RU2807181C2 - Benzimidazole derivative or its salt, agricultural and horticultural insecticidal and acaricidal product containing specified compound, and method of its use - Google Patents

Abstract

FIELD: agriculture; horticulture.

SUBSTANCE: group of inventions relates to a benzimidazole derivative represented by the general formula (1)

and also refers to an agricultural and horticultural insecticidal and acaricidal agent containing a benzimidazole derivative or a salt thereof as an active ingredient, also refers to a method of applying an agricultural and horticultural insecticidal and acaricidal agent comprising applying an effective amount of a benzimidazole derivative or a salt thereof to plants or soil, also refers to an anti-ectoparasite agent in animals containing an effective amount of a benzimidazole derivative or a salt thereof as an active ingredient, also refers to an anti-endoparasite agent in animals containing an effective amount of a benzimidazole derivative or a salt thereof as an active ingredient, also refers to the use of a benzimidazole derivative or a salt thereof in the manufacture of an ectoparasite control agent also refers to the use of a benzimidazole derivative or a salt thereof in the manufacture of an endoparasite control agent.

EFFECT: group of inventions ensures the development of an agricultural and horticultural insecticidal and acaricidal product that has less impact on natural enemies of beneficial insects and is endowed with the activity of penetration and movement of substances in plants, from the point of view of the appearance of pests resistant to existing drugs, the impact on environmental biology and labor savings during operation.

10 cl, 8 tbl, 20 ex

Description

Field of technology

[0001]

The present invention relates to an agricultural and horticultural insecticidal and acaricidal agent containing a benzimidazole derivative or a salt thereof as an active ingredient and a method for its use.

Field of technology

[0002]

It has now been documented that benzimidazole derivatives can be used as insecticidal agents (for example, see Patent Literatures 1 and 2); however, these literatures do not describe a benzimidazole derivative having a specific N-sulfonyl group, such as an N-alkylsulfonyl group, at the 1-position. These literatures do not describe a benzimidazole derivative in which a pyridyl group is attached at the 2-position, but do not describe the compound having a particular N-sulfonyl group such as an alkylsulfonyl group at position 1, or its insecticidal effect (for example, see Non-Patent Literature 1 and 2).

List of cited literature

Patent literature

[0003]

Patent Literature 1: International Publication No. WO2012/086848

Patent Literature 2: International Publication No. WO2013/018928

Non-patent literature

[0004]

Non-Patent Literature 1: Advanced Synthesis & Catalysis (2015), 357(7), 1416-1424

Non-patent Literature 2: Yingyong Huaxue (2007), 24(5), 507-511

The essence of the invention

Technical problem

[0005]

In plant production in the field of agriculture, horticulture and the like, damage caused by pests and the like is still serious, and there is a need to develop an agricultural and horticultural insecticidal and acaricidal agent having a new effect, less impact on natural enemies of beneficial insects and endowed with activity penetration and movement of substances in plants, from the point of view of the emergence of pests resistant to existing drugs, the impact on environmental biology and labor savings during operation.

Solution

[0006]

The inventors of the present invention have conducted intensive research to solve the above problems and found that the benzimidazole derivative represented by the general formula (1), wherein a pyridyl group is attached at the 2-position and a specific N-sulfonyl group is present at the 1-position, or a salt thereof, exhibits not only good effect in the control of agricultural and horticultural pests, but can solve the above problem, thereby creating the present invention.

[0007]

Thus, the present invention relates to

[1] A benzimidazole derivative represented by the general formula (1)

[Formula 1]

,

where R represents (a1) (C ₁ -C ₈ )alkyl group; (a2) (C ₃ -C ₈ )cycloalkyl group; (a3) (C ₃ -C ₈ )cycloalkyl (C ₁ -C ₈ )alkyl group; (a4) a halogen(C ₁ -C ₈ )alkyl group; (a5) (C ₂ -C ₈ )alkenyl group; (a6) (C ₂ -C ₈ )alkynyl group; (a7) an aryl group or (a8) an aryl group having from 1 to 5 substituents, which may be the same or different and selected from (a) a halogen atom, (b) a (C ₁ -C ₆ ) alkyl group, (c) halogen(C ₁ -C ₆ )alkyl group, (d) (C ₁ -C ₆ )alkoxy group, (e) halogen(C ₁ -C ₆ )alkoxy group, (f) (C ₁ -C ₆ )alkylthio group , (g) halogen(C ₁ -C ₆ )alkylthio group, (h) (C ₁ -C ₆ )alkylsulfinyl group, (i) halogen(C ₁ -C ₆ )alkylsulfinyl group, (j) (C ₁ -C ₆ ) alkylsulfonyl group, (k) a halogen(C ₁ -C ₆ )alkylsulfonyl group and (l) a tri(C ₁ -C ₆ )alkylsilyl group, where the alkyl groups may be the same or different;

R ¹ represents a (b1) (C ₁ -C ₈ )alkyl group; (b2) a halogen(C ₁ -C ₈ )alkyl group; (b3) (C ₃ -C ₈ )cycloalkyl group; (b4) a halogen(C ₃ -C ₈ )cycloalkyl group; (b5) (C ₃ -C ₈ )cycloalkyl (C ₁ -C ₈ )alkyl group; (b6) a halogen(C ₃ -C ₈ )cycloalkyl(C ₁ -C ₈ )alkyl group; (b7) (C ₂ -C ₈ )alkenyl group; (b8) a halogen(C ₂ -C ₈ )alkenyl group; (b9) (C ₂ -C ₈ )alkynyl group; (b10) halogen(C ₂ -C ₈ )alkynyl group; (b11) an aryl group; (b12) an aryl group having from 1 to 5 substituents, which may be the same or different and selected from (a) a halogen atom, (b) a (C ₁ -C ₆ ) alkyl group, (c) a halogen (C ₁ -C ₆ )alkyl group, (d) (C ₁ -C ₆ )alkoxy group, (e) halogen(C ₁ -C ₆ )alkoxy group, (f) (C ₁ -C ₆ )alkylthio group, (g) halogen( C ₁ -C ₆ )alkylthio group, (h) (C ₁ -C ₆ )alkylsulfinyl group, (i) halogen(C ₁ -C ₆ )alkylsulfinyl group, (j) (C ₁ -C ₆ )alkylsulfinyl group, ( k) a halogen(C ₁ -C ₆ )alkylsulfonyl group and (l) a tri(C ₁ -C ₆ )alkylsilyl group, where the alkyl groups may be the same or different; (b13) aryl(C ₁ -C ₈ )alkyl group; (b14) aryl(C ₁ -C ₆ )alkyl group having from 1 to 5 substituents, which may be the same or different and selected from (a) a halogen atom, (b) a (C ₁ -C ₆ )alkyl group, ( c) halogen(C ₁ -C ₆ )alkyl group, (d) (C ₁ -C ₆ )alkoxy group, (e) halogen(C ₁ -C ₆ )alkoxy group, (f) (C ₁ -C ₆ ) alkylthio group, (g) halogen(C ₁ -C ₆ )alkylthio group, (h) (C ₁ -C ₆ )alkylsulfinyl group, (i) halogen(C ₁ -C ₆ )alkylsulfinyl group, (j) (C ₁ -C ₆ )alkylsulfonyl group, (k) halogen(C ₁ -C ₆ )alkylsulfonyl group and (l) tri(C ₁ -C ₆ )alkylsilyl group, the alkyl group may be the same or different; (b15) an aromatic heterocyclic group; (b16) an aromatic heterocyclic group having from 1 to 3 substituents, which may be the same or different and selected from (a) a halogen atom, (b) a (C ₁ -C ₆ )alkyl group, (c) a halogen (C ₁ - C ₆ )alkyl group, (d) (C ₁ -C ₆ )alkoxy group, (e) halogen(C ₁ -C ₆ )alkoxy group, (f) (C ₁ -C ₆ )alkylthio group, (g) halogen (C ₁ -C ₆ )alkylthio group, (h) (C ₁ -C ₆ )alkylsulfinyl group, (i) halogen(C ₁ -C ₆ )alkylsulfinyl group, (j) (C ₁ -C ₆ )alkylsulphonyl group, (k) a halogen(C ₁ -C ₆ )alkylsulfonyl group and (l) a tri(C ₁ -C ₆ )alkylsilyl group, where the alkyl groups may be the same or different; (b17) (C ₁ -C ₈ )alkoxy(C ₁ -C ₈ )alkyl group; (b18) (C ₁ -C ₈ )alkylthio(C ₁ -C ₈ )alkyl group; (b19) (C ₁ -C ₈ )alkylsulfinyl(C ₁ -C ₈ )alkyl group or (b20) (C ₁ -C ₈ )alkylsulfonyl(C ₁ -C ₈ )alkyl group.

X represents O, S, SO, SO ₂ or NR ² where R ² represents a hydrogen atom, a (C ₁ -C ₆ )alkyl group, a (C ₁ -C ₆ )alkylcarbonyl group, (C ₁ -C ₆ ) an alkoxycarbonyl group, a (C ₁ -C ₆ )alkylsulfonyl group or a halogen(C ₁ -C ₆ )alkylsulfonyl group, or R ² may be attached to R ¹ to form, together with the nitrogen atom to which R ² is attached, 5-8- membered saturated nitrogen-containing aliphatic heterocycle, optionally having from 1 to 5 substituents, where the substituent is selected from a (C ₁ -C ₆ )alkyl group, (C ₁ -C ₆ )alkylcarbonyl group, (C ₁ -C ₆ )alkoxycarbonyl group, (C ₁ -C ₆ )alkylsulfonyl group, halogen(C ₁ -C ₆ )alkylsulfonyl group and (C ₁ -C ₆ )alkylenedioxy group, where the two hydroxy groups in the alkylenedioxy group may be attached to the same carbon atom or to different atoms carbon of a nitrogen-containing aliphatic heterocycle;

Y may be the same or different and represents (c1) a halogen atom or (c2) a (C ₁ -C ₈ )alkyl group;

m represents 0, 1, 2 or 3;

Z may be the same or different and represents (d1) a halogen atom; (d2) (C ₁ -C ₈ )alkyl group; (d3) (C ₃ -C ₈ )cycloalkyl group; (d4) (C ₃ -C ₈ )cycloalkyl (C ₁ -C ₈ )alkyl group; (d5) halogen(C ₃ -C ₈ )cycloalkyl(C ₁ -C ₈ )alkyl group; (d6) halogen(C ₁ -C ₈ )alkyl group; (d7) halogen(C ₁ -C ₈ )alkoxy group; (d8) halogen(C ₁ -C ₈ )alkylthio group; (d9) a halogen(C ₁ -C ₈ )alkylsulfinyl group or (d10) a halogen(C ₁ -C ₈ )alkylsulfonyl group and

n represents 0, 1, 2, 3 or 4, or a salt thereof;

[0008]

[2] a benzimidazole derivative according to [1], where R represents (a1) (C ₁ -C ₈ )alkyl group; (a2) (C ₃ -C ₈ )cycloalkyl group; (a3) (C ₃ -C ₈ )cycloalkyl (C ₁ -C ₈ )alkyl group; (a4) a halogen(C ₁ -C ₈ )alkyl group; (a5) (C ₂ -C ₈ )alkenyl group; (a6) (C ₂ -C ₈ )alkynyl group; (a7) an aryl group or (a8) an aryl group having from 1 to 5 substituents, which may be the same or different and selected from (a) a halogen atom, (b) a (C ₁ -C ₆ ) alkyl group, (c) halogen(C ₁ -C ₆ )alkyl group, (d) (C ₁ -C ₆ )alkoxy group, (e) halogen(C ₁ -C ₆ )alkoxy group, (f) (C ₁ -C ₆ )alkylthio group , (g) halogen(C ₁ -C ₆ )alkylthio group, (h) (C ₁ -C ₆ )alkylsulfinyl group, (i) halogen(C ₁ -C ₆ )alkylsulfinyl group, (j) (C ₁ -C ₆ )alkylsulfonyl group and (k) halogen(C _{1 -C6} )alkylsulfonyl group;

R ¹ represents a (b1) (C ₁ -C ₈ )alkyl group; (b2) a halogen(C ₁ -C ₈ )alkyl group; (b3) (C ₃ -C ₈ )cycloalkyl group; (b4) a halogen(C ₃ -C ₈ )cycloalkyl group; (b5) (C ₃ -C ₈ )cycloalkyl (C ₁ -C ₈ )alkyl group; (b6) a halogen(C ₃ -C ₈ )cycloalkyl(C ₁ -C ₈ )alkyl group; (b7) (C ₂ -C ₈ )alkenyl group; (b8) a halogen(C ₂ -C ₈ )alkenyl group; (b9) (C ₂ -C ₈ )alkynyl group; (b10) halogen(C ₂ -C ₈ )alkynyl group; (b11) an aryl group; (b12) an aryl group having from 1 to 5 substituents, which may be the same or different and selected from (a) a halogen atom, (b) a (C ₁ -C ₆ ) alkyl group, (c) a halogen (C ₁ -C ₆ )alkyl group, (d) (C ₁ -C ₆ )alkoxy group, (e) halogen(C ₁ -C ₆ )alkoxy group, (f) (C ₁ -C ₆ )alkylthio group, (g) halogen( C ₁ -C ₆ )alkylthio group, (h) (C ₁ -C ₆ )alkylsulfinyl group, (i) halogen(C ₁ -C ₆ )alkylsulfinyl group, (j) (C ₁ -C ₆ )alkylsulphonyl group and ( k) halogen(C ₁ -C ₆ )alkylsulfonyl group; (b13) aryl(C ₁ -C ₈ )alkyl group; (b14) aryl(C ₁ -C ₆ )alkyl group having from 1 to 5 substituents, which may be the same or different and selected from (a) a halogen atom, (b) a (C ₁ -C ₆ )alkyl group, ( c) halogen(C ₁ -C ₆ )alkyl group, (d) (C ₁ -C ₆ )alkoxy group, (e) halogen(C ₁ -C ₆ )alkoxy group, (f) (C ₁ -C ₆ ) alkylthio group, (g) halogen(C ₁ -C ₆ )alkylthio group, (h) (C ₁ -C ₆ )alkylsulfinyl group, (i) halogen(C ₁ -C ₆ )alkylsulfinyl group, (j) (C ₁ -C ₆ )alkylsulfonyl group and (k) halogen(C ₁ -C ₆ )alkylsulfonyl group; (b15) an aromatic heterocyclic group or (b16) an aromatic heterocyclic group having from 1 to 3 substituents, which may be the same or different and selected from (a) a halogen atom, (b) a (C ₁ -C ₆ )alkyl group, ( c) halogen(C ₁ -C ₆ )alkyl group, (d) (C ₁ -C ₆ )alkoxy group, (e) halogen(C ₁ -C ₆ )alkoxy group, (f) (C ₁ -C ₆ ) alkylthio group, (g) halogen(C ₁ -C ₆ )alkylthio group, (h) (C ₁ -C ₆ )alkylsulfinyl group, (i) halogen(C ₁ -C ₆ )alkylsulfinyl group, (j) (C ₁ -C ₆ )alkylsulfonyl group and (k) halogen(C ₁ -C ₆ )alkylsulfonyl group;

X represents O, S, SO, SO ₂ or NR ² where R ² represents a hydrogen atom, a (C ₁ -C ₆ )alkyl group, a (C ₁ -C ₆ )alkylcarbonyl group, (C ₁ -C ₆ ) alkoxycarbonyl group, (C ₁ -C ₆ )alkylsulfonyl group or halogen (C ₁ -C ₆ )alkylsulfonyl group),

Y may be the same or different and represents (c1) a halogen atom or (c2) a (C ₁ -C ₈ )alkyl group;

m represents 0, 1, 2 or 3;

Z may be the same or different and represents (d1) a halogen atom; (d2) (C ₁ -C ₈ )alkyl group; (d3) (C ₃ -C ₈ )cycloalkyl group; (d4) (C ₃ -C ₈ )cycloalkyl (C ₁ -C ₈ )alkyl group; (d5) halogen(C ₃ -C ₈ )cycloalkyl(C ₁ -C ₈ )alkyl group; (d6) halogen(C ₁ -C ₈ )alkyl group; (d7) halogen(C ₁ -C ₈ )alkoxy group; (d8) halogen(C ₁ -C ₈ )alkylthio group; (d9) a halogen(C ₁ -C ₈ )alkylsulfinyl group or (d10) a halogen(C ₁ -C ₈ )alkylsulfonyl group and

n represents 0, 1, 2, 3 or 4, or a salt thereof;

[0009]

[3] a benzimidazole derivative according to [1], where R represents (a1) (C ₁ -C ₈ )alkyl group; (a2) (C ₃ -C ₈ )cycloalkyl group; (a4) a halogen(C ₁ -C ₈ )alkyl group; (a7) an aryl group or (a8) an aryl group having from 1 to 5 substituents, which may be the same or different and selected from (a) a halogen atom, (b) a (C ₁ -C ₆ ) alkyl group, (c) halogen(C ₁ -C ₆ )alkyl group, (d) (C ₁ -C ₆ )alkoxy group, (e) halogen(C ₁ -C ₆ )alkoxy group, (f) (C ₁ -C ₆ )alkylthio group , (g) halogen(C ₁ -C ₆ )alkylthio group, (h) (C ₁ -C ₆ )alkylsulfinyl group, (i) halogen(C ₁ -C ₆ )alkylsulfinyl group, (j) (C ₁ -C ₆ ) alkylsulfonyl group, (k) a halogen(C ₁ -C ₆ )alkylsulfonyl group and (l) a tri(C ₁ -C ₆ )alkylsilyl group, where the alkyl groups may be the same or different;

R ¹ represents a (b1) (C ₁ -C ₈ )alkyl group; (b2) a halogen(C ₁ -C ₈ )alkyl group; (b3) (C ₃ -C ₈ )cycloalkyl group; (b5) (C ₃ -C ₈ )cycloalkyl (C ₁ -C ₈ )alkyl group; (b11) an aryl group; (b12) an aryl group having from 1 to 5 substituents, which may be the same or different and selected from (a) a halogen atom, (b) a (C ₁ -C ₆ ) alkyl group, (c) a halogen (C ₁ -C ₆ )alkyl group, (d) (C ₁ -C ₆ )alkoxy group, (e) halogen(C ₁ -C ₆ )alkoxy group, (f) (C ₁ -C ₆ )alkylthio group, (g) halogen( C ₁ -C ₆ )alkylthio group, (h) (C ₁ -C ₆ )alkylsulfinyl group, (i) halogen(C ₁ -C ₆ )alkylsulfinyl group, (j) (C ₁ -C ₆ )alkylsulfinyl group, ( k) a halogen(C ₁ -C ₆ )alkylsulfonyl group and (l) a tri(C ₁ -C ₆ )alkylsilyl group, where the alkyl groups may be the same or different; (b13) aryl(C ₁ -C ₈ )alkyl group; (b14) aryl(C ₁ -C ₆ )alkyl group having from 1 to 5 substituents, which may be the same or different and selected from (a) a halogen atom, (b) a (C ₁ -C ₆ )alkyl group, ( c) halogen(C ₁ -C ₆ )alkyl group, (d) (C ₁ -C ₆ )alkoxy group, (e) halogen(C ₁ -C ₆ )alkoxy group, (f) (C ₁ -C ₆ ) alkylthio group, (g) halogen(C ₁ -C ₆ )alkylthio group, (h) (C ₁ -C ₆ )alkylsulfinyl group, (i) halogen(C ₁ -C ₆ )alkylsulfinyl group, (j) (C ₁ -C ₆ )alkylsulfonyl group, (k) halogen(C ₁ -C ₆ )alkylsulfonyl group and (l) tri(C ₁ -C ₆ )alkylsilyl group, where the alkyl groups may be the same or different; (b17) (C ₁ -C ₈ )alkoxy(C ₁ -C ₈ )alkyl group; (b18) (C ₁ -C ₈ )alkylthio(C ₁ -C ₈ )alkyl group or (b20) (C ₁ -C ₈ )alkylsulfonyl(C ₁ -C ₈ )alkyl group,

X represents O, S, SO, SO ₂ or NR ² where R ² represents a (C ₁ -C ₆ )alkyl group, (C ₁ -C ₆ )alkylcarbonyl group or (C ₁ -C ₆ )alkylsulfonyl group, or R ² can be attached to R ¹ to form, together with the nitrogen atom to which R ² is attached, a 5-8 membered saturated nitrogen-containing aliphatic heterocycle, optionally having from 1 to 5 substituents, where the substituent is selected from (C ₁ -C ₆ )alkyl group, (C ₁ -C ₆ )alkylcarbonyl group, (C ₁ -C ₆ )alkoxycarbonyl group, (C ₁ -C ₆ )alkylsulfonyl group, halogen (C ₁ -C ₆ )alkylsulfonyl group and (C ₁ -C ₆ )alkylenedioxy groups, where two oxy groups in the alkylenedioxy group can be attached to the same carbon atom or to different carbon atoms of the nitrogen-containing aliphatic heterocycle;

Y may be the same or different and represents (c1) a halogen atom;

m represents 0 or 1;

Z may be the same or different and represents a (d1) halogen atom or (d2) (C ₁ -C ₈ )alkyl group and

n represents 0, 1 or 2, or a salt thereof;

[0010]

[4] a benzimidazole derivative according to [1], where R represents an (a1) (C ₁ -C ₈ )alkyl group; R ¹ represents (b1) a halogen(C ₁ -C ₈ )alkyl group; m represents 0 and n represents 0 or its salt;

[0011]

[5] an agricultural and horticultural insecticidal and acaricidal agent containing a benzimidazole derivative or a salt thereof according to any of [1] to [4] as an active ingredient;

[6] a method of applying an agricultural and horticultural insecticidal and acaricidal agent, comprising applying to plants or soil an effective amount of a benzimidazole derivative or a salt thereof in accordance with any of [1]-[4];

[7] an anti-ectoparasite agent in animals, containing an effective amount of a benzimidazole derivative or a salt thereof according to any of [1] to [4] as an active ingredient;

[8] an endoparasite control agent in animals containing an effective amount of a benzimidazole derivative or a salt thereof according to any one of [1] to [4] as an active ingredient.

Positive effect of the invention

[0012]

The benzimidazole derivative of the present invention, wherein a pyridyl group is attached at the 2-position and a particular N-sulfonyl group is present at the 1-position, or a salt thereof, not only has a good effect as an agricultural and horticultural insecticidal and acaricidal agent, but also has an effect on pests parasitizing on companion animals such as dogs and cats, or on companion animals such as cows and sheep.

Description of Embodiments of the Invention

[0013]

In the definition of the general formula (1), representing a benzimidazole derivative wherein a pyridyl group is attached at position 2 and a particular N-sulfonyl group is present at position 1, of the present invention or a salt thereof, the term “halogen” means “halogen atom” and refers to the atom fluorine, chlorine atom, bromine atom or iodine atom.

[0014]

The term "(C ₁ -C ₈ )alkyl group" refers to straight or branched alkyl groups having from 1 to 8 carbon atoms, such as methyl group, ethyl group, normal propyl group, isopropyl group, normal butyl group, isobutyl group, secondary butyl group, tertiary butyl group, normal pentyl group, isopentyl group, tertiary pentyl group, neopentyl group, 2,3-dimethylpropyl group, 1-ethylpropyl group, 1-methylbutyl group, 2-methylbutyl group, normal hexyl group, isohexyl group , 2-hexyl group, 3-hexyl group, 2-methylpentyl group, 3-methylpentyl group, 1,1,2-trimethylpropyl group, 3,3-dimethylbutyl group, normal heptyl group, 2-heptyl group, 3-heptyl group , 2-methylhexyl group, 3-methylhexyl group, 4-methylhexyl group, isoheptyl group and normal octyl group, the term "(C ₂ -C ₈ )alkenyl group" refers to straight or branched alkenyl groups having from 2 to 8 carbon atoms such as vinyl group, allylic group, isopropenyl group, 1-butenyl group, 2-butenyl group, 2-methyl-2-propenyl group, 1-methyl-2-propenyl group, 2-methyl-1-propenyl group, pentenyl group, 1-hexenyl group, 3,3-dimethyl-1-butenyl group, heptenyl group and octenyl group, and the term "(C ₂ -C ₈ )alkynyl group" refers to straight or branched alkynyl groups having from 2 to 8 carbon atoms such as ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 3-methyl-1-propynyl group, 2-methyl-3-propynyl group , pentynyl group, 1-hexynyl group, 3-methyl-1-butynyl group, 3,3-dimethyl-1-butynyl group, heptynyl group and octinyl group.

[0015]

The term "(C ₁ -C ₆ )alkyl group" refers to straight or branched alkyl groups having from 1 to 6 carbon atoms, such as methyl group, ethyl group, normal propyl group, isopropyl group, normal butyl group, isobutyl group, secondary butyl group, tertiary butyl group, normal pentyl group, isopentyl group, tertiary pentyl group, neopentyl group, 2,3-dimethylpropyl group, 1-ethylpropyl group, 1-methylbutyl group, 2-methylbutyl group, normal hexyl group, isohexyl group , 2-hexyl group, 3-hexyl group, 2-methylpentyl group, 3-methylpentyl group, 1,1,2-trimethylpropyl group and 3,3-dimethylbutyl group, the term "(C ₂ -C ₆ )alkenyl group" refers to straight or branched alkenyl groups having from 2 to 6 carbon atoms, such as vinyl group, allylic group, isopropenyl group, 1-butenyl group, 2-butenyl group, 2-methyl-2-propenyl group, 1-methyl-2 -propenyl group, 2-methyl-1-propenyl group, pentenyl group, 1-hexenyl group and 3,3-dimethyl-1-butenyl group, and the term “(C ₂ -C ₆ )alkynyl group” refers to straight or branched alkynyl groups having from 2 to 6 carbon atoms, such as ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 3-methyl-1-propynyl group, 2-methyl-3-propynyl group, pentynyl group, 1-hexynyl group, 3-methyl-1-butynyl group and 3,3-dimethyl-1-butynyl group.

[0016]

The term "(C ₃ -C ₈ )cycloalkyl group" refers to cyclic alkyl groups having from 3 to 8 carbon atoms, such as cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group and cyclooctyl group, and the term "( "C ₁ -C ₈ "alkoxy group" refers to straight or branched alkoxy groups having from 1 to 8 carbon atoms, such as methoxy group, ethoxy group, normal propoxy group, isopropoxy group, normal butoxy group, secondary butoxy group, tertiary butoxy group group, normal pentyloxy group, isopentyloxy group, tertiary pentyloxy group, neopentyloxy group, 2,3-dimethylpropyloxy group, 1-ethylpropyloxy group, 1-methylbutyloxy group, normal hexyloxy group, isohexyloxy group, 1,1,2-trimethylpropyloxy group, normal heptyloxy group and normal octyloxy group.

[0017]

The term "(C ₃ -C ₆ )cycloalkyl group" refers to cyclic alkyl groups having from 3 to 6 carbon atoms, such as cyclopropyl group, cyclobutyl group, cyclopentyl group and cyclohexyl group, and the term "(C ₁ -C ₆ ) "alkoxy group" refers to straight or branched alkoxy groups having from 1 to 6 carbon atoms, such as methoxy group, ethoxy group, normal propoxy group, isopropoxy group, normal butoxy group, secondary butoxy group, tertiary butoxy group, normal pentyloxy group, isopentyloxy group, tertiary pentyloxy group, neopentyloxy group, 2,3-dimethylpropyloxy group, 1-ethylpropyloxy group, 1-methylbutyloxy group, normal hexyloxy group, isohexyloxy group and 1,1,2-trimethylpropyloxy group.

[0018]

The term "(C ₁ -C ₈ )alkylthio group" refers to straight or branched alkylthio groups having from 1 to 8 carbon atoms, such as methylthio group, ethylthio group, normal propylthio group, isopropylthio group, normal butylthio group, secondary butylthio group , tertiary butylthio group, normal pentylthio group, isopentylthio group, tertiary pentylthio group, neopentylthio group, 2,3-dimethylpropylthio group, 1-ethylpropylthio group, 1-methylbutylthio group, normal hexylthio group, isohexylthio group, 1,1,2-trimethylpropylthio group, normal heptylthio group and normal octylthio group, the term "(C ₁ -C ₈ )alkylsulfinyl group" refers to straight or branched alkylsulfinyl groups having from 1 to 8 carbon atoms, such as methylsulfinyl group, ethylsulfinyl group, normal propylsulfinyl group, isopropylsulfinyl group, normal butylsulfinyl group, secondary butylsulfinyl group, tertiary butylsulfinyl group, normal pentylsulfinyl group, isopentylsulfinyl group, tertiary pentylsulfinyl group, neopentylsulfinyl group, 2,3-dimethylpropylsulfinyl group, 1-ethylpropylsulfinyl group, 1-methylbutylsulfinyl group, normal g exylsulfinyl group, isohexylsulfinyl group, 1,1,2-trimethylpropylsulfinyl group, normal heptylsulfinyl group and normal octylsulfinyl group, and the term "(C ₁ -C ₈ )alkylsulfonyl group" refers to straight or branched alkylsulfonyl groups having from 1 to 8 carbon atoms, such such as methylsulfonyl group, ethylsulfonyl group, normal propylsulfonyl group, isopropylsulfonyl group, normal butylsulfonyl group, secondary butylsulfonyl group, tertiary butylsulfonyl group, normal pentylsulfonyl group, isopentylsulfonyl group, tertiary pentylsulfonyl group, neopentylsulfonyl group, 2,3-dimethylpropylsulfonyl group, 1-ethylpropylsulfonyl group, 1-methylbutylsulfonyl group, normal hexylsulfonyl group, isohexylsulfonyl group, 1,1,2-trimethylpropylsulfonyl group, normal heptylsulfonyl group and normal octylsulfonyl group.

[0019]

The term "(C ₁ -C ₆ )alkylthio group" refers to straight or branched alkylthio groups having from 1 to 6 carbon atoms, such as methylthio group, ethylthio group, normal propylthio group, isopropylthio group, normal butylthio group, secondary butylthio group , tertiary butylthio group, normal pentylthio group, isopentylthio group, tertiary pentylthio group, neopentylthio group, 2,3-dimethylpropylthio group, 1-ethylpropylthio group, 1-methylbutylthio group, normal hexylthio group, isohexylthio group and 1,1,2-trimethylpropylthio group group, the term "(C ₁ -C ₆ )alkylsulfinyl group" refers to straight or branched alkylsulfinyl groups having from 1 to 6 carbon atoms, such as methylsulfinyl group, ethylsulfinyl group, normal propylsulfinyl group, isopropylsulfinyl group, normal butylsulfinyl group, secondary butylsulfinyl group, tertiary butylsulfinyl group, normal pentylsulfinyl group, isopentylsulfinyl group, tertiary pentylsulfinyl group, neopentylsulfinyl group, 2,3-dimethylpropylsulfinyl group, 1-ethylpropylsulfinyl group, 1-methylbutylsulfinyl group, normal hexylsulfinyl group, isohexylsulfinyl group and 1,1 ,2 -trimethylpropylsulfonyl group, and the term "(C ₁ -C ₆ )alkylsulfonyl group" refers to straight or branched alkylsulfonyl groups having from 1 to 6 carbon atoms, such as methylsulfonyl group, ethylsulfonyl group, normal propylsulfonyl group, isopropylsulfonyl group, normal butylsulfonyl group group, secondary butylsulfonyl group, tertiary butylsulfonyl group, normal pentylsulfonyl group, isopentylsulfonyl group, tertiary pentylsulfonyl group, neopentylsulfonyl group, 2,3-dimethylpropylsulfonyl group, 1-ethylpropylsulfonyl group, 1-methylbutylsulfonyl group, normal hexylsulfonyl group, isohexylsulfonyl group and 1, 1,2-trimethylpropylsulfonyl group.

[0020]

The above "(C ₁ -C ₈ )alkyl group", "(C ₂ -C ₈ )alkenyl group", "(C ₂ -C ₈ )alkynyl group", "(C ₃ -C ₈ )cycloalkyl group", " (C ₁ -C ₈ )alkoxy group", "(C ₁ -C ₈ )alkylthio group", "(C ₁ -C ₈ )alkylsulfinyl group" or "(C ₁ -C ₈ )alkylsulfonyl group" may be replaced by one or several halogen atoms in a substitutable position, and when the number of halogen atoms to be used in the substitution is two or more, these halogen atoms may be the same or different. Each group substituted by one or more halogens is defined as a "halogen(C ₁ -C ₈ )alkyl group", "halogen(C ₂ -C ₈ )alkenyl group", "halogen(C ₂ -C ₈ )alkynyl group", "halogen(C ₃ -C ₈ )cycloalkyl group", "halogen(C ₁ -C ₈ )alkoxy group", "halogen(C ₁ -C ₈ )alkylthio group", "halogen(C ₁ -C ₈ )alkylsulfinyl group "or "halogen(C ₁ -C ₈ )alkylsulfonyl group."

[0021]

The above "(C ₁ -C ₆ )alkyl group", "(C ₂ -C ₆ )alkenyl group", "(C ₂ -C ₆ )alkynyl group", "(C ₃ -C ₆ )cycloalkyl group", " (C ₁ -C ₆ )alkoxy group", "(C ₁ -C ₆ )alkylthio group", "(C ₁ -C ₆ )alkylsulfinyl group" or "(C ₁ -C ₆ )alkylsulfonyl group" may be replaced by one or several halogen atoms in a substitutable position, and when the number of halogen atoms to be used in the substitution is two or more, these halogen atoms may be the same or different. Each group substituted by one or more halogens is defined as a "halogen(C ₁ -C ₆ )alkyl group", "halogen(C ₂ -C ₆ )alkenyl group", "halogen(C ₂ -C ₆ )alkynyl group", "halogen(C ₃ -C ₆ )cycloalkyl group", "halogen(C ₁ -C ₆ )alkoxy group", "halogen(C ₁ -C ₆ )alkylthio group", "halogen(C ₁ -C ₆ )alkylsulfinyl group "or "halogen(C ₁ -C ₆ )alkylsulfonyl group."

[0022]

Expressions “(C ₁ -C ₆ )”, “(C ₂ -C ₆ )”, “(C ₃ -C ₆ )”, “(C ₁ -C ₈ )”, “(C ₂ -C ₈ )” , “(C ₃ -C ₈ )” and the like refer to a range of carbon numbers of various substituents. The above definition also applies to the group to which the above substituent is attached, and for example, "(C ₃ -C ₈ )cycloalkyl(C ₁ -C ₈ )alkyl group" refers to a straight or branched cycloalkyl group having from 3 to 8 atoms carbon bonded to a straight or branched alkyl group having from 1 to 8 carbon atoms.

[0023]

The term "aryl group" refers to aromatic hydrocarbon groups having from 6 to 10 carbon atoms, such as the phenyl group, 1-naphthyl group and 2-naphthyl group.

[0024]

The term "aromatic heterocyclic group" refers to 5-6 membered monocyclic aromatic heterocyclic groups having from 1 to 5 heteroatoms, such as an oxygen atom, a nitrogen atom and a sulfur atom, such as furyl, thienyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, oxadizolyl, thiadiazolyl, triazolyl, tetrazolyl and triazinyl; and 9 to 18 membered aromatic fused heterocyclic groups having from 1 to 5 heteroatoms such as an oxygen atom, a nitrogen atom and a sulfur atom, such as quinolyl, isoquinolyl, quinazolyl, quinoxalyl, benzofuranyl, benzothienyl, benzoxazolyl, benzoisooxazolyl, benzothiazolyl, benzimidazolyl , benzotriazolyl, indolyl, indazolyl, pyrrolopyridinyl, imidazopyridinyl, imidazopyrazinyl, pyrazolopyridinyl, pyrazolothienyl and pyrazolotriazinyl.

[0025]

The term "saturated nitrogen-containing aliphatic heterocycle" refers to 5-8 membered saturated nitrogen-containing aliphatic heterocycles having at least one (preferably 1 or 2) nitrogen atom and, in addition, optionally having 1 to 2 heteroatoms, such as an oxygen atom and a sulfur atom, such as pyrrolidine, piperidine, morpholine and piperazine.

[0026]

The term "(C ₁ -C ₆ )alkylcarbonyl group" refers to alkylcarbonyl groups consisting of a straight or branched alkyl group having from 1 to 6 carbon atoms and a carbonyl group such as an acetyl group, propionyl group, butyryl group, isobutyryl group , normal butylcarbonyl group, isobutylcarbonyl group, secondary butylcarbonyl group, tertiary butylcarbonyl group, normal pentylcarbonyl group, isopentylcarbonyl group, tertiary pentylcarbonyl group, neopentylcarbonyl group, 2,3-dimethylpropylcarbonyl group, 1-ethylpropylcarbonyl group, 1-methylbutylcarbonyl group, 2-methylbutylcarbonyl group, normal hexylcarbonyl group, isohexylcarbonyl group, 2-hexylcarbonyl group, 3-hexylcarbonyl group, 2-methylpentylcarbonyl group, 3-methylpentylcarbonyl group, 1,1,2-trimethylpropylcarbonyl group, 3,3-dimethylbutylcarbonyl group.

[0027]

The term "(C ₁ -C ₆ )alkoxycarbonyl group" refers to alkoxycarbonyl groups consisting of a straight or branched alkoxy group having from 1 to 6 carbon atoms and a carbonyl group such as methoxycarbonyl group, ethoxycarbonyl group, normal propoxycarbonyl group, isopropoxycarbonyl group group, normal butoxycarbonyl group, secondary butoxycarbonyl group, tertiary butoxycarbonyl group, normal pentyloxycarbonyl group, isopentyloxycarbonyl group, tertiary pentyloxycarbonyl group, neopentyloxycarbonyl group, 2,3-dimethylpropyloxycarbonyl group, 1-ethylpropyloxycarbonyl group, 1-methylbutyloxycarbonyl group, normal hexyloxycarbonyl group, isohexyloxycarbonyl group and 1,1,2-trimethylpropyloxycarbonyl group.

[0028]

The term "tri(C ₁ -C ₆ )alkylsilyl groups" refers to straight or branched trialkylsilyl groups having from 1 to 6 carbon atoms, such as trimethylsilyl group, triethylsilyl group, tertiary butyldimethylsilyl group, ethyldimethylsilyl group, isopropyldimethylsilyl group and n-propyldimethylsilyl group group. In this case, these alkyl groups may be the same or different.

[0029]

Examples of the term "(C ₁ -C ₆ )alkylenedioxy group" include methylenedioxy group and ethylenedioxy group. The two hydroxy groups in an alkylenedioxy group may be attached to the same carbon atom or to different carbon atoms of the nitrogen-containing aliphatic heterocycle.

[0030]

Examples of the salt of the benzimidazole derivative represented by the general formula (1) of the present invention include salts of inorganic acids such as hydrochlorides, sulfates, nitrates and phosphates, salts of organic acids such as acetates, fumarates, maleates, oxalates, methanesulfonates, benzenesulfonates, and etc. -toluenesulfonates, and salts with an inorganic or organic base such as sodium ion, potassium ion, calcium ion and trimethylammonium.

[0031]

The benzimidazole derivative represented by the general formula (1) of the present invention and its salt may have one asymmetric center in the structural formula, and the present invention covers all optical isomers and mixtures of these isomers in any ratio.

[0032]

In the benzimidazole derivative represented by the general formula (1) of the present invention, or a salt thereof, it is preferable

R represents (a1) (C ₁ -C ₈ )alkyl group; (a2) (C ₃ -C ₈ )cycloalkyl group; (a4) a halogen(C ₁ -C ₈ )alkyl group; (a7) an aryl group or (a8) an aryl group having from 1 to 5 substituents, which may be the same or different and selected from (a) a halogen atom, (b) a (C ₁ -C ₆ ) alkyl group, (c) halogen(C ₁ -C ₆ )alkyl group, (d) (C ₁ -C ₆ )alkoxy group, (e) halogen(C ₁ -C ₆ )alkoxy group, (f) (C ₁ -C ₆ )alkylthio group , (g) halogen(C ₁ -C ₆ )alkylthio group, (h) (C ₁ -C ₆ )alkylsulfinyl group, (i) halogen(C ₁ -C ₆ )alkylsulfinyl group, (j) (C ₁ -C ₆ ) alkylsulfonyl group, (k) a halogen(C ₁ -C ₆ )alkylsulfonyl group and (l) a tri(C ₁ -C ₆ )alkylsilyl group, where the alkyl groups may be the same or different);

R ¹ represents a (b1) (C ₁ -C ₈ )alkyl group; (b2) a halogen(C ₁ -C ₈ )alkyl group; (b3) (C ₃ -C ₈ )cycloalkyl group; (b5) (C ₃ -C ₈ )cycloalkyl (C ₁ -C ₈ )alkyl group; (b11) an aryl group; (b12) an aryl group having from 1 to 5 substituents, which may be the same or different and selected from (a) a halogen atom, (b) a (C ₁ -C ₆ ) alkyl group, (c) a halogen (C ₁ -C ₆ )alkyl group, (d) (C ₁ -C ₆ )alkoxy group, (e) halogen(C ₁ -C ₆ )alkoxy group, (f) (C ₁ -C ₆ )alkylthio group, (g) halogen( C ₁ -C ₆ )alkylthio group, (h) (C ₁ -C ₆ )alkylsulfinyl group, (i) halogen(C ₁ -C ₆ )alkylsulfinyl group, (j) (C ₁ -C ₆ )alkylsulfinyl group, ( k) a halogen(C ₁ -C ₆ )alkylsulfonyl group and (l) a tri(C ₁ -C ₆ )alkylsilyl group, where the alkyl groups may be the same or different); (b13) aryl(C ₁ -C ₈ )alkyl group; (b14) aryl(C ₁ -C ₆ )alkyl group having from 1 to 5 substituents, which may be the same or different and selected from (a) a halogen atom, (b) a (C ₁ -C ₆ )alkyl group, ( c) halogen(C ₁ -C ₆ )alkyl group, (d) (C ₁ -C ₆ )alkoxy group, (e) halogen(C ₁ -C ₆ )alkoxy group, (f) (C ₁ -C ₆ ) alkylthio group, (g) halogen(C ₁ -C ₆ )alkylthio group, (h) (C ₁ -C ₆ )alkylsulfinyl group, (i) halogen(C ₁ -C ₆ )alkylsulfinyl group, (j) (C ₁ -C ₆ )alkylsulfonyl group, (k) halogen(C ₁ -C ₆ )alkylsulfonyl group and (l) tri(C ₁ -C ₆ )alkylsilyl group, where the alkyl groups may be the same or different); (b17) (C ₁ -C ₈ )alkoxy(C ₁ -C ₈ )alkyl group; (b18) (C ₁ -C ₈ )alkylthio(C ₁ -C ₈ )alkyl group or (b20) (C ₁ -C ₈ )alkylsulfonyl(C ₁ -C ₈ )alkyl group,

X represents O, S, SO, SO ₂ or NR ² where R ² represents a (C ₁ -C ₆ )alkyl group, (C ₁ -C ₆ )alkylcarbonyl group or (C ₁ -C ₆ )alkylsulfonyl group. Alternatively, R ² can be attached to R ¹ to form, together with the nitrogen atom to which R ² is attached, a 5-8 membered saturated nitrogen-containing aliphatic heterocycle, optionally having from 1 to 5 substituents, where the substituent is selected from (C ₁ -C ₆ )alkyl group, (C ₁ -C ₆ )alkylcarbonyl group, (C ₁ -C ₆ )alkoxycarbonyl group, (C ₁ -C ₆ )alkylsulfonyl group, halogen (C ₁ -C ₆ )alkylsulfonyl group and (C ₁ - C ₆ )alkylenedioxy groups, where two hydroxy groups in the alkylenedioxy group can be attached to the same carbon atom or to different carbon atoms of the nitrogen-containing aliphatic heterocycle,

Y may be the same or different and represents a (c1) halogen atom,

m stands for 0 or 1,

Z may be the same or different and represents a (d1) halogen atom or (d2) (C ₁ -C ₈ )alkyl group,

n stands for 0, 1 or 2.

Further, preferably, R is an (a1) (C ₁ -C ₆ )alkyl group, R ¹ is a (b1) halogen (C ₁ -C ₆ )alkyl group, and m and n are 0.

[0033]

The benzimidazole derivative represented by the general formula (1) of the present invention or a salt thereof can be produced, for example, by the production method shown below, but the present invention is not limited to this.

[0034]

Obtaining method 1

[Formula 2]

,

where R, R ¹ , X, Y, Z, m and n are as above, and hal represents a halogen atom.

[0035]

Production method in step [A]

The nitrile compound represented by the general formula (2-2) can be prepared by reacting the compound represented by the general formula (2-3) and the compound represented by the general formula (4) in the presence of a base and an inert solvent.

[0036]

Examples of the base used in the present reaction include inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogencarbonate and potassium hydrogencarbonate, acetates such as sodium acetate and potassium acetate, alkali metal alkoxides such as tertiary potassium butoxide, sodium methoxide and sodium ethoxide; tertiary amines such as triethylamine, diisopropylethylamine and 1,8-diazabicyclo[5,4,0]undec-7-ene, nitrogen-containing aromatic compounds such as pyridine and dimethylaminopyridine, and these bases are used in amounts typically ranging from 1 to 10 times the molar amount relative to the compound represented by the general formula (4).

[0037]

An example of an inert solvent used in the present reaction may be any solvent as long as it does not interfere with the reaction, and examples may include inert solvents such as aromatic hydrocarbons such as benzene, toluene and xylene, halogenated hydrocarbons such as methylene chloride, chloroform and carbon tetrachloride; halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene, straight or cyclic ethers such as diethyl ether, methyl tert-butyl ether, dioxane and tetrahydrofuran, esters such as ethyl acetate, amides such as dimethylformamide and dimethylacetamide, ketones such as acetone and methyl ethyl ketone, polar solvents such as dimethyl sulfoxide, 1,3-dimethyl-2-imidazolidinone and N-methylpyrrolidone (NMP), and one of these inert solvents can be used alone, or two or more of them can be used in mixture .

[0038]

The present reaction is an equimolar reaction and therefore each reactant is used in equal numbers of moles, but either reactant can also be used in excess. The reaction temperature can range from room temperature to the boiling point of the inert solvent used, and the reaction time varies depending on the size of the reaction and the reaction temperature, but can range from a few minutes to 48 hours.

[0039]

After completion of the reaction, the desired compound is isolated in a conventional manner from the reaction system containing the desired compound, and the desired compound, if necessary, can be obtained by purification by recrystallization or column chromatography. Alternatively, the next step can be carried out without isolating the intermediate product from the reaction system.

[0040]

Production method step [B]

A carboxylic acid compound represented by the general formula (2-1) can be prepared by reacting a nitrile compound represented by the general formula (2-2) in the presence of a base and an inert solvent.

[0041]

Examples of the base used in the present reaction include inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogencarbonate and potassium hydrogencarbonate, acetates such as sodium acetate and potassium acetate, and these bases are used in an amount typically in the range of 1 to 10 times the number of moles relative to the compound represented by the general formula (2-2).

[0042]

Examples of the inert solvent used in the present reaction may be any solvent as long as it does not interfere with the reaction, and examples may include inert solvents such as aromatic hydrocarbons such as benzene, toluene and xylene, halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene, straight or cyclic ethers such as diethyl ether, methyl tert-butyl ether, dioxane and tetrahydrofuran, amides such as dimethylformamide and dimethylacetamide, ketones such as acetone and methyl ethyl ketone, polar solvents such as dimethyl sulfoxide and 1,3- dimethyl-2-imidazolidinone, alcohols such as methanol, ethanol, propanol, isopropyl alcohol and water, and one of these inert solvents may be used alone or two or more of them may be used in mixture.

[0043]

After completion of the reaction, the desired compound is isolated in a conventional manner from the reaction system containing the desired compound, and the desired compound can be obtained by purification by recrystallization or column chromatography, if necessary.

[0044]

Production method step [C]

An amide compound represented by the general formula (2) can be prepared by reacting a carboxylic acid compound represented by the general formula (2-1) and a diamino compound represented by the general formula (3) in the presence of a condensing agent, a base and an inert solvent.

[0045]

Examples of the condensing agent used in the present reaction may include diethyl phosphorocyanidate (DEPC), carbonyldiimidazole (CDI), 1,3-dicyclohexylcarbodiimide (DCC), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC) or its hydrochloride, chlorocarboxylic acid esters and 2-chloro-1-methylpyridinium iodide, and these agents are used in an amount suitable for application selected from the range of 1 to 1.5 mole times of the compound represented by the general formula (2-1).

[0046]

Examples of the base used in the present reaction include inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogencarbonate and potassium hydrogencarbonate, acetates such as sodium acetate and potassium acetate, alkali metal alkoxides such as tertiary potassium butoxide, sodium methoxide and sodium ethoxide; tertiary amines such as triethylamine, diisopropylethylamine and 1,8-diazabicyclo[5,4,0]undec-7-ene, nitrogen-containing aromatic compounds such as pyridine and dimethylaminopyridine (DMAP), and these bases are used in quantities suitable for application , typically in the range of 0.1 to 10 times the number of moles relative to the compound represented by the general formula (2-1).

[0047]

An example of an inert solvent used in the present reaction may be any solvent as long as it does not interfere with the reaction, and examples may include inert solvents such as aromatic hydrocarbons such as benzene, toluene and xylene, halogenated hydrocarbons such as methylene chloride, chloroform and carbon tetrachloride; halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene, straight or cyclic ethers such as diethyl ether, methyl tert-butyl ether, dioxane and tetrahydrofuran, esters such as ethyl acetate, amides such as dimethylformamide and dimethylacetamide, ketones such as acetone and methyl ethyl ketone, polar solvents such as dimethyl sulfoxide, 1,3-dimethyl-2-imidazolidinone, and nitrogen-containing aromatic compounds such as pyridine, and one of these inert solvents may be used alone, or two or more of them may be used in the mixture.

[0048]

The present reaction is an equimolar reaction and therefore each reactant is used in equal numbers of moles, but either reactant can also be used in excess. The reaction temperature can range from room temperature to the boiling point of the inert solvent used, and the reaction time varies depending on the size of the reaction and the reaction temperature, but can range from a few minutes to 48 hours.

[0049]

After completion of the reaction, the desired compound is isolated in a conventional manner from the reaction system containing the desired compound, and the desired compound, if necessary, can be obtained by purification by recrystallization or column chromatography. Alternatively, the next step can be carried out without isolating the intermediate product from the reaction system.

[0050]

Production method step [D]

The benzimidazole derivative represented by the general formula (1-1) can be prepared by reacting the amide compound represented by the general formula (2) in the presence of an acid and an inert solvent.

[0051]

Examples of the acid used in the reaction may include inorganic acids such as hydrochloric acid, sulfuric acid, nitric acid, organic acids such as formic acid, acetic acid, propionic acid, trifluoroacetic acid and benzoic acid, sulfonic acids such as methanesulfonic acid , trifluoromethanesulfonic acid and p-toluenesulfonic acid, and phosphoric acids, and these acids are used in a suitable amount suitably selected from the range of 0.01 to 10 times the mole amount relative to the amide compound represented by the general formula (1-1).

[0052]

An example of an inert solvent used in the present reaction may be any solvent as long as it does not interfere with the reaction, and examples may include inert solvents such as aromatic hydrocarbons such as benzene, toluene and xylene, halogenated hydrocarbons such as methylene chloride, chloroform and carbon tetrachloride; halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene, straight or cyclic ethers such as diethyl ether, methyl tert-butyl ether, dioxane and tetrahydrofuran, esters such as ethyl acetate, amides such as dimethylformamide and dimethylacetamide, ketones such as acetone and methyl ethyl ketone, polar solvents such as dimethyl sulfoxide, 1,3-dimethyl-2-imidazolidinone and N-methylpyrrolidone (NMP), and one of these inert solvents can be used alone, or two or more of them can be used in mixture .

[0053]

After completion of the reaction, the desired compound is isolated in a conventional manner from the reaction system containing the desired compound, and the desired compound, if necessary, can be obtained by purification by recrystallization or column chromatography.

[0054]

Production method stage [E]

The benzimidazole derivative represented by the general formula (1) can be prepared by reacting the benzimidazole derivative represented by the general formula (1-1) and the corresponding sulfonyl chloride in the presence of an inert solvent and base.

[0055]

Examples of the base used in the present reaction include inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogencarbonate, potassium hydrogencarbonate and sodium hydride, acetates such as sodium acetate and potassium acetate, alkali metal alkoxides such as potassium tert-butoxide, sodium methoxide and sodium ethoxide; tertiary amines such as triethylamine, diisopropylethylamine and 1,8-diazabicyclo[5,4,0]undec-7-ene, nitrogen-containing aromatic compounds such as pyridine and dimethylaminopyridine, and these bases are used in an amount suitable for application, usually in ranging from 1 to 10 times the number of moles relative to the compound represented by the general formula (1-1).

[0056]

An example of the inert solvent used in the present reaction may be any solvent as long as it does not interfere with the reaction, and examples may include aromatic hydrocarbons such as benzene, toluene and xylene, halogenated hydrocarbons such as methylene chloride, chloroform and carbon tetrachloride; halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene, straight or cyclic ethers such as diethyl ether, tetrahydrofuran (THF) and dioxane, and one of these inert solvents may be used alone or two or more of them may be used in mixture .

[0057]

The sulfonyl chloride used in the present reaction is not particularly limited as long as it is a sulfonyl chloride represented by the formula: RSO ₂ Cl (R is as described above). The present reaction is an equimolar reaction and therefore each reactant is used in equal numbers of moles, but either reactant can also be used in excess.

[0058]

The reaction temperature in the present reaction may generally be in the range from about 0ºC to the boiling point of the solvent used, and the reaction time is variable, depending on the scale of the reaction and the reaction temperature, but at the same time can be suitably selected from the range from a few minutes to 48 hours.

[0059]

After completion of the reaction, the desired compound is isolated in a conventional manner, and the desired compound, if necessary, is obtained by purification by recrystallization, distillation or column chromatography.

[0060]

Hereinafter, specific examples of the compounds of the present invention are provided below. In the table below, Me refers to the methyl group, Et refers to the ethyl group, n-Pr refers to the normal propyl group, iso-Pr refers to the isopropyl group, n-Bu refers to the normal butyl group, tert-Bu refers to the tertiary butyl group, n-Pen refers to the normal pentyl group, n-Hex refers to the normal hexyl group, c-Pr refers to the cyclopropyl group, c-Pen refers to the cyclopentyl group, c-Hex refers to the cyclohexyl group, c-Hep refers to the cycloheptyl group, Ac refers to the acetyl group, pTol refers to the p-tolyl group, Ph refers to the phenyl group, Bn refers to the benzyl group and TMS refers to the trimethylsilyl group. Physical property is indicated by melting points (ºC) or H ¹ -NMR. H ¹ NMR data are shown in Table 8.

[0061]

[Formula 3]

[0062]

[Table 1]

Table 1

Connection number R ¹ X Y ¹ Y ² Y ³ Z ¹ Z ² Z ³ Z ⁴ R Physical property 1-1 CF ₃ CH ₂ O H H H H H H H Et 99-101 1-2 CF ₃ CF ₂ CH ₂ O H H H H H H H Et 105-106 1-3 CF ₃ CF ₂ CH ₂ O H H H H H H H Me 170-172 1-4 CF ₃ CF ₂ CH ₂ O H H H H H H H n-Pr 89-90 1-5 CF ₃ CF ₂ CH ₂ O H H H H H H H n-Bu 86-87 1-6 CF ₃ CF ₂ CH ₂ O H H H H H H H c-Pr 97-98 1-7 CF ₃ CF ₂ CH ₂ O H H H H H H H CF ₃ 104-106 1-8 CF ₃ CF ₂ CH ₂ O H H H H H H H pTol 133-135 1-9 CF ₃ CF ₂ CH ₂ O H H H H H Br H Et 154-159 1-10 CF ₃ CF ₂ CH ₂ O H H H H Br H H Et 130-131 1-11 CF ₃ CF ₂ CH ₂ O H H H H H H Br Et 1-12 CF ₃ CF ₂ CH ₂ O H H H H H Cl H Et 159-161 1-13 CF ₃ CF ₂ CH ₂ O H H H H Cl H H Et 119-120 1-14 CF ₃ CF ₂ CH ₂ O H H H H Cl Cl H Et 177-178 1-15 CF ₃ CF ₂ CH ₂ O H H H H Br Br H Et 184-186 1-16 CF ₃ CF ₂ CH ₂ O H H H H Br H Br Et 1-17 CF ₃ CF ₂ CH ₂ O H H H H Me Me H Et 148-149 1-18 CF ₃ CF ₂ CH ₂ O Cl H H H H H H Et 88-90 1-19 CHF ₂ CF ₂ CH ₂ O H H H H H H H Et 77-78 1-20 CF ₃ CF ₂ CF ₂ CH ₂ O H H H H H H H Et 99-101 1-21 CF ₃ CF ₂ CF ₂ CH ₂ O H H H H H Br H Et 137-138 1-22 CF ₃ CF ₂ CF ₂ CH ₂ O H H H H Br H H Et 110-112 1-23 (CF ₃ ) ₂ CH O H H H H H H H Et 102-104 1-24 CF ₃ CHFCF ₂ CH ₂ O H H H H H H H Et 93-94 1-25 CF ₃ CH ₂ NMe H H H H H H H Et

[0063]

[Table 2]

table 2

Number
conn. R ¹ X Y ¹ Y ² Y ³ Z ¹ Z ² Z ³ Z ⁴ R Physical
property 1-26 CF ₃ CH ₂ NAc H H H H H H H Et 1-27 CF ₃ CH ₂ NSO ₂ Et H H H H H H H Et 1-28 CF ₃ CF ₂ CH ₂ NMe H H H H H H H Et 1-29 CF ₃ CF ₂ CH ₂ NAc H H H H H H H Et 1-30 CF ₃ CF ₂ CH ₂ NSO ₂ Et H H H H H H H Et 1-31 CF ₃ S H H H H H H H Et 1-32 CF ₃ SO H H H H H H H Et 1-33 CF ₃ SO ₂ H H H H H H H Et 1-34 CF ₃ CH ₂ S H H H H H H H Et 1-35 CF ₃ CH ₂ SO H H H H H H H Et 1-36 CF ₃ CH ₂ SO ₂ H H H H H H H Et 1-37 CF ₃ CF ₂ CH ₂ S H H H H H H H Et 1-38 CF ₃ CF ₂ CH ₂ SO H H H H H H H Et 1-39 CF ₃ CF ₂ CH ₂ SO ₂ H H H H H H H Et 1-40 4-CF ₃ SPh O H H H H H H H Et 135-136 1-41 4-CF ₃ SOPh O H H H H H H H Et 120-121 1-42 4-CF ₃ SO ₂ Ph O H H H H H H H Et 122-123 1-43 4-CF ₃ SBN O H H H H H H H Et 118-119 1-44 4-CF ₃ SOBn O H H H H H H H Et 110-111 1-45 CF ₃ CF ₂ CH ₂ O H H H H H H H _CH2Cl 113-115 1-46 4-CF ₃ OPh O H H H H H H H Et 137-138 1-47 n-Bu O H H H H H H H Et 84-85 1-48 n-Pen O H H H H H H H Et 68-69 1-49 n-Hex O H H H H H H H Et 67-68 1-50 ts-Pen O H H H H H H H Et 81-82 1-51 ts-Hep O H H H H H H H Et 103-104

[0064]

[Formula 4]

[0065]

[Table 3]

Table 3

Connection number R ¹ X Y ¹ Y ² Y ⁴ Z ¹ Z ² Z ³ Z ⁴ R Physical property 2-1 CF ₃ CF ₂ CH ₂ O H H H H H H H Et NMR

[0066]

[Formula 5]

[0067]

[Table 4]

Table 4

Connection number R ¹ X Y ² Y ³ Y ⁴ Z ¹ Z ² Z ³ Z ⁴ R Physical property 3-1 CF ₃ CF ₂ CH ₂ O H H H H H H H Et 93-94

[0068]

[Formula 6]

[0069]

[Table 5]

Table 5

Connection number R ¹ X Y ¹ Y ³ Y ⁴ Z ¹ Z ² Z ³ Z ⁴ R Physical property 4-1 CF ₃ CF ₂ CH ₂ O H H H H H H H Et

[0070]

[Formula 7]

[0071]

[Table 6]

Table 6

Connection number R ¹ X Y ¹ Physical property 5-1 n-Pr O H 90-91 5-2 iso-Pr O H 105-106 5-3 c-Hex O H 124-125 5-4 tert-BuCH ₂ CH ₂ O H 136-137 5-5 CH ₃ OCH ₂ CH ₂ O H 111-112 5-6 CH ₃ SCH ₂ CH ₂ O H 68-69 5-7 CH ₃ SO ₂ CH ₂ CH ₂ O H 152-153 5-8 4-TMSPh O H 147-149 5-9 CF ₃ CH ₂ O Cl 102-105 5-10 CHF ₂ CF ₂ CH ₂ O Cl 98-99 5-11 CF ₃ CF ₂ CF ₂ CF ₂ CF ₂ CF ₂ CH ₂ CH ₂ O H 86-87 5-12 CHF ₂ CF ₂ CF ₂ CF ₂ CF ₂ CF ₂ CH ₂ O H 77-78 5-13 Me S H 137-138 5-14 n-Pr S H 110-111 5-15 n-Pr SO H 118-119 5-16 n-Pr SO ₂ H 134-135 5-17 n-Bu S H 99-100 5-18 ts-Pen S H 135-136 5-19 c-Hex S H 158-159 5-20 c-PrCH ₂ S H 125-126 5-21 Bn S H 105-106 5-22 Bn SO H NMR 5-23 Bn SO ₂ H NMR 5-24 n-Bu N(n-Bu) H 102-103 5-25 n-Bu NMe H NMR

In formula (1a), R represents an ethyl group, Y ² , Y ³ , Z ¹ , Z ² , Z ³ and Z ⁴ each represent a hydrogen atom.

[0072]

[Formula 8]

[0073]

[Table 7]

Table 7

Connection number N(R ¹ )R ² Y ¹ Physical property 6-1 H NMR 6-2 H NMR 6-3 H NMR

In formula (1a-1), R represents an ethyl group, Y ² , Y ³ , Z ¹ , Z ² , Z ³ and Z ⁴ each represent a hydrogen atom.

[0074]

[Table 8]

Table 8

Connection number Data ¹ H-NMR (CDCl ₃ ) 2-1 8.33 (dd, 1H), 7.97-7.91 (m, 1H), 7.89-7.81 (m, 2H), 7.50-7.43 (m, 2H), 7. 16 (dd, 1H), 4.89 (lat, 2H), 3.32 (kv, 2H), 1.21 (t, 3H) 5-22 9.02 (m, 1H), 8.13 (dd, 1H), 8.01 (m, 1H), 7.88 (m, 1H), 7.70 (dd, 1H), 7.52 (m , 2H), 7.25 (m, 3H), 4.43 (d, 1H), 4.17 (d, 1H), 3.17 (q, 2H), 1.08 (t, 3H) 5-23 9.16 (m, 1H), 8.20 (dd, 1H), 8.01 (m, 1H), 7.91 (m, 2H), 7.53 (m, 2H), 7.28 (m , 3H), 7.23 (m, 2H), 4.69 (s, 2H), 3.22 (sq, 2H), 1.06 (t, 3H) 5-25 8.55 (d, 1H), 8.00 (m, 1H), 7.85 (dd, 1H), 7.80 (dd, 1H), 7.40 (m, 2H), 6.53 (d , 1H), 3.58 (t, 2H), 3.13 (m, 5H), 1.62 (m, 2H), 1.37 (m, 2H), 1.04 (t, 3H), 0 .97 (t, 3H) 6-1 8.56 (d, 1H), 7.99 (dd, 1H), 7.85 (dd, 1H), 7.79 (dd, 1H), 7.40 (m, 2H), 6.68 (d , 1H), 3.66 (m, 4H), 3.11 (sq, 2H), 1.67 (m, 5H), 1.51 (t, 1H), 1.04 (t, 3H) 6-2 8.57 (m, 1H), 7.99 (m, 1H), 7.88 (dd, 1H), 7.80 (m, 1H), 7.41 (m, 2H), 6.72 (d , 1H), 4.02 (s, 4H), 3.82 (t, 4H), 3.12 (sq, 2H), 1.80 (t, 4H), 1.04 (t, 3H) 6-3 8.57 (d, 1H), 8.00 (m, 1H), 7.88 (dd, 1H), 7.80 (m, 1H), 7.42 (m, 2H), 6.70 (d , 1H), 4.36 (m, 2H), 4.16 (sq, 2H), 3.12 (m, 4H), 2.59 (m, 1H), 2.01 (m, 2H), 1 .79 (m, 2H), 1.28 (t, 3H), 1.04 (t, 3H)

[0075]

An agricultural and horticultural insecticidal and acaricidal agent containing a benzimidazole derivative represented by the general formula (1) of the present invention, or a salt thereof as an active ingredient, is suitable for controlling various pests that can damage paddy rice, fruit trees, vegetables, etc. crops and ornamental flowering plants. Target pests include, for example, agricultural and forest pests, horticultural pests, stored grain pests, plant health pests, other pests such as nematodes or mites, etc.

[0076]

Examples of the above pests or nematodes include the following.

Examples of order typesLepidoptera includeParasa consocia,Anomis mesogona,Papilio xuthus,Matsumuraeses azukivora,Ostrinia scapulalis,Spodoptera exempta,Hyphantria cunea,Ostrinia furnacalis,Pseudaletia separata,Tinea translucens,Bactra furfurana,Parnara guttata,Marasmia exigua,Parnara guttata,Sesamia inferens,Brachmia triannulla,Monema flavescens,trichoplusia ni,Pleuroptya ruralis,Cystidia couaggaria,Lampides boeticus,Cephonodes hylas,Helicoverpa armigera,Phalerodonta manleyi,Eumeta japonica,Pieris brassicae,Malacosoma neustria testacea,Stathmopoda masinissa,Cuphodes diospyrosella,Archips xylosteanus,Agrotis segetum,Tetramoera schistaceana,Papilio machaon hippocrates,Endoclyta sinensis,Lyonetia prunifoliella,Phyllonorycter ringoneella,Cydia kurokoi,Eucoenogenes aestuosa,Lobesia botrana,Latoia sinica,Euzophera batangensis,Phalonidia mesotypa,Spilosoma imparilis,Glyphodes pyloalis,Olethreutes mori,Tineola bisselliella,Endoclyta excrescens,Nemapogon granellus,Synanthedon hector,Cydia pomonella,Plutella xylostella,Cnaphalocrocis medinalis,Sesamia calamistis,Scirpophaga incertulas,Pediasia teterrellus,Phthorimaea operculella,Stauropus fagi persimilis,Etiella zinckenella,Spodoptera exigua,Palpifer sexnotata,Spodoptera mauritia,Scirpophaga innotata,Xestia c-nigrum,Spodoptera depravata,Ephestia kuehniella,Angerona prunaria,Clostera anastomosis,Pseudoplusia includens,Matsumuraeses falcana,Helicoverpa assulta,Autographa nigrisigna,Agrotis ipsilon,Euproctis pseudoconspersa,Adoxophyes orana,Caloptilia theivora,Homona magnanima,Ephestia elutella,Eumeta minuscula,Clostera anachoreta,Heliothis maritima,Sparganothis pilleriana,Busseola fusca,Euproctis subflava,Biston robustum,Heliothis zea,Aedia leucomelas,Narosoideus flavidorsalis,Viminia rumicis,Bucculatrix pyrivorella,Grapholita molesta,Spulerina astaurota,Ectomyelois pyrivorella,Chilo suppressalis,Acrolepiopsis sapporensis,Plodia interpunctella,Hellula undalis,Sitotroga cerealella,Spodoptera litura, species of the familyTortricidae (Eucosma aporema),Acleris comariana,Scopelodes contractus,Orgyia thyellina,Spodoptera frugiperda,Ostrinia zaguliaevi,Naranga aenescens,Andraca bipunctata,Paranthrene regalis,Acosmeryx castanea,Phyllocnistis toparcha,Endopiza viteana,Eupoecillia ambiguella,Anticarsia gemmatalis,Cnephasia cinereipalpana,Lymantria dispar,Dendrolimus spectabilis,Leguminivora glycinivorella,Maruca testulalis,Matsumuraeses phaseoli,Caloptilia soyella,Phyllocnistis citrella,Omiodes indicata,Archips fuscocupreanus,Acanthoplusia agnata,Bambalinasp.,Carposina niponensis,Conogethes punctiferalis,Synanthedonsp.,Lyonetia clerkella,Papilio helenus,Colias erate poliographus,Phalera flavescens, species of the familyPieridae, such asPieris rapae crucivora and Pieris rapae,Euproctis similis,Acrolepiopsis suzukiella,Ostrinia nubilalis,Mamestra brassicae,Ascotis selenaria,Phtheochroides clandestina,Hoshinoa adumbratana,Odonestis pruni japonensis,triaena intermedia,Adoxophyes orana fasciata,Grapholita inopinata,Spilonota ocellana,Spilonota lechriaspis,Illiberis pruni,Argyrestia conjugella,Caloptilia zachrysa,Archips breviplicanus,Anomis flava,Pectinophora gossypiella,Notarcha derogata,Diaphania indica,Heliothis virescens AndEarias cupreoviridis.

[0077]

Examples of species of the order Hemiptera include Nezara antennata , Stenotus rubrovittatus , Graphosoma rubrolineatum , trigonotylus coelestialium , Aeschynteles maculatus , Creontiades pallidifer , Dysdercus cingulatus , Chrysomphalus ficus , Aonidiella aurantii , Graptopsaltria nigrofuscata , Blis sus leucopterus , Icerya purchasi , Piezodorus hybneri , Lagynotomus elongatus , Thaia subrufa , Scotinophara lurida , Sitobion ibarae , Stariodes iwasakii , Aspidiotus destructor , Taylorilygus pallidulus , Myzus mumecola , Pseudaulacaspis prunicola , Acyrthosiphon pisum , Anacanthocoris striicornis , Ectometopterus micantulus , Eysarcoris lewisi , Molipteryx fuliginosa , Cicadella viridis , Rhopalosophum rufiabdominalis , Saissetia oleae , trialeurodes vaporariorum , Aguriahana quercus , Lygus spp., Euceraphis punctipennis , Andaspis kashicola , Coccus pseudomagnoliarum , Cavelerius saccharivorus , Galeatus spinifrons , Macrosiphoniella sanborni , Aonidiella citrina , Halyomorpha mista , Stephanitis fasciicarina , Trioza camphorae , Leptocorisa chinensis , Tri oza quercicola , Uhlerites latius , Erythroneura comes , Paromius exiguus , Duplaspidiotus claviger , Nephotettix nigropictus , Halticiellus insularis , Perkinsiella saccharicida , Psylla malivorella , Anomomeura mori , Pseudococcus longispinis , Pseudaulacaspis pentagona , Pulvinaria kuwacola , Apolygus lucorum , Togo hemipterus , Toxopter a aurantii , Saccharicoccus sacchari , Geoica lucifuga , Numata muiri , Comstockaspis perniciosa , Unaspis citri , Aulacorthum solani , Eysarcoris ventralis , Bemisia argentifolii , Cicadella spectra , Aspidiotus hederae , Liorhyssus hyalinus , Calophya nigridorsalis , Sogatella furcifera , Megoura crassicauda , Brevicoryne brassicae , Aphis glycines , Leptocorisa oratorius , Ne photettix virescens , Uroeucon formosanum , Cyrtopeltis tennuis , Bemisia tabaci , Lecanium persicae , Parlatoria theae , Pseudaonidia paeoniae , Empoasca onukii , Plautia stali , Dysaphis tulipae , Macrosiphum euphorbiae , Stephanitis pyrioides , Ceroplastes ceriferus , Parlatoria camelliae , Apolygus spinolai , Nephotettix cincticeps , Glaucias subpu nctatus , Orthotylus flavosparsus , Rhopalosiphum maidis , Peregrinus maidis , Eysarcoris parvus , Cimex lectularius , Psylla abieti , Nilaparvata lugens , Psylla tobirae , Eurydema rugosum , Schizaphis piricola , Psylla pyricola , Parlatoreopsis pyri , Stephanitis nashi , Dysmicoccus wistariae , Lepholeucaspis japonica , Sappaphis piri , Lipaphis erysimi , Neotoxoptera formosana , Rhopalosophum nymphaeae , Edwardsiana rosae , Pinnaspis aspidistrae , Psylla alni , Speusotettix subfusculus , Alnetoidia alneti , Sogatella panicicola , Adelphocoris lineolatus , Dysdercus poecilus , Parlatoria ziziphi , Uhlerites debile , Laodelphax striatellus , Eurydema pulchrum , Cletus trigonus , Clovia punctata , Empoasca sp. , Coccus hesperidum , Pachybrachius luridus , Planococcus kraunhiae , Stenotus binotatus , Arboridia apicalis , Macrosteles fascifrons , Dolycoris baccarum , Adelphocoris triannulatus , Viteus vitifolii , Acanthocoris sordidus , Leptocorisa acuta , Macropes obnubilus , Cletus punctiger , Riptortus clavatus , Paratrioza cockerelli , Aphrophora costalis , Lygus disponsi , Lygus saundersi , Crisicoccus pini , Empoasca abietis , Crisicoccus matsumotoi , Aphis craccivora , Megacopta punctatissimum , Eysarcoris guttiger , Lepidosaphes beckii , Diaphorina citri , Toxoptera citricidus , Planococcus citri , Dialeurodes citri , Aleurocanthus spiniferus , Pseudococcus citriculus , Zyginella ci tri, Pulvinaria citricola , Coccus discrepans , Pseudaonidia duplex , Pulvinaria aurantii , Lecanium corni , Nezara viridula , Stenodema calcaratum , Rhopalosiphum padi , Sitobion akebiae , Schizaphis graminum , Sorhoanus tritici , Brachycaudus helichrysi , Carpocoris purpureipennis , Myzus persicae , Hyalopterus pruni , Aphis farinose yanagicola , Metasalis populi , Unaspis yanonensis , Mesohomotoma camphorae , Aphis spiraecola , Aphis pomi , Lepidosaphes ulmi , Psylla mali , Heterocordylus flavipes , Myzus malisuctus , Aphidonuguis mali , Orientus ishidai , Ovatus malicolens , Eriosoma lanigerum , Ceroplastes rubens and Aphis gossypii .

[0078]

Examples of species of the order Coleoptera include Xystrocera globosa , Paederus fuscipes , Eucetonia roelofsi , Callosobruchus chinensis , Cylas formicarius , Hypera postica , Echinocnemus squameus , Oulema oryzae , Donacia provosti , Lissorhoptrus oryzophilus , Colasposoma dauricum , Euscepes postfasciatus , Epilachna varivestis , Acanthoscelides obtectus , Diabrotica virgifera virgifera , Involvulus cupreus , Aulacophora femoralis , Bruchus pisorum , Epilachna vigintioctomaculata , Carpophilus dimidiatus , Cassida nebulosa , Luperomorpha tunebrosa , Phyllotreta striolata , Psacothea hilaris , Aeolesthes chrysothrix , Curculio sikkimensis , Carpophil us hemipterus , Oxycetonia jucunda , Diabrotica spp., Mimela splendens , Sitophilus zeamais , tribolium castaneum , Sitophilus oryzae , Palorus subdepressus , Melolontha japonica , Anoplophora malasiaca , Neatus picipes , Leptinotarsa decemlineata , Diabrotica undecimpunctata howardi , Sphenophorus venatus , Crioceris quatuordecimpunctata , Conotrachelus nenuphar , Ceuth orhynchidius albosuturalis , Phaedon brassicae , Lasioderma serricorne , Sitona japonicus , Adoretus tenuimaculatus , Tenebrio molitor , Basilepta balyi , Hypera nigrirostris , Chaetocnema concinna , Anomala cuprea , Heptophylla picea , Epilachna vigintioctopunctata , Diabrotica longicornis , Eucetonia pilifera , Agriotes spp., Attagenus unicolor japonicus , Pagria signata , Anomala rufocuprea , Palorus ratzeburgii , Alphitobius laevigatus , Anthrenus verbasci , Lyctus brunneus , tribolium confusum , Medythia nigrobilineata , Xylotrechus pyrrhoderus , Epitrix cucumeris , Tomicus piniperda , Monochamus alternatus , Popillia japonica , Epicauta gorhami , Sitophilus zeamais , Rhynchites heros , Listroderes costirostris , Callosobruchus maculatus , Phyllobius armatus , Anthonomus pomorum , Linaeidea aenea and Anthonomus grandis .

[0079]

Examples of species of the order Diptera include Culex pipiens pallens , Pegomya hyoscyami , Liriomyza huidobrensis , Musca domestica , Chlorops oryzae , Hydrellia sasakii , Agromyza oryzae , Hydrellia griseola , Hydrellia griseola , Ophiomyia phaseoli , Dacus cucurbitae , Drosophila suz ukii , Rhacochlaena japonica , Muscina stabulans , species of the family Phoridae , such as Megaselia spiracularis , Clogmia albipunctata , Tipula aino , Phormia regina , Culex tritaeniorhynchus , Anopheles sinensis , Hylemya brassicae , Asphondylia sp., Delia platura , Delia antiqua , Rhagoletis cerasi , Culex pipiens molestus Forskal , Ceratitis capitata , Bradysia agrestis , Pegomya cunicularia , Liriomyza sativae , Liriomyza bryoniae , Chromatomyia horticola , Liriomyza chinensis , Culex quinquefasciatus , Aedes aegypti , Aedes albopictus , Liriomyza trifolii, Liriomyza sativae , Dacus dorsalis , Dacus tsuneonis , Sitodiplosis mosellana , Mer omuza nigriventris , Anastrepha ludens and Rhagoletis pomonell a.

[0080]

Examples of species of the order Hymenoptera include Pristomyrmex pungens , species of the family Bethylidae , Monomorium pharaonis , Pheidole noda , Athalia rosae , Dryocosmus kuriphilus , Formica fusca japonica , species of the subfamily Vespinae , Athalia infumata infumata , Arge pagana , Athalia japonica , Acromyrm ex spp., Solenopsis spp., Arge mali and Ochetellus glaber .

[0081]

Examples of species of the order Orthoptera include Homorocoryphus lineosus , Gryllotalpa sp., Oxya hyla intricata , Oxya yezoensis , Locusta migratoria , Oxya japonica , Homorocoryphus jezoensis and Teleogryllus emma .

[0082]

Examples of species of the order Thysanoptera include Selenothrips rubrocinctus , Stenchaetothrips biformis , Haplothrips aculeatus , Ponticulothrips diospyrosi , Thrips flavus , Anaphothrips obscurus , Liothrips floridensis , Thrips simplex , Thrips nigropilosus , Heliothrips haemorrhoidalis , Ps eudodendrothrips mori , Microcephalothrips abdominalis , Leeuwenia pasanii , Litotetothrips pasaniae , Scirtothrips citri , Haplothrips chinensis , Mycterothrips glycines , Thrips setosus , Scirtothrips dorsalis , Dendrothrips minowai , Haplothrips niger , Thrips tabaci , Thrips alliorum , Thrips hawaiiensis , Haplothrips kurdjumovi , Chirothrips manicatus , Frankliniella intonsa , Thrips coloratus , Franklinella occidentalis , Thrips palmi , Frankliniella lilivora and Liothrips vaneeckei .

[0083]

Examples of order typesAcari includeLeptothrombidium akamushi,Tetranychus ludeni,Dermacentor variabilis,Tetranychus truncatus,Ornithonyssus bacoti,Demodex canis,Tetranychus viennensis,Tetranychus kanzawai, species of the familyIxodidae, such asRhipicephalus sanguineus,Cheyletus malaccensis,Tyrophagus putrescentiae,Dermatophagoides farinae,Latrodectus hasseltii,Dermacentor taiwanensis,Acaphylla theavagrans,Polyphagotarsonemus latus,Aculops lycopersici,Ornithonyssus sylvairum,Tetranychus urticae,Eriophyes chibaensis,Sarcoptes scabiei,Haemaphysalis longicornis,Ixodes scapularis,Tyrophagus similis,Cheyletus eruditus,Panonychus citri,Cheyletus moorei,Brevipalpus phoenicis,Octodectes cynotis,Dermatophagoides ptrenyssnus,Haemaphysalis flava,Ixodes ovatus,Phyllocoptruta citri,Aculus schlechtendali,Panonychus ulmi,Amblyomma americanum,Dermanyssus gallinae,Rhyzoglyphus robini and Sancassaniasp.

[0084]

Examples of species of the order Isoptera include Reticulitermes miyatakei , Incisitermes minor , Coptotermes formosanus , Hodotermopsis japonica , Reticulitermes sp., Reticulitermes flaviceps amamianus , Glyptotermes kushimensis , Coptotermes guangzhoensis , Neotermes koshunensis , Glyptotermes kodam ai , Glyptotermes satsumensis , Cryptotermes domesticus , Odontotermes formosanus , Glyptotermes nakajimai , Pericapritermes nitobei and Reticulitermes speratus .

[0085]

Examples of species of the order Blattodea include Periplaneta fuliginosa , Blattella germanica , Blatta orientalis , Periplaneta brunnea , Blattella lituricollis , Periplaneta japonica and Periplaneta americana .

[0086]

Examples of species in the order Siphonaptera include Pulex irritans , Ctenocephalides felis, and Ceratophyllus gallinae .

[0087]

Examples of Nematoda phylum species include Nothotylenchus acris , Aphelenchoides besseyi , Pratylenchus penetrans , Meloidogyne hapla , Meloidogyne incognita , Globodera rostochiensis , Meloidogyne javanica , Heterodera glycines , Pratylenchus coffeae , Pratylenchus neglectus and Tylenchus semipenetrans .

[0088]

Examples of Mollusca phylum species include those such as Pomacea canaliculata , Achatina fulica , Meghimatium bilineatum , Lehmannina valentiana , Limax flavus and Acusta despecta sieboldiana .

[0089]

In addition, the agricultural and horticultural insecticide of the present invention also has a strong insecticidal effect on Tuta absoluta .

[0090]

In addition, ticks and ticks that parasitize animals are also included among the target pests.

Further, ticks and ticks that parasitize animals are also included among the target pests, and examples include species of the familyIxodidae, such asBoophilus microplus,Rhipicephalus sanguineus,Haemaphysalis longicornis,Haemaphysalis flava,Haemaphysalis campanulata,Haemaphysalis concinna,Haemaphysalis japonica,Haemaphysalis kitaokai,Haemaphysalis ias,Ixodes ovatus,Ixodes nipponensis,Ixodes persulcatus,Amblyomma testudinarium,Haemaphysalis megaspinosa,Dermacent or Reticulatus AndDermacentor taiwanensis;Dermanyssus gallinae; species of the genusOrnithonyssus, such asOrnithonyssus sylviarum AndOrnithonyssus bursa; family speciesTrombiculidae, such asEutrombicula wichmanni,Leptothrombidium akamushi,Leptothrombidium pallidum,Leptothrombidium fuji,Leptothrombidium tosa,Neotrombicula autumnalis,Eutrombicula alfreddugesi AndHelenicula Miyagawai; family speciesCheyletidae, such asCheyletiella yasguri,Cheyletiella parasitivorax AndCheyletiella blakei; superfamily speciesSarcoptoidea, such asPsoroptes cuniculi,Chorioptes bovis,Otodectes cynotis,Sarcoptes scabiei AndNotoedres cati; and family speciesDemodicidae, such asDemodex canis.

[0091]

Other target pests include fleas, including ectoparasitic wingless insects belonging to the order Siphonaptera , more specifically species belonging to the families Pulicidae and Ceratophyllidae . Examples of species classified in the family Pulicidae include Ctenocephalides canis , Ctenocephalides felis , Pulex irritans , Echidnophaga gallinacea , Xenopsylla cheopis , Leptopsylla segnis , Nosopsyllus fasciatus and Monopsyllus anisus .

[0092]

Other target pests include ectoparasites, such as species of the suborder Anoplura , such as Haematopinus eurysternus , Haematopinus asini , Dalmalinia ovis , Linognathus vituli , Haematopinus suis , Phthirus pubis and Pediculus capitis ; species of the suborder Mallophaga , such as trichodectes canis ; and blood-sucking dipteran insect pests such as Tabanus trigonus , Culicoides schultzei and Simulium ornatum . In addition, examples of endoparasites include nematodes such as lungworms , whipworms, knotworms, endogastric parasitic worms, roundworms and filarial worms; cestodes such as Spirometra erinacei , Diphyllobothrium latum , Dipylidium caninum , Multiceps multiceps , Echinococcus granulosus and Echinococcus multilocularis ; flukes such as Schistosoma japonicum and Fasciola hepatica ; and protozoa such as coccidia, Plasmodium , intestinal Sarcocystis , Toxoplasma and Cryptosporidium .

[0093]

More detailed examples of endoparasites include:

species of the order Enoplida , such as subgenus trichuris (whipworms) ( Trichuris spp.), subgenus Capillaria (roundworms) ( Capillaria spp.), subgenus Torikomosoidesu ( Trichomosoides spp.), and subgenus trichinella (genus Trichinella ) ( Trichinella spp.);

species of the order Rhabditia , such as the subgenus Micronema ( Micronema spp.) and the subgenus Strongyloides ( Strongyloides spp.);

species of the order Strongylida , e.g. subgenus Strongylus (strongyles) ( Stronylus spp.), subgenus triodontophorus ( Triodontophorus spp.), subgenus Oesophagodontus ( Oesophagodontus spp.), subgenus trichonema ( Trichonema spp.), subgenus Gyalocephalus ( Gyalocephalus spp.), subgenus Cylindropharynx ( Cylindropharynx spp.), subgenus Poteriostomum ( Poteriostomum spp.), subgenus Cyclococercus ( Cylicocercus spp.), subgenus Cylicostephanus ( Cylicostephanus spp.), subgenus Oesophagostomum ( Oesophagostomum genus) ( Oesophagostomum spp.), subgenus Chabertia ( Chabertia spp.) , subgenus Stephanurus ( Stephanurus dentatus) ( Stephanurus spp.), subgenus Ancylostoma (Old World hookworm) ( Ancylostoma spp.), subgenus Uncinaria ( Uncinaria spp.), and subgenus Bunostomum ( Bunostomum spp.); subgenus Globocephalus ( Globocephalus spp.), subgenus Syngamus (syngamus worms) ( Syngamus spp.), subgenus Cyathostoma ( Cyathostoma spp.), subgenus Metastrongylus (lungworms) ( Metastrongylus spp.), subgenus Dictyocaulus ( Dictyocaulus spp.), subgenus Muellerius ( Muellerius spp.), subgenus Protostrongylus ( Protostrongylus spp.) Neostrongylus ( Neostrongylus spp.), subgenus Cystocaulus ( Cystocaulus spp.), subgenus Pneumostrongylus ( Pneumostrongylus spp.), subgenus Spicocaulus ( Spicocaulus spp.), subgenus Elaphostrongylus ( Elaphostrongylus spp.) , subgenus Parelaphostrongylus ( Parelaphostrongylus spp.) Crenosoma ( Crenosoma spp.), subgenus Paracrenosoma ( Parelaphostrongylus spp.), subgenus Angiostrongylus ( angiostrongylus worms) ( Angiostrongylus spp.), subgenus Aelurosutrongylus ( Aelurosutrongylus spp.), subgenus Filaroides ( Filaroides spp.) , subgenus Parafilaroides ( Parafilaroides spp.), subgenus trichostrongylus ( Trichostrongylus spp.), subgenus Haemonchus (haemonchus worm) ( Haemonchus spp.), subgenus Ostertagia ( Ostertagia spp.), subgenus Marshallagia ( Marshallagia spp.), subgenus Cooperia ( Cooperia spp.), subgenus Nematodirus (nematode) ( Nematodirus spp.), subgenus Hyostrongylus ( Hyostrongylus spp.), subgenus Obeliscoides ( Obeliscoides spp.), subgenus Amidostomum ( Amidostomum spp.) and subgenus Ollulanus ( Ollulanus spp.);

[0094]

species of the order Oxyurida , such as subgenus Oxyuris (horse pinworms) ( Oxyuris spp.), subgenus Enterobius (pinworms) ( Enterobius spp.), subgenus Passalurus ( Passalurus spp.), subgenus Syphacia ( Syphacia spp.), subgenus Aspiculuris ( Aspiculuris spp. .) and subgenus Heterakis ( Heterakis spp.);

[0095]

species of the order Ascaridia , such as subgenus Ascaris (roundworms) ( Ascaris spp.), subgenus Toxascaris ( Toxascaris spp.), subgenus Toxocara (canine roundworms) ( Toxocara spp.), subgenus Parascaris (parascaris equorum) ( Parascaris spp.), Anisakis subgenus ( Anisakis spp.) and Ascaridia subgenus (roundworms) ( Ascaridia spp.);

species of the order Spirurida (spiruroids), such as the subgenus Gnathostoma (gnathostoma spinigerm) ( Gnathostoma spp.), subgenus Physaloptera ( Physaloptera spp.), subgenus Thelazia ( Thelazia spp.), subgenus Gongylonema ( Gongylonema spp.), subgenus Habronema ( Habronema spp. .), subgenus Parabronema ( Parabronema spp.), subgenus Draschia ( Draschia spp.) and subgenus Dracunculus (Guinea worms) ( Dracunculus spp.);

[0096]

species of the order Filariida , such as subgenus Stephanofilaria ( Stephanofilaria spp.), Parafilaria ( Parafilaria spp.), subgenus Setaria ( Setaria spp.), subgenus Loa ( Loa spp.), subgenus Dirofilaria (dog heartworms) ( Dirofilaria spp.) , subgenus Litomosoides ( Litomosoides spp.), subgenus Brugia ( Brugia spp.), subgenus Wuchereria (heartworms) ( Wuchereria spp.), and subgenus Onchocerca ( Onchocerca spp.), and

[0097]

species of the order Gigentorhynchida , such as the subgenus Filicollis ( Filicollis spp.), subgenus Moniliforumis ( Moniliforumis spp.), subgenus Macracanthorhynchus ( Maracanthorhynchus spp.), and subgenus Prosthenorchis ( Prosthenorchis spp.).

[0098]

An anti-endoparasite agent containing a benzimidazole derivative represented by the general formula (1) of the present invention or a salt thereof as an active ingredient is effective not only against parasites that live in the body of an intermediate or final host, but also against parasites that live in the body of the reservoir host. The benzimidazole derivative represented by the general formula (1) of the present invention or a salt thereof is effective against parasites at each stage of their development. For example, in the case of protozoa, the compound is effective against their cysts, precystic forms and trophozoites; schizonts and amoeboid forms at the asexual stage; gametocytes, gametes and zygotes at the sexual stage; sporozoites, etc. In the case of nematodes, the compound is effective against their eggs, larvae and adults. The compound of the present invention is capable of not only combating parasites in a living body, but even preventing parasitic infection by introducing it into the environment as a route of infection. For example, soil-borne infection, that is, infection from the soil of agricultural fields and parks, can be prevented; percutaneous infection through water in rivers, lakes, swamps, rice fields, etc.; oral infection from feces of animals such as dogs and cats; oral infection from sea fish, freshwater fish, crustaceans, shellfish, raw meat of domestic animals, etc.; infection from mosquitoes, gadflies, flies, cockroaches, ticks and ticks, fleas, lice, killer bugs, trombiculid mites, etc.; etc.

[0099]

When the compounds of the present invention are used to control endoparasites in domestic mammals and birds, the compounds of the present invention can be administered in an effective amount along with pharmaceutically acceptable additives orally, parenterally by injection (intramuscular, subcutaneous, intravenous or intraperitoneal); subcutaneously by dipping, spraying, bathing, washing, pouring and staining and dusting, or intranasally. The compounds of the present invention can be administered through molded articles such as chips, wafers, tapes, collars, ear tags, limb bands and identification tags. The compounds of the present invention are administered in any dosage form suitable for the route of administration.

[0100]

The dosage form may be a solid preparation such as a dust preparation, granules, a wettable powder, a feed pellet, a tablet, a pellet, a lozenge and a molded article containing the active ingredient, a liquid preparation such as an injection liquid, an oral liquid, a liquid preparation , applied to the skin or whole, pour-on preparation, spot-on preparation, pourable, emulsion and semi-solid preparation such as ointment and gel.

The solid preparation can generally be used for oral administration, or for subcutaneous administration, or for application to the environment after dilution with water and the like. The solid preparation can be prepared by mixing the active ingredient with a suitable carrier and, if necessary, with an adjuvant, and preparing the mixture in the desired dosage form. Examples of the carrier include an inorganic carrier such as a carbonate, hydrogen carbonate, phosphate, alumina, silica or clay, or an organic carrier such as a saccharide, cellulose, cereal flour or starch.

[0101]

The injection liquid can be administered intravenously, intramuscularly or subcutaneously. The injection liquid can be prepared by dissolving the active ingredient in a suitable solvent and, if necessary, adding additives such as a solubilizer, acid, base, buffer salt, antioxidant and protectant. Examples of suitable solvents include water, ethanol, butanol, benzyl alcohol, glycerin, propylene glycol, polyethylene glycol, N-methylpyrrolidone and mixtures thereof, physiologically acceptable vegetable oils and synthetic oils suitable for injection. Examples of solubilizers include polyvinylpyrrolidone, polyoxyethylated castor oil, polyoxyethylated sorbitan ester and the like. Examples of the protectants include benzyl alcohol, trichlorobutanol, p-hydroxybenzoic acid esters, n-butanol and the like.

[0102]

The oral liquid can be administered directly or after dilution and can be prepared in the same manner as the injectable liquid.

[0103]

The flowable emulsion and the like can be administered directly or after dilution transdermally or by application to the environment.

[0104]

A liquid preparation applied to the skin is administered by dripping, spreading, rubbing, spraying, splashing, or dipping (soaking, bathing, or washing) and can be prepared in the same manner as an injectable liquid.

[0105]

Drenches and spot-on products are dripped or sprayed onto a limited area of the skin so that they penetrate the skin and act systemically. Top-on preparations and spot-on preparations can be prepared by dissolving, suspending or emulsifying the active ingredient in a suitable skin-friendly solvent or mixture of solvents. Additives such as surfactant, colorant, absorbent, antioxidant, UV protection and adhesive can be added as needed. Examples of suitable solvents include water, alcohol, glycol, polyethylene glycol, polypropylene glycol, glycerin, benzyl alcohol, phenylethanol, phenoxyethanol, ethyl acetate, butyl acetate, benzyl benzoate, propylene glycol dimonomethyl ether, diethylene glycol monobutyl ether, acetone, methyl ethyl ketone, aromatic and/or aliphatic hydrocarbons. Yes, vegetable or synthetic oils, DMF, liquid paraffin, light liquid paraffin, silicone, dimethylacetamide, N-methylpyrrolidone or 2,2-dimethyl-4-hydroxymethylene-1,3-dtoxolane. Examples of the absorption enhancer include DMSO, isopropyl myristate, pelargonic acid dipropylene glycol, silicone oil, fatty acid esters, triglycerides and aliphatic alcohols. Examples of antioxidants include sulfites, metabisulfites, ascorbic acid, butylhydroxytoluene, butylhydroxyanisole and tocopherol.

[0106]

The emulsion can be administered orally, subcutaneously or by injection. An emulsion can be prepared by dissolving the active ingredient in a hydrophobic phase or a hydrophilic phase and homogenizing the resulting solution with another liquid phase together with an appropriate emulsifier and, if necessary, additives such as a colorant, an absorbent agent, a protecting agent, an antioxidant, a light filter and thickener.

[0107]

Examples of hydrophobic phases (oils) include paraffin oil, silicone oil, sesame oil, almond oil, castor oil, synthetic triglycerides, ethyl stearate, di-n-butyryl adipate, hexyl laurate, pelargonic acid dipropylene glycol, C ₁₆ -C branched chain fatty acid esters ₁₈ saturated fatty acids, isopropyl myristate, isopropyl palmitate, C ₁₂ -C esters ₁₈ saturated alcohols with caprylic/capric acid, isopropyl stearate, oleyl oleate, decyl oleate, ethyl oleate, ethyl lactate, fatty acid ester waxes, dibutyl phthalate, diisopropyl adipate, isotridecyl alcohol, 2-octyldodecane ol , cetyl stearyl alcohol and oleyl alcohol.

[0108]

Examples of hydrophilic phases include water, propylene glycol, glycerol and sorbitol.

[0109]

Examples of nonionic surfactant emulsifiers include polyoxyethylated castor oil, polyoxyethylated sorbitan monoolefinic acid, sorbitan monostearate, glycerol monostearate, polyoxyethyl stearate and polyglycol alkylphenol ether; amphoteric surfactants such as disodium N-lauryl-β-iminodipropionate and lecithin; anionic surfactants such as sodium lauryl sulfate, aliphatic alcohol sulfate ester, monoethanolamine mono/dialkyl polyglycol orthophosphate salt; and cationic surfactants such as cetyltrimethylammonium chloride.

[0110]

Examples of other additives include carboxymethyl cellulose, methyl cellulose, polyacrylate, alginate, gelatin, gum arabic, polyvinylpyrrolidone, polyvinyl alcohol, methyl vinyl ether, maleic anhydride copolymers, polyethylene glycol, waxes and colloidal silica.

[0111]

The semi-solid preparation is administered by application or distribution on the skin or administration generally. The gel can be prepared by adding a thickener to a solution prepared in the same manner as an injection, sufficient to obtain a clear, viscous, ointment-like substance.

[0112]

In the case where the anti-endoparasite agent of the present invention is used as a drug for animals, non-human mammalian or avian species, the optimal amount (effective amount) of the active ingredient varies depending on the purpose (treatment or prevention), the type of infectious parasite, type and severity of infection, dosage form, etc., but in general the oral daily dose is in the range of about 0.0001 to 10,000 mg/kg body weight, and the parenteral daily dose is in the range of about 0. 0001 to 10000 mg/kg body weight. This dose may be given as a single dose or divided into several doses.

[0113]

The concentration of the active ingredient in the endoparasite control agent of the present invention is generally from about 0.001 to 100% by weight, preferably from about 0.001 to 99% by weight, and more preferably from about 0.005 to 20% by weight. The endoparasite control agent of the present invention may be a composition that can be administered directly, or a highly concentrated composition that must be diluted to a suitable concentration before use.

[0114]

The endoparasite control agent of the present invention can be used in combination with any existing endoparasite control agent to enhance or complement its effect. In such combination use, two or more active ingredients may be mixed and formulated into one preparation before administration, or two or more different preparations may be administered separately.

[0115]

An agricultural and horticultural insecticidal and acaricidal agent containing a benzimidazole derivative represented by the general formula (1) of the present invention or a salt thereof as an active ingredient has a remarkable control effect against the above-described pests that damage lowland crops, field crops, fruit trees, vegetables, other crops, ornamental flowering plants, etc. The desired effect can be obtained when the agricultural and horticultural insecticidal and acaricidal agent is applied in seedling nurseries, rice fields, fields, fruit trees, vegetables, other crops, ornamental flowering plants and etc. and their seeds, in paddy field water, on foliage, in growing medium such as soil, etc. around the expected time of pest infestation, i.e. before infestation or after infestation is confirmed. In particularly preferred embodiments, the application of an agricultural and horticultural insecticidal and acaricidal agent utilizes so-called plant penetration and movement. That is, nursery soil, planting pit soil, plant support, irrigation water, hydroponic growing water, or the like are treated with an agricultural and horticultural insecticidal and acaricidal agent to enable crops, ornamental flowering plants, etc. to truly absorb the compound invention by roots from the soil or otherwise.

[0116]

Examples of beneficial plants to which the agricultural and horticultural insecticidal and acaricidal agent of the present invention can be applied include, but are not limited to, cereals (eg, rice, barley, wheat, rye, oats, corn, etc.), legumes (eg , soybeans, adzuki beans, beans, green peas, kidney beans, peanuts, etc.), fruit trees and fruits (such as apples, citrus fruits, pears, grapes, peaches, plums, cherries, walnuts, chestnuts, almonds, bananas, etc.), leafy and fruit vegetables (e.g. cabbage, tomatoes, spinach, broccoli, lettuce, onions, spring onions (garlic and Welsh onions), green peppers, eggplant, strawberries, pepper crops, okra, Chinese garlic, etc.), root vegetables (such as carrots, potatoes, sweet potatoes, taro, radishes, turnips, lotus roots, burdock roots, garlic, Chinese green onions, etc.), processing grains (such as , cotton, hemp, beets, hops, sugar cane, sugar beets, olives, rubber, coffee, tobacco, tea, etc.), pumpkins (such as Japanese pumpkins, cucumbers, watermelons, oriental sweet melons, melons, etc. etc.), pasture grass (such as orchard grass, sorghum, timothy, clover, alfalfa, etc.), turf grass (such as Korean turfgrass, bentgrass, etc.), spice and aromatic crops, and ornamental crops (e.g. lavender, rosemary, thyme, parsley, pepper, ginger, etc.), ornamental flowering plants (e.g. chrysanthemum, rose, carnation, orchid, tulip, lily, etc.), garden trees (e.g. ginkgo trees, cherry trees, Japanese aucuba, etc.) and forest trees (e.g. Abies sachalinensis , Picea jezoensis , pine, yellow cedar, Japanese cedar, hinoki cypress, eucalyptus, etc.).

[0117]

The above-mentioned “plants” also include plants having herbicide resistance acquired through classical breeding techniques or genetic recombination techniques. Examples of such herbicide resistance include resistance to HPPD inhibitors such as isoxaflutole; ALS inhibitors such as imazethapyr and thifensulfuronmethyl; EPSP synthase inhibitors such as glyphosate; glutamine synthetase inhibitors such as glufosinate; acetyl-CoA carboxylase inhibitors such as sethoxydim; or other herbicides such as bromoxynil, dicamba and 2,4-D.

[0118]

Examples of plants that are resistant to herbicides through classical breeding techniques include varieties of canola, wheat, sunflower and rice that are resistant to the imidazolinone family of ALS-inhibiting herbicides such as imazethapyr, and such plants are sold under the trade name Clearfield (registered trademark). Also included are soybean varieties that are resistant to the sulfonylurea family and ALS-inhibiting herbicides such as thifensulfuron methyl through classical breeding and are sold under the trade name STS soybean. Also included are plants having tolerance to acetyl-CoA carboxylase inhibitors such as trionoxime herbicides and aryloxyphenoxypropionic acid herbicides through classical breeding, such as SR corn and the like.

Plants with resistance to acetyl-CoA carboxylase inhibitors are described in Proc. Natl. Acad. Sci. USA, 87, 7175-7179 (1990), and the like. In addition, acetyl-CoA carboxylase mutants resistant to acetyl-CoA carboxylase inhibitors are described in Weed Science, 53, 728-746 (2005), and the like, and when the gene for such an acetyl-CoA carboxylase mutant is introduced into plants By using gene recombination or introducing a resistance-conferring mutation into plant acetyl-CoA carboxylase, plants can be created that are resistant to acetyl-CoA carboxylase inhibitors. Alternatively, by introducing a nucleic acid into plant cells that causes a base substitution mutation (a typical example of this method is the chimeraplasty method (Gura T. 1999. Repairing the Genome's Spelling Mistakes. Science 285: 316-318)) to provide site-specific replacement can mutations in amino acids encoded by the acetyl-CoA carboxylase gene, ALS gene and the like, plants, plants resistant to acetyl-CoA carboxylase inhibitors, ALS inhibitors and the like, can be constructed. The agricultural and horticultural insecticidal and acaricidal agent of the present invention can also be applied to these plants.

[0119]

Further, typical toxins expressed in genetically modified plants include the insecticidal proteins of Bacillus cereus or Bacillus popilliae ; Bacillus thuringiensis δ-endotoxins such as Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 and Cry9C, and other insecticidal proteins such as VIP1, VIP2, VIP3 and VIP3A; insecticidal nematode proteins; toxins produced by animals such as scorpion toxins, spider toxins, bee toxins and insect-specific neurotoxins; filamentous fungal toxins; plant lectins; agglutinin; protease inhibitors such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin and papain inhibitors; ribosome inactivating proteins (RIPs), such as ricin, corn RIP, abrin, luffin, saporin and bryodin; steroid metabolizing enzymes such as 3-hydroxysteroid oxidase, ecdysteroid UDP-glucosyltransferase and cholesterol oxidase; ecdysone inhibitors; HMG-CoA reductase; ion channel inhibitors such as sodium channel inhibitors and calcium channel inhibitors; juvenile hormone esterase; diuretic hormone receptors; stilbene synthase; bibenzyl synthase; chitinase; and glucanase.

[0120]

Also included are hybrid toxins, partially deficient toxins and modified toxins derived from the following: δ-endotoxin proteins such as Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1, Cry9C, Cry34Ab and Cry35Ab, as well as other insecticidal proteins such as VIP1, VIP2, VIP3 and VIP3A. A hybrid toxin can be produced by combining some domains of these proteins differently than the original combination in nature, using a recombination technique. A known partial deficiency toxin is the Cry1Ab toxin, in which part of the amino acid sequence has been removed. In a modified toxin, one or more amino acids of a naturally occurring toxin are replaced.

Examples of the above toxins and genetically modified plants capable of synthesizing these toxins are described in EP-A-0374753, WO 93/07278, WO 95/34656, EP-A-0427529, EP-A-451878, WO 03/052073, etc. d.

[0121]

Due to the toxins contained in such genetically modified plants, the plants exhibit resistance to pests, particularly Coleopteran pests, Hemipteran pests, Diptera pests, Lepidopteran pests and nematodes. The above-described technologies as well as the agricultural and horticultural insecticidal and acaricidal agent of the present invention can be used in combination or systematically.

[0122]

To control target pests, the agricultural and horticultural insecticidal and acaricidal agent of the present invention, with or without appropriate dilution or suspension in water, is applied to plants potentially infested with the target insect pests or nematodes, in an amount effective to control the insect pests or nematodes. For example, foliar feeding and seed treatments such as dipping, pollination and calcium peroxide coating can be used to control insect pests and nematodes that can damage crops such as fruit trees, grains and vegetables. In addition, tillage and the like may also be performed to enable plants to absorb agrochemicals into their roots. Examples of such treatments include whole soil tillage, planting row tillage, bed tillage, seedling tillage, planting hole treatment, plant stem treatment, top dressing, paddy box treatment and water incorporation. In addition, incorporation into hydroponic culture media, fumigation, trunk injection and the like can also be performed.

Moreover, the agricultural and horticultural insecticidal and acaricidal agent of the present invention, with or without appropriate dilution or suspension in water, etc. can be applied to areas potentially infested by pests in an amount effective for pest control. For example, it can be directly applied to stored grain pests, household pests, sanitation pests, forest pests, etc., and can also be used to coat residential building materials, fumigation treatments, or as a bait formulation.

[0123]

Examples of seed treatment methods include immersing the seeds in a dilute or undiluted liquid of a liquid or solid composition to penetrate the agrochemicals into the seeds; mixing or powder coating seeds with a solid or liquid composition to adhere the composition to seed surfaces; coating the seeds with a mixture of agrochemicals and an adhesive carrier such as resins and polymers; and applying a solid or liquid preparation near the seeds at the same time as sowing.

The term "seed" in the above seed treatment refers to the body of the plant, which is in the early stages of cultivation and is used for plant propagation. Examples include, in addition to the so-called seed, the plant body for vegetative propagation, such as a bulb, tuber, seed potato, clove, scion, disc-shaped stem and stem used for cutting.

The term "soil" or "growing medium" in the method of the present invention for the use of agricultural and horticultural insecticides refers to a supporting medium for growing crops, in particular, a supporting medium that allows crop plants to spread their roots therein, and the materials are not particularly limited if they allow plants to grow. Examples of supporting media include so-called soils, seedling mats and water, and specific examples of materials include sand, pumice, vermiculite, diatomaceous earth, agar, gelling substances, high molecular weight substances, rock wool, glass wool, wood, wood chips and bark.

[0124]

Examples of methods of application to crop foliage or to pests of stored grain, household pests, pests of sanitation, forest pests, etc. include application of a liquid composition such as an emulsifiable concentrate and a fluid or solid composition such as a wettable powder and water-dispersible granules after appropriate dilution with water; use of a dust-like preparation; and fumigation.

Examples of soil application methods include applying a water-diluted or undiluted liquid formulation to plant stems, seedling beds and the like, applying granules to plant stems, seedling beds and the like, applying a dust formulation, wettable powder, water-dispersible granules, granules and the like on the soil and subsequent application of the composition to the entire soil before sowing or replanting; and applying dust, wettable powder, water-dispersible granules, granules and the like to planting holes, planting rows and the like before sowing or planting.

[0125]

For example, powdered preparation, water-dispersible granules, granules and the like can be applied to paddy rice growing boxes, although the suitable composition may vary depending on the time of application, in other words, depending on the stage of cultivation, for example, as the time of sowing , greening period and planting time. Formulations such as dust, water-dispersible granules and granules can be mixed into nursery soil. For example, such a composition is introduced into the soil of the bed, covering the soil, or into the entire soil. Simply put, nursery soil and this composition can be layered alternately.

When applied to rice fields, solid formulation such as jumbo, pack, granules and water-dispersible granules or liquid formulation such as flowable and emulsifiable concentrate are usually applied to flooded rice fields. During the rice planting period, the suitable formulation, as is, or after mixing with fertilizer, can be applied to or injected into the soil. In addition, the emulsifiable concentrate, flowable and the like can be applied to a rice field water supply source such as a water inlet and an irrigation device. In this case, the treatment can be carried out with water supply and thus save labor.

[0126]

In the case of field crops, their seeds, cultivation media near their plants, or the like can be treated from sowing to sowing. In the case of plants whose seeds are sown directly in the field, in addition to direct seed treatment, it is preferable to treat the plant stems during cultivation. In particular, the treatment can be carried out, for example, by applying granules to the soil or soaking the soil with the composition in diluted water or undiluted liquid form. Another preferred treatment method is to introduce granules into the culture medium before sowing.

In the case of transplanted crop plants, preferred examples of plant-to-plant treatments include, in addition to direct seed treatment, soaking the seedling beds with the composition in liquid form and applying granules to the seedling beds. Also included is treating planting holes with granules and introducing granules into the culture medium near planting points during fixed planting.

The agricultural and horticultural insecticidal and acaricidal agent of the present invention is generally used in the form of a composition convenient for use, which is prepared by a conventional method for preparing agrochemical compositions.

That is, the benzimidazole derivative represented by the general formula (1) of the present invention, or a salt thereof and a corresponding inactive carrier and, if necessary, an adjuvant, are mixed in a suitable ratio and at the stage of dissolution, separation, suspension, mixing, impregnation, adsorption and/or adhesion agents, constitute a form suitable for use, such as suspension concentrate, emulsifiable concentrate, soluble concentrate, wettable powder, water-dispersible granules, granules, dust preparation, tablets and packaging.

[0127]

The composition (agricultural and horticultural insecticidal and acaricidal or animal parasite control agent) of the present invention, in addition to the active ingredient, may optionally contain an additive commonly used for agrochemical compositions or animal parasite control agents. Examples of additives include carriers such as solid or liquid carriers, surfactants, dispersants, wetting agents, binders, tackifiers, thickeners, colorants, dispensers, tack/flow agents, antifreeze, anti-caking agents, disintegrants and stabilizing agents. agents. If necessary, preservatives, plant fragments, etc. can be used as an additive. One of these additives can be used alone, or two or more of them can be used in combination.

[0128]

Examples of solid supports include natural minerals such as quartz, clay, kaolinite, pyrophyllite, sericite, talc, bentonite, acid clay, attapulgite, zeolite and diatomite; inorganic salts such as calcium carbonate, ammonium sulfate, sodium sulfate and potassium chloride; organic solid carriers such as synthetic silicic acid, synthetic silicates, starch, cellulose and plant powders (eg sawdust, coconut shells, corn cobs, tobacco stalks, etc.); plastic carriers such as polyethylene, polypropylene and polyvinylidene chloride; urea; hollow inorganic materials; hollow plastic materials; and colloidal silica (white carbon black). One of these solid carriers may be used alone, or two or more of them may be used in combination.

[0129]

Examples of liquid carriers include alcohols, including monohydric alcohols such as methanol, ethanol, propanol, isopropanol and butanol, and polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, hexylene glycol, polyethylene glycol, polypropylene glycol and glycerin; polyol compounds such as propylene glycol ether; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone and cyclohexanone; ethers such as ethyl ether, dioxane, ethylene glycol monoethyl ether, dipropyl ether and tetrahydrofuran; aliphatic hydrocarbons such as normal paraffin, naphthene, isoparaffin, kerosene and mineral oil; aromatic hydrocarbons such as benzene, toluene, xylene, solvent naphtha and alkylnaphthalene; halogenated aliphatic hydrocarbons such as dichloromethane, chloroform and carbon tetrachloride; esters such as ethyl acetate, diisopropyl phthalate, dibutyl phthalate, dioctyl phthalate and dimethyl adipate; lactones such as γ-butyrolactone; amides such as dimethylformamide, diethylformamide, dimethylacetamide and N-alkylpyrrolidinone; nitriles such as acetonitrile; sulfur compounds such as dimethyl sulfoxide; vegetable oils such as soybean oil, canola oil, cottonseed oil and castor oil; and water. One of these liquid carriers may be used alone, or two or more of them may be used in combination.

[0130]

Examples of surfactants used as a dispersant or wetting/distributing agent include nonionic surfactants such as sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester, sucrose fatty acid ester, polyoxyethylene fatty acid ester, polyoxyethylene resin acid ester, polyoxyethylene fatty acid diester, polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether, polyoxyethylene alkyl phenyl ether, polyoxyethylene dialkyl phenyl ether, polyoxyethylene alkyl phenyl ether formaldehyde condensates, polyoxyethylene and polyoxypropylene block copolymers, polyoxypropylene block polymers tyrol and polyoxyethylene, alkyl ester of block copolymer of polyoxyethylene and polypropylene , polyoxyethylene alkylamine, polyoxyethylene fatty acid amide, bis(phenyl ether), polyalkylene benzyl phenyl ether, polyoxyalkylene styryl phenyl ether, acetylenediol, polyoxyalkylene acetylenediol, ester type silicone, fluorinated surfactants, polyoxyethylene castor oil and polyoxyethylene hydrogenated castor oil; anionic surfactants such as alkyl sulfates, polyoxyethylene alkyl ether sulfates, polyoxyethylene alkyl phenyl ether sulfates, polyoxyethylene styryl phenyl ether sulfates, alkyl benzene sulfonates, alkyl aryl sulfonates, lignosulfonates, alkyl sulfosuccinates, naphthalene sulfonates, alkyl naphthalene sulfonates, naphthalene sulfonate condensate salts onic acid and formaldehyde, salts of condensates of alkylnaphthalene sulfonic acid and formaldehyde, salts fatty acids, polycarboxylic acid salts, polyacrylates, N-methyl fatty acid sarcosinates, resinates, polyoxyethylene alkyl ether phosphates and polyoxyethylene alkyl phenyl ether phosphates; cationic surfactants including alkylamine salts such as laurylamine hydrochloride, stearylamine hydrochloride, oleylamine hydrochloride, stearylamine acetate, stearylamine propylamine acetate, alkyltrimethylammonium chloride and alkyldimethylbenzalkonium chloride; and amphoteric surfactants such as amino acid or betaine type amphoteric surfactants. One of these surfactants can be used alone, or two or more of them can be used in combination.

[0131]

Examples of binders or tackifiers include carboxymethylcellulose or its salts, dextrin, soluble starch, xanthan gum, guar gum, sucrose, polyvinylpyrrolidone, acacia, polyvinyl alcohol, polyvinyl acetate, sodium polyacrylate, polyethylene glycols with an average molecular weight of 6,000 to 20,000. , polyethylene oxides with an average molecular weight of 100,000 to 5,000,000, phospholipids (e.g., cephalin, lecithin, etc.), cellulose powder, dextrin, modified starch, polyaminocarboxylic acid chelating compounds, cross-linked polyvinylpyrrolidone, maleic acid-styrene copolymers, copolymers (met )acrylic acid, polyhydric alcohol polymer half-esters and dicarboxylic acid anhydride, water-soluble polystyrene sulfonates, paraffin, terpene, polyamide resins, polyacrylates, polyoxyethylene, waxes, polyvinyl ether, alkylphenol formaldehyde condensates and synthetic resin emulsions.

[0132]

Examples of thickeners include water-soluble polymers such as xanthan gum, guar gum, diutan gum, carboxymethylcellulose, polyvinylpyrrolidone, carboxyvinyl polymers, acrylic polymers, starch compounds and polysaccharides; and inorganic fine powders such as high quality bentonite and colloidal silica (white carbon).

[0133]

Examples of dyes include inorganic pigments such as iron oxide, titanium oxide and Prussian blue; and organic dyes such as alizarin dyes, azo dyes and metal phthalocyanine dyes.

[0134]

Examples of antifreeze include polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol and glycerin.

[0135]

Examples of adjuvants that serve to prevent caking or facilitate grinding include polysaccharides (starch, alginic acid, mannose, galactose, etc.), polyvinylpyrrolidone, colloidal silicon dioxide (white carbon black), ester gum, petroleum resin, sodium tripolyphosphate, sodium hexametaphosphate , metal stearates, cellulose powder, dextrin, methacrylate copolymers, polyvinylpyrrolidone, polyaminocarboxylic acid chelating compounds, sulfonated styrene isobutylene maleic anhydride copolymers and starch-polyacrylonitrile graft copolymers.

[0136]

Examples of stabilizing agents include drying agents such as zeolite, quicklime and magnesium oxide; antioxidants such as phenolic compounds, amino compounds, sulfur compounds and phosphoric acid compounds; and ultraviolet absorbers such as salicylic acid compounds and benzophenone compounds.

[0137]

Examples of preservatives include potassium sorbate and 1,2-benzothiazolin-3-one. In addition, other adjuvants, including functional distribution agents, activity enhancers such as metabolic inhibitors (piperonyl butoxide, etc.), antifreeze agents (propylene glycol, etc.), antioxidants (BHT, etc.), can also be used if necessary. d.) and ultraviolet absorbers.

[0138]

The amount of the active ingredient in the agricultural and horticultural insecticidal and acaricidal agent of the present invention can be adjusted as necessary, and generally the amount of the active ingredient is suitably selected from the range of 0.01 to 90 parts by weight in 100 parts by weight of the agricultural and horticultural insecticide . For example, in the case where the agricultural and horticultural insecticide is a dust preparation, granules, emulsifiable concentrate or wettable powder, an amount of active ingredient from 0.01 to 50 parts by weight (0.01 to 50% by weight relative to the total) is suitable. mass of agricultural and horticultural insecticidal and acaricidal agent).

[0139]

Application rates for the agricultural and horticultural insecticidal and acaricidal agents of the present invention may vary depending on various factors, e.g., purpose, target pest, crop growing conditions, pest infestation trends, weather, environmental conditions, dosage form, method of application, location of application , time of application, etc., but generally the consumption of the active ingredient is suitably selected from the range of 0.001 g to 10 kg, preferably 0.01 g to 1 kg per 10 ares, depending on the purpose.

In addition, to expand the range of target pests and the appropriate time for pest control or to reduce its dose, the agricultural and horticultural insecticidal and acaricidal agent of the present invention can be used after mixing with other agricultural and horticultural insecticidal and acaricidal agent, acaricides, nematicides, microbicides, biopesticides and/or the like. In addition, the agricultural and horticultural insecticidal and acaricidal agent can be used after mixing with herbicides, plant growth regulators, fertilizers and/or the like, depending on the situation.

[0140]

Examples of such additional agricultural and horticultural insecticides, acaricides and nematicides used for the above purposes include 3,5-xylylmethylcarbamate (XMC), crystalline protein toxins produced by Bacillus thuringiensis , such as Bacillus thuringiensis aizawai , Bacillus thuringiensis israelensis , Bacillus thuringiensis japonensis , Bacillus thuringiensis kurstaki and Bacillus thuringiensis tenebrionis , BPMC, insecticidal compounds derived from Bt toxin, CPCBS (chlorphensone), DCIP (dichlorodiisopropyl ether), DD (1,3-dichloropropene), DDT, NAC, O-4-dimethylsulfamoylphenyl O, O- diethylphosphorothioate (DSP), O-ethyl O-4-nitrophenylphenylphosphonothioate (EPNN), tripropyl isocyanurate (TPIC), acrinatrine, azadirachtin, azinphos-methyl, acequinocyl, acetamiprid, acetoprole, acephate, abamectin, avermectin-B, amidoflumet, amitraz, alanicarb, aldicarb, aldoxycarb, aldrin, alpha-endosulfan, alpha-cibetospermethrin, alpha-cybendazine isoamidophos, isoxathione, isofenphos, isoprocarb (MIPC), ivermectin, imitsiafos, imidacloprid, imiprotrin, indoxacarb, esfenvalerate, etiophencarb, ethion, ethiprole, etoxazole, etofenprox, etoprofos, etrimphos, emamectin, emamectin-benzoate, endosulfan, empentrin, oxamyl, oxydemetone-methyl, oxydeprophos (ESP), oxybendazole, oxfendazole, potassium oleate, sodium oleate, cadusafos, cartap, carbaryl, carbosulfan, carbofuran, gamma-cyhalothrin, xylylcarb , quinalphos, kinoprene, quinomethionate, cloetocarb, clothianidin, clofentesine, chromafenozide, chlorantraniliprole, chlorethoxyphos, chlordimeform, chlordane, chlorpyrifos, chlorpyrifos-methyl, chlorfenapyr, chlorfensone, chlorfenvinfos, chlorfluazuron, chlorobenzilate, chlorobenzoate, keltan (dicofol), salithion, cyanophos ( CYAP), diafenthiuron, diamidaphos, cyantraniliprole, theta-cypermethrin, dienochlor, cyenopyrafen, dioxabenzophos, diophenolan, sigma-cypermethrin, dichlorofenthion (ECP), cycloprothrin, dichlorvos (DDVP), disulfoton, dinotefuran, cyhalothrin, cyphenothrin, cyfluthrin, diflub enzuron, cyflumetofen , difluvidazine, cyhexatin, cypermethrin, dimethylvinphos, dimethoate, dimefluthrin, silaflufen, cyromazine, spinetoram, spinosad, spirodiclofen, spirotetramate, spiromesifen, sulfluramide, sulfrophos, sulfoxaflor, zeta-cypermethinatin, diazinon, tau-fluvalinate, dazomet, thiacloprid, thiamethoxam, thiodicarb , thiocyclam, thiosultap, thiosultap-sodium, thionazine, thiometon, deet, dieldrin, tetrachlorvinphos, tetradifon, tetramethylfluthrin, tetramethrin, tebupirimphos, tebufenozide, tebufenpyrad, tefluthrin, teflubenzuron, demeton-S-methyl, tramephos, trafamethosphos , triazuron, trichlamide, trichlorfon (DEP), triflumuron, tolfenpyrad, naled (BRP), nithiazine, nitenpyram, novaluron, noviflumuron, hydroprene, vaniliprole, vamdothion, parathion, parathion-methyl, halfenprox, halofenozide, bistrifluron, bisultap, hydramethylnon, hydroxypropyl starch, binapacryl, biphenazate, bifenthrin , pymetrozine, pyraclofos, pyrafluprol, pyridafention, pyridaben, pyridalyl, pyrifluquinazone, pyriprole, pyriproxyfen, pirimicarb, pyrimidifen, pirimifos-methyl, pyrethrins, fipronil, phenazachine, fenamiphos, bromopropylate, fenitrothion (MEP), fenoxycarb, phenothiocarb, phenothrin , fenobucarb, fensulfothione, fenthion (MPP), phentoate (PAP), fenvalerate, fenpiroximate, fenpropathrine, fenbendazole, fosthiazate, formetanate, butathiophos, buprofezin, furatiocarb, parallethrin, fluacripyrim, fluazinam, fluazuron, fluensulfone, flucycloxuron, flucitrinate, fluvalinate, flu pyrazophos, flufenerim, flufenoxuron, flufenzine, flufenprox, fluproxifen, flubrocitrinate, flubendiamide, flumethrin, flurimfen, prothiophos, protrifenbut, flonicamid, propafos, propargite (BPPS), profenofos, profluthrin, propoxur (PHC), bromopropylate, beta-cyfluthrin, hexaflumuron, hexythiaz ox, heptenophos, permethrin, benclothiaz, bendiocarb, bensultap, benzoximate, benfuracarb, phoxim, phosphalone, fostiazate, fostietan, phosphamidon, phosphocarb, phosmet (PMP), polynactins, formetanate, formotion, phorate, machine oil, malathion, milbemycin, milbemycin-A, milbemectin, mecarbam, mesulfenphos, methomyl, metaldehyde, metaflumizone, methamidophos, metam-ammonium, metham-sodium, methiocarb, methidathione (DMTP), methyl isothiocyanate, methylneodecanamide, methyl parathion, methoxadiazone, methoxychlor, methoxyfenozide, metofluthrin, methoprene, meth olcarb, meperfluthrin, mevinfos, monocrotophos , monosultap, lambda-cyhalothrin, ryanodine, lufenuron, resmethrin, lepimectin, rotenone, levamisole hydrochloride, fenbutatine oxide, morantel tartarate, methyl bromide, tricyclohexyltin hydroxide (cyhexatin), calcium cyanamide, calcium polysulfide, sulfur and nicotine sulfate.

[0141]

Examples of agricultural and horticultural microbicides used for the same purposes as above include aureofungin, asaconazole, azithiram, acipetac, acibenzolar, acibenzolar-S-methyl, azoxystrobin, anilazine, amisulbrom, ampropylphos, amethoctradine, allylic alcohol, aldimorph, amobam, isothianil, isovaledione, isopyrazam, isoprothiolane, ipconazole, iprodione, iprovalicarb, iprobenfos, imazalil, iminoctadin, iminoctadine-albesylate, iminoctadine-triacetate, imibenconazole, uniconazole, uniconazole-P, echlomesol, edifenphos, etaconazole, etaboxam, ethirimol, this, it xikhin, etridiazole, enestroburin, epoxiconazole, oxadixil, hydroxycarboxin, copper 8-quinolinolate, oxytetracycline, copper oxinate, oxpoconazole, oxpoconazole fumarate, oxolinic acid, octylinone, ofurac, orysastrobin, metam sodium, kasugamycin, carbamorph, carpropamide, carbene dazim, carboxin, carvone , quinazamide, quinacetol, quinoxifene, quinomethionate, captafol, captan, chiralaxyl, quinconazole, quintozene, guazatin, kufraneb, cuprobam, gliodin, griseofulvin, climbazole, cresol, kresoxim-methyl, chlozolinate, clotrimazole, chlorobentiazone, chloraniformethane, chloranil, chlorquinox, chloropicrin , chlorphenazole, chlordinitronaphthalene, chlorothalonil, chloroneb, zarilamide, salicylanilide, cyazofamide, diethylpyrocarbonate, diethofencarb, cyclofuramide, diclocimet, dichlozolin, diclobutrazol, dichlofluanid, cycloheximide, diclomesin, dichloran, dichlorphen, dichlon, disulfiram, ditalifos, dithianon, diniconazole, diniconazole-M , cineb, dinocap, dinoctone, dinosulfone, dinoterbone, dinobuton, dinopentone, dipyrithione, diphenylamine, difenoconazole, cyflufenamide, diflumetorim, cyproconazole, cyprodinil, ciprofuram, cipendazole, simeconazole, dimethyrimol, dimethomorph, cymoxanil, dimoxystrobin, methyl bromide, cyram, silthiopham, streptomycin , spiroxamine, sultropen, sedaxane, zoxamide, dazomet, thiadiazine, thiadinil, thiadifluoro, thiabendazole, thioximide, thiochlorfenfim, thiophanate, thiophanate-methyl, thiophene, thioquinox, quinomethionate, tifluzamide, thiram, decafentine, teknazen , teklofthalam, tecoram, tetraconazole, debacarb , dehydroacetic acid, tebuconazole, tebufloquine, dodicine, dodine, dodecylbenzenesulfonate, copper (II) bis-ethylenediamine (DBEDC), dodemorph, drazoxolone, triadimenol, triadimefon, triazbutyl, triazoxide, triamiphos, triarimol, trichlamide, tricyclazole, triticonazole, tridemorph, oxide tributyltin, triflumizole, trifloxystrobin, triforin, tolylfluanid, tolclofos-methyl, natamycin, nabam, nitrotalisopropyl, nitrostyrene, nuarimol, nonylphenol copper sulfonate, galacrinate, validamycin, valifenalate, harpin protein, bixafen, picoxystrobin, picobenzamide, bithionol, bitertanol, hydroxyisoxazole, hydroxyisoxazole -potassium, binapacryl, biphenyl, piperaline, hymexazole, pyraoxystrobin, pyracarbolide, pyraclostrobin, pyrazophos, pyramethostrobin, pyriophenone, pyridinitrile, pyrifenox, piribencarb, pyrimethanil, piroxychlor, piroxifur, pyroquilone, vinclozolin, famoxadone, fenapanil, fenamidone, fenamino sulf, fenarimol, phenytropan , fenoxanil, ferimzone, ferbam, fentin, fenpiclonil, fenpirazamine, fenbuconazole, fenfuram, fenpropidine, fenpropimorph, fenhexamide, phthalide, butiobate, butylamine, bupyrimate, fuberidazole, blasticidin-S, furamethpyr, furalaxyl, fluacripyrim, fluazinam, flu oxastrobin, fluotrimazole, fluopicolide , fluopyram, fluorimide, furcarbanil, fluxapyroxad, fluquinconazole, furconazole, furconazole-cis, fludioxonil, flusilazole, flusulfamide, flutianil, flutolanil, flutriafol, furfural, furmecyclox, flumetover, flumorph, proquinazid, prochloraz, procymidone, proti ocarb, prothioconazole, propamocarb, propiconazole , propineb, furofanate, probenazole, bromuconazole, hexachlorobutadiene, hexaconazole, hexylthiophos, betoxazine, benalaxyl, benalaxyl-M, benodanil, benomyl, pefurazoate, benquinox, penconazole, benzamorph, pencycuron, benzohydroxamic acid, bentaluron, benthiazole , benthiavalicarb-isopropyl, penthiopyrad, penflufen, boscalid, fosdifen, fosetil, fosetyl-Al, polyoxins, polyoxorim, polycarbamate, folpet, formaldehyde, machine oil, maneb, mancozeb, mandipropamide, myclozolin, myclobutanil, mildiomycin, milneb, mecarbinzide, metasulfocarb, metazoxolone, metam, metham-na triy , metalaxyl, metalaxyl-M, methiram, methylisothiocyanate, meptyldinocap, metconazole, metsulfovax, metfuroxam, metominostrobin, metrafenone, mepanipyrim, mefenoxam, meptildinocap, mepronil, mebenil, iodomethane, rabenzazole, benzalkonium chloride, basic copper chloride, basic sulf at copper, inorganic microbicides such as silver, sodium hypochlorite, copper hydroxide, wettable sulfur, calcium polysulfide, potassium bicarbonate, sodium bicarbonate, sulfur, copper sulfate anhydride, nickel dimethyldithiocarbamate, copper compounds such as copper 8-quinolinolate (copper oxine), zinc sulfate and pentahydrate copper sulfate.

[0142]

Examples of herbicides used for the same purposes as above include 1-naphthylacetamide, 2,4-PA, 2,3,6-TBA, 2,4,5-T, 2,4,5-TB, 2, 4-D, 2,4-DB, 2,4-DEB, 2,4-DEP, 3,4-DA, 3,4-DB, 3,4-DP, 4-CPA, 4-CPB, 4- CPP, MCP, MCPA, MCPA-thioethyl, MCPB, ioxynil, aclonifen, azaphenidine, acifluorfen, aziprothrin, azimsulfuron, asulam, acetochlor, atrazine, atratone, anisuron, anilofos, aviglycine, abscisic acid, amicarbazone, amidosulfuron, amitrol, aminocyclo pyrachlor, aminopyralide , amibuzin, amiprofos-methyl, ametridione, ametrine, alachlor, allidochlor, alloxydim, alorac, isouron, isocarbamide, isoxachlortol, isoxapirifop, isoxaflutole, isoxaben, isocyl, isonoruron, isoproturon, isopropalin, isopolynate, isomethiosine, inabenfid, ipazine, ipfencarbazone , iprimidam , imazaquin, imazapic, imazapyr, imazamethapyr, imazamethabenz, imazamethabenz-methyl, imazamox, imazethapyr, imazosulfuron, indaziflam, indanofan, indolebutyric acid, uniconazole-P, eglinasine, esprocarb, etamethsulfuron, etamethsulfuron-methyl, ethalfluralin, etiolate, these losate-ethyl, etidimuron, etinophen, etifon, ethoxysulfuron, ethoxyphene, etnipromide, etofumesate, etobenzanide, epronaz, erbon, endothal, oxadiazone, oxadiargyl, oxaziclomephone, oxasulfuron, oxapirazone, oxyfluorfen, oryzalin, orthosulfamuron, orbencarb, cafenstrol, cambendichlor, carbasulam , carfentrazone, carfentrazone- ethyl, carbutylate, carbetamide, carboxazole, hisalofop, hisalofop-P, hisalofop-ethyl, xylachlor, quinoclamine, quinonamide, quinclorac, quinmerac, cumiluron, cliodinate, glyphosate, glufosinate, glufosinate-P, credazine, clethodim, cloxiphonac, clodinafop, clodinafop- Prompargil, chlortoluron, clopiralid, cloproxyd, cloprop, chlorbromuron, clofop, clomazon, chlometoxinyl, chlormetoxyphen, clomeupoprop, chlorusifop, chlorosyums, chlorocoly, chloramben, mixers-mixers, chloridazone, chlorimuron, chlorimuron-ethyl, chlorfuron, chloride, chloride, chlor Rtiamid, chlortoluron, chlornitrophen, chlorfenac, chlorfenprop, chlorbufam, chlorflurazol, chlorflurenol, chlorprocarb, chlorprofam, chlormequat, chloreturon, chloroxynil, chloroxuron, chloropon, saflufenacil, cyanazine, cyanathrine, di-allate, diuron, dietamquat, dicamba, cycluron, cycloate, cycloxydim, diclosulam, cyclosulfamuron, dichlorprop, dichlorprop-P, dichlorbenil, diclofop, diclofop-methyl, dichlormate, dichlorourea, diquat, cisanilide, disul, siduron, dithiopyr, dinitramine, cynidone-ethyl, dinosam, cinosulfuron, dinoseb, dinoterb, dinophenate, dinopro p, cyhalofop-butyl, diphenamide, difenoxuron, diphenopentene, difenzoquat, cybutrin, cyprazine, cyprazole, diflufenican, diflufenzopyr, dipropetrin, cypromide, cyperquat, gibberellin, simazine, dimexano, dimethachlor, dimidazone, dimethamethrin, dimethenamid, simethrine, sim ethon, dimepiperate, dimefuron, cinmethylin, swep, sulglycapine, sulfotrione, sulfallate, sulfentrazone, sulfosulfuron, sulfometuron, sulfometuron-methyl, secbumetone, sethoxydim, sebutylazine, terbacil, daimuron, dazomet, dalapon, thiazafluron, tiazopyr, thiencarbazone, thiencarbazone-methyl, ti ocarbazil, thioclorim, thiobencarb, thidiazimine, thidiazuron, thifensulfuron, thifensulfuron-methyl, desmedipham, desmethrin, tetrafluron, tenylchlor, tebutam, tebuthiuron, terbumetone, tepraloxydim, tefuryltrione, tembotrion, delachlor, terbacil, terbucarb, terbuchlor, terbutylazine, terbutryn, then pramezone, tralkoxydim, triaziflam, triasulfuron, tri-allate, trietazine, tricamba, triclopyr, tridifan, tritak, tritosulfuron, triflusulfuron, triflusulfuron-methyl, trifluralin, trifloxysulfuron, tripropindan, tribenuron-methyl, tribenuron, trifop, trifopsim, trimeturon, napthalam, naproanilide, napropamide, nicosulfuron, nitralin, Nitrofen, nitrofluurfen, nipiraclofen, Neburon, Norfluurason, Norururon, Barban, Paclobotrazole, Parakvat, Parafluron, Galoxid, Galoxifop, Galoxifop-P, Galoxifop-Meatyl, Halosafen, Halosufuron, Galosifuron-Mean, Piclores, Bicipropeny, Bicipropyron, Bicipropen Piribak, bispiribak- sodium, pydanone, pinoxaden, bifenox, piperophos, hymexazole, pyraclonil, pyrasulfotol, pyrazoxifene, pyrazosulfuron, pyrazosulfuron-ethyl, pyrazolate, bilanafos, pyraflufen-ethyl, pyriclor, pyridafol, pyrithiobac, pyrithiobac-sodium, pyridate, pyrifthalide, pyributicarb, pyribenzoxy m, pirimisulfan, primisulfuron, pyriminobac-methyl, pyroxasulfone, pyroxulam, fenasulam, phenizofam, fenuron, fenoxasulfone, fenoxaprop, fenoxaprop-P, fenoxaprop-ethyl, phenothiol, fenoprop, phenobenzuron, fentiaprop, fenteracol, phentrazamide, phenmedipham, phenmedipham-ethyl, butachlor, butafenacil, butamifos, butiuron, butidazole, butylate, buturon, butenachlor, butroxydim, butralin, flazasulfuron, flamprop, furyloxifene, prinachlor, primisulfuron-methyl, fluazifop, fluazifop-P, fluazifop-butyl, fluazolate, fluroxypyr, fluotiuron, fluometuron , fluoroglycophene, flurochloridone, fluorodifen, fluornitrophen, fluoromidine, flucarbazone, flucarbazone sodium, fluchloralin, flucetosulfuron, flutiacet, flutiacet-methyl, flupirsulfuron, flufenacet, flufenican, flufenpir, flupropacil, flupropanate, flupoxam, flumioxazin, flumiclorac, flumiclorac-pentyl, flumipropin, flumesin, fluometuron, flumetsulam, fluridone, flurtamone, fluroxypyr, pretilachlor, proxan, proglinazine, procyazine, prodiamine, prosulfalin, prosulfuron, prosulfocarb, propaquizafop, propachlor, propazine, propanil, propyzamide, propisochlor, prohydrojasmone, propyrisulfuron, profame, profluazole , profluralin, prohexadione- calcium, propoxycarbazone, propoxycarbazone sodium, profoxydim, bromacil, brompyrazone, prometrin, prometone, bromoxynil, bromphenoxime, bromobutide, bromobonil, florasulam, hexachloracetone, hexazinone, petoxamide, benzazolin, penoxulam, pebulate, beflutamide, vernolate, perflui don, bencarbazone, benzadox, benzipram, benzylaminopurine, benzthiazuron, benzphendizone, bensulide, bensulfuron-methyl, benzoylprop, benzobicyclone, benzophenap, benzofluorine, bentazone, pentanochlor, benthiocarb, pendimethalin, pentoxazone, benfluralin, benfuresate, fosamine, fomesafen, foramsulfuron, forch lorfenuron, maleic acid hydrazide, mecoprop, mecoprop-P, medinoterb, mezosulfuron, mezosulfuron-methyl, mesotrione, mesoprazine, metoprotrin, metazachlor, metazol, metazosulfuron, metabenzthiazuron, metamitron, metamifop, metham, metalpropalin, methiuron, methiozolin, methiobencarb, methyldimron, methoxuron, met osulam, metsulfuron, metsulfuron- methyl, metflurazone, metobromuron, methobenzuron, metometon, metolachlor, metribuzin, mepiquat chloride, mefenacet, mefluidide, monalide, monisuron, monuron, monochloroacetic acid, monolinuron, molinate, morphamquat, iodosulfuron, iodosulfuron-methyl-na trium, iodobonil, iodomethane, lactofen , linuron, rimsulfuron, lenacyl, rodetanil, calcium peroxide and methyl bromide.

[0143]

Examples of biopesticides used for the same purposes as above include viral preparations such as nuclear polyhedrosis viruses (NPV), granulosa viruses (GV), cytoplasmic polyhedrosis viruses (CPV) and entomopoxia viruses (EPV); microbial pesticides used as an insecticide or nematicide, such as Monacrosporium phymatophagum , Steinernema carpocapsae , Steinernema kushidai and Pasteuria penetrans ; microbial pesticides used as microbicides such as Trichoderma lignorum , Agrobacterium radiobactor , avirulent Erwinia carotovora and Bacillus subtilis ; and biopesticides used as a herbicide, such as Xanthomonas campestris . Such combined use of the insecticidal and acaricidal agricultural and horticultural agent of the present invention with the above biopesticide in the form of a mixture can be expected to give the same effect as above.

[0144]

Other examples of biopesticides include natural predators such as Encarsia formosa , Aphidius colemani , Aphidoletes aphidimyza , Diglyphus isaea , Dacnusa sibirica , Phytoseiulus persimilis , Amblyseius cucumeris and Orius sauteri ; microbial pesticides such as Beauveria brongniartii ; and pheromones such as (Z)-10-tetradecenyl acetate, (E, Z)-4,10-tetradecadienyl acetate, (Z)-8-dodecenyl acetate, (Z)-11-tetradecenyl acetate, (Z)-13-icosene-10 -one and 14-methyl-1-octadecene.

[0145]

Examples of the preparation of typical compounds of the present invention and their intermediates will be described in more detail hereinafter, but the present invention is not limited to these examples.

Example

[0146]

Reference example 1

An example of obtaining an intermediate compound (2-2)

Method for producing 5-cyano-2-(2,2,3,3,3-pentafluoropropyloxy)pyridine

[Formula 9]

2-Chloro-5-cyanopyridine (4.16 g, 30 mmol) was dissolved in NMP (60 ml), 2,2,3,3,3-pentafluoropropanol (6.77 g, 1.5 equivalents) and potassium carbonate were added (12.4 g, 3.0 equivalents) and then the solution was heated at 100 ° C and reacted for 2 hours. After cooling the reaction solution to room temperature, water and ethyl acetate were added to separate the solution, and the organic layer was washed with saturated brine and then dried over sodium sulfate. After distilling off the solvent, purification was carried out by column chromatography to obtain the desired compound (7.03 g, 93% yield).

[0147]

Reference example 2

Method for producing 6-(2,2,3,3,3-pentafluoropropyloxy)nicotinic acid

[Formula 10]

5-Cyano-2-(2,2,3,3,3-pentafluoropropyloxy)pyridine (6.02 g, 24 mmol) obtained in the above step was dissolved in ethanol and water (30 ml) and sodium hydroxide (9 .60 g, 10 equivalents) and the solution was refluxed for 2 hours. After cooling the solution to room temperature for neutralization in an ice bath, a 10% hydrochloric acid solution was added dropwise and extraction was carried out with ethyl acetate. The organic layer was washed with brine and then dried over sodium sulfate. The solvent was distilled off to obtain a mixture containing mainly the desired compound (6.40 g).

[0148]

Reference Example 3

Method for producing 2-(2-(2,2,3,3,3-pentafluoropropyloxy)pyridin-5-yl)benzimidazole

[Formula 11]

6-(2,2,3,3,3-Pentafluoropropyloxy)nicotinic acid (1.47 g, 5.4 mmol) was dissolved in pyridine (10 ml), phenylenediamine (0.70 g, 1.2 equivalents) was added. DMAP (0.13 g, 0.2 equivalents) and EDC · HCl (1.54 g, 1.5 equivalents) and then the solution was reacted for 3 hours at room temperature. Water and ethyl acetate were added to separate the solution, and the organic layer was washed successively with 10% hydrochloric acid, aqueous potassium carbonate, and brine, and dried over sodium sulfate. The solvent was distilled off. The residue was dissolved in NMP (10 ml), p-toluenesulfonic acid monohydrate (3.08 g, 3 equivalents) was added and the solution was then reacted for 1 hour at 140ºC. After cooling the solution to room temperature, an aqueous solution of potassium carbonate and ethyl acetate were added to separate the solution. The organic layer was washed with brine and dried over sodium sulfate. After distilling off the solvent, purification was carried out by column chromatography to obtain the desired compound (0.67 g, 36% yield (from previous step)).

[0149]

Receipt example 1

Method for producing 2-(2-(2,2,3,3,3-pentafluoropropyloxy)pyridin-5-yl)-1-ethanesulfonyl benzimidazole (compound number 1-2)

[Formula 12]

2-(2-(2,2,3,3,3-Pentafluoropropyloxy)pyridin-5-yl)benzimidazole (610 mg, 1.8 mmol) obtained in the above step was dissolved in THF (10 ml) and at room temperature, 60% sodium hydroxide (108 mg, 1.5 equivalents) was added with stirring. After reacting for 10 minutes, ethanesulfonyl chloride (463 mg, 2.0 equivalents) was added and reacted for 1 hour. Water and ethyl acetate were added successively, the organic layer was washed successively with aqueous potassium carbonate and brine, and dried over sodium sulfate. After distilling off the solvent, the concentrated residue was purified by column chromatography to obtain the desired compound (695 mg, 89% yield).

[0150]

Examples of formulations are shown hereinafter, but the present invention is not limited to them. In the formulation examples, “part” means part by weight.

[0151]

Composition example 1

Compound of the present invention 10 parts Xylene 70 parts N-methylpyrrolidone 10 parts Blend of polyoxyethylene nonylphenyl ether and calcium alkylbenzenesulfonate 10 parts

The above ingredients are mixed homogeneously to dissolve to obtain an emulsifiable concentrate formulation.

[0152]

Composition example 2

Compound of the present invention 3 parts Clay powder 82 parts Diatomite powder 15 parts

The above ingredients are mixed uniformly and then crushed to obtain a powdered preparation.

[0153]

Composition example 3

Compound of the present invention 5 parts Mixture of bentonite powder and clay powder 90 parts Calcium lignosulfonate 5 parts

The above ingredients are mixed homogeneously. After adding the appropriate volume of water, the mixture is kneaded, granulated and dried to obtain a granular composition.

[0154]

Composition example 4

Compound of the present invention 20 parts Kaolin and synthetic highly dispersed silicic acid 75 parts Blend of polyoxyethylene nonylphenyl ether and calcium alkylbenzenesulfonate 5 parts

The above ingredients are mixed uniformly and then ground to obtain a wettable powder composition.

[0155]

Example of receiving 5

Compound of the present invention 20 parts Polyoxyethylene lauryl ether 3 parts Sodium dioctyl sulfosuccinate 3.5 parts Dimethyl sulfoxide 37 parts 2-Propanol 36.5 parts

The above ingredients are uniformly mixed to dissolve to obtain a water-soluble thickener composition.

[0156]

Example of getting 6

Compound of the present invention 2 parts Dimethyl sulfoxide 10 parts 2-Propanol 35 parts Acetone 53 parts

The above ingredients are mixed uniformly to dissolve to obtain a liquid spray preparation.

[0157]

Example of receiving 7

Compound of the present invention 5 parts Hexylene glycol 50 parts Isopropanol 45 parts

The above ingredients are mixed uniformly to dissolve to obtain a liquid preparation for transdermal administration.

[0158]

Example of getting 8

Compound of the present invention 5 parts Propylene glycol monomethyl ether 50 parts Dipropylene glycol 45 parts

The above ingredients are mixed uniformly to dissolve to obtain a liquid preparation for transdermal administration.

[0159]

Example of getting 9

Compound of the present invention 2 parts Light liquid paraffin 98 parts

The above ingredients are mixed homogeneously to dissolve to obtain a liquid preparation for transdermal administration (drip).

[0160]

Example of getting 10

Compound of the present invention 2 parts Light liquid paraffin 58 parts Olive oil 30 parts ODO-H 9 parts ShinEtsu Silicone 1 part

The above ingredients are mixed homogeneously to dissolve to obtain a liquid preparation for transdermal administration (drip).

[0161]

Hereinafter, examples of tests in connection with the present invention are shown, but the present invention is not limited to them.

[0162]

Case Study 1

Test for effectiveness against green peach aphid ( Myzus persicae )

Chinese cabbage was planted in plastic pots (diameter: 8 cm, height: 8 cm), green peach aphids were propagated on the plants, and the number of surviving green peach aphids in each pot was counted. The benzimidazole derivatives represented by the general formula (1) of the present invention or their salts were separately dispersed in water and diluted to 500 ppm. Agrochemical dispersions were applied to the foliage of potted Chinese cabbage plants. After air drying the plants, the pots were stored in a greenhouse. 6 days after foliar feeding, the number of surviving green peach aphids on Chinese cabbage in each pot was counted, the control rate was calculated according to the formula below, and the control effectiveness was evaluated according to the criteria shown below.

[0163]

[Expression 1]

Destruction rate=100-{(T×Ca)/(Ta×C)}×100

[0164]

Ta: number of survivors before foliar application in the treated area

T: number of survivors after foliar application in the treated area

Ca: number of survivors before foliar application in an untreated area

C: number of survivors after foliar application in untreated area

[0165]

Indicators

A: The destruction rate is 100%.

B: The destruction rate is 90 to 99%.

C: The destruction rate is 80 to 89%.

D: The destruction rate ranges from 50 to 79%.

[0166]

As a result, compounds 1-3, 1-9, 1-10, 1-20, 1-24, 1-41, 1-42, 5-15, 5-17 and 5-24 of the present invention showed an activity level assessed like A.

[0167]

Case Study 2

Insecticidal test on the little brown leafhopper ( Laodelphax striatellus )

The benzimidazole derivative represented by the general formula (1) of the present invention or its salts were separately dispersed in water and diluted to 500 ppm. Rice plant seedlings (variety: Nihonbare) were immersed in agrochemical dispersions for 30 seconds. After air drying, each seedling was placed in a separate glass tube and inoculated with ten 3rd instar larvae of the small brown planthopper, and the glass tubes were then sealed with cotton swabs. At 8 days post-inoculation, survival rates were calculated from the number of surviving larvae and dead larvae, the adjusted mortality rate was calculated using the formula shown below, and insecticidal effectiveness was assessed according to the criteria shown below.

[0168]

[Expression 2]

Adjusted Mortality Rate (%)=(Untreated Site Survival Rate - Treatment Site Survival Rate)/(Untreated Site Survival Rate)×100

[0169]

Indicators:

A: The adjusted mortality rate is 100%.

B: The adjusted mortality rate is 90 to 99%.

C: The adjusted mortality rate is 80 to 89%.

D: Adjusted mortality rate is 50 to 79%.

[0170]

As a result, compounds 1-7, 1-10, 1-12, 1-13, and 5-15 of the present invention showed an activity level of A.

[0171]

Case Study 3

Insecticidal test for diamondback moth ( Plutella xylostella )

Adult reed moths were released onto Chinese cabbage seedlings and allowed to lay eggs on them. 2 days after the release of adults, Chinese cabbage seedlings with laid eggs were immersed for about 30 seconds in agrochemical dispersions diluted to 500 ppm, each containing a different benzimidazole derivative represented by the general formula (1) of the present invention, or a salt thereof in as an active ingredient. After air drying, the seedlings were stored in a thermostatic chamber at 25ºC. 6 days after the dip treatment, the number of hatched larvae per plot was counted, the adjusted mortality rate was calculated according to the formula below, and insecticidal effectiveness was assessed according to the criteria of Test Example 2. This trial was performed in triplicate using 10 adult reed moths per plot. .

[0172]

[Expression 3]

Adjusted Mortality Rate (%)=(Number of hatched larvae in untreated area - Number of hatched larvae in treated area)/(Number of hatched larvae in untreated area)×100

[0173]

As a result of connections 1-2, 1-3, 1-4, 1-6, 1-7, 1-9, 1-10, 1-12, 1-13, 1-14, 1-15, 1-17 , 1-18, 1-19, 1-20, 1-21, 1-22, 1-23, 1-24, 1-40, 1-41, 1-42, 1-44, 1-45, 3 -1, 5-2, 5-10, 5-12, 5-15, 5-18, 5-19 and 5-24 of the present invention showed an activity level rated as A.

[0174]

Case Study 4

Acaricidal effect on the two-spotted spider mite ( Tetranychus urticae )

A leaf disk with a diameter of 2 cm was prepared from bean leaves, and the leaf disk was placed on moistened filter paper. Adult female two-spotted spider mites were inoculated onto moistened filter paper and then onto 50 ml of an agrochemical dispersion prepared by diluting a composition containing a benzimidazole derivative represented by the general formula (1) of the present invention or its salt as an active ingredient to adjust each of the concentrations to 500 ppm, sprayed evenly onto a turntable. After spraying, it was left in a thermostatic chamber at 25ºC. Two days after treatment with the agrochemical dispersion, the number of dead mites was counted, the adjusted mortality rate was calculated according to the formula shown below, and the acaricidal effectiveness was evaluated according to the criteria of Test Example 2. This test was performed twice using 10 adult female two-spotted spider mites per plot.

[Expression 4]

Adjusted mortality (%)=(Number of dead ticks in untreated area - Number of dead ticks in treated area)/(Number of dead ticks in untreated area)×100

[0175]

As a result of connections 1-1, 1-2, 1-3, 1-4, 1-5, 1-10, 1-12, 1-13, 1-14, 1-15, 1-17, 1-18 , 1-19, 1-20, 1-22, 1-23, 1-24, 1-40, 1-41, 1-42, 1-43, 1-44, 1-45, 1-46, 1 -47, 1-48, 1-49, 1-50, 1-51, 3-1, 5-1, 5-2, 5-3, 5-4, 5-5, 5-6, 5-8 , 5-9, 5-10, 5-11, 5-12, 5-14, 5-17, 5-18, 5-19, 5-20, 5-21, 5-24, 5-25 and 6 -1 of the present invention showed a level of activity rated D or higher.

[0176]

Case study 5

Test to evaluate the effect on the motility of Haemonchus nematode larvae ( Haemonchus contortus )

A solution of the benzimidazole derivative represented by the general formula (1) of the present invention or a salt thereof, diluted in DMSO, was placed in each well of a 96-well plate containing a predetermined prepared solution to obtain a final concentration of 50 ppm. Twenty L-1 stage Haemonchus nematode larvae were released and left for 4 days before their motility was examined. The degree of mobility impairment at each treatment site was adjusted and calculated based on the effectiveness of the obstruction by DMSO alone and scored according to the criteria shown below.

[0177]

Indicators:

A: The adjusted incidence of motor impairment is 100%

B: Adjusted rate of motor impairment is 99% to 90%

C: Adjusted rate of motor impairment is 89% to 80%

D: Adjusted incidence of motor impairment is 79% to 50%

[0178]

As a result, compounds 1-9, 1-15, and 1-40 of the present invention showed an activity level of A.

[0179]

Case study 6

Test to evaluate the effects on motility of canine heartworm larvae ( Dirofilaria immitis )

Five hundred stage L-1 canine heartworm larvae diluted in a predetermined prepared solution were inoculated into each well of a 96-well plate, and a solution of the benzimidazole derivative represented by the general formula (1) of the present invention diluted in DMSO or a salt thereof was added to the final concentration 50 ppm The larvae were then allowed to stand for 3 days and their motility was examined. The degree of mobility impairment at each treatment site was adjusted and calculated based on the effectiveness of the obstruction by DMSO alone, and the effectiveness of the treatment was assessed according to the criteria shown below.

[0180]

Indicators

A: The adjusted incidence of motor impairment is 100%

B: Adjusted rate of motor impairment is 99% to 90%

C: Adjusted rate of motor impairment is 89% to 80%

D: Adjusted incidence of motor impairment is 79% to 50%

[0181]

As a result, compounds 1-9, 1-15 and 1-40 of the present invention showed an activity level of A.

Industrial applicability

[0182]

The compound of the present invention is highly effective in controlling a wide range of agricultural and horticultural pests and mites and is thus useful.

Claims (90)

1. A benzimidazole derivative represented by the general formula (1) [Formula 1] where R represents (a1) (C ₁ -C ₈ )alkyl group; (a2) (C ₃ -C ₈ )cycloalkyl group; (a4) a halogen(C ₁ -C ₈ )alkyl group; (a8) an aryl group having 1 substituent, which is a (b) (C ₁ -C ₆ )alkyl group; R ¹ represents (b1) (C ₁ -C ₈ )alkyl group; (b2) a halogen(C ₁ -C ₈ )alkyl group; (b3) (C ₃ -C ₈ )cycloalkyl group; (b5) (C ₃ -C ₈ )cycloalkyl (C ₁ -C ₈ )alkyl group; (b12) an aryl group having 1 substituent selected from (e) a halogen(C ₁ -C ₆ )alkoxy group, (g) a halogen(C ₁ -C ₆ )alkylthio group, (i) a halogen(C ₁ -C ₆ ) alkylsulfinyl group, (k) a halogen(C ₁ -C ₆ )alkylsulfonyl group and (l) a tri(C ₁ -C ₆ )alkylsilyl group, where the alkyl groups may be the same or different; (b13) aryl(C ₁ -C ₈ )alkyl group; (b14) an aryl(C ₁ -C ₈ )alkyl group having 1 substituent which is selected from (g) a halogen(C ₁ -C ₆ )alkylthio group, and (i) a halogen(C ₁ -C ₆ )alkylsulfinyl group; (b17) (C ₁ -C ₈ )alkoxy(C ₁ -C ₈ )alkyl group; (b18) (C ₁ -C ₈ )alkylthio(C ₁ -C ₈ )alkyl group; (b20) (C ₁ -C ₈ )alkylsulfonyl (C ₁ -C ₈ )alkyl group; X represents O, S, SO, SO ₂ or NR ² where R ² represents a (C ₁ -C ₆ )alkyl group or R ² can be attached to R ¹ to form together with the nitrogen atom to which R ² is attached , a 5-8 membered saturated nitrogen-containing aliphatic heterocycle, optionally having from 1 to 5 substituents, where the substituent is selected from a (C ₁ -C ₆ )alkoxycarbonyl group and a (C ₁ -C ₆ )alkylenedioxy group, where two hydroxy groups in the alkylenedioxy group can be attached to the same carbon atom or to different carbon atoms of a nitrogen-containing aliphatic heterocycle; Y represents (c1) a halogen atom; m represents 0 or 1; Z can be the same or different and represents (d1) a halogen atom; or (d2) (C ₁ -C ₈ )alkyl group; And n represents 0, 1 or 2, or its salt, where the aryl group is an aromatic hydrocarbon group having from 6 to 10 carbon atoms. 2. A benzimidazole derivative according to claim 1, where R represents (a1) (C ₁ -C ₈ )alkyl group; (a4) a halogen(C ₁ -C ₈ )alkyl group; R ¹ represents (b1) (C ₁ -C ₈ )alkyl group; (b2) a halogen(C ₁ -C ₈ )alkyl group; (b3) (C ₃ -C ₈ )cycloalkyl group; (b5) (C ₃ -C ₈ )cycloalkyl (C ₁ -C ₈ )alkyl group; (b12) an aryl group having 1 substituent selected from (e) a halogen(C ₁ -C ₆ )alkoxy group, (g) a halogen(C ₁ -C ₆ )alkylthio group, (i) a halogen(C ₁ -C ₆ ) alkylsulfinyl group, (k) a halogen(C ₁ -C ₆ )alkylsulfonyl group and (l) a tri(C ₁ -C ₆ )alkylsilyl group, where the alkyl groups may be the same or different; (b13) aryl(C ₁ -C ₈ )alkyl group; (b14) an aryl(C ₁ -C ₈ )alkyl group having 1 substituent selected from (g) a halogen(C ₁ -C ₆ )alkylthio group and (i) a halogen(C ₁ -C ₆ )alkylsulfinyl group; (b17) (C ₁ -C ₈ )alkoxy (C ₁ -C ₈ ) alkyl group; or (b18) (C ₁ -C ₈ )alkylthio (C ₁ -C ₈ ) alkyl group; X represents O, S, or NR ² where R ² represents a (C ₁ -C ₆ )alkyl group, or R ² can be attached to R ¹ to form, together with the nitrogen atom to which R ² is attached, 5- 8-membered saturated nitrogen-containing aliphatic heterocycle; Y represents (c1) a halogen atom; m represents 0 or 1; Z can be the same or different and represents (d1) a halogen atom; (d2) (C ₁ -C ₈ )alkyl group; And n is 0, 1 or 2; or its salt. 3. A benzimidazole derivative according to claim 1, where R represents (a1) (C ₁ -C ₈ )alkyl group; (a2) (C ₃ -C ₈ )cycloalkyl group; (a4) a halogen(C ₁ -C ₈ )alkyl group; R ¹ represents (b1) (C ₁ -C ₈ )alkyl group; (b2) a halogen(C ₁ -C ₈ )alkyl group; (b3) (C ₃ -C ₈ )cycloalkyl group; (b12) an aryl group having 1 substituent selected from (e) a halogen(C ₁ -C ₆ )alkoxy group, (g) a halogen(C ₁ -C ₆ )alkylthio group, (i) a halogen(C ₁ -C ₆ ) alkylsulfinyl group, (k) a halogen(C ₁ -C ₆ )alkylsulfonyl group and (l) a tri(C ₁ -C ₆ )alkylsilyl group, where the alkyl groups may be the same or different; (b14) an aryl(C ₁ -C ₈ )alkyl group having 1 substituent which is selected from (g) a halogen(C ₁ -C ₆ )alkylthio group, and (i) a halogen(C ₁ -C ₆ )alkylsulfinyl group; X represents O, S, SO, or NR ² where R ² represents a (C ₁ -C ₆ )alkyl group, Y represents (c1) halogen atom, m represents 0 or 1, Z can be the same or different and represents (d1) halogen atom or (d2) (C ₁ -C ₈ )alkyl group and n is 0, 1 or 2; or its salt. 4. Benzimidazole derivative according to claim 1, where R represents (a1) (C ₁ -C ₈ )alkyl group; R ¹ represents (b1) a halogen(C ₁ -C ₈ )alkyl group; or (b12) an aryl group having 1 substituent selected from (e) a halogen(C ₁ -C ₆ )alkoxy group, (g) a halogen(C ₁ -C ₆ )alkylthio group, (i) a halogen(C ₁ -C ₆ ) alkylsulfinyl group, (k) a halogen(C ₁ -C ₆ )alkylsulfonyl group and (l) a tri(C ₁ -C ₆ )alkylsilyl group, where the alkyl groups may be the same or different; X represents O, m represents 0, and Z may be the same or different and represents (d1) a halogen atom; n is 0, 1 or 2; or its salt. 5. An agricultural and horticultural insecticidal and acaricidal agent containing a benzimidazole derivative or a salt thereof according to one of claims 1 to 4 as an active ingredient. 6. A method of using an agricultural and horticultural insecticidal and acaricidal agent, comprising applying to plants or soil an effective amount of a benzimidazole derivative or a salt thereof in accordance with one of claims 1 to 4. 7. An agent for controlling ectoparasites in animals, containing an effective amount of a benzimidazole derivative or a salt thereof according to one of claims 1 to 4 as an active ingredient. 8. An agent for controlling endoparasites in animals, containing an effective amount of a benzimidazole derivative or a salt thereof according to one of claims 1 to 4 as an active ingredient. 9. The use of a benzimidazole derivative or its salt in accordance with one of claims 1 to 4 in the manufacture of a means of combating ectoparasites. 10. The use of a benzimidazole derivative or its salt in accordance with one of claims 1 to 4 in the manufacture of an endoparasite control agent.