HK40006665A

HK40006665A - Novel benzylamide compound, method for producing the same, and miticide

Info

Publication number: HK40006665A
Application number: HK19130209.0A
Authority: HK
Inventors: 今井哲弥; S·K·库玛瓦特; M·K·辛格; P·K·乔汉; A·V·谢尔克; R·K·辛格; R·吉舍尔; A·巴特
Original assignee: 日本欧爱特农业科技株式会社
Priority date: 2016-07-18
Filing date: 2017-07-14
Publication date: 2020-05-22

Description

Novel benzamide compound, process for producing the same, and acaricide

Technical Field

The present invention relates to a novel benzamide compound, a method for preparing the same, and an acaricide containing the same.

Background

Since mites resistant to acaricides have appeared in recent years due to long-term use of acaricides, it has been difficult to achieve control by using known acaricides.

Under such circumstances, development of a novel acaricide expected to achieve excellent acaricidal activity is urgently required.

For example, patent literature (PTL)1) discloses a compound represented by the following formula (a):

wherein R is⁵Represents substituted or unsubstituted C_1-20Alkyl, substituted or unsubstituted amino, N-containing heterocycle, etc., and it is reported that this compound exhibits acaricidal activity.

However, in PTL 1, a urea compound is mainly produced, and although R therein is also produced⁵Amide compounds which are alkyl, haloalkyl, aryl or cycloalkyl groups, but wherein R is not disclosed⁵Amide compounds which are benzyl groups. In addition, PTL 1 does not disclose at all that the above compound (a) exhibits ovicidal activity.

CITATION LIST

Patent document

PTL 1: japanese patent laid-open application No. 2011-042611

Summary of The Invention

Technical problem

It is an object of the present invention to provide a novel benzamide compound or a salt thereof which exhibits acaricidal activity.

It is another object of the present invention to provide a process for producing a benzamide compound or a salt thereof.

It is another object of the present invention to provide a novel miticide containing a benzamide compound or a salt thereof.

Solution to the problem

The present inventors have conducted extensive studies to achieve the above object and have succeeded in synthesizing a compound having acaricidal activity represented by the following formula (1) or a salt thereof. The present inventors have conducted other studies based on the above findings. Thus, the present invention has been completed.

More specifically, the present invention includes the following embodiments:

item 1:

a benzamide compound represented by the formula (1):

or a salt thereof,

wherein R is¹Is represented by C_1-6Alkyl or C_1-6A haloalkyl group;

R²and R³Are the same or different and each represents hydrogen, halogen, cyano, nitro, C_1-6Alkyl radical, C_1-6Haloalkyl, C_1-6Alkoxy radical, C_1-6Haloalkoxy, C_1-6Alkoxy radical C_1-6Alkyl radical, C_1-6Halogenoalkoxy radical C_1-6Alkyl radical, C_3-8Cycloalkyl or C_3-8Cycloalkyl radical C_1-6An alkyl group;

R⁴represents hydrogen, formyl, C_1-6Alkyl radical, C_1-6Haloalkyl, C_1-6Alkoxy radical, C_1-6Haloalkoxy, C_1-6Alkoxy radical C_1-6Alkyl radical, C_1-6Halogenoalkoxy radical C_1-6Alkyl radical, C_3-8Cycloalkyl radical, C_3-8Cycloalkyl radical C_1-6Alkyl radical, C_1-6Alkylcarbonyl group, C_1-6Halogenoalkylcarbonyl group, C_1-6Alkoxycarbonyl group, C_1-6Halogenoalkoxycarbonyl, arylcarbonyl, aryloxycarbonyl, C_2-6Alkenyl radical, C_2-6Haloalkenyl, C_2-6Alkynyl, C_2-6Halogenated alkynyl, C_1-6Alkylsulfonyl radical, C_1-6Haloalkylsulfonyl group, C_1-6Alkylsulfinyl radical, C_1-6Haloalkylsulfinyl radical, C_1-6Alkylthio radical, C_1-6Halogenoalkylthio, aryl C_1-6Alkyl, arylsulfonyl, arylsulfinyl, arylthio or heterocycle, all of which are defined as R⁴The substituents of (a) may be optionally further substituted;

R⁵and R⁶Are the same or different and each represents hydrogen, halogen, C_1-6Alkyl or C_1-6A haloalkyl group; r⁵And R⁶Together with the carbon atoms, may or may not be bonded to each other via at least one heteroatom to form a 3-to 8-membered ring;

R⁷、R⁸、R⁹、R¹⁰and R¹¹Identical or different and each represents hydrogen, halogen, nitro, cyano, hydroxy, formyl, C_1-6Alkyl radical, C_1-6Haloalkyl, C_1-6Alkoxy radical, C_1-6Haloalkoxy, C_1-6Alkoxy radical C_1-6Alkyl radical, C_1-6Halogenoalkoxy radical C_1-6Alkyl radical, C_3-8Cycloalkyl radical, C_3-8Cycloalkyl radical C_1-6Alkyl radical, C_1-6Alkylcarbonyl group, C_1-6Halogenoalkylcarbonyl, arylcarbonyl, aryloxycarbonyl, C_1-6Alkoxycarbonyl group, C_1-6Halogenoalkoxycarbonyl, C_1-6Cyanoalkyl, C_1-6Cyanoalkoxy group, C_2-6Alkenyl radical, C_2-6Haloalkenyl, C_2-6Alkynyl, C_2-6Halogenated alkynyl, C_1-6Alkylsulfonyl radical, C_1-6Haloalkylsulfonyl group, C_1-6Alkylsulfinyl radical, C_1-6Haloalkylsulfinyl radical, C_1-6Alkylthio radical, C_1-6Halogenoalkylthio, C_3-8Cycloalkylsulfonyl radical, C_3-8Cycloalkyl sulfinyl radical, C_3-8Cycloalkylthio radical, C_3-8Cycloalkyl radical C_1-6Alkylsulfonyl radical, C_3-8Cycloalkyl radical C_1-6Alkylsulfinyl radical, C_3-8Cycloalkyl radical C_1-6Alkylthio radical, C_1-6Alkoxy radical C_1-6Alkylsulfonyl radical, C_1-6Alkoxy radical C_1-6Alkylsulfinyl radical, C_1-6Alkoxy radical C_1-6Alkylthio radical, C_2-6Alkenyloxy radical, C_2-6Haloalkenyloxy, C_2-6Alkynyloxy, C_2-6Haloalkynyloxy, C_1-6Alkylsulfonyloxy, C_1-6Haloalkylsulfonyloxy, C_1-6Alkylsulfinyloxy, C_1-6Haloalkylsulfinyloxy, carboxy, OCN, SCN, SF₅Substituted or unsubstituted amino, aryl C_1-6Alkyl, aryloxy, aryl C_1-6Alkoxy, arylsulfonyl, arylsulfinyl, arylthio, aryl C_1-6Alkylsulfonyl, aryl C_1-6Alkylsulfinyl, aryl C_1-6Alkylthio, heterocyclic C_1-6Alkyl or heterocycloxy, all of which may be optionally further substituted;

R⁷and R⁸、R⁸And R⁹、R⁹And R¹⁰Or R¹⁰And R¹¹Together with the phenyl ring to which they are bonded may or may not be bonded to each other via at least one heteroatom to form a 3-to 8-membered ring;

x represents oxygen or sulfur; and is

n represents an integer of 0 to 2.

Item 2:

the benzamide compound or salt thereof according to item 1, wherein R¹Is C_1-6A haloalkyl group.

Item 3:

the benzamide compound or salt thereof according to item 1 or 2, wherein R²And R³Are identical or different and each represents halogen, cyano or C_1-6An alkyl group.

Item 4:

the benzamide compound or salt thereof according to any one of items 1 to 3, wherein R⁴Is hydrogen or C_1-6An alkyl group.

Item 5:

the benzamide compound or salt thereof according to any one of items 1 to 4, wherein R⁷、R⁸、R⁹、R¹⁰And R¹¹Are the same or different and each represents hydrogen, halogen, nitro, C_1-6Alkyl radical, C_1-6Haloalkyl, C_1-6Alkoxy radical, C_1-6Haloalkoxy, C_1-6Alkylsulfonyl radical, C_1-6Haloalkylsulfonyl group, C_1-6Alkylsulfinyl radical, C_1-6Haloalkylsulfinyl radical, C_1-6Alkylthio radical, C_1-6A haloalkylthio group, a substituted or unsubstituted amino group, an aryl group or a heterocycle.

Item 6:

the benzamide compound or a salt thereof according to any one of the preceding items, wherein the benzamide compound is represented by formula (1-3):

wherein

R³Represents halogen;

R⁴represents hydrogen, C_1-6Alkyl or C_1-6A haloalkyl group;

R⁵and R⁶Are identical or different and each represents hydrogen or halogen;

x represents O or S;

l represents a single bond, O or S;

X¹、X²and X³Identical or different and each represents halogen; and is

X⁴、X⁵And X⁶Identical or different and each represents hydrogen or halogen.

Item 7:

the benzamide compound or salt thereof according to any one of the preceding items, wherein X⁴、X⁵And X⁶Identical or different and each represents halogen.

Item 8:

the benzamide compound or salt thereof according to any one of the preceding items, wherein R⁵And R⁶Identical or different and each represents hydrogen, fluorine, chlorine or bromine.

Item 9:

the benzamide compound or salt thereof according to any one of the preceding items, wherein R⁵And R⁶Identical or different and each represents hydrogen, fluorine or chlorine.

Item 10:

the benzamide compound or salt thereof according to any one of the preceding items, wherein R⁵And R⁶Are identical or different and each represents hydrogen or fluorine.

Item 11:

the benzamide compound or salt thereof according to any one of the preceding items, wherein R⁵And R⁶Is hydrogen.

Item 12:

the benzamide compound or salt thereof according to any one of the preceding items, wherein R⁴Represents hydrogen, methyl or ethyl。

Item 13:

the benzamide compound or salt thereof according to any one of the preceding items, wherein L is O or S.

Item 14:

the benzamide compound or salt thereof according to any one of the preceding items, wherein X is O.

Item 15:

the benzamide compound or salt thereof according to any one of the preceding items, wherein R³Is fluorine, chlorine or bromine.

Item 16:

the benzamide compound or salt thereof according to any one of the preceding items, wherein R³Is fluorine or chlorine.

Item 17:

the benzamide compound or salt thereof according to any one of the preceding items, wherein R³Is fluorine.

Item 18:

the benzamide compound or salt thereof according to any one of the preceding items, wherein X¹、X²And X³Identical or different and each represents fluorine, chlorine or bromine.

Item 19:

the benzamide compound or salt thereof according to any one of the preceding items, wherein X¹、X²And X³Identical or different and each represents fluorine or chlorine.

Item 20:

the benzamide compound or salt thereof according to any one of the preceding items, wherein X⁴、X⁵And X⁶Identical or different and each represents fluorine, chlorine or bromine.

Item 21:

the benzamide compound or salt thereof according to any one of the preceding items, wherein X⁴、X⁵And X⁶Identical or different and each represents fluorine or chlorine.

Item 22:

a benzamide compound selected from the group consisting of: compounds 1A-12, 1A-14, 1A-42, 1A-43, 1A-24, 1A-47, 1A-48, 1A-49, 1A-51, 1A-52, 1A-53, 1A-54, 1A-56, 1A-58, 1A-59, 1A-60, 1A-62, 1A-69, 1A-72, 1A-73, 1A-74, 1A-75, 1A-76, 1A-77, 1A-78, 1A-82, 1A-83, 1A-91, 1A-92, 1A-112, 1A-116, 1A-117, 1A-137, 1A-138, 1B-28, 1B-39, 1B-53, 1A-60, 1A-62, 1A-112, 1A-116, 1A-117, 1A-137, 1A-138, 1B-28, 1B-39, 1, 1B-54, 1B-56, 1B-79, 1B-80, 1B-86 and 1B-87, or salts thereof.

Item 23:

a benzamide compound selected from the group consisting of: compounds 1A-14, 1A-42, 1A-47, 1A-48, 1A-49, 1A-51, 1A-54, 1A-56, 1A-58, 1A-59, 1A-62, 1A-73 and 1A-75, or a salt thereof.

Item 24:

the benzamide compound or a salt thereof according to any one of the preceding items, wherein the benzamide compound is represented by formula (1-4):

wherein

R³Represents halogen;

R⁴represents hydrogen, methyl or ethyl;

R⁵and R⁶Are the same or different and each represents hydrogen, halogen, C_1-6Alkyl or C_1-6A haloalkyl group;

R¹²、R¹³、R¹⁴、R¹⁵and R¹⁶Identical or different and each represents hydrogen, halogen, nitro, cyano, hydroxy, formyl, C_1-6Alkyl radical, C_1-6Haloalkyl, C_1-6Alkoxy radical, C_1-6Haloalkoxy, C_1-6Alkoxy radical C_1-6Alkyl radical, C_1-6Halogenoalkoxy radical C_1-6Alkyl radical, C_3-8Cycloalkyl radical, C_3-8Cycloalkyl radical C_1-6Alkyl radical, C_1-6Alkylcarbonyl group, C_1-6Halogenoalkylcarbonyl, arylcarbonyl, aryloxycarbonyl, C_1-6Alkoxycarbonyl group, C_1-6Halogenoalkoxycarbonyl, C_1-6Cyanoalkyl, C_1-6Cyanoalkoxy group, C_2-6Alkenyl radical, C_2-6Haloalkenyl, C_2-6Alkynyl, C_2-6Halogenated alkynyl, C_1-6Alkylsulfonyl radical, C_1-6Haloalkylsulfonyl group, C_1-6Alkylsulfinyl radical, C_1-6Haloalkylsulfinyl radical, C_1-6Alkylthio radical, C_1-6Halogenoalkylthio, C_3-8Cycloalkylsulfonyl radical, C_3-8Cycloalkyl sulfinyl radical, C_3-8Cycloalkylthio radical, C_3-8Cycloalkyl radical C_1-6Alkylsulfonyl radical, C_3-8Cycloalkyl radical C_1-6Alkylsulfinyl radical, C_3-8Cycloalkyl radical C_1-6Alkylthio radical, C_1-6Alkoxy radical C_1-6Alkylsulfonyl radical, C_1-6Alkoxy radical C_1-6Alkylsulfinyl radical, C_1-6Alkoxy radical C_1-6Alkylthio radical, C_2-6Alkenyloxy radical, C_2-6Haloalkenyloxy, C_2-6Alkynyloxy, C_2-6Haloalkynyloxy, C_1-6Alkylsulfonyloxy, C_1-6Haloalkylsulfonyloxy, C_1-6Alkylsulfinyloxy, C_1-6Haloalkylsulfinyloxy, carboxy, OCN, SCN, SF₅Substituted or unsubstituted amino, aryl C_1-6Alkyl, aryloxy, aryl C_1-6Alkoxy, arylsulfonyl, arylsulfinyl, arylthio, aryl C_1-6Alkylsulfonyl, aryl C_1-6Alkylsulfinyl, arylC_1-6Alkylthio, heterocyclic C_1-6Alkyl or heterocycloxy, all of which may be optionally further substituted;

x represents oxygen or sulfur; and is

X¹、X²And X³Identical or different and each represents halogen.

Item 25:

Item 26:

Item 27:

Item 28:

Item 29:

Item 30:

the benzamide compound or salt thereof according to any one of the preceding items, wherein X¹、X²And X³Is fluorine.

Item 31:

according to any of the preceding itemsThe benzamide compound or a salt thereof described above, wherein R⁴Represents hydrogen or methyl.

Item 32:

the benzamide compound or salt thereof according to any one of the preceding items, wherein R⁴Represents hydrogen.

Item 33:

the benzamide compound or salt thereof according to any one of the preceding items, wherein R⁵And R⁶Identical or different and each represents hydrogen or halogen.

Item 34:

the benzamide compound or salt thereof according to any one of the preceding items, wherein R⁵And R⁶Each represents hydrogen.

Item 35:

the benzamide compound or salt thereof according to any one of the preceding items, wherein R¹²、R¹³、R¹⁴、R¹⁵And R¹⁶Are the same or different and each represents hydrogen, halogen, cyano, C_1-6Haloalkyl, C_1-6Haloalkoxy or C_1-6An alkylthio group.

Item 36:

a benzamide compound selected from the group consisting of: compounds 1A-27, 1A-28, 1A-29, 1A-63, 1A-65, 1A-66, 1A-67, 1A-68, 1A-93, 1A-94, 1A-95, 1A-96, 1A-102, 1A-103, 1A-104, 1A-105, 1A-106, 1A-107, 1A-108, 1A-109, 1A-110, 1A-111, 1A-113, 1A-114, 1A-118, 1A-119, 1A-120, 1A-121, 1A-122, 1A-123, 1A-124, 1A-125, 1A-127, 1A-128, 1A-140, 1A-141, 1A-142, 1A-143, 1A-144, 1A-145, 1A-146, 1A-147, 1A-148, 1A-149, 1B-4, 1B-5, 1B-6, 1B-11, 1B-12, 1B-13, 1B-14, 1B-15, 1B-16, 1B-17, 1B-18, 1B-19, 1B-20, 1B-21, 1B-26, 1B-27, 1B-29, 1B-30, 1B-31, 1B-32, 1B-33, 1B-34, 1B-35, 1B-37, 1B-38, 1B-40, 1B-41 and 1B-43, or a salt thereof.

Item 37:

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

step (d): obtaining a thioether compound represented by formula (1-1) by reacting a thiol compound represented by formula (6) with an alkylating agent represented by formula (7):

wherein R is¹、R²、R³、R⁴、R⁵、R⁶、R⁷、R⁸、R⁹、R¹⁰、R¹¹And X is as defined above and G represents a leaving group; and

a step (e): obtaining a benzamide compound represented by formula (1-2) by reacting a thioether compound represented by formula (1-1) with an oxidizing agent:

wherein R is¹、R²、R³、R⁴、R⁵、R⁶、R⁷、R⁸、R⁹、R¹⁰、R¹¹And X is as defined above, n' represents 1 or 2.

Item 38:

a process for the preparation of the benzamide compound and its salt according to any of the preceding items, further comprising the following step (c):

step (c): obtaining a thiol compound represented by formula (6) by reacting a sulfonyl chloride compound represented by formula (5) with a reducing agent:

wherein R is²、R³、R⁴、R⁵、R⁶、R⁷、R⁸、R⁹、R¹⁰、R¹¹And X is as defined above.

Item 39:

a process for the preparation of the benzamide compound and salts thereof according to any of the preceding items, further comprising the following step (b):

step (b): obtaining a sulfonyl chloride compound represented by formula (5) by chlorosulfonylating the amide compound represented by formula (4):

Item 40:

a process for the preparation of the benzamide compound and salts thereof according to any of the preceding items, further comprising the following step (a):

step (a): obtaining an amide compound represented by formula (4) by reacting an aniline compound represented by formula (2) with a benzylcarbonyl compound represented by formula (3):

wherein R is²、R³、R⁴、R⁵、R⁶、R⁷、R⁸、R⁹、R¹⁰、R¹¹And X is as defined above, and Y represents a leaving group or a hydroxyl group.

Item 41:

a pesticidal agent containing the benzamide compound according to any one of the preceding items or a salt thereof.

Item 42:

an acaricide comprising the benzamide compound or salt thereof according to any one of the preceding items.

Advantageous effects of the invention

The benzamide compound or a salt thereof of the present invention can achieve an excellent miticidal effect with a small amount.

According to the present invention, a benzamide compound and a salt thereof can be easily produced with excellent yield.

Further, according to the present invention, a novel miticide containing the benzamide compound of the present invention or a salt thereof can be provided.

Description of the embodiments

The present invention is described below. Throughout this specification, unless specifically stated otherwise, singular expressions should be understood to cover the concepts of the plural forms thereof. Thus, the singular articles (e.g., "a", "an", "the", etc. in the case of the english language) should also be construed to cover the plural concepts thereof unless specifically stated otherwise. Furthermore, unless otherwise specifically noted, the terms used herein should be understood to be used in the sense commonly used by those skilled in the art. Accordingly, unless defined otherwise, all terms and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. In case of conflict, the present specification, including definitions, will control.

1. Benzamide compound or salt thereof

The present invention relates to a compound represented by formula (1):

or a salt thereof (hereinafter sometimes referred to as "benzamide compound (1)" or "compound (1)" of the present invention), wherein R is¹、R²、R³、R⁴、R⁵、R⁶、R⁷、R⁸、R⁹、R¹⁰、R¹¹X and n are as defined above.

Next, terms in this specification are described below.

In the present specification, the number of substituents of a group defined by "optionally substituted" or "substituted" where it may be substituted is not particularly limited, and is one or more. In addition, unless otherwise indicated, the description of each group applies when the group is part of or a substituent on another group.

“C_1-6Alkyl "means a straight or branched chain saturated hydrocarbon group having 1 to 6 carbon atoms.

“C_2-6Alkenyl "means a straight or branched unsaturated hydrocarbon group having 2 to 6 carbon atoms and containing 1 to 3 double bonds.

“C_2-6Alkynyl "means a straight or branched chain unsaturated hydrocarbon group having 2 to 6 carbon atoms and containing 1 triple bond.

“C_3-8Cycloalkyl "means cyclic alkyl groups having 3 to 8 carbon atoms, and includes those having a partial bridging structure.

“C_1-6Alkoxy "means" C_1-6Alkyloxy ", and" C_1-6Definition of alkyl moiety with respect to "C" above_1-6Alkyl groups "are the same.

"aryl" means a monocyclic or polycyclic aromatic hydrocarbon.

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

Specific examples of each group as used in the present specification are shown below.

Examples of halogen include, but are not particularly limited to, fluorine, chlorine, bromine, iodine, and the like.

C_1-6Examples of the alkyl group include, but are not particularly limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, n-hexyl and the like C_1-6Straight or branched chain alkyl.

C_1-6Examples of the haloalkyl group include, but are not particularly limited to, fluoromethyl, chloromethyl, bromomethyl, iodomethyl, difluoromethyl, trifluoromethyl, 2,2, 2-trifluoroethyl, pentafluoroethyl, 3,3, 3-trifluoropropyl, 4,4, 4-trifluorobutyl, pentafluoroisobutyl and the like, C substituted with 1 to 9 and preferably 1 to 5 halogen atoms_1-6Straight or branched chain alkyl.

C_1-6Examples of the alkoxy group include, but are not particularly limited to, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy and the like C_1-6Straight or branched alkoxy.

C_1-6Examples of the haloalkoxy group 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, pentafluoroisobutoxy and the like, which are substituted with 1 to 9, preferably 1 to 5 halogen atoms_1-6Straight or branched alkoxy.

C_1-6Alkoxy radical C_1-6Examples of alkyl groups 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 the like wherein C is_1-6Straight or branched chain alkyl by C_1-6Straight or branched alkoxy-substituted alkoxyalkyl.

C_1-6Halogenoalkoxy radical C_1-6Examples of the alkyl group include, but are not particularly limited to, fluoromethoxymethyl, chloromethoxymethyl, bromomethoxymethyl, iodomethoxymethyl, difluoromethoxymethyl, trifluoromethoxy methyl, 2,2, 2-trifluoroethoxymethyl and the like, straight-chain or branched alkoxyalkyl groups substituted with 1 to 9, preferably 1 to 5 halogen atoms.

C_3-8Examples of cycloalkyl groups include, but are not particularly limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, and the like.

C_3-8Cycloalkyl radical C_1-6Examples of alkyl groups include, but are not particularly limited to, cyclopropylmethyl, cyclobutylethyl, cyclopentylmethyl, cyclohexylmethyl, and the like.

C_1-6Examples of the alkylcarbonyl group include, but are not particularly limited to, methylcarbonyl (acetyl), ethylcarbonyl (propionyl), n-propylcarbonyl (butyryl), isopropylcarbonyl (isobutyryl), n-butylcarbonyl (valeryl), isobutylcarbonyl (isovaleryl), sec-butylcarbonyl, tert-butylcarbonyl and the like C_1-6Straight or branched chain alkylcarbonyl.

C_1-6Examples of the haloalkylcarbonyl group 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 the like substituted with 1 to 9 and preferably 1 to 5 pro-halogensSub-substituted C_1-6Straight or branched chain alkylcarbonyl.

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

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

C_1-6Examples of the alkoxycarbonyl group include, but are not particularly limited to, methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl, n-butoxycarbonyl, isobutoxycarbonyl, sec-butoxycarbonyl, tert-butoxycarbonyl and the like C_1-6Straight or branched chain alkoxycarbonyl.

C_1-6Examples of the haloalkoxycarbonyl group include, but are not particularly limited to, fluoromethoxycarbonyl, chloromethoxycarbonyl, bromomethoxycarbonyl, iodomethoxycarbonyl, dichloromethoxycarbonyl, trichloromethoxycarbonyl, difluoromethoxycarbonyl, trifluoromethoxy carbonyl, 2,2, 2-trifluoroethoxymethyl, pentafluoroethoxycarbonyl, 3,3, 3-trifluoropropoxycarbonyl, 4,4, 4-trifluorobutoxycarbonyl, pentafluoroisopropoxycarbonyl and the like which are substituted with 1 to 9, preferably 1 to 5 halogen atoms_1-6Straight or branched chain alkoxycarbonyl.

Cyano group C_1-6Examples of the alkyl group 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 the like, C substituted with cyano group_1-6Straight or branched chain alkyl.

Cyano group C_1-6Examples of alkoxy include cyanomethoxy, cyanoethoxy, cyano-n-propoxy, cyano-isopropoxy, cyano-n-butylCyano-substituted C such as oxy, cyano-isobutoxy, cyano-sec-butoxy, cyano-tert-butoxy, cyano-hexyloxy_1-6Straight or branched alkoxy.

C_2-6Examples of alkenyl groups include, but are not particularly limited to, vinyl, allyl, 2-butenyl, 3-butenyl, 1-methylallyl, and the like.

C_2-6Examples of the haloalkenyl group include, but are not particularly limited to, 2-dichlorovinyl, 2-dibromovinyl, 2-difluorovinyl, 2-dibromovinyl, 3-difluoro-2-allyl, 4, 4-difluoro-3-butenyl, 4,4, 4-trifluoro-2-butenyl, and the like.

C_2-6Examples of alkynyl include, but are not particularly limited to, ethynyl, 2-propynyl (propargyl), 1-methyl-2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, and the like.

C_2-6Examples of the haloalkynyl group include, but are not particularly limited to, fluoroethynyl, bromoethynyl, chloroethynyl, iodoethynyl, 3,3, 3-trifluoro-1-propynyl and the like.

C_1-6Examples of the alkylsulfonyl group include, but are not particularly limited to, methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, isopropylsulfonyl, n-butylsulfonyl, isobutylsulfonyl, sec-butylsulfonyl, tert-butylsulfonyl and the like C_1-6A linear or branched alkylsulfonyl group.

C_1-6Examples of the haloalkylsulfonyl group include, but are not particularly limited to, fluoromethylsulfonyl group, chloromethylsulfonyl group, bromomethylsulfonyl group, iodomethylsulfonyl group, dichloromethylsulfonyl group, trichloromethylsulfonyl group, difluoromethylsulfonyl group, trifluoromethylsulfonyl group, chlorodifluoromethylsulfonyl group, bromodifluoromethylsulfonyl group, dichlorofluoromethylsulfonyl group, 2,2, 2-trichloroethylsulfonyl group, 2,2, 2-trifluoroethylsulfonyl group, pentafluoroethylsulfonyl group and the like, which are substituted with 1 to 9 and preferably 1 to 5 halogen atoms_1-6A linear or branched alkylsulfonyl group.

C_1-6Examples of alkylsulfinyl groups includeBut not particularly limited to, C such as methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, isopropylsulfinyl, n-butylsulfinyl, isobutylsulfinyl, sec-butylsulfinyl, tert-butylsulfinyl_1-6A linear or branched alkylsulfinyl group.

C_1-6Examples of the haloalkylsulfinyl group 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 the like, which are substituted with 1 to 9 and preferably 1 to 5 halogen atoms_1-6A linear or branched alkylsulfinyl group.

C_1-6Examples of the alkylthio group include, but are not particularly limited to, methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, sec-butylthio, tert-butylthio and the like, C_1-6Straight or branched alkylthio.

C_1-6Examples of the haloalkylthio group include, but are not particularly limited to, fluoromethylthio group, chloromethylthio group, bromomethylthio group, iodomethylthio group, dichloromethylthio group, trichloromethylthio group, difluoromethylthio group, trifluoromethylthio group, chlorodifluoromethylthio group, bromodifluoromethylthio group, dichlorofluoromethylthio group, 2,2, 2-trichloroethylthio group, 2,2, 2-trifluoroethylthio group, pentafluoroethylthio group and the like, which are substituted with 1 to 9 and preferably 1 to 5 halogen atoms_1-6Straight or branched alkylthio.

C_3-8Examples of cycloalkylsulfonyl include, but are not particularly limited to, cyclopropylsulfonyl, cyclobutylsulfonyl, cyclopentylsulfonyl, cyclohexylsulfonyl, and the like.

C_3-8Examples of cycloalkylsulfinyl include, but are not particularly limited to, cyclopropylsulfinyl, cyclobutylsulfinyl, cyclopentylsulfinylAlkyl, cyclohexylsulfinyl, and the like.

C_3-8Examples of cycloalkylthio include, but are not particularly limited to, cyclopropylthio, cyclobutylthio, cyclopentylthio, cyclohexylthio, and the like.

C_3-8Cycloalkyl radical C_1-6Examples of alkylsulfonyl include, but are not particularly limited to, cyclopropylmethylsulfonyl, 2-cyclopropylethylsulfonyl, 3-cyclopropylpropylsulfonyl, cyclohexylmethylsulfonyl, and the like.

C_3-8Cycloalkyl radical C_1-6Examples of the alkylsulfinyl group include, but are not particularly limited to, cyclopropylmethylsulfinyl group, 2-cyclopropylethylsulfinyl group, 3-cyclopropylpropylsulfinyl group, cyclohexylmethylsulfinyl group and the like.

C_3-8Cycloalkyl radical C_1-6Examples of the alkylthio group include, but are not particularly limited to, cyclopropylmethylthio, 2-cyclopropylethylthio, 3-cyclopropylpropylthio, cyclohexylmethylthio and the like.

C_1-6Alkoxy radical C_1-6Examples of alkylsulfonyl include, but are not particularly limited to, methoxymethylsulfonyl, ethoxymethylsulfonyl, n-propoxymethylsulfonyl, isopropoxymethylsulfonyl, n-butoxymethylsulfonyl, sec-butoxymethylsulfonyl, tert-butoxymethylsulfonyl, methoxyethylsulfonyl and the like wherein C_1-6Straight-chain or branched alkylsulfonyl by C_1-6Linear or branched alkoxy-substituted alkoxyalkyl sulfonyl.

C_1-6Alkoxy radical C_1-6Examples of the alkylsulfinyl group include, but are not particularly limited to, methoxymethylsulfinyl group, ethoxymethylsulfinyl group, n-propoxymethylsulfinyl group, isopropoxymethylsulfinyl group, n-butoxymethylsulfinyl group, sec-butoxymethylsulfinyl group, tert-butoxymethylsulfinyl group, 2-methoxyethylsulfinyl group and the like wherein C is_1-6Straight-chain or branched alkylsulfinyl radicals bound by C_1-6A linear or branched alkoxy-substituted alkoxyalkyl sulfinyl group.

C_1-6Alkoxy radical C_1-6Examples of alkylthio include, but are not particularly limited to, methoxymethylthio, ethoxymethylthio, n-propoxymethylthio, isopropoxymethylthio, n-butoxymethylthio, sec-butoxymethylthio, tert-butoxymethylthio, 2-methoxyethylthio and the like wherein C is_1-6Straight-chain or branched alkylthio by C_1-6Linear or branched alkoxy-substituted alkoxyalkylthio.

C_2-6Examples of alkenyloxy include, but are not particularly limited to, vinyloxy, 1-propenyloxy, isopropenyloxy, allyloxy, 2-butenyloxy, 3-butenyloxy, 1-methylallyloxy, and the like.

C_2-6Examples of the haloalkenyloxy group include, but are not particularly limited to, 2-dichlorovinyloxy, 2-dibromovinyloxy, 2-difluorovinyloxy, 2-dibromovinyloxy, 3-difluoro-2-allyloxy, 4, 4-difluoro-3-butenyloxy, 4,4, 4-trifluoro-2-butenyloxy and the like.

C_2-6Examples of alkynyloxy include, but are not particularly limited to, ethynyloxy, 2-propynyloxy, 1-methyl-2-propynyloxy, 1-dimethyl-2-propynyloxy, 1-butynyloxy, 2-butynyloxy, 3-butynyloxy, and the like.

C_2-6Examples of the haloalkynyloxy group include, but are not particularly limited to, fluoroethynyloxy group, bromoethynyloxy group, chloroethynyloxy group, iodoethynyloxy group, 3,3, 3-trifluoro-1-propynyloxy group and the like.

C_1-6Examples of the alkylsulfonyloxy group include, but are not particularly limited to, methylsulfonyloxy, ethylsulfonyloxy, n-propylsulfonyloxy, isopropylsulfonyloxy, n-butylsulfonyloxy, isobutylsulfonyloxy, sec-butylsulfonyloxy, tert-butylsulfonyloxy and the like C_1-6A linear or branched alkylsulfonyl group.

C_1-6Examples of haloalkylsulfonyloxyIncluding, but not particularly limited to, fluoromethylsulfonyloxy, chloromethylsulfonyloxy, bromomethylsulfonyloxy, iodomethylsulfonyloxy, dichloromethylsulfonyloxy, trichloromethylsulfonyloxy, difluoromethylsulfonyloxy, trifluoromethylsulfonyloxy, chlorodifluoromethylsulfonyloxy, bromodifluoromethylsulfonyloxy, dichlorofluoromethylsulfonyloxy, 2,2, 2-trichloroethylsulfonyloxy, 2,2, 2-trifluoroethylsulfonyloxy, pentafluoroethylsulfonyloxy and the like, C substituted with 1 to 9 and preferably 1 to 5 halogen atoms_1-6Straight or branched chain alkylsulfonyloxy.

C_1-6Examples of the alkylsulfinyloxy group include, but are not particularly limited to, methylsulfinyloxy, ethylsulfinyloxy, n-propylsulfinyloxy, isopropylsulfinyloxy, n-butylsulfinyloxy, isobutylsulfinyloxy, sec-butylsulfinyloxy, tert-butylsulfinyloxy and the like_1-6Linear or branched alkylsulfinyloxy.

C_1-6Examples of the haloalkylsulfinyloxy group include, but are not particularly limited to, fluoromethylsulfinyloxy group, chloromethylsulfinyloxy group, bromomethylsulfinyloxy group, iodomethylsulfinyloxy group, dichloromethylsulfinyloxy group, trichloromethylsulfinyloxy group, difluoromethylsulfinyloxy group, trifluoromethylsulfinyloxy group, chlorodifluoromethylsulfinyloxy group, bromodifluoromethylsulfinyloxy group, dichlorofluoromethylsulfinyloxy group, 2,2, 2-trichloroethylsulfinyloxy group, 2,2, 2-trifluoroethylsulfinyloxy group, pentafluoroethylsulfinyloxy group and the like, which are substituted with 1 to 9 and preferably 1 to 5 halogen atoms_1-6Linear or branched alkylsulfinyloxy.

Examples of the substituted or unsubstituted amino group include, but are not particularly limited to, an amino group, a monoalkylamino group, a dialkylamino group, a monoacylamino group, and the like. Examples of the alkyl group include the above-mentioned C_1-6Alkyl groups, and the like. Examples of the acyl group include the above-mentioned C_1-6Alkoxycarbonyl, haloalkoxycarbonyl, arylcarbonylAnd the like.

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

Aryl radical C_1-6Examples of alkyl groups include, but are not particularly limited to, benzyl, phenylethyl, phenyl-n-propyl, and the like.

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

Aryl radical C_1-6Examples of alkoxy groups include, but are not particularly limited to, benzyloxy, phenoxyethoxy, phenoxy-n-propoxy, phenyl-n-butoxy, 1-naphthylmethoxy, 2-naphthylmethoxy, and the like.

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

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

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

Aryl radical C_1-6Examples of alkylsulfonyl include, but are not particularly limited to, benzylsulfonyl, phenylethylsulfonyl, phenyl-n-propylsulfonyl, phenyl-n-butylsulfonyl, 1-naphthylmethylsulfonyl, 2-naphthylmethylsulfonyl, and the like.

Aryl radical C_1-6Examples of the alkylsulfinyl group include, but are not particularly limited to, benzylsulfinyl group, phenylethylsulfinyl group, phenyl-n-propylsulfinyl group, phenyl-n-butylsulfinyl group, 1-naphthylmethylsulfinyl group, 2-naphthylmethylsulfinyl group and the like.

Aryl radical C_1-6Examples of the alkylthio group include, but are not particularly limited to, benzylthio, phenylethylthio, phenyl-n-propylthio, phenyl-n-butylthio, 1-naphthylmethylthio, 2-naphthylmethylthio and the like.

All aryl groups mentioned above may be optionally 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 heterocyclic groups 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, thiadiazolinyl, triazolyl, triazolinyl, triazolyl, tetrazolyl, tetrazolinyl, pyridyl, dihydropyridinyl, tetrahydropyridyl, piperidyl, oxazinyl, dihydrooxazinyl, morpholinyl, thiazinyl, dihydrothiazinyl, thiomorpholinyl (thiamorpholino), pyridazinyl, dihydropyridazinyl, hexahydropyridazinyl, oxadiazolyl, dihydrooxadiazolyl, tetrahydrooxadiazolyl, dihydrooxazinyl, pyrazolidinyl, thiazolinolinyl, thiamorpholinyl, thiadiazolyl, thiadiazinyl, dihydrothiadiazinyl, tetrahydrothiadiazinyl, pyrimidinyl, dihydropyrimidyl, tetrahydropyrimidinyl, hexahydropyrimidyl, pyrazinyl, dihydropyrazinyl, tetrahydropyrazinyl, piperazinyl, triazinyl, dihydrotriazinyl, tetrahydrotriazinyl, hexahydrotriazinyl, tetrazinyl, dihydrotetrazinyl, indolyl, indolinyl, isoindolyl, indazolyl, quinazolinyl, dihydroquinazolinyl, tetrahydroquinazolinyl, carbazolyl, benzoxazolyl, benzisoxazolyl, benzthiazolyl, benzisothiazolyl, benzisothiazolinyl, benzimidazolyl, indazolyl, quinolinyl, dihydroquinolinyl, tetrahydroquinolinyl, isoquinolinyl, dihydroisoquinolinyl, tetrahydroisoquinolinyl, pyridoindolyl, dihydrobenzoxazinyl, dihydrobenzisoxazolyl, tetrazolyl, tetrazolinyl, indolizinyl, dihydrotetrazolinyl, hexahydrotetrazolinyl, hexahydropyrimidyl, indolizinyl, quinazolinyl, quinazolin,Linyl, dihydroLinyl, tetrahydroA linyl group, a phthalazinyl group, a dihydrophthalazinyl group, a tetrahydrophthalazinyl group, a quinoxalinyl group, a dihydroquinoxalinyl group, a tetrahydroquinoxalinyl group, a purinyl group, a dihydrobenzotriazinyl group, a dihydrobenzotetrazinyl group, a phenothiazinylfuranyl group, a benzofuranyl group, a chromanyl group (chromanyl), a benzothienyl group, and the like.

These heterocyclic groups include those substituted at any substitutable position with oxo or thione groups.

Heterocycle C_1-6Examples of alkyl groups include, but are not particularly limited to, 2-pyridylmethyl, 3-pyridylmethyl, 2-pyrazinylmethyl, pyrimidinylmethyl, 2-quinolylmethyl and the like.

Examples of the heterocyclic oxy group include, but are not particularly limited to, 2-pyridyloxy, 3-pyridyloxy, 2-pyrazinyloxy, pyrimidyloxy, 2-quinolylmethyloxy and the like.

All heterocycles 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).

R⁵And R⁶Together with the carbon atoms to which they are bonded may or may not be bonded to each other via at least one heteroatom to form a 3-to 8-membered ring.

Examples of the 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 the 3-to 8-membered ring include, but are not particularly limited to, cyclopropane, cycloheptane and the like C_3-8A cycloalkyl group; tetrahydropyran, piperidine and the like heterocycles.

R⁷And R⁸、R⁸And R⁹、R⁹And R¹⁰Or R¹⁰And R¹¹Together with the phenyl rings to which they are bonded may or may not be bonded to each other via at least one heteroatom to form a 3-to 8-membered ring. Examples of the 3 to 8 membered ring include: c_3-8Cycloalkyl, aryl, heterocyclic, and the like. C_3-8Cycloalkyl, aryl and heterocycle are as defined above.

Examples of the "substituent" of the above-substituted group include, but are not particularly limited to, halogen, nitro, cyano, hydroxy, formyl, C_1-6Alkyl radical, C_1-6Haloalkyl, C_1-6Alkoxy radical, C_1-6Haloalkoxy, C_1-6Alkoxy radical C_1-6Alkyl radical, C_1-6Halogenoalkoxy radical C_1-6Alkyl radical, C_3-8Cycloalkyl radical, C_3-8Cycloalkyl radical C_1-6Alkyl radical, C_1-6Alkylcarbonyl group, C_1-6Halogenoalkylcarbonyl, arylcarbonyl, aryloxycarbonyl, C_1-6Alkoxycarbonyl group, C_1-6Halogenoalkoxycarbonyl, C_1-6Cyanoalkyl, C_1-6Cyanoalkoxy group, C_2-6Alkenyl radical, C_2-6Haloalkenyl, C_2-6Alkynyl, C_2-6Halogenated alkynyl, C_1-6Alkylsulfonyl radical, C_1-6Haloalkylsulfonyl group, C_1-6Alkylsulfinyl radical, C_1-6Haloalkylsulfinyl radical, C_1-6Alkylthio radical, C_1-6Halogenoalkylthio, C_3-8Cycloalkylsulfonyl radical, C_3-8Cycloalkyl sulfinyl radical, C_3-8Cycloalkylthio radical, C_3-8Cycloalkyl radical C_1-6Alkylsulfonyl radical, C_3-8Cycloalkyl radical C_1-6Alkylsulfinyl radical, C_3-8Cycloalkyl radical C_1-6Alkylthio radical, C_1-6Alkoxy radical C_1-6Alkylsulfonyl radical, C_1-6Alkoxy radical C_1-6Alkylsulfinyl radical, C_1-6Alkoxy radical C_1-6Alkylthio radical, C_2-6Alkenyloxy radical, C_2-6Haloalkenyloxy, C_2-6Alkynyloxy, C_2-6Haloalkynyloxy, C_1-6Alkylsulfonyloxy, C_1-6Haloalkylsulfonyloxy, C_1-6Alkylsulfinyloxy, C_1-6Haloalkylsulfinyloxy, carboxy, OCN, SCN, SF₅Substituted or unsubstituted amino, aryl C_1-6Alkyl, aryloxy, aryl C_1-6Alkoxy, arylsulfonyl, arylsulfinyl, arylthio, aryl C_1-6Alkylsulfonyl, aryl C_1-6Alkylsulfinyl, aryl C_1-6Alkylthio, heterocyclic C_1-6Alkyl, heterocycloxy, and the like. Among these substituents, preferred substituents are halogen, nitro, C_1-6Alkyl radical, C_1-6Haloalkyl, C_1-6Alkoxy radical, C_1-6Haloalkoxy, C_1-6Alkylsulfonyl radical, C_1-6Haloalkylsulfonyl group, C_1-6Alkylsulfinyl radical, C_1-6Haloalkylsulfinyl radical, C_1-6Alkylthio radical, C_1-6Haloalkylthio, substituted or unsubstituted amino, aryl and heterocyclic, and more preferred substituents are fluoro, chloro, nitro, methyl, ethyl, trifluoromethyl, methoxy and trifluoromethoxy.

Preferred substituted aryl groups are halogen-substituted aryl, C_1-6Alkyl-substituted aryl, C_1-6Haloalkyl-substituted aryl, halogen and C_1-6Aryl substituted by haloalkyl, C_1-6Alkoxy-substituted aryl, C_1-6Haloalkoxy substituted aryl and C_1-6Alkylthio substituted aryl. More preferred substituted aryl groups are chloro-substituted aryl, fluoro-substituted aryl, trifluoromethyl-substituted aryl, chloro-and trifluoromethyl-substituted aryl, trifluoromethoxy-substituted aryl and methoxy-substituted aryl and methylthio-substituted aryl.

Preferred substituted heterocyclic groups are halogen-substituted heterocycles, C_1-6Alkyl-substituted heterocycles, C_1-6Haloalkyl-substituted heterocycles, C_1-6Alkoxy-substituted heterocycles, C_1-6Haloalkoxy substituted heterocycle and C_1-6Alkylthio substituted heterocycles. More preferred substituted heterocyclic groups are chloro-substituted heterocyclic rings, fluoro-substituted heterocyclic rings, trifluoromethyl-substituted heterocyclic rings, trifluoromethoxy-substituted heterocyclic rings, methoxy-substituted heterocyclic rings, and methylthio-substituted heterocyclic rings.

The salt of the compound represented by formula (1) may be any type of salt as long as it is agriculturally acceptable. Examples of the salt include inorganic acid salts such as hydrochloride, sulfate, nitrate, and the like; organic acid salts such as acetate and methanesulfonate; alkali metal salts such as sodium salt and potassium salt; alkaline earth metal salts such as magnesium salts and calcium salts; quaternary ammonium salts such as dimethylammonium and triethylammonium; and the like.

X represents oxygen or sulfur.

The symbol n represents an integer of 0 to 2.

Among the compounds (1) of the present invention, preferred are those wherein R is¹Is C_1-6Haloalkyl compounds and more preferred compounds (1) are those wherein R is¹A compound that is trifluoromethyl or trifluoroethyl.

Among the compounds (1) of the present invention, preferred are those wherein R is²Is hydrogen, halogen or C_1-6Alkyl group, and more preferred compound (1) is one wherein R is²A compound that is fluorine, chlorine, bromine or methyl.

Among the compounds (1) of the present invention, preferred are those wherein R is³Is hydrogen, halogen or C_1-6Alkyl group, and more preferred compound (1) is one wherein R is³A compound that is fluorine, chlorine, bromine, methyl or trifluoromethyl.

Among the compounds (1) of the present invention, preferred are those wherein R is⁴Is hydrogen, C_1-6Alkyl radical, C_2-6Alkenyl radical, C_2-6Alkynyl or C_1-6Haloalkyl compounds, and more preferred compounds (1) are those wherein R is⁴A compound which is hydrogen, methyl, ethyl, n-propyl, n-butyl, 3,3, 3-trifluoro-n-propyl, pentafluoroisopropyl or propargyl.

Among the compounds (1) of the present invention, preferred are those wherein R is⁵And R⁶Are the same or different and each represents hydrogen, halogen or C_1-6Alkyl group, and more preferred compound (1) is one wherein R is⁵And R⁶A compound which is hydrogen, fluorine, methyl, isopropyl or tert-butyl.

Among the compounds (1) of the present invention, preferred are compoundsIs wherein R is⁷、R⁸、R⁹、R¹⁰And R¹¹Is a compound of: hydrogen, halogen, nitro, cyano, C_1-6Alkyl radical, C_1-6Haloalkyl, C_1-6Alkoxy radical, C_1-6Haloalkoxy, C_1-6Alkylsulfonyl radical, C_1-6Haloalkylsulfonyl group, C_1-6Alkylsulfinyl radical, C_1-6Haloalkylsulfinyl radical, C_1-6Alkylthio radical, C_1-6A haloalkylthio group, a substituted or unsubstituted amino group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic ring, or a substituted or unsubstituted heterocyclyloxy group; more preferred compounds are those wherein R is⁷、R⁸、R⁹、R¹⁰And R¹¹Is a compound of: hydrogen, halogen, nitro, C_1-6Alkyl radical, C_1-6Haloalkyl, C_1-6Alkoxy radical, C_1-6Haloalkoxy, C_1-6Alkylsulfonyl radical, C_1-6Haloalkylsulfonyl group, C_1-6Alkylsulfinyl radical, C_1-6Haloalkylsulfinyl radical, C_1-6Alkylthio radical, C_1-6A haloalkylthio group, a substituted or unsubstituted amino group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic ring; and another more preferred compound (1) is wherein R is⁷、R⁸、R⁹、R¹⁰And R¹¹Is a compound of: hydrogen, fluorine, chlorine, bromine, nitro, methyl, ethyl, n-propyl, isopropyl, tert-butyl, n-pentyl, trifluoromethyl, methoxy, ethoxy, n-propoxy, trifluoromethoxy, trifluoromethylsulfonyl, trifluoromethylthio, methylsulfonyl, methylthio, NH₂Phenyl, 2-chlorophenyl, 4-chlorophenyl, 3, 4-dichlorophenyl, 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 3, 5-difluorophenyl, 2-chloro-4-fluorophenyl, 2-trifluoromethylphenyl, 3-trifluoromethylphenyl, 4-trifluoromethylphenyl, 3-chloro-5-trifluoromethylphenyl, 4-chloro-3-trifluoromethylphenyl, 2-trifluoromethoxyphenyl, 3-trifluoromethoxyphenyl, 4-methoxyphenyl, 2-methylphenylthio, 5-trifluoromethyl-2-pyridyl or 5-pyrimidyl, ethylthio, n-propylthioPhenyl, isopropylthio, difluoromethylthio, 4-phenylphenyl, 4-cyanophenyl, 3-chlorophenyl, 2,3, 4-trichlorophenyl, 3-trifluoromethoxyphenyl, 2,2, 2-trifluoroethylthio, 2- (methylthio) -phenyl, 2, 3-dichlorophenyl, 2,3, 4-trifluorophenyl, 2, 4-dichlorophenyl, 2, 5-dichlorophenyl, 3, 4-difluorophenyl, 3- (benzo [ d ] phenyl][1,3]Dioxol-5-yl) phenyl, 3, 5-dichlorophenyl, 4- (ethylsulfanyl) -phenyl, 4-acetylphenyl or 4- (dimethylamino) -phenyl.

Alternatively, among the compounds (1) of the present invention, preferred is a compound wherein R is¹is-CH₂C(X¹)(X²)(X³) A compound of (1), wherein X¹、X²And X³Identical or different and each represents halogen; more preferred compounds (1) are those wherein X¹、X²And X³A compound which is the same or different and each represents fluorine, chlorine or bromine; another more preferred compound (1) is wherein X¹、X²And X³A compound which is the same or different and each represents fluorine or chlorine; and the most preferred compound (1) is wherein X¹、X²And X³A compound that is fluorine.

Among the compounds (1) of the present invention, preferred are those wherein R is²A compound which is methyl.

Among the compounds (1) of the present invention, preferred are those wherein R is³A compound that is halogen; more preferred compounds are those wherein R is³A compound that is fluorine, chlorine or bromine; another more preferred compound is that wherein R³A compound that is fluorine or chlorine; and the most preferred compounds are those wherein R is³A compound that is fluorine.

Among the compounds (1) of the present invention, preferred are those wherein R is⁴Is hydrogen, C_1-6Alkyl or C_1-6A haloalkyl compound; more preferred compounds (1) are those wherein R is⁴A compound that is hydrogen, methyl or ethyl; more preferred compounds (1) are those wherein R is⁴A compound which is hydrogen or methyl; and the most preferred compound (1) is wherein R⁴A compound which is hydrogen.

Among the compounds (1) of the present invention, preferred are those wherein R is⁵And R⁶A compound that is hydrogen or halogen; more preferred compounds are those wherein R is⁵And R⁶A compound which is the same or different and each represents hydrogen, fluorine, chlorine or bromine; another more preferred compound is that wherein R⁵And R⁶A compound which is the same or different and each represents hydrogen, fluorine or chlorine; even further more preferred compounds are those wherein R is⁵And R⁶A compound which is the same or different and each represents hydrogen or fluorine; and the most preferred compound (1) is wherein R⁵And R⁶A compound which is hydrogen.

Among the compounds (1) of the present invention, preferred are those wherein R is⁷、R⁸、R¹⁰And R¹¹A compound which is hydrogen.

Among the compounds (1) of the present invention, preferred are those wherein R is⁹is-L-CH₂-C(X⁴)(X⁵)(X⁶) Wherein L is a single bond, oxygen or sulfur and X⁴、X⁵And X⁶Are identical or different and each represents hydrogen or halogen; more preferred compounds (1) are those wherein L is oxygen or sulfur and X⁴、X⁵And X⁶A compound which is the same or different and each represents halogen; another more preferred compound (1) is one wherein L is oxygen or sulfur and X⁴、X⁵And X⁶A compound which is the same or different and each represents fluorine, chlorine or bromine; and still further more preferred is compound (1) wherein L is oxygen or sulfur and X⁴、X⁵And X⁶A compound which is the same or different and each represents fluorine or chlorine.

Among the compounds (1) of the present invention, preferred compounds are those in which X is oxygen or sulfur, and more preferred compounds (1) are those in which X is oxygen.

Among the compounds (1) of the present invention, preferred compounds are those wherein n is 0.

Among the compounds (1) of the present invention, preferred are those wherein R is⁷、R⁸、R¹⁰And R¹¹Is hydrogen and R⁹A compound which is a group of the formula:

wherein is and R⁹The point of attachment of adjacent carbons; r¹²、R¹³、R¹⁴、R¹⁵And R¹⁶Is hydrogen, halogen, nitro, cyano, hydroxy, formyl, C_1-6Alkyl radical, C_1-6Haloalkyl, C_1-6Alkoxy radical, C_1-6Haloalkoxy, C_1-6Alkoxy radical C_1-6Alkyl radical, C_1-6Halogenoalkoxy radical C_1-6Alkyl radical, C_3-8Cycloalkyl radical, C_3-8Cycloalkyl radical C_1-6Alkyl radical, C_1-6Alkylcarbonyl group, C_1-6Halogenoalkylcarbonyl, arylcarbonyl, aryloxycarbonyl, C_1-6Alkoxycarbonyl group, C_1-6Halogenoalkoxycarbonyl, C_1-6Cyanoalkyl, C_1-6Cyanoalkoxy group, C_2-6Alkenyl radical, C_2-6Haloalkenyl, C_2-6Alkynyl, C_2-6Halogenated alkynyl, C_1-6Alkylsulfonyl radical, C_1-6Haloalkylsulfonyl group, C_1-6Alkylsulfinyl radical, C_1-6Haloalkylsulfinyl radical, C_1-6Alkylthio radical, C_1-6Halogenoalkylthio, C_3-8Cycloalkylsulfonyl radical, C_3-8Cycloalkyl sulfinyl radical, C_3-8Cycloalkylthio radical, C_3-8Cycloalkyl radical C_1-6Alkylsulfonyl radical, C_3-8Cycloalkyl radical C_1-6Alkylsulfinyl radical, C_3-8Cycloalkyl radical C_1-6Alkylthio radical, C_1-6Alkoxy radical C_1-6Alkylsulfonyl radical, C_1-6Alkoxy radical C_1-6Alkylsulfinyl radical, C_1-6Alkoxy radical C_1-6Alkylthio radical, C_2-6Alkenyloxy radical, C_2-6Haloalkenyloxy, C_2-6Alkynyloxy, C_2-6Halogenated alkynesOxy radical, C_1-6Alkylsulfonyloxy, C_1-6Haloalkylsulfonyloxy, C_1-6Alkylsulfinyloxy, C_1-6Haloalkylsulfinyloxy, carboxy, OCN, SCN, SF₅Substituted or unsubstituted amino, aryl C_1-6Alkyl, aryloxy, aryl C_1-6Alkoxy, arylsulfonyl, arylsulfinyl, arylthio, aryl C_1-6Alkylsulfonyl, aryl C_1-6Alkylsulfinyl, aryl C_1-6Alkylthio, heterocyclic C_1-6Alkyl or heterocycloxy, all of which may be optionally further substituted; more preferred compounds are those wherein R is¹²、R¹³、R¹⁴、R¹⁵And R¹⁶Are the same or different and each represents hydrogen, halogen, cyano, C_1-6Haloalkyl, C_1-6Haloalkoxy or C_1-6A compound of an alkylthio group; and another more preferred compound is wherein R⁹Is a compound of: phenyl, 2-fluorophenyl, 2-chlorophenyl, 2-trifluoromethoxyphenyl, 2- (methylthio) phenyl, 2, 3-dichlorophenyl, 2, 4-dichlorophenyl, 2-chloro-4-fluorophenyl, 2,3, 4-trifluorophenyl, 2,3, 4-trichlorophenyl, 3-fluorophenyl, 3-chlorophenyl, 3-trifluoromethylphenyl, 3-trifluoromethoxyphenyl, 3, 4-difluorophenyl, 3, 4-dichlorophenyl, 3, 5-difluorophenyl, 3, 5-dichlorophenyl, 3-trifluoromethyl-4-chloro-phenyl, 3-chloro-5-trifluoromethyl-phenyl, 3,4, 5-trifluorophenyl, 4-fluorophenyl, 2- (methylthio) phenyl, 2, 3-dichlorophenyl, 3, 4-trifluoromethyl-phenyl, 3-chloro-5-trifluoromethyl-phenyl, 3,4, 5-trifluoro-phenyl, 4-fluorophenyl, 2-trifluoro-fluorophenyl, 4-chlorophenyl, 4-bromophenyl, 4-methylphenyl, 4-methoxyphenyl, 4-trifluoromethylphenyl, 4-trifluoromethoxyphenyl, 4-cyanophenyl, 4-phenylphenyl, 4-acetylphenyl, 4- (dimethylamino) phenyl, 4- (methylthio) phenyl or 4- (ethylthio) 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 in the scope of the compound (1). For example, when the compound (1) has an optical isomer, an optical isomer separated from a racemate is also included in the scope of the compound (1). Each of such isomers can be obtained as a single compound by known synthetic and separation means (e.g., concentration, solvent extraction, column chromatography, recrystallization, etc.). 2. Process for preparing benzamide compounds and salts thereof

The method for preparing the benzamide compound (1) (compound (1-1) and compound (1-2)) of the present invention is not limited, and the benzamide compound (1) can be prepared by steps 1 to 5 represented by reaction scheme 1 below:

[ reaction scheme 1]

Wherein R is¹、R²、R³、R⁴、R⁵、R⁶、R⁷、R⁸、R⁹、R¹⁰、R¹¹X and n are as defined above.

Step 1

An amide compound represented by formula (4) (hereinafter may be referred to as "compound (4)") can be produced by reacting an aniline compound represented by formula (2) (hereinafter may be referred to as "compound (2)") with a benzylcarbonyl compound represented by formula (3) (reaction scheme 2):

[ reaction scheme 2]

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 sulfonic acids C_1-6An alkyl ester; andsubstituted or unsubstituted aryl sulfonate. Examples of the substituent include the above-mentioned substituents such as halogen and C_1-6A haloalkyl group.

Step 1A (when Y is a leaving group)

The phenylacetamide compound represented by the formula (4) (hereinafter may be referred to as "compound (4)") can be produced by reacting an aniline compound represented by the formula (2) (hereinafter may be referred to as "compound (2)") with a benzylcarbonyl compound represented by the formula (3A) (reaction scheme 3):

[ reaction scheme 3]

Wherein R is²、R³、R⁴、R⁵、R⁶、R⁷、R⁸、R⁹、R¹⁰、R¹¹And X is as defined above. Y' represents a leaving group.

Examples of the benzylcarbonyl compound (3A) include, but are not particularly limited to, substituted or unsubstituted phenylacetyl halides such as phenylacetyl chloride, phenylacetyl bromide and the like; and substituted or unsubstituted phenylacetates such as ethyl phenylacetate and methyl phenylacetate.

The ratio used between the aniline compound (2) and the benzylcarbonyl compound (3A) in the reaction is not particularly limited and thus may be appropriately selected from a wide range. About 1 to 5 moles of the benzylcarbonyl compound (3A) and preferably about equimolar to 1.2 moles of the benzylcarbonyl compound are generally used with respect to 1 mole of the aniline compound (2).

The above-mentioned reaction may be carried out in the absence or presence of a base. In the above case, the reaction is preferably carried out in the presence of a base. Known bases can be widely used as the base, and examples of the base include: alkali metal carbonates such as sodium carbonate, potassium carbonate, cesium carbonate, potassium bicarbonate, and sodium bicarbonate; alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; alkali metal hydrides such as inorganic bases such as sodium hydride and potassium hydride; alkali metal alkoxides such as sodium methoxide, sodium ethoxide, and potassium tert-butoxide; organic bases such as pyridine, triethylamine, diethylamine, dimethylamine, methylamine, imidazole, benzimidazole, diisopropylethylamine, 4-dimethylaminopyridine, piperidine and the like; and the like. Any of these bases is used alone or in combination of two or more types thereof.

The base may be used in an excess amount of usually about 1 to 10 moles and preferably about 1 to 5 moles with respect to 1 mole of the aniline compound (2). When an organic base such as triethylamine, pyridine or the like is used, it may be used in a large excess to also serve as a reaction solvent.

The above-mentioned reaction is carried out in a suitable solvent or without any solvent. When the above-mentioned reaction is carried out in a solvent, the solvent is not limited as long as the solvent is inactive to the above-mentioned reaction. Examples of such solvents include: fatty acid or alicyclic hydrocarbon-based solvents such as n-hexane, cyclohexane, and n-heptane; aromatic hydrocarbon-based solvents such as benzene, chlorobenzene, toluene, xylene, and the like; halogenated hydrocarbon-based solvents such as dichloromethane, 1, 2-dichloroethane, chloroform, and carbon tetrachloride; ether-based solvents such as diethyl ether, Tetrahydrofuran (THF), 1, 4-dioxane, and the like; ester solvents such as methyl acetate and ethyl acetate; acetonitrile; amide-based solvents such as N, N-Dimethylformamide (DMF); and sulfoxide-based solvents such as dimethyl sulfoxide. Any of these solvents may be used alone or a combination of two or more types thereof may be used as needed.

The reaction temperature of the above-mentioned reaction is not particularly limited, and it is usually in the range between-10 ℃ and the boiling point of the solvent used, and preferably 0 to 25 ℃. The reaction time varies depending on, for example, the reaction temperature, and the reaction is usually completed within about 0.5 to 24 hours.

Step 1B (when Y is hydroxy)

As another method for obtaining the phenylacetamide compound (4), the compound (4) can be produced by reacting the aniline compound (2) with a phenylacetic acid compound represented by the formula (3B) (hereinafter may be referred to as "compound (3B)") (reaction scheme 4):

[ reaction scheme 4]

The ratio used between the aniline compound (2) and the phenylacetic acid compound (3B) in the reaction is not particularly limited and thus can be appropriately selected from a wide range. About 1 to 5 moles of the phenylacetic acid compound (3B) and preferably about equimolar to 1.2 moles of the phenylacetic acid compound are generally used with respect to 1 mole of the aniline compound (2).

The above-mentioned reaction may be carried out in the absence or presence of a condensing agent. In the above case, the above-mentioned reaction is preferably carried out in the presence of a condensing agent. Known condensing agents can be used as the condensing agent and examples of the condensing agent include 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide (EDCI HCl), 1-Hydroxybenzotriazole (HOBT), 1- [ bis (dimethylamino) methylene ] -1H-1,2, 3-triazolo [4,5-b ] pyridinium-3-oxide Hexafluorophosphate (HATU), bis (2-oxo-3-oxazolidinyl) phosphonic acid chloride (BOP-C1), propylphosphonic anhydride (T3P), and the like. Any of these condensing agents is used alone or in combination of two or more types thereof.

The condensing agent may be used in an excess amount of usually 1 to 10 moles and preferably about 1 to 3 moles with respect to 1 mole of the aniline compound (2).

The above-mentioned reaction is carried out in a suitable solvent or without any solvent. When the above-mentioned reaction is carried out in a solvent, the solvent is not limited as long as the solvent is inactive to the above-mentioned reaction. Examples of such solvents include: fatty acid or alicyclic hydrocarbon-based solvents such as n-hexane, cyclohexane, and n-heptane; aromatic hydrocarbon-based solvents such as benzene, chlorobenzene, toluene, xylene, and the like; halogenated hydrocarbon-based solvents such as dichloromethane, 1, 2-dichloroethane, chloroform, carbon tetrachloride, and the like; ether-based solvents such as diethyl ether, THF, and 1, 4-dioxane; ester solvents such as methyl acetate and ethyl acetate; acetonitrile; amide solvents such as DMF; and sulfoxide-based solvents such as dimethyl sulfoxide. Any of these solvents may be used alone, or a combination of two or more types of these solvents may be used as needed.

The reaction temperature of the above-mentioned reaction is not particularly limited and it is usually in the range between-10 ℃ and the boiling point of the solvent used and preferably in the range between-5 ℃ and the boiling point of the solvent. The reaction time varies depending on, for example, the reaction temperature, and the reaction is usually completed within about 0.25 to 24 hours.

Step 1C

Note that, as a method for producing the phenylacetamide compound (4), a phenylacetic acid halide compound (3C) obtained by reacting the phenylacetic acid compound (3B) with a halogenating agent may be used as a raw material.

The above-mentioned reaction may be carried out in the presence of a base. Any of the same bases as those described above may be used as the base, and preferred examples of the base include organic bases such as triethylamine, pyridine, di-isopropylamine, 4-diisopropylethylamine, 4-dimethylaminopyridine, lutidine, and the like, and this base may also be used in excess to also serve as the reaction solvent.

Examples of halogenating agents include, but are not particularly limited to, POCl₃、POBr₃、SOCl₂、SO₂Cl₂Oxalyl chloride.

Generally, 1 to 10 moles of the halogenating agent and preferably about 1 to 5 moles of the halogenating agent can be used relative to 1 mole of the aniline compound (2).

The above-mentioned reaction is carried out in a suitable solvent or without any solvent. When the above-mentioned reaction is carried out in a solvent, the solvent is not limited as long as the solvent is inactive to the above-mentioned reaction. As such solvents, the above-mentioned solvents are listed. Any of these solvents may be used alone or a combination of two or more types thereof may be used as needed.

The aniline compound (2), the benzylcarbonyl compound (3A), the phenylacetic acid compound (3B) and the phenylacetic acid halide compound (3C) used as starting materials in step 1 are known compounds or compounds which can be easily prepared by known methods.

The compound (4) obtained by the method shown in step 1 is easily isolated from the reaction mixture to be purified by using typical separation means and purification means (e.g., filtration, solvent extraction, distillation, recrystallization, column chromatography, etc.).

After the reaction is completed, the compound (4) can be provided for the next reaction without separation from the reaction system.

Step 2A sulfonyl chloride compound represented by formula (5) (hereinafter may be referred to as "compound (5)") can be produced by chlorosulfonating an amide compound (4) (reaction scheme 5):

[ reaction scheme 5]

The agent for chlorosulfonation is not particularly limited and includes, for example, chlorosulfonic acid and the like. When chlorosulfonic acid is used, this step may be performed in one step. For chlorosulfonation, a two-step process (including sulfonation followed by chlorination) may be used. The sulfonyl chloride compound (5) can be prepared by: reacting an amide compound with a sulfonating agent to produce HOSO₂-substituted amide compound, followed by the reaction containing HOSO₂The amide compound of (a) is reacted with a chlorinating agent.

The agent for sulfation is not particularly limited, and chlorosulfonic acid, sulfuric acid, for example, are provided. Examples of chlorinating agents for chlorination include, but are not particularly limited to, chlorine, POCl₃、SOCl₂、SO₂Cl₂And oxalyl chloride.

When chlorosulfonic acid is used, the ratio used between the amide compound (4) and chlorosulfonic acid in the reaction is not particularly limited and may be appropriately selected from a wide range. About 1 to 50 moles of chlorosulfonic acid and preferably about 1 to 20 moles of chlorosulfonic acid are generally used with respect to 1 mole of the amide compound (4).

When the sulfonating agent and the chlorinating agent are used, the ratio used between the sulfonating agent and the chlorinating agent in the reaction between the amide compound (4) and the sulfonating agent is not particularly limited and may be appropriately selected from a wide range. About 1 to 50 moles of the sulfonating agent and preferably about 1 to 20 moles of the sulfonating agent are generally used with respect to 1 mole of the amide compound (4). The ratio used between the amide compound (4) and the chlorinating agent in the reaction between the two is not particularly limited and may be appropriately selected from a wide range. About 1 to 50 moles of sulfuric acid and preferably 1 to 20 moles of sulfuric acid are generally used with respect to 1 mole of the amide compound (1).

The above-mentioned reaction is carried out in a suitable solvent or without any solvent. When the above-mentioned reaction is carried out in a solvent, the solvent is not limited as long as the solvent is inactive to the above-mentioned reaction. As examples of such solvents, the same solvents as those described above are listed. Any of these solvents may be used alone or a combination of two or more types thereof may be used as needed.

The reaction temperature of the above-mentioned reaction is not particularly limited, and it is generally in the range between-20 ℃ and the boiling point of the solvent used, preferably-10 ℃ to 150 ℃, and more preferably 0 to 100 ℃. The reaction time varies depending on, for example, the reaction temperature and the reaction is usually completed within about 0.25 to 24 hours.

The sulfonyl chloride compound (5) obtained by the method shown in step 2 is easily separated from the reaction mixture to be purified by using typical separation means and purification means (e.g., filtration, solvent extraction, distillation, recrystallization, column chromatography, etc.).

After the reaction is completed, the sulfonyl chloride compound (5) can be provided for the next reaction without being separated from the reaction system.

Step 3

The thiol compound represented by formula (6) (hereinafter may be referred to as "compound (6)") can be produced by reacting a sulfonyl chloride compound (5) with a reducing agent (reaction scheme 6):

[ reaction scheme 6]

The ratio used between the sulfonyl chloride compound (5) and the reducing agent in the reaction is not particularly limited and may be appropriately selected from a wide range. About 1 to 50 moles of the reducing agent and more preferably about 1 to 20 moles of the reducing agent are generally used relative to 1 mole of the sulfonyl chloride compound (5).

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

The above-mentioned reaction is carried out in a suitable solvent. The solvent is not limited as long as the solvent is inactive to the reaction. As examples of such solvents, the same solvents as those described above are listed. Any of these solvents may be used alone or a combination of two or more types thereof may be used as needed.

The reaction temperature of the above-mentioned reaction is not particularly limited and it is generally in the range between-20 ℃ and the boiling point of the solvent used, preferably-10 ℃ to 150 ℃, and more preferably 20 to 120 ℃. The reaction time varies depending on, for example, the reaction temperature and the reaction is usually completed within about 0.25 to 24 hours.

The thiol compound (6) obtained by the method shown in step 3 is easily isolated from the reaction mixture to be purified by using typical separation means and purification means (e.g., filtration, solvent extraction, distillation, recrystallization, column chromatography, etc.).

After the reaction is completed, the thiol compound (6) can be supplied for the next reaction without being separated from the reaction system.

A process for producing a thioether compound represented by the formula (1-1) or a salt thereof

Examples of the method for preparing the thioether compound represented by formula (1-1) include, but are not limited to, preparation route 1, preparation route 2, preparation route 3, preparation route 4, and the like, which are described below.

Preparation route 1 (step 4)

The thioether compound (1-1) can be produced by reacting the thiol compound (6) with an alkyl reagent represented by the formula (7) (which may be referred to as "alkyl reagent (7) hereinafter) (reaction scheme 7):

[ reaction scheme 7]

Wherein R is¹、R²、R³、R⁴、R⁵、R⁶、R⁷、R⁸、R⁹、R¹⁰、R¹¹And X is as defined above, and G represents a leaving group.

As examples of the leaving group, the same leaving groups as those described above are listed.

The ratio used between the thiol compound (6) and the alkyl reagent (7) in the reaction is not particularly limited and may be appropriately selected from a wide range. About 1 to 10 moles of the alkyl reagent (7) and preferably about 1 to 5 moles of the alkyl reagent are generally used with respect to 1 mole of the thiol compound (6).

Examples of the alkyl reagent (7) include, but are not particularly limited to, methyl iodide, ethyl bromide and the like C_1-6An alkyl halide; c such as trifluoroiodomethane, trifluoromethyl bromide, trifluoroiodoethane, trifluoroethyl bromide_1-6A haloalkyl halide; and the like.

The above-mentioned reaction may be carried out in the presence of a base. In the above case, the above-mentioned reaction is preferably carried out in the presence of a base. As examples of the base, conventionally known bases can be widely used, and any of the same bases as those described above can be used.

Generally, 1 to 10 moles of the base and preferably about 1 to 3 moles of the base may be used with respect to 1 mole of the thiol compound (6). When an organic base such as triethylamine, pyridine or the like is used, it may be used in a large excess to also serve as a reaction solvent.

The above-mentioned reaction can be carried out by further adding a radical initiator. Examples of the radical initiator include, but are not particularly limited to, sulfurous acid adducts such as sulfurous acid, sulfite, Rongalit (product name, sodium formaldehyde sulfoxylate), and the like. The base and the radical initiator may be used in combination.

When a radical initiator is used, as an additive amount thereof, usually 0.1 to 10 moles of the radical initiator and preferably about 0.1 to 5 moles of the radical initiator may be used with respect to 1 mole of the thiol compound (6).

The above-mentioned reaction is carried out in a suitable solvent. Examples of the solvent include: fatty acid or alicyclic hydrocarbon-based solvents such as n-hexane, cyclohexane, and n-heptane; aromatic hydrocarbon-based solvents such as benzene, chlorobenzene, toluene, xylene, and the like; halogenated hydrocarbon-based solvents such as dichloromethane, 1, 2-dichloroethane, chloroform, carbon tetrachloride, and the like; ether-based solvents such as diethyl ether, THF, 1, 4-dioxane, and the like; ester-based solvents such as methyl acetate, ethyl acetate, and the like; acetonitrile; amide-based solvents such as DMF, N-dimethylacetamide, N-methyl-2-pyrrolidone, and the like; sulfoxide-based solvents such as dimethylsulfoxide; alcohol-based solvents, such as aprotic polar solvents like sulfolane, methanol, ethanol, isopropanol, and the like; water; and the like. Any of these solvents may be used alone or a combination of two or more types thereof may be used as needed.

The reaction temperature of the above-mentioned reaction is not particularly limited, and it is generally in the range between-20 ℃ and the boiling point of the solvent used, preferably-10 ℃ to 60 ℃, and more preferably 0 to 50 ℃. The reaction time varies depending on, for example, the reaction temperature and the reaction is usually completed within about 0.25 to 24 hours.

The thioether compound (1-1) obtained by the method shown in step 4 is easily separated from the reaction mixture to be purified by using typical separation means and purification means (e.g., filtration, solvent extraction, distillation, recrystallization, column chromatography, etc.).

After the reaction is completed, the thioether compound (1-1) can be provided for the next reaction without separation from the reaction system.

Preparation route2

The compound represented by the formula (1-1a) (hereinafter may be referred to as "compound (1-1 a)") can be produced by reacting a thioether compound represented by the formula (1-1a) with a compound represented by the formula (7'): r4 '-G (hereinafter may be referred to as "Compound (7') (reaction scheme 8) to prepare a thioether compound represented by formula (1-1b) (hereinafter may be referred to as" Compound (1-1b) "):

[ reaction scheme 8]

Wherein R is¹、R²、R³、R⁵、R⁶、R⁷、R⁸、R⁹、R¹⁰、R¹¹And X is as defined above, and R^4’Represents a formyl group, C_1-6Alkyl radical, C_1-6Haloalkyl, C_1-6Alkoxy radical, C_1-6Haloalkoxy, C_1-6Alkoxy radical C_1-6Alkyl radical, C_1-6Halogenoalkoxy radical C_1-6Alkyl radical, C_3-8Cycloalkyl radical, C_3-8Cycloalkyl radical C_1-6Alkyl radical, C_1-6Alkylcarbonyl group, C_1-6Halogenoalkylcarbonyl group, C_1-6Alkoxycarbonyl group, C_1-6Halogenoalkoxycarbonyl, arylcarbonyl, aryloxycarbonyl, C_2-6Alkenyl radical, C_2-6Haloalkenyl, C_2-6Alkynyl, C_2-6Halogenated alkynyl, C_1-6Alkylsulfonyl radical, C_1-6Haloalkylsulfonyl group, C_1-6Alkylsulfinyl radical, C_1-6Haloalkylsulfinyl radical, C_1-6Alkylthio radical, C_1-6Halogenoalkylthio, aryl C_1-6Alkyl, arylsulfonyl, arylsulfinyl, arylthio and heterocycle, and these groups may be optionally further substituted. G represents a leaving group.

As examples of the leaving group, leaving groups such as those described above are listed.

The ratio used between the thioether compound (1-1a) and the compound (7') in the reaction is not particularly limited and may be appropriately selected from a wide range. About 1 to 10 moles of the compound (7 ') and preferably about equimolar to 5 moles of the compound (7') are generally used with respect to 1 mole of the thioether compound (1-1 a).

The above-mentioned reaction may be carried out in the presence of a base. In the above case, the above-mentioned reaction is preferably carried out in the presence of a base. Generally known bases can be used and any of the same bases as those described above can be used as the base.

The base may be used in a stoichiometric amount or in an excess amount to the above-mentioned amount with respect to 1 mole of the thioether compound (1-1 a). Preferably, 1 to 10 times the base and more preferably 1 to 5 times the base may be used in excess. When an organic base such as triethylamine, pyridine or the like is used, it may be used in a large excess to also serve as a reaction solvent.

The above-mentioned reaction is carried out in a suitable solvent. Examples of the solvent include: fatty acid or alicyclic hydrocarbon-based solvents such as n-hexane, cyclohexane, and n-heptane; aromatic hydrocarbon-based solvents such as benzene, chlorobenzene, toluene, xylene, and the like; halogenated hydrocarbon-based solvents such as dichloromethane, 1, 2-dichloroethane, chloroform, carbon tetrachloride, and the like; ether-based solvents such as diethyl ether, THF, 1, 4-dioxane, and the like; ester solvents such as methyl acetate and ethyl acetate; acetonitrile; amide-based solvents such as DMF, N-dimethylacetamide, N-methyl-2-pyrrolidone, and the like; sulfoxide-based solvents such as dimethylsulfoxide; alcohol-based solvents, such as aprotic polar solvents like sulfolane, methanol, ethanol, and isopropanol; and water. Any of these solvents may be used alone or a combination of two or more types thereof may be used as needed.

The reaction temperature of the above-mentioned reaction is not particularly limited and it is generally in the range between-20 ℃ and the boiling point of the solvent used, preferably-10 ℃ to 60 ℃, and more preferably 20 to 50 ℃. The reaction time varies depending on, for example, the reaction temperature and the reaction is usually completed within about 0.25 to 24 hours.

The thioether compound (1-1b) obtained by the method shown in step 4 is easily separated from the reaction mixture to be purified by using typical separation means and purification means (e.g., filtration, solvent extraction, distillation, recrystallization, column chromatography, etc.).

After the reaction is completed, the thioether compound (1-1b) can be provided for the next reaction without separation from the reaction system.

The thioether compound (1-1) can be prepared not only according to the above-mentioned preparation routes but also according to preparation routes 3,4 and 5.

Preparation route 3

The thioether compound (1-1a) can be produced by reacting an aniline compound (which may be referred to as "compound (8)" hereinafter) with a phenylacetic acid compound (3) (reaction scheme 9):

[ reaction scheme 9]

Wherein R is¹、R²、R³、R⁵、R⁶、R⁷、R⁸、R⁹、R¹⁰、R¹¹X and Y are as defined above.

Preparation route 3A (when Y is a leaving group)

The thioether compound (1-1a) can be produced by reacting the aniline compound (8) with the benzylcarbonyl compound (3A) (reaction scheme 10):

[ reaction scheme 10]

Wherein R is²、R³、R⁴、R⁵、R⁶、R⁷、R⁸、R⁹、R¹⁰、R¹¹And X is as defined above, and Y' represents a leaving group.

Examples of the benzylcarbonyl 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 can be prepared according to the method described in WO 2007/131680.

The ratio used between the aniline compound (8) and the benzylcarbonyl compound (3A) in the reaction is not particularly limited and thus may be appropriately selected from a wide range. About 1 to 5 moles of the benzylcarbonyl compound (3A) and preferably about equimolar to 1.2 moles of the benzylcarbonyl compound (3A) are generally used with respect to 1 mole of the aniline compound (8).

The above-mentioned reaction may be carried out in the absence or presence of a base. In the above case, the above-mentioned reaction is preferably carried out in the presence of a base. As an example of the base, any of the same bases as those shown above in step 1 may be used. Any of these bases is used alone or in combination of two or more types thereof.

A stoichiometric amount of the base or an excess amount of the base more than mentioned above may be used relative to 1 mole of the aniline compound (8).

Preferably, 1 to 5 times the amount of the base may be used in excess. When an organic base such as triethylamine, pyridine or the like is used, it may be used in a large excess to also serve as a reaction solvent.

The above-mentioned reaction is carried out in a suitable solvent or without any solvent. When the above-mentioned reaction is carried out in a solvent, any of the same solvents as those shown above in step 1 may be used. Any of these solvents may be used alone or a combination of two or more types thereof may be used as needed.

The reaction temperature of the above-mentioned reaction is not particularly limited and it is generally in the range between-20 ℃ and the boiling point of the solvent used and preferably 0 to 50 ℃. The reaction time varies depending on, for example, the reaction temperature and the reaction is usually completed within about 0.5 to 24 hours.

The aniline compound (8) used as a starting material is a known compound or a compound which can be easily prepared by a known method.

The thioether compound (1-1a) is easily separated from the reaction mixture to be purified by using typical separation means and purification means (e.g., filtration, solvent extraction, distillation, recrystallization, column chromatography, etc.).

After the reaction is completed, the thioether compound (1-1a) can be provided for the next reaction without separation from the reaction system.

Step 3B (when Y is hydroxy)

As another method for obtaining the phenylacetamide compound (1-1a), the compound (1-1a) can be produced by reacting the aniline compound (8) with the phenylacetic acid compound (3B) (reaction scheme 11):

[ reaction scheme 11]

Wherein R is¹、R²、R³、R⁵、R⁶、R⁷、R⁸、R⁹、R¹⁰、R¹¹And X is as defined above.

The ratio used between the aniline compound (8) and the phenylacetic acid compound (3B) in the reaction is not particularly limited and thus may be appropriately selected from a wide range. About 1 to 5 moles of the phenylacetic acid compound (3B) and preferably equimolar to 1.2 moles of the phenylacetic acid compound (3B) are generally used with respect to 1 mole of the aniline compound (8).

The above-mentioned reaction may be carried out in the absence or presence of a condensing agent. In the above case, the above-mentioned reaction is preferably carried out in the presence of a condensing agent. As examples of the condensing agent, the same condensing agents as those shown in step 1B are listed. Any of these condensing agents is used alone or in combination of two or more types thereof.

The condensing agent may be used in a stoichiometric amount or in an excess amount to the above-mentioned amount with respect to 1 mole of the aniline compound (8). Preferably, the condensing agent may be used in an excess of about 1 to 5 times.

The above-mentioned reaction may be carried out in the absence or presence of a base. In the above case, the above-mentioned reaction is preferably carried out in the presence of a base. Any of the same bases as those shown in step 1 above may be used as the base. Any of these bases is used alone or in combination of two or more types thereof.

A stoichiometric amount of the base or an excess amount of the base more than mentioned above may be used relative to 1 mole of the aniline compound (8). Preferably, about 1 to 5 times the amount of the base may be used in excess. When an organic base such as triethylamine, pyridine or the like is used, it may be used in a large excess to also serve as a reaction solvent.

The reaction temperature of the above-mentioned reaction is not particularly limited and it is usually in the range between-20 ℃ and the boiling point of the solvent used, and is preferably 0 to 25 ℃. The reaction time varies depending on, for example, the reaction temperature and the reaction is usually completed within about 0.5 to 24 hours.

Preparation route 3C

Note that, as a method for producing the phenylacetamide compound (1-1a), a phenylacetic acid halide compound (3C) obtained by reacting a phenylacetic acid compound (3B) with a halogenating agent can be used as a material.

The above-mentioned reaction may be carried out in the presence of a base. Any of the same bases as those described above can be used as the base, and preferred examples of the base include organic bases such as triethylamine, pyridine, di-isopropylamine, 4-diisopropylethylamine, 4-dimethylaminopyridine, and lutidine. The base may be used in excess to also serve as a reaction solvent.

Examples of halogen reagents include, but are not particularly limited to, POCl₃、POBr₃、SOCl₂、SO₂Cl₂And oxalyl chloride.

The above-mentioned reaction is carried out in a suitable solvent or without any solvent. When the above-mentioned reaction is carried out in a solvent, the solvent is not limited as long as the solvent is inactive to the above-mentioned reaction. As examples of such solvents, the above-mentioned solvents are listed. Any of these solvents may be used alone or a combination of two or more types thereof may be used as needed.

The reaction temperature of the above-mentioned reaction is not particularly limited and it is usually in the range between 10 ℃ and the boiling point of the solvent used and preferably in the range between-5 ℃ and the boiling point of the solvent. The reaction time varies depending on, for example, the reaction temperature, and the reaction is usually completed within about 0.25 to 24 hours.

Preparation route 4

The thioether compound (1-1) can be produced by reacting a thioether compound (hereinafter may be referred to as "compound (9)") with an amide compound represented by the formula (10) (hereinafter may be referred to as "compound (10)") (reaction scheme 12):

[ reaction scheme 12]

Wherein R is¹、R²、R³、R⁴、R⁵、R⁶、R⁷、R⁸、R⁹、R¹⁰、R¹¹And X is as defined above, and Z represents a leaving group.

The ratio used between the thioether compound (9) and the amide compound (10) in the reaction is not particularly limited and may be appropriately selected from a wide range. About 1 to 10 moles of the amide compound (10) are generally used and preferably about equimolar to 5 moles of the amide compound (10) are used relative to 1 mole of the thioether compound (9).

The above-mentioned reaction may be carried out in the absence or presence of a base. In the above case, the above-mentioned reaction is preferably carried out in the presence of a base. Any of the same bases as those shown above in step 1 may be used as the base. Any of these bases is used alone or in combination of two or more types thereof.

1 to 10 moles of the base and preferably about 1 to 5 moles of the base are generally used with respect to 1 mole of the aniline compound (9).

The reaction temperature of the above-mentioned reaction is not particularly limited and it is generally in the range between-10 ℃ and the boiling point of the solvent used and preferably between-0 ℃ and the boiling point of the solvent. The reaction time varies depending on, for example, the reaction temperature and the reaction is usually completed within about 0.5 to 24 hours.

The thioether compound (9) used as starting material can be prepared according to the processes described in EP3002279 and WO 2012/176856.

The thioether compound (1-1) is easily separated from the reaction mixture to be purified by using typical separation means and purification means (e.g., filtration, solvent extraction, distillation, recrystallization, column chromatography, etc.).

Step 5

The benzamide compound represented by the formula (1-2) (hereinafter may be referred to as "compound (1-2)") can be produced by reacting the thioether compound represented by the formula (1-1) with an oxidizing agent (reaction scheme 13):

[ reaction scheme 13]

Wherein R is¹、R²、R³、R⁴、R⁵、R⁶、R⁷、R⁸、R⁹、R¹⁰、R¹¹X and n' are as described above.

The ratio used between the benzamide compound (1-1) and the oxidizing agent in the reaction is not particularly limited and may be appropriately selected from a wide range. About 1 to 10 moles of the oxidizing agent and preferably about equimolar to 5 moles of the oxidizing agent are generally used relative to 1 mole of the benzamide compound (1-1).

The above-mentioned reaction may be carried out in the presence of an oxidizing agent. As the oxidizing agent, any of known oxidizing agents can be used as long as the oxidizing agent can effect the oxidation of the sulfide to the sulfoxide, and examples of the oxidizing agent include the following combinations: peracids such as performic acid, peracetic acid, pertrifluoroacetic acid, perbenzoic acid, m-chloroperoxybenzoic acid (mCPBA), and orthocarbonylperbenzoic acid; alkyl hydroperoxides such as hydrogen peroxide, tert-butyl hydroperoxide and cumene hydroperoxide; and titanium tetraalkoxides such as titanium tetraisopropoxide; dichromate salts such as sodium dichromate and potassium dichromate; and permanganates such as permanganic acid, sodium permanganate, and potassium permanganate; and the like. Any one of these oxidizing agents alone or a combination of two or more types thereof is used.

The oxidizing agent may be used in an excess amount of the stoichiometric amount or in an excess amount more than the above-mentioned amount relative to 1 mole of the benzamide compound (1-1). Preferably, 1 to 10 times the oxidizing agent and more preferably about 1 to 5 times the oxidizing agent may be used.

The above-mentioned reaction can be further carried out by adding a catalyst.

The above-mentioned reaction is carried out in a suitable solvent. Examples of the solvent include: fatty acid or alicyclic hydrocarbon-based solvents such as n-hexane, cyclohexane, and n-heptane; aromatic hydrocarbon-based solvents such as benzene, chlorobenzene, toluene, xylene, and the like; halogenated hydrocarbon-based solvents such as dichloromethane, 1, 2-dichloroethane, chloroform, carbon tetrachloride, and the like; ether-based solvents such as diethyl ether, THF, 1, 4-dioxane, and the like; ester solvents such as methyl acetate and ethyl acetate; acetonitrile; amide-based solvents such as DMF, N-dimethylacetamide, N-methyl-2-pyrrolidone, and the like; sulfoxide-based solvents such as dimethylsulfoxide; alcohol-based solvents, such as aprotic polar solvents like sulfolane, methanol, ethanol, isopropanol, etc. Any of these solvents may be used alone or a combination of two or more types thereof may be used as needed.

The reaction temperature of the above-mentioned reaction is not particularly limited, and it is generally in the range between-20 ℃ and the boiling point of the solvent used, preferably-10 ℃ to 60 ℃, and more preferably 20 to 50 ℃. The reaction time varies depending on, for example, the reaction temperature, and the reaction is usually completed within about 0.25 to 24 hours.

The thioether compound (1-2) obtained by the method shown in step 5 is easily isolated from the reaction mixture to be purified by using typical separation means and purification means (e.g., filtration, solvent extraction, distillation, recrystallization, chromatography, etc.).

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

When the compound (1) has regioisomers, each regioisomer can be separated by a commonly used separation step (e.g., silica gel chromatography).

Pest control agent

The compound (1) of the present invention is useful as an active ingredient of a pest control agent. Examples of the pest control agent include agents for controlling pests, mites, nematodes or soil pests (agricultural and horticultural insecticides, acaricides, nematicides or soil insecticides) which cause problems in both agricultural and horticultural fields; animal ectoparasite-controlling agents (e.g., flea-killing agents, acaricides (ixodicide), and pezidine (pedivulicididon)), and the like.

For use as an active ingredient of a pest control agent, the compound (1) of the present invention may be used as it is without other components. However, it is generally preferred to use the compound by: in combination with a solid carrier, a liquid carrier or a gaseous carrier (propellant) and optionally in combination with a surfactant and other adjuvants for pharmaceutical preparations, and formulating the resulting mixture into various forms (e.g., oily solutions, emulsions, wettable powders, flowable formulations, granules, powders, aerosols, fumigants, etc.) according to known preparation methods.

The compound (1) of the present invention is contained in these preparations usually in a proportion of 0.01 to 95% by weight and preferably 0.1 to 50% by weight.

Examples of the solid carrier that can be used in the formulation include solid carriers in the form of fine powder or particles, such as clays (e.g., kaolin clay, diatomaceous earth, synthetic hydrated silica, bentonite, Fubasami clay, and acid clay), talc, ceramics, other inorganic minerals (e.g., diatomaceous earth, quartz, sulfur, activated carbon, calcium carbonate, and hydrated silica gel), 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 methyl ethyl ketone), 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), amides (e.g., N-dimethylformamide and N, N-dimethylacetamide), halogenated hydrocarbons (e.g., dichloromethane, trichloroethane, and carbon tetrachloride), dimethyl sulfoxide, soybean oil, cottonseed oil, and other vegetable oils, and the like.

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

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

Examples of adjuvants used in pharmaceutical preparations include fixatives, dispersants, stabilizers, and the like.

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

Examples of the stabilizer include PAP (isopropyl acid phosphate), BHT (2, 6-di-tert-butyl-4-methylphenol), BHA (a 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.

As for the pest control agent of the present invention, it is preferable to use compound (1) as it is or by dilution with water or the like. The pest control agent of the present invention can be used by mixing with: for example, other pest control agents (e.g., known insecticides, nematocides, tickicides, fungicides), herbicides, plant growth control agents, synergists, soil conditioners, animal feeds, and the like, or they may be used simultaneously with these agents without mixing.

The amount of the pest control agent of the present invention is not limited, and may be appropriately selected from a wide range according to various conditions (e.g., concentration of active ingredient, form of formulation, type of disease and pest to be treated, type of plant, severity of disease, application time, application method, chemicals to be used in combination (insecticide, nematicide, acaricide, fungicide, herbicide, plant growth control agent, synergist, soil conditioner, etc.), and amount and type of fertilizer).

When used as an insecticide, the compound (1) of the present invention is usually used at 0.01g/100m²To 500g/100m²And preferably 1g/100m²To 200g/100m²The amount of (c) is used.

When used as acaricides, the compound (1) of the present invention is usually used at 0.1g/100m²To 500g/100m²And preferably 1g/100m²To 200g/100m²The amount of (c) is used.

When emulsions, wettable powders, flowable formulations, etc. are used by dilution with water, the concentration is from 0.1ppm to 1,000ppm and preferably from 1ppm to 500 ppm. Granules, powders and the like can be used as such without dilution.

The compounds (1) of the present invention are characterized by having particularly excellent acaricidal activity and a broad activity spectrum.

The compound (1) of the present invention can be effectively used as an agricultural and horticultural insecticide, acaricide, nematicide or soil insecticide. Specifically, the compound (1) of the present invention is effective for controlling pests such as aphids such as myzus persicae and aphis gossypii; back borer (diamondback moth), cabbage looper, common cutworm, apple leaf roller moth, sandfly, tobacco moth larva, gypsy moth, rice leaf roller, tea leaf roller moth, potato beetle, yellow dawnia (cucurbit leaf beetle), boll weevil, plant hopper, leafhopper, scale insect, bed bug, whitefly, thrips, grasshopper, flower fly, chafer, black cutworm, rootworm, ant, and agricultural insect pests; gastropod animals such as slugs and snails; rat mites, cockroaches, houseflies, housemosquitoes and other insects which harm sanitation; grain storage insects such as wheat moth, callosobruchus chinensis, tribolium castaneum, pink tick and the like; insects such as bagworms, black carpet beetles, and terrestrial termites which harm clothing and insects which harm houses and home furnishings; mites such as tetranychus urticae, tetranychus cinnabarinus, tetranychus citriodorus, tetranychus zerumbet (Kanzawaspider mite), tetranychus ulmi (European red mite) (fruit tree tetranychus), guangming, tetranychus citriodorus, and root mites (bulbus mite); house dust mites such as Tyrophagus putrescentiae (Tyrophagus putrescentiae), Dermatophagoides farinae (Dermatophagoides farinae), and Pachyrhizus carinata (Chelacaropsis moorei); and the like, and soil pests such as plant-parasitic nematodes such as root-knot nematodes, cyst nematodes, root-rot nematodes, white tip nematodes, strawberry leaf bud nematodes, pine wood nematodes and the like; zoophotida, tidea, and the like; and the like.

The pest control agent of the present invention can also effectively control various pests having resistance to chemicals such as organophosphorus agents, carbamate agents, synthetic pyrethroid agents and neonicotinoid agents.

References, such as scientific literature, patents, and patent applications, cited herein are hereby incorporated by reference to the same extent as if each document were specifically set forth in its entirety. As used herein, an or is used when the "at least one or more" items listed in a 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 above-mentioned explanation and the following manufacturing examples and examples are not provided to limit the present invention, but only for illustrative purposes. Accordingly, the scope of the invention is not limited to the embodiments and these examples specifically described herein and is limited only by the scope of the claims.

Preparation example 1:

preparation of N- (2-fluoro-4-methylphenyl) -2- (4- (trifluoromethoxy) phenyl) acetamide (4-14)

To a solution of 2-fluoro-4-methylaniline (2-14; 1.1g,8.79mmol,1 eq) and 2- (4- (trifluoromethoxy) phenyl) acetic acid (3 b-14; 2.12g,9.67mmol,1.1 eq) in pyridine (10ml) at 0 deg.C was slowly added POCl₃(1.6ml,17.58mmol,2 equiv.). The reaction was maintained at the same temperature for an additional 15 minutes. The reaction mixture was then quenched in ice and the product was extracted with ethyl acetate. The combined organic layers were washed with 1N HCl solution followed by brine solution, dried over sodium sulfate, filtered and concentrated under reduced pressure to give 2.20g of crude product 4-14 as a yellow solid. The crude product thus obtained was further used as such without any purification.

¹H NMR(CDCl₃):8.10(t,J＝8.6Hz,1H),7.39-7.37(m,2H),7.25-7.23(m,3H),6.92-6.85(m,2H),3.75(s,2H),2.29(s,3H)。

Preparation example 2:

preparation of 5- (2- (4- (trifluoromethoxy) phenyl) acetamide) -4-fluoro-2-methylbenzene-1-sulfonyl chloride (5-14)

Chlorosulfonic acid (14.0g,120mmol,18 equiv.) was added to N- (2-fluoro-4-methylphenyl) at a temperature below 50 deg.C) -2- (4- (trifluoromethoxy) phenyl) acetamide (4-14; 2.20g,6.72mmol,1 eq). The reaction mixture was then stirred at room temperature overnight. The reaction mixture was then quenched in ice and the product was extracted with ethyl acetate. The combined organic layers were washed by distilled water, dried over sodium sulfate, filtered and concentrated under reduced pressure to give 2.60g of crude product 5-14 as a dark viscous oil. The crude product thus obtained was further used as such without any purification.¹H NMR(CDCl₃):9.08(d,J＝7.6Hz,1H),7.39-7.36(m,2H),7.25-7.24(m,3H),7.12(d,J＝10.8Hz,1H),3.79(s,2H),2.71(s,3H)。

Preparation example 3:

preparation of N- (2-fluoro-5-mercapto-4-methylphenyl) -2- (4- (trifluoromethoxy) phenyl) acetamide (6-14)To a mixture of 5- (2- (4- (trifluoromethoxy) phenyl) acetamide) -4-fluoro-2-methylbenzene-1-sulfonyl chloride (5-14; 2.60g,6.11mmol,1 eq) in toluene (20ml) was added triphenylphosphine (4.8g,18.35mmol,3 eq) at room temperature. The reaction was then heated to 100 ℃ and held for 3 hours. The reaction mixture was allowed to cool to room temperature and all volatiles were distilled off by a rotary evaporator. The crude product thus obtained was purified by column chromatography on silica gel using a mixture of ethyl acetate and n-hexane as an eluent, to obtain 1.0g of the title compounds 6 to 14 as off-white solids.

¹H NMR(CDCl₃):8.26(d,J＝7.6Hz,1H),7.38-7.36(m,2H),7.25-7.21(m,3H),6.87(d,J＝10.8Hz,1H),3.74(s,2H),3.30(s,1H),2.25(s,3H)。

Example 1:

n- (5- (2,2, 2-trifluoroethylthio) -2-fluoro-4-methylphenyl) -2- (4- (trifluoromethoxy) phenyl) acetyl Preparation of amine (1A-14)

To a cooled mixture of N- (2-fluoro-5-mercapto-4-methylphenyl) -2- (4- (trifluoromethoxy) phenyl) acetamide (6-14; 1.00g,2.78mmol,1 eq) in DMF (10ml) was added cesium carbonate (0.90g,2.78mmol,1 eq) followed by sodium formaldehyde sulfoxylate (0.33g,2.78mmol,1 eq). Trifluoroiodoethane (0.639g,3.06mmol,1.1 equiv.) was then added slowly to this mixture at 0 ℃ and the resulting mixture was stirred at room temperature for 6 hours. The reaction mixture was then poured into distilled water and extracted with dichloromethane. The combined organic layers were washed with distilled water, dried over sodium sulfate, filtered and concentrated under reduced pressure to obtain the crude product. The crude product thus obtained was purified by column chromatography on silica gel using a mixture of ethyl acetate and n-hexane as an eluent, to obtain 0.95g of the title compounds 1A-14 as pale yellow solids.

Preparation example 4:

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

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

¹H NMR(CDCl₃):δ8.14-8.10(m,1H),7.25(bs,1H),6.93-6.88(m,2H),2.31(s,3H),2.20(s,3H)。

Preparation example 5:

preparation of 5-acetamido-4-fluoro-2-toluene-1-sulfonyl chloride

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

¹H NMR(CDCl₃):δ9.09(d,J＝7.6Hz,1H),7.48(bs,1H),7.14(d,J＝10.8Hz,1H),2.72(s,3H),2.25(s,3H)。

Preparation example 6:

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

To a mixture of 5-acetamido-4-fluoro-2-methylbenzene-1-sulfonyl chloride (7.00g,26.34mmol,1 eq) in glacial acetic acid (60ml) was added zinc dust (34.44g,526.80mmol,20 eq) portionwise 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 a bed of celite. The organic layer was washed well with distilled water, dried over sodium sulfate, filtered and concentrated under reduced pressure to give 3.64g of crude product as a pale yellow solid. The crude product thus obtained was further used as such without any purification.

¹H NMR(CDCl₃):δ8.25(d,J＝7.6Hz,1H),7.29(bs,1H),6.89(d,J＝11.6Hz,1H),3.34(bs,1H),2.26(s,3H),2.20(s,3H)。

Preparation example 7:

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

¹H NMR(CDCl₃):δ8.49(d,J＝8.0Hz,1H),7.29(bs,1H),6.96(d,J＝11.6Hz,1H),3.42-3.35(q,J＝9.6Hz,2H),2.41(s,3H),2.21(s,3H)。

Preparation example 8:

preparation of 5- (2,2, 2-trifluoroethylthio) -2-fluoro-4-methylaniline

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

¹H NMR(CDCl₃):δ6.98(d,J＝9.2Hz,1H),6.86(d,J＝11.6Hz,1H),3.64(bs,2H),3.32-3.25(q,J＝9.6Hz,2H),2.36(s,3H)。

Example 2:

preparation of N- (5- (2,2, 2-trifluoroethylthio) -2-fluoro-4-methylphenyl) -2-phenylacetamide (1A-1)

To a cooled solution of 5- (2,2, 2-trifluoroethylthio) -2-fluoro-4-methylaniline (0.10g,0.42mmol,1 equivalent) in chloroform (10ml) was added triethylamine (0.046g,0.46mmol,1.1 equivalents), followed by slow addition of 2Phenyl acetyl chloride (0.068g,0.44mmol,1.05 equiv). The resulting mixture was then stirred at room temperature for 14 hours. The reaction mixture was then poured into NaHCO₃The product was dissolved and extracted by dichloromethane. The combined organic layers were then washed with distilled water followed by brine solution, dried over sodium sulfate, filtered and concentrated under reduced pressure to give 0.125g of the title product as an off-white solid.

Example 3:

process for producing N- (5- (2,2, 2-trifluoroethylthio) -2-fluoro-4-methylphenyl) -2- (2-chlorophenyl) acetamide (1A-3) Preparation of

To a cooled solution of 5- (2,2, 2-trifluoroethylthio) -2-fluoro-4-methylaniline (0.05g,0.21mmol,1 eq) in dichloromethane (10ml) was added triethylamine (0.042g,0.42mmol,2.0 eq) followed by slow addition of 2- (2-chlorophenyl) acetyl chloride (0.04g,0.21mmol,1 eq). The resulting mixture was then stirred at room temperature for 14 hours. The reaction mixture was then poured into NaHCO₃The product was dissolved and extracted by dichloromethane. The combined organic layers were then washed with distilled water followed by brine solution, dried over sodium sulfate, filtered and concentrated under reduced pressure to give the crude product. The crude product thus obtained was purified by column chromatography on silica gel using a mixture of ethyl acetate and n-hexane as an eluent to obtain 0.07g of the title compound as a brown solid.

Example 4:

n- (5- (2,2, 2-trifluoroethylthio) -2-fluoro-4-methylphenyl) -2- (2, 5-dichlorophenyl) acetamide (1A- 4) Preparation of

To a cooled mixture of 5- (2,2, 2-trifluoroethylthio) -2-fluoro-4-methylaniline (0.05g,0.21mmol,1 eq) and 2- (2, 5-dichlorophenyl) acetic acid (0.05g,0.25mmol,1.2 eq) in pyridine (3ml) was added POCl very slowly₃(0.08g,0.52mmol,2.5 equiv.). After a few minutes, the reaction mixture is,the reaction mixture was poured into ice and the product was extracted with ethyl acetate. The combined organic layers were then washed successively with 1N HCl and distilled water, dried over sodium sulfate, filtered and concentrated under reduced pressure to give the crude product. The crude product thus obtained was purified by column chromatography on silica gel using a mixture of ethyl acetate and n-hexane as an eluent, to obtain 0.023g of the title compound as a pale yellow solid.

Example 5:

2- (4- (ethylthio) phenyl) -N- (2-fluoro-4-methyl-5- ((2,2, 2-trifluoroethyl) thio) phenyl) acetyl Preparation of amine (1B-1)

To a cooled mixture of 5- (2,2, 2-trifluoroethylthio) -2-fluoro-4-methylaniline (0.20g,0.835mmol,1 eq) and 2- (4- (ethylthio) phenyl) acetic acid (0.186g,1.021mmol,1.2 eq) in pyridine (3ml) was added POCl very slowly₃(0.08g,5.348mmol,6.4 equiv.). After a few minutes, the reaction mixture was poured into ice and the product was extracted with ethyl acetate. The combined organic layers were then washed successively with 1N HCl and distilled water, dried over sodium sulfate, filtered and concentrated under reduced pressure to give the crude product. The crude product thus obtained was purified by column chromatography on silica gel using a mixture of ethyl acetate and n-hexane as an eluent to obtain 0.18g of the title compound as a yellow solid.

Example 6:

n- (2-fluoro-4-methyl-5- ((2,2, 2-trifluoroethyl) thio) phenyl) -2- (4- (propylthio) phenyl) acetyl Preparation of amine (1B-2)

To a cooled mixture of 5- (2,2, 2-trifluoroethylthio) -2-fluoro-4-methylaniline (0.20g,0.835mmol,1 eq) and 2- (4- (propylthio) phenyl) acetic acid (0.327g,1.556mmol,1.8 eq) in pyridine (3ml) was added POCl very slowly₃(0.08g,5.348mmol,6.4 equiv.). After a few minutes, the reaction was mixedThe mixture was poured into ice and the product was extracted with ethyl acetate. The combined organic layers were then washed successively with 1N HCl and distilled water, dried over sodium sulfate, filtered and concentrated under reduced pressure to give the crude product. The crude product thus obtained was purified by column chromatography on silica gel using a mixture of ethyl acetate and n-hexane as an eluent to obtain 0.13g of the title compound as a yellow solid.

Example 7:

n- (2-fluoro-4-methyl-5- ((2,2, 2-trifluoroethyl) thio) phenyl) -2- (4- (isopropylthio) phenyl) ethyl Preparation of amide (1B-3)

To a cooled mixture of 5- (2,2, 2-trifluoroethylthio) -2-fluoro-4-methylaniline (0.20g,0.835mmol,1 eq) and 2- (4- (isopropylthio) phenyl) acetic acid (0.155g,0.737mmol,0.8 eq) in pyridine (3ml) was added POCl very slowly₃(0.08g,5.348mmol,6.4 equiv.). After a few minutes, the reaction mixture was poured into ice and the product was extracted with ethyl acetate. The combined organic layers were then washed successively with 1N HCl and distilled water, dried over sodium sulfate, filtered and concentrated under reduced pressure to give the crude product. The crude product thus obtained was purified by column chromatography on silica gel using a mixture of ethyl acetate and n-hexane as an eluent to obtain 0.12g of the title compound as a yellow solid.

Example 8:

the compounds shown in tables 1 to 4 were prepared by methods similar to those described in examples 1 to 7 or described in the specification, except for the compounds obtained in examples 1 to 7.

Tables 2 and 4 show the compounds of the invention thus obtained¹H-NMR data.

Abbreviations in tables 1 to 4 are as shown below.

F: fluorineAnd Cl: chlorine, Br: bromine, Me: methyl group, Et: ethyl, n-Pr: n-propyl group, i-Pr: isopropyl group, n-Bu: n-butyl, t-Bu: t-butyl, n-Pent: n-pentyl, CF₃: trifluoromethyl, OMe: methoxy, OEt: ethoxy radical, OCF₃: trifluoromethoxy, SCF₃: trifluoromethylthio, SMe: methylthio radical, NH₂: amino group, NO₂: nitro, Ph: phenyl, S: sulfur atom, O: oxygen atom, Ac: acetyl, CHF₂: a difluoromethyl group.

TABLE 1

TABLE 2

TABLE 3

TABLE 4

The following are formulation examples, wherein "parts" means "parts by weight".

Formulation example 1: emulsion and method of making

10 parts of each of the compounds according to the invention are dissolved in 45 parts of Solvesso 150 and 35 parts of N-methylpyrrolidone. To this was added 10 parts of an emulsifier (trade name: Sorpol 3005X, manufactured by Toho Chemical Industry Co., Ltd.). The mixture was mixed by stirring to give a 10% emulsion.

Formulation example 2: wettable powders

20 parts of each of the compounds of the present invention were 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 silica and 54 parts of clay. The mixture was mixed by stirring with a juice mixer to obtain a 20% wettable powder.

Formulation example 3: granules

To 5 parts of each of the compounds of the present invention, 2 parts of sodium dodecylbenzenesulfonate, 10 parts of bentonite and 83 parts of clay were added, and each mixture was thoroughly mixed by stirring. To which an appropriate amount of water was added. The resulting mixture was further stirred and granulated with a granulator. The granules were air dried to give 5% granules.

Formulation example 4: powder preparation

1 part of each of the compounds of the present invention was dissolved in an appropriate amount of acetone. To this was added 5 parts of a fine powder of synthetic hydrated silica, 0.3 parts of isopropyl acid phosphate (PAP) and 93.7 parts of clay. The mixture was mixed by stirring with a juice mixer and the acetone was removed by evaporation to give a 1% powder.

Formulation example 5: flowable formulation

20 parts of each of the compounds according to the invention are mixed with 20 parts of water containing 3 parts of polyoxyethylene tristyryl phenyl ether phosphate triethanolamine and 0.2 part of Rhodorsil 426R. The mixture was subjected to wet milling with a DYNO-Mill and mixed with 60 parts of water containing 8 parts of propylene glycol and 0.32 part of xanthan gum to obtain a 20% aqueous suspension.

Test examples are given below to demonstrate that the compounds of the present invention can be used as active ingredients of acaricides.

Test example 1 (acaricidal test against Tetranychus urticae)

A piece of non-woven fabric (4.5X 5.5cm) was suspended inside the plastic cup by means of a cut made in the lid of the plastic cup. After pouring water into the cup, the cup was covered with a lid. Then, kidney bean leaves (about 3.5X 4.5cm) were placed on the fully wetted nonwoven fabric. Another bean leaf with two-spotted spider mite (about 30 mite specimens) was placed on top of the first leaf, and the fabric and leaf were placed in a thermostatic chamber with a temperature of 25 ± 2 ℃ and a humidity of 40%.

A miticidal formulation containing the compound of the present invention (200ppm) was prepared by adding an aqueous solution (100ppm) of Sorpol 355 (produced by Tobo kagakuco. ltd.) to a methanol solution of the compound of the present invention.

These miticidal formulations were sprayed onto the leaves, and the leaves were air-dried and placed in a thermostatic chamber (25. + -. 2 ℃ and 50% humidity). The mortality of tetranychus urticae was calculated after 2 days.

Compounds exhibiting a mortality rate of 50% or greater are as follows:

compound number: 1A-2, 1A-5, 1A-8, 1A-12, 1A-13, 1A-14, 1A-15, 1A-20, 1A-23, 1A-24, 1A-27, 1A-28, 1A-30, 1A-33, 1A-42, 1A-43, 1A-45, 1A-46, 1A-47, 1A-48, 1A-49, 1A-50, 1A-51, 1A-52, 1A-53, 1A-54, 1A-55, 1A-56, 1A-57, 1A-58, 1A-59, 1A-60, 1A-62, 1A-63, 1A-65, 1A-67, 1A-68, 1A-72, 1A-73, 1A-74, 1A-75, 1A-76, 1A-77, 1A-78, 1A-82, 1A-83, 1A-85, 1A-86, 1A-87, 1A-88, 1A-90, 1A-91, 1A-92, 1A-93, 1A-94, 1A-95, 1A-96, 1A-97, 1A-103, 1A-104, 1A-107, 1A-108, 1A-109, 1A-111, 1A-112, 1A-113, 1A-114, 1A-116, 1A-117, 1A-118, 1A-119, 1A-120, 1A-121, 1A-122, 1A-121, 1A-123, 1A-126, 1A-127, 1A-128, 1B-1, 1B-2, 1B-3, 1B-5, 1B-7, 1B-8, 1B-9, 1B-10, 1B-11, 1B-12, 1B-15, 1B-16, 1B-17, 1B-18, 1B-19, 1B-20, 1B-22, 1B-23, 1B-24, 1B-25, 1B-26, 1B-27, 1B-28, 1B-29, 1B-30, 1B-32, 1B-33, 1B-34, 1B-35, 1B-36, 1B-37, 1B-38, 1B-39, 1B-16, 1B-41, 1B-43, 1B-48, 1B-49, 1B-50, 1B-54, 1B-55, 1B-56, 1B-57, 1B-58, 1B-59, 1B-61, 1B-62, 1B-63, 1B-64, 1B-65, 1B-66, 1B-67, 1B-68, 1B-69, 1B-70, 1B-71, 1B-72, 1B-73, 1B-74, 1B-76, 1B-77, 1B-78, 1B-79, 1B-80, 1B-82, 1B-83, 1B-87, 1B-90, 1B-96, 1B-97, 1B-98, 1B-99, 1B-100, 1B-101 and 1B-102.

Test example 2 (ovicidal test against Tetranychus urticae)

A piece of non-woven fabric (4.5X 5.5cm) was suspended inside the plastic cup by means of a cut made in the lid of the plastic cup. After pouring water into the cup, the cup was covered with a lid. Then, kidney bean leaves (about 3.5X 4.5cm) were placed on the fully wetted nonwoven fabric. 20 female tetranychus urticae adults were placed on top of the leaves, and the fabric and leaves were placed in a thermostatic chamber with a temperature of 25 + -2 deg.C and a humidity of 40% and 16L 8D.

The next day, after the number of female adults was adjusted to 20 again, 2ml of an acaricidal formulation containing the compound of the present invention (200ppm) prepared in the same manner as in test example 1 was sprayed onto the leaves, and the leaves were air-dried and placed in a constant-temperature chamber (25 ± 2 ℃ and 50% humidity). The ovicidal rate of tetranychus urticae was calculated 6 days after spraying the miticidal formulation. Compounds exhibiting a mortality rate of 50% or greater at 500ppm are as follows:

compound number: 1A-2, 1A-8, 1A-12, 1A-13, 1A-14, 1A-20, 1A-23, 1A-27, 1A-33, 1A-42, 1A-43, 1A-47, 1A-48, 1A-49, 1A-50, 1A-51, 1A-52, 1A-53, 1A-54, 1A-55, 1A-56, 1A-57, 1A-58, 1A-59, 1A-60, 1A-61, 1A-63, 1A-65, 1A-67, 1A-68, 1A-69, 1A-70, 1A-71, 1A-72, 1A-73, 1A-74, 1A-76, 1A-77, 1A-78, 1A-82, 1A-83, 1A-85, 1A-86, 1A-87, 1A-88, 1A-90, 1A-91, 1A-93, 1A-94, 1A-95, 1A-96, 1B-1, 1B-2, 1B-3, 1B-5, 1B-7, 1B-8, 1B-9, 1B-10, 1B-11, 1B-12, 1B-15, 1B-16, 1B-17, 1B-18, 1B-19, 1B-20, 1B-22, 1B-23, 1B-24, 1B-25, 1B-26, 1B-27, 1B-28, 1B-29, 1B-30, 1B-32, 1B-33, 1B-34, 1B-35, 1B-36, 1B-37, 1B-38, 1B-39, 1B-41, 1B-43, 1B-48, 1B-49, 1B-50, 1B-54, 1B-55, 1B-56, 1B-57, 1B-58, 1B-59, 1B-61, 1B-62, 1B-63, 1B-64, 1B-65, 1B-66, 1B-67, 1B-68, 1B-69, 1B-70, 1B-71, 1B-72, 1B-73, 1B-74, 1B-76, 1B-77, 1B-68, 1B-78, 1B-79, 1B-80, 1B-82, 1B-83, 1B-86, 1B-87, 1B-88, 1B-90, 1B-96, 1B-97, 1B-98, 1B-99, 1B-100 and 1B-101.

(Note)

It is understood that the patents, patent applications, and documents cited herein are incorporated by reference as if the contents were specifically described herein. This application claims priority from PCT application No. PCT/IB2016/055523 and indian patent application No. 201611024522, the entire contents of which are incorporated herein by reference.

[ Industrial Applicability ]

The present invention provides novel benzamide compounds, a method for preparing the same, and acaricides, and thus the present invention is particularly useful in the agricultural industry.

Claims

1. A benzamide compound represented by the formula (1):

or a salt thereof,

wherein R is¹Is represented by C_1-6Alkyl or C_1-6A haloalkyl group;

R²and R³Are the same or different and each represents hydrogen, halogen, cyano, nitro, C_1-6Alkyl, aryl, heteroaryl, and heteroaryl,C_1-6Haloalkyl, C_1-6Alkoxy radical, C_1-6Haloalkoxy, C_1-6Alkoxy radical C_1-6Alkyl radical, C_1-6Halogenoalkoxy radical C_1-6Alkyl radical, C_3-8Cycloalkyl or C_3-8Cycloalkyl radical C_1-6An alkyl group;

R⁴represents hydrogen, formyl, C_1-6Alkyl radical, C_1-6Haloalkyl, C_1-6Alkoxy radical, C_1-6Haloalkoxy, C_1-6Alkoxy radical C_1-6Alkyl radical, C_1-6Halogenoalkoxy radical C_1-6Alkyl radical, C_3-8Cycloalkyl radical, C_3-8Cycloalkyl radical C_1-6Alkyl radical, C_1-6Alkylcarbonyl group, C_1-6Halogenoalkylcarbonyl group, C_1-6Alkoxycarbonyl group, C_1-6Halogenoalkoxycarbonyl, arylcarbonyl, aryloxycarbonyl, C_2-6Alkenyl radical, C_2-6Haloalkenyl, C_2-6Alkynyl, C_2-6Halogenated alkynyl, C_1-6Alkylsulfonyl radical, C_1-6Haloalkylsulfonyl group, C_1-6Alkylsulfinyl radical, C_1-6Haloalkylsulfinyl radical, C_1-6Alkylthio radical, C_1-6Halogenoalkylthio, aryl C_1-6Alkyl, arylsulfonyl, arylsulfinyl, arylthio or heterocycle, all of which are defined as R⁴Each of the substituents of (a) may be optionally further substituted;

R⁵and R⁶Are the same or different and each represents hydrogen, halogen, C_1-6Alkyl or C_1-6A haloalkyl group; r⁵And R⁶Together with the carbon atoms to which they are bonded may or may not be bonded to each other via at least one heteroatom to form a 3-to 8-membered ring;

x represents oxygen or sulfur; and is

n represents an integer of 0 to 2.

2. The benzamide compound or salt thereof according to claim 1, wherein R¹Is C_1-6A haloalkyl group.

3. The benzamide compound or salt thereof according to claim 1 or 2, wherein R²And R³Are identical or different and each represents halogen, cyano or C_1-6An alkyl group.

4. The benzamide compound or salt thereof according to any one of claims 1 to 3, wherein R⁴Is hydrogen or C_1-6An alkyl group.

5. The benzamide compound or salt thereof according to any one of claims 1 to 4, wherein R⁷、R⁸、R⁹、R¹⁰And R¹¹Are the same or different and each represents hydrogen, halogen, nitro, C_1-6Alkyl radical, C_1-6Haloalkyl, C_1-6Alkoxy radical, C_1-6Haloalkoxy, C_1-6Alkylsulfonyl radical, C_1-6Haloalkylsulfonyl group, C_1-6Alkylsulfinyl radical, C_1-6Haloalkylsulfinyl radical, C_1-6Alkylthio radical, C_1-6A haloalkylthio group, a substituted or unsubstituted amino group, an aryl group or a heterocycle.

6. A process for producing the benzamide compound or salt thereof according to any one of claims 1 to 5, comprising at least one step selected from the group consisting of the following steps (d) and (e):

7. The process for producing a benzamide compound and a salt thereof according to claim 6, further comprising the following step (c):

8. The process for producing a benzamide compound and a salt thereof according to claim 7, further comprising the following step (b):

9. The process for producing a benzamide compound and a salt thereof according to claim 8, further comprising the step (a) of:

10. A pesticidal agent comprising the benzamide compound or a salt thereof according to any one of claims 1 to 5.

11. An acaricide comprising the benzamide compound or a salt thereof according to any one of claims 1 to 5.