Indian Patents
Title of Invention

COMPOSITIONS CONTAINING MALONONITRILE COMPOUNDS
Abstract The present invention provides a malononitrile compound represented by the formula (I): wherein any one of X1, X2, X3 and X4 is CR100, wherein R100 is a group represented by the formula: the other three of X1, X2, X3 and X4 each represent nitrogen or CR5, provided that 1 to 3 of X1, X2, X3 and X4 represent nitrogen, and Z represents oxygen, sulfur or NR6, which has pest-controlling activity.
Full Text or CR5, provided that one to three of X1, X2, X3 and X4 represent nitrogen, Z represents oxygen, sulfur or NR6,
R5 independently represents halogen, cyano, nitro, hydroxyl, 5 mercapto, formyl, SF5, carboxyl, C1-C5 alkyl optionally substituted with one or more halogen, C2-C5 alkenyl optionally substituted with one or more halogen, C2-C5 ^^ alkynyl optionally substituted with one or more halogen,
C3-C6 cycloalkyl optionally substituted with halogen or one 10 or more C1-C3 alkyl, C1-C5 alkoxy optionally substituted with one or more halogen, C3-C6 alkenyloxy optionally substituted with one or more halogen, C3-C6 alkynyloxy optionally substituted with one or more halogen, C1-C5 alkylthio optionally substituted with one or more halogen, 15 C3-C5 alkenylthio optionally substituted with one or more halogen, C3-C5 alkynylthio optionally substituted with one or more halogen, C1-C5 alkylsulfinyl optionally substituted with one or more halogen, C1-C5 alkylsulfonyl optionally substituted with one or more halogen, C2-C6 alkylcarbonyl 20 optionally substituted with one or more halogen, C2-C5 alkoxycarbonyl optionally substituted with one or more halogen, a group represented by NR10R1:L, a group represented by C (=X5)NR12R13, a group represented by (CH2)mQ, a group represented by C (=NOR17) R18, a group represented by 25 C(OR19)R20R21, or hydrogen,
R6 represents C1-C5 alkyl optionally substituted with one or more halogen, C3-C5 alkenyl optionally substituted with one or more halogen, C3-C5 alkynyl optionally substituted with one or more halogen, C3-C6 cycloalkyl optionally 5 substituted with one or more halogen, (C1-C5 alkoxy
optionally substituted with one or more halogen)C1-C3 alkyl, C1-C5 alkylsulfinyl optionally substituted with one or more ^ halogen, C1-C5 alkylsulfonyl optionally substituted with
one or more halogen, C2-C6 alkylcarbonyl optionally 10 substituted with one or more halogen, C2-C5 alkoxycarbonyl optionally substituted with one or more halogen, a group represented by C (=X5)NR12R13, a group represented by (CH2)mQ, or hydrogen, and
when two CR5, or CR5 and NR6 are adjacent to each other, 15 they may be taken together to represent C2-C6 alkanediyl or C4-C6 alkenediyl optionally substituted with one or more halogen, in which at least one methylene group forming the alkanediyl or the alkenediyl may be substituted with oxygen, sulfur or NR7,
20 R7 represents C1-C5 alkyl optionally substituted with one or more halogen, C3-C5 alkenyl optionally substituted with one or more halogen, C3-C5 alkynyl optionally substituted with one or more halogen, C3-C6 cycloalkyl optionally substituted with one or more halogen, C2-C6 alkylcarbonyl 25 optionally substituted with one or more halogen, C2-C5

alkoxycarbonyl optionally substituted with one or more halogen, or hydrogen,
R10 and R11 each represent C1-C5 alkyl optionally substituted with one or more halogen, C3-C5 alkenyl 5 optionally substituted with one or more halogen, C3-C5
alkynyl optionally substituted with one or more halogen, C3-C6 cycloalkyl optionally substituted with one or more ^ halogen, (C1-C5 alkoxy optionally substituted with one or
more halogen)C1-C3 alkyl, C1-C5 alkylsulfinyl optionally 10 substituted with one or more halogen, C1-C5 alkylsulfonyl optionally substituted with one or more halogen, C2-C6 alkylcarbonyl optionally substituted with one or more halogen, C2-C5 alkoxycarbonyl optionally substituted with one or more halogen, or hydrogen, 15 or the group represented by NR10R1:L is 1-pyrrolyl, R12 and R13 each represent C1-C5 alkyl optionally substituted with one or more halogen, C3-C5 alkenyl
rf
optionally substituted with one or more halogen, C3-C5 alkynyl optionally substituted with one or more halogen, 20 C3-C6 cycloalkyl optionally substituted with one or more halogen, a group represented by (CH2)mQ/ or hydrogen, or R12 and R13 are taken together to represent C2-C6 alkanediyl optionally substituted with one or more halogen or C4-C6 alkenediyl optionally substituted with one or more 25 halogen,

R17 and R18 each represent C1-C5 alkyl optionally substituted with one or more halogen, C3-C5 alkenyl optionally substituted with one or more halogen, C3-C5 alkynyl optionally substituted with one or more halogen, 5 C3-C6 cycloalkyl optionally substituted with one or more halogen, a group represented by (CH2)mQ, or hydrogen, R19 represents C1-C5 alkyl optionally substituted with one or more halogen, C3-C5 alkenyl optionally substituted with one or more halogen, C3-C5 alkynyl optionally substituted 10 with one or more halogen, C3-C6 cycloalkyl optionally substituted with one or more halogen, (C1-C5 alkoxy optionally substituted with one or more halogen)C1-C3 alkyl, C1-C5 alkylsulfinyl optionally substituted with one or more halogen, C1-C5 alkylsulfonyl optionally substituted with 15 one or more halogen, C2-C6 alkylcarbonyl optionally
substituted with one or more halogen, C2-C5 alkoxycarbonyl optionally substituted with one or more halogen, a group represented by C (=X5) NR12R13, a group represented by (CH2)mQ, trialkylsilyl, or hydrogen, 20 R20 and R21 each represent C1-C5 alkyl optionally
substituted with one or more halogen, C2-C5 alkenyl optionally substituted with one or more halogen, C2-C5 alkynyl optionally substituted with one or more halogen, C3-C6 cycloalkyl optionally substituted with one or more 25 halogen, or hydrogen,

Q represents aryl optionally substituted with R14 n times, R14 independently represents C1-C5 alkyl optionally substituted with one or more halogen, C3-C6 cycloalkyl optionally substituted with one or more halogen, C1-C5 alkoxy optionally substituted with one or more halogen, Cl- C5 alkylthio optionally substituted with one or more halogen, C3-C5 alkenylthio optionally substituted with one or more halogen, C3-C5 alkynylthio optionally substituted with one or more halogen, C1-C5 alkylsulfinyl optionally substituted with one or more halogen, C1-C5 alkylsulfonyl optionally substituted with one or more halogen, C2-C6 alkylcarbonyl optionally substituted with one or more halogen, C2-C5 alkoxycarbonyl optionally substituted with one or more halogen, or halogen,
25
m and n each represent an integer of 0 to 5, and X5 represents oxygen or sulfur (hereinafter, referred to as the present compound); a pesticidal composition comprising an effective amount of the present compound and an inert carrier, and a method for controlling a pest comprising applying an effective amount of the present compound to said pest or a place where said pest inhabits.
Mode for Carrying Out the Invention
5
r10
15
In the present invention, the "alkanediyl" represents a chain saturated hydrocarbon group in which two different
constituting carbon atoms have a free valence. The "alkenediyl" represents a chain hydrocarbon group having one or two double bonds in which two different constituting carbon atoms have a free valence.
5 In the present invention, the "fluoroalkyl" represents
alkyl substituted with one or two fluorine atoms. The description of C1-C6 or the like means the total number of ^ carbon atoms constituting a substituent.
In the present invention, examples of the C1-C5 alkyl 10 optionally substituted with one or more halogen represented by R1 or R2 include C1-C3 alkyl optionally substituted with one or more halogen; specifically, methyl, ethyl, propyl, 1-methylethyl, 2,2-dimethylpropyl, chloromethyl, fluoromethyl, difluoromethly, trifluoromethyl, 2,2,2- 15 trifluoroethyl and a 1,1,2,2-tetrafluoroethyl; and 1,1- diemethylethyl.
Examples of the C2-C5 alkenyl optionally substituted with one or more halogen include vinyl, 2,2-difluorovinyl, 1,2,2-trifluorovinyl, 1-propenyl and 2-propenyl. 20 Examples of the C2-C5 alkynyl optionally substituted
with one or more halogen include ethynyl, 1-propynyl, 2- propynyl and 3,3,3-trifluoro-l-propynyl.
Examples of the C1-C5 alkoxy optionally substituted with one or more halogen represented by R2 include C1-C3 25 alkyl optionally substituted with one or more halogen, such
as methoxy, ethoxy, 1-methylethoxy, fluoromethoxy,
difluoromethoxy, trifluoromethoxy, 2,2,2-trifluoroethoxy
and 1,1,2,2-tetrafluoroethoxy; and butoxy.
Examples of the C1-C5 alkyl optionally substituted 5 with one or more halogen represented by R3 or R4 include
methyl, ethyl, 1-methylethyl, 2-methylpropyl, propyl, butyl, 3-methylbutyl, 2,2-dimethylpropyl, fluoromethyl, ^^ chloromethyl, 2,2-difluoroethyl, 2,2-dichloroethyl, 3,3-
difluoropropyl, 3,3-dichloropropyl, trifluoromethyl, 10 trichloromethyl, 2,2,2-trifluoroethyl, 2,2,2-trichloroethyl, 3,3,3-trifluoropropyl, 3,3,3-trichloropropyl, 2,2- difluoropropyl, 3,3-difluorobutyl, l-bromo-2,2,2- trifluoroethyl, l-chloro-2,2,2-trifluoroethyl, 1,2,2,2- tetrafluoroethyl, pentafluoroethyl, 2,2,3,3,3- 15 pentafluoropropyl, 1,1,2,2-tetrafluoroethyl and 2,2,3,3- tetrafluoropropyl.
Examples of the C2-C5 alkenyl optionally substituted
r~with one or more halogen include vinyl, allyl, 1-propenyl, 3-butenyl, 2-methyl-1-propenyl, 3-methyl-2-butenyl, 3- 20 pentenyl, 4-pentenyl, 3-methyl-3-butenyl, 4-methyl-3-
pentenyl, 1-chlorovinyl, 2-chlorovinyl, 1-fluorovinyl, 2- fluorovinyl, 2,2-dichlorovinyl, 2,2-dibromovinyl, 2,2- difluorovinyl, 1,2,2-trifluorovinyl, 1-
(trifluoromethyl)vinyl, 2-chloro-2-propenyl, 3-chloro-2- 25 propenyl, 2-fluoro-2-propenyl, 3-fluoro-2-propenyl, 3,3- dichloro-2-propenyl, 3,3-dibromo-2-propenyl, 3,3-difluoro- 2-propenyl, 2,3,3-trifluoro-2-propenyl, 2- (trifluoromethyl)-2-propenyl, 2,3,3,3-tetrafluoro-l- propenyl, 1,2,3,3,3-pentafluoro-l-propenyl, 3,4,4- trifluoro-3-butenyl, 3,4,4,4-tetrafluoro-2-butenyl, 2,3,4,4,4-pentafluoro-2-butenyl and 4,5,5-trifluoro-4- pentenyl.
Examples of the C2-C5 alkynyl optionally substituted with one or more halogen include ethynyl, 1-propynyl, 2- propynyl, 1-butynyl, 3-methyl-l-butynyl, 3-chloro-2- propynyl, 3,3,3-trifluoro-l-propynyl and 4,4,4-trifluoro-2- butynyl.
Examples of the C3-C5 cycloalkyl optionally substituted with one or more halogen include cyclopropyl, 2,2-dichlorocyclopropyl, 2,2-difluorocyclopropyl, 2,2,3,3- tetrafluorocyclopropyl, 2,2-dichlorocyclobutyl, 2,2- difluorocyclobutyl, 2,2,3,3-tetrafluorocyclobutyl, cyclobutyl, cyclopentyl and cyclohexyl.
Examples of the C4-C5 cycloalkenyl optionally substituted with one or more halogen include 2-fluoro-2- cyclopentenyl.
Examples of the C2-C6 alkanediyl optionally substituted with one or more halogen represented by R3 and R4 together include ethylene, propylene, trimethylene and tetramethylene.
Examples of the C4-C6 alkenediyl optionally substituted with one or more halogen include 2-butynylene and 2-pentenylene.
Examples of the halogen represented by R5 or R14 5 include fluorine, chlorine, bromine and iodine.
Examples of the C1-C5 alkyl optionally substituted with one or more halogen represented by R5, R6, R7, R10, R11, ^ R12, R13, R14, R17, R18, R19, R20 or R21 include methyl, ethyl,
1-methylethyl, 1-ethtylethyl, 1,1-dimethylethyl, propyl, 1- 10 methylpropyl, 1-ethtylpropyl, 1,1-dimethylpropyl, 2,2-
dimethylpropyl, 1,2-dimethylpropyl, 1,1,2-trimethylpropyl, butyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, pentyl, fluoromethyl, chloromethyl, bromomethyl, iodomethyl, difluoromethyl, chlorodifluoromethyl, bromodifluoromethyl, 15 trifluoromethyl, dichloromethyl, trichloromethyl, 1-
chloroethyl, 1-bromoethyl, 1-iodoethyl, 1-fluoroethyl, 2- chloroethyl, 2-bromoethyl, 2-iodoethyl, 2-fluoroethyl, 2,2- difluoroethyl, 2,2,2-trifluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl, 2,2,2-trifluoro-l-chloroethyl, 3- 20 fluoropropyl, 3-chloropropyl, 1-fluoro-l-methylethyl, 1-
chloro-l-methylethyl, 1-bromo-l-methylethyl, 2-chloro-l,1- dimethylethyl, 1,1-difluoroethyl, 2-fluoro-l,1- dimethylethyl, heptafluoropropyl, 1,1,2,2,3,3- hexafluoropropyl, 4-chlorobutyl, 4-fluorobutyl, 5- 25 chloropentyl and 5-fluoropentyl.
Examples of the C2-C5 alkenyl optionally substituted with one or more halogen represented by R5, R20 or R21 include vinyl, 1-methylvinyl, 1-propenyl, 1-methyl-l- propenyl, 2-methyl-1-propenyl, 1,2-dimethyl-l-propenyl, 2- 5 propenyl, l-methyl-2-propenyl, 2-methyl-2-propenyl, 1,1- dimethyl-2-propenyl, 1,2-dimethyl-2-propenyl, 2,2- difluorovinyl, 2-chloro-2-propenyl, 2,2-dichloro-2-propenyl, 2-bromo-2-propenyl, 2,2-dibromo-2-propenyl and 2-fluoro-2- propenyl.
10 Examples of the C3-C5 alkenyl optionally substituted
with one or more halogen represented by R6, R7, R10, R11, R12, R13, R17, R18 or R19 include 2-propenyl, l-methyl-2-propenyl, 2-methyl-2-propenyl, 1,l-dimethyl-2-propenyl, 1,2-dimethyl- 2-propenyl, 2-chloro-2-propenyl, 2,2-dichloro-2-propenyl, 15 2-bromo-2-propenyl, 2,2-dibromo-2-propenyl, 2-fluoro-2- propenyl and 2,2-difluoro-2-propenyl.
Examples of the C2-C5 alkynyl optionally substituted with one or more halogen represented by R5, R20 or R21 include ethynyl, 1-propynyl, 2-propynyl and 3,3,3- 20 trifluoro-l-propynyl.
Examples of the C3-C5 alkynyl optionally substituted with one or more halogen represented by R6, R7, R10, R11, R12, R13, R17, R18 or R19 include 1-propynyl, 2-propynyl and 3,3,3-trifluoro-l-propynyl. 25 Examples of the C3-C6 cycloalkyl optionally substituted with halogen or C1-C3 alkyl represented by R5 include cyclopropyl, 1-methylcyclopropyl, 2,2- dichlorocyclopropyl, 2,2-dichloro-l-mehtylcyclopropyl, 2,2- difluorocyclopropyl, 2,2-difluoro-l-methylcyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.
Examples of the C3-C6 cycloalkyl optionally substituted with one or more halogen represented by R6, R7, R10, R11, R12, R13, R14, R17, R18, R19, R20 or R21 include cyclopropyl, 2,2-dichlorocyclopropyl, 2,2-
difluorocyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.
Examples of the C1-C5 alkoxy optionally substituted with one or more halogen represented by R5 or R14 include methoxy, ethoxy, propoxy, trifluoromethoxy, bromodifluoromethoxy, difluoromethoxy, fluoromethoxy, chlorodifluoromethoxy, pentafluoroethoxy, 2,2,2- trifluoroethoxy and 1,1,2,2-tetrafluoroethoxy.
Examples of the C3-C6 alkenyloxy optionally substituted with one or more halogen represented by R5 include 1-propenyloxy, 2-propenyloxy and 2,2-difluoro-2- propenyloxy.
Examples of the C3-C6 alkynyloxy optionally substituted with one or more halogen represented by R5 include 2-propynyloxy and 2-butynyloxy.
Examples of the (C1-C5 alkoxy optionally substituted with one or more halogen) C1-C3 alkyl represented by R6, R10,
R11 or R19 include methoxymethyl, ethoxymethyl, 1- methoxyethyl, 1-ethoxyethyl and trifluoromethoxymethyl.
Examples of the C1-C5 alkylthio optionally substituted with one or more halogen represented by R5 or R14 include methylthio, ethylthio, trifluoromethylthio, chlorodifluoromethylthio, bromodifluoromethylthio, dibromofluoromethylthio, 2,2,2-trifluoroethylthio, 1,1,2,2- tetrafluoroethylthio and pentafluoroethylthio.
Examples of the C3-C5 alkenylthio optionally substituted with one or more halogen represented by R5 or R14 include 2-propenylthio and 2,2-difluoro-2-propenylthio.
Examples of the C3-C5 alkynylthio optionally substituted with one or more halogen represented by R5 or R14 include 2-propynylthio, 2-butynylthio and 3,3,3- trifluoro-l-propynyl.
Examples of the C1-C5 alkylsulfinyl optionally substituted with one or more halogen represented by R5, R6, R10, R11 or R14 include methylsulfinyl, ethylsulfinyl and trifluoromethylsulfinyl.
Examples of the C1-C5 alkylsulfonyl optionally substituted with one or more halogen represented by R5, R6, R10, R11, R14 or R19 include methylsulfonyl and trifluoromethylsulfonyl.
Examples of the C2-C6 alkylcarbonyl optionally substituted with one or more halogen represented by R5, R6,
R7, R10, R11, R14 or R19 include acetyl, propionyl, 2,2- dimethylpropionyl and trifluoroacetyl.
Examples of the C2-C5 alkoxycarbonyl represented by R5' R6, R7, R10, Rn, R14 or R19 include methoxycarbonyl, ethoxycarbonyl, 1-methylethoxycarbonyl and t-butoxycarbonyl.
Examples of the trialkylsilyl represented by R19 include trimethylsilyl, triisopropylsilyl and t- butyldimethylsilyl.
Examples of the C2-C6 alkanediyl optionally substituted with one or more halogen represented by two CR5 or CR5 and NR6 together include propylene, trimethylene, tetramethylene, ethyleneoxy, dimethyleneoxy, ethylenethio and dimethylenethio.
Examples of the C4-C6 alkenediyl optionally substituted with one or more halogen include 2-butenylene and 2-pentenylene.
Examples of the C2-C6 alkanediyl optionally substituted with one or more halogen represented by R12 and R13 together include ethylene, propylene, trimethylene and tetramethylene.
Examples of the C4-C6 alkenediyl optionally substituted with one or more halogen include 2-butenylene and 2-pentenylene.
Examples of the group represented by C (OR19) R20R21 include 1-hydroxy-l-methylethyl, 1-methyl-l-methoxyethyl
and 1-methyl-1-propargyloxyethyl.
Aspects of the present compound include the following compounds:
5 a malononitrile compound of the formula (I) in which
R1 is hydrogen;
a malononitrile compound of the formula (I) in which R2 is methyl;
a malononitrile compound of the formula (I) in which 10 R1 and R2 are hydrogen;
a malononitrile compound of the formula (I) in which R1 is hydrogen and R2 is methyl;
a malononitrile compound of the formula (I) in which R1 is C1-C3 alkyl optionally substituted with one or more 15 halogen or hydrogen, and R2 is C1-C3 alkyl optionally substituted with one or more halogen, C2-C5 alkenyl optionally substituted with one or more halogen, C2-C5 alkynyl optionally substituted with one or more halogen, hydrogen or cyano; 20 a malononitrile compound of the formula (I) in which
R1 is hydrogen and R2 is C1-C3 alkyl optionally substituted with one or more halogen or hydrogen;
a malononitrile compound of the formula (I) in which R3 is hydrogen;
25 a malononitrile compound of the formula (I) in which
R4 is C2-C5 alkenyl optionally substituted with one or more halogen;
a malononitrile compound of the formula (I) in which R4 is vinyl;
5 a malononitrile compound of the formula (I) in which
R4 is 2-propenyl;
a malononitrile compound of the formula (I) in which R4 is 2,2-difluorovinyl;
a malononitrile compound of the formula (I) in which 10 R4 is 1-(trifluoromethyl)vinyl;
a malononitrile compound of the formula (I) in which R4 is 3,3-difluoro-2-propenyl;
a malononitrile compound of the formula (I) in which R4 is 2, 3, 3-trifluoro-2-propenyl; 15 a malononitrile compound of the formula (I) in which
R4 is 3, 3,3-trifluoro-l-propenyl;
a malononitrile compound of the formula (I) in which R4 is C2-C5 alkynyl optionally substituted with one or more halogen;
20 a malononitrile compound of the formula (I) in which
R4 is C1-C5 fluoroalkyl;
a malononitrile compound of the formula (I) in which R4 is fluoromethyl;
a malononitrile compound of the formula (I) in which 25 R4 is 2,2-difluoroethyl;
a malononitrile compound of the formula (I) in which R4 is 2,2,2-trifluoroethyl;
a malononitrile compound of the formula (I) in which R4 is pentafluoroethyl;
5 a malononitrile compound of the formula (I) in which
R4 is 3,3,3-trifluoropropyl;
a malononitrile compound of the formula (I) in which J R4 is 2,2, 3,3,3-pentafluoropropyl;
a malononitrile compound of the formula (I) in which 10 R4 is C3-C6 cycloalkyl optionally substituted with one or more halogen;
a malononitrile compound of the formula (I) in which R4 is 2,2-dichlorocyclopropyl;
a malononitrile compound of the formula (I) in which 15 R4 is cyclopropyl;
a malononitrile compound of the formula (I) in which R4 is cyclobutyl;
a malononitrile compound of the formula (I) in which R3 and R4 each represent C1-C3 alkyl optionally substituted 20 with one or more halogen, C2-C5 alkenyl optionally substituted with one or more halogen, C2-C3 alkynyl optionally substituted with one or more halogen, C3-C5 cycloalkyl optionally substituted with one or more halogen or hydrogen, or R3 and R4 are taken together to represent 25 C2-C6 alkanediyl optionally substituted with one or more
halogen;
a malononitrile compound of the formula (I) in which R3 is hydrogen, and R4 represents C1-C3 alkyl optionally substituted with one or more halogen, C2-C5 alkenyl 5 optionally substituted with halogen, or C2-C5 alkynyl
optionally substituted with one or more halogen, or R3 and R4 are taken together to form C2-C6 alkanediyl optionally substituted halogen;
a malononitrile compound of the formula (I) in which 10 R3 is hydrogen, and R4 is vinyl or 2-propenyl;
a malononitrile compound of the formula (I) in which R3 is hydrogen, and R4 is 2,2-difluorovinyl, 1- (trifluoromethyl)vinyl, 3,3-difluoro-2-propenyl, 2,3,3- trifluoro-2-propenyl or 3,3,3-trifluoro-l-propenyl; 15 a malononitrile compound of the formula (I) in which
R3 is hydrogen, and R4 is fluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 1,1,1,2,2,2-pentafluoroethyl, 3,3,3- trifluoropropyl or 2,2,3,3,3-pentafluoropropyl;
a malononitrile compound of the formula (I) in which 20 R3 is hydrogen, and R4 is cyclopropyl, cyclobutyl or 2,2- dichlorocyclopropyl;
a malononitrile compound of the formula (I) in which R1, R2 and R3 are hydrogen, and R4 is vinyl or 2-propenyl; a malononitrile compound of the formula (I) in which 25 R1, R2 and R3 are hydrogen, and R4 is 2,2-difluorovinyl, 1- (trifluoromethyl)vinyl, 3,3-difluoro-2-propenyl, 2,3,3- trifluoro-2-propenyl or 3,3,3-trifluoro-l-propenyl;
a malononitrile compound of the formula (I) in which R1 and R3 are hydrogen, R2 is methyl, and R4 is 2,2- 5 difluorovinyl, 1-(trifluoromethyl)vinyl, 3,3-difluoro-2-
propenyl, 2,3,3-trifluoro-2-propenyl or 3,3,3-trifluoro-l- propenyl;
a malononitrile compound of the formula (I) in which R1, R2 and R3 are hydrogen, and R4 is fluoromethyl, 2,2- 10 difluroethyl, 2,2,2-trifluoroethyl, pentafluoroethyl, 3,3,3-trifluoropropyl or 2,2,3,3,3-pentafluoropropyl;
a malononitrile compound of the formula (I) in which R1 and R3 are hydrogen, R2 is methyl, and R4 is fluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, pentafluoroethyl, 15 3,3,3-trifluoropropyl or 2,2,3,3,3-pentafluoropropyl;
a malononitrile compound of the formula (I) in which R1, R2 and R3 are hydrogen, and R4 is cyclopropyl, cyclobutyl or 2,2-dichlorocyclopropyl;
a malononitrile compound of the formula (I) in which 20 R1 is hydrogen and R2 is C1-C3 alkyl optionally substituted with one or more halogen or hydrogen;
a malononitrile compound of the formula (I) in which R1 is C1-C3 alkyl optionally substituted with one or more halogen or hydrogen, and R2 is C1-C3 alkyl optionally 25 substituted with one or more halogen, C1-C3 alkoxy
optionally substituted with one or more halogen, C2-C5 alkenyl optionally substituted with one or more halogen, C2-C5 alkynyl optionally substituted with one or more halogen, hydrogen or cyano;
a malononitrile compound of the formula (I) in which R3 and R4 each represent C1-C5 alkyl optionally substituted with one or more halogen, C2-C5 alkenyl optionally substituted with one or more halogen, C2-C5 alkynyl optionally substituted with one or more halogen, C3-C5 cycloalkyl optionally substituted with one or more halogen, or hydrogen, or R3 and R4 are taken together to form C2-C6 alkanediyl optionally substituted with one or more halogen;
a malononitrile compound of the formula (I) in which R3 is hydrogen and R4 is C1-C5 alkyl optionally substituted with one or more halogen, C2-C5 alkenyl optionally substituted with one or more halogen, C2-C5 alkynyl optionally substituted with one or more halogen, or R3 and R4 are taken together to form C2-C6 alkanediyl optionally substituted with one or more halogen;
a malononitrile compound of the formula (I) in which R1 is hydrogen, R2 is C1-C3 alkyl optionally substituted with one or more halogen or hydrogen, and R3 and R4 each represent C1-C3 alkyl optionally substituted with one or more halogen, C2-C5 alkenyl optionally substituted with one or more halogen, C2-C5 alkynyl optionally substituted with
one or more halogen, C3-C5 cycloalkyl optionally substituted with one or more halogen, or hydrogen, or R3 and R4 are taken together to form C2-C6 alkanediyl optionally substituted with one or more halogen;
a malononitrile compound of the formula (I) in which R1 is C1-C3 alkyl optionally substituted with one or more halogen or hydrogen, R2 is C1-C3 alkyl optionally substituted with one or more halogen, C1-C3 alkoxy optionally substituted with one or more halogen, C2-C5 alkenyl optionally substituted with one or more halogen, C2-C5 alkynyl optionally substituted with one or more halogen, hydrogen or cyano, and R3 and R4 each represent C1-C5 alkyl optionally substituted with one or more halogen, C2-C5 alkenyl optionally substituted with one or more halogen, C2-C5 alkynyl optionally substituted with one or more halogen, C3-C5 cycloalkyl optionally substituted with one or more halogen or hydrogen, or R3 and R4 are taken together to form C2-C6 alkanediyl optionally substituted with one or more halogen;
a malononitrile compound of the formula (I) in which R1 is hydrogen, R2 is C1-C3 alkyl optionally substituted with one or more halogen, or hydrogen, and R3 and R4 each represent C1-C3 alkyl optionally substituted with one or more halogen, C2-C5 alkenyl optionally substituted with one or more halogen, C2-C5 alkynyl optionally substituted with
one or more halogen, C3-C5 cycloalkyl optionally substituted with one or more halogen, or hydrogen, or R3 and R4 are taken together to form C2-C6 alkanediyl optionally substituted with one or more halogen;
5 a malononitrile compound of the formula (I) in which
R1 is C1-C3 alkyl optionally substituted with one or more halogen, or hydrogen, R2 is C1-C3 alkyl optionally substituted with one or more halogen, C1-C3 alkoxy optionally substituted with one or more halogen, C2-C5 10 alkenyl optionally substituted one or more halogen, C2-C5 alkynyl optionally substituted with one or more halogen, hydrogen or cyano, R3 is hydrogen, and R4 is C1-C5 alkyl optionally substituted with one or more halogen, C2-C5 alkenyl optionally substituted with one or more halogen or 15 C2-C5 alkyl optionally substituted with one or more halogen, or R3 and R4 are taken together to form C2-C6 alkanediyl optionally substituted with one or more halogen;
a malononitrile compound of the formula (I) in which Z is NR6, X1 is nitrogen, and X2, X3 and X4 each are CR5; 20 a malononitrile compound of the formula (I) in which Z
is oxygen, X1 is nitrogen, and X2, X3 and X4 each are CR5;
a malononitrile compound of the formula (I) in which Z is sulfur, X1 is nitrogen, and X2, X3 and X4 each are CR5;
a malononitrile compound of the formula (I) in which Z 25 is NR6, X2 is nitrogen, and X1, X3 and X4 each are CR5;
a malononitrile compound of the formula (I) in which Z is oxygen, X2 is nitrogen, and X1, X3 and X4 each are CR5;
a malononitrile compound of the formula (I) in which Z is sulfur, X2 is nitrogen, and X1, X3 and X4 each are CR5;
5 a malononitrile compound of the formula (I) in which Z
is NR6, X1 and X2 are nitrogen, and X3 and X4 each are CR5;
a malononitrile compound of the formula (I) in which Z ^ is NR6, X1 and X3 are nitrogen, and X2 and X4 each are CR5;
a malononitrile compound of the formula (I) in which Z 10 is oxygen, X1 and X3 are nitrogen, and X2 and X4 each are CR5;
a malononitrile compound of the formula (I) in which Z is oxygen, X2 and X3 are nitrogen, and X1 and X4 each are CR5;
15 a malononitrile compound of the formula (I) in which Z
is sulfur, X1 and X3 are nitrogen, and X2 and X4 each are CR5;
a malononitrile compound of the formula (I) in which Z is sulfur, X2 and X3 are nitrogen, and X1 and X4 each are 20 CR5;
a malononitrile compound of the formula (I) in which Z is NR6, X1, X2 and X3 are nitrogen, and X4 is CR5;
a malononitrile compound represented by the formula
(I-i)

a malononitrile compound of the formula (I-i) in which any one of X3 and X4 is a carbon atom bound to cyclopropyl;
a malononitrile compound of the formula (I-i) in which any one of X3 and X4 is a carbon atom bound to 1- 5 methylcyclopropyl;
a malononitrile compound of the formula (I-i) in which any one of X3 and X4 is a carbon atom bound to propargyloxy;
a malononitrile compound of the formula (I-i) in which 10 any one of X3 and X4 is a carbon atom bound to 2- butynyloxy;
a malononitrile compound of the formula (I-i) in which any one of X3 and X4 is a carbon atom bound to 3- butynyloxy;
15 a malononitrile compound of the formula (I-i) in which
any one of X3 and X4 is a carbon atom bound to methylthio ;
a malononitrile compound of the formula (I-i) in which any one of X3 and X4 is a carbon atom bound to trifluoromethylthio; 20 a malononitrile compound of the formula (I-i) in which
any one of X3 and X4 is a carbon atom bound to propargylthio;
a malononitrile compound of the formula (I-i) in which any one of X3 and X4 is a carbon atom bound to 25 methylsulfinyl;
a malononitrile compound of the formula (I-i) in which any one of X3 and X4 is a carbon atom bound to trifluoromethylsulfynyl;
a malononitrile compound of the formula (I-i) in which 5 any one of X3 and X4 is a carbon atom bound to methylsulfonyl;
a malononitrile compound of the formula (I-i) in which any one of X3 and X4 is a carbon atom bound to trifluoromethylsulfonyl;
10 a malononitrile compound of the formula (I-i) in which
any one of X3 and X4 is a carbon atom bound to cyano;
a malononitrile compound of the formula (I-i) in which any one of X3 and X4 is a carbon atom bound to a bromine atom;
15 a malononitrile compound of the formula (I-i) in which
any one of X3 and X4 is a carbon atom bound to a chlorine atom;
a malononitrile compound of the formula (I-i) in which any one of X3 and X4 is a carbon atom bound to a fluorine
20 atom;
a malononitrile compound of the formula (I-i) in which any one of X3 and X4 is a carbon atom bound to nitro;
a malononitrile compound of the formula (I-i) in which X3 is a carbon atom bound to halogen, cyano or nitro;
25 a malononitrile compound of the formula (I-i) in which
X3 is a carbon atom bound to C1-C5 alkylthio optionally substituted with one or more halogen, C1-C5 alkylsulfynyl optionally substituted with one or more halogen or C1-C5 alkylsulfonyl optionally substituted with one or more 5 halogen;
a malononitrile compound of the formula (I-i) in which X3 is a carbon atom bound to C1-C5 alkyl optionally substituted with one or more halogen, C2-C5 alkenyl optionally substituted with one or more halogen, C2-C5 10 alkynyl optionally substituted with one or more halogen or C3-C6 alkynyl optionally substituted with one or more halogen;
a malononitrile compound of the formula (I-i) in which X3 is a carbon atom bound to C1-C5 alkoxy optionally 15 substituted with one or more halogen, C3-C6 alkenyloxy optionally substituted with one or more halogen, C3-C6 alkynyloxy optionally substituted with one or more halogen or C3-C6 alkynyl optionally substituted with one or more halogen;
20 a malononitrile compound of the formula (I-i) in which
X4 is a carbon atom bound to halogen, cyano or nitro; a malononitrile compound of the formula (I-i) in which X4 is a carbon atom bound to C1-C5 alkylthio optionally substituted with one or more halogen, C1-C5 alkylsulfinyl 25 optionally substituted with one or more halogen or C1-C5

a malononitrile compound of the formula (I-ii) in which Z is NR6 and R6 is 1-methylethyl;
a malononitrile compound of the formula (I-ii) in which X4 is a carbon atom bound to 1-methylethyl;
a malononitrile compound of the formula (I-ii) in which Z is NR6 and R6 is 1,1-dimethylethyl;
a malononitrile compound of the formula (I-ii) in which X4 is a carbon atom bound to 1,1-dimethylethyl;
a malononitrile compound of the formula (I-ii) in which Z is NR6 and R6 is 2,2-dimethylpropyl;
a malononitrile compound of the formula (I-ii) in which X4 is a carbon atom bound to 2,2-dimethylpropyl;
a malononitrile compound of the formula (I-ii) in which X4 is a carbon atom bound to trifluoromethyl;
a malononitrile compound of the formula (I-ii) in which X4 is a carbon atom bound to pentafluoroethyl;
a malononitrile compound of the formula (I-ii) in which X4 is a carbon atom bound to 1-methylvinyl;
a malononitrile compound of the formula (I-ii) in which X4 is a carbon atom bound to ethynyl;
a malononitrile compound of the formula (I-ii) in which Z is NR6 and R6 is 2-propargyl;
a malononitrile compound of the formula (I-ii) in which Z is NR6 and R6 is cyclopropyl;
a malononitrile compound of the formula (I-ii) in
which X4 is a carbon atom bound to cyclopropyl;
a malononitrile compound of the formula (I-ii) in which Z is NR6 and R6 is 1-methylcyclopropyl;
a malononitrile compound of the formula (I-ii) in 5 which X4 is a carbon atom bound to 1-methylcyclopropyl;
a malononitrile compound of the formula (I-ii) in which X4 is a carbon atom bound to propargyloxy;
a malononitrile compound of the formula (I-ii) in which X4 is a carbon atom bound to 2-butynyloxy; 10 a malononitrile compound of the formula (I-ii) in
which X4 is a carbon atom bound to 3-butynyloxy;
a malononitrile compound of the formula (I-ii) in which X4 is a carbon atom bound to methylthio;
a malononitrile compound of the formula (I-ii) in 15 which X4 is a carbon atom bound to trifluoromethylthio;
a malononitrile compound of the formula (I-ii) in which X4 is a carbon atom bound to propargylthio;
a malononitrile compound of the formula (I-ii) in which X4 is a carbon atom bound to methylsulfinyl; 20 a malononitrile compound of the formula (I-ii) in
which X4 is a carbon atom bound to trifluoromethylsulfinyl;
a malononitrile compound of the formula (I-ii) in which X4 is a carbon atom bound to methylsulfonyl;
a malononitrile compound of the formula (I-ii) in 25 which X4 is a carbon atom bound to trifluoromethylsulfonyl;
a malononitrile compound of the formula (I-ii) in which X4 is a carbon atom bound to cyano;
a malononitrile compound of the formula (I-ii) in which X4 is a carbon atom bound to a bromine atom;
5 a malononitrile compound of the formula (I-ii) in
which X4 is a carbon atom bound to a chlorine atom;
a malononitrile compound of the formula (I-ii) in which X4 is a carbon atom bound to a fluorine atom;
a malononitrile compound of the formula (I-ii) in 10 which X4 is a carbon atom bound to nitro;
a malononitrile compound of the formula (I-ii) in which X4 is a carbon atom bound to halogen, cyano or nitro;
a malononitrile compound of the formula (I-ii) in which X4 is a carbon atom bound to C1-C5 alkylthio 15 optionally substituted with one or more halogen, C1-C5 alkylsulfinyl optionally substituted with one or more halogen or C1-C5 alkylsulfonyl optionally substituted with one or more halogen;
a malononitrile compound of the formula (I-ii) in 20 which X4 is a carbon atom bound to C1-C5 alkyl optionally substituted with one or more halogen, C2-C5 alkenyl optionally substituted with one or more halogen, C2-C5 alkynyl optionally substituted with one or more halogen or C3-C6 alkynyl optionally substituted with one or more 25 halogen;

or more halogen, C1-C5 alkoxy optionally substituted with one or more halogen, C2-C5 alkenyl optionally substituted with one or more halogen, C2-C5 alkynyl optionally substituted with one or more halogen, cyano or hydrogen;
5 R3 and R4 each represent C1-C5 alkyl optionally substituted with one or more halogen, C2-C5 alkenyl optionally substituted with one or more halogen, C2-C5 alkynyl optionally substituted with one or more halogen, C3-C5 cycloalkyl optionally substituted with one or more halogen, 10 C4-C5 cycloalkenyl optionally substituted with one or more halogen, or hydrogen,
or R3 and R4 are taken together to represent C2-C6 alkanediyl optionally substituted with one or more halogen or C4-C6 alkenediyl optionally substituted with one or more 15 halogen;
R5 represent halogen, cyano, nitro, formyl, SF5, C1-C5 alkyl optionally substituted with one or more halogen, C2- C5 alkenyl optionally substituted with one or more halogen, C2-C5 alkynyl optionally substituted with one or more 20 halogen, C3-C6 cycloalkyl optionally substituted with one or more halogen or one or more C1-C3 alkyl, C1-C5 alkoxy optionally substituted with one or more halogen, C3-C6 alkenyloxy optionally substituted with one or more halogen, C3-C6 alkynyloxy optionally substituted with one or more 25 halogen, C1-C5 alkylthio optionally substituted with one or
more halogen, C3-C5 alkenylthio optionally substituted with one or more halogen, C3-C5 alkynylthio optionally substituted with one or more halogen, C1-C5 alkylsulfinyl optionally substituted with one or more halogen, C1-C5 5 alkylsulfonyl optionally substituted with one or more
halogen, C2-C6 alkylcarbonyl optionally substituted with one or more halogen, a group represented by C (OR19) R20R21, or hydrogen,R6 represents C1-C5 alkyl optionally substituted
t
with one or more halogen, 10 R19 represents C1-C5 alkyl optionanlly substituted with one or more halogen, C3-C5 alkynyl optionanlly substituted with one or more halogen, or hydrogen, and R20 and R21 each represent C1-C5 alkyl optionanlly substituted with one or more halogen,or hydrogen; 15 a malononitrile compound of the formula (Il-i) in
which R1 is hydrogen,
R2 is C1-C5 alkyl optionally substituted with one or more halogen, or hydrogen,
R3 and R4 each are C1-C5 alkyl optionally substituted with 20 one or more halogen, C2-C5 alkenyl optionally substituted with one or more halogen, or hydrogen,
R5 is halogen, C1-C5 alkyl optionally substituted with one or more halogen, C3-C6 cycloalkyl optionally substituted with one or more halogen, C1-C5 alkoxy optionally 25 substituted with one or more halogen, C3-C6 alkenyloxy
optionally substituted with one or more halogen, C3-C6 alkynyloxy optionally substituted with one or more halogen, C1-C5 alkylthio optionally substituted with one or more halogen, C1-C5 alkylsulfinyl optionally substituted with 5 one or more halogen, C1-C5 alkylsulfonyl optionally
substituted with one or more halogen, a group represented by C(OR19)R20R21, or hydrogen, and
R6 is C1-C5 alkyl optionally substituted with one or more halogen,
10 R19 represents C1-C5 alkyl optionanlly substituted with one or more halogen, C3-C5 alkynyl optionanlly substituted with one or more halogen, or hydrogen, and R20 and R21 each represent C1-C5 alkyl optionanlly substituted with one or more halogen,or hydrogen; 15 a malononitrile compound of the formula (Il-i) in
which R1 and R2 are hydrogen, R3 is hydrogen,
R4 is C1-C5 alkyl optionally substituted with one or more halogen or C2-C5 alkenyl optionally substituted with one or 20 more halogen,
R5 is C1-C5 alkyl optionally substituted with one or more halogen, and
R6 is C1-C5 alkyl optionally substituted with one or more halogen;
25 a malononitrile compound of the formula (Il-i) in

optionally substituted with one or more halogen, C3-C5 cycloalkyl optionally substituted with one or more halogen, C4-C5 cycloalkenyl optionally substituted with one or more halogen, or hydrogen, 5 or R3 and R4 are taken together to represent C2-C6
alkanediyl optionally substituted with one or more halogen or C4-C6 alkenediyl optionally substituted with one or more halogen,
R5 represents halogen, cyano, nitro, formyl, SF5, C1-C5 10 alkyl optionally substituted with one or more halogen, C2- C5 alkenyl optionally substituted with one or more halogen, C2-C5 alkynyl optionally substituted with one or more halogen, C3-C6 cycloalkyl optionally substituted with one or more halogen or one or more C1-C3 alkyl, C1-C5 alkoxy 15 optionally substituted with one or more halogen, C3-C6
alkenyloxy optionally substituted with one or more halogen, C3-C6 alkynyloxy optionally substituted with one or more ** halogen, C1-C5 alkylthio optionally substituted with one or
more halogen, C3-C5 alkenylthio optionally substituted with 20 one or more halogen, C3-C5 alkynylthio optionally
substituted with one or more halogen, C1-C5 alkylsulfinyl optionally substituted with one or more halogen, C1-C5 alkylsulfonyl optionally substituted with one or more halogen C2-C6 alkylcarbonyl optionally substituted with one 25 or more halogen, a group represented by C (OR19) R20R21, or
hydrogen,
R19' represents C1-C5 alkyl optionanlly substituted with one or more halogen, C3-C5 alkynyl optionanlly substituted with 5 one or more halogen, or hydrogen, and
R20 and R21 each represent C1-C5 alkyl optionanlly substituted with one or more halogen,or hydrogen;
a malononitrile compound of the formula (Il-ii) in which R1 is hydrogen, 10 R2 is C1-C5 alkyl optionally substituted with one or more halogen, or hydrogen,
R3 and R4 each are C1-C5 alkyl optionally substituted with one or more halogen, C2-C5 alkenyl optionally substituted with one or more halogen, or hydrogen, 15 R5 is halogen, C1-C5 alkyl optionally substituted with one or more halogen, C3-C6 cycloalkyl optionally substituted with one or more halogen, C1-C5 alkoxy optionally substituted with one or more halogen, C3-C6 alkenyloxy optionally substituted with one or more halogen, C3-C6 20 alkynyloxy optionally substituted with one or more halogen, C1-C5 alkylthio optionally substituted with one or more halogen, C1-C5 alkylsulfinyl optionally substituted with one or more halogen C1-C5 alkylsulfonyl optionally substituted with one or more halogen, a group represented 25 by C(OR19)R20R21, or hydrogen,

with one or more halogen, C2-C5 alkenyl optionally substituted with one or more halogen, C2-C5 alkynyl optionally substituted with one or more halogen, or hydrogen,
5 R2 represents C1-C5 alkyl optionally substituted with one or more halogen, C1-C5 alkoxy optionally substituted with one or more halogen, C2-C5 alkenyl optionally substituted ^ with one or more halogen, C2-C5 alkynyl optionally
substituted with one or more halogen, cyano or hydrogen, 10 R3 and R4 each represent C1-C5 alkyl optionally substituted with one or more halogen, C2-C5 alkenyl optionally substituted with one or more halogen, C2-C5 alkynyl optionally substituted with one or more halogen, C3-C5 cycloalkyl optionally substituted with one or more halogen, 15 C4-C5 cycloalkenyl optionally substituted with one or more halogen, or hydrogen,
or R3 and R4 are taken together to represent C2-C6 alkanediyl optionally substituted with one or more halogen or C4-C6 alkenediyl optionally substituted with one or more 20 halogen,
R5 represents halogen, cyano, nitro, formyl, SF5, C1-C5 alkyl optionally substituted with one or more halogen, C2- C5 alkenyl optionally substituted with one or more halogen, C2-C5 alkynyl optionally substituted with one or more 25 halogen, C3-C6 cycloalkyl optionally substituted with one
or more halogen or one or more C1-C3 alkyl, C1-C5 alkoxy optionally substituted with one or more halogen, C3-C6 alkenyloxy optionally substituted with one or more halogen, C3-C6 alkynyloxy optionally substituted with one or more 5 halogen, C1-C5 alkylthio optionally substituted with one or more halogen, C3-C5 alkenylthio optionally substituted with one or more halogen, C3-C5 alkynylthio optionally ^ substituted with one or more halogen, C1-C5 alkylsulfinyl
optionally substituted with one or more halogen, C1-C5 10 alkylsulfonyl optionally substituted with one or more
halogen, C2-C6 alkylcarbonyl optionally substituted with one or more halogen, a group represented by C (OR19) R20R21, or hydrogen, and
R6 represents C1-C5 alkyl optionally substituted with one 15 or more halogen,
R19 represents C1-C5 alkyl optionanlly substituted with one or more halogen, C3-C5 alkynyl optionanlly substituted with one or more halogen, or hydrogen, and R20 and R21 each represent C1-C5 alkyl optionanlly 20 substituted with one or more halogen,or hydrogen;
a malononitrile compound of the formula (II-iii) in which R1 is hydrogen,
R2 is C1-C5 alkyl optionally substituted with one or more halogen, or hydrogen, 25 R3 and R4 each are C1-C5 alkyl optionally substituted with
one or more halogen, C2-C5 alkenyl optionally substituted with one or more halogen, or hydrogen,
R5 is halogen, C1-C5 alkyl optionally substituted with one or more halogen, C3-C6 cycloalkyl optionally substituted 5 with one or more halogen, C1-C5 alkoxy optionally
substituted with one or more halogen, C3-C6 alkenyloxy optionally substituted with one or more halogen, C3-C6 ^ alkynyloxy optionally substituted with one or more halogen,
C1-C5 alkylthio optionally substituted with one or more 10 halogen, C1-C5 alkylsulfinyl optionally substituted with one or more halogen, C1-C5 alkylsulfonyl optionally substituted with one or more halogen, a group represented by C(OR19)R20R21, or hydrogen,
R6 is C1-C5 alkyl optionally substituted with one or more 15 halogen,
R19 represents C1-C5 alkyl optionanlly substituted with one or more halogen, C3-C5 alkynyl optionanlly substituted with one or more halogen, or hydrogen, and R20 and R21 each represent C1-C5 alkyl optionanlly 20 substituted with one or more halogen,or hydrogen;
a malononirtile compound of the formula (II-iii) in which R1 and R2 are hydrogen, R3 is hydrogen,
R4 is C1-C5 alkyl optionally substituted with one or more 25 halogen or C2-C5 alkenyl optionally substituted with one or

one or more halogen, C2-C5 alkenyl optionally substituted with one or more halogen, C2-C5 alkynyl optionally substituted with one or more halogen, cyano or hydrogen, R3 and R4 each represent C1-C5 alkyl optionally substituted 5 with one or more halogen, C2-C5 alkenyl optionally substituted with one or more halogen, C2-C5 alkynyl optionally substituted with one or more halogen, C3-C5 cycloalkyl optionally substituted with one or more halogen, C4-C5 cycloalkenyl optionally substituted with one or more 10 halogen, or hydrogen,
or R3 and R4 are taken together to represent C2-C6 alkanediyl optionally substituted with one or more halogen or C4-C6 alkenediyl optionally substituted with one or more halogen,
15 R5 represents halogen, cyano, nitro, formyl, SF5, C1-C5
alkyl optionally substituted with one or more halogen, C2- C5 alkenyl optionally substituted with one or more halogen, C2-C5 alkynyl optionally substituted with one or more halogen, C3-C6 cycloalkyl optionally substituted with one 20 or more halogen or one or more C1-C3 alkyl, C1-C5 alkoxy optionally substituted with one or more halogen, C3-C6 alkenyloxy optionally substituted with one or more halogen, C3-C6 alkynyloxy optionally substituted with one or more halogen, C1-C5 alkylthio optionally substituted with one or 25 more halogen, C3-C5 alkenylthio optionally substituted with
one or more halogen, C3-C5 alkynylthio optionally substituted with one or more halogen, C1-C5 alkylsulfinyl optionally substituted with one or more halogen, C1-C5 alkylsulfonyl optionally substituted with one or more 5 halogen, C2-C6 alkylcarbonyl optionally substituted with
one or more halogen, a group represented by C (OR19) R20R21, or hydrogen,
R19 represents C1-C5 alkyl optionanlly substituted with one 10 or more halogen, C3-C5 alkynyl optionanlly substituted with one or more halogen, or hydrogen, and R20 and R21 each represent C1-C5 alkyl optionanlly substituted with one or more halogen,or hydrogen;
a malononitrile compound of the formula (Il-iv) in 15 which R1 is hydrogen,
R2 is C1-C5 alkyl optionally substituted with one or more halogen, or hydrogen,
R3 and R4 each are C1-C5 alkyl optionally substituted with one or more halogen, C2-C5 alkenyl optionally substituted 20 with one or more halogen, or hydrogen,
R5 is halogen, C1-C5 alkyl optionally substituted with one or more halogen, C3-C6 cycloalkyl optionally substituted with one or more halogen, C1-C5 alkoxy optionally substituted with one ore more halogen, C3-C6 alkenyloxy 25 optionally substituted with one or more halogen, C3-C6
alkynyloxy optionally substituted with one or more halogen, C1-C5 alkylthio optionally substituted with one or more halogen, C1-C5 alkylsulfinyl optionally substituted with one or more halogen, C1-C5 alkylsulfonyl optionally 5 substituted with one or more halogen, a group represented by C(OR19)R20R21, or hydrogen,
R19 represents C1-C5 alkyl optionanlly substituted with one or more halogen, C3-C5 alkynyl optionanlly substituted with 10 one or more halogen, or hydrogen, and
R20 and R21 each represent C1-C5 alkyl optionanlly substituted with one or more halogen,or hydrogen;
a malononitrile compound of the formula (Il-iv) in which R1 and R2 are hydrogen, 15 R3 is hydrogen,
R4 is C1-C5 alkyl optionally substituted with one or more halogen, or C2-C5 alkenyl optionally substituted with one or more halogen, and
R5 is C1-C5 alkyl optionally substituted with one or more 20 halogen;
a malononitrile compound of the formula (Il-iv) in which R1 and R2 are hydrogen, R3 is hydrogen,
R4 is 2,2,2-trifluoroethyl, and 25 R5 is C1-C5 alkyl optionally substituted with one or more

or C4-C6 alkenediyl optionally substituted with one or more halogen,
R5 represents halogen, cyano, nitro, formyl, SF5, C1-C5 alkyl optionally substituted with one or more halogen, C2- 5 C5 alkenyl optionally substituted with one or more halogen, C2-C5 alkynyl optionally substituted with one or more halogen, C3-C6 cycloalkyl optionally substituted with one ^ or more halogen or one or more C1-C3 alkyl, C1-C5 alkoxy
optionally substituted with one or more halogen, C3-C6 10 alkenyloxy optionally substituted with one or more halogen, C3-C6 alkynyloxy optionally substituted with one or more halogen, C1-C5 alkylthio optionally substituted with one or more halogen, C3-C5 alkenylthio optionally substituted with one or more halogen, C3-C5 alkynylthio optionally 15 substituted with one or more halogen, C1-C5 alkylsulfinyl optionally substituted with one or more halogen, C1-C5 alkylsulfonyl optionally substituted with one or more halogen, C2-C6 alkylcarbonyl optionally substituted with one or more halogen, a group represented by C (OR19) R20R21, or 20 hydrogen,
R19 represents C1-C5 alkyl optionanlly substituted with one or more halogen, C3-C5 alkynyl optionanlly substituted with one or more halogen, or hydrogen, and 25 R20 and R21 each represent C1-C5 alkyl optionanlly
substituted with one or more halogen,or hydrogen;
a malononitrile compound of the formula (II-v) in which R1 is hydrogen,
R2 is C1-C5 alkyl optionally substituted with one or more 5 halogen, or hydrogen,
R3 and R4 each are C1-C5 alkyl optionally substituted with one or more halogen, C2-C5 alkenyl optionally substituted with one or more halogen, or hydrogen,
R5 is halogen, C1-C5 alkyl optionally substituted with one 10 or more halogen, C3-C6 cycloalkyl optionally substituted with one or more halogen, C1-C5 alkoxy optionally substituted with one or more halogen, C3-C6 alkenyloxy optionally substituted with one or more halogen, C3-C6 alkynyloxy optionally substituted with one or more halogen, 15 C1-C5 alkylthio optionally substituted with one or more halogen, C1-C5 alkylsulfinyl optionally substituted with one or more halogen, C1-C5 alkylsulfonyl optionally substituted with one or more halogen, a group represented by C (OR19)R20R21, or hydrogen,
20
R19 represents C1-C5 alkyl optionanlly substituted with one or more halogen, C3-C5 alkynyl optionanlly substituted with one or more halogen, or hydrogen, and R20 and R21 each represent C1-C5 alkyl optionanlly 25 substituted with one or more halogen,or hydrogen;

R2 represents C1-C5 alkyl optionally substituted with one or more halogen, C1-C5 alkoxy optionally substituted with one or more halogen, C2-C5 alkenyl optionally substituted with one or more halogen, C2-C5 alkynyl optionally 5 substituted with one or more halogen, cyano or hydrogen,
R3 and R4 each represent C1-C5 alkyl optionally substituted with one or more halogen, C2-C5 alkenyl optionally substituted with one or more halogen, C2-C5 alkynyl optionally substituted with one or more halogen, C3-C5 10 cycloalkyl optionally substituted with one or more halogen, C4-C5 cycloalkenyl optionally substituted with one or more halogen, or hydrogen,
or R3 and R4 are taken together to represent C2-C6 alkanediyl optionally substituted with one or more halogen 15 or C4-C6 alkenediyl optionally substituted with one or more halogen,
R5 represents halogen, cyano, nitro, formyl, SF5, C1-C5 alkyl optionally substituted with one or more halogen, C2- C5 alkenyl optionally substituted with one or more halogen, 20 C2-C5 alkynyl optionally substituted with one or more
halogen, C3-C6 cycloalkyl optionally substituted with one or more halogen or one or more C1-C3 alkyl, C1-C5 alkoxy optionally substituted with one or more halogen, C3-C6 alkenyloxy optionally substituted with one or more halogen, 25 C3-C6 alkynyloxy optionally substituted with one or more
halogen, C1-C5 alkylthio optionally substituted with one or more halogen, C3-C5 alkenylthio optionally substituted with one or more halogen, C3-C5 alkynylthio optionally substituted with one or more halogen, C1-C5 alkylsulfinyl 5 optionally substituted with one or more halogen, C1-C5 alkylsulfonyl optionally substituted with one or more halogen, C2-C6 alkylcarbonyl optionally substituted with one or more halogen, a group represented by C (OR19) R20R21, or hydrogen,
10 R19 represents C1-C5 alkyl optionanlly substituted with one or more halogen, C3-C5 alkynyl optionanlly substituted with one or more halogen, or hydrogen, and R20 and R21 each represent C1-C5 alkyl optionanlly substituted with one or more halogen,or hydrogen; 15 a malononitrile compound of the formula (Il-vi) in
which R1 is hydrogen,
R2 is C1-C5 alkyl optionally substituted with one or more
rv
halogen, or hydrogen,
R3 and R4 each represent C1-C5 alkyl optionally substituted 20 with one or more halogen, C2-C5 alkenyl optionally substituted with one or more halogen, or hydrogen, R5 represents halogen, C1-C5 alkyl optionally substituted with one or more halogen, C3-C6 cycloalkyl optionally substituted with one or more halogen, C1-C5 alkoxy 25 optionally substituted with one or more halogen, C3-C6
alkenyloxy optionally substituted with one or more halogen, C3-C6 alkynyloxy optionally substituted with one or more halogen, C1-C5 alkylthio optionally substituted with one or more halogen, C1-C5 alkylsulfinyl optionally substituted 5 with one or more halogen, C1-C5 alkylsulfonyl optionally substituted with one or more halogen, a group represented by C(OR19)R20R21, or hydrogen,
'-S
R19 represents C1-C5 alkyl optionanlly substituted with one 10 or more halogen, C3-C5 alkynyl optionanlly substituted with one or more halogen, or hydrogen, and R20 and R21 each represent C1-C5 alkyl optionanlly substituted with one or more halogen,or hydrogen;
a malononitrile compound of the formula (Il-vi) in 15 which R1 and R2 are hydrogen, R3 is hydrogen,
R4 is C1-C5 alkyl optionally substituted with one or more halogen, or C2-C5 alkenyl optionally substituted with one or more halogen, and 20 R5 is C1-C5 alkyl optionally substituted with one or more halogen;
a malononitrile compound of the formula (Il-vi) in which R1 and R2 are hydrogen, R3 is hydrogen, 25 R4 is 2,2,2-trifluoroethyl, and

or R3 and R4 are taken together to represent C2-C6 alkanediyl optionally substituted with one or more halogen or C4-C6 alkenediyl optionally substituted with one or more halogen,
5 R5 represents halogen, cyano, nitro, formyl, SF5, C1-C5
alkyl optionally substituted with one or more halogen, C2- C5 alkenyl optionally substituted with one or more halogen, ^ C2-C5 alkynyl optionally substituted with one or more
halogen, C3-C6 cycloalkyl optionally substituted with one 10 or more halogen or one or more C1-C3 alkyl, C1-C5 alkoxy optionally substituted with one or more halogen, C3-C6 alkenyloxy optionally substituted with one or more halogen, C3-C6 alkynyloxy optionally substituted with one or more halogen, C1-C5 alkylthio optionally substituted with one or 15 more halogen, C3-C5 alkenylthio optionally substituted with one or more halogen, C3-C5 alkynylthio optionally substituted with one or more halogen, C1-C5 alkylsulfinyl optionally substituted with one or more halogen, C1-C5 alkylsulfonyl optionally substituted with one or more 20 halogen, C2-C6 alkylcarbonyl optionally substituted with
one or more halogen, a group represented by C (OR19) R20R21, or hydrogen,
R19 represents C1-C5 alkyl optionanlly substituted with one 25 or more halogen, C3-C5 alkynyl optionanlly substituted with
one or more halogen, or hydrogen, and
R20 and R21 each represent C1-C5 alkyl optionanlly
substituted with one or more halogen, or hydrogen;
a malononitrile compound of the formula (Il-vii) in 5 which R1 is hydrogen,
R2 is C1-C5 alkyl optionally substituted with one or more halogen, or hydrogen,
R3 and R4 each are C1-C5 alkyl optionally substituted with one or more halogen, C2-C5 alkenyl optionally substituted 10 with one or more halogen, or hydrogen,
R5 is halogen, C1-C5 alkyl optionally substituted with one or more halogen, C3-C6 cycloalkyl optionally substituted with one or more halogen, C1-C5 alkoxy optionally substituted with one or more halogen, C3-C6 alkenyloxy 15 optionally substituted with one or more halogen, C3-C6
alkynyloxy optionally substituted with one or more halogen, C1-C5 alkylthio optionally substituted with one or more halogen, C1-C5 alkylsulfinyl optionally substituted with one or more halogen, C1-C5 alkylsulfonyl optionally 20 substituted with one or more halogen, a group represented by C(OR19)R20R21, or hydrogen,
R19 represents C1-C5 alkyl optionanlly substituted with one or more halogen, C3-C5 alkynyl optionanlly substituted with 25 one or more halogen, or hydrogen, and

hydrogen,
R2 represents C1-C5 alkyl optionally substituted with one or more halogen, C1-C5 alkoxy optionally substituted with one or more halogen, C2-C5 alkenyl optionally substituted 5 with one or more halogen, C2-C5 alkynyl optionally
substituted with one or more halogen, cyano or hydrogen, R3 and R4 each represent C1-C5 alkyl optionally substituted with one or more halogen, C2-C5 alkenyl optionally substituted with one or more halogen, C2-C5 alkynyl 10 optionally substituted with one or more halogen, C3-C5
cycloalkyl optionally substituted with one or more halogen, C4-C5 cycloalkenyl optionally substituted with one or more halogen, or hydrogen,
or R3 and R4 are taken together to represent C2-C6 15 alkanediyl optionally substituted with one or more halogen or C4-C6 alkenediyl optionally substituted with one or more halogen,
R5 represents halogen, cyano, nitro, formyl, SF5, C1-C5 alkyl optionally substituted with one or more halogen, C2- 20 C5 alkenyl optionally substituted with one or more halogen, C2-C5 alkynyl optionally substituted with one or more halogen, C3-C6 cycloalkyl optionally substituted with one or more halogen or one or more C1-C3 alkyl, C1-C5 alkoxy optionally substituted with one or more halogen, C3-C6 25 alkenyloxy optionally substituted with one or more halogen,
C3-C6 alkynyloxy optionally substituted with one or more halogen, C1-C5 alkylthio optionally substituted with one or more halogen, C3-C5 alkenylthio optionally substituted with one or more halogen, C3-C5 alkynylthio optionally substituted with one or more halogen, C1-C5 alkylsulfinyl optionally substituted with one or more halogen, C1-C5 alkylsulfonyl optionally substituted with one or more halogen, C2-C6 alkylcarbonyl optionally substituted with one or more halogen, a group represented by C (OR19) R20R21, or hydrogen,
R19 represents C1-C5 alkyl optionanlly substituted with one or more halogen, C3-C5 alkynyl optionanlly substituted with one or more halogen, or hydrogen, and R20 and R21 each represent C1-C5 alkyl optionanlly substituted with one or more halogen,or hydrogen;
a malononitrile compound of the formula (II-viii) in which R1 is hydrogen,
R2 is C1-C5 alkyl optionally substituted with one or more halogen, or hydrogen,
R3 and R4 each are C1-C5 alkyl optionally substituted with one or more halogen, C2-C5 alkenyl optionally substituted with one or more halogen, or hydrogen,
R5 is halogen, C1-C5 alkyl optionally substituted with one or more halogen, C3-C6 cycloalkyl optionally substituted
with one or more halogen, C1-C5 alkoxy optionally substituted with one or more halogen, C3-C6 alkenyloxy optionally substituted with one or more halogen, C3-C6 alkynyloxy optionally substituted with one or more halogen, 5 C1-C5 alkylthio optionally substituted with one or more halogen, C1-C5 alkylsulfinyl optionally substituted with one or more halogen, C1-C5 alkylsulfonyl optionally substituted with one or more halogen, a group represented by C(OR19)R20R21, or hydrogen,
10
R19 represents C1-C5 alkyl optionanlly substituted with one or more halogen, C3-C5 alkynyl optionanlly substituted with one or more halogen, or hydrogen, and R20 and R21 each represent C1-C5 alkyl optionanlly 15 substituted with one or more halogen, or hydrogen;
a malononitrile compound of the formula (II-viii) in which R1 and R2 are hydrogen,
r-N
R3 is hydrogen,
R4 is C1-C5 alkyl optionally substituted with one or more 20 halogen, or C2-C5 alkenyl optionally substituted with one or more halogen, and
R5 is C1-C5 alkyl optionally substituted with one or more halogen ;
25 a malononitrile compound of the formula (II-viii) in

C4-C5 cycloalkenyl optionally substituted with one or more halogen, or hydrogen,
or R3 and R4 are taken together to represent C2-C6 alkanediyl optionally substituted with one or more halogen 5 or C4-C6 alkenediyl optionally substituted with one or more halogen,
Rs represents halogen, cyano, nitro, formyl, SF5, C1-C5 alkyl optionally substituted with one or more halogen, C2- C5 alkenyl optionally substituted with one or more halogen, 10 C2-C5 alkynyl optionally substituted with one or more , halogen, C3-C6 cycloalkyl optionally substituted with one or more halogen or one or more C1-C3 alkyl, C1-C5 alkoxy optionally substituted with one or more halogen, C3-C6 alkenyloxy optionally substituted with one or more halogen, 15 C3-C6 alkynyloxy optionally substituted with one or more
halogen, C1-C5 alkylthio optionally substituted with one or more halogen, C3-C5 alkenylthio optionally substituted with one or more halogen, C3-C5 alkynylthio optionally substituted with one or more halogen, C1-C5 alkylsulfinyl 20 optionally substituted with one or more halogen, C1-C5 alkylsulfonyl optionally substituted with one or more halogen, C2-C6 alkylcarbonyl optionally substituted with one or more halogen, a group represented by C (OR19) R20R21, or hydrogen,
25 R6 represents C1-C5 alkyl optionally substituted with one
or more halogen,
R19 represents C1-C5 alkyl optionanlly substituted with one or more halogen, C3-C5 alkynyl optionanlly substituted with one or more halogen, or hydrogen, and 5 R20 and R21 each represent C1-C5 alkyl optionanlly substituted with one or more halogen,or hydrogen;
a malononitrile compound of the formula (Il-ix) in which R1 is hydrogen,
R2 is C1-C5 alkyl optionally substituted with one or more 10 halogen, or hydrogen,
R3 and R4 each are C1-C5 alkyl optionally substituted with one or more halogen, C2-C5 alkenyl optionally substituted with one or more halogen, or hydrogen,
R5 is halogen, C1-C5 alkyl optionally substituted with one 15 or more halogen, C3-C6 cycloalkyl optionally substituted with one or more halogen, C1-C5 alkoxy optionally substituted with one or more halogen, C3-C6 alkenyloxy optionally substituted with one or more halogen, C3-C6 alkynyloxy optionally substituted with one or more halogen, 20 C1-C5 alkylthio optionally substituted with one or more halogen, C1-C5 alkylsulfinyl optionally substituted with one or more halogen, C1-C5 alkylsulfonyl optionally substituted with one or more halogen, a group represented by C(OR19)R20R21, or hydrogen, 25 R6 is C1-C5 alkyl optionally substituted with one or more
halogen,
R19 represents C1-C5 alkyl optionanlly substituted with one or more halogen, C3-C5 alkynyl optionanlly substituted with one or more halogen, or hydrogen, and 5 R20 and R21 each represent C1-C5 alkyl optionanlly substituted with one or more halogen,or hydrogen;
a malononitrile compound of the formula (Il-ix) in which R1 and R2 are hydrogen, R3 is hydrogen,
10 R4 is C1-C5 alkyl optionally substituted with one or more halogen, or C2-C5 alkenyl optionally substituted with one or more halogen,
R5 is C1-C5 alkyl optionally substituted with one or more halogen, and
15 R6 is C1-C5 alkyl optionally substituted with one or more halogen;
a malononitrile compound of the formula (Il-ix) in which R1 and R2 are hydrogen, R3 is hydrogen, 20 R4 is 2,2,2-trifluoroethyl,
R5 is C1-C5 alkyl optionally substituted with one or more halogen, and
R6 is C1-C5 alkyl optionally substituted with one or more halogen;
25 a malononitrile compound represented by the formula

halogen;
R5 represent halogen, cyano, nitro, formyl, SF5, C1-C5 alkyl optionally substituted with one or more halogen, C2- C5 alkenyl optionally substituted with one or more halogen, 5 C2-C5 alkynyl optionally substituted with one or more
halogen, C3-C6 cycloalkyl optionally substituted with one or more halogen or one or more C1-C3 alkyl, C1-C5 alkoxy optionally substituted with one or more halogen, C3-C6 alkenyloxy optionally substituted with one or more halogen, 10 C3-C6 alkynyloxy optionally substituted with one or more
halogen, C1-C5 alkylthio optionally substituted with one or more halogen, C3-C5 alkenylthio optionally substituted with one or more halogen, C3-C5 alkynylthio optionally substituted with one or more halogen, C1-C5 alkylsulfinyl 15 optionally substituted with one or more halogen, C1-C5 alkylsulfonyl optionally substituted with one or more halogen, C2-C6 alkylcarbonyl optionally substituted with one or more halogen, a group represented by C (OR19) R20R21, or hydrogen,
20 R6 represents C1-C5 alkyl optionally substituted with one or more halogen,
R19 represents C1-C5 alkyl optionanlly substituted with one or more halogen, C3-C5 alkynyl optionanlly substituted with one or more halogen, or hydrogen, and 25 R20 and R21 each represent C1-C5 alkyl optionanlly
substituted with one or more halogen,or hydrogen;
a malononitrile compound of the formula (II-x) in which R1 is hydrogen,
R2 is C1-C5 alkyl optionally substituted with one or more 5 halogen, or hydrogen,
R3 and R4 each are C1-C5 alkyl optionally substituted with one or more halogen, C2-C5 alkenyl optionally substituted with one or more halogen, or hydrogen,
R5 is halogen, C1-C5 alkyl optionally substituted with one 10 or more halogen, C3-C6 cycloalkyl optionally substituted with one or more halogen, C1-C5 alkoxy optionally substituted with one or more halogen, C3-C6 alkenyloxy optionally substituted with one or more halogen, C3-C6 alkynyloxy optionally substituted with one or more halogen, 15 C1-C5 alkylthio optionally substituted with one or more halogen, C1-C5 alkylsulfinyl optionally substituted with one or more halogen, C1-C5 alkylsulfonyl optionally
v
substituted with one or more halogen, a group represented by C(OR19)R20R21, or hydrogen, and 20 R6 is C1-C5 alkyl optionally substituted with one or more halogen,
R19 represents C1-C5 alkyl optionanlly substituted with one or more halogen, C3-C5 alkynyl optionanlly substituted with one or more halogen, or hydrogen, and 25 R20 and R21 each represent C1-C5 alkyl optionanlly

with one or more halogen, C2-C5 alkenyl optionally substituted with one or more halogen, C2-C5 alkynyl optionally substituted with one or more halogen, or hydrogen,
5 R2 represents C1-C5 alkyl optionally substituted with one or more halogen, C1-C5 alkoxy optionally substituted with one or more halogen, C2-C5 alkenyl optionally substituted with one or more halogen, C2-C5 alkynyl optionally substituted with one or more halogen, cyano or hydrogen, 10 R3 and R4 each represent C1-C5 alkyl optionally substituted with one or more halogen, C2-C5 alkenyl optionally substituted with one or more halogen, C2-C5 alkynyl optionally substituted with one or more halogen, C3-C5 cycloalkyl optionally substituted with one or more halogen, 15 C4-C5 cycloalkenyl optionally substituted with one or more halogen, or hydrogen,
or R3 and R4 are taken together to represent C2-C6 alkanediyl optionally substituted with one or more halogen or C4-C6 alkenediyl optionally substituted with one or more 20 halogen,
R5 represents halogen, cyano, nitro, formyl, SF5, C1-C5 alkyl optionally substituted with one or more halogen, C2- C5 alkenyl optionally substituted with one or more halogen, C2-C5 alkynyl optionally substituted with one or more 25 halogen, C3-C6 cycloalkyl optionally substituted with one
or more halogen or one or more C1-C3 alkyl, C1-C5 alkoxy optionally substituted with one or more halogen, C3-C6 alkenyloxy optionally substituted with one or more halogen, C3-C6 alkynyloxy optionally substituted with one or more 5 halogen, C1-C5 alkylthio optionally substituted with one or more halogen, C3-C5 alkenylthio optionally substituted with one or more halogen, C3-C5 alkynylthio optionally substituted with one or more halogen, C1-C5 alkylsulfinyl optionally substituted with one or more halogen, C1-C5 10 alkylsulfonyl optionally substituted with one or more
halogen C2-C6 alkylcarbonyl optionally substituted with one or more halogen, a group represented by C (OR19) R20R21, or hydrogen,
R19 represents C1-C5 alkyl optionanlly substituted with one 15 or more halogen, C3-C5 alkynyl optionanlly substituted with one or more halogen, or hydrogen, and R20 and R21 each represent C1-C5 alkyl optionanlly
r-N
^ substituted with one or more halogen, or hydrogen;
a malononitrile compound of the formula (Il-xi) in 20 which R1 is hydrogen,
R2 is C1-C5 alkyl optionally substituted with one or more halogen, or hydrogen,
R3 and R4 each are C1-C5 alkyl optionally substituted with one or more halogen, C2-C5 alkenyl optionally substituted 25 with one or more halogen, or hydrogen,
R5 is halogen, C1-C5 alkyl optionally substituted with one or more halogen, C3-C6 cycloalkyl optionally substituted with one or more halogen, C1-C5 alkoxy optionally substituted with one or more halogen, C3-C6 alkenyloxy 5 optionally substituted with one or more halogen, C3-C6
alkynyloxy optionally substituted with one or more halogen, C1-C5 alkylthio optionally substituted with one or more halogen, C1-C5 alkylsulfinyl optionally substituted with one or more halogen C1-C5 alkylsulfonyl optionally 10 substituted with one or more halogen, a group represented by C(OR19)R20R21, or hydrogen,
R19 represents C1-C5 alkyl optionanlly substituted with one or more halogen, C3-C5 alkynyl optionanlly substituted with one or more halogen, or hydrogen, and 15 R20 and R21 each represent C1-C5 alkyl optionanlly substituted with one or more halogen, or hydrogen;
a malononitrile compound of the formula (Il-xi) in which R and R are hydrogen, R3 is hydrogen,
20 R4 is C1-C5 alkyl optionally substituted with one or more
halogen or C2-C5 alkenyl optionally substituted with one or more halogen, and
R5 is C1-C5 alkyl optionally substituted with one or more halogen;
25 a malononitrile compound of the formula (Il-xi) in

C4-C5 cycloalkenyl optionally substituted with one or more halogen, or hydrogen,
or R3 and R4 are taken together to represent C2-C6 alkanediyl optionally substituted with one or more halogen 5 or C4-C6 alkenediyl optionally substituted with one or more halogen,
R5 represents halogen, cyano, nitro, formyl, SF5, C1-C5 alkyl optionally substituted with one or more halogen, C2- C5 alkenyl optionally substituted with one or more halogen, 10 C2-C5 alkynyl optionally substituted with one or more
halogen, C3-C6 cycloalkyl optionally substituted with one or more halogen or one or more C1-C3 alkyl, C1-C5 alkoxy optionally substituted with one or more halogen, C3-C6 alkenyloxy optionally substituted with one or more halogen, 15 C3-C6 alkynyloxy optionally substituted with one or more
halogen, C1-C5 alkylthio optionally substituted with one or more halogen, C3-C5 alkenylthio optionally substituted with one or more halogen, C3-C5 alkynylthio optionally substituted with one or more halogen, C1-C5 alkylsulfinyl 20 optionally substituted with one or more halogen, C1-C5 alkylsulfonyl optionally substituted with one or more halogen C2-C6 alkylcarbonyl optionally substituted with one or more halogen, a group represented by C (OR19) R20R21, or hydrogen,
25 R19 represents C1-C5 alkyl optionanlly substituted with one
or more halogen, C3-C5 alkynyl optionanlly substituted with one or more halogen, or hydrogen, and R20 and R21 each represent C1-C5 alkyl optionanlly substituted with one or more halogen,or hydrogen; 5 a malononitrile compound of the formula (Il-xii) in
which R1 is hydrogen,
R2 is C1-C5 alkyl optionally substituted with one or more halogen, or hydrogen,
R3 and R4 each are C1-C5 alkyl optionally substituted with 10 one or more halogen, C2-C5 alkenyl optionally substituted with one or more halogen, or hydrogen,
R5 is halogen, C1-C5 alkyl optionally substituted with one or more halogen, C3-C6 cycloalkyl optionally substituted with one or more halogen, C1-C5 alkoxy optionally 15 substituted with one or more halogen, C3-C6 alkenyloxy optionally substituted with one or more halogen, C3-C6 alkynyloxy optionally substituted with one or more halogen, C1-C5 alkylthio optionally substituted with one or more halogen, C1-C5 alkylsulfinyl optionally substituted with 20 one or more halogen C1-C5 alkylsulfonyl optionally
substituted with one or more halogen, a group represented by C(OR19)R20R21, or hydrogen,
R19 represents C1-C5 alkyl optionanlly substituted with one or more halogen, C3-C5 alkynyl optionanlly substituted with 25 one or more halogen, or hydrogen, and

hydrogen,
R2 represents C1-C5 alkyl optionally substituted with one or more halogen, C1-C5 alkoxy optionally substituted with one or more halogen, C2-C5 alkenyl optionally substituted 5 with one or more halogen, C2-C5 alkynyl optionally
substituted with one or more halogen, cyano or hydrogen, R3 and R4 each represent C1-C5 alkyl optionally substituted with one or more halogen, C2-C5 alkenyl optionally substituted with one or more halogen, C2-C5 alkynyl 10 optionally substituted with one or more halogen, C3-C5
cycloalkyl optionally substituted with one or more halogen, C4-C5 cycloalkenyl optionally substituted with one or more halogen, or hydrogen,
or R3 and R4 are taken together to represent C2-C6 15 alkanediyl optionally substituted with one or more halogen or C4-C6 alkenediyl optionally substituted with one or more halogen,
R5 represents halogen, cyano, nitro, formyl, SF5, C1-C5 alkyl optionally substituted with one or more halogen, C2- 20 C5 alkenyl optionally substituted with one or more halogen, C2-C5 alkynyl optionally substituted with one or more halogen, C3-C6 cycloalkyl optionally substituted with one or more halogen or one or more C1-C3 alkyl, C1-C5 alkoxy optionally substituted with one or more halogen, C3-C6 25 alkenyloxy optionally substituted with one or more halogen,
C3-C6 alkynyloxy optionally substituted with one or more halogen, C1-C5 alkylthio optionally substituted with one or more halogen, C3-C5 alkenylthio optionally substituted with one or more halogen, C3-C5 alkynylthio optionally 5 substituted with one or more halogen, C1-C5 alkylsulfinyl optionally substituted with one or more halogen, C1-C5 alkylsulfonyl optionally substituted with one or more halogen C2-C6 alkylcarbonyl optionally substituted with one or more halogen, a group represented by C (OR19) R20R21, or 10 hydrogen,
R19 represents C1-C5 alkyl optionanlly substituted with one or more halogen, C3-C5 alkynyl optionanlly substituted with one or more halogen, or hydrogen, and R20 and R21 each represent C1-C5 alkyl optionanlly 15 substituted with one or more halogen,or hydrogen;
a malononitrile compound of the formula (II-xiii) in which R1 is hydrogen,
R2 is C1-C5 alkyl optionally substituted with one or more halogen, or hydrogen, 20 R3 and R4 each are C1-C5 alkyl optionally substituted with one or more halogen, C2-C5 alkenyl optionally substituted with one or more halogen, or hydrogen,
R5 is halogen, C1-C5 alkyl optionally substituted with one or more halogen, C3-C6 cycloalkyl optionally substituted 25 with one or more halogen, C1-C5 alkoxy optionally
substituted with one or more halogen, C3-C6 alkenyloxy optionally substituted with one or more halogen, C3-C6 alkynyloxy optionally substituted with one or more halogen, C1-C5 alkylthio optionally substituted with one or more 5 halogen, C1-C5 alkylsulfinyl optionally substituted with one or more halogen C1-C5 alkylsulfonyl optionally substituted with one or more halogen, a group represented by C(OR19)R20R21, or hydrogen,
R19 represents C1-C5 alkyl optionanlly substituted with one 10 or more halogen, C3-C5 alkynyl optionanlly substituted with one or more halogen, or hydrogen, and R20 and R21 each represent C1-C5 alkyl optionanlly substituted with one or more halogen,or hydrogen;
a malononitrile compound of the formula (II-xiii) in 15 which R1 and R2 are hydrogen, R3 is hydrogen,
R4 is C1-C5 alkyl optionally substituted with one or more halogen or C2-C5 alkenyl optionally substituted with one or more halogen, and 20 R5 is C1-C5 alkyl optionally substituted with one or more halogen;
a malononitrile compound of the formula (II-xiii) in which R1 and R2 are hydrogen, R3 is hydrogen, 25 R4 is 2,2,2-trifluoroethyl, and

optionally substituted with one or more halogen, or hydrogen,
R2 represents C1-C5 alkyl optionally substituted with one or more halogen, C1-C5 alkoxy optionally substituted with 5 one or more halogen, C2-C5 alkenyl optionally substituted with one or more halogen, C2-C5 alkynyl optionally substituted with one or more halogen, cyano or hydrogen, ^^ R3 and R4 each represent C1-C5 alkyl optionally substituted
with one or more halogen, C2-C5 alkenyl optionally 10 substituted with one or more halogen, C2-C5 alkynyl
optionally substituted with one or more halogen, C3-C5 cycloalkyl optionally substituted with one or more halogen, C4-C5 cycloalkenyl optionally substituted with one or more halogen, or hydrogen, 15 or R3 and R4 are taken together to represent C2-C6
alkanediyl optionally substituted with one or more halogen or C4-C6 alkenediyl optionally substituted with one or more
r-v
halogen, and E1 represents a leaving group (e.g. chlorine, bromine, iodine, methanesulfonyloxy, 20 trifluoromethanesulfonyloxy or toluenesulfonyloxy).
The reaction is usually performed in a solvent in the presence of a base.
A solvent used in the reaction includes acid amide such as N,N-dimethylformamide, ether such as diethyl ether 25 or tetrahydrofran, organic sulfur such as dimethyl
sulfoxide or sulfolane, halogenated hydrocarbon such as 1,2-dichloroethane or chlorobenzene, aromatic hydrocarbon such as toluene or xylene, and a mixture thereof.
A base used in the reaction includes an inorganic base 5 such as sodium hydride, sodium carbonate or potassium
carbonate, an alkali metal alkoxide such as potassium-t- butoxide, and an organic base such as 4- dimethylaminopyridine, 1,4-diazabicyclo[2.2.2]octane or 1,8-diazabicyclo[5.4.0]-7-undecene. 10 The amount of a base used in the reaction is usually 1
to 10 moles per 1 mole of the compound (a).
The amount of the compound (b) used in the reaction is usually 1 to 10 moles per 1 mole of the compound (a).
The reaction temperature is usually in the range of - 15 20 to 100°C. The reaction time is usually in the range of 1 to 24 hours.
After completion of the reaction, the present compound represented by the formula (I) can be isolated by subjecting the reaction mixture to post-treatment, for 20 example, by addition of the reaction mixture into water followed by extraction with an organic solvent and then concentration of the extract. The isolated present compound represented by the formula (I) may be purified by chromatography, recrystallization or the like, if necessary.
25


solvent used in the reaction includes acid amide such as N,N-dimethylformamide, ether such as diethyl ether or tetrahydrofran, halogenated hydrocarbon such as chloroform, 1,2-dichloroethane or chlorobenzene, aromatic hydrocarbon 5 such as toluene or xylene, alcohol such as methanol, ethanol or isopropanol and a mixture thereof.
The reaction may be performed in the presence of a base, if necessary. A base used in the reaction includes tetrabutylammonium hydroxide. 10 The amount of a base used in the reaction is usually
0.01 to 0.5 moles per 1 mole of the compound (e).
The amount of malononitrile used in the reaction is usually 1 to 10 moles per 1 mole of the compound (e).
The reaction temperature is usually in the range of - 15 20 to 200°C. The reaction time is usually in the range of 1 to 24 hours.
The reaction may be performed while water produced by the reaction is removed from the reaction system, if necessary.
20 After completion of the reaction, the compound (f) can
be isolated by subjecting the reaction mixture to post- treatment, for example, by addition of the reaction mixture into water followed by extraction with an organic solvent and then concentration of the extract. The isolated 25 compound (f) may be purified by chromatography,
recrystallization or the like, if necessary.
(Second process)
(1) In a case that R2 is C1-C5 alkyl optionally substituted with halogen, C2-C5 alkenyl optionally substituted with halogen, or alkenyl optionally substituted with halogen;
The compound (a) can be prepared by reacting the compound (f) with an organometallic compound.
The reaction is usually performed in a solvent.
A solvent used in the reaction includes ether such as diethyl ether or tetrahydrofuran, aromatic hydrocarbon such as toluene or xylene, and a mixture thereof.
An organometallic compound used in the reaction includes an organic magnesium compound such as methylmagnesium iodide, ethylmagnesium bromide, isopropylmagnesium bromide, vinylmagnesium bromide, ethylmagnesium bromide or dimethylmagnesium, an organic lithium compound such as methyllithium, an organic zinc compound such as diethylzinc, and an organic copper compound such as trifluoromethylcopper.
The amount of an organometallic compound used in the reaction is usually 1 to 10 moles per 1 mole of the compound (f).
The reaction may be performed in the presence of a
copper salt, if necessary. A copper salt used in the reaction includes copper(I) iodide and copper(I) bromide. The amount of a copper salt used in the reaction is usually 0.05 to 1 mole per 1 mole of the compound (f).
5 The reaction temperature is usually in the range of -
20 to 100°C. The reaction time is usually in the range of 1 to 24 hours.
^m^ After completion of the reaction, the compound (a) can
be isolated by subjecting the reaction mixture to post- 10 treatment, for example, by addition of the reaction mixture into water followed by extraction with an organic solvent and then concentration of the extract. The isolated compound (a) may be purified by chromatography, recrystallization or the like, if necessary.
15
(2) In a case that R2 is hydrogen;
The compound (a) can be prepared by subjecting the compound (f) to a reducing reaction.
The reducing reaction is usually performed in a 20 solvent.
A solvent used in the reaction includes ether such as diethyl ether or tetrahydrofuran, aromatic hydrocarbon such as toluene or xylene, alcohol such as methanol, ethanol or propanol, water, and a mixture thereof. 25 A reducing agent used in the reaction includes sodium borohydride.
The amount of a reducing agent used in the reaction is usually 0.25 to 2 moles per 1 mole of the compound (f).
The reaction temperature is usually in the range of 0 5 to 50°C. The reaction time is usually in the range of a second to 24 hours.
After completion of the reaction, the compound (a) can be isolated by subjecting the reaction mixture to post- treatment, for example, by addition of the reaction mixture 10 into water followed by extraction with an organic solvent and then concentration of the extract. The isolated compound (a) may be purified by chromatography, recrystallization or the like, if necessary.
15 (3) In a case that R2 is cyano;
The compound (a) can be prepared by reacting the compound (f) with a cyanide salt.
The reaction is usually performed in a solvent.
A solvent used in the reaction includes ether such as 20 diethyl ether or tetrahydrofuran, aromatic hydrocarbon such as toluene or xylene, and a mixture thereof.
A cyanide salt used in the reaction includes tetrabutylammonium cyanide.
The amount of cyanide used in the reaction is usually 25 1 to 10 moles per 1 mole of the compound (f).

such as toluene or xylene, and a mixture thereof.
A base used in the reaction includes an inorganic base such as sodium hydride, sodium carbonate or potassium carbonate, an alkali metal alkoxide such as potassium-t- 5 butoxide, and an organic base such as 4-
dimethylaminopyridine, 1,4-diazabicyclo[2.2.2]octane or 1,8-diazabicyclo[5.4.0]-7-undecene.
The amount of a base used in the reaction is usually 1 to 10 moles per 1 mole of the compound (b).
10 The amount of malononitrile used in the reaction is
usually 1 to 10 moles per 1 mole of the compound (b).
The reaction temperature is usually in the range of - 20 to 100°C. The reaction time is usually in the range of 1 to 24 hours.
15 After completion of the reaction, the compound (d) can
be isolated by subjecting the reaction mixture to post- treatment, for example, by addition of the reaction mixture into water followed by extraction with an organic solvent and then concentration of the extract. The isolated
20 compound (d) may be purified by chromatography, recrystallization or the like, if necessary.
(Reference Process 3)
The compound (d) may be also prepared by the following 25 method:

The reaction may be also performed while water produced by the reaction is removed form the reaction system, if necessary.
After completion of the reaction, the compound (h) can 5 be isolated by subjecting the reaction mixture to post-
treatment, for example, by addition of the reaction mixture into water followed by extraction with an organic solvent and then concentration of the extract. The isolated compound (h) may be purified by chromatography, 10 recrystallization or the like, if necessary.
(Second step)
The compound (d) can be also prepared by reacting the compound (h) with a reducing agent. 15 The reaction is usually performed in a solvent.
A solvent used in the reaction includes alcohol such as methanol, ethanol, isopropyl alcohol or t-butyl alcohol, ether such as diethyl ether or tetrahydrofuran, halogenated hydrocarbon such as 1,2-dichloroethane or chlorobenzene, 20 aromatic hydrocarbon such as toluene or xylene, and a mixture thereof.
A reducing agent used in the reaction includes sodium borohydride, lithium borohydride and diisopropylaluminum hydride.
25 The amount of a reducing agent used in the reaction,

wherein E1, R1 and R2 are as defined above, and E2 represents a leaving group (e.g. chlorine, methoxy, ethoxy, 1-imidazolyl, 1-pyrazolyl, dimethylamino, 1-piperidyl, or N-methyl-N-methoxyamino.
5 That is, the compound (e) can be prepared by reacting
the compound (i) with an organometallic compound represented by R1-M (e.g. an organic magnesium compound such as methylmagnesium iodide, ethylmagnesium bromide, isopropylmagnesium bromide, vinylmagnesium bromide, 10 ethynylmagnesium bromide or dimethylmagnesium, an organic lithium compound such as methyllithium, an organic zinc compound such as diethylzinc, or an organic copper compound such as trifluoromethylcopper) or a reducing agent (e.g. lithium aluminum hydride or diisobutylaluminum hydride). 15 The compound (j) can be prepared by reacting the
compound (i) with an organometallic compound represented by R1-M (e.g. an organic magnesium compound such as
rs
methylmagnesium iodide, ethylmagnesium bromide, isopropylmagnesium bromide, vinylmagnesium bromide, 20 ethynylmagnesium bromide or dimethylmagnesium, an organic lithium compound such as methyllithium, an organic zinc compound such as diethylzinc, or an organic copper compound such as trifluoromethylcopper) or a reducing agent (e.g. lithium aluminum hydride or diisobutylaluminum hydride). 25 In addition, the compound (c) can be prepared by


wherein E1 and E3 are as defined above, R6"1 represents Cl- C5 alkyl optionally substituted with halogen, C3-C6 alkyl optionally substituted with halogen, C2-C5 alkenyl optionally substituted with halogen, or alkynyl optionally substituted with halogen, R5"2 independently represents Cl- C5 alkyl optionally substituted with halogen, C3-C6 cycloalkyl optionally substituted with halogen, or hydrogen, and R6"2 represents C1-C5 alkyl optionally substituted with halogen, C2-C5 alkenyl optionally substituted with halogen, C2-C5 alkynyl optionally substituted with halogen, C3-C6 cycloalkyl optionally substituted with halogen, (C1-C5 alkyloxy optionally substituted with halogen)C1-C3 alkyl, C1-C5 alkylsulfinyl optionally substituted with halogen, C1-C5 alkylsulfonyl optionally substituted with halogen, C2-C6 alkylcarbonyl optionally substituted with halogen, C2-C5 alkoxycarbonyl optionally substituted with halogen, a group represented by C (=X5) NR12R13 (wherein X5, R12 and R13 are as defined above) or a group represented by (CH2)mQ (wherein m and Q are defined above).
(Reference Process 8)
Among the compound (j), the compound (j-3) can be prepared, for example, according to a route shown in the following scheme:






(Reference Process 17)
The compounds (c) , (e), (i) and (j) in which X1 is nitrogen atom, each of X2, X3 and X4 is CR6 and Z represents 5 an oxygen atom, which are isoxazole, can be synthesized according to a method described in Houben-Weyl, Methoden der Organischen Chemi, Hetarene III, Teil.l, p.45-204.
(Reference Process 18) 10 The compounds (c), (e) , (i) and (j) in which X1 is
nitrogen, X2, X3 and X4 each are CR5 and Z represents sulfur, which are isothiazole, can be synthesized according to a method described in Houben-Weyl, Methoden der Organischen Chemi, Hetarene III, Teil.l, p.668-788.
15
(Reference Process 19)
The compounds (c), (e), (i) and (j) in which X2 is nitrogen, X1, X3 and X4 each are CR5 and Z represents NR6, which are imidazole, can be synthesized according to a 20 method described in Houben-Weyl, Methoden der Organischen Chemi, Hetarene III, Teil.3, p.1-192.
(Reference Process 20)
The compound (c), (e), (i) and (j) in which X2 is nitrogen, X1, X3 and X4 each are CR5 and Z represents oxygen,
which are 1,3-oxazole, can be synthesized according to a method described in Houben-Weyl, Methoden der Organischen Chemi, Hetarene III, Teil.l, p.891-1012.
5 (Reference Process 21)
The compounds (c) , (e) , (i) and (j) in which X2 is nitrogen, X1, X3 and X4 each are CR5 and Z represents sulfur, which are 1,3-thiazole, can be synthesized according to a method described in Houben-Weyl, Methoden der Organischen 10 Chemi, Hetarene III, Teil.3, p.1-361.
(Reference Process 22)
The compounds (c) , (e), (i) and (j) in which X1 and X3 are nitrogen, X2 and X4 each are CR5 and Z represents oxygen, 15 which are 1,2,4-oxadiazole, can be synthesized according to a method described in Houben-Weyl, Methoden der Organischen Chemi, Hetarene III, Teil.3, p.409-518.
(Reference Process 23) 20 The compounds (c), (e), (i) and (j) in which X2 and X3
are nitrogen, X1 and X4 each are CR5 and Z represents oxygen, which are 1,3,4-oxadiazole, can be synthesized according to a method described in Houben-Weyl, Methoden der Organischen Chemi, Hetarene III, Teil.3, p.526-630.
(Reference Prcess 24)
The compounds (c) , (e), (i) and (j) in which X1 and X3 are nitrogen, X2 and X4 each are CR5 and Z represents sulfur, which are 1,2,4-thiadiazole, can be synthesized according 5 to a method described in Houben-Weyl, Methoden der Organischen Chemi, Hetarene III, Teil.4, p.105-148.
(Reference Process 25)
The compounds (c), (e), (i) and (j) in which X1 and X4 10 are nitrogen, X2 and X3 each are CR5 and Z represents sulfu, which are 1,2,5-thiadiazole, can be synthesized according to a method described in Houben-Weyl, Methoden der Organischen Chemi, Hetarene III, Teil.4, p.152-168.
15 (Reference Process 26)
The compounds (c), (e), (i) and (j) in which X2 and X3 are nitrogen, X1 and X4 each are CR5 and Z represents sulfur, which are 1,3,4-thiadiazole, can be synthesized according to a method described in Houben-Weyl, Methoden der 20 Organischen Chemi, Hetarene III, Teil.4, p.189-298.
(Reference Process 27)
The compounds (c) , (e) , (i) and (j) in which X1 and X2 are nitrogen, X3 and X4 each are CR5 and Z represents NR6, 25 which are 1,2,3-triazole, can be synthesized according to a

method described in Houben-Weyl, Methoden der Organischen Chemi, Hetarene III, Teil.4, p.305-389.
(Reference Process 28)
The compounds (c) , (e) , (i) and (j) in which X1 and X3 are nitrogen, X2 and X4 each are CR5 and Z represents NR6, which are 1,2,4-triazole, can be synthesized according to a method described in Houben-Weyl, Methoden der Organischen Chemi, Hetarene III, Teil.4, p.479-586.
Pests against which the present compound has controlling effect include harmful arthropods such as insects and mites, and harmful nematodes. More specifically, examples thereof are listed below.
15
Hemiptera:
Delphacidae such as Laodelphax striatellus, Nilaparvata lugens, Sogatella furcifera and the like,
Deltocephalidae such as Nephotettix cincticeps, Nephotettix 20 virescens and the like,
Aphididae such as Aphis gossypii, Myzus persicae and the like,
10
Pentatomidae and Alydidae, such as Nezara antennata, Riptortus clavetus, Plautia stall, Halyomorpha mista, 25 Eysarcoris lewisi, Eysarcoris parvus, and the like,

Aleyrodidae such as Trialeurodes vaporariorum, Bemisia argentifolii and the like,
Diaspididae, Coccidae and Margarodidae, such as Aonidiella aurantii, Comstockaspis perniciosa, Unaspis citri, 5 Ceroplastes rubens, Icerya purchasi and the like, Tingidae,
Psyllidae, and the like; Lepidoptera:
10 Pyralidae such as Chilo suppressalis, Cnaphalocrocis
medinalis, Notarcha derogata, Plodia interpunctella and the like,
Noctuidae such as Spodoptera litura, Pseudaletia separata, Trichoplusia spp., Heliothis spp., Helicoverpa spp. and the 15 like,
Pieridae such as Pieris rapae and the like, Tortricidae such as Adoxophyes spp., Grapholita molesta, Cydia pomonella and the like,
Carposinidae such as Carposina niponensis and the like, 20 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 gossypiella and the like, 25 Arctiidae such as Hyphantria cunea and the like,
Tineidae such as Tinea translucens, Tineola bisselliella and the like;
Diptera:
Culicidae such as Culex pipiens pallens, Culex tritaeniorhynchus, Culex quinquefasciatus and the like, Aedes spp. such as Aedes aegypti, Aedes albopictus and the like,
Anopheles spp. such as Anopheles sinensis and the like, Chironomidae,
Muscidae such as Musca domestica, Muscina stabulans and the like,
Calliphoridae, Sarcophagidae, Fanniidae,
Anthomyiidae such as Delia platura, Delia antiqua and the like,
Tephritidae,
Drosophilidae,
Psychodidae,
Simuliidae,
Tabanidae,
Stomoxys spp.,
Agromyzidae, and the like;
Coleoptera:
Corn rootworms such as Diabrotica virgifera virgifera, Diabrotica undecimpunctata howardi and the like, Scarabaeidae such as Anomala cuprea, Anomala rufocuprea and 5 the like,
Rhynchophoridae, Curculionidae and Bruchidae, such as Sitophilus zeamais, Lissorhoptrus oryzophilus, Callosobruchus chienensis and the like,
Tenebrionidae such as Tenebrio molitor, Tribolium castaneum 10 and the like,
Chrysomelidae such as Oulema oryzae, Aulacophora femoralis, Phyllotreta striolata, Leptinotarsa decemlineata and. the like,
Anobiidae,
15 Epilachna spp. such as Epilachna vigintioctopunctata and the like, Lyctidae, Bostrychidae, Cerambycidae, 20 Paederus fuscipes, and the like;
Blattaria: 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, Bethylidae,
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 schlechtendali, and the like,
Tarsonemidae such as Polyphagotarsonemus latus, and the like,
Tenuipalpidae, Tuckerellidae,
5 Ixodidae such as Haemaphysalis longicornis, Haemaphysalis flava, Dermacentor variabilis, Ixodes ovatus, Ixodes persulcatus, Boophilus microplus, and the like, ^ Acaridae such as Tyrophagus putrescentiae, and the like,
Epidermoptidae such as Dermatophagoides farinae, 10 Dermatophagoides ptrenyssnus, and the like,
Cheyletidae such as Cheyletus eruditus, Cheyletus malaccensis, Cheyletus moorei, and the like, Dermanyssidae, and the like;
15 Araneae: Chiracanthium japonicum, Latrodectus hasseltii, and the like;
Chilopoda: Thereuonema hilgendorfi, Scolopendra subspinipes, and the like;
20
Diplopoda: Oxidus gracilis, Nedyopus tambanus, and the like;
Isopoda: Armadillidium vulgare, and the like;
Gastropoda: Limax marginatus, Limax flavus, and the like;
Nematoda: Pratylenchus coffeae, Pratylenchus fallax, Heterodera glycines, Globodera rostochiensis, Meloidogyne hapla, Meloidogyne incognita, and the like.
Although the pesticidal composition of the present invention may be the present compound itself, it is usually formulated into a preparation by mixing with a solid carrier, a liquid carrier and/or a gaseous carrier and, further, if necessary, adding a surfactant and other adjuvants for formulation. That is, the pesticidal composition of the present invention usually contains the present compound and further contains an inert carrier. Such a preparation includes an emulsion, an oil, a shampoo preparation, a flowable preparation, a powder, a wettable agent, a granule, a paste, a microcapsule, a foam, an aerosol, a carbon dioxide gas preparation, a tablet, and a resin preparation. These preparations may be used in the form of a poison bait, a pesticide coil, an electric pesticide mat, a smoking preparation, a fumigant, or a sheet.
A preparation of the pesticidal composition of the present invention contains usually 0.1 to 95% by weight of the present compound.
A solid carrier used for formulation includes finely- divided powder or granules of clay (e.g., kaolin clay, diatomaceous earth, bentonite, Fubasami clay, acid clay, etc.), synthetic hydrated silicon oxide, talc, ceramics, 5 other inorganic minerals (e.g., sericite, quartz, sulfur,
activated carbon, calcium carbonate, hydrated silica, etc.) or chemical fertilizers (e.g., ammonium sulfate, ammonium phosphate, ammonium nitrate, ammonium chloride, urea, etc.).
A liquid carrier includes aromatic or aliphatic 10 hydrocarbons (e.g., xylene, toluene, alkylnaphthalene,
phenylxylylethane, kerosine, gas oil, hexane, cyclohexane, etc.), halogenated hydrocarbons (e.g., chlorobenzene, dichloromethane, dichloroethane, trichloroethane, etc.), alcohols (e.g., methanol, ethanol, isopropyl alcohol, 15 butanol, hexanol, benzyl alcohol, ethylene glycol, etc.),
ethers (e.g., diethyl ether, ethylene glycol dimethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, propylene glycol monomethyl ether, tetrahydrofuran, dioxane, etc.), esters (e.g., ethyl 20 acetate, butyl acetate, etc.), ketones (e.g., acetone,
methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, etc.), nitriles (e.g., acetonitrile, isobutyronitrile, etc.), sulfoxides (e.g., dimethyl sulfoxide, etc.), acid amides (e.g., N,N-dimethylformamide, N,N-dimethylacetamide, 25 etc.), vegetable oil (e.g., soybean oil, cottonseed oil,
etc.), vegetable essential oils (e.g., orange oil, hyssop oil, lemon oil, etc.), and water.
A gaseous carrier includes butane gas, chlorofluoro carbon gas, liquefied petroleum gas (LPG), dimethyl ether, 5 and carbonic acid gas.
A surfactant includes alkyl sulfate ester salts, alkyl sulfonates, alkyl aryl sulfonates, alkyl aryl ethers and f**^ polyoxyethylenated products thereof, polyethylene glycol
ethers, polyvalent alcohol esters and sugar alcohol 10 derivatives.
Other adjuvants for formulation include binders, dispersants and stabilizers, specifically, for example, casein, gelatin, polysaccharides (e.g., starch, gum arabic, cellulose derivatives, alginic acid, etc.), lignin 15 derivatives, bentonite, sugars, synthetic water-soluble polymers (e.g., polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acid, etc.), PAP (acidic isopropyl phosphate), BHT (2,6-di-t-butyl-4-methylphenol) , BHA (a mixture of 2-t- butyl-4-methoxyphenol and 3-t-butyl-4-methoxyphenol), 20 vegetable oils, mineral oils, fatty acids and fatty acid esters.
A base material for a resin preparation includes polyvinyl chloride and polyurethane. A plasticizer such as phthalic acid ester (e.g., dimethyl phthalate, dioctyl 25 phthalate, etc.), adipic acid ester or stearic acid may be
added to these base materials, if necessary.
The resin preparation can be obtained by kneading the present compound into the base material by using a conventional kneader, followed by molding such as injection molding, extrusion molding or press molding. The resulting resin preparation may be formed into the shape of a plate, a film, a tape, a net, a string or the like via a further step of molding, cutting, or the like, if necessary. These resin preparations may be made into an animal collar, an animal ear tag, a sheet preparation, a lead, or a horticultural post.
A base material of a poison bait includes cereal powder, vegetable oil, sugar and crystalline cellulose. An antioxidant such as dibutylhydroxytoluene or nordihydroguaiaretic acid, a preservative such as dehydroacetic acid, an agent for preventing children or pets from erroneously eating such as hot pepper powder, and a pest-attractive perfume such as cheese perfume, onion perfume or peanut oil may be added to the base material, if necessary.
The pesticidal composition of the present invention is used by applying it to pests directly and/or habitats of pests (e.g., plants, animals, soil, etc.).
When the pesticidal composition of the present
invention is used for controlling pests in agriculture and forestry, the application amount is usually 1 to 100,000 g/ha, preferably 10 to 1,000 g/ha of the active ingredient. When the pesticidal composition of the present invention is 5 the form of an emulsion, a wettable agent, a flowable agent, or a microcapsule, it is usually used as a dilution with water containing 1 to 10,000 ppm of the active ingredient. fy When the pesticidal composition of the present invention is
the form of powder or a granule, it is usually used as it 10 is. These preparations may be sprayed as they are on
plants to be protected from pests. In addition, soil can be treated with these preparations to control pests living in the soil. Seedbeds before planting or planting holes or plant feet on planting can be also treated with these 15 preparations. Further, a sheet preparation of the
pesticidal composition of the present invention may be applied by winding it around plants, locating it near plants, laying it on the soil surface at the plant feet, or the like.
20 When the pesticidal composition of the present
invention is used for a control of pests of epidemic, the application amount is usually 0.001 to 100 mg/m3 of the active ingredient for application to space, and 0.001 to 100 mg/m2 of the active ingredient for application to a 25 plane. The pesticidal composition in the form of an
emulsion, wettable agent or a flowable agent is usually applied as a dilution with water containing 0.01 to 10,000 ppm of the active ingredient. The pesticidal composition in the form of an oil, an aerosol, a smoking preparation or 5 a poison bait is usually applied as it is.
When the pesticidal composition of the present invention is used for controlling parasites living outside f*^ of a livestock such as a cow, a horse, a pig, a sheep, a
goat or a chicken, or a small animal such as a dog, a cat, 10 a rat or a mouse, it can be used for said animal by a known method in the veterinary filed. Specifically, when systemic control is intended, the pesticidal composition is administered, for example, as a tablet, a mixture with feed, a suppository or an injection (e.g., intramuscularly, 15 subcutaneously, intravenously, intraperitoneally, etc.). When non-systemic control is intended, a method of using the pesticidal composition of the present invention includes spraying, pour-on treatment or a spot-on treatment with the pesticidal composition in the form of an oil or an 20 aqueous liquid, washing an animal with the pesticidal composition in the form of a shampoo preparation, and attachment of a collar or a ear tag made of the pesticidal composition in the form of a resin preparation to an animal. When administered to an animal, the amount of the present 25 compound is usually in the range of 0.01 to 1,000 mg per 1
kg body weight of the animal.
The pesticidal composition of the present invention may be used in admixture or combination with other insecticides, nematocides, acaricides, germicides, herbicides, plant growth regulators, synergists, fertilizers, soil conditioners, animal feed, and the like.
The active ingredient of such insecticide or acaricide includes 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; organic phosphorus compounds such as dichlorvos, fenitrothion, cyanophos, profenofos, sulprofos, phenthoate, isoxathion, tetrachlorvinphos, fenthion, chlorpyriphos, diazinon, acephate, terbufos, phorate, chlorethoxyfos, fosthiazate, ethoprophos, cadusafos and methidathion; carbamate compounds such as propoxur, carbaryl, metoxadiazone, fenobucarb, methomyl, thiodicarb, alanycarb, benfuracarb, oxamyl, aldicarb and methiocarb; benzoylphenylurea compounds such as lufenuron, chlorfluazuron, 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 dinotefuran; N-phenylpyrazole 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; fluacrypyrim; etoxazole; fenazaquin; acequinocyl; hexythiazox; clofentezine; fenbutatin oxide; dicofol, propargite; abamectin; milbemectin; amitraz; cartap; bensultap; thiocyclam; endosulfan; spirodiclofen; spiromesifen; and azadirachtin.
The active ingredient of such germicide includes strobilurin compounds such as azoxystrobin; organic phosphorus compounds such as tolclofos-methyl; azole compounds such as triflumizole, pefurazoate and difenoconazole; fthalide; flutolanil; validamycin; probenazole; diclomezine; pencycuron; dazomet; kasugamycin; IBP; pyroquilon; oxolinic acid; tricyclazole; ferimzone; mepronil; EDDP; isoprothiolane; carpropamid; diclocymet;
furametpyr; fludioxonil; procymidone; and diethofencarb. Examples
The present invention will be explained in more detail by the following Production Examples, Formulation Examples and Experimental Examples, but the present invention is not limited to them.
First, Production Examples of the present compound will be described.
Production Example 1
1.32 g of 3-t-butyl-5-(chloromethyl)-lH-pyrazole hydrochloride and 1.13 g of (3,3,3-
trifluoropropyl)malononitrile were dissolved in 21 ml of N,N-dimethylformamide, and 1.93 g of potassium carbonate was then added under ice-cooling. The mixture was stirred at room temperature for 3 hours. After water was added, the reaction mixture was extracted with methyl-t-butyl ether. The organic layer was washed with water, dried over anhydrous magnesium sulfate, filtered, and then concentrated under reduced pressure. The residue was recrystallized from hexane-ethyl acetate to obtain 1.35 g of a compound represented by the following formula:























































6-(tetrahydro-2H-pyran-2-yloxy)-4-hexyn-3-one which is prepared by a method described in J.Org.Chem.,67,9200 (2002), by the following method.
4.49 g of 2,2-dimethyl-6-(tetrahydro-2H-pyran-2- 5 yloxy)-4-hexyn-3-one was dissolved in 20 ml of methanol,
and 1.30 g of sodium methoxide and 1.53 g of hydroxylamine hydrochloride were added. The mixture was stirred at 70°C f*^ for 2 hours. The reaction mixture was cooled to room
temperature and then adjusted to pH 2 with concentrated 10 hydrochloric acid. The mixture was stirred at room
temperature for 18 hours. After aqueous saturated sodium hydrogen carbonate was added, the reaction mixture was extracted with ethyl acetate. The extract was washed with aqueous saturated sodium chloride, dried over anhydrous 15 sodium sulfate and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 1.12 g of (3-t-butyl-isoxazol-5- yl)methanol.
1H-NMR(CDC13, TMS, 8(ppm) ) : 1.33(9H, s), 4.74(2H, s), 20 6.16(1H, s)
Reference Production Example 4-2 3-t-Butyl-5-(chloromethyl)-isoxazole hours under ice-cooling. The reaction mixture was added to 0.5 N hydrochloric acid under ice-cooling and then extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, filtered and then 5 concentrated under reduced pressure. The residue was
subjected to silica gel column chromatography to obtain 0.32 g of [(2-ethylthio-l-methylimidazol-5- yl)methyl]malononitrile.
1H-NMR(CDC13, TMS, 5(ppm)): 1.31{3H, t), 3.06(2H, q), 10 ' 3.34(2H, d), 3.59(3H, s), 3.93(1H, t) , 7.14(1H, s)
Then, Formulation Examples will be described. The term "part" represents a part by weight. In addition, the present compound will be designated by the aforementioned 15 compound numbers.
Formulation Example 1
25
9 Parts of any one of the present compounds (1) to (70) is dissolved in 37.5 pats of xylene and 37.5 parts of 20 N,N-dimethylformamide. Thereto 10 parts of polyoxyethylene styryl phenyl ether and 6 parts of calcium dodecylbenzenesulfonate are added and mixed by stirring thoroughly to obtain an emulsion.
Formulation Example 2

5 Parts of SORPOL 5060 (registered trade name for TOHO Chemical Industry Co., LTD.) is added to 40 parts of any one of the present compounds (1) to (70) and mixed thoroughly. Then, 32 parts of CARPLEX #80 (registered 5 trade name for Shionogi & Co., Ltd., synthetic anhydrous silicon oxide fine powder) and 23 parts of 300 mesh diatomaceous earth are added thereto and mixed with a juice mixer to obtain a wettable preparation.
10 Formulation Example 3
3 Parts of any one of the present compounds (1) to (70), 5 parts of synthetic hydrous silicon oxide fine powder, 5 parts of sodium dodecylbenzenesulfonate, 30 parts of bentonite and 57 parts of clay are mixed by stirring 15 thoroughly. To this mixture an appropriate amount of water is added. The mixture is further stirred, granulated with a granulator, and then air-dried to obtain a granule.
Formulation Example 4 20 4.5 Parts of any one of the present compounds (1) to
(70), 1 part of synthetic hydrous silicon oxide fine powder, 1 part of Dorires B (manufactured by Sankyo) as a flocculant, and 7 parts of clay are mixed thoroughly with a mortar and then by stirring with a juice mixer. To the 25 resultant mixture 86.5 parts of cut clay is added and mixed

by stirring thoroughly to obtain a powder.
Formulation Example 5
10 Parts of any one of the present compounds (1) to 5 (70), 35 parts of white carbon containing 50 parts of
polyoxyethylene alkylether sulfate ammonium salt, and 55 parts of water are mixed and then finely-divided by a wet grinding method to obtain a preparation.
10 Formulation Example 6
0.5 Parts of any one of the present compounds (1) to (70) is dissolved in 10 parts of dichloromethane. This solution is mixed with 89.5 parts of Isopar M (isoparaffin registered trade name for Exxon Chemical) to obtain an oil
15
Formulation Example 7
0.1 Parts of any one of the present compounds (1) to (70) and 49.9 parts of NEO-THIOZOL (Chuo Kasei Co., Ltd.) are placed in an aerosol can. An aerosol valve is fitted 20 to the can and the can is then charged with 25 parts of
25
dimethyl ether and 25 parts of LPG. The can is shaken and an actuator is fitted to the can to obtain an oily aerosol
Formulation Example 8
An aerosol container is charged with a mixture of 0.6

parts of any one of the present compounds (1) to (70), 0.01 part of BHT, 5 parts of xylene, 3.39 parts of a deodorized kerosine and 1 part of an emulsifying agent [Atmos 300 (registered trade name for Atmos Chemical Ltd.)] and 50 parts of distilled water. A valve part is attached to the container and the container is then charged with 40 parts of a propellant (LPG) through the valve under increased pressure to obtain an aqueous aerosol.
Then, it will be demonstrated by Experimental Examples that the present compound is effective as the active ingredient of a pesticidal composition. The present compound will be designated by the aforementioned compound numbers.
Experimental Example 1
Preparations of the present compounds (1), (2), (3), (4), (5), (6), (8), (9), (11), (12), (13), (15), (16), (17), (18), (19), (21), (22), (23), (24), (25), (26), (27), (29), (31), (32), (34), (35), (36), (37), (38), (39), (40), (41), (42), (43), (45), (47), (50), (52), (53), (54), (62), (64), (65), (67) and (68) obtained according to Formulation Example 5 were diluted so that the active ingredient concentration was 500 ppm to prepare experimental pesticidal solutions.
In a polyethylene cup, 50 g of molding Bonsoru 2 (manufactured by Sumitomo Chemical Co., Ltd.) was put and 10 to 15 seeds of rice were planted. The rice plants were grown until the second foliage leaf was developed and then 5 cut into the same height of 5 cm. The experimental
pesticidal solution prepared as described above was sprayed in an amount of 20 ml/cup on the rice plants. After the pesticidal solution sprayed onto the rice plants was dried, the rice plants were put into a plastic cup for preventing 10 the escape of test pests. 30 first-instar larvae of
Nilaparvata lugens were released into the plastic cup and the cup was sealed with a lid and then left in a greenhouse (25°C) . On the sixth day after release of Nilaparvata lugens larvae, the number of parasitic Nilaparvata lugens 15 on the rice plants was examined.
As a result, in treatments with the present compounds (1), (2), (3), (4), (5), (6), (8), (9), (11), (12), (13), (15), (16), (17), (18), (19), (21), (22), (23), (24), (25), (26), (27), (29), (31), (32), (34), (35), (36), (37), (38), 20 (39), (40), (41), (42), (43), (45), (47), (50), (52), (53), (54), (62), (64), (65), (67) and (68), the number of the parasitic pest was 3 or less.
Experimental Example 2 25 Preparations of the present compounds (1), (2), (4),
(5), (6), (8), (11), (15), (17), (19), (24), (25), (27), (35), (36), (37), (38), (39), (40), (41), (42), (45), (47), (48), (49), (50), (52), (53), (54), (62), (65), (66), (67) and (7 0) obtained according to Formulation Example 5 were 5 diluted with water so that the active ingredient concentration was 500 ppm to prepare experimental pesticidal solutions.
In a polyethylene cup cucumber was planted and grown until the first foliage leaf was developed. About 20 Aphis 10 gossypii were made to parasitize the cucumber. One day
after, the pesticidal solution was sprayed in an amount of 20 ml/cup on the cucumber. Sixth days after, the number of the Aphis gossypii was examined.
As a result, in treatments with the present compounds 15 (1), (2), (4), (5), (6), (8), (11), (15), (17), (19), (24), (25), (27), (35), (36), (37), (38), (39), (40), (41), (42), (45), (47), (48), (49), (50), (52), (53), (54), (62), (65), (66), (67) and (70), the number of the parasitic pest six days after the treatments was 3 or less.
20
Experimental Example 3
Preparations of the present compounds (1), (2), (3), (4), (5), (6), (8), (9), (10), (11), (12), (13), (14), (15), (16), (17), (18), (19), (21), (22), (23), (24), (25), (26), 25 (27), (31), (34), (35), (36), (37), (38), (39), (40), (42),
(47), (50), (52), (54), (66), (67) and (68) obtained according to Formulation Example 5 were diluted with water so that the active ingredient concentration was 500 ppm to prepare experimental pesticidal solutions.
5 A filter paper having a diameter of 5.5 cm was spread
on the bottom of a polyethylene cup having a diameter of 5.5 cm and 0.7 ml of the experimental pesticidal solution was added dropwise onto the filter paper. As a bait 30 mg of sucrose was uniformly placed on the filter paper. Into 10 the polyethylene cup, 10 female Musca domestica imagoes
were released and the cup was sealed with a lid. After 24 hours, the number of surviving Musca domestica was examined and the death rate of the pest was calculated.
As a result, in treatments with the present compounds 15 (1), (2), (3), (4), (5), (6), (8), (9), (10), (11), (12),
(13), (14), (15), (16), (17), (18), (19), (21), (22), (23), (24), (25), (26), (27), (31), (34), (35), (36), (37), (38), (39), (40), (42), (47), (50), (52), (54), (66), (67) and (68), the death rate of the pest was 90% or more.
20
Experimental Example 4
Preparations of the present compounds (2), (4), (5), (6), (8), (9), (11), (12), (13), (15), (17), (18), (19), (21), (24), (25), (26), (27), (35), (36), (37), (38), (40), 25 (41), (42), (47), (50), (52), (54), (62), (64), (65), (66)
and (68) obtained according to Formulation Example 5 were diluted with water so that the active ingredient concentration was 500 ppm to prepare experimental pesticidal solutions;
5 A filter paper having a diameter of 5.5 cm was spread
on the bottom of a polyethylene cup having a diameter of 5.5 cm and 0.7 ml of the experimental pesticidal solution was added dropwise onto the filter paper. As a bait 30 mg of sucrose was uniformly placed on the filter paper. Into 10 the polyethylene cup, two male Blattalla germanica imagoes were released and the cup was sealed with a lid. After 6 days, the number of surviving Blattalla germanica was examined and the death rate of the pest was calculated.
As a result, in treatments with the present compounds
15 (2) , (4), (5), (6) , (8), (9) , (11) , (12) , (13) , (15) , (17)
(18), (19), (21), (24) , (25) , (26) , (27) , (35) , (36) , (37)
(38) , (40), (41), (42) , (47) , (50) , (52) , (54) , (62) , (64)
(65), (66) and (68), the death rate of the pest was 100%.

20 Experimental Example 5
Preparations of the present compounds (1), (2), (4), (5), (6), (8), (9), (11), (12), (13), (14), (15), (16), (17), (18), (19), (21), (22), (23), (24), (25), (26), (27), (31), (33), (34), (35), (36), (37), (38), (39), (40), (42), 25 (43), (47), (48), (50), (52), (53), (54), (62), (64), (65),
(66), (67), (68) and (70) obtained according to Formulation Example 5 were diluted with water so that the active ingredient concentration was 500 ppm to prepare experimental pesticidal solutions.
5 0.7 ml of the experimental pesticidal solution was
added to 100 mL of ion-exchanged water (active ingredient concentration: 3.5 ppm). Into the solution, 20 last-instar larvae of Culex pipiens pallens were released. After one day, the surviving number was examined and the death rate 10 of the pest was calculated.
As a result, in treatments with the present compounds (1), (2), (4), (5), (6), (8), (9), (11), (12), (13), (14),
(15) , (16) , (17) , (18) , (19) , (21), (22), (23) , (24), (25) ,
(26), (27), (31), (33), (34) , (35), (36), (37), (38), (39) ,
15 (40) , (42), (43) , (47), (48) , (50), (52), (53), (54), (62),
(64) , (65), (66) , (67), (68) and (70), the death rate of

the pest was 95% or more.
Industrial Applicability 20 The malononitrile compound represented by the formula
(I) is useful as an active ingredient of a pesticidal composition.

Documents:

2573-CHENP-2006 CORRESPONDENCE OTHERS 21-12-2011.pdf

2573-CHENP-2006 FORM-13 16-05-2012.pdf

2573-chenp-2006 abstract.pdf

2573-CHENP-2006 AMENDED CLAIMS 16-05-2012.pdf

2573-CHENP-2006 AMENDED PAGES OF SPECIFICATION 16-05-2012.pdf

2573-CHENP-2006 AMENDED PAGES OF SPECIFICATION. 1 16-05-2012.pdf

2573-chenp-2006 claims.pdf

2573-chenp-2006 correspondence others.pdf

2573-chenp-2006 description (complete) -1.pdf

2573-chenp-2006 description (complete) -2.pdf

2573-chenp-2006 description (complete).pdf

2573-CHENP-2006 EXAMINATION REPORT REPLY RECEIVED 16-05-2012.pdf

2573-chenp-2006 form-1.pdf

2573-CHENP-2006 FORM-13 14-01-2008.pdf

2573-chenp-2006 form-18.pdf

2573-CHENP-2006 FORM-3 16-05-2012.pdf

2573-chenp-2006 form-3.pdf

2573-chenp-2006 form-5.pdf

2573-CHENP-2006 OTHER PATENT DOCUMENT 16-05-2012.pdf

2573-chenp-2006 pct.pdf

2573-CHENP-2006 POWER OF ATTORNEY 16-05-2012.pdf

2573-chenp-2006 power of attorney.pdf


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Patent Number 254581
Indian Patent Application Number 2573/CHENP/2006
PG Journal Number 47/2012
Publication Date 23-Nov-2012
Grant Date 21-Nov-2012
Date of Filing 13-Jul-2006
Name of Patentee SUMITOMO CHEMICAL COMPANY, LIMITED
Applicant Address 27-1, Shinkawa 2-chome, Chuo-ku, Tokyo, 1048260
Inventors:
# Inventor's Name Inventor's Address
1 MITSUDERA, Hiromasa 31-8, Machikaneyama-cho, Toyonaka-shi, Osaka, 5600043
2 OTAKA, Ken 11-18, Kashima-machi Kubo Aza-sorimachi, Iwaki-shi, Fukushima, 9718144
3 FUJIWARA, Jun 6-15, Takezono-cho, Ashiya-shi, Hyogo, 6590055
PCT International Classification Number C07D231/12,261/08,275/02,263/32,277/32
PCT International Application Number PCT/JP2005/000629
PCT International Filing date 2005-01-13
PCT Conventions:
# PCT Application Number Date of Convention Priority Country
1 2004-009149 2004-01-16 Japan