JP2001064258A - Heterocyclic dicarboxylic acid diamide derivative, and insecticide for agriculture and horticulture and method for using the same - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain the subject new derivative useful as an agricultural and horticultural insecticide suitable for controlling insect pests, such as agricultural insect pests, forestry insect pests, horticultural insect pests, sanitary insect pests, and nematodes, which injure paddy rice, fruit trees, vegetables, other crops, flowering plants, and so on. SOLUTION: A compound of formula I R1 to R3 are each H, a (halogenated) 3 to 6C cycloalkyl, or the like, provided that R1 and R2 are simultaneously not H; HeT is a group of formula II [(p) is 0 or 1], or the like; X is a halogen, cyano, nitro, or the like; (n) is 0 to 3; B1 to B4 are each C or N; Y is a halogen, cyano, nitro, phenyl, or the like; (m) is 1 to 5; z1 and Z2 are each 0 or S}, for example, 3-[4-(heptafluoro-2-propyl)-2-methylphenyl]aminocarbonyl-4- pyridinecarboxylic acid 2-propylamide. The compound of formula I can be produced, for example, by a method comprising obtaining a compound of formula IV from a diester compound of formula III (R is a 1 to 3C alkyl) as a starting substance.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

TECHNICAL FIELD The present invention relates to a heterocyclic dicarboxylic acid diamide derivative, an agricultural and horticultural insecticide containing the compound as an active ingredient, and a method of using the same.

[0002]

2. Description of the Related Art JP-A-6-25190, JP-A-9-1990
Although some compounds of the heterocyclic dicarboxylic acid diamide derivative of the present invention are disclosed in JP-A-323974, WO9944492, JP-A-12-7661, JP-A-12-103708 and the like, insecticides for agricultural and horticultural use are disclosed. There is no description or suggestion that it is useful as an agent.

[0003]

The present inventors have conducted intensive studies to develop a novel agricultural and horticultural insecticide. As a result, the heterocyclic dicarboxylic acid diamide derivative represented by the general formula (I) of the present invention was obtained. Are novel compounds not described in the literature, and have found a novel use as agricultural and horticultural insecticides, including the compounds disclosed in the prior art, and have completed the present invention.

[0004]

The present invention provides a compound of the general formula (I)

Embedded image[Wherein, R¹, R^TwoAnd R^ThreeMay be the same or different
And hydrogen atom, C_Three-C₆Cycloalkyl group, halo C_Three-C₆Shi
Chloroalkyl group or -A¹-(R^Four) R (where A ¹Is C₁
 -C₈Alkylene group, C_Three-C₆Alkenylene group or C_Three-C₆A
A ruquinylene group;^FourMay be the same or different,
Hydrogen atom, halogen atom, cyano group, nitro group, halo C
₁-C₆Alkyl group, C_Three-C₆Cycloalkyl group, halo C_Three-C₆
Cycloalkyl group, C₁-C₆Alkoxycarbonyl group;
One or different di C₁-C₆Alkoxyphosphoryl
Groups, which may be the same or different₁-C₆Alkoxythiopho
Sphoryl group, diphenylphosphino group, diphenylphosphine
Hono group, phenyl group,

[0005] The same or different, a halogen atom,
C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, C ₁ -C ₆ alkylthio group, halo C ₁ -C ₆ alkylthio group A C ₁ -C ₆ alkylsulfinyl group, a halo C ₁ -C ₆ alkylsulfinyl group, C _1-
A substituted phenyl group having at least one substituent selected from a C ₆ alkylsulfonyl group or a halo C ₁ -C ₆ alkylsulfonyl group, a heterocyclic group, which may be the same or different, a halogen atom, a C ₁ -C ₆ alkyl Group, halo C ₁ -C ₆ alkyl group, C _1-
C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, C ₁ -C ₆ alkylthio group, halo C ₁ -C ₆ alkylthio group, C ₁ -C ₆ alkylsulfinyl group, halo C ₁ -C ₆ alkylsulfinyl group, A substituted heterocyclic group having at least one substituent selected from a C ₁ -C ₆ alkylsulfonyl group or a halo C ₁ -C ₆ alkylsulfonyl group, or —A ² —R ⁵ (where A ² is —O— , −
S -, - SO -, - SO 2 -, - N (R 6) - ( wherein, R
⁶ is a hydrogen atom, C ₁ -C ₆ alkylcarbonyl group, halo C _1-
C ₆ alkylcarbonyl group, C ₁ -C ₆ alkoxycarbonyl group, phenylcarbonyl group,

[0006] A halogen atom,
C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, C ₁ -C ₆ alkylthio group, halo C ₁ -C ₆ alkylthio group , C ₁ -C ₆ alkylsulfinyl group, halo C ₁ -C ₆ alkylsulfinyl group, C _1-
A substituted phenylcarbonyl group having at least one substituent selected from a C ₆ alkylsulfonyl group or a halo C ₁ -C ₆ alkylsulfonyl group, a phenyl C ₁ -C ₄ alkoxycarbonyl group, which may be the same or different, and a halogen atom , C ₁ -C ₆
Alkyl group, halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, C ₁ -C ₆ alkylthio group,
Selected from halo C ₁ -C ₆ alkylthio, C ₁ -C ₆ alkylsulfinyl, halo C ₁ -C ₆ alkylsulfinyl, C ₁ -C ₆ alkylsulfonyl and halo C ₁ -C ₆ alkylsulfonyl And a substituted phenyl C ₁ -C ₄ alkoxycarbonyl group, C ₁ -C ₆ alkylsulfonyl group or halo C ₁ -C ₆ alkylsulfonyl group having one or more substituents on the ring. ), - C (= O) - or -C (= NOR ⁷⁾ - (wherein, R ⁷ is a hydrogen atom, C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C ₃ -C ₆ alkenyl group, halo C ₃ -C ₆ alkenyl group, C ₃ -C ₆ alkynyl, cyclo C ₃ -C ₆ alkyl group, a phenyl C ₁ -C ₄ alkyl radical or

They may be the same or different and include halogen atoms, C ₁ -C ₆ alkyl groups, halo C ₁ -C ₆ alkyl groups, C ₁ -C ₆
Alkoxy group, halo C ₁ -C ₆ alkoxy group, C ₁ -C ₆ alkylthio group, halo C ₁ -C ₆ alkylthio group, C ₁ -C ₆ alkylsulfinyl group, halo C ₁ -C ₆ alkylsulfinyl group,
A substituted phenyl C ₁ -C ₄ alkyl group having at least one substituent selected from a C ₁ -C ₆ alkylsulfonyl group and a halo C ₁ -C ₆ alkylsulfonyl group on a ring. ) And R
⁵ is a hydrogen atom, C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C ₃ -C ₆ alkenyl group, halo C ₃ -C ₆ alkenyl group, C
₃ -C ₆ alkynyl group, halo C ₃ -C ₆ alkynyl, C ₃ -C ₆ cycloalkyl group, halo C ₃ -C ₆ cycloalkyl group, C ₁ -C ₆
Alkoxy C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkylthio C _1-
C ₆ alkyl group, formyl group, C ₁ -C ₆ alkylcarbonyl group, halo C ₁ -C ₆ alkylcarbonyl group, C ₁ -C ₆ alkoxycarbonyl group, mono C ₁ -C ₆ alkylaminocarbonyl group, identical or different Di C ₁ -C ₆ alkylaminothiocarbonyl group, mono C ₁ -C ₆ alkylaminothiocarbonyl group, which may be the same or different di C ₁ -C ₆ alkylaminothiocarbonyl group, which may be the same or different Di C ₁ -C ₆ alkoxyphosphoryl group, which may be the same or different, di C ₁ -C ₆
Alkoxythiophosphoryl group, phenyl group,

[0008] The same or different, a halogen atom,
C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, C ₁ -C ₆ alkylthio group, halo C ₁ -C ₆ alkylthio group , C ₁ -C ₆ alkylsulfinyl group, halo C ₁ -C ₆ alkylsulfinyl group, C _1-
A substituted phenyl group having at least one substituent selected from a C ₆ alkylsulfonyl group or a halo C ₁ -C ₆ alkylsulfonyl group, a phenyl C ₁ -C ₄ alkyl group, which may be the same or different, a halogen atom, ₁ -C ₆ alkyl group, halo C ₁ -C ₆
Alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, C ₁ -C ₆ alkylthio group, halo C ₁ -C ₆ alkylthio group, C ₁ -C ₆ alkylsulfinyl group, halo C _1- A substituted phenyl C ₁ -C ₄ alkyl group having on the ring one or more substituents selected from a C ₆ alkyl sulfinyl group, a C ₁ -C ₆ alkyl sulfonyl group or a halo C ₁ -C ₆ alkyl sulfonyl group,
Heterocyclic group or

The halogen atom, a C ₁ -C ₆ alkyl group, a halo C ₁ -C ₆ alkyl group, a C ₁ -C ₆
Alkoxy group, halo C ₁ -C ₆ alkoxy group, C ₁ -C ₆ alkylthio group, halo C ₁ -C ₆ alkylthio group, C ₁ -C ₆ alkylsulfinyl group, halo C ₁ -C ₆ alkylsulfinyl group,
It represents a heterocyclic group having at least one substituent selected from a C ₁ -C ₆ alkylsulfonyl group and a halo C ₁ -C ₆ alkylsulfonyl group. ), And r represents an integer of 1 to 4. ). However, this excludes the case where both R ¹ and R ² represent a hydrogen atom. R ¹ and R ² may be mutually the same or different, and may be interrupted by 1 to 3 hetero atoms selected from an oxygen atom, a sulfur atom or a nitrogen atom.
A C ₃ -C ₆ alkylene group can also be indicated. Het represents a heterocyclic group represented by the following Q1 to Q22.

[0010]

Embedded image

[0011]

Embedded image

(Wherein X may be the same or different and may be the same or different, such as halogen atom, cyano group, nitro group, C ₃ -C ₆ cycloalkyl group, halo C ₃ -C ₆ cycloalkyl group) Tri C ₁ -C ₆ alkylsilyl group, phenyl group, which may be the same or different, a halogen atom, C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo
C ₁ -C ₆ alkoxy group, C ₁ -C ₆ alkylthio group, halo C ₁ -C
₆ alkylthio group, C ₁ -C ₆ alkylsulfinyl group, halo C ₁ -C ₆ alkylsulfinyl group, C ₁ -C ₆ alkylsulfonyl group or halo C ₁ -C ₆ 1 or more substituents selected from an alkylsulfonyl group Having a substituted phenyl group, a heterocyclic group,

A halogen atom,
 C₁-C₆Alkyl group, halo C₁-C₆Alkyl group, C₁-C₆Al
Coxy group, halo C₁-C₆Alkoxy group, C₁-C₆Alkyl
O group, halo C₁-C₆Alkylthio group, C₁-C₆Alkylsul
Finyl group, halo C₁-C₆Alkylsulfinyl group, C₁-
C₆Alkylsulfonyl group or halo C₁-C₆Alkylsulfo
Substituted hetero having one or more substituents selected from nyl group
Ring group or -A^Three-R⁸(Where A^ThreeIs -O-, -S-,-
SO-, -SO_Two -, -N (R⁶)-(Where R ⁶Is before
Same as above. ), -C (= O)-, -C (= NOR⁷) −
(Where R⁷Is the same as above. ), C₁-C₆Alkylene group,
Halo C₁-C₆Alkylene group, C_Two-C₆Alkenylene group, halo
 C_Two-C₆Alkenylene group, C_Two-C₆Alkynylene group or halo
 C_Three-C₆Represents an alkynylene group,

(1) .A^ThreeIs -O-, -S-, -SO-,-
SO_Two -Or -N (R⁶)-(Where R⁶Is the same as above
Same. ), R⁸Is halo C_Three-C₆Cycloalkyl
Group, halo C _Three-C₆Cycloalkenyl group, phenyl group, same
Or different, a halogen atom, C₁-C₆Alkyl
Group, halo C₁-C₆Alkyl group, C₁-C₆Alkoxy group, halo
 C₁-C₆Alkoxy group, C₁-C₆Alkylthio group, halo C₁-
C₆Alkylthio group, C₁-C₆Alkylsulfinyl group, ha
B C₁-C₆Alkylsulfinyl group, C₁-C₆Alkylsul
Honyl group or halo C₁-C₆Select from alkylsulfonyl groups
Substituted phenyl group having one or more substituents, heterocycle
Group, which may be the same or different, a halogen atom, C ₁-C₆A
Ruquil group, halo C₁-C₆Alkyl group, C₁-C₆Alkoxy
Group, halo C₁-C₆Alkoxy group, C₁-C₆Alkylthio group,
Halo C₁-C₆Alkylthio group, C₁-C₆Alkylsulfini
Le group, halo C₁-C₆Alkylsulfinyl group, C₁-C₆Al
Killsulfonyl group or halo C₁-C₆Alkylsulfonyl group
A substituted heterocyclic group having at least one substituent selected from
Is

-A ⁴ -R ⁹ (where A ⁴ is a C ₁ -C ₆ alkylene group, a halo C ₁ -C ₆ alkylene group, a C ₃ -C ₆ alkenylene group, a halo C ₃ -C ₆ alkenylene group, A C ₃ -C ₆ alkynylene group or a halo C ₃ -C ₆ alkynylene group, wherein R ⁹ is a hydrogen atom, a halogen atom, a C ₃ -C ₆ cycloalkyl group, a halo C _3-
C ₆ cycloalkyl group, C ₁ -C ₆ alkoxycarbonyl group,
A phenyl group, which may be the same or different, a halogen atom,
C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, C ₁ -C ₆ alkylthio group, halo C ₁ -C ₆ alkylthio group , C ₁ -C ₆ alkylsulfinyl group, halo C ₁ -C ₆ alkylsulfinyl group, C _1-
A substituted phenyl group having one or more substituents selected from a C ₆ alkylsulfonyl group or a halo C ₁ -C ₆ alkylsulfonyl group, or

-A ⁵ -R ¹⁰ (where A ⁵ is -O-, -S
—, —SO—, —SO ₂ — or —C (＝ O);
¹⁰ is a C ₁ -C ₆ alkyl group, a halo C ₁ -C ₆ alkyl group, C ₃ -C ₆
Alkenyl group, halo C ₃ -C ₆ alkenyl group, C ₃ -C ₆ cycloalkyl group, halo C ₃ -C ₆ cycloalkyl group may phenyl group, the same or different, a halogen atom, C ₁ -C ₆ alkyl Group, halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, C ₁ -C ₆ alkylthio group,
Selected from halo C ₁ -C ₆ alkylthio, C ₁ -C ₆ alkylsulfinyl, halo C ₁ -C ₆ alkylsulfinyl, C ₁ -C ₆ alkylsulfonyl and halo C ₁ -C ₆ alkylsulfonyl A substituted phenyl group having at least one substituent, a heterocyclic group or the same or different, a halogen atom, a C ₁ -C ₆ alkyl group, a halo C ₁ -C ₆ alkyl group,
₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, C ₁ -C ₆ alkylthio group, halo C ₁ -C ₆ alkylthio group, C ₁ -C ₆ alkylsulfinyl group, halo C ₁ -C ₆ alkylsulfinyl A substituted heterocyclic group having at least one substituent selected from a group, a C ₁ -C ₆ alkylsulfonyl group and a halo C ₁ -C ₆ alkylsulfonyl group. ). ),

(2) .A^ThreeIs -C (= O)-or -C (= N
OR⁷)-(Wherein, R⁷Is the same as above. ), R
⁸Is a hydrogen atom, C₁-C₆Alkyl group, halo C₁-C₆Alkyl
Group, C _Two-C₆Alkenyl group, halo C_Two-C₆Alkenyl group, C
_Three-C₆Cycloalkyl group, halo C _Three-C₆Cycloalkyl group,
 C₁-C₆Alkoxy group, C₁-C₆Alkylthio group, mono C₁-
C₆Alkylamino group, di C which may be the same or different₁-C₆
Alkylamino group, phenyl group, same or different
, Halogen atom, C₁-C₆Alkyl group, halo C₁-C₆Al
Kill group, C₁-C₆Alkoxy group, halo C₁-C₆Alkoxy
Group, C₁-C₆Alkylthio group, halo C₁-C₆Alkylthio
Group, C₁-C₆Alkylsulfinyl group, halo C₁-C₆Archi
Rusulfinyl group, C₁-C₆Alkylsulfonyl group or ha
B C₁-C₆One or more selected from alkylsulfonyl groups
A substituted phenyl group having a substituent,

Phenylamino group, same or different
, Halogen atom, C₁-C₆Alkyl group, halo C₁-C₆Al
Kill group, C₁-C₆Alkoxy group, halo C₁-C₆Alkoxy
Group, C₁-C₆Alkylthio group, halo C₁-C₆Alkylthio
Group, C₁-C₆Alkylsulfinyl group, halo C₁-C₆Archi
Rusulfinyl group, C₁-C₆Alkylsulfonyl group or ha
B C ₁-C₆One or more selected from alkylsulfonyl groups
Substituted phenylamino group having a substituent on the ring, heterocyclic group
Or the same or different, a halogen atom, C ₁-
C₆Alkyl group, halo C₁-C₆Alkyl group, C₁-C₆Alkoki
Si group, halo C₁-C₆Alkoxy group, C₁-C₆Alkylthio
Group, halo C₁-C₆Alkylthio group, C₁-C₆Alkylsulf
Ynyl group, halo C₁-C₆Alkylsulfinyl group, C₁-C₆
Alkylsulfonyl group or halo C₁-C₆Alkylsulfoni
Substituted heterocycle having one or more substituents selected from
Represents a group,

(3) A ³ is a C ₁ -C ₆ alkylene group, halo C _1-
When C ₆ alkylene group, C ₂ -C ₆ alkenylene group, halo C ₂ -C ₆ alkenylene group, C ₂ -C ₆ alkynylene group or halo C ₃ -C ₆ alkynylene group, R ⁸ is a hydrogen atom, a halogen atom , C ₃ -C ₆ cycloalkyl group, halo C ₃ -C ₆ cycloalkyl group, C ₁ -C ₆ alkoxycarbonyl group, the same or different tri-C ₁ may be -C ₆ alkylsilyl group, a phenyl group, the same or May be different, halogen atom, C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo
C ₁ -C ₆ alkoxy group, C ₁ -C ₆ alkylthio group, halo C _1-
C ₆ alkylthio group, C ₁ -C ₆ alkylsulfinyl group, one or more substituents selected from halo C ₁ -C ₆ alkylsulfinyl group, C ₁ -C ₆ alkylsulfonyl group or halo C ₁ -C ₆ alkylsulfonyl group A substituted phenyl group having a group, a heterocyclic group,

The same or different, a halogen atom,
C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, C ₁ -C ₆ alkylthio group, halo C ₁ -C ₆ alkylthio group , C ₁ -C ₆ alkylsulfinyl group, halo C ₁ -C ₆ alkylsulfinyl group, C _1-
A substituted heterocyclic group having one or more substituents selected from a C ₆ alkylsulfonyl group or a halo C ₁ -C ₆ alkylsulfonyl group, or —A ⁶ -R ¹¹ (where A ⁶ is —O—, —S −, −
SO- or -SO ₂ - indicates, R ¹¹ is C ₃ -C ₆ cycloalkyl group, halo C ₃ -C ₆ cycloalkyl group, a phenyl group, the same or different and a halogen atom, C ₁ -C ₆ Alkyl group, halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo
C ₁ -C ₆ alkoxy group, C ₁ -C ₆ alkylthio group, halo C _1-
C ₆ alkylthio group, C ₁ -C ₆ alkylsulfinyl group, one or more substituents selected from halo C ₁ -C ₆ alkylsulfinyl group, C ₁ -C ₆ alkylsulfonyl group or halo C ₁ -C ₆ alkylsulfonyl group A substituted phenyl group having a group,

A heterocyclic group, which may be the same or different, and
Gen atom, C₁-C₆Alkyl group, halo C ₁-C₆Alkyl group,
 C₁-C₆Alkoxy group, halo C₁-C₆Alkoxy group, C₁-C₆
Alkylthio group, halo C₁-C₆Alkylthio group, C₁-C₆A
Rukylsulfinyl group, halo C ₁-C₆Alkylsulfini
Group, C₁-C₆Alkylsulfonyl group or halo C₁-C₆Al
Having one or more substituents selected from killsulfonyl groups
Substituted heterocyclic group or -A ⁷-R¹²(Where A⁷Is C₁-C₆A
Alkylene group, halo C₁-C₆Alkylene group, C_Two-C₆Alkene
Len group, halo C_Two-C₆Alkenylene group, C_Two-C₆Alkinile
Or halo C_Three-C₆An alkynylene group;¹²Is hydrogen
Atom, halogen atom, C_Three-C₆Cycloalkyl group, halo C
_Three-C₆Cycloalkyl group, C₁-C₆Alkoxy group, halo C₁-
C₆Alkoxy group, C₁-C₆Alkylthio group, halo C₁-C₆A
Lucylthio group, C₁-C₆Alkylsulfinyl group, halo C
₁-C₆Alkylsulfinyl group, C₁-C₆Alkylsulfoni
Le group, halo C₁-C₆Alkylsulfonyl group,

A phenyl group, which may be the same or different, a halogen atom, a C ₁ -C ₆ alkyl group, a halo C ₁ -C ₆ alkyl group, a C ₁ -C ₆ alkoxy group, a halo C ₁ -C ₆ alkoxy group, C
₁ -C ₆ alkylthio group, halo C ₁ -C ₆ alkylthio group, C _1-
C ₆ alkyl sulfinyl group, halo C ₁ -C ₆ alkyl sulfinyl group, C ₁ -C ₆ alkyl sulfonyl group or halo C ₁ -C ₆
A substituted phenyl group having at least one substituent selected from an alkylsulfonyl group, a phenoxy group, which may be the same or different, a halogen atom, a C ₁ -C ₆ alkyl group, a halo C ₁ -C
₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, C ₁ -C ₆ alkylthio group, halo C ₁ -C ₆ alkylthio group, C ₁ -C ₆ alkylsulfinyl group, halo C ₁ A substituted phenoxy group having at least one substituent selected from a -C ₆ alkylsulfinyl group, a C ₁ -C ₆ alkylsulfonyl group or a halo C ₁ -C ₆ alkylsulfonyl group,

A phenylthio group, which may be the same or different, a halogen atom, a C ₁ -C ₆ alkyl group, a halo C ₁ -C ₆ alkyl group, a C ₁ -C ₆ alkoxy group, a halo C ₁ -C ₆ alkoxy group, C ₁ -C ₆ alkylthio group, halo C ₁ -C ₆ alkylthio group, C ₁ -C ₆ alkylsulfinyl group, halo C ₁ -C ₆ alkylsulfinyl group, C ₁ -C ₆ alkylsulfonyl group or halo C ₁ -C A substituted phenylthio group having one or more substituents selected from ₆ alkylsulfonyl groups, a heterocyclic group or may be the same or different, a halogen atom, a C ₁ -C ₆ alkyl group, a halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, C ₁ -C ₆ alkylthio group, halo C ₁
-C ₆ alkylthio group, C ₁ -C ₆ alkyl sulfinyl group,
It represents a substituted heterocyclic group having at least one substituent selected from halo C ₁ -C ₆ alkylsulfinyl, C ₁ -C ₆ alkylsulfonyl and halo C ₁ -C ₆ alkylsulfonyl. ). ). ), And n represents an integer of 0 to 3.

X can form a condensed ring together with an adjacent atom on the hetero ring, and the condensed rings may be the same or different and include a halogen atom, a C ₁ -C ₆ alkyl group. , Halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo
C ₁ -C ₆ alkoxy group, C ₁ -C ₆ alkylthio group, halo C _1-
C ₆ alkylthio group, C ₁ -C ₆ alkyl sulfinyl group, halo C ₁ -C ₆ alkyl sulfinyl group, C ₁ -C ₆ alkyl sulfonyl group, halo C ₁ -C ₆ alkyl sulfonyl group, phenyl group,

The same or different, a halogen atom,
C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, C ₁ -C ₆ alkylthio group, halo C ₁ -C ₆ alkylthio group , C ₁ -C ₆ alkylsulfinyl group, halo C ₁ -C ₆ alkylsulfinyl group, C _1-
A substituted phenyl group having one or more substituents selected from a C ₆ alkylsulfonyl group or a halo C ₁ -C ₆ alkylsulfonyl group, a heterocyclic group, which may be the same or different, a halogen atom, a C ₁ -C ₆ alkyl Group, halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, C
₁ -C ₆ alkylthio group, halo C ₁ -C ₆ alkylthio group, C _1-
C ₆ alkylsulfinyl group, halo C ₁ -C ₆ alkylsulfinyl group, C ₁ -C ₆ alkylsulfonyl group or halo C ₁ -C ₆
It may have one or more substituents selected from a substituted heterocyclic group having one or more substituents selected from an alkylsulfonyl group.

W is O, S or NR ¹³ (wherein R ¹³ is C
₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C ₃ -C ₆ alkenyl group, halo C ₃ -C ₆ alkenyl group, C ₃ -C ₆ alkynyl group, halo C ₃ -C ₆ alkynyl group, C ₁ -C ₆ alkoxy group, phenyl group, which may be the same or different, a halogen atom, C
₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, C ₁ -C ₆ alkylthio group, halo C ₁ -C ₆ alkylthio group, C ₁ -C ₆ alkylsulfinyl group, halo C ₁ -C ₆ alkylsulfinyl group, C ₁ -C ₆
A substituted phenyl group having at least one substituent selected from an alkylsulfonyl group or a halo C ₁ -C ₆ alkylsulfonyl group, a phenyl C ₁ -C ₆ alkyl group or a same or different, a halogen atom, a C _1- C ₆ alkyl group, halo C
₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, C ₁ -C ₆ alkylthio group, halo C ₁ -C ₆ alkylthio group, C ₁ -C ₆ alkylsulfinyl group, halo C ₁ -C ₆ alkylsulfinyl group, C ₁ -C ₆ alkylsulfonyl group or halo C ₁ -C ₆ 1 or more substituted phenyl C ₁ -C ₆ alkyl having a substituent on the ring selected from an alkylsulfonyl group Represents a group. ), And p and q represent an integer of 0 to 1, which may be the same or different. ), And B ¹ , B ² , B ³ and B ⁴ may be the same or different and represent a carbon atom or a nitrogen atom.

Y may be the same or different, and
Child, cyano group, nitro group, halo C_Three-C₆Cycloalkyl
Group, phenyl group, which may be the same or different,
Child, C ₁-C₆Alkyl group, halo C₁-C₆Alkyl group, C₁-C₆
Alkoxy group, halo C₁-C₆Alkoxy group, C₁-C₆Archi
Luthio group, halo C₁-C₆Alkylthio group, C₁-C₆Alkyl
Sulfinyl group, halo C₁-C₆Alkylsulfinyl group,
 C₁-C₆Alkylsulfonyl group or halo C₁-C₆Alkyls
Substitution having one or more substituents selected from a rufonyl group
Phenyl group, heterocyclic group, same or different, halo
Gen atom, C₁-C₆Alkyl group, halo C₁-C₆Alkyl group,
 C₁-C₆Alkoxy group, halo C₁-C₆Alkoxy group, C₁-C₆
Alkylthio group, halo C₁-C₆Alkylthio group, C₁-C₆A
Rukylsulfinyl group, halo C₁-C₆Alkylsulfini
Group, C₁-C₆Alkylsulfonyl group or halo C₁-C₆Al
Having one or more substituents selected from killsulfonyl groups
Substituted heterocyclic group or -A^Three-R⁸(Where A^ThreeAnd R⁸Is
Same as above. ), And m represents an integer of 1 to 5.

Y can form a condensed ring together with adjacent carbon atoms on the aromatic ring, and the condensed rings may be the same or different and include a halogen atom, a C ₁ -C ₆ alkyl Group, halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, C ₁ -C ₆ alkylthio group, halo C
₁ -C ₆ alkylthio group, C ₁ -C ₆ alkylsulfinyl group,
Halo C ₁ -C ₆ alkylsulfinyl group, C ₁ -C ₆ alkylsulfonyl group, halo C ₁ -C ₆ alkylsulfonyl group, phenyl group, which may be the same or different, a halogen atom, C ₁ -C ₆
Alkyl group, halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, C ₁ -C ₆ alkylthio group,
Selected from halo C ₁ -C ₆ alkylthio, C ₁ -C ₆ alkylsulfinyl, halo C ₁ -C ₆ alkylsulfinyl, C ₁ -C ₆ alkylsulfonyl and halo C ₁ -C ₆ alkylsulfonyl A substituted phenyl group having one or more substituents,

A heterocyclic group or the same or different, a halogen atom, a C ₁ -C ₆ alkyl group, a halo C ₁ -C ₆ alkyl group, a C ₁ -C ₆ alkoxy group, a halo C ₁ -C ₆ alkoxy group A C ₁ -C ₆ alkylthio group, a halo C ₁ -C ₆ alkylthio group, a C ₁ -C ₆ alkylsulfinyl group, a halo C ₁ -C ₆ alkylsulfinyl group, a C ₁ -C ₆ alkylsulfonyl group or a halo C _1- It may have one or more substituents selected from a substituted heterocyclic group having one or more substituents selected from a C ₆ alkylsulfonyl group. Z ¹ and Z ² represent an oxygen atom or a sulfur atom.

However, (1). Het indicates Q2, Q6, Q7 or Q9, and B ¹ ,
When B ² , B ³ and B ⁴ simultaneously represent a carbon atom, Ym
Is 3-chloro-2-methyl, 3-chloro-2,6-diethyl, 5-chloro-2-methyl, 2,6-diethyl, 4-chloro-2-fluoro and 2-ethyl- 6
-Excluding the methyl group. (2) .Het represents ^{Q4, B 1, B 2,} B 3 and, if B ⁴ represents a carbon atom at the same time, the Ym 2,5-dichloro group, 2,4-difluoro group, 2,6-difluoro Group, 3
-Chloro-2-methyl group, 5-chloro-2-methyl group,
5-fluoro-2-methyl group, 2,6-dimethyl group,
2,6-diethyl group, 2-ethyl-6-methyl group, 2-
A methoxy-5-nitro group, a 2-methoxy-5-methyl group, a 2,6-diethoxy group, a 3-bromo-2-methyl group, a 3-fluoro-2-methyl group, a 3-iodo-2-methyl group, 3-cyano-2-methyl group, 3-difluoromethoxy-2-methyl group, 5-chloro-2-ethyl group,
2,5-dimethyl group, 2,3-dichloro group, 3-chloro-2,6-diethyl group, 4-trifluoromethyl group, 3
-Methoxycarbonyl-2-methyl group, 3-trifluoromethyl-2-methyl group, 3,5-dichloro-2,6-
Excludes diethyl group, 3,4-dichloro group, 3-methoxycarbonylmethyloxy-2-methyl group, 2-methyl-3-nitro group and 4-trifluoromethoxy group.

(3). Het represents Q9, R ² and R ³ simultaneously represent a hydrogen atom, Xn represents a 2-phenyl group,
R ¹ represents an n-propyl group or an i-propyl group,
When B ¹ , B ² , B ³ and B ⁴ simultaneously represent a carbon atom, Ym excludes a 4-pentafluoroethyl-2-methyl group. (4). Het indicates Q10, B ¹ , B ² , B ³ and B ⁴
Represents simultaneously a carbon atom, Ym is 5-chloro-2-
Excluding a methyl group, a 5-fluoro-2-methyl group and a 2,5-dimethyl group], a pesticide for agricultural and horticultural use and a method for using the same.

[0032]

BEST MODE FOR CARRYING OUT THE INVENTION In the definition of the general formula (I) of the heterocyclic dicarboxylic diamide derivative of the present invention, "halogen atom" means a chlorine atom, bromine atom, iodine atom or fluorine atom, and "C _1- “C ₆ alkyl” means, for example, a straight or branched chain such as methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, n-pentyl, n-hexyl and the like. A haloC ₁ -C ₆ alkyl ”means a straight-chain or branched carbon atom substituted by one or more halogen atoms which may be the same or different. The term “halo C ₃ -C ₆ cycloalkyl” means an alkyl group having 1 to 6 atoms, and “halo C ₃ -C ₆ cycloalkyl” is an alicyclic group having 3 to 6 carbon atoms substituted by one or more halogen atoms which may be the same or different. Represents a hydrocarbon group of the formula, "C ₁ -C ₈ alkylene" is methylene And linear or branched alkylene groups having 1 to 8 carbon atoms such as ethylene, propylene, trimethylene, dimethylmethylene, tetramethylene, isobutylene, dimethylethylene and octamethylene.

"Heterocyclic group" means pyridyl, pyridine-N-oxide, pyrimidinyl, furyl, tetrahydrofuryl, thienyl, tetrahydrothienyl, tetrahydropyranyl, tetrahydrothiopyranyl, oxazolyl. Group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group, thiadiazolyl group, imidazolyl group, triazolyl group, a heterocyclic group such as a pyrazolyl group, and `` R ¹ and R ² are bonded to each other, and may be different, an oxygen atom, and also a good C ₃ -C ₆ alkylene "is interrupted by 1-3 heteroatoms selected from oxygen, sulfur atom or nitrogen atom, for example azetidine ring, pyrrolidine ring, pyrroline ring, Piperidine ring, imidazolidine ring, imidazoline ring, oxazolidine ring, thiazolidine , Isoxazolidine ring, isothiazolidine ring, tetrahydropyridine ring, piperazine ring, morpholine ring, thiomorpholine ring, dioxazine ring, dithiazine ring, indole ring, benzo [b] furan ring, benzo [b] thiophene ring, quinoline ring, isoquinoline ring , Naphthyridine ring, quinoxaline ring and the like.

"X can form a condensed ring together with adjacent atoms on the hetero ring" means, for example, an indole ring, a benzo [b] furan ring, a benzo [b] thiophene ring, a quinoline Ring, isoquinoline ring, naphthyridine ring, quinoxaline ring, cinnoline ring and the like. "Y can form a fused ring together with adjacent carbon atoms on an aromatic ring" means, for example, naphthalene, tetrahydronaphthalene, indene, indane, quinoline, quinazoline, chroman, isochroman, indole, indoline Benzodioxane, benzodioxol, benzofuran, dihydrobenzofuran, benzothiophene, dihydrobenzothiophene, benzoxazole, benzothiazole, benzimidazole, indazole and the like.

The heterocyclic dicarboxylic acid diamide derivative represented by the general formula (I) of the present invention may contain an asymmetric carbon atom or an asymmetric center in its structural formula, and the optical isomers and diastereomers may not be present. In some cases, the present invention includes all the optical isomers and the mixtures containing them in any ratio. Further, the heterocyclic dicarboxylic acid diamide derivative represented by the general formula (I) of the present invention has a structure in which a geometric isomer derived from a carbon-carbon double bond or a carbon-nitrogen double bond exists in its structural formula. However, the present invention encompasses all geometric isomers and mixtures containing them in any proportion. The heterocyclic dicarboxylic acid diamide derivative represented by the general formula (I) of the present invention can be produced, for example, by a production method illustrated below.

Manufacturing method 1

Embedded image (Where R ¹ , R ² , Het, B ¹ , B ² , B ³ ,
B ⁴ , X, Y, m and n are as defined above, hal represents a halogen atom, and R represents a C ₁ -C ₃ alkyl group. )

The diester represented by the general formula (VIII) is hydrolyzed in the presence of an acid or alkali to give a dicarboxylic acid represented by the general formula (VII), and the dicarboxylic acid is converted to an acid in the presence of a dehydrating agent. After forming the anhydride (VI), in the presence or absence of an inert solvent, reacted with a substituted aromatic amine represented by the general formula (V), the general formula (IV-1) and (IV-2) Amides represented by the following formula, and reacting with a dehydrating agent in the presence or absence of an inert solvent without isolation or isolation of the amides, general formula (III)
Represented by the general formula (II-1) in the presence or absence of an inert solvent without isolation or isolation of the imides
Alternatively, the heterocyclic dicarboxylic acid diamide derivative represented by the general formula (I-1) can be produced by reacting with an amine represented by the general formula (II-2) or a salt thereof.

(1-1). General formula (VIII) → General formula (VII) Examples of the inert solvent that can be used in this reaction include water, water-soluble solvents such as methanol, ethanol, and propanol, and a mixed solvent of water and a water-soluble solvent. Can be used. As the base used for the hydrolysis, for example, sodium hydroxide, hydroxides of alkali metal atoms such as potassium hydroxide can be used, the amount of which is based on the diesters represented by the general formula (VIII) 2
What is necessary is just to select and use suitably from the range of 10 to 10 equivalents.
Further, as the acid, for example, inorganic acids such as hydrochloric acid and sulfuric acid, and organic acids such as trifluoroacetic acid can be used, and the amount of the acid used is a catalytic amount with respect to the diester represented by the general formula (VIII). Good, in the range of 0.001 to 0.1 equivalent.

The reaction can be carried out at room temperature or under reflux of the inert solvent to be used. The reaction time is not fixed depending on the reaction scale, the reaction temperature and the like, but may be appropriately selected from the range of several minutes to 48 hours. good. After the completion of the reaction, the desired product can be produced by isolating the desired product from the reaction system containing the desired product by a conventional method and, if necessary, purifying the product by a recrystallization method, a distillation method, a column chromatography method or the like. After the completion of this reaction, the target product can be used for the next reaction without isolation.

(1-2). General formula (VII) → General formula (VI) As the inert solvent that can be used in this reaction, any solvent that does not significantly inhibit the progress of this reaction may be used.Examples include halogenated hydrocarbons such as dichloromethane, chloroform, and carbon tetrachloride. , Aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene, linear or cyclic ethers such as methylcellosolve, diethyl ether, diisopropyl ether, dioxane and tetrahydrofuran, and organic acids such as acetic acid and trifluoroacetic acid Can be used, and these inert solvents can be used alone or in combination. Further, by using an excess of a dehydrating agent, it can be used as a substitute for an inert solvent. As the dehydrating agent, for example, dehydrating agents such as acetic anhydride and trifluoroacetic anhydride can be used.
The compound may be appropriately selected from the range of equimolar to excess molar with respect to the compound represented by (VII), and is preferably used in an equimolar amount.

The reaction temperature may be appropriately selected from the room temperature to the boiling point of the inert solvent to be used. When no inert solvent is used, the reaction may be carried out in the boiling point of the dehydrating agent to be used. The reaction time is not constant depending on the reaction temperature, the reaction scale, etc.
It may be performed within a range of 48 hours. After the completion of the reaction, the desired product can be produced by isolating the desired product from the reaction system containing the desired product by a conventional method and, if necessary, purifying the product by a recrystallization method, a distillation method, a column chromatography method or the like. After completion of this reaction, the target product can be used for the next reaction without isolation.

(1-3). General formula (VI) → General formula (IV-1) + General formula (IV-2) As the inert solvent that can be used in this reaction, any solvent that does not significantly inhibit the progress of this reaction may be used, such as benzene and toluene. , Aromatic hydrocarbons such as xylene, methylene chloride, chloroform, carbon tetrachloride, chlorobenzene,
Halogenated hydrocarbons such as dichlorobenzene, linear or cyclic ethers such as diethyl ether, dioxane, and tetrahydrofuran; esters such as ethyl acetate; amides such as dimethylformamide and dimethylacetamide;
Acids such as acetic acid, dimethyl sulfoxide, 1,3-dimethyl-2-imidazolidinone, and inert solvents such as water can be exemplified. These inert solvents may be used alone or as a mixture of two or more. Can be.

Since this reaction is an equimolar reaction, each reactant may be used in an equimolar amount, but any of the reactants can be used in excess. This reaction can be carried out under dehydration conditions as needed. The reaction can be carried out at a temperature from room temperature to the reflux of the used inert solvent. The reaction time is not fixed depending on the reaction scale, the temperature and the like, but may be appropriately selected from the range of several minutes to 48 hours. After the completion of the reaction, the desired product can be produced by isolating the desired product from the reaction system containing the desired product by a conventional method and, if necessary, purifying the product by a recrystallization method, a distillation method, a column chromatography method or the like. After completion of this reaction, the target product can be used for the next reaction without isolation. (1-4). General formula (IV-1) + General formula (IV-2) → General formula (II
I) The target compound can be produced by carrying out the same reaction as in (1-2). After the completion of this reaction, the target product can be used for the next reaction without isolation. (1-5). General formula (III) → General formula (I-1) Examples of the inert solvent usable in this reaction include (1-
In addition to the inert solvents exemplified in 2), pyridines can also be used.

Since this reaction is an equimolar reaction, the general formula (I
The amines represented by I-1) or the amine salts represented by the general formula (II-2) may be used in an equimolar amount to the imides represented by the general formula (III). Can also be used. When using an amine salt represented by the general formula (II-2) in this reaction, a base is required to generate a free amine in the reaction system, and an inorganic base or an organic base should be used as the base. As the inorganic base, for example, sodium hydroxide, potassium hydroxide, sodium carbonate, hydroxides of alkali metal atoms such as potassium carbonate, carbonates and the like,
As the organic base, for example, triethylamine, pyridine, 4-dimethylaminopyridine, 1,8-diazabicyclo [5,4,0] -7-undecene and the like can be exemplified. It may be appropriately selected and used in the range of equimolar to excess molar with respect to the amine salt represented by II-2).

The reaction temperature may be appropriately selected from the range of -10 ° C to the boiling point of the inert solvent used, preferably from 0 ° C to 1 ° C.
What is necessary is just to carry out in the range of 50 degreeC. The reaction time is not fixed depending on the reaction temperature, the reaction scale and the like, but may be in the range of several minutes to 48 hours. After the completion of the reaction, the desired product can be produced by isolating the desired product from the reaction system containing the desired product by a conventional method and, if necessary, purifying the product by a recrystallization method, a distillation method, a column chromatography method or the like.

The compound represented by the general formula (VIII), which is a starting compound for this reaction, can be prepared by a known method [for example, J. Am. Am. Ch
em. Soc. , 63 , 1762 (1941); H
heterocyclic Chem. , 21, 1431
(1984); Indian Chem. So
c. , 1982 , 1372; Org. Chem. ,
14 , 723 (1949), Heterocycle
s, 27 , 1489 (1988); Am. Che
m. Soc. , 78 , 2220 (1956); Pr
akt. Chem. , 311 , 807 (1969), T
etrahedron, 36 , 1801 (1980),
JP-A-6-122684, U.S. Pat.
Nos. 14,580 and 3,686,171,
J. Med. Chem. , 27 , 1396 (198
4). Heterocyclic Chem. , 1
2 , 1303 (1975) and 15 , 1477 (197)
8), id. 16 , 1141 (1979), id. 17 , 443
(1982), 21 , 689 (1984), Bei
l. , 25III , 2028; JP-A-52-77086; Am. Chem. Soc. , 81 , 2456
(1956); Org. Chem. , 37 , 322
4 (1972), JP-A-62-175480,

JP-A-62-230782, JP-A-60-69083, JP-A-60-185873, JP-A-61-109790, JP-A-62-2
No. 77385, JP-A-63-295575,
JP-A-63-99067, JP-A-64-7547
No. 4, JP-A-64-90118, Pharmaceutical Magazine,
84 , 416 (1964); Chem. and Pha
rm. Bull. , 5 , 277 (1957); Che
m. Research (S), 1989, 196, Ch
em. Pharm. Bull. , 20 (7), 1513
(1972); Heterocyclic Che
m. , 27 , 579 (1990), Tetrahedr.
on, 53 (42), 14497 (1997), 41
(7 ) , 1199 (1985); Chem. Ber. ,
107 , 3036 (1974); Heterocycy
click Chem. 23 , 110 3 (1986);
5 , 125 (1968); Org. Chem. , 2
6 , 468 (1961)].

Manufacturing method 2.

Embedded image (Where R ¹ , R ² , Het, B ¹ , B ² , B ³ ,
B ⁴ , X, Y, hal, m and n are as defined above,
X ′ represents a halogen atom or a nitro group. X excludes a hydrogen atom or a nitro group. )

By reacting the heterocyclic dicarboxylic imide derivative represented by the general formula (III-1) with a reactant corresponding to X in the presence of an inert solvent, the compound represented by the general formula (III) is obtained. Heterocyclic dicarboxylic imide derivative, the heterocyclic dicarboxylic imide derivative (III) is isolated or not isolated amines represented by the general formula (II-1) or the general formula (II-2) or By reacting with a salt, a heterocyclic dicarboxylic diamide derivative represented by the general formula (I-1) can be produced. (2-1) General formula (III-1) → General formula (III) Org. Chem. , 42 , 3415 (1
977), Tetrahedron, 25 , 5921
(1969), Synthesis, 1984 , 66.
7, Chem. Lett. , 1973 , 471; O
rg. Chem. , 39, 3318 (1974), the same 3
9 , 3327 (1974) and the like. (2-2). General formula (III) → General formula (I-1) This reaction can be produced according to the production method (1-5).

Manufacturing method 3.

Embedded image (Where R ¹ , R ² , Het, B ¹ , B ² , B ³ ,
B ⁴ , X, Y, hal, m and n are the same as above. )

The heterocyclic dicarboxylic anhydride derivative represented by the general formula (VI-1) is reacted with an aromatic ring amine represented by the general formula (V) in the presence of an inert solvent to give a compound represented by the general formula (VI-1) Amides represented by (IV-1 ′) and (IV-2 ′), and reacting with a dehydrating agent in the presence or absence of an inert solvent without isolation or isolation of the amides, The heterocyclic dicarboxylic acid imide derivative represented by the general formula (III-2) is subjected to a catalytic hydrogen reduction reaction with or without isolating the heterocyclic dicarboxylic imide derivative (III-2) to obtain a compound represented by the general formula (III III-3), a heterocyclic dicarboxylic imide derivative represented by the following general formula (III-3): III), and isolating or isolating the heterocyclic dicarboxylic imide derivative (III). The heterocyclic dicarboxylic acid diamide derivative represented by the general formula (I-1) by reacting with an amine represented by the general formula (II-1) or the general formula (II-2) or a salt thereof Can be manufactured. (3-1). General formula (VI-1) → General formula (IV-1 ') + General formula (IV-
2 ′) The target compound can be produced by carrying out the reaction in the same manner as in Production method (1-3). (3-2). General formula (IV-1 ') + General formula (IV-2') → General formula (I
II-2) This reaction can be carried out in the same manner as in Production method (1-4) to produce the desired product.

(3-3). General formula (III-2) → General formula (III
-3) As the inert solvent that can be used in the present reaction, any solvent that does not significantly inhibit the progress of the present reaction may be used, and for example, alcohols such as methanol, ethanol, and propanol, diethyl ether, dioxane, and linear chains such as tetrahydrofuran, etc. Acids such as cyclic ethers and acetic acid can be exemplified, and these inert solvents can be used alone or in combination of two or more. Examples of the catalytic reduction catalyst used in this reaction include palladium carbon, Raney nickel,
Palladium black, platinum black and the like can be exemplified, and the amount of use is appropriately selected from the range of 0.1 to 10% by weight based on the heterocyclic dicarboxylic acid imide derivative represented by the general formula (III-2). You can use it. This reaction is performed in a hydrogen atmosphere, and the hydrogen pressure may be appropriately selected from the range of 1 to 10 atm. The reaction can be carried out at a temperature from room temperature to the reflux temperature of the inert solvent to be used. The reaction time is not fixed depending on the reaction scale, the reaction temperature and the like, but may be appropriately selected from several minutes to 48 hours. After completion of the reaction, the desired product can be isolated from the reaction system containing the desired product according to a conventional method, and the desired product can be produced by purification by recrystallization, column chromatography or the like, if necessary. In addition, it is also possible to use the next reaction step without isolating the target substance from the reaction system.

(3-4). General formula (III-3) → General formula (II
I) As the inert solvent used in this reaction, an acidic solvent can be used, and examples thereof include aqueous hydrochloric acid, aqueous hydrobromic acid, aqueous hydroiodic acid, aqueous sulfuric acid, acetic acid, and trifluoroacetic acid. These acidic solvents can be used alone or in combination of two or more. Further, these acidic solvents and ethers such as tetrahydrofuran and dioxane can be mixed and used. Examples of the diazotizing agent include diazotizing agents such as sodium nitrite, nitrosyl hydrogen sulfate, and alkyl nitrite.The amount of these used is the heterocyclic dicarboxylic acid represented by the general formula (III-3). What is necessary is just to select suitably from the range of an equivalent amount or an excess amount with respect to an imide derivative. The reaction temperature can be from -50 ° C to room temperature to the reflux temperature of the inert solvent used, and the reaction time is not fixed depending on the reaction scale, the reaction temperature, etc., but may be appropriately selected within the range of several minutes to 48 hours. good.

As the metal salt to be added after the formation of the diazonium salt, for example, metal salts such as cuprous chloride, cuprous bromide, potassium iodide, copper cyanide, potassium xanthogensan, and sodium mercaptan can be used. Can,
The amount of use may be appropriately selected from a range of 1 equivalent or more relative to the heterocyclic dicarboxylic imide derivative represented by the general formula (III-3). After completion of the reaction, the desired product can be isolated from the reaction system containing the desired product according to a conventional method, and the desired product can be produced by purification by recrystallization, column chromatography or the like, if necessary. In addition, it is also possible to use the next reaction step without isolating the target substance from the reaction system.
This reaction is described in Org. Synth. , IV, 160 (196)
3), ibid., III, 809 (1959); Am. Ch
em. Soc. , 92 , 3520 (1970). (3-5). General formula (III) → General formula (I-1) The reaction can be carried out in the same manner as in Production method (1-5) to produce the desired product.

Manufacturing method 4.

Embedded image (Where R ¹ , R ² , Het, B ¹ , B ² , B ³ ,
B ⁴ , X, Y, hal, m and n are the same as above. )

The heterocyclic dicarboxylic acid imide derivative represented by the general formula (III-2) and the amine represented by the general formula (II-1) or (II-2) or a salt thereof are converted into an inert solvent. To give a heterocyclic dicarboxylic acid diamide derivative represented by the general formula (I-3), and isolating or not isolating the heterocyclic dicarboxylic acid diamide derivative (I-3) to perform catalytic hydrogen reduction The reaction is performed to obtain a heterocyclic dicarboxylic acid diamide derivative represented by the general formula (I-2) .The heterocyclic dicarboxylic acid diamide derivative (I-2) is isolated or not isolated, and a diazotization reaction is performed. The heterocyclic dicarboxylic acid diamide derivative represented by the general formula (I-1) can be produced by adding a salt. (4-1). General formula (III-2) → General formula (I-3) In this reaction, the target product can be produced in the same manner as in Production method (1-5). (4-2). General formula (I-3) → General formula (I-2) In this reaction, the target compound can be produced in the same manner as in Production method (3-3). (4-3). General formula (I-2) → General formula (I-1) In this reaction, the target compound can be produced in the same manner as in Production method (3-4).

Manufacturing method 5.

Embedded image (Wherein, R ¹ , R ² , R ³ , Het, B ¹ , B ² ,
B ³ , B ⁴ , X, Y, m and n are the same as described above. )

The heterocyclic dicarboxylic anhydride represented by the general formula (VI) is combined with the amines represented by the general formula (II-1) or (II-2) or salts thereof in the presence of an inert solvent. By reacting below, a heterocyclic dicarboxylic acid amide represented by the general formula (IV-3) is obtained, and the heterocyclic dicarboxylic acid amide is isolated or not isolated, and R ² represents a hydrogen atom. In the case of the heterocyclic dicarboxylic acid amides (IV-3), a condensation reaction is carried out in the presence of a condensing agent to obtain a compound represented by the general formula (IX), and the compound (IX) is isolated or not isolated. Reacting with an aromatic amine represented by the general formula (V-1) in the presence of an inert solvent,
In the case of heterocyclic dicarboxylic acid amides (IV-3) in which R ² of the heterocyclic dicarboxylic acid amides (IV-3) represents other than a hydrogen atom, an aromatic ring amine represented by the general formula (V-1) By performing a condensation reaction in the presence of a condensing agent, the compound represented by the general formula (I-5) or the general formula (I
The heterocyclic dicarboxylic phthalic acid diamide derivative represented by -4) can be produced.

Alternatively, by reacting a heterocyclic dicarboxylic anhydride represented by the general formula (VI) with an aromatic ring amine represented by the general formula (V-1) in the presence of an inert solvent, formula
A heterocyclic dicarboxylic acid amide represented by (IV-4), and isolating or not isolating the heterocyclic dicarboxylic acid amide (IV-4), a heterocyclic dicarboxylic acid in which R ³ represents a hydrogen atom In the case of amides (IV-4), a condensation reaction is performed in the presence of a condensing agent,
A compound represented by the general formula (IX-1), and isolating or not isolating the compound (IX-1), the compound represented by the general formula (IX-1) in the presence of an inert solvent:
(II-1) or an amine represented by the general formula (II-2) or a salt thereof, and when R ³ is a heterocyclic dicarboxylic amide (IV-4) other than a hydrogen atom, the compound represented by the general formula ( II-1) or the general formula (II-
Formula (I-1) or Formula (I-) by subjecting an amine represented by 2) or a salt thereof to a condensation reaction in the presence of a condensing agent.
4) A heterocyclic dicarboxylic acid diamide derivative represented by the following formula can be produced. (5-1). General formula (VI) → General formula (IV-3) or General formula (IV-
4) The target compound can be produced by carrying out the reaction in the same manner as in Production method (1-3). (5-2). General formula (IV-3) or → General formula (IX) or General formula
(IV-4) → general formula (IX-1) Med. Chem. , 10 , 982 (19
The target product can be produced according to the method described in 67). (5-3). General formula (IV-3) or General formula (IV-4) → General formula (I
-Four)

The heterocyclic dicarboxylic acid amide derivative represented by the general formula (IV-3) or (IV-4) is combined with the general formula (II-1) or (I-1)
It can be produced by reacting an amine represented by I-2) or the general formula (V-1) in the presence of a condensing agent and an inert solvent. This reaction can be carried out, if necessary, in the presence of a base. As the inert solvent used in this reaction,
For example, tetrahydrofuran, diethyl ether, dioxane, chloroform, methylene chloride and the like can be exemplified. The condensing agent used in this reaction may be any one used in the usual amide synthesis, such as Mukaiyama reagent (2-chloro-N-methylpyridinium iodide), DCC (1,3-dicyclohexylcarbodiimide), CDI (Carbonyldiimidazole), DEPC
(Diethyl cyanophosphate) and the like, and its use amount is equimolar to excess with respect to the heterocyclic dicarboxylic acid amide derivative represented by the general formula (IV-3) or (IV-4). What is necessary is just to select and use suitably from the range of mol.

As the base that can be used in this reaction, for example, organic bases such as triethylamine and pyridine and inorganic bases such as potassium carbonate can be exemplified. What is necessary is just to select and use suitably from the equimolar to excess molar range with respect to the heterocyclic dicarboxylic amide derivative represented by Formula (IV-4). Reaction temperature is 0 ° C
The reaction can be carried out in the boiling point range of the inert solvent used, and the reaction time is not fixed depending on the reaction scale, the reaction temperature and the like, but is in the range of several minutes to 48 hours. After completion of the reaction, the desired product can be isolated from the reaction system containing the desired product according to a conventional method, and the desired product can be produced by purification by recrystallization, column chromatography or the like, if necessary.

(5-4). General formula (IX) → General formula (I-5) or General formula (IX-1) → General formula (I-1) The reaction is carried out in the same manner as in Production method (1-5) to produce the desired product be able to.

Manufacturing Method 6.

Embedded image (Where R, R ¹ , R ² , Het, B ¹ , B ² , B ³ ,
B ⁴ , X, Y, hal, m and n are the same as above. )

A heterocyclic dicarboxylic acid ester derivative represented by the general formula (X) is halogenated in the presence or absence of an inert solvent to obtain a heterocyclic dicarboxylic acid halide represented by the general formula (XI), The heterocyclic dicarboxylic acid halides (XI)
Is reacted with an aromatic amine represented by the general formula (V) in the presence of an inert solvent and a base without isolation or a heterocyclic dicarboxylic acid represented by the general formula (IV-3) As an amide, the heterocyclic dicarboxylic acid amide (IV-3) is subjected to a hydrolysis reaction in the presence or absence of an inert solvent without or without isolation, and represented by the general formula (IV-1) Heterocyclic dicarboxylic acid amides represented, said heterocyclic dicarboxylic acid amides (IV-
The condensation reaction is carried out by isolating or not isolating 1),
X-1) represented by a heterocyclic dicarboxylic acid isoimide derivative, the heterocyclic dicarboxylic acid isoimide derivative (IX-1) and an amine represented by the general formula (II-1) or the general formula (II-2) Alternatively, the heterocyclic dicarboxylic acid diamide derivative represented by the general formula (I-1) can be produced by reacting with a salt thereof.

(6-1). General formula (X) → General formula (XI) As the inert solvent that can be used in this reaction, any solvent that does not significantly inhibit the progress of this reaction may be used.Examples include aromatic hydrocarbons such as benzene, toluene, and xylene. Halogenated hydrocarbons such as methylene chloride, chloroform and carbon tetrachloride, chlorinated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene, chain or cyclic ethers such as diethyl ether, dioxane and tetrahydrofuran, and esters such as ethyl acetate And the like. These inert solvents can be used alone or in combination of two or more. As the halogenating agent, for example, a halogenating agent such as thionyl chloride, phosphorus oxychloride, and phosphorus trichloride can be used.
What is necessary is just to select and use suitably from the range of 1-10 equivalent with respect to the heterocyclic dicarboxylic acid ester derivative represented by (VII). The reaction can be carried out at a temperature of from 0 ° C. to the reflux temperature of the inert solvent to be used. The reaction time is not fixed depending on the reaction scale, the reaction temperature and the like, but may be appropriately selected within a range from several minutes to 48 hours. After completion of the reaction, the desired product can be isolated from the reaction system containing the desired product according to a conventional method, and the desired product can be produced by purification by recrystallization, column chromatography or the like, if necessary. In addition, it is also possible to use the next reaction step without isolating the target substance from the reaction system.

(6-2). General formula (XI) → General formula (IV-3) As the inert solvent that can be used in this reaction, for example, the inert solvents exemplified in the production method (1-3) can be used. As the base, an inorganic base or an organic base can be used.For example, as the inorganic base, a hydroxide of an alkali metal atom such as sodium hydroxide or potassium hydroxide, and as the organic base, an organic base such as triethylamine or pyridine is used. Can be used in an amount of 0.5 to 0.5 to the heterocyclic dicarboxylic acid halide represented by the general formula (VII-1).
What is necessary is just to select and use suitably from the range of 3 equivalents. Since this reaction is an equimolar reaction, each reactant may be used in an equimolar amount.However, the aromatic ring represented by the general formula (V) is used for the heterocyclic dicarboxylic acid halide represented by the general formula (XI). The amide can be appropriately selected from the range of 0.5 to 2 equivalents. The reaction can be carried out at a temperature of from 0 ° C. to the reflux temperature of the inert solvent to be used. The reaction time is not fixed depending on the reaction scale, the reaction temperature and the like, but may be appropriately selected within a range from several minutes to 48 hours. After completion of the reaction, the desired product can be isolated from the reaction system containing the desired product according to a conventional method, and the desired product can be produced by purification by recrystallization, column chromatography or the like, if necessary. In addition, it is also possible to use the next reaction step without isolating the target substance from the reaction system.

(6-3). General formula (IV-3) → General formula (IV-1) In this reaction, the target compound can be produced according to the production method (1-1). (6-4). General formula (IV-1) → General formula (IX-1) In this reaction, the target compound can be produced according to the production method (5-2). (6-5). General formula (IX-1) → General formula (I-1) In this reaction, the target compound can be produced according to the production method (1-5).

Manufacturing method 7.

Embedded image (Where R ¹ , R ² , Het, B ¹ , B ² , B ³ ,
B ⁴ , X, Y, hal, m and n are the same as above. )

The heterocyclic dicarboxylic acid represented by the general formula (VII) is halogenated in the presence of a halogenating agent to form a compound represented by the general formula (X
II) and then the acid halides
(XII) in the presence or absence of an inert solvent, the general formula (V)
By reacting with a substituted aromatic amine represented by the general formula (IX-1) and (III) to obtain a heterocyclic dicarboxylic acid isoimide and a heterocyclic dicarboxylic acid imide. By reacting with an amine represented by the general formula (II-1) or the general formula (II-2) or a salt thereof in the presence or absence of an inert solvent without separation or isolation, the general formula The heterocyclic dicarboxylic acid diamide derivative represented by (I-1) can be produced. (7-1) General formula (VII) → General formula (XII) In this reaction, the desired product can be produced according to the production method (6-1). (7-2) General formula (XII) → General formulas (IX-1) and (III) The reaction can be carried out in the same manner as in Production method (6-2) to produce the desired product. (7-3) General formulas (IX-1) and (III) → General formula (I-1) The reaction can be carried out in the same manner as in Production method (1-5) to produce the desired product.

Manufacturing Method 8

Embedded image (Where R ¹ , R ² , Het, B ¹ , B ² , B ³ ,
B ⁴ , X, Y, hal, m and n are the same as above. )

The heterocyclic carboxylic acid amide represented by the general formula (XIII-1) or (XIII-2) is orthometalated using a metal reagent such as butyllithium, and then reacted with carbon dioxide. The compound is converted into a heterocyclic dicarboxylic acid amide derivative represented by the general formula (IV-3) or (IV-4), and then processed in the same manner as in Production Methods (5-2) to (5-4). The heterocyclic dicarboxylic diamide derivative represented by the general formula (I-1), (I-4) or (I-5) can be produced. (8-1). General formula (XIII-1) or General formula (XIII-2) → General formula (IV-3) or General formula (IV-4) Org. Chem. , 29 , 853 (19
After ortholithiation according to the method described in (64), the compound can be produced by introducing carbon dioxide into the mixture at -80 ° C to room temperature. After completion of the reaction, the desired product can be isolated from the reaction system containing the desired product according to a conventional method, and the desired product can be produced by purification by recrystallization, column chromatography or the like, if necessary.

Manufacturing method 9

Embedded image

(Wherein R ¹ , R ² , Het, X, Y, h
al, m and n are the same as above. This reaction is an oxidation reaction of a nitrogen atom in a heterocycle, and is generally performed by reacting a heterocyclic dicarboxylic imide represented by the general formula (III-4) with an oxidizing agent in the presence of an inert solvent. The heterocyclic dicarboxylic imide derivative represented by the formula (III-5) is obtained by isolating or not isolating the heterocyclic dicarboxylic imide derivative (III-5). The heterocyclic dicarboxylic acid diamide derivative represented by the general formula (I-6) can be produced by reacting with an amine represented by II-2) or a salt thereof.

(9-1) General formula (III-4) → General formula (III-
5) The inert solvent that can be used in this reaction may be any solvent that does not inhibit the progress of this reaction, such as methylene chloride,
Examples thereof include chloroform, carbon tetrachloride, chlorobenzene, water, acetic acid, ethyl acetate, and trifluoroacetic acid. These inert solvents can be used alone or as a mixture of two or more. Examples of the oxidizing agent used in this reaction include hydrogen peroxide, m-chloroperbenzoic acid, peracetic acid and the like. The reaction temperature of this reaction is 0 ° C
１００100 ° C., the reaction time is the reaction scale,
The temperature is not fixed depending on the reaction temperature, but may be appropriately selected in the range of several minutes to 48 hours. (9-2) General formula (III-5) → General formula (I-6) This reaction can be produced according to the production method (1-5).

The representative examples of the heterocyclic dicarboxylic diamide derivatives represented by the general formula (I) of the present invention are shown in Tables 1 to 3 below.
Although shown in Table 3, the present invention is not limited to these. General formula (I)

Embedded image

[0076]

[0077]

[0078]

[0079]

[0080]

[0081]

[0082]

[0083]

[0084]

[0085]

[0086]

[0087]

[0088]

[0089]

[0090]

[0091]

[0092]

[0093]

[0094]

[0095]

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119]

[0120]

[0121]

[0122]

[0123]

[0124]

[0125]

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133]

[0134]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148]

[0149]

[0150]

[0151]

[0152]

[0153]

[0154]

[0155]

[0156]

[0157]

[0158]

[0159]

[0160]

[0161]

[0162]

[0163]

[0164]

[0165]

[0166]

[0167]

[0168] In Tables 1 to 33, "Ac" represents an acetyl group,
“Ph” represents a phenyl group, “Pyr” represents a pyridyl group,
"C-" indicates an alicyclic hydrocarbon group.

The agricultural and horticultural insecticide containing the heterocyclic dicarboxylic acid diamide derivative represented by the general formula (I) of the present invention as an active ingredient can be used for various agricultural and forestry plants that damage rice, fruit trees, vegetables, other crops, flowers and the like. It is suitable for controlling pests such as horticulture, stored grain pests, sanitary pests, nematodes, and the like. For example, Adelaphys orana fasciata, Adoxophyes sp., Graphholita inopinata, Nasihime Shingui (Grapho
lita molesta, legume mini squirt (Leguminivora glyci)
nivorella), Kuwahamaki (Olethreutes mori), Canohosoga (Caloptilia thevivora), Apple hosoga (Calo)
ptilia zachrysa, Kimmon Hosoga (Phyllonorycter)
ringoniella), Nashihosoga (Spulerrina astaurot)
a), cabbage butterfly (Piers rapae crucivora), giant tobacco (Heliothis sp.), codling moth (Laspey)
resia pomonella) and diamondback moth (Plutella xylostella)
), Apple turtle (Argyresthia conjugell)
a), peach sink moth (Carposina niponensis),

Glyphode (Chilo suppressalis), Cob beetle (Cnaphalocrocis medinalis), Chamadara (Ephestia elutella), Kwanomeiga (Glyphode)
s pyloalis, Sankameiga (Scirpophaga incertula)
s), scorpion parsley (Parnara guttata), armyworm (Pseudaletia separata), rice armyworm (Sesamia)
inferens), Spodoptera litura (Spodoptera litura),
Lepidopteran pests, such as the armyworm (Spodoptera exigua), the leafhopper (Macrosteles fascifron)
s), leafhopper (Nephotettix cincticeps),
Brown planthopper (Nilaparvata lugens), white-spotted planthopper (Sogatella furcifera), orange lice (Diaphori)
na citri, whitefly (Aleurolobus taonaba)
e), whiteflies (Bemisia tabaci), whiteflies (Trialeurodes vaporariorum), flies (Lipaphis erysimi), peach aphids (Myzus persicae), hornworms (Ceroplastes)
ceriferus), Peanut (Pulvinaria a)
urantii), Citrus Insect (Pseudaonidia d)
uplex), pear beetle (Comstockaspis pern)
iciosa), Unaspis yanonensis
Hemiptera pests such as the nematode (Pratylenchuss)
p.), Japanese beetle (Anomala rufocuprea), Japanese beetle (Popillia japonica), Tobacco beetle (Lasioderm)
a serricorne), Flycatcher beetle (Lyctusbrunneus)
), A ladybird (Epilachna vigintiotop)
unctata), adzuki beetle (Callosobruchus chinensi)
s),

Weevil (Listroderes costirostr)
is), the weevil (Sitophilus zeamais), the cotton weevil (Anthonomus gradis gradis), the rice weevil (Lissorhoptrus oryzophilus), the rice weevil (Aula)
cophora femoralis), rice beetle (Oulema ory)
zae), the flea beetle (Phyllotreta striolata)
), Pine bark beetle (Tomicus piniperda), Colorado potato beetle (Leptinotarsa decemlineata),
Mexican beetle (Epilachna varivestis),
Beetle pests such as corn rootworms (Diabrotica sp.), Sea flies (Dacus (Zeugodacus) cucurbitae), citrus fruit flies (Dacus (Bactrocera) dorsalis), rice leaf flies (Agromyza oryzae), onions (Deli)
a antiqua), Fly (Delia platura), Soybean Thrips (Asphondylia sp.), Housefly (Musca do
mestica), Culex pipiens pipiens, and other dipteran pests such as Platynench
us coffeae), potato cyst nematode (Globoder)
a rostochiensis), root-knot nematode (Meloidogyne)
sp.), Tangerine nematode (Tylenchulus semipenetr)
ans), Nepenthes nematode (Aphelenchus avena)
e), Agarene nematode (Aphelenchoides ritzemabos)
It has a strong insecticidal effect against pests of the order Nematodes such as i).

The agricultural and horticultural insecticides containing the heterocyclic dicarboxylic acid diamide derivative represented by the general formula (I) of the present invention as an active ingredient are useful for paddy field crops, field crops, fruit trees, vegetables, other crops and flowers and the like. Since it has a remarkable controlling effect on the pests that cause damage, paddy fields, fields, fruit trees, vegetables before or at the time when the pests are confirmed to occur, in accordance with the time when the pests are predicted to occur The desired effect of the agricultural and horticultural insecticide of the present invention can be exhibited by treating paddy water, foliage, or soil of other crops, flowers and the like.

The agricultural and horticultural insecticide of the present invention is generally used after being formulated into a convenient form according to the conventional method for agricultural chemicals. That is, the heterocyclic dicarboxylic acid diamide derivative represented by the general formula (I) is dissolved, separated, and suspended by mixing these in an appropriate inert carrier or in an appropriate ratio together with an auxiliary as necessary. The mixture may be mixed, impregnated, adsorbed or adhered and formulated into an appropriate dosage form, for example, a suspension, emulsion, liquid, wettable powder, granule, powder, tablet or the like. The inert carrier that can be used in the present invention may be either solid or liquid. Examples of the material that can be a solid carrier include soybean flour, cereal flour, wood flour, bark flour, saw flour, and tobacco stem flour. , Walnut shell powder, bran, cellulose powder, residue after extraction of plant extract, synthetic polymers such as pulverized synthetic resins, clays (eg, kaolin, bentonite, acid clay), talcs (eg, talc, pyrophyllide, etc.), Silicas (for example, diatomaceous earth, silica sand, mica, white carbon [a synthetic high-dispersion silicic acid also referred to as hydrous finely divided silicon or hydrous silicic acid, some of which contain calcium silicate as a main component depending on the product]), activated carbon, sulfur powder, Inorganic mineral powders such as pumice, calcined diatomaceous earth, crushed bricks, fly ash, sand, calcium carbonate, calcium phosphate, ammonium sulfate, phosphorous ammonium, ammonium nitrate,
Urea, chemical fertilizers such as salt and salt, compost and the like,
These are used alone or in the form of a mixture of two or more.

The material which can be a liquid carrier is selected from those having a solvent function per se and those capable of dispersing the active ingredient compound with the aid of an auxiliary agent without the solvent function. The following carriers can be exemplified as typical examples. These can be used alone or in the form of a mixture of two or more. Examples thereof include water, alcohols (eg, methanol, ethanol, isopropanol, butanol). , Ethylene glycol and the like), 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, etc.) Dimethylacetamide, etc.), nitriles (eg, acetonitrile, etc.), dimethylsulfoxides and the like.

Examples of the other adjuvants include the following representative adjuvants. These adjuvants are used according to the purpose, and may be used alone or, in some cases, in combination of two or more adjuvants. In some cases, however, it is possible to use no auxiliaries. Surfactants are used for the purpose of emulsifying, dispersing, solubilizing and / or wetting the active ingredient compound, such as polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether, and polyoxyethylene higher fatty acid. Ester, polyoxyethylene resin acid ester, polyoxyethylene sorbitan monolaurate, polyoxyethylene sorbitan monooleate, alkyl aryl sulfonate, naphthalene sulfonic acid condensate,
Surfactants such as lignin sulfonate and higher alcohol sulfate can be exemplified. For the purpose of stabilizing the dispersion of the active ingredient compound, adhering and / or binding, the following auxiliaries can be used. For example, casein, gelatin, starch, methylcellulose, carboxymethylcellulose can be used. Auxiliaries such as gum arabic, polyvinyl alcohol, pine oil, bran oil, bentonite, and lignin sulfonate can also be used.

The following auxiliaries can be used to improve the flowability of the solid product. For example, auxiliaries such as wax, stearate and alkyl phosphate can be used. As peptizers for suspension products, auxiliary agents such as, for example, naphthalenesulfonic acid condensates, condensed phosphates and the like can also be used. As an antifoaming agent, for example, an auxiliary agent such as silicone oil can be used. The compounding ratio of the active ingredient compound can be adjusted according to need. For example, 0.01 to 50% by weight in the case of powder or granules, and 0.01 to 50% in the case of emulsion or wettable powder. % By weight is appropriate.

The agricultural and horticultural insecticide of the present invention is used as it is for controlling various pests, or is appropriately diluted or suspended with water or the like to form an effective amount for controlling the pests. It may be used by applying it to crops to be produced or places where generation is not preferable. The amount used of the agricultural and horticultural insecticide of the present invention depends on various factors, for example, the purpose, the target pest, the growth status of the crop, the tendency of the pest to occur, the weather, the environmental conditions, the dosage form, the application method, the application place, the application time, etc. Although it fluctuates, the active ingredient compound may be appropriately selected from the range of 0.1 g to 10 kg per 10 ales depending on the purpose. Agricultural and horticultural insecticides of the present invention are further pests to be controlled, other agricultural and horticultural insecticides, acaricides, nematicides for the purpose of extending the proper period of control, or reducing the amount of medicine, synergistic effect , Fungicides, biological pesticides, and the like, and can also be used by mixing with herbicides, plant growth regulators, fertilizers, and the like, depending on the use situation.

Other agricultural and horticultural insecticides, acaricides, and nematicides used for this purpose include, for example, ethion, trichlorfon, methamidophos, acephate, dichlorvos, mevinphos, monocrotophos, malathion, dimethoate, formothione, mecarbam. , Bamidion,
Thiometon, disulfoton, oxydeprophos, nared, methyl parathion, fenitrothion, cyanophos, propaphos, fenthion, prothiophos, propenophos, isofenphos, temefos, fentoate, dimethylvinphos, chlorfevinphos, tetrachlorvinphos, foxime, isoxathion, pyraclophos, Methidathion, chloropyrifos, chlorpyrifos
Methyl, pyridafenthion, diazinon, pirimiphosmethyl, fosalon, phosmet, dioxabenzophos, quinalphos, terbuphos, etoprophos, cassaphos, mesurfenphos, DPS (NK-0795), phosphocarb, fenamiphos, isoamidophos, phosthiazate, isazophos, enaprophos, fenthion, phosthiophene, phosthiophene Diclofenthion, thionazine, sulprophos, fensulfotion, diamidaphos, pyrethrin, allethrin,

Praletrin, resmethrin, permethrin, tefluthrin, bifenthrin, fenpropatrin, cypermethrin, alpha cypermethrin, cyhalothrin, lambda cyhalothrin, deltamethrin, acrinatrine, fenvalerate, esfenvalerate, flucitrinate, fluvalinate, cycloproline Trin, Etofenprox, Halfenprox,
Silafluofen, flucitrinate, fluvalinate, mesomil, oxamyl, thiodicarb, aldicarb, alanib, cartap, metlcarb, xylicalub, propoxur, phenoxycarb, fenobcarb, ethiophencarb, phenothiocarb, bifenazate, BPMC, carbaryl, pirimicarb, furimicarb, carbamifuran, pirimicarb Fratiothiocarb, benflacarb, aldoxycarb, diafenthiuron, diflubenzuron, teflubenzuron, hexaflumuron, novalron, lufenuron, flufenoxuron,
Chlorfluazuron, fenbutatin oxide, tricyclohexyltin hydroxide, sodium oleate, potassium oleate, methoprene, hydroprene, binapacryl, amitraz,

Dicofol, quercene, chlorbenzylate, phenisobromolate, tetradiphone, bensultap, benzomate, tebufenozide, methoxyfenozide, chromafenozide, propargite, acequinosyl, endosulfan, diophenolan, chlorfenapyr, fenpyroximate, tolfenpyrad, epronilate, fipronilate, fipronilate, fipronilate, fipronilate Hexythiazox, nicotine sulfate, nitenpyram, acetamiprid, thiacloprid, imidacloprid, thiamethoxam, clothianidin, nidinotefuran, fluazinam, pyriproxyfen, hydramethylnon, pyrimidifen, pyridaben, cyromazine, TP
IC (tripropyl isocyanurate), pymetrozine, clofentezin, buprofezin, thiocyclam, phenazaquin, quinomethionate, indoxacarb, polynactin complex, milbemectin, abamectin, emamectin benzoate, spinosad, BT
(Bacillus thuringiensis), Azadirachtin,
Chloronicotinyl compounds such as rotenone, hydroxypropyl starch, levamisole hydrochloride, metham sodium, morantel tartrate, dazomet, triclamide, bastria, monacrosporium fimatopagum, albendazole, oxybendazole, oxfenzazole, fenbendazole, etc. , Carbamate-based compounds, pyrethroid-based compounds, macrolide-based compounds, organophosphorus-based compounds, and other agricultural and horticultural insecticides, acaricides, or nematicides.

Examples of agricultural and horticultural fungicides used for the same purpose include sulfur, lime-sulfur mixture, basic copper sulfate, iprovenphos, edifenphos, tolclofos-methyl, thiram, polycarbamate, zineb, manzeb, mancozeb. , Propineb, thiophanate, thiophanate methyl, benomyl, iminoctadine acetate, iminoctadine albesilate, mepronil, flutranil, pencyclon, framethopyr, thifluzamide, metalaxyl, oxadixyl, carpropamide, diclofluanid, flusulfamide, chlorothalonil N, clesoxinil methyl N -9425), hymexazole, eclomethol, fluoroimide, procymidone, vinclozolin, iprodione, triadimefon, triflumizo , Bitertanol, triflumizole, ipconazole, fluconazole, propiconazole, difenoconazole, microbutanyl, tetraconazole, hexaconazole, tebuconazole, imibenconazole, prochloraz, pefurazoate, cyproconazole, isoprothiolane, fenarimol, pyrimethanil, mepanipilim Phenox, fluazinam, triforine, diclomedin, azoxystrobin,
Agricultural and horticultural fungicides such as thiadiazine, captan, probenazole, acibenzofural-S-methyl (CGA-245704), fusalide, tricyclazole, pyroquilon, quinomethionate, oxolinic acid, dithianone, kasugamycin, validamycin, polyoxin, blasticidin, streptomycin and the like. Can be

Similarly, herbicides include, for example, glyphosate, sulfosate, glufosinate, bialaphos, butamiphos, esprocarb, prosulfocarb, benthiocarb, pyributicarb, ashram, linuron, dimuron, bensulfuron-methyl, cyclosulfamuron, sinosulfuron, pyrathiol Zosulfuron-ethyl, azimsulfuron, imazosulfuron, tenylchlor, alachlor, pretilachlor, clomeprop, etobenzanide, mefenacet, pendimethalin, bifenox, acifluofen, lactofen, cyhalofop-butyl, ioxynil, bromobutide, alloxydim, cetoxydim, napropamide, napropamide Pyrazolate, benzofenap, pyraflufen-ethyl, imaza Le, sulfentrazone, cafe down stroke - le, Bentokisazon, Okisazoazon, paraquat, diquat, pyriminobac, simazine, atrazine, dimethametryn, triaziflam, benfuresate, Furci asset-methyl, quizalofop-ethyl,
Compounds having herbicides such as bentazone and calcium peroxide can be exemplified, but the present invention is not limited to these. In addition, the said compound name shows a general name except special mention.

Examples of biological pesticides include nuclear polyhedrosis virus (NPV), granulosis virus (GV), cytoplasmic polyhedrosis virus (CPV), and insect poxvirus (Entomopox). virus, EPV), Monoclosporium fimatopagum (Mona
a microbial pesticide such as crosporium phymatophagum, Steina-nema carpocapsae, Steinernema carpocapsae, Steinernema kushidai, Pasturia penetrans, etc .;
Lignolan (Trichoderma lignorum), Agrobacterium radiobactor
), Nonpathogenic Erwinia carotobola (Erwinia car
otovora), Bacillus subtilis
The same effects can be expected by mixing and using a microbial pesticide used as a fungicide such as Xanthomonas campestris (Xanthomonas campestris) and a biological pesticide used as a herbicide such as Xanthomonas campestris.

Further, as biopesticides, for example, encarsia bee (Encarsia formosa), koreman abra wase (Ap
hidius colemani), Aphid flies (Aphidoletes)
aphidimyza) and the European bee (Diglyphus isaea)
), Natural beneficiaries such as the beetle (Dacnusa sibirica);
Microbial pesticides such as Beurveria brongniartii, (Z) -10-tetradecenyl acetate,
(E, Z) -4,10-tetradecadinyl 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 together with a pheromone agent such as 1-octadecene.

[0185]

The present invention will be described in more detail with reference to the following Examples, which by no means limit the present invention. Embodiment 1 FIG. (1-1). Production of N- [4- (heptafluoro-2-propyl) -2-methylphenyl] pyridine-3,4-dicarboximide. Dissolve 1.50 g of pyridine-3,4-dicarboxylic anhydride and 2.75 g of 4- (heptafluoro-2-propyl) -2-methylaniline in 10 ml of THF, and add 3
A time reaction was performed. After completion of the reaction, the solvent was distilled off under reduced pressure, trifluoroacetic anhydride (20 ml) was added to the obtained residue, and the mixture was reacted under reflux for 3 hours. After completion of the reaction, the solvent was distilled off under reduced pressure to obtain crude N- [4- (heptafluoro-2).
-Propyl) -2-methylphenyl] pyridine-3,4
-Dicarboximide was obtained quantitatively.

(1-2). 3- [4- (heptafluoro-2-propyl) -2-methylphenyl] aminocarbonyl-4-pyridinecarboxylic acid-2-propylamide (Compound No. 230) and 4- [4- (heptafluoro-2-propyl) Production of -2-methylphenyl] aminocarbonyl-3-pyridinecarboxylic acid-2-propylamide (Compound No. 512). 4.1 g of N- [4- (heptafluoro-2-propyl) -2-methylphenyl] pyridine-3,4-dicarboximide is dissolved in 10 ml of dioxane, 0.8 g of isopropylamine is added to the solution, and room temperature is added. For 8 hours. After completion of the reaction, the solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel column chromatography using a mixed solvent of hexane / ethyl acetate = 2/1 as an eluent,
(Compound No. 230) 2.1 g and (Compound No. 51)
2) 1.8 g were obtained as white crystals. Physical properties: Compound No 230 m. p. 234-236 ° C Yield 45% Compound No. 512 m. p. 206-208 ° C Yield 39%

Embodiment 2 (2-1). 5-bromo-3- [4- (heptafluoro-2-propyl) -2-methylphenyl] aminocarbonyl-1-phenyl-4-pyrazolecarboxylic acid 2-propylamide (Compound No. 1382) and 5-bromo-
4- [4- (heptafluoro-2-propyl) -2-methylphenyl] aminocarbonyl-1-phenyl-3-
Pyrazolcarboxylic acid 2-propylamide (Compound No.
Production of 1414) 500 mg of 5-bromo-1-phenyl-3,4-pyrazoledicarboxylic acid was dissolved in 10 ml of thionyl chloride and reacted at reflux temperature for 2 hours. After the completion of the reaction, thionyl chloride was distilled off under reduced pressure to obtain a crude acid chloride. This compound was dissolved in THF (2 ml), and heptafluoro-2-propyl) -2-methylaniline (420 mg) and triethylamine (410 mg) were dissolved in THF (10 ml).
Was dropped. After dropping, isopropylamine 470m
g was added at 0 ° C. and reacted at room temperature for 2 hours. After the reaction,
The triethylamine hydrochloride was filtered off, and the mother liquor was concentrated.
The resulting residue was purified by silica gel column chromatography using ethyl acetate / n-hexane as an eluent to give 5-bromo-3- [4- (heptafluoro-2).
-Propyl) -2-methylphenyl] aminocarbonyl-1-phenyl-4-pyrazolecarboxylic acid 2-propylamide (Compound No. 1382) 360 mg, 5-bromo-4- [4- (heptafluoro-2-propyl)-
2-Methylphenyl] aminocarbonyl-1-phenyl-3-pyrazolecarboxylic acid 2-propylamide (Compound No. 1414) (360 mg) was obtained as white crystals. Physical properties: Compound No. 1382 m.p. p. 164-166 ° C Yield 36% Compound No. 1414 m. p. 167-169 ° C Yield 36%

Embodiment 3 (3-1). Preparation of 2-chloro-4- [4- (heptafluoro-2-propyl) -2-methylphenyl] aminocarbonyl-3-pyridinecarboxylic acid 2.78 g of diisopropylamine was added to 20 ml of anhydrous THF.
, And 18 ml of n-butyllithium hexane solution (1.53M) was added dropwise at -78 ° C under an argon atmosphere.
After stirring at −78 ° C. for 1 hour, 4- (heptafluoro-2-propyl) -2 2-chloro-4-pyridinecarboxylate
A solution of 5.17 g of -methylanilide dissolved in 100 ml of THF was added dropwise at -78 ° C. After dropping, -78 ° C
For 2 hours, and carbon dioxide gas was blown for 1 hour. Thereafter, the temperature was raised to room temperature, 200 ml of 1N hydrochloric acid was added, and the mixture was extracted with ethyl acetate. After the organic layer was dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure to obtain a crude target compound.
70 g (82% yield) were obtained as an amorphous solid. This was used for the next reaction without further purification.

(3-2). 2-chloro-4- [4-
(Heptafluoro-2-propyl) -2-methylphenyl] aminocarbonyl-3-pyridinecarboxylic acid 2-
Production of propylamide (Compound No. 524) 500 mg of 2-chloro-4- [4- (heptafluoro-2-propyl) -2-methylphenyl] aminocarbonyl-3-pyridinecarboxylic acid was dissolved in 10 ml of t-butylmethyl ether. , Trifluoroacetic anhydride 340mg
Was added and stirred at room temperature for 2 hours. After confirming the disappearance of the raw materials by TLC, 330 mg of isopropylamine was added, and the mixture was further stirred at room temperature for 2 hours. After completion of the reaction, ethyl acetate was added, and the reaction solution was washed with water, a saturated aqueous solution of sodium hydrogen carbonate and saturated saline in this order, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel column chromatography using ethyl acetate / n-hexane as an eluent to give the desired product 46 as white crystals.
0 mg was obtained. Physical properties m.
p. 275-277 ° C Yield 84%

Embodiment 4 (4-1). Preparation of N- [4- (heptafluoro-2-propyl) -2-methylphenyl] pyridine-2,3-dicarboximide-1-oxide N- [4- (heptafluoro-2-propyl) -2-oxide [Methylphenyl] pyridine-2,3-dicarboximide (3.1 g) was dissolved in chloroform (25 ml), and m-chloroperbenzoic acid (5.0 g) was added at room temperature. After stirring at room temperature for 3 hours, a saturated aqueous sodium hydrogen carbonate solution was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, a saturated aqueous solution of sodium bicarbonate and saturated saline in this order, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel column chromatography using ethyl acetate / n-hexane as an eluent to obtain 820 mg (yield: 84%) of the desired product. (4-2). 3- [4- (heptafluoro-2-propyl) -2-methylphenyl] aminocarbonyl-2-
Production of (2-propyl) aminocarbonylpyridine-N-oxide (Compound No. 804) N- [4- (heptafluoro-2-propyl) -2-methylphenyl] pyridine-2,3-dicarboximide-
400 mg of 1-oxide was dissolved in 10 ml of THF, 200 mg of isopropylamine was added, and the mixture was stirred at room temperature for 5 hours. After completion of the reaction, the solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel column chromatography using ethyl acetate / n-hexane as an eluent to obtain 290 mg of the desired product as white crystals. Physical properties m. p. 108-110 ° C Yield 63%

[0191] Representative preparation examples and test examples of the present invention are shown below, but the present invention is not limited thereto.
In the preparation examples, “parts” means “parts by weight”. Formulation Example 1 Compounds listed in Tables 1-33 50 parts Xylene 40 parts Mixture of polyoxyethylene nonylphenyl ether and calcium alkylbenzenesulfonate 10 parts The above are uniformly mixed and dissolved to form an emulsion. Formulation Example 2. Compounds listed in Tables 1-33 3 parts Clay powder 82 parts Diatomaceous earth powder 15 parts The above are uniformly mixed and pulverized to obtain a powder.

Formulation Example 3 Compounds listed in Tables 1-33 5 parts Mixed powder of bentonite and clay 90 parts Calcium ligninsulfonate 5 parts Mix uniformly, add an appropriate amount of water, knead, granulate,
Dry to granules. Formulation Example 4. Compounds listed in Tables 1-33 20 parts Kaolin and synthetic highly dispersed silicic acid 75 parts Mixture of polyoxyethylene nonylphenyl ether and calcium alkylbenzenesulfonate 5 parts I do.

Test Example 1 Diamondback moth (Plutella xylostella)
Insecticidal test. Adult Chinese moths were released to Chinese cabbage seedlings to lay eggs, and two days after release, Chinese cabbage seedlings with spawning eggs were shown in Tables 1 to 33.
It was immersed for about 30 seconds in a drug solution diluted to 500 ppm with a drug containing the compound shown in the table as an active ingredient, air-dried, and allowed to stand in a constant temperature room at 25 ° C. Six days after the immersion in the chemical, the number of hatching insects was investigated.
The mortality was calculated by the following equation. 3 units in 10 wards per ward [number 1]

As a result, Compound Nos. 13, 18, 32,
54, 55, 57, 127, 136, 230, 242,
258, 464, 484, 512, 524, 737, 7
85, 794, 795, 804, 805, 821, 98
9,990,1009,1095,1110,112
7, 1158, 1189, 1204, 1220, 122
1, 1247, 1249, 1251, 1255, 126
7, 1269, 1271, 1275, 1303, 130
6, 1313, 1320, 1414, 1429, 147
3, 1505, 1548, and 1549 showed a corrected mortality of 90% or more.

Test Example 2 Anthracite (Adoxo
phyes sp.). Tea leaves were immersed for about 30 seconds in a medicinal solution prepared by diluting a drug containing the compounds described in Tables 1 to 33 into an active ingredient to 500 ppm, air-dried, and then placed in a 9 cm-diameter plastic petri dish, and inoculated with a larva of Anemonium brassicae. Later, 25
The sample was placed in a constant temperature room at 70 ° C. and a humidity of 70%. Eight days after the inoculation, the number of live and dead insects was examined, the mortality was calculated by the following formula, and the judgment was made according to the judgment criteria of Test Example 1. 10 wards per ward, 3 stations [number 2]

As a result, Compound Nos. 13, 18, 55,
57, 127, 136, 230, 464, 484, 51
2, 524, 737, 794, 795, 805, 82
1, 989, 1009, 1048, 1095, 112
7, 1189, 1204, 1220, 1247, 124
9, 1251, 1255, 1303, 1313, 147
3, 1505, 1548, and 1549 showed a corrected mortality of 90% or more.

[0197]

The insecticide for agricultural and horticultural use containing the heterocyclic dicarboxylic acid diamide derivative represented by the general formula (I) of the present invention as an active ingredient is excellent against pests such as, for example, moth moth, edible fleas. It has a controlling effect.

──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. ⁷ Identification symbol FI Theme coat ゛ (Reference) C07D 231/16 C07D 231/16 237/24 237/24 239/28 239/28 241/24 241/24 261 / 06 261/06 263/30 263/30 275/02 275/02 275/03 277/56 277/56 307/54 307/54 333/40 333/40 275/02 (72) Inventor Hideo Takaishi Hyogo (72) Inventor Kazuyuki Sakata 5-6-301 Hondamachi, Kawachinagano City, Osaka (72) Inventor Masayuki Morimoto 1-28, Nishinoyamacho, Kawachinagano City, Osaka Prefecture 305 (72) Inventor Akira Seo 2-3-19-1 Kimigaoka, Hashimoto City, Wakayama Prefecture

Claims (7)

[Claims] 1. A compound of the general formula (I)[Wherein, R¹, R^TwoAnd R^ThreeMay be the same or different
And hydrogen atom, C_Three-C₆Cycloalkyl group, halo C_Three-C₆Shi
Chloroalkyl group or -A¹-(R^Four) R (where A ¹Is C₁
 -C₈Alkylene group, C_Three-C₆Alkenylene group or C_Three-C₆A
A ruquinylene group;^FourMay be the same or different,
Hydrogen atom, halogen atom, cyano group, nitro group, halo C
₁-C₆Alkyl group, C_Three-C₆Cycloalkyl group, halo C_Three-C₆
Cycloalkyl group, C₁-C₆Alkoxycarbonyl group;
One or different di C₁-C₆Alkoxyphosphoryl
Groups, which may be the same or different₁-C₆Alkoxythiopho
Sphoryl group, diphenylphosphino group, diphenylphosphine
Hono group, phenyl group, which may be the same or different, halogen
Atom, C₁-C₆Alkyl group, halo C₁-C₆Alkyl group, C
₁-C₆Alkoxy group, halo C₁-C₆Alkoxy group, C₁-C₆A
Lucylthio group, halo C₁-C₆Alkylthio group, C₁-C₆Al
Killsulfinyl group, halo C₁-C₆Alkylsulfinyl
Group, C₁-C₆Alkylsulfonyl group or halo C₁-C₆Archi
Having one or more substituents selected from rusulfonyl groups
A substituted phenyl group, a heterocyclic group, which may be the same or different,
Halogen atom, C₁-C₆Alkyl group, halo C₁-C₆Alkyl
Group, C₁-C₆Alkoxy group, halo C₁-C₆Alkoxy group, C
₁-C₆Alkylthio group, halo C₁-C₆Alkylthio group, C₁-
C₆Alkylsulfinyl group, halo C₁-C₆Alkylsulf
Ynyl group, C₁-C₆Alkylsulfonyl group or halo C₁-C₆
One or more substituents selected from alkylsulfonyl groups
Having a substituted heterocyclic group or -A^Two-R^Five(Where A^Two Is -O
-, -S-, -SO-, -SO_Two-, -N (R⁶)-(Expression
Medium, R⁶Is a hydrogen atom, C₁-C₆Alkylcarbonyl group, c
B C₁-C₆Alkylcarbonyl group, C₁-C₆Alkoxycal
Bonyl group, phenylcarbonyl group, same or different
Good, halogen atom, C₁-C₆Alkyl group, halo C₁-C₆A
Ruquil group, C₁-C₆Alkoxy group, halo C ₁-C₆Alkoxy
Group, C₁-C₆Alkylthio group, halo C₁-C₆Alkylthio
Group, C₁-C₆Alkylsulfinyl group, halo C₁-C₆Archi
Rusulfinyl group, C₁-C₆Alkylsulfonyl group or ha
B C₁-C₆One or more selected from alkylsulfonyl groups
Substituted phenylcarbonyl group having a substituent, phenyl C
₁-C_FourAlkoxycarbonyl group, same or different
, Halogen atom, C₁-C₆Alkyl group, halo C₁-C₆Al
Kill group, C₁-C₆Alkoxy group, halo C₁-C₆Alkoxy
Group, C₁-C₆Alkylthio group, halo C₁-C₆Alkylthio
Group, C₁-C₆Alkylsulfinyl group, halo C₁-C₆Archi
Rusulfinyl group, C₁-C₆Alkylsulfonyl group or ha
B C₁-C₆One or more selected from alkylsulfonyl groups
Substituted phenyl having substituents on the ring C₁-C_FourAlkoxyka
Rubonyl group, C₁-C₆Alkylsulfonyl group or halo C₁-
C₆It represents an alkylsulfonyl group. ), -C (= O)-
Is -C (= NOR⁷)-(Where R⁷Is a hydrogen atom, C₁-
C₆Alkyl group, halo C₁-C₆Alkyl group, C_Three-C₆Alkene
Le group, halo C_Three-C₆Alkenyl group, C_Three-C₆Alkynyl group,
Cyclo C_Three-C₆Alkyl group, phenyl C₁-C_FourAlkyl group
May be the same or different; a halogen atom, C₁-C₆
Alkyl group, halo C₁-C₆Alkyl group, C₁-C₆Alkoxy
Group, halo C₁-C₆Alkoxy group, C₁-C₆Alkylthio group,
Halo C₁-C₆Alkylthio group, C₁-C₆Alkylsulfini
Le group, halo C₁-C₆Alkylsulfinyl group, C₁-C₆Al
Killsulfonyl group or halo C₁-C₆Alkylsulfonyl group
Substituted substituents having at least one substituent selected from
Nil C₁-C_FourShows an alkyl group. ) And R^FiveIs hydrogen field
Child, C₁-C₆Alkyl group, halo C₁-C₆Alkyl group, C_Three-C₆
Alkenyl group, halo C_Three-C₆Alkenyl group, C_Three-C₆Archi
Nyl group, halo C_Three-C₆Alkynyl group, C_Three-C₆Cycloalkyl
Le group, halo C_Three-C₆Cycloalkyl group, C₁-C₆Alkoxy
 C₁-C₆Alkyl group, C₁-C₆Alkylthio C₁-C₆Alkyl
Group, formyl group, C₁-C₆Alkylcarbonyl group, halo C
₁-C₆Alkylcarbonyl group, C₁-C₆Alkoxycarboni
Group, mono C₁-C₆An alkylaminocarbonyl group, identical or
May be different di C₁-C₆Alkylaminocarbonyl
Group, thing C₁-C₆Alkylaminothiocarbonyl group, identical
Or different C₁-C₆Alkylaminothiocarbo
Nyl group, di C which may be the same or different₁-C₆Alkoxyho
Suphoryl group, di C which may be the same or different₁-C₆Alkoki
Cythiophosphoryl group, phenyl group, same or different
Good, halogen atom, C₁-C₆Alkyl group, halo C₁-C₆A
Ruquil group, C₁-C₆Alkoxy group, halo C₁-C₆Alkoxy
Group, C ₁-C₆Alkylthio group, halo C₁-C₆Alkylthio
Group, C₁-C₆Alkylsulfinyl group, halo C₁-C₆Archi
Rusulfinyl group, C₁-C₆Alkylsulfonyl group or ha
B c₁-C₆One or more selected from alkylsulfonyl groups
Substituted phenyl group having a substituent, phenyl C₁-C_FourArchi
Groups, which may be the same or different, a halogen atom, C ₁-C₆
Alkyl group, halo C₁-C₆Alkyl group, C₁-C₆Alkoxy
Group, halo C₁-C₆Alkoxy group, C₁-C₆Alkylthio group,
Halo C₁-C₆Alkylthio group, C₁-C₆Alkylsulfini
Le group, halo C₁-C₆Alkylsulfinyl group, C₁-C₆Al
Killsulfonyl group or halo C₁-C₆Alkylsulfonyl group
Substituted substituents having at least one substituent selected from
Nil C₁-C_FourAlkyl group, heterocyclic group or the same or different
May be a halogen atom, C₁-C₆Alkyl group, halo C
₁-C₆Alkyl group, C₁-C₆Alkoxy group, halo C₁-C₆Al
Coxy group, C₁-C₆Alkylthio group, halo C₁-C₆Alkyl
Thio group, C₁-C₆Alkylsulfinyl group, halo C₁-C₆A
Rukylsulfinyl group, C₁-C₆Alkylsulfonyl group or
Is halo C₁-C₆One or more selected from alkylsulfonyl groups
The heterocyclic group having the above substituent is shown. ), And r is 1
Shows an integer of ~ 4. ). Where R¹And R^TwoIs
Excluding the case where a hydrogen atom is shown. Also, R¹And R^TwoAre each other
May be the same or different and may be an oxygen atom, a sulfur
1 to 3 heteroatoms selected from atoms or nitrogen atoms
May be interrupted by C_Three-C₆Show alkylene group
Can also. Het is a heterocyclic ring represented by the following Q1 to Q22.
Represents a group. Embedded image(Wherein X may be the same or different, and a halogen atom,
Cyano group, nitro group, C_Three-C₆Cycloalkyl group, halo C_Three
-C₆Cycloalkyl group, tri C which may be the same or different₁
-C₆Alkylsilyl group, phenyl group, same or different
Also good, halogen atom, C₁-C₆Alkyl group, halo C₁-C₆
Alkyl group, C₁-C₆Alkoxy group, halo C₁-C₆Alkoki
Si group, C₁-C₆Alkylthio group, halo C₁-C₆Alkylthio
Group, C₁-C₆Alkylsulfinyl group, halo C₁-C₆Archi
Rusulfinyl group, C₁-C₆Alkylsulfonyl group or ha
B C₁-C₆One or more selected from alkylsulfonyl groups
Substituted phenyl group having a substituent, heterocyclic group, same or different
May be a halogen atom, C₁-C₆Alkyl group, halo
 C₁-C₆Alkyl group, C₁-C₆Alkoxy group, halo C₁-C₆A
Lucoxy group, C₁-C₆Alkylthio group, halo C₁-C₆Archi
Luthio group, C₁-C₆Alkylsulfinyl group, halo C₁-C₆
Alkylsulfinyl group, C₁-C₆Alkylsulfonyl group
Or halo C₁-C₆1 selected from an alkylsulfonyl group
A substituted heterocyclic group having the above substituent or -A^Three-R⁸(formula
Medium, A^ThreeIs -O-, -S-, -SO-, -SO_Two −, −
N (R⁶)-(Where R⁶Is the same as above. ), -C (=
O)-, -C (= NOR⁷)-(Wherein, R⁷Is the same as above
Same. ), C₁-C₆Alkylene group, halo C₁-C₆Alkylene
Group, C_Two-C₆Alkenylene group, halo C_Two-C₆Alkenylene
Group, C _Two-C₆Alkynylene group or halo C_Three-C₆Alkynylene
(1) .A^ThreeIs -O-, -S-, -SO-, -S
O_Two -Or -N (R⁶)-(Where R⁶Is the same as above
Same. ), R⁸Is halo C_Three-C₆Cycloalkyl
Group, halo C _Three-C₆Cycloalkenyl group, phenyl group, same
Or different, a halogen atom, C₁-C₆Alkyl
Group, halo C₁-C₆Alkyl group, C₁-C₆Alkoxy group, halo
 C₁-C₆Alkoxy group, C₁-C₆Alkylthio group, halo C₁-
C₆Alkylthio group, C₁-C₆Alkylsulfinyl group, ha
B C₁-C₆Alkylsulfinyl group, C₁-C₆Alkylsul
Honyl group or halo C₁-C₆Select from alkylsulfonyl groups
Substituted phenyl group having one or more substituents, heterocycle
Group, which may be the same or different, a halogen atom, C ₁-C₆A
Ruquil group, halo C₁-C₆Alkyl group, C₁-C₆Alkoxy
Group, halo C₁-C₆Alkoxy group, C₁-C₆Alkylthio group,
Halo C₁-C₆Alkylthio group, C₁-C₆Alkylsulfini
Le group, halo C₁-C₆Alkylsulfinyl group, C₁-C₆Al
Killsulfonyl group or halo C₁-C₆Alkylsulfonyl group
A substituted heterocyclic group having at least one substituent selected from
Is -A^Four-R⁹(Where A^FourIs C₁-C₆Alkylene group, halo
 C₁-C₆Alkylene group, C_Three-C₆Alkenylene group, halo C_Three-
C₆Alkenylene group, C_Three-C₆Alkynylene group or halo C_Three-
C₆An alkynylene group;⁹Is a hydrogen atom, a halogen atom
Child, C_Three-C₆Cycloalkyl group, halo C_Three-C₆Cycloalkyl
Group, C₁-C₆Alkoxycarbonyl group, phenyl group,
May be one or different, halogen atom, C₁-C₆Alkyl
Group, halo C₁-C₆Alkyl group, C₁-C₆Alkoxy group, halo
 C₁-C₆Alkoxy group, C₁-C₆Alkylthio group, halo C₁-
C₆Alkylthio group, C₁-C₆Alkylsulfinyl group, ha
B C₁-C₆Alkylsulfinyl group, C₁-C₆Alkylsul
Honyl group or halo C₁-C₆Select from alkylsulfonyl groups
A substituted phenyl group having one or more substituents or -A
^Five-R^Ten(Where A^FiveIs -O-, -S-, -SO-, -S
O_Two-Or -C (= O), and R^TenIs C₁-C₆Alkyl
Group, halo C₁-C₆Alkyl group, C_Three-C₆Alkenyl group, halo
C_Three-C₆Alkenyl group, C_Three-C₆Cycloalkyl group, halo C_Three-
C₆Cycloalkyl group, phenyl group, same or different
Good, halogen atom, C₁-C₆Alkyl group, halo C₁-C₆A
Ruquil group, C₁-C₆Alkoxy group, halo C₁-C₆Alkoxy
Group, C₁-C₆Alkylthio group, halo C₁-C₆Alkylthio
Group, C₁-C₆Alkylsulfinyl group, halo C₁-C₆Archi
Rusulfinyl group, C₁-C₆Alkylsulfonyl group or ha
B C₁-C₆One or more selected from alkylsulfonyl groups
A substituted phenyl group, a heterocyclic group or the same or
Or a halogen atom, C₁-C₆Alkyl
Group, halo C₁-C₆Alkyl group, C₁-C₆Alkoxy group, halo
 C₁-C₆Alkoxy group, C₁-C₆Alkylthio group, halo C₁-
C₆Alkylthio group, C₁-C₆Alkylsulfinyl group, ha
B C₁-C₆Alkylsulfinyl group, C₁-C₆Alkylsul
Honyl group or halo C₁-C₆Select from alkylsulfonyl groups
A substituted heterocyclic group having one or more substituents. )
Is shown. ) And (2) .A^ThreeIs -C (= O)-or -C
(= NOR⁷)-(Wherein, R⁷Is the same as above. Place to show)
If R⁸Is a hydrogen atom, C₁-C₆Alkyl group, halo C₁-C₆A
Ruquil group, C _Two-C₆Alkenyl group, halo C_Two-C₆Alkenyl
Group, C_Three-C₆Cycloalkyl group, halo C _Three-C₆Cycloalkyl
Group, C₁-C₆Alkoxy group, C₁-C₆Alkylthio group,
No C₁-C₆Alkylamino group, which may be the same or different
 C₁-C₆Alkylamino group, phenyl group, same or different
May be a halogen atom, C₁-C₆Alkyl group, halo C₁-
C₆Alkyl group, C₁-C₆Alkoxy group, halo C₁-C₆Arco
Xyl group, C₁-C₆Alkylthio group, halo C₁-C₆Alkyl
O group, C₁-C₆Alkylsulfinyl group, halo C₁-C₆Al
Killsulfinyl group, C₁-C₆An alkylsulfonyl group or
Halo C₁-C₆One or more selected from alkylsulfonyl groups
A substituted phenyl group having a substituent, a phenylamino group,
Same or different, halogen atom, C₁-C₆Archi
Le group, halo C₁-C₆Alkyl group, C₁-C₆Alkoxy group, ha
B C₁-C₆Alkoxy group, C₁-C₆Alkylthio group, halo C
₁-C₆Alkylthio group, C₁-C₆Alkylsulfinyl group,
Halo C₁-C₆Alkylsulfinyl group, C₁-C₆Alkyls
Ruphonyl group or halo C₁-C₆Select from alkylsulfonyl groups
Substituted phenyla having one or more selected substituents on a ring
A amino group, a heterocyclic group or the same or different,
Logen atom, C₁-C₆Alkyl group, halo C₁-C₆Alkyl
Group, C₁-C₆Alkoxy group, halo C₁-C₆Alkoxy group, C
₁-C₆Alkylthio group, halo C₁-C₆Alkylthio group, C₁-
C₆Alkylsulfinyl group, halo C₁-C₆Alkylsulf
Ynyl group, C₁-C₆Alkylsulfonyl group or halo C₁-C₆
One or more substituents selected from alkylsulfonyl groups
A substituted heterocyclic group having (3).^ThreeIs C₁-C₆Archire
Halo C₁-C₆Alkylene group, C_Two-C₆Alkenylene
Group, halo C_Two-C₆Alkenylene group, C_Two-C₆Alkynylene group
Or halo C_Three-C₆When an alkynylene group is represented, R⁸Is hydrogen
Atom, halogen atom, C_Three-C₆Cycloalkyl group, halo C
_Three-C₆Cycloalkyl group, C₁-C₆Alkoxycarbonyl
Group, tri C which may be the same or different₁-C₆Alkylsilyl
Group, phenyl group, which may be the same or different,
Child, C₁-C₆Alkyl group, halo C₁-C₆Alkyl group, C₁-C₆
Alkoxy group, halo C₁-C₆Alkoxy group, C₁-C₆Archi
Luthio group, halo C₁-C₆Alkylthio group, C₁-C₆Alkyl
Sulfinyl group, halo C₁-C₆Alkylsulfinyl group,
 C₁-C₆Alkylsulfonyl group or halo C₁-C₆Alkyls
Substitution having one or more substituents selected from a rufonyl group
Phenyl group, heterocyclic group, same or different, halo
Gen atom, C₁-C₆Alkyl group, halo C₁-C₆Alkyl group,
 C₁-C₆Alkoxy group, halo C₁-C₆Alkoxy group, C₁-C₆
Alkylthio group, halo C₁-C₆Alkylthio group, C ₁-C₆A
Rukylsulfinyl group, halo C₁-C₆Alkylsulfini
Group, C₁-C₆Alkylsulfonyl group or halo C₁-C₆Al
Having one or more substituents selected from killsulfonyl groups
Substituted heterocyclic group or -A⁶-R¹¹(Where A⁶Is -O-,
-S-, -SO- or -SO_Two -Indicates R¹¹Is C_Three-C₆
Cycloalkyl group, halo C_Three-C₆Cycloalkyl group,
Nil group, which may be the same or different, a halogen atom, C₁-
C₆Alkyl group, halo C₁-C₆Alkyl group, C₁-C₆Alkoki
Si group, halo C₁-C₆Alkoxy group, C₁-C₆Alkylthio
Group, halo C₁-C₆Alkylthio group, C₁-C₆Alkylsulf
Ynyl group, halo C₁-C₆Alkylsulfinyl group, C₁-C₆
Alkylsulfonyl group or halo C₁-C₆Alkylsulfoni
Substituted phenyl having one or more substituents selected from
Groups, heterocyclic groups, which may be the same or different,
Child, C₁-C₆Alkyl group, halo C₁-C₆Alkyl group, C₁-C₆
Alkoxy group, halo C₁-C₆Alkoxy group, C₁-C₆Archi
Luthio group, halo C₁-C₆Alkylthio group, C₁-C₆Alkyl
Sulfinyl group, halo C₁-C₆Alkylsulfinyl group,
 C₁-C₆Alkylsulfonyl group or halo C₁-C₆Alkyls
Substitution having one or more substituents selected from a rufonyl group
Heterocyclic group or -A⁷-R¹²(Where A⁷Is C₁-C₆Archire
Halo C₁-C₆Alkylene group, C_Two-C₆Alkenylene
Group, halo C_Two-C₆Alkenylene group, C_Two-C₆Alkynylene group
Or halo C_Three-C₆An alkynylene group;¹²Is hydrogen field
Child, halogen atom, C_Three-C₆Cycloalkyl group, halo C_Three-
C₆Cycloalkyl group, C₁-C₆Alkoxy group, halo C ₁-C₆
Alkoxy group, C₁-C₆Alkylthio group, halo C₁-C₆Al
Kirthio group, C₁-C₆Alkylsulfinyl group, halo C₁-
C₆Alkylsulfinyl group, C₁-C₆Alkylsulfonyl
Group, halo C₁-C₆Alkylsulfonyl group, phenyl group,
May be one or different, halogen atom, C₁-C₆Alkyl
Group, halo C₁-C₆Alkyl group, C₁-C₆Alkoxy group, halo
 C₁-C₆Alkoxy group, C₁-C₆Alkylthio group, halo C₁-
C₆Alkylthio group, C₁-C₆Alkylsulfinyl group, ha
B C₁-C₆Alkylsulfinyl group, C₁-C₆Alkylsul
Honyl group or halo C₁-C₆Select from alkylsulfonyl groups
A substituted phenyl group having one or more substituents,
A xy group, which may be the same or different, a halogen atom, C₁-
C₆Alkyl group, halo C₁-C₆Alkyl group, C₁-C₆Alkoki
Si group, halo C₁-C₆Alkoxy group, C₁-C₆Alkylthio
Group, halo C₁-C₆Alkylthio group, C₁-C₆Alkylsulf
Ynyl group, halo C₁-C₆Alkylsulfinyl group, C₁-C₆
Alkylsulfonyl group or halo C₁-C₆Alkylsulfoni
Substituted pheno having one or more substituents selected from
A xy group, a phenylthio group, which may be the same or different,
Logen atom, C₁-C₆Alkyl group, halo C₁-C₆Alkyl
Group, C₁-C₆Alkoxy group, halo C₁-C₆Alkoxy group, C
₁-C₆Alkylthio group, halo C₁-C₆Alkylthio group, C₁-
C₆Alkylsulfinyl group, halo C₁-C₆Alkylsulf
Ynyl group, C₁-C₆Alkylsulfonyl group or halo C₁-C₆
One or more substituents selected from alkylsulfonyl groups
Having a substituted phenylthio group, a heterocyclic group or the same or
May be different, halogen atom, C₁-C₆Alkyl group, ha
B C₁-C₆Alkyl group, C₁-C₆Alkoxy group, halo C₁-C₆
Alkoxy group, C₁-C₆Alkylthio group, halo C₁-C₆Al
Kirthio group, C₁-C₆Alkylsulfinyl group, halo C₁-
C₆Alkylsulfinyl group, C₁-C₆Alkylsulfonyl
Group or halo C₁-C₆Selected from alkylsulfonyl groups
A substituted heterocyclic group having one or more substituents is shown. )
You. ). ), And n represents an integer of 0 to 3.
X is condensed with an adjacent atom on the hetero ring.
Can form a fused ring, wherein the fused rings are the same or different
May be a halogen atom, C₁-C₆Alkyl group, halo C₁-
C₆Alkyl group, C₁-C₆Alkoxy group, halo C₁-C₆Arco
Xyl group, C₁-C₆Alkylthio group, halo C₁-C₆Alkyl
O group, C₁-C₆Alkylsulfinyl group, halo C₁-C₆Al
Killsulfinyl group, C₁-C₆Alkylsulfonyl group, ha
B C₁-C₆Alkylsulfonyl group, phenyl group, the same or
May be different, halogen atom, C₁-C₆Alkyl group, ha
B C₁-C₆Alkyl group, C₁-C₆Alkoxy group, halo C₁-C₆
Alkoxy group, C₁-C₆Alkylthio group, halo C₁-C₆Al
Kirthio group, C₁-C₆Alkylsulfinyl group, halo C₁-
C₆Alkylsulfinyl group, C₁-C₆Alkylsulfonyl
Group or halo C₁-C₆Selected from alkylsulfonyl groups
A substituted phenyl group having one or more substituents, a heterocyclic group or
Same or different, halogen atom, C₁-C₆A
Ruquil group, halo C₁-C₆Alkyl group, C₁-C₆Alkoxy
Group, halo C₁-C₆Alkoxy group, C₁-C₆Alkylthio group,
Halo C₁-C₆Alkylthio group, C₁-C₆Alkylsulfini
Le group, halo C₁-C₆Alkylsulfinyl group, C₁-C₆Al
Killsulfonyl group or halo C₁-C₆Alkylsulfonyl group
A substituted heterocyclic group having one or more substituents selected from
It can also have one or more substituents selected from: W
Is O, S or NR¹³(Where R¹³Is C₁-C₆Alkyl
Group, halo C₁-C₆Alkyl group, C_Three-C₆Alkenyl group, halo
 C_Three-C₆Alkenyl group, C_Three-C₆Alkynyl group, halo C_Three-C₆
Alkynyl group, C₁-C₆Alkoxy group, phenyl group, same
Or different, a halogen atom, C₁-C₆Alkyl
Group, halo C₁-C₆Alkyl group, C₁-C₆Alkoxy group, halo
 C₁-C₆Alkoxy group, C₁-C₆Alkylthio group, halo C₁-
C₆Alkylthio group, C₁-C₆Alkylsulfinyl group, ha
B C₁-C₆Alkylsulfinyl group, C₁-C₆Alkylsul
Honyl group or halo C₁-C₆Select from alkylsulfonyl groups
A substituted phenyl group having one or more substituents,
Le C₁-C₆Alkyl group or may be the same or different,
Halogen atom, C₁-C₆Alkyl group, halo C₁-C₆Alkyl
Group, C₁-C₆Alkoxy group, halo C₁-C₆Alkoxy group, C
₁-C₆Alkylthio group, halo C₁-C₆Alkylthio group, C₁-
C₆Alkylsulfinyl group, halo C₁-C₆Alkylsulf
Ynyl group, C₁-C₆Alkylsulfonyl group or halo C₁-C₆
One or more substituents selected from alkylsulfonyl groups
Substituted phenyl C on the ring₁-C₆Shows an alkyl group. )
And p and q are the same or different, and
Indicates a number. ) And B¹, B^Two, B^Three, B^FourIs the same or
May be different and represent a carbon atom or a nitrogen atom. Y is
May be the same or different and include a halogen atom, a cyano group,
Toro group, halo C_Three-C₆Cycloalkyl group, phenyl group,
May be one or different, halogen atom, C ₁-C₆Alkyl
Group, halo C₁-C₆Alkyl group, C₁-C₆Alkoxy group, halo
 C₁-C₆Alkoxy group, C₁-C₆Alkylthio group, halo C₁-
C₆Alkylthio group, C₁-C₆Alkylsulfinyl group, ha
B C₁-C₆Alkylsulfinyl group, C₁-C₆Alkylsul
Honyl group or halo C₁-C₆Select from alkylsulfonyl groups
Substituted phenyl group having one or more substituents, heterocycle
Group, which may be the same or different, a halogen atom, C₁-C₆A
Ruquil group, halo C₁-C₆Alkyl group, C₁-C₆Alkoxy
Group, halo C₁-C₆Alkoxy group, C₁-C₆Alkylthio group,
Halo C₁-C₆Alkylthio group, C₁-C₆Alkylsulfini
Le group, halo C₁-C₆Alkylsulfinyl group, C₁-C₆Al
Killsulfonyl group or halo C₁-C₆Alkylsulfonyl group
A substituted heterocyclic group having at least one substituent selected from
Is -A^Three-R⁸(Where A^ThreeAnd R⁸Is the same as above. )
And m represents an integer of 1 to 5. Also, Y is adjacent to the aromatic ring
Forming fused rings with the bonded carbon atoms
And the condensed rings may be the same or different, and halogen
Atom, C₁-C₆Alkyl group, halo C₁-C₆Alkyl group, C₁-
C₆Alkoxy group, halo C₁-C₆Alkoxy group, C₁-C₆Al
Kirthio group, halo C₁-C₆Alkylthio group, C₁-C₆Archi
Rusulfinyl group, halo C₁-C₆Alkylsulfinyl
Group, C₁-C₆Alkylsulfonyl group, halo C₁-C₆Alkyl
A sulfonyl group, a phenyl group, which may be the same or different,
Halogen atom, C₁-C₆Alkyl group, halo C₁-C₆Alkyl
Group, C₁-C₆Alkoxy group, halo C₁-C₆Alkoxy group, C
₁-C₆Alkylthio group, halo C₁-C₆Alkylthio group, C₁-
C₆Alkylsulfinyl group, halo C₁-C₆Alkylsulf
Ynyl group, C₁-C₆Alkylsulfonyl group or halo C₁-C₆
One or more substituents selected from alkylsulfonyl groups
Having a substituted phenyl group, a heterocyclic group or the same or different
May be a halogen atom, C₁-C₆Alkyl group, halo C
₁-C₆Alkyl group, C₁-C₆Alkoxy group, halo C₁-C₆Al
Coxy group, C₁-C₆Alkylthio group, halo C₁-C₆Alkyl
Thio group, C₁-C₆Alkylsulfinyl group, halo C₁-C₆A
Rukylsulfinyl group, C₁-C₆Alkylsulfonyl group or
Is halo C₁-C₆One or more selected from alkylsulfonyl groups
One or more selected from substituted heterocyclic groups having the above substituents
May be substituted. Z ¹And Z^TwoIs oxygen source
Represents a hydrogen atom or a sulfur atom. However, (1). Het indicates Q2, Q6, Q7 or Q9 and B¹,
B^Two, B^ThreeAnd B^FourIs simultaneously a carbon atom, Ym
Is a 3-chloro-2-methyl group, 3-chloro-2,6-di
Ethyl group, 5-chloro-2-methyl group, 2,6-diethyl
Group, 4-chloro-2-fluoro group and 2-ethyl-6
-Excluding the methyl group. (2). Het indicates Q4 and B¹, B^Two, B^ThreeAnd B^FourBut
When simultaneously indicating a carbon atom, Ym is 2,5-dichloro
Group, 2,4-difluoro group, 2,6-difluoro group, 3
-Chloro-2-methyl group, 5-chloro-2-methyl group,
5-fluoro-2-methyl group, 2,6-dimethyl group,
2,6-diethyl group, 2-ethyl-6-methyl group, 2-
Methoxy-5-nitro group, 2-methoxy-5-methyl
Group, 2,6-diethoxy group, 3-bromo-2-methyl
Group, 3-fluoro-2-methyl group, 3-iodo-2-me
Tyl group, 3-cyano-2-methyl group, 3-difluoromethyl
A toxic-2-methyl group, a 5-chloro-2-ethyl group,
2,5-dimethyl group, 2,3-dichloro group, 3-chloro
-2,6-diethyl group, 4-trifluoromethyl group, 3
-Methoxycarbonyl-2-methyl group, 3-trifluoro
Romethyl-2-methyl group, 3,5-dichloro-2,6-
Diethyl group, 3,4-dichloro group, 3-methoxycarbo
Nylmethyloxy-2-methyl group, 2-methyl-3-ni
Excludes toro and 4-trifluoromethoxy groups. (3). Het indicates Q9 and R^TwoAnd R^ThreeIs a hydrogen source at the same time
Xn represents a 2-phenyl group;¹Is n-p
A ropyl group or an i-propyl group;¹, B^Two, B^Three
And B^FourIs simultaneously a carbon atom, Ym is 4-pen
Excludes the tafluoroethyl-2-methyl group. (4). Het indicates Q10 and B¹, B^Two, B^ThreeAnd B^Four
Represents simultaneously a carbon atom, Ym is 5-chloro-2-
Methyl group, 5-fluoro-2-methyl group and 2,5-di
Heterocyclic dicarboxylic acid diamine represented by
Derivatives. 2. Het indicates Q1, Q2, Q3 or Q4.
Then R¹Is C_Three-C₆Cycloalkyl group, halo C_Three-C₆Cyclo
Alkyl group or -A¹ − (R^Four) R (where A¹Is C₁-
C₈An alkylene group;^FourMay be the same or different
Hydrogen, halogen, cyano, nitro, C
₁-C₆Alkoxycarbonyl groups, which may be the same or different
The C₁-C₆Alkoxyphosphoryl group, same or different
Good di C ₁-C₆Alkoxythiophosphoryl group, phenyl
Group, which may be the same or different, a halogen atom, C₁-C₆A
Ruquil group, halo C₁-C₆Alkyl group, C₁-C₆Alkoxy
Group, halo C₁-C₆Alkoxy group, C₁-C₆Alkylthio group,
Halo C₁-C₆Alkylthio group, C ₁-C₆Alkylsulfini
Le group, halo C₁-C₆Alkylsulfinyl group, C₁-C₆Al
Killsulfonyl group or halo C₁-C₆Alkylsulfonyl group
Substituted phenyl having one or more substituents selected from
Group, pyridyl group, which may be the same or different,
Child, C₁-C₆Alkyl group, halo C₁-C₆Alkyl group, C₁-C₆
Alkoxy group, halo C₁-C₆Alkoxy group, C₁-C₆Archi
Luthio group, halo C₁-C₆Alkylthio group, C₁-C₆Alkyl
Sulfinyl group, halo C₁-C₆Alkylsulfinyl group,
 C₁-C₆Alkylsulfonyl group or halo C₁-C₆Alkyls
Substitution having one or more substituents selected from a rufonyl group
Pyridyl group or -A^Two-R^Five(Where A^TwoIs -O-,-
S-, -SO-, -SO_Two-, -N (R⁶)-(Wherein
R⁶Is a hydrogen atom, C₁-C₆Alkylcarbonyl group, halo C
₁-C₆Alkylcarbonyl group or C₁-C₆Alkoxycarbo
Represents a nyl group. ) Or -C (= NOR⁷)-(Where R
⁷Is a hydrogen atom, C₁-C₆Alkyl group or halo C₁-C₆Archi
Represents a hydroxyl group. ) And R^FiveIs a hydrogen atom, C₁-C₆Archi
Le group, halo C₁-C₆Alkyl group, C₁-C₆Cycloalkyl
Group, halo C₁-C₆Cycloalkyl group, phenyl group, same or
May be different, a halogen atom, C₁-C₆Alkyl group,
Halo C₁-C₆Alkyl group, C₁-C₆Alkoxy group, halo C₁-
C₆Alkoxy group, C₁-C₆Alkylthio group, halo C₁-C₆A
Lucylthio group, C₁-C₆Alkylsulfinyl group, halo C
₁-C₆Alkylsulfinyl group, C₁-C₆Alkylsulfoni
Or halo C₁-C₆Selected from alkylsulfonyl groups
A substituted phenyl group having one or more substituents, pyridyl
Group, which may be the same or different, a halogen atom, C₁-C₆A
Ruquil group, halo C₁-C₆Alkyl group, C₁-C₆Alkoxy
Group, halo C₁-C₆Alkoxy group, C₁-C₆Alkylthio group,
Halo C₁-C₆Alkylthio group, C₁-C₆Alkylsulfini
Le group, halo C₁-C₆Alkylsulfinyl group, C₁-C₆Al
Killsulfonyl group or halo C₁-C₆Alkylsulfonyl group
A substituted pyridyl group having at least one substituent selected from
Is shown. ), And r represents an integer of 1 to 4. )
Then R^TwoAnd R^ThreeMay be the same or different, and a hydrogen atom
Or C₁-C₆X and Y are the same or different
Halogen, cyano, nitro,
Nil group, which may be the same or different, a halogen atom, C₁-
C₆Alkyl group, halo C₁-C₆Alkyl group, C₁-C₆Alkoki
Si group, halo C₁-C₆Alkoxy group, C₁-C₆Alkylthio
Group, halo C₁-C₆Alkylthio group, C₁-C₆Alkylsulf
Ynyl group, halo C₁-C₆Alkylsulfinyl group, C₁-C₆
Alkylsulfonyl group or halo C₁-C₆Alkylsulfoni
Substituted phenyl having one or more substituents selected from
Group, pyridyl group, which may be the same or different, halogen
Atom, C₁-C₆Alkyl group, halo C₁-C₆Alkyl group, C₁-
C₆Alkoxy group, halo C₁-C₆Alkoxy group, C₁-C₆Al
Kirthio group, halo C₁-C₆Alkylthio group, C₁-C₆Archi
Rusulfinyl group, halo C₁-C₆Alkylsulfinyl
Group, C₁-C₆Alkylsulfonyl group or halo C₁-C₆Archi
Having one or more substituents selected from rusulfonyl groups
Substituted pyridyl group or -A^Three-R⁸(Where A^ThreeIs -O
-, -S-, -SO-, -SO_Two−, C₁-C₆Alkylene
Group, halo C₁-C₆Alkylene group, C_Two-C₆Alkenylene group,
Halo C_Two-C₆Alkenylene group, C_Two-C₆Alkynylene group or
Halo C_Three-C₆An alkenylene group; (1). A^ThreeIs -O-, -S-, -SO- or -SO_Two−
, R⁸Is a phenyl group, which may be the same or different
, Halogen atom, C₁-C₆Alkyl group, halo C₁-C₆Al
Kill group, C₁-C₆Alkoxy group, halo C₁-C₆Alkoxy
Group, C₁-C₆Alkylthio group, halo C₁-C₆Alkylthio
Group, C₁-C₆Alkylsulfinyl group, halo C₁-C₆Archi
Rusulfinyl group, C₁-C₆Alkylsulfonyl group or ha
B C₁-C₆One or more selected from alkylsulfonyl groups
A substituted phenyl group having a substituent, a pyridyl group, the same or
May be different, halogen atom, C₁-C₆Alkyl group, ha
B C₁-C₆Alkyl group, C₁-C₆Alkoxy group, halo C₁-C₆
Alkoxy group, C₁-C₆Alkylthio group, halo C₁-C₆Al
Kirthio group, C₁-C₆Alkylsulfinyl group, halo C₁-
C₆Alkylsulfinyl group, C₁-C₆Alkylsulfonyl
Group or halo C₁-C₆Selected from alkylsulfonyl groups
A substituted pyridyl group having at least one substituent or -A^Four-R
⁹(Where A^FourIs C₁-C₆Alkylene group, halo C₁-C₆Al
Kylene group, C_Three-C₆Alkenylene group, halo C_Three-C₆Alkene
Len group, C_Three-C₆Alkynylene group or halo C_Three-C₆Alkini
Represents a len group;⁹Is a hydrogen atom, a halogen atom or -A
^Five-R^Ten(Where A^FiveIs -O-, -S-, -SO- or-
SO_Two-Indicates R^TenIs C₁-C₆Alkyl group, halo C₁-C₆
Alkyl group, C_Three-C₆Alkenyl group, halo C_Three-C₆Alkene
Group, C_Three-C₆Cycloalkyl group or halo C_Three-C₆Cycloa
Represents a alkyl group. ). ), (2) .A^ThreeIs C₁-C₆Alkylene group, halo C₁-C₆Alkylene
Group, C_Two-C₆Alkenylene group, halo C_Two-C₆Alkenylene
Group, C_Two-C₆Alkynylene group or halo C_Three-C₆Alkynylene
When denoting a group,⁸Is a hydrogen atom, a halogen atom, C_Three-C₆
Cycloalkyl group, halo C_Three-C₆Cycloalkyl group, identical
Or a different bird C₁-C₆Alkylsilyl group,
Nil group, which may be the same or different, a halogen atom, C₁-
C₆Alkyl group, halo C₁-C₆Alkyl group, C₁-C₆Alkoki
Si group, halo C₁-C₆Alkoxy group, C₁-C₆Alkylthio
Group, halo C₁-C₆Alkylthio group, C₁-C₆Alkylsulf
Ynyl group, halo C₁-C₆Alkylsulfinyl group, C₁-C₆
Alkylsulfonyl group or halo C ₁-C₆Alkylsulfoni
Substituted phenyl having one or more substituents selected from
Group, pyridyl group, which may be the same or different, halogen
Atom, C₁-C₆Alkyl group, halo C₁-C₆Alkyl group, C₁-
C₆Alkoxy group, halo C₁-C₆Alkoxy group, C₁-C₆Al
Kirthio group, halo C₁-C₆Alkylthio group, C₁-C₆Archi
Rusulfinyl group, halo C₁-C₆Alkylsulfinyl
Group, C₁-C₆Alkylsulfonyl group or halo C₁-C₆Archi
Having one or more substituents selected from rusulfonyl groups
Substituted pyridyl group or -A⁶-R¹¹(Where A⁶Is -O
-, -S-, -SO- or -SO_Two-Indicates R¹¹Is-
A⁷-R¹²(Where A⁷Is C₁-C₆Alkylene group, halo C₁-
C₆Alkylene group, C_Two-C₆Alkenylene group, halo C_Two-C₆A
Lucenylene group, C_Two-C₆Alkynylene group or halo C_Three-C₆A
A ruquinylene group;¹²Is a hydrogen atom, a halogen atom,
 C₁-C₆Alkoxy group, halo C₁-C₆Alkoxy group, C₁-C₆
Alkylthio group, halo C₁-C₆Alkylthio group, C₁-C₆A
Rukylsulfinyl group, halo C₁-C₆Alkylsulfini
Group, C₁-C₆Alkylsulfonyl group or halo C₁-C₆Al
Represents a killsulfonyl group. ). )
Then B¹And B^FourEach represents a carbon atom;^TwoAnd B^Three
May be the same or different and represent a carbon atom or a nitrogen atom.
Then Z¹And Z^TwoThe complex according to claim 1, wherein represents an oxygen atom.
Cyclic dicarboxylic acid diamide derivatives. 3. X may be the same or different and represents a halogen atom, a nitro group, a halo C ₁ -C ₆ alkyl group, a halo C ₁ -C ₆ alkoxy group or a halo C ₁ -C ₆ alkylthio group; The heterocyclic dicarboxylic acid diamide derivative according to claim 2, wherein represents an integer of 0 to 3. 4. Y is the same or different, and halogen
Atom, C₁-C₆Alkyl group, halo C₁-C₆Alkyl group, C₁-
C₆Alkoxy group, halo C₁-C₆Alkoxy group, C₁-C₆Al
Kirthio group, halo C₁-C₆Alkylthio group, halo C₁-C₆A
Lucoxyhalo C₁-C₆Alkoxy group, halo C₁-C₆Alkoki
Shihalo C₁-C₆Alkylthio group, halo C ₁-C₆Alkylsul
Finyl group or halo C₁-C₆Represents an alkylsulfonyl group
And m is an integer of 1 to 5;
Rubonic acid diamide derivatives. 5. R¹Is C₁-C₆Alkyl group, C₁-C₆Arco
Kiss C₁-C₈Alkyl group, C₁-C₆Alkylthio C₁-C₈Al
Kill group, C₁-C₆Alkylsulfinyl C₁-C₈Alkyl group
Or C₁-C₆Alkylsulfonyl C₁-C₈Represents an alkyl group
Then R^TwoAnd R ^ThreeMay be the same or different, and a hydrogen atom
Or a heterocyclic dicarboxylic acid according to claim 4, which represents a methyl group.
Diamide derivatives. 6. A pesticide for agricultural and horticultural use, comprising the heterocyclic dicarboxylic acid diamide derivative according to claim 1 as an active ingredient. 7. A method for using an agricultural and horticultural chemical, which comprises applying an effective amount of the agricultural and horticultural chemical according to claim 6 to a target crop or soil to control pests from a useful crop.