Indian Patents
Title of Invention

MALONONITRILE COMPOUND AND A COMPOSITION COMPRISING THE SAME
Abstract The present invention provides a malononitrile compound represented by the formula (I): and a composition comprising the same. The malononitrile compound has an efficient pesticidal activity and can control pests effectively.
Full Text

DESCRIPTION
TITLE OF THE INVENTION
MALONONITRILE COMPOUNDS AND USE THEREOF
TECHNICAL FIELD
The present invention relates a malononitrile compound having six-membered ring containing nitrogen atoms and a use thereof .
BACKGROUND ART
Compounds having pesticidal activity have been developed and practically used for pest control-
The object of the present invention is to provide a compound having excellent pesticidal activity against pests, a pesticide composition comprising said compound as an active ingredient and a method for controlling pests applying said compound•
DISCLOSURE OF THE INVENTION
The present invention is a malononitrile compound represented by the formula (I) :


wherein, in the formula,
R1 represents a C1-C5 alkyl group optionally substituted by one
or more halogen atoms, a C2-C5 alkenyl group optionally
substituted by one or more halogen atoms, a C2-C5 alkynyl group
optionally substituted by one or more halogen atoms or a hydrogen
atom;
R2 represents a C1-C5 alkyl group optionally substituted by one
or more halogen atoms, a C1-C5 alkoxy group optionally
substituted by one or more halogen atoms, a C2-C5 alkenyl group
optionally substituted by one or more halogen atoms, a C2-C5
alkynyl group optionally substituted by one or more halogen atoms,
a cyano group or a hydrogen atom;
each of R3 andR4 is represents a C1-C5 alkyl group optionally
substituted by one or more halogen atoms, a C2-C5 alkenyl group
optionally substituted by one or more halogen atoms, a C2-C5
alkynyl group optionally substituted by one or more halogen atoms,
a C3-C5 cycloalkyl group optionally substituted by one or more
halogen atoms t aC5-C6 cycloalkenyl group optionally substituted
by one or more halogen atoms or a hydrogen atom,
or represents a C2-C6 alkanediyl group optionally substituted
by one or more halogen atoms or a C4 -C6 alkenediyl group optionally
substituted by one or more halogen atoms in each of which R3
and R4 couple one another at the ends thereof;
each of X1, X2 and X3 represents a nitrogen atom or CR6, with
the proviso that two or three of X1, X2 and X3 represent a nitrogen

atom;
R6 represents a hydrogen atom or R5;
each of R5s represents a halogen atom, a cyano group, a nitro group, a hydroxyl group, a mercapto group, a formyl group, a SF5 group, a carboxyl group, a C1-C5 alkyl group optionally substituted by one or more halogen atoms, a C2-C5 alkenyl group optionally substituted by one or more halogen atoms, a C2-C5 alkynyl group optionally substituted by one or more halogen atoms, a C3-C5 cycloalkyl group optionally substituted by one or more halogen atoms, a C1-C5 alkoxy group optionally substituted by one or more halogen atoms, a C3-C6 alkenyloxy group optionally substituted by one or more halogen atoms, a C3-C6 alkynyloxy group optionally substituted by one or more halogen atoms, a C1-C5 alkylthio group optionally substituted by one or more halogen atoms, a C3-C5 alkenylthio group optionally substituted by one or more halogen atoms, a C3-C5 alkynylthio group optionally substituted by one or more halogen atoms, a C1-C5 alkylsulfinyl group optionally substituted by one or more halogen atoms, a C1-C5 alkylsulf onyl group optionally substituted by one or more halogen atoms, a C2-C6 alkylcarbonyl group optionally substituted by one or more halogen atoms, a C2-C5 alkoxycarbonyl group optionally substituted by one or more halogen atoms, a group designated by -NR10R1X, a group designated by - C ( =X5) NR12R13 or a group designated by — C(=NOR14)R15, or where m is 2 and two carbon atoms to couple two R5s are adjacent.

may represent a C3-C6 alkanediyl group or a C3-C6 alkenediyl group each of which is formed by coupling of the two R5s at the ends thereof, furthermore, in this conditions, a methylene group structuring said C3-C6 alkanediyl group or said C3-C6 alkenediyl group may be replaced by 0, S(0)r or NR16 and a carbon atom structuring saidC3-C6 alkanediyl group or saidC3-C6 alkenediyl group may be coupled with a halogen atom or a C1-C3 alkoxy group optionally substituted by one or more halogen atoms instead of hydrogen atom(s);
each of R10 and R1X represents a C1-C5 alkyl group optionally substituted by one or more halogen atoms, a C3-C5 alkenyl group optionally substituted by one or more halogen atoms, a C3-C5 alkynyl group optionally substituted by one or more halogen atoms, a C3-C5 cycloalkyl group optionally substituted by one or more halogen atoms, a (C1-C5 alkoxy optionally substituted by one or more halogen atoms) C1-C3 alkyl group, a C1-C5 alkylsulfonyl group optionally substituted by one or more halogen atoms, a C2-C6 alkylcarbonyl group optionally substituted by one or more halogen atoms, a C2-C5 alkoxycarbonyl group optionally substituted by one or more halogen atoms or a hydrogen atom, or represents a C2-C6 alkanediyl group optionally substituted by one or more halogen atoms or a C4 -C6 alkenediyl group optionally substituted by one or more halogen atoms in each of which R10 and R11 are coupled with one another at the ends thereof; each of R12 and R13 represents a C1-C5 alkyl group optionally

substituted by one or more halogen atoms, a C3-C5 alkenyl group optionally substituted by one or more halogen atoms, a C3-C5 alkynyl group optionally substituted by one or more halogen atoms, a C3-C5 cycloalkyl group optionally substituted by one or more
halogen atoms, a group designated by — (CH2)nQ1 or a hydrogen atom,
or represents a C2-C6 alkanediyl group optionally substituted by one or more halogen atoms or a C4 -C6 alkenediyl group optionally substituted by one or more halogen atoms in each of which R12 and R13 are coupled with one another at the ends thereof; A represents an oxygen atom, a sulfur atom or a (CH2)n; each of R14 and R15 represents a C1-C5 alkyl group optionally substituted by one or more halogen atoms, a C3-C5 alkenyl group optionally substituted by one or more halogen atoms, a C3-C5 alkynyl group optionally substituted by one or more halogen atoms, a C3-C5 cycloalkyl group optionally substituted by one or more
halogen atoms, a group designated by -(CH2)nQ2 or a hydrogen
atom;
each of Q1 andQ2 represents a phenyl group which may be substituted
by a group selected from the group consisted of a C1-C5 alkyl
group optionally substituted by one or more halogen atoms, a
CI - C5 alkoxy group optionally substituted by one or more halogen
atoms, a C1-C5 alkylthio group optionally substituted by one
or more halogen atoms and a halogen atom;
R16 represents a C1-C3 alkyl group; m represents an integer of

from 0 to 2; n represents an integer of from 0 to 3; r represents
an integer of from 0 to 2; and
X represents an oxygen atom or a sulfur atom.
(Said malononitrile compound is referred to as "the compound
of the present invention" hereinafter.) The present invention
further provides a pesticide composition comprising the compound
of the present invention as an active ingredient, a method for
controlling pests comprising applying an effective amount of
the compound of the present invention to pests or at a habitat
of pests and use of the compound of the present invention for
pest control.
EMBODIMENT OF THE INVENTION
In the present invention, "alkanediyl group" represents a group having free valency on two of different carbon atoms structuring a saturated chain hydrocarbon, and "alkenediyl group" represents a group having free valency on two of different carbon atoms structuring a chain hydrocarbon having one or two double bonds.
In the compound of the present invention: a Cl-C5 alkyl group optionally substituted by one or more halogen atoms represented by R1, R2, R3, R4, R5, R10, R11, R12, R13, R14 and R15 includes, for example, a methyl group, an ethyl group, a propyl group, an isopropyl group, a t-butyl group, a 2, 2-dimethylpropyl

group, a chloromethyl group, a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a 2,2,2-trifluoroethyl group and a 1,1,2,2-tetrafluoroethyl group;
a C2-C5 alkenyl group optionally substituted by one or more
halogen atoms represented by R1, R2, R3, R4 and R5 includes, for
example, a vinyl group, a 2,2-difluorovinyl group, a
1,2,2-trifluorovinyl group, a 1-propenyl group and an allyl
group;
a C2-C5 alkynyl group optionally substituted by one or more
halogen atoms represented by R1, R2, R3, R4 and R5 includes, for
example, an ethynyl group, a 1-propynyl group, a propargyl group
and a 3,3,3-trifluoro-1-propynyl group;
a CI -C5 alkoxy group optionally substituted by one or more halogen
atoms represented by R2 and R5 includes, for example, a methoxy
group, an ethoxy group, a 1-methylethoxy group, a
trifluoromethoxy group, a difluoromethoxy group, a
2,2,2-trifluoroethoxy group and a 1,1,2,2-tetrafluoroethoxy
group;
a C3-C5 cycloalkyl group optionally substituted by one or more
halogen atoms represented by R3, R4, R5, R10, R11, R12, R13, R14
and R15 includes, for example, a cyclopropyl group, a
2,2-dichlorocyclopropylgroup, a2,2-difluorocyclopropylgroup,
a 2,2,3,3-tetrafluorocyclopropyl group, a
2,2-dichlorocyclobutyl group, a 2,2-difluorocyclobutyl group.

a 2,2,3,3-tetrafluorocyclobutyl group, a cyclobutyl group and
a cyclopentyl group;
a C5-C6 cycloalkenyl group optionally substituted by one or more
halogen atoms represented by R3 and R4 includes, for example,
a 2-fluoro-2-cyclopentenyl group;
a C2-C6 alkanediyl group optionally substituted by one or more
halogen atoms represented by the combination of R3 and R4, that
of R10 and R11, and that of R12 and R13 includes, for example,
an ethylene group, a propylene group, a trimethylene group and
a tetramethylene group;
a C4-C6 alkenediyl group optionally substituted by one or more
halogen atoms represented by the combination of R3 and R4, that
of R10 and R11, and that of R12 and R13 includes, for example,
a 2-butene-l,4-diyl group and a 2-pentene-l,5-diyl group;
a C3-C6 alkenyloxy group optionally substituted by one or more
halogen atoms represented by R5 includes, for example, anallyloxy
group, a 1-methyl-2-propenyloxy group, a
1,1-dimethyl-2-propenyloxy group, a 2-methyl-2-propenyloxy
group, al-butenyloxygroup, a2-butenyloxygroup, a3-butenyloxy
group, a 1-chloro-2-propenyloxy group, al-bromo-2-propenyloxy
group, a 2-chloro-2-propenyloxy group and a
3,3-dichloro-2-propenyloxy group;
a C3-C6 alkynyloxy group optionally substituted by one or more
halogen atoms represented by R5 includes, for example, a
propargyloxy group, a 2-butynyloxy group, a 3-butynyloxy group.

a 2-pentynyloxy group, a 3-pentynyloxy group, a
3-chloro-2-propynyloxy group, a 3-bromo-2-propynyloxy group,
a 1-methyl-2-propynyloxy group, a 4-chloro-2-butynyloxy group,
a 4,4-difluoro-2-butynyloxy group, a
4,4,4-trifluoro-2-butynyloxy group and
1,1-dimethyl-2-propynyloxy group;
a C1-C5 alkylthio group optionally substituted by one or more
halogen atoms represented by R5 includes, for example, a
methylthio group, a trifluoromethylthio group, a
2,2,2-trifluoroethylthio group and a
1,1,2,2-tetrafluoroethyltio group;
a C3-C5 alkenylthio group optionally substituted by one or more
halogen atoms represented by R5 includes, for example, a
1-propenylthio group, a 2-propenylthio group and a
2,2-difluoro-2-propenylthio group;
a C3-C5 alkynylthio group optionally substituted by one or more
halogen atoms represented by R5 includes, for example, a
propargylthio group, a 2-butynylthio group and a
3,3,3-trifluoro-1-propynylthio group;
a C1-C5 alkylsulfinyl group optionally substituted by one or
more halogen atoms represented by R5 includes, for example, a
methylsulfinyl group and a trifluoromethylsulfinyl group;
a C1-C5 alkylsulfonyl group optionally substituted by one or
more halogen atoms represented by R5, R10 and R11 includes, for
example, a methylsulfonyl group and a trifluoromethylsulfonyl

group;
a C2-C6 alkylcarbonyl group optionally substituted by one or more halogen atoms represented by R5, R10 and R11 includes, for example, an acetyl group, apropionyl group and a trifluoroacetyl group;
a C2-C5 alkoxycarbonyl group optionally substituted by one or
more halogen atoms represented by R5, R10 and R11 includes, for
example, a methoxycarbonyl group and a
2,2,2-trifluoroethoxycarbonyl group;
a C3-C5 alkenyl group optionally substituted by one or more
halogen atoms represented by R10, Ru, R12, R13, R14 and R15 includes,
for example, a 1-propenyl group and an allylgroup;
a C3-C5 alkynyl group optionally substituted by one or more
halogen atoms represented by R10, R11, R12, R13, R14 and R15 includes,
for example, a 1-propynyl group, a propargyl group and a
3,3,3-trifluoro-1-propynyl group;
a (C1-C5 alkoxy optionally substituted by one or more halogen
atoms) C1-C3 alkyl group represented by R10 and R11 includes,
for example, a methoxymethyl group, an ethoxymethyl group, a
1-methoxyethyl group, a 1-ethoxyethyl group and a
trifluoromethoxymethyl group;
where two carbon atoms to couple two R5s are adjacent, a C3-C6
alkanediyl group represented by the couple of said two R5s
includes, for example, a trimethylene group, a propylene group,
a 2,2-dimethylpropane-l,4-diyl group, a

1, l-dimethylpropane-l,3-diyl group and a tetramethylene group; where two carbon atoms to couple two R5s are adjacent, a C3-C6 alkenediyl group represented by the couple of said two R5s includes, for example, a 2-butene-l,4-diyl group and a 2-pentene-l,5-diyl group; and
a C1-C3 alkyl group represented by R16 includes, for example, a methyl group, an ethyl group and a propyl group.
A method for producing the compound of the present invention is described hereinafter.
The compound of the present invention can be produced, for example, according to the following (Production Method 1) to (Production Method 3).

same meaning described above, and Z represents a halogen atom, a methanesulfonyloxy group, a trifluoromethanesulfonyloxy group or a toluenesulfonyloxy group.]
The reaction is usually carried out in a solvent under the presence of a base.

The solvent used for the reaction includes, for example, amides such as N,N-dimethylformamide and the like, ethers such as diethylether, tetrahydrofuran and the like, organic sulfurs such as dimethylsulfoxide, sulfolane and the like, halogenated hydrocarbons such as 1,2-dichloroethane, chlorobenzene and the like, aromatic hydrocarbons such as toluene, xylene and the like, and the mixture thereof.
The base used for the reaction includes, for example, inorganic bases such as sodium hydride, sodium carbonate, potassium carbonate and the like, alkali metal alkoxides such as potassium-t-butoxide and the like, and organic bases such as 4-(dimethylamino)pyridine, 1,4-diazabicyclo[2.2.2]octane, l,8-diazabicyclo[5.4.0]-7-undecene and the like.
The amount of the base used for the reaction is usually 1 to 10 moles per 1 mole of the compound (a).
The amount of the compound (b) used for the reaction is usually 1 to 10 moles per 1 mole of the compound (a).
The reaction temperature of the reaction is usually in
the range of -20 to 100 *C, and the reaction time is usually in the range of 1 to 24 hours.
After the reaction has finished, the compound of the present invention represented by the formula (I) can be isolated by subjecting the reaction mixture to ordinary post-treatment such as the reaction mixture poured into water, extracting with an organic solvent, followed by concentrating the extract. The

isolated compound represented by the formula (I) of the present invention may be, if required, purified by chromatography, recrystallization and the like.

[In the formula, R1, R2, R3, R4, R5, X1, X2 and X5 represent the same meaning described above, and Z represents a halogen atom, a methanesulfonyloxy group, a trifluoromethanesulfonyloxy group or a toluenesulfonyloxy group.]
The reaction is usually carried out in a solvent under the presence of a base.
The solvent used for the reaction includes, for example, amides such as N,N-dimethylformamide and the like, ethers such as diethylether, tetrahydrofuran and the like, organic sulfurs such as dimethylsulfoxide, sulfolane and the like, halogenated hydrocarbons such as 1,2-dichloroethane, chlorobenzene and the like, aromatic hydrocarbons such as toluene, xylene and the like, and the mixture thereof.
The base used for the reaction includes, for example, inorganic bases such as sodium hydride, sodium carbonate.

potassium carbonate and the like, alkali metal alkoxides such as potassium-t-butoxide and the like, and organic bases such as 4 - (dimethylamino) pyridine ,1,4- diazabicyclo [2.2.2] octane, l,8-diazabicyclo[5.4.0]-7-undecene and the like.
The amount of the base used for the reaction is usually 1 to 10 moles per 1 mole of the compound (q).
The amount of the compound (r) used for the reaction is usually 1 to 10 moles per 1 mole of the compound (q).
The reaction temperature of the reaction is usually in
the range of -20 to 100 "C, and the reaction time is usually in the range of 1 to 24 hours.
After the reaction has finished, the compound of the present invention represented by the formula (I) can be isolated by subjecting the reaction mixture to ordinary post-treatment such as the reaction mixture poured into water, extracting with an organic solvent, followed by concentrating the extract. The isolated compound represented by the formula (I) of the present invention may be, if required, purified by chromatography, recrystallization and the like.
(Production Method 3)
Among the compound of the present invention, the compound (I-a) may be also produced by the following method.


[In the formula, R1, R2, R3, R4, X1 , X2 , X3 and Z represent the same meaning described above; R5"1 represents a cyano group, a CI -C5 alkoxy group optionally substituted by one or more halogen atoms, a C3-C5 alkenyloxy group optionally substituted by one or more halogen atoms, a C3-C5 alkynyloxy group optionally substituted by one or more halogen atoms, aCl-C5 alkylthio group optionally substituted by one or more halogen atoms, a C3-C5 alkenylthio group optionally substituted by one or more halogen atoms, a C3-C5 alkynylthio group optionally substituted by one
or more halogen atoms or a group represented by — NR10R1:L; R10, and R11 represent the same meaning described above; and M1 represents sodium atom or potassium atom.]
The reaction is usually carried out in a solvent with or without the presence of a base.
The solvent used for the reaction includes, for example, amides such as N,N-dimethylformamide and the like, ethers such as diethylether, tetrahydrofuran and the like, organic sulfurs such as dimethylsulfoxide, sulfolane and the like, halogenated hydrocarbons such as 1, 2-dichloroethane, chlorobenzene and the like, aromatic hydrocarbons such as toluene, xylene and the like, and the mixture thereof.

The base used for the reaction includes, for example, inorganic bases such as sodium hydride, sodium carbonate, potassium carbonate and the like, alkali metal alkoxides such as potassium-t-butoxide and the like, and organic bases such as 4 - (dimethylamino) pyridine ,1,4- diazabicyclo [2.2.2] octane, l,8-diazabicyclo[5.4.0]-7-undecene and the like. The amount of the base used for the reaction is usually 1 to 10 moles per 1 mole of the compound (I-b).
The amount of R5"1 —H or R5'1—M1 used for the reaction is usually 1 to 10 moles per 1 mole of the compound (I-b).
The reaction temperature of the reaction is usually in
the range of -20 to 100 *C, and the reaction time is usually in the range of 1 to 24 hours.
After the reaction has finished, the compound of the present invention represented by the formula (I-a) can be isolated by subjecting the reaction mixture to ordinary post-treatment such as the reaction mixture poured into water, extracting with an organic solvent, followed by concentrating the extract. The isolated compound (I-a) may be, if required, purified by chromatography, recrystallization and the like.
The compound (a) can be produced, for example, by the following method. (Referential Production Method 1)


The compound (d) can be produced by subjecting the compound (c) to reaction with a malononitrile.
The reaction is usually carried out in a solvent. The solvent used for the reaction includes, for example, amides such as N,N-dimethylformamide and the like, ethers such as diethylether, tetrahydrofuran and the like, halogenated hydrocarbons such as chloroform, 1,2-dichloroethane, chlorobenzene and the like, aromatic hydrocarbons such as toluene, xylene and the like, alcohols such as methanol, ethanol, isopropanol and like, and the mixture thereof.
The reaction is, if required, carried out under the presence of a base, and the base used includes, for example, tetrabutyl ammonium hydroxide and the like.

The amount of the base used for the reaction is usually 0.01 to 0.5 moles per 1 mole of the compound (c).
The amount of the malononitrile used for the reaction is usually 1 to 10 moles per 1 mole of the compound (c).
The reaction temperature of the reaction is usually in
the range of -20 to 200 *C, and the reaction time is usually in the range of 1 to 24 hours.
The reaction may be, if required, performed along with removing the water generated by the reaction out of the reaction system.
After the reaction has finished, the compound (d) can be isolated by subjecting the reaction mixture to ordinary post-treatment such as the reaction mixture poured into water, extracting with an organic solvent, followed by concentrating the extract. The isolated compound (d) may be, if required, purified by chromatography, recrystallization and the like.
Step (1-2)
(1) In the case that R2 represents a C1-C5 alkyl group optionally substituted by one or more halogen atoms, a C2-C5 alkenyl group optionally substituted by one or more halogen atoms, a C2-C5 alkynyl group optionally substituted by one or more halogen atoms.
The compound (a) can be produced by subjecting the compound (d) to reaction with an organometallic compound (R2—M : wherein

M represents Mgl, MgBr, MgCl or Li.).
The reaction is usually carried out in a solvent, if required, under the presence of a copper salt.
The solvent used for the reaction includes, for example, ethers such as diethylether, tetrahydrofuran and the like, aromatic hydrocarbons such as toluene, xylene and the like, and the mixture thereof.
R2—M used for the reaction includes, for example, an organic magnesium compound such as methyl magnesium iodide, ethyl magnesium bromide, isopropyl magnesium bromide, vinyl magnesium bromide, ethynyl magnesium bromide, dimethyl magnesium and the like, an organic lithium compound such as methyl lithium and the like, an organic zinc compound such as diethyl zinc and the like, and an organic copper compound such as trifluoromethyl copper and the like.
The amount of the organometallic compound (R2—M) used for the reaction is usually 1 to 10 moles per 1 mole of the compound (d).
The copper salt used for the reaction includes, for example, copper iodide (I), copper bromide (I) and the like.
The amount of the copper salt used for the reaction is usually 1 mole or less per 1 mole of the compound (d).
The reaction temperature of the reaction is usually in
the range of -20 to 100 °C, and the reaction time is usually in the range of 1 to 24 hours.

After the reaction has finished, the compound (a) can be isolated by subjecting the reaction mixture to ordinary post-treatment such as the reaction mixture poured into water, extracting with an organic solvent, followed by concentrating the extract. The isolated compound (a) may be, if required, purified by chromatography, recrystallization and the like.
(2) In the case that R2 represents a hydrogen atom.
The compound (a) can be produced by subjecting the compound (d) to reductive reaction.
The reduction reaction is usually carried out in a solvent.
The solvent used for the reaction includes, for example, ethers such as diethylether, tetrahydrofuran and the like, aromatic hydrocarbons such as toluene, xylene and the like, alcohols such as methanol, ethanol, isopropanol and like, and the mixture thereof.
The reducing agent used for the reaction includes, for example, sodium borohydride.
The amount of the reducing agent used for the reaction is usually 0.25 to 2 moles per 1 mole of the compound (d).
The reaction temperature of the reaction is usually in
the range of 0 to 50 t, and the reaction time is usually in the range of the instant to 24 hours.
After the reaction has finished, the compound (a) can be isolated by subjecting the reaction mixture to ordinary

post-treatment such as the reaction mixture poured into water, extracting with an organic solvent, followed by concentrating the extract. The isolated compound (a) may be, if required, purified by chromatography, recrystallization and the like.
(3) In the case that R2 represents a cyano group.
The compound (a) can be produced by subjecting the compound (d) to reaction with a metal cyanide compound.
The reduction reaction is usually carried out in a solvent.
The solvent used for the reaction includes, for example, ethers such as diethylether, tetrahydrofuran and the like, aromatic hydrocarbons such as toluene, xylene and the like, and the mixture thereof.
The metal cyanide compound used for the reaction includes, for example, sodium cyanide, potassium cyanide and copper cyanide.
The amount of the metal cyanide compound used for the reaction is usually 1 to 10 moles per 1 mole of the compound (d).
The reaction temperature of the reaction is usually in
the range of -20 to 100 °C, and the reaction time is usually in the range of 1 to 24 hours.
After the reaction has finished, the compound (a) can be isolated by subjecting the reaction mixture to ordinary post-treatment such as the reaction mixture poured into water.

extracting with an organic solvent, followed by concentrating the extract. The isolated compound (a) may be, if required, purified by chromatography, recrystallization and the like.

an ethyl group.]
The compound (c) can be produced, for example, by subjecting the compound (e) to reaction with an organometallic
compound (R1—M : wherein M represents Mgl, MgBr, MgCl or Li) or with a reducing agent.
(1) In the case of subjecting to reaction with R1—M
The organometallic compound represented by R1—M used for the reaction includes, for example, an organic magnesium compound such as methyl magnesium iodide, ethyl magnesium bromide, isopropyl magnesium bromide, vinyl magnesium bromide, ethynyl magnesium bromide, dimethyl magnesium and the like, and an organic lithium compound such as methyl lithium and the like.
The amount of RX~M used for the reaction is usually 1 to 10 moles per 1 mole of the compound (e).

The solvent used for the reaction includes, for example, ethers such as diethylether, tetrahydrofuran and the like, aromatic hydrocarbons such as toluene, xylene and the like, and the mixture thereof.
The reaction temperature of the reaction is usually in
the range of -20 to 100 *C, and the reaction time is usually in the range of the instant to 24 hours.
After the reaction has finished, the compound (c) can be isolated by subjecting the reaction mixture to ordinary post-treatment such as the reaction mixture poured into water, extracting with an organic solvent, followed by concentrating the extract.. The isolated compound (c) may be, if required, purified by chromatography, recrystallization and the like. (2) In the case of subjecting to reaction with a reducing agent
The reducing agent used for the reaction includes lithium aluminum hydride, diisobutyl aluminum hydride and the like.
The amount of the reducing agent used for the reaction is usually 0.25 to 5 moles per 1 mole of the compound (e).
The solvent used for the reaction includes, for example, ethers such as diethylether, tetrahydrofuran and the like, aromatic hydrocarbons such as toluene, xylene and the like, and the mixture thereof.
The reaction temperature of the reaction is usually in
the range of 0 to 50 °C, and the reaction time is usually in the range of 1 to 24 hours.

After the reaction has finished, the compound (c) can be isolated by subjecting the reaction mixture to ordinary post-treatment such as the reaction mixture poured into water, extracting with an organic solvent, followed by concentrating the extract. The isolated compound (c) may be, if required, purified by chromatography, recrystallization and the like.
(Referential Production Method 3)
The compound (e-4) among the compound (e) can be produced, for example, according to the method synthesizing 5-pyrimidinecarboxylates disclosed in Synthesis, 2002, p.720-722.

[ In the formula, R21; m and n represent the same meaning described above; R5"1 represents ahydroxyl group, amercapto group, a Cl-C5 alkyl group optionally substituted by one or more halogen atoms, a C3-C5 cycloalkyl group optionally substituted by one or more halogen atoms, a C2-C5 alkenyl group optionally substituted by one or more halogen atoms, a C2-C5 alkynyl group optionally substituted by one or more halogen atoms, a C1-C5 alkoxy group

optionally substituted by one or more halogen atoms, a C1-C5 alkylthio group optionally substituted by one or more halogen
atoms, a group designated by ~COOR21 or a hydrogen atom; each of the groups designated by R5"2 represents a C1-C5 alkyl group optionally substituted by one or more halogen atoms, a C3-C5 cycloalkyl group optionally substituted by one or more halogen atoms, a C2-C5 alkenyl group optionally substituted by one or more halogen atoms, aC2-C5 alkynyl group optionally substituted
by one or more halogen atoms, a group designated by — COOR21 or a hydrogen atom; with the proviso that any one of R5"1 and R5"2
is a group designated by — COOR2X; R22 represents a methyl group, an ethyl group, a sodium atom or potassium atom.]
(Referential Production Method 4)
The compound (e-7) among the compound (e) can be produced, for example, by subjecting a compound (1) obtained according to the method disclosed in Eur. J. Med. Chem, Vol. 15, p. 157-163 to esterification.


[In the formula, R21 and m represent the same meaning described above, and R52 represents a C1-C5 alkyl group optionally substituted by one or more halogen atoms.]
The reaction of Step (6-2) can be carried out, for example, by subjecting the compound (1) to dissolution in an alcohol compound represented by R21OH, and then addition of an acid (sulfuric acid and the like), followed by heating under reflux.
(Referential Production Method 5)
The compound (e-8) among the compound (e) can be produced, for example, by the following method.


optionally substituted by one or more halogen atoms, a C3-C5 cycloalkyl group optionally substituted by one or more halogen atoms, a C2-C5 alkenyl group optionally substituted by one or more halogen atoms, a C2-C5 alkynyl group optionally substituted by one or more halogen atoms, a hydroxyl group or a hydrogen atom.]
(Referential Production Method 6)
Some of the compound shown by the formula (e-9) among the compound (e) can be produced, for example, according to the following method with using the compound (n) produced according to the method disclosed in J. Med. Chem, Vol. 30, p.239-249.



The reaction is usually carried out in a solvent under the presence of a base.
The solvent used for the reaction includes, for example, amides such as N,N-dimethylformamide and the like, ethers such as diethylether, tetrahydrofuran and the like, organic sulfurs such as dimethylsulfoxide, sulfolane and the like, halogenated hydrocarbons such as 1,2-dichloroethane, chlorobenzene and the like, aromatic hydrocarbons such as toluene, xylene and the like, and the mixture thereof.

The base used for the reaction includes, for example, inorganic bases such as sodium hydride, sodium carbonate, potassium carbonate and the like, alkali metal alkoxides such as potassium-t-butoxide and the like, and organic bases such as 4-(dimethylamino)pyridine, l,4-diazabicyclo[2.2.2]octane, 1,8-diazabicyclot5.4.0]-7-undecene and the like.
The amount of the base used for the reaction is usually 1 to 10 moles per 1 mole of the compound (b).
The amount of the malononitrile used for the reaction is usually 1 to 10 moles per 1 mole of the compound (b).
The reaction temperature of the reaction is usually in
the range of -20 to 100 *C, and the reaction time is usually in the range of 1 to 24 hours.
After the reaction has finished, the compound (b) can be isolated by subjecting the reaction mixture to ordinary post-treatment such as the reaction mixture poured into water, extracting with an organic solvent, followed by concentrating the extract. The isolated compound (b) may be, if required, purified by chromatography, recrystallization and the like.
Among of the compound (q), the compound in which R4 is aCl-C5 alkyl group optionally substituted by one or more halogen atoms, a C2-C5 alkenyl group optionally substituted by one or more halogen atoms or a C2-C5 alkynyl group optionally substituted by one or more halogen atoms, may be produced according to the method disclosed in J. Chem. Soc. PERKIN. TRANS.

1, 1991, p.2589-2592.
(Referential Production Method 9)
The compound (r) can be produced, for example, from the compound (c) or the compound (e) according the scheme described below. Namely, the compound (s) which is produced by subjecting the compound (c) or the compound (e) to reaction with an
organometallic compound represented by R2—M (, illustrated as example are Grignard reagent and an organolithium compound,) or a reducing agent (, illustrated as example are aluminum lithium hydride and diisobutyl aluminum hydride), is subjected to reaction with halogenating agent (, illustrated as example are thionyl chloride and phosphorus oxychloride), or the compound (s) is subjected to reaction with a trifluoromethanesulfonic anhydride, a methanesulfonyl chloride or a toluenesulfonyl chloride under the presence of a base.


the same meaning described above.]
(Referential Production Method 10)
Among the compound (r), the compound (r-1) may be also produced by subjecting the compound (t) to reaction with a halogenating agent. The halogenating agent used for the reaction includes, for example, N-Bromosuccinimide and N-Cholorosuccinimide.

The embodiment of the compound of the present invention includes, for example, the following compounds: a malononitrile compound represented by the formula (I) wherein R1 is a hydrogen atom;
a malononitrile compound represented by the formula (I) wherein R2 is a methyl group; a malononitrile compound represented by the formula (I) wherein

R1 and R2 are hydrogen atoms;
a malononitrile compound represented by the formula (I) wherein
R1 is a hydrogen atom and R2 is a methyl group;
a malononitrile compound represented by the formula (I) wherein
R3 is a hydrogen atom;
a malononitrile compound represented by the formula (I) wherein
R4 is a C2-C5 alkenyl group optionally substituted by one or
more halogen atoms;
a malononitrile compound represented by the formula (I) wherein
R4 is a vinyl group;
a malononitrile compound represented by the formula (I) wherein
R4 is a 2-propenyl group;
a malononitrile compound represented by the formula (I) wherein
R4 is a 2,2-difluorovinyl group;
a malononitrile compound represented by the formula (I) wherein
R4 is a 1-(trifluoromrthyl)vinyl group;
a malononitrile compound represented by the formula (I) wherein
R4 is a 3,3-difluoro-2-propenyl group;
a malononitrile compound represented by the formula (I) wherein
R4 is a 2,3,3-trifluoro-2-propenyl group;
a malononitrile compound represented by the formula (I) wherein
R4 is a 3,3,3-trifluoro-1-propenyl group;
a malononitrile compound represented by the formula (I) wherein
R4 is a C2-C5 alkynyl group optionally substituted by one or
more halogen atoms;

a malononitrile compound represented by the formula (I) wherein
R4 is a C1-C5 fluoroalkyl group;
a malononitrile compound represented by the formula (I) wherein
R4 is a fluoromethyl group;
a malononitrile compound represented by the formula (I) wherein
R4 is a 2,2-difluoroethyl group;
a malononitrile compound represented by the formula (I) wherein
R4 is a 2,2,2-trifluoroethyl group;
a malononitrile compound represented by the formula (I) wherein
R4 is a pentafluoroethyl group;
a malononitrile compound represented by the formula (I) wherein
R4 is a 3,3,3-trifluoropropyl group;
a malononitrile compound represented by the formula (I) wherein
R4 is a 2,2,3,3,3-pentafluoropropyl group;
a malononitrile compound represented by the formula (I) wherein
R4 is a C3-C5 cycloalkyl group optionally substituted by one
or more halogen atoms;
a malononitrile compound represented by the formula (I) wherein
R4 is a 2,2-dichlorocyclopropyl group;
a malononitrile compound represented by the formula (I) wherein
R4 is a cyclopropyl group;
a malononitrile compound represented by the formula (I) wherein
R4 is a cyclobutyl group;
a malononitrile compound represented by the formula (I) wherein
R3 is a hydrogen atom and R4 is a C1-C5 alkyl group optionally

substituted by one or more halogen atoms, a C2-C5 alkenyl group optionally substituted by one or more halogen atoms, a C2-C5 alkynyl group optionally substituted by one or more halogen atoms, a C3-C5 cycloalkyl group optionally substituted by one or more halogen atoms, or a C5-C6 cycloalkenyl group optionally substituted by one or more halogen atoms;
a malononitrile compound represented by the formula (I) wherein R3 is a hydrogen atom and R4 is a C2-C5 alkenyl group optionally substituted by one or more halogen atoms, a C2-C5 alkynyl group optionally substituted by one or more halogen atoms, or a C3-C5 cycloalkyl group optionally substituted by one or more halogen atoms;
a malononitrile compound represented by the formula (I) wherein R3 is a hydrogen atom, R4 is a C2-C5 alkenyl group optionally substituted by one or more halogen atoms, a C2-C5 alkynyl group optionally substituted by one or more halogen atoms or a C3-C5 cycloalkyl group optionally substituted by one or more halogen atoms, X1 and X2 are nitrogen atoms, and X3 is CR6; a malononitrile compound represented by the formula (I) wherein R3 is a hydrogen atom, R4 is a C2-C5 alkenyl group optionally substituted by one or more halogen atoms, a C2-C5 alkynyl group optionally substituted by one or more halogen atoms or a C3-C5 cycloalkyl group optionally substituted by one or more halogen atoms, X1 and X3 are nitrogen atoms, and X2 is CR6; a malononitrile compound represented by the formula (I) wherein

R3 is a hydrogen atom, R4 is a C2-C5 alkenyl group optionally
substituted by one or more halogen atoms, a C2-C5 alkynyl group
optionally substituted by one or more halogen atoms or a C3-C5
cycloalkyl group optionally substituted by one or more halogen
atoms, X2 and X3 are a nitrogen atom, and X1 is CR6;
a malononitrile compound represented by the formula (I) wherein
R3 is a hydrogen atom and R4 is a vinyl group or a 2-propenyl
group;
a malononitrile compound represented by the formula (I) wherein
R3 is a hydrogen atom and R4 is a 2,2-difluorovinyl group, a
1-(trifluoromethyl)vinyl group, a 3,3-difluoro-2-propenyl
group, a 2,3,3-trifluoro-2-propenyl group or a
3,3,3-trifluoro-l-propenyl group;
a malononitrile compound represented by the formula (I) wherein
R3 is a hydrogen atom and R4 is a fluoromethyl group, a
2,2-difluoroethyl group, a 2,2,2-trifluoroethyl group, a
1,1,2,2,2-pentafluoroethyl group, a 3,3,3-trifluoropropyl
group or a 2,2,3,3,3-pentafluoropropyl group;
a malononitrile compound represented by the formula (I) wherein
R3 is a hydrogen atom and R4 is a cyclopropyl group, a cyclobutyl
group or a 2,2-dichlorocyclopropyl group;
a malononitrile compound represented by the formula (I) wherein
R1, R2 and R3 are hydrogens atom and R4 is a C2-C5 alkenyl group
optionally substituted by one or more halogen atoms, a C2-C5
alkynyl group optionally substituted by one or more halogen atoms

or a C3-C5 cycloalkyl group optionally substituted by one or
more halogen atoms;
a malononitrile compound represented by the formula (I) wherein
R1, R2 and R3 are hydrogen atoms and R4 is a vinyl group or a
2-propenyl group;
a malononitrile compound represented by the formula (I) wherein
R1, R2 and R3 are hydrogen atoms and R4 is a 2,2-difluorovinyl
group, a 1-(trifluoromethyl)vinyl group, a
3,3-difluoro-2-propenyl group, a 2,3,3-trifluoro-2-propenyl
group or a 3,3,3-trifluoro-l-propenyl group;
a malononitrile compound represented by the formula (I) wherein
R1 and R3 are hydrogen atoms, R2 is a methyl group and R4 is a
2,2-difluorovinyl group, a 1-(trifluoromethyl)vinyl group, a
3,3-difluoro-2-propenyl group, a 2,3,3-trifluoro-2-propenyl
group, a 3,3,3-trifluoro-l-propenyl group;
a malononitrile compound represented by the formula (I) wherein
R1, R2 and R3 are hydrogen atoms and R4 is a fluoromethyl group,
a 2,2-difluoroethyl group, a 2,2,2-trifluoroethyl group, a
pentafluoroethyl group, a 3,3,3-trifluoropropyl group or a
2,2,3,3,3-pentafluoropropyl group;
a malononitrile compound represented by the formula (I) wherein
R1 and R3 are hydrogen atoms, R2 is a methyl group and R4 is a
fluoromethyl group, a 2,2-difluoroethyl group, a
2,2,2-trifluoroethyl group, a pentafluoroethyl group, a
3,3,3-trifluoropropyl group or a 2,2,3,3,3-pentafluoropropyl

group;
a malononitrile compound represented by the formula (I) wherein
R1, R2 and R3 are hydrogen atoms and R4 is a cyclopropyl group,
a cyclobutyl group or a 2,2-dichlorocyclopropyl group;
a malononitrile compound represented by the formula (I) wherein
R1 and R3 are hydrogen atoms and R4 is a C2-C5 alkenyl group
optionally substituted by one or more halogen atoms, a C2-C5
alkynyl group optionally substituted by one or more halogen atoms
or a C3-C5 cycloalkyl group optionally substituted by one or
more halogen atoms;
a malononitrile compound represented by the formula (I) wherein
X1, X2 or X3 is CR6 and R6 is a hydrogen atom;
a malononitrile compound represented by the formula (I) wherein
X1 is CR6 and R6 is a hydrogen atom;
a malononitrile compound represented by the formula (I) wherein
X2 is CR6 and R6 is a hydrogen atom;
a malononitrile compound represented by the formula (I) wherein
X3 is CR6 and R6 is a hydrogen atom;
a malononitrile compound represented by the formula (I) wherein
X3 is CR6 and R6 is R5;
a malononitrile compound represented by the formula (I) wherein
X1, X2 or X3 is CR6, R6 is a hydrogen atom and R5 is a nitro group,
aCl-C5 alkyl group optionally substituted by one or more halogen
atoms, a C2-C5 alkenyl group optionally substituted by one or
more halogen atoms, aC2-C5 alkynyl group optionally substituted

by one or more halogen atoms, a C1-C5 alkoxy group optionally
substituted by one or more halogen atoms, a C3-C6 alkenyloxy
group optionally substituted by one or more halogen atoms, a
C3-C6 alkynyloxy group optionally substituted by one or more
halogen atoms, a C1-C5 alkylthio group optionally substituted
by one or more halogen atoms, an alkylsulfinyl group optionally
substituted by one or more halogen atoms or an alkylsulfonyl
group optionally substituted by one or more halogen atoms;
a malononitrile compound represented by the formula (I) wherein
X1, X2 or X3 is CR6, R6 is a hydrogen atom, m is 1 and R5 is a
cyano group;
a malononitrile compound represented by the formula (I) wherein
X1, X2 or X3 is CR6, R6 is a hydrogen atom, m is 1 and R5 is a
fluorine atom;
a malononitrile compound represented by the formula (I) wherein
X1, X2 or X3 is CR6, R6 is a hydrogen atom, m is 1 and R5 is a
chlorine atom;
a malononitrile compound represented by the formula (I) wherein
X1, X2 or X3 is CR6, R6 is a hydrogen atom, m is 1 and R5 is a
bromine atom;
a malononitrile compound represented by the formula (I) wherein
X1, X2 or X3 is CR6, R6 is a hydrogen atom, m is 1 and R5 is a
methyl group;
a malononitrile compound represented by the formula (I) wherein
X1, X2 or X3 is CR6, R6 is a hydrogen atom, m is 1 and R5 is a

ethyl group;
a malononitrile compound represented by the formula (I) wherein
X1, X2 or X3 is CR6, R6 is a hydrogen atom, m is 1 and R5 is an
isopropyl group;
a malononitrile compound represented by the formula (I) wherein
X1, X2 or X3 is CR6, R6 is a hydrogen atom, m is 1 and R5 is a
t-butyl group;
a malononitrile compound represented by the formula (I) wherein
X1, X2 or X3 is CR6, R6 is a hydrogen atom, m is 1 and R5 is a
1-fluoro-l-methylethyl group;
a malononitrile compound represented by the formula (I) wherein
X1, X2 or X3 is CR6, R6 is a hydrogen atom, m is 1 and R5 is a
trifluoromethyl group;
a malononitrile compound represented by the formula (I) wherein
X1, X2 or X3 is CR6, R6 is a hydrogen atom, m is 1 and R5 is a
pentafluoroethyl group;
a malononitrile compound represented by the formula (I) wherein
X1, X2 or X3 is CR6, R6 is a hydrogen atom, m is 1 and R5 is a
propargyl group;
a malononitrile compound represented by the formula (I) wherein
X1, X2 or X3 is CR6, R6 is a hydrogen atom, m is 1 and R5 is a
vinyl group;
a malononitrile compound represented by the formula (I) wherein
X1, X2 or X3 is CR6, R6 is a hydrogen atom, m is 1 and R5 is a
propargyloxy group;

a malononitrile compound represented by the formula (I) wherein
X1, X2 or X3 is CR6, R6 is a hydrogen atom, m is 1 and R5 is a
2-butynyloxy group;
a malononitrile compound represented by the formula (I) wherein
X1, X2 or X3 is CR6, R6 is a hydrogen atom, m is 1 and R5 is a
3-butynyloxy group;
a malononitrile compound represented by the formula (I) wherein
a malononitrile compound represented by the formula (I) wherein
X1, X2 or X3 is CR6, R6 is a hydrogen atom, m is 1 and R5 is a
methoxy group;
a malononitrile compound represented by the formula (I) wherein
X1, X2 or X3 is CR6, R6 is a hydrogen atom, m is 1 and R5 is a
methylthio group;
a malononitrile compound represented by the formula (I) wherein
X1, X2 or X3 is CR6, R6 is a hydrogen atom, m is 1 and R5 is a
trifluoromethylthio group;
a malononitrile compound represented by the formula (I) wherein
X1, X2 or X3 is CR6, R6 is a hydrogen atom, m is 1 and R5 is a
trifluoromethylsulfinyl group;
a malononitrile compound represented by the formula (I) wherein
X1, X2 or X3 is CR6, R6 is a hydrogen atom, m is 1 and R5 is a
trifluoromethylsulfonyl group;
a malononitrile compound represented by the formula (I) wherein
X1, X2 or X3 is CR6, R6 is a hydrogen atom, m is 1 and R5 is a
nitro group;

a malononitrile compound represented by the formula (I) wherein X1, X2 or X3 is CR6, R6 is a hydrogen atom, m is 1 and R5 is a dimethylamino group;
a malononitrile compound represented by the formula (I) wherein X1, X2 and X3 are nitrogen atoms and R5 is a nitro group, a C1-C5 alkyl group optionally substituted by one or more halogen atoms, a C2-C5 alkenyl group optionally substituted by one or more halogen atoms, a C2-C5 alkynyl group optionally substituted by one or more halogen atoms, a C1-C5 alkoxy group optionally substituted by one or more halogen atoms, a C3-C6 alkenyloxy group optionally substituted by one or more halogen atoms, a C3-C6 alkynyloxy group optionally substituted by one or more halogen atoms, a C1-C5 alkylthio group optionally substituted by one or more halogen atoms, an alkylsulfinyl group optionally substituted by one or more halogen atoms or an alkylsulfonyl group optionally substituted by one or more halogen atoms;


substituted by one or more halogen atoms, a C2-C5 alkynyl group optionally substituted by one or more halogen atoms or a hydrogen atom;
R2 represents a C1-C5 alkyl group optionally substituted by one or more halogen atoms, a C1-C5 alkoxy group optionally substituted by one or more halogen atoms, a C2-C5 alkenyl group optionally substituted by one or more halogen atoms, a C2-C5 alkynyl group optionally substituted by one or more halogen atoms, a cyano group or a hydrogen atom;
each of R3 andR4 is represents a C1-C5 alkyl group optionally substituted by one or more halogen atoms, a C2-C5 alkenyl group optionally substituted by one or more halogen atoms, a C2-C5 alkynyl group optionally substituted by one or more halogen atoms, a C3-C5 cycloalkyl group optionally substituted by one or more halogen atoms, aC5-C6 cycloalkenyl group optionally substituted by one or more halogen atoms or a hydrogen atom, or represents a C2-C6 alkanediyl group optionally substituted by one or more halogen atoms or a C4 -C6 alkenediyl group optionally substituted by one or more halogen atoms in each of which R3 and R4 couple one another at the ends thereof; R5a represents a hydrogen atom, halogen atom, a cyano group, a nitro group, a hydroxyl group, a mercapto group, a f ormyl group, a SF5 group, a carboxyl group, a C1-C5 alkyl group optionally substituted by one or more halogen atoms, a C2-C5 alkenyl group optionally substituted by one or more halogen atoms, a C2-C5

alkynyl group optionally substituted by one or more halogen atoms , a C3-C5 cycloalkyl group optionally substituted by one or more halogen atoms, a C1-C5 alkoxy group optionally substituted by one or more halogen atoms, a C3-C6 alkenyloxy group optionally substituted by one or more halogen atoms, a C3-C6 alkynyloxy group optionally substituted by one or more halogen atoms, a C1-C5 alkylthio group optionally substituted by one or more halogen atoms, a C3-C5 alkenylthio group optionally substituted by one or more halogen atoms, aC3-C5 alkynylthio group optionally substituted by one or more halogen atoms, a C1-C5 alkylsulfinyl group optionally substituted by one or more halogen atoms, a C1-C5 alkylsulf onyl group optionally substituted by one or more halogen atoms, a C2-C6 alkylcarbonyl group optionally substituted by one or more halogen atoms, a C2-C5 alkoxycarbonyl group optionally substituted by one or more halogen atoms, a group designated by -NR10Rn, a group designated by ~C(=X5)NR12R13 or a group designated by -C(=NOR14)R15,
each of R10 and R11 represents a C1-C5 alkyl group optionally substituted by one or more halogen atoms, a C3-C5 alkenyl group optionally substituted by one or more halogen atoms, a C3-C5 alkynyl group optionally substituted by one or more halogen atoms, a C3-C5 cycloalkyl group optionally substituted by one or more halogen atoms, a (C1-C5 alkoxy optionally substituted by one or more halogen atoms) C1-C3 alkyl group, a C1-C5 alkylsulf onyl group optionally substituted by one or more halogen atoms, a

C2-C6 alkylcarbonyl group optionally substituted by one or more halogen atoms, a C2-C5 alkoxycarbonyl group optionally substituted by one or more halogen atoms or a hydrogen atom, or represents a C2-C6 alkanediyl group optionally substituted by one or more halogen atoms or a C4 -C6 alkenediyl group optionally substituted by one or more halogen atoms in each of which R10 and R11 are coupled with one another at the ends thereof; each of R12 and R13 represents a C1-C5 alkyl group optionally substituted by one or more halogen atoms, a C3-C5 alkenyl group optionally substituted by one or more halogen atoms, a C3-C5 alkynyl group optionally substituted by one or more halogen atoms, a C3-C5 cycloalkyl group optionally substituted by one or more
halogen atoms, a group designated by — (CH2)nQ1 or a hydrogen atom,
or represents a C2-C6 alkanediyl group optionally substituted by one or more halogen atoms or a C4 -C6 alkenediyl group optionally substituted by one or more halogen atoms in each of which R12 and R13 are coupled with one another at the ends thereof; each of R14 and R15 represents a C1-C5 alkyl group optionally substituted by one or more halogen atoms, a C3-C5 alkenyl group optionally substituted by one or more halogen atoms, a C3-C5 alkynyl group optionally substituted by one or more halogen atoms , a C3-C5 cycloalkyl group optionally substituted by one or more
halogen atoms, a group designated by ~(CH2)nQ2 or a hydrogen atom; each of Q1 and Q2 represents a phenyl group which may be

substituted by a group selected from the group consisted of a C1-C5 alkyl group optionally substituted by one or more halogen atoms, a C1-C5 alkoxy group optionally substituted by one or more halogen atoms, a C1-C5 alkylthio group optionally substituted by one or more halogen atoms and a halogen atom; and X5 represents an oxygen atom or a sulfur atom.
a malononitrile compound represented by the formula (XII) H R1 R2 R3

)m ti^N NC/XCN
, wherein, in the formula,
R1 represents a C1-C5 alkyl group optionally substituted by one
or more halogen atoms, a C2-C5 alkenyl group optionally
substituted by one or more halogen atoms, a C2-C5 alkynyl group
optionally substituted by one or more halogen atoms or a hydrogen
atom;
R2 represents a C1-C5 alkyl group optionally substituted by one
or more halogen atoms, a C1-C5 alkoxy group optionally
substituted by one or more halogen atoms, a C2-C5 alkenyl group
optionally substituted by one or more halogen atoms, a C2-C5
alkynyl group optionally substituted by one or more halogen atoms,
a cyano group or a hydrogen atom;
each of R3 andR4 is represents a C1-C5 alkyl group optionally
substituted by one or more halogen atoms, a C2-C5 alkenyl group

optionally substituted by one or more halogen atoms, a C2-C5 alkynyl group optionally substituted by one or more halogen atoms, a C3-C5 cycloalkyl group optionally substituted by one or more halogen atoms, a C5-C6 cycloalkenyl group optionally substituted by one or more halogen atoms or a hydrogen atom, or represents a C2-C6 alkanediyl group optionally substituted by one or more halogen atoms or a C4 -C6 alkenediyl group optionally substituted by one or more halogen atoms in each of which R3 and R4 couple one another at the ends thereof; R5 represents a halogen atom, a cyano group, a nitro group, a hydroxyl group, a mercapto group, a formyl group, a SF5 group, a carboxyl group, a C1-C5 alkyl group optionally substituted by one or more halogen atoms, a C2-C5 alkenyl group optionally substituted by one or more halogen atoms, a C2-C5 alkynyl group optionally substituted by one or more halogen atoms, a C3-C5 cycloalkyl group optionally substituted by one or more halogen atoms, a C1-C5 alkoxy group optionally substituted by one or more halogen atoms, a C3-C6 alkenyloxy group optionally substituted by one or more halogen atoms, a C3-C6 alkynyloxy group optionally substituted by one or more halogen atoms, a C1-C5 alkylthio group optionally substituted by one or more halogen atoms, a C3-C5 alkenylthio group optionally substituted by one or more halogen atoms, a C3-C5 alkynylthio group optionally substituted by one or more halogen atoms, a C1-C5 alkylsulfinyl group optionally substituted by one or more halogen atoms, a

C1-C5 alkylsulf onyl group optionally substituted by one or more halogen atoms, a C2-C6 alkylcarbonyl group optionally substituted by one or more halogen atoms, a C2-C5 alkoxycarbonyl group optionally substituted by one or more halogen atoms, a group designated by — NR^R11, a group designated by — C (=X5) NR12R13 or a group designated by — C(=NOR14)R15,
each of R10 and R11 represents a C1-C5 alkyl group optionally substituted by one or more halogen atoms, a C3-C5 alkenyl group optionally substituted by one or more halogen atoms, a C3-C5 alkynyl group optionally substituted by one or more halogen atoms, a C3-C5 cycloalkyl group optionally substituted by one or more halogen atoms, a (C1-C5 alkoxy optionally substituted by one or more halogen atoms) C1-C3 alkyl group, a C1-C5 alkylsulf onyl group optionally substituted by one or more halogen atoms, a C2-C6 alkylcarbonyl group optionally substituted by one or more halogen atoms, a C2-C5 alkoxycarbonyl group optionally substituted by one or more halogen atoms or a hydrogen atom, or represents a C2-C6 alkanediyl group optionally substituted by one or more halogen atoms or a C4-C6 alkenediyl group optionally substituted by one or more halogen atoms in each of which R10 and R11 are coupled with one another at the ends thereof; each of R12 and R13 represents a C1-C5 alkyl group optionally substituted by one or more halogen atoms, a C3-C5 alkenyl group optionally substituted by one or more halogen atoms, a C3-C5 alkynyl group optionally substituted by one or more halogen atoms,

a C3-C5 cycloalkyl group optionally substituted by one or more
halogen atoms, a group designated by -(CH2)nQ1 or a hydrogen atom,
or represents a C2-C6 alkanediyl group optionally substituted by one or more halogen atoms or a C4 -C6 alkenediyl group optionally substituted by one or more halogen atoms in each of which R12 and R13 are coupled with one another at the ends thereof; each of R14 and R15 represents a C1-C5 alkyl group optionally substituted by one or more halogen atoms, a C3-C5 alkenyl group optionally substituted by one or more halogen atoms, a C3-C5 alkynyl group optionally substituted by one or more halogen atoms, a C3-C5 cycloalkyl group optionally substituted by one or more
halogen atoms, a group designated by — (CH2)nQ2 or a hydrogen atom; each of Q1 and Q2 represents a phenyl group which may be substituted by a group selected from the group consisted of a C1-C5 alkyl group optionally substituted by one or more halogen atoms, a C1-C5 alkoxy group optionally substituted by one or more halogen atoms, a C1-C5 alkylthio group optionally substituted by one or more halogen atoms and a halogen atom; and X5 represents an oxygen atom or a sulfur atom; and m represents an integer 0 to 2. a malononitrile compound represented by the formula (XIII)


, wherein, in the formula, R1, R2, R3, R4, and R5 represent the same meaning described the definition of the formula (XII) and m represents an integer 0 to 3;
a malononitrile compound represented by the formula (XIV)
, wherein, in the formula, R1, R2, R3, R4, and R5 represent the same meaning described the definition of the formula (XII) and m represents an integer 0 to 2;
a malononitrile compound represented by the formula (XV)

, wherein, in the formula, R1, R2, R3, R4 and R5a represent the same meaning described the definition of the formula (XI);
a malononitrile compound represented by the formula (XVI)

, wherein, in the formula, R1, R2, R3, R4, and R5 represent the same meaning described the definition of the formula (XII) and

m represents an integer 0 to 2;
a malononitrile compound represented by the formula (XI) wherein R3 is a hydrogen atom and R4 is a C1-C5 alkyl group optionally substituted by one or more halogen atoms, a C2-C5 alkenyl group optionally substituted by one or more halogen atoms, a C2-C5 alkynyl group optionally substituted by one or more halogen atoms, a C3-C5 cycloalkyl group optionally substituted by one or more halogen atoms or a malononitrile compound being a C5-C6 cycloalkenyl group optionally substituted by one or more halogen atoms;
amalononitrilecompoundrepresented by theformula (XII) wherein R3 is a hydrogen atom and R4 is a C1-C5 alkyl group optionally substituted by one or more halogen atoms, a C2-C5 alkenyl group optionally substituted by one or more halogen atoms, a C2-C5 alkynyl group optionally substituted by one or more halogen atoms, a C3-C5 cycloalkyl group optionally substituted by one or more halogen atoms or a malononitrile compound being a C5-C6 cycloalkenyl group optionally substituted by one or more halogen atoms;
a malononitrile compound represented by the formula (XIII) wherein R3 is a hydrogen atom and R4 is a C1-C5 alkyl group optionally substituted by one or more halogen atoms, a C2-C5 alkenyl group optionally substituted by one or more halogen atoms, a C2-C5 alkynyl group optionally substituted by one or more

halogen atoms, a C3-C5 cycloalkyl group optionally substituted by one or more halogen atoms or a malononitrile compound being a C5-C6 cycloalkenyl group optionally substituted by one or more halogen atoms;
amalononitrile compoundrepresentedby the formula (XIV) wherein R3 is a hydrogen atom and R4 is a C1-C5 alkyl group optionally substituted by one or more halogen atoms, a C2-C5 alkenyl group optionally substituted by one or more halogen atoms, a C2-C5 alkynyl group optionally substituted by one or more halogen atoms , a C3-C5 cycloalkyl group optionally substituted by one or more halogen atoms or a malononitrile compound being a C5-C6 cycloalkenyl group optionally substituted by one or more halogen atoms;
a malononitrile compound represented by the formula (XV) wherein R3 is a hydrogen atom and R4 is a C1-C5 alkyl group optionally substituted by one or more halogen atoms, a C2-C5 alkenyl group optionally substituted by one or more halogen atoms, a C2-C5 alkynyl group optionally substituted by one or more halogen atoms, a C3-C5 cycloalkyl group optionally substituted by one or more halogen atoms or a malononitrile compound being a C5-C6 cycloalkenyl group optionally substituted by one or more halogen
atoms;
amalononitrile compound represented by the formula (XVI) wherein
R3 is a hydrogen atom and R4 is a C1-C5 alkyl group optionally

substituted by one or more halogen atoms, a C2-C5 alkenyl group optionally substituted by one or more halogen atoms, a C2-C5 alkynyl group optionally substituted by one or more halogen atoms, a C3-C5 cycloalkyl group optionally substituted by one or more halogen atoms or a malononitrile compound being a C5-C6 cycloalkenyl group optionally substituted by one or more halogen atoms;
a malononitrile compound represented by the formula (XI), the formula (XII) or the formula (XIII) wherein R5 or R5a is a nitro group, a C1-C5 alkyl group optionally substituted by one or more halogen atoms, a C1-C5 alkyl group optionally substituted by one or more halogen atoms, a C2-C5 alkenyl group optionally substituted by one or more halogen atoms, a C2-C5 alkynyl group optionally substituted by one or more halogen atoms, a C1-C5 alkoxy group optionally substituted by one or more halogen atoms, a C3-C6 alkenyloxy group optionally substituted by one or more halogen atoms, a C3-C6 alkynyloxy group optionally substituted by one or more halogen atoms, a C1-C5 alkylthio group optionally substituted by one or more halogen atoms, an alkylsulf inyl group optionally substituted by one or more halogen atoms or an alkylsulf onyl group optionally substituted by one or more halogen atoms;
a malononitrile compound represented by the formula (XI) or the formula (XII) wherein R5 or R5a is a cyano group;

a malononitrile compound represented by the formula (XI) or the
formula (XII) wherein R5 or R5a is a fluorine atom;
a malononitrile compound represented by the formula (XI) or the
formula (XII) wherein R5 or R5a is a chlorine atom;
a malononitrile compound represented by the formula (XI) or the
formula (XII) wherein R5 or R5a is a bromine atom;
a malononitrile compound represented by the formula (XI) or the
formula (XII) wherein R5 or R5a is a methyl group;
a malononitrile compound represented by the formula (XI) or the
formula (XII) wherein R5 or R5a is an ethyl group;
a malononitrile compound represented by the formula (XI) or the
formula (XII) wherein R5 or R5a is an isopropyl group;
a malononitrile compound represented by the formula (XI) or the
formula (XII) wherein R5 or R5a is a t-butyl group;
a malononitrile compound represented by the formula (XI) or the
formula (XII) wherein R5 or R5a is a 1-f luoro-1-methylethyl group;
a malononitrile compound represented by the formula (XI) or the
formula (XII) wherein R5 or R5a is a trifluoromethyl group;
a malononitrile compound represented by the formula (XI) or the
formula (XII) wherein R5 or R5a is a pentafluoroethyl group;
a malononitrile compound represented by the formula (XI) or the
formula (XII) wherein R5 or R5a is an ethynyl group;
a malononitrile compound represented by the formula (XI) or the
formula (XII) wherein R5 or R5a is a propargyl group;
a malononitrile compound represented by the formula (XI) or the

formula (XII) wherein R5 or R5a is a vinyl group;
a malononitrile compound represented by the formula (XI) or the
formula (XII) wherein R5 or R5a is a propargyloxy group;
a malononitrile compound represented by the formula (XI) or the
formula (XII) wherein R5 or R5a is a 2-butynyloxy group;
a malononitrile compound represented by the formula (XI) or the
formula (XII) wherein R5 or R5a is a 3-butynyloxy group;
a malononitrile compound represented by the formula (XI) or the
formula (XII) wherein R5 or R5a is a methoxy group;
a malononitrile compound represented by the formula (XI) or the
formula (XII) wherein R5 or R5a is a methylthio group;
a malononitrile compound represented by the formula (XI) or the
formula (XII) wherein R5 or R5a is a trifluoromethylthio group;
a malononitrile compound represented by the formula (XI) or the
formula (XII) wherein R5 or R5a is a trifluoromethylsulfinyl
group;
a malononitrile compound represented by the formula (XI) or the
formula (XII) wherein R5 or R5a is a trifluoromethylsulfonyl
group;
a malononitrile compound represented by the formula (XI) or the
formula (XII) wherein R5 or R5a is a nitro group; and
a malononitrile compound represented by the formula (XI) or the
formula (XII) wherein R5 or R5a is a dimethylamino group.
The pests against which the present invention compound

has control activity may include, for example, arthropods such as insect pests and acarine pests and the like, and nematode pests. Specific examples are listed below:
Hemiptera:
Delphacidae such as Laodelphax striatellus, Nilaparvata lugens, Sogatella furcifera and the like,
Deltocephalidae such as Nephotettix cincticeps, Nephotettix virescens and the like,
Aphididae such as Aphis gossypii, Myzus persicae and the like,
Pentatomidae such as Nezara antennata, Riptortus clavetus, Eysarcoris lewis!, Eysarcoris parvus, Plautia stall, Halyomorpha mista and the like,
Aleyrodidae such as Trialeurodes vaporariorum, Bemisia argentifolii and the like,
Coccidae such as Aonidiella aurantii, Comstockaspis perniciosa, Unaspis citri, Ceroplastes rubens, Icerya purchasi and the like,
Tingidae,
Psyllidae, and the like;
Lepidoptera:
Pyralidae such as Chilo suppressalis, Cnaphalocrocis medinalis, Notarcha derogata, Plodia interpunctella and the like,

Noctuidae such as Spodoptera lltura, Pseudaletla separata,
Thoricoplusia spp., Heliothis spp., Helicoverpa spp. and the
like,
Pieridae such as Pieris rapae and the like, Tortricidae such as Adoxophyes spp., Grapholita molest a,
Cydia pomonella and the like,
Carposinidae such as Carposlna niponensis and the like, Lyonetiidae such as Lyonetia spp. and the like, Lymantriidae such as Lymantria spp. , Euproctis spp. , and
the like,
Yponomeutidae such as Plutella xylostella and the like, Gelechiidae such as Pectinophora gossyplella and the like, Arctiidae such as Hyphantrla cunea and the like, Tineidae such as Tinea translucens, Tlneola blsselllella
and the like;
Diptera:
Calicidae such as Culex plplens pallens, Culex trltaeniorhynchus, Culex guinquefasclatus and the like,
Aedes spp. such as Aedes aegypti, Aedes alboplctus and the like.
Anopheles spp. such as Anopheles sinensis and the like,
Chironomidae,
Muscidae such as Musca domestlca, Musclna stabulans and the like,

Calliphoridae, Sarcophagidae, Fanniidae,
Anthomyiidae such as Delia platura, Delia antiqua and the like,
Tephritidae,
Drosophilidae,
Psychodidae,
Tabanidae,
Simuliidae,
Stomoxyidae,
Agromyzidae, and the like;
Coleoptera:
Diabrotica spp. such as Dlabrotlca vlrglfera vlrglfera, Diabrotlca undeclmpunctata howardl and the like,
Scarabaeidae such as Anomala cuprea, Anomala rufocuprea and the like,
Curculionidae such as Sitophilus zeamais, Lissorhoptrus oryzophllus, Callosobruchuys chlenensls and the like,
Tenebrionidae such as Tenebrlo molltor, Trlbollum castaneum and the like,
Chrysomelidae such as Oulema oryzae, Aulacophora femoralls, Phyllotreta strlolata, Leptlnotarsa decemllneata and the like.

Anobiidae,
Epilachna spp. such as Epilachna vigintioctopunctata and the like,
Lyctidae,
Bostrychidae,
Cerambycidae,
Paederus fuscipes;
Blattodea: Blattella germanica, Periplaneta fuliginosa, Periplaneta americana, Periplaneta brunnea, Blatta orientalis and the like;
Thysanoptera: Thrips palmi, Thrips tabaci, Frankliniella occidentalis, Frankliniella intonsa and the like;
Hymenoptera: Formicidae , Vespidae, bethylid wasp, Tenthredinidae such as Athalia japonica, and the like;
Orthoptera: Gryllotalpidae, Acrididae, and the like;
Aphaniptera: Ctenocephalides felis, Ctenocephalides canis, Pulex irritans, Xenopsylla cheopis, and the like;
Anoplura: Pediculus humanus corporis, Phthirus pubis, Haematopinus eurysternus, Dalmalinia ovis, and the like;
Isoptera: Reticulitermes speratus, Coptotermes formosanus, and the like;
Acarina:
Tetranychidae such as Tetranychus urticae, Tetranychus kanzawai, Panonychus citri, Panonychus ulmi, Oligonychus spp. , and the like.

Eriophyidae such as Aculops pelekassi, Aculus schlechtendal i,, and the like,
Tarsonemidae such as Polyphagotarsonemus latus, and the like,
Tenuipalpidae,
Tuckerellidae,
Ixodidae such as Haemaphysalls longicornis, Haemaphysalis flava, Dermacentor talwanlcus, Ixodes ovatus, Ixodes persulcatus, Boophllus mlcroplus, and the like,
Acaridae such as Tyrophagus putrescentiae, and the like,
Epidermoptidae such as Dermatophagoldes farlnae, Dermatophagoldes ptrenyssnus, and the like,
Cheyletidae such as Cheyletus erudltus, Cheyletus malaccensls, Cheyletus moorel, and the like,
Dermanyssidae;
Araneae: Chiracanthlumjaponicum, Latrodectushasseltll, and the like;
Chilopoda: Thereuonema hllgendorfi, Scolopendra subsplnlpes, and the like;
Diplopoda: Oxidus gracilis, Nedyopus tambanus, and the like;
Isopoda: Armadillidiurn vulgare, and the like;
Gastropoda: Limaxmarginatus, Limax flavus, and the like;
Nematoda: Pratylenchus coffeae, Pratylenchus fallax.

Heterodera glycines, Globodera rostochiensis, Meloidogyne hapla, Meloidogyne incognita, and the like.
The pesticide composition of the present invention contains the present invention compound and an inert carrier. Generally, it is a formulation obtained by mixing the present invention compound and a carrier such as a solid carrier, a liquid carrier and a gaseous carrier, and if necessary, adding a surfactant and other adjuvant for formulation. The formulation includes, for example, an emulsifiable concentrate, an oil solution, a shampoo formulation, a f lowable , a dust, a wettable powder, a granule, a paste formulation, a microcapsule, a foam, an aerosol, a carbon dioxide gas formulation, a tablet, a resin preparation and the like. These formulations can be converted to use into a poison bait, a mosqito coil, an electric mosquito mat, a smoking agent, a fumigant or sheet.
In the pesticide composition of the present invention, the present invention compound is usually contained in an amount of 0.1% to 95% by weight.
The solid carrier for formulation includes, for example, a fine power and a granule of clays (e.g., kaolin clay, diatomite, bentonite, Fubasami clay, acid clay, etc.), synthetic hydrated silicon oxide, talc, ceramic, other inorganic minerals (e.g., sericite, quartz, sulfur, activated carbon, calcium carbonate, hydrated silica) or chemical fertilizers (e.g. , ammonium sulfate.

ammonium phosphate, ammonium nitrate, ammonium chloride, urea) .
The liquid carrier for formulation includes, for example, aromatic or aliphatic hydrocarbons (e.g., xylene, toluene, alkylnaphthalene, phenylxylylethane, kerosine, light oil, 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, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, propylene glycol monomethyl ether, tetrahydrofuran, dioxane), esters (e.g., ethyl acetate, butyl acetate), ketones (e.g., acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone), nitriles (e.g., acetonitrile, isobutyronitrile), sulfoxides (e.g., dimethylsulfoxide), acid amides (e.g., N,N-dimethylformamide, N,N-dimethylacetamide), vegetable oils (e.g., soy bean oil, cotton seed oil), vegetable essential oils (e.g., orange oil, hyssop oil, lemon oil) and water.
The gaseous carrier for formulation includes, for example, butane gas, chlorof luorocarbons, liquefied petroleum gas (LPG) , dimethyl ether, carbon dioxide and the like.
The surfactant for formulation includes, for example, alkyl sulfate salts, alkylsulfonic acid salts, alkylarylsulfonic acid salts, alkyl aryl ethers and their polyoxyethylene derivatives, polyethylene glycol ethers,

polyhydric alcohol esters, and sugar alcohol derivatives.
The other adjuvant for formulation includes, for example, binders, dispersants and stabilizers, and specifically for example, casein, gelatin, polysaccharides (e.g., starch, gum arable, 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 (a mixture of 2-t-butyl-4-methoxyphenol and 3-t-butyl-4-methoxyphenol), vegetable oils, mineral oils, fatty acids, and fatty acid esters.
The base for resin formulation includes, for example, polyvinyl chloride, polyurethane and the like. To these bases, if necessary, a plasticizer such as phthalate (e.g., dimethyl phthalate, dioctyl phthalate), adipate and stearate maybe added. The resin formulation can be obtained by kneading the compound into the base using a known kneader and then formulating by injectionmolding, extrusion molding, press molding and the like, and further, if necessary, via a process for molding, cutting and the like, the resin formulation can be converted into a resin preparation such as board, film, tape, net, string and the like. These resin preparations can be converted into, for example, an animal collar, an animal ear tag, a sheet formulation, an attraction string, a gardening stick.
A base for the poison bait includes, for example, grain

powders, vegetable oils, sugars, and crystalline cellulose, and further, if necessary, 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 may be added to the base.
Pests can be controlled by applying an effective amount of the present invention compound to pests directly and/or habitats of pests (e.g., plant, animal, soil). Usually the formulation of the pesticide composition of the present invention is used as the present invention compound.
When the pesticide composition of the present invention is used for a control of pests in agriculture and forestry, the application amount is usually 1 to 10,000 g/ha, preferably 10 to 1,000 g/ha, as an active ingredient. The emulsifiable concentrates, wettable powders, flowables, and microcapsule formulations are usually applied after dilution with water to have an active ingredient concentration of 1 to 10, 000 ppm, while dusts and granules are usually applied as such. These formulations may be sprayed directly to the plant to be protected from pests. The pests living in a soil can be controlled by treating the soil with these formulations, and the formulations can also be applied to treat seedbeds prior to the planting plants or to treat planting holes or plant bottoms in the planting.

Furthermore, the sheet formulation of the pesticide composition of the present invention can be applied by a method such as winding around plants, stretching in the vicinity of plants and laying on the soil surface at the plant bottom.
When the pesticide composition of the present invention is used for a control of epidemic, the application amount is usually 0.001 to 10 mg/m3 as an active ingredient in case of application for open space, and 0.001 to 100 mg/m2 as an active ingredient in case of application for plane surface. The emulsifiable conscentrate, wettable powders, flowables, and microcapsule formulations are usually applied after dilution with water to have an active ingredient concentration of 0.01 to 10,000 ppm, while oil solutions, aerosols, smoking agents and poison baits are usually applied as such.
When the pesticide composition of the present invention is used for a control of parasite living outside of a livestock such as caw, horse, pig, sheep, goat and chicken, and a small animal such as dog, cat, rat and mouse, the pesticide composition can be applied to said animal by a veterinarily known method. Specifically, for systemic control, the pesticide composition is administered by means of, for example, a tablet, a mixture with feed, a suppository or an injection (e.g., intramuscular, subcutaneous, intravenous, intraperitoneal), and for non-systemic control, it is applied by a method such as spraying an oil solution or an aqueous liquid formulation, carrying out

pour-on treatment or spot-on treatment, washing said animal with a shcimpoo formulation, attaching the resin formulation on said animal as a collar or an ear-tag, and the like. When the present invention compound is administered to an animal, its amount is usually in the range of 0.1 to 1,000 mg/kg body weight of the animal.
The pesticide composition of the present invention can also be used in admixture or combination with other insecticides, nematocides, acaricides, fungicides, herbicides, plant growth regulators, synergists, fertilizers, soil conditioners, animal feeds, and the like.
The active ingredients of such other insecticide and acaricide include, for example, pyrethroid compounds such as allethrin, tetramethrin, prallethrin, phenothrin, resmethrin, cyphenothrin, permethrin, cypermethrin, alpha-cypermethrin, zeta-cypermethrin, deltamethrin, tralomethrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, flumethrin, imiprothrin, etofenprox, fenvalerate, esfenvalerate, fenpropathrin, silafluofen, bifenthrin, transfluthrin, flucythrinate, tau-fluvalinate, acrinathrin and tefluthrin; organophosphorus compounds such as dichlorvos, fenitrothion, cyanophos, profenofos, sulprofos, phenthoate, isoxathion, tetrachlorvinphos, fenthion, chlorpyriphos, diazinon, acephate, terbufos, phorate, chlorethoxyfos, fosthiazate, ethoprophos, cadusaf os andmethidathion; carbamate compounds such as propoxur,

carbaryl, metoxadiazone, fenobucarb, methomyl, thiodicarb, alanycarb, benfuracarb, oxamyl, aldicarb and methiocarb; benzoylphenylurea compounds such as luf enuron, chlorf luazuron, hexaflumuron, diflubenzuron, triflumuron, teflubenzuron, flufenoxuron, fluazuron, novaluron and triazuron; juvenile hormone-like substances such as pyriproxyfen, methoprene, hydroprene and fenoxycarb; neonicotinoid compounds such as acetamiprid, nitenpyram, thiacloprid, thiamethoxam and dinotef uran; N-phenyl-pyrazole compounds such as acetoprole and ethiprole; benzoylhydrazine compounds such as tebufenozide, chromafenozide, methoxyfenozide and halofenozide; diafenthiuron; pymetrozine; flonicamid; triazamate; buprofezin; spinosad; emamectin benzoate; chlorfenapyr; indoxacarb MP; pyridalyl; cyromazine; fenpyroximate; tebufenpyrad; tolfenpyrad; pyridaben; pyrimidifen; f luacrypyrim; etoxazole; fenazaquin; acequinocyl; hexythiazox; clofentezine; fenbutatin oxide; dicofol, propargite; abamectin; milbemectin; amitraz; cartap; bensultap; thiocyclam; endosulfan; spirodiclofen; spiromesifen; and azadirachtin.
The active ingredients of such other fungicide include, for example, strobilurin compounds such as azoxystrobin; organophosphorus compounds such as tolclofos-methyl; azole compounds such as trif lumizole, pefurazoate anddifenoconazole; fthalide; flutolanil; validamycin; probenazole; diclomezine;

pencycuron; dazomet; kasugamycin; IBP; pyroquilon; oxolinic acid; tricyclazole; ferimzone; mepronil; EDDP; isoprothiolane; carpropamid; diclocymet; furametpyr; fludioxonil; procymidone; and diethofencarb.
The present invention is construed in more detail by production examples, formulation examples and test examples, but should not be limited thereto. Firstly, production examples of the compound of the present invention are illustrated.
Production Example 1
0.21 g of 2-t-butyl-5-chloromethylpyrimidine and 0.19 g of (3,3,3-trifluoropropyl)malononitrile were dissolved in 10 ml of N,N-dimethylformamide and then added with 0.16 g of potassium carbonate under ice cooling, followed by stirring at a room temperature for overnight. The reaction mixture was added with saturated brine, followed by extraction with t-butylmethylether. The organic phase was washed by saturated brine and then dried with an anhydrous sodium sulfate, followed by concentration under reduced pressure. The residue was subjected to a silica gel column chromatography to obtain 0.22 g of
[(2-t-butylpyrimidine-5-yl)methyl](3,3,3-trifluoropropyl)ma lononitrile ( , which is referred to as the compound of the present invention (1) hereinafter).

1H-NMR (CDC13, TMS) , 6 (ppm) : 1.44 (9H, s) , 2.28-2.32 (2H, m) , 2.52-2.26 (2Hf m), 3.24 (2H, s), 8.74 (2H, s)
Production Example 2
0.15 g of 2-t-butyl-5-chloromethylpyrazine and 0.13 g of (3,3,3-trifluoropropyl)malononitrile were dissolved in 5 ml of N,N-dimethylformamide and then added with O.llg of potassium carbonate under ice cooling, followed by stirring at a room temperature for overnight.
The reaction mixture was added with saturated brine, followed by extraction with t-butylmethylether. The organic phase was washed by saturated brine and then dried with an anhydrous sodium sulfate, followed by concentration under reduced pressure. The residue was subjected to a silica gel column chromatography to obtain 0.13 g of
[(2-1-butylpyrazine- 5-yl)methyl](3,3,3-trifluoropropyl)malo nonitrile (which is referred to as the compound of the present invention (2) hereinafter).
1H-NMR (CDCI3, TMS),δ(ppm) : 1.45 (9H, s), 2.37-2.41 (2H, m), 2.55-2.64 (2H, m), 3.47 (2H, s), 8.55 (1H, s), 8.70 (1H, s)
Production Example 3
0.12 g of 3-t-butyl-6-chloromethylpyridazine and 0.10 g of (3,3,3-trifluoropropyl)malononitrile were dissolved in 5 ml of N,N-dimethylf ormamide and then added with 0 .087 g of potassium

carbonate under ice cooling, followed by stirring at a room temperature for overnight. The reaction mixture was added with saturated brine, followed by extraction with t-butylmethylether. The organic phase was washed by saturated brine and then dried with an anhydrous sodium sulfate, followed by concentration under reduced pressure. The residue was subjected to a silica gel column chromatography to obtain 0.15 g of
[(6-t-butylpyridazine-3-yl)methyl](3,3,3-trifluoropropyl)ma lononitrile (, which is referred to as the compound of the present invention (3) hereinafter).
1H-NMR (CDC13, TMS),δ(ppm) : 1.48 (9H, s), 2.37-2.41 (2H, m) , 2.60-2.64 (2H, m), 3.65 (2H, s), 7.51 (1H, d), 7.61 (1H, d)
Production Example 4
100 mg of 5-chlorometyl»2-methylthiopyrimidine and 93 mg of (3,3,3-trifluoropropyl)malononitrile were dissolved in 3 ml of N,N-dimethylf ormamide and then added with 80 mg of potassium carbonate under ice cooling, followed by stirring at a room temperature for overnight. The reaction mixture was added with saturated brine, followed by extraction with t-butylmethylether. The organic phase was washed by saturated brine and then dried with an anhydrous sodium sulfate, followed by concentration under reduced pressure. The residue was subjected to a silica gel column chromatography to obtain 0.10

g of
[(2-methylthiopyrimidine-5-yl)methyl](3,3,3-trifluoropropyl )malononitrile (, which is referred to as the compound of the present invention (4) hereinafter).
1H-NMR (CDC13, TMS), 6 (ppm) : 2.26-2.30 (2H, m) , 2.51-2.63 (2H, m), 2.60 (3H, s), 3.20 (2H, s), 8.57 (2H, s)
Production Example 5
0.84 g of [(2-methylthiopyrimidine-5-yl)methyl](3,3,3-trifluoropropyl )malononitrile was dissolved in 30 ml of chloroform and then added with 0 .97 g of m-chloroperbenzoic acid under ice cooling, followed by stirring at a room temperature for 6 hours. The reaction mixture was successively washed by 3 % aqueous solution of sodium thiosulf ate and by saturated aqueous solution of sodium hydrogen carbonate. The organic phase was dried with an anhydrous sodium sulfate, followed by concentration under reduced pressure to obtain 0.76 g of
[(2-methanesulfonylpyrimidine-5-yl)methyl](3,3,3-trifluorop ropyl)malononitrile (, which is referred to as the compound of the present invention (5) hereinafter).
1H-NMR (DMSO-d6/ TMS), δ (ppm) : 2.50-2.56 (2H, m) , 2.61-2.72 (2H, m), 3.45 (3H, s), 3.77 (2H, s), 9.12 (2H, s)
Production Example 6

0.50 g of [(2-methanesulfonylpyrimidine-5-yl)methyl] (3, 3,3 -trifluorop ropyl)malononitrile was dissolved in 5 ml of dimethylsulf oxide and then added with 0.10 g of potassium cyanide, followed by stirring at a room temperature for 8 hours. The reaction mixture was added with water, followed by extraction with t-butylmethylether. The organic phase was successively washed by saturated aqueous solution of sodium hydrogen carbonate and by saturated brine and then dried with an anhydrous sodium sulfate, followed by concentration under reduced pressure. The residue was subjected to a silica gel column chromatography to obtain 0.12 g of
[(2-cyanopyrimidine-5-yl)methyl](3,3,3-trifluoropropyl)malo nonitrile ( , which is referred to as the compound of the present invention (6) hereinafter).
1H-NMR (CDC13, TMS), 6 (ppm) : 2.35-2.40 (2H, m) , 2.55-2.64 (2H, m), 3.36 (2H, s), 8.95 (2H, s)
Production Example 7
70 mg of propargylalcohol was dissolved in 10 ml of tetrahydrofuran and then added with 50 mg of sodium hydride (60 % oiliness) under stirring at a room temperature. Then, being stirred at a room temperature for one hour. Successively, the reaction mixture was added with 400 mg of [(2-methanesulfonylpyrimidine-5-yl)methyl](3,3,3-trifluorop

ropyl)malononitrile and then further stirred at a room temperature for 3 hours, and the reaction mixture was added with saturated aqueous solution of ammoniumchloride, followed by extraction with t -butylmethylether. The organic phase was washed by saturated brine and then dried with an anhydrous sodium sulfate, followed by concentration under reduced pressure. The residue was subjected to a silica gel column chromatography to obtain 0.10 g of
{[2-(propargyloxy)pyrimidine-5-yl]methyl}(3,3,3-trifluoropr opyl)malononitrile (, which is referred to as the compound of the present invention (7) hereinafter).
1H-NMR (CDC13, TMS), δ (ppm) : 2.26-2.31 (2H, m) , 2.50 (1H, t), 2.54-2.61 (2H, m), 3.23 (2H, s), 5.07 (2H, d), 8.61 (2H, s)
Production Example 8
50 mg of 2-butyne-l-ol was dissolved in 5 ml of tetrahydrof uran and then added with 30 mg of sodium hydride (60 % oiliness) at a room temperature, followed by stirring at a room temperature for one hour. Successively, the reaction mixture was added with 250 mg of
[(2-methanesulfonylpyrimidine-5-yl)methyl](3,3,3-trifluorop ropyl)malononitrile, followed by stirring at a room temperature for 3 hours. The reaction mixture was added with saturated aqueous solution of ammoniumchloride, followed by extraction with t-butylmethylether. The organic phase was washed by saturated

brine and then dried with an anhydrous sodium sulfate, followed by concentration under reduced pressure. The residue was subjected to a silica gel column chromatography to obtain 0.10 g of
{[2-(2-butynyloxy)pyrimidine-5-yl]methyl}(3,3,3-trifluoropr opyl)malononitrile ( f which is referred to as the compound of the present invention (8) hereinafter).
1H-NMR (CDCI3, TMS) , 6 (ppm) : 1.87 (3H, t) , 2.26-2.30 (2H, m) , 2.54-2.61 (2H, m), 3.22 (2H, s), 5.03 (2H, q), 8.60 (2H, s)
Production Example 9
0.24 g of 5-chloromethyl-2-methylpyrimidine and 0.27 g of (3,3,3-trifluoropropyl)malononitrile were dissolved in 5 ml of N,N-dimethylformamide and then added with 0 . 32 g of potassium carbonate under ice cooling, followed by stirring at a room temperature for overnight. The reaction mixture was added with saturated brine, followed by extraction with t-butylmethylether. The organic phase was washed by saturated brine and then dried with an anhydrous sodium sulfate, followed by concentration under reduced pressure. The residue was subjected to a silica gel column chromatography to obtain 0.11 g of
[(2-methylpyrimidine-5-yl)methyl](3,3,3-trifluoropropyl)mal ononitrile ( , which is referred to as the compound of the present invention (9) hereinafter).

1H-NMR (CDCI3, TMS), 6 (ppm) : 2.27-2.31 (2H, m) , 2.54-2.61 (2H, m), 2.80 (3Hf s), 3.24 (2H, s), 8.71 (2Hf s)
Production Example 10
1.0 g of 5-chloromethyl-2-isopropylpyrimidine and 0.95 g of (3,3,3-trifluoropropyl)malononitrile were dissolved in 15 ml of N,N-dimethylformamide and then added with 0.81 g of potassium carbonate under ice cooling, followed by stirring at a room temperature for overnight. The reaction mixture was added with saturated brine, followed by extraction with t-butylmethylether. The organic phase was washed by saturated brine and then dried with an anhydrous sodium sulfate, followed by concentration under reduced pressure. The residue was subjected to a silica gel column chromatography to obtain 0.40g of
[(2-isopropylpyrimidine- 5-yl)methyl](3,3,3-trifluoropropyl) malononitrile (,which is referred to as the compound of the present invention (10) hereinafter).
1H-NMR (CDCI3, TMS),δ(ppm) : 1-38 (6H, d) , 2.28-2.32 (2H, m) , 2.55-2.61 (2H, m), 3.24 (2H, s), 3.28 (1H, m), 8.73 (2H, s)
Production Example 11
0.75 g of 5-bromomethyl-2-phenylpyrimidine and 0.49 g of (3,3,3-trifluoropropyl)malononitrile were dissolved in 15 ml of N,N-dimethylformamide and then added with 0.42 g of potassium

carbonate under ice cooling, followed by stirring at a room temperature for overnight. The reaction mixture was added with saturated brine, followed by extraction with t-butylmethylether. The organic phase was washed by saturated brine and then dried with an anhydrous sodium sulfate, followed by concentration under reduced pressure. The residue was subjected to a silica gel column chromatography to obtain 0.42 g of
[(2-phenylpyrimidine-5-yl)methyl](3,3,3-trifluoropropyl)mal ononitrile ( , which is referred to as the compound of the present invention (11) hereinafter).
1H-NMR (CDC13, TMS), δ (ppm) : 2.30-2.34 (2H, m) , 2.53-2.65 (2H, m), 3.31 (2H, s), 7.49-7.55 (3H, m), 8.47-8.50 (2H, m), 8.86 (2H, s)
Production Example 12
0.16 g of 5-(chloromethyl)pyrimidine and 0.15 g of (3,3,3-trifluoropropyl)malononitrile were dissolved in 5 ml of N,N-dimethylformamide and then added with 0.13 g of potassium carbonate under ice cooling, followed by stirring at a room temperature for overnight. The reaction mixture was added with saturated brine, followed by extraction with t-butylmethylether. The organic phase was washed by saturated brine and then dried with an anhydrous sodium sulfate, followed by concentration under reduced pressure. The residue was

subjected to a silica gel column chromatography to obtain 0.11 g of
[(pyrimidine-5-yl)methyl](3 , 3 , 3-trifluoropropyl)malononitri le ( , which is referred to as the compound of the present invention (12) hereinafter).
1H-NMR (CDC13, TMS) , 6 (ppm) : 2.30-2.34 (2H, m) , 2.53-2.65 (2H, m), 3.29 (2H, s), 8.84 (2H, s), 9.32 (1H, s)
Production Example 13
0.18 g of 4-t-butyl-2-chloromethylpyrimidine and 0.16 g of (3,3, 3-trif luoropropyl )malononitrile were dissolved in 5 ml of N,N-dimethy If ormeimide and then added with 0.14 g of potassium carbonate under ice cooling, followed by stirring at a room temperature for overnight. The reaction mixture was added with saturated brine, followed by extraction with t-butylmethylether. The organic phase was washed by saturated brine and then dried with an anhydrous sodium sulfate, followed by concentration under reduced pressure. The residue was subjected to a silica gel column chromatography to obtain 0.08 g of
[(4-t-butylpyrimidine-2-yl)methyl] (3, 3,3-trifluoropropyl)ma lononitrile (,which is referred to as the compound of the present invention (13) herein after).
1H-NMR (CDCI3, TMS), 6 (ppm) : 1.39 (9H, s), 2.42-2.46 (2H, m) , 2.59-2.70 (2H, m), 3.64 (2H, s), 7.29 (1H, d), 8.65 (1H, d)

Production Example 14
0.50 g of 5-bromomethyl-2-chloropyrimidine and 0.39 g of (3,3,3-trifluoropropyl)malononitrile were dissolved in 10 ml of N,N-dimethylformamide and then added with 0.33 g of potassium carbonate under ice cooling, followed by stirring at a room temperature for overnight. The reaction mixture was added with saturated brine, followed by extraction with t-butylmethylether. The organic phase was washed by saturated brine and then dried with an anhydrous sodium sulfate, followed by concentration under reduced pressure. The residue was subjected to a silica gel column chromatography to obtain 0.21 g of
[(2-chloropyrimidine-5-yl)methyl](3,3,3-trifluoropropyl)mal ononitrile represented by the formula as shown below (, which is referred to as the compound of the present invention (14) hereinafter).
1H-NMR (CDC13, TMS), d (ppm) : 2.30-2.35 (2H, m) , 2.53-2.65 (2H, m), 3.27 (2H, s), 8.71 (2H, s)
Production Example 15
80 mg of 4-bromomethyl-2-chloropyrimidine and 63 mg of (3,3, 3-trif luoropropyl)malononitrile were dissolved in 3 ml of N,N-dimethylformamide and then added with 53 mg of potassium carbonate under ice cooling, followed by stirring at a room

temperature for overnight. The reaction mixture was added with saturated brine, followed by extraction with t-butylmethylether. The organic phase was washed by saturated brine and then dried with an anhydrous sodium sulfate, followed by concentration under reduced pressure. The residue was subjected to a silica gel column chromatography to obtain 0.07 g of
[(2-chloropyrimidine-4-yl)methyl](3,3,3-trifluoropropyl)mal ononitrile ( , which is referred to as the compound of the present invention (15) hereinafter).
1H-NMR (CDC13, TMS), 6 (ppm) : 2.37-2.41 (2H, m) , 2.55-2.67 (2H, m), 3.44 (2H, s), 7.36 (1H, d), 8.73 (1H, d)
Production Example 16
0.58 g of 5-bromomethyl-2-trifluoromethylpyrimidine and 0.39 g of (3, 3, 3-trif luoropropyl)malononitrile were dissolved in 10 ml of N,N-dimethylformamide and then added with 0.33 g of potassium carbonate under ice cooling, followed by stirring at a room temperature for overnight. The reaction mixture was added with saturated brine, followed by extraction with t-butylmethylether. The organic phase was washed by saturated brine and then dried with an anhydrous sodium sulfate, followed by concentration under reduced pressure. The residue was subjected to a silica gel column chromatography to obtain 0.55 g of

[(2-trifluoromethylpyrimidine-5-yl)methyl](3,3,3-trifluorop ropyl)malononitrile (, which is referred to as the compound of the present invention (16) hereinafter).
1H-NMR (CDC13, TMS) , 6 (ppm) : 2.35-2.39 (2H, m) , 2.55-2.65 (2H, m), 3.38 (2H, s), 9.00 (2H, s)
Production Example 17
0.30 g of 5-bromomethyl-2-trifluoromethylpyrimidine and 0.13 g of allylmalononitrile were dissolved in 5 ml of N,N-dimethylformamide and then added with 0.17 g of potassium carbonate under ice cooling, followed by stirring at a room temperature for overnight. The reaction mixture was added with saturated brine, followed by extraction with t-butylmethylether. The organic phase was washed by saturated brine and then dried with an anhydrous sodium sulfate, followed by concentration under reduced pressure. The residue was subjected to a silica gel column chromatography to obtain 0.23 g of
allyl[(2-trifluoromethylpyrimidine-5-yl)methyl]malononitril e (, which is referred to as the compound of the present invention (17) hereinafter).
^-NMR (CDCI3, TMS), Production Example 18

0.30 g of 5-bromomethyl-2-trifluoromethylpyrimidine and 0.15 g of 3-butenylmalononitrile were dissolved in 5 ml of N,N-dimethylformamide and then added with 0.17 g of potassium carbonate under ice cooling, followed by stirring at a room temperature for overnight. The reaction mixture was added with saturated brine, followed by extraction with t-butylmethylether. The organic phase was successively washed by saturated brine and then dried with an anhydrous sodium sulfate, followed by concentration under reduced pressure. The residue was subjected to a silica gel column chromatography to obtain 0.21 g of
3-butenyl[(2-trifluorometylpyrimidine-5-yl)methyl]malononit rile (, which is referred to as the compound of the present invention (18) hereinafter).
1H —NMR (CDCI3, TMS) , δ (ppm) : 2.14-2.18 (2H, m) , 2.51-2.56 (2H, m), 3.33 (2H, s), 5.16-5.24 (2H, m), 5.83 (1H, m), 8.94 (2H,
s)
Production Example 19
0.17 g of 5-chloromethyl-2-isopropylpyrimidine and 0.11 g of allylmalononitrile were dissolved in 3 ml of N,N-dimethylformamide and then added with 0.14 g of potassium carbonate under ice cooling, followed by stirring at a room temperature for overnight. The reaction mixture was added with saturated brine, followed by extraction with

t-butylmethylether. The organic phase was washed by saturated brine and then dried with an anhydrous sodium sulfate, followed by concentration under reduced pressure. The residue was subjected to a silica gel column chromatography to obtain 0.12 g of allyl[(2-isopropylpyrimidine-5-yl)methyl]malononitrile (, which is referred to as the compound of the present invention (19) hereinafter).
1H-NMR (CDCI3, TMS),δ(ppm) : 1.37 (6H, d) , 2.78 (2H, d) , 3.17 (2H, s), 3.27 (1H, m), 5.45-5.53 (2H, m), 5.95 (1H, m), 8.72 (2H, s)
Production Example 20
80 mg of 2-(bromomethyl)pyrazine and 100 mg of (3,3,3-trifluoropropyl)malononitrile were dissolved in 3 ml of N,N-dimethylformamide and then added with 86 mg of potassium carbonate under ice cooling, followed by stirring at a room temperature for overnight. The reaction mixture was added with saturated brine, followed by extraction with t-butylmethylether. The organic phase was washed by saturated brine and then dried with an anhydrous sodium sulfate, followed by concentration under reduced pressure. The residue was subjected to a silica gel column chromatography to obtain 0.10
g of
[(pyrazine-2-yl)methyl](3,3,3-trifluoropropyl)malononitrile
(, which is referred to as the compound of the present invention

(20) hereinafter).
1H-NMR (CDCI3, TMS), δ (ppm) : 2.37-2.41 (2H, m) , 2.55-2.64 (2H, m), 3.52 (2H, s), 8.64-8.66 (3H, m)
Production Example 21
0.27 g of 3-bromomethyl-6-chloropyridazine and 0.21 g of (3,3,3-trifluoropropyl)malononitrile were dissolved in 5 ml of N,N-dimethylformamide and then added with 0.18 g of potassium carbonate under ice cooling, followed by stirring at a room temperature for overnight. The reaction mixture was added with saturated brine, followed by extraction with t-butylmethylether. The organic phase was washed by saturated brine and then dried with an anhydrous sodium sulfate, followed by concentration under reduced pressure. The residue was subjected to a silica gel column chromatography to obtain 0.20 g of
[(6-chloropyridazine-3-yl)methyl](3,3,3-trifluoropropyl)mal ononitrile ( , which is referred to as the compound of the present invention (21) hereinafter).
1H-NMR (CDCI3, TMS), 6 (ppm) : 2.36-2.41 (2H, m) , 2.54-2.65 (2H, m), 3.69 (2H, s), 7.59 (1H, d), 7.64 (1H, d)
Production Example 22
0.23 g of 2-bromomethyl-5-methoxycarbonylpyrimidine and 0.16 g of (3, 3,3-trif luoropropyl )malononitrile were dissolved

in 5 ml of N,N-dimethylformamide and then added with 0.14 g of potassium carbonate under ice cooling, followed by stirring at a room temperature for overnight. The reaction mixture was added with saturated brine, followed by extraction with t-butylmethylether. The organic phase was washed by saturated brine and then dried with an anhydrous sodium sulfate, followed by concentration under reduced pressure- The residue was subjected to a silica gel column chromatography to obtain 0.21 g of
[(5-methoxycarbonyl-2-yl)methyl](3,3,3-trifluoropropyljmalo nonitrile (, which is referred to as the compound of the present invention (22) hereinafter).
^-NMR (CDC13, TMS) , d (ppm) : 2.42-2.46 (2H, m) , 2.58-2.69 (2H, m), 3.73 (2H, s), 4.01 (3H, s), 9.31 (2H, s)
Production Example 23
0.34 g of 2-chloromethyl-6,7-dihydro-5H-cyclopentapyrimidine

and 0.33 g of (3,3,3-trifluoropropyl)malononitrile were dissolved in 5 ml of N,N-dimethylformamide and then added with 0.28 g of potassium carbonate under ice cooling, followed by stirring at a room temperature for overnight. The reaction mixture was added with saturated brine, followed by

t-butylmethylether. The organic phase was washed by saturated
brine and then dried with an anhydrous sodium sulfate, followed
by concentration under reduced pressure. The residue was
subjected to a silica gel column chromatography to obtain 0.44
g of
[(6,7-dihydro-5H-cyclopentapyrimidine-2-yl)methyl](3,3,3-tr
ifluoropropyl)malononitrile

and 114 mg of (3, 3, 3-trifluoropropyl)malononitrile were dissolved in 3 ml of N,N-dimethylformamide and then added with 97 mg of potassium carbonate under ice cooling, followed by

stirring at a room temperature for overnight. The reaction mixture was added with saturated brine, followed by extraction with t-butylmethylether. The organic phase was washed by saturated brine and then dried with an anhydrous sodium sulfate, followed by concentration under reduced pressure. The residue was subjected to a silica gel column chromatography to obtain 0.19 g of
[(7,7-dimethyl-6,7-dihydro-5H-cyclopentapyrimidine-2-yl)met hyl1(3,3,3-trifluoropropyl)malononitrile

Production Example 25
0.30 g of 5-bromomethyl-2-trifluoromethylpyrimidine and 0.13 g of propargylmalononitrile were dissolved in 5 ml of N,N-dimethylformamide and then added with 0.17 g of potassium carbonate under ice cooling, followed by stirring at a room temperature for overnight. The reaction mixture was added with saturated brine, followed by extraction with

t-butylmethylether. The organic phase was successively washed by saturated brine and then dried with an anhydrous sodium sulfate, followed by concentration under reduced pressure. The residue was subjected to a silica gel column chromatography to obtain 0.17 g of
(propargyl)[(2-trifluoromethylpyrimidine-5-yl)methyl]malono nitrile (, which is referred to as the compound of the present invention (25) hereinafter).
1H-NMR (CDC13, TMS),δ(ppm) : 2.59 (1H, t), 3.03 (2H, d) , 3.50 (2H, s), 9.02 (2H, s)
Production Example 26
0.20 g of 5-bromomethyl-2-trifluoromethylpyrimidine and 0.30 g of 2,2f 3,3-tetrafluoropropylmalononitrile were dissolve in 5 ml of N,N-dimethylformamide and then added with 0.23 g of potassium carbonate under ice cooling, followed by stirring at a room temperature for overnight. The reaction mixture was added with saturated brine, followed by extraction with t-butylmethylether. The organic phase was successively washed by saturated brine and then dried with an anhydrous sodium sulfate, followed by concentration under reduced pressure. The residue was subjected to a silica gel column chromatography to obtain 0.24 g of
(2,2,3,3-tetrafluoropropyl)[(2-trifluoromethylpyrimidine-5-yl)methyl]malononitrile (, which is referred to as the compound

of the present invention (26) hereinafter).
1H-NMR (CDCI3, TMS), δ(ppm) : 3.00 (2H, t), 3.60 (2H, s), 5.96 (1H, tt), 9.06 (2H, s)
Production Example 27
0.40 g of 2-chloromethyl-7,7-dimethyl-6,7-dihydro-5H-cyclopentapyrimi dine and 0.22 g of allylmalononitrile were dissolved in 10 ml of N,N-dimethylf ormamide and then added with 0 . 28 g of potassium carbonate under ice cooling, followed by stirring at a room temperature for overnight. The reaction mixture was added with saturated brine, followed by extraction with t-butylmethylether.
The organic phase was washed by saturated brine and then dried with an anhydrous sodium sulfate, followed by concentration under reduced pressure. The residue was subjected to a silica gel column chromatography to obtain 0.34 g of
allyl[(7,7-dimethyl-6,7-dihydro-5H-cyclopentapyrimidine-2-y 1) methyl ]malononitrile (, which is referred to as the compound of the present invention (27) hereinafter).


Production Example 28
0.40 g of 2-chloromethyl-7,7-dimethyl-6,7-dihydro-5H-cyclopentapyrimi dine and 0-24 g of 3-butenylmalononitrile were dissolved in 3 ml of N,N-dimethylformamide and then said mixed liquid was added with 0.28 g of potassium carbonate along with agitation under ice cooling, followed by stirring at a room temperature for overnight. The reaction mixture was added with saturated brine, followed by extraction with t-butylmethylether. The organic phase was washed by saturated brine and then dried with an anhydrous sodium sulfate, followed by concentration under reduced pressure. The residue was subjected to a silica gel column chromatography to obtain 0.29 g of
3-butenyl[(7,7-dimethyl-6 f 7-dihydro-5H-cyclopentapyrimidine - 2-yl)methyl] malononitrile
































0.27 g of 2-t-butyl-5-pyrimidinecarboxylic acid methyl ester was dissolved in 10 ml of tetrahydrof uran under a nitrogen atmosphere and then dropped with 3.0 ml of toluene solution of diisobutylaluminum hydride (1 mole/L) under ice cooling, followed by stirring as itself for one hour. The reaction mixture was poured into saturated brine, followed by extraction with ethylacetate. The organic phase was dried with an anhydrous sodium sulfate, followed by concentration under reduced pressure. The residue was subjected to a silica gel column chromatography to obtain 0.09 g of (2-t-buylpyrimidine-5-yl)methanol represented by above formula.
^-NMR (CDC13, TMS) , 6 (ppm) : 1.45 (9H, s) , 4.72 (2H, brs) ,8.69 (2H, s)
Referential Production Example 3
2-t-butyl-5-chloromethylpyrimidine (, represented by the following formula)

0.25 g of (2-t-butylpyrimidine-5-yl)methanol was dissolved with 5 ml of chloroform and then added with 0.2 g of thionylchloride, followed by heating under reflux for one hour. The reaction mixture was cooled down to a room temperature, followed by concentration under reduced pressure. The residue

was added with water and saturated aqueous solution of sodium hydrogen carbonate, followed by extraction with ethylacetate. The organic phase was dried with an anhydrous sodium sulfate, followed by concentration under reduced pressure to obtain 0.21 g of 2-t-butyl-5-chloromethylpyrimidine.
Referential Production Example 4
2-chloro-5-methylpyrimidine (, represented by the following formula)

Above remarked compound produced by the method described in Aust. J. Chem., Vol. 26, p.443-447.
Referential Production Example 5
5-bromomethyl-2-chloropyrimidine (, represented by the following formula)

0.40 g of 2-chloro-5-methylpyrimidine was dissolved in 15 ml of carbontetrachloride and then added with 0.83 g of N-bromosuccinimide and 0.05 g of azobisisobutyronitrile, followed by heating under reflux for 8 hours . The reaction mixture was cooled down to a room temperature and then filtrated, followed

by the filtrate being concentrated under reduced pressure. The residue was subjected to a silica gel column chromatography to obtain 0.27 g of 5-bromomethyl-2-chloropyrimidine represented by above formula. 1H-NMR (CDCI3, TMS),δ(ppm) : 4.43 (2Hf s), 8.67 (2H, s)
Referential Production Example 6
3-chloro-6-methylpyridazine (, represented by the following formula)

5.0 g of 6-methyl-2H-pyridazine-3-one and 28 g of phosphorus oxychloride were mixed, followed by heating under reflux for 2 hours. The reaction mixture was cooled down to a room temperature and then poured into ice water, followed by extraction with ethylacetate. The organic phase was dried with an anhydrous sodium sulfate, followed by concentration under reduced pressure to obtain 1.6 gof 3-chloro-6-methylpyridazine.
Referential Production Example 7
3-bromomethyl-6-chloropyridazine (, represented by the following formula)


1.0 g of 3-chloro-6-methylpyridazine was dissolved in 20 ml of carbontetrachloride and then added with 1.4 g of N-bromosuccinimide and 0.13 g of azobisisobutyronitrile, followed by heating under reflux for 8 hours . The reaction mixture was cooled down to a room temperature and then filtrated, followed by the filtrate being concentrated under reduced pressure. The residue was subjected to a silica gel column chromatography to obtain 0.27 g of 3-bromomethyl-6-chloropyridazine represented by above formula.
1H-NMR (CDC13, TMS)δ(ppm) : 4.56 (2H, s), 7.38 (1H, d) , 7.44 (1H, d)
Formulation Examples are exemplified below. In addition, "part" means a part by weight. The present invention compounds are designated by their compound numbers shown in Tables 1.
Formulation Example 1
9 Parts of each of the present invention compounds (1) to (28) are dissolved in 37.5 parts of xylene and 37.5 parts of dimethylformamide, and 10 parts of polyoxyethylene styryl phenyl ether and 6 parts of calcium dodecylbenzenesulf onate are added thereto, followed by well stirring and mixing, to give an emulsifiable concentrate for each compound.
Formulation Example 2
To 40 parts of each of the present invention compounds (1) to (28) are added 5 parts of SORPOL 5060 (registered trade

name for TOHO KAGAKU KOGYO), followed by well mixing. To the mixture are added 32 parts of CARPLEX #80 (registered trade name for SHIONOGI & Co., synthetic hydrated silicone oxide fine powder) and 23 parts of 300 mesh diatomaceous earth, followed by mixing with juice mixer, to give a wettable powder for each compound.
Formulation Example 3
To 3 parts of each of the present invention compounds (1) to (28) are added 5 parts of synthetic hydrated silicon oxide fine powder, 5 parts of sodium dodecylbenzenesulfonate, 30 parts of bentonite, and 57 parts of clay, followed by well stirring and mixing. Then an appropriate amount of water is added to this mixture, followed by further stirring, granulating with a granulator, and air drying, to give a granule for each compound.
Formulation Example 4
4.5 Parts of each of the present invention compounds (1) to (28), 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 juice 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
10 Parts of each of the present invention compounds (1) to (28), 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
0.5 Parts of each of the present invention compounds (1) to (28) are dissolved in 10 parts of dichloromethane, and the resulting solution is mixed with 89.5parts of Iso-Par M (isoparaffine: registered trade name for EXXON CHEMICAL LTD) to give an oil solution.
Formulation Example 7
0.1 Parts of each of the present invention compounds (1) to (28) and 49.9 parts of NEO-CHIOZOL (CHUO KASEI Co. , LTD) are charged into aerosol can, and aerosol valve is fixed to the can. Then 25 parts of dimethyl ether and 25 parts of LPG are filled in the can, followed by shaking and fitting an actuator on it, to give an oil aerosol.
Formulation Example 8
0.6 Parts of each of the present invention compounds (1) to (28), 0.01 parts of BHT, 5 parts of xylene, 3.39 parts of deodorized kerosene and 1 part of emulsifier [Atmos 300(registered trade name for ATMOS CHEMICAL LTD)] are mixed and dissolved. The solution obtained and 50 parts of distilled water are charged into aerosol container, and a valve is fixed to the container. 40 Parts of propellant (LPG) are charged under pressure through the valve to give an aqueous aerosol.

The following test example will demonstrate that the present invention compounds have a pesticidal activity as active ingredient of a composition for controlling pests. The present invention compounds are designated by their compound numbers shown in Tables.
Test Example 1
The formulation obtained according to Formulation Example 5 using the present invention compounds (1), (2), (3), (7), (8), (9), (10), (11), (13), (14), (15), (16), (17), (18), (19), (24), (26) and (28) respectively, was diluted with water so that the active ingredient concentration came to 500 ppm to prepare a pesticidal solution for test.
Fifty grams of molding Bonsoru 2 (available from Sumitomo Chemical Co. , Ltd. ) was put into a polyethylene cup, and 10 to 15 seeds of rice were planted in the polyethylene cup. Then rice plants were grown until the second foliage leaves developed and then cut into the same height of 5 cm. The pesticidal solution for test prepared above was sprayed at the rate of 20 ml/cup to these rice plants. After the pesticidal solution sprayed onto the rice plants were dried, they were put into a plastic cup for escape prevention of test pests, and thirty first-instar larvae of Nilaparvata lugens were set free on the rice plants, followed by covering the plastic cup with a lid. Then the plastic cup was left in a greenhouse (25QC). On the sixth 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 present invention compounds (1), (2), (3), (7), (8), (9), (10), (11), (13), (14), (15), (16), (17), (18), (19), (24), (26) and (28), the number of parasitic Nilaparvata lugens was not greater than 3.
Test Example 2
The formulation obtained according to Formulation Example 5 using the present invention compounds (1), (7), (8), (9), (10), (14), (16), (18) and (26) respectively, was diluted with water so that the active ingredient concentration came to 500 ppm to prepare a pesticidal solution for test.
A polyethylene cup was seeded with cucumber and a plant was grown until the first true leaf was developed, on which about twenty Aphis gossypii are allowed to be parasitic. On the next day, the above pesticidal solution for test was sprayed at a ratio of 20 ml/cup to the cucumber plant. On the sixth day after the application, the number of Aphis gossypii was examined.
As a result, in the treatment with each of the present invention compounds (1), (7), (8), (9), (10), (14), (16), (18) and (26), the number of parasitic Nilaparvata lugens on the sixth day after the treatment was not greater than 3.
Test Example 3
The formulation obtained according to Formulation Example

5 using the present invention compounds
(1), (2), (3), (7), (8), (9), (10), (11), (13), (14), (16), (17),
(18) and (19) respectively, was diluted with water so that the active ingredient concentration came to 500 ppm to prepare a pesticidal solution for test.
On the bottom of a polyethylene cup having a diameter of 5.5 cm, a filter paper having the same diameter was laid, and 0. 7 ml of the above pesticidal solution for test was added dropwise on the filter paper, followed by putting 30 mg of sucrose on it uniformly as a bait. Ten female Musca domestica imagoes were set free in the polyethylene cup and covered it with a lid. After 24 hours, the number of surviving Musca domestica was examined and the rate of dead pests was calculated.
As a result, in the treatment with each of the present invention compounds (1), (2), (3), (7), (8), (9), (10), (11), (13), (14), (16), (17), (18) and (19) the rate of dead pests was 90% or more.
Test Example 4
The formulation obtained according to Formulation Example 5 using the present invention compounds
(1), (6), (9), (10), (12), (13), (14), (16), (17), (18), (19) and (20) respectively, was diluted with water so that the active ingredient concentration came to 500 ppm to prepare a pesticidal solution for test.
On the bottom of a polyethylene cup having a diameter of

5.5 cm, a filter paper having the same diameter was laid, and 0. 7 ml of the above pesticidal solution for test was added dropwise on the filter paper, followed by putting 30 mg of sucrose on it uniformly as a bait. Two male Blattella germanica imagoes were set free in the polyethylene cup and covered it with a lid. After 6 days, the number of surviving Blattella germanica was examined and the rate of dead pests was calculated.
As a result, in the treatment with each of the present invention compounds (1), (6), (9), (10), (12), (13), (14), (16), (17), (18), (19) and (20), the rate of dead pests was 100%.
Test Example 5
The formulation obtained according to Formulation Example 5 using the present invention compounds (1), (2), (3), (4), (6), (7), (8), (9), (10), (11), (13), (14), (16), (17), (18), (19), (21), (22), (23), (25) and (26) respectively, was diluted with water so that the active ingredient concentration came to 500 ppm to prepare a pesticidal solution for test.
0.7 ml of above pesticidal solution for test was added to 100 ml of ion exchanged water (active ingredient concentration: 3.5 ppm). Twenty last-instar larvae of Culex pipiens pallens were set free in the solution. After one day, the number of surviving Culex pipiens pallens was examined and the rate of dead pests was calculated.
As a result, in the treatment with each of the present invention compounds (1), (2), (3), (4), (6), (7), (8), (9), (10),

(11), (13), (14), (16), (17), (18), (19), (21), (22), (23), (25) and (26), the rate of dead pests was 100%.
INDUSTRIAL APPLICABILITY
Pests can be controlled by using the pesticide composition containing the compound of the present invention as an active ingredient.




XT Til S~*t- A T"m r
wherein, in the formula, , v ^
V ..\ R1 represents a C1-C5 alkyl group optionally substituted by one i?" ^
c\> »
or more halogen atoms, a C2-C5 alkenyl group optionally \t
substituted by one or more halogen atoms, a C2-C5 alkynyl group
optionally substituted by one or more halogen atoms or a hydrogen
atom;
R2 represents a C1-C5 alkyl group optionally substituted by one
or more halogen atoms, a C1-C5 alkoxy group optionally
substituted by one or more halogen atoms, a C2-C5 alkenyl group
optionally substituted by one or more halogen atoms, a C2-C5
alkynyl group optionally substituted by one or more halogen atoms,
a cyano group or a hydrogen atom;
each of R3 andR4 is represents a C1-C5 alkyl group optionally
substituted by one or more halogen atoms, a C2-C5 alkenyl group
optionally substituted by one or more halogen atoms, a C2-C5
alkynyl group optionally substituted by one or more halogen atoms,
a C3-C5 cycloalkyl group optionally substituted by one or more
halogen atoms, a C5-C6 cycloalkenyl group optionally substituted

by one or more halogen atoms or a hydrogen atom, or represents a C2-C6 alkanediyl group optionally substituted by one or more halogen atoms or a C4-C6 alkenediyl group optionally substituted by one or more halogen atoms in each of which R3 and R4 couple one another at the ends thereof; each of X1, X2 and X3 represents a nitrogen atom or CR6, with the proviso that two or three of X1, X2 and X3 represent a nitrogen atom;
R6 represents a hydrogen atom or R5;
each of R5s represents a halogen atom, a cyano group, a nitro group, a hydroxyl group, a mercapto group, a formyl group, a SF5 group, a carboxyl group, a C1-C5 alkyl group optionally substituted by one or more halogen atoms, a C2-C5 alkenyl group optionally substituted by one or more halogen atoms, a C2-C5 alkynyl group optionally substituted by one or more halogen atoms, a C3-C5 cycloalkyl group optionally substituted by one or more halogen atoms, a C1-C5 alkoxy group optionally substituted by one or more halogen atoms, a C3-C6 alkenyloxy group optionally substituted by one or more halogen atoms, a C3-C6 alkynyloxy group optionally substituted by one or more halogen atoms, a C1-C5 alkylthio group optionally substituted by one or more halogen atoms, a C3-C5 alkenylthio group optionally substituted by one or more halogen atoms, aC3-C5 alkynylthio group optionally substituted by one or more halogen atoms, a C1-C5 alkylsulfinyl group optionally substituted by one or more halogen atoms, a

C1-C5 alkylsulfonyl group optionally substituted by one or more halogen atoms, a C2-C6 alkylcarbonyl group optionally substituted by one or more halogen atoms, a C2-C5 alkoxycarbonyl group optionally substituted by one or more halogen atoms, a group designated by —NR10R11, a group designated by - C (=X5 )NR12R13 or a group designated by — C(=NOR14)R15, or
where m is 2 and two carbon atoms to couple two R5s are adjacent, may represent a C3-C6 alkanediyl group or a C3-C6 alkenediyl group each of which is formed by coupling of the two R5s at the ends thereof, furthermore, in this conditions, a methylene group structuring saidC3-C6 alkanediyl group or saidC3-C6 alkenediyl group may be replaced by 0, S(0)r or NR16 and a carbon atom structuring saidC3-C6 alkanediyl group or saidC3-C6 alkenediyl group may be coupled with a halogen atom or a C1-C3 alkoxy group optionally substituted by one or more halogen atoms instead of hydrogen atom(s);
each of R10 and R11 represents a C1-C5 alkyl group optionally substituted by one or more halogen atoms, a C3-C5 alkenyl group optionally substituted by one or more halogen atoms, a C3-C5 alkynyl group optionally substituted by one or more halogen atoms, a C3-C5 cycloalkyl group optionally substituted by one or more halogen atoms, a (C1-C5 alkoxy optionally substituted by one or more halogen atoms) C1-C3 alkyl group, a C1-C5 alkylsulfonyl group optionally substituted by one or more halogen atoms, a C2-C6 alkylcarbonyl group optionally substituted by one or more

halogen atoms, a C2-C5 alkoxycarbonyl group optionally substituted by one or more halogen atoms or a hydrogen atom, or represents a C2-C6 alkanediyl group optionally substituted by one or more halogen atoms or a C4 -C6 alkenediyl group optionally substituted by one or more halogen atoms in each of which R10 and R11 are coupled with one another at the ends thereof; each of R12 and R13 represents a C1-C5 alkyl group optionally substituted by one or more halogen atoms, a C3-C5 alkenyl group optionally substituted by one or more halogen atoms, a C3-C5 alkynyl group optionally substituted by one or more halogen atoms, a C3-C5 cycloalkyl group optionally substituted by one or more
halogen atoms, a group designated by — (CH2)nQ1 or a hydrogen atom,
or represents a C2-C6 alkanediyl group optionally substituted by one or more halogen atoms or a C4 -C6 alkenediyl group optionally substituted by one or more halogen atoms in each of which R12 and R13 are coupled with one another at the ends thereof; A represents an oxygen atom, a sulfur atom or a (CH2)n; each of R14 and R15 represents a C1-C5 alkyl group optionally substituted by one or more halogen atoms, a C3-C5 alkenyl group optionally substituted by one or more halogen atoms, a C3-C5 alkynyl group optionally substituted by one or more halogen atoms, a C3-C5 cycloalkyl group optionally substituted by one or more
halogen atoms, a group designated by — (CH2)nQ2 or a hydrogen atom;

each of Q1 and Q2 represents a phenyl group which may be substituted
by a group selected from the group consisted of a C1-C5 alkyl
group optionally substituted by one or more halogen atoms, a
C1-C5 alkoxy group optionally substituted by one or more halogen
atoms, a C1-C5 alkylthio group optionally substituted by one
or more halogen atoms and a halogen atom;
R16 represents a C1-C3 alkyl group; m represents an integer of
from 0 to 2; n represents an integer of from 0 to 3; r represents
an integer of from 0 to 2; and
X5 represents an oxygen atom or a sulfur atom.
2. The malononitrile compound according to claiml, wherein R3
is a hydrogen atom and R4 is a C1-C5 alkyl group optionally
substituted by one or more halogen atoms, a C2-C5 alkenyl group
optionally substituted by one or more halogen atoms, a C2-C5
alkynyl group optionally substituted by one or more halogen atoms,
a C3-C5 cycloalkyl group optionally substituted by one or more
halogen atoms or a C5-C6 cycloalkenyl group optionally
substituted by one or more halogen atoms.
3. The malononitrile compound according to claiml, which is
represented by the formula (XI):


, wherein R1 represents a CI -C5 alkyl group optionally substituted by one or more halogen atoms, a C2-C5 alkenyl group optionally substituted by one or more halogen atoms, a C2-C5 alkynyl group optionally substituted by one or more halogen atoms or a hydrogen atom;
R2 represents a C1-C5 alkyl group optionally substituted by one or more halogen atoms, a C1-C5 alkoxy group optionally substituted by one or more halogen atoms, a C2-C5 alkenyl group optionally substituted by one or more halogen atoms, a C2-C5 alkynyl group optionally substituted by one or more halogen atoms, a cyano group or a hydrogen atom;
each of R3 andR4 is represents a C1-C5 alkyl group optionally substituted by one or more halogen atoms, a C2-C5 alkenyl group optionally substituted by one or more halogen atoms, a C2-C5 alkynyl group optionally substituted by one or more halogen atoms, a C3-C5 cycloalkyl group optionally substituted by one or more halogen atoms, a C5-C6 cycloalkenyl group optionally substituted by one or more halogen atoms or a hydrogen atom, or represents a C2-C6 alkanediyl group optionally substituted by one or more halogen atoms or a C4 -C6 alkenediyl group optionally substituted by one or more halogen atoms in each of which R3 and R4 couple one another at the ends thereof; R5a represents a hydrogen atom, halogen atom, a cyano group, anitrogroup, ahydroxyl group, amercapto group, a f ormyl group,

a SF5 group, a carboxyl group, a C1-C5 alkyl group optionally substituted by one or more halogen atoms, a C2-C5 alkenyl group optionally substituted by one or more halogen atoms, a C2-C5 alkynyl group optionally substituted by one or more halogen atoms, a C3-C5 cycloalkyl group optionally substituted by one or more halogen atoms, a C1-C5 alkoxy group optionally substituted by one or more halogen atoms, a C3-C6 alkenyloxy group optionally substituted by one or more halogen atoms, a C3-C6 alkynyloxy group optionally substituted by one or more halogen atoms, a C1-C5 alkylthio group optionally substituted by one or more halogen atoms, a C3-C5 alkenylthio group optionally substituted by one or more halogen atoms, a C3 -C5 alkynylthio group optionally substituted by one or more halogen atoms, a C1-C5 alkylsulfinyl group optionally substituted by one or more halogen atoms, a C1-C5 alkylsulf onyl group optionally substituted by one or more halogen atoms, a C2-C6 alkylcarbonyl group optionally substituted by one or more halogen atoms, a C2-C5 alkoxycarbonyl group optionally substituted by one or more halogen atoms, a group designated by —NR10RU, a group designated by — C (=X5) NR12R13 or a group designated by -C(=NOR14)R15,
each of R10 and R11 represents a C1-C5 alkyl group optionally substituted by one or more halogen atoms, a C3-C5 alkenyl group optionally substituted by one or more halogen atoms, a C3-C5 alkynyl group optionally substituted by one or more halogen atoms, a C3-C5 cycloalkyl group optionally substituted by one or more

halogen atoms, a (C1-C5 alkoxy optionally substituted by one or more halogen atoms) C1-C3 alkyl group, a C1-C5 alkylsulfonyl group optionally substituted by one or more halogen atoms, a C2-C6 alkylcarbonyl group optionally substituted by one or more halogen atoms, a C2-C5 alkoxycarbonyl group optionally substituted by one or more halogen atoms or a hydrogen atom, or represents a C2-C6 alkanediyl group optionally substituted by one or more halogen atoms or a C4 -C6 alkenediyl group optionally substituted by one or more halogen atoms in each of which R10 and R11 are coupled with one another at the ends thereof; each of R12 and R13 represents a C1-C5 alkyl group optionally substituted by one or more halogen atoms, a C3-C5 alkenyl group optionally substituted by one or more halogen atoms, a C3-C5 alkynyl group optionally substituted by one or more halogen atoms, a C3-C5 cycloalkyl group optionally substituted by one or more
halogen atoms, a group designated by ~ (CH2)nQ1 or a hydrogen atom,
or represents a C2-C6 alkanediyl group optionally substituted by one or more halogen atoms or a C4 -C6 alkenediyl group optionally substituted by one or more halogen atoms in each of which R12 and R13 are coupled with one another at the ends thereof; each of R14 and R15 represents a C1-C5 alkyl group optionally substituted by one or more halogen atoms, a C3-C5 alkenyl group optionally substituted by one or more halogen atoms, a C3-C5 alkynyl group optionally substituted by one or more halogen atoms,

a C3-C5 cycloalkyl group optionally substituted by one or more
halogen atoms, a group designated by —(CH2)nQ2 or a hydrogen atom; each of Q1 and Q2 represents a phenyl group which may be substituted by a group selected from the group consisted of a C1-C5 alkyl group optionally substituted by one or more halogen atoms, a C1-C5 alkoxy group optionally substituted by one or more halogen atoms, a C1-C5 alkylthio group optionally substituted by one or more halogen atoms and a halogen atom; and X5 represents an oxygen atom or a sulfur atom.


a cyano group or a hydrogen atom;
each of R3 andR4 is represents a C1-C5 alkyl group optionally substituted by one or more halogen atoms, a C2-C5 alkenyl group optionally substituted by one or more halogen atoms, a C2-C5 alkynyl group optionally substituted by one or more halogen atoms, a C3-C5 cycloalkyl group optionally substituted by one or more halogen atoms , a C5-C6 cycloalkenyl group optionally substituted by one or more halogen atoms or a hydrogen atom, or represents a C2-C6 alkanediyl group optionally substituted by one or more halogen atoms or a C4 -C6 alkenediyl group optionally substituted by one or more halogen atoms in each of which R3 and R4 couple one another at the ends thereof; R5 represents a halogen atom, a cyano group, a nitro group, a hydroxyl group, a mercapto group, a formyl group, a SF5 group, a carboxyl group, a C1-C5 alkyl group optionally substituted by one or more halogen atoms, a C2-C5 alkenyl group optionally substituted by one or more halogen atoms, a C2-C5 alkynyl group optionally substituted by one or more halogen atoms, a C3-C5 cycloalkyl group optionally substituted by one or more halogen atoms, a C1-C5 alkoxy group optionally substituted by one or more halogen atoms, a C3-C6 alkenyloxy group optionally substituted by one or more halogen atoms, a C3-C6 alkynyloxy group optionally substituted by one or more halogen atoms, a C1-C5 alkylthio group optionally substituted by one or more halogen atoms, a C3-C5 alkenylthio group optionally substituted

by one or more halogen atoms, a C3 -C5 alkynylthio group optionally substituted by one or more halogen atoms, a C1-C5 alkylsulfinyl group optionally substituted by one or more halogen atoms, a C1-C5 alkylsulf onyl group optionally substituted by one or more halogen atoms, a C2-C6 alkylcarbonyl group optionally substituted by one or more halogen atoms , a C2-C5 alkoxycarbonyl group optionally substituted by one or more halogen atoms, a group designated by -NR10RX1, a group designated by -C(=X5)NR12R13 or a group designated by — C(=NOR14)R15,
each of R10 and R11 represents a C1-C5 alkyl group optionally substituted by one or more halogen atoms, a C3-C5 alkenyl group optionally substituted by one or more halogen atoms, a C3-C5 alkynyl group optionally substituted by one or more halogen atoms, a C3-C5 cycloalkyl group optionally substituted by one or more halogen atoms, a (C1-C5 alkoxy optionally substituted by one or more halogen atoms) C1-C3 alkyl group, a C1-C5 alkylsulf onyl group optionally substituted by one or more halogen atoms, a C2-C6 alkylcarbonyl group optionally substituted by one or more halogen atoms, a C2-C5 alkoxycarbonyl group optionally substituted by one or more halogen atoms or a hydrogen atom, or represents a C2-C6 alkanediyl group optionally substituted by one or more halogen atoms or a C4 - C6 alkenediyl group optionally substituted by one or more halogen atoms in each of which R10 and R11 are coupled with one another at the ends thereof; each of R12 and R13 represents a C1-C5 alkyl group optionally

substituted by one or more halogen atoms, a C3-C5 alkenyl group optionally substituted by one or more halogen atoms, a C3-C5 alkynyl group optionally substituted by one or more halogen atoms, a C3-C5 cycloalkyl group optionally substituted by one or more
halogen atoms, a group designated by ~(CH2)nQl or a hydrogen atom,
or represents a C2-C6 alkanediyl group optionally substituted
by one or more halogen atoms or a C4 -C6 alkenediyl group optionally
substituted by one or more halogen atoms in each of which R12
and R13 are coupled with one another at the ends thereof;
each of R14 and R15 represents a C1-C5 alkyl group optionally
substituted by one or more halogen atoms, a C3-C5 alkenyl group
optionally substituted by one or more halogen atoms, a C3-C5
alkynyl group optionally substituted by one or more halogen atoms,
a C3-C5 cycloalkyl group optionally substituted by one or more
halogen atoms, a group designated by —(CH2)nQ2 or a hydrogen atom; each of Q1 and Q2 represents a phenyl group which may be substituted by a group selected from the group consisted of a C1-C5 alkyl group optionally substituted by one or more halogen atoms, a C1-C5 alkoxy group optionally substituted by one or more halogen atoms, a C1-C5 alkylthio group optionally substituted by one or more halogen atoms and a halogen atom; and X5 represents an oxygen atom or a sulfur atom; and m represents an integer 0 to 2.



A pesticide composition comprising 0.1 to 95% weight of the malonitrile compound according to claim 1, as an active ingredient and an inert carrier.
9. A method for controlling pests comprising applying an effective amount of the / ^i malononitrile compound according to claim 1 to pests or at a habitat of pests. / | g^
i
Dated this 31st day of December 2004

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1500-che-2004-correspondnece-others.pdf

1500-che-2004-correspondnece-po.pdf

1500-che-2004-description(complete).pdf

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Patent Number 222622
Indian Patent Application Number 1500/CHE/2004
PG Journal Number 47/2008
Publication Date 21-Nov-2008
Grant Date 20-Aug-2008
Date of Filing 31-Dec-2004
Name of Patentee SUMITOMO CHEMICAL COMPANY, LIMITED
Applicant Address 27-1, SHINKAWA 2-CHOME, CHUO-KU, TOKYO 104-8260,
Inventors:
# Inventor's Name Inventor's Address
1 OHSHITA JUN 8-7-20-310 HON-MACHI, TOYONAKA-SHI, OSAKA,
PCT International Classification Number C07D209/12
PCT International Application Number N/A
PCT International Filing date
PCT Conventions:
# PCT Application Number Date of Convention Priority Country
1 2004-009151 2004-01-16 Japan