Indian Patents
Title of Invention

ORGANIC SULFUR COMPOUNDS AND USE THEREOF
Abstract ABSTRACT A compound Given by the fomula [1): (I) has an excellent controlling activity against noxious arthropods.
Full Text DESCRIPTION ORGANIC SULFUR COMPOUNDS AND USE THEREOF
Technical Field
The present invention relates to organic sulfur compounds and noxious arthropod controlling use thereof.
Background Art
Many arthropods controlling agents have been developed and practically used.
Disclosure of Invention
The present invention provides novel compounds having an excellent activity against noxious arthropods.
Namely, the present invention provides an organic sulfur compound given by the following formula [I]:

wherein
R1 represents a C3-C6 fluoroalkyl group,
R2 represents a cyano group, a group represented by C (=0)R
or a group represented by C(=S)R ,
R3 represents a hydrogen atom, a halogen atom or a C1-C4
alkyl group,
R4 represents a C1-C5 fluoroalkyl group,
R5 and R6 independently represent a C1-C4 alkoxy group, an
amino group optionally substituted by one or two C1-C4 alkyl
group(s) or a C2-C5 cyclic amino group.

n represents 0, 1 or 2;
(may refer as the present compound, hereinafter), a noxious arthropod controlling agent comprising the present compound and an inert carrier and a method for controlling noxious arthropods applying an effective amount of the present compound to noxious arthropods or at a habitat of noxious arthropods.
Mode of Carrying Out the Invention
In the present invention, the mention of C1-C4 and the like means the total number of carbon atoms which comprises each substituents. And in the present invention, the mention of fluoroalkyl group means an alkyl group substiuted one or more fluorine atom[s) are substituted at carbon atoms.
Examples of C3-C6 fluoroalkyi group represented by R1 in the formula (I) includes
C3 fluoroalkyi group such as 2--fluoropropyl group, 2,2-difluoropropyl group, 3-fluoropropyl group, 3,3-difluoropropyl group, 3,3,3-trifluoropropyl group, 2,2,3,3,3-pentafluoropropyl group, 2,2,3,3-tetrafluoropropyl group and 2,2,2-trifluoro-(1-trifluoromethyl)ethyl group; C4 fluoroalkyi group such as 2-fluorobutyl group, 2,2-difluorobutyl group, 3-fluorobutyl group, 3,3-difluorobutyl group, 4-fluorobutyl group, 4,4-difluorobutyl group, 4,4,4-rrifluorobutyl group, 3,3,4,4,4-pentafiuorobutyl group, 2, 2, 3, 4, 4-pentaf 1-uorobutyl group and 2,2,3,3,4,4,4-heptafluorobutyl group;

C5 fluoroalkyl group such as 2-fluoropentyl group, 2,2-
difluoropentyl group, 3-fluoropentyl group, 3,3-
difluoropentyl group, 4-fluoropentyl group, 4,4-
difluoropentyl group, 5-fluoropentyl group, 5,5-
difluoropentyl group, 5,5,5-trifluoropentyl group,
4,4,5,5,5-pentafluoropentyl group, 3,3,4,4,5,5,5-
heptafluoropentyl group, 2,2,3,3,4,4,5,5-octafluoropentyl
group and 2,2,3,3,4,4,5,5,5-nonafluoropentyl group;
C6 fluoroalkyl group such as 2-fluorohexyl group, 2,2-
difluorohexyl group, 3-fluorohexyl group, 3,3-difluorohexyl
group, 4-fluorohexyl group, 4,4-difluorohexyl group, 5-
fluorohexyl group, 5,5-difluorohexyl group, 6-fluorohexyl
group, 6,6-difluorohexyl group, 6, 6,6-trifluorohexyl group,
5,5,6,6,6-pentsfluorohexyl group, 4,4,5,5,6,6,6-
heptafluorohexyl group, 3,3,4,4,5,5,6,6,6-nonafluorohexyl
group and 2,2,3,3,4,4,5,5,6,6,6-undecafluorohexyl group.
Examples of C1-C5 fluoroalkyl group represented by R' in the formula (I) includes
C1-C2 fluoroalkyl group such as fluoromethyl group, difluoromethyl group, trifluoromethyl group, 1-fluoroethyl group, 2-fluoroethyl group, 1,1-difluoroethyl group, 2,2-fluoroethyl group, 2,2,2-trifluoroethyl group and 1,1,2,2,2-pentafluoroethyl group;
C3 fluoroalkyl group such as 1-fluoropropyl group, 1,1-difluoropropyl group, 2-fluoropropyl group, 2,2-difluoropropyl group, 3-fluoropropyl group, 3,3-difluoropropyl group, 3,3,3-trifluoropropyl group, 1,1,2,2,3,3,3-heptafluoropropyl group, 2,2,3,3,3-

pentafluoropropyl group, 2,2,2-trifluoro-(1-crifluoromethyDethyl group, 1, 2, 2, 2-tetraf luoro-(1-trifluoromethyl)ethyl group and 2, 2, 3, 3-tetrafluoroprpyl group;
C-S fluoroalkyl group such as 1-fluorobutyl group, 1,1-
difluorobutyl groups 2-fluorobutyl group, 2,2-difluorobutyl
group, S-fluorobutyl group, 3,3-difluorobutyl group, 4-
fluorobutyl group, 4,4-difluorobutyl group, 4,4,4-
trifluorobutyl group, 3,3,4,4,4-pentafluorobutyl group,
2,2,3,4,4-pentafluorobutyl group and 2,2,3,3,4,4,4-
heptafluorobutyl group;
C5 fluoroalkyl group such as 1-fluoropentyl group, 1,1-
difluoropentyl group, 2-fluoropentyl group, 2,2-
difluoropentyl group, 3-fluoropentyl group, 3,3-
difluoropentyl group, 4-fluoropentyl group, 4,4-
difluoropentyl group, 5-fluoropentyl group, 5,5-
difluoropentyl group, 5,5,5-trifluoropentyl group,
4,4,5,5,5-pentafluoropentyl group, 3,3,4,4,5,5,5-
heptafluoropentyl group, 2 , 2, 3, 3, 4 , 4,5, 5-octafluoropentyl
group and 2,2,3,3,4,4,5,5,5-nonafluoropentyl group.
Examples of 01-04 alkyl group represented by K^ in the formula (I) includes methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group and tert-butyl group.
Examples of C1-C4 alkoxy group represented by R^ and R^ in the formula (I) includes methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, isobutoxy

group and tert-butoxy group.
Examples of amino group optionally substituted by one or two C1-C4 alkyl group(s) represented by R^ and R^ in the formula (I) includes amino group, methylamino group, ethyiamino groupf propylamine group, 2-propylamino group, butylamino group, isobutylamino group, tert-butylamino group and dimethylamino group.
Examples of C2-C5 cyclic amino group represented by R^ and R^ in nhe formula (I) includes 1-aziridino group, 1-
azetidinyl group, 1-pyrrolizinyi group and 1-piperidino group.
Examples of the embodiment of the present compounds include as following: An organic sulfur compound wherein n is 2 in the formula
(I) ;
An organic sulfur compound wherein R2 is a cyano group or a group represented by C(-0)R5 in the formula (I); An organic sulfur compound wherein R2 is a cyano group in the formula (I);
An organic sulfur compound wherein R2 is a group represented by C(=0)R5 and R5 is an amino group optionally substituted by one or two C1-C4 alkyl group(s) in the formula (I); An organic sulfur compound wherein R5 is a group represented by C(=C)R5 and R5' is an amino group in the formula (I); An organic sulfur compound wherein R5 is a halogen atom in the formula (1);

An organic sulfur compound wherein R3 is a fluorine atom or a chlorine atom in the formula (I);
An organic sulfur compound wherein R4 is a C1-C3 fluoroalkyl
group in the formula (I);
An organic sulfur compound wherein R4 is a trifluoromethyl
group in the formula (I);
An organic sulfur compound wherein R4 is a 1,1,2,2,2-
pentafluoroethyl group in the formula (I);
An organic sulfur compound wherein R4 is a 1,1,2,2,3,3,3-
heptafluoropropyl group in the formula (I);
An organic sulfur compound wherein n is 2 and R4 is a C1-C3
fluoroalkyl group in the formula (I) ;
An organic sulfur compound wherein n is 2 and R4 is a
trifluoromethyl group in the formula (I);
An organic sulfur compound wherein n is 2 and R4 is a
1,1,2,2,2-pentafluoroethyl group in the formula (I);
An organic sulfur compound wherein n is 2 and R4 is a
1,1,2,2,3,3,3-heptafluoropropyl group in the formula (I);
An organic sulfur compound wherein n is 2 and R4 is a cyano group or a group represented by C(=0)R4 in the formula (I); A.n organic sulfur compound wherein n is 2 and R4 is a cyano group in the formula (I);
An organic sulfur compound wherein n is 2, R is a group represented by C(=C)R- and R5 is an amino group optionally substituted by one or two C1-C4 alkyl group(s) in the formula [I);

An organic sulfur compound wherein n is 2, R2 is a group
represented by C(=0)R5 and R5 is an amino group in the
formula (I);
An organic sulfur compound wherein n is 2 and R3 is a
halogen atom in the formula (I);
An organic sulfur compound wherein n is 2 and R3 is a
fluorine atom cr a chlorine atom in the formula (I);
An organic sulfur compound wherein R2 is a cyano group or a group represented by C(=0)R5 and R3 is a halogen atom in the
formula (I);
An organic sulfur compound wherein R2 is a cyano group and R2
is a halogen atom in the formula (I);
An organic sulfur compound wherein R2 is a group represented
by C(=0>R5, R5 is an amino group optionally substituted by
one or two Cl-C4 alkyl group (s) and R3 is a halogen atom in
the formula (I);
An organic sulfur compound wherein R2 is a group represented
by C(=0)R5, R5 is an amino group and R3 is a halogen atom in
the formula (I);
An organic sulfur compound wherein R2 is a cyano group or a group represented by C(=0)R6 and V? is a fluorine atom or a chlorine atom in the formula (I); An organic sulfur compound wherein R2 is a cyano group and R3
is a fluorine atom or a chlorine atom iri the formula (Xi; An organic sulfur compound wherein R2 is a group represented by C(=0}R4, R5 is an amino group optionally substituted by one or two C1-C4 alkyl group(s) and R3 is a fluorine atom or

a chlorine atom in the formula (I);
An organic sulfur compound wherein R2 is a group represented by C (=0) R5, R5 is an amino group and R3 is a fluorine atom or a chlorine atom in the formula (I);
An organic sulfur compound wherein n is 2, R2 is a cyano
group or a group represented by C(=0)R5 and R3 is a halogen
atom in the formula (I);
An organic sulfur compound wherein n is 2, R2 is a cyano
group and R-3 is a halogen atom in the formula (I) ;
An organic sulfur compound wherein n is 2, R2 is a group
represented by C(=0)R5, R5 is an amino group optionally
substituted by one or two C1-C4 alkyl group(s) and R3 is a
halogen atom in the formula (I);
An organic sulfur compound wherein n is 2, R2 is a group
represented by C{=0)R5, R5 is an amino group and R3 is a
halogen atom in the formula (I);
An organic sulfur compound wherein n is 2, R2 is a cyano
group or a group represented by C(=0)R5 and R3 is a fluorine
atom cr a chlorine atom in the formula (I);
An organic sulfur compound wherein n is 2, R2 is a cyano
group and R3 is a fluorine atom or a chlorine atom in the
formula (I);
An organic sulfur compound wherein n is 2, R2 is a group
represented by C(=0)R5, R5 is an amino group optionally
substituted by one or two C1-C4 alkyl group (s) and R3 is a
fluorine atom or a chlorine atom in the formula (I);
An organic sulfur compound wherein n is 2, R2 is a group

represented by C(=0)R5, R5 is an amino group and R3 is a fluorine atom or a chlorine atom in the formula (I);
An organic sulfur compound wherein R3 is a hydrogen atom or
a halogen atom in the formula (I);
An organic sulfur compound wherein R3 is a hydrogen atom or
a C1-C4 alkyl group in the formula (!);
An organic sulfur compound wherein R3 is a halogen atom or a
C1-C4 alkyl group in the formula (I);
An organic sulfur compound wherein R3 is a hydrogen atom or
a halogen atom and R4is a C1-C3 fluoroalkyl group in the
formula (I);
An organic sulfur compound wherein R3 is a hydrogen atom or
a C1-C4 alkyl group and R4is a C1-C3 fluoroalkyl group in
the formula (I) ;
An organic sulfur compound wherein R3 is a halogen atom or a
C1-C4 alkyl group and R4is a C1-C3 fluoroalkyl group in the
formula (I).
Next, production method of the present compound is described.
For example, the present compound can be produced by following (Production Method 1) to (Production Method 12).
(Produotion Method 1)
The compound (1-2) which R3 is C1-C4 alkyl group in the present compound can be produced, for example, by making react the following compound (a) and the compound (I-l).


wherein R1, R2}, R4 and n have the same meaning as described above, R3-1 represents a C1-C4 alkyl group, X represents a leaving group such as a chlorine atom, a bromine atom, an iodine atom, a inethanesulfonyloxy group, a p-toluenesulfonyloxy group and trifluoromethanesulfonyloxy group.
The reaction is usually carried out in a solvent and in the presence of a base.
The solvent used for. the reaction includes, for example, acid amides such as W,N-dimethylformamide and the like, ethers such as diethyl ether, tetrahydrofuran and the like, organic sulfurs such as dimethylsulfoxide, sulfolane and the like, halogenated hydrocarbons such as chloroform, 1,2-dichloroethane, chlorobenzene and the like, aromatic hydrocarbons such as toluene, xylene and the like, water and the mixture thereof.
The base used for the reaction includes, for example, inorganic bases such as sodium hydride, sodium hydroxide, potassium hydroxide, potassium carbonate and the like, alkaline metal alkoxides such as sodium methoxide, potassium tert-butoxide and the like, alkaline metal amides such as lithium diisopropyiamide and the like and organic bases such as triethylamine, 1,4-diazabicyclo t2.2.2]octane, 1,8-dia2abicyclot5.4.0]-T-undecene and the like. The amount of base used for the reaction is usually 1 to IC moles based on

1 mole of the compound {I-l).
The amount of the compound (a) used for the reaction is usually 1 to 10 moles based on 1 mole of the compound (I-
1) .
The reaction temperature is usually in the range of -100 to 100 °C and the reaction period is usually 1 to 24 hours.
After the reaction has finished, the compound (I-
2) can be isolated by subjecting post-treatment such as
pouring the reaction mixture into water, extracting with an
organic solvent, followed by concentrating the organic layer.
The isolated compound (1-2) may be purified, if necessary,
by chromatography, recrystallization and the like.
(Production Method 2)
The compound (1-3) which R3 is a hydrogen atom or a C1-C4 alkyl group in the present compound can be produced, for example, by making react the following compound {c) and the compound Id).


example, acid amides such as N,N-dimethylformamide and the like, ethers such as diethyl ether, tetrahydrofuran and the like, organic sulfurs such as dimethylsulfoxide, sulfolane and the like, halogenated hydrocarbons such as chloroform, 1,2-dichloroethane, chlorobenzene and the like, aromatic hydrocarbons such as toluene, xylene and the like, water and the mixture thereof.
The base used for the reaction includes, for example, inorganic bases such as sodium hydride, sodium hydroxide, potassium hydroxide, potassium carbonate and the like, alkaline metal alkoxides such as sodium methoxide, potassium tert-butoxide and the like, alkaline metal amides such as lithium diisopropylamide and the like and organic bases such as triethylamine, 1,4-diazabicyclo[2.2.2]octane, 1,8-diazabicyclo [5 .-^ . 0]-7-undecene and the like. The amount of base used for the reaction is usually 1 to 10 moles based on 1 mole of the compound (d) .
The amount of the compound (c) used for the reaction is usually 1 to 10 moles based on 1 mole of the compound (d).
The reaction temperature is usually in the range of -100 to 100 °C and the reaction period is usually 1 to 24 hours.
After the reaction has finished, the compound (I-3)can be isolated by subjecting post-treatment such as pouring the reaction mixture into water, extracting with an organic solvent, followed by concentrating the organic layer. The isolated compound (1-3) may be purified, if necessary, by chromatography, recrystallization and the like.

The compound (1-4) which R- is a halogen atom in the present compound can be produced, for example, according to {Production Method 3) or (Production Method 4). (Production Method 3)
The production method by making react the compound (I-l) and halogenating agent (e) in the presence of a base.

wherein R^, R^, R' and n have the same meaning as described
above, R"'"'^ represents a halogen atom.
The reaction is usually carried out in a solvent and in the presence of a base.
The solvent used for the reaction includes, for example, acid amides such as N,N-dimethylformaraide and the like, ethers such as diethyl ether, tetrahydrofuran and the like, organic sulfurs such as dimethylsulfoxide, sulfolane and the like, halogenated hydrocarbons such as chloroform, 1,2-dichloroethane, chlorobenzene and the like, aromatic hydrocarbons such as toluene, xylene and the like, water and the mixture thereof.
The base used for the reaction includes, for example, inorganic bases such as sodium hydride, sodium hydroxide, potassium hydroxide, potassium carbonate and the like, alkaline metal alkoxides such as sodium methoxide, potassium tert-butoxide and the like, alkaline metal amides such as lithium diisopropylamide and the like and organic bases such as triethylamine, 1,4-diasabicyclo L2.2.2]octene, 1,8-

diazabicyclo [5 . 4 . 0 J-"/-undecene and the like. The amount of base used for the reaction is usually 1 to 10 moles based on 1 mole of the compound (1-1} .
The halogenating agent (e) used for the reaction includes, for example, halogenated hydrocarbons such as carbontetrachloride, hexachloroethane and the like, halogens such as fluorine, chlorine, bromine and iodine, haloganeted succinimide such as N-chloro succinimide, N-bromo suGcinimide, N-iodo succinimide and the like, N-fluoropyridinium salt such as 1-fluoro-2,4,6-trimethylpyridiniuJTi trifluoromethanesulfonate, 1,1'-difluoro-2,2'-bipyridinium bistetrafluoroborate and the like, copper halide such as copper(II) chloride, copper (II) brorriide and the like.
The amount of halogenating agent (e) used for the reaction is usually 1 to 10 moles based on 1 mole of the compound (I-l).
The reaction temperature is usually in the range of -100 to 100 °C and Che reaction period is usually 1 to 24 hours.
After the reaction has finished, the compound (I-4)can be isolated by subjecting post-treatment such as pouring the reaction mixture into water, extracting with an organic solvent, followed by concentrating the organic layer. The isolated compound (1-4) may be purified, if necessary, by chromatography, recrystallization and the like.
(Production Method 4)
The production method by miaking react the compound


The reaction is carried out without a solvent or in a solvent.
The solvent used for the reaction includes, for example, halogenated hydrocarbons such as chloroform, carbontetrachloride, 1,2-dichloroethane, chlorobenzene and the like, aromatic hydrocarbons such as toluene, xylene and the like, aliphatic nitriles such as acetonitrile, propionitrile and the like, aliphatic carboxylic acids such as acetic acid, carbon disulfide, water and the mixture thereof.
The haiogenating agent (f) used for the reaction includes, for example, halogens such as fluorine, chlorine, broFTLine and iodine- hydrogen halides such as hydrogen fluoride, hydrogen chloride, hydrogen bromide and hydrogen iodide, halogenated sulfur compound such as thionyl chloride, thionyl bromide, sulfuryl chloride and the like, halogenated phosphorus compound such as phosphorus trichloride, phosphorus tribromide, phosphorus pentachloride, phosphorus oxychloride and the like.
The amount of halogenating agent (f) used for the I reaction is usually 1 to 10 moles based on 1 mole of the compound (I-l).

The reaction temperature is usually in the range of -100 to 200 °C and the reaction period is usually 1 to 24 hours.
After the reaction has finished, the compound (I-4)can be isolated by subjecting post-treatment such as pouring the reaction mixture into water, extracting with an organic solvent, followed by concentrating the organic layer. The isolated compound (1-4) may be purified, if necessary, by chromatography, recrystallization and the like.
The compound (1-5) which R^ is a group represented by
Ct=C)R^ and R^ is a C1-C4 alkoxy group, an amino group optionally substituted by one or two C1-C4 alkyl group (s) or a C2-C5 cyclic amino group in the present compound can be produced, for example, according to (Production Method 5) or
(Production .Method 6) .
(Production Method 5)

wherein R^, R-^, R^, R^ and n have the same meaning as described above, Z represents a halogen atom. (Step 5-1)
The compound (i) can be produced by making react the compound (g) and halogenating agent (h). The reaction is carried out without a solvent or in a solvent.
The solvent used for the reaction includes, fcr

example, halogenated hydrocarbons such as chloroform, dichloromethane, 1,2-dichloroethar)e, chlorohenzene and the like, aromatic hydrocarbons such as toluene, xylene and the like.
The halogenating agent (h) used for the reaction includes, for example, oxalyl chloride, thionyl chloride, thionyl bromide, phosphorus trichloride, phosphorus tribromide and phosphorus pentachloride. The amount of halogenating agent (h) used for the reaction is usually 1 mole to excess based on 1 mole of the compound (g).
The reaction temperature is usually in the range of -20 to 100 °C and the reaction period is usually 1 to 24 hours.
After the reaction has finished, the compound (i)can be isolated by subjecting a treartment such as concentrating the reaction mixture. The isolated compound (i) may be purified by distillation and the like, (Step 5-2)
The reaction is usually carried out in a solvent and in the presence of a base.
The solvent used for the reaction includes, for example, acid amides such as N,N-dimethylformamide and the like, ethers such as diethyl ether, tetrahydrofuran and the like, organic sulfurs such as dimethylsulfoxide, sulfolane and the like, halogenated hydrocarbons such as chloroforin, 1,2-dichioroethane, chlorobenzene and the like, aromatic hydrocarbons such as toluene, xylene and the like, water and the mixture thereof.
The base used for the reaction includes, for example.

inorganic bases such as sodium hydride, sodium hydroxide, potassium hydroxide, potassium carbonate and the like and organic bases such as triethylamine, 1,4-diazabicyclo[2.2.2]octane, 1,8-diazabicyclo[5.4.0]-7-undecene and the like. The amount of base used for the reaction is usually 1 to 10 moles based on 1 mole of the compound (i).
The amount of the compound (j) used for the reaction is usually 1 to 10 moles based on 1 mole of the compound (i).
The reaction temperature is usually in the range of -20 to loo °C and the reaction period is usually 1 to 24 hours.
After the reaction has finished, the compound (I-5) can be isolated by subjecting post-treatment such as pouring the reaction mixture into water, extracting with an organic solvent, followed by concentrating the organic layer. The isolated compound (1-5) may be purified, if necessary, by chromatography, recrystallization and the like.


in the presence of a condensing agent.
The solvent used for the reaction includes, for example, ethers such as diethyl ether, tetrahydrofuran and the like, organic sulfurs such as dimethylsulfoxide, sulfolane and the like, halogenated hydrocarbons such as chloroform, 1,2-dichloroethane, chlorobenzene and the like and aromatic hydrocarbons such as toluene, xylene and the like.
The condensing agent used for the reaction includes, for example, dicyclohexylcarbodiimide, N-[3-dimethylaminopropyl)-N'-ethylcarbodiimide, carbonyldiimidazole and the like.
The amount of condensing agent used for the reaction is usually 1 to 10 moles based on 1 mole of the compound (g).
The amount of the compound (j) used for the reaction is usually 1 to 10 moles based on 1 mole of the compound (q).
The reaction temperature is usually in the range of -20 to 100 "C and the reaction period is usually 1 to 24 hours.
After the reaction has finished, the compound (I-5)can be isolated by subjecting a treatment such as pouring the reaction mixture into water, extracting with an organic solvent, followed by concentrating the organic layer. The isolated compound (1-5) may be purified, if necessary, by chromatography, recrystallization and the like.
{Production Method 7)
The compound (1-1} which R"^ is a hydrogen atom in the present compound can be produced, for example, by making


wherein R"'", R^, R", X and n have the same meaning as described above.
The reaction is usually carried out in a solvent and in the presence of a base.
The solvent used for the reaction includes, for example, acid amides such as N,N-dimethylformamide and the like, ethers such as diethyl ether, tetrahydrofuran and the like, organic sulfurs such as dimethylsulfoxide, sulfclane and the like, halogenated hydrocarbons such as chlcroform, 1,2-dichloroethane, chlorobenzene and the like, aromatic hydrocarbons such as toluene, xylene and the like, water and the mixture thereof.
The base used for the reaction includes, for example, inorganic bases such as sodium hydride, sodium hydroxide, potassium hydroxide, potassium carbonate and the like, alkali metal alkoxides such as sodium methoxide, potassium tert-butoxide and the like, alkali metal amides such as lithium diisopropyl amide and the like and organic bases such as triethylamine, 1,4-dia2abicyclo[2.2.2]octane, 1,8-diazabicyclo[5.4.0]-7-undecene and the like. The amount of base used for the reaction is usually 1 to 10 moles based on 1 mole of the compound (k).
The amount of the compound (c) used for the reaction is usually 1 to 10 moles based on 1 mole of the corr.pcund (k) .

The reaction temperature is usually in the range of -100 to 100 °C and the reaction period is usually 1 to 24 hours.
After the reaction has finished, the compound (I-l)can be isolated by subjecting post-treatment such as pouring the reaction mixture into water, extracting with an organic solvent^ followed by concentrating the organic layer. The isolated compound (I-l) may be purified, if necessary, by chromatography, recrystallization and the like.
(Production Method 8)
The compound (1-8) which R^ is a group represented by C(=0)R", R^ is an amino group optionally substituted by one or two Cl-C^ alkyl group(s) or a C2-C5 cyclic amino group and r. is 2 in the present compound can also be produced by making the compound (1-7), which R^ is a group represented by C(=0)R-, R^ is a C1-C4 alkoxy group and n is 2, react with the compound (p) .

wherein R"', R"^ and R^ have the same meaning as described above, R""-" represents a C1-C4 alkoxy group, B^"^ represents an amino group optionally substituted by one or two C1-C4
alkyl group (s) or a C2-C5 cyclic amino group.
The reaction is usually carried out in a solvent.
The solvent used for the reaction includes, for example, ethers such as diethyl ether, terrahydrofuran and

the like, organic sulfurs such as dimethylsulfoxide, sulfolane and the like, halogenated hydrocarbons such as chloroform, 1,2-dichloroethane, chlorobenzene and the like, aromatic hydrocarbons such as toluene, xylene and the like.
The amount of the compound (p) used for the reaction is usually 1 to 10 moles based on 1 mole of the compound (I-1) .
The reaction temperature is usually in the range of -20 to 100 'C and the reaction period is usually 1 to 24 hours.
After the reaction has finished, the compound (I-8)can be isolated by subjecting a post-treatment such as of concentrating the reaction mixture. The isolated compound (1-8) may also be purified, if necessary, by chromatography, reorystallization and the like.
(Production Method 9}
The compound (1-9) which R^ is a group represented by C(=S)R^ in the present compound can also be produced by
making the compound (1-5) which R^ is a group represented by C(=C)R^ react with the sulfurnating agent (q).

wherein R", R^, R', R' and n have the same meaning as
described above.
'> The reaction is usually carried out in a solvent.
The solvent used for the reaction includes, for

example, haiogenated hydrocarbons such as chloroform, 1,2-dichloroethane, chlorobenzene and the like, aromatic hydrocarbons such as toluene, xylene and the like.
The sulfurnating agent (q) used for the reaction includes, for example, inorganic sulfur compounds such as hydrogen sulfide, organic sulfur compounds such as phosphorus pentasuliide and the like and 2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane 2,4-disulfide and the like.
The amount of the sulfurnating agent (q) used for the reaction is usually 0,5 to 10 moles based on 1 mole of the compound (1-5) .
The reaction temperature is usually in the range of 0 to 250 "C and the reaction period is usually 1 to 72 hoi:rs.
After the reaction has finished, the compound (I-9)can be isolated by subj ecting a post-treatment such as of concentrating the reaction mixture. The isolated compound {1-9) may be purified, if necessary, by chromatography, recrystallization and the like.
The compound (I-IO) which n is 0 in the present compound can be produced, for example, by according to (Production Method 10) or (Production Method 11).
(Production Method 10)
The production method by making react the compound (r) and
the compound (m).


The reaction is usually carried out in a solvent and in the presence of a base.
The solvent used for the reaction includes, for example, acid amides such as N, N~dimethylformamide and the like, ethers such as diethyl ether, tetrahydrofuran and the like, organic sulfurs such as dimethylsulfoxide, sulfolane and the like, halogenated hydrocarbons such as chloroform, 1, 2-dichloroethane, chlorobenzene and the like, aromatic hydrocarbons such as toluene, xylene and the like, water and the mixture thereof.
The base used for the reaction includes, for example, inorganic bases such as sodium hydride, sodium hydroxide, potassium hydroxide, potassium carbonate and the like, alkali metal alkoxides such as sodium methoxide, potassium tert-butcxide and the like, alkali metal amides such as lithium diisopropyl amide and the like and organic bases such as triethylamine, l,4-diazabicyclo[2.2.2]octane, 1,8-diazabicyclo[5.4.0]~7-undecene and the like.
The amount of base used for the reaction is usually 1 to 10 moles based on 1 mole of the compound (r).
The amount of the compound (m) used for the reaction is usually 1 to 10 moles based on 1 mole of the compound (r).
The reaction temperature is usually in the range of -20 to lOQ 'C and the reaction period is usually 1 to 24

hours.
After the reaction has finished, the compound (I-10)can be isolated by subjecting post-treatment such as pouring the reaction mixture into water, extracting with an organic solvent, followed by concentrating the organic layer. The isolated compound (I-IO) may be purified, if necessary, hy chromatography, recrystallization and the like.

The reaction is usually carried out in a solvent and in the presence of a base.
The solvent used for the reaction includes, for example, acid am.ides such as N, N-dimethylf ormamide and the like, ethers such as diethyl ether, tetrahydrofuran and the like, organic sulfurs such as dimethylsulfoxide, sulfolane and the like, halogenated hydrocarbons such as chloroform, 1,2-dichloroethane, chlorobensene and th$ like, aromatic hydrocarbons such as toluene, xylene and the like, water and the mixture thereof.
The base used for the reaction includes, for example, inorganic bases such as sodium hydride, sodium hydroxide, potassium hydroxide, potassium carbonate and the like,

alkali metal alkoxides such as sodium methoxide, potassium tert-butoxide and the like, alkali metal amides such as lithium diisopropyl amide and the like and organic bases such as triethylamine, 1, 4"diazabicyclo[2.2.2}octane, 1,8-diazabicyclo(5 . 4.0]-7-undecene and the like. The amount of base used for the reaction is usually 1 to 10 moles based on 1 mole of the compound (o).
The amount of the compound (s) used for the reaction is usually 1 to 10 moles based on 1 mole of the compound (o).
The reaction temperature is usually in the range of -20 to 100 °C and the reaction period is usually 1 to 24 hours.
After the reaction has finished, the compound {1-10)can be isolated by subjecting post-treatment such as pouring the reaction mixture into water, extracting with an organic solvent, followed by concentrating the organic layer. The isolated compound (I-IO) may be purified, if necessary, by chromatography, recrystallization and the like.
(Production Method 12)
The compound (I-ll) which n is 1 or 2 in the present compound can be produced by making the compound (I-IO) oxidize.


The reaction is usually carried out in a solvent and in the presence of a oxidizing agent.
The solvent used for the reaction includes, for example, alcohols such as methanol, sthanol and the like, halogenated hydrocarbons such as dichloromethane, chloroform and the like, aromatic hydrocarbons such as toluene, xylene and the :.ike, aliphatic carboxylio acids such as acetic acid, trifluoroacetic acid and the like, water and the mixture thereof.
The oxidizing agent used for the reaction includes, for example, peracids such as peracetic acid, trifluoroperacetic acid, m-chloroperbenzoic acid and the like, halogen molecules such as chlorine and bromine, halogenated succinimides such as N-chlorosuccinimide, perhalogenated compounds such as perchloric acid or its salts, periodic acid or its salts and the like, permanganates such as potassium permanganate and the like, chromic acid salts such as potassiuiri chromate and the like and hydrogen peroxide. The amount of oxidizing agent used for the reaction is usually 1 to 10 moles based on 1 mole of the compound (I-IO).
The reaction temperature is usually in the range of -5Q to 200 X and the reaction period is usually 1 to 72 hours.
After the reaction has finished, the compound (I-11)can be isolated by subjecting post-treatment such as pouring the reaction mixture into water, extracting with an organic solvent, followed by concentrating the organic layer. The isolated compound (I-ll) may be purified, if necessary,

by chromatography, recrystallization and the like.
Next, the production method of intermediate compounds for production of the present compounds is explained as
Reference Production Method.
(Reference Production Method 1-1)
The compound (g) can be produced by making the compound (I-
6) hydrolyze in the presence of an acid.

wherein R', R^, R* and n have the same meaning as described above, R^'" represents a methoxy group or an ethoxy group.
The reaction is usually carried out in the presence of water and usually in an organic solvent.
The organic solvent used for the reaction includes, for example, alcohols such as methanol, ethanol and the like, ethers such as diethyl ether, tetrahydrofuran and the like, organic sulfurs such as dimethylsulfoxide, sulfolane and the like, halogenated hydrocarbons such as chloroform, 1,2-dichloroethane, chlorobenzene and the like, aromatic hydrocarbons such as toluene, xylene and the like, aliphatic carboxylic acids such as formic acid, acetic acid and the like and the mixture thereof.
The acid used the reaction includes, for example, ) inorganic acids such as hydrochloric acid, sulfuric acid and the like.

The amount of an acid used for the reaction is usually 1 to 10 moles based on 1 mole of the compound (1-6).
The reaction temperature is usually in the range of -20 to 100 "C and the reaction period is usually 1 to 24 hours.
After the reaction has finished, the compound (g)can be isolated by subjecting post-treatment such as pouring water to the reaction mixture, extracting with an organic solvent, followed by concentrating the organic layer. The isolated compound (g} may be purified, if necessary, by chromatography, recrystallization and the like.
(Reference Production Method 1-2)
The compound (g) can be produced by making the compound (I-6) hydrolyze in the presence of a base.
The reaction is usually carried out in the presence of water and usually in an organic solvent.
The organic solvent used for the reaction includes, for example, alcohols such as methanol, ethanol and the like, ethers such as diethyl ether, tetrahydrofuran and the like, organic sulfurs such as dimethylsulfoxide, sulfolane and the like, aromatic hydrocarbons such as toluene, xylene and the like and the mixture thereof.
The base used for the reaction includes, for example, inorganic bases such as sodium hydroxide, potassium hydroxide and the like.
The amount of a base used for the reaction is us'L^ally 1 to 10 moles based on 1 mole of the compound (1-6).
The reaction temperature is usually in the range of -

20 to 100 °C and the reaction period is usually 1 to 24 hours.
After the reaction has finished, the compound (g/oan be isolated by subjecting post-treatment such as pouring water and an acid to the reaction mixture, extracting with an organic solvent, followed by concentrating the organic layer. The isolated compound (g) may be purified, if necessary, by chromatography, recrystallization and the like.
(Reference Production Method 2)
The compound (d-1) which R^~^ is a C1-C4 alkyl group in the compound (d) can be produced by making react the below compound (a) and the compound {k).

wherein R^, R^, R^"'^,n and X have the same meaning aa described above.
The reaction is usually carried out in a solvent and in the presence of a base.
The solvent used for the reaction includes, for example, acid amides such as N,N-dimethylformamide and the like, ethers such as diethyl ether, tetrahydrofuran and the like, organic sulfurs such as dimethylsulfoxide, sulfolane and the like, halogenated hydrocarbons such as chloroform, 1,2-dichloroethane, chlorobenzene and the like, aromatic hydrocarbons such as toluene, xylene and the like, water and the irdxture thereof.

The base used for the reaction includes, for example, inorganic bases such as sodium hydride, sodium hydroxide, potassium hydroxide, potassium carbonate and the like, alkaline metal alkoxides such as sodium methoxide, potassium tert-bu"coxide and the like, alkaline metal amides such as lithium diisopropylamide and the like and organic bases such as triethylamine, 1,4-diazabicyclo[2.2.2]octane, 1,B-d-iazabicyclo [5 . 4 . 0 j -7-undecene and the like . The amount of base used for the reaction is usually 1 to 10 moles based on 1 mole of the compound (k).
The amount of the compound (a) used for the reaction is usually 1 to 10 moles based on 1 mole of the compound (k).
The reaction temperature is usually in the range of -20 to 100 °C and the reaction period is usually 1 to 24 hours.
After the reaction has finished, the compound (d-Dean be isolated by subjecting post-treatment such as pouring the reaction mixture into water, extracting with an organic solvent, followed by concentrating the organic layer. The isolated compound (d-1) may be purified, if necessary, by chromatography, recrystallization and the like.
(Reference Production Method 3)
The compound (k-l) which n is D and the compound {k-2) which
n is 1 or 2 can be produced, for example, according to
following scheme .


(Step Ill-l-a)
The compound (k-1) can be produced by making react the compound (1) and the compound (m).
The reaction is usually carried out in a solvent and in the presence of a base.
The solvent used for the reaction includes, for example, acid amides such as H,N-dimethylformamide and the like, ethers such as diethyl ether, tetrahydrofuran and the like, organic sulfurs such as dimethylsulfoxide, sulfolane and the like, halogenated hydrocarbons such as chloroform, 1,2-dichloroethane, chlorobenzene and the like, aromatic hydrocarbons such as toluene, xylene and the like, water and the rriixture thereof.
The base used for the reaction includes, for example, inorganic bases such as sodium hydride, sodium hydroxide, potassium hydroxide, potassium carbonate and the like, alkaline metal alkoxides such as sodium methoxide, potassium tert-butoxide and the like, alkaline metal amides such as lithium diisopropylamide and the like and organic bases such as triethylamine, 1,4-diazabicyclo[2,2.2]octane, 1,8-diazabicyclo[5 . 4.0]-7-undecene and the like.

The amount of base used for the reaction is usually 1 to 10 moles based on 1 mole of the compound (1).
The amount of the compound {m} used for the reaction is usually 1 to 10 moles based on 1 mole of the compound [1> .
The reaction temperature is usually in the range of -20 to 100 °C and the reaction period is usually 1 to 24 hours.
After the reaction has finished, the compound (k-Dcan be isolated by subjecting post-treatment such as pouring the reaction mixture into water, extracting with an organic solvent, followed by concentrating the organic layer. The isolated compound (k-1) may be purified, if necessary, by chromatography, recrystallization and the like. {Step Ill-l-b)
The compound (k-1) can also be produced by making react the compound (n) and the compound (o) .
The reaction is usually carried out in a solvent and in the presence of a base. The solvent used for the reaction includes, for example, acid amides such as N,N-dimethylformamide and the like, ethers such as diethyl ether, tetrahydrofuran and the like, organic sulfurs such as dimethylsulfoxide, sulfolane and the like, halogenated hydrocarbons such as chloroform, 1,2-dichloroethane, chlorobenzene and the like, aromatic hydrocarbons such as toluene, xylene and the like, water and the mixture thereof. The base used for the reaction includes, for example, inorganic bases such as sodium hydride, sodium hydroxide, potassium hydroxide, potassium carbonate and the like, alkaline m.etal alkcxides such as scdium methoxide, potassium

tert-butoxide and the like, alkaline metal amides such as lithium diisopropylamide and the like and organic bases such as triethylamine, 1,4-diazabicyclo[2.2.2]octane, 1,8-diazabicyclo[5.4.0]-7-undecene and the like. The amount of base used for the reaction is usually 1 to 10 moles based on 1 mole of the compound (o) .
The amount of the compound {n) used for the reaction is usually 1 to 10 moles based on 1 mole of the compound (o).
The reaction temperature is usually in the range of -20 to 100 "C and the reaction period is usually 1 to 24 hours.
After the reaction has finished, the compound (k-1)can be isolated by subjecting post-treatment such as pouring the reaction mixture into water, extracting with an organic solvent, followed by concentrating the organic layer, The isolated compound (k-1) may be purified, if necessary, by chromatography, recrystallization and the like.
(Step III-2)
The compound {k-2) can be produced, for example, by making the compound (k-1) oxidize.
The reaction is usually carried out in the presence of a solvent and in the presence of a oxidizing agent.
The solvent used for the reaction includes, for example, alcohols such as methanol, ethanol and the like, halogenated hydrocarbons such as dichloromethane, chloroform =nd the like, aromatic hydrocarbons such as toluene, xylene and the like, aliphatic carboxylic acids such as acetic acid, Lrifluorcacetic acid and the like, water and the mixture

thereof.
The oxidizing agent used for the reaction includes, for example, peracids such as peracetic acid, trifluoroperacetic acid, m-chloroperbenzoic acid and the like, halogen molecules such as chlorine and bromine, halogenated succinimides such as N-chlorosuccinimide, perhslogenated compounds such as perchloric acid or its salts, periodic acid or its salts and the like, permanganates such as potassium permanganate and the like, chromic acid salts such as potassium chromate and the like and hydrogen peroxide. The amount of oxidizing agent used for the reaction is usually 1 to 10 moles based on 1 mole of the compound (k-l).
The reaction temperature is usually in the range of -50 to 200 °C and the reaction period is usually 1 to 72 hours.
After the reaction has finished, the compound (k-2)can be isolated by subjecting a treatment such as pouring the reaction mixture into water, extracting with an organic solvent, followed by concentrating the organic layer. The isolated compound [k-2) may be purified, if necessary, by chromatography, recrystallization and the like.
The above mentioned compound (o) and (s) each can be produced, for example, by the same method described in The Journal of Organic Chemistry, 27(1),p. 93 — 95(1962) and
HETEROCYCLES, 24(5), p. 1331-134 6(193 6).
The above mentioned compound (t) can be produced, for

example, by the same method described in The Journal of Organic Chemistry, 18, p.1112-1115 (1953) .
The noxious arthropods against which the present compound has control activity may include insect pests, acarine pests and the like. Specific examples are listed b e 10'vi:
Hemiptera:
Delphacidae such as Laodelphax striatellus, Nilaparvaza lugens, Sogatella furcifera and the like,
Deltocephalidae such as Nephotettix cincticeps, Nephotettlx vlrescans and "he like,
Aphididae such as Aphis gossypii, Myzus persicae, Brevlooryne bras sicae, Macrosiphum euphorbias, Aulacorthum solani, P.hopa las iphum padi, Toxoptera clzricidus and the like,
Fentatomidae such as Nezara antennata, Riptortus clavetus, Eysarcoris lewisi, Eysarcorls parvus, Plautia stali, Halyomorpha mista, Stenotus rubrovietatus, Trigonotylus ruficornis and the like,
Aleyrodidae such as Trialeurodes vaporarioru/n, Bemisia argentifolii and the like,
Coccidae such as Aonidiella aurantii, Comstockaspis verniciosa, Unaspis citri, Ceroplastes ruhens, Icerya purchasi and the like,
Tingidae,
Cirr.icidae such as Cimex lectularius,
Psyllidae, and the like;

Lepidoptera:
Pyralidae such as Chilo suppressalis, Cnaphalocrocis wedinalis, Notarcha derogate, Plodia interpunctella, Maruca testulalis, Hellula undalis, PedJr^cta—tgifeeiiTrliuA and the
Woctuidae such as Spodoptera litura, Pseudaletla separata, Thoricoplusia spp., Heliothis spp., Helicoverpa spp. and the like,
Pieridae such as Pieris rapae and the like,
Tortricidae such as Adoxophyes spp., Grapholita mclesta, Cydla pomonella and the like,
Carposinidae such as Carposina niponensis and the like,
Lyonetiidae such as Lyonetia spp. and the like,
Lymantriidae such as Lymantria spp., Euproctis spp., and the like,
Yponomeutidae such as Plutella xylostella and the like,
Graciliariidae such as Caloptilia theivora, Phyllonorycter ringoneella, and the like,
Gelechiidae such as Pectinophora gossypiella and the like,
Arctiidae such as Hyphantria cunea and the like,
Tineidae such as Tinea translucens, Tineola bisselliella and the like;
Diptera;
Calicidae such as Culex pipiens pallens, Culex

tritaenicrhynchus, Culex quinquefasciatus and the like,
Aedes spp. such as Aedes aegypti, Aedes alhopictus and the like,
Anopheles spp. such as Anopheles sinensis and the like,
Chironomidae,
Muscidae such as Musca domestica, Muscina st&bulans and rhe like,
Calliphoridae,
Sa rcophagidae,
Fanniidae.
Anthomyiidae such as Delia platura, Delia antiqua and the like,
Agromyzidae such as Liriomyza trifolii,
Tephritidae,
Drosophilidae,
Phoridae such as Megaselia spiracularis,
Psychodidae such as Clogmia albipunctata,
Tabanidae,
Simuliidae,
Stomcxyidae, and the like;
Coleoptera:
Diabrotica spp. such as Diahrotica virgifera virgifera, Diabrotica undecimpunctata howardi and the like, Scarabaeidae such as Anomala cuprea, Anomala
rufocuprea and the like,
Curculionidae such as Sitcphilus zeamais, Lissorhoptrus oryzophiluSf Callosobruchuys chienensis and

the like,
Tenebrionidae such as Tenebrio molltor, Tribolium castansum and the like,
Chrysomelidae such as Oulema oryzae, Aulacophora
femoralis, Phyllotreta striolata, Leptinotarsa decemlineata
and the li^e,
Dermestidae such as Dermestes maculates,
Anobiidaef
Epilachna spp. such as Epilachna viglntioctopunctata and the like,
Lyctidae,
Ecstrychidae,
Cerambycidae,
Cerambycidae,
Paederus fuscipes and the like;
Blettodea: Blattslla germanica, Perlplaneta fuliglnosa, Periplaneta americana, Perlplaneta brunnea^ Blatta orientalis and the like;
Thysanoptera: Thrips palmi, Thrlps tabaci, Frankliniella occidentalis, Frankliniella intonsa, Scirtothrips dorsalis and the like;
Hyrr.enoptera:
Formicidae such as Monoraorium pharaosis, Formica fusca japonica^ Ochetellus glaber^ Pristomyrmex pungens^ Pheldole noda, linepithema bumile and the like,
Vespidae,
bethylid wasp,

Tsnthredinidae such as Athalia japonica, and the like;
Orthoptera: Gryllotalpidae, Acrididae, Gryllidae and -he like;
Aphaniptera: Ctenocephalides felis, CtenocQphalides can is, PuJex irritans, Xancpsylla cheopis, and the like;
Anoplura: 'Pedxculus humanus corporis, Phthirus pubis, Haematopinus eurysternus, Dalmslini-B—ev-±-a, Haemaopinus suis and the like;
Isoptera; Reticulitermes speratus, Coptotexmes farrnosanus, Phinoterir.itidae such as Reticulitermes flavipes , Reticulitermss hesperus, Reticulltermes virginlcus, Reticulitermes tibialis, Heterotermes aureus and the like, Kalotermitidae such as Jncisitermes minor and the like; dampwood termites such as Zooterinopsis nevadensis and the like;
Acarina:
Tetranychidae such as Tetranychus urticae, Tetranychus kanzawal, Panonychus cxtri, Fanonychus ulmi, Oligonychus spp., and the like,
Eriophyidae such as Aculops lycopers, Aculops
pelekassl, Aculus schlechtendali, and the like,
I Tarsonemidae such as Polyphagotarsonemus latus, and
the like,
Tenuipalpidae,
Tuckerellidae,
Ixodidae such as Haemaphysalis longiccrnis,

Haemaphysalis flava, Dermacentor variabilis, Haemaphysalis flava, Dermacentor taiwanicus, Ixodes ovatus, Ixodes persulcatus, Ixodes scapularis, Boophilus microplus, Amblyomma americanum, Rhipicephalus sanguineus and the like,
Acaridae such as Tyrophagus putrescentiae, and the like,
Epiderinoptidae such as Dermatophagoides farinae, Dermstophagoides ptrenyssnus, and the like,
Cheyletidae such as Cheyletus eruditus, Cheyletus malaccensis, Cheyletus moorei, and the like,
Ornithonyssus baooti, Ornithonyssus sylvairum,
Dermanyssidas such as Dermanyssus gallinae;
chiggers such as Leptotrombidium akamushi,
Araneae: Chiracanzhium japonicum, Lazrodect-js hasseltii, and the like;
Chilopoda: Thereuonema kilgendorfi, Scclopendra svbspinipes, and the like;
Diplopoda: Oxidus gracilis, Nedyopus tambanus, and the like;
Isopoda; P.rmadillidium vulgare, and the like;
Gastropoda: Limax marginatus, Limax flaws, and the like.
The noxious arthropod controlling agent of the present invention comprises the present compound and a inert carrier. Usually the present compound is mixed with a solid carrier, a liquid carrier and/or a gaseous carrier, and if necessary, added a surfactant end other adjuvant for

formulation to formulate to an emulsifiable concentrate, an oil solution, a shampoo formulation, a flowable , a dust, a wettable powder, a granule, a paste formulation, a microcapsule, a foam, an aerosol, a carbon dioxide gas formulation, a tablet and a resin formulation. These formulations iriay be converted to use into a poison bait, a mcsqito coil, an electric mosquito mat, a smoking agent, a fumigant or sheet.
In the noxious arthropod controlling agent of the present invention, the present compound is usually contained in an amount of 0.1% to 95% by weight.
The solid carrier for formulation includes, for example, a fine power and a granule of clays (e.g., kaolin clay, diatomite, bentonire, Fubasami clay, acid clay, etc.), synthetic hydrated silicon oxide, talc, ceramic, other inorganic minerals {e.g., sericite, quartz, sulfur, activated carbon, calcium carbonate, hydrated silica) or chemical fertilizers {e.g., ammonium sulfate, ammonium phosphate, ammonium nitrate, ammonium chloride, urea).
The liquid carrier for formulation includes, for example, aromatic or aliphatic hydrocarbons (e.g., xylene, toluene, alkylnaphthalene, phenylxylylethane, kerosine, ■ light oil, hexane, cyclohexane), halogenated hydrocarbons
(e.g., chlorobenzene, dichloromethane, dichioroethane, rrichloroet-hane) , alcohols (e.g., rriethanol, ethanol, isopropyl alcohol, butanol, hexanol, ethylene glycol), ethers (e.g., diethyl ether, ethylene glycol dimethyl ether,

diethylsne glycol monomethyl ether, diethyiene glycol monoethyl ether, propylene glycol monomethyl ether, tetrahydrofuran, dioxane) , esters (e.g., ethyl acerate, butyl acetate), ketones (e.g., acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone), nitriles (e.g., acetonitrile, isobutyronitrile), sulfoxides (e.g., dimethylsulfoxide) , acid amides (e.g. , N,N-dimethylformarr.ids, W,N-dimethylacetamide), vegetable oils (e.g., soy bean oil, cotton seed oil), vegetable essential oils (e.g., orange oil, hyssop oil, lemon oil) and water.
The gaseous carrier for formulation includes, for example, butane gas, flon gas, liquefied petroleum gas (L?G), dimethyl ether, carbon dioxide and nhe like.
The surfactant includes, for example, alkyl sulfate salts, aikylsulfonic acid salts, a1kylarylsulfonic acid salts, alkyl aryl ethers and their polyoxyethylene derivatives, polyethylene glycol ethers, polyhydric alcohol esters, and sugar alcohol derivatives.
The other adjuvant for formulation includes, binders, dispersants, stabilizers and the like, and specifically for example, casein, gelatin, polysaccharides (e.g., starch, gum arable, cellulose derivatives, alginic acid), lignin derivatives, bentonite, sugars, synthetic water-soluble polymers (e.g., polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acid), rAP (isopropyl acid phosphate), BHT (2,6-di-t-butyl-4-methylphenol) , BHA (a mixture of 2-t-buiiyl-4-ir.ethoxyphenol and 3-t-butyl-4-methoxyphenol) , vegetable oils.

mineral oils, fatty acids, and fatty acid esters.
The base for resin formulation includes, for example, polyvinyl chloride based copolynier, polyurethane and the like. To these bases, if necessary, a plasticizer such as phthalates (e.g., dimethyl phthaiate, dioctyl phthalate), adipates and stearic acid may be added. The resin formulation can be obtained by kneading the compound into the base using a known kneader and then formulating by injection molding, extrusion molding, press molding and the like, and further, if necessary, via a process for molding, cutting and the like, the resin formulation having a specific form can be converted into a resin formulation such as board, film, tape, net, string and the like. These resin formulations can be converted into, for example, an animal collar, an animal ear tag, a sheet formulation, an attraction string, a gardening stick.
A base for the poison bait includes, for example, grain powders, vegetable oils, sugars, and crystalline cellulose, and further, if necessary, antioxidants such as dibutylhydroxytoluene and nordihydrog'uaiaretic acid, preservatives such as dehydroacetic acid, agents for preventing children and pets from erroneously eating such as hot pepper powder, and pest-attractive flavors such as cheese flavor, onion flavor and peanut oil may be added to the base.
The noxious arthropod controlling agent of the present invention is used, for example, by applying to

noxious arthropods directly and/or at a habitat of noxious arthropods such as plant, animal soil and the like.
When the noxious arthropod controlling agent of the present invention is used for a control of pests in agriculture and forestry, the application amount is usually 1 to 10,000 g/ha, preferably 10 to 500 g/ha, as an active ingredient. The emuisifiable concentrates, wettable powders, flowables, and microcapsule formulations are usually applied after dilution with water to have an active ingredient concentration of 1 to 1,000 ppm, while dusts and granules ere usually applied as such. These formulations may be sprayed directly to the plant to be protected from noxious arthropods. The noxious arthropods living in the soil can be controlled by treating the soil with these formulations, and the formulations can also be applied to treat seedbeds prior to the planting plants or to treat planting holes or plant bottoms in the planting. Furthermore, the sheet formulation of the noxious arthropod controlling agent of the present invention can be applied by a method such as winding around plants, stretching in the vicinity of plants and laying on the soil surface at the plant bottom.
When the noxious arthropod controlling agent of the present invention is used for a control of epidemic, the application amount is usually 0.001 to 10 mg/m^ as an active ingredient in case of application for open space, and 0-001 !:o ICO mg/m^ as an active ingredient in case of application for plane surface. The emuisifiable concentrates, wettable

powders and flowables are usually applied after dilution with water to have an active ingredient concentration cf 0.01 to 10,000 Ppm, while oil solutions, aerosols, smoking agents and poison baits are usually applied as such.
When the noxious arthropod controlling agent of the present invention is used for a control of parasite living outside of a livestock such as cow, horse, pig, sheep, goat and chicken, and a small animal such as dog, cat, rat and mouse, the noxious arthropod controlling agent of the present invention can be applied to said animal by a veterinarily known method. Specifically, for systemic control, the noxious arthropod controlling agent of the present invention is administered by means of, for example, a tablet, a mixture with feed, a suppository or an injection (e.g., intramuscular, subcutaneous, intravenous, intraperitoneal), and for non-systemic control, it is applied by a method such as spraying an oil solution or an aqueous liquid formulation, carrying out pour-on treatment or spot-on treatment, washing said animal with a shampoo formulation, attaching the resin formulation on said animal as a collar or an ear-tag, and the like. When it is administered to an animal, the amount of the present com,pound is usually in the range of 0.1 to 1,000 mg/kg body weight of the animal.
The noxious arthropod controlling agent of the present invention can also be used in admixture or corr-bination with other insecticides, nematocides, acaricides.

fungicides, herbicides, plant growth regulators, synergists, fertilizers, soil conditioners, animal feeds, and the like.
The active ingredients of such other insecticide and acaricide include, for example, pyrethroid compounds such as allethrin, tetramethrin, prallethrin, phenothrirj, 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, flucythrinare, tau-fluvalinate, acrinathrin, teiluthrin, cycloprothrin, empenthrin, 2,3,5,6-tetrafluoro-4-methoxymethylbenzyl 3- (2-methyl-l-propenyl)-2,2-dimethylcyclopropancarboxylate,
2,3,5,5-tetrafluoro-4-methoxymethylbenzyl 3~(1-propenyl)-2,2-dimethylcyclopropancarboxylate and
2,3,5,6-tetrafluoro-4-methylbenzyl 3-(1-propenyl)-2,2-dimethylcyclopropancarboxylate; organophosphorus compounds such as dichlorvos, fenitrothion, cyanophos, profenofcs, 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, novalurcn and

triazuron; juvenile horrticne-iike substances such as pyriproxyfens methoprene, hydroprene and fenoxycarb; neonicotinoid compounds such as acetaraiprid, nitenpyram, thiacloprid, thiamethoxam, dinotefuran and clothianidin; "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; pyridalyl; cyromazine; fenpyroximate; tebuf enpyrad; tolfenpyrad; pyridaben; pyrimidifen; f luacrypyrirr.; etoxazole; f enazaquin; acequinocyl ; hexythiazoK,- clofentezine; fenbutatin oxide; dicofoi, propargite; abamectin; milbemectin; amitraz; cartap; bensuitap; thiocyclam; endosulfan; spirodiclofen; spiremes ifen; Flubendiamide; and azadirachtin.
The other fungicide include, for example, strobilurin compounds such as azoxystrobin; organophosphorus compounds such as tolclofos-methyl; azole compounds such as triflumizole, pefurazoate and difenoconazole; phthalide; flutolanil; validamycin; probenazole; diclomezine; pencycuron; dazomet; kasugamycin; IBP; pyroquilon; oxolinic acid; tricyclazole; ferimzone; mepronil; EDDP; isoprothiolane; carpropamid; diclocymet; furametpyr; fludioxonil; procymidone; and diethofencarb.
The present invention is constructed in mere detail by production examples, formulation examples, test examples

and the like.
Firstly, production examples of the present compound are illustrated.
Production Example 1
0.5 g of i-iodo-3,3,3-trifluoropropane and 0.5 g of (3,3,3-trifluoropropylsulfonyl)acetonitrile were dissolved to 20 ml of N,N-dimethylformamide. 0.1 g of sodium hydride [60% in oil) was added thereto at room temperature, and the mixturethe mixture was stirred for 24 hours at the same temperature. Then 10 % hydrochloric acid was added to the reaction mixture and the mixturethe mixture was extracted by ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium chloride, dried over anhydrous magnesium^ sulfate, then concentrated under reduced pressure. The obuained residue was subjected to silica gel chromatography to obtain 1.44 q of 5,5,5-trifluoro-2-(3,3,3-trifluoropropylsulfonyl)pentanenitrile (referred as the present compound (1), hereinafter). The present compound (1)

1H-NMR{CDCl3,TMS):5(ppm)4.00-4.07(m,IH),3.44-3.62 (m,2H) ,2.72-2.8"? lm,2H) ,2.3 6-2.64 (m, 4H)
Production Exam.p 1 e 2
0.7 g of 2,2,3,3,3-pentafluoropropyl

trifluoromethansulfonate and 0.5 g of {3,3,3-trifiuoropropylsulfonyl)acetonitrile were dissolved to 20 ml of N,N-dimethylformamide. 0.3 g of potassium carbonate was added thereto at room temperature, and the mixturethe mixture was stirred for 40 hours at the same temperature. Then 10 % hydrochloric acid was added to the reaction mixture and the mixturethe mixture was eKtracted by ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, then concentrated under reduced pressure. The obtained residue was subj ected to silica gel chromatography to obtain 0.40 g of 4,4,5,5,5-pentafiuoro-2-(3,3/3-trifIuoropropylsulfonyl)pentanenitrile (referred as the present compound (2), hereinafter). The present compound (2)

-H-NMR(CDCl3 ,TMS) :5 (ppm) 4 .22 (dd, IH} , 3 . 54-3 . 72 (m, 2H) , 2 . 76-
3.05 (m,4H)
Production Example 3
0.6 g of l~iodo-3,3y4,4/4-pentafluorobutane and 0.4 g of (3,3,3-trifIuoropropylsulfonyl)acetonitrile were dissolved to 20 ml of N,K-dimethylformamide. 0.09 g of sodium hydride (60% in oil) was added thereto at room tem.perature, and the mixturethe mixture was stirred for 20 hours at the same temperature. Then 10 % hydrochloric acid was added to the reaction mixture and the mixturethe mixrure

was extracted by ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, then concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 1.44 g of 5,5,6,6,6-pentafluoro-2-(3,3,3-trifluoropropylsulfonyl)hexanenitrile (referred as the present compound (3), hereinafter). The present compound (3)

Production Example 4
0.9 g of 2, 2, 3, 3, 4, 4,-a-heptafluorobutyl triiluoromethansulfonate and 0.5 g of (3,3,3-
trifluoropropylsulfonyl)acetonitrile were dissolved to 20 ml of N,N-dimethylformamide. 0.3 g of potassium carbonate was added thereto at room temperature, and the mixturethe mixture was stirred for 2 3 hours at the same temperature. Then 10 % hydrochloric acid was added to the reaction mixture and the mixture was extracted by ethyl acetate. The organic layer was washed with saturated aqu&ous solution of sodium chloride, dried over anhydrous magnesium sulfate, then concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 0.40 g of 4,4,5,5,6,6,6-heptafluoro-2-(3,3,3-trif luoropropylsulfonyl)hexanenitrile {referred as the


Production Example 5
0.8 g of l-iodo-3,3,4,4,5,5,5-heptafluoropentane and 0.5 g of {3,3f3-trifluoropropylsulfonyl)acetonitrile were
dissolved to 20 ml of N, N-dimethylf ormarnide. 0.1 g of sodium hydride (50% in oil) was added thereto at room temperature, and the mixture was stirred for 24 hours at the same temperature. Then 10 % hydrochloric acid was added to the reaction rriixture and the mixture was extracted by ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, then concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 0,45 g of 5,5,6,6,7,7,7-heptafluoro-2-(3,3,3-trifluoropropylsulfonyl)heptanenitrile (referred as the present compound (5), hereinafter). The present compound (5)


Production Example 6
1.3 g of 2,2,3,3,4,4,5,5-octafluoropentyl trifluoromethansulfonate and 0.7 g of (3,3,3-trifluoropropylsulfonyl)acetonitrile were dissolved to 30 ml of N,N-dimethylformamide. 0.5 g of potassium carbonate was added thereto at room temperature, and the mixture was stirred for 20 hours at the same temperature. Then 10 % hydrochloric acid was added to the reaction mixture and the mixture was extracted by ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, then concentrated under reduced pressure. The obtained residue was subj ected to silica gel chromatography to obtain 0.32 g of 4,4,5,5,6,6,7,7-octafluoro-2- (3,3,3-
trifluoropropylsulfonyl)heptanenitrile (referred as the present compound (5), hereinafter). The present compound (6)


and -the mixture was stirred for 6 hours at the same temperature. Then 10 % hydrochloric acid was added to the reaction mixture and the mixture was extracted by ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, then concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 0.59 g of 5,5,6,6,7,7,8,8,8-nonafluoro-2-(3,3,3-trifluoropropylsulfonyl)octanenitrile (referred as the present compound (7), hereinafter). The present compound (7)

Production Example 8
0.6 g of l-iodo-3,3,4,4,4-pentafluorobutane and 0.4 g of (3,3,4,4,4-pentafluorobutylsulfonyl)acetonitrile were dissolved to 50 ml of N,N-dimethylformamide. 0.5 g of sodium, hydride (60 % in oil) was added thereto at room temperature, and the mixture was stirred for 4 days at the same temperature. Then 10 % hydrochloric acid was added to the reaction mixture and the mixture was extracted by ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, then concentrated under reduced pressure. The obtained residue was subjected to silica gel


Production Example 9
0.7 g of 2,2,3,3,4,4,^-heptaflucrobutyl trifluoromethansulfonate and 0.5 g of (3,3,4,4,4-pentafluorobutylsulfonyl)acetonitrile were dissolved to 20 ml of W,N-dimethylformamide. 0.3 g of potassium carbonate was added thereto at room temperature, and the mixture was stirred for 40 hours at the same temperature. Then IC % hydrochloric acid was added to the reaction mixture and the mixture was extracted by ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, then concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 0.38 g of 4,4,5,5,6,6,6-heptafluoro-2-(3,3,4,4,4-pentafluorobutylsulfonyl)hexanenitrile (referred as the present compound (9), hereinafter). The present compound (9)


Prod-uction Example 10
l.S g of l-iodo-3, 3, 4,'5,4-pentafluorobutane and 2.0 g of (3,3,4,4,5,5,5-heptafluoropentylsulfonyl)acetonitrile were dissolved to 50 ml of N,N-dimethylformamide. 0.3 g of sodium hydride (60 % in oil) was added thereto at room temperature, and rhe mixture was stirred for 20 hours at the same remperature. Then 10 % hydrochloric acid was added to the reaction mixture and the mixture was extracted by ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, then concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 1.43 g of 2-(3,3,4,4,5,5,5-heptafluoropentylsulfonyl)-5,5,6,6,6-
per.tailuorohexanenitrile (referred as the present compound (10) , hereinafter) . The present compound (10)


Production Example 11
0.2 g of iodomethane and 0.5 g of S,5,6,6,6-pentafluoro-2- (3,3,S-trifluoropropylsulfonyl)hexanenitriie were dissolved fo 20 ml of N, N-diinethylformamide. 0.06 g of sodi-am hydride (50 % in oil) was added thereto at room temperature, and the mixture was stirred for 20 hours at the same temperature. Then 10 % hydrochloric acid was added to the reaction mixture and the mixture was extracted by ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, then concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 0.35 g of 2-methyl-5,5,5,6,6-pentafluoro-2-(3,3,3-trifluoropropylsulfonyl)hexanenitrile (referred as the present compound (11), hereinafter). The present compound (11)

Production Example 12
0.3 g of iodomethane and 0.7 g of 4,4,5,5,6,6,6-heptafluoro-2-(3,3,3-trifluoropropylsulfonyl)hexanenitrile were dissolved to 30 ml of N,N-dimethylformamide. 0.07 g of sodium hydride (60 % in oil) was added thereto at room temperature, and the mixture was stirred for 24 hours at the same temperature. Then 10 % hydrochloric acid was added to

the reaction mixture and the mixture was extracted by ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, then concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 0.32 g of 4,4,5,5,6,6,6-heptaf luoro-2-me:ihyl-2- (3,3,3-
trifluoropropylsulfonyl)hexanenitrile (referred as the present compound (12), hereinafter). The present compound (12)

Production Example 13
0.2 g of iodomethane and 0.5 g of 5,5,6,6,6-pentafluoro-2-(3,3,4,4,4-
pentafluorobutylsulfonyl)hexanenitrile were dissolved to 20 ml of K,N-dimethylformamide. 0.05 g of sodium hydride (60 % in oil) was added thereto at room temperature, and the mixture was stirred for 20 hours at the same temperature. Then 10 % hydrochloric acid was added to the reaction mixture and the mixture was extracted by ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, then concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain

0.49 q of 2-methyl-5,5,6,5,6-pentafluoro-2-(3,3,4,4,4-pentafluorobutylsulfonyl)hexanenitrile (referred as the present compound (13), hereinafter). The present compound (13)

Production Example 14
0.2 g of iodomethane and 0.5 g of 5,5,6,6,6-pentafiuoro-2- (3,3,4,4,5,5,5~
heptaf luoroper.tylsulfonyl) hexanenitrile were dissolved to 20 ml of N,N-dirriethylformamide. 0.05 g of sodium hydride (60 % in oil) was added thereto at room temperature, and the mixture was stirred for 2 days at the same temperature. Then 10 % hydrochloric acid was added to the reaction mixture and the mixture was extracted by ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, then concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 0.49 g of 2-(3,3,4,4,5,5,5-heptafluoropentylsulfonyl)-2-methyl-5,5,6,6,6-pentafluorohexanenitrile (referred as the present compound (14), hereinafter). The present compound (14)


Production Example 15
0.2 g of iodoethane and 0.5 g of 5,5,5,6,6-pentafluoro-2-(3,3,3-trifluoropropylsulfonyl)hexanenitrile were dissolved to 2 0 ml of N,N-dimethylformamide. 0.06 g of
sodium hydride (60 % in oil) was added thereto at room temperature, and the mixture was stirred for 10 hours at the same temperature. Then 10 % hydrochloric acid was added to the reaction mixture and the m.ixture was extracted by ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, then concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 0.37 g of 2-ethyl-5,5,5,6,6-pentafluoro-2- (3,3,3-trifluoropropylsulfonyl)hexanenitrile (referred as the present compound (15), hereinafter). The present compound (15)


0.2 g of 1-iodopropane and 0.5 g of 5,5,6,6,6-pentafluoro-2- (3,3,3-trifluoropropylsulfonyl)hexanenitrile were dissolved to 20 ml of N,N-diinethylformamide. 0.06 g of sodiurri hydride (60 % in oil) was added thereto at room temperature, and the mixture was stirred for 24 hours at the same temperature. Then 10 % hydrochloric acid was added to the reaction mixture and rhe mixture 'was extracted by ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, then concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 0.38 g of 5,5,6,5, 6-pentafluoro-2-propyl-2- [3,3,3-trifluoropropylsulfonYl)hexanenitrile (referred as the present compound (16), hereinafter). The present compound fl6)

Production Example 17
0.2 g of 2-iodopropane and 0.5 g of 5,5,6,6,6-
pentafluoro-2-(3,3,3-trifluoropropylsulfonyl)hexanenitrile were dissolved to 20 ml of N,N-dimethylformamide. 0.06 g of sodium hydride (62 % in oil) vjas added thereto at roorri temperature, and the mixture was stirred for 6 hours at the same temperature, for 2 hours at 60 °C and for 6 hours at

90 °C. Then 10 % hydrochloric acid was added to the reaction mixture and the mixture was extracted by ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, then concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 0.13 g of 5,5,6,6,6-pentafluoro-2-(2-propyl)-2-(3,3,3-trifluoropropylsulfonyl)hexanenitrile (referred as the present compound (17), hereinafter). The present compound (17)

Production Example 18
0.3 g of 1-iodobutane and 0.5 g of 5,5,6,6,6-pentafluoro-2-(3,3,3-trifluoropropylsulfonyl)hexanenitrile were dissolved to 20 ml of N,N-dimethylformamide. 0.06 g of sodium hydride (60 % in oil) was added thereto at room temperature, and the mixture was stirred for 8 hours at the same temperature. Then 10 % hydrochloric acid was added to the reaction mixture and the mixture was extracted by ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, then concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 0.28 g of 2-butYl-5,5,6,6,6-

pentafluorc-2- (3,3,3-trifluoropropylsulfonyl)hexanenitrile (referred as the present compound (18), hereinafter). The present compound (18)

Production Example 19
0.3 g of 1-iodopentane and 0.5 g cf 5,5,6,6,5-pentafluoro-2-(3,3,3-trifluoropropylsulfonyl)hexanenitrile were dissolved to 20 ml of N,W-dimethylformamide. 0.06 g of sodium hydride (60 % in oil) was added thereto at room temperature, and the mixture was stirred for 20 hours at the same temperature. Then 10 % hydrochloric acid was added to the reaction mixture and the mixture was extracted by ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium chloride, dried over anhydrous m.agnesium sulfate, then concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 0.28 g of 2-(3,3,4,4,4-pentafluorobutyl)-2- (3,3,3-
trifluoropropylsulfonyl)heptanenitrile (referred as the present compound (19), hereinafter). The present compound (19)


Production Example 20
0.5 g of 5,5,6,6,6-pentafluoro-2-(3,3,3-trifluoropropylsuufonyl)hexanenitrile was dissolved to 20 ml of tetrahydrofuran. 0.06 g of sodium hydride {60 % in oil)
was added thereto at 0 'C, and the mixture was stirred for 0.5 hours at the same temperature. Then 0.4 g of 1-fluoro-2,4, 6-trimethylpyridiniurr, trifluoromethanesulfonate was added to the mixture at the same temperature and the mixture was stirred for 0.5 hours. Furthermore, the mixture was stirred at room temperature for 10 hours. After that, 10 % hydrochloric acid was added to the reaction mixture and the mixture was extracted by ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, then concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 0.37 g of 2,5,5,6,6,6-hexafluoro-2-(3,3,3-
trifluoropropylsulfonyl)hexanenitrile (referred as the present compound (20), hereinafter). The present compound (20)


Production Example 21
0.5 g of 5,5,6,6,6-pentafluoro-2-(3, 3, 3-trifluoropropyls-uuforjyl)hex5nenitrile was dissolved to 20 ml of tetrahydrofuran. 0.06 g of sodium hydride (60 % in oil) was added thereto at 0 °C, and the mixture was stirred for 0.5 hours at the same temperature. Then 0.2 g of N-chloro succinimide was added to the mixture at the same temperature and the mixture was stirred for 0.5 hours. Furthermore, the mixture was stirred at room temperature for 3 days. After that, 10 % hydrochloric acid was added to the reaction mixture and the mixture was extracted by ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, then concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 0.15 g of 2-chloro-5,5,6,6,6-hentafluoro-2-{3,3,3-trifluoropropylsulfonyl)hexanenitrile (referred as the present compound 121), hereinafter). The present compound (21}


Production Example 22
2.0 g of 1-10(10-4,4,4-trifluorobutane and 2.0 g of methyl (3,3,3-trifluoropropylsulfonyl)acetate were dissolved to 20 ml of N, N-dimethylformamide. 1.2 g of potassium carbonate was added thereto at room temperature, and the mixture was stirred for 20 hours at the same temperature. Then 10 % hydrochloric acid was added to the reaction mixture and the mixture was extracted by ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, then concentrated under reduced pressure. The obtained residue was subj ected to silica gel chromatography to obtain 0.80 g of methyl 6,6,6-trifluoro-2-( 3,3,3-
trifluoroprcpylsulionyl) hexanoate (referred as the present compound (22) , hereinafter) . The present compound (22}

Production Example 23
1.2 g of l-iodo-S,3,4,4,4-pentafluorobutane and 1.0 g of methyl (3,3,3-trifluoropropylsulfonyl)acetate were dissolved to 20 ml of N,N-dimethylformamide. 0.6 g of
potassium carbonate was added thereto at room temperature, and it was stirred for 30 hours at the same temperature. Then 10 % hydrochloric acid was added to the reaction

mixture and the mixture was extracted by ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, then concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 1.20 g of methyl 5,5,6,6,6-pentafluoro-2-(3,3,3-trifluoropropylsulfonyl) hexanoate (referred as the present compound (23), hereinafter). The present compound (23)

Production Example 24
4.8 g of l-iodo-3,3,4,4,4-pentafluorobutane and 5.0 g of methyl [3,3,4,4,4-pentafluorobutylsulfonyl)acetate were dissolved to 50 ml of N,N-dimethylformamide. 0.7 g of sodium hydride (60 % in oil) was added thereto at room temperature, and the mixture was stirred for 2 days at the same temperature. Then 10 % hydrochloric acid was added to the reaction mixture and the mixture was extracted by ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, then concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 4.69 g of methyl 5,5,6,6,6-pentafluoro-2- {3,3,4,4,4-pentafluorobutylsulfonyl) hexanoate


Production Example 25
0.5 g of 5,5,6,6,6-pentafluoro-2-{3,3,3-
trifluoropropylsulfonyl)hexanoic acid was dissolved to 10 ml cf dichloromethane. 2 drops of N,N-dimethylformamide and 0.2 ml of oxalyl chloride were subsequently added dropwise thereto at room temperature, then the mixture was stirred for 2 hours at the same temperature. Then the reaction mixture was concentrated under reduced pressure. The obtained residue was dissolved to 20 ml of tetrahydrofuran and 0.1 g of tert-butyl alcohol and 0.2 ml of triethylamine were added dropwise at room temperature. The mixture was stirred at the same temperature for 1 hour-. Saturated aqueous solution of aminonium chloride was added to the reaction mixture and the mixture was extracted by ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 0.42 g of tert-butyl 5,5,G,6,6-pentaflucro-2-(3,3,3-trifluoropropylsulfonyl)hexanoate (referred as the present compound (25), hereinafter).


Production Example 26
0.4 g of iodomethane and 1.0 g of methyl 5,5,6,6,6-pentafluoro-2- (3,3, 3-trif luoropropylsulf onyl) haxaniMiOQtre were dissolved to 20 ml of K,N-dimethylformamide. 0.1 g of sodium hydride (60 % in oil) was added thereto at room temperature, and the mixture was stirred for 3 hours at the same temperature. Then 10 % hydrochloric acid was added to the reaction mixture and the mixture was extracted by ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, then concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 0.73 g of methyl 2-methyl-5,5,6,6,G-pentafluoro-2- (3,3,3-
trifluoropropylsulfonyl)hexanoate [referred as the present compound (26), hereinafter). The present compound (26)


Production Example 27
0.4 g of iodoethane and 1.0 g of methyl 5,5,6,6,6-pentafluoro-2- (3,3, 3-trif luoropropylsulf onyl) hoxanan'oato were dissolved to 20 ml of N,N-dimethylformamide. 0.1 g of sodiun) hydride (60 % in oil}- was added thereto at room temperature, and the mixture was stirred for 20 hours at the same temperature. Then 10 % hydrochloric acid was added to the reaction mixture and the mixture was extracted by ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, then concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 0.A5 g of methyl 2-ethyl-5,5,6,6,6-peritafluoro-2-(3,3,3-trifluoropropylsulfonyl)hexanoate (referred as the present compound (27), hereinafter). The present compound (27)

Production Example 28
0.4 g of l-iodopropane and 1.0 g of methyl 5,5,6,6,6-pentafluoro-2- (3, 3, 3-trif luoropropylsulf onyl) hcnanonoQt^y were dissolved to 20 ml of N,N-dimethylformamide. 0.1 g of sodium hydride (50 % in oil) was added thereto at room temperature, and the mixture was stirred for 20 hours at the

same temperature. Then 10 % hydrochloric acid was added to the reaction mixture and the mixture was extracted by ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, then concentrated under reduced pressure. The obtained residue was subjected to silica gel chrorriatography to obtain 0.S9 g of methyl 5,5,6,6,5-pentaflucro~2-propyl-2~(3, 3, 3-
trifluoropropylsulfonyl)hexanoate (referred as the present compound (28), hereinafter). The present compound (2 8)

Production Example 29
0.05 g of sodium hydride (50 % in oil) was added to a solution of 0.5 g of methyl 5,5,6,6,6-pentafluoro-2-(3,3,3-trif luoropropylsulf onyl) hoi^iancnoatc in 20 ml of tetrahydrofuran at 0 °C and the mixture was stirred for 0.5 hours at the same temperature. Then 0.4 g of 1-fluoro-2, 4 , 6-trimethylpyridinium trifluoromethanesulfonate was added thereto and the mixture was stirred for 0.5 hour. Furthermore, the mixture was stirred at room temperature for 10 hours. 10 % hydrochloric acid was added to the reaction m.ixture and the mixture was extracted by ethyl acetate. The organic layer was washed with saturated aqueous solution of

sodium chloride, dried over anhydrous magnesium sulfate,
then concentrated under reduced pressure. The obtained
residue was subjected to silica gel chromatography to obtain
0.39 g of methyl 2,5,5,6,6,6-hexafluoro-2-(3,3,3-
trifluoropropylsulfonyl)hexanoate (referred as the present
compound (29), hereinafter).
The present compound (29)

Production Example 30
0.7 g of iodomethane and 2.0 g of methyl 5,5,6,6,6-pentafluoro-2- (3,3,4,4,4-
pentafluorobutylsulfonyl)hexanenoate were dissolved to 50 ml of N,N-dimethylf ormamide. 0.2 g of sodium hydride (60 % in oil) was added thereto at room temperature, and the mixture was stirred for 4 hours at the same temperature. Then 10 % hydrochloric acid was added to the reaction mixture and the mixture was extracted by ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, then concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 1.20 g of methyl 2-methyl-5,5,6, 6, 6-pentafluoro-2-(3,3, 4,4,4-pentafluorobutylsulfonyl)hexanoate (referred as the present compound (30) , hereinafter) .


Production Example 31
0.5 g of 5,5, 6,6,6-pentafluoro-2-(3,3,3-trifluoropropylsulfonyl)hexanoic acid was dissolved to 10 ml of dichloromethane. 2 drops of N,N-dimethylformamide and 0.2 rrJ of oxalyl chloride were subsequently added dropwise thereto at room temperature, then the mixture was stirred for 2 hours at the same temperature. Then the reaction ir,ixture was concentrated under reduced pressure. The obtained residue was dissolved to 20 ml of tetrahydrofuran and 0.2 g of ammonia (30 % (w/w) aqueous solution) was added dropwise thereto at room temperature. The mixture was stirred at the same temperature for 2 hours, Saturated aqueous solution of ammonium chloride was added to the reaction mixture and the mixture was extracted by ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 0.24 g of 5,5,6, 6, 6-pentafluoro-2-(3,3,3-trifluoropropylsulfonyl)hexanamide (referred as the present compound (31)^ hereinafter). The present compound (31)


NMR(CDCl3,TMS]:5(ppm)6.34(bs,IH),5.73(bs,IH),3.73(dd,IH},3.2 1-3.4 2(m,2H),2.64-2.7 3(m,2H),2.12-2.4 8(m,4H)
Production E^onple 32
0.5 g of 5,5, 6,6,6-pentafluoro-2-(3,3,3-trifluoropropylsulfonyl)hexanoic acid was dissolved to 10 ml of dichloromethane. 2 drops of N,N-dimethylformamide and 0,2 ml ot oxalyl chloride were subsequently added dropwise thereto at room temperature, then the mixture was stirred for 1 hour at the same temperature. Then the reaction mixture was concentrated under reduced pressure. The obtained residue was dissolved to 20 ml of tetrahydrofuran and 0.3 g of methylamine (40 % (w/w) aqueous solution) was added dropwise thereto at room temperature. The mixture was stirred at the same temperature for 2 hours. Saturated aqueous solution of ammonium chloride was added to the reaction mixture and the mixture was extracted by ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 0.26 g of N-methyl-5,5,6,6,6-pentafluoro-2-(3,3, 3-triflucrcpropylsulfonyl}hexanamide (referred as the present compound (32), hereinafter). The present compound (32)


Production Example 33
0.5 g of 5,5,6f6,6-pentafluoro-2-(3,3,3-trifluoropropylsulfonyl)hexanoic acid was dissolved to 10 ml of dichloromethane. 2 drops of N,N-dimethylformamide and 0.2 m] of oxalyl chloride were subsequently added dropwise thereto at room temperature, then the mixture was stirred for 1 hour at the same temperature. Then the reaction mixture was concentrated under reduced pressure. The obtained residue was dissolved to 20 ml of tetrahydrofuran and 0.5 g of dimethylamine (40 % (w/w) aqueous solution) was added dropwise thereto at room temperature. The mixture was stirred at the same temperature for 2 hours. Saturated aqueous solution of ammonium chloride was added to the reaction mixture and the mixture was extracted by ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 0.30 g of N, N-dimethyl-5,5,6,6,6-pentafluoro-2-[3,3,3-trifluoropropylsulfonyl)hexanamide (referred as the present compound (33), hereinafter). The present compound (33)


production Example 34
1.l g of 2-methyl-5, 5, 6,6, 6-per)tafluoro-2-(3,3, 3-trifluoropropylsulfonyl)hexanoic acid was dissolved to 20 ml of dichloromethane. 2 drops of N,N-dimethylformamide and 0.5 ml of oxalyl chloride was subsequently added dropwise ::hereto at room cemperature, then the mixture was stirred for 2 hours at the same temperature. Then the reaction m.ixture was concentrated under reduced pressure. The obtained residue was dissolved to 20 ml of tetrahydrofuran and 0.5 g of ammonia (30 % (w/w] aqueous solution} was added dropwise thereto at room temperature. The mixture was stirred at the same temperature for 2 hours. Saturated aqueous solution of ammonium chloride was added to the reaction mixture and the mixture was extracted by ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 0.76 g of 2-methyl-5,5,6,6,6-pentaflucrc-2- (3,3,3-trifluoropropylsulfonyl)hexanamide (referred as the present compound (34), hereinafter}. The present compound (34)


Production Example 35
1.1 g of 2-methyl-5,5,6,6,6-pentafluoro-2-{3,3,3-trifluoropropylsulfonyl)hexanoic acid was dissolved to 20 ml of dichloromethane. 2 drops of N,H-dimethylformamide and
0,5 ml of oxalyl chloride was subsequently added dropwise thereto at room temperature, then the mixture was stirred for 2 hours at the same temperature. Then the reaction mixture was concentrated under reduced pressure. The obtained residue was dissolved to 20 ml of tetrahydrofuran and 0.7 g of methylamine (30 % (w/w) aqueous solution) was added dropwise thereto at room temperature. The mixture was stirred at the same temperature for 2 hours. Saturated aqueous solution of ammonium chloride was added to the reaction mixture and the mixture was extracted by ethyl acetate, The organic layer was washed with saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 0.70 g of N-methyl~2-methyl-5, 5, 6, 6,6-pentafluoro-2-(3,3,3-
trif luoropropylsulfonyl) hexanamide (referred as the present compound (35), hereinafter). The present compound (35)


Production Example 5 6
0.5 g of 5,5,6,6,6-pentafluoro-2-(3,3,3-trifluoropropylsulfonyl)hexanoic acid was dissolved to 10 ml
of diohloromethane. 2 drops of N,N-dimethylformamide and 0.2 ml of oxalyl chloride was subsequently added dropwise thereto at room temperature, then the mixture was stirred for 1 hour at the same temperature. Then the reaction mixture was concentrated under reduced pressure. The obtained residue was dissolved to 2 0 ml of tetrahydrofuran and 1.0 g of dimethylamine (40 % (w/w) aqueous solution) was added dropwise thereto at room temperature. The mixture was stirred at the same temperature for 4 hours. Saturated aqueous solution of ammonium chloride was added to the reaction mixture and the mixture was extracted by ethyl acetaue. The organic layer was washed with saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 0.97 g of 5,5,6,6,6-pentafluoro-2-(3, 3,3-trifluoropropylsulfonyl)-N,N-2-dimethyl-2-methylhexanaraide (referred as the present compound (36), hereinafter).


Production Example 37
0.5 g of 2-methyl-5,5, 6, 6, 6-pentaflvoro~2- (3,3,3~ trifluoropropylsulfonyl)hexanoic acid was dissolved to 20 ml
of dichloromethane . 1 drop of N, N-dimethylf ormamide and 0.2 ml of oxalyi chloride were subsequently added dropwise thereto at room temperature, then the mixture was stirred for 2 hours at the same temperature. Then the reaction m.ixture was concentrated under reduced pressure. The obtained residue was dissolved to 20 ml of tetrahydrofuran and 0.2 g of ethylamine {70 % (w/w) aqueous solution) was added dropwise thereto at room temperature. The mixture was stirred at the same temperature for 8 hours. Saturated aqueous solution of ammonium chloride was added to the reaction mixture and the mixture was extracted by ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 0.41 g of N-ethyl-2-methyl-5,5,6,6,6-pentafluoro-2-(3,3,3-
trifluoropropylsulfonyl)hexanamide (referred as the present compound (37), hereinafter).


Production Example 38
0.5 g of 2-ethyl~5,5,6,6,6-pentafluoro-2-(3,3,3-trif luoropropylsulfonyl) hexanoic acid was dissolved to 20 ml of dichloromethar.e . 1 drop of N, N-dimethylformamide and 0.2 ml of oxalyl chloride was subsequently added dropwise thereto at room temperature, then the mixture was stirred for 2 hours at the same temperature. Then the reaction m.ixture was concentrated under reduced pressure. The obtained residue was dissolved T:O 20 ml of tetrahydrofuran and 0.2 g of ammonia (30 % (w/w) aqueous solution) was added dropwise thereto at room temperature. The mixture was stirred at the same temperature for 1 hour. Saturated aqueous solution of ammonium chloride was added to the reaction mixture and the mixture was extracted by ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 0.37 g of 2-ethyl-5,5,6,6,6-pentafluoro-2- (3,3,3-triflucropropylsulfonyI)hexanamide
(referred as the present compound (38), hereinafter).
The present compound (38)


Production Example 39
0.6 g of l-iodo-4,4,4-trifluorobutane and 0.5 g of
(3,3,3-trifluoropropylsulfonyi)acetonitrile were dissolved to 20 ml of N, N-diraethylformainide. 0.1 g of sodium hydride
'60 % in oil) was added thereto at room temperature, and the mixture was stirred for 10 hours at the same temperature. Then 10 % hydrochloric acid was added to the reaction mixture and the mixtisre was extracted by ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, then concentrated under reduced pressure, The obtained residue was subjected to silica gel chromatography to obtain 0.57 g of 6,6,6-trifluoro-2~(3,3,3-trifluoropropylsulfonyl) hexanenitrile (referred as the present compound (39), hereinafter). The present compound (39)


0.5 g of 2-methyl-5,5,6,6,6-pentafluoro-2-(3,3,3-trifluoropropylsulfonyhexanoic acid was dissolved to 20 ml of dichloromethane. 2 drops of N,N-dimethylformamide and 0.2 ml of oxalyl chloride were subsequently added dropwise
thereto at room temperature, then the mixture was stirred for 2 hours at the same temperature. Then the reaction mixture was concentrated under reduced pressure. The obtained residue was dissolved to 20 ml of tetrahydrofuran and 0.2 g of propylamine was added dropwise to it. The mixture was stirred at the same temperature for 14 hours. Saturated aqueous solution of ammonium chloride was added to the reaction mixture and the mixture was extracted by ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 0.26 g of 2-methyl-N-propyl-5,5,6,6,6-pentafluoro-2-(3,3,3-
trifluoropropylsulfonyDhexanaraide (referred as the present compound (40), hereinafter). The present compound (40)


trifluoropropylsulfonyDhexanoic acid wa-s dissolved to 20 ml of dichloromethane. 2 drops of N.N-dimethylformamide and 0.2 ml of oxalyl chloride were subsequently added dropwise thereto at room temperature, then the mixture was stirred for 2 hours at the same temperature. Then the reaction mixture was concentrated under reduced pressure. The obtained residue was dissolved to 20 ml of tetrahydrofuran and 0.2 g of isopropylamine was added dropwise thereto at room temperature. The mixture was stirred at the same temperature for 14 hours. Saturated aqueous solution of aTniTionium chloride was added to the reaction mixture and the mixture was extracted by ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 0.25 g of N-isopropyi-2-raethyl-5,5,G,6,6-pentafluoro-2-(3,3,5-trifluoropropylsulfonyDhexanamide (referred as the present compound (41) , hereinafter) . The present compound (41)


Of niethyl (3, 3, 4, 4, 5, 5, S-heptafluoropentylsulfonyl} acetate were dissolved to 20 ml of N,N-dimethylformamide. 0.1 g of sodium hydride (60 % in oil) was added thereto at room temperature, and the mixture was stirred for 3 days at the same temperature. Then 10 % hydrochloric acid was added to the reaction mixture and the mixture was extracted by ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, then concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 1.12 g of methyl 2-(3,3,4,4,5,5,5-heptafluoropentylsulfonyl)-5, 5, 6, 6, 6-pentafluorohexanoate (referred as the present compound (42), hereinafter). The present compound (42)

Production Example 43
0.2 g of iodomethane and 0.6 g of methyl 2-(3,3,4,4,5,5,5-heptafluoropentylsulfonyl)-5,5,6,6,6-pentafluorohexanoate were dissolved to 20 ml of N,N-dimethylformamide. 0.1 g of sodium hydride (60 % in oil) was added thereto at room temperature, and the mixture was stirred for 10 hours at the same temperature. Then 10 % hydrochloric acid was added to the reaction mixture and the mixture was extracted by ethyl acetate. The organic layer

was washed with saturated aqueous solutxon of sodium. chloride, dried over anhydrous magnesium sulfate, then concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain O.41 g of methyl 2-(3,3,4,4,5,5,5-heptafluoropentylsulfonyl)-2-
methyl-5,5,6,6,6-pentafluorohexanoate (referred as the
present coinpound (43), hereinafter).
The present compound (43)

Production Example 44
0.4 g of iodomethane and 1.0 g of methyl 6,6,6-trifluoro-2- (3,3,3-trifluoropropylsulfonyl)hexanoate were dissolved to 20 ml of N,N-dimethylformamide. 0.1 g of sodium hydride (60 % in oil) was added thereto at room temperature, and the mixture was stirred for 10 hours at the same temperature. Then 10 % hydrochloric acid was added to the reaction mixture and the mixture was extracted by ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, then concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 0.85 g of methyl 2-methyl-6,6,6-trifluoro-2- [3,3,3-trifluoropropylsulfonyl)hexanoate (referred as the present compound (44), hereinafter).


Production Example A5
0.2 g of iodomethane and 0.5 g of 6, 6, 6-trifluoro'2-(3,3,3-trifluQropropylsulfonyl)hGxanenitrile were dissolved
to 20 ml of N,N-dimethylformamide. 0.06 g of sodium hydride (60 % in oil) was added thereto at room temperature, end the mixture was stirred for 10 hours at the same temperature. Then 10 % hydrochloric acid was added to the reaction mixture and the mixture was extracted by ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, then concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 0.3V g of 2-raethyl-6,6,6-trifluoro-2-(3,3,3-trifluoropropylsulfonyl)hexanenitrile (referred as the present compound (45), hereinafter). The present compound (45)


Production Example 4 6
1.0 g of l-iodo--3,3,4,4,4-pentafluorobutane and 1.0 g of ethyl 2-(3,3,3-trifluoropropylsulfonyl)propionate were dissolved to 20 ml of dimethylsulfoxide. 0.2 g of sodium hydride (60 % in oil) was added thereto at room temperature, and the mixture was stirred for 10 hours at the same temperature, for A hours at 60 °C then for 4 hours at gO^C. After that, the reaction mixture was cooled to room temperature, then 10 % hydrochloric acid was added to the reaction mixture and the mixture was extracted by ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, then concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain O.47 g of ethyl 2-methyl-5,5,6,6,5-pentafluoro-2-(3,3,3-tri£luoropropylsulfonyl)hexanoate (referred as the present compound (46), hereinafter). The present compound (45)


dropwise with 2.0 g of 2-bromo-5,5,6,6,6-
pentafluorohexanenitrile at the same temperature, followed by stirring at room temperature for 0.5 hours. The reaction mixture was added with 10 % hydrochloric acid, followed by extraction with ethyl acetate. The organic layer was subsequently washed with 10 % hydrochloric acid and saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The obtained residue was subjected to a silica gel chromatography to obtain 1.6 g of 5,5,6,6,6-pentafluoro-2-(3,3,3-trifluoropropylthio) hexanenitrile (referred as the present compound (47), hereinafter) .

Production Example 48
After dissolving 0.5 g of S-(3,3, 3-trifluoropropyl) benzenethioate to 20 ml of tetrahydrofuran, this solution was added with 0.4 ml of sodium methoxide (28 % (w/w) methanol solution) under ice cooling; and then being added dropwise with 0.6 g of 2-bromo-5,5,6,6, 6-
pentafluorohexanenitrile at the same temperature, followed by stirring at room temperature for 1 hour. The reaction mixture was added with 10 % hydrochloric acid, followed by extraction with ethyl acetate. The organic layer was

subsequently washed with 10 % hydrochloric acid and saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The obtained residue was dissolved to 20 ml of chloroform, added with 0.5 g of peracetic acid (32 % (w/w) acetic acid solution) under ice cooling, and then stirred at the same temperature for 4 hours. The reaction mixture was raised to room temperature, and poured into water, then the mixture was extracted by ethyl acetate. The organic layer was subsequently washed with saturated aqueous solution of sodium hydrogencarbonate and saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 0.4 g of 5, 5, 6, 5, S-pentaf luoro-2-(3, 3, 3-trifluoropropylsulfinyl)
hexanenitrile (referred as the present compound (48), hereinafter). The present compound (48)

Production Example 4 9
1.1 g of 2-methyl-5,5,6,6,6-pentafluoro-2- O.B.B-trifluoropropylsulfonyDhexanoic acid was dissolved to 20 ml of dichloroTT.ethane. This solution was subsequently added

dropwise with 2 drops of N,N-dimethylformamide and 0.5 mi of oxalyl chloride at room temperature, and then stirred at the same temperature for 2 hours. The reaction mixture was concentrated under reduced pressure. The obtained residue was dissolved to 20 ml of tetrahydrofuran, followed by dropwise addition of 0.5 g of ammonia (30 % (w/w> aqueous solution) St room temperature; and then being stirred at the same temperature for 10 hours. The reaction mixture was added with saturated aqueous solution of ammonium chloride, followed by extraction with ethyl acetate. The organic layer was concentrated under reduced pressure. The obtained residue was added with the mixture of 1.2 g of 2,4-bis(4-methoxyphenyl)-1,3-dithia-2,^-diphosphetane 2,4-disulfide and 20 ml of toluene, followed by heating under refluxing for 10 hours. The reaction mixture was dropped to a room temperature, followed by concentration under reduced pressure. The obtained residue was subjected to a silica gel chromatography to obtain 0.47 g of 2-methyl-5,5,5,6,6-pentafluoro-2- (3,3,3-
trifluoropropylsulfonyl)hexanthioamide (referred as the present compound (49), hereinafter). The present compound (49)


After dissolving 0.5 g of 5,5,6,5,6-pentafluoro-2-(3,3,B-trifluoropropylthio)
hexanenitrile and 0.2 g of iodomethane with 20 ml of tetrahydrofuran, this solution was added with 1.6 ml of sodium bis(trimethylsilyl)amide (1 M tetrahydrofuran solution) at -78 "C. This mixture was stirred at the same temperature for 0.5 hours. The reaction mixture was added with 10 % hydrochloric acid, followed by extraction with ethyl acetate. The organic layer was subsequently washed with 10 % hydrochloric acid and saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The obtained residue was subjected to a silica gel chromatography to obtain 0.4 g of 2-methyl-5,5,6,6, 6-pentafluoro-2-(3,3,3-trifluoropropylthic}hexanenitrile (referred as the present compound (50), hereinafter).

Production Example 51
5.7 g of l-iodo-3,3,4,4, 5, 5, 5-heptafluoropentane and 5.0 g of methyl (3,3,4,4,4-pentafluorobutylsulfonyl)acetate were dissolved to 50 ml of N,N-dimethylformamide. This solution was added with 0.7 g of sodium hydride (60 % in oil) at room: temperature, followed by stirring at the same temperature for 3 days. The reaction mixture was added with

10 % hydrochloric acid, followed by extraction with ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The obtained residue was subjected to a silica gel chromatography to obtain 1,80 g of methyl 5,5,6,6,7,7,7-heptafluoro-2- (3, 3, •3, 4, 4-
pentafluorobutylsulfonyl)heptanoate (referred as the present compound (51), hereinafter). The present compound (51)

Production Example 52
0.4 g of iodomethane and 1.3 g of methyl 5,5,6,6,7,7,7-heptafluoro-2-(3,3,4,4,4-
pentafluorobutylsulfonyl)heptanoate were dissolved to 50 ml of N,N-dimethylforraamide. This solution was added with 0.1 g of sodium hydride (60 % in oil) at room temperature, followed by stirring at the same temperature for 3 hours. The reaction mixture was added with 10 % hydrochloric acid, followed by extraction with etbyl acetate. The organic layer was washed with saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The obtained residue was subjected to a silica gel chromatography to obtain 1.30

g of methyl 5, 5, 6, 6, 7, 7, 7-heptafluoro-2-methyl-2-(3, 3, 4, 4,-3-pentafluorobutylsulfonyl)heptanoate (referred as the present compound (52), hereinafter). The present compound (52)

Production Example 53
0.4 g of l-iodo-3r3,3-trifluoropropane and 0.5 g of
(3,3,4,4,4-pentafluorobutylsulfonyl)acetonitrile were dissolved to 20 ml of NfN-dimethylformamide. This solution was added with 0.08 g of sodium hydride (50 % in oil) at room temperature, followed by stirring at the same temperature for 20 hours. The reaction mixture was added with 10 % hydrochloric acid, followed by extraction with ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The obtained residue was subjected to a silica gel chromatography to obtain 0.26 g of 2-(3,3,4,4,4-pentafluorobutylsulfonyl)-5,5,5-trifluoropentanenitrile (referred as the present compound
(53), hereinafter).
The present compound (53)


Production Example 54
0.6 g of l-iodo-3,3,4,4,5,5,5-heptafluoropentane and 0.5 g of (S/SMf'i, 4-pentafluorobutylsulfonyl) acetonitrile were dissolved to 20 ml of N,N-dimethylformamide. This solution was added with 0.08 g of sodium hydride [60 % in oil) at room temperature, followed by stirring at the same temperature for 2 4 hours, The reaction mixture was added with 10 % hydrochloric acid, followed by extraction with ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The obtained residue was subjected to a silica gel chromatography to obtain 0.30 g of 5,5,6,6,7,7,7-heptafluoro-2- (3,3,4,4,4-
pentafluorobutylsulfonyl)heptanenitrile (referred as the present compound (54), hereinafter). The present compound (54)


Production Example 55
0.5 g of 5,5,6,6,7,7,~heptafluoro-2-^3,3,4,4,4-pentaf luorobutylsulfonyl} heptanoic acid was dissolved to 20 ml of dichloromethane. This solution was subsequently added dropwise with 2 drops of N,N-dimethylformamide and 0.1 ml of Qxaiyl chloride at room temperature, and then stirred at the same temperature for 2 hours. The reaction mixture was concentrated .under reduced pressure. The obtained residue was dissolved to 20 ml of tetrahydrofuran, followed by dropwise addition of 0.2 g of ammonia (30 % (w/w) aqueous solution) at room temperature; and then being stirred at the same temperature for 2 hours. The reaction mixture was added with saturated aqueous solution of ammonium chloride, followed by extraction with ethyl acetate. The organic layer was concentrated .under reduced pressure. The obtained residue was subjected to a silica gel chromatography to obtain 0.31 g of 5,5,6,6,7,7,7-heptafluoro-2-(3,3,4,4,4-pentafluorobutylsulfonyl)heptaneamide (referred as the present compound (55), hereinafter). The present compound (55)

Production Example 5 6
1.1 g of 5, 5, 6, 6,7,7,7-heptafluoro-2-methyl-2-(3,3,4,4,4-

pentaf luorobutylslfonyl) heptanoic acid was dissolved to 20 ml of dichloromethane. This solution was subsequently added dropwise with 2 drops of N,N-dimethylformamide and 0.4 ml of oxalyl chloride at room temperature, and then stirred at the same temperature for 2 hours. The reaction mixture was concentrated under reduced pressure. The obtained residue was dissolved to 50 ml of tetrahydrofuran, followed by dropwise addition of 0.4 g of ammonia (30 % (w/w) aqueous solution) at room temperature; and then being stirred at the same temperature for 2 hours. The reaction mixture was added with saturated aqueous solution of ammonium chloride, fcllowed by extraction with ethyl acetate. The organic layer was coricentrated under reduced pressure. The obtained residue was subjected to a silica gel chromatography to obtain 0.60 g of 5,5,5,6,7,7,7-heptafluoro-2-methyl-2-{3, 3,4,4,4-
pentafluorobutylsulfonyl)heptaneamide (referred as the present compound (56) , hereinafter) . The present compound (56)


this solution was added with 0.4 g of peracetic acid (32 % (w/w) acetic acid solution) under ice cooling, stirred at the same temperature for 2 hours, and then further stirred at room temperature for 10 hours. The reaction mixture was poured into water, followed by extraction with ethyl acetate. The organic layer was subsequently washed with saturated aqueous solution of sodium hydrogencarbonate and saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The obtained residue was subjected to a silica gel chromatography to obtain 0.25 g of 2-methyl-5,5,6,6,5-pentafluoro-2-{3,3,3-
trifluoropropylsulfinyl)hexanenitrile (referred as the present compound (57), hereinafter). The present compound (57)

Production Example 58
0.8 g of methyl 5,5,6,6,6-pentafluoro-2-(3, 3 , 3-trifluoropropylsulfonyl)
hexanoate was dissolved to 50 ml of tetrahydrofuran. This solution was added with 0.08 g of sodium hydride (60 % in oil) at room temperature, followed by stirring at the same temperature for 0.5 hours; and then being added with 0.3 g of N-chlorosuccinimide at the same temperature, followed by

stirring for 4 hours. The reaction mixture was added with 10 % hydrochloric acid, followed by extraction with ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The obtained residue was subjected to a silica gel chromatography to obtain 0.60 g of methyl 2-chloro-5,5,6,6, 6-pentaf l-uoro-2- (3,3,3-
trifluoiropropylsulfonyl) hexanoate (referred as the present compound (58), hereinafter). The present compound (58)

Production Example 59
0.5 g of methyl 2-chloro-5,5,6, 6,6-pentafluoro-2-(3,3,3-
trifluotopropylsulfonyl)hexanoate was dissolved to 50 ml of methanol. This solution was added with 0.5 ml of ammonia (7 M methanol solution) at room temperature, followed by stirring at the same temperature for 2 hours. The reaction mixture was concentrated under reduced pressure. The obtained residue was subjected to a silica gel chromatography to obtain 0.15 g of 2-chloro-5,5,6,6,6-pentaf l-aoro-2- (3, 3, 3-trifluoropropylsulfonyl)hexanamide (referred as the present


Production Example 60
0.5 g of 5,5,6,6,6-pentafluoro-2-(3,3,4,4,4-pentafluorobutylsulfonyl)hexanoic acid was dissolved to 20 ml of dichloromethane. This solution was subsequently added dropwise with 2 drops of N,N-dimethylformamide and 0.2 ml of cxalyl chloride at room temperature, followed by stirring at the same temperature for 4 hours. The reaction mixture was concentrated under reduced pressure. The obtained residue was dissolved to 20 ml of tetrahydrofuran, followed by dropwise addition of 0.2 g of ammonia (30 % (w/w) aqueous solution) at room temperature; and then being stirred at the same temperature for 2 days. The reaction mixture was added with saturated aqueous solution of ammonium chloride, followed by extraction with ethyl acetate. The organic layer was concentrated under reduced pressure. The obtained residue was subjected to a silica gel chromatography to obtain 0.20 g of 5,5,6,6,6-pentafluoro-2-(3,3,4,4,4-pentafluorobutylsulfonyl)hexanamide (referred as the present compound (60), hereinafter). ■ The present compound (60)


Production Example 61
0.3 g of 2-methyl-5,5,6,6,6-pentafluoro-2-(3,3,4,4,4-pentaf luorobutylsulfonyl) hexanoic acid was dissolved to 20 ml of dichloromethane. This solution was subsequently added dropwise with 2 drops of N,N-dimethylformamide and 0.3 ml of oxalyl chloride at room temperature, followed by stirring at the same temperature for 4 hours. The reaction mixture was concentrated under reduced pressure. -The obtained residue was dissolved to 20 ml of tetrahydrofuran, followed by dropwise addition of 0,3 g of ammonia (30 % (w/w) aqueous solution) St room temperature; and then being stirred at the same temperature for 2 days. The reaction mixture was added with saturated aqueous solution of ammonium chloride, followed by extraction with ethyl acetate. The organic layer was concentrated under reduced pressure. The obtained residue was subjected to a silica gel chromatography to obtain 0.60 g of 2-methyl-5,5,6,6,6-pentafluoro-2-(3,3,4,4,4-
pentafluorobutylsulfonyl)hexanamide (referred as the present compound (61), hereinafter). The present compound (61}


Production Example 62
After dissolving 2.0 g of" 5,5,6, 6, 6-pentafluoro-2-(3,3,3-trifluoropropylthio)
hexanenitrile with 50 ml of methanol, this solution was added with 12.5 ml of sodium methoxide (28 % (w/w) methanol solution) at room temperature, followed by stirring at the same temperature for 15 hours. This reaction mixture was added with 10 % hydrochloric acid, followed by extraction with ethyl acetate. The organic layer was subsequently washed with 10 % hydrochloric acid and saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The obtained residue was subjected to a silica gel chromatography to obtain 0.8 g of methyl 5,5,6,6,6-pentailuoro-2-(3,3,3-trifluoropropylthio)hexanoate (referred as the present compound (62), hereinafter). The present compound (62)

-K'Nl^R[CDCl3 ,TMS) :5 (ppm) 3.79(s,3H), 3.31(t,lH), 2.72-2.S0(m,2H}, 1.93-2.48(m,6H)

production Example 63
After dissolving 0.3 g of methyl 5,5,6,6,6-pentafluoro-2-(3,3,3-trifluoropropylthio)hexanoate with 20 ml of chloroform, this solution was added with 0.2 g of peracetic acid (32 % (w/w) acetic acid solution) under ice cooling, followed by stirring at room temperature for 6 hours. The reaction m.ixture was poured into water, followed by extraction with ethyl acetate. The organic layer was subsequently washed with saturated aqueous solution of sodium hydrogencarbonate and saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The obtained residue was subjected to a silica gel chromatography to obtain 0.18 g of methyl 5,5,6,6,6-pentafluoro-2-(3,3,3-trifluoropropylsulfinyl)
hexanoate (referred as the present compound (63), hereinafter). The present compound (63)

Production Example 64
0.5 g of methyl 2,5,5,6,6,6-hexafluoro-2-(3,3,3-
trifluoropropylsulionyl)
hexanoate was dissolved to 20 ml of methanol. This solution
was added with 0.5 ml of ammonia (7 M methanol solution) at

room temperature, followed by stirring at the same temperature for 0.5 hours; and then being further added with 5 ml of ammonia (7 M methanol solution), followed by stirring at the same temperature for 2 hours. The reaction mixture was concentrated under reduced pressure. The obtained residue was subjected to a silica gel chromatography to obtain 0.37 g of 2,5,5,6,6,6-hexafluoro-2-(3, 3, 3-trifluoropropylsulfonyl)
hexanamide (referred as the present compound (54), hereinafter) . The present compound (54]

Production Example 65
2.0 g of methyl 5,5,6,6,6-pentafluoro-2-(3,3, 3-trifluoropropylsulfonyl)
hexanoate was dissolved to 50 mil of tetrahydrofuran. This solution was added with 0.21 g of sodium hydride {60 % in oil) under ice cooling, followed by stirring at the same temperature for 0.5 hours; and then being added with 0.9 g of N-bromosuccinimide, followed by stirring at room temperature for 12 hours. The reaction mixture was added with 10 % hydrochloric acid, followed by extraction with ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium chloride, dried over anhydrous

magnesium sulfate, and then concentrated under reduced
pressure. The obtained residue was subjected to a silica
gel chromatography to obtain 0.30 g of methyl 2-bromo-
5,5,6,6, 6-pentafluoro-2- (3, 3, 3-
trifluoropropylsulfonyl)hexanoate (referred as the present
compound (65), hereinafter).
The present compound (65)

Production Example 65
1.0 g of methyl 2-(3,3,4,4,5,5,5-heptafluoropentylsulfonyl)-5,5,6,6, 6-pentafluorohexanoate was dissolved to 50 ml of tetrahydrofuran. This solution was added with 0.08 g of sodium hydride (60 % in oil) at 0 "C, followed by stirring at the same temperature for 0.5 hours; and subsequently being added with 0.6 g of 1-fluoro-2,4,6-trimethylpyridiniura trifluoromethanesulfonate at the same temperature, followed by stirring for 1 hour. The reaction mixture was added with 10 % hydrochloric acid, followed by extraction with ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The obtained residue was subjected to a silica gel chromatography to obtain 0.75 g of methyl 2-(3,3,4,4,5,5,5-heptafluoropentylsulfonyl)-


Production Example 67
1.5 g of methyl 2-(3 , 3 , 4 /'^ . 5, 5, 5-heptafluoropentylsulfonyl)-2, 5, 5, 6, 6, 6-
hexafluorchexanoate was dissolved to 30 ml of methanol. This solution was added with 1.3 ml of ammonia (7 M methanol solution) at room temperature, followed by stirring at the same temperature for 24 hours. The reaction mixture was concentrated under reduced pressure. The obtained residue was subjected to a silica gel chromatography to obtain 1.10 g of 2-(3,3,4,4,5,5,5-heptafluoropentylsulfonyl)-2,5,5,5,6,6-
hexafluorohexanamide {referred as the present compound (67), hereinafter). The present compound (57)


Production Example 68
After dissolving 0.3 g of methyl 5,5,6,6,6-pentafluQro-2-(3,3,3-trifluoropropylthio)hexanoate and 0.12
g of iodomethane with 20 ml of tetrahydrofuran, this mixture was added with 0.9 ml of sodi\im bis (trimethylsil^j'l) amide (1 M tetrahydrofuran solution) at 0 "C. The mixture was stirred at the same temperature for 1 hour. The reaction mixture was added with 10 % hydrochloric acid, followed by extraction with ethyl acetate. The organic layer was subsequently washed with 10 % hydrochloric acid and saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The obtained residue was subjected to a silica gel chromatography to obtain 0.3 g of methyl 2-methyl-5,5,6,6,6-pentafluoro-2-(3,3, 3-
trifluoropropvlthio)hexanoate (referred as the present compound (68), hereinafter).

Production Example 69
1.0 g of methyl 2,5,5,6,6,6-hexafluoro-2-(3,3,3-
trifluoropropyisulfonyl)
hexanoate was dissolved to 30 ml of methanol. This solution
was added with 3.8 ml of methylamine [2 M m,ethanol solution)

at room temperature, followed by stirring at the same temperature for 2 hours. The reaction mixture was concentrated under reduced pressure. The obtained residue was subjected to a silica gel chromatography to obtain 0.92 g of 2,5,5,6,6,6-hexafluoro-N-raethyl-2-(3,3,3-trif luoropropylsulf onyl) hexanamide (referred as the present compound (69), hereinafter). The present compound (69)

Production Example 70
After dissolving 1.0 g of methyl 2-methyl-5,5,6,6,6-pentafluoro-2-(3,3,3-
■crifluoropropylthio)hexanoate with 50 ml of methanol, this solution was added with an aqueous solution of potassium hydroxide (a mixed solution of 0.9 g of potassium hydroxide and 5 ml of water) at room temperature, and then stirred at the same temperature for 1 day. The reaction mixture was added with 10 % hydrochloric acid, followed by extraction with ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The obtained residue was dissolved to 20 ml of dichloromethane; and then being subsequently added drcpwise with 2 drops of N,N-dimethylformamide and 0.4 ml of

oxalyl chloride at room temperature, and then stirred at the same temperature for 1 hour. The reaction mixture was concentrated under reduced pressure. The obtained residue was dissolved to 20 ml of tetrahydrofuran, and then added dropwise with 0.4 g of ammonia (30 % (w/w) aqueous solution) at room temperature; and then being stirred at the same temperature for 1 hour. The reaction mixture was added with saturated aqueous solution of ammonium chloride, followed by extraction with ethyl acetate. The organic layer was concentrated under reduced pressure. The obtained residue was subjected to a silica gel chromatography to obtain 0.25 g of 2-methyl~5,5,6,6,6-pentafluoro-2-(3,3,3-trifluoropropylthio)hexanamide (referred as the present compound (70), hereinafter).

Producticn Example 71
After dissolving 4.4. g of methyl 2-methyl-5, 5, 6, 6, 6-pentafluoro-2-(3,3,3-
trifluoropropylthio)hexanoate with 30 ml of chloroform, this solution was added with 2.9 g of peracetic acid (32 % (w/w) acetic acid solution) under ice cooling, and then being stirred at the same temperature for 4 hours. The reaction mixture was poured into water, followed by extraction with ethyl acetate. The organic layer was subsequently washed

with saturated aqueous solution of sodium hydrogencarbonate and saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The obtained residue was subjected to a silica gel chromatography to obtain 1.10 g of methyl 2-methyl-5,5,6,6,6-pentafluoro-2-(3,3,3-
trifluoropropylsulfinyl)hexanoate (referred as the present compound (71i, hereinafter). The present compound (71)

Production Example 72
1.0 g of methyl 2-(3,3,4,4 , 4-pentafluorobutylsulfonyl)-5,5,6,6,6-pentafluorohexanoate was dissolved to 50 ml of tetrahydrofuran. This solution was added with 0.09 g of sodium hydride (60 % in oil) at room temperature, and then stirred at the same temperature for 0.5 hours; and subsequently toeing added with 0.7 g of 1-fluoro-2,4,5-trimethylpyridinium trifluoromethanesulfonate at the same temperature, followed by stirring for 3 hours. The reaction mixture was added with 10 % hydrochloric acid, followed by > extraction with ethyl acetate.
The organic layer was washed with saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate.

and then concentrated under reduced pressure. The obtained residue was subjected to a sili.ca gel chromatography to obtain 0.78 g of methyl 2,5,5,6,6,6-hexafluoro-2-(3,3,4,4,4-pentafluorobutylsulfonyl)hexanoate (referred as the present
compound (72), hereinafter). The present compound (72)

Production Example 73
0.6 g of methyl 2, 5, 5, 6, 6, 6-hexaf luoro-2-(3, 3, ^3, 4, 4-pentailuorobutylsulfonyl)hexanoate was dissolved to 2 0 ml of methanol- This solution was added with 0.6 ml of ammonia (7 M methanol solution) at room temperature, and then stirred at the same temperature for 12 hours. The reaction mixture was concentrated under reduced pressure. The obtained residue was subjected to a silica gel chromatography to obtain 0.45 g of 2,5,5,6,6,6-hexafluoro-2-(3,3,4,4,4-pentafluorobutylsulfonyl)hexanamide (referred as the present compound (73) , hereinafter) . The present compound (73)


Production Example 14
After dissolving 0.5 g of methyl 2,5,5,6,6,6-hexafluoro-2-{3,3,3-trifluoropropylsulfonyl) hexanoate with 30 ml of methanol, this solution was added with an aqueous solution of potassium hydroxide{a mixed solution of 0.4 g of potassium hydroxide and 5 ml of water) at roorr, temperature, followed by stirring at the same temperature for 12 hours. The reaction mixture was added with 10 % hydrochloric aoid, followed by extraction with ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure, The residue was dissolved to 2 0 ml of dichloromethane; and then being subsequently added dropwise with 2 drops of N,K-dimethylformamide and 0.2 ml of oxalyl chloride at room temperature, followed by stirring at the same temperature for 2 hours. The reaction mixture was concentrated under reduced pressure. The obtained residue was dissolved to 30 ml of tetrahydrofuran, and then added dropwise with 0.4 g of dimethylamine {40 % (w/w) aqueous solution) at room temperature; and then being stirred at the same temperature for 2 hours. The reaction mixture was added with saturated aqueous solution of ammonium chloride, followed by extraction with ethyl acetate. The organic layer was concentrated under reduced pressure. The obtained residue was subjected to a silica gel chromatography to obtain 0.26 g of K,N-dimethyl-2,5,5, 6, 6,6-hexafluoro-2-(3,3,3-

trifluoropropyisulfonyl}hexanamide (referred as the present compound (74) , hereinafter) . The present compound (74)

Production Example 7 5
1.0 g of methyl 2-chloro-5, 5 , 6, 6, 5-pentafluoro-2-(3,3,3-
trifluoropropylsulfonyi)hexanoate was dissolved to 30 ml of methanol. This solution was added with 3.6 ml of methylamine (2 M methanol solution) at room temperature, and then stirred at the same temperature for 16 hours. The reaction mixture was concentrated under reduced pressure. The obtained residue was subjected to a silica gel chromatography to obtain 0.15 g of 2-chloro-N-methyl-5,5,6,6,6-pentafluoro-2-(3,3,3-
trifluoropropylsulfonyl)hexanamide (referred as the present compound (75), hereinafter). The present compound (75)


Production Example 76
1.0 g of l-iodo-3,3,3-trifluoropropane and 1.0 g of methyl (3/3,3-trifluoropropylsulfonyl)acetate were dissolved to 20 ml of diraethylsulfoxide. This solution was added with 0.6 g of potassium carbonate at room temperature, and then stirred at the same temperature for 16 hours. The reaction mixture was added with 10 % hydrochloric acid, followed by extraction with ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The obtained residue was subjected to a silica gel chromatography to obtain 0.42 g of methyl 5,5,5-trifluoro-2-(3,3,3-trifluoropropylsulfonyl)pentanoate (referred as the present compound (76), hereinafter). The present compound (76)

Production Example 77
1.0 g of methyl 5,5,5-trifluoro-2-(3,3,3-trifluoropropylsulfonyl)pentanoate was dissolved to 30 ml of
tetrahydrofuran. This solution was added with 0.12 g of sodium hydride (60 % in oil) at room remperature, followed by stirring at the same temperature for 0.5 hours; and then being added with 0.4 g of N-chlorosuccinimide at the same

temperature, followed by stirring for 2 hours. The reaction mixture was added with 10 % hydrochloric acid, followed by extraction with ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The obtained residue was subjected to a silica gel chromatography to obtain 0.65 g of methyl 2-chloro-5,5,5-trifluoro-2-(3,3,3-trifluoropropylsulfonyl) pentanate (referred as the present compound (77), hereinafter). The present compound (77)

Production Example 78
2.0 g of mefe^^y^ l-iodo-4, 4, 4-trif luorobutane and 2.0 g of (3,3,3-trifluoropropylsulfonyl)acetate were dissolved to 30 ml of dimethylsulfoxide. This solution was added with 1.2 g of potassium carbonate at room temperature, followed by stirring at the same temperature for 3 days. The reaction mixture was added with 10 % hydrochloric acid, followed by extraction with ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The obtained residue was subjected to a silica gel chromatography to obtain 1.50

g of methyl 6, 5,6-trifluoro-2-(3,3,3-
trifluoropropylsulfonyl)hexanate (referred as the present compound (78), hereinafter). The present compound (78)

Production Example 79
1.0 g of methyl 6,6,6-trifluoro-2-(3,3,3-trifluoropropylsulfonyl)hexanoate was dissolved to 30 ml of tetrahydrofuran. This solution was added with 0.12 g of sodium hydride (60 % in oil) at room temperature, followed by stirring at the same temperature for 0.5 hours; and then being added with 0.4 g of N-chlorosuccinimide at the same temperature, followed by stirring for 4 hours. The reaction mixture was added with 10 % hydrochloric acid, followed by extraction with ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The obtained residue was subjected to a silica gel chromatography to obtain 0.96 g of methyl 2-chloro-6, 6, 6-trifluoro-2-(3,3,3-trifluoropropylsulfonyl) hexanoate (referred as the present compound (75), hereinafter) . The present compound (7 9)


Production Example 80
0.8 g of methyl 2-chloro-6,6,6-trifluoro-2-(3,3,3-trifluoropropvlsulfonyl)
hexanoate was dissolved to 20 ml of methanol. This solution was added vith 0.? ml of ammonia (V M methanol solution) at room temperature, followed by stirring at the same -emperature for 10 hours. The reaction mixture was concentrated under reduced pressure. The obtained residue was subjected to a silica gel chromatography to obtain 0.51 g of 2-chloro-6,6,6-trifluoro-2-(3, 3, 3-triflucropropylsulfonyl)
hexanamide (referred as the present compound (80), hereinafter). The present compound (BO )

Production Exarnple 81
1.0 g of methyl 2-chloro-5, 5, 5-trifiuoro-2-(3,3,3-trifluoropropylsulfonyl)

pentanoate was dissolved to 30 nl of methanol. This
solution was added with 1.2 ml of ammonia (7 M methanol
solution) at room temperature, followed by stirring at the
same temperature for 14 hours. The reaction mixture was
concentrated under reduced pressure. The obtained residue
was subjected to a silica gel chromatography to obtain 0.52
g of 2-chlcro-5,5,5-trifluoro-2-(3,3,3-
trifluoroprcpylsulfonyl)
pentanamide (referred as the present compound (81),
hereinafter).
The present compound (81)

Production Example 82
2.S g of l-iodo-3,3,4,4,5,5,5-heptafluoropentane and 2.0 g of methyl (3 , 3, 3-trif luoroprcpylsulf or.yl) acetate were dissolved to 30 ml of diroethylsulfoxide. This solution was added with 0.34 g of sodium hydride (60 % in oil) at room temperature, and then stirred at the same temperature for 14 hours. The reaction mixture was added with 10 % hydrochloric acid, followed by extraction with ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium chloride, dried over anhydrous magnesium, sulfate, and then concentrated under reduced pressure. The obtained residue was subjected to a silica gel chromatography to

obtain 2.30 g of methyl 5,5,6,6,7,7,7-heptaflucro*2-{3,3,3-trifluoropropylsulfonylheptanoate (referred as the present compound (82), hereinafter). The present compound (82)

Productor. Example 83
1.0 g of methyl 5,5,6,6,7,7,7-heptafluoro-2-(3,3,5-trif luoropropyls"ulf onyl) heptanoate was dissolved ~ o 3 0 ir.l of terrahydrofuran. This solution was added with 0.0 9 g ot sodium hydride (60 % in oil) at room temperature, end then stirrsd at the same temperature for 0.5 hours; and then being added with C.3 g of N-chlorosuccinimide at the same temperature, followed by srirring for 1 hour, and then the reaction mixture was added with 10 % hydrochloric acid, followed by extraction with ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium, chloride, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The obtained residue was subjected to a silica gel chromatography to obtain 0.93 g of methyl 2-chloro-5,5,6,6,7,7,7-heptafluoro~2-(3,3,3-trifluoropropylsulfonyl)heptanoate (referred as the present compound (83) , hereinafter) . The present compound (83)


Production Exaraple 84
C.7 g of methyl 2-chlcro-5,5,6, 6, 7,7, 7-heptafluoro-2-(3,3,3-
trifluoropropylsulfonyl)heptanoate was dissolved to 30 ml of methanol This solution was added with 0.6 ml of ammonia (7 M methc.no 1 solution) at room temperature, and then stirred at the same temperature for 10 hours. The reaction mixture w'as concentrated under reduced pressure. The obtained residue was subjected to a silica gel chromatography tc obtain 0.50 g of 2-chloro-5,5,6,6,7,7,7-heptafluoro-2-(3,3,3-
trifluoropropylsulfonyl)heptanamide (referred as the present compound (54), hereinafter). The present compound (S4)

Production Example 85
7.0 g of l-iodo-3,3,4,4,5,5,6,6,6-nonafluorohexane and 4.4 g of m.ethyl (3, 3, 3-trif luoropropylsulf onyl} acetate

were dissolved to 50 ml of dimethylsulfoxide. This solution was added with 2.59 g of potassium carbonate at room temperature. This mixture was stirred at 60 °C for 2 days. The reaction mixture was dropped to about a room temperature. The reaction mixture was added with 10 % hydrochloric acid, followed by extraction with ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The obtained residue was Subjected to a silica gel chromatography to obtain 1.50 g of methyl 5,5,6,6,7,T , B,8,8-nonafluoro-2-(3,3,3- , -rifluoropropylsulfonyl)octanoate (referred as the present compound (85), hereinafter). The present compound (85}

Production Example 86
1.0 g of methyl 5,5,6,6,7,7,8,8,8-nonafiuoro-2-(3,3,3-
trifluoropropylsulfonyl)octanoate was dissolved to 30 ml of tetrahvdrofuran. This solution was added with 0.08 g of sodium hydride (60 % in oil) at room temperature followed by stirring at "he same tem.perature for 0.5 hours; and when being added with 0.3 g of N-chlorosuccinimide at the same tem.perature, followed by stirring for 16 hours. The

reaction mixture was added with 10 % hydrochloric acid, followed by extraction with ethyl acetate. The organic Layer was washed with saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The obtained residue was subjected to a silica gel chromatography to obtain 0.89 5 of methyl 2-chloro-5,5,6,6,7,7,8,S, 8-nonafiuoro-2-{3,3,3-trifluoropropylsulfonyl)octanoate {referred as the present compound (66), hereinafter). the present compound (86)

Production Example 87
0.8 g of methyl 2-chlorc-5,5,6, 6,7,7,8,8,8-nonafluoro-2- (3,3,3-
trifluoropropyisulfonyl)octanoate was dissolved to 20 ml of methanol. 1?his solution was added with 1.1 ml of ammonia (7 M methanol solution) at room temperature, followed by stirring at the same temperature for 12 hours. The reaction mixture was concentrated under reduced pressure. The obtained residue was subjected to a silica gel chromatography to obtain 0.45 g of 2-chloro-5,5,6,6,7,7,8,3,3-nonafluoro-2-(3,3,3-
trifluoropropylsulfcr.yl) octanamide (referred as the present compound (87), hereinafter).


Production Example 88
2.0 g of methyl 5, 5, 6, 6, 6-pentaf iuoro-2-(3, 3, 4 , 4 , 4~ pentafluorobutylsulfonyl)hexanoate was dissolved to 30 ml of ciiTieth-.'lsulf cxide. This solution was added with 0.19 g of sodiuip. hydride (5C % in cil) at room temperature, followed by stirring at the same temperature for 0.5 hours; and then being added wich 1.3 g of copper(II) chloride at the same temperature, followed by stirring for 12 hours. The reaction mixture was added with 10 % hydrochloric acid, followed by extraction with ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The 'obtained residue was subjected to a silica gel chromatography to obtain 1.70 g of methyl 2-chloro-5,5,6,6,6-pentafluoro-2-(3,3,4,4,4-pentafluorobutylsulfonyl)hexanate (referred as the present compound (88) , hereinafter) . The present compound (38)


2.92(m,6K)
Production Example 89
1.5 g of methyl 2-chloro-5,5,6,6,6-pentafluoro-2-(3,3,4,4,4-
pentafluorobutylsulfonyl)hexanoate was dissolved to 30 ml of methanol. This solution was sdded with 1.4 ml of ammonia (7 M methanol solution) at room temperature, followed by stirring at the same temperature for 16 hours. The reaction mixture was concentrated under reduced pressure. The obtained residue was subjected to a silica gel chromatography to obtain 1.10 g of 2-chloro-5,5,6,6,6-pentafiuoro-2- (3,3,4,4,4-
pentafluorobutylsulfonyl)hexanamide (referred as the present compound (35), hereinafter). The present compound (89)

The present compounds (90) to (103) shown belovj were preduced by the similer method described above,
The present compound (90)
















































































































































































Reference Production Example 1
9,6 g of l-brorao-3,3,3-trif luoropropane and 5 g of thiobenzoic acid were dissolved to 30 ml of H,N-dimethylformamide, and 1.45 g of sodium hydride (60 % in oil; was added thereto under ice cooling. The mixture was srirred at room temperature for 12 hours. 10 % hydrochlcric acid was added to the reaction mixture and the mixture was extracted by ethyl acetate. The organic layer was washed respectively with 10 % hydrochloric acid and saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel chromatography to obtain 6.90 g cf 3-( 3 , 3, 3-trif luoropropyl) benzer.ethicate given by the below formula:

"H-NMR(CDC1:, ,TMS) :5 [ppm) 7. 97 (d,2H) ,7 .5B-
7.62(m,lH),7.4 7(dd,2H),3.24 (t,2H) , 2.4^-2.56(m,2H)
Reference Production Example 2
9.9 g of l-iodo-3, 3, 4, 4, 4-pentafluorobutane and 5 g of thiobenzoic acid were dissolved to 30 ml of N,N-dimethylformam.ide, and 5.0 g of potassium carbonate was added thereto under ice cooling. The mixture was stirred at room temperature for 20 hours. 10 % hydrochloric acid was added to the reaction mixture ana the mixture was extracted

by erhyl acerate. The organic layer was washed respectively with 10 % hydrochloric acid and saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel chromatography to obtain 7.90 g of 3-{3, 3, 4, ^5, 4^pentaf luorobutyl) benzenethioate given by zne below formula:

Reference Production Example 3
2.Q g of l-iodo-3, 3, 4, 4 , 5, 5, 5-heptaf luoroper.tane and 0.9 g of thiobenzoic acid were dissolved to 20 ml of N,N-dimethylformamide, and 0.9 g of potassium carbonate was added thereto under ice cooling. The mixture was srirred at room temperature for 20 hours. 10 % hydrochloric acid was added to the reaction mixture and the mixture was extracted by ethyl acetate. The organic layer was washed respectively with 10 % hydrochloric acid and saturated aqueous solution of sodium chloride, dried over anhydrous m.agnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel chromatography to obtain 1.75 g of S-(3,3,4,4,5,5,5-heptafluoropentyl) benzenethioare given by the below formula:


Reference Production Example 4
10 g of S-{3,3,3-trifluoropropyl) benzenethioate was dissolved to 50 ml of tetrahydrofuran and 8.4 ml of sodium methoxide (28 % [w/w] methanol solution) was added thereto under ice cooling. Furthermore, 5.1 g of bromoacetoniorile was added dropwise thereto and the mixture was stirred at room temperature for 2 hours. 10 % hydrochloric acid was added to the reaction mixture and the mixture was extracted by ethyl acetate. The organic layer was washed respectively with 10 % hydrochloric acid and saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was dissolved to 40 ml of acetic acid and 20 ml of peracecic acid (32 % (w/w) acetic acid solution) was added thereto under ice cooling. Then the mixture was stirred at 50 "C for 10 hours. The reaction mixture was dropped to room temperature and poured into water, then extracted by ethyl acetate. The organic layer was washed respectively with saturated aqueous solution of sodium hydrogen carbonate and saturated aqueous solution of sodium chloride, dried over anhydrous magnesim sulfate and concentrated under reduced pressure. The obtained residue was subjected no silica gel

chromatography to obtain 7.04g ox (3,3,3-triiluoropropylsulfonyl) acetonitrile given by the below

Reference Production Example 5
7.1 g of S-(3,3,4,4,4-pentafluorobutyl) benzenethioate was dissolved to 50 ml of tetrahydrcfuran and 4.3 ml of sodium methoxide {2S % (w/w) methanol solution) ■was added -hereto under ice coding. Furthermore, 30 . g of bromoacetoritrile was added dropwise thereto and the rr.ix-ure was stirred at room, temperature for 20 hours. 10 % hydrochloric acid was added to the reaction mixture and the mixture -was extracted by ethyl acetate. The organic layer was washed respectively wiith 10 % hydrochloric acid and saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was dissolved to 40 ml of scenic acid and 20 TT.l of psracetic acid (32 % (w/w) acetic acid solution) was added thereto under ice cooling. Then the mixture was stirred at 60C for 8 hours. The reaction mixture was dropped to room temperature and poured into water, then extracted by ethyl acetate. The organic layer was washed respectively with saturated aqueous solution of sodium hydrogen carbonate and saturated aqueous solution of sodium chloride, dried ever anhydrous magnesium sulfate and

concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 5.47g of (3,3,4,4,4-pentafluorobutylsulfonyl) acetonitrile given by the below formula;

Reference Production Example S
9.7 g of S-(3,3,4,4,5,5,5-heptafluoropentyl) benzenethioaie was dissolved to 30 ml of tetrahydrcf"jrar. and 5.7 ml of sodium methoxide (28 % (w/w) methanol solution) was added thereto under ice cooling. Furthermore, 5.5 g or bromoacetcnitrile was added dropwise thereto and the mixture was srirred at room temperature for 10 hours, 10 % hydrochloric acid was added to the reaction mixture and the mixture was extracted by ethyl acetate. The organic layer was washed respectively with 10 % hydrochloric acid and saturated aqueous solution of sodium, chloride, dried ever anhydrous rriagnesium sulfate and concentrated under reduced pressure. The residue was dissolved to 40 ml of acetic acid and 20 ml of peracetic acid (32 % (w/w) acetic acid solution) was added thereto under ice cooling. Then the mixture was stirred at 60 "C for 5 hours. The reaction m.ixture was dropped to room, temperature and poured into water, then extracted by ethyl acetate. The organic layer was washed respectively with saturated aqueous solution cf sodium hydrogen carbonate and saturated aqueous solution of

sodium chloride, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 6.54 g of S- (3,3,4,4,5,5,5-heptafluoropentylsulfonyl) acetonitrile given by the below formula:

Reference Production Example 7
10 g of methyl thioglycolate and 21 g of 1-iodo-5,3,3-criflucropropane were dissclved to 200 ml of K, K-dimethylfcrrr.ariide and 13 g of potassium carbonate was added thereto under ice cooling. The mixture was stirred at room temperavure for 20 hours. 10 % hydrochloric acid was added to -he reacuion mixture and the mixture was extracted by ethyl acetate. The organic layer was washed respectively with 10 % hydrochloric acid and saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was dissolved to 100 ml of acetic acid and 5C vr.l of peracetic acid (32 % (w/w) acetic acid solution) was added thereto under ice coding. Then the mixture was stirred at 60 °C for 15 hours. The reaction mixture was cooled to room temperature and poured into water, then extracted by ethyl acetate. The organic layer was washed respectively with saturated aquecus solution of sodium hydrogen carbonate and saturated aqueous solution of sodium chloride, dried over

anhydrous magnesium sulfate and concentrated under reduced pressure, The obtained residue was subjected to silica gel chromatography to obtain 14.1 g of methyl (3,3,3-triflucropropylsulfonyl) acetate given by the below formula:

Reference Production Example 6
10 g of methyl thioglycolate and 26 g of 1-iodo-3, 3, 4 , 4, 4-pentaf luorobutane were dissolved to 100 rr.l of N,K-dimsthylforrriam.ide and 13 g of potassium carbonate was added thereT:o under ice cooling. The ir.ixture was stirred ar room temperature for 2 0 hours. 10 % hydrochloric acid was added to -he reaction mixture and rhe rriixture was extract:ed by ethyl acetate. The organic layer was washed respectively v.'ith 10 % hydrochloric acid and saturated aqueous solunion of sodium chloride, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was dissolved to 100 ml of acetic acid and 50 ml of peracetic acid (32 % (w/w) acetic acid solution) was added thereto under ice cooling. Then the mixture was stirred at 60 "Z for 16 hours. The reaction mixture was cooled to room temperature and poured into water, then extracted by ethyl acetate. The organic layer was washed respectively with saturated aqueous solution of sodium hydrogen carbonate and saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and concentrated under reduced

pressure. The obtained residue was subjected no silica gel chromatography to obtain 23.1 g of methyl (3,3,4,4,4-pentafluorobutylsulfonyl) acetate given by the below

Reference Production Example 9
5 g of methyl thioglycolate and 15 g of 1-iodo-3,3,4,4,5,5/5-heptafluoropentane were dissolved to 50 ml of N N-dimethylfbrmamide and 6.5 g of potassium carbonate was added thereto under ice cooling. The mixture was stirred at room temperature for 10 hours. 10 % hydrochloric acid was added to the reaction miixture and the mixture was extracted by ethyl acetate. The organic layer was washed respectively with 10 % hydrochloric acid and saturated aqueous solution of sodium chloride^ dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was dissolved to 50 ml cf acetic acid and 20 ml of peracetic acid (32 % (w/w) acetic acid solution) was added theretc under ice cooling. Then the mixture was stirred at 60 °C for 4 hours. The reaction mixture was cooled to room temperature and poured into water, then extracted by ethyl acetate. The organic layer was washed respectively with saturated aqueous solution of sodium hydrogen carbcnate and saturated aqueous solution cf sodium chloride, dried over anhydrous magnesium sulfate and concentrated under reduced

pressure. The obtained residue was subjected to silica gel chromatography to obtain 12.6 g of methyl (3,3,4,4,5,5,5-heprailuoropentylsulfonyl) acetate given by the below formula :

Reference Production Example 10
0.3 g of methyl 5,5,6,6,6-pentafiuorc-2-(3,3,3-triflboropylsulfony onyl) nexanoate was dissolved to 30ml of methanol. An aqueous solution of potassuim, hydroxide (a mixed solution of 0.3 g of potassium hydroxide and 5 ml of water) was added thereto at room temperature and the mixture was stirred at rhe same temperature for 24 hours. 10 % hydrochloric acid was added to nhe reaction mixture and the m.^xture was extracted by ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium, chloride , dried over anhydrous magnesium sulfate and ocncenrraoed under reduced pressure to obtain 0.2S g of 5 , 5,c,6,6-pentafluoro-2-{3,3,3-
tri fluoropropylsulfonyl]hexanoic acid given by the below formula:


Reference Production Example 11
0.5 g of methyl 2-methyl-5,5,6,6,6-pentafluoro-2-(3,3,4,4, 4-pentaf luorobutylsTjlfonyl) hexanoate was dissolved to 30 ml o^ methanol. An aqueous solution of potassium hydroxide (a mixed solution of 0.3 g of potassium hydroxide and 5 ml of water) was added thereto at room temperature and the mixture was stirred at the same temperature for 6 hours. 10 % hydrochloric acid was added to the reaction m.ixture and the miixture was extracted by ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium chlcride, dried ever anhydrous magnesium sulfate and concentrated under reduced pressure to obtain 0.4£ g of 2-methyl/ 5 6, i, 6-pen-sf luoro-2-' (3,3,4,4,4-pentafluorcbutylsulfonyl)hexanoic acid given by the below

Reference Production Example 12
0.5 g of methyl 2-ethyl-5,5,6,6,6-pent5fluoro-2-
(3,3,3-trifluoropropylsulfonyl)hexanoate was dissolved to 30 ml of methanol. An aqueous solution of potassium hydroxide
(a mixed soluticn of 0.3 g cf potassium hydroxide and 5 n:;! of water} was added thereto at room temperature and the mixture was stirred at the same tem,perature for 10 hours.

IC % hydrochloric acid was added to the reaction mixture and rhs mixture was extracted by ethyl acetate. The organic layer was washed wirh saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain 0.48 g of 2-ethy 1-5, 5, 6, 5, o-pentaf luoro-2- {3,3,3-
trifluoropropylsulfonyl)hexanoic acid given by the below formula;

Reference Production Example 13
20 g of ethyl 2-mercaptopropionate and 33 c of 1-iodo-3,3,3-triflucropropane were dissolved to 200 ml cf N,K-dimethylformamide and 21 g of potassiuiri carbonate was added thereto under ice cooling. The mixture was stirred at room temperature for 4 hours. 10 % hydrochloric acid was added to the reaction mixture and the mixture was extracted by ethyl acetate. The organic layer was washed respectively with ID % hydrochloric acid and saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was dissolved to 100 mil of acetic acid and 30 ml of peracetic acid (30 % (w/w) acetic acid solution) was added thereto under ice cooling. Then the mixture was stirred at 60 "C fcr 4 hours. The reaction mixture was dropped to room

temperature and poured into water, then extracted by ethyl acetate. The organic layer was washed respectively with saturated aqueous solution of sodium hydrogen carbonate and saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 35.3 g of ethyl 2-(3,3,3-trifluoropropylsulfcnyl) propionate given by the below

Referential Production Example 14
40 g of 5, 5, 6, 6, 6-pentafluorohexanenitrile was added dropwise with 11 mil of brorriine and 2 ml of phosphorus tribromide at room temperature, followed by stirring at 90 "C for £ hours. The reaction mixture was dropped to room temperature. The reaction mixture was poured into water, followed by extraction wirh ethyl acetate. The organic layer was subsequently washed with saturated aqueous solution of sodiumi thiosulfate and saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfare, and then concentrated under reduced pressure. The obtained residue was subjected to silica gel chromiatography to obtain 17.5 g of 2--bromo-5, 5, 6, 6, 6-pentafluorohexanenicrile given by the below formula:


Referential Production Example 15
0.5 g of methyl 5,5,6,6,7,7,7-heptafluoro-2-(3,3,4,4,4-
pentafluorob-utylsuifonyl) heptanoate was dissolved to 30 ml or methanol, added with an aqueous solution of potassium hydroxide(a mixed solution of 0.3 g of potassium hydroxide and 5 ml of water at room oemperaturs, and then stirred -z the same temperature ::or 2 days. The reaotion mixture was added with 10 % hydrochloric acid, followed by extraction with erhyl acetate. The organic layer was washed with saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure to obtain 0.48 g of 5,5,6,6,7,7,7-heptafluoro-2- [3,3,4,4,4-
pentsfluorofcutylsulfonyi)heptancic acid given by the below formula:


1.2 g of methyl 5, 5, 6, 6, 7, 7, -heptailuoro-2-methvi-2" (3,3,4,4,4-
pentafluorobu-cylsulfonyl) heptanoate was dissolved tc 30 ml of merhanol, added with an aqueous solution of potassiuir. hydroxide(3 mixed solution of 0.8 g of potassium hydroxide and 10 ml of water) at room temperature, and rhen stirred at the same temperature for 2 days. The reaction mixture was added with 10 % hydrochloric acid, followed by extraction wizh ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium chloride, dried over anhydrous miagnesiurr. sulfate^ and then concentrated under reduced pressure to obtain 1.10 g cf 5,5,6,6,7,7,7-hepraflucro-2-methyl-2- (3,3,4,4,4-

Referential Production Example 17
0.5 g of methyl 5,5,6,6,6-pentafluoro-2-(3,3,4,4,4-pentafluorobutylsulfonyl)hexanoate vias dissolved to 50 ml cf methanol, added with an aqueous solution of potassium hydroxide(s mixed solution of 0.4 g of potassium hydroxide and 5 ml of water) at room temperature, and then stirred at the same temperature for 1 day. The reaction mixture was added with 10 % hydrochloric acid, followed by extraction

with ethyl acetate, The organic layer was washed with sanurated aqueous solution of sodium chloride, dried over anhydrous magnesiure, sulfate, and then concentrated under reduced pressure to obtain C.48 g of 5,5,6,6,6-pent3fiuoro-2-(5,3,4,4,4-

Referential Production Example 16
0.9 g of methyl 2-rriethyl-S , 5, 6, 6, 6-pentaf luoro-2-(3,2,4,4,4-
pentafluorobutylsulfonyl)hexanoate was dissolved to 50 ml of methanol, added with an aqueous solution of per. as slum hydroxide (a mixed solution of 0.7 g of potassium hydroxide and 5 m.l of water) at room remperature, and then stirred at the same temperature for 1 cay. The reaction mixture was added with 10 % hydrochloric acid, followed by exraction with ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure to obtain C.78 g of 2-methyl-5,5,6,6,6-pentaflucro-2- (3, 3,4, 4, 4-pentafluorobutylsulf onyl) hexanoic acid given by the below formula:


Fcrmulation Examples are exemplified below. In addition, "part" means part by weight.
Formulation Examp1e 1
9 parts of each of uhe present compounds (1) to (103) are dissolved in 37.5 parts of xylene and 37.5 parts of N,K-dimethylformide , and 10 parts of polycxyethylene styryl phenyl ether ana 6 parts of calcium dodecylbenzenes sulfonate are added therero, followed by stirring and mixing well, to give an emulsifiable concentrate for each compound.
Formulation Example 2
To 40 parts of each of the present compounds (1) to (103) are added 5 parts of SORPCL 5060 (registered trade name for TOHO KAGAKU KOGYO), followed by mixing well. To the mixture are added 32 parts of CAP.PLEX #80 (registered trade name for SHIONOGI & Co., synthetic hydrated silicone oxide fine powder) and 23 parts of 300 mesh diatomaceous earth, followed by mixing with a juice mixer, to give a well table powder for each compound.
formulation Example 3
To 3 parts of each of the present compounds (1) tc (103) are added 5 parts of synthetic hydrated silicon oxide

fine powder, 5 parts of sodium dodecyibenzenesulfonate, 30 parts of bentonite, and 57 parts of clay, followed by stirring and mixing well. Then an appropriate amount of water is added to this mixture, followed by further stirring, granulating with a granulator, and air drying, to give a granule for each compound.
Formulation Example 4
4.5 parts of each of the present compounds (1) to . (103), 1 part of synthetic hydrated silicon oxide fine powder, 1 part of Doriresu B (Sankyo Co., Ltd,) as a flocculant and 7 parts of clay are well mixed with a mortar, followed by stirring and mixing with a juice nixer. To the resulting mixture are added Be.5 parts of cut clay, followed by stirring and mixing well, to give a dust for each compound .
Formulation Example 5
10 parts of each of the present compounds (1) to (103), 35 parts of white carbon containing 50 parts of pclyoxyethylene alkyl ether sulfate ammonium salt and 55 psrts of water are mixed and pulverized by the wet grinding method to give a formulation for each compound.
Formulation Example 6
0.5 parts of each of the present compounds (1) to (103) are dissolved in 10 parts of dichloromethane, and the resulting solution is mixed with 89.5parts of Iso-Par M (isoparaffine: registered trade name for EXXON CHEMICAL LTD) to give an oil solution.
Formulating Example 7
0-1 parts of each of the present compounds (1) to

{1C3) and 49.9 parts of NEO-CKIOZOL (CHUO KASEI Co., LTD) are charged into aerosol can, and aerosol valve is fixed to the can. Then 25 parts of dimethyl ether and 25 parts of LPG are filled in the can, followed and fitting an actuator on it, to give an oil aerosol. Formulation Example 8 0.6 parts of each of the present compounds (1) to
1103), 0.01 parts of BHT, 5 parts of xylene, 3.39 parts of deodorized kerosene and 1 part of emulsifier [Atmos 300(registered trade name for ATMOS CHEMICAL LTD)J are mixed and dissolved. The solution obtained and 50 parts of distilled water are charged into aerosol container, and a valve is fixed to the container. 4C Farts of propellant
(L?C-} are charged -finder pressure through the valve to give an aqueous aerosol.
The following test example will demonstrate that the present compounds are useful as an active ingredient of noxious arthropod controlling agent. Test Example 1
The formulation obtained in Formulation Example 5 using the present compounds (1), (2), (3), (4), (5), (5), (8), (9), (11), (12), (13), (14), (15), (16), (17), (18), (20), (21), (22), (23), (24), (25), (26), (27), (29), (30), (31), (32), (33), (34), (35), (36), (37), (38), (39), (40), (41), (44), (45), (46), (47), (48), (49), (50), (52), (53), (55), (56), (57), (58), (59), (60), (61), (63), (64), (65), (67), (68), (71), (72), (73), (74), (75), (78), (79), (80), (81), (62), (83), (84), (86), (87), (88), (S9) , (9C), (SI),

(33), (94), (96), (57), (100), (101), (102) and (103) respectively, was diluted with water so that the active ingredient concentration came to 55.6 ppm to prepare a test solution.
50 g of molding Bonsoru 2 (available from Sumitomo Chemical Co., Ltd.) was put into a polyethylene cup having five holes of 5 ran in diameter, and 10 to 15 seeds of rice were planted in the polyethylene cup. The rice plants were grown until the second, foliage leaves developed and then treated with the rest solution, which had been prepared as described above and was absorbed in a volume of 45 ml from the bottom, of the cup. The rice plants were left in a greenhouse at 25 C for 6 days and then cut into the same height of 5 cm.. Thirty first-ins tar larvae of brown. plant hoppers (Nilaparvata lugens) were set free on the rice plants, which were then left in the greenhouse ao 25°C. On the 6th day after the release of brown planthopper larvae, the number of brown planthoppsrs parasitic on the rice plants was examined. As a result, in the treatment with each of the present compounds (1), (2), (3), (4), (5), (6), (8), (9), (11), (12), (13) , (14) , (15) , (16) , (17) , (13) , (20) , (21) , (22) , (23) , (24), (25), (26), (27), (29), (30), (31), (32), (33), (34), (35), (36), (37), (38), (3 9), (40), (41), (44), (45), (46), (47), (48), (49), (50), (52), (53), (55), (56), (57), (58), (59) , (60) , (61) , (63) , (64) , (65) , (67) , (68) , (71) , (72) , (73) , (74) , (75) , (78) , (79) , (80) , (81) , (82) , (83) , (84) , (86) , (87) , (86) , (8 9) , (90) , (91) , (93) , (94) , (96), (97) , (100), (101), (102) and (103), the number of parasitic insects on the 6th day after the

trsatment was not greater than 3.
Test Example 2
The formulation obtained according to Formulation Example 5 using the present compounds (i), (2), (3), {4),

On the bottoiT, of a polyethylene cup having s diarrieter of 5.5 cm, a filter paper having the same diameter was laid, and 0,7 ml of the above test solution was added dropwise on the filter paper, followed by putting 30 mg of sucrose on it uniformly as a bait. Ten female Musca domastlca imagoes were set free in the polyethylene cup and coverea it with a lid. After 24 hours, the number of surviving and dead Musca domestica was examined and the rate of dead pests was calculated.
As a result, in the treatment with each of the present compounds (1), (2), (3), (4), (5), (6), (8), (9), (10), (11), (12), (13), (14), (15), (16), (17), (16), (19), (20) , (21), (22) , (23), (25), (26), (26) , (29) , (30), (31) ,



was calculated.
As a result, in the treatment with each of the present compounds (1), (2), (3), (4), (5), (6), (7), (8), (9), (10), (11), (12), (13), (14), (15), (16), (17), (20), (21), (23), (26), (29), (30), (31), (32), (33), (34), (35), (36), (37), (38), (39), (40), (41), (44), (45), (46), (47), (49), (50), (52), {53), (55), (56), (57), (58), (59), {60), (61), (63), (64), (65), (67), (68), (69), (70), (71), (72), (73), (74), (75), (78), (79), (80), (81), (84), (86),' (87), (38), (89), (90), (91), (S3), (94), (96), (97), (100), (101), (102) and (103) the rate of dead pests was 100%.
Tes- Ex.arr.ple 4
The formulation obtained according to Formula-Lion Example 5 using the present compounds (1), (2), (3), (4), (5), (6), (7), (8), (9), (10), (11), (12), (13), (14), (15), (16), (1'), (18), (19), (20), (21), (22), (23), (24), (25), (26), (29), (30), (31), (32), (33), (34), (35), (36), (5"), (3S), (39), (40), (41), (42) (45), (46), (47), (49), (50), (51) , (52) , (53) , (56) , (57) , (58) , (59) , (60) , (61) , (63) , (65), (67), (66), (69), (70), (71), (72), (73), (74), (75), (76), (78), (79), (80), (81), (82), (83), (84), ,(36), (87), (88), (89), (90), (91), (92), (93), (94), (95), (96), (97), (100), (102) and (103) respectively, was diluted with water so that the active ingredient concentration came to 500 ppm to prepare a test solution.
0.7 ml of above test solution was added to 100 KI of ion exchanged water (active ingredient concentration: 3.5 ppm) . Twenty last-instar larvae of Cuiex pipiens paller.s

were set free in the solution. After one day, the number of
surviving and dead Culex pipiens pallens was examined and
the rate of dead pests was calculated.
As a result, in the treatment with each of the
present compounds (1) , (2) , (3) , (4) , (5) , (6), [7) , (6) , (9), (10), (11), (12), (13), (14), (15), (16), (17), (18), (19), (20), (21), (22), (23), (24), (25), (26), (29), (50), (51), (32), (33), (34), (35), (36), (37), (33), (39), (40), (41) , (42) , (45) , (46) , (47), (4 9)., (50) , (51) , (52) , (53) , (56) , (57) , (58) , (59) , (60) , (61) , (63) , (65) , (67) , (68) , (69), (7 0), (71), (72), (73), (74), (75), (76), (7 8), (79), (60), (61), (62), (83) , (34), (86) , (87), (88), (89) , (90) , (91) , (92) , (93) , '94; , i'95) , (96) , (97) , (IOC) , (102) and (103), the rate of dead pests was not less than 90 %.
Industrial Applicability
The present compounds are useful for an active ingredient or noxious arthropod agent.

CLAIMS
1. An organic sulfur compound given by the formula [I]:

R1 represents a C3-C6 fluoroalkyl group,
R2 represents a cyano group, a group represented by C(=0)R5
or a group represented by C( = S)R6,
R6 represents a hydrogen atom, a halogen atom or a Cl-C4
alkyl group,
R4 represen-s a C1-C5 flucrcalkyl group,
R5 and R6 independennly represent a C1-C4 alkoxy group, an
amino group optionally subsni-uzed by one or two C1-C4 alkyl
group (s) or a C2-C5 oyclic air.ino group,
n represents C, 1 or 2.
2. T'ns organic sulfur compound according to claim 1, wherein n is 2,
3. The organic sulfur compound according to claim 1, wherein ?." is a cyano group or a group represented by C(=0)R . 4 . The organic sulfur compound according to claim 1, wherein R2 is a cyano group.
5. The organic sulfur compound according to claim 1,
wherein R2 is a group represented by C(=0)R5 and R5 is an
am.ino group optionally substituted by one or two C1-C4 alkyl
group (s) .
6. The organic sulfur compound according to claim 1,
wherein R2 is a group represented by C(=0)R5 and R5 is an

arr.ino group.
7. The organic sulfur compound according to claim 1,
wherein R3 is a halogen atom.
8. A noxious arthropod controlling agent comprising the
organic sulfur compound according to claim 1 and an inert
carrier.
9. A method for controlling noxious arthropods applying
an effective amount of the organic sulfur compound according
to claim; 1 ro noxious arthropods or at a habitat of noxious
arthropods.
10. Use of the compound according to claim 1 for noxious
arthropod control,

Documents:

3106-CHENP-2008 AMENDED CLAIMS 17-02-2015.pdf

3106-CHENP-2008 AMENDED PAGES OF SPECIFICATION 17-02-2015.pdf

3106-CHENP-2008 CORRESPONDENCE OTHERS 21-04-2014.pdf

3106-CHENP-2008 EXAMINATION REPORT REPLY RECEIVED 17-02-2015.pdf

3106-CHENP-2008 FORM-1 17-02-2015.pdf

3106-CHENP-2008 FORM-13 19-05-2009.pdf

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3106-CHENP-2008 FORM-3 22-12-2008.pdf

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3106-chenp-2008 abstract.pdf

3106-chenp-2008 claims.pdf

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3106-CHENP-2008 CORRESPONDENCE OTHERS 17-02-2014.pdf

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Patent Number 266129
Indian Patent Application Number 3106/CHENP/2008
PG Journal Number 15/2015
Publication Date 10-Apr-2015
Grant Date 06-Apr-2015
Date of Filing 20-Jun-2008
Name of Patentee SUMITOMO CHEMICAL COMPANY LIMITED
Applicant Address 27-1, SHINKAWA 2-CHOME, CHUO-KU, TOKYO 104-8260
Inventors:
# Inventor's Name Inventor's Address
1 MIYAZAKI, HIROYUKI 5-2-10-503, NAKAYAMASATSUKIDAI, TAKARAZUKA-SHI, HYOGO
PCT International Classification Number C07C317/44
PCT International Application Number PCT/JP06/322322
PCT International Filing date 2006-11-01
PCT Conventions:
# PCT Application Number Date of Convention Priority Country
1 2005-336721 2005-11-22 Japan
2 2006-156916 2006-06-06 Japan