JP2010120858A - Pest control composition - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a composition having excellent control effects to pests. <P>SOLUTION: The pest control composition contains an organic sulfur compound represented by formula (I) [wherein, R<SP>1</SP>is a 1-5C haloalkyl having at least one fluorine, or the like; R<SP>2</SP>, R<SP>3</SP>are each H, alkyl, or the like; R<SP>4</SP>is cyano, alkoxycarbonyl, amido, or the like; R<SP>5</SP>is H, halogen, or the like; R<SP>6</SP>is fluoroalkyl; (m) is an integer of 0 to 4; (n) is an integer of 0 to 2], and a pyrazole compound such as a compound known in a general name of pyriprole; and a method for controlling the pest includes applying the composition to the pest or a pest-living place. <P>COPYRIGHT: (C)2010,JPO&INPIT

Description

  The present invention relates to a pest control composition containing an organic sulfur compound represented by the following formula (a) and a pyrazole compound represented by the following formula (b).

Pyrazole compounds such as 1- [2,6-dichloro-4- (trifluoromethyl) phenyl-3-acetyl-4- (methylsulfinyl) -5-amino-1H-pyrazole are useful as active ingredients of pest control agents (For example, Patent Document 1).
Depending on the control target, a better control effect may be required.

Special table 2008-517025 gazette

  This invention makes it a subject to provide the composition which has the outstanding control effect suitable for control of a pest.

〔式中、
Ｒ¹は少なくとも１個のフッ素原子を有するＣ１−Ｃ５ハロアルキル基、ハロゲン原子で置換されていてもよいＣ３−Ｃ５アルケニル基、ハロゲン原子で置換されていてもよいＣ３−Ｃ５アルケニルオキシ基、ハロゲン原子で置換されていてもよいＣ３−Ｃ５アルキニル基又はハロゲン原子で置換されていてもよいＣ３−Ｃ５アルキニルオキシ基を表し、
Ｒ²はハロゲン原子で置換されていてもよいＣ１−Ｃ４アルキル基、ハロゲン原子で置換されていてもよいＣ１−Ｃ４アルコキシ基、ハロゲン原子で置換されていてもよいＣ１−Ｃ４アルキルチオ基、ハロゲン原子又は水素原子を表し、
（但し、Ｒ¹がハロゲン原子で置換されていてもよいＣ３−Ｃ５アルケニルオキシ基又はハロゲン原子で置換されていてもよいＣ３−Ｃ５アルキニルオキシ基である場合、Ｒ²はハロゲン原子で置換されていてもよいＣ１−Ｃ４アルキル基又は水素原子である。）
Ｒ³はＣ１−Ｃ４アルキル基、ハロゲン原子又は水素原子を表し、
Ｒ⁴はシアノ基、Ｃ(＝Ｑ)ＯＲ⁷又はＣ(＝Ｑ)Ｎ(Ｒ⁸)₂を表し、
Ｒ⁵は水素原子、ハロゲン原子又はＣ１−Ｃ４アルキル基を表し、
Ｒ⁶はＣ１−Ｃ５フルオロアルキル基を表し、
Ｑは酸素原子又は硫黄原子を表し、
Ｒ⁷はＣ１−Ｃ４アルキル基を表し、
Ｒ⁸は各々独立して水素原子又はＣ１−Ｃ４アルキル基を表すか、２つのＲ⁸が末端で結合してＣ２−Ｃ７アルキレン基を表し、
ｍは０〜４の整数を表し、
ｎは０、１又は２を表す。〕
で示される有機硫黄化合物と、
下記式（II）

〔式中、
Ｘ¹はシアノ基又はアセチル基を表し、Ｘ²はメチルチオ基、フルオロメチルチオ基、ジフルオロメチルチオ基、トリフルオロメチルチオ基、エチルチオ基、メチルスルフィニル基、フルオロメチルスルフィニル基、ジフルオロメチルスルフィニル基、トリフルオロメチルスルフィニル基又はエチルスルフィニル基を表し、Ｘ³はアミノ基、（２−ピリジルメチル）アミノ基、（ピラジニルメチル）アミノ基又は（４−ヒドロキシ−３−メトキシベンジリデン）アミノ基を表す。〕
で示されるピラゾール化合物とを含有する組成物が、有害生物に対して優れた防除効力を有することを見出し、本発明に到った。 As a result of intensive studies to find a composition having an excellent control effect, the present inventor has found that the following formula (I)

[Where,
R ¹ is a C1-C5 haloalkyl group having at least one fluorine atom, a C3-C5 alkenyl group optionally substituted with a halogen atom, a C3-C5 alkenyloxy group optionally substituted with a halogen atom, a halogen atom A C3-C5 alkynyl group which may be substituted with or a C3-C5 alkynyloxy group which may be substituted with a halogen atom,
R ² is a C1-C4 alkyl group optionally substituted with a halogen atom, a C1-C4 alkoxy group optionally substituted with a halogen atom, a C1-C4 alkylthio group optionally substituted with a halogen atom, a halogen atom Or represents a hydrogen atom,
(However, when R ¹ is a C3-C5 alkenyloxy group which may be substituted with a halogen atom or a C3-C5 alkynyloxy group which may be substituted with a halogen atom, R ² is substituted with a halogen atom. It may be a C1-C4 alkyl group or a hydrogen atom.)
R ³ represents a C1-C4 alkyl group, a halogen atom or a hydrogen atom,
R ⁴ represents a cyano group, C (= Q) OR ⁷ or C (= Q) N (R ⁸ ) ₂ ,
R ⁵ represents a hydrogen atom, a halogen atom or a C1-C4 alkyl group,
R ⁶ represents a C1-C5 fluoroalkyl group,
Q represents an oxygen atom or a sulfur atom,
R ⁷ represents a C1-C4 alkyl group,
R ⁸ is either a hydrogen atom or a C1-C4 alkyl group each independently, the two R ⁸ are bonded at the ends represents a C2-C7 alkylene group,
m represents an integer of 0 to 4,
n represents 0, 1 or 2. ]
An organic sulfur compound represented by
Following formula (II)

[Where,
X ¹ represents a cyano group or an acetyl group, and X ² represents a methylthio group, a fluoromethylthio group, a difluoromethylthio group, a trifluoromethylthio group, an ethylthio group, a methylsulfinyl group, a fluoromethylsulfinyl group, a difluoromethylsulfinyl group, or trifluoromethyl. A sulfinyl group or an ethylsulfinyl group is represented, and X ³ represents an amino group, a (2-pyridylmethyl) amino group, a (pyrazinylmethyl) amino group, or a (4-hydroxy-3-methoxybenzylidene) amino group. ]
It has been found that a composition containing a pyrazole compound represented by the formula (1) has an excellent control effect against pests, and has reached the present invention.

That is, the present invention includes the following inventions.
[Invention 1]
A pest control composition comprising an organic sulfur compound represented by the following formula (I) and a pyrazole compound represented by the following formula (II).
[Invention 2]
In formula (I), R ¹ may be a C3-C5 alkenyl group optionally substituted with a halogen atom, a C3-C5 alkenyloxy group optionally substituted with a halogen atom, or a C3 optionally substituted with a halogen atom. The composition according to invention 1, which is a C3-C5 alkynyloxy group optionally substituted with a -C5 alkynyl group or a halogen atom.
[Invention 3]
In formula (I), R ¹ is a C1-C5 haloalkyl group having at least one fluorine atom and at least one chlorine atom, or a C1-C5 haloalkyl group having at least one fluorine atom and at least one bromine atom. The composition according to invention 1, wherein
[Invention 4]
The composition according to invention 1, wherein in formula (I), R ¹ is a C1-C5 haloalkyl group having at least one fluorine atom, and R ² and R ³ are hydrogen atoms.
[Invention 5]
In the formula (I), R ¹ is a C1-C5 haloalkyl group having at least one fluorine atom, R ² is a C1-C4 alkyl group optionally substituted with a halogen atom, and R ³ is a hydrogen atom The composition according to claim 1.
[Invention 6]
In the formula (I), R ¹ is a C1-C5 haloalkyl group having at least one fluorine atom, R ² is a C1-C4 alkoxy group which may be substituted with a halogen atom, and is substituted with a halogen atom. The composition according to invention 1, wherein the composition is a C1-C4 alkylthio group or a halogen atom, and R ³ is a hydrogen atom.
[Invention 7]
The pyrazole compound represented by the formula (II) is 1- [2,6-dichloro-4- (trifluoromethyl) phenyl-3-cyano-4- (difluoromethylthio) -5-[(2-pyridylmethyl) amino]. -1H-pyrazole,
1- [2,6-dichloro-4- (trifluoromethyl) phenyl-3-cyano-4- (ethylsulfinyl) -5-amino-1H-pyrazole or 1- [2,6-dichloro-4- (tri The composition according to any one of Inventions 1 to 6, which is fluoromethyl) phenyl-3-acetyl-4- (methylsulfinyl) -5-amino-1H-pyrazole.
[Invention 8]
The pyrazole compound represented by the formula (II) is 1- [2,6-dichloro-4- (trifluoromethyl) phenyl-3-cyano-4- (difluoromethylthio) -5-[(2-pyridylmethyl) amino]. It is -1H-pyrazole, The composition of any one of Claims 1-6.
[Invention 9]
In formula (I), R ¹ may be a C3-C5 alkenyl group optionally substituted with a halogen atom, a C3-C5 alkenyloxy group optionally substituted with a halogen atom, or a C3 optionally substituted with a halogen atom. -C5 alkynyl group or a C3-C5 alkynyloxy group optionally substituted by a halogen atom,
The pyrazole compound represented by the formula (II) is 1- [2,6-dichloro-4- (trifluoromethyl) phenyl-3-cyano-4- (difluoromethylthio) -5-[(2-pyridylmethyl) amino]. -1H-pyrazole,
1- [2,6-dichloro-4- (trifluoromethyl) phenyl-3-cyano-4- (ethylsulfinyl) -5-amino-1H-pyrazole or 1- [2,6-dichloro-4- (tri The composition of invention 1 which is fluoromethyl) phenyl-3-acetyl-4- (methylsulfinyl) -5-amino-1H-pyrazole.
[Invention 10]
In formula (I), R ¹ is a C1-C5 haloalkyl group having at least one fluorine atom and at least one chlorine atom, or a C1-C5 haloalkyl group having at least one fluorine atom and at least one bromine atom. And
The pyrazole compound represented by the formula (II) is 1- [2,6-dichloro-4- (trifluoromethyl) phenyl-3-cyano-4- (difluoromethylthio) -5-[(2-pyridylmethyl) amino]. -1H-pyrazole,
1- [2,6-dichloro-4- (trifluoromethyl) phenyl-3-cyano-4- (ethylsulfinyl) -5-amino-1H-pyrazole or 1- [2,6-dichloro-4- (tri The composition of invention 1 which is fluoromethyl) phenyl-3-acetyl-4- (methylsulfinyl) -5-amino-1H-pyrazole.
[Invention 11]
In the formula (I), R ¹ is a C1-C5 haloalkyl group having at least one fluorine atom, R ² and R ³ are hydrogen atoms,
The pyrazole compound represented by the formula (II) is 1- [2,6-dichloro-4- (trifluoromethyl) phenyl-3-cyano-4- (difluoromethylthio) -5-[(2-pyridylmethyl) amino]. -1H-pyrazole,
1- [2,6-dichloro-4- (trifluoromethyl) phenyl-3-cyano-4- (ethylsulfinyl) -5-amino-1H-pyrazole or 1- [2,6-dichloro-4- (tri The composition of invention 1 which is fluoromethyl) phenyl-3-acetyl-4- (methylsulfinyl) -5-amino-1H-pyrazole.
[Invention 12]
In the formula (I), R ¹ is a C1-C5 haloalkyl group having at least one fluorine atom, R ² is a C1-C4 alkyl group optionally substituted with a halogen atom, and R ³ is a hydrogen atom And
The pyrazole compound represented by the formula (II) is 1- [2,6-dichloro-4- (trifluoromethyl) phenyl-3-cyano-4- (difluoromethylthio) -5-[(2-pyridylmethyl) amino]. -1H-pyrazole,
1- [2,6-dichloro-4- (trifluoromethyl) phenyl-3-cyano-4- (ethylsulfinyl) -5-amino-1H-pyrazole or 1- [2,6-dichloro-4- (tri The composition of claim 1 which is fluoromethyl) phenyl-3-acetyl-4- (methylsulfinyl) -5-amino-1H-pyrazole.
[Invention 13]
In the formula (I), R ¹ is a C1-C5 haloalkyl group having at least one fluorine atom, R ² is a C1-C4 alkoxy group which may be substituted with a halogen atom, and is substituted with a halogen atom. A C1-C4 alkylthio group or a halogen atom, R ³ is a hydrogen atom,
The pyrazole compound represented by the formula (II) is 1- [2,6-dichloro-4- (trifluoromethyl) phenyl-3-cyano-4- (difluoromethylthio) -5-[(2-pyridylmethyl) amino]. -1H-pyrazole,
1- [2,6-dichloro-4- (trifluoromethyl) phenyl-3-cyano-4- (ethylsulfinyl) -5-amino-1H-pyrazole or 1- [2,6-dichloro-4- (tri The composition of invention 1 which is fluoromethyl) phenyl-3-acetyl-4- (methylsulfinyl) -5-amino-1H-pyrazole.
[Invention 14]
In formula (I), R ¹ may be a C3-C5 alkenyl group optionally substituted with a halogen atom, a C3-C5 alkenyloxy group optionally substituted with a halogen atom, or a C3 optionally substituted with a halogen atom. -C5 alkynyl group or a C3-C5 alkynyloxy group optionally substituted by a halogen atom,
The pyrazole compound represented by the formula (II) is 1- [2,6-dichloro-4- (trifluoromethyl) phenyl-3-cyano-4- (difluoromethylthio) -5-[(2-pyridylmethyl) amino]. The composition of invention 1 which is -1H-pyrazole.
[Invention 15]
In formula (I), R ¹ is a C1-C5 haloalkyl group having at least one fluorine atom and at least one chlorine atom, or a C1-C5 haloalkyl group having at least one fluorine atom and at least one bromine atom. And
The pyrazole compound represented by the formula (II) is 1- [2,6-dichloro-4- (trifluoromethyl) phenyl-3-cyano-4- (difluoromethylthio) -5-[(2-pyridylmethyl) amino]. The composition of invention 1 which is -1H-pyrazole.
[Invention 16]
In the formula (I), R ¹ is a C1-C5 haloalkyl group having at least one fluorine atom, R ² and R ³ are hydrogen atoms,
The pyrazole compound represented by the formula (II) is 1- [2,6-dichloro-4- (trifluoromethyl) phenyl-3-cyano-4- (difluoromethylthio) -5-[(2-pyridylmethyl) amino]. The composition according to invention 1, which is -1H-pyrazole.
[Invention 17]
In the formula (I), R ¹ is a C1-C5 haloalkyl group having at least one fluorine atom, R ² is a C1-C4 alkyl group optionally substituted with a halogen atom, and R ³ is a hydrogen atom And
The pyrazole compound represented by the formula (II) is 1- [2,6-dichloro-4- (trifluoromethyl) phenyl-3-cyano-4- (difluoromethylthio) -5-[(2-pyridylmethyl) amino]. The composition of claim 1 which is -1H-pyrazole.
[Invention 18]
In the formula (I), R ¹ is a C1-C5 haloalkyl group having at least one fluorine atom, R ² is a C1-C4 alkoxy group which may be substituted with a halogen atom, and is substituted with a halogen atom. A C1-C4 alkylthio group or a halogen atom, R ³ is a hydrogen atom,
The pyrazole compound represented by the formula (II) is 1- [2,6-dichloro-4- (trifluoromethyl) phenyl-3-cyano-4- (difluoromethylthio) -5-[(2-pyridylmethyl) amino]. The composition of invention 1 which is -1H-pyrazole.
[Invention 19]
A pest control method comprising applying the composition according to any one of the inventions 1 to 18 to a pest or a habitat of the pest.
[Invention 20]
Use of the composition according to any one of Inventions 1 to 18 for controlling pests.

  The control composition of the present invention has excellent efficacy in controlling pests.

  In the control composition of the present invention, an organic sulfur compound represented by the formula (I) (hereinafter referred to as the present organic sulfur compound) and a pyrazole compound represented by the formula (II) (hereinafter referred to as the present pyrazole compound) Is preferably in the range of 1000: 1 to 1: 1000, more preferably 500: 1 to 1: 500, 100: 1 to 1: 100, 10: 1 to 1:10.

In the present specification, the “halogen atom” means a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.
Examples of the “C1-C5 haloalkyl group having at least one fluorine atom” include a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a 1-fluoroethyl group, a 2-fluoroethyl group, and 1,1-difluoroethyl. Group, 2,2-difluoroethyl group, 2,2,2-trifluoroethyl group, 1,1,2,2,2-pentafluoroethyl group,
1-fluoropropyl group, 1,1-difluoropropyl group, 2-fluoropropyl group, 2,2-difluoropropyl group, 3-fluoropropyl group, 3,3-difluoropropyl group, 3,3,3-trifluoro Propyl group, 1,1,2,2,3,3,3-heptafluoropropyl group, 2,2,3,3,3-pentafluoropropyl group, 2,2,2-trifluoro- (1-tri Fluoromethyl) ethyl group, 1,2,2,2-tetrafluoro- (1-trifluoromethyl) ethyl group, 2,2,3,3-tetrafluoropropyl group,
1-fluorobutyl group, 1,1-difluorobutyl group, 2-fluorobutyl group, 2,2-difluorobutyl group, 3-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, 2,2 , 3,3,4,4,4-heptafluorobutyl group,
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, 2,2,3,3,4,4,5, 5,5-nonafluoropentyl group,
3-chloro-3,3-difluoropropyl group, 1-chloro-1,3,3,3-tetrafluoropropyl group, 2,3-dichloro-2,3,3-trifluoropropyl group, 2,2- Dichloro-3,3,3-trifluoropropyl group,
2-chloro-2,4,4,4-tetrafluorobutyl group, 3,4-dichloro-3,4,4-trifluorobutyl group, 3,3-dichloro-4,4,4-trifluorobutyl group 4-chloro-1,1,2,3,3,4,4-heptafluorobutyl group, 3,3-dichloro-4,4,4-trifluorobutyl group, 3,4-dichloro-3,4 , 4-trifluorobutyl group,
5-chloro-2,2,3,4,4,5,5-heptafluoropentyl group, 4,4-dichloro-5,5,5-trifluoropentyl group, 4,5-dichloro-4,5, 5-trifluoropentyl group,
2,2-dibromo-3,3,3-trifluoropropyl group, 2-bromo-3,3,3-trifluoropropyl group, 2,3-dibromo-3,3-difluoropropyl group, 3-bromo- 3,3-difluoropropyl group, 1-bromo-1,3,3,3-tetrafluoropropyl group, 1-bromo-2,2,3,3,3-pentafluoropropyl group, 1,3-dibromo- 2,2,3,3-tetrafluoropropyl group, 3-bromo-2,3,3-trifluoropropyl group, 3-bromo-2,2,3,3-tetrafluoropropyl group, 2,3-dibromo -2,3,3-trifluoropropyl group, 3-bromo-3,3-difluoropropyl group,
2-bromo-2,4,4,4-tetrafluorobutyl group, 2-bromo-3,3,4,4,4-pentafluorobutyl group, 2,4-dibromo-3,3,4,4- Tetrafluorobutyl group, 4-bromo-3,4,4-trifluorobutyl group, 4-bromo-3,3,4,4-tetrafluorobutyl group, 3,4-dibromo-3,4,4-tri Fluorobutyl group, 4-bromo-4,4-difluorobutyl group, 4-bromo-3,3,4,4-tetrafluorobutyl group,
5-bromo-4,4,5,5-tetrafluoropentyl group, 1-bromo-2,2,3,3,4,4,5,5,5-nonafluoropentyl group, 1,1-dibromo- 2,2,3,3,4,4,5,5,5-nonafluoropentyl group,
2-bromo-3,3,4,4,5,5,6,6,6-nonafluorohexyl group, 2,2-dibromo-3,3,4,4,5,5,6,6,6 -Nonafluorohexyl group etc. are mentioned.
Examples of the “C3-C5 alkenyl group optionally substituted with a halogen atom” include 2-propenyl group, 3-butenyl group, 4-pentenyl group, 5-hexenyl group, 6-heptenyl group, 7-octenyl group, 1 -Propenyl group, 2-butenyl group, 3-pentenyl group, 4-hexenyl group, 5-heptenyl group, 6-octenyl group, 2-methyl-1-propenyl group, 3-methyl-2-butenyl group, 4-methyl -3-pentenyl group, 5-methyl-4-hexenyl group, 6-methyl-5-heptenyl group, 1-methyl-1-propenyl group, 2-methyl-2-butenyl group, 3-methyl-3-pentenyl group 4-methyl-4-hexenyl group, 5-methyl-5-heptenyl group, 1,2-dimethyl-1-propenyl group, 2,3-dimethyl-2-butenyl group, 3,4-dimethyl- -Pentenyl group, 4,5-dimethyl-4-hexenyl group, 5,6-dimethyl-5-heptenyl group, 1-methyl-2-propenyl group, 2-methyl-3-butenyl group, 3-methyl-4- Pentenyl group, 4-methyl-5-hexenyl group, 5-methyl-6-heptenyl group, 2-methyl-2-propenyl group, 3-methyl-3-butenyl group, 4-methyl-4-pentenyl group, 5- Methyl-5-hexenyl group, 6-methyl-6-heptenyl group, 3,3-difluoro-2-propenyl group, 4,4-difluoro-3-butenyl group, 3,4,4-trifluoro-3-butenyl Group, 5,5-difluoro-4-pentenyl group, 6,6-difluoro-5-hexenyl group, 7,7-difluoro-6-heptenyl group, 4,4,4-trifluoro-2-butenyl group, 4 -Bro -4,4-difluoro-2-butenyl group, 3-chloro-4,4,4-trifluoro-2-butenyl group, 5-bromo-4-chloro-4,5,5-trifluoro-2-pentenyl group Group, 4,4,5,5,6,6,6-heptafluoro-2-hexenyl group, 3-methyl-4,4,4-trifluoro-2-butenyl group, 3-methyl-4,4, 5,5,5-pentafluoro-2-pentenyl group, 3-methyl-4,4,5,5,6,6,6-heptafluoro-2-hexenyl group, 3- (trifluoromethyl) -2- Pentenyl group, 3-ethyl-4,4,5,5,5-pentafluoro-2-pentenyl group, 3-ethyl-4,4,5,5,6,6,6-heptafluoro-2-hexenyl group Etc.
Examples of the “C3-C5 alkenyloxy group optionally substituted with a halogen atom” include 2-propenyloxy group, 3-butenyloxy group, 4-pentenyloxy group, 5-hexenyloxy group, 6-heptenyloxy group, 7 -Octenyloxy group, 2-butenyloxy group, 3-pentenyloxy group, 4-hexenyloxy group, 5-heptenyloxy group, 6-octenyloxy group and the like can be mentioned.
Examples of the “C3-C5 alkynyl group optionally substituted with a halogen atom” include 2-propynyl group, 3-butynyl group, 4-pentynyl group, 5-hexynyl group, 6-heptynyl group, 7-octynyl group, 1-methyl-2-propynyl group, 2-methyl-3-butynyl group, 3-methyl-4-pentynyl group, 4-methyl-5-hexynyl group, 5-methyl-6-heptynyl group, 6-methyl-7 -Octynyl group, 1-methyl-5-hexynyl group, 1-ethyl-5-hexynyl group, 1,1-dimethyl-5-hexynyl group, 2-methyl-5-hexynyl group, 2-ethyl-5-hexynyl group 2,2-dimethyl-5-hexynyl group, 3-methyl-5-hexynyl group, 3-ethyl-5-hexynyl group, 3,3-dimethyl-5-hexynyl group, 4-methyl-5-hexene Sinyl group, 4-ethyl-5-hexynyl group, 4,4-dimethyl-5-hexynyl group, 1-propynyl group, 2-butynyl group, 3-pentynyl group, 4-hexynyl group, 5-heptynyl group, 6- Octynyl group, 3,3,3-trifluoro-1-propynyl group, 4,4,4-trifluoro-2-butynyl group, 5,5,5-trifluoro-3-pentynyl group, 6,6,6 -Trifluoro-4-hexynyl group, 7,7,7-trifluoro-5-heptynyl group, 8,8,8-trifluoro-6-octynyl group and the like.
Examples of the “C3-C5 alkynyloxy group optionally substituted with a halogen atom” include 2-propynyloxy group, 3-butynyloxy group, 4-pentynyloxy group, 5-hexynyloxy group, 6-heptynyloxy group, 7 -Octynyloxy group, 1-methyl-2-propynyloxy group, 2-methyl-3-butynyloxy group, 3-methyl-4-pentynyloxy group, 4-methyl-5-hexynyloxy group, 5-methyl-6-heptynyloxy Group, 6-methyl-7-octynyloxy group, 2-butynyloxy) methyl group, (3-pentynyloxy group, 4-hexynyloxy group, 5-heptynyloxy group, 6-octynyloxy group, 4,4,4-trifluoro- 2-butynyloxy group, 5,5,5-trifluoro-3-pentynyloxy group, 6 6,6-trifluoro-4-hexynyloxy group, 7,7,7- trifluoro-5 Hepuchiniruokishi group and the like.
Examples of the “C1-C4 alkyl group optionally substituted with a halogen atom” include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a tert-butyl group, a fluoromethyl group, and a chloromethyl group. Bromomethyl group, difluoromethyl group, trifluoromethyl group, trichloromethyl group and the like.
Examples of the “C1-C4 alkoxy group optionally substituted with a halogen atom” include a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a butoxy group, an isobutoxy group, a tert-butoxy group, and a trifluoromethoxy group. Can be mentioned.
Examples of the “C1-C4 alkylthio group optionally substituted with a halogen atom” include a methylthio group, an ethylthio group, a propylthio group, an isopropylthio group, a butylthio group, an isobutylthio group, a tert-butylthio group, and a trifluoromethylthio group. Is mentioned.
Examples of the “C1-C5 fluoroalkyl group” include a trifluoromethyl group, 1,1,2,2,2-pentafluoroethyl group, 1,1,2,2,3,3,3-heptafluoropropyl group. Etc.
Examples of the “C1-C4 alkyl group” include methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group and the like.

As this organic sulfur compound, for example, in formula (I), R ¹ may C3-C5 optionally substituted with a halogen atom alkenyl group, an optionally substituted C3-C5 alkenyloxy group with a halogen atom, a halogen atom An organic sulfur compound which is a C3-C5 alkynyl group which may be substituted with or a C3-C5 alkynyloxy group which may be substituted with a halogen atom;
In formula (I), R ¹ is a C1-C5 haloalkyl group having at least one fluorine atom and at least one chlorine atom, or a C1-C5 haloalkyl group having at least one fluorine atom and at least one bromine atom. An organic sulfur compound as a group;
In formula (I), R ¹ may be a C3-C5 alkenyl group optionally substituted with a halogen atom, a C3-C5 alkenyloxy group optionally substituted with a halogen atom, or a C3 optionally substituted with a halogen atom -C5 alkynyl group or a halogen atom with optionally substituted C3-C5 alkynyloxy group, an organic sulfur compound R ² and R ³ are hydrogen atoms;
In formula (I), R ¹ is a C1-C5 haloalkyl group having at least one fluorine atom and at least one chlorine atom, or a C1-C5 haloalkyl group having at least one fluorine atom and at least one bromine atom. An organic sulfur compound which is a group and R ² and R ³ are hydrogen atoms;
An organic sulfur compound represented by formula (I), wherein R ¹ is a C1-C5 haloalkyl group having at least one fluorine atom, and R ² and R ³ are hydrogen atoms;
In the formula (I), R ¹ is a C1-C5 haloalkyl group having at least one fluorine atom, R ² is a C1-C4 alkyl group optionally substituted with a halogen atom, and R ³ is a hydrogen atom An organic sulfur compound;
In the formula (I), R ¹ is a C1-C5 haloalkyl group having at least one fluorine atom, R ² is a C1-C4 alkoxy group which may be substituted with a halogen atom, and is substituted with a halogen atom. it is also be C1-C4 alkylthio group or a halogen atom, an organic sulfur compound R ³ is a hydrogen atom, and the like.

This organic sulfur compound, when the asymmetric carbon ^{to which R 4} and ^{R 5} are ^attached, R 1, ^{R 2} and ^{R 3} different is based on the asymmetric carbon ^{to which R} 1, ^{R 2} and ^{R 3} are bonded, Although a stereoisomer exists, what contains an active stereoisomer in arbitrary ratios can be used for this invention.
This organic sulfur compound can be produced, for example, by the following (Production Method 1) to (Production Method 12).

［式中、Ｒ¹、Ｒ²、Ｒ³、Ｒ⁴、Ｒ⁶、ｍ及びｎは前記と同じ意味を表し、Ｒ^5-1はＣ１−Ｃ４アルキル基を表し、Ｘは塩素原子、臭素原子、ヨウ素原子、メタンスルホニルオキシ基、p−トルエンスルホニルオキシ基及びトリフルオロメタンスルホニルオキシ基等の脱離基を表す。］
該反応は通常溶媒中、塩基の存在下で行われる。
反応に用いられる溶媒としては、例えばＮ，Ｎ−ジメチルホルムアミド等の酸アミド、ジエチルエーテル、テトラヒドロフラン等のエーテル、ジメチルスルホキシド、スルホラン等の有機硫黄、クロロホルム、１，２−ジクロロエタン、クロロベンゼン等のハロゲン化炭化水素、トルエン、キシレン等の芳香族炭化水素、水及びそれらの混合物が挙げられる。
該反応に用いられる塩基としては、例えば水素化ナトリウム、水酸化ナトリウム、水酸化カリウム、炭酸カリウム等の無機塩基、ナトリウムメトキシド、カリウム tert−ブトキシド等のアルカリ金属アルコキシド、リチウムジイソプロピルアミド等のアルカリ金属アミド及びトリエチルアミン、１，４−ジアザビシクロ［２．２．２］オクタン、１，８−ジアザビシクロ［５．４．０］−７−ウンデセン等の有機塩基が挙げられる。反応に用いられる塩基の量は、化合物（I-1）１モルに対して通常１〜１０モルの割合である。
反応に用いられる化合物（a）の量は、化合物（I-1）１モルに対し、通常１〜１０モルの割合である。
該反応の反応温度は通常−１００〜１００℃の範囲であり、反応時間は通常１〜２４時間の範囲である。
反応終了後は、反応混合物を水に注加し、有機溶媒抽出してから、濃縮する等の後処理操作を行うことにより化合物（I-2）を単離することができる。単離された化合物（I-2）は必要に応じてクロマトグラフィー、再結晶等によりさらに精製することもできる。 (Production method 1)
Among the present organic sulfur compounds, compound (I-2) in which R ⁵ is a C1-C4 alkyl group can be produced by reacting compound (a) with compound (I-1).

[Wherein R ¹ , R ² , R ³ , R ⁴ , R ⁶ , m and n represent the same meaning as described above, R ^5-1 represents a C1-C4 alkyl group, X represents a chlorine atom, a bromine atom Represents a leaving group such as iodine atom, methanesulfonyloxy group, p-toluenesulfonyloxy group, and trifluoromethanesulfonyloxy group. ]
The reaction is usually performed in a solvent in the presence of a base.
Examples of the solvent used in the reaction include acid amides such as N, N-dimethylformamide, ethers such as diethyl ether and tetrahydrofuran, organic sulfurs such as dimethyl sulfoxide and sulfolane, and halogenations such as chloroform, 1,2-dichloroethane and chlorobenzene. Examples include hydrocarbons, aromatic hydrocarbons such as toluene and xylene, water, and mixtures thereof.
Examples of the base used in the reaction include inorganic bases such as sodium hydride, sodium hydroxide, potassium hydroxide and potassium carbonate, alkali metal alkoxides such as sodium methoxide and potassium tert-butoxide, and alkali metals such as lithium diisopropylamide. And organic bases such as amide and triethylamine, 1,4-diazabicyclo [2.2.2] octane, 1,8-diazabicyclo [5.4.0] -7-undecene. The amount of the base used in the reaction is usually 1 to 10 moles per 1 mole of compound (I-1).
The amount of compound (a) used in the reaction is usually 1 to 10 moles per 1 mole of compound (I-1).
The reaction temperature of the reaction is usually in the range of −100 to 100 ° C., and the reaction time is usually in the range of 1 to 24 hours.
After completion of the reaction, the compound (I-2) can be isolated by performing post-treatment operations such as pouring the reaction mixture into water, extraction with an organic solvent, and concentration. The isolated compound (I-2) can be further purified by chromatography, recrystallization or the like, if necessary.

［式中、Ｒ¹、Ｒ²、Ｒ³、Ｒ⁴、Ｒ⁶、ｍ、ｎ及びＸは前記と同じ意味を表し、Ｒ^5-2は水素原子又はＣ１−Ｃ４アルキル基を表す。］
該反応は通常溶媒中、塩基の存在下で行われる。
反応に用いられる溶媒としては、例えばＮ，Ｎ−ジメチルホルムアミド等の酸アミド、ジエチルエーテル、テトラヒドロフラン等のエーテル、ジメチルスルホキシド、スルホラン等の有機硫黄、クロロホルム、１，２−ジクロロエタン、クロロベンゼン等のハロゲン化炭化水素、トルエン、キシレン等の芳香族炭化水素、水及びそれらの混合物が挙げられる。
該反応に用いられる塩基としては、例えば水素化ナトリウム、水酸化ナトリウム、水酸化カリウム、炭酸カリウム等の無機塩基、ナトリウムメトキシド、カリウム tert−ブトキシド等のアルカリ金属アルコキシド、リチウムジイソプロピルアミド等のアルカリ金属アミド及びトリエチルアミン、１，４−ジアザビシクロ［２．２．２］オクタン、１，８−ジアザビシクロ［５．４．０］−７−ウンデセン等の有機塩基が挙げられる。反応に用いられる塩基の量は、化合物（d）１モルに対して通常１〜１０モルの割合である。
反応に用いられる化合物（c）の量は、化合物（d）１モルに対し、通常１〜１０モルの割合である。
該反応の反応温度は通常−１００〜１００℃の範囲であり、反応時間は通常１〜２４時間の範囲である。
反応終了後は、反応混合物を水に注加し、有機溶媒抽出してから、濃縮する等の後処理操作を行うことにより化合物（I-3）を単離することができる。単離された化合物（I-3）は必要に応じてクロマトグラフィー、再結晶等によりさらに精製することもできる。 (Production method 2)
Among the present organic sulfur compounds, compound (I-3) in which R ⁵ is a hydrogen atom or a C1-C4 alkyl group can be produced by reacting compound (c) with compound (d).

[Wherein, R ¹ , R ² , R ³ , R ⁴ , R ⁶ , m, n and X represent the same meaning as described above, and R ^5-2 represents a hydrogen atom or a C1-C4 alkyl group. ]
The reaction is usually performed in a solvent in the presence of a base.
Examples of the solvent used in the reaction include acid amides such as N, N-dimethylformamide, ethers such as diethyl ether and tetrahydrofuran, organic sulfurs such as dimethyl sulfoxide and sulfolane, and halogenations such as chloroform, 1,2-dichloroethane and chlorobenzene. Examples include hydrocarbons, aromatic hydrocarbons such as toluene and xylene, water, and mixtures thereof.
Examples of the base used in the reaction include inorganic bases such as sodium hydride, sodium hydroxide, potassium hydroxide and potassium carbonate, alkali metal alkoxides such as sodium methoxide and potassium tert-butoxide, and alkali metals such as lithium diisopropylamide. And organic bases such as amide and triethylamine, 1,4-diazabicyclo [2.2.2] octane, 1,8-diazabicyclo [5.4.0] -7-undecene. The amount of the base used in the reaction is usually 1 to 10 moles relative to 1 mole of the compound (d).
The amount of the compound (c) used in the reaction is usually 1 to 10 moles relative to 1 mole of the compound (d).
The reaction temperature of the reaction is usually in the range of −100 to 100 ° C., and the reaction time is usually in the range of 1 to 24 hours.
After completion of the reaction, the compound (I-3) can be isolated by performing post-treatment operations such as pouring the reaction mixture into water, extraction with an organic solvent, and concentration. The isolated compound (I-3) can be further purified by chromatography, recrystallization or the like, if necessary.

［式中、Ｒ¹、Ｒ²、Ｒ³、Ｒ⁴、Ｒ⁶、ｍ及びｎは前記と同じ意味を表し、Ｒ^5-3はハロゲン原子を表す。］
該反応は通常溶媒中、塩基の存在下で行われる。
反応に用いられる溶媒としては、例えばＮ，Ｎ−ジメチルホルムアミド等の酸アミド、ジエチルエーテル、テトラヒドロフラン等のエーテル、ジメチルスルホキシド、スルホラン等の有機硫黄、クロロホルム、１，２−ジクロロエタン、クロロベンゼン等のハロゲン化炭化水素、トルエン、キシレン等の芳香族炭化水素、水及びそれらの混合物が挙げられる。
該反応に用いられる塩基としては、例えば水素化ナトリウム、水酸化ナトリウム、水酸化カリウム、炭酸カリウム等の無機塩基、ナトリウムメトキシド、カリウムtert−ブトキシド等のアルカリ金属アルコキシド、リチウムジイソプロピルアミド等のアルカリ金属アミド及びトリエチルアミン、１，４−ジアザビシクロ［２．２．２］オクタン、１，８−ジアザビシクロ［５．４．０］−７−ウンデセン等の有機塩基が挙げられる。反応に用いられる塩基の量は、化合物（I-1）１モルに対して通常１〜１０モルの割合である。
該反応に用いられるハロゲン化剤（e）としては、例えば四塩化炭素、ヘキサクロロエタン等のハロゲン化炭化水素、フッ素、塩素、臭素、ヨウ素のハロゲン、Ｎ−クロロコハク酸イミド、Ｎ−ブロモコハク酸イミド、Ｎ−ヨードコハク酸イミド等のハロゲン化スクシンイミド、１−フルオロ−２，４，６−トリメチルピリジニウム トリフルオロメタンスルホナート、１，１’−ジフルオロ−２，２’−ビピリジニウム ビステトラフルオロボレート等のＮ−フルオロピリジニウム塩、塩化銅（2価）、臭化銅（2価）等の無機塩が挙げられる。
反応に用いられるハロゲン化剤（e）の量は、化合物（I-1）１モルに対し、通常１〜１０モルの割合である。
該反応の反応温度は通常−１００〜１００℃の範囲であり、反応時間は通常１〜２４時間の範囲である。
反応終了後は、反応混合物を水に注加し、有機溶媒抽出してから、濃縮する等の後処理操作を行うことにより化合物（I-4）を単離することができる。単離された化合物（I-4）は必要に応じてクロマトグラフィー、再結晶等によりさらに精製することもできる。 (Production method 3)
Among the organic sulfur compounds, compounds wherein R ⁵ is halogen atom (I-4) may be Compound (I-1) with a halogenating agent and (e) is prepared by reacting in the presence of a base it can.

[Wherein, R ¹ , R ² , R ³ , R ⁴ , R ⁶ , m and n represent the same meaning as described above, and R ^5-3 represents a halogen atom. ]
The reaction is usually performed in a solvent in the presence of a base.
Examples of the solvent used in the reaction include acid amides such as N, N-dimethylformamide, ethers such as diethyl ether and tetrahydrofuran, organic sulfurs such as dimethyl sulfoxide and sulfolane, and halogenations such as chloroform, 1,2-dichloroethane and chlorobenzene. Examples include hydrocarbons, aromatic hydrocarbons such as toluene and xylene, water, and mixtures thereof.
Examples of the base used in the reaction include inorganic bases such as sodium hydride, sodium hydroxide, potassium hydroxide and potassium carbonate, alkali metal alkoxides such as sodium methoxide and potassium tert-butoxide, and alkali metals such as lithium diisopropylamide. And organic bases such as amide and triethylamine, 1,4-diazabicyclo [2.2.2] octane, 1,8-diazabicyclo [5.4.0] -7-undecene. The amount of the base used in the reaction is usually 1 to 10 moles per 1 mole of compound (I-1).
Examples of the halogenating agent (e) used in the reaction include halogenated hydrocarbons such as carbon tetrachloride and hexachloroethane, fluorine, chlorine, bromine, iodine halogen, N-chlorosuccinimide, N-bromosuccinimide, N-fluoro such as halogenated succinimide such as N-iodosuccinimide, 1-fluoro-2,4,6-trimethylpyridinium trifluoromethanesulfonate, 1,1′-difluoro-2,2′-bipyridinium bistetrafluoroborate Examples include inorganic salts such as pyridinium salts, copper chloride (divalent), copper bromide (divalent).
The amount of the halogenating agent (e) used in the reaction is usually 1 to 10 moles per 1 mole of the compound (I-1).
The reaction temperature of the reaction is usually in the range of −100 to 100 ° C., and the reaction time is usually in the range of 1 to 24 hours.
After completion of the reaction, the compound (I-4) can be isolated by performing post-treatment operations such as pouring the reaction mixture into water, extraction with an organic solvent, and concentration. The isolated compound (I-4) can be further purified by chromatography, recrystallization or the like, if necessary.

［式中、Ｒ¹、Ｒ²、Ｒ³、Ｒ⁴、Ｒ^5-3、Ｒ⁶、ｍ及びｎは前記と同じ意味を表す。］
該反応は無溶媒若しくは溶媒中で行われる。
反応に用いられる溶媒としては、例えばクロロホルム、四塩化炭素、１，２−ジクロロエタン、クロロベンゼン等のハロゲン化炭化水素、トルエン、キシレン等の芳香族炭化水素、アセトニトリル、プロピオニトリル等の脂肪族ニトリル、酢酸等の脂肪族カルボン酸、二硫化炭素、水及びそれらの混合物が挙げられる。
該反応に用いられるハロゲン化剤(f)としては、例えばフッ素、塩素、臭素、ヨウ素のハロゲン、フッ化水素、塩化水素、臭化水素、ヨウ化水素のハロゲン化水素、塩化チオニル、臭化チオニル、塩化スルフリル等のハロゲン化硫黄化合物、三塩化リン、三臭化リン、五塩化リン、オキシ塩化リン等のハロゲン化リン化合物があげられる。
反応に用いられるハロゲン化剤(f)の量は、化合物(I-1）１モルに対し、通常１〜１０モルの割合である。
該反応の反応温度は通常−１００〜２００℃の範囲であり、反応時間は通常１〜２４時間の範囲である。
反応終了後は、反応混合物を水に注加し、有機溶媒抽出してから、濃縮する等の後処理操作を行うことにより化合物(I-4)を単離することができる。単離された化合物(I-4）は必要に応じてクロマトグラフィー、再結晶等によりさらに精製することもできる。 (Production Method 4)
Among the present organic sulfur compounds, compound (I-4) wherein R ⁵ is a halogen atom can be produced by reacting compound (I-1) with halogenating agent (f).

[Wherein, R ¹ , R ² , R ³ , R ⁴ , R ^5-3 , R ⁶ , m and n represent the same meaning as described above. ]
The reaction is carried out without solvent or in a solvent.
Examples of the solvent used in the reaction include halogenated hydrocarbons such as chloroform, carbon tetrachloride, 1,2-dichloroethane, and chlorobenzene, aromatic hydrocarbons such as toluene and xylene, aliphatic nitriles such as acetonitrile and propionitrile, Aliphatic carboxylic acids such as acetic acid, carbon disulfide, water and mixtures thereof.
Examples of the halogenating agent (f) used in the reaction include fluorine, chlorine, bromine, iodine halogen, hydrogen fluoride, hydrogen chloride, hydrogen bromide, hydrogen iodide hydrogen halide, thionyl chloride, thionyl bromide. And sulfur halide compounds such as sulfuryl chloride, and phosphorus halide compounds such as phosphorus trichloride, phosphorus tribromide, phosphorus pentachloride and phosphorus oxychloride.
The amount of the halogenating agent (f) used in the reaction is usually 1 to 10 moles per mole of the compound (I-1).
The reaction temperature is usually in the range of −100 to 200 ° C., and the reaction time is usually in the range of 1 to 24 hours.
After completion of the reaction, the compound (I-4) can be isolated by performing post-treatment operations such as pouring the reaction mixture into water, extraction with an organic solvent, and concentration. The isolated compound (I-4) can be further purified by chromatography, recrystallization or the like, if necessary.

［式中、Ｒ¹、Ｒ²、Ｒ³、Ｒ^5-1、Ｒ⁶、ｍ及びｎは前記と同じ意味を表し、Ｚはハロゲン原子を表し、Ｒ⁷⁸はＯＲ⁷又はＮ(Ｒ⁸）₂を表す（Ｒ⁷及びＲ⁸は前記と同じ意味を表す）。］
（工程５−１）
化合物（i）は、化合物（g）とハロゲン化剤（h）とを反応させることにより製造することができる。
該反応は無溶媒若しくは溶媒中で行うことができる。
反応に用いられる溶媒としては、例えばクロロホルム、ジクロロメタン、１，２−ジクロロエタン、クロロベンゼン等のハロゲン化炭化水素、トルエン、キシレン等の芳香族炭化水素が挙げられる。
反応に用いられるハロゲン化剤（h）としては、例えば塩化オキサリル、塩化チオニル、臭化チオニル、三塩化リン、三臭化リン及び五塩化リンが挙げられる。反応に用いられるハロゲン化剤（h）の量は、化合物（g）１モルに対し、通常１モル〜溶媒量の割合である。
該反応の反応温度は通常−２０〜１００℃の範囲であり、反応時間は通常１〜２４時間の範囲である。
反応終了後は、反応混合物を濃縮する等の操作を行うことにより化合物（i）を単離することができる。単離された化合物（i）は蒸留等によりさらに精製することもできる。
（工程５−２）
該反応は通常溶媒中、塩基の存在下で行われる。
反応に用いられる溶媒としては、例えばＮ，Ｎ−ジメチルホルムアミド等の酸アミド、ジエチルエーテル、テトラヒドロフラン等のエーテル、ジメチルスルホキシド、スルホラン等の有機硫黄、クロロホルム、１，２−ジクロロエタン、クロロベンゼン等のハロゲン化炭化水素、トルエン、キシレン等の芳香族炭化水素、水及びそれらの混合物が挙げられる。
該反応に用いられる塩基としては、例えば水素化ナトリウム、水酸化ナトリウム、水酸化カリウム、炭酸カリウム等の無機塩基及びトリエチルアミン、１，４−ジアザビシクロ［２．２．２］オクタン、１，８−ジアザビシクロ［５．４．０］−７−ウンデセン等の有機塩基が挙げられる。反応に用いられる塩基の量は、化合物（i）１モルに対して通常１〜１０モルの割合である。
反応に用いられる化合物（j）の量は、化合物（i）１モルに対し、通常１〜１０モルの割合である。
該反応の反応温度は通常−２０〜１００℃の範囲であり、反応時間は通常１〜２４時間の範囲である。
反応終了後は、反応混合物を水に注加し、有機溶媒抽出してから、濃縮する等の後処理操作を行うことにより化合物（I-5）を単離することができる。単離された化合物（I-5）は必要に応じてクロマトグラフィー、再結晶等によりさらに精製することもできる。 (Production method 5)
Among the organic sulfur compounds, the compound (I-5) in which R ⁴ is C (═O) OR ⁷ or C (═O) N (R ⁸ ) ₂ is obtained by combining the compound (i) and the compound (j). A method of producing by reacting.

[Wherein R ¹ , R ² , R ³ , R ^5-1 , R ⁶ , m and n represent the same meaning as described above, Z represents a halogen atom, and R ⁷⁸ represents OR ⁷ or N (R ⁸ ) ₂ (R ⁷ and R ⁸ represent the same meaning as described above). ]
(Step 5-1)
Compound (i) can be produced by reacting compound (g) with halogenating agent (h).
The reaction can be carried out without solvent or in a solvent.
Examples of the solvent used in the reaction include halogenated hydrocarbons such as chloroform, dichloromethane, 1,2-dichloroethane, and chlorobenzene, and aromatic hydrocarbons such as toluene and xylene.
Examples of the halogenating agent (h) used in the reaction include oxalyl chloride, thionyl chloride, thionyl bromide, phosphorus trichloride, phosphorus tribromide and phosphorus pentachloride. The amount of the halogenating agent (h) used in the reaction is usually 1 mol to the amount of the solvent with respect to 1 mol of the compound (g).
The reaction temperature of the reaction is usually in the range of -20 to 100 ° C, and the reaction time is usually in the range of 1 to 24 hours.
After completion of the reaction, the compound (i) can be isolated by performing an operation such as concentrating the reaction mixture. The isolated compound (i) can be further purified by distillation or the like.
(Step 5-2)
The reaction is usually performed in a solvent in the presence of a base.
Examples of the solvent used in the reaction include acid amides such as N, N-dimethylformamide, ethers such as diethyl ether and tetrahydrofuran, organic sulfurs such as dimethyl sulfoxide and sulfolane, and halogenations such as chloroform, 1,2-dichloroethane and chlorobenzene. Examples include hydrocarbons, aromatic hydrocarbons such as toluene and xylene, water, and mixtures thereof.
Examples of the base used in the reaction include inorganic bases such as sodium hydride, sodium hydroxide, potassium hydroxide and potassium carbonate, triethylamine, 1,4-diazabicyclo [2.2.2] octane, and 1,8-diazabicyclo. And organic bases such as [5.4.0] -7-undecene. The amount of the base used in the reaction is usually 1 to 10 moles per mole of compound (i).
The amount of the compound (j) used in the reaction is usually 1 to 10 moles relative to 1 mole of the compound (i).
The reaction temperature of the reaction is usually in the range of -20 to 100 ° C, and the reaction time is usually in the range of 1 to 24 hours.
After completion of the reaction, the compound (I-5) can be isolated by performing post-treatment operations such as pouring the reaction mixture into water, extraction with an organic solvent, and concentration. The isolated compound (I-5) can be further purified by chromatography, recrystallization or the like, if necessary.

［式中、Ｒ¹、Ｒ²、Ｒ³、Ｒ^5-1、Ｒ⁶、ｍ及びｎは前記と同じ意味を表し、Ｒ⁷⁸はＯＲ⁷又はＮ(Ｒ⁸)₂を表す（Ｒ⁷及びＲ⁸は前記と同じ意味を表す）。］
該反応は通常溶媒中、縮合剤の存在下で行われる。
反応に用いられる溶媒としては、ジエチルエーテル、テトラヒドロフラン等のエーテル、ジメチルスルホキシド、スルホラン等の有機硫黄、クロロホルム、１，２−ジクロロエタン、クロロベンゼン等のハロゲン化炭化水素、トルエン、キシレン等の芳香族炭化水素が挙げられる。
反応に用いられる縮合剤としては、例えばジシクロヘキシルカルボジイミド、Ｎ−（３−ジメチルアミノプロピル）−Ｎ′−エチルカルボジイミド、カルボニルジイミダゾール等が挙げられる。
反応に用いられる縮合剤の量は、化合物（g）１モルに対し、通常１〜１０モルの割合である。
反応に用いられる化合物（j）の量は、化合物（g）１モルに対し、通常１〜１０モルの割合である。
該反応の反応温度は通常−２０〜１００℃の範囲であり、反応時間は通常１〜２４時間の範囲である。
反応終了後は、反応混合物を濃縮する等の操作を行うことにより化合物（I-5）を単離することができる。単離された化合物（I-5）は必要に応じてクロマトグラフィー、再結晶等によりさらに精製することもできる。 (Production method 6)
Among the organic sulfur compounds, the compound (I-5) in which R ⁴ is C (═O) OR ⁷ or C (═O) N (R ⁸ ) ₂ is obtained by combining the compound (g) and the compound (j). It can be produced by reacting.

^{Wherein, R 1, R 2, R} 3, R 5-1, R 6, m and n are as defined above, R ⁷⁸ represents OR ⁷ or _{^{N (R 8) 2 (R}} 7 and R ⁸ represents the same meaning as described above). ]
The reaction is usually performed in a solvent in the presence of a condensing agent.
Solvents used in the reaction include ethers such as diethyl ether and tetrahydrofuran, organic sulfur such as dimethyl sulfoxide and sulfolane, halogenated hydrocarbons such as chloroform, 1,2-dichloroethane and chlorobenzene, and aromatic hydrocarbons such as toluene and xylene. Is mentioned.
Examples of the condensing agent used in the reaction include dicyclohexylcarbodiimide, N- (3-dimethylaminopropyl) -N′-ethylcarbodiimide, carbonyldiimidazole, and the like.
The amount of the condensing agent used in the reaction is usually 1 to 10 moles per mole of the compound (g).
The amount of compound (j) used in the reaction is usually 1 to 10 moles per mole of compound (g).
The reaction temperature of the reaction is usually in the range of -20 to 100 ° C, and the reaction time is usually in the range of 1 to 24 hours.
After completion of the reaction, the compound (I-5) can be isolated by performing an operation such as concentrating the reaction mixture. The isolated compound (I-5) can be further purified by chromatography, recrystallization or the like, if necessary.

［式中、Ｒ¹、Ｒ²、Ｒ³、Ｒ⁴、Ｒ⁶、Ｘ、ｍ及びｎは前記と同じ意味を表す。］
該反応は通常溶媒中、塩基の存在下で行われる。
反応に用いられる溶媒としては、例えばＮ，Ｎ−ジメチルホルムアミド等の酸アミド、ジエチルエーテル、テトラヒドロフラン等のエーテル、ジメチルスルホキシド、スルホラン等の有機硫黄、クロロホルム、１，２−ジクロロエタン、クロロベンゼン等のハロゲン化炭化水素、トルエン、キシレン等の芳香族炭化水素、水及びそれらの混合物が挙げられる。
該反応に用いられる塩基としては、例えば水素化ナトリウム、水酸化ナトリウム、水酸化カリウム、炭酸カリウム等の無機塩基、ナトリウムメトキシド、カリウム tert−ブトキシド等のアルカリ金属アルコキシド、リチウムジイソプロピルアミド等のアルカリ金属アミド及びトリエチルアミン、１，４−ジアザビシクロ［２．２．２］オクタン、１，８−ジアザビシクロ［５．４．０］−７−ウンデセン等の有機塩基が挙げられる。反応に用いられる塩基の量は、化合物（ｋ）１モルに対して通常１〜１０モルの割合である。
反応に用いられる化合物（c）の量は、化合物（k）１モルに対し、通常１〜１０モルの割合である。
該反応の反応温度は通常−１００〜１００℃の範囲であり、反応時間は通常１〜２４時間の範囲である。
反応終了後は、反応混合物を水に注加し、有機溶媒抽出してから、濃縮する等の後処理操作を行うことにより化合物（I-1）を単離することができる。単離された化合物（I-1）は必要に応じてクロマトグラフィー、再結晶等によりさらに精製することもできる。 (Production method 7)
Among the present organic sulfur compounds, compound (I-1) in which R ⁵ is a hydrogen atom can be produced by reacting compound (c) with compound (k).

[Wherein R ¹ , R ² , R ³ , R ⁴ , R ⁶ , X, m and n represent the same meaning as described above. ]
The reaction is usually performed in a solvent in the presence of a base.
Examples of the solvent used in the reaction include acid amides such as N, N-dimethylformamide, ethers such as diethyl ether and tetrahydrofuran, organic sulfurs such as dimethyl sulfoxide and sulfolane, and halogenations such as chloroform, 1,2-dichloroethane and chlorobenzene. Examples include hydrocarbons, aromatic hydrocarbons such as toluene and xylene, water, and mixtures thereof.
Examples of the base used in the reaction include inorganic bases such as sodium hydride, sodium hydroxide, potassium hydroxide and potassium carbonate, alkali metal alkoxides such as sodium methoxide and potassium tert-butoxide, and alkali metals such as lithium diisopropylamide. And organic bases such as amide and triethylamine, 1,4-diazabicyclo [2.2.2] octane, 1,8-diazabicyclo [5.4.0] -7-undecene. The amount of the base used for the reaction is usually 1 to 10 moles relative to 1 mole of the compound (k).
The amount of the compound (c) used for the reaction is usually 1 to 10 moles relative to 1 mole of the compound (k).
The reaction temperature of the reaction is usually in the range of −100 to 100 ° C., and the reaction time is usually in the range of 1 to 24 hours.
After completion of the reaction, the compound (I-1) can be isolated by performing post-treatment operations such as pouring the reaction mixture into water, extraction with an organic solvent, and concentration. The isolated compound (I-1) can be further purified by chromatography, recrystallization or the like, if necessary.

〔式中、Ｒ¹、Ｒ²、Ｒ³、Ｒ⁵、Ｒ⁶、Ｒ⁷、Ｒ⁸、ｍ及びｎは前記と同じ意味を表す。〕
該反応は通常溶媒中で行われる。
反応に用いられる溶媒としては、ジエチルエーテル、テトラヒドロフラン等のエーテル、ジメチルスルホキシド、スルホラン等の有機硫黄、クロロホルム、１，２−ジクロロエタン、クロロベンゼン等のハロゲン化炭化水素、トルエン、キシレン等の芳香族炭化水素が挙げられる。
反応に用いられる化合物（p）の量は、化合物（I-7）１モルに対し、通常１〜１０モルの割合である。
該反応の反応温度は通常−２０〜１００℃の範囲であり、反応時間は通常１〜２４時間の範囲である。
反応終了後は、反応混合物を濃縮する等の操作を行うことにより化合物（I-8）を単離することができる。単離された化合物（I-8）は必要に応じてクロマトグラフィー、再結晶等によりさらに精製することもできる。 (Production method 8)
Among the present organic sulfur compounds, R ⁴ is C (═O) N (R ⁸ ) ₂ and n is 2 (I-8). In the present organic sulfur compound, R ⁴ is C (═O It can also be produced by reacting compound (I-7), which is OR ⁷ and n is 2, with compound (p).

[Wherein, R ¹ , R ² , R ³ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , m, and n represent the same meaning as described above. ]
The reaction is usually performed in a solvent.
Solvents used in the reaction include ethers such as diethyl ether and tetrahydrofuran, organic sulfur such as dimethyl sulfoxide and sulfolane, halogenated hydrocarbons such as chloroform, 1,2-dichloroethane and chlorobenzene, and aromatic hydrocarbons such as toluene and xylene. Is mentioned.
The amount of the compound (p) used in the reaction is usually 1 to 10 moles relative to 1 mole of the compound (I-7).
The reaction temperature of the reaction is usually in the range of -20 to 100 ° C, and the reaction time is usually in the range of 1 to 24 hours.
After completion of the reaction, the compound (I-8) can be isolated by performing an operation such as concentrating the reaction mixture. The isolated compound (I-8) can be further purified by chromatography, recrystallization or the like, if necessary.

〔式中、Ｒ¹、Ｒ²、Ｒ³、Ｒ⁵、Ｒ⁶、Ｒ⁷⁸、ｍ及びｎは前記と同じ意味を表す。〕
該反応は通常溶媒中で行われる。
反応に用いられる溶媒としては、クロロホルム、１，２−ジクロロエタン、クロロベンゼン等のハロゲン化炭化水素、トルエン、キシレン等の芳香族炭化水素が挙げられる。
該反応に用いられる硫黄化剤（ｑ）としては、例えば硫化水素、五硫化二りん等の無機硫黄化合物、２，４−ビス（４−メトキシフェニル）−１，３−ジチア−２，４−ジホスフェタン ２，４−ジスルフィド等の有機硫黄化合物が挙げられる。
該反応に用いられる硫黄化剤（q）の量は、化合物（I-5）１モルに対し、通常０．５〜１０モルの割合である。
該反応の反応温度は通常０〜２５０℃の範囲であり、反応時間は通常１〜７２時間の範囲である。
反応終了後は、反応混合物を濃縮する等の操作を行うことにより化合物（I-9）を単離することができる。単離された化合物（I-9）は必要に応じてクロマトグラフィー、再結晶等によりさらに精製することもできる。 (Production method 9)
Among the organic sulfur compounds, R ⁴ is C (= S) OR ⁷ or C (= S) N (R 8) 2 in which compound (I-9) may, R ⁴ of the organic sulfur compound C ( It can also be produced by reacting the compound (I-5) which is ═O) OR ⁷ or C (═O) N (R ⁸ ) ₂ with the sulfurizing agent (q).

[Wherein R ¹ , R ² , R ³ , R ⁵ , R ⁶ , R ⁷⁸ , m and n represent the same meaning as described above. ]
The reaction is usually performed in a solvent.
Examples of the solvent used in the reaction include halogenated hydrocarbons such as chloroform, 1,2-dichloroethane, and chlorobenzene, and aromatic hydrocarbons such as toluene and xylene.
Examples of the sulfurizing agent (q) used in the reaction include inorganic sulfur compounds such as hydrogen sulfide and diphosphorus pentasulfide, and 2,4-bis (4-methoxyphenyl) -1,3-dithia-2,4- And organic sulfur compounds such as diphosphetane 2,4-disulfide.
The amount of the sulfurizing agent (q) used in the reaction is usually 0.5 to 10 mol with respect to 1 mol of the compound (I-5).
The reaction temperature of the reaction is usually in the range of 0 to 250 ° C., and the reaction time is usually in the range of 1 to 72 hours.
After completion of the reaction, the compound (I-9) can be isolated by performing an operation such as concentrating the reaction mixture. The isolated compound (I-9) can be further purified by chromatography, recrystallization or the like, if necessary.

［式中、Ｒ¹、Ｒ²、Ｒ³、Ｒ⁴、Ｒ^5-2、Ｒ⁶、ｍ及びＸは前記と同じ意味を表す。］
該反応は通常溶媒中、塩基の存在下で行われる。
反応に用いられる溶媒としては、例えばＮ，Ｎ−ジメチルホルムアミド等の酸アミド、ジエチルエーテル、テトラヒドロフラン等のエーテル、ジメチルスルホキシド、スルホラン等の有機硫黄、クロロホルム、１，２−ジクロロエタン、クロロベンゼン等のハロゲン化炭化水素、トルエン、キシレン等の芳香族炭化水素、水及びそれらの混合物が挙げられる。
該反応に用いられる塩基としては、例えば水素化ナトリウム、水酸化ナトリウム、水酸化カリウム、炭酸カリウム等の無機塩基、ナトリウムメトキシド、カリウム tert−ブトキシド等のアルカリ金属アルコキシド、リチウムジイソプロピルアミド等のアルカリ金属アミド及びトリエチルアミン、１，４−ジアザビシクロ［２．２．２］オクタン、１，８−ジアザビシクロ［５．４．０］−７−ウンデセン等の有機塩基が挙げられる。
反応に用いられる塩基の量は、化合物（r）１モルに対して通常１〜１０モルの割合である。
反応に用いられる化合物（m）の量は、化合物（r）１モルに対し、通常１〜１０モルの割合である。
該反応の反応温度は通常−２０〜１００℃の範囲であり、反応時間は通常１〜２４時間の範囲である。
反応終了後は、反応混合物を水に注加し、有機溶媒抽出してから、濃縮する等の後処理操作を行うことにより化合物（I-10）を単離することができる。単離された化合物（I-10）は必要に応じてクロマトグラフィー、再結晶等によりさらに精製することもできる。 (Production method 10)
Among the organic sulfur compounds, the compound (I-10) in which n is 0 can be produced, for example, by the method shown in Production Method 10 or Production Method 11.
The method to manufacture by making a compound (r) and a compound (m) react.

[Wherein R ¹ , R ² , R ³ , R ⁴ , R ^5-2 , R ⁶ , m and X represent the same meaning as described above. ]
The reaction is usually performed in a solvent in the presence of a base.
Examples of the solvent used in the reaction include acid amides such as N, N-dimethylformamide, ethers such as diethyl ether and tetrahydrofuran, organic sulfurs such as dimethyl sulfoxide and sulfolane, and halogenations such as chloroform, 1,2-dichloroethane and chlorobenzene. Examples include hydrocarbons, aromatic hydrocarbons such as toluene and xylene, water, and mixtures thereof.
Examples of the base used in the reaction include inorganic bases such as sodium hydride, sodium hydroxide, potassium hydroxide and potassium carbonate, alkali metal alkoxides such as sodium methoxide and potassium tert-butoxide, and alkali metals such as lithium diisopropylamide. And organic bases such as amide and triethylamine, 1,4-diazabicyclo [2.2.2] octane, 1,8-diazabicyclo [5.4.0] -7-undecene.
The amount of the base used for the reaction is usually 1 to 10 moles relative to 1 mole of the compound (r).
The amount of the compound (m) used in the reaction is usually 1 to 10 moles relative to 1 mole of the compound (r).
The reaction temperature of the reaction is usually in the range of -20 to 100 ° C, and the reaction time is usually in the range of 1 to 24 hours.
After completion of the reaction, the compound (I-10) can be isolated by performing post-treatment operations such as pouring the reaction mixture into water, extraction with an organic solvent, and concentration. The isolated compound (I-10) can be further purified by chromatography, recrystallization or the like, if necessary.

［式中、Ｒ¹、Ｒ²、Ｒ³、Ｒ⁴、Ｒ^5-2、Ｒ⁶、ｍ及びＸは前記と同じ意味を表す。］
該反応は通常溶媒中、塩基の存在下で行われる。
反応に用いられる溶媒としては、例えばＮ，Ｎ−ジメチルホルムアミド等の酸アミド、ジエチルエーテル、テトラヒドロフラン等のエーテル、ジメチルスルホキシド、スルホラン等の有機硫黄、クロロホルム、１，２−ジクロロエタン、クロロベンゼン等のハロゲン化炭化水素、トルエン、キシレン等の芳香族炭化水素、水及びそれらの混合物が挙げられる。
該反応に用いられる塩基としては、例えば水素化ナトリウム、水酸化ナトリウム、水酸化カリウム、炭酸カリウム等の無機塩基、ナトリウムメトキシド、カリウム tert−ブトキシド等のアルカリ金属アルコキシド、リチウムジイソプロピルアミド等のアルカリ金属アミド類及びトリエチルアミン、１，４−ジアザビシクロ［２．２．２］オクタン、１，８−ジアザビシクロ［５．４．０］−７−ウンデセン等の有機塩基が挙げられる。反応に用いられる塩基の量は、化合物（o）１モルに対して通常１〜１０モルの割合である。
反応に用いられる化合物（s）の量は、化合物（o）１モルに対し、通常１〜１０モルの割合である。
該反応の反応温度は通常−２０〜１００℃の範囲であり、反応時間は通常１〜２４時間の範囲である。
反応終了後は、反応混合物を水に注加し、有機溶媒抽出してから、濃縮する等の後処理操作を行うことにより化合物（I-10）を単離することができる。単離された化合物（I-10）は必要に応じてクロマトグラフィー、再結晶等によりさらに精製することもできる。 (Production method 11)
Among the present organic sulfur compounds, compound (I-10) in which n is 0 can be produced by reacting compound (s) with compound (o).

[Wherein R ¹ , R ² , R ³ , R ⁴ , R ^5-2 , R ⁶ , m and X represent the same meaning as described above. ]
The reaction is usually performed in a solvent in the presence of a base.
Examples of the solvent used in the reaction include acid amides such as N, N-dimethylformamide, ethers such as diethyl ether and tetrahydrofuran, organic sulfurs such as dimethyl sulfoxide and sulfolane, and halogenations such as chloroform, 1,2-dichloroethane and chlorobenzene. Examples include hydrocarbons, aromatic hydrocarbons such as toluene and xylene, water, and mixtures thereof.
Examples of the base used in the reaction include inorganic bases such as sodium hydride, sodium hydroxide, potassium hydroxide and potassium carbonate, alkali metal alkoxides such as sodium methoxide and potassium tert-butoxide, and alkali metals such as lithium diisopropylamide. Examples include amides and organic bases such as triethylamine, 1,4-diazabicyclo [2.2.2] octane, 1,8-diazabicyclo [5.4.0] -7-undecene. The amount of the base used for the reaction is usually 1 to 10 moles per mole of the compound (o).
The amount of the compound (s) used in the reaction is usually 1 to 10 moles relative to 1 mole of the compound (o).
The reaction temperature of the reaction is usually in the range of -20 to 100 ° C, and the reaction time is usually in the range of 1 to 24 hours.
After completion of the reaction, the compound (I-10) can be isolated by performing post-treatment operations such as pouring the reaction mixture into water, extraction with an organic solvent, and concentration. The isolated compound (I-10) can be further purified by chromatography, recrystallization or the like, if necessary.

［式中、Ｒ¹、Ｒ²、Ｒ³、Ｒ⁴、Ｒ^5-2、Ｒ⁶及びｍは前記と同じ意味を表し、ｎ’は1又は２を表す。］
該反応は、酸化剤の存在下、通常溶媒の存在下で行われる。
反応に用いられる溶媒としては、例えばメタノール、エタノール等のアルコール、ジクロロメタン、クロロホルム等のハロゲン化炭化水素、トルエン、キシレン等の芳香族炭化水素、酢酸、トリフルオロ酢酸等の脂肪族カルボン酸、水及びそれらの混合物が挙げられる。
該反応に用いられる酸化剤としては、例えば過酢酸、トリフルオロ過酢酸、ｍ−クロロ過安息香酸等の有機過酸化物、塩素、臭素のハロゲン分子、Ｎ−クロロコハク酸イミド等の含ハロゲンイミド、過塩素酸（若しくはその塩）、過ヨウ素酸（若しくはその塩）等のハロゲン化物、過マンガン酸カリウム等の過マンガン酸塩、クロム酸カリウム等のクロム酸塩及び過酸化水素が挙げられる。反応に用いられる酸化剤の量は、化合物（I-10）１モルに対して通常１〜１０モルの割合である。
該反応の反応温度は通常−５０〜２００℃の範囲であり、反応時間は通常１〜７２時間の範囲である。
反応終了後は、反応混合物を水に注加し、有機溶媒抽出してから、濃縮する等の操作を行うことにより、化合物（I-11）を単離することができる。単離した化合物（I-11）は、必要に応じてクロマトグラフィー、再結晶等でさらに精製することもできる。 (Production method 12)
Among the present organic sulfur compounds, compound (I-11) wherein n is 1 or 2 can be produced, for example, by oxidizing compound (I-10).

[Wherein, R ¹ , R ² , R ³ , R ⁴ , R ^5-2 , R ⁶ and m represent the same meaning as described above, and n ′ represents 1 or 2. ]
The reaction is carried out in the presence of an oxidizing agent, usually in the presence of a solvent.
Examples of the solvent used in the reaction include alcohols such as methanol and ethanol, halogenated hydrocarbons such as dichloromethane and chloroform, aromatic hydrocarbons such as toluene and xylene, aliphatic carboxylic acids such as acetic acid and trifluoroacetic acid, water and A mixture thereof may be mentioned.
Examples of the oxidizing agent used in the reaction include organic peroxides such as peracetic acid, trifluoroperacetic acid, and m-chloroperbenzoic acid, halogen molecules such as chlorine and bromine, halogen-containing imides such as N-chlorosuccinimide, Examples thereof include halides such as perchloric acid (or a salt thereof) and periodic acid (or a salt thereof), permanganates such as potassium permanganate, chromates such as potassium chromate, and hydrogen peroxide. The amount of the oxidizing agent used in the reaction is usually 1 to 10 moles per mole of the compound (I-10).
The reaction temperature of the reaction is usually in the range of −50 to 200 ° C., and the reaction time is usually in the range of 1 to 72 hours.
After completion of the reaction, the compound (I-11) can be isolated by pouring the reaction mixture into water, extracting the mixture with an organic solvent, and concentrating the mixture. The isolated compound (I-11) can be further purified by chromatography, recrystallization or the like, if necessary.

  Next, the production method of the intermediate used for the production of the present organic sulfur compound will be described in the reference production method.

［式中、Ｒ¹、Ｒ²、Ｒ³、Ｒ⁵、Ｒ⁶、ｍ及びｎは前記と同じ意味を表し、Ｒ^7-3はメチル基又はエチル基を表す。］
該反応は酸又は塩基、並びに水の存在下、通常有機溶媒中で行われる。
反応に用いられる有機溶媒としては、メタノール、エタノール等のアルコール、ジエチルエーテル、テトラヒドロフラン等のエーテル、ジメチルスルホキシド、スルホラン等の有機硫黄、クロロホルム、１，２−ジクロロエタン、クロロベンゼン等のハロゲン化炭化水素、トルエン、キシレン等の芳香族炭化水素、蟻酸、酢酸等の脂肪族カルボン酸及びそれらの混合物が挙げられる。
反応に用いられる塩基としては、例えば水酸化ナトリウム、水酸化カリウム等の無機塩基が挙げられる。
反応に用いられる酸としては、例えば塩酸、硫酸等の無機酸が挙げられる。
反応に用いられる酸又は塩基の量は、化合物（I-6）１モルに対し、通常１〜１０モルの割合である。
該反応の反応温度は通常−２０〜１００℃の範囲であり、反応時間は通常１〜２４時間の範囲である。
反応終了後は、反応混合物に必要に応じて水及び／又は酸を加え、有機溶媒抽出してから、濃縮する等の操作を行うことにより化合物（g）を単離することができる。単離された化合物（g）は必要に応じてクロマトグラフィー、再結晶等によりさらに精製することもできる。 (Reference production method 1)
Compound (g) can be produced by hydrolyzing compound (I-6).

[Wherein, R ¹ , R ² , R ³ , R ⁵ , R ⁶ , m and n represent the same meaning as described above, and R ^7-3 represents a methyl group or an ethyl group. ]
The reaction is usually carried out in an organic solvent in the presence of an acid or base and water.
Organic solvents used in the reaction include alcohols such as methanol and ethanol, ethers such as diethyl ether and tetrahydrofuran, organic sulfur such as dimethyl sulfoxide and sulfolane, halogenated hydrocarbons such as chloroform, 1,2-dichloroethane and chlorobenzene, toluene And aromatic hydrocarbons such as xylene, aliphatic carboxylic acids such as formic acid and acetic acid, and mixtures thereof.
Examples of the base used for the reaction include inorganic bases such as sodium hydroxide and potassium hydroxide.
Examples of the acid used for the reaction include inorganic acids such as hydrochloric acid and sulfuric acid.
The amount of the acid or base used in the reaction is usually 1 to 10 mol per 1 mol of compound (I-6).
The reaction temperature of the reaction is usually in the range of -20 to 100 ° C, and the reaction time is usually in the range of 1 to 24 hours.
After completion of the reaction, the compound (g) can be isolated by performing an operation such as adding water and / or acid to the reaction mixture as necessary, extracting with an organic solvent, and then concentrating. The isolated compound (g) can be further purified by chromatography, recrystallization or the like, if necessary.

［式中、Ｒ⁴、Ｒ^5-1、Ｒ⁶、ｎ及びＸは前記と同じ意味を表す。］
該反応は通常溶媒中、塩基の存在下で行われる。
反応に用いられる溶媒としては、例えばＮ，Ｎ−ジメチルホルムアミド等の酸アミド、ジエチルエーテル、テトラヒドロフラン等のエーテル、ジメチルスルホキシド、スルホラン等の有機硫黄、クロロホルム、１，２−ジクロロエタン、クロロベンゼン等のハロゲン化炭化水素、トルエン、キシレン等の芳香族炭化水素、水及びそれらの混合物が挙げられる。
該反応に用いられる塩基としては、例えば水素化ナトリウム、水酸化ナトリウム、水酸化カリウム、炭酸カリウム等の無機塩基、ナトリウムメトキシド、カリウム tert−ブトキシド等のアルカリ金属アルコキシド、リチウムジイソプロピルアミド等のアルカリ金属アミド及びトリエチルアミン、１，４−ジアザビシクロ［２．２．２］オクタン、１，８−ジアザビシクロ［５．４．０］−７−ウンデセン等の有機塩基が挙げられる。
反応に用いられる塩基の量は、化合物（k）１モルに対して通常１〜１０モルの割合である。
反応に用いられる化合物（a）の量は、化合物（k）１モルに対し、通常１〜１０モルの割合である。
該反応の反応温度は通常−２０〜１００℃の範囲であり、反応時間は通常１〜２４時間の範囲である。
反応終了後は、反応混合物を水に注加し、有機溶媒抽出してから、濃縮する等の後処理操作を行うことにより化合物（d-1）を単離することができる。単離された化合物（d-1）は必要に応じてクロマトグラフィー、再結晶等によりさらに精製することもできる。 (Reference production method 2)
Among the compounds (d), the compound (d-1) in which R ⁵ is a C1-C4 alkyl group can be produced, for example, by reacting the following compound (a) with the compound (k).

[Wherein, R ⁴ , R ^5-1 , R ⁶ , n and X represent the same meaning as described above. ]
The reaction is usually performed in a solvent in the presence of a base.
Examples of the solvent used in the reaction include acid amides such as N, N-dimethylformamide, ethers such as diethyl ether and tetrahydrofuran, organic sulfurs such as dimethyl sulfoxide and sulfolane, and halogenations such as chloroform, 1,2-dichloroethane and chlorobenzene. Examples include hydrocarbons, aromatic hydrocarbons such as toluene and xylene, water, and mixtures thereof.
Examples of the base used in the reaction include inorganic bases such as sodium hydride, sodium hydroxide, potassium hydroxide and potassium carbonate, alkali metal alkoxides such as sodium methoxide and potassium tert-butoxide, and alkali metals such as lithium diisopropylamide. And organic bases such as amide and triethylamine, 1,4-diazabicyclo [2.2.2] octane, 1,8-diazabicyclo [5.4.0] -7-undecene.
The amount of the base used in the reaction is usually 1 to 10 moles relative to 1 mole of the compound (k).
The amount of the compound (a) used in the reaction is usually 1 to 10 moles relative to 1 mole of the compound (k).
The reaction temperature of the reaction is usually in the range of -20 to 100 ° C, and the reaction time is usually in the range of 1 to 24 hours.
After completion of the reaction, the compound (d-1) can be isolated by performing post-treatment operations such as pouring the reaction mixture into water, extraction with an organic solvent, and concentration. The isolated compound (d-1) can be further purified by chromatography, recrystallization or the like, if necessary.

［式中、Ｒ⁴、Ｒ⁶、Ｘ及びｎ’は前記と同じ意味を表す。］
（工程III−１−ａ）
化合物（k-1）は、例えば化合物（l）と化合物（m）とを反応させることにより製造することができる。
該反応は通常溶媒中、塩基の存在下で行われる。
反応に用いられる溶媒としては、例えばＮ，Ｎ−ジメチルホルムアミド等の酸アミド、ジエチルエーテル、テトラヒドロフラン等のエーテル、ジメチルスルホキシド、スルホラン等の有機硫黄、クロロホルム、１，２−ジクロロエタン、クロロベンゼン等のハロゲン化炭化水素、トルエン、キシレン等の芳香族炭化水素、水及びそれらの混合物が挙げられる。
該反応に用いられる塩基としては、例えば水素化ナトリウム、水酸化ナトリウム、水酸化カリウム、炭酸カリウム等の無機塩基、ナトリウムメトキシド、カリウム tert−ブトキシド等のアルカリ金属アルコキシド、リチウムジイソプロピルアミド等のアルカリ金属アミド及びトリエチルアミン、１，４−ジアザビシクロ［２．２．２］オクタン、１，８−ジアザビシクロ［５．４．０］−７−ウンデセン等の有機塩基が挙げられる。
反応に用いられる塩基の量は、化合物（l）１モルに対して通常１〜１０モルの割合である。
反応に用いられる化合物（m）の量は、化合物（l）１モルに対し、通常１〜１０モルの割合である。
該反応の反応温度は通常−２０〜１００℃の範囲であり、反応時間は通常１〜２４時間の範囲である。
反応終了後は、反応混合物を水に注加し、有機溶媒抽出してから、濃縮する等の後処理操作を行うことにより化合物（k-1）を単離することができる。単離された化合物（k-1）は必要に応じてクロマトグラフィー、再結晶等によりさらに精製することもできる。
（工程III−１−ｂ）
化合物（k-1）は、例えば化合物（n）と化合物（o）とを反応させることにより製造することもできる。
該反応は通常溶媒中、塩基の存在下で行われる。反応に用いられる溶媒としては、例えばＮ，Ｎ−ジメチルホルムアミド等の酸アミド、ジエチルエーテル、テトラヒドロフラン等のエーテル、ジメチルスルホキシド、スルホラン等の有機硫黄、クロロホルム、１，２−ジクロロエタン、クロロベンゼン等のハロゲン化炭化水素、トルエン、キシレン等の芳香族炭化水素、水及びそれらの混合物が挙げられる。
該反応に用いられる塩基としては、例えば水素化ナトリウム、水酸化ナトリウム、水酸化カリウム、炭酸カリウム等の無機塩基、ナトリウムメトキシド、カリウム tert−ブトキシド等のアルカリ金属アルコキシド、リチウムジイソプロピルアミド等のアルカリ金属アミド類及びトリエチルアミン、１，４−ジアザビシクロ［２．２．２］オクタン、１，８−ジアザビシクロ［５．４．０］−７−ウンデセン等の有機塩基が挙げられる。反応に用いられる塩基の量は、化合物（o）１モルに対して通常１〜１０モルの割合である。
反応に用いられる化合物（n）の量は、化合物（o）１モルに対し、通常１〜１０モルの割合である。
該反応の反応温度は通常−２０〜１００℃の範囲であり、反応時間は通常１〜２４時間の範囲である。
反応終了後は、反応混合物を水に注加し、有機溶媒抽出してから、濃縮する等の後処理操作を行うことにより化合物（k-1）を単離することができる。単離された化合物（k-1）は必要に応じてクロマトグラフィー、再結晶等によりさらに精製することもできる。 (Reference production method 3)
Among the compounds (k), the compound (k-1) in which n is 0 and the compound (k-2) in which n is 1 or 2 can be produced, for example, by the method shown below.

[Wherein, R ⁴ , R ⁶ , X and n ′ represent the same meaning as described above. ]
(Process III-1-a)
Compound (k-1) can be produced, for example, by reacting compound (l) with compound (m).
The reaction is usually performed in a solvent in the presence of a base.
Examples of the solvent used in the reaction include acid amides such as N, N-dimethylformamide, ethers such as diethyl ether and tetrahydrofuran, organic sulfurs such as dimethyl sulfoxide and sulfolane, and halogenations such as chloroform, 1,2-dichloroethane and chlorobenzene. Examples include hydrocarbons, aromatic hydrocarbons such as toluene and xylene, water, and mixtures thereof.
Examples of the base used in the reaction include inorganic bases such as sodium hydride, sodium hydroxide, potassium hydroxide and potassium carbonate, alkali metal alkoxides such as sodium methoxide and potassium tert-butoxide, and alkali metals such as lithium diisopropylamide. And organic bases such as amide and triethylamine, 1,4-diazabicyclo [2.2.2] octane, 1,8-diazabicyclo [5.4.0] -7-undecene.
The amount of the base used for the reaction is usually 1 to 10 moles relative to 1 mole of the compound (l).
The amount of the compound (m) used in the reaction is usually 1 to 10 moles relative to 1 mole of the compound (l).
The reaction temperature of the reaction is usually in the range of -20 to 100 ° C, and the reaction time is usually in the range of 1 to 24 hours.
After completion of the reaction, the compound (k-1) can be isolated by performing post-treatment operations such as pouring the reaction mixture into water, extraction with an organic solvent, and concentration. The isolated compound (k-1) can be further purified by chromatography, recrystallization or the like, if necessary.
(Process III-1-b)
Compound (k-1) can also be produced, for example, by reacting compound (n) with compound (o).
The reaction is usually performed in a solvent in the presence of a base. Examples of the solvent used in the reaction include acid amides such as N, N-dimethylformamide, ethers such as diethyl ether and tetrahydrofuran, organic sulfurs such as dimethyl sulfoxide and sulfolane, and halogenations such as chloroform, 1,2-dichloroethane and chlorobenzene. Examples include hydrocarbons, aromatic hydrocarbons such as toluene and xylene, water, and mixtures thereof.
Examples of the base used in the reaction include inorganic bases such as sodium hydride, sodium hydroxide, potassium hydroxide and potassium carbonate, alkali metal alkoxides such as sodium methoxide and potassium tert-butoxide, and alkali metals such as lithium diisopropylamide. Examples include amides and organic bases such as triethylamine, 1,4-diazabicyclo [2.2.2] octane, 1,8-diazabicyclo [5.4.0] -7-undecene. The amount of the base used for the reaction is usually 1 to 10 moles per mole of the compound (o).
The amount of compound (n) used in the reaction is usually 1 to 10 moles per mole of compound (o).
The reaction temperature of the reaction is usually in the range of -20 to 100 ° C, and the reaction time is usually in the range of 1 to 24 hours.
After completion of the reaction, the compound (k-1) can be isolated by performing post-treatment operations such as pouring the reaction mixture into water, extraction with an organic solvent, and concentration. The isolated compound (k-1) can be further purified by chromatography, recrystallization or the like, if necessary.

(Process III-2)
Compound (k-2) can be produced, for example, by oxidizing compound (k-1).
The reaction is carried out in the presence of an oxidizing agent, usually in the presence of a solvent.
Examples of the solvent used in the reaction include alcohols such as methanol and ethanol, halogenated hydrocarbons such as dichloromethane and chloroform, aromatic hydrocarbons such as toluene and xylene, aliphatic carboxylic acids such as acetic acid and trifluoroacetic acid, water and A mixture thereof may be mentioned.
Examples of the oxidizing agent used in the reaction include organic peroxides such as peracetic acid, trifluoroperacetic acid, and m-chloroperbenzoic acid, halogen molecules such as chlorine and bromine, halogen-containing imides such as N-chlorosuccinimide, Examples thereof include halides such as perchloric acid (or a salt thereof) and periodic acid (or a salt thereof), permanganates such as potassium permanganate, chromates such as potassium chromate, and hydrogen peroxide. The amount of the oxidizing agent used for the reaction is usually 1 to 10 moles per mole of the compound (k-1).
The reaction temperature of the reaction is usually in the range of −50 to 200 ° C., and the reaction time is usually in the range of 1 to 72 hours.
After completion of the reaction, the compound (k-2) can be isolated by pouring the reaction mixture into water, extracting the mixture with an organic solvent, and concentrating the mixture. The isolated compound (k-2) can be further purified by chromatography, recrystallization or the like, if necessary.

  The compounds (o) and (r) are described in, for example, The Journal of Organic Chemistry, 27 (1), p. 93-95 (1962) and HETEROCYCLES, 24 (5), p. Each can be produced according to the method described in 1331-1346 (1986).

The compound (s) can be produced, for example, according to the method described in The Journal of Organic Chemistry, 18, p.1112-1116 (1953).
The compounds (a), (c), (j), (m), (n) and (p) are known products or can be produced according to known production methods.

As this pyrazole compound, for example, in Formula (II), X ¹ is a cyano group, X ² is a difluoromethylthio group, and X ³ is a (2-pyridylmethyl) amino group (hereinafter referred to as pyriprol and );
A pyrazole compound represented by formula (II), wherein X ¹ is a cyano group, X ² is a fluoromethylthio group, and X ³ is a (pyrazinylmethyl) amino group;
In formula (II), X ¹ is an acetyl group, X ² is a methylsulfinyl group, and X ³ is an amino group (hereinafter referred to as acetoprole);
In formula (II), X ¹ is a cyano group, X ² is an ethylsulfinyl group, and X ³ is an amino group, a pyrazole compound (hereinafter referred to as ethiprole);
In formula (II), a pyrazole compound in which X ¹ is a cyano group, X ² is a trifluoromethylthio group, and X ³ is a (4-hydroxy-3-methoxybenzylidene) amino group, and the like can be given.

This pyrazole compound has stereoisomers based on the 1st and 3rd asymmetric carbons on the cyclopropane ring, but the present invention uses compounds containing active stereoisomers in any ratio. can do.
This pyrazole compound can be produced, for example, by a method described in JP-A-63-316771, JP-T 2000-502095, JP-T 2001-506664, or the like. Commercially available compounds can also be used.

  Examples of pests for which the pest control composition of the present invention is effective include harmful insects and harmful mites. More specifically, the following are mentioned.

Hemiptera: Insects such as Laodelphax striatellus, Nilaparvata lugens, Sogatella furcifera, Nephotettix cincticeps, Nephotettimpca Leafhoppers, cotton aphids (Aphis gossypii), peach aphids (Myzus persicae), radish aphids (Brevicoryne brassicae), snowy aphids (Aphis spiraecola), tulip beetles (Macrosiphum euphorbiae), aphid sols Aphids (Rhopalosiphum padi), citrus aphids (Toxoptera citricidus), peach beetles (Hyalopterus pruni) chinensis), stink bugs (Eysarcoris parvus), stink bugs (Halyomorpha mista), stink bugs (Trialeurodes vaporariorum), tobacco whitefly (Bemisia tabaci), citrus whitefly (Dialeurodes citri), Dialeurodes citri Whitefly, Aonidiella aurantii, Sanchez scale insect (Comstockaspis perniciosa), Citrus snow scale (Unaspis citri), Ruby beetle (Ceroplastes rubens), Icerya purchasi, Fujikonae scale krak Scale insects such as Pseudoococcus longispinis and Pseudaulacaspis pentagona, bedbugs such as Cimex lectularius, bed bugs, etc.

Lepidoptera: Chilo suppressalis, Tryporyza incertulas, Cnaphalocrocis medinalis, Notarcha derogata, Plodia interpunctella, Ostrinia furiscal (Ostrinia furiscalis) Common moths such as Pediasia teterrellus, Spodoptera litura, Spodoptera exigua, Pseudaletia separata, Mamestra brassicae, Agrotis ipsilon, Agrotis ipsilon, Agrotis ipsilon, Heliotis, Helicoberpa, etc., White butterflies, such as Pieris rapae, Adoxofies, Grapholita molesta, Leguminivora glycinivorella, Azuki beetle (Matsumuraeses azukivora), Apple coca (Adoxophyes orana fasciata), Chanokokumonmonaki (Adoxophyes honmai.), Chamonaki (Homona magnanima), Midlekakumonamaki (Archips fuscocupreanus), Codling moth (Cydia pomonella), etc. ringoneella, Carposina niponensis, etc., Rionetia genus, Scots moth, Limantria, Euplottis, etc., Plutella xylostella, etc., Pectinophora gossypiella Potatoes such as potato moth (Phthorimaea operculella), hitoragers such as Hyphantria cunea, Hirosukoga such as tiger (Tinea translucens), moth (Tineola bisselliella) and the like.

Thrips of the order of thrips: Frankliniella occidentalis, Thrips parmi, Scirtothrips dorsalis, Thrips tabaci, etc.

Diptera: Culex pipiens pallens, Culex tritaeniorhynchus, Culex quinquefasciatus, etc., Aedes aegypti, Aedes albopictus, etc. Genus Anopheles, Chironomidae, Musca domestica, Muscina stabulans, and other houseflies, fly flies, fungi, flies, fly flies such as Delia platura, Delia antiqua, flies (Agromyza oryzae), rice leaf fly (Hydrellia griseola), tomato leaf fly, (Liriomyza sativae), bean leaf fly (Liriomyza trifolii), leafhopper (Chromatomyia horticola) and other leafhoppers (Chromatomyia horticola), Dacus cucurbitae) Fruit flies such as fruit flies (Ceratitis capitata), fruit flies, fruit flies such as Megaselia spiracularis, butterflies such as Clogmia albipunctata, flies such as flies, Tabanus trigonus Etc.

Coleoptera: Western corn root worms (Diabrotica virgifera virgifera), corn root worms such as Southern corn root worms (Diabrotica undecimpunctata howardi), Douganebubui (Anomala cuprea), Japanese beetle (Anomala rufocuprea), Japanese beetle (Popillia japonica) Genus, maize weevil (Sitophilus zeamais), water weevil (Lissorhoptrus oryzophilus), azuki beetle (Callosobruchuys chienensis), weevil (Echinocnemus squameus), cotton weevil (Anthonomus grandis), sweet weevil Grub beetles such as Tenebrio molitor, Tribolium castaneum,
Rice beetles (Oulema oryzae), leaf beetle (Aulacophora femoralis), leaf beetle (Phyllotreta striolata), leaf beetle (Leptinotarsa decemlineata), leaf beetle, Anthrenus verbasci (Lasioderma serricorne) and other species, Epilachna vigintioctopunctata and other epilacunas, Lyctus brunneus, pine beetle (Tomicus piniperda) and other species, and Longhorn beetles such as Anoplophora malasiaca), click beetles (Agriotes spp.), And long-horned beetle (Paederus fuscipes).

Pterodoptera: Locusta migratoria, Gryllotalpa africana, Oxya yezoensis, Oxya japonica, crickets, etc.

Lepidoptera: Cat fleas (Ctenocephalides felis), dog fleas (Ctenocephalides canis), human fleas (Pulex irritans), keops rat fleas (Xenopsylla cheopis), etc.

Lice insect pests: white lice (Pediculus humanus corporis), white lice (Phthirus pubis), cattle lice (Haematopinus eurysternus), sheep lice (Dalmalinia ovis), pig lice (Haematopinus suis), etc.

Hymenoptera: Monomorium pharaosis, Black ants (Formica fusca japonica), Rugliari (Ochetellus glaber), Amphidia (Pristomyrmex pungens), Giant ants (Pheidole noda), Hachiriari (Acromyrmex spp.), Firesis p Such as ants, wasps, scallops, bees (Athalia rosae), Japanese bees (Athalia japonica), etc.

Cockroaches: cockroaches (Blattella germanica), black cockroach (Periplaneta fuliginosa), cockroach (Periplaneta americana), cockroach (Periplaneta brunnea), cockroaches such as cockroach (Blatta orientalis), ants (Coptotermes formosanus), American ant termite (Incisitermes minor), Daikoku termite (Cryptotermes domesticus), Taiwan termite (Odontotermes formosanus), Koshun termite (Neotermes koshunensis), Satsuma termite (Glyptotermes snakatanto) Termites (Glyptotermes fuscus), white termites (Glyptotermes kodamai), white termites (Glyptotermes kushimensis), termites (Hodotermopsis japonica), white-tailed termites (Coptotermes guangzhoensis), Rami termite Termites (Reticulitermes flaviceps amamianus), Kang Mont termites (Reticulitermes sp.), Takasago termite (Nasutitermes takasagoensis), Nitobe termites (Pericapritermes nitobei), warrior termite (Sinocapritermes mushae) termites such as such.

Acarid pests: Spider spider mites (Tetranychus urticae), Spider spider mites (Tetranychus kanzawai), Spider spider mites (Panonychus citri) Ripe spider mites (Panonychus ulmi), Spider mites (Aculops pelekassi), Rick mite Citrus (Aculops) Tomato rustic mites (Aculops lycopersici), Chinese radish mites (Calacarus carinatus), Chinese radish mites (Acaphylla theavagrans), Green rustic mites (Eriophyes chibaensis), apple rustic mites (Aculus schlechtendali), mussels moth, Scarlet mites (Brevipalpus phoenicis) and other spider mites, mosquito spider mites (Haemaphysalis longicornis), Scarlet tick (Haemaphysalis flava), Dermacentor taiwanicus, American dock tick (Dermacentorx varieties) tick such as odes ovatus, tick (Ixodes persulcatus), black legged tick (Ixodes scapularis), lone star tick (Amblyomma americanum), boophilus microplus, Rhipicephalus sanguineus Mushroom mites such as Octodectes cynotis, mite mites such as Sacroptes scabiei, mite mites such as Demodex canis, Tyrophagus putrescentiae, mite mite such as tyrophagus similimato farinae), leopard mites such as Dermatophagoides ptrenyssnus, thorn mites such as Cheyletus malaccensis, tick mites such as nit bait, nits airum), cucumbers such as Dermanyssus gallinae, tsutsugamushi such as Leptotrombidium akamushi, spiders such as Chiracanthium japonicum and Latrodectus hasseltii.

Lip and leg class: Gezi (Thereuonema hilgendorfi), Tobismkade (Scolopendra subspinipes), etc.
Double-legged class: zelkova (Oxidus gracilis), red scallop (Nedyopus tambanus), etc.
Isopods: Armadillidium vulgare, etc.
Gastropoda: Limax marginatus, Limax flavus, etc.

The pest control composition of the present invention may be only the present organic sulfur compound and the present pyrazole compound, but is usually mixed with a solid carrier, a liquid carrier and / or a gaseous carrier, and if necessary, a surfactant or other preparation. Emulsions, oils, shampoos, flowables, powders, wettable powders, granules, pastes, microcapsules, foams, aerosols, carbon dioxide, tablets, resin formulations, etc. It was formulated into a form. These preparations may be used after being processed into poison baits, mosquito coils, electric mosquito mats, fumigants, fumigants, and sheets.
These preparations usually contain 0.1 to 95% by weight in the total amount of the present organic sulfur compound and the present pyrazole compound.

  Examples of solid carriers used for formulation include clays (kaolin clay, diatomaceous earth, bentonite, fusami clay, acidic clay), synthetic hydrous silicon oxide, talc, ceramics, and other inorganic minerals (sericite, quartz, sulfur). , Activated carbon, calcium carbonate, hydrated silica, etc.), fine powders and granular materials such as chemical fertilizers (ammonium sulfate, phosphorous acid, ammonium nitrate, ammonium chloride, urea, etc.).

  Examples of the liquid carrier include aromatic or aliphatic hydrocarbons (xylene, toluene, alkylnaphthalene, phenylxylylethane, kerosene, light oil, hexane, cyclohexane, etc.), halogenated hydrocarbons (chlorobenzene, dichloromethane, dichloroethane, trichloroethane). Etc.), alcohols (methanol, ethanol, isopropyl alcohol, butanol, hexanol, ethylene glycol, etc.), ethers (diethyl ether, ethylene glycol dimethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, propylene glycol monomethyl ether, tetrahydrofuran, dioxane, etc.) ), Esters (ethyl acetate, butyl acetate, etc.), ketones (acetone, methyl ethyl keto) , Methyl isobutyl ketone, cyclohexanone, etc.), nitriles (acetonitrile, isobutyronitrile, etc.), sulfoxides (dimethyl sulfoxide, etc.), acid amides (N, N-dimethylformamide, N, N-dimethylacetamide, etc.), pyrrolidone (N-methyl-2-pyrrolidone, N-octyl-2-pyrrolidone, etc.), propylene carbonate, ethyl lactate, 1,3-dimethyl-2-imidazolidinone, vegetable oil (soybean oil, cottonseed oil, etc.), plant essential oil ( Orange oil, hyssop oil, lemon oil, etc.) and water.

  Examples of the gaseous carrier include butane gas, chlorofluorocarbon gas, liquefied petroleum gas (LPG), dimethyl ether, carbon dioxide gas, and the like.

  Examples of surfactants include alkyl sulfate salts, alkyl sulfonates, alkyl aryl sulfonates, alkyl aryl ethers and polyoxyethylenates thereof, polyethylene glycol ethers, polyhydric alcohol esters, and sugar alcohol derivatives. It is done.

  Other formulation adjuvants include fixing agents, dispersants and stabilizers, such as casein, gelatin, polysaccharides (starch, gum arabic, cellulose derivatives, alginic acid, etc.), lignin derivatives, bentonite, saccharides, Synthetic water-soluble polymers (polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acids, etc.), PAP (isopropyl acid phosphate), BHT (2,6-di-t-butyl-4-methylphenol), BHA (2-t- Butyl-4-methoxyphenol and 3-t-butyl-4-methoxyphenol), vegetable oils, mineral oils, fatty acids and fatty acid esters.

Examples of the base material of the resin preparation include vinyl chloride polymers, polyurethanes, etc., and these base materials include phthalic acid esters (dimethyl phthalate, dioctyl phthalate, etc.), adipic acid esters as necessary. Further, a plasticizer such as stearic acid may be added. The resin formulation is obtained by kneading the compound in the base material using a normal kneading apparatus, and then molding by injection molding, extrusion molding, press molding, etc., and if necessary, through further steps such as molding, cutting, It can be processed into resin preparations such as plate, film, tape, net, and string. These resin preparations are processed, for example, as animal collars, animal ear tags, sheet preparations, attracting strings, or gardening supports.
Examples of the bait base include cereal flour, vegetable oil, sugar, crystalline cellulose and the like, and if necessary, antioxidants such as dibutylhydroxytoluene and nordihydroguaiaretic acid, and preservatives such as dehydroacetic acid. Additives for preventing accidental eating by children and pets such as pepper powder, pests such as cheese flavor, onion flavor, peanut oil and the like are added.

  The pest control composition of the present invention is used, for example, by being applied directly to harmful arthropods and / or by applying to harmful habitats (plants, animal bodies, soil, etc.).

  When the pest control composition of the present invention is used for controlling agricultural and forestry pests, the application amount is usually 1 to 10,000 g / ha, preferably 10 to 500 g / ha, in total amount of the present organic sulfur compound and the present pyrazole compound. . Emulsions, wettable powders, flowables, microcapsules, etc. are usually diluted with water so that the total of the present organic sulfur compound and the present pyrazole compound is 1 to 1000 ppm, and powders, granules, etc. are usually used as they are. To do. These formulations may be applied directly to plants that are to be protected from harmful arthropods. By treating these preparations in the soil, harmful arthropods that inhabit the soil can be controlled, and these preparations can be treated on the nursery before planting, It can also be processed. Furthermore, the sheet preparation of the harmful arthropod control agent of the present invention can be applied by a method such as wrapping around a plant, installing in the vicinity of the plant, or laying on the soil surface of the plant source.

  The harmful arthropod control agent of the present invention can be used in farmland such as fields, paddy fields, lawns, orchards, and without causing phytotoxicity to crops cultivated in the farmland. It may be possible to control harmful arthropods on the ground.

Specific examples of such crops include the following crops.
Agricultural crops: corn, rice, wheat, barley, rye, oat, sorghum, cotton, soybean, peanut, buckwheat, sugar beet, rapeseed, sunflower, sugarcane, tobacco, etc.
Vegetables: Solanum vegetables (eggplants, tomatoes, peppers, peppers, potatoes, etc.), Cucurbitaceae vegetables (cucumbers, pumpkins, zucchini, watermelons, melons, etc.), cruciferous vegetables (radish, turnip, horseradish, kohlrabi, Chinese cabbage, cabbage) , Mustard, broccoli, cauliflower, etc.), asteraceae vegetables (burdock, shungiku, artichoke, lettuce, etc.), liliaceae vegetables (leek, onion, garlic, asparagus), celeryaceae vegetables (carrot, parsley, celery, American scallop, etc.) ), Red crustacean vegetables (spinach, chard, etc.), persimmon vegetables (perilla, mint, basil, etc.), strawberry, sweet potato, yam, taro, etc.
Bridegroom,
Foliage plant,
Fruit trees; pears (apples, pears, Japanese pears, quince, quince, etc.), nuclear fruits (peaches, plums, nectarines, umes, sweet cherry, apricots, prunes, etc.), citrus (satsuma mandarin, orange, lemon, lime, grapefruit) ), Nuts (chestnut, walnut, hazel, almond, pistachio, cashew nut, macadamia nut, etc.), berries (blueberry, cranberry, blackberry, raspberry, etc.), grape, oyster, olive, loquat, banana, coffee, Date palm, coconut palm, etc.
Trees other than fruit trees: Cha, mulberry, flowering trees, street trees (ash, birch, dogwood, eucalyptus, ginkgo, lilac, maple, oak, poplar, redwood, fu, sycamore, zelkova, black bean, peach tree, Tsuga, rat, pine, Spruce, yew) etc.

The above crops include HPPD inhibitors such as isoxaflutol, ALS inhibitors such as imazetapyr and thifensulfuron methyl, EPSP synthase inhibitors, glutamine synthase inhibitors, acetyl CoA carboxylase inhibitors, herbicides such as bromoxynil Also included are crops that have been rendered resistant to resistance by classical breeding methods or genetic engineering techniques.
Examples of crops to which tolerance has been imparted by classical breeding methods include, for example, imidazolinone herbicide-resistant Clearfield (registered trademark) sulfonylurea-based ALS-inhibiting types such as canola and thifensulfuron-methyl Examples include herbicide-resistant STS soybeans. Similarly, SR corn and the like are examples of crops to which tolerance has been imparted to acetyl CoA carboxylase inhibitors such as trion oxime and aryloxyphenoxypropionic acid herbicides by classical breeding methods. Crops that have been rendered tolerant to acetyl CoA carboxylase inhibitors are Procedures of the National Academy of Sciences of the United States of America (Proc. Natl. Acad. Sci. USA) 87, 7175-7179 (1990). A mutant acetyl CoA carboxylase resistant to an acetyl CoA carboxylase inhibitor has been reported in Weed Science 53, 728-746 (2005), and the like. By introducing a mutation related to imparting resistance into a crop acetyl-CoA carboxylase, a crop resistant to the acetyl-CoA carboxylase inhibitor can be produced. Furthermore, nucleic acid introduced with a base substitution mutation represented by chimera plastic technology (Gura T. 1999. Repairing the Genome's Spelling Mistakes. Science 285: 316-318.) Is introduced into a crop cell (acetyl CoA carboxylase). By generating site-specific amino acid substitution mutations in the (herbicide target) gene, crops resistant to (acetyl CoA carboxylase inhibitor / herbicide) can be created.

  Examples of crops to which tolerance is imparted by genetic recombination technology include glyphosate and glufosinate-resistant corn varieties, such as Roundup Ready (registered trademark) and Liberty Link (registered trademark). Already sold by name.

Examples of the crops include crops that can synthesize selective toxins known in the genus Bacillus using genetic recombination techniques.
Examples of insecticidal toxins expressed in such genetically modified plants include insecticidal proteins derived from Bacillus cereus and Bacillus popillie; Cry1Ab derived from Bacillus thuringiensis , Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C, etc., insecticidal proteins such as VIP1, VIP2, VIP3 or VIP3A; nematode-derived insecticidal proteins; Toxins produced by animals such as insect-specific neurotoxins; filamentous fungi toxins; plant lectins; agglutinins; trypsin inhibitors, serine protease inhibitors Agents, protease inhibitors such as patatin, cystatin, papain inhibitor; ribosome inactivating protein (RIP) such as lysine, corn-RIP, abrin, saporin, bryodin; 3-hydroxysteroid oxidase, ecdysteroid-UDP-glucosyl Steroid metabolic enzymes such as transferase and cholesterol oxidase; ecdysone inhibitor; HMG-CoA reductase; ion channel inhibitors such as sodium channel inhibitor and calcium channel inhibitor; juvenile hormone esterase; diuretic hormone receptor; stilbene synthase; Synthase; chitinase; glucanase and the like.
Further, as toxins expressed in such genetically modified crops, insecticidal proteins such as Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C, and other insecticidal proteins such as VIP1, VIP2, VIP3 or VIP3A Also included are hybrid toxins, partially defective toxins, and modified toxins. Hybrid toxins are produced by new combinations of different domains of these proteins using recombinant technology. As a toxin lacking a part, Cry1Ab lacking a part of the amino acid sequence is known. In the modified toxin, one or more amino acids of the natural toxin are substituted.
Examples of these toxins and recombinant plants capable of synthesizing these toxins are disclosed in, for example, EP-A-0374753, WO93 / 07278, WO95 / 34656, EP-A-0427529, EP-A-451878, WO03 / 052073, etc. Are listed.
The toxins contained in these recombinant plants particularly confer resistance to Coleoptera pests, Diptera pests, and Lepidoptera pests.

  In addition, genetically modified plants that contain one or more insecticidal pest resistance genes and express one or more toxins are already known and some are commercially available. Examples of these genetically modified plants include YieldGuard (registered trademark) (a corn variety expressing Cry1Ab toxin), YieldGuard Rootworm (registered trademark) (a corn variety expressing Cry3Bb1 toxin), YieldGuard Plus (registered trademark) (maize variety expressing Cry1Ab and Cry3Bb1 toxin), Herculex I (registered trademark) (phosphino to confer resistance to Cry1Fa2 toxin and glufosinate Corn varieties expressing tricine N-acetyltransferase (PAT)), NuCOTN33B <(registered trademark)> (cotton varieties expressing Cry1Ac toxin), Volgaard I (Bollg) rd I) <registered trademark> (cotton variety expressing Cry1Ac toxin), Volgard II (registered trademark) (cotton variety expressing Cry1Ac and Cry2Ab toxin), VIPCOT <registered trademark> (expressing VIP toxin) Cotton cultivars), NewLeaf <registered trademark> (potato cultivar expressing Cry3A toxin), Natureguard Agurisure GT Advantage (NatureGuard <Agriure <registered trademark> GT Advantage> (GA21 glyphosate resistant trait), Aggresure CB Advantage (Agriure <(R)> CB Advantage) (Bt11 corn borer (CB) trait), Protector (<Trademark>), and the like.

The crops include those given the ability to produce an anti-pathogenic substance having a selective action using genetic recombination technology.
Examples of anti-pathogenic substances include PR proteins (described in PRPs, EP-A-0392225); sodium channel inhibitors, calcium channel inhibitors (virus-produced KP1, KP4, KP6 toxins, etc.) Stilbene synthase; bibenzyl synthase; chitinase; glucanase; peptide antibiotics, heterocyclic antibiotics, protein factors involved in plant disease resistance (called plant disease resistance genes) , Described in WO03 / 000906), and the like. Such anti-pathogenic substances and genetically modified plants that produce them are described in EP-A-0392225, WO95 / 33818, EP-A-0353191, and the like.

When the pest control composition of the present invention is used for epidemics, the application amount is usually 0.001 to 10 mg / m ³ in total when the organic sulfur compound and the pyrazole compound are applied to the space. When applied to 0.001 to 100 mg / m ² . Emulsions, wettable powders, flowables, etc. are usually diluted with water so that the total concentration of the present organic sulfur compound and the present pyrazole compound is 0.01 to 10000 ppm. The poison bait is usually applied as it is.

When the pest control composition of the present invention is used to control ectoparasites of cattle, horses, pigs, sheep, goats, chickens, small animals such as dogs, cats, rats, mice, etc., it is well known in veterinary medicine. It can be used for animals by oral or parenteral administration. Specifically, for the purpose of systemic suppression, for example, tablets (including sugar-coated tablets and film-coated tablets), pills, capsules, granules, fine granules, powders, emulsions, suspensions , Oral preparations such as films; and injections (eg, subcutaneous injections, intravenous injections, intramuscular injections, intraperitoneal injections, drops, sustained-release injections), suppositories (eg, rectal seats) Agents, vaginal suppositories), implants (embedded tablets, molded with biodegradable polymers as base materials, encapsulated in capsules of biocompatible metals such as titanium and releasing active ingredients at a constant rate And the like) and the like. In the case of oral administration, the above preparation can be used by mixing with feed.
In the case of non-systemic suppression, for example, spraying an oil or aqueous solution, applying external preparations (eg, transdermal preparations, ointments), pour-on treatment or spot-on treatment, It is used by a method such as washing the animal or attaching the resin preparation to the animal with a collar or ear tag. The total amount of the present organic sulfur compound and the present ester compound when administered to an animal body is usually in the range of 0.1 to 1000 mg with respect to 1 kg body weight of the animal.

In the pharmaceutical dosage forms used in the above veterinary administration methods, various organic or inorganic carrier substances commonly used as pharmaceutical materials are used, and excipients, lubricants, binders, disintegrants in solid preparations; It is blended as a solvent, a solubilizing agent, a suspending agent, a tonicity agent, a buffering agent, a soothing agent and the like in a liquid preparation. If necessary, preparation additives such as preservatives, antioxidants, colorants, sweeteners and the like can also be used. Preferable examples of the excipient include lactose, sucrose, D-mannitol, D-sorbitol, starch, pregelatinized starch, dextrin, crystalline cellulose, low-substituted hydroxypropylcellulose, sodium carboxymethylcellulose, gum arabic, dextrin, pullulan , Light anhydrous silicic acid, synthetic aluminum silicate, magnesium aluminate metasilicate and the like. Preferable examples of the lubricant include magnesium stearate, calcium stearate, talc, colloidal silica and the like. Preferable examples of the binder include pregelatinized starch, sucrose, gelatin, gum arabic, methylcellulose, carboxymethylcellulose, sodium carboxymethylcellulose, crystalline cellulose, sucrose, D-mannitol, trehalose, dextrin, pullulan, hydroxypropylcellulose, hydroxy Examples thereof include propylmethylcellulose and polyvinylpyrrolidone. Preferable examples of the disintegrant include lactose, sucrose, starch, carboxymethylcellulose, carboxymethylcellulose calcium, croscarmellose sodium, carboxymethylstarch sodium, light anhydrous silicic acid, low substituted hydroxypropylcellulose and the like. Preferable examples of the solvent include water for injection, physiological saline, Ringer's solution, alcohol, propylene glycol, polyethylene glycol, sesame oil, corn oil, olive oil, cottonseed oil and the like. Preferable examples of the solubilizer include polyethylene glycol, propylene glycol, D-mannitol, trehalose, benzyl benzoate, ethanol, trisaminomethane, cholesterol, triethanolamine, sodium carbonate, sodium citrate, sodium salicylate, sodium acetate. Etc. Suitable examples of the suspending agent include surfactants such as stearyltriethanolamine, sodium lauryl sulfate, laurylaminopropionic acid, lecithin, benzalkonium chloride, benzethonium chloride, glyceryl monostearate; for example, polyvinyl alcohol, polyvinyl Examples include hydrophilic polymers such as pyrrolidone, sodium carboxymethylcellulose, methylcellulose, hydroxymethylcellulose, hydroxyethylcellulose, and hydroxypropylcellulose; polysorbates, polyoxyethylene hydrogenated castor oil, and the like. Preferable examples of the tonicity agent include sodium chloride, glycerin, D-mannitol, D-sorbitol, glucose and the like. Preferable examples of the buffer include buffers such as phosphate, acetate, carbonate and citrate. Preferable examples of the soothing agent include benzyl alcohol. Preferable examples of the preservative include p-hydroxybenzoates, chlorobutanol, benzyl alcohol, phenethyl alcohol, dehydroacetic acid, sorbic acid and the like. Preferable examples of the antioxidant include sulfite and ascorbate. Suitable examples of the coloring agent include water-soluble edible tar dyes (eg, edible dyes such as edible red Nos. 2 and 3, edible yellows 4 and 5, edible blue Nos. 1 and 2, and water-insoluble lake dyes ( Examples thereof include aluminum salts of the water-soluble edible tar pigments, natural pigments (eg, β-carotene, chlorophyll, bengara, etc.).
Injectables contain active ingredients as dispersants (eg, polysorbate 80, polyoxyethylene hydrogenated castor oil 60, polyethylene glycol, carboxymethyl cellulose, sodium alginate, etc.), preservatives (eg, methyl paraben, propyl paraben, benzyl alcohol, Chlorobutanol, phenol, etc.), isotonic agents (eg, sodium chloride, glycerin, D-mannitol, D-sorbitol, glucose, etc.) and other aqueous solvents (eg, distilled water, physiological saline, Ringer's solution, etc.) or oily It is produced by dissolving, suspending or emulsifying in a solvent (eg, olive oil, sesame oil, cottonseed oil, vegetable oil such as corn oil, propylene glycol, etc.). At this time, additives such as a solubilizing agent (eg, sodium salicylate, sodium acetate, etc.), a stabilizer (eg, human serum albumin), a soothing agent (eg, benzyl alcohol, etc.) may be used as desired. The injection solution is usually filled in a suitable ampoule.
The pest control composition of the present invention can also be used as a sustained-release preparation. Examples of the sustained-release preparation include microcapsules (for example, microspheres) produced by an underwater drying method (o / w method, w / o / w method, etc.), a phase separation method, a spray drying method, or a method equivalent thereto. -Microcapsules, microparticles, etc.), and those molded with biocompatible polymers.

  The pest control composition of the present invention is mixed with other insecticides, nematicides, acaricides, fungicides, herbicides, plant growth regulators, synergists, fertilizers, soil improvers, animal feeds, etc. Or it can also use together.

  Hereinafter, the present invention will be described in more detail with reference to production examples of the present organic sulfur compound, formulation examples and test examples of the pest control composition of the present invention, but the present invention is not limited to these examples.

  First, the reference manufacture example of this organic sulfur compound is shown.

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）４．００−４．０７（ｍ，１Ｈ）、３．４４−３．６２（ｍ，２Ｈ）、２．７２−２．８７（ｍ，２Ｈ）、２．３６−２．６４（ｍ，４Ｈ） Reference production example 1
0.6 g of 1-iodo-3,3,3-trifluoropropane and 0.5 g of (3,3,3-trifluoropropylsulfonyl) acetonitrile were dissolved in 20 ml of N, N-dimethylformamide. To this, 0.1 g of sodium hydride (60% oily) was added at room temperature, and the mixture was stirred at the same temperature for 24 hours. Then, 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue is subjected to silica gel chromatography and described as 5,5,5-trifluoro-2- (3,3,3-trifluoropropylsulfonyl) pentanenitrile (hereinafter referred to as the present organic sulfur compound (1)). ) 1.44 g was obtained.
This organic sulfur compound (1)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 4.00 to 4.07 (m, 1H), 3.44 to 3.62 (m, 2H), 2.72-2.87 (m , 2H), 2.36-2.64 (m, 4H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）４．２２（ｄｄ，１Ｈ）、３．５４−３．７２（ｍ，２Ｈ）、２．７６−３．０６（ｍ，４Ｈ） Reference production example 2
0.7 g of 2,2,3,3,3-pentafluoropropyl trifluoromethanesulfonic acid and 0.5 g of (3,3,3-trifluoropropylsulfonyl) acetonitrile were dissolved in 20 ml of N, N-dimethylformamide. To this was added 0.3 g of potassium carbonate at room temperature, and the mixture was stirred at the same temperature for 40 hours. Then, 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 4,4,5,5,5-pentafluoro-2- (3,3,3-trifluoropropylsulfonyl) pentanenitrile (hereinafter referred to as the present organic sulfur compound (2 ) 0.40 g was obtained.
This organic sulfur compound (2)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 4.22 (dd, 1H), 3.54-3.72 (m, 2H), 2.76-3.06 (m, 4H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）４．０１−４．０８（ｍ，１Ｈ）、３．４４−３．６２（ｍ，２Ｈ）、２．７３−２．８８（ｍ，２Ｈ）、２．２８−２．６２（ｍ，４Ｈ） Reference production example 3
0.6 g of 1-iodo-3,3,4,4,4-pentafluorobutane and 0.4 g of (3,3,3-trifluoropropylsulfonyl) acetonitrile were dissolved in 20 ml of N, N-dimethylformamide. To this, 0.09 g of sodium hydride (60% oily) was added at room temperature, and the mixture was stirred at the same temperature for 20 hours. Then, 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 5,5,6,6,6-pentafluoro-2- (3,3,3-trifluoropropylsulfonyl) hexanenitrile (hereinafter referred to as the present organic sulfur compound (3 ) 1.44 g was obtained.
This organic sulfur compound (3)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 4.01-4.08 (m, 1H), 3.44-3.62 (m, 2H), 2.73-2.88 (m , 2H), 2.28-2.62 (m, 4H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）４．２２（ｄｄ，１Ｈ）、３．５５−３．７２（ｍ，２Ｈ）、２．７８−３．１０（ｍ，４Ｈ） Reference production example 4
Trifluoromethanesulfonic acid 2,2,3,3,4,4,4-heptafluorobutyl (0.9 g) and (3,3,3-trifluoropropylsulfonyl) acetonitrile (0.5 g) were added to N, N-dimethylformamide (20 ml). Dissolved. To this was added 0.3 g of potassium carbonate at room temperature, and the mixture was stirred at the same temperature for 28 hours. Then, 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 4,4,5,5,6,6,6-heptafluoro-2- (3,3,3-trifluoropropylsulfonyl) hexanenitrile (hereinafter referred to as the present organic compound). 0.40 g was obtained.
This organic sulfur compound (4)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 4.22 (dd, 1H), 3.55-3.72 (m, 2H), 2.78-3.10 (m, 4H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）４．０４−４．０８（ｍ，１Ｈ）、３．４６−３．６３（ｍ，２Ｈ）、２．７３−２．８８（ｍ，２Ｈ）、２．３４−２．６４（ｍ，４Ｈ） Reference production example 5
0.8 g of 1-iodo-3,3,4,4,5,5,5-heptafluoropentane and 0.5 g of (3,3,3-trifluoropropylsulfonyl) acetonitrile in 20 ml of N, N-dimethylformamide Dissolved. To this, 0.1 g of sodium hydride (60% oily) was added at room temperature, and the mixture was stirred at the same temperature for 24 hours. Then, 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, and 5,5,6,6,7,7,7-heptafluoro-2- (3,3,3-trifluoropropylsulfonyl) heptanenitrile (hereinafter referred to as the present organic compound). 0.45 g was obtained.
This organic sulfur compound (5)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 4.04-4.08 (m, 1H), 3.46-3.63 (m, 2H), 2.73-2.88 (m , 2H), 2.34-2.64 (m, 4H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）６．０５（ｔｔ，１Ｈ）、４．２１（ｄｄ，１Ｈ）、３．５０−３．７１（ｍ，２Ｈ）、２．７０−３．０９（ｍ，４Ｈ） Reference production example 6
Trifluoromethanesulfonic acid 2,2,3,3,4,4,5,5-octafluoropentyl 1.3 g and (3,3,3-trifluoropropylsulfonyl) acetonitrile 0.7 g were mixed with N, N-dimethylformamide. Dissolved in 30 ml. To this was added 0.5 g of potassium carbonate at room temperature, and the mixture was stirred at the same temperature for 20 hours. Then, 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, and 4,4,5,5,6,6,7,7-octafluoro-2- (3,3,3-trifluoropropylsulfonyl) heptanenitrile (hereinafter, This is described as the organic sulfur compound (6).) 0.32 g was obtained.
This organic sulfur compound (6)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 6.05 (tt, 1H), 4.21 (dd, 1H), 3.50-3.71 (m, 2H), 2.70- 3.09 (m, 4H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）４．０２−４．０８（ｍ，１Ｈ）、３．４５−３．６３（ｍ，２Ｈ）、２．７３−２．８６（ｍ，２Ｈ）、２．３４−２．６３（ｍ，４Ｈ） Reference production example 7
1-iodo-3,3,4,4,5,5,6,6,6-nonafluorohexane (1.3 g) and (3,3,3-trifluoropropylsulfonyl) acetonitrile (0.7 g) were added to N, N- Dissolved in 30 ml of dimethylformamide. To this was added 0.1 g of potassium carbonate at room temperature, and the mixture was stirred at the same temperature for 6 hours. Then, 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, and 5,5,6,6,7,7,8,8,8-nonafluoro-2- (3,3,3-trifluoropropylsulfonyl) octanenitrile (hereinafter referred to as “5”) This is referred to as the organic sulfur compound (7).) 0.59 g was obtained.
This organic sulfur compound (7)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 4.02-4.08 (m, 1H), 3.45-3.63 (m, 2H), 2.73-2.86 (m , 2H), 2.34-2.63 (m, 4H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）４．０４−４．０９（ｍ，１Ｈ）、３．４８−３．６８（ｍ，２Ｈ）、２．６７−２．８２（ｍ，２Ｈ）、２．３１−２．６１（ｍ，４Ｈ） Reference production example 8
0.6 g of 1-iodo-3,3,4,4,4-pentafluorobutane and 0.4 g of (3,3,4,4,4-pentafluorobutylsulfonyl) acetonitrile in 50 ml of N, N-dimethylformamide Dissolved. To this was added 0.5 g of sodium hydride (60% oily) at room temperature, and the mixture was stirred at the same temperature for 4 days. Then, 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 5,5,6,6,6-pentafluoro-2- (3,3,4,4,4-pentafluorobutylsulfonyl) hexanenitrile (hereinafter referred to as this organic compound). This is referred to as sulfur compound (8).) 2.66 g was obtained.
This organic sulfur compound (8)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 4.04-4.09 (m, 1H), 3.48-3.68 (m, 2H), 2.67-2.82 (m , 2H), 2.31-2.61 (m, 4H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）４．２２（ｄｄ，１Ｈ）、３．５６−３．７６（ｍ，２Ｈ）、２．６８−３．１０（ｍ，４Ｈ） Reference production example 9
Trifluoromethanesulfonic acid 2,2,3,3,4,4,4-heptafluorobutyl 0.7 g and (3,3,4,4,4-pentafluorobutylsulfonyl) acetonitrile 0.5 g were mixed with N, N- Dissolved in 20 ml of dimethylformamide. To this was added 0.3 g of potassium carbonate at room temperature, and the mixture was stirred at the same temperature for 40 hours. Then, 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 4,4,5,5,6,6,6-heptafluoro-2- (3,3,4,4,4-pentafluorobutylsulfonyl) hexanenitrile ( Hereinafter, this organic sulfur compound (9) is described.) 0.38 g was obtained.
This organic sulfur compound (9)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 4.22 (dd, 1H), 3.56-3.76 (m, 2H), 2.68-3.10 (m, 4H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）４．０７（ｄｄ，１Ｈ）、３．４８−３．６７（ｍ，２Ｈ）、２．３２−２．８５（ｍ，６Ｈ） Reference production example 10
1.8 g of 1-iodo-3,3,4,4,4-pentafluorobutane and 2.0 g of (3,3,4,4,5,5,5-heptafluoropentylsulfonyl) acetonitrile were added to N, N- Dissolved in 50 ml of dimethylformamide. To this was added 0.3 g of sodium hydride (60% oily) at room temperature, and the mixture was stirred at the same temperature for 20 hours. Then, 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, and 2- (3,3,4,4,5,5,5-heptafluoropentylsulfonyl) -5,5,6,6,6-pentafluorohexanenitrile ( Hereinafter, this organic sulfur compound (10) is described.) 1.43 g was obtained.
This organic sulfur compound (10)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 4.07 (dd, 1H), 3.48-3.67 (m, 2H), 2.32-2.85 (m, 6H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）３．４０−３．５８（ｍ，２Ｈ）、２．７３−２．８８（ｍ，２Ｈ）、２．１６−２．５８（ｍ，４Ｈ）、１．８３（ｓ，３Ｈ） Reference production example 11
0.2 g of iodomethane and 0.5 g of 5,5,6,6,6-pentafluoro-2- (3,3,3-trifluoropropylsulfonyl) hexanenitrile were dissolved in 20 ml of N, N-dimethylformamide. To this was added 0.06 g of sodium hydride (60% oily) at room temperature, and the mixture was stirred at the same temperature for 20 hours. Then, 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, and 2-methyl-5,5,6,6,6-pentafluoro-2- (3,3,3-trifluoropropylsulfonyl) hexanenitrile (hereinafter referred to as the present organic compound). 0.35 g was obtained.
This organic sulfur compound (11)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 3.40-3.58 (m, 2H), 2.73-2.88 (m, 2H), 2.16-2.58 (m , 4H), 1.83 (s, 3H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）３．４８−３．６５（ｍ，２Ｈ）、２．６１−３．１３（ｍ，４Ｈ）、２．００（ｄ，３Ｈ） Reference 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 in 30 ml of N, N-dimethylformamide Dissolved. To this was added 0.07 g of sodium hydride (60% oily) at room temperature, and the mixture was stirred at the same temperature for 24 hours. Then, 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, and 4,4,5,5,6,6,6-heptafluoro-2-methyl-2- (3,3,3-trifluoropropylsulfonyl) hexanenitrile ( Hereinafter, this organic sulfur compound (12) is described.) 0.32 g was obtained.
This organic sulfur compound (12)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 3.48-3.65 (m, 2H), 2.61-3.13 (m, 4H), 2.00 (d, 3H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）３．４２−３．６１（ｍ，２Ｈ）、２．６８−２．８２（ｍ，２Ｈ）、２．１８−２．５８（ｍ，４Ｈ）、１．８４（ｓ，３Ｈ） Reference 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 in 20 ml of N, N-dimethylformamide Dissolved. To this, 0.05 g of sodium hydride (60% oily) was added at room temperature and stirred at the same temperature for 20 hours. Then, 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, and 2-methyl-5,5,6,6,6-pentafluoro-2- (3,3,4,4,4-pentafluorobutylsulfonyl) hexanenitrile ( Hereinafter, this organic sulfur compound (13) is described.) 0.49 g was obtained.
This organic sulfur compound (13)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 3.42 to 3.61 (m, 2H), 2.68 to 2.82 (m, 2H), 2.18 to 2.58 (m , 4H), 1.84 (s, 3H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）３．４２−３．６１（ｍ，２Ｈ）、２．６８−２．８２（ｍ，２Ｈ）、２．１８−２．５８（ｍ，４Ｈ）、１．８４（ｓ，３Ｈ） Reference production example 14
0.2 g of iodomethane and 0.5 g of 5,5,6,6,6-pentafluoro-2- (3,3,4,4,5,5,5-heptafluoropentylsulfonyl) hexanenitrile were added to N, N- Dissolved in 20 ml of dimethylformamide. To this was added 0.05 g of sodium hydride (60% oily) at room temperature, and the mixture was stirred at the same temperature for 2 days. Then, 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to give 2- (3,3,4,4,5,5,5-heptafluoropentylsulfonyl) -2-methyl-5,5,6,6,6-penta. 0.49 g of fluorohexanenitrile (hereinafter referred to as the present organic sulfur compound (14)) was obtained.
This organic sulfur compound (14)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 3.42 to 3.61 (m, 2H), 2.68 to 2.82 (m, 2H), 2.18 to 2.58 (m , 4H), 1.84 (s, 3H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）３．３９−３．５８（ｍ，２Ｈ）、２．７２−２．８４（ｍ，２Ｈ）、２．３２−２．５６（ｍ，４Ｈ）、２．０６−２．２６（ｍ，２Ｈ）、１．２８（ｔ，３Ｈ） Reference production example 15
0.2 g of iodoethane and 0.5 g of 5,5,6,6,6-pentafluoro-2- (3,3,3-trifluoropropylsulfonyl) hexanenitrile were dissolved in 20 ml of N, N-dimethylformamide. To this, 0.06 g of sodium hydride (60% oily) was added at room temperature and stirred at the same temperature for 10 hours. Then, 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, and 2-ethyl-5,5,6,6,6-pentafluoro-2- (3,3,3-trifluoropropylsulfonyl) hexanenitrile (hereinafter referred to as the present organic compound). This is referred to as a sulfur compound (15).) 0.37 g was obtained.
This organic sulfur compound (15)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 3.39-3.58 (m, 2H), 2.72-2.84 (m, 2H), 2.32-2.56 (m , 4H), 2.06-2.26 (m, 2H), 1.28 (t, 3H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）３．３８−３．５８（ｍ，２Ｈ）、２．７２−２．８６（ｍ，２Ｈ）、２．３２−２．５８（ｍ，４Ｈ）、１．９５−２．１１（ｍ，２Ｈ）、１．５８−１．７２（ｍ，２Ｈ）、１．１０（ｔ，３Ｈ） Reference Production Example 16
Dissolve 0.2 g of 1-iodopropane and 0.5 g of 5,5,6,6,6-pentafluoro-2- (3,3,3-trifluoropropylsulfonyl) hexanenitrile in 20 ml of N, N-dimethylformamide. I let you. To this, 0.06 g of sodium hydride (60% oily) was added at room temperature and stirred at the same temperature for 24 hours. Then, 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 5,5,6,6,6-pentafluoro-2-propyl-2- (3,3,3-trifluoropropylsulfonyl) hexanenitrile (hereinafter referred to as this organic compound). (Referred to as sulfur compound (16).) 0.38 g was obtained.
This organic sulfur compound (16)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 3.38-3.58 (m, 2H), 2.72-2.86 (m, 2H), 2.32-2.58 (m , 4H), 1.95-2.11 (m, 2H), 1.58-1.72 (m, 2H), 1.10 (t, 3H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）３．３９−３．６０（ｍ，２Ｈ）、２．７０−２．８７（ｍ，２Ｈ）、２．２６−２．６２（ｍ，５Ｈ）、１．３５（ｄ，３Ｈ）、１．２７（ｄ，３Ｈ） Reference Production Example 17
Dissolve 0.2 g of 2-iodopropane and 0.5 g of 5,5,6,6,6-pentafluoro-2- (3,3,3-trifluoropropylsulfonyl) hexanenitrile in 20 ml of N, N-dimethylformamide. I let you. To this, 0.06 g of sodium hydride (60% oily) was added at room temperature, and the mixture was stirred at the same temperature for 6 hours, at 60 ° C. for 2 hours, and further at 90 ° C. for 6 hours. Extracted with. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, and 5,5,6,6,6-pentafluoro-2- (2-propyl) -2- (3,3,3-trifluoropropylsulfonyl) hexanenitrile ( Hereinafter, referred to as the present organic sulfur compound (17).) 0.13 g was obtained.
This organic sulfur compound (17)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 3.39-3.60 (m, 2H), 2.70-2.87 (m, 2H), 2.26-2.62 (m , 5H), 1.35 (d, 3H), 1.27 (d, 3H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）３．３８−３．５８（ｍ，２Ｈ）、２．７２−２．８６（ｍ，２Ｈ）、２．３２−２．５８（ｍ，４Ｈ）、１．９４−２．１１（ｍ，２Ｈ）、１．３８−１．６５（ｍ，４Ｈ）、１．００（ｔ，３Ｈ） Reference Production Example 18
Dissolve 0.3 g of 1-iodobutane and 0.5 g of 5,5,6,6,6-pentafluoro-2- (3,3,3-trifluoropropylsulfonyl) hexanenitrile in 20 ml of N, N-dimethylformamide. It was. To this was added 0.06 g of sodium hydride (60% oily) at room temperature, and the mixture was stirred at the same temperature for 8 hours. Then, 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, and 2-butyl-5,5,6,6,6-pentafluoro-2- (3,3,3-trifluoropropylsulfonyl) hexanenitrile (hereinafter referred to as the present organic compound). 0.28 g was obtained.
This organic sulfur compound (18)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 3.38-3.58 (m, 2H), 2.72-2.86 (m, 2H), 2.32-2.58 (m , 4H), 1.94-2.11 (m, 2H), 1.38-1.65 (m, 4H), 1.00 (t, 3H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）３．３８−３．５８（ｍ，２Ｈ）、２．７２−２．８６（ｍ，２Ｈ）、２．３２−２．５８（ｍ，４Ｈ）、１．９４−２．１１（ｍ，２Ｈ）、１．３８−１．６５（ｍ，６Ｈ）、１．００（ｔ，３Ｈ） Reference Production Example 19
Dissolve 0.3 g of 1-iodopentane and 0.5 g of 5,5,6,6,6-pentafluoro-2- (3,3,3-trifluoropropylsulfonyl) hexanenitrile in 20 ml of N, N-dimethylformamide. I let you. To this was added 0.06 g of sodium hydride (60% oily) at room temperature, and the mixture was stirred at the same temperature for 20 hours. Then, 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, and 2- (3,3,4,4,4-pentafluorobutyl) -2- (3,3,3-trifluoropropylsulfonyl) heptanenitrile (hereinafter referred to as the present). 0.28 g of organic sulfur compound (19) is obtained.
This organic sulfur compound (19)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 3.38-3.58 (m, 2H), 2.72-2.86 (m, 2H), 2.32-2.58 (m , 4H), 1.94-2.11 (m, 2H), 1.38-1.65 (m, 6H), 1.00 (t, 3H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）３．５４−３．６７（ｍ，２Ｈ）、２．３９−２．８８（ｍ，６Ｈ） Reference Production Example 20
0.5 g of 5,5,6,6,6-pentafluoro-2- (3,3,3-trifluoropropylsulfonyl) hexanenitrile was dissolved in 20 ml of tetrahydrofuran. To this, 0.06 g of sodium hydride (60% oily) was added at 0 ° C., and the mixture was stirred at the same temperature for 0.5 hour. Subsequently, 0.4 g of 1-fluoro-2,4,6-trimethylpyridinium trifluoromethanesulfonate was added at the same temperature and stirred for 0.5 hours. The mixture was further stirred at room temperature for 10 hours, 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 2,5,5,6,6,6-hexafluoro-2- (3,3,3-trifluoropropylsulfonyl) hexanenitrile (hereinafter referred to as the present organic sulfur compound). (Described as (20).) 0.37 g was obtained.
This organic sulfur compound (20)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 3.54 to 3.67 (m, 2H), 2.39-2.88 (m, 6H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）３．６６−３．８４（ｍ，２Ｈ）、２．４２−２．９２（ｍ，６Ｈ） Reference Production Example 21
0.5 g of 5,5,6,6,6-pentafluoro-2- (3,3,3-trifluoropropylsulfonyl) hexanenitrile was dissolved in 20 ml of tetrahydrofuran. To this, 0.06 g of sodium hydride (60% oily) was added at 0 ° C., and the mixture was stirred at the same temperature for 0.5 hour. Subsequently, 0.2 g of N-chlorosuccinimide was added at the same temperature and stirred for 0.5 hours. After further stirring at room temperature for 3 days, 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, and 2-chloro-5,5,6,6,6-pentafluoro-2- (3,3,3-trifluoropropylsulfonyl) hexanenitrile (hereinafter referred to as the present organic compound). 0.15 g was obtained.
This organic sulfur compound (21)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 3.66-3.84 (m, 2H), 2.42-2.92 (m, 6H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）３．８９（ｓ，３Ｈ）、３．８２−３．８８（ｍ，１Ｈ）、３．３０−３．５０（ｍ，２Ｈ）、２．６２−２．７７（ｍ，２Ｈ）、２．１０−２．２４（ｍ，４Ｈ）、１．６４−１．７５（ｍ，２Ｈ） Reference Production Example 22
2.0 g of 1-iodo-4,4,4-trifluorobutane and 2.0 g of methyl (3,3,3-trifluoropropylsulfonyl) acetate were dissolved in 20 ml of N, N-dimethylformamide. To this was added 1.2 g of potassium carbonate at room temperature, and the mixture was stirred at the same temperature for 20 hours. Then, 10% hydrochloric acid was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, and methyl 6,6,6-trifluoro-2- (3,3,3-trifluoropropylsulfonyl) hexanoate (hereinafter referred to as the present organic sulfur compound (22)). .) 0.80 g was obtained.
This organic sulfur compound (22)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 3.89 (s, 3H), 3.82-3.88 (m, 1H), 3.30-3.50 (m, 2H), 2.62-2.77 (m, 2H), 2.10-2.24 (m, 4H), 1.64-1.75 (m, 2H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）３．９０（ｓ，３Ｈ）、３．８６−３．９４（ｍ，１Ｈ）、３．３８−３．５１（ｍ，２Ｈ）、２．６３−２．７８（ｍ，２Ｈ）、２．３８−２．５３（ｍ，２Ｈ）、２．１８−２．３４（ｍ，２Ｈ） Reference Production Example 23
1.2 g of 1-iodo-3,3,4,4,4-pentafluorobutane and 1.0 g of methyl (3,3,3-trifluoropropylsulfonyl) acetate were dissolved in 20 ml of N, N-dimethylformamide. . To this was added 0.6 g of potassium carbonate at room temperature, and the mixture was stirred at the same temperature for 30 hours. Then, 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, and methyl 5,5,6,6,6-pentafluoro-2- (3,3,3-trifluoropropylsulfonyl) hexanoate (hereinafter referred to as the present organic sulfur compound ( 23).) 1.20 g was obtained.
This organic sulfur compound (23)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 3.90 (s, 3H), 3.86-3.94 (m, 1H), 3.38-3.51 (m, 2H), 2.63-2.78 (m, 2H), 2.38-2.53 (m, 2H), 2.18-2.34 (m, 2H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）３．９１（ｓ，３Ｈ）、３．８９−３．９７（ｍ，１Ｈ）、３．４４−３．５１（ｍ，２Ｈ）、２．５８−２．７３（ｍ，２Ｈ）、２．３９−２．５３（ｍ，２Ｈ）、２．２０−２．３４（ｍ，２Ｈ） Reference Production Example 24
4.8 g of 1-iodo-3,3,4,4,4-pentafluorobutane and 5.0 g of methyl (3,3,4,4,4-pentafluorobutylsulfonyl) acetate in 50 ml of N, N-dimethylformamide Dissolved in. To this was added 0.7 g of sodium hydride (60% oily) at room temperature, and the mixture was stirred at the same temperature for 2 days. Then, 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain methyl 5,5,6,6,6-pentafluoro-2- (3,3,4,4,4-pentafluorobutylsulfonyl) hexanoate (hereinafter referred to as the present product). 4.69 g of organic sulfur compound (24) is obtained.
This organic sulfur compound (24)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 3.91 (s, 3H), 3.89-3.97 (m, 1H), 3.44-3.51 (m, 2H), 2.58-2.73 (m, 2H), 2.39-2.53 (m, 2H), 2.20-2.34 (m, 2H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）３．７５−３．８２（ｍ，１Ｈ）、３．３８−３．５２（ｍ，２Ｈ）、２．６３−２．７８（ｍ，２Ｈ）、２．１８−２．４６（ｍ，４Ｈ）、１．５３（ｓ，９Ｈ） Reference Production Example 25
0.5 g of 5,5,6,6,6-pentafluoro-2- (3,3,3-trifluoropropylsulfonyl) hexanoic acid was dissolved in 10 ml of dichloromethane. To this, 2 drops of N, N-dimethylformamide and then 0.2 ml of oxalyl chloride were successively added dropwise at room temperature. After stirring at the same temperature for 2 hours, the reaction mixture was concentrated under reduced pressure. The obtained residue was dissolved in 20 ml of tetrahydrofuran, and 0.1 g of tert-butyl alcohol and 0.2 ml of triethylamine were added dropwise thereto at room temperature. After stirring at the same temperature for 1 hour, a saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, and tert-butyl 5,5,6,6,6-pentafluoro-2- (3,3,3-trifluoropropylsulfonyl) hexanoate (hereinafter referred to as the present organic sulfur). It describes as a compound (25).) 0.42g was obtained.
This organic sulfur compound (25)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 3.75-3.82 (m, 1H), 3.38-3.52 (m, 2H), 2.62-2.78 (m , 2H), 2.18-2.46 (m, 4H), 1.53 (s, 9H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）３．８８（ｓ，３Ｈ）、３．４３−３．５２（ｍ，２Ｈ）、２．６３−２．７８（ｍ，２Ｈ）、２．０８−２．５４（ｍ，４Ｈ）、１．７０（ｓ，３Ｈ） Reference Production Example 26
0.4 g of iodomethane and 1.0 g of methyl 5,5,6,6,6-pentafluoro-2- (3,3,3-trifluoropropylsulfonyl) hexanoate were dissolved in 20 ml of N, N-dimethylformamide. . To this, 0.1 g of sodium hydride (60% oily) was added at room temperature and stirred at the same temperature for 3 hours, 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, and methyl 2-methyl-5,5,6,6,6-pentafluoro-2- (3,3,3-trifluoropropylsulfonyl) hexanoate (hereinafter referred to as this). 0.73 g of organic sulfur compound (26) is obtained.
This organic sulfur compound (26)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 3.88 (s, 3H), 3.43 to 3.52 (m, 2H), 2.63 to 2.78 (m, 2H), 2.08-2.54 (m, 4H), 1.70 (s, 3H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）３．８８（ｓ，３Ｈ）、３．３３−３．６５（ｍ，２Ｈ）、２．０６−２．７７（ｍ，８Ｈ）、１．０４（ｔ，３Ｈ） Reference Production Example 27
0.4 g of iodoethane and 1.0 g of methyl 5,5,6,6,6-pentafluoro-2- (3,3,3-trifluoropropylsulfonyl) hexanoate were dissolved in 20 ml of N, N-dimethylformamide. . To this was added 0.1 g of sodium hydride (60% oily) at room temperature, and the mixture was stirred at the same temperature for 20 hours. Then, 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, and methyl 2-ethyl-5,5,6,6,6-pentafluoro-2- (3,3,3-trifluoropropylsulfonyl) hexanoate (hereinafter referred to as the present). 0.45 g of organic sulfur compound (27) is obtained.
This organic sulfur compound (27)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 3.88 (s, 3H), 3.33-3.65 (m, 2H), 2.06-2.77 (m, 8H), 1.04 (t, 3H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）３．８７（ｓ，３Ｈ）、３．３２−３．６６（ｍ，２Ｈ）、１．９６−２．７６（ｍ，８Ｈ）、１．１６−１．５８（ｍ，２Ｈ）、１．０１（ｔ，３Ｈ） Reference Production Example 28
0.4 g of 1-iodopropane and 1.0 g of methyl 5,5,6,6,6-pentafluoro-2- (3,3,3-trifluoropropylsulfonyl) hexanoate were added to 20 ml of N, N-dimethylformamide. Dissolved. To this was added 0.1 g of sodium hydride (60% oily) at room temperature, and the mixture was stirred at the same temperature for 20 hours. Then, 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain methyl 5,5,6,6,6-pentafluoro-2-propyl-2- (3,3,3-trifluoropropylsulfonyl) hexanoate (hereinafter referred to as the present product). 0.89 g of organic sulfur compound (28).
This organic sulfur compound (28)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 3.87 (s, 3H), 3.32-3.66 (m, 2H), 1.96-2.76 (m, 8H), 1.16 to 1.58 (m, 2H), 1.01 (t, 3H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）４．００（ｓ，３Ｈ）、３．２６−３．５６（ｍ，２Ｈ）、２．０９−２．８０（ｍ，６Ｈ） Reference Production Example 29
0.5 g of methyl 5,5,6,6,6-pentafluoro-2- (3,3,3-trifluoropropylsulfonyl) hexanoate was dissolved in 20 ml of tetrahydrofuran, and then sodium hydride (60 % Oily) 0.05 g was added and stirred at the same temperature for 0.5 hour. Subsequently, 0.4 g of 1-fluoro-2,4,6-trimethylpyridinium trifluoromethanesulfonate was added at the same temperature and stirred for 0.5 hours. The mixture was further stirred at room temperature for 10 hours, 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain methyl 2,5,5,6,6,6-hexafluoro-2- (3,3,3-trifluoropropylsulfonyl) hexanoate (hereinafter referred to as the present organic sulfur). This is referred to as the compound (29).) 0.39 g was obtained.
This organic sulfur compound (29)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 4.00 (s, 3H), 3.26-3.56 (m, 2H), 2.09-2.80 (m, 6H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）３．９０（ｓ，３Ｈ）、３．４６−３．５３（ｍ，２Ｈ）、２．４５−２．７２（ｍ，３Ｈ）、２．０９−２．３４（ｍ，３Ｈ）、１．７１（ｓ，３Ｈ） Reference Production Example 30
50 g of N, N-dimethylformamide 0.7 g of iodomethane and 2.0 g of 5,5,6,6,6-pentafluoro-2- (3,3,4,4,4-pentafluorobutylsulfonyl) hexanoate Dissolved in. To this, 0.2 g of sodium hydride (60% oily) was added at room temperature and stirred at the same temperature for 4 hours. Then, 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, and methyl 2-methyl-5,5,6,6,6-pentafluoro-2- (3,3,4,4,4-pentafluorobutylsulfonyl) hexanoate. (Hereinafter referred to as the present organic sulfur compound (30).) 1.20 g was obtained.
This organic sulfur compound (30)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 3.90 (s, 3H), 3.46-3.53 (m, 2H), 2.45-2.72 (m, 3H), 2.09-2.34 (m, 3H), 1.71 (s, 3H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）６．３４（ｂｓ，１Ｈ）、５．７３（ｂｓ，１Ｈ）、３．７３（ｄｄ，１Ｈ）、３．２１−３．４２（ｍ，２Ｈ）、２．６４−２．７３（ｍ，２Ｈ）、２．１２−２．４８（ｍ，４Ｈ） Reference production example 31
0.5 g of 5,5,6,6,6-pentafluoro-2- (3,3,3-trifluoropropylsulfonyl) hexanoic acid was dissolved in 10 ml of dichloromethane. To this, 2 drops of N, N-dimethylformamide and then 0.2 ml of oxalyl chloride were successively added dropwise at room temperature. After stirring at the same temperature for 2 hours, the reaction mixture was concentrated under reduced pressure. The obtained residue was dissolved in 20 ml of tetrahydrofuran, and 0.2 g of ammonia (30% (w / w) aqueous solution) was added dropwise thereto at room temperature. After stirring at the same temperature for 2 hours, a saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 5,5,6,6,6-pentafluoro-2- (3,3,3-trifluoropropylsulfonyl) hexanamide (hereinafter referred to as the present organic sulfur compound (31 ) 0.24 g was obtained.
This organic sulfur compound (31)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 6.34 (bs, 1H), 5.73 (bs, 1H), 3.73 (dd, 1H), 3.21-3.42 ( m, 2H), 2.64-2.73 (m, 2H), 2.12-2.48 (m, 4H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）６．２２（ｂｓ，１Ｈ）、３．６３（ｄｄ，１Ｈ）、３．１８−３．３９（ｍ，２Ｈ）、２．９４（ｄ，３Ｈ）、２．６０−２．７３（ｍ，２Ｈ）、２．０８−２．５０（ｍ，４Ｈ） Reference Production Example 32
0.5 g of 5,5,6,6,6-pentafluoro-2- (3,3,3-trifluoropropylsulfonyl) hexanoic acid was dissolved in 10 ml of dichloromethane. To this, 2 drops of N, N-dimethylformamide and then 0.2 ml of oxalyl chloride were successively added dropwise at room temperature. After stirring at the same temperature for 1 hour, the reaction mixture was concentrated under reduced pressure. The obtained residue was dissolved in 20 ml of tetrahydrofuran, and 0.3 g of methylamine (40% (w / w) aqueous solution) was added dropwise thereto at room temperature. After stirring at the same temperature for 2 hours, a saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, and N-methyl-5,5,6,6,6-pentafluoro-2- (3,3,3-trifluoropropylsulfonyl) hexanamide (hereinafter referred to as the present organic compound). 0.26 g was obtained.
This organic sulfur compound (32)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 6.22 (bs, 1H), 3.63 (dd, 1H), 3.18-3.39 (m, 2H), 2.94 ( d, 3H), 2.60-2.73 (m, 2H), 2.08-2.50 (m, 4H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）４．３１（ｄｄ，１Ｈ）、３．１９−３．５３（ｍ，２Ｈ）、３．２１（ｓ，３Ｈ）、３．０９（ｓ，３Ｈ）、２．５７−２．７０（ｍ，２Ｈ）、１．９８−２．５４（ｍ，４Ｈ） Reference Production Example 33
0.5 g of 5,5,6,6,6-pentafluoro-2- (3,3,3-trifluoropropylsulfonyl) hexanoic acid was dissolved in 10 ml of dichloromethane. To this, 2 drops of N, N-dimethylformamide and then 0.2 ml of oxalyl chloride were successively added dropwise at room temperature. After stirring at the same temperature for 1 hour, the reaction mixture was concentrated under reduced pressure. The obtained residue was dissolved in 20 ml of tetrahydrofuran, and 0.5 g of dimethylamine (40% (w / w) aqueous solution) was added dropwise thereto at room temperature. After stirring at the same temperature for 2 hours, a saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, and N, N-dimethyl-5,5,6,6,6-pentafluoro-2- (3,3,3-trifluoropropylsulfonyl) hexanamide (hereinafter, This organic sulfur compound (33) is described.) 0.30 g was obtained.
This organic sulfur compound (33)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 4.31 (dd, 1H), 3.19-3.53 (m, 2H), 3.21 (s, 3H), 3.09 ( s, 3H), 2.57-2.70 (m, 2H), 1.98-2.54 (m, 4H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）６．６２（ｂｓ，１Ｈ）、５．７４（ｂｓ，１Ｈ）、３．２０−３．４１（ｍ，２Ｈ）、２．６４−２．７８（ｍ，２Ｈ）、２．０８−２．５４（ｍ，４Ｈ）、１．６８（ｓ，３Ｈ） Reference Production Example 34
1.1 g of 2-methyl-5,5,6,6,6-pentafluoro-2- (3,3,3-trifluoropropylsulfonyl) hexanoic acid was dissolved in 20 ml of dichloromethane. To this, 2 drops of N, N-dimethylformamide and then 0.5 ml of oxalyl chloride were successively added dropwise at room temperature. After stirring at the same temperature for 2 hours, the reaction mixture was concentrated under reduced pressure. The obtained residue was dissolved in 20 ml of tetrahydrofuran, and 0.5 g of ammonia (30% (w / w) aqueous solution) was added dropwise thereto at room temperature. After stirring at the same temperature for 2 hours, a saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to give 2-methyl-5,5,6,6,6-pentafluoro-2- (3,3,3-trifluoropropylsulfonyl) hexanamide (hereinafter referred to as the present organic compound). 0.76 g was obtained.
This organic sulfur compound (34)

_{^{1 H-NMR (CDCl 3,}} TMS): δ (ppm) 6.62 (bs, 1H), 5.74 (bs, 1H), 3.20-3.41 (m, 2H), 2.64- 2.78 (m, 2H), 2.08-2.54 (m, 4H), 1.68 (s, 3H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）６．５６（ｂｓ，１Ｈ）、３．１４−３．３９（ｍ，２Ｈ）、２．９１（ｄ，３Ｈ）、２．６０−２．７４（ｍ，２Ｈ）、２．０３−２．５３（ｍ，４Ｈ）、１．６７（ｓ，３Ｈ） Reference Production Example 35
1.1 g of 2-methyl-5,5,6,6,6-pentafluoro-2- (3,3,3-trifluoropropylsulfonyl) hexanoic acid was dissolved in 20 ml of dichloromethane. To this, 2 drops of N, N-dimethylformamide and then 0.5 ml of oxalyl chloride were successively added dropwise at room temperature. After stirring at the same temperature for 2 hours, the reaction mixture was concentrated under reduced pressure. The obtained residue was dissolved in 20 ml of tetrahydrofuran, and 0.7 g of methylamine (40% (w / w) aqueous solution) was added dropwise thereto at room temperature. After stirring at the same temperature for 2 hours, a saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, and N, 2-dimethyl-5,5,6,6,6-pentafluoro-2- (3,3,3-trifluoropropylsulfonyl) hexanamide (hereinafter, This is referred to as the organic sulfur compound (35).) 0.70 g was obtained.
This organic sulfur compound (35)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 6.56 (bs, 1H), 3.14-3.39 (m, 2H), 2.91 (d, 3H), 2.60- 2.74 (m, 2H), 2.03-2.53 (m, 4H), 1.67 (s, 3H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）３．３７（ｄｄ，２Ｈ）、３．１６（ｂｓ，６Ｈ）、１．９８−２．８８（ｍ，６Ｈ）、１．８２（ｓ，３Ｈ） Reference Production Example 36
0.5 g of 5,5,6,6,6-pentafluoro-2- (3,3,3-trifluoropropylsulfonyl) hexanoic acid was dissolved in 10 ml of dichloromethane. To this, 2 drops of N, N-dimethylformamide and then 0.2 ml of oxalyl chloride were successively added dropwise at room temperature. After stirring at the same temperature for 1 hour, the reaction mixture was concentrated under reduced pressure. The obtained residue was dissolved in 20 ml of tetrahydrofuran, and 1.0 g of dimethylamine (40% (w / w) aqueous solution) was added dropwise thereto at room temperature. After stirring at the same temperature for 4 hours, a saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, and 5,5,6,6,6-pentafluoro-2- (3,3,3-trifluoropropylsulfonyl) -N, N, 2-trimethylhexaneamide ( Hereinafter, this organic sulfur compound (36) is described.) 0.97 g was obtained.
This organic sulfur compound (36)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 3.37 (dd, 2H), 3.16 (bs, 6H), 1.98-2.88 (m, 6H), 1.82 ( s, 3H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）６．５７（ｂｓ，１Ｈ）、３．１３−３．４４（ｍ，４Ｈ）、２．６１−２．７４（ｍ，２Ｈ）、２．０１−２．５２（ｍ，４Ｈ）、１．６６（ｓ，３Ｈ）、１．１８（ｔ，３Ｈ） Reference Production Example 37
0.5 g of 2-methyl-5,5,6,6,6-pentafluoro-2- (3,3,3-trifluoropropylsulfonyl) hexanoic acid was dissolved in 20 ml of dichloromethane. To this, one drop of N, N-dimethylformamide and then 0.2 ml of oxalyl chloride were successively added dropwise at room temperature. After stirring at the same temperature for 2 hours, the reaction mixture was concentrated under reduced pressure. The obtained residue was dissolved in 20 ml of tetrahydrofuran, and 0.2 g of ethylamine (70% (w / w) aqueous solution) was added dropwise thereto at room temperature. After stirring at the same temperature for 8 hours, a saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, and N-ethyl-2-methyl-5,5,6,6,6-pentafluoro-2- (3,3,3-trifluoropropylsulfonyl) hexanamide ( Hereinafter, this organic sulfur compound (37) is described.) 0.41 g was obtained.
This organic sulfur compound (37)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 6.57 (bs, 1H), 3.13-3.44 (m, 4H), 2.61-2.74 (m, 2H), 2.01-2.52 (m, 4H), 1.66 (s, 3H), 1.18 (t, 3H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）６．５９（ｂｓ，１Ｈ）、５．８２（ｂｓ，１Ｈ）、３．１９−３．４８（ｍ，２Ｈ）、２．６２−２．７６（ｍ，２Ｈ）、２．１１−２．５２（ｍ，６Ｈ）、１．１０（ｔ，３Ｈ） Reference Production Example 38
0.5 g of 2-ethyl-5,5,6,6,6-pentafluoro-2- (3,3,3-trifluoropropylsulfonyl) hexanoic acid was dissolved in 20 ml of dichloromethane. To this, one drop of N, N-dimethylformamide and then 0.2 ml of oxalyl chloride were successively added dropwise at room temperature. After stirring at the same temperature for 2 hours, the reaction mixture was concentrated under reduced pressure. The obtained residue was dissolved in 20 ml of tetrahydrofuran, and 0.2 g of ammonia (30% (w / w) aqueous solution) was added dropwise thereto at room temperature. After stirring at the same temperature for 1 hour, a saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to give 2-ethyl-5,5,6,6,6-pentafluoro-2- (3,3,3-trifluoropropylsulfonyl) hexanamide (hereinafter referred to as the present organic compound). This is referred to as a sulfur compound (38).) 0.37 g was obtained.
This organic sulfur compound (38)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 6.59 (bs, 1H), 5.82 (bs, 1H), 3.19-3.48 (m, 2H), 2.62- 2.76 (m, 2H), 2.11-2.52 (m, 6H), 1.10 (t, 3H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）３．９０−３．９７（ｍ，１Ｈ）、３．４１−３．５９（ｍ，２Ｈ）、２．６８−２．８８（ｍ，２Ｈ）、１．７８−２．３６（ｍ，６Ｈ） Reference Production Example 39
0.6 g of 1-iodo-4,4,4-trifluorobutane and 0.5 g of (3,3,3-trifluoropropylsulfonyl) acetonitrile were dissolved in 20 ml of N, N-dimethylformamide. To this was added 0.1 g of sodium hydride (60% oily) at room temperature, and the mixture was stirred at the same temperature for 10 hours. Then, 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue is subjected to silica gel chromatography and described as 6,6,6-trifluoro-2- (3,3,3-trifluoropropylsulfonyl) hexanenitrile (hereinafter referred to as the present organic sulfur compound (39)). ) 0.57 g was obtained.
This organic sulfur compound (39)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 3.90-3.97 (m, 1H), 3.41-3.59 (m, 2H), 2.68-2.88 (m , 2H), 1.78-2.36 (m, 6H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）６．６２（ｂｓ，１Ｈ）、３．１１−３．３８（ｍ，４Ｈ）、２．００−２．７４（ｍ，６Ｈ）、１．６６（ｓ，３Ｈ）、１．４５−１．７０（ｍ，２Ｈ）、０．９４（ｔ，３Ｈ） Reference Production Example 40
0.5 g of 2-methyl-5,5,6,6,6-pentafluoro-2- (3,3,3-trifluoropropylsulfonyl) hexanoic acid was dissolved in 20 ml of dichloromethane. To this, 2 drops of N, N-dimethylformamide and then 0.2 ml of oxalyl chloride were successively added dropwise at room temperature. After stirring at the same temperature for 2 hours, the reaction mixture was concentrated under reduced pressure. The obtained residue was dissolved in 20 ml of tetrahydrofuran, and 0.2 g of propylamine was added dropwise thereto at room temperature. After stirring at the same temperature for 14 hours, a saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, and 2-methyl-N-propyl-5,5,6,6,6-pentafluoro-2- (3,3,3-trifluoropropylsulfonyl) hexanamide ( Hereinafter, this organic sulfur compound (40) is described.) 0.26 g was obtained.
This organic sulfur compound (40)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 6.62 (bs, 1H), 3.11-3.38 (m, 4H), 2.00-2.74 (m, 6H), 1.66 (s, 3H), 1.45-1.70 (m, 2H), 0.94 (t, 3H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）６．４０（ｂｓ，１Ｈ）、４．０５−４．１８（ｍ，１Ｈ）、３．１０−３．３９（ｍ，２Ｈ）、２．６０−２．７８（ｍ，２Ｈ）、１．９８−２．５２（ｍ，４Ｈ）、１．６５（ｓ，３Ｈ）、１．１９（ｄｄ,６Ｈ） Reference Production Example 41
0.5 g of 2-methyl-5,5,6,6,6-pentafluoro-2- (3,3,3-trifluoropropylsulfonyl) hexanoic acid was dissolved in 20 ml of dichloromethane. To this, 2 drops of N, N-dimethylformamide and then 0.2 ml of oxalyl chloride were successively added dropwise at room temperature. After stirring at the same temperature for 2 hours, the reaction mixture was concentrated under reduced pressure. The obtained residue was dissolved in 20 ml of tetrahydrofuran, and 0.2 g of isopropylamine was added dropwise thereto at room temperature. After stirring at the same temperature for 14 hours, a saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, and N-isopropyl-2-methyl-5,5,6,6,6-pentafluoro-2- (3,3,3-trifluoropropylsulfonyl) hexanamide ( Hereinafter, this organic sulfur compound (41) is described.) 0.25 g was obtained.
This organic sulfur compound (41)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 6.40 (bs, 1H), 4.05-4.18 (m, 1H), 3.10-3.39 (m, 2H), 2.60-2.78 (m, 2H), 1.98-2.52 (m, 4H), 1.65 (s, 3H), 1.19 (dd, 6H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）３．９１−３．９５（ｍ，１Ｈ）、３．９１（ｓ，３Ｈ）、３．４１−３．５３（ｍ，２Ｈ）、２．６２−２．７７（ｍ，２Ｈ）、２．３８−２．５４（ｍ，２Ｈ）、２．１９−２．３４（ｍ，２Ｈ） Reference Production Example 42
0.9 g of 1-iodo-3,3,4,4,4-pentafluorobutane and 1.1 g of methyl (3,3,4,4,5,5,5-heptafluoropentylsulfonyl) acetate -Dissolved in 20 ml of dimethylformamide. To this was added 0.1 g of sodium hydride (60% oily) at room temperature, and the mixture was stirred at the same temperature for 3 days. Then, 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, and methyl 2- (3,3,4,4,5,5,5-heptafluoropentylsulfonyl) -5,5,6,6,6-pentafluorohexanoate. (Hereinafter referred to as the present organic sulfur compound (42).) 1.12 g was obtained.
This organic sulfur compound (42)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 3.91-3.95 (m, 1H), 3.91 (s, 3H), 3.41-3.53 (m, 2H), 2.62-2.77 (m, 2H), 2.38-2.54 (m, 2H), 2.19-2.34 (m, 2H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）３．８９（ｓ，３Ｈ）、３．４７−３．５６（ｍ，２Ｈ）、２．６１−２．７８（ｍ，２Ｈ）、１．９５−２．５６（ｍ，４Ｈ）、１．７１（ｓ，３Ｈ） Reference 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 added to N, N -Dissolved in 20 ml of dimethylformamide. To this was added 0.1 g of sodium hydride (60% oily) at room temperature, and the mixture was stirred at the same temperature for 10 hours. Then, 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to give 2- (3,3,4,4,5,5,5-heptafluoropentylsulfonyl) -2-methyl-5,5,6,6,6-penta. 0.41 g of methyl fluorohexanoate (hereinafter referred to as the present organic sulfur compound (43)) was obtained.
This organic sulfur compound (43)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 3.89 (s, 3H), 3.47-3.56 (m, 2H), 2.61-2.78 (m, 2H), 1.95-2.56 (m, 4H), 1.71 (s, 3H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）３．８６（ｓ，３Ｈ）、３．３１−３．５５（ｍ，２Ｈ）、２．６２−２．７５（ｍ，２Ｈ）、１．９５−２．３３（ｍ，４Ｈ）、１．６７（ｓ，３Ｈ）、１．４３−１．８０（ｍ，２Ｈ） Reference 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 in 20 ml of N, N-dimethylformamide. To this was added 0.1 g of sodium hydride (60% oily) at room temperature, and the mixture was stirred at the same temperature for 10 hours. Then, 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, and methyl 2-methyl-6,6,6-trifluoro-2- (3,3,3-trifluoropropylsulfonyl) hexanoate (hereinafter referred to as the present organic sulfur compound ( 44).) 0.85 g was obtained.
This organic sulfur compound (44)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 3.86 (s, 3H), 3.31-3.55 (m, 2H), 2.62-2.75 (m, 2H), 1.95-2.33 (m, 4H), 1.67 (s, 3H), 1.43-1.80 (m, 2H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）３．４０−３．５５（ｍ，２Ｈ）、２．７３−２．８８（ｍ，２Ｈ）、１．８５−２．３４（ｍ，６Ｈ）、１．８０（ｓ，３Ｈ） Reference Production Example 45
0.2 g of iodomethane and 0.5 g of 6,6,6-trifluoro-2- (3,3,3-trifluoropropylsulfonyl) hexanenitrile were dissolved in 20 ml of N, N-dimethylformamide. To this, 0.06 g of sodium hydride (60% oily) was added at room temperature and stirred at the same temperature for 10 hours. Then, 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to give 2-methyl-6,6,6-trifluoro-2- (3,3,3-trifluoropropylsulfonyl) hexanenitrile (hereinafter referred to as the present organic sulfur compound (45 ) 0.37 g was obtained.
This organic sulfur compound (45)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 3.40-3.55 (m, 2H), 2.73-2.88 (m, 2H), 1.85-2.34 (m , 6H), 1.80 (s, 3H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）４．３３（ｑ，２Ｈ）、３．４６−３．５３（ｍ，２Ｈ）、２．６３−２．７８（ｍ，２Ｈ）、２．０８−２．５４（ｍ，４Ｈ）、１．６９（ｓ，３Ｈ）、１．３４（ｔ，３Ｈ） Reference Production Example 46
1.0 g of 1-iodo-3,3,4,4,4-pentafluorobutane and 1.0 g of ethyl 2- (3,3,3-trifluoropropylsulfonyl) propionate were dissolved in 20 ml of dimethyl sulfoxide. To this, 0.2 g of sodium hydride (60% oily) was added at room temperature, and the mixture was stirred at the same temperature for 10 hours, at 60 ° C. for 4 hours, and further at 90 ° C. for 4 hours, and then the reaction mixture was allowed to cool to room temperature. 10% hydrochloric acid was added and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain ethyl 2-methyl-5,5,6,6,6-pentafluoro-2- (3,3,3-trifluoropropylsulfonyl) hexanoate (hereinafter referred to as the present product). 0.47 g of organic sulfur compound (46) is obtained.
This organic sulfur compound (46)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 4.33 (q, 2H), 3.46-3.53 (m, 2H), 2.62-2.78 (m, 2H), 2.08-2.54 (m, 4H), 1.69 (s, 3H), 1.34 (t, 3H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）３．６７（ｔ，１Ｈ）、２．８９−３．０４（ｍ，２Ｈ）、２．１０−２．５８（ｍ，６Ｈ） Reference Production Example 47
S- (3,3,3-trifluoropropyl) = benzenethioate (1.8 g) was dissolved in tetrahydrofuran (100 ml), and sodium methoxide (28% (w / w) methanol solution) (1.5 ml) was added under ice cooling. Was added. To the mixture, 2.0 g of 2-bromo-5,5,6,6,6-pentafluorohexanenitrile was added dropwise under ice cooling, and the mixture was stirred at room temperature for 0.5 hour. 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with 10% hydrochloric acid and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography, and 5,5,6,6,6-pentafluoro-2- (3,3,3-trifluoropropylthio) hexanenitrile (hereinafter, represented by the following formula). 1.6 g of this organic sulfur compound (referred to as the present organic sulfur compound (47)) was obtained.
This organic sulfur compound (47)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 3.67 (t, 1H), 2.89-3.04 (m, 2H), 2.10-2.58 (m, 6H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）３．６２−３．６９（ｍ，１Ｈ）、２．９８−３．３８（ｍ，２Ｈ）、２．２５−２．８２（ｍ，６Ｈ） Reference production example 48
S- (3,3,3-trifluoropropyl) = benzenethioate 0.5 g was dissolved in tetrahydrofuran 20 ml, and sodium methoxide (28% (w / w) methanol solution) 0.4 ml was added under ice cooling. Was added. To the mixture, 0.6 g of 2-bromo-5,5,6,6,6-pentafluorohexanenitrile was added dropwise under ice cooling, and the mixture was stirred at room temperature for 1 hour. 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with 10% hydrochloric acid and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was dissolved in 20 ml of chloroform, and 0.5 g of peracetic acid (32% (w / w) acetic acid solution) was added thereto under ice cooling, followed by stirring at the same temperature for 4 hours. The reaction mixture was warmed to room temperature, poured into water, and extracted with ethyl acetate. The organic layer was washed successively with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography, and 5,5,6,6,6-pentafluoro-2- (3,3,3-trifluoropropylsulfinyl) hexanenitrile (hereinafter, represented by the following formula). 0.4 g of this organic sulfur compound (referred to as “48”) was obtained.
This organic sulfur compound (48)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 3.62-3.69 (m, 1H), 2.98-3.38 (m, 2H), 2.25-2.82 (m , 6H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）８．０３（ｂｓ，１Ｈ）、７．８０（ｂｓ，１Ｈ）、３．１９−３．４４（ｍ，２Ｈ）、２．０８−２．７８（ｍ，６Ｈ）、１．８５（ｓ，３Ｈ） Reference Production Example 49
1.1 g of 2-methyl-5,5,6,6,6-pentafluoro-2- (3,3,3-trifluoropropylsulfonyl) hexanoic acid was dissolved in 20 ml of dichloromethane. To this, 2 drops of N, N-dimethylformamide and then 0.5 ml of oxalyl chloride were successively added dropwise at room temperature. After stirring at the same temperature for 2 hours, the reaction mixture was concentrated under reduced pressure. The obtained residue was dissolved in 20 ml of tetrahydrofuran, 0.5 g of ammonia (30% (w / w) aqueous solution) was added thereto at room temperature, and the mixture was stirred at the same temperature for 10 hours. A saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate and concentrated under reduced pressure. A mixture in which 1.2 g of 2,4-bis (4-methoxyphenyl) -1,3-dithia-2,4-diphosphetane 2,4-disulfide and 20 ml of toluene were added to the resulting residue was heated to reflux for 10 hours. . The reaction mixture allowed to cool to room temperature was concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, and 2-methyl-5,5,6,6,6-pentafluoro-2- (3,3,3-trifluoropropylsulfonyl) hexanethioamide (hereinafter referred to as the present organic compound). 0.47 g was obtained.
This organic sulfur compound (49)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 8.03 (bs, 1H), 7.80 (bs, 1H), 3.19-3.44 (m, 2H), 2.08- 2.78 (m, 6H), 1.85 (s, 3H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）２．９８（ｔ，２Ｈ）、２．０８−２．５８（ｍ，６Ｈ）、１．７１（ｓ，３Ｈ） Reference production example 50
5,5,6,6,6-pentafluoro-2- (3,3,3-trifluoropropylthio) hexanenitrile (0.5 g) and iodomethane (0.2 g) were dissolved in tetrahydrofuran (20 ml). 1.6 ml of sodium bis (trimethylsilyl) amide (1M-tetrahydrofuran solution) was added. After stirring at the same temperature for 0.5 hour, 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with 10% hydrochloric acid and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography, and 2-methyl-5,5,6,6,6-pentafluoro-2- (3,3,3-trifluoropropylthio) hexane represented by the following formula: 0.4 g of nitrile (hereinafter referred to as the present organic sulfur compound (50)) was obtained.
This organic sulfur compound (50)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 2.98 (t, 2H), 2.08-2.58 (m, 6H), 1.71 (s, 3H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）３．９１（ｓ，３Ｈ）、３．９０−３．９７（ｍ，１Ｈ）、３．４１−３．５４（ｍ，２Ｈ）、２．２０−２．７３（ｍ，６Ｈ） Reference Production Example 51
5.7 g of 1-iodo-3,3,4,4,5,5,5-heptafluoropentane and 5.0 g of methyl (3,3,4,4,4-pentafluorobutylsulfonyl) acetate were added to N, N -Dissolved in 50 ml of dimethylformamide, 0.7 g of sodium hydride (60% oily) was added thereto at room temperature, and the mixture was stirred at the same temperature for 3 days. 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain methyl 5,5,6,6,7,7,7-heptafluoro-2- (3,3,4,4,4-pentafluorobutylsulfonyl) heptanoate. (Hereinafter referred to as the present organic sulfur compound (51).) 1.80 g was obtained.
This organic sulfur compound (51)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 3.91 (s, 3H), 3.90-3.97 (m, 1H), 3.41-3.54 (m, 2H), 2.20-2.73 (m, 6H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）３．８８（ｓ，３Ｈ）、３．４７−３．５４（ｍ，２Ｈ）、２．０８−２．７３（ｍ，６Ｈ）、１．７１（ｓ，３Ｈ） Reference Production Example 52
0.4 g of iodomethane and 1.3 g of 5,5,6,6,7,7,7-heptafluoro-2- (3,3,4,4,4-pentafluorobutylsulfonyl) heptanoic acid methyl -Dissolved in 50 ml of dimethylformamide, 0.1 g of sodium hydride (60% oily) was added thereto at room temperature, and the mixture was stirred at the same temperature for 3 hours. 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 5,5,6,6,7,7,7-heptafluoro-2-methyl-2- (3,3,4,4,4-pentafluorobutylsulfonyl. ) 1.30 g of methyl heptanoate (hereinafter referred to as the present organic sulfur compound (52)) was obtained.
This organic sulfur compound (52)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 3.88 (s, 3H), 3.47-3.54 (m, 2H), 2.08-2.73 (m, 6H), 1.71 (s, 3H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）４．０４−４．０８（ｍ，１Ｈ）、３．４７−３．６６（ｍ，２Ｈ）、２．３５−２．８１（ｍ，６Ｈ） Reference Production Example 53
Dissolve 0.4 g of 1-iodo-3,3,3-trifluoropropane and 0.5 g of (3,3,4,4,4-pentafluorobutylsulfonyl) acetonitrile in 20 ml of N, N-dimethylformamide. At room temperature, 0.08 g of sodium hydride (60% oily) was added and stirred at the same temperature for 20 hours. 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to give 2- (3,3,4,4,4-pentafluorobutylsulfonyl) -5,5,5-trifluoropentanenitrile (hereinafter referred to as the present organic sulfur compound (53 ) 0.26 g was obtained.
This organic sulfur compound (53)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 4.04-4.08 (m, 1H), 3.47-3.66 (m, 2H), 2.35-2.81 (m , 6H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）４．１６−４．２２（ｍ，１Ｈ）、３．５０−３．６８（ｍ，２Ｈ）、２．３３−２．８８（ｍ，６Ｈ） Reference production example 54
0.6 g of 1-iodo-3,3,4,4,5,5,5-heptafluoropentane and 0.5 g of (3,3,4,4,4-pentafluorobutylsulfonyl) acetonitrile were added to N, N- Dissolved in 20 ml of dimethylformamide. To this was added 0.08 g of sodium hydride (60% oily) at room temperature, and the mixture was stirred at the same temperature for 24 hours. Then, 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, and 5,5,6,6,7,7,7-heptafluoro-2- (3,3,4,4,4-pentafluorobutylsulfonyl) heptanenitrile ( Hereinafter, this organic sulfur compound (54) is described.) 0.30 g was obtained.
This organic sulfur compound (54)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 4.16-4.22 (m, 1H), 3.50-3.68 (m, 2H), 2.33-2.88 (m , 6H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）６．３１（ｂｓ，１Ｈ）、５．７３（ｂｓ，１Ｈ）、３．７２−３．７８（ｍ，１Ｈ）、３．２４−３．４５（ｍ，２Ｈ）、２．１２−２．７４（ｍ，６Ｈ） Reference production example 55
0.5 g of 5,5,6,6,7,7,7-heptafluoro-2- (3,3,4,4,4-pentafluorobutylsulfonyl) heptanoic acid was dissolved in 20 ml of dichloromethane. To this, 2 drops of N, N-dimethylformamide and then 0.1 ml of oxalyl chloride were successively added dropwise at room temperature. After stirring at the same temperature for 2 hours, the reaction mixture was concentrated under reduced pressure. The obtained residue was dissolved in 20 ml of tetrahydrofuran, and 0.2 g of ammonia (30% (w / w) aqueous solution) was added dropwise thereto at room temperature. After stirring at the same temperature for 2 hours, a saturated aqueous ammonium chloride solution was added to the reaction mixture, extracted with ethyl acetate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, and 5,5,6,6,7,7,7-heptafluoro-2- (3,3,4,4,4-pentafluorobutylsulfonyl) heptanamide ( Hereinafter, this organic sulfur compound (55) is described.) 0.31 g was obtained.
This organic sulfur compound (55)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 6.31 (bs, 1H), 5.73 (bs, 1H), 3.72-3.78 (m, 1H), 3.24- 3.45 (m, 2H), 2.12-2.74 (m, 6H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）６．６３（ｂｓ，１Ｈ）、５．７６（ｂｓ，１Ｈ）、３．２０−３．４５（ｍ，２Ｈ）、２．０８−２．７３（ｍ，６Ｈ）、１．７０（ｓ，３Ｈ） Reference production example 56
1.1 g of 5,5,6,6,7,7,7-heptafluoro-2-methyl-2- (3,3,4,4,4-pentafluorobutylsulfonyl) heptanoic acid was dissolved in 20 ml of dichloromethane. It was. To this, 2 drops of N, N-dimethylformamide and then 0.4 ml of oxalyl chloride were successively added dropwise at room temperature. After stirring at the same temperature for 2 hours, the reaction mixture was concentrated under reduced pressure. The obtained residue was dissolved in 50 ml of tetrahydrofuran, and 0.4 g of ammonia (30% (w / w) aqueous solution) was added dropwise thereto at room temperature. After stirring at the same temperature for 2 hours, a saturated aqueous ammonium chloride solution was added to the reaction mixture, extracted with ethyl acetate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 5,5,6,6,7,7,7-heptafluoro-2-methyl-2- (3,3,4,4,4-pentafluorobutylsulfonyl. ) Heptanamide (hereinafter referred to as the present organic sulfur compound (56)) 0.60 g was obtained.
This organic sulfur compound (56)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 6.63 (bs, 1H), 5.76 (bs, 1H), 3.20-3.45 (m, 2H), 2.08- 2.73 (m, 6H), 1.70 (s, 3H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）２．９８−３．２１（ｍ，２Ｈ）、２．６０−２．８２（ｍ，２Ｈ）、２．０４−２．５４（ｍ，４Ｈ）、１．６８（ｓ，２Ｈ）、１．５９（ｓ，１Ｈ） Reference Production Example 57
0.6 g of 2-methyl-5,5,6,6,6-pentafluoro-2- (3,3,3-trifluoropropylthio) hexanenitrile is dissolved in 30 ml of chloroform, and peracetic acid ( After adding 0.4 g of a 32% (w / w) acetic acid solution), the mixture was stirred at the same temperature for 2 hours and further at room temperature for 10 hours. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed successively with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography, and 2-methyl-5,5,6,6,6-pentafluoro-2- (3,3,3-trifluoropropylsulfinyl) hexane represented by the following formula: 0.25 g of a diastereomer mixture of nitrile (hereinafter referred to as the present organic sulfur compound (57)) was obtained.
This organic sulfur compound (57)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 2.98-3.21 (m, 2H), 2.60-2.82 (m, 2H), 2.04-2.54 (m , 4H), 1.68 (s, 2H), 1.59 (s, 1H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）３．９７（ｓ，３Ｈ）、３．５２−３．９２（ｍ，２Ｈ）、２．１８−２．９１（ｍ，６Ｈ） Reference Production Example 58
0.8 g of methyl 5,5,6,6,6-pentafluoro-2- (3,3,3-trifluoropropylsulfonyl) hexanoate was dissolved in 50 ml of tetrahydrofuran. To this, 0.08 g of sodium hydride (60% oily) was added at room temperature, and the mixture was stirred at the same temperature for 0.5 hour. 0.3 g of N-chlorosuccinimide was added to the mixture at room temperature and stirred for 4 hours, 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, and methyl 2-chloro-5,5,6,6,6-pentafluoro-2- (3,3,3-trifluoropropylsulfonyl) hexanoate (hereinafter referred to as the present product). 0.60 g of organic sulfur compound (58) was obtained.
This organic sulfur compound (58)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 3.97 (s, 3H), 3.52-3.92 (m, 2H), 2.18-2.91 (m, 6H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）６．８８（ｂｓ，１Ｈ）、６．０２（ｂｓ，１Ｈ）、３．３８−３．７４（ｍ，２Ｈ）、２．１３−２．９５（ｍ，６Ｈ） Reference Production Example 59
0.5 g of methyl 2-chloro-5,5,6,6,6-pentafluoro-2- (3,3,3-trifluoropropylsulfonyl) hexanoate was dissolved in 50 ml of methanol. To this, 0.5 ml of ammonia (7M methanol solution) was added at room temperature, and the mixture was stirred at the same temperature for 2 hours. The reaction mixture was concentrated under reduced pressure, and the resulting residue was subjected to silica gel chromatography to give 2-chloro-5,5,6,6,6-pentafluoro-2- (3,3,3-trifluoropropylsulfonyl). ) Hexanamide (hereinafter referred to as the present organic sulfur compound (59)) 0.15 g was obtained.
This organic sulfur compound (59)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 6.88 (bs, 1H), 6.02 (bs, 1H), 3.38-3.74 (m, 2H), 2.13 2.95 (m, 6H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）６．４１（ｂｓ，１Ｈ）、５．７３（ｂｓ，１Ｈ）、３．７４−３．７９（ｍ，１Ｈ）、３．２０−３．４５（ｍ，２Ｈ）、２．０８−２．７４（ｍ，６Ｈ） Reference Production Example 60
0.5 g of 5,5,6,6,6-pentafluoro-2- (3,3,4,4,4-pentafluorobutylsulfonyl) hexanoic acid was dissolved in 20 ml of dichloromethane. To this, 2 drops of N, N-dimethylformamide and then 0.2 ml of oxalyl chloride were successively added dropwise at room temperature. After stirring at the same temperature for 4 hours, the reaction mixture was concentrated under reduced pressure. The obtained residue was dissolved in 20 ml of tetrahydrofuran, and 0.2 g of ammonia (30% (w / w) aqueous solution) was added dropwise thereto at room temperature. After stirring at the same temperature for 2 days, a saturated aqueous ammonium chloride solution was added to the reaction mixture, extracted with ethyl acetate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 5,5,6,6,6-pentafluoro-2- (3,3,4,4,4-pentafluorobutylsulfonyl) hexanamide (hereinafter referred to as the present organic compound). 0.20 g was obtained.
This organic sulfur compound (60)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 6.41 (bs, 1H), 5.73 (bs, 1H), 3.74-3.79 (m, 1H), 3.20- 3.45 (m, 2H), 2.08-2.74 (m, 6H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）６．６９（ｂｓ，１Ｈ）、６．０１（ｂｓ，１Ｈ）、３．２２−３．４６（ｍ，２Ｈ）、２．０８−２．７３（ｍ，６Ｈ）、１．６９（ｓ，３Ｈ） Reference Production Example 61
0.8 g of 2-methyl-5,5,6,6,6-pentafluoro-2- (3,3,4,4,4-pentafluorobutylsulfonyl) hexanoic acid was dissolved in 20 ml of dichloromethane. To this, 2 drops of N, N-dimethylformamide and then 0.3 ml of oxalyl chloride were successively added dropwise at room temperature. After stirring at the same temperature for 4 hours, the reaction mixture was concentrated under reduced pressure. The obtained residue was dissolved in 20 ml of tetrahydrofuran, and 0.3 g of ammonia (30% (w / w) aqueous solution) was added dropwise thereto at room temperature. After stirring at the same temperature for 2 days, a saturated aqueous ammonium chloride solution was added to the reaction mixture, extracted with ethyl acetate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, and 2-methyl-5,5,6,6,6-pentafluoro-2- (3,3,4,4,4-pentafluorobutylsulfonyl) hexanamide ( Hereinafter, this organic sulfur compound (61) is described.) 0.60 g was obtained.
This organic sulfur compound (61)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 6.69 (bs, 1H), 6.01 (bs, 1H), 3.22-3.46 (m, 2H), 2.08- 2.73 (m, 6H), 1.69 (s, 3H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）３．７９（ｓ，３Ｈ）、３．３１（ｔ，１Ｈ）、２．７２−２．９０（ｍ，２Ｈ）、１．９３−２．４８（ｍ，６Ｈ） Reference Production Example 62
2.0 g of 5,5,6,6,6-pentafluoro-2- (3,3,3-trifluoropropylthio) hexanenitrile was dissolved in 50 ml of methanol, and sodium methoxide (28% (W / w) methanol solution) 12.5 ml was added and stirred at the same temperature for 15 hours. 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with 10% hydrochloric acid and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography, and methyl 5,5,6,6,6-pentafluoro-2- (3,3,3-trifluoropropylthio) hexanoate (hereinafter referred to as the following formula) This is referred to as the present organic sulfur compound (62).) 0.8 g was obtained.
This organic sulfur compound (62)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 3.79 (s, 3H), 3.31 (t, 1H), 2.72-2.90 (m, 2H), 1.93- 2.48 (m, 6H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）３．８６（ｓ，１．２Ｈ）、３．８４（ｓ，１．８Ｈ）、３．５７−３．６９（ｍ，１Ｈ）、２．１３−３．１４（ｍ，８Ｈ） Reference Production Example 63
Methyl 5,5,6,6,6-pentafluoro-2- (3,3,3-trifluoropropylthio) hexanoate (0.3 g) was dissolved in 20 ml of chloroform, and peracetic acid (32% ( After adding 0.2 g of w / w) acetic acid solution), the mixture was warmed to room temperature and stirred for 6 hours. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed successively with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography, and methyl 5,5,6,6,6-pentafluoro-2- (3,3,3-trifluoropropylsulfinyl) hexanoate represented by the following formula: 0.18 g of a stereomer mixture (hereinafter referred to as the present organic sulfur compound (63)) was obtained.
This organic sulfur compound (63)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 3.86 (s, 1.2H), 3.84 (s, 1.8H), 3.57-3.69 (m, 1H), 2.13-3.14 (m, 8H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）６．５４（ｂｓ，１Ｈ）、５．８８（ｂｓ，１Ｈ）、３．３０−３．５８（ｍ，２Ｈ）、２．１４−２．８３（ｍ，６Ｈ） Reference production example 64
0.5 g of methyl 2,5,5,6,6,6-hexafluoro-2- (3,3,3-trifluoropropylsulfonyl) hexanoate was dissolved in 20 ml of methanol. To this, 0.5 ml of ammonia (7M methanol solution) was added at room temperature, and the mixture was stirred at the same temperature for 0.5 hour. Further, 5 ml of ammonia (7M methanol solution) was added and stirred at the same temperature for 2 hours. The reaction mixture was concentrated under reduced pressure, and the resulting residue was subjected to silica gel chromatography to obtain 2,5,5,6,6,6-hexafluoro-2- (3,3,3-trifluoropropylsulfonyl) hexane. 0.37 g of amide (hereinafter referred to as the present organic sulfur compound (64)) was obtained.
This organic sulfur compound (64)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 6.54 (bs, 1H), 5.88 (bs, 1H), 3.30-3.58 (m, 2H), 2.14 2.83 (m, 6H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）３．９６（ｓ，３Ｈ）、３．７５−４．０１（ｍ，２Ｈ）、２．３５−２．９２（ｍ，６Ｈ） Reference Production Example 65
2.0 g of methyl 5,5,6,6,6-pentafluoro-2- (3,3,3-trifluoropropylsulfonyl) hexanoate was dissolved in 50 ml of tetrahydrofuran. To this, 0.21 g of sodium hydride (60% oily) was added under ice cooling, and the mixture was stirred at the same temperature for 0.5 hour. N-bromosuccinimide 0.9g was added here, and after heating up a reaction mixture to room temperature, it stirred for 12 hours. 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, and methyl 2-bromo-5,5,6,6,6-pentafluoro-2- (3,3,3-trifluoropropylsulfonyl) hexanoate (hereinafter referred to as this). 0.30 g was obtained.
This organic sulfur compound (65)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 3.96 (s, 3H), 3.75-4.01 (m, 2H), 2.35-2.92 (m, 6H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）４．００（ｓ，３Ｈ）、３．３４−３．６１（ｍ，２Ｈ）、２．０９−２．８１（ｍ，６Ｈ） Reference production example 66
1.0 g of methyl 2- (3,3,4,4,5,5,5-heptafluoropentylsulfonyl) -5,5,6,6,6-pentafluorohexanoate was dissolved in 50 ml of tetrahydrofuran, At 0 ° C., 0.08 g of sodium hydride (60% oily) was added, and the mixture was stirred at the same temperature for 0.5 hour. 0.6 g of 1-fluoro-2,4,6-trimethylpyridinium trifluoromethanesulfonate was added to the mixture at 0 ° C., and the mixture was stirred for 1 hour. 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to give 2- (3,3,4,4,5,5,5-heptafluoropentylsulfonyl) -2,5,5,6,6,6-hexafluorohexane. 0.75 g of methyl acid (hereinafter referred to as the present organic sulfur compound (66)) was obtained.
This organic sulfur compound (66)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 4.00 (s, 3H), 3.34-3.61 (m, 2H), 2.09-2.81 (m, 6H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）６．５４（ｂｓ，１Ｈ）、５．８９（ｂｓ，１Ｈ）、３．３４−３．６２（ｍ，２Ｈ）、２．１０−２．８２（ｍ，６Ｈ） Reference Production Example 67
2- (3,3,4,4,5,5,5-heptafluoropentylsulfonyl) -2,5,5,6,6,6-hexafluorohexanoic acid methyl 1.5g was dissolved in methanol 30ml. . To this, 1.3 ml of ammonia (7M methanol solution) was added at room temperature, and the mixture was stirred at the same temperature for 24 hours. The reaction mixture was concentrated under reduced pressure, and the resulting residue was subjected to silica gel chromatography to give 2- (3,3,4,4,5,5,5-heptafluoropentylsulfonyl) -2,5,5,6. , 6,6-hexafluorohexanamide (hereinafter referred to as the present organic sulfur compound (67)) 1.10 g was obtained.
This organic sulfur compound (67)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 6.54 (bs, 1H), 5.89 (bs, 1H), 3.34-3.62 (m, 2H), 2.10 − 2.82 (m, 6H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）３．７８（ｓ，３Ｈ）、２．７３−２．７９（ｍ，２Ｈ）、１．９６−２．４１（ｍ，６Ｈ）、１．５０（ｓ，３Ｈ） Reference production example 68
Methyl 5,5,6,6,6-pentafluoro-2- (3,3,3-trifluoropropylthio) hexanoate (0.3 g) and iodomethane (0.12 g) were dissolved in tetrahydrofuran (20 ml). 0.9 ml of sodium bis (trimethylsilyl) amide (1M-tetrahydrofuran solution) was added. After stirring at the same temperature for 1 hour, 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with 10% hydrochloric acid and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography, and 2-methyl-5,5,6,6,6-pentafluoro-2- (3,3,3-trifluoropropylthio) hexane represented by the following formula: 0.3 g of methyl acid (hereinafter referred to as the present organic sulfur compound (68)) was obtained.
This organic sulfur compound (68)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 3.78 (s, 3H), 2.73-2.79 (m, 2H), 1.96-2.41 (m, 6H), 1.50 (s, 3H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）６．５８（ｂｓ，１Ｈ）、３．２６−３．５８（ｍ，２Ｈ）、２．９９（ｄ，３Ｈ）、２．０４−２．８２（ｍ，６Ｈ） Reference Production Example 69
1.0 g of methyl 2,5,5,6,6,6-hexafluoro-2- (3,3,3-trifluoropropylsulfonyl) hexanoate was dissolved in 30 ml of methanol. To this was added 3.8 ml of methylamine (2M-methanol solution) at room temperature, and the mixture was stirred at the same temperature for 2 hours. The reaction mixture was concentrated under reduced pressure, and the resulting residue was subjected to silica gel chromatography to obtain 2,5,5,6,6,6-hexafluoro-N-methyl-2- (3,3,3-trifluoro. 0.92 g of propylsulfonyl) hexanamide (hereinafter referred to as the present organic sulfur compound (69)) was obtained.
This organic sulfur compound (69)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 6.58 (bs, 1H), 3.26-3.58 (m, 2H), 2.99 (d, 3H), 2.04- 2.82 (m, 6H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）６．６０（ｂｓ，１Ｈ）、５．４９（ｂｓ，１Ｈ）、２．７３（ｔ，２Ｈ）、１．９６−２．４４（ｍ，６Ｈ）、１．５１（ｓ，３Ｈ） Reference production example 70
1.0 g of methyl 2-methyl-5,5,6,6,6-pentafluoro-2- (3,3,3-trifluoropropylthio) hexanoate is dissolved in 50 ml of methanol, and an aqueous potassium hydroxide solution at room temperature (A total amount of a mixed solution of 0.9 g of potassium hydroxide and 5 ml of water) was added and stirred at the same temperature for 1 day. 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was dissolved in 20 ml of dichloromethane. To this, 2 drops of N, N-dimethylformamide and then 0.4 ml of oxalyl chloride were successively added dropwise at room temperature. After stirring at the same temperature for 1 hour, the reaction mixture was concentrated under reduced pressure. The obtained residue was dissolved in 20 ml of tetrahydrofuran, and 0.4 g of ammonia (30% (w / w) aqueous solution) was added dropwise thereto at room temperature. After stirring at the same temperature for 1 hour, a saturated aqueous ammonium chloride solution was added to the reaction mixture, extracted with ethyl acetate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 2-methyl-5,5,6,6,6-pentafluoro-2- (3,3,3-trifluoropropylthio) hexanamide (hereinafter referred to as the present organic compound). 0.25 g was obtained.
This organic sulfur compound (70)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 6.60 (bs, 1H), 5.49 (bs, 1H), 2.73 (t, 2H), 1.96-2.44 ( m, 6H), 1.51 (s, 3H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）３．８４（ｓ，１．２Ｈ）、３．８２（ｓ，１．８Ｈ）、２．０６−２．８４（ｍ，８Ｈ）、１．５３（ｓ，１．２Ｈ）、１．５２（ｓ，１．８Ｈ） Reference production example 71
4.4 g of methyl 2-methyl-5,5,6,6,6-pentafluoro-2- (3,3,3-trifluoropropylthio) hexanoate was dissolved in 30 ml of chloroform and peracetic acid was cooled with ice. After adding 2.9 g (32% (w / w) acetic acid solution), the mixture was stirred for 4 hours. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed successively with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography, and 2-methyl-5,5,6,6,6-pentafluoro-2- (3,3,3-trifluoropropylsulfinyl) hexane represented by the following formula: 1.10 g of a methyl diastereomer mixture (hereinafter referred to as the present organic sulfur compound (71)) was obtained.
This organic sulfur compound (71)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 3.84 (s, 1.2 H), 3.82 (s, 1.8 H), 2.06-2.84 (m, 8 H), 1.53 (s, 1.2H), 1.52 (s, 1.8H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）４．００（ｓ，３Ｈ）、３．３３−３．６０（ｍ，２Ｈ）、２．０８−２．８１（ｍ，６Ｈ） Reference production example 72
1.0 g of methyl 2- (3,3,4,4,4-pentafluorobutylsulfonyl) -5,5,6,6,6-pentafluorohexanoate was dissolved in 50 ml of tetrahydrofuran, and hydrogenated at room temperature. Sodium chloride (60% oily) 0.09 g was added and stirred at the same temperature for 0.5 hour. To this mixture, 0.7 g of 1-fluoro-2,4,6-trimethylpyridinium trifluoromethanesulfonate was added at room temperature and stirred for 3 hours. 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, and methyl 2,5,5,6,6,6-hexafluoro-2- (3,3,4,4,4-pentafluorobutylsulfonyl) hexanoate (hereinafter referred to as “hexafluoromethyl”). This is referred to as the organic sulfur compound (72).) 0.78 g was obtained.
This organic sulfur compound (72)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 4.00 (s, 3H), 3.33-3.60 (m, 2H), 2.08-2.81 (m, 6H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）６．５５（ｂｓ，１Ｈ）、５．９１（ｂｓ，１Ｈ）、３．３３−３．６１（ｍ，２Ｈ）、２．０４−２．８３（ｍ，６Ｈ） Reference production example 73
0.6 g of methyl 2,5,5,6,6,6-hexafluoro-2- (3,3,4,4,4-pentafluorobutylsulfonyl) hexanoate was dissolved in 20 ml of methanol. To this, 0.6 ml of ammonia (7M methanol solution) was added at room temperature, and the mixture was stirred at the same temperature for 12 hours. The reaction mixture was concentrated under reduced pressure, and the resulting residue was subjected to silica gel chromatography to obtain 2,5,5,6,6,6-hexafluoro-2- (3,3,4,4,4-pentafluoro 0.45 g of (butylsulfonyl) hexanamide (hereinafter referred to as the present organic sulfur compound (73)) was obtained.
This organic sulfur compound (73)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 6.55 (bs, 1H), 5.91 (bs, 1H), 3.33-3.61 (m, 2H), 2.04- 2.83 (m, 6H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）３．３２−３．５５（ｍ，２Ｈ）、３．２９（ｄ，３Ｈ）、３．１０（ｓ，３Ｈ）、２．１４−２．９７（ｍ，６Ｈ） Reference production example 74
0.5 g of methyl 2,5,5,6,6,6-hexafluoro-2- (3,3,3-trifluoropropylsulfonyl) hexanoate is dissolved in 30 ml of methanol, and an aqueous potassium hydroxide solution (water) at room temperature. The total amount of a mixed solution of 0.4 g of potassium oxide and 5 ml of water) was added and stirred at the same temperature for 12 hours. 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was dissolved in 20 ml of dichloromethane. To this, 2 drops of N, N-dimethylformamide and then 0.2 ml of oxalyl chloride were successively added dropwise at room temperature. After stirring at the same temperature for 2 hours, the reaction mixture was concentrated under reduced pressure. The obtained residue was dissolved in 30 ml of tetrahydrofuran, and 0.4 g of dimethylamine (40% (w / w) aqueous solution) was added dropwise thereto at room temperature. After stirring at the same temperature for 2 hours, a saturated aqueous ammonium chloride solution was added to the reaction mixture, extracted with ethyl acetate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, and N, N-dimethyl-2,5,5,6,6,6-hexafluoro-2- (3,3,3-trifluoropropylsulfonyl) hexanamide ( Hereinafter, this organic sulfur compound (74) is described.) 0.26 g was obtained.
This organic sulfur compound (74)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 3.32-3.55 (m, 2H), 3.29 (d, 3H), 3.10 (s, 3H), 2.14 2.97 (m, 6H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）６．９５（ｂｓ，１Ｈ）、３．３５−３．７５（ｍ，２Ｈ）、２．９６（ｄ，３Ｈ）、２．０５−２．９８（ｍ，６Ｈ） Reference production example 75
1.0 g of methyl 2-chloro-5,5,6,6,6-pentafluoro-2- (3,3,3-trifluoropropylsulfonyl) hexanoate was dissolved in 30 ml of methanol. To this, 3.6 ml of methylamine (2M-methanol solution) was added at room temperature and stirred at the same temperature for 16 hours. The reaction mixture was concentrated under reduced pressure, and the resulting residue was subjected to silica gel chromatography to give 2-chloro-N-methyl-5,5,6,6,6-pentafluoro-2- (3,3,3- 0.15 g of trifluoropropylsulfonyl) hexanamide (hereinafter referred to as the present organic sulfur compound (75)) was obtained.
This organic sulfur compound (75)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 6.95 (bs, 1H), 3.35-3.75 (m, 2H), 2.96 (d, 3H), 2.05- 2.98 (m, 6H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）３．９０（ｓ，３Ｈ）、３．８８−３．９４（ｍ，１Ｈ）、３．３６−３．５２（ｍ，２Ｈ）、２．６２−２．７８（ｍ，２Ｈ）、２．３８−２．５３（ｍ，２Ｈ）、２．２４−２．４８（ｍ，２Ｈ） Reference production example 76
1.0 g of 1-iodo-3,3,3-trifluoropropane and 1.0 g of methyl (3,3,3-trifluoropropylsulfonyl) acetate were dissolved in 20 ml of dimethyl sulfoxide. To this was added 0.6 g of potassium carbonate at room temperature, and the mixture was stirred at the same temperature for 16 hours. Then, 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, and methyl 5,5,5-trifluoro-2- (3,3,3-trifluoropropylsulfonyl) pentanoate (hereinafter referred to as the present organic sulfur compound (76)). 0.42 g was obtained.
This organic sulfur compound (76)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 3.90 (s, 3H), 3.88-3.94 (m, 1H), 3.36-3.52 (m, 2H), 2.62-2.78 (m, 2H), 2.38-2.53 (m, 2H), 2.24-2.48 (m, 2H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）３．９７（ｓ，３Ｈ）、３．５８−３．８８（ｍ，２Ｈ）、２．３５−２．８８（ｍ，６Ｈ） Reference Production Example 77
1.0 g of methyl 5,5,5-trifluoro-2- (3,3,3-trifluoropropylsulfonyl) pentanoate was dissolved in 30 ml of tetrahydrofuran. To this, 0.12 g of sodium hydride (60% oily) was added at room temperature, and the mixture was stirred at the same temperature for 0.5 hour. After adding 0.4 g of N-chlorosuccinimide at room temperature and stirring for 2 hours, 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, and methyl 2-chloro-5,5,5-trifluoro-2- (3,3,3-trifluoropropylsulfonyl) pentanoate (hereinafter referred to as the present organic sulfur compound ( 77).) 0.65 g was obtained.
This organic sulfur compound (77)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 3.97 (s, 3H), 3.58-3.88 (m, 2H), 2.35-2.88 (m, 6H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）３．８９（ｓ，３Ｈ）、３．８０−３．９０（ｍ，１Ｈ）、３．２８−３．５０（ｍ，２Ｈ）、２．６０−２．７８（ｍ，２Ｈ）、２．０９−２．２７（ｍ，４Ｈ）、１．６２−１．７５（ｍ，２Ｈ） Reference production example 78
2.0 g of 1-iodo-4,4,4-trifluorobutane and 2.0 g of methyl (3,3,3-trifluoropropylsulfonyl) acetate were dissolved in 30 ml of dimethyl sulfoxide. To this was added 1.2 g of potassium carbonate at room temperature, and the mixture was stirred at the same temperature for 3 days. Then, 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, and methyl 6,6,6-trifluoro-2- (3,3,3-trifluoropropylsulfonyl) hexanoate (hereinafter referred to as the present organic sulfur compound (78)). .) 1.50 g was obtained.
This organic sulfur compound (78)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 3.89 (s, 3H), 3.80-3.90 (m, 1H), 3.28-3.50 (m, 2H), 2.60-2.78 (m, 2H), 2.09-2.27 (m, 4H), 1.62-1.75 (m, 2H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）３．９６（ｓ，３Ｈ）、３．５３−３．８４（ｍ，２Ｈ）、２．１２−２．７９（ｍ，６Ｈ）、１．７２−２．０２（ｍ，２Ｈ） Reference Production Example 79
1.0 g of methyl 6,6,6-trifluoro-2- (3,3,3-trifluoropropylsulfonyl) hexanoate was dissolved in 30 ml of tetrahydrofuran. To this, 0.12 g of sodium hydride (60% oily) was added at room temperature, and the mixture was stirred at the same temperature for 0.5 hour. After adding 0.4 g of N-chlorosuccinimide at room temperature and stirring for 4 hours, 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, and methyl 2-chloro-6,6,6-trifluoro-2- (3,3,3-trifluoropropylsulfonyl) hexanoate (hereinafter referred to as the present organic sulfur compound ( 79).) 0.96 g was obtained.
This organic sulfur compound (79)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 3.96 (s, 3H), 3.53-3.84 (m, 2H), 2.12-2.79 (m, 6H), 1.72 to 2.02 (m, 2H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）６．９３（ｂｓ，１Ｈ）、６．２０（ｂｓ，１Ｈ）、３．３６−３．７４（ｍ，２Ｈ）、２．１３−２．８１（ｍ，６Ｈ）、１．６１−２．０１（ｍ，２Ｈ） Reference production example 80
0.8 g of methyl 2-chloro-6,6,6-trifluoro-2- (3,3,3-trifluoropropylsulfonyl) hexanoate was dissolved in 20 ml of methanol. To this, 0.9 ml of ammonia (7M methanol solution) was added at room temperature, followed by stirring at the same temperature for 10 hours. The reaction mixture was concentrated under reduced pressure, and the resulting residue was subjected to silica gel chromatography to give 2-chloro-6,6,6-trifluoro-2- (3,3,3-trifluoropropylsulfonyl) hexanamide ( Hereinafter, this organic sulfur compound (80) is described.) 0.51 g was obtained.
This organic sulfur compound (80)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 6.93 (bs, 1H), 6.20 (bs, 1H), 3.36-3.74 (m, 2H), 2.13 2.81 (m, 6H), 1.61-2.01 (m, 2H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）６．９３（ｂｓ，１Ｈ）、６．３６（ｂｓ，１Ｈ）、３．３８−３．７３（ｍ，２Ｈ）、２．２１−２．９２（ｍ，６Ｈ） Reference production example 81
1.0 g of methyl 2-chloro-5,5,5-trifluoro-2- (3,3,3-trifluoropropylsulfonyl) pentanoate was dissolved in 30 ml of methanol. To this, 1.2 ml of ammonia (7M methanol solution) was added at room temperature and stirred at the same temperature for 14 hours. The reaction mixture was concentrated under reduced pressure, and the resulting residue was subjected to silica gel chromatography to give 2-chloro-5,5,5-trifluoro-2- (3,3,3-trifluoropropylsulfonyl) pentanamide ( Hereinafter, this organic sulfur compound (81) is described.) 0.62 g was obtained.
This organic sulfur compound (81)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 6.93 (bs, 1H), 6.36 (bs, 1H), 3.38-3.73 (m, 2H), 2.21- 2.92 (m, 6H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）３．９１（ｓ，３Ｈ）、３．８７−３．９５（ｍ，１Ｈ）、３．３６−３．５２（ｍ，２Ｈ）、２．２１−２．７８（ｍ，６Ｈ） Reference production example 82
2.8 g of 1-iodo-3,3,4,4,5,5,5-heptafluoropentane and 2.0 g of methyl (3,3,3-trifluoropropylsulfonyl) acetate were dissolved in 30 ml of dimethyl sulfoxide. . To this, 0.34 g of sodium hydride (60% oily) was added at room temperature and stirred at the same temperature for 14 hours, 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, and methyl 5,5,6,6,7,7,7-heptafluoro-2- (3,3,3-trifluoropropylsulfonyl) heptanoate (hereinafter referred to as the present). 2.30 g of organic sulfur compound (82) is obtained.
This organic sulfur compound (82)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 3.91 (s, 3H), 3.87-3.95 (m, 1H), 3.36-3.52 (m, 2H), 2.21-2.78 (m, 6H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）３．９７（ｓ，３Ｈ）、３．５３−３．９０（ｍ，２Ｈ）、２．３０−２．９１（ｍ，６Ｈ） Reference production example 83
1.0 g of methyl 5,5,6,6,7,7,7-heptafluoro-2- (3,3,3-trifluoropropylsulfonyl) heptanoate was dissolved in 30 ml of tetrahydrofuran. To this, 0.09 g of sodium hydride (60% oily) was added at room temperature, and the mixture was stirred at the same temperature for 0.5 hour. After adding 0.3 g of N-chlorosuccinimide at room temperature and stirring for 1 hour, 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel chromatography to obtain methyl 2-chloro-5,5,6,6,7,7,7-heptafluoro-2- (3,3,3-trifluoropropylsulfonyl) heptanoate. (Hereinafter referred to as the present organic sulfur compound (83).) 0.93 g was obtained.
This organic sulfur compound (83)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 3.97 (s, 3H), 3.53-3.90 (m, 2H), 2.30-2.91 (m, 6H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）６．８８（ｂｓ，１Ｈ）、５．９４（ｂｓ，１Ｈ）、３．３７−３．７３（ｍ，２Ｈ）、２．１４−２．９６（ｍ，６Ｈ） Reference production example 84
0.7 g of methyl 2-chloro-5,5,6,6,7,7,7-heptafluoro-2- (3,3,3-trifluoropropylsulfonyl) heptanoate was dissolved in 30 ml of methanol. To this, 0.6 ml of ammonia (7M methanol solution) was added at room temperature, followed by stirring at the same temperature for 10 hours. The reaction mixture was concentrated under reduced pressure, and the resulting residue was subjected to silica gel chromatography to give 2-chloro-5,5,6,6,7,7,7-heptafluoro-2- (3,3,3- 0.50 g of trifluoropropylsulfonyl) heptanamide (hereinafter referred to as the present organic sulfur compound (84)) was obtained.
This organic sulfur compound (84)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 6.88 (bs, 1H), 5.94 (bs, 1H), 3.37-3.73 (m, 2H), 2.14 2.96 (m, 6H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）３．９２（ｓ，３Ｈ）、３．８７−３．９５（ｍ，１Ｈ）、３．３８−３．５２（ｍ，２Ｈ）、２．２０−２．７８（ｍ，６Ｈ） Reference production example 85
1-Iodo-3,3,4,4,5,5,6,6,6-nonafluorohexane (7.0 g) and methyl (3,3,3-trifluoropropylsulfonyl) acetate (4.4 g) were added to dimethyl sulfoxide (50 ml). Dissolved in. To this, 2.59 g of potassium carbonate was added at room temperature. The reaction mixture was heated to 60 ° C. and stirred for 2 days, then allowed to cool to near room temperature, 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, and methyl 5,5,6,6,7,7,8,8,8-nonafluoro-2- (3,3,3-trifluoropropylsulfonyl) octanoate ( Hereinafter referred to as the present organic sulfur compound (85).) 1.50 g was obtained.
This organic sulfur compound (85)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 3.92 (s, 3H), 3.87-3.95 (m, 1H), 3.38-3.52 (m, 2H), 2.20-2.78 (m, 6H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）３．９７（ｓ，３Ｈ）、３．５８−３．９２（ｍ，２Ｈ）、２．３３−２．９４（ｍ，６Ｈ） Reference production example 86
1.0 g of methyl 5,5,6,6,7,7,8,8,8-nonafluoro-2- (3,3,3-trifluoropropylsulfonyl) octanoate was dissolved in 30 ml of tetrahydrofuran. To this, 0.08 g of sodium hydride (60% oily) was added at room temperature, and the mixture was stirred at the same temperature for 0.5 hour. After adding 0.3 g of N-chlorosuccinimide at room temperature and stirring for 16 hours, 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, and 2-chloro-5,5,6,6,7,7,8,8,8-nonafluoro-2- (3,3,3-trifluoropropylsulfonyl). 0.89 g of methyl octoate (hereinafter referred to as the present organic sulfur compound (86)) was obtained.
This organic sulfur compound (86)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 3.97 (s, 3H), 3.58-3.92 (m, 2H), 2.33-2.94 (m, 6H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）６．８８（ｂｓ，１Ｈ）、５．９３（ｂｓ，１Ｈ）、３．３８−３．７７（ｍ，２Ｈ）、２．１５−２．９８（ｍ，６Ｈ） Reference production example 87
0.8 g of methyl 2-chloro-5,5,6,6,7,7,8,8,8-nonafluoro-2- (3,3,3-trifluoropropylsulfonyl) octanoate was dissolved in 20 ml of methanol. It was. To this, 1.1 ml of ammonia (7M-methanol solution) was added at room temperature and stirred at the same temperature for 12 hours. The reaction mixture was concentrated under reduced pressure, and the resulting residue was subjected to silica gel chromatography to give 2-chloro-5,5,6,6,7,7,8,8,8-nonafluoro-2- (3,3 , 3-trifluoropropylsulfonyl) octanamide (hereinafter referred to as the present organic sulfur compound (87)) 0.45 g was obtained.
This organic sulfur compound (87)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 6.88 (bs, 1H), 5.93 (bs, 1H), 3.38-3.77 (m, 2H), 2.15 2.98 (m, 6H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）３．９８（ｓ，３Ｈ）、３．６３−３．９３（ｍ，２Ｈ）、２．２９−２．９２（ｍ，６Ｈ） Reference production example 88
2.0 g of methyl 5,5,6,6,6-pentafluoro-2- (3,3,4,4,4-pentafluorobutylsulfonyl) hexanoate was dissolved in 30 ml of dimethyl sulfoxide. To this, 0.19 g of sodium hydride (60% oily) was added at room temperature, and the mixture was stirred at the same temperature for 0.5 hour. 1.9 g of copper (II) chloride was added to the mixture at room temperature and stirred for 12 hours, 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, and methyl 2-chloro-5,5,6,6,6-pentafluoro-2- (3,3,4,4,4-pentafluorobutylsulfonyl) hexanoate. (Hereinafter referred to as the present organic sulfur compound (88).) 1.70 g was obtained.
This organic sulfur compound (88)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 3.98 (s, 3H), 3.63-3.93 (m, 2H), 2.29-2.92 (m, 6H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）６．８６（ｂｓ，１Ｈ）、５．９３（ｂｓ，１Ｈ）、３．４０−３．７８（ｍ，２Ｈ）、２．１３−２．９５（ｍ，６Ｈ） Reference 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 in 30 ml of methanol. To this, 1.4 ml of ammonia (7M methanol solution) was added at room temperature and stirred at the same temperature for 16 hours. The reaction mixture was concentrated under reduced pressure, and the resulting residue was subjected to silica gel chromatography to give 2-chloro-5,5,6,6,6-pentafluoro-2- (3,3,4,4,4- 1.10 g of pentafluorobutylsulfonyl) hexanamide (hereinafter referred to as the present organic sulfur compound (89)) was obtained.
This organic sulfur compound (89)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 6.86 (bs, 1H), 5.93 (bs, 1H), 3.40-3.78 (m, 2H), 2.13 2.95 (m, 6H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）４．００（ｓ，３Ｈ）、３．２６−３．５８（ｍ，２Ｈ）、２．１２−２．８０（ｍ，６Ｈ） Reference production example 90
1.0 g of methyl 5,5,6,6,7,7,7-heptafluoro-2- (3,3,3-trifluoropropylsulfonyl) heptanoate was dissolved in 30 ml of tetrahydrofuran, and hydrogenated at room temperature. Sodium (60% oily) 0.09 g was added and stirred at the same temperature for 0.5 hour. To the mixture, 0.7 g of 1-fluoro-2,4,6-trimethylpyridinium trifluoromethanesulfonate was added at room temperature and stirred for 10 hours. 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain methyl 2,5,5,6,6,7,7,7-octafluoro-2- (3,3,3-trifluoropropylsulfonyl) heptanoate (hereinafter referred to as “heptanoic acid methyl ester”). This is referred to as the organic sulfur compound (90).) 0.90 g was obtained.
This organic sulfur compound (90)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 4.00 (s, 3H), 3.26-3.58 (m, 2H), 2.12-2.80 (m, 6H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）６．５８（ｂｓ，１Ｈ）、５．９２（ｂｓ，１Ｈ）、３．２６−３．５８（ｍ，２Ｈ）、２．１９−２．８３（ｍ，６Ｈ） Reference production example 91
0.7 g of methyl 2,5,5,6,6,7,7,7-octafluoro-2- (3,3,3-trifluoropropylsulfonyl) heptanoate was dissolved in 30 ml of methanol. To this, 0.7 ml of ammonia (7M methanol solution) was added at room temperature and stirred at the same temperature for 10 hours. The reaction mixture was concentrated under reduced pressure, and the resulting residue was subjected to silica gel chromatography to obtain 2,5,5,6,6,7,7,7-octafluoro-2- (3,3,3-trifluoro. Propylsulfonyl) heptanamide (hereinafter referred to as the present organic sulfur compound (91)) 1.10 g was obtained.
This organic sulfur compound (91)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 6.58 (bs, 1H), 5.92 (bs, 1H), 3.26-3.58 (m, 2H), 2.19- 2.83 (m, 6H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）３．９０（ｓ，３Ｈ）、３．８８−３．９６（ｍ，１Ｈ）、３．３８−３．５５（ｍ，２Ｈ）、２．５４−２．７３（ｍ，２Ｈ）、２．２３−２．５０（ｍ，４Ｈ） Reference production example 92
1.6 g of 1-iodo-3,3,3-trifluoropropane and 2.0 g of methyl (3,3,4,4,4-pentafluorobutylsulfonyl) acetate were dissolved in 50 ml of dimethyl sulfoxide. To this was added 0.3 g of sodium hydride (60% oily) at room temperature, and the mixture was stirred at the same temperature for 19 hours. Then, 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, and methyl 2- (3,3,4,4,4-pentafluorobutylsulfonyl) -5,5,5-trifluoropentanoate (hereinafter referred to as the present organic sulfur compound ( 92).) 1.20 g was obtained.
This organic sulfur compound (92)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 3.90 (s, 3H), 3.88-3.96 (m, 1H), 3.38-3.55 (m, 2H), 2.54-2.73 (m, 2H), 2.23-2.50 (m, 4H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）３．９７（ｓ，３Ｈ）、３．６２−３．９１（ｍ，２Ｈ）、２．３７−２．８８（ｍ，６Ｈ） Reference Production Example 93
1.0 g of methyl 2- (3,3,4,4,4-pentafluorobutylsulfonyl) -5,5,5-trifluoropentanoate was dissolved in 30 ml of tetrahydrofuran. To this, 0.11 g of sodium hydride (60% oily) was added at room temperature, and the mixture was stirred at the same temperature for 0.5 hour. To this mixture, 0.4 g of N-chlorosuccinimide was added at room temperature and stirred for 10 hours, 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, and methyl 2-chloro-2- (3,3,4,4,4-pentafluorobutylsulfonyl) -5,5,5-trifluoropentanoate (hereinafter referred to as the present). 0.75 g of organic sulfur compound (93) was obtained.
This organic sulfur compound (93)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 3.97 (s, 3H), 3.62-3.91 (m, 2H), 2.37-2.88 (m, 6H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）６．８７（ｂｓ，１Ｈ）、６．０１（ｂｓ，１Ｈ）、３．３５−３．８０（ｍ，２Ｈ）、２．１９−２．９２（ｍ，６Ｈ） Reference production example 94
0.5 g of methyl 2-chloro-2- (3,3,4,4,4-pentafluorobutylsulfonyl) -5,5,5-trifluoropentanoate was dissolved in 50 ml of methanol. To this, 0.5 ml of ammonia (7M methanol solution) was added at room temperature and stirred at the same temperature for 18 hours. The reaction mixture was concentrated under reduced pressure, and the resulting residue was subjected to silica gel chromatography to give 2-chloro-2- (3,3,4,4,4-pentafluorobutylsulfonyl) -5,5,5-tri 1.10 g of fluoropentanamide (hereinafter referred to as the present organic sulfur compound (94)) was obtained.
This organic sulfur compound (94)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 6.87 (bs, 1H), 6.01 (bs, 1H), 3.35-3.80 (m, 2H), 2.19- 2.92 (m, 6H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）３．９３−３．９７（ｍ，１Ｈ）、３．９１（ｓ，３Ｈ）、３．４１−３．５５（ｍ，２Ｈ）、２．２１−２．７３（ｍ，６Ｈ） Reference production example 95
1-Iodo-3,3,4,4,5,5,5-heptafluoropentane (2.3 g) and (3,3,4,4,4-pentafluorobutylsulfonyl) acetate (2.0 g) were added to dimethylsulfoxide (50 ml) Dissolved in. To this was added 0.3 g of sodium hydride (60% oily) at room temperature, and the mixture was stirred at the same temperature for 26 hours. Then, 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain methyl 5,5,6,6,7,7,7-heptafluoro-2- (3,3,4,4,4-pentafluorobutylsulfonyl) heptanoate. (Hereinafter referred to as the present organic sulfur compound (95)) 1.40 g was obtained.
This organic sulfur compound (95)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 3.93-3.97 (m, 1H), 3.91 (s, 3H), 3.41-3.55 (m, 2H), 2.21-2.73 (m, 6H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）３．９８（ｓ，３Ｈ）、３．６２−３．９２（ｍ，２Ｈ）、２．１９−２．９４（ｍ，６Ｈ） Reference production example 96
1.3 g of methyl 5,5,6,6,7,7,7-heptafluoro-2- (3,3,4,4,4-pentafluorobutylsulfonyl) heptanoate was dissolved in 30 ml of tetrahydrofuran. To this, 0.11 g of sodium hydride (60% oily) was added at room temperature, and the mixture was stirred at the same temperature for 0.5 hour. To this mixture, 0.4 g of N-chlorosuccinimide was added at room temperature and stirred for 10 hours, 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to give 2-chloro-5,5,6,6,7,7,7-heptafluoro-2- (3,3,4,4,4-pentafluorobutylsulfonyl. ) 0.91 g of methyl heptanoate (hereinafter referred to as the present organic sulfur compound (96)) was obtained.
This organic sulfur compound (96)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 3.98 (s, 3H), 3.62-3.92 (m, 2H), 2.19-2.94 (m, 6H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）６．８８（ｂｓ，１Ｈ）、５．９５（ｂｓ，１Ｈ）、３．３９−３．７８（ｍ，２Ｈ）、２．１４−２．９６（ｍ，６Ｈ） Reference production example 97
Dissolve 0.8 g of methyl 2-chloro-5,5,6,6,7,7,7-heptafluoro-2- (3,3,4,4,4-pentafluorobutylsulfonyl) heptanoate in 50 ml of methanol I let you. To this, 0.7 ml of ammonia (7M methanol solution) was added at room temperature and stirred at the same temperature for 18 hours. The reaction mixture was concentrated under reduced pressure, and the resulting residue was subjected to silica gel chromatography to give 2-chloro-5,5,6,6,7,7,7-heptafluoro-2- (3,3,4, 0.60 g of 4,4-pentafluorobutylsulfonyl) heptanamide (hereinafter referred to as the present organic sulfur compound (97)) was obtained.
This organic sulfur compound (97)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 6.88 (bs, 1H), 5.95 (bs, 1H), 3.39-3.78 (m, 2H), 2.14 2.96 (m, 6H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）３．８７（ｓ，３Ｈ）、３．８０−３．８８（ｍ，１Ｈ）、３．２６−３．５０（ｍ，２Ｈ）、２．５９−２．７８（ｍ，２Ｈ）、２．０３−２．１８（ｍ，４Ｈ）、１．４４−１．７２（ｍ，４Ｈ） Reference production example 98
2.2 g of 1-iodo-5,5,5-trifluoropentane and 2.0 g of methyl (3,3,3-trifluoropropylsulfonyl) acetate were dissolved in 30 ml of dimethyl sulfoxide. To this was added 0.3 g of sodium hydride (60% oily) at room temperature, and the mixture was stirred at the same temperature for 20 hours. Then, 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, and methyl 7,7,7-trifluoro-2- (3,3,3-trifluoropropylsulfonyl) heptanoate (hereinafter referred to as the present organic sulfur compound (98)). .) 1.69 g was obtained.
This organic sulfur compound (98)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 3.87 (s, 3H), 3.80-3.88 (m, 1H), 3.26-3.50 (m, 2H), 2.59-2.78 (m, 2H), 2.03-2.18 (m, 4H), 1.44-1.72 (m, 4H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）３．９４（ｓ，３Ｈ）、３．５０−３．８１（ｍ，２Ｈ）、２．５５−２．８０（ｍ，３Ｈ）、２．０５−２．３２（ｍ，３Ｈ）、１．５０−１．８０（ｍ，４Ｈ） Reference Production Example 99
1.0 g of methyl 7,7,7-trifluoro-2- (3,3,3-trifluoropropylsulfonyl) heptanoate was dissolved in 30 ml of tetrahydrofuran. To this, 0.11 g of sodium hydride (60% oily) was added at room temperature, and the mixture was stirred at the same temperature for 0.5 hour. To this mixture, 0.4 g of N-chlorosuccinimide was added at room temperature and stirred for 10 hours, 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, and methyl 2-chloro-7,7,7-trifluoro-2- (3,3,3-trifluoropropylsulfonyl) heptanoate (hereinafter referred to as the present organic sulfur compound ( 99).) 0.80 g was obtained.
This organic sulfur compound (99)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 3.94 (s, 3H), 3.50-3.81 (m, 2H), 2.55-2.80 (m, 3H), 2.05-2.32 (m, 3H), 1.50-1.80 (m, 4H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）６．８８（ｂｓ，１Ｈ）、５．９８（ｂｓ，１Ｈ）、３．３４−３．７８（ｍ，２Ｈ）、２．５８−２．８１（ｍ，３Ｈ）、２．０１−２．２８（ｍ，３Ｈ）、１．４０−１．８２（ｍ，４Ｈ） Reference production example 100
0.6 g of methyl 2-chloro-7,7,7-trifluoro-2- (3,3,3-trifluoropropylsulfonyl) heptanoate was dissolved in 30 ml of methanol. To this, 0.7 ml of ammonia (7M methanol solution) was added at room temperature, and the mixture was stirred at the same temperature for 3 days. The reaction mixture was concentrated under reduced pressure, and the resulting residue was subjected to silica gel chromatography to give 2-chloro-7,7,7-trifluoro-2- (3,3,3-trifluoropropylsulfonyl) heptanamide ( Hereinafter, this organic sulfur compound (100) is described.) 0.46 g was obtained.
This organic sulfur compound (100)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 6.88 (bs, 1H), 5.98 (bs, 1H), 3.34-3.78 (m, 2H), 2.58- 2.81 (m, 3H), 2.01-2.28 (m, 3H), 1.40-1.82 (m, 4H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）３．８９（ｓ，３Ｈ）、３．８０−３．８８（ｍ，１Ｈ）、３．２６−３．５４（ｍ，２Ｈ）、２．５９−２．８０（ｍ，３Ｈ）、２．００−２．２６（ｍ，３Ｈ）、１．６５−１．７８（ｍ，２Ｈ） Reference production example 101
1.4 g of p-toluenesulfonic acid 4,4,5,5,5-pentafluoropentyl and 1.0 g of methyl (3,3,3-trifluoropropylsulfonyl) acetate were dissolved in 50 ml of dimethyl sulfoxide. To this, 0.2 g of sodium hydride (60% oily) was added at room temperature, and then the temperature was raised to 90 ° C. After stirring at the same temperature for 6 hours, 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, and methyl 6,6,7,7,7-pentafluoro-2- (3,3,3-trifluoropropylsulfonyl) heptanoate (hereinafter referred to as the present organic sulfur compound ( 101).) 0.70 g was obtained.
This organic sulfur compound (101)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 3.89 (s, 3H), 3.80-3.88 (m, 1H), 3.26-3.54 (m, 2H), 2.59-2.80 (m, 3H), 2.00-2.26 (m, 3H), 1.65-1.78 (m, 2H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）３．９６（ｓ，３Ｈ）、３．５０−３．８５（ｍ，２Ｈ）、２．６１−２．７８（ｍ，３Ｈ）、１．７５−２．４０（ｍ，５Ｈ） Reference production example 102
0.5 g of methyl 6,6,7,7,7-pentafluoro-2- (3,3,3-trifluoropropylsulfonyl) heptanoate was dissolved in 30 ml of tetrahydrofuran. To this, 0.05 g of sodium hydride (60% oily) was added at room temperature, and the mixture was stirred at the same temperature for 0.5 hour. The mixture was added with 0.2 g of N-chlorosuccinimide at room temperature and stirred for 10 hours, 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, and methyl 2-chloro-6,6,7,7,7-pentafluoro-2- (3,3,3-trifluoropropylsulfonyl) heptanoate (hereinafter referred to as the present product). 0.38 g of organic sulfur compound (102) was obtained.
This organic sulfur compound (102)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 3.96 (s, 3H), 3.50-3.85 (m, 2H), 2.61-2.78 (m, 3H), 1.75-2.40 (m, 5H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）６．９５（ｂｓ，１Ｈ）、６．３０（ｂｓ，１Ｈ）、３．３５−３．７８（ｍ，２Ｈ）、２．６１−２．８０（ｍ，３Ｈ）、１．６２−２．３２（ｍ，５Ｈ） Reference production example 103
0.3 g of methyl 2-chloro-6,6,7,7,7-pentafluoro-2- (3,3,3-trifluoropropylsulfonyl) heptanoate was dissolved in 30 ml of methanol. To this, 0.3 ml of ammonia (7M methanol solution) was added at room temperature, and the mixture was stirred at the same temperature for 20 hours. The reaction mixture was concentrated under reduced pressure, and the resulting residue was subjected to silica gel chromatography to give 2-chloro-6,6,7,7,7-pentafluoro-2- (3,3,3-trifluoropropylsulfonyl). ) Heptanamide (hereinafter referred to as the present organic sulfur compound (103)) 0.23 g was obtained.
This organic sulfur compound (103)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 6.95 (bs, 1H), 6.30 (bs, 1H), 3.35-3.78 (m, 2H), 2.61- 2.80 (m, 3H), 1.62-2.32 (m, 5H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）３．９０（ｓ，３Ｈ）、３．８８−３．９８（ｍ，１Ｈ）、３．３８−３．５４（ｍ，２Ｈ）、２．２３−２．７８（ｍ，６Ｈ） Reference production example 104
5.0 g of 1,2-dichloro-1,1,2-trifluoro-4-iodobutane and 3.8 g of methyl (3,3,3-trifluoropropylsulfonyl) acetate were dissolved in 100 ml of dimethyl sulfoxide. To this was added 0.7 g of sodium hydride (60% oily) at room temperature, and the mixture was stirred at the same temperature for 3 days. Then, 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, and methyl 5,6-dichloro-5,6,6-trifluoro-2- (3,3,3-trifluoropropylsulfonyl) hexanoate (hereinafter referred to as the present organic sulfur). 1.50 g was obtained.
This organic sulfur compound (104)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 3.90 (s, 3H), 3.88-3.98 (m, 1H), 3.38-3.54 (m, 2H), 2.23-2.78 (m, 6H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）３．９７（ｓ，３Ｈ）、３．５９−３．８８（ｍ，２Ｈ）、２．３８−３．０８（ｍ，６Ｈ） Reference production example 105
1.0 g of the organic sulfur compound (104) was dissolved in 30 ml of tetrahydrofuran. To this, 0.1 g of sodium hydride (60% oily) was added at room temperature, and the mixture was stirred at the same temperature for 0.5 hour. After adding 0.3 g of N-chlorosuccinimide at room temperature and stirring for 16 hours, 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain methyl 2,5,6-trichloro-5,6,6-trifluoro-2- (3,3,3-trifluoropropylsulfonyl) hexanoate (hereinafter referred to as the present product). 0.85 g of organic sulfur compound (105) was obtained.
This organic sulfur compound (105)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 3.97 (s, 3H), 3.59-3.88 (m, 2H), 2.38-3.08 (m, 6H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）６．８６（ｂｓ，１Ｈ）、５．９０（ｂｓ，１Ｈ）、３．３４−３．７８（ｍ，２Ｈ）、２．４０−３．０９（ｍ，６Ｈ） Reference production example 106
0.6 g of the organic sulfur compound (105) was dissolved in 30 ml of methanol. To this, 0.6 ml of ammonia (7M methanol solution) was added at room temperature, and the mixture was stirred at the same temperature for 16 hours. The reaction mixture was concentrated under reduced pressure, and the resulting residue was subjected to silica gel chromatography to obtain 2,5,6-trichloro-5,6,6-trifluoro-2- (3,3,3-trifluoropropylsulfonyl). ) Hexamide (hereinafter referred to as the present organic sulfur compound (106)) 0.40 g was obtained.
This organic sulfur compound (106)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 6.86 (bs, 1H), 5.90 (bs, 1H), 3.34-3.78 (m, 2H), 2.40- 3.09 (m, 6H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）３．９２（ｓ，３Ｈ）、３．８８−３．９５（ｍ，１Ｈ）、３．３８−３．５２（ｍ，２Ｈ）、２．６３−２．７８（ｍ，２Ｈ）、２．２４−２．５５（ｍ，４Ｈ） Reference production example 107
1.2 g of 1,4-dibromo-1,1,2,2-tetrafluorobutane and 1.0 g of methyl (3,3,3-trifluoropropylsulfonyl) acetate were dissolved in 30 ml of dimethyl sulfoxide. To this, 0.2 g of sodium hydride (60% oily) was added at room temperature. After stirring at the same temperature for 3 days, 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, and methyl 6-bromo-5,5,6,6-tetrafluoro-2- (3,3,3-trifluoropropylsulfonyl) hexanoate (hereinafter referred to as the present organic sulfur). Compound (107).) 0.50 g was obtained.
This organic sulfur compound (107)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 3.92 (s, 3H), 3.88-3.95 (m, 1H), 3.38-3.52 (m, 2H), 2.63-2.78 (m, 2H), 2.24-2.55 (m, 4H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）３．９７（ｓ，３Ｈ）、３．５０−３．９４（ｍ，２Ｈ）、２．３０−２．９２（ｍ，６Ｈ） Reference production example 108
0.4 g of this organic sulfur compound (107) was dissolved in 30 ml of dimethyl sulfoxide. To this, 0.04 g of sodium hydride (60% oily) was added at room temperature, and the mixture was stirred at the same temperature for 0.5 hour. After adding 0.4 g of anhydrous cupric chloride to the mixture at room temperature and stirring for 4 hours, 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain methyl 6-bromo-2-chloro-5,5,6,6-tetrafluoro-2- (3,3,3-trifluoropropylsulfonyl) hexanoate (hereinafter referred to as “hexanoic acid methyl ester”). This is referred to as the present organic sulfur compound (108).) 0.40 g was obtained.
This organic sulfur compound (108)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 3.97 (s, 3H), 3.50-3.94 (m, 2H), 2.30-2.92 (m, 6H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）６．８７（ｂｓ，１Ｈ）、５．９８（ｂｓ，１Ｈ）、３．３８−３．７５（ｍ，２Ｈ）、２．１８−２．９５（ｍ，６Ｈ） Reference Production Example 109
0.3 g of this organic sulfur compound (108) was dissolved in 20 ml of methanol. To this, 0.2 ml of ammonia (7M methanol solution) was added at room temperature and stirred at the same temperature for 14 hours. The reaction mixture was concentrated under reduced pressure, and the resulting residue was subjected to silica gel chromatography to give 6-bromo-2-chloro-5,5,6,6-tetrafluoro-2- (3,3,3-trifluoro 0.19 g of propylsulfonyl) hexanamide (hereinafter referred to as the present organic sulfur compound (109)) was obtained.
This organic sulfur compound (109)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 6.87 (bs, 1H), 5.98 (bs, 1H), 3.38-3.75 (m, 2H), 2.18- 2.95 (m, 6H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）３．８８（ｓ，３Ｈ）、３．７５−３．８５（ｍ，１Ｈ）、３．２８−３．４９（ｍ，２Ｈ）、１．３３−２．７８（ｍ，７Ｈ）、１．１５（ｄ，３Ｈ） Reference production example 110
2.0 g of 4,4,4-trifluoro-3-methylbutyl p-toluenesulfonate and 1.6 g of methyl (3,3,3-trifluoropropylsulfonyl) acetate were dissolved in 50 ml of dimethyl sulfoxide. To this, 0.3 g of sodium hydride (60% oily) was added at room temperature. The reaction mixture was heated to 60 ° C., stirred at the same temperature for 20 hours, and then allowed to cool to near room temperature. 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, and methyl 6,6,6-trifluoro-5-methyl-2- (3,3,3-trifluoropropylsulfonyl) hexanoate (hereinafter referred to as the present organic sulfur compound ( 201).) 0.83 g was obtained.
This organic sulfur compound (201)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 3.88 (s, 3H), 3.75-3.85 (m, 1H), 3.28-3.49 (m, 2H), 1.33-2.78 (m, 7H), 1.15 (d, 3H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）３．９６（ｓ，３Ｈ）、３．５０−３．８６（ｍ，２Ｈ）、１．４２−２．８１（ｍ，７Ｈ）、１．１８（ｄｄ，３Ｈ） Reference Production Example 111
0.7 g of the organic sulfur compound (201) was dissolved in 30 ml of tetrahydrofuran. To this, 0.1 g of sodium hydride (60% oily) was added at room temperature, and the mixture was stirred at the same temperature for 0.5 hour. 0.3 g of N-chlorosuccinimide was added to the mixture at room temperature and stirred for 10 hours, 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, and methyl 2-chloro-6,6,6-trifluoro-5-methyl-2- (3,3,3-trifluoropropylsulfonyl) hexanoate (hereinafter referred to as the present). 0.70 g of organic sulfur compound (202) is obtained.
This organic sulfur compound (202)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 3.96 (s, 3H), 3.50-3.86 (m, 2H), 1.42-2.81 (m, 7H), 1.18 (dd, 3H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）６．８８（ｂｓ，１Ｈ）、５．９９（ｂｓ，１Ｈ）、３．３３−３．６８（ｍ，２Ｈ）、１．３５−２．８１（ｍ，７Ｈ）、１．１７（ｄ，３Ｈ） Reference production example 112
0.6 g of the organic sulfur compound (202) was dissolved in 30 ml of methanol. To this, 0.6 ml of ammonia (7M methanol solution) was added at room temperature, and the mixture was stirred at the same temperature for 3 days. The reaction mixture was concentrated under reduced pressure, and the resulting residue was subjected to silica gel chromatography to give 2-chloro-6,6,6-trifluoro-5-methyl-2- (3,3,3-trifluoropropylsulfonyl). ) Hexanamide (hereinafter referred to as the present organic sulfur compound (203)) 0.45 g was obtained.
This organic sulfur compound (203)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 6.88 (bs, 1H), 5.99 (bs, 1H), 3.33-3.68 (m, 2H), 1.35 2.81 (m, 7H), 1.17 (d, 3H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）３．８９（ｓ，３Ｈ）、３．７８−３．８４（ｍ，１Ｈ）、３．２８−３．５０（ｍ，２Ｈ）、１．４３−２．７８（ｍ，９Ｈ）、１．００（ｄｔ，３Ｈ） Reference production example 113
2.7 g of p-toluenesulfonic acid 3- (trifluoromethyl) pentyl and 2.0 g of methyl (3,3,3-trifluoropropylsulfonyl) acetate were dissolved in 30 ml of dimethyl sulfoxide. To this, 1.2 g of potassium carbonate was added at room temperature. The reaction mixture was heated to 60 ° C., stirred at the same temperature for 4 days, and then allowed to cool to near room temperature. 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue is subjected to silica gel chromatography and described as methyl 5- (trifluoromethyl) -2- (3,3,3-trifluoropropylsulfonyl) heptanoate (hereinafter referred to as the present organic sulfur compound (204)). ) 1.20 g was obtained.
This organic sulfur compound (204)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 3.89 (s, 3H), 3.78-3.84 (m, 1H), 3.28-3.50 (m, 2H), 1.43-2.78 (m, 9H), 1.00 (dt, 3H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）３．９６（ｓ，３Ｈ）、３．５０−３．８５（ｍ，２Ｈ）、１．４３−２．８０（ｍ，９Ｈ）、１．０１（ｔ，３Ｈ） Reference production example 114
1.1 g of this organic sulfur compound (204) was dissolved in 30 ml of tetrahydrofuran. To this, 0.1 g of sodium hydride (60% oily) was added at room temperature, and the mixture was stirred at the same temperature for 0.5 hour. After adding 0.4 g of N-chlorosuccinimide at room temperature and stirring for 1 hour, 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, and methyl 2-chloro-5- (trifluoromethyl) -2- (3,3,3-trifluoropropylsulfonyl) heptanoate (hereinafter referred to as the present organic sulfur compound (205 ) 0.40 g was obtained.
This organic sulfur compound (205)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 3.96 (s, 3H), 3.50-3.85 (m, 2H), 1.43-2.80 (m, 9H), 1.01 (t, 3H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）６．８８（ｂｓ，１Ｈ）、６．０３（ｂｓ，１Ｈ）、３．３１−３．７８（ｍ，２Ｈ）、１．４２−２．８０（ｍ，９Ｈ）、１．０１（ｔ，３Ｈ） Reference production example 115
0.9 g of this organic sulfur compound (205) was dissolved in 20 ml of methanol. To this, 0.9 ml of ammonia (7M methanol solution) was added at room temperature and stirred at the same temperature for 16 hours. The reaction mixture was concentrated under reduced pressure, and the obtained residue was subjected to silica gel chromatography to give 2-chloro-5- (trifluoromethyl) -2- (3,3,3-trifluoropropylsulfonyl) heptanamide (hereinafter referred to as “heptanamide”). This is referred to as the present organic sulfur compound (206).) 0.65 g was obtained.
This organic sulfur compound (206)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 6.88 (bs, 1H), 6.03 (bs, 1H), 3.31-3.78 (m, 2H), 1.42- 2.80 (m, 9H), 1.01 (t, 3H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）３．８９（ｓ，３Ｈ）、３．７８−３．８９（ｍ，１Ｈ）、３．２４−３．５０（ｍ，２Ｈ）、１．４９−２．７８（ｍ，７Ｈ）、１．０３（ｓ，９Ｈ） Reference production example 116
2.9 g of 4,4-dimethyl-3- (trifluoromethyl) pentyl p-toluenesulfonate and 2.0 g of methyl (3,3,3-trifluoropropylsulfonyl) acetate were dissolved in 30 ml of dimethyl sulfoxide. To this, 1.2 g of potassium carbonate was added at room temperature. The reaction mixture was heated to 90 ° C., stirred at the same temperature for 6 hours, and then allowed to cool to near room temperature. 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain methyl 6,6-dimethyl-5- (trifluoromethyl) -2- (3,3,3-trifluoropropylsulfonyl) heptanoate (hereinafter referred to as the present organic sulfur compound). (Described as (207).) 2.00 g was obtained.
This organic sulfur compound (207)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 3.89 (s, 3H), 3.78-3.89 (m, 1H), 3.24-3.50 (m, 2H), 1.49-2.78 (m, 7H), 1.03 (s, 9H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）３．９５（ｓ，３Ｈ）、３．４９−３．８３（ｍ，２Ｈ）、１．６０−２．９０（ｍ，７Ｈ）、１．０５（ｓ，９Ｈ） Reference Production Example 117
The organic sulfur compound (207) (1.9 g) was dissolved in tetrahydrofuran (30 ml). To this, 0.2 g of sodium hydride (60% oily) was added at room temperature, and the mixture was stirred at the same temperature for 0.5 hour. 0.6 g of N-chlorosuccinimide was added to the mixture at room temperature and stirred for 1 hour, 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, and methyl 2-chloro-6,6-dimethyl-5- (trifluoromethyl) -2- (3,3,3-trifluoropropylsulfonyl) heptanoate (hereinafter, This is referred to as the organic sulfur compound (208).) 0.40 g was obtained.
This organic sulfur compound (208)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 3.95 (s, 3H), 3.49-3.83 (m, 2H), 1.60-2.90 (m, 7H), 1.05 (s, 9H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）６．８８（ｂｓ，１Ｈ）、５．８６（ｂｓ，１Ｈ）、３．３３−３．７８（ｍ，２Ｈ）、１．５０−２．８９（ｍ，７Ｈ）、１．０５（ｓ，９Ｈ） Reference production example 118
1.0 g of this organic sulfur compound (208) was dissolved in 50 ml of methanol. To this, 1.0 ml of ammonia (7M methanol solution) was added at room temperature, and the mixture was stirred at the same temperature for 18 hours. The reaction mixture was concentrated under reduced pressure, and the resulting residue was subjected to silica gel chromatography to give 2-chloro-6,6-dimethyl-5- (trifluoromethyl) -2- (3,3,3-trifluoropropyl). 0.53 g of sulfonyl) heptanamide (hereinafter referred to as the present organic sulfur compound (209)) was obtained.
This organic sulfur compound (209)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 6.88 (bs, 1H), 5.86 (bs, 1H), 3.33-3.78 (m, 2H), 1.50- 2.89 (m, 7H), 1.05 (s, 9H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）３．８８−３．９５（ｍ，１Ｈ）、３．３５−３．６０（ｍ，２Ｈ）、１．５０−２．９６（ｍ，７Ｈ）、１．２０（ｄ，３Ｈ） Reference Production Example 119
1.0 g of p-toluenesulfonic acid 4,4,4-trifluoro-3-methylbutyl and 0.7 g of (3,3,3-trifluoropropylsulfonyl) acetonitrile were dissolved in 50 ml of dimethyl sulfoxide. To this was added 0.5 g of potassium carbonate at room temperature, followed by stirring at the same temperature for 16 hours. 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 6,6,6-trifluoro-5-methyl-2- (3,3,3-trifluoropropylsulfonyl) hexanenitrile (hereinafter referred to as the present organic sulfur compound (210 ) 0.50 g was obtained.
This organic sulfur compound (210)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 3.88-3.95 (m, 1H), 3.35-3.60 (m, 2H), 1.50-2.96 (m , 7H), 1.20 (d, 3H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）３．９９（ｓ，３Ｈ）、３．２４−３．５２（ｍ，２Ｈ）、２．５８−２．８０（ｍ，２Ｈ）、１．４２−２．１４（ｍ，７Ｈ）、１．００（ｔ，３Ｈ） Reference production example 120
1.0 g of this organic sulfur compound (204) was dissolved in 30 ml of tetrahydrofuran. To this, 0.1 g of sodium hydride (60% oily) was added at room temperature, and the mixture was stirred at the same temperature for 0.5 hour. To the mixture, 0.8 g of 1-fluoro-2,4,6-trimethylpyridinium trifluoromethanesulfonate was added at room temperature and stirred for 1 hour, 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, and methyl 2-fluoro-5- (trifluoromethyl) -2- (3,3,3-trifluoropropylsulfonyl) heptanoate (hereinafter referred to as the present organic sulfur compound (211) ) 0.77 g was obtained.
This organic sulfur compound (211)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 3.99 (s, 3H), 3.24-3.52 (m, 2H), 2.58-2.80 (m, 2H), 1.42-2.14 (m, 7H), 1.00 (t, 3H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）６．５８（ｂｓ，１Ｈ）、６．１６（ｂｓ，１Ｈ）、３．２６−３．５３（ｍ，２Ｈ）、１．４３−２．８０（ｍ，９Ｈ）、１．００（ｄ，３Ｈ） Reference production example 121
0.6 g of the present organic sulfur compound (211) was dissolved in 30 ml of methanol. To this, 0.6 ml of ammonia (7M methanol solution) was added at room temperature, and the mixture was stirred at the same temperature for 3 days. The reaction mixture was concentrated under reduced pressure, and the resulting residue was subjected to silica gel chromatography to give 2-fluoro-5- (trifluoromethyl) -2- (3,3,3-trifluoropropylsulfonyl) heptanamide (hereinafter referred to as “fluorofluorosulfonylsulfonyl” heptanamide). , Referred to as the present organic sulfur compound (212).) 0.32 g was obtained.
This organic sulfur compound (212)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 6.58 (bs, 1H), 6.16 (bs, 1H), 3.26-3.53 (m, 2H), 1.43- 2.80 (m, 9H), 1.00 (d, 3H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）６．５７（ｂｓ，１Ｈ）、５．６９（ｂｓ，１Ｈ）、３．１３−３．４２（ｍ，２Ｈ）、２．６０−２．７７（ｍ，２Ｈ）、１．４０−２．３６（ｍ，７Ｈ）、１．６７（ｓ，３Ｈ）、１．００（ｓ，３Ｈ） Reference Production Example 122
The organic sulfur compound (204) (1.1 g) and iodomethane (0.4 g) are dissolved in N, N-dimethylformamide (30 ml). After stirring, 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with 10% hydrochloric acid and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was dissolved in 20 ml of methanol, an aqueous potassium hydroxide solution (total amount of a mixed solution of 0.5 g of potassium hydroxide and 5 ml of water) was added at room temperature, and the mixture was stirred at the same temperature for 6 hours. 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was dissolved in 20 ml of dichloromethane. To this, 2 drops of N, N-dimethylformamide and then 0.2 ml of oxalyl chloride were successively added dropwise at room temperature. After stirring at the same temperature for 2 hours, the reaction mixture was concentrated under reduced pressure. The obtained residue was dissolved in 20 ml of tetrahydrofuran, and 0.3 g of ammonia (30% (w / w) aqueous solution) was added dropwise thereto at room temperature. After stirring at the same temperature for 10 hours, a saturated aqueous ammonium chloride solution was added to the reaction mixture, extracted with ethyl acetate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to give 2-methyl-5- (trifluoromethyl) -2- (3,3,3-trifluoropropylsulfonyl) heptanamide (hereinafter referred to as the present organic sulfur compound (213)). 0.30 g was obtained.
This organic sulfur compound (213)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 6.57 (bs, 1H), 5.69 (bs, 1H), 3.13-3.42 (m, 2H), 2.60- 2.77 (m, 2H), 1.40-2.36 (m, 7H), 1.67 (s, 3H), 1.00 (s, 3H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）３．９１（ｄｄ，１Ｈ）、３．３７−３．６０（ｍ，２Ｈ）、１．４５−２．９８（ｍ，９Ｈ）、１．０３（ｔ，３Ｈ） Reference Production Example 123
3.0 g of 3- (trifluoromethyl) pentyl methanesulfonate and 2.6 g of (3,3,3-trifluoropropylsulfonyl) acetonitrile were dissolved in 50 ml of dimethyl sulfoxide. To this, 1.8 g of potassium carbonate was added at room temperature, and the temperature was raised to 60 ° C., followed by stirring at the same temperature for 3 days. The reaction mixture was allowed to cool to near room temperature, 10% hydrochloric acid was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, and 5- (trifluoromethyl) -2- (3,3,3-trifluoropropylsulfonyl) heptanenitrile (hereinafter referred to as the present organic sulfur compound (214)). 3.00 g was obtained.
This organic sulfur compound (214)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 3.91 (dd, 1H), 3.37-3.60 (m, 2H), 1.45-2.98 (m, 9H), 1.03 (t, 3H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）３．５０−３．６５（ｍ，２Ｈ）、１．４６−２．９０（ｍ，９Ｈ）、１．０４（ｔ，３Ｈ） Reference production example 124
0.9 g of this organic sulfur compound (214) was dissolved in 20 ml of tetrahydrofuran. To this, 0.1 g of sodium hydride (60% oily) was added at room temperature, and the mixture was stirred at the same temperature for 0.5 hour. Subsequently, 0.8 g of 1-fluoro-2,4,6-trimethylpyridinium trifluoromethanesulfonate was added at the same temperature and stirred for 2 hours. 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to give 2-fluoro-5- (trifluoromethyl) -2- (3,3,3-trifluoropropylsulfonyl) heptanenitrile (hereinafter referred to as the present organic sulfur compound (215)). 0.50 g was obtained.
This organic sulfur compound (215)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 3.50 to 3.65 (m, 2H), 1.46 to 2.90 (m, 9H), 1.04 (t, 3H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）３．６３−３．８２（ｍ，２Ｈ）、１．４５−２．９０（ｍ，９Ｈ）、１．０４（ｔ，３Ｈ） Reference production example 125
0.9 g of this organic sulfur compound (214) was dissolved in 20 ml of tetrahydrofuran. To this, 0.1 g of sodium hydride (60% oily) was added at room temperature, and the mixture was stirred at the same temperature for 0.5 hour. Subsequently, 0.3 g of N-chlorosuccinimide was added at the same temperature and stirred for 2 hours. 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, and 2-chloro-5- (trifluoromethyl) -2- (3,3,3-trifluoropropylsulfonyl) heptanenitrile (hereinafter referred to as the present organic sulfur compound (216)). 0.52 g was obtained.
This organic sulfur compound (216)

_{^{1 H-NMR (CDCl 3,}} TMS): δ (ppm) 3.63-3.82 (m, 2H), 1.45-2.90 (m, 9H), 1.04 (t, 3H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）３．３５−３．５３（ｍ，２Ｈ）、１．４２−２．９８（ｍ，９Ｈ）、１．８０（ｓ，３Ｈ）、１．０３（ｔ，３Ｈ） Reference Production Example 126
0.9 g of this organic sulfur compound (214) and 0.4 g of iodomethane were dissolved in 20 ml of N, N-dimethylformamide. To this was added 0.1 g of sodium hydride (60% oily) at room temperature, and the mixture was stirred at the same temperature for 20 hours. Then, 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to give 2-methyl-5- (trifluoromethyl) -2- (3,3,3-trifluoropropylsulfonyl) heptanenitrile (hereinafter referred to as the present organic sulfur compound (217). 0.64 g was obtained.
This organic sulfur compound (217)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 3.35-3.53 (m, 2H), 1.42-2.98 (m, 9H), 1.80 (s, 3H), 1.03 (t, 3H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）３．８９（ｓ，３Ｈ）、３．７８−３．８５（ｍ，１Ｈ）、３．２５−３．５０（ｍ，２Ｈ）、１．４８−２．９８（ｍ，８Ｈ）、０．８９−１．０２（ｍ，６Ｈ） Reference Production Example 127
5.0 g of 4-methyl-3- (trifluoromethyl) pentyl methanesulfonate and 4.7 g of methyl (3,3,3-trifluoropropylsulfonyl) acetate were dissolved in 100 ml of dimethyl sulfoxide. To this, 2.8 g of potassium carbonate was added at room temperature. The reaction mixture was heated to 60 ° C., stirred at the same temperature for 3 days, and then allowed to cool to near room temperature. 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, and methyl 6-methyl-5- (trifluoromethyl) -2- (3,3,3-trifluoropropylsulfonyl) heptanoate (hereinafter referred to as the present organic sulfur compound (218)). ) 4.10 g was obtained.
This organic sulfur compound (218)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 3.89 (s, 3H), 3.78-3.85 (m, 1H), 3.25-3.50 (m, 2H), 1.48-2.98 (m, 8H), 0.89-1.02 (m, 6H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）３．９５（ｓ，３Ｈ）、３．４９−３．８４（ｍ，２Ｈ）、１．５８−２．８４（ｍ，８Ｈ）、０．９３−１．０６（ｍ，６Ｈ） Reference production example 128
The organic sulfur compound (218) (4.0 g) was dissolved in tetrahydrofuran (100 ml). To this, 0.4 g of sodium hydride (60% oily) was added at room temperature, and the mixture was stirred at the same temperature for 0.5 hour. To the mixture, 1.4 g of N-chlorosuccinimide was added at room temperature and stirred for 1 hour, 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, and methyl 2-chloro-6-methyl-5- (trifluoromethyl) -2- (3,3,3-trifluoropropylsulfonyl) heptanoate (hereinafter referred to as the present organic compound). This is referred to as a sulfur compound (219).) 2.83 g was obtained.
This organic sulfur compound (219)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 3.95 (s, 3H), 3.49-3.84 (m, 2H), 1.58-2.84 (m, 8H), 0.93-1.06 (m, 6H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）６．８７（ｂｓ，１Ｈ）、５．９４（ｂｓ，１Ｈ）、３．３５−３．７６（ｍ，２Ｈ）、１．４８−２．８２（ｍ，８Ｈ）、０．９４−１．０５（ｍ，６Ｈ） Reference Production Example 129
1.0 g of this organic sulfur compound (219) was dissolved in 50 ml of methanol. To this, 1.0 ml of ammonia (7M methanol solution) was added at room temperature, and the mixture was stirred at the same temperature for 16 hours. The reaction mixture was concentrated under reduced pressure, and the resulting residue was subjected to silica gel chromatography to give 2-chloro-6-methyl-5- (trifluoromethyl) -2- (3,3,3-trifluoropropylsulfonyl). 0.75 g of heptane amide (hereinafter referred to as the present organic sulfur compound (220)) was obtained.
This organic sulfur compound (220)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 6.87 (bs, 1H), 5.94 (bs, 1H), 3.35-3.76 (m, 2H), 1.48- 2.82 (m, 8H), 0.94-1.05 (m, 6H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）３．８９（ｓ，３Ｈ）、３．７８−３．８５（ｍ，１Ｈ）、３．２５−３．５０（ｍ，２Ｈ）、１．３０−２．７８（ｍ，１１Ｈ）、０．９４（ｔ，３Ｈ） Reference production example 130
3.0 g of 3- (trifluoromethyl) -hexyl methanesulfonate and 2.8 g of methyl (3,3,3-trifluoropropylsulfonyl) acetate were dissolved in 50 ml of dimethyl sulfoxide. To this, 1.7 g of potassium carbonate was added at room temperature. The reaction mixture was heated to 60 ° C., stirred at the same temperature for 2 days, and then allowed to cool to near room temperature. 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue is subjected to silica gel chromatography, and described as methyl 5- (trifluoromethyl) -2- (3,3,3-trifluoropropylsulfonyl) octanoate (hereinafter referred to as the present organic sulfur compound (221)). ) 1.90 g was obtained.
This organic sulfur compound (221)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 3.89 (s, 3H), 3.78-3.85 (m, 1H), 3.25-3.50 (m, 2H), 1.30-2.78 (m, 11H), 0.94 (t, 3H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）３．９５（ｓ，３Ｈ）、３．５０−３．８０（ｍ，２Ｈ）、１．３０−２．８０（ｍ，１１Ｈ）、０．９５（ｔ，３Ｈ） Reference Production Example 131
1.7 g of the present organic sulfur compound (221) was dissolved in 50 ml of tetrahydrofuran. To this, 0.2 g of sodium hydride (60% oily) was added at room temperature, and the mixture was stirred at the same temperature for 0.5 hour. To the mixture, 0.6 g of N-chlorosuccinimide was added at room temperature and stirred for 2 hours, 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, and methyl 2-chloro-5- (trifluoromethyl) -2- (3,3,3-trifluoropropylsulfonyl) octanoate (hereinafter referred to as the present organic sulfur compound (222)). ).) 1.20 g was obtained.
This organic sulfur compound (222)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 3.95 (s, 3H), 3.50-3.80 (m, 2H), 1.30-2.80 (m, 11H), 0.95 (t, 3H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）６．８７（ｂｓ，１Ｈ）、５．９５（ｂｓ，１Ｈ）、３．３４−３．７８（ｍ，２Ｈ）、１．３２−２．８０（ｍ，１１Ｈ）、０．９５（ｔ，３Ｈ） Reference production example 132
1.0 g of the organic sulfur compound (222) was dissolved in 30 ml of methanol. To this, 1.0 ml of ammonia (7M methanol solution) was added at room temperature, and the mixture was stirred at the same temperature for 4 days. The reaction mixture was concentrated under reduced pressure, and the resulting residue was subjected to silica gel chromatography to give 2-chloro-5- (trifluoromethyl) -2- (3,3,3-trifluoropropylsulfonyl) octanamide (hereinafter referred to as “chloromethane”). This is referred to as the organic sulfur compound (223).) 0.60 g was obtained.
This organic sulfur compound (223)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 6.87 (bs, 1H), 5.95 (bs, 1H), 3.34-3.78 (m, 2H), 1.32- 2.80 (m, 11H), 0.95 (t, 3H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）３．８９（ｓ，１．５Ｈ）、３．８８（ｓ，１．５Ｈ）、３．８４−３．９５（ｍ，１Ｈ）、３．３０−３．６３（ｍ，６Ｈ）、１．６３−２．８２（ｍ，６Ｈ） Reference Production Example 133
1.0 g of p-toluenesulfonic acid 4,4,4-trifluoro-3-methoxy-butyl and 0.8 g of methyl (3,3,3-trifluoropropylsulfonyl) acetate were dissolved in 50 ml of dimethyl sulfoxide. To this, 0.4 g of potassium carbonate was added at room temperature, and the mixture was stirred at room temperature for 4 days. The temperature was further raised to 60 ° C., stirred at the same temperature for 20 hours, and then allowed to cool to near room temperature. 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, and methyl 6,6,6-trifluoro-5-methoxy-2- (3,3,3-trifluoropropylsulfonyl) hexanoate (hereinafter referred to as the present organic sulfur compound ( 224).) 0.62 g was obtained.
This organic sulfur compound (224)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 3.89 (s, 1.5H), 3.88 (s, 1.5H), 3.84-3.95 (m, 1H), 3.30-3.63 (m, 6H), 1.63-2.82 (m, 6H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）３．９５（ｓ，３Ｈ）、３．４９−３．８９（ｍ，３Ｈ）、３．５６（ｓ，３Ｈ）、１．７８−２．９１（ｍ，６Ｈ） Reference Production Example 134
0.8 g of this organic sulfur compound (224) was dissolved in 30 ml of tetrahydrofuran. To this, 0.1 g of sodium hydride (60% oily) was added at room temperature, and the mixture was stirred at the same temperature for 0.5 hour. After adding 0.3 g of N-chlorosuccinimide at room temperature and stirring for 1 hour, 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, and methyl 2-chloro-6,6,6-trifluoro-5-methoxy-2- (3,3,3-trifluoropropylsulfonyl) hexanoate (hereinafter referred to as the present product). 0.50 g of organic sulfur compound (225) is obtained.
This organic sulfur compound (225)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 3.95 (s, 3H), 3.49-3.89 (m, 3H), 3.56 (s, 3H), 1.78- 2.91 (m, 6H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）６．８８（ｂｓ，１Ｈ）、５．９８（ｂｓ，１Ｈ）、３．３７−３．８０（ｍ，３Ｈ）、３．５８（ｓ，３Ｈ）、１．６６−２．８６（ｍ，６Ｈ） Reference Production Example 135
0.4 g of this organic sulfur compound (225) was dissolved in 20 ml of methanol. To this, 0.4 ml of ammonia (7M methanol solution) was added at room temperature, and the mixture was stirred at the same temperature for 2 days. The reaction mixture was concentrated under reduced pressure, and the resulting residue was subjected to silica gel chromatography to give 2-chloro-6,6,6-trifluoro-5-methoxy-2- (3,3,3-trifluoropropylsulfonyl). ) Hexamide (hereinafter referred to as the present organic sulfur compound (226)) 0.28 g was obtained.
This organic sulfur compound (226)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 6.88 (bs, 1H), 5.98 (bs, 1H), 3.37-3.80 (m, 3H), 3.58 ( s, 3H), 1.66-2.86 (m, 6H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）３．８９（ｓ，３Ｈ）、３．８１−３．９３（ｍ，１Ｈ）、３．３０−３．５２（ｍ，２Ｈ）、２．１３−３．００（ｍ，５Ｈ）、２．２３（ｓ，１．５Ｈ）、２．２２（ｓ，１．５Ｈ）、１．５８−２．０８（ｍ，２Ｈ） Reference Production Example 136
Methanesulfonic acid 4,4,4-trifluoro-3-methylthio-butyl 5.0 g and methyl (3,3,3-trifluoropropylsulfonyl) acetate 4.6 g were dissolved in dimethyl sulfoxide 50 ml. To this, 0.8 g of sodium hydride (60% oily) was added at room temperature. The reaction mixture was heated to 60 ° C., stirred at the same temperature for 5 days, and then allowed to cool to near room temperature. 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, and methyl 6,6,6-trifluoro-5-methylthio-2- (3,3,3-trifluoropropylsulfonyl) hexanoate (hereinafter referred to as the present organic sulfur compound ( 227).) 2.00 g was obtained.
This organic sulfur compound (227)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 3.89 (s, 3H), 3.81-3.93 (m, 1H), 3.30-3.52 (m, 2H), 2.13-3.00 (m, 5H), 2.23 (s, 1.5H), 2.22 (s, 1.5H), 1.58-2.08 (m, 2H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）３．９７（ｓ，１．５Ｈ）、３．９６（ｓ，１．５Ｈ）、３．５０−３．８５（ｍ，２Ｈ）、１．７０−３．１０（ｍ，７Ｈ）、２．２３（ｓ，１．５Ｈ）、２．２２（ｓ，１．５Ｈ） Reference Production Example 137
1.0 g of this organic sulfur compound (227) was dissolved in 30 ml of tetrahydrofuran. To this, 0.1 g of sodium hydride (60% oily) was added at room temperature, and the mixture was stirred at the same temperature for 0.5 hour. 0.3 g of N-chlorosuccinimide was added to the mixture at room temperature and stirred for 2 hours, 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, and methyl 2-chloro-6,6,6-trifluoro-5-methylthio-2- (3,3,3-trifluoropropylsulfonyl) hexanoate (hereinafter referred to as the present product). 0.80 g of organic sulfur compound (228) is obtained.
This organic sulfur compound (228)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 3.97 (s, 1.5H), 3.96 (s, 1.5H), 3.50-3.85 (m, 2H), 1.70-3.10 (m, 7H), 2.23 (s, 1.5H), 2.22 (s, 1.5H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）６．８７（ｂｓ，１Ｈ）、５．８７（ｂｓ，１Ｈ）、３．３８−３．７８（ｍ，２Ｈ）、２．２２（ｓ，３Ｈ）、１．５０−３．０８（ｍ，７Ｈ） Reference Production Example 138
0.7 g of the present organic sulfur compound (228) was dissolved in 20 ml of methanol. To this, 0.7 ml of ammonia (7M methanol solution) was added at room temperature, and the mixture was stirred at the same temperature for 16 hours. The reaction mixture was concentrated under reduced pressure, and the resulting residue was subjected to silica gel chromatography to give 2-chloro-6,6,6-trifluoro-5-methylthio-2- (3,3,3-trifluoropropylsulfonyl). ) Hexamide (hereinafter referred to as the present organic sulfur compound (229)) 0.42 g was obtained.
This organic sulfur compound (229)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 6.87 (bs, 1H), 5.87 (bs, 1H), 3.38-3.78 (m, 2H), 2.22 ( s, 3H), 1.50-3.08 (m, 7H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）３．９９−４．１３（ｍ，１Ｈ）、３．４０−３．６４（ｍ，２Ｈ）、１．６６−３．６４（ｍ，１０Ｈ） Reference Production Example 139
1.0 g of 4,4,4-trifluoro-3-methylthio-butyl methanesulfonate and 0.8 g of (3,3,3-trifluoropropylsulfonyl) acetonitrile were dissolved in 30 ml of dimethyl sulfoxide. To this was added 0.5 g of potassium carbonate at room temperature, and the temperature was raised to 60 ° C., followed by stirring at the same temperature for 2 days. The reaction mixture was allowed to cool to near room temperature, 10% hydrochloric acid was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 6,6,6-trifluoro-5-methylthio-2- (3,3,3-trifluoropropylsulfonyl) hexanenitrile (hereinafter referred to as the present organic sulfur compound (230 ) 0.49 g was obtained.
This organic sulfur compound (230)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 3.99-4.13 (m, 1H), 3.40-3.64 (m, 2H), 1.66-3.64 (m , 10H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）６．９７（ｂｓ，１Ｈ）、６．５１（ｂｓ，１Ｈ）、３．３５−３．８０（ｍ，２Ｈ）、１．３５−２．８３（ｍ，７Ｈ）、１．１９（ｄ，３Ｈ） Reference production example 140
2.0 g of methanesulfonic acid 4,4,5,5,5-pentafluoro-3-methyl-pentyl and 1.7 g of methyl (3,3,3-trifluoropropylsulfonyl) acetate were dissolved in 50 ml of dimethyl sulfoxide. . To this, 1.0 g of potassium carbonate was added at room temperature, the temperature was raised to 60 ° C., the mixture was stirred at the same temperature for 7 days, and then allowed to cool to near room temperature. 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 0.5 g of methyl 6,6,7,7,7-pentafluoro-5-methyl-2- (3,3,3-trifluoropropylsulfonyl) heptanoate. Obtained. This was dissolved in 20 ml of tetrahydrofuran. To this, 0.1 g of sodium hydride (60% oily) was added at room temperature, and the mixture was stirred at the same temperature for 0.5 hour. After adding 0.2 g of N-chlorosuccinimide to the mixture at room temperature and stirring for 2 hours, 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was dissolved in 20 ml of methanol, 0.5 ml of ammonia (7M methanol solution) was added thereto at room temperature, and the mixture was stirred at the same temperature for 30 hours. The reaction mixture was concentrated under reduced pressure, and the resulting residue was subjected to silica gel chromatography to give 2-chloro-6,6,7,7,7-pentafluoro-5-methyl-2- (3,3,3- 0.22 g of trifluoropropylsulfonyl) heptanamide (hereinafter referred to as the present organic sulfur compound (231)) was obtained.
This organic sulfur compound (231)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 6.97 (bs, 1H), 6.51 (bs, 1H), 3.35-3.80 (m, 2H), 1.35 2.83 (m, 7H), 1.19 (d, 3H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）３．８７（ｓ，３Ｈ）、３．８２−３．８８（ｍ，１Ｈ）、３．２５−３．５０（ｍ，２Ｈ）、２．６０−２．７６（ｍ，２Ｈ）、２．０３−２．２８（ｍ，４Ｈ）、１．９６（ｔ，１Ｈ）、１．４５−１．６５（ｍ，４Ｈ） Reference Production Example 141
1.0 g of 6-chloro-1-hexyne and 2.0 g of methyl (3,3,3-trifluoropropylsulfonyl) acetate were dissolved in 50 ml of dimethyl sulfoxide. To this, 0.3 g of sodium hydride (60% oily) was added at room temperature, and the mixture was stirred at the same temperature for 12 hours, at 60 ° C. for 2 hours, and at 90 ° C. for 10 hours. The reaction mixture was allowed to cool to near room temperature, 10% hydrochloric acid was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 1.50 g of methyl 2- (3,3,3-trifluoropropylsulfonyl) -7-octynoate (hereinafter referred to as the present organic sulfur compound (301)). Obtained.
This organic sulfur compound (301)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 3.87 (s, 3H), 3.82-3.88 (m, 1H), 3.25-3.50 (m, 2H), 2.60-2.76 (m, 2H), 2.03-2.28 (m, 4H), 1.96 (t, 1H), 1.45-1.65 (m, 4H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）３．９６（ｓ，３Ｈ）、３．２５−３．４９（ｍ，２Ｈ）、２．６０−２．８０（ｍ，２Ｈ）、２．１９−２．５４（ｍ，４Ｈ）、１．９７（ｔ，１Ｈ）、１．４５−１．７６（ｍ，４Ｈ） Reference Production Example 142
0.6 g of this organic sulfur compound (301) was dissolved in 30 ml of tetrahydrofuran. To this, 0.1 g of sodium hydride (60% oily) was added at room temperature, and the mixture was stirred at the same temperature for 10 minutes. After adding 0.5 g of 1-fluoro-2,4,6-trimethylpyridinium trifluoromethanesulfonate to the mixture at room temperature and stirring for 16 hours, 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, and methyl 2-fluoro-2- (3,3,3-trifluoropropylsulfonyl) -7-octynoate (hereinafter referred to as the present organic sulfur compound (302)). 0.32 g was obtained.
This organic sulfur compound (302)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 3.96 (s, 3H), 3.25-3.49 (m, 2H), 2.60-2.80 (m, 2H), 2.19-2.54 (m, 4H), 1.97 (t, 1H), 1.45-1.76 (m, 4H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）６．５４（ｂｓ，１Ｈ）、６．００（ｂｓ，１Ｈ）、３．２７−３．５５（ｍ，２Ｈ）、２．６３−２．８０（ｍ，２Ｈ）、２．１９−２．５４（ｍ，４Ｈ）、１．９７（ｔ，１Ｈ）、１．５０−１．７６（ｍ，４Ｈ） Reference Production Example 143
This organic sulfur compound (302) 0.2g was dissolved in methanol 20ml. To this, 0.3 ml of ammonia (7M methanol solution) was added at room temperature and stirred at the same temperature for 10 hours. The reaction mixture was concentrated under reduced pressure, and the resulting residue was subjected to silica gel chromatography to give 2-fluoro-2- (3,3,3-trifluoropropylsulfonyl) -7-octinamide (hereinafter referred to as the present organic sulfur compound). (Described as (303).) 0.12 g was obtained.
This organic sulfur compound (303)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 6.54 (bs, 1H), 6.00 (bs, 1H), 3.27-3.55 (m, 2H), 2.63- 2.80 (m, 2H), 2.19-2.54 (m, 4H), 1.97 (t, 1H), 1.50-1.76 (m, 4H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）３．９４（ｓ，３Ｈ）、３．４７−３．８０（ｍ，２Ｈ）、２．５５−２．８０（ｍ，３Ｈ）、２．１９−２．３２（ｍ，３Ｈ）１．９７（ｔ，１Ｈ）、１．５５−１．８４（ｍ，４Ｈ） Reference Production Example 144
1.0 g of the organic sulfur compound (301) was dissolved in 30 ml of tetrahydrofuran. To this, 0.1 g of sodium hydride (60% oily) was added at room temperature, and the mixture was stirred at the same temperature for 10 minutes. After adding 0.4 g of N-chlorosuccinimide at room temperature and stirring for 6 hours, 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, and methyl 2-chloro-2- (3,3,3-trifluoropropylsulfonyl) -7-octynoate (hereinafter referred to as the present organic sulfur compound (304)). 0.89 g was obtained.
This organic sulfur compound (304)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 3.94 (s, 3H), 3.47-3.80 (m, 2H), 2.55-2.80 (m, 3H), 2.19-2.32 (m, 3H) 1.97 (t, 1H), 1.55-1.84 (m, 4H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）６．９２（ｂｓ，１Ｈ）、６．２２（ｂｓ，１Ｈ）、３．３７−３．８０（ｍ，２Ｈ）、２．５５−２．８１（ｍ，３Ｈ）、２．１３−２．３２（ｍ，３Ｈ）１．９８（ｔ，１Ｈ）、１．４５−１．８８（ｍ，４Ｈ） Reference Production Example 145
0.8 g of this organic sulfur compound (304) was dissolved in 30 ml of methanol. To this was added 1.0 ml of ammonia (7M methanol solution) at room temperature, and then the mixture was heated to 60 ° C. and stirred for 20 hours. The reaction mixture was allowed to cool to near room temperature and then concentrated under reduced pressure. The resulting residue was subjected to silica gel chromatography to give 2-chloro-2- (3,3,3-trifluoropropylsulfonyl) -7-octamide. (Hereinafter referred to as the present organic sulfur compound (305).) 0.51 g was obtained.
This organic sulfur compound (305)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 6.92 (bs, 1H), 6.22 (bs, 1H), 3.37-3.80 (m, 2H), 2.55- 2.81 (m, 3H), 2.13-2.32 (m, 3H) 1.98 (t, 1H), 1.45-1.88 (m, 4H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）３．８５（ｓ，３Ｈ）、３．２６−３．６１（ｍ，２Ｈ）、２．６０−２．７８（ｍ，２Ｈ）、１．９６（ｔ，１Ｈ）、１．８８−２．２９（ｍ，４Ｈ）、１．５６（ｓ，３Ｈ）、１．２５−１．６９（ｍ，４Ｈ） Reference Production Example 146
1.0 g of the organic sulfur compound (301) was dissolved in 30 ml of dimethyl sulfoxide. To this, 0.1 g of sodium hydride (60% oily) was added at room temperature, and the mixture was stirred at the same temperature for 10 minutes. After adding 0.5 g of methyl iodide to the mixture at room temperature and stirring for 1 day, 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, and methyl 2-methyl-2- (3,3,3-trifluoropropylsulfonyl) -7-octynoate (hereinafter referred to as the present organic sulfur compound (306)). 0.95 g was obtained.
This organic sulfur compound (306)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 3.85 (s, 3H), 3.26-3.61 (m, 2H), 2.60-2.78 (m, 2H), 1.96 (t, 1H), 1.88-2.29 (m, 4H), 1.56 (s, 3H), 1.25-1.69 (m, 4H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）６．５４（ｂｓ，１Ｈ）、５．６９（ｂｓ，１Ｈ）、３．１５−３．４５（ｍ，２Ｈ）、２．６１−２．７４（ｍ，２Ｈ）、１．９８（ｔ，１Ｈ）、１．８６−２．２９（ｍ，４Ｈ）、１．５８（ｓ，３Ｈ）、１．３５−１．６８（ｍ，４Ｈ） Reference Production Example 147
0.9 g of the organic sulfur compound (306) was dissolved in 30 ml of methanol. After adding 1.2 ml of ammonia (7M methanol solution) at room temperature, the temperature was raised to 60 ° C. and stirred for 20 hours. The reaction mixture was allowed to cool to near room temperature and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to give 2-methyl-2- (3,3,3-trifluoropropylsulfonyl) -7-octamide. (Hereinafter referred to as the present organic sulfur compound (307).) 0.69 g was obtained.
This organic sulfur compound (307)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 6.54 (bs, 1H), 5.69 (bs, 1H), 3.15-3.45 (m, 2H), 2.61- 2.74 (m, 2H), 1.98 (t, 1H), 1.86-2.29 (m, 4H), 1.58 (s, 3H), 1.35-1.68 (m, 4H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）４．０８−４．１７（ｍ，１Ｈ）、３．８８（ｓ，３Ｈ）、３．３０−３．５０（ｍ，２Ｈ）、２．２６−２．７８（ｍ，６Ｈ）、２．０７（ｔ，１Ｈ） Reference production example 148
2.0 g of 3-butynyl p-toluenesulfonate and 2.1 g of methyl (3,3,3-trifluoropropylsulfonyl) acetate were dissolved in 30 ml of dimethyl sulfoxide. To this was added 0.4 g of sodium hydride (60% oily) at room temperature, and the mixture was stirred at the same temperature for 4 days. Then, 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 0.90 g of methyl 2- (3,3,3-trifluoropropylsulfonyl) -5-hexynoate (hereinafter referred to as the present organic sulfur compound (308)). Obtained.
This organic sulfur compound (308)

_{^{1 H-NMR (CDCl 3,}} TMS): δ (ppm) 4.08-4.17 (m, 1H), 3.88 (s, 3H), 3.30-3.50 (m, 2H), 2.26-2.78 (m, 6H), 2.07 (t, 1H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）３．９６（ｓ，３Ｈ）、３．２５−３．５０（ｍ，２Ｈ）、２．３５−２．８１（ｍ，６Ｈ）、２．０４（ｔ，１Ｈ） Reference Production Example 149
0.8 g of this organic sulfur compound (308) was dissolved in 30 ml of tetrahydrofuran. To this, 0.1 g of sodium hydride (60% oily) was added at room temperature, and the mixture was stirred at the same temperature for 10 minutes. 0.9 g of 1-fluoro-2,4,6-trimethylpyridinium trifluoromethanesulfonate was added to the mixture at room temperature and stirred for 12 hours, 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, and methyl 2-fluoro-2- (3,3,3-trifluoropropylsulfonyl) -5-hexynoate (hereinafter referred to as the present organic sulfur compound (309)). 0.62 g was obtained.
This organic sulfur compound (309)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 3.96 (s, 3H), 3.25-3.50 (m, 2H), 2.35-2.81 (m, 6H), 2.04 (t, 1H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）６．５２（ｂｓ，１Ｈ）、５．８４（ｂｓ，１Ｈ）、３．３０−３．６０（ｍ，２Ｈ）、２．３５−２．８３（ｍ，６Ｈ）、２．０４（ｔ，１Ｈ） Reference production example 150
0.5 g of the organic sulfur compound (309) was dissolved in 30 ml of methanol. To this, 0.7 ml of ammonia (7M methanol solution) was added at room temperature and stirred at the same temperature for 20 hours. The reaction mixture was concentrated under reduced pressure, and the resulting residue was subjected to silica gel chromatography to give 2-fluoro-2- (3,3,3-trifluoropropylsulfonyl) -5-hexinamide (hereinafter referred to as the present organic sulfur compound ( 310).) 0.23 g was obtained.
This organic sulfur compound (310)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 6.52 (bs, 1H), 5.84 (bs, 1H), 3.30-3.60 (m, 2H), 2.35- 2.83 (m, 6H), 2.04 (t, 1H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）３．８７（ｓ，３Ｈ）、３．８５−３．９３（ｍ，１Ｈ）、３．２６−３．５０（ｍ，２Ｈ）、２．６０−２．７７（ｍ，２Ｈ）、２．１５−２．３４（ｍ，４Ｈ）、２．０２（ｔ，１Ｈ）、１．５９−１．７１（ｍ，２Ｈ） Reference Production Example 151
2.0 g of 4-pentynyl p-toluenesulfonate and 2.0 g of methyl (3,3,3-trifluoropropylsulfonyl) acetate were dissolved in 30 ml of dimethyl sulfoxide. To this, 1.2 g of potassium carbonate was added at room temperature, followed by stirring at 60 ° C. for 4 hours and at 90 ° C. for 1 hour. The reaction mixture was allowed to cool to near room temperature, 10% hydrochloric acid was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 0.90 g of methyl 2- (3,3,3-trifluoropropylsulfonyl) -6-heptinate (hereinafter referred to as the present organic sulfur compound (311)). Obtained.
This organic sulfur compound (311)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 3.87 (s, 3H), 3.85-3.93 (m, 1H), 3.26-3.50 (m, 2H), 2.60-2.77 (m, 2H), 2.15-2.34 (m, 4H), 2.02 (t, 1H), 1.59-1.71 (m, 2H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）３．９７（ｓ，３Ｈ）、３．２５−３．５２（ｍ，２Ｈ）、２．２８−２．８２（ｍ，６Ｈ）、２．０２（ｔ，１Ｈ）、１．５１−１．８６（ｍ，２Ｈ） Reference Production Example 152
1.0 g of the organic sulfur compound (311) was dissolved in 30 ml of tetrahydrofuran. To this, 0.1 g of sodium hydride (60% oily) was added at room temperature, and the mixture was stirred at the same temperature for 10 minutes. 1.0 g of 1-fluoro-2,4,6-trimethylpyridinium trifluoromethanesulfonate was added to the mixture at room temperature and stirred for 10 hours, 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, and methyl 2-fluoro-2- (3,3,3-trifluoropropylsulfonyl) -6-heptinate (hereinafter referred to as the present organic sulfur compound (312)). 0.95 g was obtained.
This organic sulfur compound (312)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 3.97 (s, 3H), 3.25-3.52 (m, 2H), 2.28-2.82 (m, 6H), 2.02 (t, 1H), 1.51-1.86 (m, 2H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）６．５１（ｂｓ，１Ｈ）、５．８７（ｂｓ，１Ｈ）、３．２９−３．５８（ｍ，２Ｈ）、２．２９−２．８０（ｍ，６Ｈ）、２．０３（ｔ，１Ｈ）、１．６１−１．８８（ｍ，２Ｈ） Reference production example 153
0.5 g of this organic sulfur compound (312) was dissolved in 20 ml of methanol. To this, 0.7 ml of ammonia (7M methanol solution) was added at room temperature, and the mixture was stirred at the same temperature for 16 hours. The reaction mixture was concentrated under reduced pressure, and the resulting residue was subjected to silica gel chromatography to give 2-fluoro-2- (3,3,3-trifluoropropylsulfonyl) -6-heptinamide (hereinafter referred to as the present organic sulfur compound ( 313).) 0.22 g was obtained.
This organic sulfur compound (313)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 6.51 (bs, 1H), 5.87 (bs, 1H), 3.29-3.58 (m, 2H), 2.29- 2.80 (m, 6H), 2.03 (t, 1H), 1.61-1.88 (m, 2H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）３．８７（ｓ，３Ｈ）、３．８０−３．９０（ｍ，１Ｈ）、３．２４−３．５０（ｍ，２Ｈ）、２．５９−２．７６（ｍ，２Ｈ）、２．０８−２．２６（ｍ，４Ｈ）、１．９６（ｔ，１Ｈ）、１．３８−１．６０（ｍ，６Ｈ） Reference production example 154
3.0 g of 6-heptynyl p-toluenesulfonate and 2.6 g of methyl (3,3,3-trifluoropropylsulfonyl) acetate were dissolved in 50 ml of dimethyl sulfoxide. 1.6 g of potassium carbonate was added thereto at room temperature, the temperature was raised to 90 ° C., and the mixture was stirred at the same temperature for 6 hours. The reaction mixture was allowed to cool to near room temperature, 10% hydrochloric acid was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 0.80 g of methyl 2- (3,3,3-trifluoropropylsulfonyl) -8-noninate (hereinafter referred to as the present organic sulfur compound (314)). Obtained.
This organic sulfur compound (314)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 3.87 (s, 3H), 3.80-3.90 (m, 1H), 3.24-3.50 (m, 2H), 2.59-2.76 (m, 2H), 2.08-2.26 (m, 4H), 1.96 (t, 1H), 1.38-1.60 (m, 6H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）３．９６（ｓ，３Ｈ）、３．２１−３．５０（ｍ，２Ｈ）、２．５８−２．７９（ｍ，２Ｈ）、２．１５−２．５３（ｍ，４Ｈ）、１．９６（ｔ，１Ｈ）、１．３０−１．７０（ｍ，６Ｈ） Reference production example 155
0.6 g of the present organic sulfur compound (314) was dissolved in 50 ml of tetrahydrofuran. To this, 0.1 g of sodium hydride (60% oily) was added at room temperature, and the mixture was stirred at the same temperature for 10 minutes. After adding 0.5 g of 1-fluoro-2,4,6-trimethylpyridinium trifluoromethanesulfonate to the mixture at room temperature and stirring for 2 hours, 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, and methyl 2-fluoro-2- (3,3,3-trifluoropropylsulfonyl) -8-noninate (hereinafter referred to as the present organic sulfur compound (315)). 0.45 g was obtained.
This organic sulfur compound (315)

_{^{1 H-NMR (CDCl 3,}} TMS): δ (ppm) 3.96 (s, 3H), 3.21-3.50 (m, 2H), 2.58-2.79 (m, 2H), 2.15-2.53 (m, 4H), 1.96 (t, 1H), 1.30-1.70 (m, 6H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）６．４９（ｂｓ，１Ｈ）、５．８５（ｂｓ，１Ｈ）、３．２５−３．５５（ｍ，２Ｈ）、２．６２−２．７９（ｍ，２Ｈ）、２．１５−２．５１（ｍ，４Ｈ）、１．９６（ｔ，１Ｈ）、１．３８−１．６５（ｍ，６Ｈ） Reference Production Example 156
0.4 g of this organic sulfur compound (315) was dissolved in 30 ml of methanol. To this, 0.5 ml of ammonia (7M methanol solution) was added at room temperature, and the mixture was stirred at the same temperature for 10 hours. The reaction mixture was concentrated under reduced pressure, and the resulting residue was subjected to silica gel chromatography to give 2-fluoro-2- (3,3,3-trifluoropropylsulfonyl) -8-noninamide (hereinafter referred to as the present organic sulfur compound ( 316).) 0.20 g was obtained.
This organic sulfur compound (316)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 6.49 (bs, 1H), 5.85 (bs, 1H), 3.25-3.55 (m, 2H), 2.62- 2.79 (m, 2H), 2.15-2.51 (m, 4H), 1.96 (t, 1H), 1.38-1.65 (m, 6H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）６．２６−６．４０（ｍ，１Ｈ）、５．７６−５．８９（ｍ，１Ｈ）、３．９１−３．９８（ｍ，１Ｈ）、３．８８（ｓ，３Ｈ）、３．３５−３．５２（ｍ，２Ｈ）、２．９０−３．０４（ｍ，２Ｈ）、２．６１−２．７６（ｍ，２Ｈ） Reference Production Example 157
2.4 g of p-toluenesulfonic acid 4,4,4-trifluoro-2-butenyl and 2.0 g of methyl (3,3,3-trifluoropropylsulfonyl) acetate were dissolved in 50 ml of dimethyl sulfoxide. To this, 1.2 g of potassium carbonate was added at room temperature, followed by stirring at the same temperature for 16 hours. 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain methyl 6,6,6-trifluoro-2- (3,3,3-trifluoropropylsulfonyl) -4-hexenoate (hereinafter referred to as the present organic sulfur compound (317). ) 1.40 g was obtained.
This organic sulfur compound (317)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 6.26-6.40 (m, 1H), 5.76-5.89 (m, 1H), 3.91-3.98 (m , 1H), 3.88 (s, 3H), 3.35-3.52 (m, 2H), 2.90-3.04 (m, 2H), 2.61-2.76 (m, 2H) )

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）６．３５−６．４５（ｍ，１Ｈ）、５．８５−５．９６（ｍ，１Ｈ）、３．９６（ｓ，３Ｈ）、３．５５−３．８８（ｍ，２Ｈ）、３．０８−３．４８（ｍ，２Ｈ）、２．６５−２．８１（ｍ，２Ｈ） Reference Production Example 158
1.3 g of this organic sulfur compound (317) was dissolved in 30 ml of tetrahydrofuran. To this, 0.2 g of sodium hydride (60% oily) was added at room temperature, and the mixture was stirred at the same temperature for 10 minutes. 0.5 g of N-chlorosuccinimide was added to the mixture at room temperature and stirred for 1 hour, 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, and methyl 2-chloro-6,6,6-trifluoro-2- (3,3,3-trifluoropropylsulfonyl) -4-hexenoate (hereinafter referred to as the present organic compound). 1.10 g of the sulfur compound (318) was obtained.
This organic sulfur compound (318)

_{^{1 H-NMR (CDCl 3,}} TMS): δ (ppm) 6.35-6.45 (m, 1H), 5.85-5.96 (m, 1H), 3.96 (s, 3H), 3.55-3.88 (m, 2H), 3.08-3.48 (m, 2H), 2.65-2.81 (m, 2H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）６．３５−６．４８（ｍ，１Ｈ）、５．９２−６．０５（ｍ，１Ｈ）、４．０２（ｄｄ，１Ｈ）、３．４４−３．６２（ｍ，２Ｈ）、２．９０−３．１３（ｍ，２Ｈ）、２．７２−２．８８（ｍ，２Ｈ） Reference Production Example 159
1.7 g of p-toluenesulfonic acid 4,4,4-trifluoro-2-butenyl and 1.2 g of (3,3,3-trifluoropropylsulfonyl) acetonitrile were dissolved in 30 ml of tetrahydrofuran. To this, 0.2 g of sodium hydride (60% oily) was added at room temperature, and the mixture was stirred at the same temperature for 1 day. 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 6,6,6-trifluoro-2- (3,3,3-trifluoropropylsulfonyl) -4-hexenenitrile (hereinafter referred to as the present organic sulfur compound (319)). 0.95 g was obtained.
This organic sulfur compound (319)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 6.35-6.48 (m, 1H), 5.92-6.05 (m, 1H), 4.02 (dd, 1H), 3.44-3.62 (m, 2H), 2.90-3.13 (m, 2H), 2.72-2.88 (m, 2H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）３．８７（ｓ，３Ｈ）、３．８２−３．８８（ｍ，１Ｈ）、３．２５−３．５０（ｍ，２Ｈ）、２．６０−２．７６（ｍ，２Ｈ）、２．０３−２．２８（ｍ，４Ｈ）、１．９６（ｔ，１Ｈ）、１．４５−１．６５（ｍ，４Ｈ） Reference production example 160
2.0 g of 6-bromo-1-hexene and 2.9 g of methyl (3,3,3-trifluoropropylsulfonyl) acetate were dissolved in 50 ml of dimethyl sulfoxide. To this, 0.5 g of sodium hydride (60% oily) was added at room temperature, and then the temperature was raised to 60 ° C. and stirred for 4 hours. The reaction mixture was allowed to cool to near room temperature, 10% hydrochloric acid was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 3.10 g of methyl 2- (3,3,3-trifluoropropylsulfonyl) -7-octenoate (hereinafter referred to as the present organic sulfur compound (320)). Obtained.
This organic sulfur compound (320)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 3.87 (s, 3H), 3.82-3.88 (m, 1H), 3.25-3.50 (m, 2H), 2.60-2.76 (m, 2H), 2.03-2.28 (m, 4H), 1.96 (t, 1H), 1.45-1.65 (m, 4H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）３．９６（ｓ，３Ｈ）、３．２５−３．４９（ｍ，２Ｈ）、２．６０−２．８０（ｍ，２Ｈ）、２．１９−２．５４（ｍ，４Ｈ）、１．９７（ｔ，１Ｈ）、１．４５−１．７６（ｍ，４Ｈ） Reference Production Example 161
The organic sulfur compound (320) (2.0 g) was dissolved in tetrahydrofuran (30 ml). To this, 0.3 g of sodium hydride (60% oily) was added at room temperature, and the mixture was stirred at the same temperature for 10 minutes. 1.8 g of 1-fluoro-2,4,6-trimethylpyridinium trifluoromethanesulfonate was added to the mixture at room temperature and stirred for 2 hours, 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, and methyl 2-fluoro-2- (3,3,3-trifluoropropylsulfonyl) -7-octenoate (hereinafter referred to as the present organic sulfur compound (321)). 1.90 g was obtained.
This organic sulfur compound (321)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 3.96 (s, 3H), 3.25-3.49 (m, 2H), 2.60-2.80 (m, 2H), 2.19-2.54 (m, 4H), 1.97 (t, 1H), 1.45-1.76 (m, 4H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）６．５４（ｂｓ，１Ｈ）、６．００（ｂｓ，１Ｈ）、３．２７−３．５５（ｍ，２Ｈ）、２．６３−２．８０（ｍ，２Ｈ）、２．１９−２．５４（ｍ，４Ｈ）、１．９７（ｔ，１Ｈ）、１．５０−１．７６（ｍ，４Ｈ） Reference Production Example 162
1.2 g of the organic sulfur compound (321) was dissolved in 50 ml of methanol. To this, 1.5 ml of ammonia (7M methanol solution) was added at room temperature, and the mixture was stirred at the same temperature for 3 days. The reaction mixture was concentrated under reduced pressure, and the resulting residue was subjected to silica gel chromatography to give 2-fluoro-2- (3,3,3-trifluoropropylsulfonyl) -7-octenamide (hereinafter referred to as the present organic sulfur compound). (Described as (322).) 0.75 g was obtained.
This organic sulfur compound (322)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 6.54 (bs, 1H), 6.00 (bs, 1H), 3.27-3.55 (m, 2H), 2.63- 2.80 (m, 2H), 2.19-2.54 (m, 4H), 1.97 (t, 1H), 1.50-1.76 (m, 4H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）３．８７−３．９５（ｍ，１Ｈ）、３．３８−３．５８（ｍ，２Ｈ）、２．７０−２．８５（ｍ，２Ｈ）、２．０８−２．３１（ｍ，４Ｈ）、２．００（ｔ，１Ｈ）、１．６０−１．９２（ｍ，４Ｈ） Reference Production Example 163
1.0 g of 6-chloro-1-hexyne and 1.7 g of (3,3,3-trifluoropropylsulfonyl) acetonitrile were dissolved in 20 ml of dimethyl sulfoxide. To this, 1.2 g of potassium carbonate was added at room temperature, followed by stirring at 60 ° C. for 4 hours and at 90 ° C. for 2 hours. The reaction mixture was allowed to cool to near room temperature, 10% hydrochloric acid was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, 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 2- (3,3,3-trifluoropropylsulfonyl) -7-octynenitrile (hereinafter referred to as the present organic sulfur compound (323)). It was.
This organic sulfur compound (323)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 3.87-3.95 (m, 1H), 3.38-3.58 (m, 2H), 2.70-2.85 (m , 2H), 2.08-2.31 (m, 4H), 2.00 (t, 1H), 1.60-1.92 (m, 4H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）３．９２（ｄｄ，１Ｈ）、３．４２−３．５８（ｍ，２Ｈ）、２．７０−２．８７（ｍ，２Ｈ）、１．４４−２．２９（ｍ，１０Ｈ）、１．９８（ｔ，１Ｈ） Reference Production Example 164
1.0 g of 6-heptynyl p-toluenesulfonate and 0.8 g of (3,3,3-trifluoropropylsulfonyl) acetonitrile were dissolved in 20 ml of dimethyl sulfoxide. To this was added 0.5 g of potassium carbonate at room temperature, and the mixture was stirred at room temperature for 1 hour and at 60 ° C. for 2 days. The reaction mixture was allowed to cool to near room temperature, 10% hydrochloric acid was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 0.23 g of 2- (3,3,3-trifluoropropylsulfonyl) -8-noninenitrile (hereinafter referred to as the present organic sulfur compound (324)). .
This organic sulfur compound (324)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 3.92 (dd, 1H), 3.42-3.58 (m, 2H), 2.70-2.87 (m, 2H), 1.44-2.29 (m, 10H), 1.98 (t, 1H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）３．９１（ｄｄ，１Ｈ）、３．３８−３．５７（ｍ，２Ｈ）、１．３５−２．８７（ｍ，１４Ｈ）、１．９７（ｔ，１Ｈ） Reference Production Example 165
1.0 g of 7-octynyl p-toluenesulfonate and 0.7 g of (3,3,3-trifluoropropylsulfonyl) acetonitrile were dissolved in 30 ml of dimethyl sulfoxide. To this, 0.5 g of potassium carbonate was added at room temperature, and the mixture was stirred at room temperature for 2 hours, at 60 ° C. for 2 hours, and at 90 ° C. for 6 hours. The reaction mixture was allowed to cool to near room temperature, 10% hydrochloric acid was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 0.28 g of 2- (3,3,3-trifluoropropylsulfonyl) -9-decynenitrile (hereinafter referred to as the present organic sulfur compound (325)). It was.
This organic sulfur compound (325)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 3.91 (dd, 1H), 3.38-3.57 (m, 2H), 1.35-2.87 (m, 14H), 1.97 (t, 1H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）３．６０−３．８１（ｍ，２Ｈ）、２．７４−２．９２（ｍ，２Ｈ）、１．６０−２．６０（ｍ，８Ｈ）、１．９９（ｔ，１Ｈ） Reference Production Example 166
This organic sulfur compound (323) 0.5g was dissolved in tetrahydrofuran 20ml. To this, 0.1 g of sodium hydride (60% oily) was added at room temperature, and the mixture was stirred at the same temperature for 0.5 hour. The mixture was added with 0.2 g of N-chlorosuccinimide at room temperature and stirred for 1 hour, 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, and 2-chloro-2- (3,3,3-trifluoropropylsulfonyl) -7-octynenitrile (hereinafter referred to as the present organic sulfur compound (326)) 0 .38 g was obtained.
This organic sulfur compound (326)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 3.60-3.81 (m, 2H), 2.74-2.92 (m, 2H), 1.60-2.60 (m , 8H), 1.99 (t, 1H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）３．８５−３．９４（ｍ，１Ｈ）、３．３８−３．５８（ｍ，２Ｈ）、２．７０−２．８５（ｍ，２Ｈ）、１．３８−２．３５（ｍ，７Ｈ）、２．０１（ｔ，１Ｈ）、１．０６（ｄｄ，３Ｈ） Reference Production Example 167
1.0 g of 3-methyl-5-hexynyl methanesulfonate and 1.1 g of (3,3,3-trifluoropropylsulfonyl) acetonitrile were dissolved in 30 ml of dimethyl sulfoxide. To this, 0.2 g of sodium hydride (60% oily) was added at room temperature, and the mixture was stirred at 60 ° C. for 3 days and at 90 ° C. for 2 hours. The reaction mixture was allowed to cool to near room temperature, 10% hydrochloric acid was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, and 5-methyl-2- (3,3,3-trifluoropropylsulfonyl) -7-octynenitrile (hereinafter referred to as the present organic sulfur compound (327)) 0. .69 g was obtained.
This organic sulfur compound (327)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 3.85-3.94 (m, 1H), 3.38-3.58 (m, 2H), 2.70-2.85 (m , 2H), 1.38-2.35 (m, 7H), 2.01 (t, 1H), 1.06 (dd, 3H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）３．８７−３．９５（ｍ，１Ｈ）、３．３５−３．５６（ｍ，２Ｈ）、１．４５−２．８５（ｍ，９Ｈ）、２．０９（ｔ，１Ｈ）、１．２４（ｄｄ，３Ｈ） Reference Production Example 168
1.0 g of 4-methyl-5-hexynyl methanesulfonate and 1.1 g of (3,3,3-trifluoropropylsulfonyl) acetonitrile were dissolved in 30 ml of dimethyl sulfoxide. To this, 0.7 g of potassium carbonate was added at room temperature, and the mixture was stirred at 60 ° C. for 2 days. The reaction mixture was allowed to cool to near room temperature, 10% hydrochloric acid was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, and 6-methyl-2- (3,3,3-trifluoropropylsulfonyl) -7-octynenitrile (hereinafter referred to as the present organic sulfur compound (328)) 0. .45 g was obtained.
This organic sulfur compound (328)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 3.87-3.95 (m, 1H), 3.35-3.56 (m, 2H), 1.45-2.85 (m , 9H), 2.09 (t, 1H), 1.24 (dd, 3H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）３．８５−３．９７（ｍ，１Ｈ）、３．３５−３．５８（ｍ，２Ｈ）、２．６３−２．８５（ｍ，２Ｈ）、１．３０−２．４１（ｍ，９Ｈ）、２．００（ｔ，１Ｈ）、０．９３（ｄｔ，３Ｈ） Reference Production Example 169
0.7 g of 3-ethyl-5-hexynyl methanesulfonate and 0.7 g of (3,3,3-trifluoropropylsulfonyl) acetonitrile were dissolved in 20 ml of dimethyl sulfoxide. To this, 0.5 g of potassium carbonate was added at room temperature, and the mixture was stirred at 60 ° C. for 20 hours. The reaction mixture was allowed to cool to near room temperature, 10% hydrochloric acid was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, and 5-ethyl-2- (3,3,3-trifluoropropylsulfonyl) -7-octynenitrile (hereinafter referred to as the present organic sulfur compound (329)) 0. .40 g was obtained.
This organic sulfur compound (329)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 3.85-3.97 (m, 1H), 3.35-3.58 (m, 2H), 2.62-2.85 (m , 2H), 1.30-2.41 (m, 9H), 2.00 (t, 1H), 0.93 (dt, 3H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）３．８７（ｓ，３Ｈ）、３．７６−３．８８（ｍ，１Ｈ）、３．２３−３．５２（ｍ，２Ｈ）、２．５８−２．７８（ｍ，２Ｈ）、１．３０−２．３０（ｍ，９Ｈ）、１．９６（ｔ，１Ｈ）、０．８９（ｄｔ，３Ｈ） Reference production example 170
3.0 g of 3-ethyl-5-hexynyl methanesulfonate and 3.4 g of (3,3,3-trifluoropropylsulfonyl) acetate were dissolved in 30 ml of dimethyl sulfoxide. To this, 2.0 g of potassium carbonate was added at room temperature. The reaction mixture was heated to 60 ° C., stirred at the same temperature for 1 day, and then allowed to cool to near room temperature. 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, and methyl 5-ethyl-2- (3,3,3-trifluoropropylsulfonyl) -7-octynoate (hereinafter referred to as the present organic sulfur compound (330)). 1.30 g was obtained.
This organic sulfur compound (330)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 3.87 (s, 3H), 3.76-3.88 (m, 1H), 3.23-3.52 (m, 2H), 2.58-2.78 (m, 2H), 1.30-2.30 (m, 9H), 1.96 (t, 1H), 0.89 (dt, 3H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）３．９３（ｓ，３Ｈ）、３．４２−３．８２（ｍ，２Ｈ）、１．３２−２．８４（ｍ，１１Ｈ）、１．９５（ｔ，１Ｈ）、０．９０（ｄｔ，３Ｈ） Reference Production Example 171
1.0 g of the organic sulfur compound (330) was dissolved in 50 ml of tetrahydrofuran. To this was added 0.1 g of sodium hydride (60% oily) under ice cooling, and the mixture was stirred at the same temperature for 0.5 hour. After adding 0.4 g of N-chlorosuccinimide to the mixture and stirring for 2 hours, 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, and methyl 2-chloro-5-ethyl-2- (3,3,3-trifluoropropylsulfonyl) -7-octynoate (hereinafter referred to as the present organic sulfur compound (331)). 0.75 g was obtained.
This organic sulfur compound (331)

_{^{1 H-NMR (CDCl 3,}} TMS): δ (ppm) 3.93 (s, 3H), 3.42-3.82 (m, 2H), 1.32-2.84 (m, 11H), 1.95 (t, 1H), 0.90 (dt, 3H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）６．８６（ｂｓ，１Ｈ）、５．９５（ｂｓ，１Ｈ）、３．３３−３．８２（ｍ，２Ｈ）、１．３０−２．８０（ｍ，１１Ｈ）、１．９７（ｔ，１Ｈ）、０．９０（ｄｔ，３Ｈ） Reference Production Example 172
0.7 g of the present organic sulfur compound (331) was dissolved in 30 ml of methanol. To this, 0.7 ml of ammonia (7M methanol solution) was added at room temperature, and the mixture was stirred at the same temperature for 2 days. The reaction mixture was concentrated under reduced pressure, and the resulting residue was subjected to silica gel chromatography to give 2-chloro-5-ethyl-2- (3,3,3-trifluoropropylsulfonyl) -7-octyneamide (hereinafter referred to as “the residue”). This is described as the organic sulfur compound (332).) 0.40 g was obtained.
This organic sulfur compound (332)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 6.86 (bs, 1H), 5.95 (bs, 1H), 3.33-3.82 (m, 2H), 1.30- 2.80 (m, 11H), 1.97 (t, 1H), 0.90 (dt, 3H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）３．８９（ｄｄ，１Ｈ）、３．３９−３．５８（ｍ，２Ｈ）、２．６６−２．８６（ｍ，２Ｈ）、１．４８−２．２５（ｍ，４Ｈ）、２．１４（ｓ，１Ｈ）、２．１３（ｓ，１Ｈ）、２．０４（ｔ，１Ｈ）、１．０４０（ｓ，３Ｈ）、１．０３６（ｓ，３Ｈ） Reference Production Example 173
1.0 g of 3,3-dimethyl-5-hexynyl methanesulfonate and 1.0 g of (3,3,3-trifluoropropylsulfonyl) acetonitrile were dissolved in 30 ml of dimethyl sulfoxide. To this, 0.2 g of sodium hydride (60% oily) was added at room temperature, and the mixture was stirred at 60 ° C. for 2 days. The reaction mixture was allowed to cool to near room temperature, 10% hydrochloric acid was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, and described as 5,5-dimethyl-2- (3,3,3-trifluoropropylsulfonyl) -7-octonitrile (hereinafter referred to as the present organic sulfur compound (333)). ) 0.38 g was obtained.
This organic sulfur compound (333)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 3.89 (dd, 1H), 3.39-3.58 (m, 2H), 2.66-2.86 (m, 2H), 1.48-2.25 (m, 4H), 2.14 (s, 1H), 2.13 (s, 1H), 2.04 (t, 1H), 1.040 (s, 3H), 1 .036 (s, 3H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）６．３７−６．４８（ｍ，１Ｈ）、５．９０−６．１３（ｍ，１Ｈ）、３．４０−３．５７（ｍ，２Ｈ）、２．７０−３．１１（ｍ，４Ｈ）、１．７８（ｓ，３Ｈ） Reference Production Example 174
1.5 g of p-toluenesulfonic acid 4,4,4-trifluoro-2-butenyl and 1.2 g of 2- (3,3,3-trifluoropropylsulfonyl) propionitrile were dissolved in 30 ml of tetrahydrofuran. To this, 0.2 g of sodium hydride (60% oily) was added at room temperature, and the mixture was stirred at the same temperature for 2 days. 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 6,6,6-trifluoro-2-methyl-2- (3,3,3-trifluoropropylsulfonyl) -4-hexenenitrile (hereinafter referred to as the present organic sulfur). 0.80 g of compound (334) was obtained.
This organic sulfur compound (334)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 6.37-6.48 (m, 1H), 5.90-6.13 (m, 1H), 3.40-3.57 (m , 2H), 2.70-3.11 (m, 4H), 1.78 (s, 3H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）６．１０−６．１８（ｍ，１Ｈ）、３．９５−４．０２（ｍ，１Ｈ）、３．４０−３．６０（ｍ，２Ｈ）、２．７０−３．０８（ｍ，４Ｈ）、１．９２（ｓ，３Ｈ） Reference Production Example 175
(Process 1)
4.5 g of ethyl 4,4,4-trifluoro-3-methyl-2-butenoate was dissolved in 50 ml of tetrahydrofuran. Under ice cooling, 48 ml of diisobutylaluminum hydride (1.02 M hexane solution) was added dropwise thereto. After stirring at the same temperature for 2 hours, dilute sulfuric acid was added to the reaction mixture, and the mixture was extracted with t-butyl methyl ether. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure to obtain a crude product of 4,4,4-trifluoro-3-methyl-2-buten-1-ol.
The above crude product and 4.7 g of p-toluenesulfonyl chloride were dissolved in 50 ml of tetrahydrofuran, and 3 ml of triethylamine was added dropwise at room temperature. After stirring at the same temperature for 2 days, 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with 10% hydrochloric acid and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give p-toluenesulfonic acid 4,4,4-trifluoro-3-methyl-2- A crude product of butenyl was obtained.
(Process 2)
Dissolve 1.0 g of a crude product of 4,4,4-trifluoro-3-methyl-2-butenyl p-toluenesulfonate and 0.7 g of (3,3,3-trifluoropropylsulfonyl) acetonitrile in 20 ml of tetrahydrofuran. I let you. To this, 0.1 g of sodium hydride (60% oily) was added at room temperature, and the mixture was stirred at the same temperature for 2 days. 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 6,6,6-trifluoro-5-methyl-2- (3,3,3-trifluoropropylsulfonyl) -4-hexenenitrile (hereinafter referred to as the present organic sulfur). 0.17 g was obtained.
This organic sulfur compound (335)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 6.10-6.18 (m, 1H), 3.95-4.02 (m, 1H), 3.40-3.60 (m , 2H), 2.70-3.08 (m, 4H), 1.92 (s, 3H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）５．９６（ｔ，０．４Ｈ）、５．６５（ｔ，０．６Ｈ）、３．８０−３．９５（ｍ，１Ｈ）、３．８７（ｓ，３Ｈ）、３．３０−３．５１（ｍ，２Ｈ）、２．９２−３．１５（ｍ，２Ｈ）、２．５９−２．７８（ｍ，２Ｈ）、２．１５−２．３５（ｍ，２Ｈ）、１．０８（ｄｔ，３Ｈ） Reference Production Example 176
3.0 g of p-toluenesulfonic acid 3-trifluoromethyl-2-pentenyl and 2.3 g of methyl (3,3,3-trifluoropropylsulfonyl) acetate were dissolved in 50 ml of N, N-dimethylformamide. To this, 0.4 g of sodium hydride (60% oily) was added at room temperature, and the mixture was stirred at the same temperature for 10 hours. The reaction mixture was further stirred at 60 ° C. for 6 hours and 90 ° C. for 1 hour, and then allowed to cool to near room temperature. 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, and a mixture of (E) and (Z) of methyl 5-trifluoromethyl-2- (3,3,3-trifluoropropylsulfonyl) -4-heptenoate (hereinafter, 1.86 g of the organic sulfur compound (336) is obtained.
This organic sulfur compound (336)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 5.96 (t, 0.4 H), 5.65 (t, 0.6 H), 3.80-3.95 (m, 1 H), 3.87 (s, 3H), 3.30-3.51 (m, 2H), 2.92-3.15 (m, 2H), 2.59-2.78 (m, 2H), 2. 15-2.35 (m, 2H), 1.08 (dt, 3H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）６．１１（ｔ，０．４Ｈ）、５．７５（ｔ，０．６Ｈ）、３．９７（ｓ，１．２Ｈ）、３．９６（ｓ，１．８Ｈ）、３．０７−３．８９（ｍ，４Ｈ）、２．６１−２．８０（ｍ，２Ｈ）、２．２０−２．３５（ｍ，２Ｈ）、１．１０（ｄｔ，３Ｈ） Reference Production Example 177
1.0 g of the organic sulfur compound (336) was dissolved in 50 ml of tetrahydrofuran. To this was added 0.1 g of sodium hydride (60% oily) under ice cooling, and the mixture was stirred at the same temperature for 0.5 hour. After adding 0.3 g of N-chlorosuccinimide to the mixture and stirring for 1 hour, 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain (E), (Z) of methyl 2-chloro-5-trifluoromethyl-2- (3,3,3-trifluoropropylsulfonyl) -4-heptenoate. 0.55 g of a mixture (hereinafter referred to as the present organic sulfur compound (337)) was obtained.
This organic sulfur compound (337)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 6.11 (t, 0.4 H), 5.75 (t, 0.6 H), 3.97 (s, 1.2 H), 3. 96 (s, 1.8H), 3.07-3.89 (m, 4H), 2.61-2.80 (m, 2H), 2.20-2.35 (m, 2H), 1. 10 (dt, 3H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）４．２９（ｄｄ，１Ｈ）、４．１９（ｓ，２Ｈ）、３．７１−３．９２（ｍ，２Ｈ）、３．４３−３．５８（ｍ，２Ｈ）、２．７０−２．８５（ｍ，２Ｈ）、２．２１−２．６４（ｍ，２Ｈ）、２．５１（ｔ，１Ｈ） Reference Production Example 178
0.9 g of 2- (2-propynyloxy) ethyl methanesulfonate and 1.0 g of (3,3,3-trifluoropropylsulfonyl) acetonitrile were dissolved in 30 ml of dimethyl sulfoxide. To this, 0.7 g of potassium carbonate was added at room temperature, and the mixture was stirred at the same temperature for 6 hours and at 60 ° C. for 6 hours. The reaction mixture was allowed to cool to near room temperature, 10% hydrochloric acid was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, and described as 4- (2-propynyloxy) -2- (3,3,3-trifluoropropylsulfonyl) butanenitrile (hereinafter referred to as the present organic sulfur compound (338)). ) 0.20 g was obtained.
This organic sulfur compound (338)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 4.29 (dd, 1H), 4.19 (s, 2H), 3.71-3.92 (m, 2H), 3.43- 3.58 (m, 2H), 2.70-2.85 (m, 2H), 2.21-2.64 (m, 2H), 2.51 (t, 1H)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）：δ（ｐｐｍ）４．２０（ｓ，２Ｈ）、３．８０−３．９３（ｍ，２Ｈ）、３．４３−３．５６（ｍ，２Ｈ）、２．７０−２．８８（ｍ，２Ｈ）、２．１５−２．５６（ｍ，２Ｈ）、２．５０（ｔ，１Ｈ）、１．８７（ｓ，３Ｈ） Reference Production Example 179
0.5 g of this organic sulfur compound (338) was dissolved in 20 ml of N, N-dimethylformamide. To this, 0.1 g of sodium hydride (60% oily) was added at room temperature, and the mixture was stirred at the same temperature for 10 minutes. 0.3 g of methyl iodide was added to the mixture at room temperature and stirred for 2 hours, 10% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to give 2-methyl-4- (2-propynyloxy) -2- (3,3,3-trifluoropropylsulfonyl) butanenitrile (hereinafter referred to as the present organic sulfur compound (339). ) 0.40 g was obtained.
This organic sulfur compound (339)

¹ H-NMR (CDCl ₃ , TMS): δ (ppm) 4.20 (s, 2H), 3.80-3.93 (m, 2H), 3.43-3.56 (m, 2H), 2.70-2.88 (m, 2H), 2.15-2.56 (m, 2H), 2.50 (t, 1H), 1.87 (s, 3H)

  Next, formulation examples of the pest control composition of the present invention are shown. In addition, a part shows a weight part.

Formulation Example 1
2 parts of one organic sulfur compound selected from the group consisting of the present organic sulfur compounds (1) to (109), (201) to (231) and (301) to (339), and 7 parts of pyriprole are converted into xylene 37 In 5 parts and 37.5 parts of N, N-dimethylformamide, 10 parts of polyoxyethylene styryl phenyl ether and 6 parts of calcium dodecylbenzenesulfonate are added and mixed well with stirring to obtain an emulsion.

Formulation Example 2
5 parts of an organic sulfur compound selected from the group consisting of the present organic sulfur compounds (1) to (109), (201) to (231) and (301) to (339), and 4 parts of pyriprole are converted into xylene 37 In 5 parts and 37.5 parts of N, N-dimethylformamide, 10 parts of polyoxyethylene styryl phenyl ether and 6 parts of calcium dodecylbenzenesulfonate are added and mixed well with stirring to obtain an emulsion.

Formulation Example 3
A mixture of 20 parts of one organic sulfur compound selected from the group consisting of the present organic sulfur compounds (1) to (109), (201) to (231) and (301) to (339), and 20 parts of pyriprole, Add 5 parts of Solpol 5060 (registered trademark of Toho Chemical Co., Ltd.), mix well, add 32 parts of Carplex # 80 (registered trademark of Shionogi & Co., synthetic silicon hydroxide fine powder), 23 parts of 300 mesh diatomaceous earth, and juice Mix with mixer to obtain wettable powder.

Formulation Example 4
1 part of an organic sulfur compound selected from the group consisting of the present organic sulfur compounds (1) to (109), (201) to (231) and (301) to (339), 2 parts of pyriprole, synthetic hydrous silicon oxide Add 5 parts of fine powder, 5 parts of sodium dodecylbenzenesulfonate, 30 parts of bentonite and 57 parts of clay, mix well with stirring, add an appropriate amount of water to these mixtures, further stir and granulate with a granulator. And dried by ventilation to obtain granules.

Formulation Example 5
1.5 parts of an organic sulfur compound selected from the group consisting of the present organic sulfur compounds (1) to (109), (201) to (231) and (301) to (339), 3 parts of pyriprole, synthetic water content 1 part of silicon oxide fine powder, 1 part of Doreles B (manufactured by Sankyo Co., Ltd.) as a flocculant, and 7 parts of clay are mixed well in a mortar and then stirred and mixed with a juice mixer. 86.5 parts of cut clay is added to the resulting mixture and mixed thoroughly with stirring to obtain a powder.

Formulation Example 6
5 parts of an organic sulfur compound selected from the group consisting of the present organic sulfur compounds (1) to (109), (201) to (231) and (301) to (339); 5 parts of pyriprol; polyoxyethylene alkyl A preparation is obtained by mixing 35 parts of white carbon containing 50 parts of ether sulfate ammonium salt; and 55 parts of water and finely pulverizing the mixture by a wet pulverization method.

Formulation Example 7
One part of organic sulfur compound selected from the group consisting of the present organic sulfur compounds (1) to (109), (201) to (231) and (301) to (339), and 0.3 part of pyriprole Is dissolved in 10 parts of dichloromethane, and this is mixed with 89.5 parts of Isopar M (isoparaffin: Exxon Chemical Registration) to obtain an oil.

Formulation Example 8
0.05 part of an organic sulfur compound selected from the group consisting of the present organic sulfur compounds (1) to (109), (201) to (231) and (301) to (339), 0.05 part of pyriprole, In addition, 49.9 parts of Neothiozole (Chuo Kasei Co., Ltd.) is put in an aerosol can, and after mounting an aerosol valve, 25 parts of dimethyl ether and 25 parts of LPG are filled, and an oily aerosol is obtained by mounting an actuator.

Formulation Example 9
One organic sulfur compound selected from the group consisting of the present organic sulfur compounds (1) to (109), (201) to (231) and (301) to (339), 0.4 parts of pyriprole, An aerosol container is filled with 0.01 part of BHT, 5 parts of xylene, 3.39 parts of deodorized kerosene, and 1 part of an emulsifier {Atmos 300 (registered trademark of Atmos Chemical)} and 50 parts of distilled water. The valve part is attached, and 40 parts of propellant (LPG) is pressurized and filled through the valve to obtain an aqueous aerosol.

Formulation Example 10
2 parts of an organic sulfur compound selected from the group consisting of the present organic sulfur compounds (1) to (109), (201) to (231) and (301) to (339), and 3 parts of pyriprole are mixed with diethylene glycol monoethyl. Dissolve in 80 parts of ether and mix with 15 parts of propylene carbonate to obtain a spot-on solution.

Formulation Example 11
5 parts of one organic sulfur compound selected from the group consisting of the present organic sulfur compounds (1) to (109), (201) to (231) and (301) to (339), and 5 parts of pyriprole are mixed with diethylene glycol monoethyl. Dissolve in 70 parts of ether and mix with 20 parts of 2-octyldodecanol to obtain a pour-on solution.

Formulation Example 12
0.25 part of one organic sulfur compound selected from the group consisting of the present organic sulfur compounds (1) to (109), (201) to (231) and (301) to (339), and 0.25 parts of pyriprole To this mixture, 60 parts of Nikkor TEALS-42 (42% aqueous solution of Nikko Chemicals lauryl sulfate triethanolamine) and 20 parts of propylene glycol were added and stirred well until a homogeneous solution was obtained. In addition, the mixture is further stirred and mixed to obtain a shampoo agent in a uniform solution.

Formulation Example 13
A mixture of 0.05 g of one organic sulfur compound selected from the group consisting of the present organic sulfur compounds (1) to (109), (201) to (231) and (301) to (339), and 0.05 g of pyriprol. Is dissolved in 2 ml of propylene glycol and impregnated into a porous ceramic plate of 4.0 × 4.0 cm and a thickness of 1.2 cm to obtain a heating smoke.

Formulation Example 14
One part of the organic sulfur compound selected from the group consisting of the present organic sulfur compounds (1) to (109), (201) to (231) and (301) to (339), and 2.5 parts of pyriprole And 95 parts of ethylene-methyl methacrylate copolymer (ratio of methyl methacrylate in the copolymer: 10% by weight, Aclift WD301, manufactured by Sumitomo Chemical Co., Ltd.) using a closed pressure kneader (manufactured by Moriyama Seisakusho) Then, the obtained kneaded product is extruded from an extruder through a molding die to obtain a rod-shaped molded body having a length of 15 cm and a diameter of 3 mm.

Formulation Example 15
2.5 parts of an organic sulfur compound selected from the group consisting of the present organic sulfur compounds (1) to (109), (201) to (231) and (301) to (339), and 2.5 parts of pyriprol; 95 parts of a soft vinyl chloride resin is melt-kneaded with a closed pressure kneader (Moriyama Seisakusho), and the resulting kneaded product is extruded from an extrusion molding machine through a molding die, and a rod-shaped molded product having a length of 15 cm and a diameter of 3 mm. Get.

Formulation Example 16
1 part of an organic sulfur compound selected from the group consisting of the present organic sulfur compounds (1) to (109), (201) to (231) and (301) to (339), and 1- [2,6- 7 parts of dichloro-4- (trifluoromethyl) phenyl-3-cyano-4- (fluoromethylthio) -5-[(pyrazinylmethyl) amino] -1H-pyrazole, 37.5 parts of xylene and N, N-dimethylformamide Dissolve in 37.5 parts, add 10 parts of polyoxyethylene styryl phenyl ether and 6 parts of calcium dodecylbenzenesulfonate and stir well to obtain an emulsion.

Formulation Example 17
1 part of an organic sulfur compound selected from the group consisting of the present organic sulfur compounds (1) to (109), (201) to (231) and (301) to (339), and 1- [2,6- 4 parts of dichloro-4- (trifluoromethyl) phenyl-3-cyano-4- (fluoromethylthio) -5-[(pyrazinylmethyl) amino] -1H-pyrazole, 37.5 parts of xylene and N, N-dimethylformamide Dissolve in 37.5 parts, add 10 parts of polyoxyethylene styryl phenyl ether and 6 parts of calcium dodecylbenzenesulfonate and stir well to obtain an emulsion.

Formulation Example 18
20 parts of an organic sulfur compound selected from the group consisting of the present organic sulfur compounds (1) to (109), (201) to (231) and (301) to (339), and 1- [2,6- To a mixture of 20 parts of dichloro-4- (trifluoromethyl) phenyl-3-cyano-4- (fluoromethylthio) -5-[(pyrazinylmethyl) amino] -1H-pyrazole, Solpol 5060 (trade name of Toho Chemical) 5 Add 32 parts, mix well, add 32 parts of Carplex # 80 (registered trademark of Shionogi Pharmaceutical Co., Ltd., synthetic silicon hydroxide fine powder), 23 parts of 300 mesh diatomaceous earth, mix with a juice mixer, and add wettable powder. obtain.

Formulation Example 19
1 part of an organic sulfur compound selected from the group consisting of the present organic sulfur compounds (1) to (109), (201) to (231) and (301) to (339), 1- [2,6-dichloro -4- (trifluoromethyl) phenyl-3-cyano-4- (fluoromethylthio) -5-[(pyrazinylmethyl) amino] -1H-pyrazole, 5 parts of synthetic silicon hydroxide fine powder, sodium dodecylbenzenesulfonate Add 5 parts, 30 parts of bentonite and 57 parts of clay, stir and mix well, then add an appropriate amount of water to these mixtures, further stir, granulate with a granulator, and dry by ventilation to obtain granules. .

Formulation Example 20
1.5 parts of an organic sulfur compound selected from the group consisting of the present organic sulfur compounds (1) to (109), (201) to (231) and (301) to (339), 1- [2,6 As dichloro-4- (trifluoromethyl) phenyl-3-cyano-4- (fluoromethylthio) -5-[(pyrazinylmethyl) amino] -1H-pyrazole, 1 part of synthetic silicon hydroxide fine powder, flocculant 1 part of Doriles B (manufactured by Sankyo Co., Ltd.) and 7 parts of clay are mixed well in a mortar, and then mixed with a juice mixer. 86.5 parts of cut clay is added to the resulting mixture and mixed thoroughly with stirring to obtain a powder.

Formulation Example 21
1 part of an organic sulfur compound selected from the group consisting of the present organic sulfur compounds (1) to (109), (201) to (231) and (301) to (339); 1- [2,6-dichloro White carbon containing 5 parts of -4- (trifluoromethyl) phenyl-3-cyano-4- (fluoromethylthio) -5-[(pyrazinylmethyl) amino] -1H-pyrazole; 50 parts of polyoxyethylene alkyl ether sulfate ammonium salt 35 parts; and 55 parts of water are mixed and pulverized by a wet pulverization method to obtain a preparation.

Formulation Example 22
One organic sulfur compound selected from the group consisting of the present organic sulfur compounds (1) to (109), (201) to (231) and (301) to (339), and 1- [2, A mixture of 0.3 parts of 6-dichloro-4- (trifluoromethyl) phenyl-3-cyano-4- (fluoromethylthio) -5-[(pyrazinylmethyl) amino] -1H-pyrazole is dissolved in 10 parts of dichloromethane; This is mixed with 89.5 parts of Isopar M (isoparaffin: Exxon Chemical Registered Trademark) to obtain an oil.

Formulation Example 23
0.05 part of an organic sulfur compound selected from the group consisting of the present organic sulfur compounds (1) to (109), (201) to (231) and (301) to (339), 1- [2,6 -Dichloro-4- (trifluoromethyl) phenyl-3-cyano-4- (fluoromethylthio) -5-[(pyrazinylmethyl) amino] -1H-pyrazole, 0.05 parts, and neothiozole (Chuo Kasei Co., Ltd.) 49. 9 parts are put into an aerosol can, and after mounting an aerosol valve, 25 parts of dimethyl ether and 25 parts of LPG are filled, and an actuator is attached to obtain an oily aerosol.

Formulation Example 24
1 part of organic sulfur compounds selected from the group consisting of the present organic sulfur compounds (1) to (109), (201) to (231) and (301) to (339), 1- [2,6 -Dichloro-4- (trifluoromethyl) phenyl-3-cyano-4- (fluoromethylthio) -5-[(pyrazinylmethyl) amino] -1H-pyrazole 0.4 parts, BHT 0.01 parts, xylene 5 parts, deodorization 3.39 parts of kerosene and 1 part of emulsifier {Atmos 300 (registered trade name of Atmos Chemical)} and 50 parts of distilled water are filled in an aerosol container, a valve part is attached, and injection is performed through the valve. An aqueous aerosol is obtained by pressure filling 40 parts of an agent (LPG).

Formulation Example 25
1 part of an organic sulfur compound selected from the group consisting of the present organic sulfur compounds (1) to (109), (201) to (231) and (301) to (339), and 1- [2,6- Dissolve 3 parts of dichloro-4- (trifluoromethyl) phenyl-3-cyano-4- (fluoromethylthio) -5-[(pyrazinylmethyl) amino] -1H-pyrazole in 80 parts of diethylene glycol monoethyl ether, 15 parts of propylene is mixed to obtain a spot-on solution.

Formulation Example 26
1 part of an organic sulfur compound selected from the group consisting of the present organic sulfur compounds (1) to (109), (201) to (231) and (301) to (339), and 1- [2,6- Dissolve 5 parts of dichloro-4- (trifluoromethyl) phenyl-3-cyano-4- (fluoromethylthio) -5-[(pyrazinylmethyl) amino] -1H-pyrazole in 70 parts of diethylene glycol monoethyl ether. -Mix 20 parts octyldodecanol to obtain a pour-on solution.

Formulation Example 27
0.25 part of an organic sulfur compound selected from the group consisting of the present organic sulfur compounds (1) to (109), (201) to (231) and (301) to (339), and 1- [2, To a mixture of 0.25 parts of 6-dichloro-4- (trifluoromethyl) phenyl-3-cyano-4- (fluoromethylthio) -5-[(pyrazinylmethyl) amino] -1H-pyrazole, Nikkor TEALS-42 (Nikko) Chemicals lauryl sulfate triethanolamine 42% aqueous solution) 60 parts and propylene glycol 20 parts are added and mixed well with stirring until a homogeneous solution is added, then 19.5 parts of water is added and further stirred and mixed to obtain a uniform solution. Get a shampoo.

Formulation Example 28
0.05 g of one organic sulfur compound selected from the group consisting of the present organic sulfur compounds (1) to (109), (201) to (231) and (301) to (339), and 1- [2,6 A mixture of 0.05 g of dichloro-4- (trifluoromethyl) phenyl-3-cyano-4- (fluoromethylthio) -5-[(pyrazinylmethyl) amino] -1H-pyrazole is dissolved in 2 ml of propylene glycol, 4 It is impregnated into a porous ceramic plate having a thickness of 0.0 × 4.0 cm and a thickness of 1.2 cm to obtain a heating smoke.

Formulation Example 29
2.5 parts of one organic sulfur compound selected from the group consisting of the present organic sulfur compounds (1) to (109), (201) to (231) and (301) to (339), and 1- [2, 6-dichloro-4- (trifluoromethyl) phenyl-3-cyano-4- (fluoromethylthio) -5-[(pyrazinylmethyl) amino] -1H-pyrazole and ethylene-methyl methacrylate copolymer (Methyl methacrylate ratio in the copolymer: 10% by weight, ACRlift WD301, manufactured by Sumitomo Chemical Co., Ltd.) was melt-kneaded with a sealed pressure kneader (manufactured by Moriyama Seisakusho), and the resulting kneaded product was extruded. Extrusion is performed from a machine through a molding die to obtain a rod-shaped molded body having a length of 15 cm and a diameter of 3 mm.

Formulation Example 30
2.5 parts of an organic sulfur compound selected from the group consisting of the present organic sulfur compounds (1) to (109), (201) to (231) and (301) to (339) and 1- [2,6 -2.5 parts of dichloro-4- (trifluoromethyl) phenyl-3-cyano-4- (fluoromethylthio) -5-[(pyrazinylmethyl) amino] -1H-pyrazole and 95 parts of a soft vinyl chloride resin are sealed. The mixture is melt-kneaded with a pressure kneader (manufactured by Moriyama Seisakusho), and the resulting kneaded product is extruded from an extruder through a molding die to obtain a rod-shaped molded body having a length of 15 cm and a diameter of 3 mm.

Formulation Example 31
2 parts of an organic sulfur compound selected from the group consisting of the present organic sulfur compounds (1) to (109), (201) to (231) and (301) to (339), and 7 parts of acetoprole are converted to xylene. Dissolve in 37.5 parts and 37.5 parts of N, N-dimethylformamide, add 10 parts of polyoxyethylene styryl phenyl ether and 6 parts of calcium dodecylbenzenesulfonate, and mix well to obtain an emulsion.

Formulation Example 32
5 parts of an organic sulfur compound selected from the group consisting of the present organic sulfur compounds (1) to (109), (201) to (231) and (301) to (339), and 4 parts of acetoprole are converted to xylene. Dissolve in 37.5 parts and 37.5 parts of N, N-dimethylformamide, add 10 parts of polyoxyethylene styryl phenyl ether and 6 parts of calcium dodecylbenzenesulfonate, and mix well to obtain an emulsion.

Formulation Example 33
A mixture of 20 parts of an organic sulfur compound selected from the group consisting of the present organic sulfur compounds (1) to (109), (201) to (231) and (301) to (339), and 20 parts of acetoprole. , 5 parts of Solpol 5060 (registered trademark of Toho Chemical Co., Ltd.) was added and mixed well, 32 parts of Carplex # 80 (registered trademark of Shionogi & Co., synthetic silicon hydroxide fine powder), 23 parts of 300 mesh diatomaceous earth were added, Mix with juice mixer to get wettable powder.

Formulation Example 34
1 part of an organic sulfur compound selected from the group consisting of the present organic sulfur compounds (1) to (109), (201) to (231), and (301) to (339), 2 parts of acetoprole, synthetic hydrous oxide Add 5 parts of fine silicon powder, 5 parts of sodium dodecylbenzenesulfonate, 30 parts of bentonite and 57 parts of clay, mix well with stirring, add an appropriate amount of water to these mixtures, stir further, and produce with a granulator. Granulate and ventilate to obtain granules.

Formulation Example 35
One organic sulfur compound selected from the group consisting of the present organic sulfur compounds (1) to (109), (201) to (231) and (301) to (339), 3 parts of acetoprole, synthesis 1 part of hydrous silicon oxide fine powder, 1 part of Doreles B (manufactured by Sankyo) as a flocculant, and 7 parts of clay are mixed well in a mortar, and then stirred and mixed in a juice mixer. 86.5 parts of cut clay is added to the resulting mixture and mixed thoroughly with stirring to obtain a powder.

Formulation Example 36
5 parts of an organic sulfur compound selected from the group consisting of the present organic sulfur compounds (1) to (109), (201) to (231) and (301) to (339); 5 parts of acetoprole; polyoxyethylene A preparation is obtained by mixing 35 parts of white carbon containing 50 parts of an alkyl ether sulfate ammonium salt; and 55 parts of water and finely pulverizing them by a wet pulverization method.

Formulation Example 37
0.2 part of one organic sulfur compound selected from the group consisting of the present organic sulfur compounds (1) to (109), (201) to (231) and (301) to (339), and acetoprole 0.3 Part of the mixture is dissolved in 10 parts of dichloromethane, and this is mixed with 89.5 parts of Isopar M (isoparaffin: Exxon Chemical Registration) to obtain an oil.

Formulation Example 38
0.05 part of an organic sulfur compound selected from the group consisting of the present organic sulfur compounds (1) to (109), (201) to (231) and (301) to (339), 0.05 part of acetoprole In addition, 49.9 parts of Neothiozole (Chuo Kasei Co., Ltd.) are put in an aerosol can, and after mounting an aerosol valve, 25 parts of dimethyl ether and 25 parts of LPG are filled, and an actuator is attached to obtain an oily aerosol.

Formulation Example 39
One organic sulfur compound selected from the group consisting of the present organic sulfur compounds (1) to (109), (201) to (231) and (301) to (339), 0.4 parts of acetoprole , BHT 0.01 parts, xylene 5 parts, deodorized kerosene 3.39 parts, and emulsifier {Atmos 300 (registered trademark of Atmos Chemicals)} 1 part mixed and dissolved in distilled water container 50 parts Then, a valve portion is attached, and 40 parts of propellant (LPG) is pressurized and filled through the valve to obtain an aqueous aerosol.

Formulation Example 40
2 parts of an organic sulfur compound selected from the group consisting of the present organic sulfur compounds (1) to (109), (201) to (231) and (301) to (339), and 3 parts of acetoprole are mixed with diethylene glycol mono Dissolve in 80 parts of ethyl ether and mix with 15 parts of propylene carbonate to obtain a spot-on solution.

Formulation Example 41
5 parts of an organic sulfur compound selected from the group consisting of the present organic sulfur compounds (1) to (109), (201) to (231) and (301) to (339), and 5 parts of acetoprole are mixed with diethylene glycol mono Dissolve in 70 parts of ethyl ether and mix with 20 parts of 2-octyldodecanol to obtain a pour-on solution.

Formulation Example 42
0.25 part of one organic sulfur compound selected from the group consisting of the present organic sulfur compounds (1) to (109), (201) to (231) and (301) to (339), and acetoprol 0.25 60 parts of Nikkor TEALS-42 (42% aqueous solution of Nikko Chemicals lauryl sulfate triethanolamine) and 20 parts of propylene glycol were added to the mixture, and the mixture was stirred and mixed until a homogeneous solution was obtained. Is added and stirred sufficiently to obtain a shampoo agent in a uniform solution.

Formulation Example 43
0.05 g of one organic sulfur compound selected from the group consisting of the present organic sulfur compounds (1) to (109), (201) to (231) and (301) to (339), and 0.05 g of acetoprole The mixture is dissolved in 2 ml of propylene glycol and impregnated into a 4.0 × 4.0 cm, 1.2 cm thick porous ceramic plate to obtain a heated smoke.

Formulation Example 44
2.5 parts of an organic sulfur compound selected from the group consisting of the present organic sulfur compounds (1) to (109), (201) to (231) and (301) to (339), and acetoprol 2.5 And 95 parts of ethylene-methyl methacrylate copolymer (ratio of methyl methacrylate in the copolymer: 10% by weight, ACRIFT WD301, manufactured by Sumitomo Chemical Co., Ltd.) were melted in a closed pressure kneader (manufactured by Moriyama Seisakusho). The resulting kneaded product is extruded from an extruder through a molding die to obtain a rod-shaped molded body having a length of 15 cm and a diameter of 3 mm.

Formulation Example 45
2.5 parts of an organic sulfur compound selected from the group consisting of the present organic sulfur compounds (1) to (109), (201) to (231) and (301) to (339) and 2.5 parts of acetoprole And 95 parts of a soft vinyl chloride resin are melt-kneaded in a closed pressure kneader (Moriyama Seisakusho), and the resulting kneaded product is extruded from an extrusion molding machine through a molding die, and is formed into a rod having a length of 15 cm and a diameter of 3 mm. Get the body.

Formulation Example 46
2 parts of one organic sulfur compound selected from the group consisting of the present organic sulfur compounds (1) to (109), (201) to (231) and (301) to (339), and 7 parts of Ethiprole are converted to xylene 37 In 5 parts and 37.5 parts of N, N-dimethylformamide, 10 parts of polyoxyethylene styryl phenyl ether and 6 parts of calcium dodecylbenzenesulfonate are added and mixed well with stirring to obtain an emulsion.

Formulation Example 47
5 parts of one organic sulfur compound selected from the group consisting of the present organic sulfur compounds (1) to (109), (201) to (231) and (301) to (339), and 4 parts of Ethiprole are converted into xylene 37 In 5 parts and 37.5 parts of N, N-dimethylformamide, 10 parts of polyoxyethylene styryl phenyl ether and 6 parts of calcium dodecylbenzenesulfonate are added and mixed well with stirring to obtain an emulsion.

Formulation Example 48
A mixture of 20 parts of an organic sulfur compound selected from the group consisting of the present organic sulfur compounds (1) to (109), (201) to (231) and (301) to (339), and 20 parts of Ethiprole, Add 5 parts of Solpol 5060 (registered trademark of Toho Chemical Co., Ltd.), mix well, add 32 parts of Carplex # 80 (registered trademark of Shionogi & Co., synthetic silicon hydroxide fine powder), 23 parts of 300 mesh diatomaceous earth, and juice Mix with a mixer to obtain a wettable powder.

Formulation Example 49
1 part of an organic sulfur compound selected from the group consisting of the present organic sulfur compounds (1) to (109), (201) to (231) and (301) to (339), 2 parts of Ethiprole, synthetic hydrous silicon oxide Add 5 parts of fine powder, 5 parts of sodium dodecylbenzenesulfonate, 30 parts of bentonite and 57 parts of clay, mix well with stirring, add an appropriate amount of water to these mixtures, further stir and granulate with a granulator. And dried by ventilation to obtain granules.

Formulation Example 50
1.5 parts of an organic sulfur compound selected from the group consisting of the present organic sulfur compounds (1) to (109), (201) to (231) and (301) to (339), 3 parts of Ethiprole, synthetic water content 1 part of silicon oxide fine powder, 1 part of Doreles B (manufactured by Sankyo Co., Ltd.) as a flocculant, and 7 parts of clay are mixed well in a mortar, followed by stirring and mixing with a juice mixer. 86.5 parts of cut clay is added to the resulting mixture and mixed thoroughly with stirring to obtain a powder.

Formulation Example 51
5 parts of an organic sulfur compound selected from the group consisting of the present organic sulfur compounds (1) to (109), (201) to (231) and (301) to (339); 5 parts of ethylene glycol; polyoxyethylene alkyl A preparation is obtained by mixing 35 parts of white carbon containing 50 parts of ether sulfate ammonium salt; and 55 parts of water, and finely pulverizing them by a wet pulverization method.

Formulation Example 52
One part of organic sulfur compound selected from the group consisting of the present organic sulfur compounds (1) to (109), (201) to (231) and (301) to (339), and 0.3 part of Ethiprole Is dissolved in 10 parts of dichloromethane, and this is mixed with 89.5 parts of Isopar M (isoparaffin: Exxon Chemical Registration) to obtain an oil.

Formulation Example 53
0.05 part of an organic sulfur compound selected from the group consisting of the present organic sulfur compounds (1) to (109), (201) to (231) and (301) to (339), 0.05 part of Ethiprole, In addition, 49.9 parts of Neothiozole (Chuo Kasei Co., Ltd.) is put in an aerosol can, and after mounting an aerosol valve, 25 parts of dimethyl ether and 25 parts of LPG are filled, and an oily aerosol is obtained by mounting an actuator.

Formulation Example 54
One organic sulfur compound selected from the group consisting of the present organic sulfur compounds (1) to (109), (201) to (231), and (301) to (339), 0.4 parts of Ethiprole, An aerosol container is filled with 0.01 part of BHT, 5 parts of xylene, 3.39 parts of deodorized kerosene, and 1 part of an emulsifier {Atmos 300 (registered trademark of Atmos Chemical)} and 50 parts of distilled water. The valve portion is attached, and 40 parts of propellant (LPG) is pressure-filled through the valve to obtain an aqueous aerosol.

Formulation Example 55
2 parts of one kind of organic sulfur compound selected from the group consisting of the present organic sulfur compounds (1) to (109), (201) to (231) and (301) to (339), and 3 parts of Ethiprole to diethylene glycol monoethyl Dissolve in 80 parts of ether and mix with 15 parts of propylene carbonate to obtain a spot-on solution.

Formulation Example 56
5 parts of an organic sulfur compound selected from the group consisting of the present organic sulfur compounds (1) to (109), (201) to (231), and (301) to (339), and 5 parts of Ethiprole are mixed with diethylene glycol monoethyl. Dissolve in 70 parts of ether and mix with 20 parts of 2-octyldodecanol to obtain a pour-on solution.

Formulation Example 57
One organic sulfur compound selected from the group consisting of the present organic sulfur compounds (1) to (109), (201) to (231) and (301) to (339), and 0.25 parts of Ethiprole To this mixture, 60 parts of Nikkor TEALS-42 (42% aqueous solution of Nikko Chemicals lauryl sulfate triethanolamine) and 20 parts of propylene glycol were added and stirred well until a homogeneous solution was obtained, and then 19.5 parts of water was added. In addition, the mixture is further thoroughly stirred and mixed to obtain a shampoo agent in a uniform solution.

Formulation Example 58
A mixture of 0.05 g of one organic sulfur compound selected from the group consisting of the present organic sulfur compounds (1) to (109), (201) to (231) and (301) to (339), and 0.05 g of Ethiprole Is dissolved in 2 ml of propylene glycol and impregnated into a porous ceramic plate of 4.0 × 4.0 cm and a thickness of 1.2 cm to obtain a heating smoke.

Formulation Example 59
2.5 parts of an organic sulfur compound selected from the group consisting of the present organic sulfur compounds (1) to (109), (201) to (231) and (301) to (339), and 2.5 parts of Ethiprole And 95 parts of an ethylene-methyl methacrylate copolymer (ratio of methyl methacrylate in the copolymer: 10% by weight, ACLIFT WD301, manufactured by Sumitomo Chemical Co., Ltd.) using a sealed pressure kneader (manufactured by Moriyama Seisakusho) Then, the obtained kneaded product is extruded from an extruder through a molding die to obtain a rod-shaped molded body having a length of 15 cm and a diameter of 3 mm.

Formulation Example 60
2.5 parts of an organic sulfur compound selected from the group consisting of the present organic sulfur compounds (1) to (109), (201) to (231) and (301) to (339) and 2.5 parts of Ethiprole 95 parts of a soft vinyl chloride resin is melt-kneaded with a closed pressure kneader (Moriyama Seisakusho), and the resulting kneaded product is extruded from an extrusion molding machine through a molding die, and is a rod-shaped molded product having a length of 15 cm and a diameter of 3 mm. Get.

Formulation Example 61
1 part of an organic sulfur compound selected from the group consisting of the present organic sulfur compounds (1) to (109), (201) to (231) and (301) to (339), and 1- [2,6- 7 parts of dichloro-4- (trifluoromethyl) phenyl-3-cyano-4- (trifluoromethylthio) -5-[(4-hydroxy-3-methoxybenzylidene) amino] -1H-pyrazole is added to 37.5 xylene. And 10 parts of polyoxyethylene styryl phenyl ether and 6 parts of calcium dodecylbenzenesulfonate are mixed and mixed well with stirring to obtain an emulsion.

Formulation Example 62
1 part of an organic sulfur compound selected from the group consisting of the present organic sulfur compounds (1) to (109), (201) to (231) and (301) to (339), and 1- [2,6- 4 parts of dichloro-4- (trifluoromethyl) phenyl-3-cyano-4- (trifluoromethylthio) -5-[(4-hydroxy-3-methoxybenzylidene) amino] -1H-pyrazole are mixed with 37.5 xylene. And 10 parts of polyoxyethylene styryl phenyl ether and 6 parts of calcium dodecylbenzenesulfonate are mixed and mixed well with stirring to obtain an emulsion.

Formulation Example 63
20 parts of an organic sulfur compound selected from the group consisting of the present organic sulfur compounds (1) to (109), (201) to (231) and (301) to (339), and 1- [2,6- Solpol 5060 was added to a mixture of 20 parts dichloro-4- (trifluoromethyl) phenyl-3-cyano-4- (trifluoromethylthio) -5-[(4-hydroxy-3-methoxybenzylidene) amino] -1H-pyrazole. Add 5 parts (trade name of Toho Chemical) and mix well. Add Carplex # 80 (trade name of Shionogi & Co., synthetic silicon hydroxide fine powder) 32 parts, 23 parts of 300 mesh diatomaceous earth. Mix to obtain wettable powder.

Formulation Example 64
1 part of an organic sulfur compound selected from the group consisting of the present organic sulfur compounds (1) to (109), (201) to (231) and (301) to (339), 1- [2,6-dichloro -4- (trifluoromethyl) phenyl-3-cyano-4- (trifluoromethylthio) -5-[(4-hydroxy-3-methoxybenzylidene) amino] -1H-pyrazole, synthetic silicon hydroxide fine powder 5 parts, 5 parts of sodium dodecylbenzenesulfonate, 30 parts of bentonite and 57 parts of clay are mixed well with stirring, and then an appropriate amount of water is added to these mixtures, followed by further stirring and granulation with a granulator. Dry by ventilation to obtain granules.

Formulation Example 65
1.5 parts of an organic sulfur compound selected from the group consisting of the present organic sulfur compounds (1) to (109), (201) to (231) and (301) to (339), 1- [2,6 -Dichloro-4- (trifluoromethyl) phenyl-3-cyano-4- (trifluoromethylthio) -5-[(4-hydroxy-3-methoxybenzylidene) amino] -1H-pyrazole, 3 parts of synthetic silicon hydroxide 1 part of fine powder, 1 part of Doreles B (manufactured by Sankyo Co., Ltd.) as a flocculant, and 7 parts of clay are mixed well in a mortar, and then stirred and mixed with a juice mixer. 86.5 parts of cut clay is added to the resulting mixture and mixed thoroughly with stirring to obtain a powder.

Formulation Example 66
1 part of an organic sulfur compound selected from the group consisting of the present organic sulfur compounds (1) to (109), (201) to (231) and (301) to (339); 1- [2,6-dichloro -4- (trifluoromethyl) phenyl-3-cyano-4- (trifluoromethylthio) -5-[(4-hydroxy-3-methoxybenzylidene) amino] -1H-pyrazole 5 parts; polyoxyethylene alkyl ether sulfate A preparation is obtained by mixing 35 parts of white carbon containing 50 parts of an ammonium salt; and 55 parts of water and finely pulverizing them by a wet pulverization method.

Formulation Example 67
One organic sulfur compound selected from the group consisting of the present organic sulfur compounds (1) to (109), (201) to (231) and (301) to (339), and 1- [2, A mixture of 0.3 parts of 6-dichloro-4- (trifluoromethyl) phenyl-3-cyano-4- (trifluoromethylthio) -5-[(4-hydroxy-3-methoxybenzylidene) amino] -1H-pyrazole Is dissolved in 10 parts of dichloromethane, and this is mixed with 89.5 parts of Isopar M (isoparaffin: trade name of Exxon Chemical) to obtain an oil.

Formulation Example 68
0.05 part of an organic sulfur compound selected from the group consisting of the present organic sulfur compounds (1) to (109), (201) to (231) and (301) to (339), 1- [2,6 -Dichloro-4- (trifluoromethyl) phenyl-3-cyano-4- (trifluoromethylthio) -5-[(4-hydroxy-3-methoxybenzylidene) amino] -1H-pyrazole, 0.05 parts, and neothiozole (Chuo Kasei Co., Ltd.) After putting 49.9 parts in an aerosol can and mounting an aerosol valve, 25 parts of dimethyl ether and 25 parts of LPG are filled, and an actuator is attached to obtain an oily aerosol.

Formulation Example 69
1 part of organic sulfur compounds selected from the group consisting of the present organic sulfur compounds (1) to (109), (201) to (231) and (301) to (339), 1- [2,6 -Dichloro-4- (trifluoromethyl) phenyl-3-cyano-4- (trifluoromethylthio) -5-[(4-hydroxy-3-methoxybenzylidene) amino] -1H-pyrazole, 0.4 part, BHT0. 01 parts, 5 parts of xylene, 3.39 parts of deodorized kerosene, and 1 part of an emulsifier {Atmos 300 (registered trademark name of Atmos Chemical)} and 50 parts of distilled water are filled in an aerosol container, The part is attached and 40 parts of propellant (LPG) is pressure filled through the valve to obtain an aqueous aerosol.

Formulation Example 70
1 part of an organic sulfur compound selected from the group consisting of the present organic sulfur compounds (1) to (109), (201) to (231) and (301) to (339), and 1- [2,6- 3 parts of dichloro-4- (trifluoromethyl) phenyl-3-cyano-4- (trifluoromethylsulfinyl) -5-amino-1H-pyrazole is dissolved in 80 parts of diethylene glycol monoethyl ether, and 15 parts of propylene carbonate is dissolved in this. Are mixed to obtain a spot-on solution.

Formulation Example 71
1 part of an organic sulfur compound selected from the group consisting of the present organic sulfur compounds (1) to (109), (201) to (231) and (301) to (339), and 1- [2,6- Dichloroglycol monoethyl ether 70 parts of dichloro-4- (trifluoromethyl) phenyl-3-cyano-4- (trifluoromethylthio) -5-[(4-hydroxy-3-methoxybenzylidene) amino] -1H-pyrazole 70 parts And 20 parts of 2-octyldodecanol are mixed with this to obtain a pour-on solution.

Formulation Example 72
0.25 part of an organic sulfur compound selected from the group consisting of the present organic sulfur compounds (1) to (109), (201) to (231) and (301) to (339), and 1- [2, A mixture of 0.25 parts of 6-dichloro-4- (trifluoromethyl) phenyl-3-cyano-4- (trifluoromethylthio) -5-[(4-hydroxy-3-methoxybenzylidene) amino] -1H-pyrazole 60 parts of Nikkor TEALS-42 (42% aqueous solution of Nikko Chemicals lauryl sulfate triethanolamine) and 20 parts of propylene glycol, and after stirring and mixing until a homogeneous solution is obtained, 19.5 parts of water are added. Further, the mixture is sufficiently stirred and mixed to obtain a shampoo agent in a uniform solution.

Formulation Example 73
0.05 g of one organic sulfur compound selected from the group consisting of the present organic sulfur compounds (1) to (109), (201) to (231) and (301) to (339), and 1- [2,6 A mixture of 0.05 g of dichloro-4- (trifluoromethyl) phenyl-3-cyano-4- (trifluoromethylthio) -5-[(4-hydroxy-3-methoxybenzylidene) amino] -1H-pyrazole, It is dissolved in 2 ml of propylene glycol and impregnated into a 4.0 × 4.0 cm, 1.2 cm thick porous ceramic plate to obtain a heating smoke.

Formulation Example 74
2.5 parts of one organic sulfur compound selected from the group consisting of the present organic sulfur compounds (1) to (109), (201) to (231) and (301) to (339), and 1- [2, 2.5 parts of 6-dichloro-4- (trifluoromethyl) phenyl-3-cyano-4- (trifluoromethylthio) -5-[(4-hydroxy-3-methoxybenzylidene) amino] -1H-pyrazole; 95 parts of ethylene-methyl methacrylate copolymer (ratio of methyl methacrylate in the copolymer: 10% by weight, ACLIFT WD301, manufactured by Sumitomo Chemical Co., Ltd.) was melt-kneaded with a closed pressure kneader (Moriyama Seisakusho) The obtained kneaded product is extruded from an extrusion molding machine through a molding die to obtain a rod-shaped molded body having a length of 15 cm and a diameter of 3 mm.

Formulation Example 75
2.5 parts of an organic sulfur compound selected from the group consisting of the present organic sulfur compounds (1) to (109), (201) to (231) and (301) to (339) and 1- [2,6 -Dichloro-4- (trifluoromethyl) phenyl-3-cyano-4- (trifluoromethylthio) -5-[(4-hydroxy-3-methoxybenzylidene) amino] -1H-pyrazole and soft chloride 95 parts of vinyl resin is melt-kneaded with a closed pressure kneader (manufactured by Moriyama Seisakusho), and the resulting kneaded product is extruded from an extrusion molding machine through a molding die to obtain a rod-shaped molded body having a length of 15 cm and a diameter of 3 mm. .

  Next, it is shown as a test example that the pest control composition of the present invention has an excellent control effect against pests.

Test example 1
An acetone solution having a predetermined concentration of the organic sulfur compound and the pyrazole compound was prepared. After 1 μl of the acetone solution was dropped on the ventral side of the chest of a female German cockroach (Blattella germanica), the test insect was transferred to a plastic cup with a diameter of about 9 cm and a height of about 4.5 cm, and left at 25 ° C. with food and water. did. Seven days later, the life and death of the test insects were observed to determine the death rate. The German cockroaches tested were 10 in one test, and one cup was transferred.
The results are shown in Table 1 below.

  As a result, the pest control composition of the present invention showed high control efficacy.

  The pest control composition of the present invention has an excellent control effect against pests and is useful.

Claims (10)

Formula (I) below

[Where,
R ¹ is a C1-C5 haloalkyl group having at least one fluorine atom, a C3-C5 alkenyl group optionally substituted with a halogen atom, a C3-C5 alkenyloxy group optionally substituted with a halogen atom, a halogen atom A C3-C5 alkynyl group which may be substituted with or a C3-C5 alkynyloxy group which may be substituted with a halogen atom,
R ² represents a C1-C4 alkyl group optionally substituted with a halogen atom, a C1-C4 alkoxy group optionally substituted with a halogen atom, a C1-C4 alkylthio group optionally substituted with a halogen atom, or a hydrogen atom Represents
(However, when R ¹ is a C3-C5 alkenyloxy group which may be substituted with a halogen atom or a C3-C5 alkynyloxy group which may be substituted with a halogen atom, R ² is substituted with a halogen atom. It may be a C1-C4 alkyl group or a hydrogen atom.)
R ³ represents a C1-C4 alkyl group, a halogen atom or a hydrogen atom,
R ⁴ represents a cyano group, C (= Q) OR ⁷ or C (= Q) N (R ⁸ ) ₂ ,
R ⁵ represents a hydrogen atom, a halogen atom or a C1-C4 alkyl group,
R ⁶ represents a C1-C5 fluoroalkyl group,
Q represents an oxygen atom or a sulfur atom,
R ⁷ represents a C1-C4 alkyl group,
R ⁸ is either a hydrogen atom or a C1-C4 alkyl group each independently, the two R ⁸ are bonded at the ends represents a C2-C7 alkylene group,
m represents an integer of 0 to 4,
n represents 0, 1 or 2. ]
An organic sulfur compound represented by
Following formula (II)

[Where,
X ¹ represents a cyano group or an acetyl group, and X ² represents a methylthio group, a fluoromethylthio group, a difluoromethylthio group, a trifluoromethylthio group, an ethylthio group, a methylsulfinyl group, a fluoromethylsulfinyl group, a difluoromethylsulfinyl group, or trifluoromethyl. A sulfinyl group or an ethylsulfinyl group is represented, and X ³ represents an amino group, a (2-pyridylmethyl) amino group, a (pyrazinylmethyl) amino group, or a (4-hydroxy-3-methoxybenzylidene) amino group. ]
A pest control composition comprising a pyrazole compound represented by the formula: In formula (I), R ¹ may be a C3-C5 alkenyl group optionally substituted with a halogen atom, a C3-C5 alkenyloxy group optionally substituted with a halogen atom, or a C3 optionally substituted with a halogen atom. The composition according to claim 1, which is a -C5 alkynyl group or a C3-C5 alkynyloxy group which may be substituted with a halogen atom. In formula (I), R ¹ is a C1-C5 haloalkyl group having at least one fluorine atom and at least one chlorine atom, or a C1-C5 haloalkyl group having at least one fluorine atom and at least one bromine atom. The composition according to claim 1. The composition according to claim 1, wherein in formula (I), R ¹ is a C1-C5 haloalkyl group having at least one fluorine atom, and R ² and R ³ are hydrogen atoms. In the formula (I), R ¹ is a C1-C5 haloalkyl group having at least one fluorine atom, R ² is a C1-C4 alkyl group optionally substituted with a halogen atom, and R ³ is a hydrogen atom The composition according to claim 1. In the formula (I), R ¹ is a C1-C5 haloalkyl group having at least one fluorine atom, and R ² is a C1-C4 alkoxy group which may be substituted with a halogen atom or a halogen atom. it is also be C1-C4 alkylthio groups, the composition of claim 1 R ³ is a hydrogen atom. The pyrazole compound represented by the formula (II) is 1- [2,6-dichloro-4- (trifluoromethyl) phenyl-3-cyano-4- (difluoromethylthio) -5-[(2-pyridylmethyl) amino]. -1H-pyrazole,
1- [2,6-dichloro-4- (trifluoromethyl) phenyl-3-cyano-4- (ethylsulfinyl) -5-amino-1H-pyrazole or 1- [2,6-dichloro-4- (tri The composition according to any one of claims 1 to 6, which is fluoromethyl) phenyl-3-acetyl-4- (methylsulfinyl) -5-amino-1H-pyrazole. The pyrazole compound represented by the formula (II) is 1- [2,6-dichloro-4- (trifluoromethyl) phenyl-3-cyano-4- (difluoromethylthio) -5-[(2-pyridylmethyl) amino]. It is -1H-pyrazole, The composition of any one of Claims 1-6. A method for controlling pests, which comprises applying the composition according to any one of claims 1 to 8 to pests or habitats of pests. Use of the composition according to any one of claims 1 to 8 for controlling pests.