JP2003034671A - Benzamide derivatives and agricultural chemicals as well as use thereof - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide benzamide derivatives which show excellent action as an insecticide and mitecide. SOLUTION: The benzamide derivatives represented by the formula (I) [wherein, R is H, 1-6C alkyl or 1-6C alkoxycarbonyl, Q is 3-6C cycloalkyl, substituted phenyl or formula (II): -G-(J)q-L wherein, G is -O-, -S-, -SO-, -SO2 -, -CR<1> R<2> , -CR<1> =R<2> -, -C≡C- or -N((C=O)R<3> )- (wherein, R<1> and R<2> are H, a halogen or a 1-6C alkyl, R<3> is a 1-6C alkyl, 1-6C alkoxyalkyl, phenyl or heterocycle, etc.), J is a 1-8C alkylene or 2-8C alkenylene, etc., q is 0 or 1, L is H, halogen, CN, NO2 , 3-6C cycloalkyl, phenylcarbamoyl, phenylsufamoyle or heterocycle, etc.}, X and Y are a halogen, CN, NO2 , 3-6C cycloalkyl, phenylcarbamoyl or heterocycle, etc., B<1> , B<2> , B<3> and B<4> are N or C, Z or O or S.], agricultural chemicals containing the derivatives as effective component, and the use thereof are provided.

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to a benzamide derivative, an agricultural and horticultural agent containing the compound as an active ingredient, particularly an agricultural or horticultural insecticide or acaricide, and a method for using the same.

[0002]

2. Description of the Related Art As an agricultural chemical, JP-A-1-163152
Japanese Patent Application Laid-Open No. 3-1237773, Japanese Patent Application Laid-Open No. 9-2
68169, JP-A-56-87501, JP-A-42-5224, JP-A-3-86858, JP-A-2-42046, and JP-A-57-803.
No. 64, WO 95/25723 and Chemical Abstracts, 107: 192859 disclose compounds similar to the benzamide derivative of the present invention.

[0003]

In the production of crops such as agriculture and horticulture, damage by pests and the like is still great, and new agricultural and horticultural agents, especially agricultural and horticultural drugs, are used due to factors such as the generation of pests resistant to existing drugs. Development of insecticide is desired.
Further, various labor-saving application methods are required due to aging of farmers, and creation of agricultural and horticultural chemicals having characteristics suitable for these application methods is required.

[0004]

Means for Solving the Problems As a result of intensive studies conducted by the present inventors to develop a new agricultural and horticultural chemical, the benzamide derivative represented by the general formula (I) of the present invention was used for agricultural and horticultural purposes. The present invention has been completed by finding out that it is useful as a drug, especially as an agricultural or horticultural insecticide or acaricide.
That is, the invention has the general formula (I)

[Chemical 2] {In the formula, R is a hydrogen atom, C₁-C₆Alkyl group, same or different
Can be a halogen atom, C₁-C₆Alkoxy group, C₁-
C₆Alkylthio group, Mono C₁-C₆Alkylamino group or
One or different di C₁-C₆Is it an alkylamino group?
Substituted C having one or more substituents selected from₁-C₆Archi
Ru radical or C₁-C₆Indicates an alkoxycarbonyl group. Q is C₃-
C₆Cycloalkyl group, C₃-C₆Halocycloalkyl group,
May be one or different, halogen atom, C₁-C₆Alkyl
Base, C₁-C₆Haloalkyl group, C₁-C₆Alkoxy group, C₁-C₆
Haloalkoxy group, C₁-C₆Alkylthio group, C₁-C₆Haloa
Rukiruthio group, C₁-C₆Alkylsulfinyl group, C₁-C₆Ha
Roalkylsulfinyl group, C₁-C ₆Alkylsulfonyl
Base, C₁-C₆Haloalkylsulfonyl group, Mono C₁-C₆Archi
Luamino group, di-C which may be the same or different₁-C₆Alkyl
Amino group, Mono C₁-C₆Haloalkylamino group or same
May be different C₁-C₆Is it a haloalkylamino group?
A substituted phenyl group having one or more substituents selected from
Is the formula (II)

[0005] -G- (J) q-L ( II) ( wherein, G is -O -, - S -, - SO-, ─SO 2 -,
(Wherein, R ¹ and R ² may be the same or different, represent a hydrogen atom, a halogen atom or a C ₁ -C ₆ alkyl ^{group.), - - -CR 1 R} 2 CR 1 = CR 2 - ( wherein In the above, R ¹ and R ² are the same as above.), —C≡C— or —N ((C═O) R ³ ) —
(In the formula, R ³ is a C ₁ -C ₆ alkyl group, a C ₁ -C ₆ haloalkyl group, a C ₁ -C ₆ alkoxy group, a C ₁ -C ₆ haloalkoxy group, mono
C ₁ -C ₆ alkylamino group, which may be the same or different, di C _1-
C ₆ alkylamino group, mono C ₁ -C ₆ haloalkylamino group, di C ₁ -C ₆ haloalkylamino group which may be the same or different, C ₁ -C ₆ alkoxy C ₁ -C ₆ alkyl group, C ₁ -C ₆ haloalkoxy C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkylthio C ₁ -C ₆ alkyl group, C ₁ -C ₆ haloalkylthio C ₁ -C ₆ alkyl group, C ₁
-C ₆ alkylsulfinyl C ₁ -C ₆ alkyl group, C ₁ -C ₆ haloalkylsulfinyl C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkylsulfonyl C ₁ -C ₆ alkyl group, C ₁ -C ₆ haloalkylsulfonyl group C ₁ -C ₆ alkyl group, phenyl group, which may be the same or different, halogen atom, C ₁ -C ₆ alkyl group, C ₁ -C ₆ haloalkyl group, C ₁ -C ₆ alkoxy group, C ₁ -C ₆ Haloalkoxy group, C ₁ -C ₆ alkylthio group, C ₁ -C ₆ haloalkylthio group,
C ₁ -C ₆ alkylsulfinyl group, C ₁ -C ₆ haloalkylsulfinyl group, C ₁ -C ₆ alkylsulfonyl group, C ₁ -C ₆ haloalkylsulfonyl group, mono C ₁ -C ₆ alkylamino group, the same or different Good di C ₁ -C ₆ alkylamino group, mono C
_{A 1-} C ₆ haloalkylamino group or a substituted phenyl group having 1 or more substituents selected from the same or different di C ₁ -C ₆ haloalkylamino groups, a heterocyclic group,

Halogen atoms, which may be the same or different,
C₁-C₆Alkyl group, C₁-C₆Haloalkyl group, C₁-C₆Arco
Xy group, C₁-C₆Haloalkoxy group, C₁-C₆Alkylthio
Base, C₁-C₆Haloalkylthio group, C₁-C₆Alkyl sulfi
Nyl group, C₁-C₆Haloalkylsulfinyl group, C₁-C₆Al
Killsulfonyl group, C₁-C₆A haloalkylsulfonyl group,
Mono C₁-C₆Alkylamino group, which may be the same or different
The C₁-C₆Alkylamino group, Mono C₁-C₆Haloalkylami
Group or di-C which may be the same or different₁-C₆Halo al
A device having one or more substituents selected from a kylamino group.
Substituted heterocyclic group, phenoxy C ₁-C₆Alkyl group, same or different
Can be a halogen atom, C₁-C₆Alkyl group, C ₁-C₆
Haloalkyl group, C₁-C₆Alkoxy group, C₁-C₆Halo arco
Xy group, C₁-C₆Alkylthio group, C₁-C₆Haloalkylthio
Base, C₁-C₆Alkylsulfinyl group, C₁-C₆Haloalkyl
Sulfinyl group, C₁-C₆Alkylsulfonyl group, C₁-C₆Ha
Roalkylsulfonyl group, Mono C₁-C₆Alkylamino
Groups, which may be the same or different, di C₁-C₆Alkylamino
Group, Mono C₁-C₆A haloalkylamino group or the same or
It may be different C₁-C₆Select from haloalkylamino groups
With one or more substituents on the ring₁-C₆
Alkyl group, phenyl C₁-C₆Alkyl group, same or different
Good, halogen atom, C₁-C₆Alkyl group, C₁-C₆Ha
Lower alkyl group, C₁-C₆Alkoxy group, C₁-C₆Halo arcoki
Shi group, C₁-C₆Alkylthio group, C₁-C₆Haloalkylthio
Base, C₁-C₆Alkylsulfinyl group, C₁-C₆Haloalkyl
Sulfinyl group, C₁-C₆Alkylsulfonyl group, C₁-C₆Ha
Roalkylsulfonyl group, Mono C₁-C₆Alkylamino
Groups, which may be the same or different, di C₁-C₆Alkylamino
Group, Mono C₁-C₆A haloalkylamino group or the same or
It may be different C₁-C₆Select from haloalkylamino groups
Substituted Phenyl C Having One or More Substituents on the Ring₁-C
₆Indicates an alkyl group. ) Is shown.

J is C₁-C₈Alkylene group, C₁-C₈Halo Archi
Len group, C₂-C₈Alkenylene group, C₂-C₈Halo alkenylene
Base, C₂-C₈Alkynylene group or C₂-C₈Haloalkynylene group
And q represents an integer of 0 or 1. L is a hydrogen atom,
Rogen atom, cyano group, nitro group, C₃-C₆Cycloalk
Lu group, C₃-C₆Halocycloalkyl group, C₁-C₆Alkoxy
Base, C₁-C₆Haloalkoxy group, C ₁-C₆Alkylthio group, C₁
-C₆Haloalkylthio group, C₁-C₆Alkylsulfinyl
Base, C₁-C₆Haloalkylsulfinyl group, C₁-C₆Alkyl
Sulfonyl group, C₁-C₆Haloalkylsulfonyl group, Mono C
₁-C₆Alkylamino group, di-C which may be the same or different₁-C
₆Alkylamino group, Mono C₁-C₆A haloalkylamino group,
May be the same or different₁-C₆Haloalkylamino
Base, C₁-C₆Alkylcarbonyl group, C₁-C₆Haloalkyl mosquito
Rubonyl group, C₁-C₆Alkoxycarbonylamino group, C₁-
C₆Haloalkoxycarbonylamino group, Mono C₁-C₆Al
Kircarbamoyl group, di-C which may be the same or different₁-C₆
Alkylcarbamoyl group, phenylcarbamoyl group,
May be one or different, halogen atom, C₁-C₆Alkyl
Base, C₁-C₆Haloalkyl group, C₁-C ₆Alkoxy group, C₁-C₆
Haloalkoxy group, C₁-C₆Alkylthio group, C₁-C₆Haloa
Rukiruthio group, C₁-C₆Alkylsulfinyl group, C₁-C₆Ha
Roalkylsulfinyl group, C₁-C₆Alkylsulfonyl
Base, C₁-C₆Haloalkylsulfonyl group, Mono C₁-C₆Archi
Luamino group, di-C which may be the same or different₁-C₆Alkyl
Amino group, Mono C₁-C₆Haloalkylamino group or same
May be different C₁-C₆Is it a haloalkylamino group?
A substituted phenyl having on the ring one or more substituents selected from
A rucarbamoyl group,

Mono C ₁ -C ₆ alkylsulfamoyl group, which may be the same or different, di C ₁ -C ₆ alkylsulfamoyl group, phenylsulfamoyl group, which may be the same or different, halogen atom, C ₁ -C ₆ alkyl group, C ₁ -C ₆ haloalkyl group, C ₁ -C ₆ alkoxy group, C ₁ -C ₆ haloalkoxy group, C ₁
-C ₆ alkylthio group, C ₁ -C ₆ haloalkylthio group, C ₁ -C ₆
Alkylsulfinyl group, C ₁ -C ₆ haloalkylsulfinyl group, C ₁ -C ₆ alkylsulfonyl group, C ₁ -C ₆ haloalkylsulfonyl group, mono C ₁ -C ₆ alkylamino group, di C ₁ which may be the same or different. -C ₆ alkylamino group, mono C ₁ -C ₆
A substituted phenylsulfamoyl group having on the ring one or more substituents selected from a haloalkylamino group and diC ₁ -C ₆ haloalkylamino groups which may be the same or different,
The same or different di C ₁ -C ₆ alkoxyphosphoryl group, the same or different di C ₁ -C ₆ alkoxythiophosphoryl group, diphenylphosphino group, diphenylphosphono group, phenyl group,

Halogen atoms, which may be the same or different,
C ₁ -C ₆ alkyl group, C ₁ -C ₆ haloalkyl group, C ₁ -C ₆ alkoxy group, C ₁ -C ₆ haloalkoxy group, C ₁ -C ₆ alkylthio group, C ₁ -C ₆ haloalkylthio group, C ₁ -C ₆ alkylsulfinyl group, C ₁ -C ₆ haloalkylsulfinyl group, C ₁ -C ₆ alkylsulfonyl group, C ₁ -C ₆ haloalkylsulfonyl group,
Mono C ₁ -C ₆ alkylamino group, which may be the same or different, di C ₁ -C ₆ alkylamino group, mono C ₁ -C ₆ haloalkylamino group or which may be the same or different, di C ₁ -C ₆ haloalkylamino group A substituted phenyl group having one or more substituents selected from the group, a heterocyclic group or the same or different, a halogen atom, a C ₁ -C ₆ alkyl group, a C ₁ -C ₆ haloalkyl group, a C ₁ -C ₆ alkoxy group, C ₁ -C ₆ haloalkoxy group, C ₁
-C ₆ alkylthio group, C ₁ -C ₆ haloalkylthio group, C ₁ -C ₆
Alkylsulfinyl group, C ₁ -C ₆ haloalkylsulfinyl group, C ₁ -C ₆ alkylsulfonyl group, C ₁ -C ₆ haloalkylsulfonyl group, mono C ₁ -C ₆ alkylamino group, di C ₁ which may be the same or different. -C ₆ alkylamino group, mono C ₁ -C ₆
A haloalkylamino group or a substituted heterocyclic group having one or more substituents selected from di-C ₁ -C ₆ haloalkylamino groups which may be the same or different. ) Is shown.

X may be the same or different and may be a halogen atom, a cyano group, a nitro group, a C ₁ -C ₆ alkyl group, a C ₁ -C ₆ haloalkyl group, a C ₃ -C ₆ cycloalkyl group or a C ₃ -C. ₆ halocycloalkyl group, C ₁ -C ₆ alkoxy group, C ₁ -C ₆ haloalkoxy group, C ₁ -C ₆ alkylthio group, C ₁ -C ₆ haloalkylthio group,
C ₁ -C ₆ alkylsulfinyl group, C ₁ -C ₆ haloalkylsulfinyl group, C ₁ -C ₆ alkylsulfonyl group, C ₁ -C ₆ haloalkylsulfonyl group, mono C ₁ -C ₆ alkylamino group, the same or different Good di C ₁ -C ₆ alkylamino group, mono C
_1- C ₆ haloalkylamino group, which may be the same or different.
C ₁ -C ₆ haloalkylamino group, tri C ₁ -C ₆ alkylsilyl group which may be the same or different, phenyl group, which may be the same or different, halogen atom, C ₁ -C ₆ alkyl group, C ₁ -C ₆
Haloalkyl group, C ₁ -C ₆ alkoxy group, C ₁ -C ₆ haloalkoxy group, C ₁ -C ₆ alkylthio group, C ₁ -C ₆ haloalkylthio group, C ₁ -C ₆ alkylsulfinyl group, C ₁ -C ₆ haloalkylsulfinyl group, C ₁ -C ₆ alkylsulfonyl group, C ₁ -C ₆ haloalkylsulfonyl group, mono C ₁ -C ₆ alkylamino group, may be the same or different di C ₁ -C ₆ alkylamino group, mono A C ₁ -C ₆ haloalkylamino group or a substituted phenyl group having one or more substituents selected from the same or different di C ₁ -C ₆ haloalkylamino groups,

A phenoxy group, which may be the same or different,
Halogen atom, C₁-C₆Alkyl group, C₁-C₆Haloalkyl
Base, C₁-C₆Alkoxy group, C₁-C₆Haloalkoxy group, C₁-C
₆Alkylthio group, C₁-C₆Haloalkylthio group, C₁-C₆A
Rukylsulfinyl group, C₁-C₆Haloalkylsulfini
Lu group, C₁-C₆Alkylsulfonyl group, C₁-C₆Haloalkyl
Sulfonyl group, Mono C₁-C₆Alkylamino group, same or
It may be different C₁-C₆Alkylamino group, Mono C₁-C₆Ha
A lower alkylamino group or a dialkyl group which may be the same or different.
C₁-C₆One or more positions selected from haloalkylamino groups
A substituted phenoxy group having a substituent, a heterocyclic group, the same or different
Can be a halogen atom, C₁-C₆Alkyl group, C₁-C₆
Haloalkyl group, C₁-C₆Alkoxy group, C₁-C₆Halo arco
Xy group, C₁-C₆Alkylthio group, C₁-C₆Haloalkylthio
Base, C₁-C₆Alkylsulfinyl group, C₁-C₆Haloalkyl
Sulfinyl group, C₁-C₆Alkylsulfonyl group, C₁-C₆Ha
Roalkylsulfonyl group, Mono C₁-C₆Alkylamino
Groups, which may be the same or different, di C ₁-C₆Alkylamino
Group, Mono C₁-C₆A haloalkylamino group or the same or
It may be different C₁-C₆Select from haloalkylamino groups
A substituted heterocyclic group having one or more substituents represented by
Represents an integer of 0 to 4.

Further, adjacent Xs on the phenyl ring may be combined with each other to form a condensed ring, which may be the same or different, and may be a halogen atom, a C ₁ -C ₆ alkyl group, C
₁ -C ₆ haloalkyl group, C ₁ -C ₆ alkoxy group, C ₁ -C ₆ haloalkoxy group, C ₁ -C ₆ alkylthio group, C ₁ -C ₆ haloalkylthio group, C ₁ -C ₆ alkylsulfinyl group, C ₁ -C ₆ haloalkylsulfinyl group, C ₁ -C ₆ alkylsulfonyl group, C _1-
C ₆ haloalkylsulfonyl group, mono C ₁ -C ₆ alkylamino group, same or different di C ₁ -C ₆ alkylamino group, mono C ₁ -C ₆ haloalkylamino group, same or different di C ₁ -C ₆ haloalkyl group, a phenyl group,
May be the same or different, halogen atom, C ₁ -C ₆ alkyl group, C ₁ -C ₆ haloalkyl group, C ₁ -C ₆ alkoxy group, C ₁ -C
₆ haloalkoxy group, C ₁ -C ₆ alkylthio group, C ₁ -C ₆ haloalkylthio group, C ₁ -C ₆ alkylsulfinyl group, C ₁ -C ₆
Haloalkylsulfinyl group, C ₁ -C ₆ alkylsulfonyl group, C ₁ -C ₆ haloalkylsulfonyl group, mono C ₁ -C ₆ alkylamino group, di C ₁ -C ₆ alkylamino group which may be the same or different, mono C _{A 1-} C ₆ haloalkylamino group or a substituted phenyl group having one or more substituents selected from di-C ₁ -C ₆ haloalkylamino groups which may be the same or different, a heterocyclic group, which may be the same or different, and a halogen. Atom, C ₁ -C ₆ alkyl group, C ₁ -C ₆ haloalkyl group, C ₁ -C
₆ alkoxy group, C ₁ -C ₆ haloalkoxy group, C ₁ -C ₆ alkylthio group, C ₁ -C ₆ haloalkylthio group, C ₁ -C ₆ alkylsulfinyl group, C ₁ -C ₆ haloalkylsulfinyl group, C ₁ -
C ₆ alkylsulfonyl group, C ₁ -C ₆ haloalkylsulfonyl group, mono C ₁ -C ₆ alkylamino group, di C ₁ -C ₆ alkylamino group which may be the same or different, mono C ₁ -C ₆ haloalkylamino group Alternatively, it may have one or more substituents selected from substituted heterocyclic groups having one or more substituents selected from di-C ₁ -C ₆ haloalkylamino groups which may be the same or different.

B¹, B², B³And B^FourAre the same or different
Also, a nitrogen atom or a carbon atom is shown. Y is the same or different
Can be a halogen atom, cyano group, nitro group, C₁
-C₆Alkyl group, C₃-C₆Halocycloalkyl group, phenyl
Groups, which may be the same or different, a halogen atom, C₁-C₆A
Rukiru group, C₁-C₆Haloalkyl group, C₁-C₆An alkoxy group,
C₁-C₆Haloalkoxy group, C₁-C₆Alkylthio group, C₁-C₆
Haloalkylthio group, C ₁-C₆Alkylsulfinyl group, C
₁-C₆Haloalkylsulfinyl group, C₁-C₆Alkylsul
Honyl group, C₁-C₆Haloalkylsulfonyl group, Mono C₁-C₆
Alkylamino group, di-C which may be the same or different₁-C₆A
Lucylamino group, Mono C₁-C₆Haloalkylamino group or
May be the same or different₁-C₆Haloalkylami
A substituted phenyl having one or more substituents selected from
Group, heterocyclic group, which may be the same or different,
Child, C₁-C₆Alkyl group, C₁-C₆Haloalkyl group, C₁-C₆A
Lucoxy group, C₁-C₆Haloalkoxy group, C₁-C₆Alkylchi
O group, C₁-C₆Haloalkylthio group, C₁-C₆Alkylsulf
Inyl group, C₁-C₆Haloalkylsulfinyl group, C₁-C₆A
Rukylsulphonyl group, C₁-C₆Haloalkylsulfonyl
Group, Mono C₁-C₆Alkylamino group, the same or different
Good di C₁-C₆Alkylamino group, Mono C₁-C₆Haloalkyl
Amino group or di-C which may be the same or different₁-C₆Halo
Having one or more substituents selected from alkylamino groups
A substituted heterocyclic group or

-A-R^Four(In the formula, A is -O-, -S-,
-SO-, -SO₂-, -C (= O)-, C₁-C₆Arche
Group, C₁-C₆Haloalkylene group, C₂-C₆Alkenylene group,
C₂-C₆Haloalkenylene group, C₂-C₆Alkynylene group or C₃
-C₆Indicates a haloalkynylene group. R^FourIs a hydrogen atom, C₃-C₆
Halocycloalkyl group, C₃-C₆Halocycloalkenyl
Groups, phenyl groups, which may be the same or different, may be halogenated
Child, C₁-C₆Alkyl group, C₁-C₆Haloalkyl group, C₁-C₆A
Lucoxy group, C₁-C₆Haloalkoxy group, C₁-C₆Alkylchi
O group, C₁-C₆Haloalkylthio group, C₁-C₆Alkylsulf
Inyl group, C₁-C₆Haloalkylsulfinyl group, C₁-C₆A
Rukylsulphonyl group, C₁-C₆Haloalkylsulfonyl
Group, Mono C₁-C₆Alkylamino group, the same or different
Good di C₁-C₆Alkylamino group, Mono C₁-C₆Haloalkyl
Amino group or di-C which may be the same or different₁-C₆Halo
Having one or more substituents selected from alkylamino groups
Substituted phenyl group, heterocyclic group or the same or different
Good, halogen atom, C₁-C₆Alkyl group, C₁-C₆Haloa
Rukiru group, C₁-C₆Alkoxy group, C₁-C₆Haloalkoxy
Base, C ₁-C₆Alkylthio group, C₁-C₆A haloalkylthio group,
C₁-C₆Alkylsulfinyl group, C₁-C₆Haloalkyl sul
Finyl group, C₁-C₆Alkylsulfonyl group, C₁-C₆Haloa
Rukylsulphonyl group, Mono C₁-C₆Alkylamino group,
One or different di C₁-C₆Alkylamino group, Mono C
₁-C₆Haloalkylamino group or the same or different
Good di C₁-C₆1 or more selected from haloalkylamino groups
A substituted heterocyclic group having the above substituent is shown. ), N
Represents an integer of 1 to 5.

Further, adjacent Ys on the phenyl ring may be combined with each other to form a condensed ring, which may be the same or different, and may be a halogen atom, a C ₁ -C ₆ alkyl group, C
₁ -C ₆ haloalkyl group, C ₁ -C ₆ alkoxy group, C ₁ -C ₆ haloalkoxy group, C ₁ -C ₆ alkylthio group, C ₁ -C ₆ haloalkylthio group, C ₁ -C ₆ alkylsulfinyl group, C ₁ -C ₆ haloalkylsulfinyl group, C ₁ -C ₆ alkylsulfonyl group, C _1-
C ₆ haloalkylsulfonyl group, mono C ₁ -C ₆ alkylamino group, same or different di C ₁ -C ₆ alkylamino group, mono C ₁ -C ₆ haloalkylamino group, same or different di C ₁ -C ₆ haloalkyl group, a phenyl group,
May be the same or different, halogen atom, C ₁ -C ₆ alkyl group, C ₁ -C ₆ haloalkyl group, C ₁ -C ₆ alkoxy group, C ₁ -C
₆ haloalkoxy group, C ₁ -C ₆ alkylthio group, C ₁ -C ₆ haloalkylthio group, C ₁ -C ₆ alkylsulfinyl group, C ₁ -C ₆
Haloalkylsulfinyl group, C ₁ -C ₆ alkylsulfonyl group, C ₁ -C ₆ haloalkylsulfonyl group, mono C ₁ -C ₆ alkylamino group, di C ₁ -C ₆ alkylamino group which may be the same or different, mono C _{A 1-} C ₆ haloalkylamino group or a substituted phenyl group having one or more substituents selected from di-C ₁ -C ₆ haloalkylamino groups which may be the same or different, a heterocyclic group, which may be the same or different, and a halogen. Atom, C ₁ -C ₆ alkyl group, C ₁ -C ₆ haloalkyl group, C ₁ -C
₆ alkoxy group, C ₁ -C ₆ haloalkoxy group, C ₁ -C ₆ alkylthio group, C ₁ -C ₆ haloalkylthio group, C ₁ -C ₆ alkylsulfinyl group, C ₁ -C ₆ haloalkylsulfinyl group, C ₁ -
C ₆ alkylsulfonyl group, C ₁ -C ₆ haloalkylsulfonyl group, mono C ₁ -C ₆ alkylamino group, di C ₁ -C ₆ alkylamino group which may be the same or different, mono C ₁ -C ₆ haloalkylamino group Alternatively, it may have one or more substituents selected from substituted heterocyclic groups having one or more substituents selected from di-C ₁ -C ₆ haloalkylamino groups which may be the same or different. Z represents an oxygen atom or a sulfur atom. }
The present invention relates to a benzamide derivative represented by, an agricultural and horticultural insecticide containing the compound as an active ingredient, and a method for using the insecticide.

[0016]

BEST MODE FOR CARRYING OUT THE INVENTION In the definition of the general formula (I) of the benzamide derivative of the present invention, "halogen atom" means chlorine atom, bromine atom, iodine atom or fluorine atom, and "n-
"Is normal," s- "is secondary,
"T-" means tertiary, "i-" means iso,
“C-” represents cyclo, and “C ₁ -C ₆ alkyl” means
For example, methyl, ethyl, n-propyl, i-propyl,
n-butyl, i-butyl, s-butyl, t-butyl, n
-A linear or branched alkyl group having 1 to 6 carbon atoms such as pentyl, neopentyl, and n-hexyl,
“C ₁ -C ₆ haloalkyl” refers to a linear or branched alkyl group having 1 to 6 carbon atoms, which may be the same or different and which is substituted with one or more halogen atoms, such as trifluoromethyl. Group, difluoromethyl group, perfluoroethyl group, perfluoroisopropyl group, chloromethyl group, bromomethyl group, 1-bromoethyl group, 2,3-
A dibromopropyl group and the like can be exemplified, and “C ₁ -C ₈
"Alkylene" refers to a linear or branched alkylene group having 1 to 8 carbon atoms such as methylene, ethylene, propylene, trimethylene, dimethylmethylene, tetramethylene, isobutylene, dimethylethylene, octamethylene and the like.

The "heterocyclic group" refers to a 5- or 6-membered heterocyclic group having one or more heteroatoms selected from oxygen atom, nitrogen atom or sulfur atom, for example pyridyl group, pyridine-N-oxide group. , Pyrimidinyl group, furyl group, tetrahydrofuryl group, thienyl group, tetrahydrothienyl group, tetrahydropyranyl group, tetrahydrothiopyranyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group, thiadiazolyl group, imidazolyl group, Examples thereof include triazolyl group and pyrazolyl group, and examples of the “fused ring” include naphthalene, tetrahydronaphthalene, indene,
Examples include indane, quinoline, quinazoline, indole, indoline, chroman, isochroman, benzodioxane, benzodioxole, benzofuran, dihydrobenzofuran, benzothiophene, dihydrobenzothiophene, benzoxazole, benzothiazole, benzimidazole and indazole. it can.

The benzamide derivative represented by the general formula (I) of the present invention may contain one or more asymmetric carbon atoms or asymmetric centers in its structural formula, and may have two or more optical isomers. A body and a diastereomer may exist, and the present invention includes all optical isomers and a mixture containing them in arbitrary ratios. Further, the benzamide derivative represented by the general formula (I) of the present invention may have two geometric isomers derived from a carbon-carbon double bond in the structural formula, but the present invention is not limited to these. The present invention also includes all geometric isomers of ## STR3 ## and mixtures containing them in arbitrary proportions.

The benzamide derivative represented by the general formula (I) of the present invention can be produced, for example, by the production method illustrated below. Manufacturing method 1.

[Chemical 3] (Wherein B ¹ , B ² , B ³ , B ⁴ , X, Y, Q, R, m
And n are the same as above. However, indicating Q is -G- (J) q-L, G is -N ((C = O) R 3) - excluding. ) A benzoic acid derivative represented by the general formula (III) and the general formula (I
By reacting the aromatic amine derivative represented by V) with a condensing agent or the like in the presence of an inert solvent and a base, the benzamide derivative represented by the general formula (I) can be produced.

Examples of the condensing agent used in this reaction include diethyl cyanophosphate (DEPC), carbonyldiimidazole (CDI), 1,3-dicyclohexylcarbodiimide (DCC), chlorocarbonic acid esters, and iodide 2
-Chloro-1-methylpyridinium etc. can be illustrated. Examples of the base used in this reaction include inorganic bases and organic bases.Examples of the inorganic bases include hydroxides of alkali metal atoms such as sodium hydroxide and potassium hydroxide, sodium hydride and potassium hydride. Alkali metal hydrides, sodium ethoxide, potassium t
Examples of alkali metal salts of alcohols such as butoxide, carbonates such as sodium carbonate, potassium carbonate, sodium hydrogencarbonate and the like, and organic bases include, for example, triethylamine, pyridine, DBU, etc. It may be selected from the equimolar to excess molar range with respect to the benzoic acid derivative represented by III) and used.

The inert solvent used in this reaction may be any one which does not markedly hinder the progress of this reaction, for example, aromatic hydrocarbons such as benzene, toluene, xylene, methylene chloride, chloroform and carbon tetrachloride. Halogenated hydrocarbons such as, chlorobenzene, dichlorobenzene and other halogenated aromatic hydrocarbons, diethyl ether,
Chain or cyclic ethers such as dioxane and tetrahydrofuran, esters such as ethyl acetate, amides such as dimethylformamide and dimethylacetamide, dimethyl sulfoxide, 1,3-dimethyl-2-imidazolidinone and acetone, methyl ethyl ketone and the like. Examples thereof include active solvents, and these inert solvents may be used alone or
A mixture of two or more species can be used. Since this reaction is an equimolar reaction, each reaction agent may be used in an equimolar amount.
Any one of the reactants may be used in excess, the reaction temperature may be room temperature to the boiling point range of the inert solvent used, and the reaction time is not constant depending on the reaction scale and the reaction temperature, but is from several minutes to 48 minutes. It should be done within the range of time. After completion of the reaction, it may be isolated from the reaction system containing the desired product by a conventional method, and the desired product can be produced by refining it by recrystallization, column chromatography or the like, if necessary.

Manufacturing method 2.

[Chemical 4] (Wherein B ¹ , B ² , B ³ , B ⁴ , X, Y, Q, R, m
And n are the same as above. However, indicating Q is -G- (J) q-L, G is -N ((C = O) R 3) - excluding. Ha
l represents a halogen atom. The benzoic acid derivative represented by the general formula (III) is converted into a halogenated benzoyl derivative (V) by using a halogenating agent or the like in the presence or absence of an inert solvent, and the halogenated benzoyl derivative (V) By reacting V) with or without isolation with an aromatic amine derivative represented by the general formula (IV) in the presence of a base and an inert solvent,
A benzamide derivative represented by the general formula (I) can be produced.

1. General formula (III) → General formula (V) Examples of the halogenating agent used in this reaction include thionyl chloride, phosphorus oxychloride, phosphorus trichloride, phosphorus tribromide, phosphorus oxybromide, dichloromethyl methyl ether and the like. The halogenating agent can be exemplified, and the amount thereof is 1 to 10 with respect to the benzoic acid derivative represented by the general formula (III).
It may be used by appropriately selecting it from the range of 0 equivalent. The inert solvent used in this reaction may be any one that does not significantly hinder the progress of this reaction, for example, aromatic hydrocarbons such as benzene, toluene, xylene, and halogens such as methylene chloride, chloroform, carbon tetrachloride, etc. Examples thereof include inert solvents such as derivatized hydrocarbons, halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene, and esters such as ethyl acetate. These inert solvents may be used alone or in combination of two or more. Can be used.

The reaction temperature may be room temperature to the boiling point of the inert solvent used, and the reaction time is not constant depending on the reaction scale and reaction temperature, but may be in the range of several minutes to 48 hours. After completion of the reaction, it can be isolated from the reaction system containing the desired product by a conventional method or can be used for the next reaction without isolation. 2. General formula (V) → General formula (I) As the base or the inert solvent used in this reaction, the base or the inert solvent exemplified in Production Method 1 can be used. Since this reaction is an equimolar reaction, each reaction agent may be used in an equimolar amount, but either reaction agent can be used in excess, and the reaction temperature ranges from room temperature to the boiling point range of the inert solvent used. It can be carried out, and the reaction time is not constant depending on the reaction scale and reaction temperature, but it may be carried out within the range of several minutes to 48 hours. After completion of the reaction, it may be isolated from the reaction system containing the desired product by a conventional method, and the desired product can be produced by refining it by recrystallization, column chromatography or the like, if necessary.

Manufacturing method 3.

[Chemical 5] (Wherein B ¹ , B ² , B ³ , B ⁴ , X, Y, R, R ³ ,
Hal, m and n are the same as above. ) A compound (I-1) in which Q is NH (C═O) R ³ among the benzamide derivatives represented by the general formula (I) of the present invention.
In the case of, the nitrobenzoic acid derivative represented by the general formula (III-1) is led to an amide compound (VI-1), and the amide derivative (VI-1
-1) The nitro group is reduced to the amine derivative (VI-2) in the presence or absence of an inert solvent, and then acylated in the presence or absence of an inert solvent and in the presence of a base. It can be produced by modifying the amino group with an agent or the like.

General formula (III-1) → general formula (IV-1). This reaction can be carried out according to Production Method 1 or 2. General formula (IV-1) → general formula (IV-2). As the reduction method that can be used in this reaction, a conventional method for reducing a nitro group, for example, a method using a metal such as iron, zinc or tin and an acid such as formic acid, acetic acid or hydrochloric acid as a reducing agent, Raney nickel under a hydrogen atmosphere, Examples thereof include a method of using palladium, platinum or the like as a catalyst. Although the amounts of the reducing agent and the catalyst are not constant depending on the reducing method, they may be appropriately selected and used from the range of 0.01 mol to 100 times mol with respect to the amide derivative represented by the general formula (IV-1). The inert solvent used in this reaction may be any one which does not significantly inhibit the progress of this reaction, and examples thereof include alcohols such as methanol, ethanol and 2-propanol, tetrahydrofuran, dioxane and 1,2-dimethoxyethane. Examples thereof include ethers, acids such as formic acid, acetic acid, propionic acid, hydrochloric acid, and inert solvents such as water. These inert solvents can be used alone or in admixture of two or more. The reaction temperature can be room temperature to the boiling point range of the inert solvent used, and the reaction time is not constant depending on the reaction scale and reaction temperature, but may be several minutes to 48 hours. After completion of the reaction, it can be isolated from the reaction system containing the desired product by a conventional method or can be used for the next reaction without isolation.

General formula (IV-2) → general formula (I-1). Examples of the acylating agent used in this reaction include acetyl chloride,
Examples thereof include acid halides such as benzoyl chloride, halogenated carbonic acid esters such as methyl chlorocarbonate, ethyl chlorocarbonate and phenyl chlorocarbonate. The amino group can also be modified with halogenated carbamic acids such as dimethylcarbamoyl chloride and diphenylcarbamoyl chloride, and isocyanates such as methyl isocyanate, ethyl isocyanate and phenyl isocyanate. Examples of the base used in this reaction include inorganic bases and organic bases.Examples of the inorganic bases include hydroxides of alkali metal atoms such as sodium hydroxide and potassium hydroxide, sodium hydride and potassium hydride. Alkali metal salts of alcohols such as alkali metal hydrides, sodium ethoxide and potassium t-butoxide,
Examples of carbonates such as sodium carbonate, potassium carbonate, sodium hydrogen carbonate and the like, and organic bases include, for example, triethylamine, pyridine, DBU and the like. The inert solvent used in this reaction may be any one that does not significantly hinder the progress of this reaction, for example, aromatic hydrocarbons such as benzene, toluene, xylene, methylene chloride,
Halogenated hydrocarbons such as chloroform and carbon tetrachloride,
Halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene, tetrahydrofuran, dioxane, 1,
Examples thereof include inert solvents such as ethers such as 2-dimethoxyethane and esters such as ethyl acetate. These inert solvents can be used alone or in combination of two or more kinds.

Since this reaction is an equimolar reaction, it is sufficient to use each of the reactants in an equimolar amount. However, any one of the reactants can be used in excess, and the reaction temperature ranges from room temperature to the inert solvent used. It can be carried out in the boiling range, and the reaction time is not constant depending on the reaction scale and reaction temperature, but it may be carried out within the range of several minutes to 48 hours. After completion of the reaction, it may be isolated from the reaction system containing the desired product by a conventional method, and the desired product can be produced by refining it by recrystallization, column chromatography or the like, if necessary. Among the benzamide derivatives represented by the general formula (I) of the present invention, Q is -SO- (J) q-.
The compound represented by L or -SO _2- (J) q-L is a compound represented by Q by -S- (J) q-L by a conventional method, for example, m-chloroperbenzoic acid, hydrogen peroxide. It can be produced by oxidizing with an oxidizing agent such as. General formula (II
The benzoic acid derivative represented by I) can be produced according to a conventional method or a known method, for example, the method illustrated in the following.

Manufacturing method 4.

[Chemical 6] (In the formula, X, J, L, q and m are the same as above. A compound in which Q is -O- (J) q-L among the aromatic carboxylic acid derivatives represented by the general formula (III). (III-3) is esterified by a conventional method, for example, by heating the salicylic acid derivative (III-2) in an alcohol solvent such as ethanol in the presence of an acid catalyst such as sulfuric acid or borane trifluoride diethyl etherate to give the ester. The compound (VII-1) is treated with an alkyl halide in the presence of a base to give an ether compound (VII-2) by a Mitsunobu reaction, and the ether compound (VII-2) is converted into an ether compound (VII-2) by a conventional method such as hydroxylation. It can be produced by hydrolysis with sodium or the like.

Manufacturing method 5.

[Chemical 7] (In the formula, X, J, L, q, and m are the same as above.) Among the aromatic carboxylic acid derivatives represented by the general formula (III), Q is represented by -S- (J) q-L. Compound (III-5)
Is a known method (J. Chem. Soc. Perkin Trans. 1, p38) for the anthranilic acid derivative represented by the general formula (III-4).
5 (1984)) and led to the disulfide form (VIII),
It can be produced by reduction to thiol by a conventional method, further alkylation by various alkylation methods, and then hydrolysis.

Manufacturing method 5.

[Chemical 8] (In the formula, X, J, L, Hal, q and m are the same as above.) In the aromatic carboxylic acid derivative represented by the general formula (III), Q is -S- (J) q-L. Compound represented (III-
As an alternative to 5), for example, a salicylic acid derivative represented by the general formula (VII) is prepared by a known method (J.Org.Chem., 31 , 3980).
(1966)) and thionocarbamate compound (VII-3)
To the thiol carbamate compound (VII-4), followed by hydrolysis, modification by various alkylation methods such as alkylation, and then hydrolysis.

Typical compounds of the benzanilide derivative represented by the general formula (I) of the present invention are shown in Tables 1 to 8 below.
Although illustrated in the table, the present invention is not limited thereto. In the table, physical properties indicate melting point ° C or refractive index (° C), Paste indicates paste, "Me" indicates methyl group,
"Et" is an ethyl group, "Bu" is a butyl group, and "P"
“R” is a propyl group, “Pen” is a pentylmethyl group, “Hex” is a hexyl group, “Ph” is a phenyl group, “Pyr” is a pyridyl group, “Thi” is a thienyl group, and “Thf”. "Indicates a tetrahydrofuryl group.

General formula (I-2)

[Table 1]

[0034]

[Table 2]

[0035]

[Table 3]

[0036]

[Table 4]

[0037]

[Table 5]

[0038]

[Table 6]

[0039]

[Table 7]

[0040]

[Table 8]

General formula (I-3)

[Table 9]

General formula (I-4)

[Table 10]

General formula (I-5))

[Chemical 9]

[0044]

[Table 11]

General formula (I-6))

[Table 12]

[0046]

[Table 13]

General formula (I-7))

[Table 14]

[0048]

[Table 15]

General formula (I-8)

[Table 16]

General formula (I-9)

[Table 17]

[0051]

EXAMPLES Representative examples of the present invention will be illustrated below, but the present invention is not limited thereto. Example 1. 3-chloro-2-isopropoxy-2'-
Production of Methyl-4′-trifluoromethoxybenzanilide (Compound No. 1-98) 2-Methyl-4-trifluoromethoxyaniline 0.4
g was dissolved in 5 ml of tetrahydrofuran, 0.2 g of triethylamine was further added, and 3-chloro-2- was added under ice-water cooling.
0.5 g of isopropoxybenzoic acid chloride was added dropwise.
After dropping, the mixture was stirred for 3 hours, the reaction mixture was added to water, the desired product was extracted with ethyl acetate, the extract was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue obtained was purified by silica gel column chromatography. This gave 0.3 g of the desired product. Physical properties: melting point 76 ° C

Example 2. Production of 3,5-dichloro-2-methoxy-N-methyl-4′-trifluoromethoxybenzanilide (Compound No. 2-2) 3,5-dichloro-2-methoxy-4′-trifluoromethoxy-benzanilide 0.6 g was dissolved in 15 ml of tetrahydrofuran, 0.13 g of 85 weight percent potassium hydroxide and 1.0 ml of methyl iodide were added, and
Reflux for hours. The reaction solution was returned to room temperature, the insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography to obtain 0.42 g of the desired product. Physical properties: melting point 126 ° C

Example 3. 2-propionylamino-
Production of 2'-methyl-4'-trifluoromethoxybenzanilide (Compound No. 4-9) 2-Methyl-4-trifluoromethoxyaniline 2.4
g was dissolved in 30 ml of tetrahydrofuran, 1.1 g of pyridine was further added, and 2.5 g of 2-nitrobenzoic acid chloride was added dropwise under ice-water cooling. After dropping, the mixture was stirred for 3 hours, the reaction mixture was added to water, the desired product was extracted with ethyl acetate, the extract was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue obtained was purified by silica gel column chromatography. As a result, 4.1 g of 2-nitro-2'-methyl-4'-trifluoromethoxybenzamide was obtained. 2-
To 4.0 g of nitro-2'-methyl-4'-trifluoromethoxybenzanilide was added 40 ml of ethanol, and 5% was added.
Palladium carbon (0.3 g) was added, and then the mixture was stirred under a hydrogen atmosphere at room temperature for 5 hours, then 5% palladium carbon was removed by filtration, the filtrate was concentrated under reduced pressure into a reaction mixture, and the obtained crystals were diluted with ethanol. Washed and washed with 2-amino-2'-methyl-4'-trifluoromethoxybenzanilide 2.
5 g was obtained. 0.3 g of 2-amino-2'-methyl-4'-trifluoromethoxybenzanilide was dissolved in 10 ml of tetrahydrofuran, 0.08 g of pyridine was further added, and 0.1 g of propionyl chloride was added dropwise under cooling with ice water. After the dropwise addition, the mixture was stirred at room temperature for 3 hours, the reaction mixture was added to water, the target product was extracted with ethyl acetate, the extract was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue obtained was subjected to silica gel column chromatography. The desired product (0.3 g) was obtained by purification with. Physical properties: melting point 168 ° C

Example 4. 2-isopropylthio-2 '
-Methyl-4'-trifluoromethoxybenzanilide (Compound No. 5-12) 1.3 g of 4-trifluoromethoxyaniline was dissolved in 5 ml of tetrahydrofuran, and further triethylamine of 0.1.
8 g was added, and 1.6 g of 2-isopropylthiobenzoic acid chloride was added dropwise under ice-water cooling. After dropping, the mixture was stirred for 3 hours, the reaction mixture was added to water, the desired product was extracted with ethyl acetate, the extract was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue obtained was purified by silica gel column chromatography. This gave 1.5 g of the desired product. Physical properties: melting point 118 ° C

Example 5. Production of 3-chloro-2-methylthio-2'-methyl-4 '-[1,2,2,2-tetrafluoro-1- (trifluoromethyl) ethyl] benzanilide (Compound No. 5-3) 3- Chloro-2-methylthiobenzoic acid chloride 0.65
g was added to 20 ml of an anhydrous tetrahydrofuran solution containing 0.7 g of 2-methyl-4-[(1,2,2,2-tetrafluoro-1- (trifluoromethyl) ethyl] aniline and 0.23 g of pyridine at 0 ° C. After stirring for 1 hour, the reaction mixture was added to water, the target product was extracted with ethyl acetate, the extract was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography. Physical properties of the desired product (0.7 g) obtained by purification: melting point 129 ° C

Example 6. Production of 3-chloro-2-methylsulfinyl-2′-methyl-4 ′-[(1,2,2,2-tetrafluoro-1- (trifluoromethyl) ethyl] benzanilide (Compound No. 5-4) 3-chloro-2-methylthio-2'-methyl-4'-
0.3 g of [1,2,2,2-tetrafluoro-1- (trifluoromethyl) ethyl] benzanilide was dissolved in 5 ml of chloroform, and 0.16 g of metachloroperbenzoic acid was added under cooling with ice water. After that, the mixture was stirred for 3 hours at room temperature. Then, the reaction mixture was added to ice water, and sodium bicarbonate water was further added to make the mixture alkaline, followed by extraction with chloroform.The extract was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain a residue by silica gel column chromatography. Purification yielded 0.17 g of the desired product. Physical properties: melting point 230 ° C

Example 7. Preparation of 2-n-hexyl-2'-methyl-4'-trifluoromethoxybenzanilide (Compound No. 6-10) 2-Methyl-4-trifluoromethoxyaniline 0.4
g was dissolved in 5 ml of tetrahydrofuran, 0.13 g of triethylamine was further added, and 0.3 g of 2-n-hexylbenzoic acid chloride was added dropwise under ice-water cooling. After dropping, the mixture was stirred for 3 hours, the reaction mixture was added to water, the desired product was extracted with ethyl acetate, the extract was washed with water and dried over anhydrous magnesium sulfate,
The residue obtained by concentration under reduced pressure was purified by silica gel column chromatography to obtain 0.2 g of the desired product. Physical properties: melting point 96 ° C

Agricultural and horticultural agents containing the benzamide derivative represented by the general formula (I) of the present invention as an active ingredient, particularly agricultural and horticultural insecticides or acaricides are paddy rice, fruit trees, vegetables,
It is suitable for various agricultural and forestry that harms other crops and flowers, horticulture, pest control such as storage pests, sanitary pests, nematodes, etc., for example, an apple cockroach (Adoxophyes oranaf)
asciata), Spodoptera litura (Adoxophyes sp.)
, Apple cocoin gui (Grapholita inopinata), nashihime quince (Grapholita molesta), bean turtle (Leg)
uminivora glycinivorella), Kuwahamaki (Olethreutes)
mori), Chanohosuga (Caloptilia thevivora), Apples Hosuga (Caloptilia zachrysa), Kingmon Hosogah (Phyll)
onorycter ringoniella), Nashihosoga (Spulerrina asta)
urota), Pieris rapae crucivora (Piers rapae crucivora), Heliothis sp., Codling moth (Laspey re)
sia pomonella), diamondback moth (Plutella xylostella), apple shrew (Argyresthia conjugella), peach moth squid (Carposina niponensis), lizard (Chilo suppr)
essalis), Kobunomeiga (Cnaphalocrocis medinalis),
Chamadala (Ephestia elutella), Kwanomaiga
(Glyphodes pyloalis), Sankamaiga (Scirpophaga inc
ertulas), Parrot guttata, Pseudaletia separata, Spodoptera litura (Sesamia i)
nferens), Spodoptera litura (Spodoptera litura),

White flesh worm (Spodoptera egigua)
Such as Lepidoptera pest, Leafhopper leafhopper (Macrosteles fasci
frons), leafhopper leafhopper (Nephotettix cincticeps),
Brown planthopper (Nilaparvata lugens), White-tailed planthopper (S
ogatella furcifera), orange lice (Diaphorina ci)
tri), whitefly white grapes (Aleurolobus taonabae), whitefly white tobacco (Bemisia tabaci), whitefly whitefly (T
rialeurodes vaporariorum), porpoise aphid
(Lipaphis erysimi), green peach aphid (Myzuspersic)
ae), black weevil (Ceroplastes ceriferus), citrus scale insect (Pulvinaria aurantii), mandarin pit scale insect (Pseudaonidia duplex), pit scale insect (Comstockaspis perniciosa), stag beetle (Unaspis yanonensis) Pratylenchus sp.), Japanese beetle (Anomala rufoc)
uprea), Japanese beetle (Popilla japonica), tobacco beetle (Lasioderma serricorne), flat beetle (Lyc)
tus brunneus),

Epilachna vigin
tiotopunctata), adzuki bean weevil (Callosobruchus chin)
ensis), green weevil (Listroderes costirostris),
Weevil (Sitophilus zeamais), Boll Weevil (A
nthonomus gradis gradis), rice weevil (Lissorh)
optrus oryzophilus), the root beetle (Aulacophora femor)
alis), rice mud beetle (Oulema oryzae), beetle beetle (Phyllotreta striolata), pine beetle
(Tomicus piniperda), Colorado potato beetle (Lepti
notarsa decemlineata), Mexican bean beetle (E
pilachna varivestis), Corn rootworms (Diabrot
ica sp.) and other insect beetle insects such as Dacus (Zeugodacu
s) cucurbitae), mandarin fruit fly (Dacus (Bactrocera) do
rsalis), rice leaf fly (Agromyza oryzae), onion fly (Delia antiqua), seed fly (Dalia platura)
, Soybean Fly (Asphondylis sp.), Housefly
(Musca domestica), Culex pipiens pipien
s) and other dipterous insects
enchus coffeae), potato cyst nematode (Glabod
era rostchiensis), root-knot nematode (Meloidogyne s)
p.), citrus nematode (Tylenchulus semipenetran)
s), False-legged nematode (Aphelenchus avenae),
It has a strong insecticidal effect against the harmful insects such as Aphelenchoides ritzemabosi and the like.

The agricultural and horticultural agents containing the benzamide derivative represented by the general formula (I) of the present invention as an active ingredient, especially the agricultural and horticultural insecticides and acaricides are paddy field crops, field crops, fruit trees, vegetables, etc. Since it has a remarkable control effect against the pests that damage crops and flowers, etc., paddy fields, fields, before the occurrence of the pests or at the time when the occurrence of the pests is confirmed, in accordance with the time when the occurrence of the pests is predicted. By treating fruit trees, vegetables, other crops, seeds such as flowers, paddy water, foliage or soil, the desired effects of the agricultural and horticultural chemicals of the present invention can be achieved. The agricultural and horticultural chemicals of the present invention are generally used by formulating into a convenient shape according to a conventional method for pesticide formulation. That is, the benzamide derivative represented by the general formula (I) is dissolved, separated, suspended, mixed or impregnated by mixing these in an appropriate inert carrier or, if necessary, an auxiliary agent in an appropriate ratio. , Adsorbed or adhered to the appropriate dosage form,
For example, it may be used by formulating it into a suspension, emulsion, liquid, wettable powder, wettable granule, granule, powder, tablet, pack and the like.

The inert carrier which can be used in the present invention may be either solid or liquid, and examples of the material which can be a solid carrier include soybean flour, cereal flour, wood flour, bark flour, sawdust powder, Tobacco stem powder, walnut shell powder, bran, fibrous powder, residue after extraction of plant extracts, synthetic polymers such as ground synthetic resins, clays (eg kaolin, bentonite, acid clay), talcs (eg talc, pyrophyllite) Etc.), silica {for example, diatomaceous earth, silica sand, mica, white carbon (Synthetic highly dispersed silicic acid also called hydrous fine powder silicon, hydrous silicic acid, and some products contain calcium silicate as a main component)}, activated carbon, sulfur powder , Pumice, calcined diatomaceous earth, crushed bricks, fly ash, sand, calcium carbonate, inorganic mineral powder such as calcium phosphate, polyethylene, polypropylene Plastic carriers such as polyvinylidene chloride, ammonium sulfate, ammonium phosphate, ammonium nitrate, can be mentioned urea, fertilizer salts depreciation etc., compost and the like, which are used alone or in the form of a mixture of two or more.

The material which can be used as a liquid carrier is selected from those having solvent ability per se and those having no solvent ability but capable of dispersing the active ingredient compound with the aid of an auxiliary agent. Typical examples of the carrier include the following, which are used alone or in the form of a mixture of two or more kinds, for example, water, alcohols (for example, methanol, ethanol, isopropanol, butanol, ethylene glycol, etc.), ketones. (For example, acetone, methyl ethyl ketone, methyl isobutyl ketone,
Diisobutyl ketone, cyclohexanone, etc.), ethers (eg ethyl ether, dioxane, cellosolve,
Dipropyl ether, tetrahydrofuran etc.), aliphatic hydrocarbons (eg kerosene, mineral oil etc.), aromatic hydrocarbons (eg benzene, toluene, xylene, solvent naphtha, alkylnaphthalene etc.), halogenated hydrocarbons (eg dichloroethane) , Chloroform, carbon tetrachloride, chlorinated benzene, etc.), esters (eg ethyl acetate, diisopropyl phthalate, dibutyl phthalate, dioctyl phthalate etc.), amides (eg dimethylformamide, diethylformamide, dimethylacetamide etc.) , Nitriles (for example, acetonitrile), dimethyl sulfoxides, and the like.

As the other auxiliary agents, there may be mentioned the representative auxiliary agents exemplified below. These auxiliary agents are used depending on the purpose, and may be used alone or in some cases in combination of two or more kinds of auxiliary agents. However, in some cases it is also possible to use no adjuvant at all. Surfactants are used for the purpose of emulsifying, dispersing, solubilizing and / or wetting the active ingredient compound, for example polyoxyethylene alkyl ether, polyoxyethylene alkylaryl ether, polyoxyethylene higher fatty acid ester, polyoxyethylene. Resin acid ester, polyoxyethylene sorbitan monolaurate, polyoxyethylene sorbitan monooleate, alkylaryl sulfonate, naphthalene sulfonic acid condensate,
Examples thereof include surfactants such as lignin sulfonate and higher alcohol sulfate. In addition, for the purpose of stabilizing the dispersion of active ingredient compounds, adhering and / or binding, auxiliary agents exemplified below can be used, for example, casein, gelatin, starch, methyl cellulose, carboxymethyl cellulose, gum arabic, polyvinyl. Auxiliary agents such as alcohol, pine oil, bran oil, bentonite, lignin sulfonate and the like can also be used.

The following auxiliary agents may be used for improving the fluidity of the solid product, for example, waxes, stearates, alkyl phosphates and the like. As a deflocculant for a suspending product, an auxiliary agent such as a naphthalenesulfonic acid condensate or a condensed phosphate can be used. As the defoaming agent, for example, an auxiliary agent such as silicone oil can be used. As preservatives, 1, 2
-Benzisothiazolin-3-one, parachlorometaxylenol, butyl paraoxybenzoate and the like can also be added. Further, if necessary, a functional spreader, an activity enhancer such as a metabolic degradation inhibitor such as piperonyl butoxide, an antifreezing agent such as propylene glycol, an antioxidant such as BHT, an ultraviolet absorber and the like are added. Agents can also be added. The compounding ratio of the active ingredient compound can be adjusted according to need, and is 0.
It may be appropriately selected from the range of 01 to 90 parts by weight and used, for example, 0.01 to 50% by weight in the case of powder or granules, and 0.01 to 5% in the case of emulsion or wettable powder.
0 wt% is suitable. The agricultural and horticultural agent of the present invention is used as it is for controlling various pests, or is appropriately diluted with water or the like,
Alternatively, it may be used by applying in a suspended form an effective amount for disease control to a crop in which the outbreak of the pest is predicted or a place where the outbreak is not preferable.

The amount of the agricultural or horticultural agent of the present invention to be used depends on various factors such as purpose, target pests, growing condition of crops, pest development tendency, weather, environmental conditions, dosage form, application method, application place,
1 as an active ingredient compound, although it varies depending on the application period, etc.
It may be appropriately selected from the range of 0.001 g to 10 kg, preferably 0.01 g to 1 kg per 0 are depending on the purpose. Agricultural and horticultural agents of the present invention, further pest control pests, for the expansion of the control period, or for the purpose of reducing the amount of other agricultural and horticultural insecticides, acaricides, nematicides, fungicides, It is also possible to use it by mixing it with biological pesticides,
It is also possible to mix and use a herbicide, a plant growth regulator, a fertilizer or the like depending on the use scene. Other agricultural and horticultural insecticides used for such purposes, acaricides, nematicides, for example, ethione, trichlorfon, methamidophos,
Acephate, dichlorvos, mevinphos, monocrotophos, malathion, dimethoate, formothione, mecarbam, bamidthione, thiomethone, disulfoton, oxydeprophos, nared, methylparathione, fenitrothion, cyanophos, propaphos,

Phenthion, prothiophos, profenophos, isofenphos, temephos, fentoate, dimethylvinphos, chlorfevinphos, tetrachlorbinphos, hoxime, isoxathion, pyraclophos, metidathione, chloropyrifos, chlorpyrifos-methyl, pyridafenthion, diazinon, pyrimiphos-methyl, fosalon. , Phosmet, dioxabenzophos, quinalphos, terbufos, etoprophos, kazusaphos, mesulfenphos, DPS (NK-0795), phosphocarb, fenamiphos, isamidophos, fostiazate, isazophos, enaprophos, fenthion, fostiethane, diclofenthion, thionazine, sulprofos, fensulfone. , Diamidaphos, pyrethrin, allethrin, prala Phosphorus, resmethrin, permethrin, tefluthrin, bifenthrin, fenpropathrin, cypermethrin, alpha-cypermethrin, cyhalothrin, lambda-cyhalothrin, deltamethrin,
Acrinathrin,

Fenvalerate, esfenvalerate, flucitrinate, fluvalinate, cycloprotoline, etofenprox, halfenprox,
Silafluofen, flucitrinate, fluvalinate, mesomil, oxamyl, thiodicarb, aldicarb, alanicalub, cartap, metolcarb, xilicarb, propoxur, phenoxycarb, fenobucarb, etiophencarb, phenothiocarb, bifenazeto, BPMC, carbaryl, carmifurfan, carbofuran, carbofuran. Fratiocarb, benfuracarb, aldoxicarb, diafenthiuron, diflubenzuron, teflubenzuron, hexaflumuron, novalron, rufenuron, flufenoxuron,
Chlorfluazuron, fenbutatin oxide, tricyclohexyltin hydroxide, sodium oleate, potassium oleate, methoprene, hydroprene, vinapacryl, amitraz, dicofol, quelsen, chlorbenzilate, phenisobromolate, tetradiphone, bensultap, benzomate, Tebufenozide,

Methoxyphenozide, chromafenozide,
Propargite, acequinocyl, endosulfan, diofenolan, chlorfenapyr, fenpyroximate, tolfenpyrad, fipronil, tebufenpyrad, triazamate, etoxazole, hexithiazox, nicotine sulphate, nitenpyram, acetamipridone, thiaclotianizine, furatinamid, furatinamid, furatinamid, furatinamid, furatinamid, furatinamid, furatinamid, furatinamid, furatinamid, furatinamid, furatinamid, furatinamid, furatinamid, furatinamid, furatinamid, furatinamid, furatinamid, furatinamid, furatinamid, furatinamid, furatinamid, furatinamid, furatinamid , Pyrimidifen, pyridaben, cyromazine, TPIC (tripropyl isocyanurate), pymetrozine, clofentezine, buprofezin, thiocyclam, phenazaquin, quinomethionate, indoxacarb, polynactin complex, milbemectin, abamectin, emamectin benzoate, spinosad, T (Bacillus thuringiensis), Azadi Rakuchin, rotenone, hydroxypropyl starch, levamisole hydrochloride, metam-sodium,
Morantel tartrate, dazomet, trichlamide, bastria, agricultural and horticultural insecticides such as monacrosporium fimatopagum, miticides and nematicides can be exemplified, and as the agricultural and horticultural fungicides used for the same purpose,

For example, sulfur, lime-sulfur mixture, basic copper sulfate, iprobenphos, edifenphos, tolclofos-methyl, thiram, polycarbamate, zineb, manzeb, mancozeb, propineb, thiophanate, thiophanatemethyl, benomyl, iminoctadine acetate, iminoctadine Albesylate, mepronil, flutolanil, penciclone, flametopyr, tifluzamide, metalaxyl, oxadixyl, carpropamide, diclofluanid, fursulfamide, chlorothalonil, kresoxim methyl, phenoxanil, hymexazole, eclomezolone, fluorimide, procymidon, vinclozolin, iprodione, iprodione. Lumisole, bitertanol, triflumizole, ipconazole, fluconazo Le, propiconazole, difenoconazole, myclobutanil, Tetraconazole tetrazole, hexaconazole, tebuconazole,

Imibenconazole, prochloraz, pefurazoate, cyproconazole, isoprothiolane, phenalimol, pyrimethanil, mepanipyrim, pyrifenox, fluazinam, triforin, diclomedine, azoxystrobin, thiadiazine, captan, probenazole, acibenzofural-S-methyl ( CGA-2
45704), fusalide, tricyclazole, pyroquilon, quinomethionate, oxolinic acid, dithianon, kasugamycin, validamycin, polyoxine,
Blasticidin, it is possible to exemplify agricultural and horticultural fungicides such as streptomycin. Similarly, as herbicides, for example, glyphosate, sulfosate, glufosinate, bialaphos, butamifos, esprocarb, prosulfocarb, bench iocarb, pyributicarb, ashram,
Linuron, Daimlon, Bensulfuron-methyl, Cyclosulfamuron, Cinosulfuron, Pyrazosulfuron-ethyl, Azimsulfuron, Imazosulfuron, Tenilchlor, Araclor, Pretilachlor, Chromeprop, Etobenzanide, Mefenacet,

Pendimethalin, bifenox, acifluofen, lactofen, cyhalofop-butyl,
Aioxynil, bromobutide, alloxydim, cetoximium, napropamide, indanophan, pyrazolate, benzophenap, pyraflufen-ethyl, imazapyr, sulfentrazone, cafenstrol, bentoxazone, oxazoazone, paraquat, diquat, pyriminobac, simazine, atrazine, dimetamethrin. , Triazifram, benfresate, furthiaset methyl, quizalofop ethyl, bentazone, calcium peroxide and the like herbicides.

Examples of biological pesticides include Nuclear polyhedrosis virus (NPV), Granulosis virus (GV), Cytoplasmic polyhedrosis virus (CPV), Insect pox virus (Entomopox) virus, EPV) and other virus preparations, Monosporium fimatopagum (Mona
crosporium phymatophagum), Steinernema carpocapsae, Steinernema kushidai, Pasteuria penetrans, and other microbial pesticides and trichoderma used as nematicides.
Lignolan (Trichoderma lignorum), Agrobacterium radiobactor
), Non-pathogenic Erwinia carotobora (Erwinia car
otovora), Bacillus subtilis
The same effect can be expected by mixing with a microbial pesticide used as a bactericide such as) and a biopesticide used as a herbicide such as Xanthomonas campestris.

Further, as biological pesticides, for example, honeybee wasp (Encarsia formosa), coleman bee (Ap)
hidius colemani), gypsy fly (Aphidoletes)
aphidimyza), Yellow-bellied wasp (Diglyphus isaea)
), Mosquito beetle (Dacnusa sibirica), dust mite (Phytoseiulus persimilis), Amblyseius cucumeris, and other natural creatures such as Orius sauteri, Boberia
Microbial pesticides such as Beauveria brongniartii, (Z) -10-tetradecenyl acetate,
(E, Z) -4,10-tetradecadienyl acetate, (Z) -8-dodecenyl acetate, (Z) -1
1-tetradecenyl = acetate, (Z) -13-icosen-10-one, (Z) -8-dodecenyl = acetate, (Z) -11-tetradecenyl = acetate,
(Z) -13-icosen-10-one, 14-methyl-
It is also possible to use it together with a pheromone agent such as 1-octadecene.

Typical formulation examples and test examples of the present invention are shown below, but the present invention is not limited thereto.
In the formulation examples, “part” means “part by weight”. Formulation Example 1. Compounds described in Tables 1 to 8 10 parts Xylene 70 parts N-methylpyrrolidone 10 parts Mixture of polyoxyethylene nonylphenyl ether and calcium alkylbenzene sulfonate 10 parts The above components are uniformly mixed and dissolved to obtain an emulsion. Formulation example 2. Compounds described in Tables 1 to 8 3 parts Clay powder 82 parts Diatomaceous earth powder 15 parts The above are uniformly mixed and pulverized to obtain a powder.

[0076] Formulation example 3.   5 parts of compounds shown in Tables 1 to 8   90 parts of mixed powder of bentonite and clay   Calcium lignin sulfonate 5 parts   The above is uniformly mixed, an appropriate amount of water is added and kneaded, granulated and dried to obtain a granule. Formulation example 4.   20 parts of the compounds shown in Tables 1 to 8   Kaolin and synthetic highly dispersed silicic acid 75 parts   With polyoxyethylene nonyl phenyl ether   Mixture with calcium alkylbenzene sulfonate 5 parts   The above is uniformly mixed and pulverized to obtain a wettable powder.

Test Example 1. Diamondback moth (Plutella xylostell)
Insecticide test against a). The Chinese cabbage seedlings were released with adults of the diamondback moth and allowed to lay eggs.
500ppm of drugs containing the compounds listed in the table as active ingredients
It was dipped in the chemical solution diluted to about 30 seconds, air-dried and then allowed to stand in a thermostatic chamber at 25 ° C. Six days after the immersion in the chemical solution, the number of hatched worms was examined, the mortality rate was calculated by the following formula, and the judgment was made according to the following criteria. 1 ward 10 heads 3 stations

[0078] As a result of the above test, the compound showing the insecticidal activity of A is 1-
1,1-5, 1-17 to 1-19, 1-23 to 1-2
5, 1-28, 1-33, 1-37, 1-40 to 1-4
3, 1-45, 1-49 to 1-51, 1-53 to 1-5
6, 1-58, 1-59, 1-63 to 1-65, 1-6
7,1-70,1-73,1-74,1-76,1-7
7, 1-82, 1-85 to 1-89, 1-97 to 1-1
00, 1-103 to 1-112, 1-115, 1-11
8, 1-119, 1-120 to 1-124, 1-12
6, 1-128 to 1-130, 1-134, 1-13
9, 1-145, 1-147 to 1-149, 1-151
~ 1-155, 1-158, 1-166 to 1-168,
1-171 to 182, 2-1, 2-2, 2-6, 2-1
0, 2-13, 2-16, 3-1, 3-2, 4-16,
4-17, 4-20, 4-22, 5-3 to 5-10, 5
-17 to 5-19, 6-1, 6-2, 6-4, 6-5,
6-8, 6-10 to 6-12, 6-17, 7-2, 8-
It was 1.

Test Example 2. Namihadani (Tetranychus urti)
Acaricide) Acaricidal test A leaf disk having a diameter of 2 cm was prepared from green leaf, placed on a wet filter paper, and inoculated with a female adult, and then diluted to 500 ppm on a turntable.
50 ml of a drug solution containing the compound shown in the table as an active ingredient was uniformly sprayed, and after spraying, it was allowed to stand in a thermostatic chamber at 25 ° C. The number of living and dead insects was investigated 2 days after the drug treatment, and the number was determined according to the following criteria. 10 wards in 2 wards As a result of the above test, the compound showing the insecticidal activity of A was 1-1.
8, 1-19, 1-40 to 1-43, 1-45, 1-4
9, 1-50, 1-52, 1-64, 1-67, 1-6
8, 1-73, 1-81, 1-83, 1-84, 1-1
18-1 to 121, 1-123, 1-124, 1-12
8, 1-132, 1-134, 2-1, 2-2, 2-
It was 8,2-11, -12,3-2.

─────────────────────────────────────────────────── ─── Continuation of front page (51) Int.Cl. ⁷ Identification code FI theme code (reference) C07C 233/75 C07C 233/75 235/64 235/64 237/42 237/42 317/40 317/40 317 / 44 317/44 323/12 323/12 323/18 323/18 323/42 323/42 323/60 323/60 323/62 323/62 327/48 327/48 C07D 213/75 C07D 213/75 ( 72) Inventor Makoto Goto 1-13-6 Migamioka, Aoba-ku, Yokohama-shi, Kanagawa Prefecture 2-1-1406 (72) Masanori Tonishi 1040-1-408 Fukuda, Sakai City, Osaka Prefecture (72) Inventor: Akira Seo Wakayama Prefecture 2-3-19 Kihigaoka, Hashimoto-shi (72) Inventor Masayuki Morimoto 1-28-305 Nishinoyama-cho, Kawachinagano-shi, Osaka (72) Inventor Shinsuke Fujioka 474-1-103 F-term, Kawara-Nagano, Osaka (Reference) 4C055 AA01 BA02 BA42 BA47 BA53 BB02 BB04 BB07 BB08 CA02 CA03 CA06 CA13 CA39 CA53 CB04 CB07 CB08 DA01 4H006 A A01 AA03 AB02 BJ50 BM10 BM30 BM71 BM72 BM73 BP30 BU46 BV74 TA04 TB61 4H011 AC01 AC04 BA01 BB06 BC01 BC03 BC07 BC18 DA02 DA15 DA16 DC05 DC06 DD03

Claims (7)

[Claims] 1. The general formula (I) [Chemical 1] {In the formula, R is a hydrogen atom, C₁-C₆Alkyl group, same or different
Can be a halogen atom, C₁-C₆Alkoxy group, C₁-
C₆Alkylthio group, Mono C₁-C₆Alkylamino group or
One or different di C₁-C₆Is it an alkylamino group?
Substituted C having one or more substituents selected from₁-C₆Archi
Ru radical or C₁-C₆Indicates an alkoxycarbonyl group. Q is C₃-
C₆Cycloalkyl group, C₃-C₆Halocycloalkyl group,
May be one or different, halogen atom, C₁-C₆Alkyl
Base, C₁-C₆Haloalkyl group, C₁-C₆Alkoxy group, C₁-C₆
Haloalkoxy group, C₁-C₆Alkylthio group, C₁-C₆Haloa
Rukiruthio group, C₁-C₆Alkylsulfinyl group, C₁-C₆Ha
Roalkylsulfinyl group, C₁-C ₆Alkylsulfonyl
Base, C₁-C₆Haloalkylsulfonyl group, Mono C₁-C₆Archi
Luamino group, di-C which may be the same or different₁-C₆Alkyl
Amino group, Mono C₁-C₆Haloalkylamino group or same
May be different C₁-C₆Is it a haloalkylamino group?
A substituted phenyl group having one or more substituents selected from
Is the formula (II)       -G- (J) q-L (II) (In the formula, G is -O-, -S-, -SO-, -SO₂-,
-CR¹R²-(In the formula, R¹And R²Are the same or different
Well, hydrogen atom, halogen atom or C₁-C₆Alkyl group
Show. ),-CR¹= CR²-(In the formula, R¹And R²Is the above
Same as ), -C≡C- or -N ((C = O) R³) −
(In the formula, R³Is C₁-C₆Alkyl group, C₁-C₆Haloalkyl
Base, C₁-C₆Alkoxy group, C₁-C₆Haloalkoxy group, mono
C₁-C₆Alkylamino group, di-C which may be the same or different₁-
C₆Alkylamino group, Mono C₁-C₆Haloalkylamino
Groups, which may be the same or different, di C₁-C₆Haloalkylami
No group, C₁-C₆Alkoxy C₁-C₆Alkyl group, C₁-C₆Haloa
Lucoxy C₁-C₆Alkyl group, C₁-C₆Alkylthio C₁-C₆A
Rukiru group, C₁-C₆Haloalkylthio C₁-C₆Alkyl group, C₁
-C₆Alkylsulfinyl C₁-C₆Alkyl group, C₁-C₆Halo
Alkylsulfinyl C₁-C₆Alkyl group, C₁-C₆Alkyl
Sulfonyl C₁-C₆Alkyl group, C₁-C₆Haloalkyl sulfo
Nil C₁-C₆Alkyl group, phenyl group, the same or different
Good, halogen atom, C₁-C₆Alkyl group, C₁-C₆Haloa
Rukiru group, C₁-C₆Alkoxy group, C₁-C₆Haloalkoxy
Base, C₁-C₆Alkylthio group, C₁-C₆A haloalkylthio group,
C₁-C₆Alkylsulfinyl group, C₁-C₆Haloalkyl sul
Finyl group, C₁-C₆Alkylsulfonyl group, C₁-C₆Haloa
Rukylsulphonyl group, Mono C₁-C₆Alkylamino group,
One or different di C₁-C₆Alkylamino group, Mono C
₁-C₆Haloalkylamino group or the same or different
Good di C₁-C₆1 or more selected from haloalkylamino groups
A substituted phenyl group having the above substituent, a heterocyclic group, the same or
May be different, halogen atom, C₁-C₆Alkyl group, C
₁-C₆Haloalkyl group, C₁-C₆Alkoxy group, C₁-C₆Haloa
Lucoxy group, C₁-C₆Alkylthio group, C₁-C₆Haloalkyl
Thio group, C₁-C₆Alkylsulfinyl group, C₁-C₆Halo al
Kirsulfinyl group, C₁-C₆Alkylsulfonyl group, C₁-
C₆Haloalkylsulfonyl group, Mono C₁-C₆Alkylami
Group, di-C which may be the same or different₁-C₆Alkylamino
Group, Mono C₁-C₆A haloalkylamino group or the same or
It may be different C₁-C₆Select from haloalkylamino groups
Heterocyclic group having one or more substituents
C₁-C₆Alkyl groups, which may be the same or different, may be halogen
Atom, C₁-C₆Alkyl group, C₁-C₆Haloalkyl group, C₁-C
₆Alkoxy group, C₁-C₆Haloalkoxy group, C₁-C₆Archi
Ruthio group, C₁-C₆Haloalkylthio group, C₁-C₆Alkyls
Rufinyl group, C₁-C₆Haloalkylsulfinyl group, C₁-
C₆Alkylsulfonyl group, C₁-C₆Haloalkylsulfoni
Ru group, Mono C₁-C₆Alkylamino group, the same or different
Also good C₁-C₆Alkylamino group, Mono C₁-C₆Halo Archi
Luamino group or di-C which may be the same or different₁-C₆Ha
A ring with one or more substituents selected from
Phenoxy C on top₁-C₆Alkyl group, phenyl C₁-C₆
An alkyl group, which may be the same or different, a halogen atom,
C₁-C₆Alkyl group, C₁-C₆Haloalkyl group, C₁-C₆Arco
Xy group, C₁-C₆Haloalkoxy group, C₁-C₆Alkylthio
Base, C₁-C₆Haloalkylthio group, C₁-C₆Alkyl sulfi
Nyl group, C₁-C₆Haloalkylsulfinyl group, C₁-C₆Al
Killsulfonyl group, C₁-C₆A haloalkylsulfonyl group,
Mono C₁-C₆Alkylamino group, which may be the same or different
The C₁-C₆Alkylamino group, Mono C₁-C₆Haloalkylami
Group or di-C which may be the same or different₁-C₆Halo al
Have one or more substituents on the ring selected from a kylamino group
Substituted Phenyl C₁-C₆Indicates an alkyl group. ) Is shown.
J is C₁-C₈Alkylene group, C₁-C₈Haloalkylene group, C₂-C
₈Alkenylene group, C₂-C₈Haloalkenylene group, C₂-C₈A
Rukinylene group or C₂-C₈Represents a haloalkynylene group, q
Represents an integer of 0 or 1. L is hydrogen atom, halogen atom
Child, cyano group, nitro group, C₃-C₆Cycloalkyl group, C₃-
C₆Halocycloalkyl group, C₁-C₆Alkoxy group, C₁-C₆Ha
Lower alkoxy group, C ₁-C₆Alkylthio group, C₁-C₆Halo al
Kirthio group, C₁-C₆Alkylsulfinyl group, C₁-C₆Halo
Alkylsulfinyl group, C₁-C₆Alkylsulfonyl
Base, C₁-C₆Haloalkylsulfonyl group, Mono C₁-C₆Archi
Luamino group, di-C which may be the same or different₁-C₆Alkyl
Amino group, Mono C₁-C₆A haloalkylamino group, the same or
It may be different C₁-C₆Haloalkylamino group, C₁-C₆A
Rukylcarbonyl group, C₁-C₆Haloalkylcarbonyl
Base, C₁-C₆Alkoxycarbonylamino group, C₁-C₆Haloa
Lucoxycarbonylamino group, Mono C₁-C₆Alkylcal
Vamoyl group, di-C which may be the same or different₁-C₆Alkyl
Carbamoyl group, phenylcarbamoyl group, same or different
Can be a halogen atom, C₁-C₆Alkyl group, C₁-C₆
Haloalkyl group, C₁-C ₆Alkoxy group, C₁-C₆Halo arco
Xy group, C₁-C₆Alkylthio group, C₁-C₆Haloalkylthio
Base, C₁-C₆Alkylsulfinyl group, C₁-C₆Haloalkyl
Sulfinyl group, C₁-C₆Alkylsulfonyl group, C₁-C₆Ha
Roalkylsulfonyl group, Mono C₁-C₆Alkylamino
Groups, which may be the same or different, di C₁-C₆Alkylamino
Group, Mono C₁-C₆A haloalkylamino group or the same or
It may be different C₁-C₆Select from haloalkylamino groups
Substituted Phenyl Carbohydrate Having One or More Substituents on the Ring
Vamoyl group, Mono C₁-C₆Alkylsulfamoyl group,
One or different di C₁-C₆Alkylsulfamoyl
Group, phenylsulfamoyl group, the same or different
H, halogen atom, C₁-C₆Alkyl group, C₁-C₆Halo Archi
Lu group, C₁-C₆Alkoxy group, C ₁-C₆Haloalkoxy group, C₁
-C₆Alkylthio group, C₁-C₆Haloalkylthio group, C₁-C ₆
Alkylsulfinyl group, C₁-C₆Haloalkyl sulfi
Nyl group, C₁-C₆Alkylsulfonyl group, C₁-C₆Halo Archi
Lesulfonyl group, Mono C₁-C₆Alkylamino group, same or
Can be different C₁-C₆Alkylamino group, Mono C₁-C₆
Haloalkylamino group or may be the same or different
The C₁-C₆One or more selected from haloalkylamino groups
A substituted phenylsulfamoyl group having a substituent on the ring,
May be the same or different₁-C₆Alkoxyphosphoryl
Groups, which may be the same or different, di C₁-C₆Alkoxy thiopho
Suphoryl group, diphenylphosphino group, diphenylphos
Hono group, phenyl group, same or different, halogen
Atom, C₁-C₆Alkyl group, C₁-C₆Haloalkyl group, C₁-C
₆Alkoxy group, C₁-C₆Haloalkoxy group, C₁-C₆Archi
Ruthio group, C₁-C₆Haloalkylthio group, C₁-C₆Alkyls
Rufinyl group, C₁-C₆Haloalkylsulfinyl group, C₁-
C₆Alkylsulfonyl group, C₁-C₆Haloalkylsulfoni
Ru group, Mono C₁-C₆Alkylamino group, the same or different
Also good C₁-C₆Alkylamino group, Mono C₁-C₆Halo Archi
Luamino group or di-C which may be the same or different₁-C₆Ha
Having one or more substituents selected from lower alkylamino groups
Substituted phenyl group, heterocyclic group or the same or different
May be a halogen atom, C₁-C₆Alkyl group, C₁-C₆Halo
Alkyl group, C₁-C₆Alkoxy group, C₁-C₆Haloalkoxy
Base, C₁-C₆Alkylthio group, C₁-C₆A haloalkylthio group,
C₁-C₆Alkylsulfinyl group, C₁-C₆Haloalkyl sul
Finyl group, C₁-C₆Alkylsulfonyl group, C₁-C₆Haloa
Rukylsulphonyl group, Mono C₁-C₆Alkylamino group,
One or different di C₁-C₆Alkylamino group, Mono C
₁-C₆Haloalkylamino group or the same or different
Good di C₁-C₆1 or more selected from haloalkylamino groups
A substituted heterocyclic group having the above substituent is shown. ) Is shown. X
May be the same or different, a halogen atom, a cyano group,
Nitro group, C₁-C₆Alkyl group, C₁-C₆Haloalkyl group, C₃
-C₆Cycloalkyl group, C₃-C₆Halocycloalkyl group, C₁
-C₆Alkoxy group, C₁-C₆Haloalkoxy group, C₁-C₆Al
Kirthio group, C₁-C₆Haloalkylthio group, C₁-C₆Alkyl
Sulfinyl group, C₁-C₆Haloalkylsulfinyl group, C
₁-C₆Alkylsulfonyl group, C₁-C₆Haloalkyl sulfo
Nyl group, Mono C₁-C₆Alkylamino group, same or different
May be good C₁-C₆Alkylamino group, Mono C₁-C₆Halo al
Killamino group, di-C which may be the same or different₁-C₆Haloa
Rukylamino group, tri-C which may be the same or different₁-C₆A
Rukylsilyl group, phenyl group, same or different
H, halogen atom, C₁-C₆Alkyl group, C₁-C₆Halo Archi
Lu group, C₁-C₆Alkoxy group, C₁-C₆Haloalkoxy group, C₁
-C₆Alkylthio group, C₁-C₆Haloalkylthio group, C₁-C₆
Alkylsulfinyl group, C₁-C₆Haloalkyl sulfi
Nyl group, C₁-C₆Alkylsulfonyl group, C₁-C₆Halo Archi
Lesulfonyl group, Mono C₁-C₆Alkylamino group, same or
Can be different C₁-C₆Alkylamino group, Mono C₁-C₆
Haloalkylamino group or may be the same or different
The C₁-C₆One or more selected from haloalkylamino groups
A substituted phenyl group having a substituent, a phenoxy group, the same or
May be different, halogen atom, C₁-C₆Alkyl group, C
₁-C₆Haloalkyl group, C₁-C₆Alkoxy group, C₁-C₆Haloa
Lucoxy group, C₁-C₆Alkylthio group, C₁-C₆Haloalkyl
Thio group, C₁-C₆Alkylsulfinyl group, C₁-C₆Halo al
Kirsulfinyl group, C₁-C₆Alkylsulfonyl group, C₁-
C₆Haloalkylsulfonyl group, Mono C₁-C₆Alkylami
Group, di-C which may be the same or different₁-C₆Alkylamino
Group, Mono C₁-C₆A haloalkylamino group or the same or
It may be different C₁-C₆Select from haloalkylamino groups
A substituted phenoxy group having one or more substituents,
Cyclic groups, which may be the same or different, a halogen atom, C₁-C₆
Alkyl group, C₁-C₆Haloalkyl group, C₁-C₆Alkoxy
Base, C₁-C₆Haloalkoxy group, C₁-C₆Alkylthio group, C₁
-C₆Haloalkylthio group, C₁-C₆Alkylsulfinyl
Base, C₁-C₆Haloalkylsulfinyl group, C₁-C₆Alkyl
Sulfonyl group, C₁-C₆Haloalkylsulfonyl group, Mono C
₁-C₆Alkylamino group, di-C which may be the same or different ₁-C
₆Alkylamino group, Mono C₁-C₆Haloalkylamino group
Can be the same or different₁-C₆Haloalkyl
Substituted complex having one or more substituents selected from mino group
Represents a ring group, and m represents an integer of 0 to 4. Also, a phenyl ring
Adjacent Xs above must join together to form a condensed ring
And the condensed rings may be the same or different, halogen
Atom, C₁-C₆Alkyl group, C₁-C₆Haloalkyl group, C₁-C₆
Alkoxy group, C₁-C₆Haloalkoxy group, C₁-C₆Alkyl
Thio group, C₁-C₆Haloalkylthio group, C₁-C₆Alkylsul
Finyl group, C₁-C₆Haloalkylsulfinyl group, C₁-C₆
Alkylsulfonyl group, C₁-C₆Haloalkylsulfonyl
Group, Mono C₁-C₆Alkylamino group, the same or different
Good di C₁-C₆Alkylamino group, Mono C₁-C₆Haloalkyl
Amino group, di-C which may be the same or different₁-C₆Halo Archi
Luamino group, phenyl group, which may be the same or different,
Rogen atom, C₁-C₆Alkyl group, C₁-C₆A haloalkyl group,
C₁-C₆Alkoxy group, C₁-C₆Haloalkoxy group, C₁-C₆A
Rukiruthio group, C₁-C₆Haloalkylthio group, C₁-C₆Archi
Rusulfinyl group, C₁-C₆Haloalkylsulfinyl
Base, C₁-C₆Alkylsulfonyl group, C₁-C₆Haloalkyls
Ruphonyl group, Mono C₁-C₆Alkylamino group, same or different
You can become C₁-C₆Alkylamino group, Mono C₁-C₆Halo
Alkylamino group or di-C which may be the same or different₁
-C₆One or more substitutions selected from haloalkylamino groups
A substituted phenyl group having a group, a heterocyclic group or the same or
May be different, halogen atom, C₁-C₆Alkyl group, C₁-
C₆Haloalkyl group, C₁-C₆Alkoxy group, C₁-C₆Halo al
Coxy group, C₁-C₆Alkylthio group, C₁-C₆Haloalkyl
O group, C₁-C₆Alkylsulfinyl group, C₁-C₆Halo Archi
Rusulfinyl group, C₁-C₆Alkylsulfonyl group, C₁-C₆
Haloalkylsulfonyl group, Mono C₁-C₆Alkylamino
Groups, which may be the same or different, di C₁-C₆Alkylamino
Group, Mono C₁-C₆A haloalkylamino group or the same or
It may be different C₁-C₆Select from haloalkylamino groups
Selected from substituted heterocyclic groups having one or more substituents
It is also possible to have one or more substituents B¹, B²,
B³And B^FourMay be the same or different and may be nitrogen atom or carbon.
Indicates an elementary atom. Y may be the same or different, and halogen
Atom, cyano group, nitro group, C₁-C₆Alkyl group, C₃-C₆Ha
Cycloalkyl group, phenyl group, the same or different
Well, halogen atom, C₁-C₆Alkyl group, C₁-C₆Halo al
Kill group, C₁-C₆Alkoxy group, C₁-C₆A haloalkoxy group,
C₁-C₆Alkylthio group, C₁-C₆Haloalkylthio group, C ₁-C
₆Alkylsulfinyl group, C₁-C₆Haloalkyl sulfi
Nyl group, C₁-C₆Alkylsulfonyl group, C₁-C₆Halo Archi
Lesulfonyl group, Mono C₁-C₆Alkylamino group, same or
Can be different C₁-C₆Alkylamino group, Mono C₁-C₆
Haloalkylamino group or may be the same or different
The C₁-C₆One or more selected from haloalkylamino groups
A substituted phenyl group having a substituent, a heterocyclic group, the same or different
Can be a halogen atom, C₁-C₆Alkyl group, C₁-C₆
Haloalkyl group, C₁-C₆Alkoxy group, C₁-C₆Halo arco
Xy group, C₁-C₆Alkylthio group, C₁-C₆Haloalkylthio
Base, C₁-C₆Alkylsulfinyl group, C₁-C₆Haloalkyl
Sulfinyl group, C₁-C₆Alkylsulfonyl group, C₁-C₆Ha
Roalkylsulfonyl group, Mono C₁-C₆Alkylamino
Groups, which may be the same or different, di C₁-C₆Alkylamino
Group, Mono C₁-C₆A haloalkylamino group or the same or
It may be different C₁-C₆Select from haloalkylamino groups
Substituted heterocyclic group having one or more substituents or -A-
R^Four(In the formula, A is -O-, -S-, -SO-, -SO.
₂-, -C (= O)-, C₁-C₆Alkylene group, C₁-C₆Halo
Alkylene group, C₂-C₆Alkenylene group, C₂-C₆Halo arche
Nylene group, C₂-C₆Alkynylene group or C₃-C₆Halo alkini
A len group is shown. R^FourIs a hydrogen atom, C₃-C₆Halo cycloalk
Lu group, C₃-C₆Halocycloalkenyl group, phenyl group,
May be one or different, halogen atom, C₁-C₆Alkyl
Base, C₁-C₆Haloalkyl group, C₁-C ₆Alkoxy group, C₁-C₆
Haloalkoxy group, C₁-C₆Alkylthio group, C₁-C₆Haloa
Rukiruthio group, C₁-C₆Alkylsulfinyl group, C₁-C₆Ha
Roalkylsulfinyl group, C₁-C₆Alkylsulfonyl
Base, C₁-C₆Haloalkylsulfonyl group, Mono C₁-C₆Archi
Luamino group, di-C which may be the same or different₁-C₆Alkyl
Amino group, Mono C₁-C₆Haloalkylamino group or same
May be different C₁-C₆Is it a haloalkylamino group?
A substituted phenyl group having one or more substituents selected from
Heterocyclic groups or may be the same or different and may be halogen atoms.
Child, C₁-C₆Alkyl group, C₁-C₆Haloalkyl group, C₁-C₆A
Lucoxy group, C₁-C₆Haloalkoxy group, C₁-C₆Alkylchi
O group, C₁-C₆Haloalkylthio group, C₁-C₆Alkylsulf
Inyl group, C₁-C₆Haloalkylsulfinyl group, C₁-C₆A
Rukylsulphonyl group, C₁-C₆Haloalkylsulfonyl
Group, Mono C₁-C₆Alkylamino group, the same or different
Good di C₁-C₆Alkylamino group, Mono C₁-C₆Haloalkyl
Amino group or di-C which may be the same or different₁-C₆Halo
Having one or more substituents selected from alkylamino groups
Represents a substituted heterocyclic group. ), N is an integer from 1 to 5
Show. Also, adjacent Ys on the phenyl ring together
Fused rings can be formed and the fused rings can be the same or different.
Good, halogen atom, C₁-C₆Alkyl group, C₁-C₆Ha
Lower alkyl group, C₁-C₆Alkoxy group, C₁-C₆Halo arcoki
Shi group, C₁-C₆Alkylthio group, C₁-C₆Haloalkylthio
Base, C₁-C₆Alkylsulfinyl group, C₁-C₆Haloalkyl
Sulfinyl group, C₁-C₆Alkylsulfonyl group, C₁-C₆Ha
Roalkylsulfonyl group, Mono C₁-C₆Alkylamino
Groups, which may be the same or different, di C₁-C₆Alkylamino
Group, Mono C₁-C₆Haloalkylamino group, same or different
May be good C₁-C₆Haloalkylamino group, phenyl group,
May be the same or different, halogen atom, C₁-C₆Archi
Lu group, C₁-C₆Haloalkyl group, C₁-C₆Alkoxy group, C₁-C
₆Haloalkoxy group, C₁-C₆Alkylthio group, C₁-C₆Halo
Alkylthio group, C₁-C₆Alkylsulfinyl group, C₁-C₆
Haloalkylsulfinyl group, C₁-C₆Alkyl sulfoni
Lu group, C₁-C₆Haloalkylsulfonyl group, Mono C₁-C₆Al
Killamino group, di-C which may be the same or different₁-C₆Archi
Luamino group, Mono C₁-C₆Haloalkylamino group or the same
Or it may be different C₁-C₆Haloalkylamino group
Substituted phenyl having one or more substituents selected from
Groups, heterocyclic groups or the same or different, halogen
Atom, C₁-C₆Alkyl group, C₁-C₆Haloalkyl group, C₁-C
₆Alkoxy group, C₁-C₆Haloalkoxy group, C₁-C₆Archi
Ruthio group, C₁-C₆Haloalkylthio group, C₁-C₆Alkyls
Rufinyl group, C₁-C₆Haloalkylsulfinyl group, C₁-
C₆Alkylsulfonyl group, C₁-C₆Haloalkylsulfoni
Ru group, Mono C₁-C₆Alkylamino group, the same or different
Also good C₁-C₆Alkylamino group, Mono C₁-C₆Halo Archi
Luamino group or di-C which may be the same or different₁-C₆Ha
Having one or more substituents selected from lower alkylamino groups
Have one or more substituents selected from substituted heterocyclic groups
You can also do it. Z represents an oxygen atom or a sulfur atom. }
The benzamide derivative represented by. 2. In the general formula (I), X, R, Z, B
¹ , B ² , B ³ , B ⁴ , n and m are the same as in claim 1, and Q
Represents -G- (J) q-L, wherein J, q, and L are defined in claim 1.
And G is -O-, -S-, -SO-, -SO ₂
- or -N ((C = O) R 3) - indicates, Y is a halogen atom, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl group, C ₁ -C ₆
Haloalkoxy group, benzamide derivative according to claim 1, wherein indicating a C ₁ -C ₆ haloalkylthio group, C ₁ -C ₆ haloalkylsulfinyl group or a C ₁ -C ₆ haloalkylsulfonyl group. 3. In the general formula (I), X, Y, R,
^{Z, B 1, B 2,} B 3, B 4, n and m are the same comb in claim 1, Q represents -G- (J) q-L, L is the same comb in claim 1, G is -O -, - S -, - SO- or -SO ₂ -
, Q is 1, J is a C ₁ -C ₈ alkylene group or C _3-
The benzamide derivative according to claim 1, which represents a C ₈ alkenylene group. 4. In the general formula (I), X, R, Z, B
¹ , B ² , B ³ , B ⁴ , n and m are the same as in claim 1, and Q
There indicates -G- (J) q-L, L is the same comb in claim 1, G is -O -, - S -, - SO- or -SO ₂ - indicates, q represents 1, J Represents a C ₁ -C ₈ alkylene group or a C ₃ -C ₈ alkenylene group, Y is a halogen atom, a C ₁ -C ₆ alkyl group, a C ₁ -C ₆ haloalkyl group, a C ₁ -C ₆ haloalkoxy group,
Benzamide derivative according to claim 1, wherein indicating a C ₁ -C ₆ haloalkylthio group, C ₁ -C ₆ haloalkylsulfinyl group or a C ₁ -C ₆ haloalkylsulfonyl group. 5. An agricultural and horticultural chemical comprising the benzamide derivative according to any one of claims 1 to 4 as an active ingredient. 6. The agricultural / horticultural chemical according to claim 5, wherein the agricultural / horticultural chemical is an agricultural / horticultural insecticide or an acaricide. 7. An agricultural and horticultural chemical, which comprises treating an object plant or soil with an effective amount of the agricultural or horticultural chemical according to claim 5 or 6 for controlling harmful insects from the useful plants. how to use.