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Title:
NOVEL AMIDE COMPOUND, METHOD FOR PRODUCING THE SAME, AND MITICIDE
Document Type and Number:
WIPO Patent Application WO/2018/051252
Kind Code:
A2
Abstract:
An object of the present invention is to provide an amide compound or a salt thereof that controls a mite. The present invention provides an amide compound represented by Formula (1) : or a salt thereof, wherein R1 represents C1-6 alkyl or C1-6 haloalkyl; R2 and R3 are identical or different and each represent hydrogen, halogen, cyano, nitro, C1-6 alkyl, or the like; Q represents Q-1 or Q-2: R4 represents hydrogen, C1-6 alkyl, acetyl or the like; R5 and R6 are identical or different and each represent hydrogen, halogen, or C1-6 alkyl, or the like; HET represents 5- or 6-membered heteroaryl, R7 represents C1-6 alkyl, C1-6 haloalkyl, C3-8 cycloalkyl, C3-8 cycloalkyl C1-6 alkyl, substituted or unsubstituted aryl, substituted or unsubstituted aryl C1-6 alkyl X represents oxygen or sulfur; and n represents an integer of 0 to 2.

Inventors:
IMAI, Tetsuya (E-423, RIICO Industrial Area, Chopanki, 301707, IN)
KUMAWAT, Surendra Kumar (E-423, RIICO Industrial Area Chopanki, Rajasthan 7, 301707, IN)
SINGH, Manish Kumar (E-423, RIICO Industrial Area Chopanki, Rajasthan 7, 301707, IN)
CHAUHAN, Pramod Kumar (E-423, RIICO Industrial Area Chopanki, Rajasthan 7, 301707, IN)
BHATT, Ashish (E-423, RIICO Industrial Area Chopanki, Rajasthan 7, 301707, IN)
SURAMWAR, Nikhil Vilas (E-423, RIICO Industrial Area Chopanki, Rajasthan 7, 301707, IN)
SHELKE, Amol Vasant (E-423, RIICO Industrial Area Chopanki, Rajasthan 7, 301707, IN)
SINGH, Rajesh Kumar (E-423, RIICO Industrial Area Chopanki, Rajasthan 7, 301707, IN)
KISHORE, Ram (E-423, RIICO Industrial Area Chopanki, Rajasthan 7, 301707, IN)
Application Number:
IB2017/055542
Publication Date:
March 22, 2018
Filing Date:
September 14, 2017
Export Citation:
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Assignee:
INSECTICIDES (INDIA) LIMITED (401-402, Lusa Tower Azadpur Commercial Complex, Delhi 3, 110033, IN)
OAT AGRIO CO., LTD. (1-3-1, Kanda Ogawa-Machi Chiyoda-Ku, Tokyo 52, 1010052, JP)
International Classes:
C07D213/74; C07D213/26; C07D213/56; C07D213/61; C07D213/75; C07D213/84; C07D231/12; C07D231/14; C07D231/16; C07D231/56; C07D235/06; C07D235/24; C07D237/12; C07D249/10; C07D257/04; C07D277/30; C07D277/32; C07D285/12; C07D333/24; C07D401/04; C07D409/04; C07D417/04
Domestic Patent References:
WO2016087421A12016-06-09
WO2007131680A12007-11-22
WO2012176856A22012-12-27
Foreign References:
JP2011042611A2011-03-03
EP3002279A12016-04-06
Attorney, Agent or Firm:
GARG, Vidisha et al. (B-41, Nizamuddin East, New Delhi 3, 110013, IN)
Download PDF:
Claims:
CLAIMS

[Claim 1]

An amide compound represented by Formula

or a salt thereof,

wherein R1 represents C1_6 alkyl or C1_6 haloalkyl;

R2 and R3 are identical or different and each represents hydrogen, halogen, cyano, nitro, C1_6 alkyl, C1_6 haloalkyl, C1_6 alkoxy, C1_6 haloalkoxy, C1_6 alkoxy C1_6 alkyl, C1_6 haloalkoxy C1_6 alkyl;

Q represents Q-1 or Q-2 :

wherein R4 represents hydrogen, hydroxyl, formyl, cyano, C1_6 alkyl, C1_6 haloalkyl, C1_6 alkoxy, C1_6 haloalkoxy, C1_6 alkoxy C1_6 alkyl, C3_8 cycloalkyl, C3_8 cycloalkyl C1_6 alkyl, C1_6 alkylcarbonyl, C1_6 haloalkylcarbonyl, C1_6 alkoxycarbonyl, C1_6 haloalkoxycarbonyl, arylcarbonyl, aryloxycarbonyl, cyano C1_6 alkyl, C2-6 alkenyl, C2-6 haloalkenyl, cyano C2-6 alkenyl, C2-6 alkynyl, C2-6 haloalkynyl, cyano C2-6 alkynyl, C1_6 alkylsulfonyl, C1_6 haloalkylsulfonyl, C1_6 alkylsulfinyl, C1_6 haloalkylsulfinyl, C2-6 alkenyloxy, C2-6 alkynyloxy, aryl, aryl C1_6 alkyl, aryloxy, arylsulfonyl, arylsulfinyl, heteroaryl, all the substituents defined as R4 may optionally be further substituted;

R5 and R6 are identical or different and each represents hydrogen, halogen, C1_6 alkyl, or C1_6 haloalkyl; R5 and R6, taken together with the carbon atom, may bond to each other to form a 3- to 7-membered ring, via or not via at least one heteroatom;

R7 represents hydrogen, C1_6 alkyl, C1_6 haloalkyl, C1_6 alkoxy, C1_6 haloalkoxy, C1_6 alkoxy C1_6 alkyl, C1_6 haloalkoxy C1_6 alkyl, C1_6 alkylcarbonyl, C1_6 haloalkylcarbonyl, C1_6 alkoxycarbonyl, C1_6 haloalkoxycarbonyl, C2-6 alkenyl, C2-6 haloalkenyl, C2-6 cyanoalkenyl, C2-6 alkynyl, C2-6 haloalkynyl, C2-6 cyanoalkynyl, C3_8 cycloalkyl, C3_8 cycloalkyl C1_6 alkyl, C1_6 alkylsulfonyl, C1_6 alkylsulfinyl, C1_6 haloalkylsulfonyl, C1_6 haloalkylsulfinyl, C3_8 cycloalkylsulfonyl, C3_8 cycloalkylsulfinyl, C3_8 cycloalkyl C1_6 alkylsulfonyl, C3_8 cycloalkyl C1_6 alkylsulfinyl, C2-6 alkenyloxy, C2-6 alkynyloxy, C2-6 haloalkenyloxy, C2-6 haloalkynyloxy, aryloxy, aryl C1_6 alkoxy, heteroaryloxy, heteroaryl C1_6 alkoxy, substituted or unsubstituted aryl, substituted or unsubstituted aryl C1_6 alkyl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heteroaryl C1_6 alkyl, substituted or unsubstituted heterocyclic group, substituted or unsubstituted amino, the groups represented as R7 may optionally be further substituted with any substituents;

HET is a 5- or 6-membered heteroaryl, wherein the ring member atoms of the heteroaryl include besides carbon atoms 1, 2, 3 or 4 heteroatoms selected from N, 0 and S, and wherein the heteroaryl is unsubstituted or carries 1, 2, 3 or 4 identical or different groups R8;

R8 represents hydrogen, halogen, nitro, cyano, hydroxyl, formyl, substituted or unsubstituted amino, C1_6 alkyl, C1_6 haloalkyl, C1_6 alkoxy, C1_6 haloalkoxy, C1_6 alkoxy C1_6 alkyl, C1_6 haloalkoxy C1_6 alkyl, C1_6 alkoxycarbonyl, C1_6 haloalkoxycarbonyl, C1_6 cyanoalkyl, C1_6 cyanoalkoxy, C2-6 alkenyl, C2-6 haloalkenyl, C2-6 cyanoalkenyl, C2-6 alkynyl, C2-6 haloalkynyl, C2-6 cyanoalkynyl, C3_8 cycloalkyl, C3_8 cycloalkyl C1_6 alkyl, C1_6 alkylthio, C1_6 haloalkylthio, C3_8 cycloalkylthio, C3_8 cycloalkyl C1_6 alkylthio, C1_6 alkoxyalkylthio, C1_6 alkylsulfonyl, C1_6 alkylsulfinyl, C1_6 haloalkylsulfonyl, C1_6 haloalkylsulfinyl, C3_8 cycloalkylsulfonyl, C3_8 cycloalkylsulfinyl, C3_8 cycloalkyl C1_6 alkylsulfonyl, C3_8 cycloalkyl C1_6 alkylsulfinyl, C2-6 alkenyloxy, C2-6 alkynyloxy, C2-6 haloalkenyloxy, C2-6 haloalkynyloxy, C1_6 alkylsulfonyloxy, C1_6 alkylsulfinyloxy, C1_6 alkylcarbonyl, C1_6 haloalkylcarbonyl, carboxyl, OCN, SCN, SF5, substituted or unsubstituted aryloxy, substituted or unsubstituted aryl C1_6 alkoxy, substituted or unsubstituted arylthio, substituted or unsubstituted aryl C1_6 alkylthio, substituted or unsubstituted arylsulfonyl, substituted or unsubstituted arylsulfinyl, substituted or unsubstituted heteroaryloxy, substituted or unsubstituted arylsulfonyloxy, substituted or unsubstituted arylsulfinyloxy, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, or substituted or unsubstituted heterocyclic group, the groups represented as R8 may optionally be further substituted;

or two radicals R8 that are bound to adjacent ring member atoms of the Het group may form together with said ring member atoms a fused ring system, in such a case, HET is fused with 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocycle, wherein the ring member atoms of the fused heterocycle include besides carbon atoms 1, 2, 3 or 4 heteroatoms selected from the group of N, 0 and S, or with a substituted or unsubstituted aryl and wherein the fused carbocycle or heterocycle is unsubstituted or carries 1, 2, 3 or 4 identical or different radicals groups R8;

X represents oxygen or sulfur; and

n represents an integer of 0 to 2.

[Claim 2]

The amide compound or the salt thereof according to claim 1, wherein Q is Q-l as represented by 1A:

[Claim 3]

The amide compound or the salt thereof according to claim 1, wherein Q is Q-2 as represented by IB:

[Claim 4]

The amide compound or the salt thereof according to claim 2, wherein HET is substituted or unsubstituted pyrazole, substituted or unsubstituted thiazole or substituted or unsubstituted pyridine .

[Claim 5]

The amide compound or the salt thereof according to claim 3, wherein R7 is substituted or unsubstituted aryl or substituted or unsubstituted aryl C1-4 alkyl.

[Claim 6]

The amide compound or the salt thereof according to any of claims 1 to 5, wherein R1 is C1_6 haloalkyl.

[Claim 7]

The amide compound or the salt thereof according to any one of claims 1 to 5, wherein R2 and R3 are identical or different and each represents halogen, cyano, or C1_6 alkyl.

[Claim 8]

The amide compound or the salt thereof according to any one of claims 1 to 5, wherein R4 is hydrogen, C1_6 alkyl, or C1_6 alkylcarbonyl

[Claim 9]

A method for producing the amide compound or the salt thereof according to claim 2, comprising at least one step selected from the group consisting of following steps (d) and (e) :

Step (d) : obtaining the sulfide compound represented by Formula (ΙΑ-a) by reacting a thiol compound represented by Formula (6) with an alkylating reagent represented by Formula (7) :

wherein R1, R2, R3, R4, R5, R6, X and HET are as defined above and G represents a leaving group; and

Step (e) : obtaining an amide compound represented by Formula (ΙΑ-b) by reacting the sulfide compound represented by Formula (ΙΑ-a) with an oxidizin agent:

wherein R1, R2, R3, R4, R5, R6, X and HET are as defined above and n' represents 1 or 2.

[Claim 10]

The method for producing the amide compound or the salt thereof according to claim 9, further comprising the following step (c) :

Step (c) : obtaining a thiol compound represented by Formula (6) by reacting a sulfonylchloride compound represented by Formula (5) with a reducing agent:

wherein R2, R3, R4, R5, R6, X and HET are as defined above. [Claim 11]

The method for producing the amide compound or the salt thereof according to claim 10, further comprising the following step (b) :

Step (b) : obtaining the sulfonylchloride compound represented by Formula (5) by chlorosulfonylating a heteroaryl acetamide com ound represented by Formula (4) :

wherein R2, R3, R4, R5, R6, X and HET are as defined above. [Claim 12]

The method for producing the amide compound or the salt thereof according to claim 11, further comprising the following step (a) :

Step (a) : obtaining the heteroaryl acetamide compound represented by Formula (4) by reacting an aniline compound represented by Formula (2) with a heteroarylalkyl carbonyl compound represented by Formula (3) :

wherein R2, R3, R4, R5, R6, X and HET are as defined above and Y represents a leaving group or hydroxyl group.

[Claim 13]

A pesticide containing the amide compound or the salt thereof according to any one of claims 1 to 8.

[Claim 14]

A miticide containing the amide compound or the salt thereof according to any one of claims 1 to 8.

Description:
DESCRIPTION

Title of Invention: NOVEL AMIDE COMPOUND, METHOD FOR PRODUCING THE SAME, AND MITICIDE Technical Field

The present invention relates to a novel amide compound, method for producing the same, and miticide containing the compound. Background Art

In recent years, due to long term and heavy use of known miticides, development of resistance in various mites has been observed. As a result, the control of drug resistant mites could not be accomplished by the use of known miticides. Consequently, there is a demand for the development of new type of compounds having a miticidal activity against drug resistant as well as drug sensitive mites.

For example, Patent Literature PTL-1 (JP 2011/042611) discloses a compound represented by following Formula (A) :

wherein R 5 represents substituted or unsubstituted C 1 -20 alkyl, substituted or unsubstituted amino, N-containing heterocycles, or the like, and reports that this compound exhibits miticidal activity.

However, in PTL-1, mainly, urea compounds are produced, and in case of the amide compounds only those where R 5 is alkyl, haloalkyl, aryl, or cycloalkyl are disclosed, but the compounds of the present invention are not included. In addition, PTL 1 nowhere discloses that the above compound (A) exhibits ovicidal activity.

Patent Literature PTL-2 (WO 2016/087421) discloses some bicyclic compounds as pest control agents and one type of general structure of this publication is represented by the formula (B) :

However, this publication nowhere includes compounds of the present invention.

Citation List

Patent Literature

PTL-1: JP 2011-042611

PTL-2: WO 2016/087421

Summary of Invention

Technical Problem

An object of the present invention is to provide a novel amide compound or a salt thereof that exhibits miticidal activity.

Another object of the present invention is to provide a method for producing the amide compound or the salt thereof.

A further object of the present invention is to provide a new type of miticide containing the amide compound or the salt thereof.

Solution to Problem

The present inventors conducted extensive research to achieve the above objects, and succeeded in synthesizing a compound represented by the following Formula (1) or a salt thereof that has miticidal activity. The present inventors have conducted further research based on the above findings. The present invention has thereby been accomplished.

More specifically, the present invention includes the following embodiments:

Item 1: An amide compound represented by Formula (1)

or a salt thereof,

wherein R 1 represents C 1 _ 6 alkyl or C 1 _ 6 haloalkyl;

R 2 and R 3 are identical or different and each represents hydrogen, halogen, cyano, nitro, C 1 _ 6 alkyl, C 1 _ 6 haloalkyl, C 1 _ 6 alkoxy, C 1 _ 6 haloalkoxy, C 1 _ 6 alkoxy C 1 _ 6 alkyl, C 1 _ 6 haloalkoxy C 1 _ 6 alkyl;

Q represents Q-1 or Q-2:

wherein R 4 represents hydrogen, hydroxyl, formyl, cyano, C 1 _ 6 alkyl, C 1 _ 6 haloalkyl, C 1 _ 6 alkoxy, C 1 _ 6 haloalkoxy, C 1 _ 6 alkoxy C 1 _ 6 alkyl, C 3 _ 8 cycloalkyl, C 3 _ 8 cycloalkyl C 1 _ 6 alkyl, C 1 _ 6 alkylcarbonyl, C 1 _ 6 haloalkylcarbonyl, C 1 _ 6 alkoxycarbonyl, C 1 _ 6 haloalkoxycarbonyl, arylcarbonyl, aryloxycarbonyl, cyano C 1 _ 6 alkyl, C 2-6 alkenyl, C 2-6 haloalkenyl, cyano C 2-6 alkenyl, C 2-6 alkynyl, C 2-6 haloalkynyl, cyano C 2-6 alkynyl, C 1 _ 6 alkylsulfonyl, C 1 _ 6 haloalkylsulfonyl, C 1 _ 6 alkylsulfinyl, C 1 _ 6 haloalkylsulfinyl, C 2-6 alkenyloxy, C 2-6 alkynyloxy, aryl, aryl C 1 _ 6 alkyl, aryloxy, arylsulfonyl, arylsulfinyl, heteroaryl, all the substituents defined as R 4 may optionally be further substituted;

R 5 and R 6 are identical or different and each represents hydrogen, halogen, C 1 _ 6 alkyl, or C 1 _ 5 haloalkyl; R 5 and R 6 , taken together with the carbon atom, may bond to each other to form a 3- to 7-membered ring, via or not via at least one heteroatom;

R 7 represents hydrogen, C 1 _ 6 alkyl, C 1 _ 6 haloalkyl, C 1 _ 6 alkoxy, C 1 _ 6 haloalkoxy, C 1 _ 6 alkoxy C 1 _ 6 alkyl, C 1 _ 6 haloalkoxy C 1 _ 6 alkyl, C 1 _ 6 alkylcarbonyl, C 1 _ 6 haloalkylcarbonyl, C 1 _ 6 alkoxycarbonyl, C 1 _ 6 haloalkoxycarbonyl, C 2-6 alkenyl, C 2-6 haloalkenyl, C 2-6 cyanoalkenyl, C 2-6 alkynyl, C 2-6 haloalkynyl, C 2-6 cyanoalkynyl, C 3 _ 8 cycloalkyl, C 3 _ 8 cycloalkyl C 1 _ 6 alkyl, C 1 _ 6 alkylsulfonyl, C 1 _ 6 alkylsulfinyl, C 1 _ 6 haloalkylsulfonyl, C 1 _ 6 haloalkylsulfinyl, C 3 _ 8 cycloalkylsulfonyl, C 3 _ 8 cycloalkylsulfinyl, C 3 _ 8 cycloalkyl C 1 _ 6 alkylsulfonyl, C 3 _ 8 cycloalkyl C 1 _ 6 alkylsulfinyl, C 2-6 alkenyloxy, C 2-6 alkynyloxy, C 2-6 haloalkenyloxy, C 2-6 haloalkynyloxy, aryloxy, aryl C 1 _ 6 alkoxy, heteroaryloxy, heteroaryl C 1 _ 6 alkoxy, substituted or unsubstituted aryl, substituted or unsubstituted aryl C 1 _ 6 alkyl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heteroaryl C 1 _ 6 alkyl, substituted or unsubstituted heterocyclic group, substituted or unsubstituted amino, the groups represented as R 7 may optionally be further substituted with any substituents;

HET is a 5- or 6-membered heteroaryl, wherein the ring member atoms of the heteroaryl include besides carbon atoms 1, 2, 3 or 4 heteroatoms selected from N, 0 and S, and wherein the heteroaryl is unsubstituted or carries 1, 2, 3 or 4 identical or different groups R 8 ;

R 8 represents hydrogen, halogen, nitro, cyano, hydroxyl, formyl, substituted or unsubstituted amino, C 1 _ 6 alkyl, C 1 _ 6 haloalkyl, C 1 _ 6 alkoxy, C 1 _ 6 haloalkoxy, C 1 _ 6 alkoxy C 1 _ 6 alkyl, C 1 _ 6 haloalkoxy C 1 _ 6 alkyl, C 1 _ 6 alkoxycarbonyl, C 1 _ 6 haloalkoxycarbonyl, C 1 _ 6 cyanoalkyl, C 1 _ 6 cyanoalkoxy, C 2-6 alkenyl, C 2-6 haloalkenyl, C 2-6 cyanoalkenyl, C 2-6 alkynyl, C 2-6 haloalkynyl, C 2-6 cyanoalkynyl, C 3 _ 8 cycloalkyl, C 3 _ 8 cycloalkyl C 1 _ 6 alkyl, C 1 _ 6 alkylthio, C 1 _ 6 haloalkylthio, C 3 _ 8 cycloalkylthio, C 3 _ 8 cycloalkyl C 1 _ 6 alkylthio, C 1 _ 6 alkoxyalkylthio, C 1 _ 6 alkylsulfonyl, C 1 _ 6 alkylsulfinyl, C 1 _ 6 haloalkylsulfonyl, C 1 _ 6 haloalkylsulfinyl, C 3 _ 8 cycloalkylsulfonyl, C 3 _ 8 cycloalkylsulfinyl, C 3 _ 8 cycloalkyl C 1 _ 6 alkylsulfonyl, C 3 _ 8 cycloalkyl C 1 _ 6 alkylsulfinyl, C 2-6 alkenyloxy, C 2-6 alkynyloxy, C 2-6 haloalkenyloxy, C 2-6 haloalkynyloxy, C 1 _ 6 alkylsulfonyloxy, C 1 _ 6 alkylsulfinyloxy, C 1 _ 6 alkylcarbonyl, C 1 _ 6 haloalkylcarbonyl, carboxyl, OCN, SCN, SF 5 , substituted or unsubstituted aryloxy, substituted or unsubstituted aryl C 1 _ 6 alkoxy, substituted or unsubstituted arylthio, substituted or unsubstituted aryl C 1 _ 6 alkylthio, substituted or unsubstituted arylsulfonyl, substituted or unsubstituted arylsulfinyl, substituted or unsubstituted heteroaryloxy, substituted or unsubstituted arylsulfonyloxy, substituted or unsubstituted arylsulfinyloxy, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, or substituted or unsubstituted heterocyclic group, the groups represented as R 8 may optionally be further substituted;

or two radicals R 8 that are bound to adjacent ring member atoms of the Het group may form together with said ring member atoms a fused ring system, in such a case, HET is fused with 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocycle, wherein the ring member atoms of the fused heterocycle include besides carbon atoms 1, 2, 3 or 4 heteroatoms selected from the group of N, 0 and S, or with a substituted or unsubstituted aryl and wherein the fused carbocycle or heterocycle is unsubstituted or carries 1, 2, 3 or 4 identical or different radicals groups R 8 ;

X represents oxygen or sulfur; and

n represents an integer of 0 to 2.

Item 2 :

The amide compound or the salt thereof according to Item 1, wherein Q is Q-l as represented by 1A:

Item 3:

The amide compound or the salt thereof according to Item 1, wherein Q is Q-2 as re resented by IB:

Item 4: The amide compound or the salt thereof according to Item 2, wherein HET is substituted or unsubstituted pyrazole, substituted or unsubstituted thiazole or substituted or unsubstituted pyridine .

Item 5:

The amide compound or the salt thereof according to Item 3, wherein R 7 is substituted or unsubstituted aryl or substituted or unsubstituted aryl C 1-4 alkyl.

Item 6:

The amide compound or the salt thereof according to any of

Items 1 to 5, wherein R 1 is C 1 _ 6 haloalkyl.

Item 7 :

The amide compound or the salt thereof according to any one of Items 1 to 5, wherein R 2 and R 3 are identical or different and each represents halogen, cyano, or C 1 _ 6 alkyl.

Item 8:

The amide compound or the salt thereof according to any one of Items 1 to 5, wherein R 4 is hydrogen, C 1 _ 6 alkyl, or C 1 _ 6 alkylcarbonyl .

Item 9:

The amide compound or the salt thereof according to any one of the preceding items, wherein the amide compound is represented

(lA-la) ,

R 3 represents halogen;

R 4 represents hydrogen, C 1 _ 6 alkyl, or C 1 _ 6 alkylcarbonyl;

R 5 and R 6 are identical or different and each represent hydrogen, halogen, or C 1 _ 6 alkyl;

X represents 0 or S;

X 1 , X 2 , and X 3 are identical or different and each represent halogen;

HET represents pyrazolyl, thiazolyl, pyridyl, or imidazolyl, wherein the pyrazolyl, thiazolyl, pyridyl, and imidazolyl are unsubstituted or carry 1, 2, 3, or 4 identical or different groups R 8 ;

R 8 represents hydrogen, halogen, nitro, cyano, C 1 _ 6 alkyl, C 1 _ 6 haloalkyl, C 1 _ 6 alkoxy, C 1 _ 6 haloalkoxy, C 1 _ 6 alkylthio, C 1 _ 6 haloalkylthio, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl, the groups represented as R 8 may optionally be further substituted;

or two radicals R 8 that are bound to adjacent ring member atoms of the Het group may form together with said ring member atoms a fused ring system, in such a case, HET is fused with a substituted or unsubstituted aryl and wherein the fused carbocycle is unsubstituted or carries 1, 2, 3 or 4 identical or different groups R 8 ; and

n represents an integer of 0 to 2.

Item 10:

The amide compound or the salt thereof according to any one of the preceding items, wherein R 5 and R 6 are identical or different and each represent hydrogen, fluorine, chlorine, bromine, or C 1 _ 6 alkyl.

Item 11:

The amide compound or the salt thereof according to any one of the preceding items, wherein R 5 and R 6 are identical or different and each represent hydrogen, fluorine, chlorine, or C 1 _ 6 alkyl.

Item 12 :

The amide compound or the salt thereof according to any one of the preceding items, wherein R 5 and R 6 are identical or different and each represent hydrogen, fluorine, or C 1 _ 6 alkyl.

Item 13:

The amide compound or the salt thereof according to any one of the preceding items, wherein R 5 and R 6 are identical or different and each represent hydrogen, fluorine, methyl, or ethyl. Item 14:

The amide compound or the salt thereof according to any one of the preceding items, wherein R 4 represents hydrogen, methyl, ethyl, or acetyl.

Item 15:

The amide compound or the salt thereof according to any one of the preceding items, wherein X is 0.

Item 16:

The amide compound or the salt thereof according to any one of the preceding items, wherein R 3 is fluorine, chlorine, or bromine .

Item 17:

The amide compound or the salt thereof according to any one of the preceding items, wherein R 3 is fluorine or chlorine.

Item 18:

The amide compound or the salt thereof according to any one of the preceding items, wherein R 3 is fluorine.

Item 19:

The amide compound or the salt thereof according to any one of the preceding items, wherein X 1 , X 2 , and X 3 are identical or different and each represent fluorine, chlorine, or bromine.

Item 20:

The amide compound or the salt thereof according to any one of the preceding items, wherein X 1 , X 2 , and X 3 are identical or different and each represent fluorine or chlorine.

Item 21:

The amide compound or the salt thereof according to any one of the preceding items, wherein n represents 0 or 1.

Item 22 :

The amide compound or the salt thereof according to any one of the preceding items, wherein n represents 0.

Item 23:

The amide compound or the salt thereof according to any one of the preceding items, wherein HET represents

where a bond

intersected with a wavy line indicates the point of attachment to the parent molecule;

R A1 , R A4 , and R A5 are identical or different and each represent hydrogen, halogen, nitro, cyano, C 1 _ 6 alkyl, C 1 _ 6 haloalkyl, pyridyl, or phenyl, wherein the pyridyl and phenyl are unsubstituted or substituted with one to three substituents selected from the group consisting of halogen, C 1 _ 6 alkyl, C 1 _ 6 haloalkyl, C 1 _ 6 haloalkoxy, and C 1 _ 6 alkylthio; and

R A2 and R A3 are identical or different and each represent hydrogen, C 1 _ 6 alkyl, C 1 _ 6 haloalkyl, nitro, pyridyl, or thienyl;

R A6 , R A7 , R A8 , R A9 , R A1 °, and R A12 are identical or different and each represent hydrogen, halogen, C 1 _ 6 alkyl, or C 1 _ 6 haloalkyl; R A11 and R A13 are identical or different and each represent hydrogen, halogen, nitro, C 1 _ 6 alkyl, or C 1 _ 6 haloalkyl;

k represents an integer of 0 to 4; and

m represents an integer of 0 to 4.

Item 23A:

The amide compound or the salt thereof according to any one of the preceding items, wherein the amide compound is represented by Formula (ΙΑ-la) :

R represents halogen; R 4 represents hydrogen, methyl, or ethyl;

R 5 and R 6 are hydrogen, fluorine, methyl, or ethyl;

X represents 0;

X 1 , X 2 , and X 3 represent fluoro;

HET represents

or where a bond intersected with a wavy line indicates the point of attachment to the parent molecule;

R A1 represents nitro, chloro, cyano, bromo, trifluoromethyl, trifluoromethyl-substituted phenyl, trifluoromethoxy-substituted phenyl or fluoro-substituted phenyl;

R A2 and R A3 represent hydrogen, methyl, trifluoromethyl, ethyl, isopropyl, tert-butyl, or pyridyl;

R A4 represents halogen, 3, 5-dichlorophenyl, 3-chlorophenyl, 3- trifluoromethoxyphenyl, or 3-trifluoromethylphenyl;

R A5 represents hydrogen, halogen, C 1 _ 6 haloalkyl, unsubstituted phenyl, trifluoromethyl-substituted phenyl, or trifluoromethoxy- substituted phenyl;

R A6 , R A7 , and R A8 represent hydrogen; and

n represents an integer of 0 to 2.

Item 24:

The amide compound or the salt thereof according to any one of the preceding items, wherein the amide compound is represented by Formula (lA-la) :

R 3 represents halogen;

R 4 represents hydrogen or methyl;

R 5 and R 6 are hydrogen; X represents 0;

X 1 , X 2 , and X 3 represent fluoro;

, where a bond intersected with a wavy line indicates the point of attachment to the parent molecule;

R al represents trifluoromethoxy-substituted phenyl or fluoro- substituted phenyl;

R A2 and R A3 represent methyl;

R A4 represents halogen;

R A5 represents thienyl;

R A6 , R A7 , and R A8 represent hydrogen; and

n represents an integer of 0 to 2.

Item 25:

An amide compound selected from the group consisting of compounds 1A -1-2, lA-1-3, 1A -1- 8, 1A- 1-9, lA-1- 10, lA-1- 11, lA-1-

12, lA-1- 13, lA-1- -14, lA-1-15, 1A -1-16, lA-1-17 , ΙΑ-1-ΐε , lA-1-21 lA-1-24, 1A- 1-26, lA-1-27, 1A- -1- 29, lA-1-30, lA-1-32, 1A- 1-33, lA-1-35, 1A- 1-36, lA-1-39, 1A- -1- 40, lA-1-43, lA-1-48, 1A- 1-49, lA-1-52, 1A- 1-53, lA-1-54, 1A- -1- 55, lA-1-56, lA-1-57, 1A- 1-58, lA-1-60, 1A- 1-61, lA-1-62, 1A- -1- 63, lA-1-65, lA-1-66, 1A- 1-67, lA-1-68, 1A- 1-69, lA-1-70, 1A- -1- 71, lA-1-72, lA-1-73, 1A- 1-76, lA-1-77, 1A- 1-82, lA-1-83, 1A- 1- 84, lA-1-85, lA-1-86, 1A- 1-87, lA-1-88, 1A- 1-89, lA-1-91, 1A- -1- 92, lA-1-93, lA-1-94, 1A- 1-95, lA-1-96, 1A- 1-98, lA-1-100, 1A -1 -101 , lA-1-102, lA-1-103, lA-1-

104, lA-1-105, lA-1-106, lA-1-107, lA-1-108, lA-1-109, lA-1-110, lA-1-111, lA-1-112, lA-1-113, lA-1-114, lA-1-115, lA-1-116, lA-1- 117, lA-1-118, lA-1-119, lA-1-123, lA-1-127, lA-1-128, lA-1-130, lA-1-131, lA-1-132, lA-1-133, lA-1-134, lA-1-139, lA-1-140, lA-1- 141, lA-1-144, lA-1-147, lA-1-151, lA-1-152, lA-1-153, lA-1-154, lA-1-155, lA-1-157, lA-1-158, lA-1-160, lA-1-161, lA-1-162, lA-1- 163, lA-1-165, lA-1-169, lA-1-174, lA-1-175, lA-1-176, lA-1-186, lA-1-189, lA-1-191, lA-1-192, lA-1-194, lA-1-195, lA-1-197, lA-1- 198, lA-1-199, lA-1-200, lA-1-201, lA-1-203, lA-1-205, lA-1-211, lA-1-212, lA-1-213, lA-1-214, lA-1-217, lA-1-218, lA-1-219, lA-1- 220, lA-1-221, lA-1-222, lA-1-223, lA-1-225, lA-1-226, lA-1-227, lA-1-229, lA-1-230, lA-1-231, lA-1-232, and lA-1-233, or a salt thereof .

Item 25A:

An amide compound selected from the group consisting of compounds lA-1-2, lA-1-3, lA-1-10, lA-1-11, lA-1-12, lA-1-13, 1A- 1-14, lA-1-15, lA-1-16, lA-1-24, lA-1-29, lA-1-30, lA-1-35, lA-1- 40, lA-1-43, lA-1-49, lA-1-52, lA-1-53, lA-1-57, lA-1-58, lA-1-61, lA-1-62, lA-1-66, lA-1-67, lA-1-68, lA-1-69, lA-1-70, lA-1-71, lA-1-72, lA-1-73, lA-1-76, lA-1-77, lA-1-84, lA-1-85, lA-1-86, lA-1-87, lA-1-88, lA-1-95, lA-1-96, lA-1-98, lA-1-100, lA-1-101, lA-1-102, lA-1-104, lA-1-105, lA-1-106, lA-1-107, lA-1-108, lA-1- 109, lA-1-110, lA-1-111, lA-1-112, lA-1-113, lA-1-114, lA-1-115, lA-1-116, lA-1-117, lA-1-118, lA-1-119, lA-1-127, lA-1-128, lA-1- 130, lA-1-132, lA-1-134, lA-1-140, lA-1-141, lA-1-144, lA-1-153, lA-1-165, lA-1-169, lA-1-174, lA-1-175, lA-1-176, lA-1-186, lA-1- 192, lA-1-194, lA-1-195, lA-1-197, lA-1-198, lA-1-199, lA-1-200, lA-1-201, lA-1-211, lA-1-212, lA-1-213, lA-1-214, lA-1-217, lA-1- 218, lA-1-219, lA-1-220, lA-1-221, lA-1-223, lA-1-225, lA-1-226, lA-1-227, lA-1-229, lA-1-230, lA-1-231, and lA-1-232, or a salt thereof.

Item 26:

An amide compound selected from the group consisting of compounds lA-1-24, lA-1-122, lA-1-177, and lA-1-204, or a salt thereof .

Item 27:

The amide compound or the salt thereof according to any one of the preceding items, wherein the amide compound is represented by Formula (IB-la) :

R 3 represents halogen;

R 4 represents hydrogen or C 1 _ 6 alkyl;

R 5 and R 6 are identical or different and each represent hydrogen or C 1 _ 6 alkyl;

X represents 0 or S;

X 1 , X 2 , and X 3 are identical or different and each represent halogen;

are identical or different and each

represents hydrogen, halogen, C 1 _ 6 alkyl, C 1 _ 6 alkoxy, C 1 _ 6 haloalkyl, C 1 _ 6 haloalkoxy, C 1 _ 6 alkylthio, C 1 _ 6 ha'loalkylthio, or phenyl, wherein the phenyl is substituted with one to five substituents selected from the group consisting of halogen, C 1 _ 6 alkyl, C 1 _ 6 haloalkyl, C 1 _ 6 haloalkoxy, and C 1 _ 6 alkylthio; and n represents 0 or 1.

Item 28:

The amide compound or the salt thereof according to any one of the preceding items, wherein R 5 and R 6 are identical or different and each represent hydrogen or methyl.

Item 29:

The amide compound or the salt thereof according to any one of the preceding items, wherein R 4 represents hydrogen, methyl, ethyl, n-propyl, or isopropyl.

Item 30:

The amide compound or the salt thereof according to any one of the preceding items, wherein X is 0.

Item 31:

The amide compound or the salt thereof according to any one of the preceding items, wherein R 3 is fluorine, chlorine, or bromine. Item 32:

The amide compound or the salt thereof according to any one of the preceding items, wherein R 3 is fluorine or chlorine.

Item 33:

The amide compound or the salt thereof according to any one of the preceding items, wherein R 3 is fluorine.

Item 34:

The amide compound or the salt thereof according to any one of the preceding items, wherein X 1 , X 2 , and X 3 are identical or different and each represent fluorine, chlorine, or bromine.

Item 35:

The amide compound or the salt thereof according to any one of the preceding items, wherein X 1 , X 2 , and X 3 are identical or different and each represent fluorine or chlorine.

Item 36:

The amide compound or the salt thereof according to any one of the preceding items, wherein n represents 0.

Item 36A:

The amide compound or the salt thereof according to any one of the preceding items, wherein the amide compound is represented by Formula (IB-la) :

R 3 represents halogen;

R 4 represents hydrogen, methyl, ethyl, n-propyl, or isopropyl; R 5 and R 6 are hydrogen;

X represents 0;

X 1 , X 2 , and X 3 represent fluoro;

R B3 is fluoro and R B1 , R B2 , R B4 , and R B5 are hydrogen, or

one of R B1 , R B2 , R B3 , and R B5 is chloro and the others are hydrogen, or R B2 is trifluoromethyl, trifluoromethoxy, trifluoromethylthio, 2- trifluoromethylphenyl, 3-trifluoromethylphenyl, 4- trifluoromethylphenyl, 3-trifluoromethoxyphenyl, or 4- trifluoromethoxyphenyl, and R B1 , R B3 , R B4 , and R B5 are hydrogen, or R B3 is trifluoromethyl, trifluoromethoxy, methylthio, trifluoromethylthio, 3-chlorophenyl, 2-trifluoromethylphenyl, 3- trifluoromethylphenyl, 4-trifluoromethylphenyl, 3- trifluoromethoxyphenyl, 4-trifluoromethoxyphenyl, pentafluorophenyl, 2 , 4-dichlorophenyl, 2,4-di- (trifluoromethyl) phenyl, 3-choloro-4-trifluoromethyl-phenyl, 3,4- difluorophenyl, or 3, 5-di- (trifluoromethyl) phenyl, and R B1 , R B2 , R B4 , and R B5 are hydrogen; and

n represents 0 or 1.

Item 36B:

The amide compound or the salt thereof according to any one of the preceding items, wherein the amide compound is represented by Formula (IB-la) :

R 4 represents hydrogen, methyl, ethyl, n-propyl, or isopropyl; R 5 and R 6 are hydrogen;

X represents 0;

X 1 , X 2 , and X 3 represent fluoro;

two of R B1 , R B2 , R B3 , R B4 , and R B5 are chloro and the others are hydrogen, or

R B3 represents hydrogen, halogen, methoxy, trifluoromethyl, trifluoromethoxy, methylthio, trifluoromethylthio, trifluoromethyl-substituted phenyl, or trifluoromethoxy- substituted phenyl and R B1 , R B2 , R B4 , and R B5 are hydrogen; and n represents 0 or 1. Item 37:

The amide compound or the salt thereof according to any one of the preceding items, wherein the amide compound is represented by Formula (IB-la) :

R represents halogen;

R 4 represents hydrogen, methyl, or ethyl;

R 5 and R 6 are hydrogen;

X represents 0;

X 1 , X 2 , and X 3 represent fluoro;

two of R B1 , R B2 , R B3 , R B4 and R are chloro and the othe hydrogen, or

R B2 represents trifluoromethyl-substituted phenyl and R B1 ( R B3 R B4 and R B5 are hydrogen; and

n represents 0 or 1.

Item 38:

The amide compound or the salt thereof according to any one of the preceding items, wherein the amide compound is represented by Formula (IB-la) :

R represents halogen;

R 4 represents hydrogen;

R 5 and R 6 are hydrogen;

X represents 0;

X 1 , X 2 , and X 3 represent fluoro; two of R B1 , R B2 , R B3 , R B4 , and R B5 are chloro and the others are hydrogen, or

R B3 represents hydrogen, methoxy, or trifluoromethoxy and R B1 , R B2 , R B4 , and R B5 are hydrogen; and

n represents 0 or 1.

Item 39:

amide compound selected from the group consisting

An amide compound selected from the group consisting of compounds lB-1-2, lB-1-7, lB-1-9, and lB-1-10, or a salt thereof. Item 42:

The amide compound or the salt thereof according to any one of the preceding items, wherein the amide compound is represented b Formula (lB-2a) :

R 3 represents halogen;

R 4 represents hydrogen or C 1 _ 6 alkyl;

X represents 0 or S;

X 1 , X 2 , and X 3 are identical or different and each represent halogen;

R 7 represents C 1 _ 6 alkyl, C 1 _ 6 haloalkyl, substituted or unsubstituted pyridyl, or substituted or unsubstituted phenyl. Item 43:

The amide compound or the salt thereof according to any one of the preceding items, wherein R 4 represents hydrogen, methyl, or ethyl .

Item 44:

The amide compound or the salt thereof according to any one of the preceding items, wherein X is 0.

Item 45:

The amide compound or the salt thereof according to any one of the preceding items, wherein R 3 is fluorine, chlorine, or bromine.

Item 46:

The amide compound or the salt thereof according to any one of the preceding items, wherein R 3 is fluorine or chlorine.

Item 47:

The amide compound or the salt thereof according to any one of the preceding items, wherein R 3 is fluorine.

Item 48: The amide compound or the salt thereof according to any one of the preceding items, wherein X 1 , X 2 , and X 3 are identical or different and each represent fluorine, chlorine, or bromine.

Item 49:

The amide compound or the salt thereof according to any one of the preceding items, wherein X 1 , X 2 , and X 3 are identical or different and each represent fluorine or chlorine.

Item 50:

The amide compound or the salt thereof according to any one of the preceding items, wherein R 7 represents C 1 _ 6 alkyl, C 1 _ 6 haloalkyl, pyridyl, or phenyl, wherein the phenyl is substituted with one to five substituents selected from the group consisting of halogen, C 1 _ 6 alkyl, C 1 _ 6 haloalkyl, C 1 _ 6 haloalkoxy, C 1 _ 6 alkylthio, and C 1 _ 6 haloalkylthio .

Item 51:

An amide compound selected from the group consisting of compounds 1B-2-3, 1B-2-5, 1B-2-6, 1B-2-7, 1B-2-17, 1B-2-18, 1B-2- 21, 1B-2-25, 1B-2-29, 1B-2-31, 1B-2-32, 1B-2-33, 1B-2-37, 1B-2-38, 1B-2-49, 1B-2-50, 1B-2-51, 1B-2-52, 1B-2-59, and 1B-2-60, or a salt thereof.

Item 52 :

A method for producing the amide compound or the salt thereof according to any one of the preceding items, comprising at least one step selected from the group consisting of following steps (d) and (e) :

Step (d) : obtaining the sulfide compound represented by Formula (ΙΑ-a) by reacting a thiol compound represented by Formula (6) with an alkylating reagent represented by Formula (7) :

wherein R 1 , R 2 , R 3 , R% R 5 , R 6 , X and HET are as defined above and G represents a leaving group; and

Step (e) : obtaining an amide compound represented by Formula (ΙΑ-b) by reacting the sulfide compound represented by Formula (ΙΑ-a) with an oxidizing agent:

(1A-a) (1A-b) wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , X and HET are as defined above n' represents 1 or 2.

Item 53:

The method for producing the amide compound or the salt thereof according to any one of the preceding items, further comprising the following step (c) :

Step (c) : obtaining a thiol compound represented by Formula (6) by reacting a sulfonylchloride compound represented by Formula (5) with a reducing agent:

(5) (6)

wherein R 2 , R 3 , R 4 , R 5 , R 6 , X and HET are as defined above.

Item 54:

The method for producing the amide compound or the salt thereof according to any one of the preceding items, further comprising the following step (b) :

Step (b) : obtaining the sulfonylchloride compound represented by Formula (5) by chlorosulfonylating a heteroaryl acetamide compound represented by Formula (4) :

(4) (5) wherein R 2 , R 3 , R 4 , R 5 , R 6 , X and HET are as defined above. Item 55:

The method for producing the amide compound or the salt thereof according to any one of the preceding items, further comprising the following step (a) :

Step (a) : obtaining the heteroaryl acetamide compound represented by Formula (4) by reacting an aniline compound represented by Formula (2) with a heteroarylalkyl carbonyl compound represented by Formula (3) :

(2) (3) (4)

wherein R 2 , R 3 , R 4 , R 5 , R 6 , X and HET are as defined above and Y represents a leaving group or hydroxyl group.

Item 56:

A pesticide containing the amide compound or the salt thereof according to any one of the preceding items.

Item 57 :

A mxticide containing the amide compound or the salt thereof according to any one of the preceding items .

Item 58:

An aphicide containing the amide compound or the salt thereof according to any one of the preceding items.

Advantageous Effects of Invention

The amide compound or the salt thereof according to the present invention achieves an excellent miticidal effect with a small amount thereof. With the present invention, the amide compound and the salt thereof can simply be produced with an excellent yield.

Additionally, with the present invention, a new type of miticide containing the amide compound or the salt thereof according to the present invention can be provided.

Description of Embodiments

The present invention is described hereinafter. Throughout the entire specification, a singular expression should be understood as encompassing the concept thereof in the plural form unless specifically noted otherwise. Thus, singular articles (e.g., "a", "an", "the" and the like in case of English) should also be understood as encompassing the concept thereof in the plural form unless specifically noted otherwise. Further, the terms used herein should be understood as being used in the meaning that is commonly used in the art, unless specifically noted otherwise. Thus, unless defined otherwise, all terminologies and scientific technical terms that are used herein have the same meaning as the terms commonly understood by those skilled in the art to which the present invention pertains. In case of a contradiction, the present specification (including the definitions) takes precedence.

1. Amide compound or a salt thereof

The present invention is directed to a compound represented by Formula (1) :

or a salt thereof (hereinafter sometimes referred to as "amide (1) of the present invention" or "compound (1)"),

wherein R 1 , R 2 , R 3 , Q and n are as defined above.

Next, the terms in the present specification are described below .

In the present specification, the number of substituents of a group defined by "optionally substituted" or "substituted" is not particularly limited if it is substitutable, and is one or plural. In addition, unless otherwise indicated, the description for each group is also applied when the group is one part of or a substituent on other groups .

"C 1 _ 6 alkyl" means a linear or branched, saturated hydrocarbon group having one to six carbon atoms .

"C 1 -4 alkyl" means a linear or branched, saturated hydrocarbon group having one to four carbon atoms .

"C 2-6 alkenyl" means a linear or branched, unsaturated hydrocarbon group having two to six carbon atoms and containing one to three double bonds .

"C 2-6 alkynyl" means a linear or branched, unsaturated hydrocarbon group having two to six carbon atoms and containing one triple bond.

"C 3 _ 8 cycloalkyl" means a cyclic alkyl having three to eight carbon atoms, and includes those cyclic alkyl having a partially bridged structure.

"C 1 _ 6 alkoxy" refers to a "C 1 _ 6 alkyloxy group", and the "C 1 _ 6 alkyl" moiety is defined the same as the above-described "C 1 _ 6 alkyl".

"Aryl" means a monocyclic or polycyclic aromatic hydrocarbon. "Heterocyclic" means a saturated, unsaturated, or aromatic heterocyclic group which has at least one of nitrogen, oxygen, phosphorus and/or sulfur atoms in the ring and may be bonded at any substitutable position.

"Heteroaryl" means an aromatic heterocyclic group which has at least one of nitrogen, oxygen, and/or sulfur atoms in the ring and may be bonded at any substitutable position, wherein the ring member atoms of the heteroaryl include besides carbon atoms 1, 2, 3 or 4 heteroatoms selected from N, 0 and S.

The following shows specific examples of each group as used in this specification.

Examples of halogen include, but are not particularly limited to, fluorine, chlorine, bromine, iodine, and the like. Examples of C 1 _ 6 alkyl include, but are not particularly limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, n-hexyl, and like C 1 _ 6 straight- chain or branched-chain alkyl.

Examples of C 1 _ 6 haloalkyl include, but are not particularly limited to, fluoromethyl, chloromethyl, bromomethyl, iodomethyl, difluoromethyl, 2, 2-difluoroethyl, trifluoromethyl, 2,2,2- trifluoroethyl, pentafluoroethyl, 3, 3, 3-trifluoropropyl, 4,4,4- trifluorobutyl, heptafluoroisobutyl, and like C 1 _ 6 straight-chain or branched-chain alkyl substituted with 1 to 9, and preferably 1 to 5, halogen atoms.

Examples of C 1 _ 6 alkoxy include, but are not particularly limited to, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, and like C 1 _ 6 straight-chain or branched-chain alkoxy.

Examples of C 1 _ 6 haloalkoxy include, but are not particularly limited to, fluoromethoxy, chloromethoxy, bromomethoxy, iodomethoxy, difluoromethoxy, trifluoromethoxy, 2,2,2- trifluoroethoxy, pentafluoroethoxy, 3, 3, 3-trifluoropropoxy, 4, 4, 4-trifluorobutoxy, heptafluoroisobutoxy, and like C 1 _ 6 straight-chain or branched-chain alkoxy substituted with 1 to 9, preferably 1 to 5, halogen atoms.

Examples of C 1 _ 6 alkoxy C 1 _ 6 alkyl include, but are not particularly limited to, methoxymethyl, ethoxymethyl, n- propoxymethyl, isopropoxymethyl, n-butoxymethyl, isobutoxymethyl, sec-butoxymethyl, tert-butoxymethyl, methoxyethyl, ethoxyethyl, methoxy-n-propyl, methoxy-n-butyl, and like alkoxyalkyl in which C 1 _ 6 straight-chain or branched-chain alkyl is substituted with C 1 _ 6 straight-chain or branched-chain alkoxy.

Examples of C 1 _ 6 haloalkoxy C 1 _ 6 alkyl include, but are not particularly limited to, fluoromethoxymethyl, chloromethoxymethyl, bromomethoxymethyl, iodomethoxymethyl, difluoromethoxymethyl, trifluoromethoxymethyl, 2, 2, 2-trifluoroethoxymethyl, and like straight-chain or branched-chain alkoxyalkyl substituted with 1 to 9, preferably 1 to 5, halogen atoms. Examples of C 3 _ 8 cycloalkyl include, but are not particularly limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, and the like.

Examples of C 3 _ 8 cycloalkyl C 1 _ 6 alkyl include, but are not particularly limited to, cyclopropylmethyl, cyclobutylethyl, cyclopentylmethyl, cyclohexylmethyl, 1-cyclohexylethyl (i.e., CH(C 6 Hii) -CH 3 ) , and the like.

Examples of C 1 _ 6 alkylcarbonyl include, but are not particularly limited to, methylcarbonyl (acetyl) , ethylcarbonyl (propionyl) , n-propylcarbonyl (butyryl) , isopropylcarbonyl (isobutyryl) , n-butylcarbonyl (valeryl) , isobutylcarbonyl (isovaleryl) , see-butylcarbonyl, tert-butylcarbonyl, and like C 1 _ 6 straight-chain or branched-chain alkylcarbonyl groups.

Examples of C 1 _ 6 haloalkylcarbonyl include, but are not particularly limited to, fluoromethylcarbonyl, chloromethylcarbonyl, bromomethylcarbonyl, iodomethylcarbonyl, dichloromethylcarbonyl, trichloromethylcarbonyl, difluoromethylcarbonyl, trifluoromethylcarbonyl, chlorodifluoromethylcarbonyl, bromodifluoromethylcarbonyl, dichlorofluoromethylcarbonyl, 2, 2, 2-trichloroethylcarbonyl,

2, 2, 2-trifluoroethylcarbonyl, pentafluoroethylcarbonyl, and like C 1 _ 6 straight-chain or branched-chain alkylcarbonyl substituted with 1 to 9, and preferably 1 to 5, halogen atoms.

Examples of arylcarbonyl include, but are not particularly limited to, benzoyl, tert-butylbenzoyl, and like substituted or unsubstituted benzoyl group; 1-naphthoyl, 2- naphthoyl, and the like substituted or unsubstituted naphthoyl group.

Examples of aryloxycarbonyl include, but are not particularly limited to, phenoxycarbonyl, 4- diaminophenoxycarbonyl, 4-fluorophenoxycarbonyl, 4-tert- butylphenoxycarbonyl, and like substituted or unsubstituted phenoxycarbonyl group; 1-naphthoxycarbonyl, 2-naphthoxycarbonyl, and the like substituted or unsubstituted naphthoxycarbonyl group.

Examples of C 1 _ 6 alkoxycarbonyl include, but are not particularly limited to, methoxycarbonyl, ethoxycarbonyl, n- propoxycarbonyl, isopropoxycarbonyl, n-butoxycarbonyl, isobutoxycarbonyl, sec-butoxycarbonyl, tert-butoxycarbonyl, and like C 1 _ 6 straight-chain or branched-chain alkoxycarbonyl groups.

Examples of C 1 _ 6 haloalkoxycarbonyl include, but are not particularly limited to, fluoromethoxycarbonyl, chloromethoxycarbonyl , bromomethoxycarbonyl , iodomethoxycarbonyl , dichloromethoxycarbonyl , trichloromethoxycarbonyl , difluoromethoxycarbonyl, trifluoromethoxycarbonyl, 2,2,2- trifluoroethoxymethyl, pentafluoroethoxycarbonyl, 3,3,3- trifluoropropoxycarbonyl, 4 , 4 , 4-trifluorobutoxycarbonyl, heptafluoroisopropoxycarbonyl, and like C 1 _ 6 straight-chain or branched-chain alkoxycarbonyl substituted with 1 to 9, preferably 1 to 5, halogen atoms.

Examples of cyano C 1 _ 6 alkyl include, but are not particularly limited to, cyanomethyl, cyanoethyl, cyano-n-propyl, cyano-isopropyl, cyano-n-butyl, cyano-isobutyl, cyano-sec-butyl, cyano-tert-butyl, cyano-n-hexyl, and like C 1 _ 6 straight-chain or branched-chain alkyl substituted with a cyano group.

Examples of cyano C 1 _ 6 alkoxy include cyanomethoxy, cyanoethoxy, cyano-n-propoxy, cyano-isopropoxy, cyano-n-butoxy, cyano-iso-butoxy, cyano-sec-butoxy, cyano-tert-butoxy, cyano- hexyloxy, and like C 1 _ 6 straight-chain or branched-chain alkoxy substituted with a cyano group.

Examples of C 2-6 alkenyl include, but are not particularly limited to, vinyl, allyl, 2-butenyl, 3-butenyl, 1-methylallyl, and the like.

Examples of C 2-6 haloalkenyl include, but are not particularly limited to, 2, 2-dichlorovinyl, 2, 2-dibromovinyl, 2, 2-difluorovinyl, 3, 3-difluoro-2-allyl, 4, 4-difluoro-3-butenyl, 4 , 4 , 4-trifluoro-2-butenyl, and the like.

Examples of C 2-6 alkynyl include, but are not particularly limited to, ethynyl, 2-propynyl (propargyl) , l-methyl-2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1, l-dimethyl-2-propyn-l-yl (i.e., -C (CH 3 ) 2 -CCH) , and the like.

Examples of C 2-6 haloalkynyl include, but are not particularly limited to, fluoroethynyl, bromoethynyl, chloroethynyl, iodoethynyl, 3, 3, 3-trifluoro-l-propynyl, and the like.

Examples of C 2-6 cyanoalkenyl include, but are not particularly limited to, 2-cyanovinyl, 2, 2-dicyanovinyl, 3-cyano- 2-allyl, 3, 3-dicyano-2-allyl, 4-cyano-3-butenyl, 4, 4-dicyano-3- butenyl, 4 , 4 , 4-tricyano-2-butenyl, and the like.

Examples of C 2-6 cyanoalkynyl include, but are not particularly limited to, cyanoethynyl, 3-cyano-l-propynyl, 3,3,3- trifluoro-l-propynyl, and the like.

Examples of C 1 _ 6 alkylsulfonyl include, but are not particularly limited to, methylsulfonyl, ethylsulfonyl, n- propylsulfonyl, isopropylsulfonyl, n-butylsulfonyl, isobutylsulfonyl, sec-butylsulfonyl, tert-butylsulfonyl, and like C 1 _ 6 straight-chain or branched-chain alkylsulfonyl groups.

Examples of C 1 _ 6 haloalkylsulfonyl include, but are not particularly limited to, fluoromethylsulfonyl, chloromethylsulfonyl, bromomethylsulfonyl, iodomethylsulfonyl, dichloromethylsulfonyl, trichloromethylsulfonyl, difluoromethylsulfonyl, trifluoromethylsulfonyl, chlorodifluoromethylsulfonyl, bromodifluoromethylsulfonyl, dichlorofluoromethylsulfonyl, 2,2, 2-trichloroethylsulfonyl,

2, 2, 2-trifluoroethylsulfonyl, pentafluoroethylsulfonyl, and like C 1 _ 6 straight-chain or branched-chain alkylsulfonyl substituted with 1 to 9, and preferably 1 to 5, halogen atoms.

Examples of C 1 _ 6 alkylsulfinyl include, but are not particularly limited to, methylsulfinyl, ethylsulfinyl, n- propylsulfinyl, isopropylsulfinyl, n-butylsulfinyl, isobutylsulfinyl, sec-butylsulfinyl, tert-butylsulfinyl, and like C 1 _ 6 straight-chain or branched-chain alkylsulfinyl groups.

Examples of C 1 _ 6 haloalkylsulfinyl include, but are not particularly limited to, fluoromethylsulfinyl, chloromethylsulfinyl, bromomethylsulfinyl, iodomethylsulfinyl, dichloromethylsulfinyl, trichloromethylsulfinyl, difluoromethylsulfinyl, trifluoromethylsulfinyl, chlorodifluoromethylsulfinyl, bromodifluoromethylsulfinyl, dichlorofluoromethylsulfinyl, 2,2, 2-trichloroethylsulfinyl,

2, 2, 2-trifluoroethylsulfinyl, pentafluoroethylsulfinyl, and like C 1 _ 6 straight-chain or branched-chain alkylsulfinyl substituted with 1 to 9, and preferably 1 to 5, halogen atoms.

Examples of C 1 _ 6 alkylthio include, but are not particularly limited to, methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, sec-butylthio, tert-butylthio, and like C 1 _ 6 straight-chain or branched-chain alkylthio.

Examples of C 1 _ 6 haloalkylthio include, but are not particularly limited to, fluoromethylthio, chloromethylthio, bromomethylthio, iodomethylthio, dichloromethylthio, trichloromethylthio, difluoromethylthio, trifluoromethylthio, chlorodifluoromethylthio, bromodifluoromethylthio, dichlorofluoromethylthio, 2, 2, 2-trichloroethylthio, 2,2,2- trifluoroethylthio, pentafluoroethylthio, and like C 1 _ 6 straight- chain or branched-chain alkylthio substituted with 1 to 9, and preferably 1 to 5, halogen atoms.

Examples of C 3 _ 8 cycloalkylsulfonyl include, but are not particularly limited to, cyclopropylsulfonyl, cyclobutylsulfonyl, cyclopentylsulfonyl, cyclohexylsulfonyl, and the like.

Examples of C 3 _ 8 cycloalkylsulfinyl include, but are not particularly limited to, cyclopropylsulfinyl, cyclobutylsulfinyl, cyclopentylsulfinyl, cyclohexylsulfinyl, and the like.

Examples of C 3 _ 8 cycloalkylthio include, but are not particularly limited to, cyclopropylthio, cyclobutylthio, cyclopentylthio, cyclohexylthio, and the like.

Examples of C 3 _ 8 cycloalkyl C 1 _ 6 alkylsulfonyl include, but are not particularly limited to, cyclopropylmethylsulfonyl, 2- cyclopropylethylsulfonyl, 3-cyclopropylpropylsulfonyl, cyclohexylmethylsulfonyl, and the like.

Examples of C 3 _ 8 cycloalkyl C 1 _ 6 alkylsulfinyl include, but are not particularly limited to, cyclopropylmethylsulfinyl, 2- cyclopropylethylsulfinyl, 3-cyclopropylpropylsulfinyl, cyclohexylmethylsulfinyl, and the like. Examples of C 3 _ 8 cycloalkyl C 1 _ 6 alkylthio include, but are not particularly limited to, cyclopropylmethylthio, 2- cyclopropylethylthio, 3-cyclopropylpropylthio, cyclohexylmethylthio, and the like.

Examples of C 1 _ 6 alkoxy C 1 _ 6 alkylthio include, but are not particularly limited to, methoxymethylthio, ethoxymethylthio, n- propoxymethylthio, isopropoxymethylthio, n-butoxymethylthio, sec- butoxymethylthio, tert-butoxymethylthio, 2-methoxyethylthio, and like alkoxyalkylthio in which C 1 _ 6 straight-chain or branched- chain alkylthio is substituted with C 1 _ 6 straight-chain or branched-chain alkoxy.

Examples of C 2-6 alkenyloxy include, but are not particularly limited to, vinyloxy, 1-propenyloxy, isopropenyloxy, allyloxy, 2- butenyloxy, 3-butenyloxy, 1-methylallyloxy, and the like.

Examples of C 2-6 haloalkenyloxy include, but are not particularly limited to, 2, 2-dichlorovinyloxy, 2,2- dibromovinyloxy, 2, 2-difluorovinyloxy, 3, 3-difluoro-2-allyloxy, 4, 4-difluoro-3-butenyloxy, 4 , 4 , 4-trifluoro-2-butenyloxy, and the like.

Examples of C 2-6 alkynyloxy include, but are not particularly limited to, ethynyloxy, 2-propynyloxy, l-methyl-2-propynyloxy, 1, l-dimethyl-2-propynyloxy, 1-butynyloxy, 2-butynyloxy, 3- butynyloxy, and the like.

Examples of C 2-6 haloalkynyloxy include, but are not particularly limited to, fluoroethynyloxy, bromoethynyloxy, chloroethynyloxy, iodoethynyloxy, 3,3, 3-trifluoro-l-propynyloxy, and the like.

Examples of C 1 _ 6 alkylsulfonyloxy include, but are not particularly limited to, methylsulfonyloxy, ethylsulfonyloxy, n- propylsulfonyloxy, isopropylsulfonyloxy, n-butylsulfonyloxy, isobutylsulfonyloxy, sec-butylsulfonyloxy, tert-butylsulfonyloxy, and like C 1 _ 6 straight-chain or branched-chain alkylsulfonyl groups .

Examples of C 1 _ 6 alkylsulfinyloxy include, but are not particularly limited to, methylsulfinyloxy, ethylsulfinyloxy, n- propylsulfinyloxy, isopropylsulfinyloxy, n-butylsulfinyloxy, isobutylsulfinyloxy, see-butylsulfinyloxy, tert-butylsulfinyloxy, and like C 1 _ 6 straight-chain or branched-chain alkylsulfinyloxy groups .

Examples of substituted or unsubstituted amino include, but are not particularly limited to, amino, monoalkylamino, dialkylamino, monoacylamino, and the like. Examples of the alkyl include C 1 _ 6 alkyl mentioned above, and the like. Examples of the acyl include C 1 _ 6 alkoxycarbonyl, haloalkoxycarbonyl, arylcarbonyl mentioned above, and the like.

Examples of aryl include, but are not particularly limited to, phenyl, 1-naphthyl, 2-naphthyl, and the like.

Examples of aryl C 1 _ 6 alkyl include, but are not particularly limited to, benzyl, phenylethyl, phenyl-n-propyl, 1-methyl-l- phenyl-ethyl (i.e., -C (CH 3 ) 2 -C 6 H 5 ) , and the like. These aryl C 1 _ 6 alkyl can be further substituted at both the parts alkyl as well as aryl.

Examples of aryloxy include, but are not particularly limited to, phenoxy, 1-naphthyloxy, 2-naphthyloxy, and the like.

Examples of aryl C 1 _ 6 alkoxy include, but are not particularly limited to, benzyloxy, phenylethoxy, phenyl-n- propoxy, phenyl-n-butoxy, 1-naphthylmethoxy, 2-naphthylmethoxy, and like.

Examples of heteroaryloxy include, but are not particularly limited to, pyridinyloxy, pyrimidinyloxy, pyrazolyloxy, and the like.

Examples of heteroaryl C 1 _ 6 alkoxy include, but are not particularly limited to, pyridinylmethoxy, pyridinylethoxy, pyrimidinylethoxy, pyrazolylmethoxy, and like.

Examples of arylsulfonyl include, but are not particularly limited to, phenylsulfonyl, 1-naphthylsulfonyl, 2- naphthylsulfonyl, and the like.

Examples of arylsulfinyl include, but are not particularly limited to, phenylsulfinyl, 1-naphthylsulfinyl, 2- naphthylsulfinyl, and the like. Examples of arylthio include, but are not particularly limited to, phenylthio, 1-naphthylthio, 2-naphthylthio, and the like.

Examples of arylsulfonyloxy include, but are not particularly limited to, phenylsulfonyloxy, 1-naphthylsulfonyloxy, 2-naphthylsulfonyloxy, and the like.

Examples of arylsulfinyloxy include, but are not particularly limited to, phenylsulfinyloxy, l~naphthylsulfinyloxy, 2-naphthylsulfinyloxy, and the like.

Examples of aryl C 1 _ 6 alkylthio include, but are not particularly limited to, benzylthio, phenylethylthio, phenyl-n- propylthio, phenyl-n-butylthio, 1-naphthylmethylthio, 2- naphthylmethylthio, and the like.

Examples of HET which is basically a 5- or 6-membered heteroaryl include, but are not particularly limited to, thienyl, furyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, tetrazinyl, indolyl, isoindolyl, indazolyl, quinazolinyl, carbazolyl, benzoxazolyl, benzisoxazolyl, benzothiazolyl, benzisothiazolyl, benzimidazolyl, quinolinyl, isoquinolinyl, pyridoindolyl, cinnolinyl, phthalazinyl, quinoxalinyl, purinyl, phenothiazinylfuranyl, benzofuranyl, chromanyl, benzothienyl, and the like.

Examples of heteroaryl are similar but not limited to those mentioned above in HET examples.

Examples of heteroaryl C 1 _ 6 alkyl include, but are not particularly limited to, pyrazolylmethyl, thiazolylmethyl, oxazolylmethyl, 2-pyridylmethyl, 3-pyridylmethyl, 2- pyrazinylmethyl, pyrimidinylmethyl, 2-quinolinylmethyl, and the like. These heteroaryl C 1 _ 6 alkyl can be further substituted at both the parts alkyl as well as heteroaryl.

All the Aryls, Aryl C 1 _ 6 alkyls, Heteroaryls and Heteroaryl C 1 _ 6 alkyls, mentioned above may optionally be further substituted. Examples of the number of substituents include, but are not particularly limited to, 1 to 20 (preferably 1 to 10, and more preferably 1 to 5) .

Examples of a heterocyclic group include, but are not particularly limited to, thienyl, furyl, tetrahydrofuryl, dioxolanyl, dioxanyl, pyrrolyl, pyrrolinyl, pyrrolidinyl, oxazolyl, isoxazolyl, oxazolinyl, oxazolidinyl, isoxazolinyl, thiazolyl, isothiazolyl, thiazolinyl, thiazolidinyl, isothiazolinyl, pyrazolyl, pyrazolidinyl, imidazolyl, imidazolinyl, imidazolidinyl, oxadiazolyl, oxadiazolinyl, thiadiazolinyl, triazolyl, triazolinyl, triazolidinyl, tetrazolyl, tetrazolinyl, pyridyl, dihydropyridyl, tetrahydropyridyl, piperidyl, oxazinyl, dihydroxazinyl, morpholino, thiazinyl, dihydrothiazinyl, thiamorpholino, pyridazinyl, dihydropyridazinyl, tetrahydropyridazinyl, hexahydropyridazinyl, oxadiazinyl, dihydrooxadiazinyl, tetrahydrooxadiazinyl, thiadiazolyl, thiadiazinyl, dihydrothiadiazinyl, tetrahydrothiadiazinyl, pyrimidinyl, dihydropyrimidinyl, tetrahydropyrimidinyl, hexahydropyrimidinyl, pyrazinyl, dihydropyrazinyl, tetrahydropyrazinyl, piperazinyl, triazinyl, dihydrotriazinyl, tetrahydrotriazinyl, hexahydrotriazinyl, tetrazinyl, dihydrotetrazinyl, indolyl, indolinyl, isoindolyl, indazolyl, quinazolinyl, dihydroquinazolyl, tetrahydroquinazolyl, carbazolyl, benzoxazolyl, benzoxazolinyl, benzisoxazolyl, benzisoxazolinyl, benzothiazolyl, benzisothiazolyl, benzisothiazolinyl, benzimidazolyl, indazolinyl, quinolinyl, dihydroquinolinyl, tetrahydroquinolinyl, isoquinolinyl, dihydroisoquinolinyl, tetrahydroisoquinolinyl, pyridoindolyl, dihydrobenzoxazinyl, cinnolinyl, dihydrocinnolinyl, tetrahydrocinnolinyl, phthalazinyl, dihydrophthalazinyl, tetrahydrophthalazinyl, quinoxalinyl, dihydroquinoxalinyl, tetrahydroquinoxalinyl, purinyl, dihydrobenzotriazinyl, dihydrobenzotetrazinyl, phenothiazinylfuranyl, benzofuranyl, chromanyl, benzothienyl, and the like.

These heterocyclic groups include those substituted at any substitutable position with an oxo or thioketone group. All the heterocyclics mentioned above may optionally be further substituted. Examples of the number of substituents include, but are not particularly limited to, 1 to 20 (preferably 1 to 10, and more preferably 1 to 5) .

R 5 and R 6 , taken together with the carbon atom to which they bond, may bond to each other to form a 3- to 8-membered ring via or not via at least one heteroatom.

Examples of hetero atom in the specification include, but are not particularly limited to, an oxygen atom, a sulfur atom, a nitrogen atom, and the like. Examples of 3- to 8-membered ring include: but are not particularly limited to, cyclopropane, cycloheptane, and the like C 3 _ 8 cycloalkyl; tetrahydropyran, piperidine, and the like heterocyclic.

Examples of "substituted" or "substituents" include: but are not particularly limited to, the halogen, nitro, cyano, hydroxyl, formyl, C 1 _ 6 alkyl, C 1 _ 6 haloalkyl, C 1 _ 6 alkoxy, C 1 _ 6 haloalkoxy, C 1 _ 6 alkoxy C 1 _ 6 alkyl, C 1 _ 6 haloalkoxy C 1 _ 6 alkyl, C 3 _ 8 cycloalkyl, C 3 _ 8 cycloalkyl C 1 _ 6 alkyl, C 1 _ 6 alkylcarbonyl, C 1 _ 6 haloalkylcarbonyl, arylcarbonyl, aryloxycarbonyl, C 1 _ 6 alkoxycarbonyl, C 1 _ 6 haloalkoxycarbonyl, C 1 _ 6 cyanoalkyl, C 1 _ 6 cyanoalkoxy, C 2-6 alkenyl, C 2-6 haloalkenyl, C 2-6 alkynyl, C 2-6 haloalkynyl, C 1 _ 6 alkylsulfonyl, C 1 _ 6 haloalkylsulfonyl, C 1 _ 6 alkylsulfinyl, C 1 _ 6 haloalkylsulfinyl, C 1 _ 6 alkylthio, C 1 _ 6 haloalkylthio, C 3 _ 8 cycloalkylsulfonyl, C 3 _ 8 cycloalkylsulfinyl, C 3 _ 8 cycloalkylthio, C 3 _ 8 cycloalkyl C 1 _ 6 alkylsulfonyl, C 3 _ 8 cycloalkyl C 1 _ 6 alkylsulfinyl, C 3 _ 8 cycloalkyl C 1 _ 6 alkylthio, C 1 _ 6 alkoxy C 1 _ 6 alkylsulfonyl, C 1 _ 6 alkoxy C 1 _ 6 alkylsulfinyl, C 1 _ 6 alkoxy C 1 _ 6 alkylthio, C 2-6 alkenyloxy, C 2-6 haloalkenyloxy, C 2-6 alkynyloxy, C 2-6 haloalkynyloxy, C 1 _ 6 alkylsulfonyloxy, C 1 _ 6 haloalkylsulfonyloxy, C 1 _ 6 alkylsulfinyloxy, C 1 _ 6 haloalkylsulfinyloxy, carboxyl, OCN, SCN, SF 5 , substituted or unsubstituted amino, aryl, aryl C 1 _ 6 alkyl, aryloxy, aryl C 1 _ 6 alkoxy, arylsulfonyl, arylsulfinyl, arylthio, aryl C 1 _ 6 alkylsulfonyl, aryl C 1 _ 6 alkylsulfiny I , aryl C 1 _ 6 alkylthio, heterocyclic, heterocyclic C 1 _ 6 alkyl, heterocyclic oxy, and the like. Of these, preferable substituents are halogen, nitro, cyano, C 1 _ 6 alkyl, C 1 _ 6 haloalkyl, C 1 _ 6 alkoxy, C 1 _ 6 haloalkoxy, C 1 _ 6 alkylsulfonyl, C 1 _ 6 haloalkylsulfonyl, C 1 _ 6 alkylsulfinyl, C 1 _ 6 haloalkylsulfinyl, C 1 _ 6 alkylthio, C 1 _ 6 haloalkylthio, substituted or unsubstituted amino, aryl, and heterocyclic, and more preferable substituents are fluorine, chlorine, nitro, methyl, ethyl, trifluoromethyl, methoxy, and trifluoromethoxy .

Preferable substituted aryl groups are halogen-substituted aryl, C 1 _ 6 alkyl-substituted aryl, C 1 _ 6 haloalkyl-substituted aryl, halogen and C 1 _ 6 haloalkyl-substituted aryl, C 1 _ 6 alkoxy- substituted aryl, C 1 _ 6 haloalkoxy-substituted aryl, and C 1 _ 6 alkylthio-substituted aryl. More preferable substituted aryl groups are chlorine-substituted aryl, fluorine-substituted aryl, trifluoromethyl-substituted aryl, chlorine- and trifluoromethyl- substituted aryl, trifluoromethoxy-substituted aryl, and methoxy- substituted aryl, and methylthio-substituted aryl.

Preferable substituted heteroaryl groups are halogen- substituted heteroaryl, C 1 _ 6 alkyl-substituted heteroaryl, C 1 _ 6 haloalkyl-substituted heteroaryl, halogen and C 1 _ 6 haloalkyl — substituted heteroaryl, C 1 _ 6 alkoxy-substituted heteroaryl, C 1 _ 6 haloalkoxy-substituted heteroaryl, and C 1 _ 6 alkylthio-substituted heteroaryl. More preferable substituted heteroaryl groups are chlorine-substituted heteroaryl, fluorine-substituted heteroaryl, trifluoromethyl-substituted heteroaryl, chlorine- and trifluoromethyl-substituted heteroaryl, trifluoromethoxy- substituted heteroaryl, and methoxy-substituted heteroaryl, and methylthio-substituted heteroaryl .

Preferable substituted heterocyclic groups are halogen- substituted heterocyclic, C 1 _ 6 alkyl-substituted heterocyclic, C 1 _ 6 haloalkyl-substituted heterocyclic, C 1 _ 6 alkoxy-substituted heterocyclic, C 1 _ 6 haloalkoxy-substituted heterocyclic, and C 1 _ 6 alkylthio-substituted heterocyclic. More preferable substituted heterocyclic groups are chlorine-substituted heterocyclic, fluorine-substituted heterocyclic, trifluoromethyl-substituted heterocyclic, trifluoromethoxy-substituted heterocyclic, methoxy- substituted heterocyclic, and methylthio-substituted heterocyclic. The salts of the compounds represented by Formula (1) may be any type of salts as long as they are agriculturally acceptable. Examples of the salts include a hydrochloride salt, a sulfate salt, a nitrate salt, and like inorganic acid salts; an acetate salt, a methanesulfonic acid salt, and like organic acid salts; a sodium salt, a potassium salt, and like alkali metal salts; a magnesium salt, a calcium salt, and like alkaline earth metal salts; dimethylammonium, triethylammonium, and like quaternary ammonium salts; and the like.

X represents oxygen or sulfur.

Symbol n represents an integer of 0 to 2.

Among compounds 1 and 1A of the present invention, a preferable compound is a compound in which HET is 5- or 6- membered heteroaryl, a more preferable compound among 1 and 1A is a compound in which HET is substituted or unsubstituted pyrazole, substituted or unsubstituted thiazole, substituted or unsubstituted pyridine, substituted or unsubstituted imidazole, or substituted or unsubstituted benzimidazole, and a further preferable compound among 1 and 1A is a compound in which HET is substituted or unsubstituted pyrazole or substituted or unsubstituted thiazole or substituted or unsubstituted pyridine.

Among compounds 1 and IB of the present invention, a preferable compound is a compound in which R 7 is C 1 _ 6 alkyl, C 1 _ 6 haloalkyl, C 3 _ 8 cycloalkyl, C 3 _ 8 cycloalkyl C 1 _ 6 alkyl, substituted or unsubstituted aryl, substituted or unsubstituted aryl C 1 _ 6 alkyl, and a more preferable compound among 1 and IB is a compound in which R 7 is optionally substituted aryl or optionally substituted aryl C 1 _ 6 alkyl. Among optionally substituted aryl, preferable substituents are chloro, bromo, fluoro, methyl, trifluoromethyl, trifluoromethoxy, methylthio, trifluoromethylthio, or substituted aryl. Among optionally substituted aryl C 1 _ 6 alkyl, preferable aryl substituents are same as those described above, wherein C 1 _ 6 alkyl is preferably substituted with halogen, or C 1 _ 6 alkyl.

Among compounds 1, 1A and IB of the present invention, a preferable compound is a compound in which R 1 is C 1 _ 6 haloalkyl, and a more preferable compound among 1, 1A and IB is a compound in which R 1 is trifluoroethyl .

Among compounds 1, 1Ά and IB of the present invention, a preferable compound is a compound in which R 2 is hydrogen, halogen, or C 1 _ 6 alkyl, and a more preferable compound (1) is a compound in which R 2 is fluorine, chlorine, bromine, or methyl.

Among compounds 1, 1A and IB of the present invention, a preferable compound is a compound in which R 3 is hydrogen, halogen, or C 1 _ 6 alkyl, and a more preferable compound (1) is a compound in which R 3 is fluorine, chlorine, bromine, or methyl.

Among compounds 1, 1A and IB of the present invention, a preferable compound is a compound in which R 4 is hydrogen, C 1 _ 6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 1 _ 6 haloalkyl, or C 1 _ 6 alkylcarbonyl and a more preferable compound (1) is a compound in which R 4 is hydrogen, methyl, ethyl, n-propyl, i-propyl or acetyl.

Among compounds 1, 1A and IB of the present invention, a preferable compound is a compound in which R 5 and R 6 are identical or different and each represents hydrogen, halogen, or C 1 _ 6 alkyl, and a more preferable compound (1) is a compound in which R 5 and R 6 are hydrogen, fluorine, or methyl.

Alternatively, among compounds (1) of the present invention, a preferable compound is a compound in which R 1 is CH 2 C(X 1 ) (X 2 ) (X 3 ) wherein X 1 , X 2 , and X 3 are identical or different and each represent halogen; a more preferable compound (1) is a compound in which X 1 , X 2 , and X 3 are identical or different and each represent fluorine, chlorine, or bromine; a further more preferable compound (1) is a compound in which X 1 , X 2 , and X 3 are identical or different and each represent fluorine or chlorine; and a most preferable compound (1) is a compound in which X 1 , X 2 , and X 3 are fluorine.

Among compounds (1) of the present invention, a preferable compound is a compound in which R 2 is methyl .

Among compounds (1) of the present invention, a preferable compound is a compound in which R 3 is halogen; a more preferable compound is a compound in which R 3 is fluorine, chlorine, or bromine; a further more preferable compound is a compound in which R 3 is fluorine or chlorine; and a most preferable compound is a compound in which R 3 is fluorine.

Among compounds (1) of the present invention, a preferable compound is a compound in which R 4 is hydrogen, C 1 _ 6 alkyl, or C 1 _ 6 alkylcarbonyl; a more preferable compound (1) is a compound in which R 4 is hydrogen, methyl, or ethyl; a more preferable compound (1) is a compound in which R 4 is hydrogen or methyl; and a most preferable compound (1) is a compound in which R 4 is hydrogen.

Among compounds (1) of the present invention, a preferable compound is a compound in which R 5 and R 6 are identical or different and each represent hydrogen or C 1 _ 6 alkyl; a more preferable compound (1) is a compound in which R 5 and R 6 are identical or different and each represent hydrogen or methyl; and a most preferable compound (1) is a compound in which R 5 and R 6 are hydrogen.

Among compounds (1) of the present invention, a preferable compound is a compound in which X is oxygen or sulfur, and a more preferable compound (1) is a compound in which X is oxygen.

Among compounds (1) of the present invention, a preferable compound is a compound in which n is 0.

Among compounds (1) of the present invention, a preferable compound is a compound in which R 8 represents hydrogen, halogen, nitro, cyano, C 1 _ 6 alkyl, C 1 _ 6 haloalkyl, C 1 _ 6 alkoxy, C 1 _ 6 haloalkoxy, C 1 _ 6 alkylthio, C 1 _ 6 haloalkylthio, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl, the groups represented as R 8 may optionally be further substituted; or two radicals R 8 that are bound to adjacent ring member atoms of the Het group may form together with said ring member atoms a fused ring system, in such a case, HET is fused with a substituted or unsubstituted aryl and wherein the fused carbocycle is unsubstituted or carries 1, 2, 3 or 4 identical or different groups R 8 .

Among compounds (1) of the present invention, a preferable compound is a compound in which HET represents

intersected with a wavy line indicates the point of attachment to the parent molecule;

R A1 , R A4 , and R A5 are identical or different and each represent hydrogen, halogen, nitro, cyano, C 1 _ 6 alkyl, C 1 _ 6 haloalkyl, pyridyl, or phenyl, wherein the pyridyl and phenyl are unsubstituted or substituted with one to three substituents selected from the group consisting of halogen, C 1 _ 6 alkyl, C 1 _ 6 haloalkyl, C 1 _ 6 haloalkoxy, and C 1 _ 6 alkylthio; and

R A2 and R A3 are identical or different and each represent hydrogen, C 1 _ 6 alkyl, C 1 _ 6 haloalkyl, nitro, pyridyl, or thienyl;

R' A6 R A7 R A8 R A9 R A10 and R A12 are identical or different and each represent hydrogen, halogen, C 1 _ 6 alkyl, or C 1 _ 6 haloalkyl;

R A11 and R A13 are identical or different and each represent hydrogen, halogen, nitro, C 1 _ 6 alkyl, or C 1 _ 6 haloalkyl;

k represents an integer of 0 to 4; and

m represents an integer of 0 to 4.

' Among compounds (1) of the present invention, a preferable compound is a compound in which R 7 is a group of the formula:

where a bond intersected with a wavy line indicates the point of attachment to the parent molecule; and R B1 , R B2 , R B3 , R B4 , and R BS are identical or different and each represents hydrogen, halogen, C 1 _ 6 alkyl, C 1 _ 6 alkoxy, C 1 _ 6 haloalkyl, C 1 _ 6 haloalkoxy, C 1 _ 6 alkylthio, C 1 _ 6 haloalkylthio, or phenyl, wherein the phenyl is substituted with one to five substituents . selected from the group consisting of halogen, C 1 _ 6 alkyl, C 1 _ 6 haloalkyl, C 1 _ 6 haloalkoxy, and C 1 _ 6 alkylthio.

Among compounds (1) of the present invention, a preferable compound is a compound in which R 7 represents C 1 _ 6 alkyl, C 1 _ 6 haloalkyl, substituted or unsubstituted pyridyl, or substituted or unsubstituted phenyl.

When the compound (1) has isomers such as optical isomers, stereoisomers, regioisomers, and the like, any of the isomers and mixtures thereof are included within the scope of the compound (1) . For example, when the compound (1) has optical isomers, the optical isomer separated from a racemic body is also included within the scope of the compound (1) . Each of such isomers may be obtained as a single compound by known synthesis and separation means (e.g., concentration, solvent extraction, column chromatography, recrystallization, etc.).

2. Method for producing an amide compound (1) and a salt thereof 2A. Method for producing an amide compound (1A) and a salt thereof

No limitations are placed on the method for producing an amide compound (1A) (compound (lA-a) and compound (ΙΑ-b) ) according to the present invention, and the amide compound (1A) can be produced by Steps 1 to 5 as represented by Reaction Scheme 1 below:

[Reaction Scheme 1]

(1A-a) (1A-b)

wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , HET, X, and n' are as defined above. Step 1

A heteroarylacetamide compound (hereinafter may be referred to as "compound (4)") represented by Formula (4) can be produced by reacting an aniline compound (hereinafter may be referred to as "compound (2)") represented by Formula (2) with a heteroarylalkylcarbonyl compound (hereinafter may be referred to as "compound (3)") represented by Formula (3) (Reaction Scheme 2) :

[Reaction Scheme 2]

(2) (3)

wherein R 2 , R 3 , R 4 , R 5 , R 6 , HET, and X are as defined above.

Y represents a leaving group or a hydroxyl group, and examples of the leaving group include: halogen such as chlorine, bromine, and iodine; substituted or unsubstituted C 1 _ 6 alkyl sulfonate; and substituted or unsubstituted aryl sulfonate. Examples of the substituent include the aforementioned substituents such as halogen and C 1 _ 6 haloalkyl.

Step 1A (when Y is a leaving group)

A heteroarylacetamide compound (4) can be produced by reacting the aniline compound (2) with a heteroarylalkylcarbonyl compound (hereinafter may be referred to as "compound (3A)") represented by Formula (3A) (Reaction Scheme 3) :

[Reaction Scheme 3]

(3A) (4)

wherein R 2 , R 3 , R 4 , R 5 , R 6 , HET, and X are as defined above. Y' represents a leaving group and examples of the leaving groups are same as those described above.

Examples of the heteroarylalkylcarbonyl compound (3A) include, but are not particularly limited to, heteroarylacetyl chloride, heteroarylacetyl bromide, and the like substituted or unsubstituted heteroarylacetyl halide; and ethyl heteroarylacetate, methyl heteroarylacetate, and the like substituted or unsubstituted heteroarylacetic acid esters.

A used ratio of the aniline compound (2) and the heteroarylalkylcarbonyl compound (3A) in the reaction there between is not particularly limited and thus can appropriately be selected from a wide range. Relative to 1 mole of the aniline compound (2) , typically approximately 1 to 5 moles of the heteroarylalkylcarbonyl compound (3A) and preferably approximately equimolar to 1.2 moles thereof is used.

The aforementioned reaction can be performed under absence or presence of a base. Among the above, the reaction is performed preferably under the presence of the base. As the base, a conventionally known base can widely be used, and examples of the base include but not particularly limited to are: sodium carbonate, potassium carbonate, cesium carbonate, potassium bicarbonate, sodium bicarbonate, and the like alkali metal carbonates; sodium hydroxide, potassium hydroxide, and the like alkali metal hydroxides; alkali metal hydrides such as sodium hydride and potassium hydride, and the like inorganic bases; sodium methoxide, sodium ethoxide, potassium tert-butoxide, and the like alkali metal alkoxides; pyridine, triethylamine, diethylamine, dimethylamine, methylamine, imidazole, benzimidazole, diisopropylethylamine, 4-dimethylaminopyridine, piperidine, and the like organic bases. Any separate one of these bases or a combination of two or more types thereof is used.

Relative to 1 mole of the aniline compound (2), typically approximately 1 to 10 moles of the base and preferably approximately 1 to 5 moles thereof may excessively be used. When triethylamine, pyridine, or like an organic base is used, it can be used in large excess to serve also as a reaction solvent.

The aforementioned reaction is performed in an appropriate solvent or without any solvent. When the aforementioned reaction is carried out in the solvent, no limitations are placed on the solvent as long as the solvent is inactive with respect to the aforementioned reaction. Examples of such a solvent include: n- hexane, cyclohexane, n-heptane, and the like fatty acid or alicyclic hydrocarbon-based solvents; benzene, chlorobenzene, toluene, xylene, and the like aromatic hydrocarbon-based solvents; methylene chloride, 1, 2-dichloroethane, chloroform, and carbon tetrachloride, and the like halogenated hydrocarbon-based solvents; diethyl ether, tetrahydrofuran (THF) , 1,4-dioxane, and the like ether-based solvents; methyl acetate, ethyl acetate, and the like esters solvents; acetonitrile; N, N-dimethylformamide (DMF) and the like amide-based solvents; and dimethyl sulfoxide and the like sulfoxide-based solvents. Any one of these solvents can be used alone or a combination of two or more types thereof can be used when necessary.

Reaction temperature for the aforementioned reaction is not particularly limited, and is typically within a range between - 10 °C and a boiling point of the solvent used and preferably 0 to 25 °C. Reaction time varies depending on, for example, the reaction temperature, and the reaction typically ends in approximately 0.5 to 24 hours. Step IB (when Y is a hydroxy1 group)

As another method for obtaining the heteroarylacetamide compound (4), the compound (4) can be produced by reacting the aniline compound (2) with a heteroarylacetic acid compound (hereinafter may be referred to as "compound (3B)") represented by Formula (3B) (Reaction Scheme 4):

[Reaction Scheme 4]

(2) (3B) (4) wherein R 2 , R 3 , R 4 , R 5 , R 6 , HET, and X are as defined above.

A used ratio of the aniline compound (2) and the heteroarylacetic acid compound (3B) in the reaction there between is not particularly limited and thus can appropriately be selected from a wide range. Relative to 1 mole of the aniline compound (2) , typically approximately 1 to 5 moles of the heteroarylacetic acid compound (3B) and preferably approximately equimolar to 1.2 moles thereof is used.

The aforementioned reaction can be performed under absence or presence of a condensing agent. Among the above, the aforementioned reaction is preferably performed under the presence of the condensing agent. As the condensing agent, a conventionally known condensing agent can be used, and examples of the condensing agent include l-ethyl-3- (3-dimethylaminopropyl) carbodiimide (EDCI.HC1), 1-hydroxybenzotriazole (HOBT) , 1- [bis (dimethylamino) methylene] -lH-1, 2, 3-triazolo [4,5-b] pyridinium-3-oxide hexafluorophosphate (HATU) , bis (2-oxo-3- oxazolidinyl) phosphine acid chloride (BOP-C1) , propylphosphonic acid anhydride (T3P) , and the like. Any separate one of these condensing agents or a combination of two or more types thereof is used.

Relative to 1 mole of the aniline compound (2) , typically 1 to 10 moles of the condensing agent and preferably approximately 1 to 3 moles thereof can excessively be used.

The aforementioned reaction is performed in an appropriate solvent or without any solvent. When the aforementioned reaction is carried out in the solvent, no limitations are placed on the solvent as long as the solvent is inactive with respect to the aforementioned reaction. Examples of such a solvent include: n- hexane, cyclohexane, n-heptane, and the like fatty acid or alicyclic hydrocarbon-based solvents; benzene, chlorobenzene, toluene, xylene, and the like aromatic hydrocarbon-based solvents; methylene chloride, 1 , 2-dichloroethane, chloroform, carbon tetrachloride, and the like halogenated hydrocarbon-based solvents; diethyl ether, THF, and 1,4-dioxane, and the like ether-based solvents; methyl acetate, ethyl acetate, and the like esters solvents; acetonitrile; DMF and the like amide solvents; and dimethyl sulfoxide and the like sulfoxide-based solvents. Any one of these solvents can be used alone or a combination of two or more types of the solvents can be used when necessary.

Reaction temperature for the aforementioned reaction is not particularly limited and is typically within a range between - 10 °C and a boiling point of the solvent used and preferably within a range between -5°C and the boiling point of the solvent. Reaction time varies depending on, for example, the reaction temperature, and the reaction typically ends in approximately 0.25 to 24 hours.

Step 1C

Note that as a method for producing the heteroarylacetamide compound (4), a heteroarylacetic acid halide compound (3A, Y' = halogen) obtained by reacting the heteroarylacetic acid compound (3B) with a halogenation reagent can be used as a raw material.

The aforementioned reaction can be performed under presence of a base. As the base, any of the same bases as those described above can be used, and preferable examples of the base include triethylamine, pyridine, di-isopropylamine, 4- diisopropylethylamine, 4-dimethylaminopyridine, lutidine, and the like organic bases, and this base can also much excessively be used to act as a reaction solvent.

Examples of the halogenation reagent includes, but are not particularly limited to, P0C1 3 , POBr 3 , S0C1 2 , S0 2 C1 2 , oxalyl chloride .

Relative to 1 mole of the aniline compound (2) , typically 1 to 10 moles of the halogenation reagent and preferably approximately 1 to 5 moles thereof can be used.

The aforementioned reaction is performed in an appropriate solvent or without any solvent . When the aforementioned reaction is carried out in the solvent, no limitations are placed on the solvent as long as the solvent is inactive with respect to the aforementioned reaction. As a solvent, any one of those solvents described above, alone or a combination of two or more types thereof can be used when necessary.

Reaction temperature for the aforementioned reaction is not particularly limited and is typically within a range between - 10 °C and a boiling point of the solvent used and preferably within a range between -5°C and the boiling point of the solvent. Reaction time varies depending on, for example, the reaction temperature, and the reaction typically ends in approximately 0.25 to 24 hours.

The aniline compound (2) , the heteroarylcarbonyl compound

(3A) , the heteroarylacetic acid compound (3B) , and heteroarylacetic acid halide compound (3C) used as starting materials in Step 1 are known compounds or compounds that can easily be produced by a known method.

The compound (4) obtained by the method shown in Step 1 is easily isolated from a reaction mixture and can be purified by use of typical isolation means and purification means, for example, filtration, solvent extraction, distillation, recrystallization, column chromatography, etc.

After end of the reaction, the compound (4) can be provided for next reaction without being isolated from the reaction system.

Step 2

A sulfonyl chloride compound (hereinafter may be referred to as "compound (5)") represented by Formula (5) can be produced by chlorosulfonating the heteroarylacetamide compound (4) (Reaction Scheme 5) :

[Reaction Scheme 5]

wherein R 2 , R 3 , R 4 , R 5 , R 6 , HET, and X are as defined above.

A reagent used for the chlorosulfonation is not particularly limited, and for example, include chlorosulfonic acid, and the like. When using chlorosulfonic acid, the step can be carried out in one step. For the chlorosulfonation, a two-step method including sulfonation and then chlorination can be used. The sulfonyl chloride compound (5) can be produced by reacting the heteroarylacetamide compound (4) with a sulfonation reagent to produce an HOS0 2 -substituted amide compound and then reacting the H0SC>2-containing amide compound with a chlorination agent .

The reagent used for the sulfation is not particularly limited, and for example, chlorosulfonic acid, sulfuric acid, etc can be used. Examples of the chlorinating agent used for the chlorination include, but are not particularly limited to, chlorine, P0C1 3 , S0C1 2 , S0 2 C1 2 , and oxalyl chloride.

When the chlorosulfonic acid is used, a used ratio between the heteroarylacetamide compound (4) and the chlorosulfonic acid in the reaction there between is not particularly limited and can appropriately be selected from a wide range. Relative to 1 mole of the heteroarylacetamide compound (4), typically approximately 1 to 50 moles of chlorosulfonic acid and preferably approximately 1 to 20 moles thereof is used. When the sulfonation reagent and the chlorinating agent are used, a used ratio between the sulfonation reagent, the chlorinating agent and the heteroarylacetamide compound (4) in the reaction is not particularly limited and can appropriately be selected from a wide range., Relative to 1 mole of the heteroarylacetamide compound (4), typically approximately 1 to 50 moles of the sulfonation reagent and preferably approximately 1 to 20 moles thereof is used. A used ratio between the two in the reaction between the heteroarylacetamide compound (4) and the chlorinating agent is not particularly limited, and can appropriately be selected from a wide range. Relative to 1 mol of the heteroarylacetamide compound (1) , typically approximately 1 to 50 moles of the chlorinating agent and preferably 1 to 20 moles thereof is used.

The aforementioned reaction is performed in an appropriate solvent or without any solvent. When the aforementioned reaction is carried out in the solvent, no limitations are placed on the solvent as long as the solvent is inactive with respect to the aforementioned reaction. As examples of such a solvent, the same solvents as those described above are listed. Any one of these solvents can be used alone or a combination of two or more types thereof can be used when necessary.

Reaction temperature for the aforementioned reaction is not particularly limited, and is typically within a range between - 20°C and a boiling point of the solvent used, preferably -10°C to 150 °C, and more preferably 0 to 100 °C. Reaction time varies depending on, for example, the reaction temperature and the reaction typically ends in approximately 0.25 to 24 hours.

The sulfonyl chloride compound (5) obtained by the method shown in Step 2 is easily isolated from a reaction mixture and can be purified by use of typical isolation means and purification means, for example, filtration, solvent extraction, distillation, recrystallization, column chromatography, etc.

After end of the reaction, the sulfonyl chloride compound (5) can be provided for next reaction without being isolated from the reaction system.

Step 3

A thiol compound (hereinafter may be referred to as "compound (6)") represented by Formula (6) can be produced by reacting the sulfonyl chloride compound (5) with a reducing agent (Reaction Scheme 6) :

[Reaction Scheme 6]

(5) (6)

wherein R 2 , R 3 , R 4 , R 5 , R 6 , HET, and X are as defined above.

A used ratio between the sulfonyl chloride compound (5) and the reducing agent in the reaction there between is not particularly limited and can appropriately be selected from a wide range. Relative to 1 mole of the sulfonyl chloride compound (5) , typically approximately 1 to 50 moles of the reducing agent and more preferably approximately 1 to 20 moles thereof is used.

As the reducing agent, any of conventionally known reducing agents can widely be used, and examples of the reducing agent include: triphenylphosphine and the like phosphorous compounds; reducing agents containing metal and acid such as zinc and acid, tin (II) and acid, and iron and acid; and reducing agent red phosphorus, iodine, dichlorodimethylsilane-zinc-dimethylacetamide, lithium aluminum hydride, and the like specific reducing agents. Examples of the acid include acetic acid and the like organic acids; and hydrochloric acid, sulfuric acid, and the like inorganic acids.

The aforementioned reaction is performed in an appropriate solvent. No limitations are placed on the solvent as long as the solvent is inactive with respect to the reaction. As examples of such a solvent, the same solvents as those described above are listed. Any one of these solvents can be used alone or a combination of two or more types thereof can be used when necessary.

Reaction temperature for the aforementioned reaction is not particularly limited and is typically within a range between - 20 °C and a boiling point of the solvent used, preferably -10 °C to 150°C, and more preferably 20 to 120°C. Reaction time varies depending on, for example, the reaction temperature and the reaction typically ends in approximately 0.25 to 24 hours.

The thiol compound (6) obtained by the method shown in Step 3 is easily isolated from a reaction mixture and can be purified by use of typical isolation means and purification means, for example, filtration, solvent extraction, distillation, recrystallization, column chromatography, etc.

After end of the reaction, the thiol compound (6) can be provided for next reaction without being isolated from the reaction system.

Method for producing a sulfide compound represented by Formula (ΙΑ-a) or a salt thereof

Examples of the method for producing the sulfide compound represented by Formula (ΙΑ-a) include, but are not limited to, a production route 1, a production route 2, a production route 3, a production route 4, described below, and the like. Production route 1 (Step 4)

A sulfide compound (ΙΑ-a) can be produced by reacting the thiol compound (6) with an alkyl reagent (hereinafter may be referred to as "alkyl reagent {!)") represented by Formula (7) (Reaction Scheme 7) :

[Reaction Scheme 7]

wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , HET, and X are as defined above, and G represents a leaving group.

Examples of the leaving group are same as those described above .

A used ratio between the thiol compound (6) and the alkyl reagent (7) in the reaction there between is not particularly limited and can appropriately be selected from a wide range. Relative to 1 mole of the thiol compound (6), typically approximately 1 to 10 moles of the alkyl reagent (7) and preferably approximately 1 to 5 moles thereof is used.

Examples of the alkyl reagent (7) include, but are not particularly limited to, methyl iodide, ethyl bromide, and the like C 1 _ 6 alkyl halides; trifluoromethyl iodide, trifluoromethyl bromide, trifluoroethyl iodide, trifluoroethyl bromide, and the like C 1 _ 6 haloalkyl halides, and the like.

The aforementioned reaction can be performed under absence or presence of a base. Among the above, the aforementioned reaction is preferably performed under the presence of the base. As examples of the base, conventionally known bases can widely be used, and any of the same bases as those described above can be used.

Relative to 1 mole of the thiol compound (6) , typically 1 to 10 moles of the base and preferably approximately 1 to 3 moles thereof can be used. When triethylamine, pyridine, or like an organic base is used, it can be used in large excess to serve also as a reaction solvent.

The aforementioned reaction can be performed by further adding a radical starting agent. Examples of the radical starting agent include, but are not particularly limited to, sulfurous acid, a sulfurous acid salt, Rongalit (product name, sodium- formaldehyde-sulfoxylate) , and the like sulfurous acid adducts. The base and the radical starting agent can be used in combination.

When the radical starting agent is used, as an additive amount thereof, relative to 1 mole of the thiol compound (6), typically 0.1 to 10 moles of the radical starting agent and preferably approximately 0.1 to 5 moles thereof can be used.

The aforementioned reaction is performed in an appropriate solvent. Examples of the solvent include: n-hexane, cyclohexane n-heptane, and the like fatty acid or alicyclic hydrocarbon-based solvents; benzene, chlorobenzene, toluene, xylene, and the like aromatic hydrocarbon-based solvents; methylene chloride, 1,2- dichloroethane, chloroform, carbon tetrachloride, and the like halogenated hydrocarbon-based solvents; diethyl ether, THF, 1,4- dioxane, and the like ether-based solvents; methyl acetate, ethyl acetate, and the like ester-based solvents; acetonitrile; DMF, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, and the like amide-based solvents; dimethyl sulfoxide and the like sulfoxide- based solvents; alcohol-based solvents such as sulfolane, methanol, ethanol, isopropyl alcohol, and the like polar solvents; water; and the like. Any one of these solvents can be used alone or a combination of two or more types thereof can be used when necessary.

Reaction temperature for the aforementioned reaction is not particularly limited, and is typically within a range between - 20 °C and a boiling point of the solvent used, preferably -10 °C to 60 °C, and more preferably 0 to 50 °C. Reaction time varies depending on, for example, the reaction temperature and the reaction typically ends in approximately 0.25 to 24 hours.

The sulfide compound (ΙΑ-a) obtained by the method shown in

Step 4 is easily isolated from a reaction mixture and can be purified by use of typical isolation means and purification means, for example, filtration, solvent extraction, distillation, recrystallization, column chromatography, etc.

After end of the reaction, the sulfide compound (lA-a) can be provided for next reaction without being isolated from the reaction system.

Production Route 2

A sulfide compound (hereinafter may be referred to as "compound (lA-d)") represented by Formula (lA-d) can be produced by reacting a sulfide compound (hereinafter may be referred to as "compound (lA-c)") represented by Formula (lA-c) with a compound (hereinafter may be referred to as "compound {!')") represented by Formula (V): R 4 '-G (Reaction Scheme 8):

[Reaction Scheme 8]

(1A-c) (1 A-d)

wherein R 1 , R 2 , R 3 , R 5 , R 6 , HET, and X are as defined above, and R 4 ' represents formyl, cyano, C 1 _ 6 alkyl, C 1 _ 6 haloalkyl, C 1 _ 6 alkoxy, C 1 _ 6 haloalkoxy, C 1 _ 6 alkoxy C 1 _ 6 alkyl, C 3 _ 8 cycloalkyl, C 3 _ 8 cycloalkyl C 1 _ 6 alkyl, C 1 _ 6 alkylcarbonyl, C 1 _ 6 haloalkylcarbonyl, C 1 _ 6 alkoxycarbonyl, C 1 _ 6 haloalkoxycarbonyl, arylcarbonyl, aryloxycarbonyl, cyano C 1 _ 6 alkyl, C 2-6 alkenyl, C 2-6 haloalkenyl, cyano C 2-6 alkenyl, C 2-6 alkynyl, C 2-6 haloalkynyl, cyano C 2-6 alkynyl, C 1 _ 6 alkylsulfonyl, C 1 _ 6 haloalkylsulfonyl, C 1 _ 5 alkylsulfinyl, C 1 _ 6 haloalkylsulfinyl, C 2-6 alkenyloxy, C 2-6 alkynyloxy, aryl, aryl C 1 _ 6 alkyl, aryloxy, arylsulfonyl, arylsulfinyl, heteroaryl, all the substituents defined as R 4 may optionally be further substituted. G represents a leaving group.

Examples of the leaving group are same as those described above .

A used ratio between the sulfide compound (lA-c) and the compound (V ) in the reaction there between is not particularly limited and can appropriately be selected from a wide range. Relative to 1 mole of the former, typically approximately 1 to 10 moles of the latter and preferably approximately equimolar to 5 moles thereof is used.

The aforementioned reaction can be performed under presence of a base. As the base, conventionally known bases can be used and any of the same bases as those described above can be used.

Relative to 1 mole of the sulfide compound (lA-c) , a stoichiometric amount of the base or an excessive amount thereof over the aforementioned amount can be used. Preferably one to ten times of the base and more preferably one to five times thereof may excessively be used. When triethylamine, pyridine, or like an organic base is used, it can be used in large excess to serve also as a reaction solvent.

The aforementioned reaction is performed in an appropriate solvent. Examples of the solvent include: n-hexane, cyclohexane, n-heptane, and the like fatty acid or alicyclic hydrocarbon-based solvents; benzene, chlorobenzene, toluene, xylene, and the like aromatic hydrocarbon-based solvents; methylene chloride, 1,2- dichloroethane, chloroform, carbon tetrachloride, and the like halogenated hydrocarbon-based solvents; diethyl ether, THF, 1,4- dioxane, and the like ether-based solvents; methyl acetate, ethyl acetate, and the like esters solvents; acetonitrile; DMF, N,N- dimethylacetamide, N-methyl-2-pyrrolidone, and the like amide- based solvents; dimethyl sulfoxide and the like sulfoxide-based solvents; alcohol-based solvents such as sulfolane, methanol, ethanol, and isopropyl alcohol and the like polar solvents; and water. Any one of these solvents can be used alone or a combination of two or more types thereof can be used when necessary.

Reaction temperature for the aforementioned reaction is not particularly limited and is typically within a range between - 20°C and a boiling point of the solvent used, preferably -10°C to 60°C, and more preferably 20 to 50°C. Reaction time varies depending on, for example, the reaction temperature and the reaction typically ends in approximately 0.25 to 24 hours.

The sulfide compound (ΙΑ-d) obtained by the method shown in Reaction scheme 8 is easily isolated from a reaction mixture to be purified by use of typical isolation means and purification means, for example, filtration, solvent extraction, distillation, recrystallization, column chromatography, etc.

After end of the reaction, the sulfide compound (ΙΑ-d) can be provided for next reaction without being isolated from the reaction system.

The sulfide compound (lA-c) can be produced in accordance with not only what have been mentioned above but also production routes 3, 4, and 5.

Production Route 3

The sulfide compound (lA-c) can be produced by reacting an aniline compound (hereinafter may be referred to as "compound (8)") with a heteroarylalkylcarbonyl compound (3) (Reaction Scheme 9) :

[Reaction Scheme 9]

(8) (3) (1 A-c) wherein R 1 , R 2 , R 3 , R 5 , R 6 , HET, X, and Y are as defined above.

Production Route 3A (when Y is a leaving group)

The sulfide compound (lA-c) can be produced by reacting the aniline compound (8) with a heteroarylalkylcarbonyl compound (3A) (Reaction Scheme 10) :

[Reaction Scheme 10]

(8) (3A) ( 1A-c) wherein R 1 , R 2 , R 3 , R 5 , R 6 , HET, X and Y' are as defined above.

Examples of the heteroarylalkylcarbonyl compound (3A) include, but are not particularly limited to, the same compounds as those of Step 1A.

The aniline compound (8) used as a starting material is a known compound or can be produced according to methods described A used ratio between the aniline compound (8) and the heteroarylalkylcarbonyl compound (3A) in the reaction there between is not particularly limited and thus can appropriately be selected from a wide range. Relative to 1 mole of the former, typically approximately 1 to 5 moles of the latter and preferably approximately equimolar to 1.2 moles thereof is used.

The aforementioned reaction can be performed under absence or presence of a base. Among the above, the aforementioned reaction is preferably performed under the presence of the base. As examples of the base, any of the same bases as those shown above in Step 1 can be used. Any separate one of these bases or a combination of two or more types thereof is used.

Relative to 1 mole of the aniline compound (8) , a stoichiometric amount of the base or an excessive amount thereof over the aforementioned amount can excessively be used. Preferably one to five times of the base may excessively be used. When triethylamine, pyridine, or like an organic base is used, it can be used in large excess to serve also as a reaction solvent.

The aforementioned reaction is performed in an appropriate solvent or without any solvent. When the aforementioned reaction is carried out in the solvent, any of the same solvents as those shown above in Step 1 can be used. Any one of these solvents can be used alone or a combination of two or more types thereof can be used when necessary.

Reaction temperature for the aforementioned reaction is not particularly limited and is typically within a range between - 20 °C and a boiling point of the solvent used and preferably 0 to 50 °C. Reaction time varies depending on, for example, the reaction temperature and the reaction typically ends in approximately 0.5 to 24 hours.

The sulfide compound (lA-c) is easily isolated from a reaction mixture and can be purified by use of typical isolation means and purification means, for example, filtration, solvent extraction, distillation, recrystallization, column chromatography, etc.

After end of the reaction, the sulfide compound (lA-c) can be provided for next reaction without being isolated from the reaction system.

Production Route 3B (when Y is a hydroxyl group)

As another method for obtaining the heteroarylacetamide compound (lA-c) , the compound (lA-c) can be produced by reacting the aniline compound (8) with a heteroarylacetic acid compound (3B) (Reaction Scheme 11) :

[Reaction Scheme 11]

(8) (3B) (1 A-c) wherein R 1 , R 2 , R 3 , R 5 , R 6 , HET, and X are as defined above.

A used ratio between the aniline compound (8) and the heteroarylacetic acid compound (3B) in the reaction there between is not particularly limited and thus can appropriately be selected from a wide range. Relative to 1 mole of the former, typically approximately 1 to 5 moles of the latter and preferably equimolar to 1.2 moles thereof is used.

The aforementioned reaction can be performed under absence or presence of a condensing agent. Among the above, the aforementioned reaction is preferably performed under the presence of the condensing agent. As examples of the condensing agent, the same condensing agents as those shown in Step IB. Any separate one of these condensing agents or a combination of two or more types thereof is used.

Relative to 1 mole of the aniline compound (8) , a stoichiometric amount of the condensing agent or an excessive amount thereof over the aforementioned amount can be used. Preferably approximately one to five times of the condensing agent may excessively be used. The aforementioned reaction can be performed under absence or presence of a base. Among the above, the aforementioned reaction is preferably performed under the presence of the base. As the base, any of the same bases as those shown in Step 1 above can be used. Any separate one of these bases or a combination of two or more types thereof is used.

Relative to 1 mole of the aniline compound (8), a stoichiometric amount of the base or an excessive amount thereof over the aforementioned amount can be used. Preferably approximately 1 to 5 times of the base can excessively be used. When triethylamine, pyridine, or like an organic base is used, it can be used in large excess to serve also as a reaction solvent.

The aforementioned reaction is performed in an appropriate solvent or without any solvent. When the aforementioned reaction is carried out in the solvent, any of the same solvents as those shown in Step 1 above can be used. Any one of these solvents can be used alone or a combination of two or more types thereof can be used when necessary.

Reaction temperature for the aforementioned reaction is not particularly limited and is typically within a range between - 20 °C and a boiling point of the solvent used and preferably 0 to 25 °C. Reaction time varies depending on, for example, the reaction temperature and the reaction typically ends in approximately 0.5 to 24 hours.

Production Route 3C

Note that as a method for producing the heteroarylacetamide compound (lA-c) , a heteroarylacetic acid halide compound (3A, Y'= halogen) obtained by reacting the heteroarylacetic acid compound (3B) with a halogenation reagent can be used as a material.

The aforementioned reaction can be performed under presence of a base. As the base, any of the same bases as those described above can be used, and preferable examples of the base include triethylamine, pyridine, di-isopropylamine, 4- diisopropylethylamine, 4-dimethylaminopyridine, lutidine, and the like organic bases. The bases can much excessively be used to be also used as reaction solvents.

Examples of the halogen reagent include, but are not particularly limited to, P0C1 3 , POBr 3 , S0C1 2 , S0 2 C1 2 , and oxalyl chloride.

Relative to 1 mole of the aniline compound (2) , typically 1 to 10 moles of the halogenation reagent and preferably approximately 1 to 5 moles thereof can be used.

The aforementioned reaction is performed in an appropriate solvent or without any solvent. When the aforementioned reaction is carried out in the solvent, no limitations are placed on the solvent as long as the solvent is inactive with respect to the aforementioned reaction. As examples of such a solvent, the aforementioned solvents are listed. Any one of these solvents can be used alone or a combination of two or more types thereof can be used when necessary.

Reaction temperature for the aforementioned reaction is not particularly limited and is typically within a range between - 10 °C and a boiling point of the solvent used and preferably within a range between -5°C and the boiling point of the solvent. Reaction time varies depending on, for example, the reaction temperature, and the reaction typically ends in approximately 0.25 to 24 hours.

The sulfide compound (lA-c) is easily isolated from a reaction mixture and can be purified by use of typical isolation means and purification means, for example, filtration, solvent extraction, distillation, recrystallization, column chromatography, etc.

After end of the reaction, the sulfide compound (lA-c) can be provided for next reaction without being isolated from the reaction system.

Production Route 4

The sulfide compound (ΙΑ-a) can be produced by reacting a sulfide compound (hereinafter may be referred to as "compound (9)") with an amide compound (hereinafter may be referred to as "compound (10)") represented by Formula (10) (Reaction Scheme 12) :

[Reaction Scheme 12]

wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , HET, and X are as defined above, and Z represents a leaving group.

A used ratio between the sulfide compound (9) and the heteroacetamide compound (10) in the reaction there between is not particularly limited and can appropriately be selected from a wide range. Relative to 1 mole of the former, typically approximately 1 to 10 moles of the latter and preferably approximately equimolar to 5 moles thereof is used.

The aforementioned reaction can be performed under absence or presence of a Pd-catalyst and a ligand. Among the above, the aforementioned reaction is preferably performed under the presence of the Pd-catalyst and a ligand. As the Pd-catalyst any of known Pd-catalyst can be used. Some examples of the Pd- catalyst but not particularly limited to are palladium acetate, Pd(0Ac)2, tetrakis (triphenylphosphine) palladium (0) , Pd(PPh 3 ) 4 , bis (triphenylphosphine) palladium (II) dichloride, PdCl 2 (PPh 3 ) 2 , [1,1' -bis (diphenylphosphino) ferrocene] palladium (II ) dichloride, and the like. Examples of the ligands but not particularly limited to are, 2-dicyclohexylphosphino-2 ' , 6 ' -dimethoxybiphenyl (S-Phos) and 2-dicyclohexylphosphino-2 ' , 4 ' , 6 ' - triisopropylbiphenyl (X-Phos) , 2-di-tert-butylphosphino-3, 4, 5, 6- tetramethyl-2 ' , 4 ' , 6 ' -triisopropyl-1, 1 ' -biphenyl, 4, 7-dimethoxy- 1, 10-phenanthroline, and the like. A used ratio between the sulfide compound (9) , Pd-catalyst and the ligand in the reaction there between is not particularly limited and can appropriately be selected from a wide range. The aforementioned reaction can be performed under absence or presence of a base. Among the above, the aforementioned reaction is preferably performed under the presence of the base. As the base, any of the same bases as those shown in Step 1 above can be used. Any separate one of these bases or a combination of two or more types thereof is used.

Relative to 1 mole of the aniline compound (9) , typically 1 to 10 moles of the base and preferably approximately 1 to 5 moles thereof is used.

The aforementioned reaction is performed in an appropriate solvent or without any solvent. When the aforementioned reaction is carried out in the solvent, any of the same solvents as those shown in the Step 1 above can be used. Any one of these solvents can be used alone or a combination of two or more types thereof can be used when necessary.

Reaction temperature for the aforementioned reaction is not particularly limited and is typically within a range between - 10 °C and a boiling point of the solvent used and preferably between 0°C and the boiling point of the solvent. Reaction time varies depending on, for example, the reaction temperature and the reaction typically ends in approximately 0.5 to 24 hours.

The sulfide compound (9) used as a starting material can be produced according to methods described in EP3002279 and WO2012/176856.

The sulfide compound (1-1) is easily isolated from a reaction mixture and can be purified by use of typical isolation means and purification means, for example, filtration, solvent extraction, distillation, recrystallization, column chromatography, etc.

After end of the reaction, the sulfide compound (lA-a) can be provided for next reaction without being isolated from the reaction system.

Step 5

An amide compound (hereinafter may be referred to as "compound (lA-b)") represented by Formula (ΙΑ-b) can be produced by reacting a sulfide compound represented by Formula (LA-a) with an oxidizing agent (Reaction Scheme 13) :

[Reaction Scheme 13]

(1A-a) (1A-b) wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , HET, X, and n' are as described above .

The aforementioned reaction can be performed under presence of the oxidizing agent. As the oxidizing agent, any of known oxidizing agents can be used as long as the oxidizing agent can achieve oxidization of sulfide into sulfoxide or sulfone, and examples of the oxidizing agent include but not particularly limited to are: performic acid, peracetic acid, pertrifluoroacetic acid, perbenzoic acid, m-chloroperbenzoic acid (mCPBA) , o-carbonylperbenzoic acid, and the like peracids; hydrogen peroxide, t-butylhydroperoxide, cumene hydroperoxide, and the like alkyl hydroperoxides; and titanium tetraisopropoxide and the like titanium tetraalkoxides; sodium dichromate, potassium dichromate, and the like dichromate salts; sodium permanganate, potassium permanganate, and the like permanganates; potassium peroxymonosulfate; and the like. Any separate one of these oxidizing agents or a combination of two or more types thereof is used.

A used ratio between the amide compound (ΙΑ-a) and the oxidizing agent in the reaction there between is not particularly limited and can appropriately be selected from a wide range. Relative to 1 mole of the former, typically approximately 1 to 10 moles of the latter and preferably approximately equimolar to 5 moles thereof is used.

The aforementioned reaction can further be performed by adding a catalyst. The aforementioned reaction is performed in an appropriate solvent. Examples of the solvent include: n-hexane, cyclohexane, n-heptane, and the like fatty acid or alicyclic hydrocarbon-based solvents; benzene, chlorobenzene, toluene, xylene, and the like aromatic hydrocarbon-based solvents; methylene chloride, 1,2- dichloroethane, chloroform, carbon tetrachloride, and the like halogenated hydrocarbon-based solvents; diethyl ether, THF, 1,4- dioxane, and the like ether-based solvents; methyl acetate, ethyl acetate, and the like esters solvents; acetonitrile; DMF, N,N- dimethylacetamide, N-methyl-2-pyrrolidone, and the like amide- based solvents; dimethyl sulfoxide and the like sulfoxide-based solvents; alcohol-based solvents such as sulfolane, methanol, ethanol, isopropyl alcohol, and the like polar solvents. Any one of these solvents can be used alone or a combination of two or more types thereof can be used when necessary.

Reaction temperature for the aforementioned reaction is not particularly limited, and is typically within a range between - 20°C and a boiling point of the solvent used, preferably -10°C to 60 °C, and more preferably 20 to 50 °C. Reaction time varies depending on, for example, the reaction temperature, and the reaction typically ends in approximately 0.25 to 24 hours.

The compound (lA-b) obtained by the method shown in Step 5 is easily isolated from a reaction mixture and can be purified by use of typical isolation means and purification means, for example, filtration, solvent extraction, distillation, recrystallization, chromatography, etc.

Each compound (1A) obtained after the completion of the reactions shown in Reaction Scheme 1 to Reaction Scheme 13 may be easily isolated from the reaction mixture and purified by known isolation and purification techniques, such as filtration, solvent extraction, distillation, recrystallization, and column chromatography .

When compound (1A) has regioisomers, each regioisomer may be separated by a usual separation step, such as silica gel chromatography .

2B. Method for producing an amide compound (IB-b) and a salt thereof

No limitations are placed on the method for producing an arylcarboxamide compound (hereinafter may be referred to as "compound (IB-b)") as represented by Formula IB-b, and the arylcarboxamide compound (IB-b) can be produced by following Steps 1 to 2 represented by Reaction Scheme 14 below:

[Reaction Scheme 14]

(11) (12) (1 B-a) (1 B-b) wherein R 1 , R 2 , R 3 , R 4 , R 7 , X, and n' are as described above.

Step 1

An amide compound (hereinafter may be referred to as

"compound (lB-a)") represented by Formula (ΙΒ-a) can be produced by reacting an arylcarbonyl compound (hereinafter may be referred to as "compound (11)") represented by Formula (11) with an amine compound (hereinafter may be referred to as "compound (12)") represented by Formula (12) (Reaction Scheme 15) :

[Reaction Scheme 15]

wherein R 1 , R 2 , R 3 , R 4 , R 7 , and X are as described above. G represents a leaving group or a hydroxyl group, and examples of the leaving group include: halogen such as chlorine, bromine, and iodine; substituted or unsubstituted C X - 6 alkyl sulfonate; and substituted or unsubstituted aryl sulfonate. Examples of the substituent include the aforementioned substituents such as the halogen and the C 1 _ 6 haloalkyl.

Examples of the amine compound (12) include, but are not particularly limited to, substituted or unsubstituted C 1 _ 6 alkyl amines and the like, substituted or unsubstituted C 3 _ 8 cycloalkyl amines and the like, substituted or unsubstituted C 3 _ 8 cycloalkyl C 1 _ 6 alkyl amines and the like, substituted or unsubstituted anilines and the like, substituted or unsubstituted aryl C 1 _ 6 alkyl amines and the like, substituted or unsubstituted heteroaryl amines and the like, substituted or unsubstituted heteroaryl C 1 _ 6 alkyl amines and the like.

Production route 5: Step 1A (when G is a leaving group)

An amide compound (ΙΒ-a) can be produced by reacting the arylcarbonyl compound (hereinafter may be referred to as "compound (11A)") represented by Formula (11A) with an amine compound (12) as represented by Reaction Scheme 16:

[Reaction Scheme 16]

(1 1A) (12) (1 B-a) wherein R 1 , R 2 , R 3 , R 4 , R 7 , and X are as described above. G' represents a leaving group as mentioned above.

A used ratio of the arylcarbonyl compound (11A) and the amine compound (12) in the reaction there between is not particularly limited and thus can appropriately be selected from a wide range. Relative to 1 mole of the arylcarbonyl compound (11A) , typically approximately 1 to 5 moles of the amine (12) and preferably approximately equimolar to 1.2 moles thereof is used.

The aforementioned reaction can be performed under absence or presence of a base. Among the above, the reaction is performed preferably under the presence of the base. As the base, any of conventionally known bases can be used, examples of known bases are similar as mentioned in Step 1A of production Method 2A. Relative to 1 mole of the arylcarbonyl compound (11A) , typically approximately 1 to 10 moles of the base and preferably approximately 1 to 5 moles thereof may excessively be used. When triethylamine, pyridine, or like an organic base is used, it can be used in large excess to serve also as a reaction solvent.

The aforementioned reaction is performed in an appropriate solvent or without any solvent. When the aforementioned reaction is carried out in the solvent, no limitations are placed on the solvent as long as the solvent is inactive with respect to the aforementioned reaction. Examples of solvents are similar as mentioned in Step 1A of production Method 2A. Any one of these solvents can be used alone or a combination of two or more types thereof can be used when necessary.

Reaction temperature for the aforementioned reaction is not particularly limited, and is typically within a range between - 10 °C and a boiling point of the solvent used and preferably 0 to 25 °C. Reaction time varies depending on, for example, the reaction temperature, and the reaction typically ends in approximately 0.5 to 24 hours.

Production route 6: Step IB (when G is a hydroxyl group)

An amide compound (ΙΒ-a) can also be produced by reacting the arylcarboxylic acid compound (hereinafter may be referred to as "compound (11B)") represented by Formula (11B) with the amine compound (12), (Reaction Scheme 17):

[Reaction Scheme 17]

( 11B ) (12) (iB-a) wherein R 1 , R 2 , R 3 , R 4 , R 7 , and X are as described above.

A used ratio of the aryl carboxylic acid compound (11B) and the amine compound (12) in the reaction there between is not particularly limited and thus can appropriately be selected from a wide range. Relative to 1 mole of the aryl carboxylic acid compound (11B) typically approximately 1 to 5 moles of the amine compound (12) and preferably approximately equimolar to 1.2 moles thereof is used.

The aforementioned reaction can be performed under absence or presence of a condensing agent. Among the above, the aforementioned reaction is preferably performed under the presence of the condensing agent. As the condensing agent, a conventionally known condensing agent can be used, and examples of the condensing agent include l-ethyl-3- (3-dimethylaminopropyl) carbodiimide (EDCI-HC1) , 1-hydroxybenzotriazole (HOBT) , 1- [bis (dimethylamino) methylene] -lH-1, 2, 3-triazolo [4,5-b] pyridinium-3-oxide hexafluorophosphate (HATU) , bis (2-oxo-3- oxazolidinyl) phosphine acid chloride (B0P-C1) , propylphosphonic acid anhydride (T3P) , and the like. Any separate one of these condensing agents or a combination of two or more types thereof is used.

Relative to 1 mole of the aryl carboxylic acid compound (11B) , typically 1 to 10 moles of the condensing agent and preferably approximately 1 to 3 moles thereof can excessively be used.

The aforementioned reaction can be performed under absence or presence of a base. Among the above, the reaction is performed preferably under the presence of the base. As the base, any of conventionally known bases can be used, examples of known bases are similar as mentioned in Step 1A of production Method 2A.

Relative to 1 mole of the aryl carboxylic acid compound (11B) , typically approximately 1 to 10 moles of the base and preferably approximately 1 to 5 moles thereof may excessively be used. When triethylamine, pyridine, or like an organic base is used, it can be used in large excess to serve also as a reaction solvent .

The aforementioned reaction is performed in an appropriate solvent or without any solvent. When the aforementioned reaction is carried out in the solvent, no limitations are placed on the solvent as long as the solvent is inactive with respect to the aforementioned reaction. Examples of solvents are similar as mentioned in Step 1A of production Method 2A. Any one of these solvents can be used alone or a combination of two or more types thereof can be used when necessary.

Reaction temperature for the aforementioned reaction is not particularly limited, and is typically within a range between - 10 °C and a boiling point of the solvent used and preferably 0 to 25 °C. Reaction time varies depending on, for example, the reaction temperature, and the reaction typically ends in approximately 0.5 to 24 hours.

Production route 7: Step 1C

In another method for production of the amide compound (1B- a) , an arylcarboxylic acid halide compound (11A, G'= halogen) as mentioned in step IB, Reaction scheme 16, can be obtained by reacting the arylcarboxylic acid compound (11B) with a halogenation reagent and can be used as a raw material.

The aforementioned reaction can be performed under presence of a base. As the base, any of the same bases as those described above can be used, and preferable examples of the base include triethylamine, pyridine, di-isopropylamine, 4-diisopropylethyl amine, 4-dimethylaminopyridine, lutidine, and the like organic bases, and this base can also much excessively be used to act as a reaction solvent.

Examples of the halogenation reagent includes, but are not particularly limited to, P0C1 3 , POBr 3 , S0C1 2 , S0 2 C1 2 , oxalyl chloride .

Relative to 1 mole of the arylcarboxylic acid compound (11B) , typically 1 to 10 moles of the halogenation reagent and preferably approximately 1 to 5 moles thereof can be used.

The aforementioned reaction is performed in an appropriate solvent or without any solvent. When the aforementioned reaction is carried out in the solvent, no limitations are placed on the solvent as long as the solvent is inactive with respect to the aforementioned reaction. As such a solvent, the aforementioned solvents are listed. Any one of these solvents can be used alone or a combination of two or more types thereof can be used when necessary.

Reaction temperature for the aforementioned reaction is not particularly limited and is typically within a range between - 10 °C and a boiling point of the solvent used and preferably within a range between -5°C and the boiling point of the solvent. Reaction time varies depending on, for example, the reaction temperature, and the reaction typically ends in approximately 0.25 to 24 hours.

Production route 8 :

An amide compound (hereinafter may be referred to as "compound (lB-d)") represented by Formula (ΙΒ-d) can be produced by reacting a sulfide compound (hereinafter may be referred to as "compound (lB-c)") represented by Formula (lB-c) with a compound (7') R4'-G (Reaction Scheme 18):

[Reaction Scheme 18]

wherein R 1 , R 2 , R 3 , R 4' , R 7 , and X are as defined above.

R 4' represents formyl, cyano, C 1 _ 6 alkyl, C 1 _ 6 haloalkyl, C 1 _ 6 alkoxy, C 1 _ 6 haloalkoxy, C 1 _ 6 alkoxy C 1 _ 6 alkyl, C 3 _ 8 cycloalkyl, C 3 _ 8 cycloalkyl C 1 _ 6 alkyl, C 1 _ 6 alkylcarbonyl, C 1 _ 6 haloalkylcarbonyl, C 1 _ 6 alkoxycarbonyl, C 1 _ 6 haloalkoxycarbonyl, arylcarbonyl, aryloxycarbonyl, cyano C 1 _ 6 alkyl, C 2-6 alkenyl, C 2-6 haloalkenyl, cyano C 2-6 alkenyl, C 2-6 alkynyl, C 2-6 haloalkynyl, cyano C 2-6 alkynyl, C 1 _ 6 alkylsulfonyl, C 1 _ 6 haloalkylsulfonyl, C 1 _ 6 alkylsulfinyl, C 1 _ 6 haloalkylsulfinyl, C 2-6 alkenyloxy, C 2-6 alkynyloxy, aryl, aryl C 1 _ 6 alkyl, aryloxy, arylsulfonyl, arylsulfinyl, heteroaryl, all the substituents defined as R 4 may optionally be further substituted; and G represents a leaving group. As examples of the leaving group, the leaving groups as those described above are listed.

A used ratio between the sulfide compound (lB-c) and the compound (T ) in the reaction there between is not particularly limited and can appropriately be selected from a wide range. Relative to 1 mole of the former, typically approximately 1 to 10 moles of the latter and preferably approximately equimolar to 5 moles thereof is used.

The aforementioned reaction can be performed under absence or presence of a base. Among the above, the aforementioned reaction is preferably performed under the presence of the base. As the base, conventionally known bases can be used and any of the same bases as those described above can be used.

Relative to 1 mole of the sulfide compound (lB-c) , a stoichiometric amount of the base or an excessive amount thereof over the aforementioned amount can be used. Preferably one to ten times of the base and more preferably one to five times thereof may excessively be used. When triethylamine, pyridine, or like an organic base is used, it can be used in large excess to serve also as a reaction solvent.

The aforementioned reaction is performed in an appropriate solvent. Examples of the solvent are same as those described above .

Reaction temperature for the aforementioned reaction is not particularly limited and is typically within a range between - 20°C and a boiling point of the solvent used, preferably -10°C to 60 °C, and more preferably 20 to 50 °C. Reaction time varies depending on, for example, the reaction temperature and the reaction typically ends in approximately 0.25 to 24 hours.

The compounds (ΙΒ-a), (lB-c) and (ΙΒ-d) obtained by the methods shown in Production routes 5 to 8 are easily isolated from a reaction mixture and can be purified by the use of typical isolation means and purification means, for example, filtration, solvent extraction, distillation, recrystallization, column chromatography, etc. After end of the reaction, the sulfide compound (ΙΒ-a), (1B- c) and (ΙΒ-d) can be provided for next reaction without being isolated from the reaction system.

The amine compounds (12), used as starting compound as mentioned above are known compounds or compounds that can be easily synthesized by various known methods.

The aryl carbonyl compounds (11A and 11B) used as a starting material can be produced according to various available known methods .

Production route 9: Step-2

An arylcarboxamide compound represented by Formula (lB-b) can be produced by reacting a sulfide compound represented by Formula (IB-a) with an oxidizing agent (Reaction Scheme 19) :

[Reaction Scheme 19]

(1 B-a) (1 B-b) wherein R 1 , R 2 , R 3 , R 4 , R , X, and n' are as described above.

The aforementioned reaction can be performed under presence of the oxidizing agent. As the oxidizing agent, any of known oxidizing agents can be used as long as the oxidizing agent can achieve oxidization of sulfide into sulfoxide or sulfone, and examples of the oxidizing agent include but not particularly limited to: performic acid, peracetic acid, pertrifluoroacetic acid, perbenzoic acid, m-chloroperbenzoic acid (mCPBA) , o- carbonylperbenzoic acid, and the like peracids; hydrogen peroxide, t-butyl hydroperoxide, cumene hydroperoxide, and the like alkyl hydroperoxides; and titanium tetraisopropoxide and the like titanium tetraalkoxides; dichromate, sodium dichromate, potassium dichromate, and the like dichromate salts; sodium permanganate, potassium permanganate, and the like permanganates; potassium peroxymonosulfate, and the like. Any separate one of these oxidizing agents or a combination of two or more types thereof is used.

A used ratio between the amide compound (ΙΒ-a) and the oxidizing agent in the reaction there between is not particularly limited and can appropriately be selected from a wide range. Relative to 1 mole of the former, typically approximately 1 to 10 moles of the latter and preferably approximately equimolar to 5 moles thereof is used.

The aforementioned reaction can further be performed by adding a catalyst.

The aforementioned reaction is performed in an appropriate solvent. Examples of the solvent include: n-hexane, cyclohexane, n-heptane, and the like fatty acid or alicyclic hydrocarbon-based solvents; benzene, chlorobenzene, toluene, xylene, and the like aromatic hydrocarbon-based solvents; methylene chloride, 1,2- dichloroethane, chloroform, carbon tetrachloride, and the like halogenated hydrocarbon-based solvents; diethyl ether, THF, 1,4- dioxane, and the like ether-based solvents; methyl acetate, ethyl acetate, and the like esters solvents; acetonitrile; DMF, N,N- dimethylacetamide, N-methyl-2-pyrrolidone, and the like amide- based solvents; dimethyl sulfoxide and the like sulfoxide-based solvents; alcohol-based solvents such as sulfolane, methanol, ethanol, isopropyl alcohol, and the like polar solvents. Any one of these solvents can be used alone or a combination of two or more types thereof can be used when necessary.

Reaction temperature for the aforementioned reaction is not particularly limited, and is typically within a range between - 20 °C and a boiling point of the solvent used, preferably -10 °C to 60°C, and more preferably 20 to 50°C. Reaction time varies depending on, for example, the reaction temperature, and the reaction typically ends in approximately 0.25 to 24 hours.

The sulfide compound (ΙΒ-b) obtained by the method shown in Step 2 is easily isolated from a reaction mixture and can be purified by use of typical isolation means and purification means, for example, filtration, solvent extraction, distillation, recrystallization, chromatography, etc. Each compound (IB) obtained after the completion of the reactions shown in Reaction Scheme 14 to Reaction Scheme 19 may be easily isolated from the reaction mixture and purified by known isolation and purification techniques, such as filtration, solvent extraction, distillation, recrystallization, and column chromatography.

When compound (IB) has regioisomers, each regioisomer may be separated by a usual separation step, such as silica gel chromatography .

Pest-Controlling Agent

Compound (1) of the present invention may be used as an active ingredient of a pest-controlling agent. Examples of pest- controlling agents include agents (agricultural and horticultural insecticide, miticides, nematicides, or soil insecticides) for controlling pests, mites, nematode, or soil pests that all cause problems in the agricultural and horticultural fields; animal- ectoparasite-controlling agents (e.g., pulicide, ixodicide, and pedivulicideon) , and the like.

For use as an active ingredient of a pest-controlling agent, it is possible to use compound (1) of the present invention as is with no additional components. However, it is usually preferable to use the compound by combining with a solid carrier, liquid carrier, or gaseous carrier (propellant) , and optionally with a surfactant and other adjuvants for pharmaceutical preparation, and formulating the resulting mixture into various forms such as oil solutions, emulsions, wettable powders, flowable preparations, granules, dusts, aerosols, fumigants, or the like, according to known preparation methods.

Compound (1) of the present invention is usually contained in these formulations in a proportion of 0.01 to 95 wt%, and preferably 0.1 to 50 wt%.

Examples of solid carriers usable in the formulations include solid carriers in a fine powder or granular form, such as clay (e.g., kaolin clay, diatomaceous earth, synthetic hydrated silicon dioxide, bentonite, Fubasami clay, and acid clay) , talc, ceramic, other inorganic minerals (e.g., celite, quartz, sulfur, active carbon, calcium carbonate, and hydrated silica) , and chemical fertilizers (e.g., ammonium sulfate, ammonium phosphate, ammonium nitrate, urea, and ammonium chloride) ; and the like.

Examples of liquid carriers include water, alcohols (e.g., methanol and ethanol) , ketones (e.g., acetone and methylethylketone) , aromatic hydrocarbons (e.g., benzene, toluene, xylene, ethylbenzene, and methylnaphthalene) , aliphatic hydrocarbons (e.g., hexane, cyclohexane, kerosene, and light oil), esters (e.g., ethyl acetate and butyl acetate), nitriles (e.g., acetonitrile and isobutyronitrile) , ethers (e.g., diisopropyl ether and dioxane) , acid amides (e.g., N, N-dimethylformamide and N, W-dimethylacetamide) , halogenated hydrocarbons (e.g., dichloromethane, trichloroethane, and carbon tetrachloride) , dimethylsulfoxide, soybean oil, cottonseed oil, and like vegetable oils, and the like.

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

Examples of surfactants include alkyl sulfates, alkyl sulfonates, alkylaryl sulfonates, alkyl aryl ethers, polyoxyethylene adducts thereof, polyethylene glycol ethers, polyhydric alcohol esters, sugar alcohol derivatives, and the like.

Examples of adjuvants for pharmaceutical preparation include fixing agents, dispersants, stabilizers, and the like.

Examples of the fixing agents and dispersants include casein, gelatin, polysaccharides (e.g., starch, gum arabic, cellulose derivatives, and alginic acid) , lignin derivatives, bentonite, sugars, and water-soluble synthetic polymers (e.g., polyvinyl alcohol, polyvinyl pyrrolidone, and polyacrylic acids) .

Examples of stabilizers include PAP (acidic isopropyl phosphate), BHT (2, 6-di- tert-butyl-4-methylphenol) , BHA (mixture of 2- tert-butyl-4-methoxyphenol and 3- tert-butyl-4-methoxyphenol) , vegetable oils, mineral oils, fatty acids, and fatty acid esters, and the like.

For the pest-controlling agent of the present invention, it is preferable to use compound (1) as is, or by diluting it with water or the like. The pest-controlling agent of the present invention may be used by mixing with, for example, other pest- controlling agents, such as known insecticides, nematicides, acaricides, fungicides, herbicides, plant-growth-controlling agents, synergists, soil conditioners, animal feeds, and the like, or it may be used simultaneously with these agents without mixing.

The amount of the pest-controlling agent of the invention is not limited, and may be suitably selected from a wide range according to various conditions such as the concentration of active ingredient, the form of preparation, type of disease or pest to be treated, type of plant, severity of disease, time for application, method for application, chemicals to be used in combination (insecticide, nematicide, miticide, fungicide, herbicide, plant growth control agent, synergist, soil conditioner, etc.), and amount and type of fertilizer.

When used as a pesticide, compound (1) of the present invention is usually used in an amount of 0.01 to 500 g/100 m 2 , and preferably 1 to 200 g/100 m 2 .

When used as a miticide, compound (1) of the present invention is usually used in an amount of 0.1 to 500 g/100 m 2 , and preferably 1 to 200 g/100 m 2 .

When used as an aphicide, compound (1) of the present invention is usually used in an amount of 0.1 to 500 g/100 m 2 , and preferably 1 to 200 g/100 m 2 .

When the emulsion, wettable powder, flowable preparation, or the like is used by diluting with water, the concentration is 0.1 to 1,000 ppm, and preferably 1 to 500 ppm. The granules, dusts, or the like can be used as is without dilution.

Compound (1) of the present invention is characterized by having a particularly excellent miticidal activity and a broad spectrum of activity. Compound (1) of the present invention is effectively used as an agricultural and horticultural insecticide, miticide, nematicide, or a soil insecticide. Specifically, compound (1) of the present invention is effective for controlling pests, such as green peach aphids, cotton aphids, and like aphids; diamondback moths, cabbage armyworms, common cutworms, codling moths, bollworms, tobacco budworms, gypsy moths, rice leafrollers, smaller tea tortrix moths, Colorado potato beetles, cucurbit leaf beetles, boll weevils, plant hoppers, leafhoppers, scales, bugs, whiteflies, thrips, grasshoppers, anthomyiid flies, scarabs, black cutworms, cutworms, ants, and agricultural pest insects; slugs, snails, and like gastropods; rat mite, cockroaches, houseflies, house mosquitoes, and like hygiene-harming insects; angoumois grain moths, adzuki bean weevils, red flour beetles, mealworms, and like stored-grain insects; case making clothes moths, black carpet beetles, subterranean termites, and like clothes-harming insects and house- and household-harming insects; and the like,

mites, such as two-spotted spider mites, carmine spider mites, citrus red mites, Kanzawa spider mites, European red mites (fruit tree spider mites) , broad mites, pink citrus rust mites, bulb mites, and like plant-parasitic mites; Tyrophagus putrescentiae, Dermatophagoides farinae, Chelacaropsis moorei, and like house dust mites; and the like, and

soil pests, such as root-knot nematodes, cyst nematodes, root- lesion nematodes, white-tip nematode, strawberry bud nematode, pine wood nematode, and like plant parasitic nematodes; pill bugs, sow bugs, and like isopods; and the like.

The pest-controlling agent of the present invention is also effective for controlling various pests resistant to chemicals such as organophosphorus agents, carbamate agents, synthetic pyrethroid agents, and neonicotinoid agent.

Reference literatures such as scientific literatures, patents, and patent applications cited herein are incorporated herein by reference to the same extent that the entirety of each document is specifically described. As used herein, "or" is used when "at least one or more" matters listed in the sentence can be used.

Examples

As described above, the present invention has been explained while showing preferred embodiments to facilitate understanding. Hereinafter, the present invention is described in more detail with reference to the following Production Examples and Examples; however, the aforementioned explanation and the following Production Examples and Examples are not provided to limit the present invention, but for the sole purpose of exemplification. Thus, the scope of the present invention is not limited to embodiments and these Examples specifically described herein and is limited only by the scope of claims.

Production Example 1:

Preparation of ethyl 2- (4-chloro-3, 5-dimethyl-lH-pyrazol-l- yl) acetate [3A- ( lA-1-234 ) ]

To a mixture of 4-chloro-3, 5-dimethyl-lH-pyrazole (0.50 g, 3.85 mmol, 1 equiv.)in DMF (5 ml) was added sodium hydride (0.14 g, 5.77 mmol, 1.5 equiv.) portion-wise at 0 °C. After 10 minutes this reaction mixture was added ethyl bromoacetate (0.77 g, 4.62 mmol, 1.2 equiv.) at 0 °C. The reaction mixture was then stirred at room temperature for 2 hrs . The reaction mixture was then quenched into ice and the product was then extracted with ethyl acetate. The combined organic layer was washed by IN HCl solution followed by brine solution, dried over sodium sulfate, filtered and concentrated under reduced pressure to get 0.83 g of the crude product 3A- (lA-1-234 ) as light yellow solid. The crude product thus obtained was used further as such without any purification.

1Η NMR (CDC1 3 ) : 4.75 (s, 2H) , 4.23 (q, J = 7.2 Hz, 2H) , 2.20 (s, 3H) , 2.19 (s, 3H) , 1.28 (t, J = 7.2 Hz, 3H) .

Production Example 2:

Preparation of 2- (4-chloro-3, 5-dimethyl-lH-pyrazol-l-yl) acetic acid [3B- (lA-1-234) ]

To a stirred solution of ethyl 2- (4-chloro-3, 5-dimethyl-lH- pyrazol-l-yl) acetate (0.80 g, 3.70 mmol, 1 equiv.) in THF/water (5 ml/2 ml) was added lithium hydroxide (0.23 g, 5.55 mmol, 1.5 equiv.) at room temperature and stirred at the same temperature for 5 hrs. The pH of the reaction mixture was then made acidic by the slow addition of IN HC1 solution. The product was then extracted with ethyl acetate. The combined organic layer was washed by distilled water followed by brine solution, dried over sodium sulfate, filtered and concentrated under reduced pressure to get 0.65 g of the crude product 3B- (lA-1-234) as white solid. The crude product thus obtained was used further as such without any purification.

¾ NMR (CDC1 3 ) : 4.78 (s, 2H) , 2.20 (s, 6H) .

Production Example 3:

Preparation of 2- (4-chloro-3, 5-dimethyl-lH-pyrazol-l-yl) -N- (2- fluoro-4-methylphenyl) acetamide [4- (lA-1-234) ]

To a solution of 2-fluoro-4-methylbenzenamine (2; 0.2 g, 1.6 mmol, 1 equiv.) and 2- (4-chloro-3, 5-dimethyl-lH-pyrazol-l-yl) acetic acid (3B- (lA-1-234) ; 0.36 g, 1.92 mmol, 1.2 equiv.) in pyridine (3 ml) slowly added P0C1 3 (0.37 g, 2.40 mmol, 1.5 equiv.) at 0 °C. The reaction was then stirred at the same temperature for 15 minutes. The reaction mixture was then quenched into ice and the product was then extracted with ethyl acetate. The combined organic layer was washed by IN HC1 solution followed by brine solution, dried over sodium sulfate, filtered and concentrated under reduced pressure to get crude product. The crude product thus obtained was purified by column chromatography on silica gel with a mixture of ethyl acetate and n-hexane as an eluent to obtain 0.17 g of the title compound 4-(lA-l-234) as light yellow solid.

¾ NMR (CDCI 3 ) : 8.41 (bs, 1H) , 8.06 (t, J = 8.4 Hz, 1H) , 6.92-6.85 (m, 2H), 4.77 (s, 2H) , 2.29 (s, 3H) , 2.27 (s, 3H) , 2.26 (s, 3H) . Production Example 4 : Preparation of 5- (2- ( 4-chloro-3, 5-dimethyl-lH-pyrazol-l- yl) acetamido) -4-fluoro-2-methyIbenzene-l-sulfonyl chloride [5(- lA-1-234) ]

Chlorosulfonic acid (0.13 g, 1.11 mmol, 3 equiv.) was added to 2- (4-chloro-3, 5-dimethyl-lH-pyrazol-l-yl) -N- (2-fluoro-4- methylphenyl) acetamide (4- (lA-1-234) ; 0.11 g, 0.37 mmol, 1 equiv.) at a temperature below 50 °C. The reaction mixture was then stirred at room temperature overnight. The reaction mixture was then quenched into ice, the product was then extracted with ethyl acetate. The combined organic layer was washed by distilled water, dried over sodium sulfate, filtered and concentrated under reduced pressure to get 0.09 g of the crude product 5-(lA-l-234) as black viscous oil. The crude product thus obtained was used further as such without any purification.

1Η NMR (CDCI 3 ) : 9.17 (s, 1H) , 9.06 (d, J = 7.6 Hz, 1H) , 7.12 (d, J = 10.8 Hz, 1H), 4.82 (S, 2H) , 2.72 (s, 3H) , 2.28 (s, 6H) .

Production Example 5 :

Preparation of 2- (4-chloro-3, 5-dimethyl-lH-pyrazol-l-yl) -N- (2- fluoro-5-mercapto-4-methylphenyl) acetamide [ 6- ( lA-1-234 ) ]

To a mixture of 5- (2- (4-chloro-3, 5-dimethyl-lH-pyrazol-l- yl) acetamido) -4-fluoro-2-methylbenzene-l-sulfonyl chloride (5-1A- 1-234; 0.09 g, 0.23 mmol, 1 equiv.) in toluene (5 ml) was added triphenyl phosphine (0.24 g, 0.92 mmol, 4 equiv.) at room temperature. The reaction was then heated to 100 °C for 3 hours. The reaction mixture was cooled to room temperature and all the volatiles were distilled out by rotary evaporator. The crude product thus obtained was purified by column chromatography on silica gel with a mixture of ethyl acetate and n-hexane as an eluent to obtain 0.07 g of the title compound 6-(lA-l-234) as a light yellow solid.

2 H NMR (CDCI 3 ) : 8.53 (bs, 1H) , 8.21 (d, J = 7.6 Hz, 1H) , 6.87 (d, J = 11.2 Hz, 1H) , 4.76 (s, 3H) , 3.32 (s, 1H) , 2.27 (s, 3H) , 2.26 (s, 6H) .

Example 1 Preparation of N- (5- (2, 2, 2-trifluoroethylthio) -2-fluoro-4-methyl phenyl) -2- (4-chloro-3, 5-dimethyl-lH-pyrazol-l-yl) acetamide (lA-1- 234)

To a cooled mixture of 2- (4-chloro-3, 5-dimethyl-lH-pyrazol-l-yl) - N- (2-fluoro-5-mercapto-4-methylphenyl) acetamide (6- (lA-1-234) ;

0.07 g, 0.21 mmol, 1 equiv. ) in DMF (5 ml) was added cesium carbonate (0.08 g, 0.26 mmol, 1.2 equiv.) followed by sodium formaldehyde sulfoxylate (0.03 g, 0.26 mmol, 1.2 equiv.). To this mixture was then added slowly trifluoroethyl iodide (0.05 g, 0.26 mmol, 1.2 equiv.) at 0 °C and the resulting mixture was then stirred at room temperature for 6 hours . The reaction mixture was then poured into distilled water and extracted with dichloromethane . The combined organic layer was washed with distilled water, dried over sodium sulfate, filtered and concentrated under reduced pressure to obtain a crude product. The crude product thus obtained was purified by column chromatography on silica gel with a mixture of ethyl acetate and n-hexane as an eluent to obtain 0.06 g of the title compound 1A- 1-234 as a white solid.

1Η NMR (CDC1 3 ) : δ 8.64 (bs, 1H) , 8.45 (d, J = 7.6 Hz, 1H) , 6.94 (d, J = 11.2 Hz, 1H), 4.77 (s, 2H) , 3.37 (q, J = 9.6 Hz, 2H) , 2.41 (s, 3H) , 2.27 (s, 6H) .

Production Example 6:

Preparation of N- (2-fluoro-4-methylphenyl) acetamide

To a mixture of 2-fluoro-4-methylaniline (5.50 g, 43.95 mmol, 1 equiv. ) in chloroform (30 ml) , a solution of acetic anhydride (4.49 g, 43.95 mmol, 1 equiv.) in chloroform (20 ml) was slowly added at 0 °C. The reaction mixture was then stirred at room temperature for 3 hours. The reaction mixture was then quenched into sodium bicarbonate solution and the product was extracted with dichloromethane. The combined organic layer was washed by sodium bicarbonate solution followed by distilled water, dried over sodium sulfate, filtered and concentrated under reduced pressure to get 5.92 g of the crude product as white solid. The crude product thus obtained was further used as such without any purification .

¾ NMR (CDCI 3 ) : δ 8.14-8.10 (m, 1H) , 7.25 (bs, 1H) , 6.93-6.88 (m, 2H) , 2.31 (s, 3H) , 2.20 (s, 3H) .

Production Example 7:

Preparation of 5-acetamido-4-fluoro-2-methylbenzene-l-sulfonyl chloride

Chlorosulfonic acid (20.56 g, 176.46 mmol, 5 equiv. ) was slowly added to N- (2-fluoro-4-methylphenyl) acetamide (5.90 g, 35.29 mmol, 1 equiv.) keeping the temperature of the reaction mixture below 50 °C. The resulting mixture was then heated to 70 °C for 4 hours. After cooling to room temperature, the reaction mixture was then poured carefully into ice, the precipitate was filtered, washed well with distilled water and dried to get 7.3 g of crude product as light brown solid. The crude product thus obtained was further used as such without any purification.

¾ NMR (CDCI 3 ) : δ 9.09 (d, J = 7.6 Hz, 1H) , 7.48 (bs, 1H) , 7.14 (d, J = 10.8 Hz, 1H) , 2.72 (s, 3H) , 2.25 (s, 3H) .

Production Example 8 :

Preparation of N- (2-fluoro-5-mercapto-4-methylphenyl) acetamide

To a mixture of 5-acetamido-4-fluoro-2-methylbenzene-l- sulfonyl chloride (7.00 g, 26.34 mmol, 1 equiv.) in glacial acetic acid (60 ml) was portion-wise added zinc dust (34.44 g, 526.80 mmol, 20 equiv.) at room temperature. The resulting mixture was then refluxed for 4 hours. After cooling to room temperature, the reaction mixture was diluted with distilled water and ethyl acetate and filtered through celite bed. The organic layer was washed well by distilled water, dried over sodium sulfate, filtered and concentrated under reduced pressure to get 3.64 g of the crude product as pale yellow solid. The crude product thus obtained was further used as such without any purification. ¾ NMR (CDCI3) : δ 8.25 (d, J = 7.6 Hz, 1H) , 7.29 (bs, 1H) , 6.89 J = 11.6 Hz, 1H) , 3.34 (bs, 1H) , 2.26 (s, 3H) , 2.20 (s, 3H) .

Production Example 9:

Preparation of N- (5- (2,2, 2-trifluoroethylthio) -2-fluoro-4- methylphenyl) acetamide

To a cooled mixture of N- (2-fluoro-5-mercapto-4- methylphenyl) acetamide (3.10 g, 15.56 mmol, 1 equiv. ) in DMF (30 ml) was added cesium carbonate (5.07 g, 15.56 mmol, 1 equiv.) followed by sodium formaldehyde sulfoxylate (1.84 g, 15.56 mmol, 1 equiv.). To this mixture was then added slowly trifluoroethyl iodide (3.27 g, 15.56 mmol, 1 equiv.) and the resulting mixture was then stirred at room temperature for 6 hours. The reaction mixture was then poured into distilled water and extracted with dichloromethane. The combined organic layer was washed with distilled water, dried over sodium sulfate, filtered and concentrated under reduced pressure to get crude product. The crude product thus obtained was purified by column chromatography on silica gel with a mixture of ethyl acetate and n-hexane as an eluent to obtain 2.90 g of the title, compound as an off white solid.

¾ NMR (CDCI 3 ) : δ 8.49 (d, J = 8.0 Hz, 1H) , 7.29 (bs, 1H) , 6.96 (d, J = 11.6 Hz, 1H), 3.42-3.35 (q, J = 9.6 Hz, 2H) , 2.41 (s, 3H) , 2.21 (s, 3H) .

Production Example 10:

Preparation of 5- (2, 2, 2-trifluoroethylthio) -2-fluoro-4- methylbenzenamine

To a mixture of N- (5- (2, 2, 2-trifluoroethylthio) -2-fluoro-4- methylphenyl) acetamide (2.20 g, 7.82 mmol, 1 equiv.) in ethanol/water (30 ml/4 ml) was added concentrated HC1 (30 ml) . The resulting mixture was then refluxed for 6 hours. After cooling to room temperature, all volatiles were removed by vacuum distillation and pH of the residue was then made basic by slow addition of IN NaOH solution. The product was then extracted with ethyl acetate. The combined organic layer was then washed with distilled water followed by brine solution, dried over sodium sulfate, filtered and concentrated under reduced pressure to get crude product as a brown oil. The crude product thus obtained was further used as such without any purification.

1Η NMR (CDC1 3 ) : δ 6.98 (d, J = 9.2 Hz, 1H) , 6.86 (d, J = 11.6 Hz, 1H), 3.64 (bs, 2H) , 3.32-3.25 (q, J = 9.6 Hz, 2H) , 2.36 (s, 3H) .

Example 2 :

Preparation of N- (5- (2, 2, 2-trifluoroethylthio) -2-fluoro-4- methylphenyl) -2- (4-chloro-lH-pyrazol-l-yl) acetamide (1Ά-1-19)

To a solution of 2-fluoro-4-methyl-5- (2, 2, 2- trifluoroethylthio) aniline (8; 0.1 g, 0.41 mmol, 1 equiv. ) and 2- (4-chloro-lH-pyrazol-l-yl) acetic acid (3b—; 0.07 g, 0.41 mmol, 1.0 equiv.) in pyridine (5 ml) slowly added P0C1 3 (0.49 g, 3.21 mmol, 7.8 equiv.) at 0 °C. The reaction was further maintained at the same temperature for 15 minutes. The reaction mixture was then quenched into ice and the product was then extracted with ethyl acetate. The combined organic layer was washed by IN HC1 solution followed by brine solution, dried over sodium sulfate, filtered and concentrated under reduced pressure to get crude product. The crude product thus obtained was purified by column chromatography on silica gel with a mixture of ethyl acetate and n-hexane as an eluent to obtain 0.03 g of the title compound 1A- 1-19 as off white solid.

1Η NMR (CDCI3) : 8.49 (bs, 1H) , 8.44 (d, J = 7.6 Hz, 1H) , 7.64 (bs, 1H) , 7.55-7.52 (m, 1H) , 6.96 (d, J = 11.2 Hz, 1H) , 4.93 (s, 2H) , 3.36 (q, J = 9.6 Hz, 2H) , 2.44 (s, 3H) . Example 3 :

Preparation of N- (5- (2, 2, 2-trifluoroethylthio) -2-fluoro-4- methylphenyl) -2- (4-nitro-lH-pyrazol-l-yl) acetamide (lA-1-16)

To a solution of 2-fluoro-4-methyl-5- (2, 2, 2- trifluoroethylthio) aniline (8; 0.14 g, 0.58 mmol, 1 equiv.) and 2- (4-nitro-lH-pyrazol-l-yl) acetic acid (3b— ; 0.10 g, 0.58 mmol, 1.0 equiv. ) in pyridine (5 ml) slowly added P0C1 3 (0.49 g, 3.21 mmol, 7.8 equiv.) at 0 °C. The reaction was further maintained at the same temperature for 15 minutes. The reaction mixture was then quenched into ice and the product was then extracted with ethyl acetate. The combined organic layer was washed by IN HC1 solution followed by brine solution, dried over sodium sulfate, filtered and concentrated under reduced pressure to get crude product. The crude product thus obtained was purified by column chromatography on silica gel with a mixture of ethyl acetate and n-hexane as an eluent to obtain 0.038 g of the title compound 1A-

1-16 as off white solid.

¾ NMR (CDCI 3 ) : 8.42 (d, J = 7.6 Hz, 1H) , 8.32 (s, 1H) , 8.31 (bs, 1H) , 8.24 (s, 1H), 6.99 (d, J = 11.6 Hz, 1H) , 5.00 (s, 2H) , 3.36 (q, J = 9.6 Hz, 2H) , 2.43 (s, 3H) .

Example 4 :

Preparation of N- (5- (2, 2, 2-trifluoroethylthio) -2-fluoro-4- methylphenyl) -2- (3, 6-dichloropyridin-2-yl) acetamide (lA-1-28)

To a solution of 2-fluoro-4-methyl-5- (2, 2, 2- trifluoroethylthio) aniline (8; 0.10 g, 0.42 mmol, 1 equiv.) and

2- (3, 6-dichloropyridin-2-yl) acetic acid (3b—; 0.08 g, 0.42 mmol, 1.0 equiv.) in pyridine (2 ml) slowly added P0C1 3 (0.09 g, 0.63 mmol, 1.5 equiv.) at 0 °C. The reaction was further maintained at the same temperature for 15 minutes . The reaction mixture was then quenched into ice and the product was then extracted with ethyl acetate. The combined organic layer was washed by IN HC1 solution followed by brine solution, dried over sodium sulfate, filtered and concentrated under reduced pressure to get crude product. The crude product thus obtained was purified by column chromatography on silica gel with a mixture of ethyl acetate and n-hexane as an eluent to obtain 0.06 g of the title compound 1A- 1-28 as off white solid.

¾ NMR (CDCI 3 ) : 9.17 (bs, 1H) , 8.53 (d, J = 7.6 Hz, 1H) , 7.71 (d, J = 8.4 Hz, 1H) , 7.28-7.27 (m, 1H) , 6.97 (d, J = 11.2 Hz, 1H) , 4.09 (s, 2H) , 3.37 (q, J = 9.6 Hz, 2H) , 2.42 (s, 3H) . Example 5 :

Preparation of N- (5- (2, 2, 2-trifluoroethylthio) -2-fluoro-4- methylphenyl) -2- ( 6-methylpyridin-2-yl) acetamide (lA-1-37 )

To a solution of 2-fluoro-4-methyl-5- (2 , 2 , 2- trifluoroethylthio) aniline (8; 0.10 g, 0.42 mmol, 1 equiv.) and 2- ( 6-methylpyridin-2-yl) acetic acid (3b—; 0.06 g, 0.42 mmol, 1.0 equiv.) in pyridine (2 ml) slowly added P0C1 3 (0.09 g, 0.63 mmol, 1.5 equiv.) at 0 °C. The reaction was further maintained at the same temperature for 15 minutes. The reaction mixture was then quenched into ice and the product was then extracted with ethyl acetate. The combined organic layer was washed by IN HC1 solution followed by brine solution, dried over sodium sulfate, filtered and concentrated under reduced pressure to get crude product. The crude product thus obtained was purified by column chromatography on silica gel with a mixture of ethyl acetate and n-hexane as an eluent to obtain 0.08 g of the title compound lA-1-37 as off white solid.

1Η NMR (CDCI 3 ) : 11.14 (bs, 1H) , 8.63 (d, J = 8.0 Hz, 1H) , 7.58 (t, J = 7.6 Hz, 1H) , 7.10 (d, J = 7.6 Hz, 1H) , 7.05 (d, J = 7.6 Hz, 1H) , 6.94 (d, J = 11.2 Hz, 1H) , 3.85 (s, 2H) , 3.39 (q, J = 9.6 Hz, 2H) , 2.62 (s, 3H) , 2.40 (s, 3H) .

Example 6 :

Preparation of 5- (2, 2, 2-trifluoroethylthio) -2-fluoro-4-methyl-N- (4- (trifluoromethoxy) phenyl) benzamide ( 1B-2-7 )

To a solution of 4- (trifluoromethoxy) benzenamine [12-(lB-2- 7)]; 0.04 g, 0.22 mmol, 1 equiv.) and 5-(2,2,2- trifluoroethylthio) -2-fluoro-4-methylbenzoic acid (11; 0.06 g, 0.22 mmol, 1.0 equiv.) in pyridine (5 ml) slowly added POCI 3 (0.10 g, 0.66 mmol, 3 equiv.) at 0 °C. The reaction was further maintained at the same temperature for 15 minutes. The reaction mixture was then quenched into ice and the product was then extracted with ethyl acetate. The combined organic layer was washed by IN HC1 solution followed by brine solution, dried over sodium sulfate, filtered and concentrated under reduced pressure to get crude product. The crude product thus obtained was purified by column chromatography on silica gel with a mixture of ethyl acetate and n-hexane as an eluent to obtain 0.05 g of the title compound 1B-2-7 as off white solid.

1Η NMR (CDC1 3 ) : 8.40 (bs, 1H) , 8.30 (d, J = 8.0 Hz, 1H) , 7.70-7.68 (m, 2H), 7.23 (m, 2H) , 7.09 (d, J = 12.8 Hz, 1H) , 3.44 (q, J = 9.2 Hz, 2H) , 2.54 (s, 3H) . Example 7 :

The compounds shown in Tables 1, 2 and 3, other than the compounds obtained in Examples 1 to 6, were produced by methods similar to the methods described in Examples 1 to 6 or methods described in the description.

Tables 1, 2 and 3 show 1 H-NMR data of the thus obtained compounds of the present invention.

The abbreviations in Tables 1, 2 and 3 are as indicated below.

F: fluoro, CI: chloro, Br: bromo, Me: methyl, Et: ethyl, n-Pr: normal-propyl, i-Pr: isopropyl, n-Bu: normal-butyl, t-Bu: tert- butyl, n-Pent: normal-pentyl, Ac: acetyl, CF 3 : trifluoromethyl, OMe: methoxy, OEt : ethoxy, OCF 3 : trifluoromethoxy, SCF 3 : trifluoromethylthio, 4~N, N-Me 2 N-Ph : 4- (N, N-dimethylamino) phenyl, SMe: methylthio, NH 2 : amino, NO 2 : nitro, Ph: phenyl, S: sulfur atom, 0: oxygen atom.

Table 1 : Detail and 1 H NMR of the compounds synthesized belonging to the general structure (lA-1) :

Table 2 : Detail and 1 H NMR of the compounds synth< belonging to the general structure (lB-1) :

Table 3 : Detail and 1 Η NMR of the compounds synthesized belonging to the general structure (1B-2) :

Below are Preparation Examples in which the "parts" refers to "parts by weight."

Preparation Example 1: Emulsions

10 parts of each compound of the invention was dissolved in 45 parts of Solvesso 150 and 35 parts of A/-methylpyrrolidone . 10 parts of an emulsifier (trade name: Sorpol 3005X, produced by Toho Chemical Industry Co., Ltd.) was added thereto. The mixtures were mixed by stirring to give 10% emulsions.

Preparation Example 2 : Wettable powders

20 parts of each compound of the invention was added to a mixture of 2 parts of sodium lauryl sulfate, 4 parts of sodium lignin sulfonate, 20 parts of fine powder of synthetic hydrated silicon dioxide, and 54 parts of clay. The mixtures were mixed by stirring with a juice mixer to give 20% wettable powders. Preparation Example 3 : Granules

2 parts of sodium dodecylbenzenesulfonate, 10 parts of bentonite, and 83 parts of clay were added to 5 parts of each compound of the invention, and each mixture was sufficiently mixed by stirring. An appropriate amount of water was added thereto. The resulting mixtures were further stirred and granulated with a granulator. The granules were air-dried to give 5% granules. Preparation Example 4 : Dusts

1 part of each compound of the invention was dissolved in an appropriate amount of acetone. 5 parts of fine powder of synthetic hydrated silicon dioxide, 0.3 parts of acidic isopropyl phosphate (PAP), and 93.7 parts of clay were added thereto. The mixtures were mixed by stirring with a juice mixer, and acetone was removed by evaporation to give 1% dust.

Preparation Example 5 : Flowable preparations

20 parts of each compound of the invention was mixed with 20 parts of water containing 3 parts of polyoxyethylene tristyrylphenyl ether phosphoric acid ester triethanolamine and 0.2 parts of Rhodorsil 426R. The mixtures were subjected to wet pulverization with a DYNO-Mill, and mixed with 60 parts of water containing 8 parts of propylene glycol and 0.32 parts of xanthan gum to give 20% suspensions in water.

Test Examples are given below to demonstrate that the compounds of the invention are useful as an active ingredient for miticides . Test Example 1 (Miticidal test on Two-Spotted Spider Mites)

A piece of non-woven fabric (4.5><5.5cm) was suspended inside a plastic cup through an incision made in the lid of the plastic cup. After water was poured into the cup, the cup was covered with the lid. A kidney bean leaf (about 3.5x4.5 cm) was then placed on the sufficiently soaked, non-woven fabric. Another kidney bean leaf with two-spotted spider mites (about 30 mite samples) was placed on top of the first leaf, and the fabric and leaves were placed in a thermostatic chamber having a temperature of 25+2° C and a humidity of 40% overnight. Next morning the top leaf was removed as the mite population had already moved to the lower leaf.

Miticidal formulations containing the compound of the invention (200 ppm) were prepared by adding an aqueous solution (100 ppm) of Sorpol 355 (manufactured by Tobo Kagaku Co. Ltd.) to a methanol solution of the compound of the invention.

These miticidal formulations were sprayed onto the leaves, and the leaves were air-dried and placed in a thermostatic chamber (25±2° C and a humidity of 50%) . The mortality rate of the two- spotted spider mites was calculated after 2 days.

The compounds (from Table 1) that exhibited the mortality rate of 50% or more at 200 ppm are as follows:

Compound Nos.: lA-1-2, lA-1-3, lA-1-8, lA-1-9, lA-1-10, 1A-

The compounds (from Table 2) that exhibited the mortality rate of 50% or more at 200 ppm are as follows: 1B- 1-1, lB-1-2, IB-l--3, lB-1-7, lB-1-8, IB-l- 12, lB-1--14,

1B- 1· -17, 1B- -1 -18, 1B- 1-20, IB- -1-24, lB-1-26, lB-1- 31, lB-1- -38,

1B- 1- -39, 1B- -1· -41, 1B- 1-42, IB- -1-45, lB-1-46, lB-1- 47, lB-1- -48,

1B- 1- -49, 1B- -1· -50, 1B- 1-51, IB- -1-52, lB-1-53, lB-1- 54, lB-1- -55,

1B- 1- -56, 1B- -1- -58, 1B- 1-59, IB- -1-60, lB-1-61, lB-1- 62, lB-1- -65,

1B- 1- -66, 1B- -1 -67, 1B- 1-68, IB- -1-69, lB-1-70, lB-1- 73, lB-1- -74,

1B- 1- -75, 1B- 1- 77, lB-1 -78, lB-1 -80, IB -1-81, 1B- -1-82, 1B- 1-83.

The compounds (from Table 3) that exhibited the mortality rate of 50% or more at 200 ppm are as follows:

1B-2-3, 1B-2-5, 1B-2-6, 1B-2-7, 1B-2-18, 1B-2-21, 1B-2-25, 1B-2-29, 1B-2-31, 1B-2-32, 1B-2-33, 1B-2-37, 1B-2-38, 1B-2-49, 1B-2-50, 1B-2-51, 1B-2-52, 1B-2-59, 1B-2-60.

Test Example 2 (Ovicidal test on Two-Spotted Spider Mites)

A piece of non-woven fabric (4.5x5.5cm) was suspended inside a plastic cup through an incision made in the lid of the plastic cup. After water was poured into the cup, the cup was covered with the lid. A kidney bean leaf (about 3.5x4.5 cm) was then placed on the sufficiently soaked, non-woven fabric. Twenty female adults of two-spotted spider mite were placed on the top of the leaf, and the fabric and leaf were placed in a thermostatic chamber having a temperature of 25±2° C and a humidity of 40% and 16L8D.

The next day, after the number of the female adults was adjusted once more to 20, 2 ml of a miticidal formulation containing the compound of the invention (200 ppm) prepared in the same manner as in test example 1 was sprayed onto the leaf, and the leaf was air-dried and placed in a thermostatic chamber (25±2° C and a humidity of 50%) . The ovicidal rate of the two-spotted spider mites was calculated 6 days after the spraying of the miticidal formulation. The compounds (from Table 1) that exhibited a mortality of 50% or more at 200 ppm are as follows:

Compound Nos . : lA-1-15, lA-1-16, lA-1-18, lA-1-21, lA-1-24, lA-1- 26, lA-1-29, lA-1-30, lA-1-53, lA-1-54, lA-1-55, lA-1-56, lA-1-57, lA-1-58, lA-1-61, lA-1-62, lA-1-63, lA-1-65, lA-1-66, lA-1-67, lA-1-68, lA-1-69, lA-1-70, lA-1-71, lA-1-72, lA-1-73, lA-1-76, lA-1-77, lA-1-82, lA-1-83, lA-1-84, lA-1-85, lA-1-86, lA-1-87, lA-1-88, lA-1-89, lA-1-91, lA-1-92, lA-1-93, lA-1-94, lA-1-95, lA-1-96, lA-1-100, lA-1-101, lA-1-102, lA-1-103, lA-1-104, lA-1- 113, lA-1-114, lA-1-115, lA-1-116, lA-1-117, lA-1-118, lA-1-119, lA-1-123, lA-1-127, lA-1-128, lA-1-130, lA-1-131, lA-1-132, lA-1- 133, lA-1-134, lA-1-140, lA-1-141, lA-1-144, lA-1-147, lA-1-151, lA-1-152, lA-1-153, lA-1-154, lA-1-158, lA-1-161, lA-1-162, lA-1- 163, lA-1-191, lA-1-192, lA-1-194, lA-1-195, lA-1-199, lA-1-200, lA-1-203, lA-1-205, lA-1-211, lA-1-212, lA-1-214, lA-1-217, lA-1- 218, lA-1-219, lA-1-220, lA-1-221, lA-1-227, lA-1-229, lA-1-230, lA-1-232, lA-1-233.

The compounds (from Table 2) that exhibited the mortality rate of 50% or more at 200 ppm are as follows:

lB-1-7, lB-1-8, lB-1-9, lB-1-11, lB-1-12, lB-1-17, lB-1-24, lB-1-26, lB-1-31, lB-1-38, lB-1-39, lB-1-41, lB-1-42, lB-1-45, lB-1-48, lB-1-49, lB-1-50, lB-1-51, lB-1-52, lB-1-53, lB-1-54, lB-1-56, lB-1-65, lB-1-66, 1B-1-67, lB-1-68, lB-1-69, lB-1-70, lB-1-72, lB-1-73, lB-1-74, lB-1-75, lB-1-77, lB-1-78, lB-1-82, lB-1-83.

The compounds (from Table 3) that exhibited the mortality rate of 50% or more at 200 ppm are as follows:

1B-2-3, 1B-2-5, 1B-2-6, 1B-2-7, 1B-2-25, 1B-2-29, 1B-2-31, 1B-2-37, 1B-2-38, 1B-2-49, 1B-2-50, 1B-2-51, 1B-2-52, 1B-2-59, 1B-2-60.

Test Example 3 (Aphicidal test on cotton aphid)

A piece of non-woven fabric (4.5 x 5.5cm) was suspended inside a plastic cup through an incision made in the lid of the plastic cup. After water was poured into the cup, the cup was covered with the lid. A cucumber leaf (about 3.5x4.5 cm) was then placed on the sufficiently soaked, non-woven fabric. Another cucumber leaf with cotton aphid (about 30 aphid samples) was placed on top of the first leaf, and the fabric and leaves were placed in a thermostatic chamber having a temperature of 25±2° C and a humidity of 40% overnight. Next morning the top leaf was removed as the aphid population had already moved to the lower leaf.

Aphicidal formulations containing the compound of the invention (200 ppm) were prepared by adding an agueous solution (100 ppm) of Sorpol 355 (manufactured by Tobo Kagaku Co. Ltd.) to a methanol solution of the compound of the invention.

These aphicidal formulations were sprayed onto the leaves, and the leaves were air-dried and placed in a thermostatic chamber (25±2° C and a humidity of 50%) . The mortality rate of the cotton aphid was calculated after 3 days.

The compounds (from Table 1) that exhibited the mortality rate of 50% or more at 200 ppm are as follows:

Compound Nos . : lA-1-24, lA-1-122, lA-1-204

The compounds (from Table 2) that exhibited the mortality rate of 50% or more at 200 ppm are as follows:

lB-1-10, lB-1-75, lB-1-82, lB-1-83

Test Example 4 (Fungicidal test on Sphaerotheca fuliginea, cucumber)

Sphaerotheca fuliginea is cultured on intact cucumber plants.

Infected leaves with spores were washed with 0.01% Tween 20 solution and were passed through tissue paper. Then the filtrate was diluted with the 0.01% Tween 20 solution to obtain l><10 6 cfu spore per ml.

The solution of the compound of the invention (200ppm) was sprayed on fresh healthy two week old cucumber plants. The plants were air-dried and inoculated with freshly prepared spore suspension. The inoculated plants were then placed in green house (25° C, a humidity of 60% and 16L8D) . The percent disease control was assessed 12 days after from leaf disease area compared to control .

The compounds (from Table 1) that exhibited effective disease control at 200 ppm are as follows:

Compound Nos.: lA-1-1 Test Example 5 (Fungicidal test on Phytophthora infestans)

The mycelium of Phytophthora infestans was washed with distilled water from four day old potato slice culture box and filtered through tissue paper. The filtrate was diluted with distilled water to obtain 1*10 6 sporangia per ml.

The solution of the compound of the invention (200ppm) was sprayed on fresh healthy tomato plant at least at the three leaf stage. The plants were air-dried and inoculated with freshly prepared sporangia suspension. The inoculated plants were then placed in a dew chamber (20° C and a humidity of 100%) . One day after inoculation the plants were shifted to thermostatic chamber (20° C, a humidity of 80%, and 16L8D) . The percent disease control was assessed five days after from leaf disease area compared to control .

The compounds (from Table 2) that exhibited effective disease control at 200 ppm are as follows:

lB-1-2, lB-1-7, lB-1-9, lB-1-10

Test example 3 (Fungicidal test on Pyricularia oryzae)

A small bit of mycelium of Pyricularia oryzae was taken from a culture tube and transferred onto an oat meal agar plate aseptically. The inoculated plate was kept for 7 days at 25°C. Then plates were incubated at 25 °C for 5 days under exposure to black light blue, 16L8D. After five days the plates were fully covered with spores of fungus . The spores were washed from the plate with 0.01% Tween 20 solution and were passed through tissue paper. Then the filtrate was diluted with the 0.01% Tween 20 solution to obtain lxl0 6 cfu spore per ml.

The solution of the compound of the invention (200ppm) was sprayed on fresh healthy two week old rice plants. The plants were air-dried and inoculated with freshly prepared spore suspension. The inoculated plants were then placed in a dew chamber (25° C and a humidity of 100%) . One day after inoculation the plants were shifted to a thermostatic chamber (25° C, a humidity of 80%, and 16L8D) . The percent disease control was assessed 5-7 days after from leaf disease area compared to control .

The compounds (from Table 1) that exhibited effective disease control at 200 ppm are as follows:

Compound Nos.: lA-1-1

(Note)

It is understood that patents, patent applications and literatures cited herein are incorporated herein by reference, as if the contents thereof are specifically described herein. The present application claims priority to Indian Provisional Application Nos. 2016-11031419 and 2016-11042181, the entire content of which is incorporated herein by reference.

[Industrial Applicability]

The present invention provides novel amide compounds, methods for producing the same, and miticides, ovicides, and aphicides, and thus the present inventions are particularly useful in the agricultural industry.