 is nitro; The malononitrile compounds of formula (X) wherein R4 is 2,2-di- methylpropyl and R3 is trifluoromethyl; The malononitrile compounds of formula (X) wherein R4 is 2,2-di- methylpropyl and R6 is difluoromethoxy; The malononitrile compounds of formula (X) wherein R4 is 2,2-di- methylpropyl and R6 is trifluoromethoxy; The malononitrile compounds of formula (X) wherein R4 is 2,2-di- methylpropyl and R6 is trifluoromethylthio; The malononitrile compounds of formula (X) wherein R4 is 2,2-di- methylpropyl and R6 is 1,1,2,2-tetrafluoroethoxy; The malononitrile compounds of formula (X) wherein R4 is 2,2-di- methylpropyl and R6 is chlorine; The malononitrile compounds of formula (X) wherein R4 is 2,2-di- methylpropyl and R6 is bromine; The malononitrile compounds of formula (X) wherein R4 is 2,2-di- methylpropyl and R6 is fluorine ; The malononitrile compounds of formula (X) wherein R4 is 2,2-di- methylpropyl and R6 is cyano; The malononitrile compounds of formula (X) wherein R4 is 2,2-di- methylpropyl and R6 is nitro; The malononitrile compounds of formula (X) wherein R4 is 1-methyl- ethyl and R6 is trifluoromethyl; The malononitrile compounds of formula (X) wherein R4 is 1-methyl- ethyl and R6 is difluoromethoxy; The malononitrile compounds of formula (X) wherein R4 is 1-methyl- ethyl and R6 is trifluoromethoxy; The malononitrile compounds of formula (X) wherein R4 is 1-methyl-

ethyl and R6 is trifluoromethylthio ; The malononitrile compounds of formula (X) wherein R4 is 1-methyl- ethyl and R6 is 1,1,2,2-tetrafluoroethoxy; The malononitrile compounds of formula (X) wherein R4 is 1-methyl- ethyl and R6 is chlorine ; The malononitrile compounds of formula (X) wherein R4 is 1-methyl- ethyl and R6 is bromine; The malononitrile compounds of formula (X) wherein R4 is 1-methyl- ethyl and R6 is fluorine ; The malononitrile compounds of formula (X) wherein R4 is 1-methyl- ethyl and R6 is cyano; The malononitrile compounds of formula (X) wherein R4 is 1-methyl- ethyl and R6 is nitro.

The preferred compounds among compound (X) are the compounds wherein R6 is halogen, cyano, nitro, C1-C4 haloalkyl, C1-C4 haloalkyloxy or C1-C4 haloalkylthio ; the compounds wherein R3 and R4 are the same or different and independently C1-C5 alkyl, C2-C5 alkenyl, C2-C5 alkynyl, or hydrogen, or R3 and R4 are taken together to form Cz-Cg (halo) alkylene; or the compounds wherein n is 1 to 3 and at least one of R5 is halogen, cyano, nitro, C1-C4 haloalkyl, C1-C4 haloalkyloxy or C1-C4 (halo) alkylthio. More preferred compounds are the compounds wherein R6 is halogen, cyano, nitro, C1-C4 fluoroalkyl, Cl-C, fluoroalkyloxy or Cl-C, fluoroalkylthio ; or the compounds wherein n is 1 to 3 and at least one of R5 is halogen, cyano, nitro, C1-C4 fluoroalkyl, C1-C4 fluoroalkyloxy or C1-C4 fluoroalkylthio.

The following will describe the production processes for compounds (X).

The compounds (X) can be produced by, for example, the following (Production Process 1) to (Production Process 5).

(Production Process 1) This is a process by reacting compound (a) with compound (b) in the presence of a base. R3 R2 (RS) n R1 R2 R3 R Z (b) Ra I CN N Base on I CN N (X) (X)

wherein Ru, R2, R3, R4, R5, R6, and n are as defined above, and Z is halogen, methanesulfonyl, trifluoromethanesulfonyl, or toluenesulfonyl.

The reaction is usually carried out in a solvent. The solvent which can be used in the reaction may include acid amides such as dimethylform- amide; ethers such as diethyl ether and tetrahydrofuran; organic sulfur compounds such as dimethylsulfoxide and sulfolane; halogenated hydro- carbons such as 1,2-dichloroethane and chlorobenzene; aromatic hydro- carbons such as toluene and xylene; water; and mixtures thereof The base which can be used in the reaction may include inorganic bases such as sodium hydride, sodium hydroxide, potassium hydroxide, and potassium carbonate; alkali metal alkoxides such as sodium methoxide, sodium ethoxide, and potassium tert-butoxide; alkali metal amides such as lithium diisopropylamide; and organic bases such as 4-dimethylaminopyri- dine, 1, 4-diazabicyclo [2.2.2] octane, and 1, 8-diazabicylco [5.4.0]-7-undecene.

The amount of base used in the reaction is usually in a ratio of 1 to 10 moles relative to 1 mole of compound (a).

The reaction temperature is usually in the range of-20°C to 100°C.

The reaction time is usually in the range of 1 to 24 hours.

The amount of compound (b) used in the reaction is usually in a ratio of 1 to 10 moles relative to 1 mole of compound (a).

After the reaction, the reaction mixture is poured into water, followed

by ordinary post-treatment procedures including extraction with an organic solvent and concentration, thereby isolating the desired compounds, which may be purified by a technique such as chromatography or recrystallization.

(Production Process 2) This is a process by reacting compound (c) with compound (d) in the presence of a base. (R n R1 R 2 (run 3 R Ruz R2 R3 tR R6 < V R4 R (d) R CN N Base CN N wherein Ru, R2, R3, R4, R5, R6, n, and Z are as defined above.

The reaction is usually carried out in a solvent. The solvent which can be used in the reaction may include acid amides such as dimethylform- amide; ethers such as diethyl ether and tetrahydrofuran; organic sulfur compounds such as dimethylsulfoxide and sulfolane; halogenated hydro- carbons such as 1,2-dichloroethane and chlorobenzene; aromatic hydro- carbons such as toluene and xylene; water; and mixtures thereof.

The base which can be used in the reaction may include inorganic bases such as sodium hydride, sodium hydroxide, potassium hydroxide, and potassium carbonate; alkali metal alkoxides such as sodium methoxide, sodium ethoxide, and potassium tert-butoxide ; alkali metal amides such as lithium diisopropylamide; and organic bases such as 4-dimethylaminopyri- dine, 1, 4-diazabicyclo [2.2.2] octane, and 1, 8-diazabicylco [5.4.0]-7-undecene.

The amount of base used in the reaction is usually in a ratio of 1 to 10 moles relative to 1 mole of compound (a).

The reaction temperature is usually in the range of-20°C to 100°C.

The reaction time is usually in the range of 1 to 24 hours.

The amount of compound (b) used in the reaction is usually in a ratio of 1 to 10 moles relative to 1 mole of compound (a).

After the reaction, the reaction mixture is poured into water, followed by ordinary post-treatment procedures including extraction with an organic solvent and concentration, thereby isolating the desired compounds, which may be purified by a technique such as chromatography or recrystallization.

The compound (a) can be produced through a route, for example, as shown in the following scheme. wherein Ru, R2, R5, R6, and n are as defined above.

(Step 1) The compound (f) can be produced by reacting compound (e) with malononitrile.

The reaction is usually carried out in a solvent and in the presence of a base. The solvent which can be used in the reaction may include acid amides such as N, N-dimethylformamide; ethers such as diethyl ether and tetrahydrofuran ; halogenated hydrocarbons such as chloroform, 1,2-dichlo- roethane, and chlorobenzene; aromatic hydrocarbons such as toluene and xylene; alcohols such as methanol, ethanol, and isopropanol; and mixtures thereof.

The base which can be used in the reaction may include tetrabutyl- ammonium hydroxide. The amount of base used in the reaction is usually in a ratio of 0.01 to 0.5 mole relative to 1 mole of compound (e).

The amount of malononitrile used in the reaction is usually in a ratio of 1 to 10 moles relative to 1 mole of compound (e).

The reaction temperature is usually in the range of-20°C to 200°C.

The reaction time is usually in the range of 1 to 24 hours.

The reaction may be carried out, while removing, if necessary, water which is generated by the reaction, from the reaction system.

After the reaction, the reaction mixture is poured into water, followed by ordinary post-treatment procedures including extraction with an organic solvent and concentration, thereby isolating the desired compounds, which may be purified by a technique such as chromatography or recrystallization.

(Step 2) (1) The case where R2 is a substituent other than hydrogen and cyano: The compound (a) can be produced by reacting compound (f) with an organometallic compound.

The reaction is usually carried out in a solvent and, if necessary, in the presence of a copper salt.

The solvent which can be used in the reaction may include ethers such as diethyl ether and tetrahydrofuran; aromatic hydrocarbons such as toluene and xylene; and mixtures thereof.

The organometallic compound which can be used in the reaction may include organic magnesium compounds such as methyl magnesium iodide, ethyl magnesium bromide, isopropyl magnesium bromide, vinyl magnesium bromide, ethynyl magnesium bromide, and dimethyl magnesium; organic lithium compounds such as methyl lithium ; organic zinc compounds such as diethyl zinc; and organic copper compounds such as trifluoromethyl copper.

The amount of organometallic compound used in the reaction is usually in a ratio of 1 to 10 moles relative to 1 mole of compound (f).

The copper salt which can be used in the reaction may include copper (I) iodide and copper (I) bromide. The amount of copper salt used in the reaction is usually not greater than 1 mole relative to 1 mole of compound (f).

The reaction temperature is usually in the range of-20°C to 100°C.

The reaction time is usually in the range of 1 to 24 hours.

After the reaction, the reaction mixture is poured into water, followed by ordinary post-treatment procedures including extraction with an organic solvent and concentration, thereby isolating the desired compounds, which may be purified by a technique such as chromatography or recrystallization.

(2) The case where R2 is hydrogen: The compound (a) can be produced by subjecting compound (f) to reduction.

The reduction is usually carried out in a solvent.

The solvent which can be used in the reaction may include ethers such as diethyl ether and tetrahydrofuran; aromatic hydrocarbons such as toluene and xylene; alcohols such as methanol, ethanol, and propanol; water; and mixtures thereof.

The reducing agent which can be used in the reaction may include sodium borohydride. The amount of reducing agent used in the reaction is usually in a ratio of 0.25 to 2 moles relative to 1 mole of compound (f).

The reaction time is usually in the range of a moment to 24 hours.

The reaction temperature is usually in the range of 0°C to 50°C.

After the reaction, the reaction mixture is poured into water, followed by ordinary post-treatment procedures including extraction with an organic solvent and concentration, thereby isolating the desired compounds, which may be purified by a technique such as chromatography or recrystallization.

(3) The case where R2 is cyano: The compound (a) can be produced by reacting compound (f) with a

cyanide.

The solvent which can be used in the reaction may include ethers such as diethyl ether and tetrahydrofuran; aromatic hydrocarbons such as toluene and xylene; and mixtures thereof.

The cyanide which can be used in the reaction may include tetra- butylammonium cyanide. The amount of cyanide used in the reaction is usually in a ratio of 1 to 10 moles relative to 1 mole of compound (f).

The reaction temperature is usually in the range of-20°C to 100°C.

The reaction time is usually in the range of 1 to 24 hours.

After the reaction, the reaction mixture is poured into water, followed by ordinary post-treatment procedures including extraction with an organic solvent and concentration, thereby isolating the desired compounds, which may be purified by a technique such as chromatography or recrystallization.

(Production Process 3) The compounds wherein R1 is C1-C5 (halo) alkyl, R2 and R3 are both hydrogen, and R4 is CH2=CH can also be produced by the process as shown in the following scheme. wherein R5, R6, and n are as defined above, R"is Ci-Cg (halo) alkyl, Bu is butyl, and AIBN is azobisisobutyronitrile.

The reaction can be carried out according to the process as described in J. Am. Chem. Soc., 110,1289 (1988).

(Production Process 4) The compounds wherein R1 is cyano, R2 and R3 are both hydrogen, R4 is CH2=CH can also be produced by the process as shown in the following scheme.

wherein R5, R6, and n are as defined above, dba is dibenzylideneacetone, and dppf is 1,1'-bis (diphenylphosphino) ferrocene.

The reaction can be carried out according to the conditions as described in Tetrahedron Lett., 41,2911 (2000).

(Production Process 5) The compounds wherein Rl is Cl-C5 (halo) alkyloxy, R2 and R3 are both hydrogen, and R4 is CH=CH can also be produced by the process as shown in the following scheme. wherein R5, R6, and n are as defined above, Rl2 is Cl-C5 (halo) alkyloxy, Ph is phenyl, and THF is tetrahydrofuran.

The reaction can be carried out according to the conditions as described in J. Am. Chem. Soc., 120,6838 (1998).

The pests against which compounds (X) exhibit controlling activity may include insect pests, acarine pests, and nematode pests, specific exam- ples which are as follows: Hemiptera: Delphacidae such as Laodelphax striatellus, Nilaparvata lugens, and

Sogatella furcifera; Deltocephalidae such as Nephotettix cincticeps and Nephotettix virescens ; Aphididae such as Aphis gossypii and Myzus persicae, Pentatomidae such as Nezara antennata, Riptortus clavetus Eysarcoris lewisi, Eysarcoris parvus, Plautia stali and Halyomorpha misia ; Aleyrodidae such as Trialeurodes vaporariorum and Bemisia argen- tifoli#, Coccidae such as Aonidiella aurantii, Comstockaspis perniciosa, Un- aspis citri, Ceroplastes rubens, and Icerya purchasi ; Tingidae; Psyllidae ; Lepidoptera: Pyralidae such as Chilo suppressalis, Cnaphalocrocis medinalis, Notarcha derogata, and Plodia interpunctella ; Noctuidae such as Spodoptera litura, Pseudaletia separata, Thorico- plusia spp., Heliothis spp., and Helicoverpa spp.; Pieridae such as Pieris rapae ; Tortricidae such as Adoxophyes spp., Grapholita molesta, and Cydia pomonella ; Carposinidae such as Carposina niponensis, Lyonetiidae such as Lyonetia spp.; Lymantriidae such as Lyamantria spp. and Euproctis spp.; Yponomentidae such as Plutella xylostella ; Gelechiidae such as Pectinophora gossypiella ; Arctiidae such as Hyphantria cunea ; Tineidae such as TYnea translucens and TYneola bisselliella ; Diptera:

Calicidae such as Culex pipiens pallens, Culex tritaeniorhynchus, and Culex quinquefasciatus ; Aedes spp. such as Aedes aegypti and Aedes albopictus, Anopheles spp. such as Anopheles sinensis ; Chironomidae; Muscidae such as Musca domestica and Muscina stabulans ; Calliphoridae ; Sarcophagidae; Fanniidae; Anthomyiidae such as Delia platura and Delia antiqua ; Tephritidae; Drosophilidae ; Psychodidae; Simuliidae ; Tabanidae ; Stomoxyidae ; Agromyzidae; Coleoptera: Diabrotica spp. such as Diabrotica virgifera and Diabrotica undecim- punctata howardi ; Scarabaeidae such as Anomala cuprea and Anomala rufocuprea ; Curculionidae such as Sitophilus zeamais, Lissorhoptrus oryzophilus, and Callosobruchuys chienensis ; Tenebrionidae such as Tenebrio molitor and Tribolium castaneum ; Chrysomelidae such as Oulema oryzae, Aulacophora femoralis, Phyl- lotreta striolata, and Leptinotarsa decemlineata ; Anobiidae; Epilachna spp. such as Epilachna vigintioctopunctata ;

Lyctidae; Bostrychidae; Cerambycidae ; Paederus fuscipes; Dictyoptera: Blattella germanica, Periplaneta fuliginosa, Periplaneta americana, Periplaneta brunnea, and Blatta orientalis, Thysanoptera: Thrips palmi, Thrips tabaci, Frankliniella occidentalis, Frankliniella intonsa ; Hymenoptera: Formicidae; Vespidae; Bethylidae ; Tenthredinidae such as Athalia japonica ; Orthoptera: Gryllotalpidae; Acrididae; Siphonaptera: Ctenocephalides felis, Ctenocephalides canis, Pulex irritans, Xeno- psylla cheopis, Anoplura : Pediculus humanus corporis, Phthirus pubis, Haematopinus eurys- ternus, and Dalmalinia ovis, Isoptera: Reticulitermes speratus and Coptotermes formosanus, Acarina: Tetranychidae such as Tetranychus urticae, Tetranychus kanzawai,

Panonychus citri, Panonychus ulmi, and Oligonychus spp.; Eriophyidae such as Aculops pelekassi and Aculus schlechtendalir, Tarsonemidae such as Polyphagotarsonemus latus, Tenuipalpidae; Tuckerellidae ; Ixodidae such as Haemaphysalis longicornis, Haemaphysalis flava, Dermacentor taiwanicus, Ixodes ovatus, Ixodes persulcatus, and Boophilus microplus, Acaridae such as Tyrophagus putrescentiae, Epidermoptidae such as Dermatophagoides farinae and Dermato- phagoides ptrenyssnus, Cheyletidae such as Cheyletus eruditus, Cheyletus malaccensis, and Cheyletus moore#, Dermanyssidae; Arachnida: Chiracanthium japonicum and Latrodectus hasselti#, Chilopoda: Thereuonema hilgendorfi and Scolopendra subspinipes, Diplopoda: Oxidus gracilis and Nedyopus tambanus, Isopoda: Armadillidium vulgare ; Gastropoda: Limax marginatus and Limax flavus, Nematoda: Pratylenchus coffeae, Pratylenchus fallax, Heterodera glycines, Glo- bodera rostochiensis, Meloidogyne hapla, and Meloidogyne incognita.

When compounds (X) are used as the active ingredients of pesticide

compositions, they may be used as such without addition of any other ingre- dients. However, they are usually used in admixture with solid carriers, liquid carriers and/or gaseous carriers, and if necessary, by addition of adju- vants such as surfactants, followed by formulation into various forms such emulsifiable concentrates, oil formulations, flowables, dusts, wettable pow- ders, granules, paste formulations, microcapsule formulations, foams, aero- sol formulations, carbon dioxide gas formulations, tablets, or resin formula- tions. These formulations may be used by processing into poison baits, shampoo, mosquito coils, electric mosquito mats, smokes, fumigants, or sheets.

In these formulations, compounds (X) are usually contained each in an amount of 0.1% to 95% by weight.

The solid carrier which can be used in the formulation may include the following materials in fine powder or granular form: clays (e. g, kaolin clay, diatomaceous earth, bentonite, Fubasami clay, acid clay); talc, ceramic, and other inorganic minerals (e. g, sericite, quartz, sulfur, activated carbon, calcium carbonate, hydrated silica); and chemical fertilizers (e. g, ammonium sulfate, ammonium phosphate, ammonium nitrate, ammonium chloride, urea).

The liquid carrier may include aromatic or aliphatic hydrocarbons (e. g., xylene, toluene, alkylnaphthalene, phenylxylylethane, kerosine, light oils, hexane, cyclohexane) ; halogenated hydrocarbons (e. g., chlorobenzene, dichloromethane, dichloroethane, trichloroethane); alcohols (e. g, methanol, ethanol, isopropyl alcohol, butanol, hexanol, ethylene glycol); ethers (e. g., diethyl ether, ethylene glycol dimethyl ether, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, propylene glycol monomethyl ether, tetrahydrofuran, dioxan) ; esters (e. g, ethyl acetate, butyl acetate); ketones (e. g., acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone) ;

nitriles (acetonitrile, isobutyronitrile); sulfoxides (e. g., dimethylsulfoxide); acid amides (e. g, N, N-dimethylformamide, N, N-dimethylacetamide); vege- table oils (e. g., soy bean oil and cotton seed oil); plant essential oils (e. g., orange oil, hyssop oil, lemon oil); and water.

The gaseous carrier may include butane gas, Freon gas, liquefied petroleum gas (LPG), dimethyl ether, and carbon dioxide.

The surfactant may include alkyl sulfate salts; alkylsulfonic acid salts; alkylarylsulfonic acid salts; alkyl aryl ethers and their polyoxyethylene derivatives; polyethylene glycol ethers; polyol esters; and sugar alcohol deri- vatives.

The other adjuvants may include binders, dispersants, and stabili- zers, specific examples of which are casein, gelatin, polysaccharides (e. g, starch, gum arabic, cellulose derivatives, alginic acid), lignin derivatives, bentonite, sugars, synthetic water-soluble polymers (e. g, polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acid), PAP (isopropyl acid phosphate), BHT (2,6-di-t-butyl-4-methylphenol), BHA (mixtures of 2-t-butyl-4-methoxyphe- nol and 3-t-butyl-4-methoxyphenol), vegetable oils, mineral oils, fatty acids, and fatty acid esters.

The base material for resin formulations may include vinyl chloride polymers and polyurethanes. These base materials may contain, if neces- sary, plasticizers such as phthalic acid esters (e. g, dimethyl phthalate, di- octyl phthalate), adipic acid esters, and stearic acid. The resin formulations can be obtained by kneading the compounds into the base materials with an ordinary kneader and subsequent forming such as injection molding, extru- sion, or pressing. They can be processed, if necessary, though further form- ing and cutting into resin formulations in various shapes such as plates, films, tapes, nets, or strings. These resin formulations are processed as, for example, collars for animals, ear tags for animals, sheet formulations, at-

tractive strings, or poles for horticultural use.

The base material for poison baits may include grain powders, vege- table oils, sugars, and crystalline cellulose. If necessary, additional agents may be added, including antioxidants such as dibutylhydroxytoluene and nordihydroguaiaretic acid; preservatives such as dehydroacetic acid; agents for preventing children and pets from erroneously eating, such as hot pepper powder; and pest-attractive flavors such as cheese flavor, onion flavor, and peanut oil.

The pesticide compositions of the present invention may be used by, for example, direct application to pests and/or application to the habitats of pests (e. g, plant bodies, animal bodies, soil).

When the pesticide compositions of the present invention are used for the control of pests in agriculture and forestry, their application amounts are usually 1 to 10,000 g/ha, preferably 10 to 500 g/ha. Formulations such as emulsifiable concentrates, wettable powders, flowables, and microcapsule formulations are usually used after dilution with water to have an active ingredient concentration of 1 to 1000 ppm, while formulations such as dusts and granules are usually used as such. These formulations may be directly applied to plants to be protected from pests. These formulations can also be incorporated into soil for the control of pests inhabiting the soil, or can also be applied to beds before planting or applied to planting holes or plant bot- toms in the planting. Further, the pesticide compositions of the present invention in the form of sheet formulations can be applied by the methods in which the sheet formulations are wound around plants, disposed in the vi- cinity of plants, or laid on the soil surface at the plant bottoms.

When the pesticide compositions of the present invention are used for the prevention of epidemics, their application amounts as active ingredient amounts are usually 0.001 to 10 mg/m3 for spatial application or 0.001 to 100

mg/m2 for planar application. Formulations such as emulsifiable concen- trates, wettable powders, and flowables are usually applied after dilution with water to have an active ingredient concentration of 0.01 to 10,000 ppm, while formulations such as oil formulations, aerosols, smokes, or poison baits are usually applied as such.

When the pesticide compositions of the present invention are used for the control of external parasites on domestic animals such as cattle, sheep, goat, and fowl or small animals such as dogs, cats, rats, and mice, they can be used by the veterinarily well-known methods. As the specific methods of use, administration is achieved by, for example, tablets, feed incorporation, suppositories, or injections (e. g, intramuscular, subcutaneous, intravenous, intraperitoneal) for systemic control, or by, for example, spraying, pour-on treatment, or spot-on treatment with an oil formulation or an aqueous solu- tion, washing animals with a shampoo formulation, or attachment of a collar or ear tag prepared from a resin formulation to animals for non-systemic control. The amounts of compounds (X) when administered to animal bod- ies are usually in the range of 0.1 to 1000 mg per 1 kg weight of each animal.

The pesticide compositions of the present invention can also be used in admixture or combination with other insecticides, nematocides, acaricides, bactericides, fungicides, herbicides, plant growth regulators, synergists, fer- tilizers, soil conditioners, animal feeds, and the like.

Examples of the insecticides and acaricides include organophos- phorus compounds such as fenitrothion [O, 0-dimethyl 0- (3-methyl-4-nitro- phenyl) phosphorothioate], fenthion [O, 0-dimethyl 0- (3-methyl-4- (methy- thio) phenyl) phosphorothioate], diazinon [0, O-diethyl 0-2-isopropyl-6- methylpyrimidin-4-yl phosphorothioate], chlorpyrifos [O, O-diethyl 0-3, 5,6- trichloro-2-pyridyl phosphorothioate], DDVP [2,2-dichlorovinyl dimethyl phosphate], cyanophos [0-4-cyanophenyl O, 0-dimethyl phosphorothioate],

dimethoate [O, 0-dimethyl S- (N-methylcarbamoylmethyl) dithiophosphate], phenthoate [ethyl 2-dimethoxyphosphinothioylthio (phenyl) acetate], mala- thion [diethyl (dimethoxyphosphinothioylthio) succinate], and azinphos- methyl [S-3,4-dihydro-4-oxo-1,2,3-benzotriazin-3-ylmethyl O, 0-dimethyl phosphorodithioate]; carbamate compounds such as BPMC (2-sec-butyl- phenyl methylcarbamate), benfracarb [ethyl N- [2, 3-dihydro-2, 2-dimethyl- benzofuran-7-yloxycarbonyl (methyl) aminothio]-N-isopropyl-ß-alaninate], propoxur [2-isopropoxyphenyl N-methylcarbamate] and carbaryl [1-naphthyl N-methylcarbamate]; pyrethroid compounds such as etofenprox [2- (4- ethoxyphenyl)-2-methylpropyl-3-phenoxybenzyl ether], fenvalerate [(RS)-a- cyano-3-phenoxybenzyl (RS)-2- (4-chlorophenyl)-3-methyl-butyrate], esfen- valerate [ (S)-a-cyano-3-phenoxybenzyl (S)-2- (4-chlorophenyl)-3-methyl- butyrate], fenpropathrin [(RS)-a-cyano-3-phenoxybenzyl 2,2,3,3-tetra- methylcyclopropanecarboxylate], cypermethrin [(RS)-a-cyano-3-phenoxy- benzyl (lRS)-cis, trans-3- (2, 2-dichlorovinyl)-2, 2-dimethylcyclopropanecar- boxylate], permethrin [3-phenoxybenzyl (lRS)-cis, trans-3- (2, 2-dichloro- <BR> <BR> <BR> <BR> <BR> vinyl)-2, 2-dimethylcyclopropanecarboxylate], cyhalothrin [(RS)-a-cyano-3- phenoxybenzyl (Z)- (lRS)-cis-3- (2-chloro-3, 3, 3-trifluoroprop-1-enyl)-2,2-di- methylcyclopropanecarboxylate], deltamethrin [(S)-a-cyano-3-phenoxy- benzyl (lR)-cis-3- (2, 2-dibromovinyl)-2,2-dimethylcyclopropane-carboxylate], cycloprothrin [ (RS)-a-cyano-3-phenoxybenzyl (RS)-2, 2-dichloro- l- (4-ethoxy- phenyl) cyclopropanecarboxylate], fluvalinate [a-cyano-3-phenoxybenzyl N- (2-chloro-a, a, a-trifluoro-p-tolyl)-D-valinate], bifenthrin [2-methylbiphenyl-3- ylmethyl (Z)- (lRS)-cis-3- (2-chloro-3, 3, 3-trifluoroprop-1-enyl)-2,2-dimethyl- cyclopropanecarboxylate], 2-methyl-2- (4-bromodifluoro-methoxyphenyl)- propyl 3-phenoxybenzyl ether, tralomethrin [(S)-a-cyano-3-phenoxybenzyl (lR-cis)-3-{(lRS) (1, 2,2,2-tetrabromoethyl)}-2,2-dimethyl-cyclopropanecarbox- ylate], silafluofen [ (4-ethoxyphenyl) {3- (4-fluoro-3-phenoxyphenyl) propyl}-

dimethylsilane], d-phenothrin [3-phenoxybenzyl (lR-cis, trans)-chrysan- themate], cyphenothrin [(RS)-a-cyano-3-phenoxybenzyl (lR-cis, trans)-chry- santhemate], d-resmethrin [5-benzyl-3-furylmethyl (lR-cis, trans)-chrysan- themate], acrinathrin [(S)-a-cyano-3-phenoxybenzyl (lR, cis (Z))-2,2-dimeth- yl-3- {3-oxo-3- (1, 1, 1, 3,3,3-hexafluoropropyloxy) propenyl} cyclopropanecarbox- ylate], cyfluthrin [ (RS)-a-cyano-4-fluoro-3-phenoxybenzyl 3- (2, 2-dichloro- vinyl)-2,2-dimethylcyclopropanecarboxylate], tefluthrin [2,3,5,6-tetrafluoro- 4-methylbenzyl (lRS-cis (Z))-3- (2-chloro-3, 3,3-trifluoroprop-1-enyl)-2,2-di- methylcyclopropanecarboxylate], transfluthrin [2,3,5,6-tetrafluorobenzyl (lR-trans)-3-(2, 2-dichlorovinyl)-2, 2-dimethylcyclopropanecarboxylate], tetra- methrin [3,4,5,6-tetrahydrophthalimidomethyl (lRS)-cis, trans-chrysan- themate], allethrin [(RS)-3-allyl-2-methyl-4-oxocyclopent-2-enyl (lRS)- cis, trans-chrysanthemate], prallethrin [ (S)-2-methyl-4-oxo-3- (2-propynyl) cyclopent-2-enyl (lR)-cis, trans-chrysanthemate], empenthrin [(RS)-l-ethy- nyl-2-methyl-2-pentenyl (lR)-cis, trans-chrysanthemate], imiprothrin [2,5- dioxo-3- (prop-2-ynyl) imidazolidin-1-ylmethyl (lR)-cis,trans-2,2-dimethyl-3- (2-methylprop-1-enyl) cyclopropanecarboxylate], d-furamethrin [5- (2-pro- pynyl) furfuryl (lR)-cis, trans-chrysanthemate] and 5- (2-propynyl) furfuryl 2,2,3,3-tetramethylcyclopropanecarboxylate; neonicotinoid derivatives such as N-cyano-N'-methyl-N'- (6-chloro-3-pyridylmethyl) acetamidine; niten- pyram [N- (6-chloro-3-pyridylmethyl)-N-ethyl-N'-methyl-2-nitrovynylide ne- diamine]; thiacloprid [1- (2-chloro-5-pyridylmethyl)-2-cyanoiminothiazoline] ; thiamethoxam [3-((2-chloro-5-thiazolyl) methyl)-5-methyl-4-nitroiminotetra- hydro-1, 3,5-oxadiazine], 1-methyl-2-nitro-3- ( (3-tetrahydrofuryl) methyl)- guanidine and 1-(2-chloro-5-thiazolyl) methyl-3-methyl-2-nitroguanidine ; nitroiminohexahydro-1, 3,5-triazine derivatives; chlorinated hydrocarbons such as endosulfan [6,7,8,9,10,10-hexachloro-1,5,5a, 6,9,9a-hexahydro-6,9- methano-2,4,3-benzodioxathiepine oxide], y-BHC [1,2,3,4,5,6-hexachloro-

cyclohexane] and 1, 1-bis (chlorophenyl)-2,2,2-trichloroethanol; benzoyl- phenylurea compounds such as chlorfluazuron [1- (3, 5-dichloro-4- (3-chloro-5- trifluoromethylpyridyn-2-yloxy) phenyl)-3- (2, 6-difluorobenzoyl) urea], teflu- benzuron [1- (3, 5-dichloro-2,4-difluorophenyl)-3- (2, 6-difluorobenzoyl) urea] and flufenoxuron [1- (4- (2-chloro-4-trifluoromethylphenoxy)-2-fluorophenyl)- 3- (2, 6-difluorobenzoyl) urea]; juvenile hormone like compounds such as pyri- proxyfen [4-phenoxyphenyl 2- (2-pyridyloxy) propyl ether], methoprene [iso- propyl (2E, 4E)-11-methoxy-3, 7,11-trimethyl-2,4-dodecadienoate] and hydro- prene [ethyl (2E, 4E)-11-methoxy-3, 7,11-trimethyl-2,4-dodecadienoate]; thio- urea derivatives such as diafenthiuron [N- (2, 6-diisopropyl-4-phenoxyphen- yl)-N'-tert-butylcarbodiimide]; phenylpyrazole compounds; 4-bromo-2- (4- chlorophenyl)-l-ethoxymethyl-5-trifluoromethylpyrrol-3-carbo nitrile [chlor- fenapil]; metoxadiazone [5-methoxy-3- (2-methoxyphenyl)-1, 3,4-oxadiazol- 2 (3H)-one], bromopropylate [isopropyl 4,4'-dibromobenzilate], tetradifon [4- chlorophenyl 2,4,5-trichlorophenyl sulfone], chinomethionat [S, S-6-methyl- quinoxaline-2, 3-diyldithiocarbonate], pyridaben [2-tert-butyl-5- (4-tert- butylbenzylthio)-4-chloropyridazin-3 (2H)-one], fenpyroximate [tert-butyl (E)-4- [ (1, 3-dimethyl-5-phenoxypyrazol-4-yl) methyleneaminooxymethyl] ben- zoate], tebufenpyrad [N- (4-tert-butylbenzyl)-4-chloro-3-ethyl-1-methyl-5- pyrazolecarboxamide], polynactins complex [tetranactin, dinactin and trinactin], pyrimidifen [5-chloro-N- [2- {4- (2-ethoxyethyl)-2, 3-dimethylphen- oxy} ethyl]-6-ethylpyrimidin-4-amine], milbemectin, abamectin, ivermectin and azadirachtin [AZAD]. Examples of the synergists include bis- (2, 3,3,3- tetrachloropropyl) ether (S-421), N- (2-ethylhexyl) bicyclo [2.2.1] hept-5-ene- 2,3-dicarboximide (MGK-264) and a- [2- (2-butoxyethoxy) ethoxy]-4,5-methyl- enedioxy-2-propyltoluene (piperonyl butoxide).

The present invention will further be illustrated by the following production examples, formulation examples, and test examples; however, the

present invention is not limited only to these examples. In the formulation examples, the compound numbers are those shown in Table 1 below.

The following will describe some production examples for compounds (X).

Production Example 1 First, 0.20 g of (4-chlorobenzyl) malononitrile was dissolved in 5 ml of N, N-dimethylformamide, to which 46 mg of sodium hydride (60% in oil) was added, while stirring under ice cooling. After the evolution of hydrogen gas ceased, while stirring under ice cooling, 0.44 ml of allyl bromide was added dropwise, followed by further stirring at room temperature overnight. Then, 10% hydrochloric acid was added to the reaction mixture, which was ex- tracted with diethyl ether. The organic layer was successively washed with 10% hydrochloric acid, a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 0.13 g of 2-allyl-2- (4-chlorobenzyl) malononitrile (compound 1).

Yield: 54%; nD220 : 1.5326.

Production Example 2 Using 0.60 g of (1- (4-chlorophenyl)-1-methylethyl) malononitrile, 10 ml of N, N-dimethylformamide, 121 mg of sodium hydride (60% in oil), and 1.20 ml of allyl bromide, and according to the process described in the Pro- duction Example 1, there was obtained 0.60 g of 2-allyl-2- (l- (4-chlorophen- yl)-l-methylethyl) malononitrile (compound 2).

Yield: 85%; nid 23. 5 : 1.5354.

Production Example 3 Using 0.36 g of (1- (4-chlorophenyl)-2-methylpropyl) malononitrile, 5

ml of N, N-dimethylformamide, 75 mg of sodium hydride (60% in oil), and 0.20 ml of allyl bromide, and according to the process described in the Pro- duction Example 1, there was obtained 0.29 g of 2-allyl-2- (l- (4-chlorophen- yl)-2-methylpropyl) malononitrile (compound 3).

Yield: 69%; no"' : 1.5272.

Production Example 4 Using 0.50 g of (4-chlorobenzyl) malononitrile, 5 ml of N, N-dimethyl- formamide, 126 mg of sodium hydride (60% in oil), and 0.40 ml of 4-bromo-1- butene, and according to the process described in the Production Example 1, there was obtained 0.46 g of 2- (3-butenyl)-2- (4-chlorobenzyl) malononitrile (compound 4).

Yield: 72%; m. p.: 63.7°C.

Production Example 5 Using 1.12 g of (4- (trifluoromethyl) benzyl) malononitrile, 10 ml of N, N-dimethylformamide, 0.24 g of sodium hydride (60% in oil), and 0.63 ml of allyl bromide, and according to the process described in the Production Example 1, there was obtained 0.58 g of 2-allyl-2- (4- (trifluoromethyl) ben- zyl) malononitrile (compound 5).

Yield: 44%; m. p.: 80.2°C.

Production Example 6 Using 0.50 g of (4-cyanobenzyl) malononitrile, 5 ml of N, N-dimethyl- formamide, 132 mg of sodium hydride (60% in oil), and 0.42 ml of 4-bromo-1- butene, and according to the process described in the Production Example 1, there was obtained 0.19 g of 2- (3-butenyl)-2- (4-cyanobenzyl) malononitrile (compound 6).

Yield: 29%; m. p.: 109.4°C.

Production Example 7 Using 0.50 g of (4-cyanobenzyl) malononitrile, 5 ml of N, N-dimethyl- formamide, 132 mg of sodium hydride (60% in oil), and 0.49 ml of 5-bromo-1- pentene, and according to the process described in the Production Example 1, there was obtained 0.12 g of 2- (4-cyanobenzyl)-2- (4-pentenyl) malononitrile (compound 7).

Yield: 17%; m. p.: 91.5°C.

Production Example 8 Using 0.20 g of (2-chlorobenzyl) malononitrile, 5 ml of N, N-dimethyl- formamide, 46 mg of sodium hydride (60% in oil), and 0.44 ml of allyl bromide, and according to the process described in the Production Example 1, there was obtained 0.18 g of 2-allyl-2- (2-chlorobenzyl) malononitrile (com- pound 8).

Yield: 74%; nid 20. 5 : 1.5329.

Production Example 9 Using 0.50 g of (4-chlorobenzyl) malononitrile, 5 ml of N, N-dimethyl- formamide, 160 mg of sodium hydride (60% in oil), and 0.68 ml of cyclohexyl iodide, and according to the process described in the Production Example 1, there was obtained 0.20 g of 2- (4-chlorobenzyl)-2-cyclohexylmalononitrile (compound 9).

Yield: 28%; m. p.: 107.9°C.

Production Example 10 Using 0.56 g of (1- (4-chlorophenyl) ethyl) malononitrile, 5 ml of N, N-

dimethylformamide, 160 mg of sodium hydride (60% in oil), and 0.56 ml of 4- bromo-1-butene, and according to the process described in the Production Example 1, there was obtained 0.23 g of 2- (3-butenyl)-2- (l- (4-chlorophenyl)- ethyl) malononitrile (compound 10).

Yield: 32%; no'" : 1.5259.

Production Example 11 Using 0.50 g of (4- (trifluoromethoxy) benzyl) malononitrile, 5 ml of N, N-dimethylformamide, 123 mg of sodium hydride, and 0.35 ml of ally bromide, and according to the process described in the Production Example 1, there was obtained 0.26 g of 2-allyl-2- (4- (trifluoromethoxy) benzyl) malono- nitrile (compound 11).

Yield: 45%; no"' : 1.4682.

Production Example 12 Using 0.77 g of (1- (4- (trifluoromethoxy) phenyl-2-methylpropyl) malo- nonitrile, 5 ml of N, N-dimethylformamide, 160 mg of sodium hydride (60% in oil), and 0.55 ml of 4-bromo-l-butene, and according to the process described in the Production Example 1, there was obtained 0.30 g of 2- (3-butenyl)-2- (1- (4- (trifluoromethoxyphenyl)-2-methylpropyl) malononitrile (compound 12).

Yield: 33%; nid255 : 1. 4686.

Production Example 13 Using 2.35 g of (4-bromobenzyl) malononitrile, 50 ml of N, N-di- methylformamide, 0.44 g of sodium hydride (60% in oil), and 4.23 ml of allyl bromide, and according to the process described in the Production Example 1, there was obtained 2.33 g of 2-allyl-2- (4-bromobenzyl) malononitrile (com- pound 13).

Yield: 85%; m. p.: 61.7°C.

Production Example 14 Using 1.81 g of (4-cyanobenzyl) malononitrile, 50 ml of N, N-dimethyl- formamide, 0.44 g of sodium hydride (60% in oil), and 4.23 ml of allyl bro- mide, and according to the process described in the Production Example 1, there was obtained 1.04 g of 2-allyl-2- (4-cyanobenzyl) malononitrile (com- pound 14).

Yield: 47%; m. p.: 81.9°C.

Production Example 15 Using 0.23 g of (4- (trifluoromethoxy) benzyl) malononitrile, 5 ml of N, N-dimethylformamide, 60 mg of sodium hydride (60% in oil), and 0.20 ml of 4-bromo-1-butene, and according to the process described in the Produc- tion Example 1, there was obtained 0.16 g of 2- (3-butenyl)-2- (4- (trifluoro- methoxy) benzyl) malononitrile (compound 15).

Yield: 54%; nid 25. 5 : 1.4657.

Production Example 16 Using 0.76 g of (1- (4- (trifluoromethoxy) phenyl) ethyl) malononitrile, 5 ml of N, N-dimethylformamide, 180 mg of sodium hydride (60% in oil), and 0.61 ml of 4-bromo-1-butene, and according to the process described in the Production Example 1, there was obtained 0.36 g of 2- (3-butenyl)-2- (l- (4- (trifluoromethoxy) phenyl) ethyl) malononitrile (compound 16).

Yield: 39%; nid255 : 1. 4673.

Production Example 17 Using 0.20 g of (3-chlorobenzyl) malononitrile, 5 ml of N, N-dimethyl-

formamide, 46 mg of sodium hydride (60% in oil), and 0.44 ml of allyl bromide, and according to the process described in the Production Example 1, there was obtained 0.11 g of 2-allyl-2- (3-chlorobenzyl) malononitrile (com- pound 17).

Yield: 45%; nD2l5 : 1.5302.

Production Example 18 Using 1.74 g of (4-fluorobenzyl) malononitrile, 50 ml of N, N-di- methylformamide, 0.44 g of sodium hydride (60% in oil), and 4.23 ml of allyl bromide, and according to the process described in the Production Example 1, there was obtained 2.00 g of 2-allyl-2- (4-fluorobenzyl) malononitrile (com- pound 18).

Yield: 93%; nid 24. 5 : 1.5028.

Production Example 19 Using 0.50 g of (4-chlorobenzyl) malononitrile, 5 ml of N, N-dimethyl- formamide, 0.12 g of sodium hydride (60% in oil), and 0.33 ml of isobutyl iodide, and according to the process described in the Production Example 1, there was obtained 0.42 g of 2- (4-chlorobenzyl)-2-isobutylmalononitrile (com- pound 19).

Yield: 65%; m. p.: 73.2°C.

Production Example 20 Using 0.50 g of (2-methoxybenzyl) malononitrile, 10 ml of N, N-di- methylformamide, 0.12 g of sodium hydride (60% in oil), and 1.1 ml of allyl bromide, and according to the process described in the Production Example 1, there was obtained 0.50 g of 2-allyl-2- (2-methoxybenzyl) malononitrile (com- pound 20).

Yield: 83%; nDl35 : 1.5231.

Production Example 21 Using 0.50 g of (4-chlorobenzyl) malononitrile, 5 ml of N, N-dimethyl- formamide, 0.126 g of sodium hydride (60% in oil), and 0.47 ml of 5-brom-1- pentene, and according to the process described in the Production Example 1, there was obtained 0.49 g of 2- (4-chlorobenzyl)-2- (4-pentenyl) malononitrile (compound 21).

Yield: 72%; nid220 : 1. 5244.

Production Example 22 Using 0.50 g of (4-chlorobenzyl) malononitrile, 5 ml of N, N-dimethyl- formamide, 0.126 g of sodium hydride (60% in oil), and 0.40 g of 3-chloro-1- butene, and according to the process described in the Production Example 1, there was obtained 0.35 g of 2- (4-chlorobenzyl)-2- (l-methyl-2-propenyl)- malononitrile (compound 22).

Yield: 55%; nD225 : 1. 5284.

Production Example 23 Using 2.25 g of (3,4-dichlorobenzyl) malononitrile, 50 ml of N, N-di- methylformamide, 0.48 g of sodium hydride (60% in oil), and 1.30 ml of allyl bromide, and according to the process described in the Production Example 1, there was obtained 1.96 g of 2-allyl-2- (3, 4-dichlorobenzyl) malononitrile (compound 23).

Yield: 74%; m. p.: 71.8°C.

Production Example 24 Using 1.13 g of (2,4-dichlorobenzyl) malononitrile, 20 ml of N, N-di-

methylformamide, 0.24 g of sodium hydride (60% in oil), and 0.63 ml of allyl bromide, and according to the process described in the Production Example 1, there was obtained 0.78 g of 2-aUyl-2- (2, 4-dichlorobenzyl) malononitrile (compound 24).

Yield: 59%; nD245 : 1.5447 Production Example 25 Using 0.50 g of (4-chlorobenzyl) malononitrile, 5 ml of N, N-dimethyl- formamide, 0.16 g of sodium hydride (60% in oil), and 0.60 ml of 1-bromo-3- methyl-2-butene, and according to the process described in the Production Example 1, there was obtained 0.52 g of 2- (4-chlorobenzyl)-2- (3-methyl-2- butenyl) malononitrile (compound 25).

Yield: 77%; nid 25. 5 : 1.5263.

Production Example 26 Using 0.80 g of (1- (4-chlorophenyl)-2-methylpropyl) malononitrile, 10 ml of N, N-dimethylformamide, 0.21 g of sodium hydride (60% in oil), and 0.70 ml of 4-bromo-1-butene, and according to the process described in Pro- duction Example 1, there was obtained 0.32 g of 2- (3-butenyl)-2- (1- (4-chloro- phenyl)-2-methylpropyl) malononitrile (compound 26).

Yield: 32%; nD255 : 1.5217.

Production Example 27 Using 0.20 g of (4- (trifluoromethoxy) benzyl) malononitrile, 5 ml of N, N-dimethylformamide, 50 mg of sodium hydride (60% in oil), and 0.19 ml of 1-bromo-3-methyl-2-butene, and according to the process described in Pro- duction Example 1, there was obtained 0.19 g of 2- (3-methyl-2-butenyl)-2- (4- (trifluoromethoxy) benzyl) malononitrile (compound 27).

Yield: 74%; nD24. 5 : 1.4707.

Production Example 28 Using 0.50 g of (3-methoxybenzyl) malononitrile, 10 ml of N, N-di- methylformamide, 0.12 g of sodium hydride (60% in oil), and 1.1 ml of allyl bromide, and according to the process described in the Production Example 1, there was obtained 0.45 g of 2-allyl-2- (3-methoxybenzyl) malononitrile (com- pound 28).

Yield: 74%; nid220 : 1.5238.

Production Example 29 Using 0.50 g of (4-methoxybenzyl) malononitrile, 10 ml of N, N-di- methylformamide, 0.12 g of sodium hydride (60% in oil), and 1.1 ml of allyl bromide, and according to the process described in the Production Example 1, there was obtained 0.50 g of 2-allyl-2- (4-methoxybenzyl) malononitrile (com- pound 29).

Yield: 83%; nid220 : 1.5252.

Production Example 30 First, 0.24 g of (4- (trifluoromethoxy) benzylidene) malononitrile, 0.66 g of allyltributyltin, and 0.71 g of methyl iodide were dissolved in 10 ml of benzene, and the solution was heated to the reflux temperature. Then, 40 mg of azobis (isobutyronitrile) was added, and the mixture was stirred for 13 hours, while heating under reflux. The reaction mixture is poured into a mixture of 40 ml of hexane and 40 ml of acetonitrile, followed by phase sepa- ration. The acetonitrile layer was concentrated, and the resulting residue was subjected to silica gel thin layer chromatography to give 0.19 g of 2- allyl-2- (1- (4- (trifluoromethoxy) phenyl) ethyl) malononitrile (compound 30).

Yield: 65%; 1H-NMR (CDC13, TMS, 8 (ppm)): 1.68 (3H, d), 2.42-2.61 (2H, m), 3.25 (1H, q), 5.23-5.44 (2H, m), 5.83-5.94 (1H, m), 7.25 (2H, d), 7.40 (2H, d).

Production Example 31 Using 0.24 g of (4-(trifluoromethoxy) benzylidene) malononitrile, 10 ml of benzene, 0.66 g of allyltributyltin, 0.89 g of chloroiodomethane, and 66 mg of azobis (isobutyronitrile), and according to the process described in Production Example 30, there was obtained 0.20 g of 2-allyl-2- (1- (4- (tri- fluoromethoxy) phenyl)-2-chloroethyl) malononitrile (compound 31).

Yield: 61% ; 'H-NMR (CDC13, TMS, 8 (ppm)): 2.43-2.60 (2H, m), 3.43 (1H, dd), 4.03 (1H, dd), 4.22 (1H, dd), 5.33-5.53 (2H, m), 5.78-6.01 (1H, m), 7.35 (2H, m), 7.41 (2H, m).

Production Example 32 Using 0.50 g of (1- (4- (trifluoromethoxy) phenyl)-2-propenyl) malono- nitrile, 4 ml of N, N-dimethylformamide, 83 mg of sodium hydride (60% in oil), and 0.51 g of 4-bromo-1-butene, and according to the process described in Production Example 1, there was obtained 0.56 g of 2- (3-butenyl)-2- (l- (4- (trifluoromethoxy) phenyl)-2-propenyl) malononitrile (compound 32).

Yield: 93%; 'H-NMR (CDC13, TMS, 8 (ppm)) : 1.77-2.08 (2H, m), 2.41-2.51 (2H, m), 3.67 (1H, d), 5.07-5.18 (2H, m), 5.37-5.51 (2H, m), 5.69-5.82 (1H, m), 5.19- 5.33 (1H, m), 7.26 (2H, m), 7.45 (2H, m).

Production Example 33 Using 0.25 g of (1- (4- (trifluoromethoxy) phenyl)-2-propenyl) malono- nitrile, 2 ml of N, N-dimethylformamide, 42 mg of sodium hydride (60% in oil), and 0.45 g of allyl bromide, and according to the process described in Pro- duction Example 1, there was obtained 0.25 g of 2-allyl-2-(1-(4-(trifluoro-

methoxy) phenyl)-2-propenyl) malononitrile (compound 33).

Yield: 87%; 'H-NMR (CDC13, TMS, 8 (ppm)): 2.50-2.73 (2H, m), 3.68 (1H, d), 5.34-5.52 (4H, m), 5.83-5.97 (1H, m), 6.18-6.33 (1H, m), 7.27 (2H, m), 7.46 (2H, m).

Production Example 34 Using 0.62 g of (1- (4- (trifluoromethoxy) phenyl)-2-propenyl) malono- nitrile, 5 ml of N, N-dimethylformamide, 103 mg of sodium hydride (60% in oil), and 0.56 g of 3-bromo-1-propyne, and according to the process described in Production Example 1, there was obtained 0.59 g of 2- (2-propynyl)-2- (l- (4- (trifluoromethoxy) phenyl)-2-propenyl) malononitrile (compound 34).

Yield: 83%; 'H-NMR (CDC13, TMS, 8 (ppm)): 2.47 (1H, t), 2.74-2.93 (2H, m), 3.96 (1H, d), 5.47-5.55 (2H, m), 6.19-6.31 (1H, m), 7.28 (2H, m), 7.49 (2H, m).

Production Example 35 First, 0.41 g of 2- (3-butenyl)-2- (4-hydroxybenzyl) malononitrile and 0.76 g of dibromodifluoromethane was dissolved in 5 ml of N, N-dimethyl- formamide, and while stirring under ice-cooling, 80 mg of sodium hydride (60% in oil) was added, and the mixture was heated to 80 °C, followed by stirred for 5 hours. Then, a saturated ammonium chloride aqueous solution was added to the reaction mixture, which was extracted diethyl ether. The organic layer was successively washed with water, a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 0.16 g of 2- (3-butenyl)-2- (4- (bromodifluoromethoxy) benzyl) malononitrile (compound 35) as a low-polar compound.

Yield: 25%;

m. p.: 50.2°C.

Also given was 58mg of 2- (3-butenyl)-2- (4- (difluoromethoxy) benzyl)- malononitrile (compound 36) as a high-polar compound.

Yield: 12%; 'H-NMR (CDC13, TMS, 8 (ppm)): 2.02-2.07 (2H, m), 2.44-2.52 (2H, m), 3.21 (2H, s), 5.11-5.20 (2H, m), 5.77-5.86 (1H, m), 6.54 (1H, t), 7.16 (2H, d), 7.38 (2H, m).

Production Example 36 Using 0.43 g of (3,4- (methylenedioxy) benzyl) malononitrile, 5 ml of N, N-dimethylformamide, 100 mg of sodium hydride (60% in oil), and 0.36 g of 4-bromo-1-butene, and according to the process described in Production Example 1, there was obtained 0.42 g of 2- (3-butenyl)-2- (3, 4- (methylenedi- oxy) benzyl) malononitrile (compound 37).

Yield: 76%; 'H-NMR (CDC13, TMS, 8 (ppm)) : 1.99-2.05 (2H, m), 2.45-2.48 (2H, m), 3.14 (2H, s), 5.09-5.20 (2H, m), 5.72-5.90 (1H, m), 6.00 (2H, s), 6.82-6.85 (3H, m).

Production Example 37 First, 0.30 g of 2- (3-butenyl)-2- (4-hydroxybenzyl) malononitrile and 0.19 g of allyl bromide was dissolved in 5 ml of N, N-dimethylformamide, and 0.22 g of potassium carbonate was added, followed by stirred overnight at room temperature. Then, water was added to the reaction mixture, which was extracted diethyl ether. The organic layer was successively washed with water, a saturated sodium chloride aqueous solution, dried over anhy- drous magnesium sulfate, and then concentrated under reduced pressure.

The residue was subjected to silica gel column chromatography to give 0.34 g of 2- (3-butenyl)-2- (4- (2-propenyloxy) benzyl) malononitrile (compound 38).

Yield: 96%;

m. p.: 77.7°C.

Production Example 38 First, 0.48 g of 4-(trifluoromethoxy) benzylidenemalononitrile, 0.10 g of tetrakis (triphenylphosphine) palladium, and 0.26 g of allylmethyl carbon- ate were dissolved in 20 ml of tetrahydrofuran, and the solution was stirred at room temperature for 10 hours. Then, the residue obtained by concen- tration under reduced pressure was subjected to silica gel chromatography to give 0.56 g of 2-allyl-2- (4- (trifluoromethoxy)-a-methoxybenzyl) malononitrile (compound 39).

Yield: 89%; 'H-NMR (CDC13, TMS, 8 (ppm)): 2.66-2.79 (2H, m), 3.36 (3H, s), 4.43 (1H, s), 5.38-5.46 (2H, m), 5.85-5.99 (1H, m), 7.32 (2H, d), 7.53 (2H, d).

Production Example 39 Using 0.50 g of (4- (trifluoromethylthio) benzyl) malononitrile, 6 ml of N, N-dimethylformamide, 90 mg of sodium hydride (60% in oil), and 0.29 g of allyl bromide, and according to the process described in Production Example 1, there was obtained 0.49 g of 2-allyl-2- (4- (trifluoromethylthio) benzyl)- malononitrile (compound 41).

Yield: 84%; 'H-NMR (CDC13, TMS, 8 (ppm)): 2.69-2.75 (2H, m), 3.21 (2H, s), 5.39- 5.51 (2H, m), 5.88-6.02 (1H, m), 7.45 (2H, d), 7.70 (2H, d).

Production Example 40 Using 0.50 g of (4- (trifluoromethylthio) benzyl) malononitrile, 6 ml of N, N-dimethylformamide, 90 mg of sodium hydride (60% in oil), and 0.32 g of 4-bromo-1-butene, and according to the process described in Production Example 1, there was obtained 0.26 g of 2- (3-butenyl)-2- (4- (trifluoromethyl- thio) benzyl) malononitrile (compound 42).

Yield: 44%;

'H-NMR (CDC13, TMS, b (ppm)): 2.04-2.10 (2H, m), 2.45-2.54 (2H, m), 3.25 (2H, s), 5.10-5.22 (2H, m), 5.74-5.87 (1H, m), 7.45 (2H, d), 7.71 (2H, m).

Production Example 41 Using 0.51 g of 4- (trifluoromethylthio) benzylidenemalononitrile, 0.10 g of tetrakis (triphenylphosphine) palladium, 0.26 g of allylmethyl carbonate, and 20 ml of tetrahydrofuran, and according to the process described in Pro- duction Example 38, there was obtained 0.49 g of 2-allyl-2- (4- (trifluorometh- ylthio)-a-methoxybenzyl) malononitrile (compound 43).

Yield: 75%; 'H-NMR (CDC13, TMS, 8 (ppm)): 2.72-2.76 (2H, m), 3.38 (3H, s), 4.46 (1H, s), 5.38-5.48 (2H, m), 5.79-5.94 (1H, m), 7.56 (2H, m), 7.76 (2H, m).

Production Example 42 Using 1.76 g of (4-ethoxybenzyl) malononitrile, 30 ml of N, N-di- methylformamide, 0.40 g of sodium hydride (60% in oil), and 4.2 ml of allyl bromide, and according to the process described in the Production Example 1, there was obtained 1.30 g of 2-allyl-2- (4-ethoxybenzyl) malononitrile (com- pound 44).

Yield: 54%; m. p.: 84.3°C.

Production Example 43 Using 0.50 g of (4- (trifluoromethoxy) benzyl) malononitrile, 6 ml of N, N-dimethylformamide, 95 mg of sodium hydride (60% in oil), and 0.47 g of isopentyl bromide, and according to the process described in Production Example 1, there was obtained 0.42 g of 2- (3-methylbutyl)-2- (4- (trifluoro- methoxy) benzyl) malononitrile (compound 45).

Yield: 65%; 'H-NMR (CDC13, TMS, 8 (ppm)): 0.96 (3H, d), 1.59-1.65 (3H, m), 1.94-2.01 (2H, m), 3.20 (2H, s), 7.26 (2H, d), 7.43 (2H, d).

Production Example 44 Using 0.50 g of (4- (trifluoromethylthio) benzyl) malononitrile, 6 ml of N, N-dimethylformamide, 90 mg of sodium hydride (60% in oil), and 0.21 g of 1-chloro-2-butene, and according to the process described in Production Ex- ample 1, there was obtained 0.40 g of 2- (2-butenyl)-2- (4- (trifluoromethyl- thio) benzyl) malononitrile (compound 46).

Yield: 66%; 'H-NMR (CDC13, TMS, 8 (ppm)) : 1.72 (3H, dd, Z), 1.80 (3H, dd, E), 2.68 (2H, d, E), 2.73 (2H, d, Z), 3.18 (2H, s, Z), 3.19 (2H, s, E), 5.49-5.68 (1H, m, E, Z), 5.78-6.00 (1H, m, E, Z), 7.45 (2H, d, E, Z), 7.70 (2H, d, E, Z).

Production Example 45 Using 0.50 g of (4- (trifluoromethylthio) benzyl) malononitrile, 6 ml of N, N-dimethylformamide, 90 mg of sodium hydride (60% in oil), and 0.21 g of 3-chloro-1-butene, and according to the process described in Production Ex- ample 1, there was obtained 0.14 g of 2-(1-methyl-2-propenyl)-2-(4-(trifluoro- methylthio) benzyl) malononitrile (compound 47).

Yield: 24%; 'H-NMR (CDC13, TMS, 8 (ppm)): 1.47 (3H, d), 2.62-2.74 (1H, m), 3.19 (2H, dd), 5.35-5.46 (2H, m), 5.80-5.95 (2H, m), 7.45 (2H, d), 7.69 (2H, d).

Production Example 46 Using 1.93 g of (1- (3-chlorophenyl)-1-methylethyl) malononitrile, 30 ml of N, N-dimethylformamide, 0.39 g of sodium hydride (60% in oil), and 3.70 ml of allyl bromide, and according to the process described in the Pro- duction Example 1, there was obtained 1.14 g of 2-allyl-2- (l- (3-chlorophen- yl)-l-methylethyl) malononitrile (compound 48).

Yield: 50%; m. p.: 84.3°C.

Production Example 47

Using 0.60 g of (1-(2-chlorophenyl)-1-methylethyl) malononitrile, 10 ml of N, N-dimethylformamide, 0.12 g of sodium hydride (60% in oil), and 1.2 ml of allyl bromide, and according to the process described in the Production Example 1, there was obtained 0.60 g of 2-allyl-2- (1- (2-chlorophenyl)-1- methylethyl) malononitrile (compound 49).

Yield: 71%; nid 23. 5 : 1.5398.

Production Example 48 Using 2.01 g of (4-nitrobenzyl) malononitrile, 50 ml of N, N-dimethyl- formamide, 0.44 g of sodium hydride (60% in oil), and 4.23 ml of allyl bromide, and according to the process described in the Production Example 1, there was obtained 1.13 g of 2-allyl-2- (4-nitrobenzyl) malononitrile (com- pound 50).

Yield: 47%; m. p.: 94.2°C.

Production Example 49 Using 0.50 g of (4-chlorobenzyl) malononitrile, 5 ml of N, N-dimethyl- formamide, 0.12 g of sodium hydride (60% in oil), and 0.27 ml of isopropyl iodide, and according to the process described in the Production Example 1, there was obtained 0.19 g of 2- (4-chlorobenzyl)-2-isopropylmalononitrile (compound 51).

Yield: 31%; nD"' : 1.5229.

Production Example 50 Using 0.50 g of (4- (trifluoromethyl) benzyl) malononitrile, 21 ml of N, N-dimethylformamide, 100 mg of sodium hydride (60% in oil), and 0.45 g of 4-bromo-1-butene, and according to the process described in Production Example 1, there was obtained 0.25 g of 2- (3-butenyl)-2- (4- (trifluoromethyl)-

benzyl) malononitrile (compound 52).

Yield: 20%; 'H-NMR (CDC13, TMS, 8 (ppm)): 2.05-2. 10 (2H, m), 2.46-2.52 (2H, m), 3.28 (2H, s), 5.12-5.22 (2H, m), 5.77-5.86 (1H, m), 7.52 (2H, d), 7.69 (2H, d).

Production Example 51 Using 2.25 g of (2,3-dichlorobenzyl) malononitrile, 20 ml of N, N- dimethylformamide, 0.48 g of sodium hydride (60% in oil), and 1.30 ml of allyl bromide, and according to the process described in the Production Example 1, there was obtained 1.72 g of 2-allyl-2- (2, 3-dichlorobenzyl)- malononitrile (compound 53).

Yield: 65%; nD : 1. 5448.

Production Example 52 Using 2.25 g of (2,6-dichlorobenzyl) malononitrile, 20 ml of N, N-di- methylformamide, 0.48 g of sodium hydride (60% in oil), and 1.30 ml of allyl bromide, and according to the process described in the Production Example 1, there was obtained 2.00 g of 2-allyl-2- (2, 6-dichlorobenzyl) malononitrile (compound 54).

Yield: 75%; nD235 : 1. 5483.

Production Example 53 First, 0.50 g of 4-(trifluoromethylthio) benzylidenemalononitrile, 60 mg of tris (dibenzylideneacetone) dipalladium-chloroform complex, and 0.11 g of 1, 1'-bis (diphenylphosphino) ferrocene were added to 10 ml of tetrahydro- furan, and 0.30 g of allyl chloride and 0.39 g of trimethylsilyl cyanide were further added under an atmosphere of nitrogen, followed by stirring at 75°C for a day. The reaction mixture was then filtered through silica gel and the filtrate was concentrated. The residue was subjected to silica gel chroma-

tography to give 0.42 g of 2-allyl-2- (4- (trifluoromethylthio)-a-cyanobenzyl)- malononitrile (compound 56).

Yield: 67%; 'H-NMR (CDC13, TMS, 8 (ppm)): 2.92-3.12 (2H, m), 4.29 (1H, s), 5.59- 5.65 (2H, m), 5.81-5.98 (1H, m), 7.63 (2H, d), 7.82 (2H, d).

Production Example 54 Using 0.47 g of 4-(trifluoromethoxy) benzylidenemalononitrile, 60 mg of tris (dibenzylideneacetone) dipalladium-chloroform complex, 0.11 g of 1,1'- bis (diphenylphosphino) ferrocene, 10 ml of tetrahydrofuran, 0.30 g of allyl chloride, and 0.39 g of trimethylsilyl cyanide, and according to the process described in Production Example 53, there was obtained 0.42 g of 2-allyl-2- (4- (trifluoromethoxy)-a-cyanobenzyl) malononitrile (compound 55).

Yield: 70%; 'H-NMR (CDC13, TMS, 8 (ppm)): 2.92-3.10 (2H, m), 4.27 (1H, s), 5.58- 5.63 (2H, m), 5.91-5.97 (1H, m), 7.37 (2H, d), 7.62 (2H, d).

Production Example 55 Using 0.30 g of allylmalononitrile, 4 ml of N, N-dimethylformamide, 130 mg of sodium hydride (60% in oil), and 0.99 g of 2,4-bis (trifluoromethyl)- benzyl bromide, and according to the process described in Production Exam- ple 1, there was obtained 0.70 g of 2-allyl-2- (2, 4-bis (trifluoromethyl) benzyl)- malononitrile (compound 57).

Yield: 72%; 'H-NMR (CDC13, TMS, 8 (ppm)): 2.82 (2H, d), 3.47 (2H, s), 5.45-5.58 (2H, m), 5.89-6.05 (1H, m), 7.92 (1H, d), 7.98 (1H, d), 8.02 (1H, s).

Production Example 56 Using 0.30 g of allylmalononitrile, 4 ml of N, N-dimethylformamide, 125 mg of sodium hydride (60% in oil), and 0.85 g of 2-chloro-4- (trifluoro- methyl) benzyl bromide, and according to the process described in Production

Example 1, there was obtained 0.40 g of 2-allyl-2- (2-chloro-4- (trifluorometh- yl) benzyl) malononitrile (compound 58).

Yield: 47%; 'H-NMR (CDC13, TMS, 8 (ppm)): 2.84 (2H, d), 3.51 (2H, s), 5.41-5.56 (2H, m), 5.88-6.07 (1H, m), 7.62 (1H, d), 7.71 (1H, d), 7.83 (1H, s).

Production Example 57 Using 0.50 g of (4- (trifluoromethoxy) benzyl) malononitrile, 3 ml of N, N-dimethylformamide, 93 mg of sodium hydride (60% in oil), and 0.42 g of 1-bromo-2-butyne, and according to the process described in Production Ex- ample 1, there was obtained 0.47 g of 2- (2-butynyl)-2- (4- (trifluoromethoxy)- benzyl) malononitrile (compound 59).

Yield: 70%; 'H-NMR (CDC13, TMS, 8 (ppm)): 1.93 (3H, t), 2.85 (2H, q), 3.33 (2H, s), 7.25 (2H, d), 7.45 (2H, d).

Production Example 58 Using 0.30 g of (3-butenyl) malononitrile, 5 ml of N, N-dimethylform- amide, 110 mg of sodium hydride (60% in oil), and 0.75 g of 2-chloro-4- (tri- fluoromethyl) benzyl bromide, and according to the process described in Pro- duction Example 1, there was obtained 0.30 g of 2- (3-butenyl)-2- (2-chloro-4- (trifluoromethyl) benzyl) malononitrile (compound 60).

Yield: 39%; 'H-NMR (CDC13, TMS, 8 (ppm)): 2.10-2.17 (2H, m), 2.49-2.52 (2H, m), 3.53 (2H, s), 5.11-5.22 (2H, m), 5.72-5.88 (1H, m), 7.62 (1H, d), 7.70 (1H, d), 7.75 (1H, s).

Production Example 59 Using 0.60 g of allylmalononitrile, 8 ml of N, N-dimethylformamide, 255 mg of sodium hydride (60% in oil), and 1.55 g of 4- (methylsulfonyl) benzyl bromide, and according to the process described in Production Example 1,

there was obtained 0.64 g of 2-allyl-2- (4- (methylsulfonyl) benzyl) malono- nitrile (compound 61).

Yield: 41%; 'H-NMR (CDCl3, TMS, 8 (ppm)): 2.78 (2H, d), 3.10 (3H, s), 3.29 (2H, s), 5.45-5.53 (2H, m), 5.88-6.07 (1H, m), 7.61 (2H, d), 8.01 (2H, d).

Production Example 60 Using 1.23 g of (2,3,4,5,6-pentafluorobenzyl) malononitrile, 20 ml of N, N-dimethylformamide, 0.24 g of sodium hydride (60% in oil), and 0.63 ml of allyl bromide, and according to the process described in the Production Example 1, there was obtained 0.98 g of 2-allyl-2- (2, 3,4,5,6-pentafluoroben- zyl) malononitrile (compound 62).

Yield:68%; m. p.: 78.2°C.

Production Example 61 Using 0.15 g of allylmalononitrile, 5 ml of N, N-dimethylformamide, 62 mg of sodium hydride (60% in oil), and 0.43 g of 2-nitro-4- (trifluorometh- yl) benzyl bromide, and according to the process described in Production Example 1, there was obtained 0.32 g of 2-allyl-2- (2-nitro-4- (trifluorometh- yl) benzyl) malononitrile (compound 63).

Yield: 70%; 'H-NMR (CDC13, TMS, 8 (ppm)): 2.88 (2H, d), 3.80 (2H, s), 5.46-5.57 (2H, m), 5.88-6.05 (1H, m), 7.82 (1H, d), 7.94 (1H, d), 8.46 (1H, s).

Production Example 62 Using 0.15 g of allylmalononitrile, 5 ml of N, N-dimethylformamide, 62 mg of sodium hydride (60% in oil), and 0.44 g of 2, 6-dichloro-4- (trifluoro- methyl) benzyl bromide, and according to the process described in Production Example 1, there was obtained 0.20 g of 2-allyl-2- (2, 6-dichloro-4- (trifluoro- methyl) benzyl) malononitrile (compound 64).

Yield: 43%; 'H-NMR (CDCl3, TMS, 8 (ppm)): 2.94 (2H, d), 3.75 (1H, s), 5.50-5.58 (2H, m), 5.95-6.10 (1H, s), 7.71 (2H, s).

Production Example 63 Using 0.15 g of (3-butenyl) malononitrile, 5 ml of N, N-dimethylform- amide, 55 mg of sodium hydride (60% in oil), and 0.39 g of 2,6-dichloro-4- (trifluoromethyl) benzyl bromide, and according to the process described in Production Example 1, there was obtained 95 mg of 2- (3-butenyl)-2- (2, 6-di- chloro-4- (trifluoromethyl) benzyl) malononitrile (compound 65).

Yield: 22%; 'H-NMR (CDCl3, TMS, S (ppm)): 2.22-2.28 (2H, m), 2.49-2.57 (2H, m), 3.77 (2H, s), 5.13-5.23 (2H, m), 5.78-5.90 (1H, m), 7.69 (2H, s).

Production Example 64 Using 0.41 g of (1- (3-chlorophenyl)-2-methylpropyl) malononitrile, 5 ml of N, N-dimethylformamide, 85 mg of sodium hydride (60% in oil), and 0.22 ml of allyl bromide, and according to the process described in the Pro- duction Example 1, there was obtained 0.35 g of 2-allyl-2- (1- (3-chlorophen- yl)-2-methylpropyl) malononitrile (compound 66).

Yield: 73%; nD230 : 1.5267.

Production Example 65 Using 97 mg of (3-butenyl) malononitrile, 5 ml of N, N-dimethylform- amide, 37 mg of sodium hydride (60% in oil), and 0.25 g of 2-nitro-4- (trifluo- romethyl) benzyl bromide, and according to the process described in Produc- tion Example 1, there was obtained 0.12 g of 2- (3-butenyl)-2- (2-nitro-4- (tri- fluoromethyl) benzyl) malononitrile (compound 67).

Yield: 43%; 'H-NMR (CDC13, TMS, 8 (ppm)): 2.21-2.29 (2H, m), 2.54-2.65 (2H, m),

5.64-5.76 (2H, m), 5.82-5.98 (1H, m), 7.33 (1H, d), 8.03 (1H, m), 8.45 (1H, s).

Production Example 66 Using 0.50 g of (4-chlorobenzyl) malononitrile, 5 ml of N, N-dimethyl- formamide, 0.16 g of sodium hydride (60% in oil), and 0.33 ml of methyl iodide, and according to the process described in the Production Example 1, there was obtained 0.23 g of 2- (4-chlorobenzyl)-2-methylmalononitrile (com- pound 68).

Yield: 43%; m. p. : 91. 1°C.

Production Example 67 Using 0.30 g of allylmalononitrile, 4 ml of N, N-dimethylformamide, 124 mg of sodium hydride (60% in oil), and 0.80 g of 3-fluoro-4-(trifluoro- methyl) benzyl bromide, and according to the process described in Production Example 1, there was obtained 0.37 g of 2-allyl-2- (3-fluoro-4- (trifluoro- methyl) benzyl) malononitrile (compound 69).

Yield: 46% ; 'H-NMR (CDC13, TMS, 8 (ppm)): 2.77 (2H, d), 3.23 (2H, s), 5.43-5.54 (2H, m), 5.86-5.98 (1H, m), 7.25 (1H, m), 7.29 (1H, d), 7.65-7.72 (1H, m).

Production Example 68 Using 0.30 g of allylmalononitrile, 6 ml of N, N-dimethylformamide, 124 mg of sodium hydride (60% in oil), and 0.68 g of 4- (methylthio) benzyl bromide, and according to the process described in Production Example 1, there was obtained 0.42 g of 2-allyl-2- (4- (methylthio) benzyl) malononitrile (compound 70).

Yield: 62%; 'H-NMR (CDC13, TMS, 5 (ppm)): 2.49 (3H, s), 2.70 (2H, s), 3.16 (2H, s), 5.38-5.47 (2H, m), 5.80-5.99 (1H, m), 7.27 (2H, d), 7.28 (2H, d).

Production Example 69

Using 0.50 g of (4- (trifluoromethyl) benzyl) malononitrile, 6 ml of N, N-dimethylformamide, 98 mg of sodium hydride (60% in oil), and 0.41 g of 1-iodopropane, and according to the process described in Production Exam- ple 1, there was obtained 0.21 g of 2-propyl-2- (4- (trifluoromethyl) benzyl)- malononitrile (compound 71).

Yield: 41%; 'H-NMR (CDC13, TMS, 8 (ppm)): 1.06 (3H, t), 1.68-1.77 (2H, m), 1.88- 1.96 (2H, m), 7.48 (2H, d), 7.63 (2H, m).

Production Example 70 Using 0.50 g of (4-chlorobenzyl) malononitrile, 5 ml of N, N-dimethyl- formamide, 0.16 g of sodium hydride (60% in oil), and 0.39 ml of ethyl bromide, and according to the process described in the Production Example 1, there was obtained 0.20 g of 2- (4-chlorobenzyl)-2-ethylmalononitrile (com- pound 72).

Yield: 35%; m. p.: 70.9°C.

Production Example 71 Using 0.50 g of (4-chlorobenzyl) malononitrile, 5 ml of N, N-dimethyl- formamide, 0.16 g of sodium hydride (60% in oil), and 0.85 g of (Z)-l-bromo- 3-hexene, and according to the process described in the Production Example 1, there was obtained 0.22 g of 2- (4-chlorobenzyl)-2- ( (Z)-3-hexenyl) malono- nitrile (compound 73).

Yield: 31%; m. p.: 44.8°C.

Production Example 72 Using 0.56 g of (1- (4-chlorophenyl) ethyl) malononitrile, 5 ml of N, N- dimethylformamide, 160 mg of sodium hydride (60% in oil), and 0.46 ml of allyl bromide, and according to the process described in the Production

Example 1, there was obtained 0.29 g of 2-allyl-2- (1- (4-chlorophenyl) ethyl)- malononitrile (compound 74).

Yield: 43%; nid 25. 5 : 1.5294.

Production Example 73 Using 0.50 g of (4- (trifluoromethyl) benzyl) malononitrile, 6 ml of N, N-dimethylformamide, 98 mg of sodium hydride (60% in oil), and 0.27 g of bromoethane, and according to the process described in Production Example 1, there was obtained 0.33 g of 2-ethyl-2- (4- (trifluoromethyl) benzyl) malono- nitrile (compound 75).

Yield: 58%; 'H-NMR (CDCl3, TMS, 8 (ppm)) : 1.35 (2H, t), 2.06 (2H, q), 3.26 (2H, s), 7.52 (2H, d), 7.68 (2H, d).

Production Example 74 Using 0.56 g of (1- (4-chlorophenyl) ethyl) malononitrile, 5 ml of N, N- dimethylformamide, 160 mg of sodium hydride (60% in oil), and 0.65 ml of 1- bromo-4-pentene, and according to the process described in the Production Example 1, there was obtained 0.25 g of 2- (l- (4-chlorophenyl) ethyl)-2- (4- pentenyl) malononitrile (compound 76).

Yield: 33%; no"' : 1.5204.

Production Example 75 Using 0.50 g of (4-methylbenzyl) malononitrile, 5 ml of N, N-di- methylformamide, 0.18 g of sodium hydride (60% in oil), and 0.50 ml of allyl bromide, and according to the process described in the Production Example 1, there was obtained 0.37 g of 2-allyl-2- (4-methylbenzyl) malononitrile (com- pound 77).

Yield: 60%;

m. p.: 74.5°C.

Production Example 76 First, 0.40 g of 2- (3-butenyl)-2- (4-hydroxybenzyl) malononitrile and 0.22 g of acetic anhydride was dissolved in 5 ml of toluene, to which 0.23 g of triethylamine was added, followed by stirring overnight at room temperature.

Then, water was added to the reaction mixture, which was extracted with diethyl ether. The organic layer was successively washed with a saturated ammonium chloride aqueous solution, a saturated sodium bicarbonate aqueous solution, a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pres- sure. The residue was subjected to silica gel column chromatography to give 0.45 g of 2- (3-butenyl)-2- (4- (acetyloxy) benzyl) malononitrile (compound 78).

Yield: 95%; m. p.: 80.2°C.

Production Example 77 Using 0.50 g of (4- (trifluoromethyl) benzyl) malononitrile, 10 ml of N, N-dimethylformamide, 89 mg of sodium hydride (60% in oil), and 0.33 g of 5-bromo-1-pentene, and according to the process described in Production Ex- ample 1, there was obtained 0.16 g of 2- (4-pentenyl)-2- (4- (trifluoromethyl)- benzyl) malononitrile (compound 79).

Yield: 25%; 'H-NMR (CDC13, TMS, 8 (ppm)) : 1.84-1.87 (2H, m), 1.96-2.02 (2H, m), 2.18 (2H, t), 3.25 (2H, s), 5.05-5.11 (2H, m), 5.76-5.86 (1H, m), 7.51 (2H, d), 7.58 (2H, d).

Production Example 78 First, 0.40 g of 2- (3-butenyl)-2- (4-hydroxybenzyl) malononitrile was dissolved in 5 ml of N, N-dimethylformamide, to which 75 mg of sodium

hydride (60% in oil) was added, while stirring under ice cooling. After the evolution of hydrogen gas ceased, while stirring under ice cooling, 0.49 g of 1,1,2,2-tetrafluoro-1-iodoethane was added dropwise, followed by further stirring at room temperature overnight. Then, a saturated ammonium chloride aqueous solution was added to the reaction mixture, which was ex- tracted with diethyl ether. The organic layer was successively washed with water, a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 82 mg of 2- (3-butenyl)-2- (4- (1, 1, 2,2-tetrafluoroethoxy) benzyl) malononitrile (compound 80).

Yield: 14%; m. p.: 60.5°C.

Production Example 79 Using 0.40 g of 2-(3-butenyV-2-(4-hydroxybenzyvmalononitrile, 5 ml of N, N-dimethylformamide, 75 mg of sodium hydride (60% in oil), and 0.45 g of 2, 2,2-trifluoro-1-iodoethane, and according to the process described in the Production Example 78, there was obtained 70 mg of 2- (3-butenyl)-2- (4- (2,2,2-trifluoroethoxy) benzyl) malononitrile (compound 81).

Yield: 13%; m. p.: 58.0°C.

Production Example 80 First, 0.48 g of (4-(trifluoromethoxy) benzyliden) malononitrile and 1.0 g of ethanol was dissolved in 20 ml of tetrahydrofuran, to which 0.10 g of tetrakis (triphenylphosphine) palladium and 0.26 g of allyl methyl carbonate was added, followed by further stirring for 10 hours at room temperature.

Then, the reaction mixture was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 0.65 g of

2-allyl-2- (4- (trifluoromethoxy)-a-ethoxybenzyl) malononitrile (compound 82).

Yield: 99%; 'H-NMR (CDC13, TMS, 8 (ppm)): 1.26 (3H, t), 2.66-2.79 (2H, m), 3.36- 3.57 (2H, m), 4.54 (1H, s), 5.38-5.46 (2H, m), 5.87-5.99 (1H, m), 7.30 (2H, d), 7.55 (2H, d).

Production Example 81 Using 0.36 g of (4-cyanobenzyliden) malononitrile, 0.10 g of tetra- kis (triphenylphosphine) palladium, and 0.26 g of allyl methyl carbonate, and 20 ml of tetrahydrofuran, and according to the process described in the Production Example 38, there was obtained 0.11 g of 2-allyl-2- (4-cyano-a- methoxybenzyl) malononitrile (compound 83).

Yield: 22%; 'H-NMR (CDCl3, TMS, 8 (ppm)): 2.72-2.81 (2H, m), 3.38 (3H, s), 4.47 (1H, s), 5.39-5.49 (2H, m), 5.80-5.98 (1H, m), 7.64 (2H, d), 7.79 (2H, d).

Production Example 82 Using 0.38 g of (4-chlorobenzyliden) malononitrile, 0.10 g of tetra- kis (triphenylphosphine) palladium, and 0.26 g of allyl methyl carbonate, and 20 ml of tetrahydrofuran, and according to the process described in the Production Example 38, there was obtained 0.44 g of 2-allyl-2- (4-chloro-a- methoxybenzyl) malononitrile (compound 84).

Yield: 84%; 1H-NMR (CDC13, TMS, 8 (ppm)): 2.65-2.76 (2H, m), 3.35 (3H, s), 4.41 (1H, s), 5.37-5.47 (2H, m), 5.85-6.00 (1H, m), 7.45 (4H, bs).

Production Example 83 Using 0.41 g of (2,2-dimethylpropyl) malononitrile, 7 ml of N, N-di- methylformamide, 0.13 g of sodium hydride (60% in oil), and 0.92 g of 4- (trifluoromethyl) benzyl bromide, and according to the process described in the Production Example 1, there was obtained 0.59 g of 2- (2, 2-dimethyl-

propyl)-2- (4- (trifluoromethoxy) benzyl) malononitrile (compound 85).

Yield: 63%; 'H-NMR (CDC13, TMS, 8 (ppm)): 1.20 (9H, s), 1.94 (2H, s), 3.21 (2H, s), 7.26 (2H, d), 7.44 (2H, d).

Production Example 84 Using 1.36 g of (2,2-dimethylpropyl) malononitrile, 20 ml of N, N-di- methylformamide, 0.43 g of sodium hydride (60% in oil), and 3.00 g of 4- bromobenzyl bromide, and according to the process described in the Pro- duction Example 1, there was obtained 2.74 g of 2- (4-bromobenzyl)-2- (2, 2- dimethylpropyl) malononitrile (compound 86).

Yield: 90% ; 'H-NMR (CDC13, TMS, 8 (ppm)) : 1. 19 (9H, s), 1.91 (2H, s), 3.16 (2H, s), 7.28 (2H, d), 7.54 (2H, d).

Production Example 85 Using 0.50 g of (4- (trifluoromethoxy) benzyl) malononitrile, 8 ml of N, N-dimethylformamide, 96 mg of sodium hydride (60% in oil), and 0.57 g of isobytyl bromide, and according to the process described in the Production Example 1, there was obtained 0.31 g of 2-isobutyl-2- (4- (trifluoromethoxy)- benzyl) malononitrile (compound 87).

Yield: 51%; 'H-NMR (CDC'3, TMS, 5 (PPM)) : 1.13 (6H, d), 1.88 (2H, d), 2.13 (1H, hept), 3.20 (2H, s), 7.26 (2H, d), 7.43 (2H, d).

Production Example 86 Using 0.50 g of (4- (trifluoromethoxy) benzyl) malononitrile, 8 ml of N, N-dimethylformamide, 96 mg of sodium hydride (60% in oil), and 0.63 g of pentyl bromide, and according to the process described in the Production Example 1, there was obtained 0.45 g of 2-pentyl-2- (4- (trifluoromethoxy)- benzyl) malononitrile (compound 88).

Yield: 70%; 'H-NMR (CDC13, TMS, 8 (ppm)) : 0.93 (3H, t), 1.29-1.49 (4H, m), 1.62- 1.80 (2H, m), 1.92-1.99 (2H, m), 3.20 (2H, s), 7.26 (2H, d), 7.41 (2H, d).

Production Example 87 Using 0.50 g of (3- (trifluoromethoxy) benzyl) malononitrile, 20 ml of N, N-dimethylformamide, 92 mg of sodium hydride (60% in oil), and 0.38 g of allyl bromide, and according to the process described in the Production Example 1, there was obtained 0.54 g of 2-allyl-2- (3- (trifluoromethoxy)- benzyl) malononitrile (compound 89).

Yield: 93%; 'H-NMR (CDC'31 TMS, 5 (ppm)): 2.70-2.75 (2H, m), 3.21 (2H, s), 5.30- 5.51 (2H, m), 5.86-6.02 (1H, m), 7.25-7.50 (4H, m).

Production Example 88 Using 0.50 g of (3- (trifluoromethoxy) benzyl) malononitrile, 20 ml of N, N-dimethylformamide, 92 mg of sodium hydride (60% in oil), and 420 mg of 4-bromo-1-butene, and according to the process described in the Produc- tion Example 1, there was obtained 0.28 g of 2- (3-butenyl)-2- (3- (trifluoro- methoxy) benzyl) malononitrile (compound 90).

Yield: 46%; 'H-NMR (CDC13, TMS, 8 (ppm)): 2.00-2.09 (2H, m), 2.41-2.53 (2H, m), 3.24 (2H, s), 5.07-5.21 (2H, m), 5.73-5.89 (1H, m), 7.25-7.50 (4H, m).

Production Example 89 First, 1.0 g of (4-methoxybenzylidene) malononitrile was dissolved in 30 ml of tetrahydrofuran, to which 0.57 g of trimethylsilyl cyanide was added at room temperature under a atmosphere of nitrogen, followed by stirred for 30 minutes. Then, 5.5 ml of tetrabutylammonium fluoride (1.0 M solution of tetrahydrofuran) was added dropwise to the mixture under ice-cooling, followed by stirred for 4 hours keeping ice-cooling. Then, 0.98 g of allyl

bromide was added dropwise followed by stirring overnight at room tem- perature. Then, a saturated ammonium chloride aqueous solution was added to the reaction mixture, which was extracted diethyl ether. The organic layer was successively washed with water, a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 1.0 g of 2-allyl-2- (4-methoxy-a- cyanobenzyl) malononitrile (compound 91).

Yield: 76%; 'H-NMR (CDC13, TMS, s (ppm)): 2.98 (2H, ddd), 3.85 (3H, s), 4.26 (1H, s), 5.54-5.62 (2H, m), 5.87-6.07 (1H, m), 7.04 (2H, d), 7.47 (2H, d).

Production Example 90 Using 1.0 g of (4-methylbenzyliden) malononitrile, 30 ml of tetra- hydrofuran, 0.62 g of trimethylsilyl cyanide, 6.0 ml of tetrabutylammonium fluoride (1.0 M solution of tetrahydrofuran), and 1.08 g of allyl bromide, and according to the process described in the Production Example 89, there was obtained 1.0 g of 2-allyl-2- (4-methyl-a-cyanobenzyl) malononitrile (compound 92).

Yield: 76%; 'H-NMR (CDC13, TMS, 8 (ppm)): 2.41 (3H, s), 2.96 (2H, ddd), 4.23 (1H, s), 5.54-5.60 (2H, m), 5.87-6.01 (1H, m), 7.31 (2H, d), 7.43 (2H, d).

Production Example 91 Using 0.50 g of (4- (methoxycarbonyl) benzylidene) malononitrile, 70 mg of tris (dibenzylideneacetone) dipalladium-chloroform complex, 0.14 g of 1, l'-bis (diphenylphosphino) ferrocene, 12 ml of tetrahydrofuran, and 0.37 g of allyl chloride, and according to the process described in the Production Example 53, there was obtained 0.31 g of 2-allyl-2- (4- (methoxycarbonyl)-a- cyanobenzyl) malononitrile (compound 93).

Yield: 48%; 1H-NMR (CDC13, TMS, 8 (ppm)): 2.92-3.13 (2H, m), 3.96 (3H, s), 4.32 (1H, s), 5.57-5.65 (2H, m), 5.89-6.03 (1H, m), 7.65 (2H, d), 8.19 (2H, d).

Production Example 92 Using 0.3 g of (3-butenyl) malononitrile, 5 ml of N, N-dimethylform- amide, 0.1 g of sodium hydride (60% in oil), and 0.72 g of 3,5-bis (trifluoro- methyl) benzyl bromide, and according to the process described in the Pro- duction Example 1, there was obtained 0.12 g of 2- (3, 5-bis (trifluoromethyl)- benzyl)-2- (3-butenyl) malononitrile (compound 94).

Yield: 14%; 1H-NMR (CDC13, TMS, 8 (ppm)): 2.08-2.13 (2H, m), 2.48-2.56 (2H, m), 3.34 (2H, s), 5.14-5.23 (2H, m), 5.78-5.87 (1H, m), 7.86 (2H, s), 7.95 (1H, s).

Production Example 93 First, 0.72 g of 2, 3-dimethoxybenzyl bromide was dissolved in 3 ml of N, N-dimethylformamide, to which a suspension 0.05 g of sodium hydride (60% in oil) and 0.3 g of allylmalononitrile in 2ml of N, N-dimethylformamide was added dropwise, while stirring under ice cooling, followed by further stirring at 0°C for 4 hours. Then, 10% hydrochloric acid was added to the reaction mixture, which was extracted with ethyl acetate. The organic layer was successively washed with water, a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 0.34 g of 2-allyl-2-(2, 3-dimethoxybenzyl)- malononitrile (compound 95).

Yield: 46%; 'H-NMR (CDC13, TMS, 8 (ppm)): 2.67 (2H, d), 3.31 (2H, s), 3.88 (3H, s), 3.90 (3H, s), 5.37-5.94 (2H, m), 5.84-6.01 (1H, s), 6.90-7.06 (3H, m).

Production Example 94

Using 0.47 g of 4-vinylbenzyl chloride, 5 ml of N, N-dimethylform- amide, 0.13 g of sodium hydride (60% in oil), and 0.3 g of allylmalononitrile, and according to the process described in the Production Example 93, there was obtained 0.22 g of 2-allyl-2- (4-vinylbenzyl) malononitrile (compound 96).

Yield: 35%; 'H-NMR (CDC13, TMS, 8 (ppm)): 2.69 (2H, d), 3.19 (2H, s), 5.29 (1H, dd), 5.44 (2H, dd), 5.77 (1H, dd), 5.89-6.04 (1H, m), 6.72 (1H, dd), 7.33 (2H, d), 7.44 (2H, d).

Production Example 95 Using 0.40 g of 4-acetylbenzyl chloride, 5 ml of N, N-dimethylform- amide, 0.08 g of sodium hydride (60% in oil), and 0.2 g of allylmalononitrile, and according to the process described in the Production Example 93, there was obtained 0.25 g of 2- (4-acetylbenzyl)-2-allylmalononitrile (compound 97).

Yield: 56%; 'H-NMR (CDC13, TMS, 8 (ppm)): 2.63 (3H, s), 2.73 (2H, d), 3.22 (2H, s), 4.89-5.02 (2H, m), 5.87-6.05 (1H, m), 7.49 (2H, d), 7.97 (2H, d).

Production Example 96 Using 0.30 g of 2- (3-butenyl)-2- (4-hydroxybenzyl) malononitrile, 5 ml of N, N-dimethylformamide, 60 mg of sodium hydride (60% in oil), and 0.18 g of ethyl bromide, and according to the process described in the Production Example 78, there was obtained 255 mg of 2- (3-butenyl)-2- (4-ethoxybenzyl)- malononitrile (compound 98).

Yield: 75%; 'H-NMR (CDC13, TMS, 8 (ppm)) : 1.42 (3H, t), 1.96-2.04 (2H, m), 2.39- 2.55 (2H, m), 3.17 (2H, s), 4.04 (2H, q), 5.08-5.19 (2H, m), 5.71-5.92 (1H, m), 6.90 (2H, bd), 7.27 (2H, bd).

Production Example 97 Using 0.30 g of 2- (3-butenyl)-2- (4-hydroxybenzyl) malononitrile, 5 ml

of N, N-dimethylformamide, 60 mg of sodium hydride (60% in oil), and 0.28 g of propyl iodide, and according to the process described in the Production Example 78, there was obtained 215 mg of 2- (3-butenyl)-2- (4-propoxyben- zyl) malononitrile (compound 99).

Yield: 60%; 1H-NMR (CDCIs, TMS, 8 (ppm)) : 1.04 (3H, t), 1.72-1.87 (2H, m), 1.97- 2.04 (2H, m), 2.41-2.50 (2H, m), 3.17 (2H, s), 3.92 (2H, t), 5.08-5.20 (2H, m), 5.70-5.90 (1H, m), 6.90 (2H, bd), 7.27 (2H, bd).

Production Example 98 Using 0.30 g of 2- (3-butenyl)-2- (4-hydoroxybenzyl) malononitrile, 5 ml of N, N-dimethylformamide, 60 mg of sodium hydride (60% in oil), and 0.21 g of isopropyl bromide, and according to the process described in the Pro- duction Example 78, there was obtained 227 mg of2- (3-butenyl)-2- (4-isopro- poxybenzyl) malononitrile (compound 100).

Yield: 64%; 1H-NMR (CDCl3, TMS, 8 (ppm)) : 1.34 (6H, d), 1.97-2.04 (2H, m), 2.41- 2.52 (2H, m), 3.16 (2H, s), 4.55 (1H, hept), 5.08-5.19 (2H, m), 5.72-5.89 (1H, m), 6.89 (2H, d), 7.26 (2H, d).

Production Example 99 Using 0.72 g of 4-ethylbenzyl chloride, 5 ml of N, N-dimethylform- amide, 0.19 g of sodium hydride (60% in oil), and 0.5 g of allylmalononitrile, and according to the process described in the Production Example 93, there was obtained 0.48 g of 2-allyl-2- (4-ethylbenzyl) malononitrile (compound 101).

Yield: 57%; 1H-NMR (CDC13, TMS, 8 (ppm)): 1.25 (3H, t), 2.61-2.74 (4H, m), 3.18 (2H, s), 5.37-5.49 (2H, m), 5.88-6.03 (1H, m), 7.21-7.33 (4H, m).

Production Example 100

Using 0.79 g of 4-isopropylbenzyl chloride, 5 ml of N, N-dimethyl- formamide, 0.19 g of sodium hydride (60% in oil), and 0.5 g of allylmalono- nitrile, and according to the process described in the Production Example 93, there was obtained 0.57 g of 2-allyl-2- (4-isopropylbenzyl) malononitrile (com- pound 102).

Yield: 62%; 'H-NMR (CDC13, TMS, 8 (ppm)): 1.24 (6H, d), 2.68 (2H, d), 2.91 (1H, hept), 3.16 (2H, s), 5.38-5.47 (2H, m), 5.86-6.00 (1H, m), 7.24 (2H, d), 7.29 (2H, d).

Production Example 101 Using 0.72 g of (4-(trifluoromethoxy) benzyliden) malononitrile, 20 ml of benzene, 1.99 g of allyl tributyl tin, 0.20 g of azobis (isobutyronitrile) and 2.76 g of 1, 1-dimethylethyl iodide, and according to the process described in the Production Example 30, there was obtained 0.20 g of 2-allyl-2- (l- (4- (tri- fluoromethoxy) phenyl)-2, 2-dimethylpropyl) malononitrile (compound 103).

Yield: 61% ; nD z o. 5 : 1.4762.

Production Example 102 Using 0.23 g of (4- (trifluoromethyl) benzyl) malononitrile, 5 ml of N, N-dimethylformamide, 0.1 g of sodium hydride (60% in oil), and 0.15 g of 1-bromopentane, and according to the process described in the Production Example 1, there was obtained 0.12 g of 2-pentyl-2- (4- (trifluoromethyl) ben- zyl) malononitrile (compound 104).

Yield: 46%; 'H-NMR (CDC13, TMS, 8 (ppm)): 0.93 (3H, t), 1.34-1.45 (4H, m), 1.67- 1.79 (2H, m), 1.94-2.00 (2H, m), 3.25 (2H, s), 7.51 (2H, d), 7.68 (2H, d).

Production Example 103 Using 0.23 g of (4- (trifluoromethyl) benzyl) malononitrile, 5 ml of

N, N-dimethylformamide, 0.1 g of sodium hydride (60% in oil), and 0.15 g of 1-bromo-3-methylbutane, and according to the process described in the Production Example 1, there was obtained 0.14 g of 2- (3-methylbutyl)-2- (4- (trifluoromethyl) benzyl) malononitrile (compound 105).

Yield: 54%; 'H-NMR (CDC13, TMS, 8 (ppm)) : 0.96 (6H, d), 1.57-1.72 (3H, m), 1.96- 2.04 (2H, m), 3.25 (2H, s), 7.52 (2H, d), 7.68 (2H, d).

Production Example 104 Using 0.23 g of (4- (trifluoromethyl) benzyl) malononitrile, 5 ml of N, N-dimethylformamide, 0.1 g of sodium hydride (60% in oil), and 0.15 g of 1-bromo-3-methyl-2-butene, and according to the process described in the Production Example 1, there was obtained 0.18 g of 2- (3-methyl-2-butenyl)- 2- (4- (trifluoromethyl) benzyl) malononitrile (compound 106).

Yield: 68%; 'H-NMR (CDC13, TMS, 8 (ppm)) : 1.73 (3H, s), 1.85 (3H, s), 2.74 (2H, d), 3.23 (2H, s), 5.34 (1H, t), 7.52 (2H, d), 7.68 (2H, d).

Production Example 105 Using 0.23 g of (4- (trifluoromethyl) benzyl) malononitrile, 5 ml of N, N-dimethylformamide, 0.1 g of sodium hydride (60% in oil), and 0.14 g of 1-bromo-2-butene, and according to the process described in the Production Example 1, there was obtained 0.18 g of 2- (2-butenyl)-2- (4- (trifluoromethyl)- benzyl) malononitrile (compound 107).

Yield: 74%; 'H-NMR (CDC13, TMS, 8 (ppm)): 1.74 (Z, 3H, dd), 1.81 (E, 3H, dd), 2.68 (E, 2H, d), 2.80 (Z, 2H, d), 3.22 (E, 2H, s), 3.25 (Z, 2H, s), 5.52-5.64 (1H, m), 5.81-5.95 (1H, m), 7.52 (2H, d), 7.68 (2H, d).

Production Example 106 Using 0.23 g of (4- (trifluoromethyl) benzyl) malononitrile, 5 ml of

N, N-dimethylformamide, 0.1 g of sodium hydride (60% in oil), and 0.14 g of 3-bromo-2-methylpropen, and according to the process described in the Production Example 1, there was obtained 0.20 g of 2- (2-methyl-2-propenyl)- 2- (4- (trifluoromethyl) benzyl) malononitrile (compound 108).

Yield: 71%; 'H-NMR (CDC13, TMS, 5 (ppm)): 1.99 (3H, s), 2.71 (2H, s), 3.27 (2H, s), 5.13 (1H, d), 5.21 (1H, d), 7.54 (2H, d), 7.69 (2H, d).

Production Example 107 Using 0.23 g of (4- (trifluoromethyl) benzyl) malononitrile, 5 ml of N, N-dimethylformamide, 0.1 g of sodium hydride (60% in oil), and 0.14 g of 1-bromobutane, and according to the process described in the Production Example 1, there was obtained 0.16 g of 2-butyl-2- (4- (trifluoromethyl) ben- zyl) malononitrile (compound 109).

Yield: 57%; 'H-NMR (CDC'31 TMS, 5 (ppm)): 0.98 (3H, t), 1.45 (2H, hex), 1.67- 1.77 (2H, m), 1.95-2.01 (2H, m), 3.25 (2H, s), 7.52 (2H, d), 7.68 (2H, d).

Production Example 108 Using 0.23 g of (4- (trifluoromethyl) benzyl) malononitrile, 5 ml of N, N-dimethylformamide, 0.1 g of sodium hydride (60% in oil), and 0.14 g of 1-bromo-2-methylpropane, and according to the process described in the Production Example 1, there was obtained 0.13 g of 2- (2-methylpropyl)-2- (4- (trifluoromethyl) benzyl) malononitrile (compound 110).

Yield: 46%; 'H-NMR (C D C13, T M S, â (ppm)): 1.13 (6H, d), 1.89 (2H, d), 2.07- 2.20 (1H, m), 3.25 (2H, s), 7.52 (2H, d), 7.68 (2H, d).

Production Example 109 Using 0.23 g of (4- (trifluoromethyl) benzyl) malononitrile, 5 ml of N, N-dimethylformamide, 0.1 g of sodium hydride (60% in oil), and 0.15 g of

2-bromobutane, and according to the process described in the Production Example 1, there was obtained 0.07 g of 2- (l-methylpropyl)-2- (4- (trifluoro- methyl) benzyl) malononitrile (compound 111).

Yield: 25%; 1H-NMR (CDCl3, TMS, 5 (ppm)): 1.07 (3H, t), 1.31 (3H, d), 1.42- 1.52 (1H, m), 1.91-2.02 (2H, m), 3.23 (2H, dd), 7.53 (2H, d), 7.68 (2H, d).

Production Example 110 Using 0.23 g of (4- (trifluoromethyl) benzyl) malononitrile, 5 ml of N, N-dimethylformamide, 0.1 g of sodium hydride (60% in oil), and 0.15 g of 2-bromopentane, and according to the process described in the Production Example 1, there was obtained 0.09 g of 2- (l-methylbutyl)-2- (4- (trifluoro- methyl) benzyl) malononitrile (compound 112).

Yield: 30%; 1H-NMR (CDCl3, TMS, 8 (ppm)): 1.01 (3H, t), 1.31 (3H, d), 1.31- 1.66 (3H, m), 1.72-1.84 (1H, m), 2.00-2.10 (1H, m), 3.22 (2H, dd), 7.54 (2H, d), 7.68 (2H, d).

Production Example 111 Using 0.23 g of (4- (trifluoromethyl) benzyl) malononitrile, 5 ml of N, N-dimethylformamide, 0.1 g of sodium hydride (60% in oil), and 0.17 g of 2-bromohexane, and according to the process described in the Production Example 1, there was obtained 0.07 g of 2- (l-methylpentyl)-2- (4- (trifluoro- methyl) benzyl) malononitrile (compound 113).

Yield: 21% ; 1H-NMR (CDCl3, TMS, 8 (ppm)): 0.95 (3H, t), 1.31 (3H, d), 1.30- 1.54 (5H, m), 1.79-1.91 (1H, m), 1.98-2.07 (1H, m), 3.22 (2H, dd), 7.53 (2H, d), 7.68 (2H, d).

Production Example 112 Using 0.54 g of 2,3-difluorobenzyl bromide, 5 ml of N, N-dimethyl-

formamide, 0.1 g of sodium hydride (60% in oil), and 0.28 g of allylmalono- nitrile, and according to the process described in the Production Example 93, there was obtained 0.31 g of 2-allyl-2-(2, 3-difluorobenzyl) malononitrile (com- pound 114).

Yield: 52%; 'H-NMR (CDC13, TMS, 8 (ppm)): 2.74 (2H, d), 3.33 (2H, s), 5.41- 5.49 (2H, m), 5.88-5.99 (1H, m), 7.15-7.26 (3H, m).

Production Example 113 Using 0.69 g of (4- (2-butyloxy)) benzyl bromide, 5 ml of N, N-di- methylformamide, 0.11 g of sodium hydride (60% in oil), and 0.30 g of allylmalononitrile, and according to the process described in the Production Example 93, there was obtained 0.31 g of 2-allyl-2- (4- (2-butyloxy) benzyl)- malononitrile (compound 115).

Yield: 40%; 'H-NMR (CDC13, TMS, 8 (ppm)) : 0.97 (3H, t), 1.30 (3H, d), 1.56- 1.78 (2H, m), 2.70 (2H, d), 3.16 (2H, s), 4.27-4.35 (1H, m), 5.39-5.47 (2H, m), 5.84-6.01 (1H, m), 6.91 (2H, d), 7,27 (2H, d).

Production Example 114 Using 0.80 g of 4-fluoro-3-phenoxybenzyl bromide, 5 ml of N, N- dimethylformamide, 0.11 g of sodium hydride (60% in oil), and 0.30 g of allylmalononitrile, and according to the process described in the Production Example 93, there was obtained 0.32 g of 2-allyl-2- (4-fluoro-3-phenoxy- benzyl) malononitrile (compound 116).

Yield: 37%; 1H-NMR (CDC13, TMS, 8 (ppm)): 2.69 (2H, d), 3.10 (2H, s), 5.37- 5.47 (2H, m), 5.86-5.97 (1H, m), 7.01-7.37 (8H, m).

Production Example 115 Using 0.70 g of 4- (p-tolylthio) benzyl chloride, 5 ml of N, N-dimethyl-

formamide, 0.11 g of sodium hydride (60% in oil), and 0.30 g of allylmalono- nitrile, and according to the process described in the Production Example 93, there was obtained 0.38 g of 2-allyl-2- (4- (p-tolylthio) benzyl) malononitrile (compound 117).

Yield: 37%; 'H-NMR (CDC13, TMS, 8 (ppm)): 2.34 (3H, s), 2.69 (2H, d), 3.15 (2H, s), 5.39-5.48 (2H, m), 5.86-5.98 (1H, m), 7.23-7.25 (8H, m).

Production Example 116 Using 0.74 g of 3-phenoxybenzyl bromide, 5 ml of N, N-dimethyl- formamide, 0.11 g of sodium hydride (60% in oil), and 0.30 g of allylmalono- nitrile, and according to the process described in the Production Example 93, there was obtained 0.54 g of 2-allyl-2- (3-phenoxybenzyl) malononitrile (com- pound 118).

Yield: 67%; 'H-NMR (CDC13, TMS, 8 (ppm)): 2.70 (2H, d), 3.15 (2H, s), 5.37- 5.47 (2H, m), 5.87-5.98 (1H, m) 6.91-7.08 (6H, m), 7.28-7.37 (3H, m).

Production Example 117 Using 0.66 g of 4- (m-tolyloxy) benzyl bromide, 5 ml of N, N-dimethyl- formamide, 0.11 g of sodium hydride (60% in oil), and 0.30 g of allylmalono- nitrile, and according to the process described in the Production Example 93, there was obtained 0.38 g of 2-allyl-2- (4- (m-tolyloxy) benzyl) malononitrile (compound 119).

Yield: 45%; 1H-NMR (CDCI3, TMS, 8 (ppm)): 2.35 (3H, s), 2.71 (2H, d), 3.17 (2H, s), 5.44 (2H, dd), 5.86-6.04 (1H, m), 6.81-7.01 (4H, m), 7.20-7.35 (4H, m).

Production Example 118 Using 0.30 g of (2,4,6-trifluorobenzyl) malononitrile, 5 ml of N, N- dimethylformamide, 0.06 g of sodium hydride (60% in oil), and 0.17 g of allyl

bromide, and according to the process described in the Production Example 1, there was obtained 0.21 g of 2-allyl-2- (2, 4,6-trifluorobenzyl) malononitrile (compound 120).

Yield: 59%; 'H-NMR (CDC13, TMS, 8 (ppm)): 2.75 (2H, d), 3.31 (2H, s), 5.37- 5.46 (2H, m), 5.90-6.01 (1H, m), 6.81 (2H, dd).

Production Example 119 Using 0.84 g of 4- (4-chlorophenoxy) benzyl bromide, 5 ml of N, N- dimethylformamide, 0.11 g of sodium hydride (60% in oil), and 0.30 g of allylmalononitrile, and according to the process described in the Production Example 93, there was obtained 0.50 g of 2-allyl-2- (4- (p-chlorophenoxy) ben- zyl) malononitrile (compound 121).

Yield: 55%; 1H-NMR (CDCl3, TMS, 8 (ppm)): 2.72 (2H, d), 3.17 (2H, s), 5.41- 5.49 (2H, m), 5.88-6.00 (1H, m), 6.96-7.01 (4H, m), 7.25-7.36 (4H, m).

The following will describe some production examples for intermedi- ate compounds as reference production examples.

Reference Production Example 1 First, 1.00 g of (4-chloro-a-methylbenzylidene) malononitrile of the formula: was dissolved in 20 ml of diethyl ether, to which a catalytic amount of copper (I) iodide was added, and while stirring under ice cooling, a solution of methyl magnesium iodide in diethyl ether (prepared from 0.30 g of magne- sium, 10 ml of diethyl ether, and 0.86 ml of methyl iodide) was added drop- wise, followed by stirring for 30 minutes under ice cooling. Then, 10%

hydrochloric acid was added to the reaction mixture, which was extracted with ethyl ether. The organic layer was successively washed with 10% hydrochloric acid, a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pres- sure. The residue was subjected to silica gel column chromatography to give 0.74 g of (1-(4-chlorophenyl)-1-methylethyl) malononitrile (the inter- mediate (2)).

Yield: 69%.

Reference Production Example 2 First, 1.02 g of (4-chlorobenzylidene) malononitrile was dissolved in 20 ml of tetrahydrofuran, to which a catalytic amount of copper (I) iodide was added, and while stirring under ice cooling, a solution of isopropyl magne- sium bromide in tetrahydrofuran (prepared from 0.34 g of magnesium, 10 ml of tetrahydrofuran, and 1.46 ml of isopropyl bromide) was added dropwise, followed by stirring for 30 minutes under ice cooling. Then, 10% hydro- chloric acid was added to the reaction mixture, which became acidic and was extracted with ethyl ether. The organic layer was successively washed with 10% hydrochloric acid, a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 0.66 g of (1- (4-chlorophenyl)-2-methylpropyl) malononitrile (the inter- mediate (3)).

Yield: 52%.

Reference Production Example 3 First, 4.44 g of (4-(trifluoromethyl) benzylidene) malononitrile was dissolved in 20 ml of ethanol, and while stirring at room temperature, a sus- pension of 0.19 g of sodium borohydride in 5 ml of ethanol was added drop- wise, followed by stirring at room temperature for 30 minutes. Then, 10%

hydrochloride acid was added to the reaction mixture, which became acidic and was extracted with diethyl ether. The organic layer was successively washed with 10% hydrochloric acid, a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 2.30 g of (4- (trifluoromethyl) benzyl) malononitrile (the intermediate (4)).

Yield: 51%.

Reference Production Example 4 First, 3.00 g of (4-chloro-a-methylbenzylidene) malononitrile was dissolved in 20 ml of ethanol, and while stirring at room temperature, a sus- pension of 0.15 g of sodium borohydride in 5 ml of ethanol was added drop- wise, followed by stirring at room temperature for 30 minutes. Then, 10% hydrochloride acid was added to the reaction mixture, which was extracted with diethyl ether. The organic layer was successively washed with 10% hydrochloric acid, a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pres- sure. The residue was subjected to silica gel column chromatography to give 1.70 g of (1- (4-chlorophenyl) ethyl) malononitrile (the intermediate (6)).

Yield: 56%.

Reference Production Example 5 First, 10.0 g of 4- (trifluoromethoxy) benzaldehyde and 3.50 g of malo- nonitrile were dissolved in 60 ml of 70% (w/w) aqueous ethanol, to which a catalytic amount of benzyltrimethylammonium hydroxide was added, and the mixture was stirred at room temperature overnight. Then, a saturated aqueous sodium chloride solution was added to the reaction mixture, which was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, dried over anhydrous magne-

sium sulfate, and then concentrated under reduced pressure. The residue was recrystallized from t-butyl methyl ether and hexane to give 9.24 g of (4- (trifluoromethoxy) benzylidene) malononitrile.

Yield: 74%; 'H-NMR (CDC13, TMS, 8 (ppm)): 7.37 (2H, d), 7.76 (1H, s), 7.98 (2H, d).

Then, 2.61 g of (4- (trifluoromethoxy) benzyhdene) malononitrile was dissolved in 20 ml of tetrahydrofuran, and while stirring at room tempera- ture, a suspension of 0.11 g of sodium borohydride in 5 ml of ethanol was added dropwise, followed by stirring at room temperature for 30 minutes.

Then, 10% hydrochloric acid was added, and the mixture was extracted with diethyl ether. The organic layer was successively washed with 10% hydro- chloric acid, a saturated aqueous sodium chloride solution, dried over anhy- drous magnesium sulfate, and then concentrated under reduced pressure.

The residue was subjected to silica gel column chromatography to give 2.20 g of (4- (trifluoromethoxy) benzyl) malononitrile (the intermediate (7)).

Yield: 83%.

Reference Production Example 6 Using 1.19 g of (4-(trifluoromethoxy) benzylidene) malononitrile, 20 ml of tetrahydrofuran, a catalytic amount of copper (I) iodide, and a solution of isopropyl magnesium bromide in tetrahydrofuran (prepared from 0.39 g of magnesium, 10 ml of tetrahydrofuran, and 2.36 g of isopropyl bromide), and according to the process described in Reference Production Example 2, there was obtained 0.77 g of (1- (4- (trifluoromethoxy) phenyl)-2-methylpropyl) malo- nonitrile (the intermediate (8)).

Yield: 55%.

Reference Production Example 7 Using 1.19 g of (4- (trifluoromethoxy) benzylidene) malononitrile, 20 ml of

tetrahydrofuran, a catalytic amount of copper (I) iodide, and 12.5 ml of a solution of methyl magnesium bromide in tetrahydrofuran (about 1 M, available from Tokyo Kasei Kogyo Co., Ltd), and according to the process described in Reference Production Example 2, there was obtained 0.76 g of (1- (4- (trifluoromethoxy) phenyl) ethyl) malononitrile (the intermediate (10)).

Yield: 60%.

Reference Production Example 8 First, 4.46 g of (3,4-dichlorobenzylidene) malononitrile was dissolved in 20 ml of tetrahydrofuran, and while stirring at room temperature, a sus- pension of 0.19 g of sodium borohydride in 5 ml of ethanol was added drop- wise, followed by stirring at room temperature for 30 minutes. Then, 10% hydrochloride acid was added and the mixture was extracted with diethyl ether. The organic layer was successively washed with 10% hydrochloric acid, a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 3.15 g of (3,4-dichlorobenzyl) malononitrile (the intermediate (12)).

Yield: 70%.

Reference Production Example 9 Using 4.46 g of (2,4-dichlorobenzylidene) malononitrile, 20 ml of tetrahydrofuran, and a suspension of 0.19 g of sodium borohydride in 5 ml of ethanol, and according to the process described in Reference Production Example 8, there was obtained 3.10 g of (2,4-dichlorobenzyl) malononitrile (the intermediate (13)).

Yield: 69%.

Reference Production Example 10 First, 10.0 g of 4- (trifluoromethylthio) benzaldehyde and 2.92 g of malononitrile were dissolved in 50 ml of 70% (w/w) aqueous ethanol, to

which a catalytic amount of benzyltrimethylammonium hydroxide was add- ed, and the mixture was stirred at room temperature overnight. Then, a saturated aqueous sodium chloride solution was added to the reaction mix- ture, which was extracted with ethyl acetate. The organic layer was wash- ed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was recrystallized with a solvent system consisting of t-butyl methyl ether and hexane to give 10.5 g of (4- (trifluoromethylthio) benzylidene) malo- nonitrile.

Yield:85%; 'H-NMR (CDC13, TMS, 8 (ppm)): 7.78 (1H, s), 7.79 (2H, d), 7.93 (2H, d).

Then, 8.00 g of (4-(trifluoromethylthio) benzylidene) malononitrile and 3.35 g of benzaldehyde were dissolved in 320 ml of ethanol, and while stir- ring at room temperature, 3.41g of phenylenediamine was slowly added, and the mixture was stirred at room temperature for 5 hours. Then, the reac- tion mixture was concentrated, 300 ml of t-butyl methyl ether was added, and insoluble matters were filtered. The filtrate was concentrated and the resulting residue was subjected to silica gel chromatography to give 6.22 g of (4- (trifluoromethylthio) benzyl) malononitrile (the intermediate (14)).

Yield: 77%.

Reference Production Example 11 First, 9.78 g of malononitrile, 954 mg of tetrabutylammonium bromide, and 10.0 g of 4-bromo-1-butene were mixed, and while stirring at 0°C under an atmosphere of nitrogen, 8.3 g of potassium t-butoxide was slowly added. The mixture was further stirred at room temperature for 12 hours. Then, the reaction mixture was poured into water, followed by extraction with t-butyl methyl ether. The organic layer was washed with

water, a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 2.31 g of (3-butenyl) malononitrile (the intermediate (16)).

Yield: 26%.

Reference Production Example 12 Using 4.00 g of (4- (trifluoromethoxy) benzylidene) malononitrile, 30 ml of tetrahydrofuran, 175 mg of copper (I) bromide dimethyl sulfide complex, and 26 ml of a solution (0.98 M) of vinyl magnesium bromide in tetrahydro- furan, and according to the process described in Reference Production Ex- ample 2, there was obtained 1.60 g of (1-(4-trifluoromethoxyphenyV)-2-pro- penylmalononitrile (the intermediate (18)).

Reference Production Example 13 Using 5.00 g of (2-methoxybenzylidene) malononitrile, 40 ml of tetrahydrofuran, and a suspension of 0.31 g of sodium borohydride in 10 ml of ethanol, and according to the process described in Reference Production Example 8, there was obtained 3.56 g of (2-methoxybenzyl) malononitrile (the intermediate (20)).

Yield: 70%.

Reference Production Example 14 First, 9.18 g of (4-hydroxybenzyl) malononitrile was dissolved in 90 ml of N, N-dimethylformamide, to which 2.56 g of sodium hydride (60% in oil) was added, while stirring under ice cooling. After the evolution of hydrogen gas ceased, while stirring under ice cooling, 7.21 g of 4-bromo-1-betene was added dropwise, followed by further stirring at room temperature overnight.

Then, a saturated aqueous ammonium chloride solution was added to the reaction mixture, which was extracted with diethyl ether. The organic layer was successively washed with water, a saturated aqueous sodium chloride

solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 10.3 g of 2- (3-butenyl)-2- (4-hydroxybenzyl) malono- nitrile (the intermediate (23)).

Yield: 86%.

Reference Production Example 15 Using 5.23 g of (4-ethoxybenzylidene) malononitrile, 40 ml of tetra- hydrofuran, and a suspension of 0.35 g of sodium borohydride in 10 ml of ethanol, and according to the process described in Reference Production Example 8, there was obtained 2.76 g of (4-ethoxybenzyl) malononitrile (the intermediate (25)).

Yield: 52%.

Reference Production Example 16 Using 3.00 g of (3-chloro-a-methylbenzylidene) malononitrile of the formula: 60 ml of diethyl ether, a catalytic amount of copper (I) iodide, and methyl magnesium iodide in diethyl ether (prepared from 0.90 g of magnesium, 30 ml of diethyl ether, and 2.58 ml of methyl iodide), and according to the pro- cess described in Reference Production Example 1, there was obtained 2.33g of (1- (3-chlorophenyl)-l-methylethyl) malononitrile (the intermediate (26)).

Yield: 73%.

Reference Production Example 17 Using 3.00 g of (2-chloro-a-methylbenzylidene) malononitrile of the formula:

60 ml of diethyl ether, a catalytic amount of copper (I) iodide, and methyl magnesium iodide in diethyl ether (prepared from 0.90 g of magnesium, 30 ml of diethyl ether, and 2.58 ml of methyl iodide), and according to the process described in Reference Production Example 1, there was obtained 1.16g of (1- (2-chlorophenyl)-l-methylethyl) malononitrile (the intermediate (27)).

Yield: 36%.

Reference Production Example 18 Using 4.46 g of (2,3-dichlorobenzylidene) malononitrile, 20 ml of tetrahydrofuran, and a suspension of 0.21 g of sodium borohydride in 5 ml of ethanol, and according to the process described in Reference Production Example 8, there was obtained 3.07 g of (2,3-dichlorobenzyl) malononitrile (the intermediate (29)).

Yield: 68%.

Reference Production Example 19 Using 4.46 g of (2,6-dichlorobenzylidene) malononitrile, 20 ml of tetrahydrofuran, and a suspension of 0.21 g of sodium borohydride in 5 ml of ethanol, and according to the process described in Reference Production Example 8, there was obtained 2.73 g of (2,6-dichlorobenzyl) malononitrile (the intermediate (30)).

Yield: 61%.

Reference Production Example 20 Using 4.88 g of (2,3,4,5,6-pentafluorobenzylidene) malononitrile, 20 ml of tetrahydrofuran, and a suspension of 0.21 g of sodium borohydride in 5 ml of ethanol, and according to the process described in Reference Production

Example 8, there was obtained 2.20 g of (2,3,4,5,6-pentafluorobenzyl)- malononitrile (the intermediate (31)).

Yield: 45%.

Reference Production Example 21 Using 1.02 g of (3-chlorobenzylidene) malononitrile, 20 ml of tetra- hydrofuran, a catalytic amount of copper (I) iodide, and 10ml of isopropyl magnesium bromide in tetrahydrofuran (1.4 M), and according to the process described in Reference Production Example 2, there was obtained 0.71 g of (1- (3-chlorophenyl)-2-methylpropyl) malononitrile (the intermediate (32)).

Yield: 56%.

Reference Production Example 22 First, 13.2 g of (2,2-dimethylpropylidene) malononitrile and 10.5 g of benzaldehyde was dissolved in 800 ml of ethanol, to which 10.6 g of 1,2- phenylenediamine was added slowly while stirring, followed by stirring overnight at room temperature. Then, the reaction mixture was concen- trated under reduced pressure. Then, 300 ml of chloroform was added to the residue, the precipitate was filtered off, the filtrate was concentrated.

And the same operation was repeated once more. The residue was sub- jected to silica gel column chromatography to give 8.50 g of (2,2-dimethyl- propyl) malononitrile (the intermediate (34)).

Yield: 64%.

The intermediate compounds used in the production of the com- pounds are shown below with the compound numbers and physical data.

Intermediate (1) (4-Chlorobenzyl) malononitrile m. p.: 96.9°C.

Intermediate (2) (1- (4-ChlorophenyV-1-methylethyl) malononitrile

nD22.0.1.5372.

Intermediate (3) (1- (4-Chlorophenyl)-2-methylpropyl) malononitrile no'" : 1.5289.

Intermediate (4) (4- (Trifluoromethyl) benzyl) malononitrile m. p.: 79.1°C.

Intermediate (5) (4-Cyanobenzyl) malononitrile m. p.: 118.7°C.

Intermediate (6) (1- (4-Chlorophenyl) ethyl) malononitrile no"' : 1.5349.

Intermediate (7) <BR> <BR> (4- (Trifluoromethoxy) benzyl) malononitrile

m. p.: 88.3°C.

Intermediate (8) <BR> <BR> (1- (4- (Trifluoromethoxy) phenyl-2-methylpropyl) malononitrile 'H-NMR (CDCl3, TMS, 6 (ppm)): 0.83 (3H, d), 1.16 (3H, d), 2.29-2.45 (1H, m), 2.87 (1H, dd), 4.18 (1H, d), 7.25-7.30 (2H, m), 7.38-7.42 (2H, m).

Intermediate (9) (4-Bromobenzyl) malononitrile m. p.: 97.7°C.

Intermediate (10) (1- (4- (Trifluoromethoxy) phenyl) ethyl) malononitrile 1H-NMR (CDCl3, TMS, 8 (ppm)) : 1.65 (3H, d), 3.49 (1H, dq), 3.85 (1H, d), 7.24-7.29 (2H, m), 7.38-7.42 (2H, m).

Intermediate (11) (4-Fluorobenzyl) malononitrile

m. p.: 117.2°C.

Intermediate (12) (3,4-Dichlorobenzyl)malononitrile m. p.: 83.3°C.

Intermediate (13) (2,4-Dichlorobenzyl)malononitrile m. p.: 62.5°C.

Intermediate (14) <BR> <BR> (4-(Trifluoromethylthio) benzyVmalononitrile 1H-NMR (CDCl3, TMS, 8 (ppm)): 3.15 (2H, d), 3.95 (1H, t), 7.37 (2H, d), 7.70 (2H, d).

Intermediate (15) Allylmalononitrile 1H-NMR (CDCl3, TMS, 8 (ppm)): 2.75 (2H, dd), 3.79 (1H, t), 5.36-5.45 (2H, m), 5.75-5.94 (1H, m).

Intermediate (16) (3-Butenyl) malononitrile

1H-NMR(CDCl3, TMS, # (ppm)): 2.11-2.18 (2H, m), 2.31-2.41 (2H, m), 3.76 (1H, t), 5.16-5.26 (2H, m), 5.64-5.79 (1H, m).

Intermediate (17) (2-chlorobenzyl) malononitrile nD19.5: 1.5384.

Intermediate (18) (1-(4-Trifluoromethoxyphenyl)-2-propenyl)malononitrile 1H-NMR (CDC13, TMS, 8 (ppm)): 3.95-4.03 (2H, m), 5.40-5.53 (2H, m), 6.08-6.19 (1H, m), 7.28 (2H, d), 7.39 (2H, d).

Intermediate (19) (3-chlorob enzyl) m alononitrile no"' : 1.5403.

Intermediate (20) (2-methoxybenzyl) malononitrile nD19.5 : 1.5248.

Intermediate (21) (3-methoxybenzyl) malononitrile

m. p.: 55.5°C.

Intermediate (22) (4-methoxybenzyl) malononitrile m. p.: 89.6°C.

Intermediate (23) 2- (3-butenyl)-2- (4-hydroxybenzyl) malononitrile 'H-NMR (CDCl3, TMS, 8 (ppm)): 1.99-2.05 (2H, m), 2.43-2.51 (2H, m), 3.16 (2H, s), 4.99 (1H, bs), 5.09-5.20 (2H, m), 5.74-5.86 (1H, m), 6.85 (2H, d), 7.24 (2H, d).

Intermediate (24) (3,4- (methylenedioxy) benzyl) malononitrile 1H-NMR (CDCl3, TMS, 8 (ppm)): 3.19 (2H, d), 3.87 (1H, t), 5.98 (2H, s), 6.73-6.83 (3H, m).

Intermediate (25) (4-ethoxybenzyl) malononitrile

m. p.: 118.0°C.

Intermediate (26) (1- (3-chlorophenyl)-l-methylethyl) malononitrile nD23.0:1.5376.

Intermediate (27) (1- (2-chlorophenyl)-1-methylethyl) malononitrile

m. p.: 90.2°C.

Intermediate (28) (4-nitrobenzyl) malononitrile

m. p.: 155.7°C.

Intermediate (29) (2,3-dichlorobenzyl) malononitrile nD22.5: 1.5518.

Intermediate (30) (2,6-dichlorobenzyl)malononitrile

m. p.: 87.7°C.

Intermediate (31) (2,3,4,5,6-pentafluorobenzyl) malononitrile m. p.: 96.3°C.

Intermediate (32) (1- (3-chlorophenyl)-2-methylprpyl) malononitrile nD21.5 : 1.5268.

Intermediate (33) (4-methylbenzyl) malononitrile m. p.: 83.7°C.

Intermediate (34) (2,2-dimethylpropyl) malononitrile 1H-NMR (CDC13, TMS, 8 (ppm)) : 1.07 (9H, s), 2.04 (2H, d), 3.66 (1H, t).

Intermediate (35) (3-(trifluoromethoxy) benzyl) malononitrile

1H-NMR (CDC13, TMS, 8 (ppm)): 3.34 (2H, d), 3.97 (1H, t), 7.25- 7.50 (4H, m).

Specific examples of the compounds (X) are shown in Table 1 with their compound numbers. TABLE 1 The compounds of formula (X) : No. R1 R2 R3 R4 (R5)m 1 H H H CH=CH2-Cl 2 CH3 CH3 H CH=C2 Cl 3 H CH (CH3)2 H CH=CH2 - Cl 4 H H H CH2CH=CH2 - Cl 5 H H H CH=CH,-CF3 6 H H H CH2CH=CH2 - CN 7 H H H (CH2)2CH=CH2 - CN 8 H H H CH=CH2 2-C1 H 9 H H CH2CH2CH2CH2CH2 - Cl 10 H CH3 H CH2CH=CH2 - Cl 11 H H H CH=CH2 - OCF3 12 H CH (CH3) 2 H CH2CH=CH2 - OCF3 13 H H H CH=CH2 - Br 14 H H H CH=CH2 - CN 15 H H H CH2CH=CH2 - OCF3 16 H CH3 H CH2CH=CH2 - OCF3 17 H H H CH=CH2 3-C1 H 18 H H H CH=CH2 - F 19 H H H CH (CH3)2 - Cl TABLE 1 (contn'd) No. R1 R2 R3 R4 (R5)m R6 20 H H H CH=CH2 2-OCH3 H 21 H H H (CH2) 2CH=CH2 - Cl 22 H H CH3 CH=CH2 - Cl 23 H H H CH=CH2 3-Cl Cl 24 H H H CH=CH2 2-C1 Cl 25 H H H CH=C (CH3)2 - Cl 26 H CH (CH3)2 H CH2CH=CH2 - Cl 27 H H H CH=C (CH3)2 - OCF3 28 H H H CH=CH2 3-OCH3 H 29 H H H CH=CH2 - OCH3 30 H CH3 H CH=CH2 - OCF3 31 H CH2Cl H CH=CH,-OCF3 32 H CH=CH2 H CH2CH=CH2 - OCF3 33 H CH=CH2 H CH=CH2 - OCF3 34 H CH=CH2 H C#CH - OCF3 35 H H H CH2CH=CH2-OCBrF2 36 H H H CH2CH=CH2 - OCHF2 37 H H H CH2CH=CH2 3,4-OCH2O 38 H H H CH, CH=CH2-OCH2CH=CH2 39 H OCH3 H CH=CH2 - OCF3 40 H OCH2CF3 H CH=CH2 - OCF3 41 H H H CH=CH2 - SCF3 42 H H H CH2CH=CH2 - SCF3 43 H OCH3 H CH=CH2 - SCF3 44 H H H CH=CH2-OCH2CH3 TABLE 1 (contn'd) No. R'R 2 R 3 R 4 (R5). 45 H H H CH2CH(CH3)2 - OCF3 46 H H H CH=CHCH3 - SCF3 47 H H CH3 CH=CH2 - SCF3 48 CH3 CH3 H CH=CH, 3-C1 H 49 CH3 CH3 H CH=CH2 2-C1 H 50 H H H CH=CH2 - NO2 51 H H CH3 CH3 - Cl 52 H H H CH2CH=CH2 - CF3 53 H H H CH=CH2 2,3-Cl2 54 H H H CH=CH2 2,6-Cl2 55 H CN H CH=CH2 - OCF3 56 H CN H CH=CH2 - SCF3 57 H H H CH=CH, 2-CF3 CF3 58 H H H CH=CH2 2-Cl CF3 59 H H H C#CCH3 - OCF3 60 H H H CH2CH=CH2 2-Cl CF3 61 H H H CH=CH2 S (O), CH, 62 H H H CH=CH2 2,3,5,6-F4 F 63 H H H CH=CH2 2-NO2 CF3 64 H H H CH=CH2 2, 6-Cl2 CF3 65 H H H CH2CH=CH2 2, 6-Cl2 CF3 66 H CH (CH3) 2 H CH=CH2 3-Cl H 67 H H H CH2CH=CH2 2-NO2 CF3 68 H H H H - Cl 69 H H H CH=CH2 3-F CF3 TABLE 1 (contn'd) No. R1 R2 R3 R4 (R5)m R6 70 H H H CH=CH2 - SCH3 71 H H H C2H5 - CF3 72 H H H CH3-Cl 73 H H H (Z)-CH2CH=CHCH2CH3 - Cl 74 H CH3 H CH=CH2-Cl 75 H H H CH3 - CF3 76 H CH3 H CH2CH2CH=CH2 - Cl 77 H H H CH=CH2 - CH3 78 H H H CH2CH=CH2 - OC(=O)CH3 79 H H H (CH2) 2CH=CH2-CF, 80 H H H CH2CH=CH2 - OCF2CF2H 81 H H H CH2CH=CH2 - OCH2CF3 82 H OCH2CH3 H CH=CH2 - OCF3 83 H OCH3 H CH=CH2-CN 84 H OCH3 H CH=CH2 - Cl 85 H H H C (CH3)3 - OCF3 86 H H H C (CH3)3 - Br 87 H H H CH (CH3)2 - OCF3 88 H H H CH2CH2CH2CH3 - OCF3 89 H H H CH=CH2 3-OCF3 H 90 H H H CH2CH=CH2 3-OCF3 H 91 H CN H CH=CH2 - OCH3 92 H CN H CH=CH2-CHg 93 H CN H CH=CH2 - C(=O)OCH3 94 H H H CH2CH=CH2 3, 5-(CF3)2 H TABLE 1 (contn'd) No. R1 R2 R3 R4 (R5)m 95 H H H CH=CH2 2, 3-(OCH3)2 H 96 H H H CH=CH2 - CH=CH2 97 H H H CH=CH2 - C(=O)CH3 98 H H H CH2CH=CH2 - OCH2CH3 99 H H H CH2CH=CH2 - OCH2CH2CH3 100 H H H CH2CH=CH2 - OCH(CH3)2 101 H H H CH=CH2-CH2CH3 102 H H H CH=CH2-CH (CH3) z 103 H C (CH3)3 H CH=CH2 - OCF3 104 H H H CH2CH2CH2CH3 - CF3 105 H H H CH2CH(CH3)2 - CF3 106 H H H CH=C (CH3)2 - CF3 107 H H H CH=CHCH3 - CF3 108 H H H C (CH3)=CH2 - CF3 109 H H H CH2CH2CH3 - CF3 110 H H H CH (CH3)2 - CF3 111 H H CH3 CH2CH3 - CF3 112 H H CH3 CH2CH2CH3 - CF3 113 H H CH3 CH2CH2CH2CH3 - CF3 114 H H H CH=CH2 2,3-F2 H 115 H H H CH=CH2 - OCH(CH3)CH2CH3 116 H H H CH=CH2 3-OPh F 117 H H H CH=CH2 - S(p-CH3Ph) 118 H H H CH=CH2 3-OPh H 119 H H H CH=CH2 - O(m-CH3Ph) TABLE 1 (contn'd) No. R1 R2 R3 R4 (R5)m R6 120 H H H CH=CH2 2,6-F2 F 121 H H H CH=CH,-0 (p-CIPh) 122 H H H CH2CH(CH3)2 3-Cl Cl 123 H H H CH2CH(CH3)2 - Cl 124 H H H CH2CH (CH3) 2 - CN 125 H H H CH2CH(CH3)2 - NO2 126 H H H CH2CH (CH3) 2 3-F CF3 127 H H H CH2CH(CH3)2 3-Cl CN 128 H CH3 H CH2CH(CH3)2 - CF3 129 H CH3 H CH2CH(CH3)2 - Cl 130 H CH3 H CH2CH(CH3)2 - CN 131 H CH (CH3) 2 H CH2CH(CH3)2 - CF3 132 H H H CH2CH(CH3)2 3-CF3 H 133 H H H CH2CH(CH3)2 - CF3 134 CH3 CH3 H CH2CH(CH3)2 - CN 135 CH3 CH3 H CH2CH(CH3)2 3-Cl Cl 136 H H H CH2C (CH3)3 - CF3 137 H H H CH2C(CH3)3 - Cl 138 H H H CH2C(CH3)3 - CN 139 H H H CH2C(CH3)3 - NO2 140 H H H CH2C(CH3)3 3-Cl CF3 141 H H H CH2C (CH3) 3 3-F CN 142 H CH3 H CH2C (CH3)3 - CF3 143 H CH3 H CH2C(CH3)3 3-F CF3 144 H CH (CH3)2 H CH2C (CH3)3 3-F CF3 TABLE 1 (contn'd) No. R1 R2 R3 R4 (R5)m R6 145 H CH (CHg) 2 H CH2C(CH3)3 - CF3 146 H H H CH2C(CH3)3 3-F Cl 147 H H H CH2C(CH3)3 3-Cl F 148 H H H CH=CH2 3-Cl CF3 149 H CH3 H CH=CH2 3-F CF3 150 H H H CH=CH, 3-CF3 H 151 H H H CH=CH, 3-Cl CN 152 H H H CH2CH=CH2 3-Cl CF3E 153 H H H CH2CH=CH2 3-F CF3 154 H H H CH2CH=CH2 3-F CN 155 H H H CH2CH=CH2 3-Cl F 156 H CH3 H CH2CH=CH, 3-F Cl 157 H CH3 H CH=C (CH3)2 3-F Cl 158 H H H CH=C (CH3) 2 3-Cl CFg 159 H H H CH=C (CH3) 2 3-F CF3 160 H CH (CH3)2 H CH=C (CH3) 2 - CF3 161 H H H CH=C (CH3)2 3-CF3 H 162 H H H CH2CH=C(CH3)2 - CF3 163 H H H CH2CH=C(CH3)2 - CN 164 H H H CH2CH=C (CH3)2 - NO2 165 H H H CH2CH3 3-F CF 166 H H H CH2CH3 - CN 167 H H H CH2CH3 - Cl 168 H H H CH2CH3 - NO2 169 H CH3 H CH2CH3 - CF3 TABLE 1 (contn'd) No. R1 R2 R3 R4 (R5)m R6 170 H CH3 H CH. CHa-CN 171 H H H CH2CH2CH3 3-F Cl 172 H H H CH2CH2CH3 3-C1 F 173 H H H CH2CH2CH3 3-F CF3 174 H CH3 H CH2CH2CHg 3-CF3 H 175 H H H CH2CH3 3-CF3 H 176 H H H CH2CH2CH3 3-CF3 H 177 H CH2F H CH2CH=CH2-CF3 178 H H H CH2CH2CH3 - SCF3 179 H H H CH2CH3 - OCF3 180 H CF3 H CH, CH, 3-F CF3

The following will describe some formulation examples wherein parts represent parts by weight. The compounds (X) are designated by their compound numbers shown in Table 1.

Formulation Example 1 Nine (9) parts of each of compounds 1 to 120 is dissolved in 37.5 parts of xylene and 37.5 parts of dimethylformamide, and 10 parts of polyoxy- ethylene styryl phenyl ether and 6 parts of calcium dodecylbenzenesulfonate are added thereto, followed by well stirring and mixing, to give an emulsi- fiable concentrate for each compound.

Formulation Example 2 To 40 parts of each of compounds 1 to 120 is added 5 parts of Sorpol' 5060 (Toho Chemical Industry Co., Ltd.), followed by well mixing, and 32 parts of Carplex# &num 80 (synthetic hydrated silicone oxide fine powder; Shionogi & Co., Ltd.) and 23 parts of 300 mesh diatomaceous earth are added,

which is mixed with a mixer to give a wettable powder for each compound.

Formulation Example 3 To 3 parts of each of compounds 1 to 120 are added 5 parts of synthetic hydrated silicon oxide fine powder, 5 parts of sodium dodecylben- zenesulfonate, 30 parts of bentonite, and 57 parts of clay, followed by well stirring and mixing, and an appropriate amount of water is added to this mixture, followed by further stirring, granulation with a granulator, and air drying, to give a granule for each compound.

Formulation Example 4 First, 4.5 parts of each of compounds 1 to 120,1 part of synthetic hydrated silicon oxide fine powder, 1 part of Doriresu B (Sankyo Co., Ltd.) as a flocculant, and 7 parts of clay are well mixed with a mortar, followed by stirring and mixing with a mixer. To the resulting mixture is added 86.5 parts of cut clay, followed by well stirring and mixing, to give a dust for each compound.

Formulation Example 5 Ten parts of each of compounds 1 to 120,35 parts of white carbon containing 50 parts of polyoxyethylene alkyl ether sulfate ammonium salt, and 55 parts of water are mixed and pulverized by the wet grinding method to give a formulation for each compound.

Formulation Example 6 First, 0.5 parts of each of compounds 1 to 120 is dissolved in 10 parts of dichloromethane, which is mixed with 89.5 parts of ISOPAR'M (isoparaffin ; Exxon Chemical Co.) to give an oil formulation for each com- pound.

Formulation Example 7 First, 0.1 parts of compounds 1 to 120 and 49.9 parts of NEO- CHIOZOL (Chuo Kasei K. K.) are put into an aerosol can, to which an aerosol

valve is attached. Then, 25 parts of dimethyl ether and 25 parts of LPG are filled in the aerosol can, followed by shaking and attachment of an actuator, to give an oil-based aerosol.

Formulation Example 8 First, 0.6 parts of each of compounds 1 to 120,0.01 parts of BHT, 5 parts of xylene, 3.39 parts of deodorized kerosine, and 1 part of an emulsifier (Atmos 300; Atmos Chemical Co.) are mixed to become a solution. Then, this solution and 50 parts of distilled water are filled in an aerosol can, to which a valve part is attached, and 40 parts of a propellant (LPG) is filled under pressure through the valve in the aerosol can to give a water-based aerosol.

The following test example will demonstrate that the compounds are useful as the active ingredients of pesticide compositions. The com- pounds (X) are designated by their compound numbers shown in Table 1.

Test Example 1 Pesticidal Test against Nilaparvata lugens Each formulation of the compound 11,12,16,27,30,31,32,33,34,37, 40,41,42,47,49,52,56,58,59,60,63,64,65,67,69,71,75,79,87,88, 89, 90,98,100,102,105,106,108,109,110,114,115,116,117,118 and 119 obtained according to Formulation Example 5 was diluted with water so that the active ingredient concentration came to 500 ppm to prepare a test liquid for each compound.

Fifty grams of molding Bonsoru 2 (available from Sumitomo Chemi- cal Co., Ltd.) was put into a polyethylene cup, and 10 to 15 seeds of rice were planted in the polyethylene cup. Then rice plants were grown until the second foliage leaves developed and then cut into the same height of 5 cm.

The test liquid, which had been prepared as described above, was sprayed at the rate of 20 ml/cup onto these rice plants. After the test liquid sprayed onto the rice plants were dried, the polyethylene cup with the rice plants was

placed in a large polyethylene cup and 30 first-instar larvae of Nilaparvata lugens (brown planthopper) were set free in the large polyethylene cup, which was then kept covered and left in a greenhouse at 25°C. On the 6th day after the release of larvae of Nilaparvata lugens, the number of parasitic Nilaparvata lugens on the rice plants was examined.

As a result, in the treatment with each of the compounds described above, the number of parasitic pests on the 6th day after the treatment was not greater than 3.

Test Example 2 Pesticidal Test against Nilaparvata lugens Each formulation of the compound 11,12,16,41,45,47,49,52,54,58, 68,69,71,75,87,90,105,106,108,109 and 110 obtained according to Formulation Example 5 was diluted with water so that the active ingredient concentration came to 45.5 ppm to prepare a test liquid for each compound.

Fifty grams of molding Bonsoru 2 (available from Sumitomo Chemi- cal Co., Ltd.) was put into a polyethylene cup having five holes of 5 mm, and 10 to 15 seeds of rice were planted in the polyethylene cup. Then rice plants were grown until the second foliage leaves developed and the polyethylene cup with the rice plants was placed in a large polyethylene cup containing 55 ml of the test liquid, which had been prepared as described above. The rice plants were left in a greenhouse at 25°C for 6 days and then cut into the same height of 5 cm. Thirty first-instar larvae of Nilaparvata lugens (brown planthoppers) were set free in the large polyethylene cup, which was then kept covered and left in a greenhouse at 25°C. On the 6th day after the release of larvae of Nilaparvata lugens, the number of parasitic Nilaparvata lugens on the rice plants was examined.

As a result, in the treatment with each of the compounds described above, the number of parasitic pests on the 6th day after the treatment was not greater than 3.

Test Example 3 Pesticidal Test against Nilaparvata lugens Each formulation of the compound 1,2,3,4,5,6,8,9,10,11,12,13, 14,15,16,17,18,19,21,22,23,24,25,26,27,29,44,48,49,51,62,66, 73, 74,76 and 77 obtained according to Formulation Example 1 was diluted with water so that the active ingredient concentration came to 500 ppm to prepare a test liquid for each compound.

A bundle of 3 to 4 of cotyledons (height of 3 to 5 cm) of rice was immersed in the test liquid, which had been prepared as described above, for 1 minute. After the test liquid treated the rice plants was dried, a filter paper moistened with 1 ml of water was place on a bottom of polyethylene cup and then the bundle of cotyledons of rice was placed on it. Thirty first- instar larvae of Nilaparvata lugens (brown planthoppers) were set free in the polyethylene cup, which was then kept covered and left in a greenhouse at 25°C. On the 6th day after the release of larvae of Nilaparvata lugens, the number of parasitic Nilaparvata lugens on the rice plants was examined.

As a result, in the treatment with each of the compounds described above, the number of parasitic pests on the 6th day after the treatment was not greater than 3.

Test Example 4 Pesticidal Test against Diabrotica undecimpun- etc ta Each formulation of the compound 1,2,3,4,5,9,10,11,12,16,19,21, 22,23,24,26,66,74 and 76 obtained according to Formulation Example 1 was diluted with water so that the active ingredient concentration came to 50 ppm to prepare a test liquid for each compound.

On the bottom of a polyethylene cup of 5 cm in diameter was placed a filter paper, to which the test liquid had been prepared as described above, was added dropwise in an amount of 1 ml. One germinated seed of corn and 30 to 50 eggs of Diabrotica undecimpunctata (southern corn rootworm) was

placed on the filter paper in the polyethylene cup, which was then kept covered and left in a room at 25°C. On the 6th day after, the number of surviving larvae of Diabrotica undecimpunctata was examined.

As a result, in the treatment with each of the compounds described above, the number of surviving pests on the 6th day after was 0.

Test Example 5 Pesticidal Test against Musca domestica Each formulation of the compound 1,3,4,10,11,15,17,22,24,30,31, 32,33,34,35,36,37,39,40,41,42,43,45,46,47,52,55,56,57,58,59, 60, 64,65,66,67,68,69,71,74,75,79,82,84,89,90,92,101,102,105,107 ,108, 109,110,111,114,115 and 120 obtained according to Formulation Example 5 was diluted with water so that the active ingredient concentration came to 500 ppm to prepare a test liquid for each compound.

On the bottom of a polyethylene cup of 5.5 cm in diameter was placed a filter paper on the same size, to which the test liquid had been prepared as described above, was added dropwise in an amount of 0.7 ml, and 30 mg of sucrose as a bait was placed on it. Ten female adults of Musca domestica (house fly) were set free in the polyethylene cup, which was then kept covered. After 24 hours, their survival was examined to determine the mortality.

As a result, in the treatment with each of the compounds described above, it was exhibited the mortality of 100%.

Test Example 6 Pesticidal Test against German cockroach Each formulation of the compound 1,2,3,4,5,9,10,11,12,15,16,17, 23,30,31,32,33,36,39,40,41,42,43,46,47,52,55,56,57,58,59,60, 64, 68,69,74,79,84,89,102,109,110,114,119,120 and 121 obtained in Formulation Example 5 was diluted with water so that the active ingredient concentration came to 500 ppm to prepare a test liquid for each compound.

On the bottom of a polyethylene cup of 5.5 cm in diameter was placed

a filter paper on the same size, to which the test liquid had been prepared as described above, was added dropwise in an amount of 0.7 ml, and 30 mg of sucrose as a bait was placed on it. Two male adults of German cockroach (Blattalla germanic) were set free in the polyethylene cup, which was then kept covered. After 6 days, their survival was examined to determine the mortality.

As a result, in the treatment with each of the compounds described above, it was exhibited the mortality of 100%.

Test Example 7 Pesticidal Test against Cullex pipiens pallens Each formulation of the compound 1,2,3,4,5,6,7,9,10,11,12,13, 15,16,17,19,21,22,23,24,25,26,27,28,29,30,31,32,33,34,35,36, 37, 38,39,40,41,42,43,44,45,46,47,48,52,54,55,56,57,58,59,60,61, 63, 64,65,66,67,68,69,70,71,74,75,76,78,79,80,81,82,83,84,89,91, 92, 97,98,99,100,101,102,103,104,105,106,107,108,109,110,111,112 ,113, 115,116,118 and 121 obtained according to Formulation Example 5 was diluted with water so that the active ingredient concentration came to 500 ppm to prepare a test liquid for each compound.

In 100 ml of ion-exchanged water, the test liquid had been prepared as described above, was added dropwise in an amount of 0.7 ml (the concentration of active ingredient was 3.5 ppm). Twenty final-instar larvae of Cullex pipiens pallens (common mosquito) were set free in the solution.

After 1 days, their survival was examined to determine the mortality.

As a result, in the treatment with each of the compounds described above, it was exhibited the mortality of 100%.

Industrial Applicability The present invention makes it possible to effectively control pests such as insect pests, acarine pests, and nematode pests.