WO2017213137A1

WO2017213137A1 - Novel compound and agricultural/horticultural chemical using same as active ingredient

Info

Publication number: WO2017213137A1
Application number: PCT/JP2017/020971
Authority: WO
Inventors: 信弥逸見; 秀一薄井; 正浩畠本; 福地　俊樹
Original assignee: アグロカネショウ株式会社
Priority date: 2016-06-09
Filing date: 2017-06-06
Publication date: 2017-12-14
Also published as: JPWO2017213137A1; TW201802072A

Abstract

Provided is a novel agricultural/horticultural chemical for controlling pests in crop production such as agriculture and horticulture. An anilide compound or thioamide compound of a specific structure having a substituent shown by the formula (in the formula, R4 and R5 each independently represent a hydrogen, halogen, C1-3 alkyl group, C1-3 haloalkyl group, C1-3 alkoxy group, C1-3 haloalkoxy group, or hydroxyl group) is used as an active ingredient.

Description

Novel compounds and agricultural and horticultural agents containing the same as active ingredients

The present invention relates to a novel compound, an intermediate thereof, an agricultural and horticultural drug containing the compound as an active ingredient, and a method for using the same.

In the field of agriculture and horticulture, various agricultural and horticultural chemicals for the purpose of controlling various pests have been developed and put into practical use.

However, pesticides that have been widely used in the past do not necessarily satisfy the requirements such as the effect, spectrum, residual effect, etc., and further, the number of application times and the reduction of the applied dose. In addition, the appearance of pests that have developed resistance to conventional general pesticides is also a problem. For example, in the cultivation of vegetables, fruit trees, flower buds, tea, wheat and rice, for example, triazole agents, imidazole agents, pyrimidine agents, benzimidazole agents, dicarboximide agents, phenylamide agents, Various pathogens that have developed resistance to various types of fungicides such as strobilurins and SDHI have emerged in various places, and the control of these resistant bacteria has become difficult year by year. Also in the field of insecticides and acaricides, organophosphorus insecticides, pyrethroid insecticides, benzoylurea insecticides, diamide insecticides, organotin acaricides, etc. have been put on the market. However, resistant pests and ticks have emerged shortly after launch, and the decline in effectiveness has become a problem. Therefore, the emergence of new pesticides that exhibit sufficient control effects at low doses and have little adverse environmental impact on various pests that have developed resistance to conventional general agricultural and horticultural agents is always desired. It is rare.

Although various new agricultural and horticultural chemicals have been proposed to meet these demands, they do not necessarily meet the above demands.

Patent Documents 1 to 20 and Non-Patent Document 1 disclose carboxamide derivatives having the following structure having herbicidal activity or bactericidal activity (refer to CAS number).

Patent Document 1: Compound No. 48

Patent Document 2:

Patent Document 3:

Patent Document 4:

Patent Document 5:

Patent Document 6:

Patent Document 7:

Patent Document 8:

Patent Document 9:

Patent Document 10:

Patent Document 11:

Patent Document 12:

Patent Document 13:

Patent Document 14:

Patent Document 15:

Patent Document 16:

Patent Document 17:

Patent Document 18

Patent Document 19:

Patent Document 20:

Non-patent document 1:

However, Patent Documents 2 to 3 and 5 to 20 and Non-Patent Document 1 do not disclose a group represented by the following formula as a substituent of the aniline part of the compound.

Patent Documents 1 and 4 do not disclose a phenyl group having a substituent represented by the above formula as a substituent bonded to the nitrogen atom of the amide portion of the compound.

International Publication No. 2015/000392 Pamphlet Chinese Patent Publication No. 104877692 Chinese Patent Publication No. 101941917 Chinese Patent Publication No. 101472633 U.S. Pat. No. 4,968,343 Japanese Patent Laid-Open No. 02-25454 U.S. Pat. No. 4,750,931 European Patent Publication No. 0303415 JP-A-63-264571 European Patent Publication No. 0205821 Japanese Patent Laid-Open No. 61-280477 JP-A-61-178904 International Publication No. 82/00400 Pamplet Belgian Patent Publication No. 889773 Japanese Patent Laid-Open No. 56-43269 German Patent Publication No. 2926049 JP 54-119476 A JP 54-122728 A JP 54-32479 A JP 52-125626 A

In crop production such as agriculture and horticulture, damage by pests is still great, and development of new agricultural and horticultural drugs is desired due to factors such as resistance to existing drugs and generation of resistant pests.

As a result of intensive studies to solve the above problems, the present inventors have found that the compound represented by the following formula (1), which is a novel compound, is useful as an agricultural and horticultural drug, It has been completed.
That is, the present invention relates to the following [1] to [14].

[1] The following formula (1)

(1)
[Where
R ¹ is hydrogen, C _1-12 alkyl group, C _1-12 haloalkyl group, C _3-6 alkenyl group, C _3-6 haloalkenyl group, C _3-6 alkynyl group, C _3-6 haloalkynyl group, C _3-8 cycloalkyl group, C _3-8 halocycloalkyl group, C _3-8 cycloalkyl-C _1-6 alkyl group, C _1-6 alkoxy group, C _1-6 haloalkoxy group, C _1-6 Alkoxy C _1-6 alkyl group, C _1-6 alkylcarbonyl group, C _1-6 haloalkylcarbonyl group, C _1-6 alkoxycarbonyl group, C _1-6 haloalkoxycarbonyl group, C _1-6 alkoxy C _1-6 Alkylcarbonyl group, C _1-6 alkoxycarbonyl-carbonyl group, mono (di) C _1-6 alkylaminocarbonyl group, mono (di) C _1-6 alkylaminocarbonyl-carbonyl group, C _1-6 alkylcarbonyloxy C _1-6 alkylcarbonyl group, C _1-6 alkylsulfonyl group C _1-6 haloalkylsulfonyl group, benzyl group, cyano group, hydroxyl group or formyl group,
R ² and R ³ are each independently hydrogen, halogen, cyano group, hydroxyl group, C _1-12 alkyl group, C _1-12 haloalkyl group, C _3-8 cycloalkyl group, C _1-6 hydroxyalkyl group, C _1-12 alkoxy group, C _1-6 alkoxy C _1-6 alkyl group, C _1-6 alkylthio group, C _1-6 alkylsulfonyl group, C _1-6 alkylsulfinyl group or phenyl group (wherein the phenyl is , Halogen, C _1-12 alkyl group, C _1-12 haloalkyl group, C _3-8 cycloalkyl group, C _1-6 alkoxy group, C _3-6 alkenyloxy group, C _3-6 alkynyloxy group, C _1-6 haloalkoxy group, C _3-6 haloalkenyloxy group, C _3-6 haloalkynyloxy group, C _1-6 alkylthio group, C _1-6 alkylsulfinyl group, C _1-6 alkylsulfonyl group, C _{1 -6} haloalkylthio group, C _1-6 halo alkyl sulphates Alkenyl group, C _1-6 haloalkylsulfonyl group, the same or different groups may have 1 to 3) is selected from the group consisting of a nitro group or a cyano group,
V is

Indicate
R ⁴ and R ⁵ each independently represent hydrogen, halogen, C _1-3 alkyl group, C _1-3 haloalkyl group, C _1-3 alkoxy group, C _1-3 haloalkoxy group or hydroxyl group;
W may be the same or different, and may be hydrogen, halogen, hydroxyl group, amino group, C _1-12 alkyl group, C _1-12 haloalkyl group, C _3-8 cycloalkyl group, C _1-6 alkoxy group, mono ( Di) C _1-6 alkylamino group, C _3-6 alkenyloxy group, C _3-6 alkynyloxy group, C _1-6 haloalkoxy group, C _3-6 haloalkenyloxy group, C _3-6 haloalkynyloxy group, C _1-6 alkylthio group, C _1-6 alkylsulfinyl group, C _1-6 alkylsulfonyl group, C _1-6 haloalkylthio group, C _1-6 haloalkylsulfinyl group, C _1-6 haloalkylsulfonyl groups, C _1-6 alkoxycarbonyl group, mono (di) C _1-6 alkylaminocarbonyl group, C _1-6 hydroxyalkyl group, C _1-6 alkoxy C _1-6 alkyl group, C _1-6 alkylcarbonyloxy group, amino Carbonyl group, hydroxycarbo When it represents a nyl group, a formyl group, a nitro group or a cyano group, or when two Ws are substituted with two adjacent carbon atoms on the phenyl ring, the two Ws are bonded to each other. May form a saturated or unsaturated 5- or 6-membered ring together with the carbon atoms
X may be the same or different, and may be hydrogen, halogen, C _1-12 alkyl group, C _1-12 haloalkyl group, C _3-8 cycloalkyl group, C _1-6 alkoxy group, C _3-6 alkenyloxy group, C _3-6 alkynyloxy group, C _1-6 haloalkoxy group, C _3-6 haloalkenyloxy group, C _3-6 haloalkynyloxy group, C _1-6 alkylthio group, C _1-6 alkylsulfinyl group, C _1-6 alkylsulfonyl group, C _1-6 haloalkylthio group, C _1-6 haloalkylsulfinyl group, C _1-6 haloalkylsulfonyl group, a nitro group or a cyano group,
Y represents a (Y ¹ ) n ³ -heteroaryl-A- group or a (Y ¹ ) n ⁴ -aryl-A- group;
Y ¹ may be the same or different and is hydrogen, halogen, C _1-12 alkyl group, C _1-12 haloalkyl group, C _3-8 cycloalkyl group, C _1-6 alkoxy group, C _3-6 alkenyloxy. Group, C _3-6 alkynyloxy group, C _1-6 haloalkoxy group, C _3-6 haloalkenyloxy group, C _3-6 haloalkynyloxy group, C _1-6 alkylthio group, C _1-6 alkylsulfinyl group , C _1-6 alkylsulfonyl group, C _1-6 haloalkylthio group, C _1-6 haloalkylsulfinyl group, C _1-6 haloalkylsulfonyl group, a pentafluorosulfanyl group, C _2-6 alkenyl, C _2-6 alkynyl Group, C _1-6 alkoxy C _1-6 alkyl group, C _1-6 alkylcarbonyl group, C _1-6 haloalkylcarbonyl group, C _1-6 alkoxycarbonyl group, C _1-6 haloalkoxycarbonyl group, C _{1- 6} alkoxy C _1-6 Arukiruka Boniru group, mono (di) C _1-6 alkylaminocarbonyl group, an amino group, mono (di) C _1-6 alkylamino group, mono (di) C _1-6 alkylcarbonylamino group, a nitro group, a cyano group, An aryl group or a heteroaryl group (wherein the aryl and heteroaryl are, respectively, halogen, C _1-12 alkyl group, C _1-12 haloalkyl group, C _3-8 cycloalkyl group, C _1-6 alkoxy group, C _3-6 alkenyloxy group, C _3-6 alkynyloxy group, C _1-6 haloalkoxy group, C _3-6 haloalkenyloxy group, C _3-6 haloalkynyloxy group, C _1-6 alkylthio group, C _{1 -6} alkylsulfinyl group, C _1-6 alkylsulfonyl group, C _1-6 haloalkylthio group, C _1-6 haloalkylsulfinyl group, C _1-6 haloalkylsulfonyl group, is selected from the group consisting of a nitro group or a cyano group Having 1 to 3 identical or different groups)
Z ¹ represents an oxygen atom or a sulfur atom,
Z ² represents an oxygen atom, a sulfur atom or NR ⁶ ;
R ⁶ is hydrogen, C _1-12 alkyl group, C _1-12 haloalkyl group, C _3-6 alkenyl group, C _3-6 haloalkenyl group, C _3-6 alkynyl group, C _3-6 haloalkynyl group, C _3-8 cycloalkyl group, C _3-8 halocycloalkyl group, C _3-8 cycloalkyl-C _1-6 alkyl group, C _1-6 alkoxy group, C _1-6 haloalkoxy group, C _1-6 Alkoxy C _1-6 alkyl group, C _1-6 alkylcarbonyl group, C _1-6 haloalkylcarbonyl group, C _1-6 alkoxycarbonyl group, C _1-6 haloalkoxycarbonyl group, C _1-6 alkoxy C _1-6 Alkylcarbonyl group, C _1-6 alkoxycarbonyl-carbonyl group, mono (di) C _1-6 alkylaminocarbonyl group, mono (di) C _1-6 alkylaminocarbonyl-carbonyl group, C _1-6 alkylsulfonyl group, C _1-6 haloalkylsulfonyl group, a benzyl group, a cyano group, Shows the acid group or formyl group,
A represents an oxygen atom, sulfur atom, sulfinyl or sulfonyl group,
n ¹ and n ² each independently represent an integer of 1 to 4,
n ³ and n ⁴ each independently represents an arbitrary integer of 1 or more. ]
Or an N-oxide or salt thereof.

[2] V is 4-substituted

The compound according to the above [1], its N-oxide or a salt thereof.

[3] The compound according to [1] or [2] above, wherein R ³ represents a hydrogen atom and Y represents a (Y ¹ ) n ³ -pyridyloxy group, an N-oxide thereof or a salt thereof.

[4] A process for producing the compound according to [1] above, its N-oxide or a salt thereof, comprising the following formula (2)

(2)
[Wherein R ¹ , V ¹ , W, and n ¹ are as defined in Formula (1)]
And a compound represented by the following formula (3):

(3)
[Wherein R ² R ³ , Z ¹ , Z ² , X ¹ , Y, n ² are as defined in Formula (1)]
The manufacturing method including making the compound represented by these react.

[5] A process for producing the compound according to [1] above, its N-oxide or a salt thereof, comprising the following formula (2)

(2)
[Wherein R ¹ , V ¹ , W, and n ¹ are as defined in Formula (1)]
And a compound represented by the following formula (4):

(4)
[In the formula, Hal represents halogen, and R ² R ³ , Z ¹ , Z ² , X ¹ , Y, and n ² are as defined in Formula (1)]
The manufacturing method including making the compound represented by these react.

[6] An agricultural and horticultural drug containing the compound according to any one of [1] to [3] above, its N-oxide or a salt thereof.

[7] An agricultural and horticultural fungicide containing the compound according to any one of [1] to [3] above, its N-oxide or a salt thereof.

[8] An agricultural and horticultural insecticide containing the compound according to any one of [1] to [3] above, its N-oxide or a salt thereof.

[9] An agricultural and horticultural acaricide containing the compound according to any one of [1] to [3] above, its N-oxide or a salt thereof.

[10] Use of the agricultural and horticultural chemical according to [6] above for controlling plant pests.

[11] The use according to [10] above, wherein the pest is a pathogen.

[12] A method for controlling plant pests, comprising a step of treating pests and / or their habitats and / or seeds and / or plant propagation materials with the agricultural and horticultural agent according to [6]. .

[13] A plant pest comprising a step in which a useful crop is grown, or a place where the useful crop is grown or a growing crop is treated with the agricultural and horticultural agent according to [6]. How to prevent.

[14] A method for preparing an agrochemical composition, the method comprising a step of mixing the agricultural and horticultural chemical according to [6] above with a bulking agent and / or a surfactant.

The compound of the present invention has an excellent effect as an agricultural and horticultural agent.

In the definition of the compound of the present invention represented by the formula (I), “halogen” represents a chlorine atom, a bromine atom, an iodine atom or a fluorine atom.
“C _1-12 alkyl group” means, for example, methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, i-butyl group, s-butyl group, t-butyl group, n- Pentyl group, isopentyl group, neopentyl group, tert-pentyl group, n-hexyl group, isohexyl group, n-heptyl group, isoheptyl group, n-octyl group, isooctyl group, n-nonyl group, isononyl group, n-decyl group A linear or branched alkyl group having 1 to 12 carbon atoms, such as isodecyl group, n-undecyl group, isoundecyl group, n-dodecyl group and isododecyl;
The “C _1-12 haloalkyl group” refers to a linear or branched alkyl group having 1 to 12 carbon atoms substituted with one or more halogen atoms which may be the same or different.
The “C _3-8 cycloalkyl group” refers to a cyclic cycloalkyl group having 3 to 8 carbon atoms such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclooctyl and the like.
The “C _3-8 halocycloalkyl group” is the same as, for example, 1-chlorocyclopropyl, 2,2-difluorocyclopropyl, 2,2-dichloro-1-methylcyclopropyl, 4,4-difluorocyclohexyl, etc. A cyclic cycloalkyl group having 3 to 8 carbon atoms substituted with one or more halogen atoms which may be different is shown.
The “C _3-8 cycloalkyl-C _1-6 alkyl group” means a cyclic carbon atom having 3 to 8 carbon atoms such as cyclopropylmethyl, 1-cyclopropylethyl, cyclobutylmethyl, 2-cyclooctylpropyl, etc. A cycloalkyl-C _1-6 alkyl group;

Examples of the C _1-6 haloalkyl group include a fluoromethyl group, a chloromethyl group, a difluoromethyl group, a trifluoromethyl group, a chlorodifluoromethyl group, a bromodifluoromethyl group, a dichlorofluoromethyl group, a 1-fluoroethyl group, 2 -Fluoroethyl group, 2-chloroethyl group, 2-bromoethyl group, 2-iodoethyl group, 2,2,2-trifluoroethyl group, 2,2,2-trichloroethyl group, pentafluoroethyl group, 1-fluoroisopropyl Group, 3-fluoropropyl group, 3-chloropropyl group, 3-bromopropyl group, heptafluoropropyl group, 4-fluorobutyl group, 4-chlorobutyl, nonafluorobutyl group, 5,5,5-trifluoropentyl group 5-chloropentyl group, undecafluoropentyl group, 6,6,6- C 1-6 linear or branched alkyl substituted with 1 to 13, preferably 1 to 9, halogen atoms such as trifluorohexyl, 6-chlorohexyl, tridecafluorohexyl and the like Groups.
Examples of the C _1-12 haloalkyl group include, in addition to the groups exemplified for the C _1-6 haloalkyl group, for example, 1-fluoroheptyl group, 1-fluorooctyl group, 1-fluoroundecyl group, 1-fluorododecyl group. And a linear or branched alkyl group having 1 to 12 carbon atoms and substituted with 1 to 13, preferably 1 to 9 halogen atoms.

Examples of the C _1-6 alkoxy group include a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, a cyclopropyloxy group, an n-butoxy group, a sec-butoxy group, a tert-butoxy group, and an n-pentoxy group. And a linear or branched alkoxy group having 1 to 6 carbon atoms such as an n-hexyloxy group.
Examples of the C _1-6 haloalkoxy group include a fluoromethoxy group, a dichloromethoxy group, a trichloromethoxy group, a difluoromethoxy group, a trifluoromethoxy group, a chlorodifluoromethoxy group, a bromodifluoromethoxy group, a dichlorofluoromethoxy group, 1- Fluoroethoxy group, 2-fluoroethoxy group, 2-chloroethoxy group, 2-bromoethoxy group, 2-iodoethoxy group, 2,2,2-trifluoroethoxy group, 2,2,2-trichloroethoxy group, penta Fluoroethoxy group, 1-fluoroisopropoxy group, 3-fluoropropoxy group, 3-chloropropoxy group, 3-bromopropoxy group, 4-fluorobutoxy group, 4-chlorobutoxy group, etc., preferably 1-9 Linear or branched having 1 to 6 carbon atoms substituted with halogen atoms A chain alkoxy group is mentioned.

Examples of the C _2-6 alkenyl group include a vinyl group, 1-propenyl group, allyl group, isopropenyl group, 2-butenyl group, 3-butenyl group, 1-methyl-2-propenyl group, 2-pentenyl group, 3-pentenyl group, 4-pentenyl group, 1,1-dimethyl-2-propenyl group, 1-ethyl-2-propenyl group, 1-methyl-2-butenyl group, 1-methyl-3-butenyl group, 2- At least one double at any position such as hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, etc. Examples thereof include a linear or branched alkenyl group having 3 to 6 carbon atoms having a bond.
Examples of the C _3-6 haloalkenyl group include a 3-chloro-2-propenyl group, a 3,3-difluoro-2-allyl group, a 3,3-dichloro-2-allyl group, a 4,4,4-trimethyl group, and the like. At least one double bond at any position such as fluoro-2-butenyl group, 4,4,4-trifluoro-3-butenyl group, 5-chloro-3-pentenyl group, 6-fluoro-2-hexenyl group And a straight-chain or branched alkenyl group having 3 to 6 carbon atoms and having 1 to 13, preferably 1 to 7 halogen atoms.

Examples of the C _2-6 alkynyl group include ethynyl group, 2-propynyl group, 1-methyl-2-propynyl group, 1,1-dimethyl-2-propynyl group, 1-butynyl group, 2-butynyl group, 3 -Butynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 1,1-dimethyl-2- 3 to 6 carbon atoms having at least one triple bond at any position such as butynyl group, 1,1-dimethyl-3-butynyl group, 1-methyl-3-pentynyl group, 1-methyl-4-pentynyl group, etc. A linear or branched alkynyloxy group is mentioned.
C _3-6 haloalkynyl groups include 4,4,4-trifluoro-2-butynyl group, 5,5,5-trifluoro-3-pentynyl group, 1-methyl-3,3,3-trifluoro Linear or branched alkynyl having 3 to 6 carbon atoms and having at least one triple bond at an arbitrary position such as -2-butynyl group, 1-methyl-5,5,5-trifluoro-2-pentynyl group, etc. And an alkynyl group substituted with 1 to 9, preferably 1 to 6, halogen atoms.

The C _3-6 alkenyloxy group, can be mentioned those with group to those exemplified in the C _3-6 alkenyl group.
The C _3-6 haloalkenyloxy group, can be mentioned those with group to those exemplified in the C _3-6 haloalkenyl group.

The C _3-6 alkynyloxy group, can be mentioned those with group to those exemplified in the C _3-6 haloalkenyl group.
The C _3-6 haloalkynyl group include those attached group to those exemplified in the C _3-6 haloalkenyl group.

Examples of the C _1-6 alkylthio group include a methylthio group, an ethylthio group, an n-propylthio group, an isopropylthio group, a cyclopropylthio group, an n-butylthio group, a sec-butylthio group, a tert-butylthio group, and an n-pentylthio group. And a linear or branched alkylthio group having 1 to 6 carbon atoms such as an n-hexylthio group.

Examples of the C _1-6 alkylsulfinyl group include a methylsulfinyl group, an ethylsulfinyl group, an n-propylsulfinyl group, an isoprosulfinyl group, a cyclopropylsulfinyl group, an n-butylsulfinyl group, a sec-butylsulfinyl group, and a tert-butyl. Examples thereof include a linear or branched alkylsulfinyl group having 1 to 6 carbon atoms such as a sulfinyl group, an n-pentylsulfinyl group, and an n-hexylsulfinyl group.

Examples of the C _1-6 alkylsulfonyl group include methylsulfonyl group, ethylsulfonyl group, n-propylsulfonyl group, isoprosulfonyl group, cyclopropylsulfonyl group, n-butylsulfonyl group, sec-butylsulfonyl group, tert-butyl. Examples thereof include a linear or branched alkylsulfonyl group having 1 to 6 carbon atoms such as a sulfonyl group, an n-pentylsulfonyl group, and an n-hexylsulfonyl group.

Examples of the C _1-6 haloalkylthio group include a difluoromethylthio group, a trifluoromethylthio group, a monochloromethylthio group, a dichloromethylthio group, a trichloromethylthio group, a monobromomethylthio group, a dibromomethylthio group, a tribromomethylthio group, and a 1-fluoro group. Ethylthio group, 2-fluoroethylthio group, 2,2-difluoroethylthio group, 2,2,2-trifluoroethylthio group, 2-chloro-2,2-difluoroethylthio group, 1-chloroethylthio Group, 2-chloroethylthio group, 2,2, -dichloroethylthio group, 2,2,2-trichloroethylthio group, 2-bromoethylthio group, 2,2-dibromoethylthio group, 2,2, 2-tribromoethylthio group, pentafluoroethylthio group, 3-fluoropropylthio group, 3-chloropropylthio group, 3-bromopropylthio group, 1,3-difluoro-2-propylthio group 3,3,3-trifluoropropylthio group, 1,3-dichloro-2-propylthio group, 1,1,1-trifluoro-2-propylthio group, 1-chloro-3-fluoro-2-propylthio group 1,1,1,3,3,3-hexafluoro-2-propylthio group, 1,1,1,3,3,3-hexafluoro-2-chloro-2-propylthio group, 2,2,3 , 3,3-pentafluoropropylthio group, heptafluoroisopropylthio group, heptafluoro-n-propylthio group, 4-fluorobutylthio group, 4,4,4-trifluorobutylthio group, nonafluoro-n-butylthio group And a linear or branched alkylthio group having 1 to 6 carbon atoms substituted with 1 to 13, preferably 1 to 9 halogen atoms such as a nonafluoro-2-butylthio group.

C _1-6 haloalkylsulfinyl group includes difluoromethylsulfinyl group, trifluoromethylsulfinyl group, dichloromethylsulfinyl group, trichloromethylsulfinyl group, monobromomethylsulfinyl group, dibromomethylsulfinyl group, tribromomethylsulfinyl group, 1- Fluoroethylsulfinyl group, 2-fluoroethylsulfinyl group, 2,2-difluoroethylsulfinyl group, 2,2,2-trifluoroethylsulfinyl group, 2-chloro-2,2-difluoroethylsulfinyl group, 1-chloroethyl Sulfinyl group, 2-chloroethylsulfinyl group, 2,2, -dichloroethylsulfinyl group, 2,2,2-trichloroethylsulfinyl group, 2-bromoethylsulfinyl group, 2,2-dibromoethylsulfinyl group, 2,2 , 2-tribromoethylsulfinyl group, Pentafluoroethylsulfinyl group, 3-fluoropropylsulfinyl group, 3-chloropropylsulfinyl group, 3-bromopropylsulfinyl group, 1,3-difluoro-2-propylsulfinyl group, 3,3,3-trifluoropropylsulfinyl group 1,3-dichloro-2-propylsulfinyl group, 1,1,1-trifluoro-2-propylsulfinyl group, 1-chloro-3-fluoro-2-propylsulfinyl group, 1,1,1,3, 3,3-hexafluoro-2-propylsulfinyl group, 1,1,1,3,3,3-hexafluoro-2-chloro-2-propylsulfinyl group, 2,2,3,3,3-pentafluoro Propylsulfinyl group, heptafluoroisopropylsulfinyl group, heptafluoro-n-propylsulfinyl group, 4-fluorobutylsulfinyl group, 4,4,4-trifluorobutylsulfinyl group, nonafluoro-n-butylsulfinyl group And a linear or branched alkylsulfinyl group having 1 to 6 carbon atoms substituted with 1 to 13, preferably 1 to 9 halogen atoms such as nonafluoro-2-butylsulfinyl group.

Examples of the C _1-6 haloalkylsulfonyl group include a difluoromethylsulfonyl group, a trifluoromethylsulfonyl group, a dichloromethylsulfonyl group, a trichloromethylsulfsulfonyl group, a monobromomethylsulfonyl group, a dibromomethylsulfonyl group, and a tribromomethylsulfonyl group. 1-fluoroethylsulfonyl group, 2-fluoroethylsulfonyl group, 2,2-difluoroethylsulfonyl group, 2,2,2-trifluoroethylsulfonyl group, 2-chloro-2,2-difluoroethylsulfonyl group, 1 -Chloroethylsulfonyl group, 2-chloroethylsulfonyl group, 2,2, -dichloroethylsulfonyl group, 2,2,2-trichloroethylsulfonyl group, 2-bromoethylsulfonyl group, 2,2-dibromoethylsulfonyl group, 2,2,2-tribromoethylsulfonyl group, pentafluoroethylsulfonyl group, 3-fluoropropylsulfonyl group, 3-chloropropylsulfonyl group, 3-bromopropylsulfonyl group, 1,3-difluoro-2-propylsulfonyl group, 3,3,3-trifluoropropylsulfonyl group, 1,3-dichloro 2-propylsulfonyl group, 1,1,1-trifluoro-2-propylsulfonyl group, 1-chloro-3-fluoro-2-propylsulfonyl group, 1,1,1,3,3,3-hexafluoro -2-propylsulfonyl group, 1,1,1,3,3,3-hexafluoro-2-chloro-2-propylsulfonyl group, 2,2,3,3,3-pentafluoropropylsulfonyl group, heptafluoro 1 such as isopropylsulfonyl group, heptafluoro-n-propylsulfonyl group, 4-fluorobutylsulfonyl group, 4,4,4-trifluorobutylsulfonyl group, nonafluoro-n-butylsulfonyl group, nonafluoro-2-butylsulfonyl group ~ 13, preferably 1 ~ Examples thereof include a linear or branched alkylsulfonyl group having 1 to 6 carbon atoms, which is substituted with 9 halogen atoms.

Examples of the C _1-6 alkoxy C _1-6 alkyl group include 1 to 6 carbon atoms such as methoxymethyl group, methoxy-2-ethyl group, ethoxymethyl group, isopropoxymethyl group, tert-butoxy-1-ethyl group, and the like. A linear or branched alkoxy group having 1 to 6 carbon atoms.

Examples of the C _1-6 alkylcarbonyl group include linear or branched alkylcarbonyl groups having 1 to 6 carbon atoms such as a methylcarbonyl group, an ethylcarbonyl group, an isopropylcarbonyl group, and a tert-butylcarbonyl group.
As the C _1-6 haloalkylcarbonyl group, for example, a trifluoromethylcarbonyl group, a chloromethylcarbonyl group, a 3-bromopropylcarbonyl group, etc., preferably having 1 to 6 carbon atoms substituted with 1 to 9 halogen atoms A linear or branched alkoxy group is mentioned.

Examples of the C _1-6 alkoxycarbonyl group include linear or branched alkoxycarbonyl groups having 1 to 6 carbon atoms such as a methoxycarbonyl group, an ethoxycarbonyl group, a 1-fluoroisopropoxycarbonyl group, and a tert-butoxycarbonyl group. Is mentioned.
As the C _1-6 haloalkoxycarbonyl group, for example, 1 to 13, such as trifluoromethoxycarbonyl group, 2-chloroethoxycarbonyl group, isopropoxycarbonyl group, 2,2,2-trifluoroethoxycarbonyl group, etc. are preferable. Includes a linear or branched alkyl group having 1 to 6 carbon atoms and substituted with 1 to 9 halogen atoms.

Examples of the C _1-6 alkoxy C _1-6 alkylcarbonyl group include a methoxymethylcarbonyl group, a methoxy-2-ethylcarbonyl group, an ethoxymethylcarbonyl group, an isopropoxymethylcarbonyl group, and a tert-butoxy-1-ethyl group. Examples thereof include straight-chain or branched alkoxy having 1 to 6 carbon atoms and straight-chain or branched alkyl groups having 1 to 6 carbon atoms.

A mono (di) C _1-6 alkylamino group represents a mono C _1-6 alkylamino group or a diC _1-6 alkylamino group;
Examples of the mono C _1-6 alkylamino group include linear or branched alkylamino groups having 1 to 6 carbon atoms such as a methylamino group, an ethylamino group, and a tert-butylamino group.
Examples of the di-C _1-6 alkylamino group include linear or branched dialkylamino groups having 1 to 6 carbon atoms such as dimethylamino group, N-methyl-N-ethylamino group, and diethylamino group. .
Examples of the mono C _1-6 alkylaminocarbonyl group include linear or branched alkylaminocarbonyl groups having 1 to 6 carbon atoms such as a methylaminocarbonyl group, an ethylaminocarbonyl group, and a tert-butylaminocarbonyl group. It is done.
Examples of the di-C _1-6 alkylaminocarbonyl group include linear or branched dialkylaminocarbonyl having 1 to 6 carbon atoms such as dimethylaminocarbonyl group, Nmethyl-N-ethylaminocarbonyl group, and diethylaminocarbonyl group. Groups.

Examples of the C _1-6 hydroxyalkyl group include hydroxymethyl group, dihydroxymethyl group, 1-hydroxyethyl group, 2-hydroxyethyl group, 1,2-dihydroxyethyl group, 1-hydroxyisopropyl group, 3-hydroxypropyl group, Examples thereof include a 4-hydroxybutyl group, a 6-hydroxyhexyl group, and preferably a linear or branched alkyl group having 1 to 6 carbon atoms substituted with 1 to 2 hydroxy groups.

In the present invention, examples of the “aryl group” include phenyl group, 1-naphthyl group, 2-naphthyl group, anthracenyl group, phenanthrenyl group, acenaphthylenyl group and the like.

In the present invention, the “heteroaryl” may be monocyclic or polycyclic, and a heterocyclic group containing one or two or more of the same or different ring-constituting heteroatoms can be used. Although the kind of hetero atom is not specifically limited, For example, a nitrogen atom, an oxygen atom, a sulfur atom etc. can be illustrated. Examples of the heterocyclic group include furyl, thienyl, pyrrolyl, oxazolyl, isoxazolyl, dihydroisoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, thiadiazolyl, triazolyl , Tetrazolyl group, pyrrolidinyl group, pyridyl group, pyridazinyl group, pyrimidinyl group, pyrazinyl group, azepinyl group, oxazepinyl group, piperidinyl group, morpholinyl group and the like. Examples of the polycyclic heterocyclic group include benzofuranyl group, isobenzofuranyl group, benzothienyl group, indolyl group, isoindolyl group, indazolyl group, benzoxazolyl group, benzoisoxazolyl group, benzothiazolyl group, benzoisothiazo group. Ryl group, benzooxadiazolyl group, benzothiadiazolyl group, benzotriazolyl group, quinolyl group, isoquinolyl group, cinnolinyl group, quinazolinyl group, quinoxalinyl group, phthalazinyl group, naphthyridinyl group, purinyl group, pteridinyl group, carbazolyl group And 8- to 14-membered polycyclic heterocyclic groups such as carbolinyl group, acridinyl group, 2-acridinyl, 3-acridinyl, 4-acridinyl, 9-acridinyl, phenoxazinyl group, phenothiazinyl group and phenazinyl group.

Y represents a (Y ¹ ) n ³ -heteroaryl-A- group or a (Y ¹ ) n ⁴ -aryl-A- group, and preferred substituents include (Y ¹ ) n ³ -pyridyloxy group or ( Y ¹ ) n ⁴ -phenoxy group. n ³ and n ⁴ each independently represents an arbitrary integer of 1 or more, preferably an integer of 1 to 10, more preferably an integer of 1 to 5.
Examples of (Y ¹ ) n ³ -pyridyloxy group include 5-trifluoromethyl-2-pyridyloxy group, 3-chloro-5-iodo-2-pyridyloxy group, 5-iodo-2-pyridyloxy group, 3-fluoro-5-trifluoromethyl-2-pyridyloxy group, 3,5-dichloro-2-pyridyloxy group, 6-chloro-3-pyridyloxy group, 6-trifluoromethyl-3-pyridyloxy group, 4-pyridyloxy group can be mentioned.

Examples of the (Y ¹ ) n ⁴ -phenoxy group include a 4-trifluorophenoxy group, a 4-iodophenoxy group, a 2-fluoro-4-trifluoromethylphenoxy group, and a 2,4-dichlorophenoxy group.

In the compound of the present invention represented by the formula (I), two Ws are substituted with two adjacent carbon atoms on the phenyl ring, these Ws are bonded to each other, and each W is bonded. A saturated or unsaturated 5- or 6-membered ring may be formed together with the carbon atoms present, but for example, condensed with a phenyl ring to form an indane ring, a tetrahydronaphthalene ring, or a naphthalene ring, respectively. When a saturated or unsaturated 5- or 6-membered ring is formed, two Ws substituted by two adjacent carbon atoms on the phenyl ring are, for example, —CH ₂ CH ₂ CH ₂ —, —CH ( CH ₃ ) CH ₂ CH _2- , -CH ₂ CH ₂ CH ₂ CH _2- , -CH ₂ CH ₂ C (CH ₃ ) ₂ CH _2- , -CH = CHCH = CH-, -N = CHCH = CH- , -OCHCHCH _2- , -CH (CH ₃ ) -OC (CH ₃ ) _2- .

Examples of the salt of the compound of the present invention represented by the formula (1) include inorganic acid salts such as hydrochloride, sulfate, nitrate, and phosphate, acetate, fumarate, maleate, oxalate, Examples thereof include organic acid salts such as methanesulfonate, benzenesulfonate, and p-toluenesulfonate.

The compound of the present invention represented by the formula (1) may contain one or more asymmetric centers in the structural formula, and there are two or more optical isomers and diastereomers. In addition, the present invention includes all the optical isomers and mixtures containing them in an arbitrary ratio. Moreover, the compound represented by the said Formula (1) of this invention may contain a geometric isomer and a rotational isomer. In the structural formula, there may be two kinds of geometric isomers derived from carbon-carbon double bonds, but the present invention provides each geometric isomer, rotamer and a mixture containing them in an arbitrary ratio. Is also included.

Among the compounds of the present invention, R ¹ and R ³ are hydrogen atoms, R ² is hydrogen atom, halogen atom, C _1-3 alkyl group, C _1-3 alkoxy, C _1-3 haloalkoxy, C _1-3 alkoxy A compound showing a C _1-3 alkyl group is preferred, and a compound wherein R ² is a methyl group, an ethyl group or a propyl group is particularly preferred.
Among the compounds of the present invention, compounds in which Y represents a hydrogen atom are preferred.

Hereinafter, although the novel compound represented by the formula (1) of the present invention and a typical production method thereof are shown, the present invention is not limited to these.

Reaction formula 1

[Wherein R ¹ , R ² , R ³ , V, W, X, Y, Z ¹ , Z ² , n ¹ and n ² are as defined in the above formula (1)]

The reaction represented by the above reaction formula 1 can be carried out in the presence of a condensing agent and in the presence of a solvent and a base, or in the presence of a condensing agent and in the absence of a solvent and a base.

Solvents include aromatic hydrocarbons such as benzene, toluene, and xylene; ketones such as acetone, methyl ethyl ketone, and methyl isobutyl ketone; halogenated hydrocarbons such as chloroform and methylene chloride; water; methyl acetate, Esters such as ethyl acetate; or ethers such as tetrahydrofuran, dioxane, diethyl ether, 1,2-dimethoxyethane; water; acetonitrile, N, N-dimethylformamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide, etc. Polar solvents; alcohols such as methanol, ethanol and isopropanol, or mixed solvents of the above solvents.

Bases include organic bases such as triethylamine, pyridine, 1,8-diazabicyclo [5.4.0] undec-7-ene (DBU), 4-dimethylaminopyridine; sodium hydroxide, potassium hydroxide, etc. Alkali metal hydroxides; alkaline earth metal hydroxides such as calcium hydroxide; alkaline metal carbonates such as sodium carbonate and potassium carbonate; alkaline earth metal carbonates such as calcium carbonate; alkali metals such as sodium bicarbonate Examples thereof include hydrogen carbonates; metal alkoxides such as sodium methoxide and potassium ethoxide; metal hydrides such as sodium hydride and potassium hydride.

Examples of the condensing agent used in the reaction include 1,3-dicyclohexylcarbodiimide (DCC), 2-chloro-1-methylpyridinium iodide, carbonyldiimidazole (CDI), and trifluoroacetic anhydride. .

The reaction temperature is, for example, −30 ° C. to 150 ° C., preferably −5 ° C. to 80 ° C. After completion of the reaction, the target product may be isolated from the reaction system by a conventional method. If necessary, the target product can be produced by purification by washing with a solvent, recrystallization, column chromatography or the like.

Reaction formula 2

The reaction represented by the above reaction formula 2 can be carried out in the presence or absence of a solvent and a base.

The solvent is not particularly limited as long as it does not directly participate in this reaction, and for example, aromatic hydrocarbons such as benzene, toluene and xylene; ketones such as acetone, methyl ethyl ketone and methyl isobutyl ketone; chloroform and Halogenated hydrocarbons such as methylene chloride; esters such as methyl acetate and ethyl acetate; or ethers such as tetrahydrofuran, dioxane, diethyl ether, and 1,2-dimethoxyethane; water; acetonitrile and N, N Examples thereof include polar solvents such as dimethylformamide, N-methyl-2-pyrrolidone, and dimethyl sulfoxide, or mixed solvents of the above solvents.

Bases include organic bases such as triethylamine, pyridine, 1,8-diazabicyclo [5.4.0] undec-7-ene (DBU), 4-dimethylaminopyridine; sodium hydroxide, potassium hydroxide, etc. Alkali metal hydroxides; alkaline earth metal hydroxides such as calcium hydroxide; alkali metal carbonates such as sodium carbonate and potassium carbonate; alkaline earth metal carbonates such as calcium carbonate; alkali metals such as sodium hydrogen carbonate Examples thereof include hydrogen carbonates; metal alkoxides such as sodium methoxide and potassium ethoxide; metal hydrides such as sodium hydride and potassium hydride.

The compound represented by the formula (4) or the compound represented by the formula (3) can be produced according to the method described in Patent Document 1.

Reaction formula 3

[Wherein R ² , R ³ , V, W, X, Y, Z ¹ , Z ² , n ¹ and n ² are as defined in the above formula (1)]

(1 ′) and (5) (wherein R ⁶ is a C _1-12 alkyl group, a C _1-6 haloalkyl group, a C _3-6 alkenyl, a C _3-6 haloalkenyl, a C _3-6 alkynyl group, C _3-6 haloalkynyl group, C _3-8 cycloalkyl group, C _3-8 halocycloalkyl group, C _3-8 cycloalkyl-C _1-6 alkyl group, C _1-6 alkoxy C _1-6 alkyl group C _1-6 alkylcarbonyl group, C _1-6 haloalkylcarbonyl group, C _1-6 alkoxycarbonyl group, C _1-6 haloalkoxycarbonyl group, C _1-6 alkoxy C _1-6 alkylcarbonyl group, C _{1- 6 represents} an alkylsulfonyl group, a C _1-6 haloalkylsulfonyl group, or a cyano group.) The reaction to obtain (1 ″) from can be performed in the presence of a solvent and a base.

Reaction formula 4

From (6) and (2), the reaction to obtain (7) can be carried out in the presence or absence of a solvent and a base.

From (7) and (8), the reaction to obtain (1) can be carried out in the presence of a solvent and a base.

Although the typical compound represented by the said Formula (1) is illustrated in Table 1 thru | or Table 6, this invention is not limited to these.
The physical properties in the table indicate properties or melting points (° C.), “n-” is normal, “s-” is secondary, “t-” is tertiary, “i-” is “Me” represents a methyl group, “Et” represents an ethyl group, “Pr” represents a propyl group, “Bu” represents a butyl group, and “Hex” represents a hexyl group. In the group, “Ph” represents a phenyl group. In addition, “H” in the column of “(W) n ¹ ” or “(Y1) n ³ ” indicates that W or Y ¹ is a hydrogen atom, and “(Y1) n ³ ” The designation “5-CF3” in the column indicates that the 5-position of the pyridyl group is substituted with CF3, and others are similarly understood.

General formula (A) (In formula (1), X is H, Y is a (Y ¹ ) n ³ -pyridyloxy group at the 4-position, Z ¹ is O, and Z ² is O.)

(A)
R ³ = H, provided that the compound No. 12 shows the R ³ = Me.

General formula (B) (In formula (1), X represents H, Y represents a (Y ¹ ) n ³ -pyridyloxy group at the 2-position, Z ¹ represents O, and Z ² represents O.)

(B)
R ³ = H is shown.

Table 2

General formula (C) (In formula (1), X represents H, Y represents a (Y ¹ ) n ³ -pyridyloxy group at the ³ -position, Z ¹ represents O, and Z ² represents O.)

(C)
R ³ = H is shown.

Table 3

General formula (D) (In formula (1), X is H, Y is a (Y ¹ ) n ⁴ -phenoxy group at the 4-position, Z ¹ is O, and Z ² is O.)

(D)
R ³ = H is shown.

Table 4

General formula (E) (In formula (1), X represents H, Y represents a 5-trifluoromethylpyridyloxy group at the 4-position, Z ¹ represents O, and Z ² represents NR ⁶ )

(E)
R ³ = H is shown.

Table 5

General formula (F) (in formula (1), R ¹ and R ³ are H, R ² is Me, R ⁴ and R ⁵ are F, X is H, Y is 4-position, Z ¹ is O, Z ² is O is shown.)

(F)

Table 6

The agricultural and horticultural agent according to the present invention contains, as an active ingredient, at least one selected from the group consisting of the compound of formula (1) or an N-oxide or a salt thereof.
The amount of the active ingredient contained in the agricultural and horticultural agent of the present invention is preferably 0.01 to 90% by mass, more preferably 0.05 to 85% by mass, still more preferably 0.00%, based on the entire preparation. It is about 05 to 80% by mass.

Formulations comprising the compound of formula (1) of the present invention or an N-oxide or salt thereof as an active ingredient are one or more fungicides, insecticides, acaricides, repellents, synergists, or plant growth regulators. It can be mixed or used together with an agent. The mixture thus obtained has a broad activity spectrum.

Examples of bactericides (generic names) that can be mixed or used in combination with a preparation comprising the compound of formula (1) of the present invention or an N-oxide or salt thereof as an active ingredient are shown below. It is not limited to this.

Examples of bactericides that inhibit nucleic acid synthesis include, for example, benalaxyl, benalaxyl M, furalaxyl, metalaxyl, metalaxyl M, oxadixyl oxaxyl (Bupirimate), dimethylirimol, ethirimol, hydroxyisoxazole, hymexazole, octylinone, oxolinic acid and the like.

Bactericides that inhibit mitosis and cell division include, for example, benomyl, carbendazim, fuberidazole, thiabendazole, thiophanate, thiophanate methyl, and thiophanate methyl. ), Zoxamide, zaralamid, ethaboxam, pencycuron, fluopicolide and the like.

Examples of fungicides that inhibit respiration include diflumetorim, tolfenpyrad, tebufenpyrad, fenazaquin, pyridaben, fenpyroximate, fenpyroximate benodanil, flutolanil, mepronil, isofetamide, fluopyram, fenfuram, carboxin, oxycarboxin, oxycarboxin, oxycarboxin Thifluzamide, benzovindiflupyr, bixafen, flixapyroxad, furamethpyr, iopyrafen, p , Boscalid, pyraziflumide, pydiflumethofen, isoflucipram, azoxystrobin, coxoxystrobin, coxoxystrobin tropin, fluphenoxystrobin, picoxystrobin, pyroxystrobin, pyracrostrobin, pyramethostrobin, triclopyrmethyl kresoxim-methyl), trifloxystrobin, dimoxystrobin, phenaminestrobin, methminostrobin, orizastrobin, famoxadone, fluoxastrobin, fenamidone e), pyribencarb, cyazofamid, amisulbrom, binapacryl, meptyldinocap, dinosacap, dinocapap, dinocapap, dinocapap , Tebufloquin and the like.

Bactericides that inhibit amino acid and protein synthesis include, for example, andoprim, cyprodinil, mepanipyrim, pyrimethanil, blasticidin S, kasugamyctomomycin ), Oxytetracycline, mildiomycin and the like.

Bactericides that inhibit signal transduction include, for example, quinoxyfen, proquinazid, fenpiclonil, fludioxonil, clozolinate, iprodion, crodinone Is mentioned.

Bactericides that inhibit lipid and cell membrane synthesis include, for example, edifenphos, iprobenfos, pyrazophos, isoprothiolane, biphenyl, chloroneb, techtozane, Examples thereof include methyl (tolclofos-methyl), ecromezole, iodocarb, propamocarb, and prothiocarb.

Bactericides that inhibit cell membrane sterol biosynthesis include, for example, triforine, pyrifenox, pyrisoxazole, fenarimol, nuarimol, imazaril, oxpoconazole, oxpoconazole Pefurazoate, prochloraz, triflumizole, azaconazole, bitteranol, zylconol, ciproconazole, ciproconazole, ciproconazole diniconazole, epoxiconazole, etaconazole, fenbuconazole, fluquinconazole, fluconazole, flusilazole, flusilazole, flusilazole, flusilazole, flusilazole, flusilazole (fluconazole), fluconazole (fluconazole), fluconazole (fluconazole), fluconazole (fluconazole), fluconazole (fluconazole) flutriafol, hexaconazole, imibenconazole, ipconazole, metconazole, microbutanol, penconazole , Propiconazole, simeconazole, tebuconazole, tetraconazole, triadimolazole, triadimolazole (triadimolazole), triadimolazole (triadimolazole) , Uniconazole-P, butiobate, diclobutrazol, aldimorph, dodemorph, fenpropimorph, tridemorph (r) , Fenpropidin, piperalin, spiroxamine, fenhexamid, fenpyrazamine, florpyrafifenol, ifen Terbinafine and the like.

Bactericides that inhibit cell wall biosynthesis include, for example, validamycin, polyoxin, dimethomorph, flumorph, pyrimorph, bentiavalical, iprovalic, iproval, (Variiferate), mandipropamide, and the like.

Examples of bactericides that inhibit cell wall melanin synthesis include fthalide, pyroquilon, tricyclazole, carpropamide, diclocymet, phenoxanil and the like.

Examples of fungicides that induce resistance of host plants include, for example, probenazole, thiadinil, isothianil, laminarin, extract of mint gigantweolzol, and benzoic acid ol-Solben. -Methyl) and the like.

Examples of fungicides that inhibit the multi-acting point include copper (copper), DBEDC (complex of bis (ethylenediamine) copper-bis- (dodecylbenzenesulphonic acid)), cupric hydroxide (copper hydroxide), and nonylphenol sulfonic acid. nonylphenol sulfate, copper oxychloride, basic copper sulfate, organic copper, sulfur, sulfur, calcium sulfur, calcium sulfide DD (1,3-dichloropropene), Dazomet ( azomet, methyl bromide, methylisothiocyanate, carbam (manamzeb), manzeb, maneb, metyram, propineb, propineb Zinc sulfate, zineb, ziram, captan, captafol, holpet, chlorothalonil, dichlorfluid, tlufluid , Guazatine, imi Examples include kutadine acetate (iminoctaline acetate), iminotazine albecylate (iminoctadine-DBS), triazine (anilazine), dithianon, quinomethionate, fluorimide, and sene-stained stainless steel. .

Other fungicides include, for example, cymoxanil, fosetyl, phosphorous acid, phosphite, teclophthalam, triazoxide, flusulfamide (flusulfamide), flusulfamide (flusulfamide) dicolomezine, metasulfocarb, cyflufenamide, metraphenone, pyriophenone, dodine, fluthiain p, felimone p ), Torquerocarb (picolbutrazox), machine oil (petroleum oil), organic oil (organic oil), potassium hydrogencarbonate (carbonic acid), sodium hydrogen carbonate (sodium hydrogen) Sodium hypochlorite, calcium carbonate, benthiazole, diclobutrazol, flumetover, thiadiazin, loor di-tin in), shiitake mycelium extract, extract quinofumelin, quinoline compound described in WO 2011/081174 pamphlet, pyridazine compound described in WO 2005/121104 pamphlet, Examples thereof include a pyrazole compound described in the 2011/162397 pamphlet and a tetrazolinone compound described in the international publication 2013/162072 pamphlet.

Examples of the compound (generic name) having insecticidal activity, acaricidal activity or nematicidal activity that can be mixed or used in combination with a preparation comprising the compound of the formula (1) of the present invention or an N-oxide or salt thereof as an active ingredient are shown below. Although shown, the insecticide, acaricide or nematicide which can be mixed or used together is not necessarily limited thereto.

Examples of the organic phosphorus agent include acephate, azinephos-methyl, chlorpyrifos, diazinon, dichlorvos, dimethon-S-methyl (dimethon-S-methyl), Dimethylvinphos, disulfoton, ethion, fenitrothion, fenthion, isoxathion, malathion, methamidothio (methathidothio) ion), monocrotophos, nared, oxydeprofos, parathion, phensoate, fosalone, pirimiphos-methyl, feihion profenofos, prothiofos, propopafos, pyraclofos, salithion, sulprofos, thiomethon, tetrachlorvinphos (tetrochlorv) richlorphon), mention may be made of Bamidochin (vamidothion) and the like.

Examples of carbamate agents include alanicalcarb, bendiocarb, benfuracarb, carbaryl, carbofuran, carbosulfan, etiofencarb, ethofencarb. (Furathiocarb), isoprocarb, mesomyl, metolcarb, pirimicarb, propoxur, thiodicarb, and the like.

Examples of the organic chlorine agent include aldrin, chlordane, DDT (p, p'-DDT), endosulfan, lindane and the like.

Examples of pyrethroid agents include acrinathrin, allethrin, bifenthrin, cycloprothrin, cyfluthrin, cyhalothrin, cythothrin, cyphenthrin, and phenothrin. deltamethrin, etofenprox, fenpropathrin, fenvalerate, flucitrate, flufenprox, fulvalinate nate), furamethrin, halofenprox, imiprothrin, permethrin, phenothrin, fluretrin, pyrethrin, pyrethrin, pyrethrin, pyrethrin, pyrethrin. (Tefluthrin), tralomethrin, transfluthrin and the like.

Examples of neonicotinoids include acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, and thiaclopridum.

Examples of the diamide agent include chlorantraniprole, cyantraniprore, cyclaniliprore, tetraniliprole, and fulbenedia.

Examples of insect growth control agents such as benzoyl urea agents include bistrifluron, chlorofluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumulon ), Lufenuron, novaluron, noviflumuron, teflubenzuron, triflumuron, buprofezin, cyromazine (in), cyromazine (in), cyromazine, etc.

Examples of the phenylpyrazole agent include etiprole, fipronil, acetoprole, pyrafluoprol, pyriprole and the like.

Examples of nereistoxin agents include bensultap, cartap, thiocyclam, thiosultap, and the like.

Examples of the diacylhydrazone agent include chromafenozide, halofenozide, methoxyphenozide, tebufenozide and the like.

Examples of juvenile hormone agents include diophenolan, phenoxycarb, hydroprene, methoprene, and pyriproxyfen.

Examples of insecticidal substances produced by microorganisms include, for example, abamectin, emamectin benzoate, ivermectin, lepimectin, milbemectin, nemadectin and nemadectin. , Polyoxin complex (polyoxin), spinetram, spinosad, BT agent (Bacillus thuringiensis and insecticidal protein product) and the like.

Examples of insecticidal substances derived from natural products include anabasine, azadirachtin, deguelin, fatty acid glycerides, hydroxypropyl starch, soybean starch, and soybean. ), Nornicotine, sodium oleate (orecic acid sodium salt), machine oil (petrolium oil), propylene glycol monofatty acid ester (propylene glycol monolaurate), rape oil (rope oil), rotenone roten (on) Rubitan fatty acid esters (Sorbitan fattyacid ester), mention may be made of starch (starch) and the like.

Other insecticides include, for example, afidopyropen, brofuranilide, chlorfenapyr, diafenthiuron, didichloromezothiaz, dichromezothiaz, dichromezothiaz (Flonicamid), flometoquin, flufenerim, fluhexafone, flupyradifurone, hydramethylnon ), Indoxacarb, metaflumizone, metaldehyde, nicotine sulfate, pymetrozine, pyridalyl, spiridrofluidyl (Sulfuramid), sulfoxafluor, triflumezopyrim, tolfenpyrad, triazamate, and the like.

Examples of acaricides include acequinocyl, acinonapyr, amidoflumet, amitraz, azocyclotin, benzomate, benzomate, benzomate, benzomate. Bromopropyrate, quinomethionate, clofentezine, cienopyrafen, cyflumetofen, tricyclohexyltin hydroxide, diolformi Le (dienochlor), Jifurobidajin (diflovidazin), etoxazole (ethoxazole), Fenazafuroru (fenazaflor), fenazaquin (fenazaquin), fenbutatin oxide (fenbutatin oxide), fenothiocarb (fenothiocarb), fenpyroximate (fenpyroximate), fluacrypyrim (fluacrypyrim), hexythiazox (Hexythiazox ), Pyrimidifene, polynactin complex, propargite, piflubumide, pyridaben, spirodiclofen (spiro) iclofen), spiromesifen (spiromesifen), tebufenpyrad (tebufenpyrad), mention may be made of tetradifon (tetradifon) and the like.

As nematicides, for example, aluminum phosphide, benclothiaz, cadusafos, etoprofos, fluensulfone, fluopyram, fluopyram, fluopyram, fluopyram , Imiciafos, levamisole hydrochloride, mesulfenfos, methamfenfos, methyl isothiocyanate, mortar of tartaric acid e), oxamyl (oxamyl), thifluzamide (thifluzamide), mention may be made of Chiokisazafen (thioxazafen) and the like.

Examples of poison baits include chlorofacinone, coumatetralyl, diphacin, difluoroacetate, warfarin and the like.

The composition provided by the present invention can be used for prevention and extermination of harmful pests in agriculture, indoors, forests, livestock, sanitation, and other scenes. Specific use scenes, target pests, and usage methods are shown below, but the contents of the present invention are not limited to these.

The agricultural and horticultural pharmaceutical composition of the present invention includes agricultural crops such as food crops (rice, barley, wheat, rye, oats and other wheat, potatoes, sweet potatoes, taro, potatoes such as potatoes, soybeans, red beans, Beans such as broad beans, green beans, green beans, peanuts, corn, persimmons, buckwheat, etc., vegetables (cabbage, Chinese cabbage, radish, persimmon, broccoli, cauliflower, komatsuna), cruciferous crops, pumpkin, cucumber, watermelon, mama Cucumber, melon, zucchini, cucumber, cucumber, cucumber, aubergine, eggplant, tomato, pepper, red pepper, mushrooms, mushrooms, mushrooms, spinach, red pepper, etc. Carrot, Mitsuba, Parsley, Celery, Udon and other cereals, lettuce, burdock and other asteraceae, garlic, onion, green onions, leeks Green onions, asparagus, shiso, lotus root, etc.), mushrooms (shiitake, mushrooms, etc.), fruit trees / fruits (citrus, apple, pear, peach, plum, cherry peach, Yi, apricot, persimmon, persimmon, persimmon, no flower fruit) , Akebono, Blueberry, Raspberry, Pineapple, Mango, Kiwifruit, Banana, Strawberry, Olive, Walnut, Chestnut, Almond, etc.) Fragrance and other ornamental crops (lavender, rosemary, thyme, sage, pepper, ginger, etc.), special Crops (tobacco, tea, sugar beets, sugar cane, igusa, sesame, konjac, hops, cotton, hemp, olives, rubber, coffee, rapeseed, sunflower, mulberry, etc.), crops for pasture and feed (timothy, clover, alfalfa, etc.) Legume grass, corn, sorghum, orchard grass, etc.), turf (Korean turf, bentgrass, etc.), forest (Todomatsu, Ezomatsu, pine, hiba, cedar, camellia, etc.) and ornamental plants (kiku, rose, carnation, lily, eustoma, perennial haze, starchy, orchid, herbs, sakura, etc. , Garden trees such as Aoki, etc.).

The pests targeted by the agricultural and horticultural pharmaceutical composition of the present invention include fungi such as Mycota, Myxomycota, Bacteriomycota, Actinomycota, and the like. And can be used to control the diseases they cause.

Specific examples of diseases include rice blast (Piculararia oryzae), sesame leaf blight (Cochliobolus miyabeanus), blight (Rhizoctonia solani), brown rot (Panteoanaanatis), idiophyllia eu Seedling blight (Pythium graminicum), Brown streak (Acidovorax avene subsp. Avenae), Leaf sheath browning (Pseudomonas fuscovaginae), Bacterial blight (Xanthomonas oryzae v. Reezae p.) Of powdery mildew (Erysiphe graminis), red mold (Gi) berella zeae), red rust (Puccinia striformis, P. graminis, P. recondita, P. hordei), snow rot (Typhula sp., Micronella nivalis), black scab (U. (Tilletia caries), eye spot disease (Pseudocercosporella herpotrichoides), cloud disease (Rhynhosporum secoris), leaf blight (Septoria territory disease) tum Ikata), black spot disease (Pseudomonas syringae pv. japonica), etc .; citrus black spot disease (Diaporthe citria), common scab (Elsinoe fawceti), brown rot (Penicillium rot). citrophthora ,, P. nicotianae), black scab (Phyllostictina citricarpa), etc .; apple monilia disease, leaf spot (Diplocarpon mali), rot disease (Valsaco palli) Disease (Alternaria mary), Black Star Disease (Venturia inaequalis), black spot disease (Mycospherella poma), anthracnose disease (Colletotrichum acutatum), Glomerella singumata, red leaf disease (Botryosphaeria verumeria) (Gloodes pomigena) et al .; Venturia nashicola, V. pirina), powdery mildew (Phyllactinia mary), black spot disease (Alternaria kikuchiana), erythematosis (Gimnosporium haraenum), erythema disease (monilia fructigena) Monilinia fracticola, anthrax (Glomerella cingula), larvae of larvae (Monilinia fukuticola), black scab (Cladosporium carposis) Disease (Xanthomonas camp) estris pv. pruni) et al; Grapes black rot (Elsinoe ampelina), late rot (Colletotrichum acutatum), Glomerella cinulata, powdery mildew (Uncinula necator), rust pso , Downy mildew (Plasmopara viticola),
Black star disease (Cladosporium viticolum), basidiomycete bacterial disease (Agrobacterium vitis), etc .; oyster anthracnose (Gloeosporium kakicola), powdery mildew (Phyllactinia kakicola), deciduous leaf disease (Cercosporicus kakicola) Horn spot disease (Phomopsis sp.), Anthracnose (Colletotrichum gloeosporioids), white leaf blight (Rosellinia necatoroid erystocerosis) Anthracnose (Colletotrichum lagenariaum), powdery mildew (Sphaerotheca furiginea, Oidiopis tourica), vine blight (Didymella bursonia), vine split (Fusarium oxyspor) Seedling blight (Pythium sp., Rhizoctonia solani), etc .; Cucumber spotted bacterial disease (Pseudomonas syringae pv. Lochrymansburithampis cirva citrus var.) Melon brown spot bacterial disease (Xanthomonas campestris pv. Cucurbitae), hairy root disease (Agrobacterium rhizogens), scab (Septopmyces sp.), Etc .; Leaf blight of eggplants (Ralstonia solanacerum), etc .; Ringworm disease of tomato (Alternaria solani), leaf mold (Cladosporium fulvum), plague (Phytophthoraphestrus), smolder disease (Pseudorc disease) cichoracerum), scab (Clavibac) ter michiganense subsp. michiganense), stem rot (Pseudomonas corrugata), soft rot (Pectobacterium carotoiorum subs). Blight (Corynespora melongenae), brown rot (Paracercospora genula), brown rot (Phytophthora capsici), half body wilt (Verticillium dahliae), etc .; . Rnaria japonica), white spot disease (Cercosporella brassicae) soft rot (Pectobacterium carotovorum subsp carotovorum), Kikabyo (Verticillium dahliae) and the like;.. Cabbage Rot (Pseudomonas syringae pv marginalis), black rot (Xanthomonas campestris pv campestris Lettuce downy mildew (Rhizoctonia solani), rot disease (Pseudomonas viridiflava), spot bacterial disease (Xantampon rastropon. vitians, leek downy mildew (Peronospora destructor), black spot disease (Alternaria porri), rust disease (Puccinia allii), white silkworm (Sclerotium rulfsii), etc .; Colletotrichum truncatum, Colletotrichum trifolii, Glomerella glycines, Gloeosporium sp.),
Downy mildew (Peronospora manshurica), stem rot (Phytophthora sojae), black scab (Elsinoes glycines), black spot (Diaporthea esoleum var. Sojae), spotted bacterial disease (spot bacteria) pv. glycines) et al; Colletotrichum lindemthianum, Pseudomonas savastanoli pv. phasolicols leaf, Xanthomonas campesh i) and the like; Cercospora personata, Brown spot disease (Cercospora arachidicola) and the like; Peasy mildew (Erysiphe pisi) and the like; Blast of summer plague (Alternaria insola ), Leaf rot fungus (Rhizoctonia solani), soft rot (Pectobacterium carotovorum subb. Carrotorumum), strawberry powdery mildew (Sphaerothecium umuli), anthrax Phytophthora nicotianae, Dendroboma obscurans, Bacterial blight (Pseudomonas marginalis pv. Marginalis), etc .; Brown brown streak of tea (Pseudocercosporathee's disease, Pseudocercosporathee's disease) theae, Pestaliopsis longiseta, net blast (Exobasidium reticulatum), rice blast (Exobasidium vexans), white scab (Elsinoe leucospila), red burning (Pseudomonas sapiens. theae, scab (Xanthomonas campestris pv. theicola), etc .; tobacco red rot (Alternaria longipes), powdery mildew (Erysiphaticobacter's disease) Nicotianae, Blight disease (Ralstonia solaacearum), Cavity disease (Pectobacterium carotovorum subsp. carotovorum) and the like; Cercospora beticola, root rot (Rhiston rot) meris), seedling blight (Aphanomyces cochliodes), etc .; rose black spot (Diplocarpon rosae), powdery mildew (Sphaerotheca pannosa), etc .; Agrobacterium tumefaciens, etc .; Gray mold disease of various crops such as eggplant, cucumber and lettuce; Botrytis cinerotiarum; Sclerotinia sclerotiorum; incarnate, Fusarium nivale, Sclerotinia boreali ), Powdery mildew (Erysiphe graminis), Faringling disease (Lycoperdon perlatum, Lepista subnudo, Marasumius oreades), pseudoleaf rot (Ceratobasidium spp.), Blight disease , Leaf rot (Rhizoctonia solani), Pysium disease (Phythium periplocum, Pythium vanterpoolii), rust disease (Puccinia spp.), Dollar spot disease (Sclerotinia humamorp) Disease (Colletotrichum sp. ), Acacia shark skin blight (Botryosphaeria sp.), Anthracnose (Glomerella singulata), Hydrangea ring rot (Phoma exigua), Spot disease (Phylosticta hydrangeaoresae), Brown leaf Rot disease (Rhizoctonia solani), powdery mildew (Oidium sp.), Anthrax (Glomerella singulata), ring rot (Cercospora hydrangaleum), red scab (Gonatobotrumum erythrum) Gnosporangium yamadae, white crest feather disease Rosellinia necatrix), maple such chromone disease (Rhytisma acerinum), ring Sheath blight (Cristulariella moricola),
Blight disease (Diaporthe sp.), Subtilis spot disease (Cercospora sp.), Anthracnose disease (Colletotrichum gleosporioids), Red rot disease (Erythricium salmon. Sp.), Powdery mildew (Uncinula sp.). , White spot disease (Phomatospora albomaculans), powdery mildew (Uncinula sp., Microsphaera alphitoides), Erysiphe gracilis, Armillariamellius disease Spot disease (Septoria chinensis), blight (D aporthe melanocarpa, Diaporthe alleghaniensis), Kusunoki of anthracnose (Glomerella cingulata), gardenia of Susukabi disease (Passalora okinawaensis), leaf spot (Phaeosphaerella gardeniae), brown spot disease of Zelkova (Pseudocercospora zelkovae), if bamboo disease (Armillaria mellea) , Fistula powdery mildew (Phyllactinia magnoliae), spotted disease (Phyllostica concentrica), cherry blossoms (Nectria galligigena), root cancer (Agrobacterium disease) Odosphaera longiseta, Posphaera triactyla), Tenchuria wiesneri, larvae nuclear disease (Monilinia kasanoi), scab (Armilaria mellea), bacilli , Salicaria powdery mildew (Uncinuliella australiana), brown spot (Pseudocercospora lythracealum), ring-leaf blight (Cristulareella morocola) -Macula s), leaves blisters disease (Taphrina kusanoi), rhododendron such anthracnose (Colletotrichum gloeosporioides), Hamadarabyo (Pseudocercospora handelii), Shiromon rot (Rosellinia necatrix), too much of the branches 枯菌 nuclear disease (Sclerotium sp. ), Red blight (Cercospora sequoiae), microphage nuclear disease (Macrophopha phaseolina), red leaf blight (Ascochyta sp.), Azalea powdery mildew (Microsphaera izuensis), brown spot disease (S) , White leaf blight (Rosellinia necatrix), seedling blight (Rhizoctonia solani), leaf spot (Pseudocercospora handelii), spot disease (Phylostatica maxima), flower rot fungus nuclei ), Tsubaki root rot (Phytophthora cinnamomi), Anthracnose (Glome) ella cingula, mushroom symptom (Armillariella mellea), rose powdery mildew (Sphaerotheca pannosa, Oidium sp.), downy mildew (Peronospora spasa), spot disease (Cerocosor sero) megasperma), black scab (Marssonina rosae, Diplocarpon rosae), rot (Cryptosporella umbrina), white rot (Rosellinia necatria), cypress mushroom (Armilillo tilapia) s sp.), Erwinia herbicola pv. milletiae, poinsettia root rot (Rythium sp.), bedworm plague (Phytophathora cactorum), powdery mildew (Erysiperot disease) ), Anthracnose (Gloeosporium sp.), Brown spot (Pseudocercospora variicolor), mycorrhizal disease (Sclerotinia sclerotiorum), blight (Botrytis paeoniae), white rot (Resellid) euonymi-japonici), brown spot (Pseudocercospora destr) ctiva), pine of kelp disease (Cronartium quercuum), seedling blight (Rhizoctonia solani, Fusarium sp. , Phythium sp ,,), leaf blight (Pseudocercospora pini-densiflorae), brilliant backspot disease (Coccoidea querricola), citrus powdery mildew (Microsphaera pulch, or octo) Marsonaina brunnea, eucalyptus horn spot disease (Cercospora epicoccoids), snowy spruce symptom (Pseudocercospora spiraepica), powdery mildew (Sphaerosera spruce) Withering Nuclear disease (Sclerotinia sclerotiorum), Asagao vine split disease (Fusarium oxysporum f. Sp. Batatas), carnation powdery mildew (Oidium dianthi), gerbera powdery mildew (Sphaerothecium fouling) Sclerotinia sclerotiorum, Fusarium oxysporum, powdery mildew (Erysiphe cichoracerum), Sclerotiria sclerotium (Vertihilus lily) Goldfish grass anthracnose ( Colletotrichum gloeosporioides), powdery mildew (Oidium subgenus Reticuloidium), sclerotinia rot (Sclerotinia sclerotiorum), and cosmos of anthracnose (Colletotrichum acutatum, Gloeosporium sp.), Powdery mildew (Sphaerotheca fusca), sclerotinia rot (Sclerotinia sclerotiorum), and Periwinkle powdery mildew (Oidium sp.), Fusarium moniliforme, mycorrhizal disease (Sclerotinia sclerotiorum), sweet pea powdery mildew (Oidium sp.), Wilt disease (Fusarium sp.) ), Verticillium dahliae, Glomerella singulata, Colletotrichum gleosporioids, Glomerella singulata, powdery mildew (Oidium spider). sp. m dahliae), Eustoma anthracnose (Colletotrichum acutatum),
Stem rot (Fusarium avenaceum), powdery mildew (Oidium sp.), Mycorrhizal disease (Sclerotinia sclerotiorum), sunflower powdery mildew (Sphaerotheca fusca leaf disease, Erysiphe cicoracero spleen) Septoria helianthii), Verticillium dahliae, Petunia powdery mildew (Sphaerotheca fuligena, Oidium sp.), Sclerotia sclerotia gold, and sclerotia sclerotirum. .

Examples of pests include Lepidoptera, Coleoptera, Hemoptera, Hemoptera, Thomoptera, and Thysanoptera (Hymenoptera), fly order (Diptera), grasshopper order (Orthooptera), termite order (Isoptera), earworm (Dermaptera), Arthropoda side insect class Collembola, Arthropoda crustacea, etc. Legs (Isopada), Arthropoda spider mite (Acari), Mollusc antiogastropod primitive string tongue (Architaenioglossa), Linear animal genus genus Tyrenx (T lenchida), mention may be made of the Doriraimusu eyes, etc. of the tail gland rope. Although the specific example of these pests is shown below, a pest is not limited to these.

Examples of the Lepidoptera of the Arthropoda elegans include Lepidoptera (Helicoverpa armigera), Heliothis spp., Agrotis segetum, and Managinographia. ), Yeoga (Mamestra brassicae), Shirochimodojiyoto (Spodoptera exigua), Spodoptera atracha saga (Plutella xylostella), and the like Echinaceae (Adoxophyes honmai), Midarekae Umumakigi (Archips fusucupureanus), Chamonaki (Homona magnima) et al. (Lyonettia prunifoliella marinella), peach leaf moth (Lyonetia clarkella), and the like, Phyllocnistis citella, etc. ella), etc., etc. Negikoga of Atohigekoga Department (Acrolepiopsis sapporensis), etc. Kosukashiba of sesiidae (Synanthedon quercus), etc. Kakinohetamushiga of Nisemaikoga Department (Stathmopoda masinissa), pink bollworm of Kibaga Department (Pectinophora gossypiella), etc., Shinkuiga Department of peach fruit moth (Carposina Niponensis, etc., Iraga family Iraga (Monema flavcens), Hilohelia Oiraga (Parasa lepida), Shimerodera Contracus, etc., Chiro suprassalis Sanga a incertulas), leaf roller (Cnaphalocrocis medinalis), high Madara Roh moth (Hellulla undalis), peach Gore-moth (Conogethes punctiferlis), cotton helicopter Chrono moth (Diaphania indica), Shibatsutoga (Parapediasia teterrella), etc., of Seserichou family parnara guttata (Parnara guttata) , Swallowtail butterflies (Papilio xuthus), white butterflies (Pieris rapae crucivora), lycaenidae (Lampides boeticus), etc. sselenaria), Suzumidae shrimp glass sparrow (Agrius convolvuli), etc., Orchardaceae, Palera flavescens, etc., Physocera spp. , Such as Spirosoma imparilis, Hyphantria cunea, Grapeberry moss (Endopizia viteana), Kodlinga (Lasperesia pomonella), etc.

Coleoptera, for example, Anomala cupurea, Populus japonica, Oxycetonia jucunda, Akamula genus, etc. , Memanotus fortumi, etc., Epilachna vigintioctopuncta, etc., Anomalophalis, Anopalophora rrhoderus, potato beetle (Alacophora femoralis), rootworm species (Diabrotica spp.), killer whale beetle (Phylotretta striola), beetle potato beetle (Cassida nebulosa). Epilachna varivestis, Colorado potato beetle (Leptinotarsa decemlineata), etc., Rhychites heros, etc., Rhichinites weevil, Arimodokisushi, (Cylassoridae, Cyrassidae, etc.) Chrysanthemum weevil (Curculio sikkimensis), rice weevil (Lysorhoptrus oryzophylus), cotton weevil (Anthonomus gradis grandis), Shibaus weevil Can be mentioned.

Examples of Hemoptera Heteroptera include, for example, Eurydema rugosum, Eysarcoris lewisi, Esarsarvous, Eysarvoris Stink bugs (Platia stali), Ragwort bugs (Harymorpha mista), Relative bugs (Urochela luteovoria), Rabbit bugs, Rabbitaceae (River) , Hosoharika Mussel (Cletus puntigger), etc., Leptocorisa chinensis, etc .; Streptomyceae (Apolygus spinolai), Akajikasumi turtle (Stenothus rubrovittalus), Trichonotylus coelestialium, etc .; Insects, larvae and eggs, and the like can be given.

Examples of Homoptera are Homoptera, such as Platypleura kaempferi, Arboridia apicoli, and N. cerevisiae. , Nephotettix virescens, etc., Lamindelfax striatellus, Japanese green planta (Nilaparvata lugens), White-spotted planta (Sokatella furomofera) nctissima) and other species, Psylla pyrisuga, various citrus leafworms (Diaphorina citrii), and other species such as Bifolia citrus species. Citrus whitefly (Dialeurodes citri), Onitsu whitefly (Trialeurodes vapariorirum), etc., phyllocera family grape aphids (Viteus vitifoliii), etc., Aphidaceae Yuukiyanagiburamushi (Aicalis aphid) craccivora), cotton aphid (Aphis gossypii), potato aphid (Aulacorthum solani), radish aphid (Brevicoryne brassicae), Komi can aphid (Toxoptera aurantii), mandarin orange black aphid (Toxoptera citricidus), elder aphid (Aulacorthum magnoliae), pear Aphids (Schizophis piricola), Nasimidori aphids (Nippolachnus piri), Nisedaikon aphids (Liphaphis erysimi), Momokotera prune, Chrysanthemum kebabs Ramushi (Pleotrichophorus chrysanthemi), chrysanthemum Princess aphid (Macrosiphoniella sanborni), broad bean aphid (Megoura crassicauda), thorns aphid (Sitobion ibarae), tulip aphid (Macrosiphum euphorbiae), instead Cobb aphid (Myzus varians), green peach aphid ( Myzus persicae, Red-footed aphid (Rhopalosiph rubiabdominalis), Rhizobium aphid (Rhopalosiphum padi), Rhizobium aphid (Sitobion akebi) e), apple rotifer (Eriosoma lanigerum), etc., Iceria purchasi, etc. ), Etc., Ceraplastes ceriferus, Ruby worms (Ceroplasts rubens), etc., Aonidiella aurantii, Compostocapsis , White peach scale (Pseudaulacaspis pentagoa), Unaspis yanonensis (Unaspis yanonensis) adult like, can be cited larvae and eggs, and the like.

Thysanoptera (Thysanoptera) and to, for example, yellow tea thrips thrips family (Scirtothrips dorsalis), southern thrips (Thrips palmi), green onion thrips (Thrips tabaci), soybean mouse thrips (Thrips setosus), Hirazuhanaazamiuma (Frankliniella intonsa), mandarin orange Yellow thrips (Frankliniella occidentalis), Croton thrips (Heliotrips haemorrhoidalis), etc., Phyto thrips (Ponticothrips diospyropis) culeatus) adult, etc., it can be mentioned the larvae and eggs and the like.

Examples of bees (Hymenoptera) include, for example, the bee of the waspaceae (Athalia rosae ruficornis), the horn bee (Arge pagana), and the like. Examples include adults, larvae, eggs, and the like, such as Megachile nipponica nipponica, and other ants of the ant family, Formica japonica.

Examples of the flies (Diptera) include, for example, the soybean flies of the family Frostaceae (Asphondylia yushimai), the fruit flies of the family Frogidae (Rhacochlaena japonica), the flies of the fruit flies (Bactrocera ciraceae). Drosophila suzukii, etc., Limemya trifolii, etc., and Nabae Department of seedcorn maggot (Delia platura), onion maggot (Delia antiqua) adults such as, mention may be made of the larvae and eggs and the like.

Examples of orthoptera include, for example, the grasshopper (Rusporia lineosa) of the family Krygiriidae, the pine weevil (Truljalia hibinonis), etc., the moth of the family Kela (Glylottalpa orientis), etc. Examples include larvae and eggs.

Examples of the termites (Isoptera) include adults, larvae and eggs, such as the termite family Odontotermes formosanus.

Examples of the order Dermaptera include adults, larvae, eggs, and the like, such as Labidaura riparia.

Examples of Collembola of the Arthropoda side insect class include adults such as larvae such as Stomthulus viridis, pine moth, and larvae such as Onchiurus matsusumotoi.

Examples of the isopoda of the arthropod phylum Crustacea include adults, larvae, eggs and the like, such as Armadillium vulgare of the family Gillidae.

Examples of the mites of the arthropod arachnid (Acari) include, for example, the mite mites (Polyphagotaronemus latus), the cyclamen mite mite (Phytonemus pallidus), the mite mites (Penthaleus mahida), Brevipalpus lewisi, Brewipalpus phoenicis, etc., Mite spider mite spider mite spider mite spider mite spider mite spider mite spider mite spider mite spider mite spider mite spider mite spider mite spider mite spider mite spider mite spider mite spider mite spider mite spider mite spider mite spider mite spider mite spider mite spider mite spider mite spider mite spider mite spider mite spider mite spider mite spider mite spider mite spider mite spider mite spider mite spider mite spider mite spider mite spider mite spider mite spider mite spider mite spider mite spider mite sp (Ac (Ponyychus ulmi)), spider mite spider mite mite (Tonychuus tunawite tick) viennensis), tomato pine spider mite (Eligonychus ununguis), Etotranychus kankitus, clover spider mite (Bryobia praeosa), etc. Grape ticks (Colomerus vitis), moss mite (Aculus fockeii), chanosabi mite (Calacarus carinatus), and the like, Tyraphagus putrescentiae, Robinne tick (Rhizogiri) us robini) adults such as, mention may be made of the larvae and eggs and the like.

For example, the archaeenioglossa of the mollusc anterogastronomy, for example, Pomacea canalicula, such as the mosquito family, such as Plumonata, for example, the Achatina falica of the family Amythidae, (Migiumium bilineatum), Niwako urchinaceae (Milax gagates), Aurora amphiidae (Lehmannina valentiana), Species sect.

Examples of the Tylenchidae of the linear genital genital class (Tylenchidae) include, for example, the Anguinaceae Imogusaresenchu (Ditylenchus destructor), the Tyrencorhynus pylaenus Pylenaceae, ), Nymphaea nematode (Pratylenchus coffeae), etc., Namila nechu (Helocotylenchus dihystera), etc., potato cyst nematode (Globodera rostochiensis), etc. gyne incognita), etc., it can be mentioned, such as the sum of the Kurikonema Department of nematodes (Criconema jaejuense), strawberries main nematode (Nothotylenchus acris), etc. of Anguina family, the affection blast Lee Death Department of strawberry nematode (Aphelecchoides fragarriae), etc., etc..

For example, the long-tailed nematode (Xifinema sp.) And the trichodols family Trichodorus sp.

The pharmaceutical composition for agricultural and horticultural use of the present invention is highly safe for crops and useful organisms, and has low toxicity to various organisms such as fish and warm-blooded animals.

The pharmaceutical composition for agricultural and horticultural use of the present invention is resistant to existing agents such as benzimidazole agents, dicarboximide agents, anilinopyrimidine agents, strobilurin agents, SDHI agents, and fluazinam agents. Excellent bactericidal activity against resistant bacteria.

The pharmaceutical composition for agricultural and horticultural use of the present invention can also be used for the prevention and treatment of diseases of organs such as the skin, digestive system and respiratory system of humans, livestock and pets.

Specific examples of pathogenic bacteria that cause disease include Trichophyton rubrum and Trichophyton mentagrophytes such as trichophytic fungi, Candida albicans such as Candida fungi, Aspergillus E. coli fungi such as Candida albicans, Gram negative bacteria such as Pseudomonas aeruginosa, Gram positive bacteria such as Staphylococcus aureus, and the like.

The compound represented by the formula (1) of the agricultural and horticultural agent of the present invention includes a compound having insecticidal activity, acaricidal activity or nematicidal activity in addition to a compound having fungicidal activity, and other active compounds other than these compounds. It can also be present as a mixture. In order to control diseases and / or weeds that occur at the same time of use, it can be used in combination with a compound having fungicidal activity, herbicidal activity, or plant growth regulating activity, thereby reducing the control effort and reducing the dosage. Synergistic effects can be expected. Moreover, more effective control effects, such as a synergistic effect, can be expected by using a mixture with a repellent or a synergist.

The agricultural and horticultural chemicals of the present invention can be used as they are or in general as a pesticide. It can be used in dosage forms such as flowable agents such as agents, capsules, powders, granules, fine granules, baits, tablets, sprays, fumes, aerosols and the like. The agricultural and horticultural medicine of the present invention contains 0.1 to 99.9% by mass, preferably 0.2 to 80% by mass of the active ingredients in total.

In order to obtain the above dosage form, various agricultural chemical adjuvants conventionally used in the technical field of agricultural and horticultural medicine can be used as appropriate. Such agrochemical adjuvants can be used for the purpose of, for example, improving the effects, stabilizing, and improving dispersibility of agricultural and horticultural chemicals. Examples of the agricultural chemical adjuvant include a carrier (diluent), a spreading agent, an emulsifier, a wetting agent, a dispersing agent, a disintegrating agent, and the like.

Liquid carriers include water, aromatic hydrocarbons such as toluene and xylene, alcohols such as methanol, butanol and glycol, ketones such as acetone, amides such as dimethylformamide, sulfoxides such as dimethyl sulfoxide, methyl Mention may be made of naphthalene, cyclohexane, animal and vegetable oils, fatty acids and the like. As the solid carrier, clay, kaolin, talc, diatomaceous earth, silica, calcium carbonate, montmorillonite, bentonite, feldspar, quartz, alumina, sawdust, nitrocellulose, starch, gum arabic and the like can be used.

As the emulsifier and the dispersant, a normal surfactant can be used. For example, anionic surfactants such as higher alcohol sodium sulfate, stearyltrimethylammonium chloride, polyoxyethylene alkylphenyl ether, lauryl betaine, etc. Cationic surfactants, nonionic surfactants, amphoteric surfactants, and the like can be used. Further, spreading agents; wetting agents such as dialkyl sulfosuccinate; fixing agents such as carboxymethyl cellulose and polyvinyl alcohol; disintegrating agents such as sodium lignin sulfonate and sodium lauryl sulfate can be used.

In order to control pests such as fungi, in addition to spraying on the foliage of plants in areas where damage by these pests is or is likely to occur, soil All layers mixed, cropping application, side strip application, floor soil mixing, cell seedling treatment, planting hole treatment, plant root treatment, top dress, rice box treatment, water surface treatment, etc. Can also be used. It can also be used by soaking seeds in chemicals, seed dressing, seed treatment such as calper treatment, application to nutrient solution in nutrient solution (hydroponic) cultivation, smoke, or trunk injection.

When used, it varies depending on the type and amount of pests and the target crop / tree type, cultivation form and growth state, but generally 0.01 to 1000 g in total amount per 10 ares, preferably 0 Apply 1 to 100 g. In order to treat this, dilute with water in wettable powder, granule wettable powder, dry flowable powder, aqueous solvent, emulsion, liquid agent, flowable agent such as aqueous suspension and aqueous emulsion, capsules, etc. Generally, it may be sprayed on crops and the like at a rate of 10 to 1000 liters per 10 ares, although it varies depending on the type of plant, cultivation form and growth state. Moreover, what is necessary is just to process to a crop etc. in the state of the formulation in a powder agent, a spray agent, or an aerosol agent.

When the target pest primarily harms plants in the soil or when the drug is absorbed from the roots to control the target pest, for example, the preparation is diluted or diluted with water. Without applying to plant stock or seedling nursery, etc., spraying granules to plant seedling or seedling nursery, etc., before sowing or transplanting, powder, wettable powder, granule Method of spraying wettable powder, granule, etc. and mixing with the whole soil, before sowing or planting plant, powder, wettable powder, wettable granule powder, fine powder, fine powder on planting holes, crops etc. And the like. For wettable powders, granular wettable powders, aqueous solvents, emulsions, liquids, flowables such as aqueous suspensions and emulsions, dilute with water, generally 5 to 500 liters per 10 ares Then, it may be sprayed on the soil surface or irrigated into the soil so as to be uniform over the entire area to be treated. Powders, granules, fine granules, baits and the like may be sprayed on the soil surface so that they are evenly distributed over the entire area to be treated. Spraying or irrigation may be around the seeds, crops or trees that you want to protect from harm. Further, the active ingredient can be mechanically dispersed by tilling during or after spraying. When processing on soil, the total amount of active ingredients per 10 ares is generally 0.01, although it varies depending on the type and amount of pests and the target crop / tree type, cultivation form / growth state or soil type. -1000 g, preferably 0.1-500 g are applied.

The method of application to the seedling box of paddy rice may vary depending on the application time such as application at seeding, application at the greening period, application at the time of transplantation, etc.For example, powder, granule wettable powder, granules, fine granules etc. The wettable powder, granular wettable powder, aqueous solvent, emulsion, liquid, flowable preparation such as aqueous suspension and aqueous emulsion, capsules and the like may be used after diluted with water. It can also be applied by mixing with cultivated soil, and can be mixed with cultivated soil and powder or granules, for example, mixed with floor soil, mixed with cover soil, mixed into the entire cultivated soil, and the like. Alternatively, the culture medium and various preparations may be applied alternately in layers.

As application methods to paddy fields, solid preparations such as jumbo agents, pack agents, granules, granule wettable powders, and liquid preparations such as flowables and emulsions are usually sprayed on flooded paddy fields. In addition, at the time of rice planting, an appropriate preparation can be sprayed and injected into the soil as it is or mixed with fertilizer. In addition, by using chemicals such as wettable powder, emulsion, flowable, etc. as the source of water flowing into the paddy field such as a water mouth or an irrigation device, it can be applied labor-saving along with the supply of water.

Seed treatment methods include, for example, a method in which a liquid or solid preparation is diluted or undiluted to immerse the seed in a liquid state to attach and permeate the drug, a solid preparation or liquid preparation is mixed with the seed, Examples thereof include a method of dressing and adhering to the surface of the seed, a method of coating the seed by mixing with an adhesive carrier such as resin and polymer, and a method of spraying around the seed simultaneously with planting. The “seed” for performing the seed treatment means a plant body at an early stage of cultivation used for plant propagation. For example, in addition to seeds, nutrition for bulbs, tubers, seed buds, buds, baskets, bulbs or cuttings cultivation Mention may be made of plants for breeding. In addition, the “soil” or “cultivation carrier” of a plant when applied refers to a support for cultivating crops, particularly a support for growing roots, and the material is not particularly limited. Any material can be used as long as it can grow, so-called soil, seedling mat, water, etc. Specific materials include, for example, sand, pumice, vermiculite, diatomaceous earth, agar, gel material, polymer material, rock Examples include wool, glass wool, wood chips, and bark. When used, the total amount of active ingredients per kilogram of seed is 0.001 to 50 g, preferably 0.01 to 10 g.

As the seeding of the cultivated plant to be transplanted and the treatment of the seedling raising period, in addition to the direct treatment to the seed, the irrigation treatment of the liquid drug or the granule spraying treatment to the seedling nursery is preferable. In addition, it is also preferable to treat the granule in the planting hole at the time of planting or to mix it with the cultivation carrier in the vicinity of the transplantation site.

The agricultural and horticultural pharmaceutical composition of the present invention is intended to prevent and treat the occurrence and spread of diseases of organs such as the skin, digestive system and respiratory system that are parasitic on the body surface of humans, livestock and pets, or in the body. Can be used. In such a situation, the compound of the present invention is mixed in a small meal or feed, a suitable pharmaceutical composition that can be taken orally, such as tablets, pills containing pharmaceutically acceptable carriers and coating substances, Capsules, pastes, gels, beverages, medicinal feeds, medicinal drinking water, medicinal supplements, sustained-release large pills, other sustained-release devices designed to be retained in the gastrointestinal tract, sprays, powders, It can be administered transdermally as grease, cream, ointment, emulsion, lotion, spot-on, pour-on, shampoo and the like. In order to achieve the effect by such a method, generally 0.0001 to 0.1%, preferably 0.001 to 0.01% by weight is contained as a total amount of the active ingredient compounds.

Hereinafter, the present invention will be further described in detail with reference to Examples, Formulation Examples and Test Examples, but the scope of the present invention is not limited by these Examples, Formulation Examples and Test Examples.

Example 1.
Synthesis of (R) -2- [4-[[5- (trifluoromethyl) -2-pyridyl] oxy] phenoxy] -N-[(4-heptafluoroisopropyl) phenyl] propanamide (Compound No. 5) (Reaction Formula 1)
A solution of 261 mg (4-heptafluoroisopropyl) aniline, 327 mg (R) -2- [4-[[5- (trifluoromethyl) -2-pyridyl] oxy] phenoxy] propionic acid and 0.42 ml triethylamine in 10 ml tetrahydrofuran To the mixture, 260 mg of 2-chloro-1-methylpyridinium iodide was added little by little, and the mixture was stirred overnight at room temperature. The reaction mixture was poured into water and extracted with ethyl acetate. After washing with water and drying, the residue was purified by silica gel column chromatography (hexane: ethyl acetate = 3: 1) to obtain 420 mg (oil) of the compound shown in Table 1 (No. 5).
1H-NMR (CDCl3), δppm: 1.68 (3H, d), 4.79 (1H, q), 7.03 (2H, d), 7.13 (2H, d), 7.58 (2H, d), 7.73 (2H, d) , 7.90 (1H, dd), 8.36 (1H, bs), 8.42 (1H, s)

Example 2
(R) -2- [4-[[5- (Trifluoromethyl) -2-pyridyl] oxy] phenoxy] -N-[(2-chloro-4-heptafluoroisopropyl-6-methyl) phenyl] propane Synthesis of Amide (Compound No. 43) (Reaction Scheme 2)
To a solution of 48 ml of (2-chloro-4-heptafluoroisopropyl-6-methyl) aniline in 2 ml of N-methyl-2-pyrrolidone, (R) -2- [4-[[5- (trifluoromethyl)- 2-Pyridyl] oxy] phenoxy] propionyl chloride 430 mg was added little by little and stirred at room temperature for 2 hours. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (hexane: ethyl acetate = 3: 1) to obtain 700 mg (solid) of the target compound (No. 43) described in Table 1. The melting point of the obtained compound was 90-100 ° C.
1H-NMR (CDCl3), δppm: 1.76 (3H, d), 2.30 (3H, s), 4.87 (1H, q), 7.02 (1H, d), 7.07 (2H, d), 7.13 (2H, d) , 7.39 (1H, s), 7.52 (1H, s), 7.91 (1H, dd), 8.03 (1H, bs), 8.42 (1H, s)
From the HPLC analysis, one peak having a retention time of 16.3 minutes (R form) was confirmed.

-HPLC analysis conditions-
Column: CHIRALPAK AD 10μm 4.6mm x 250mm (manufactured by Daicel Chemical Industries)
Mobile phase: hexane / ethanol = 95/5 (V / V), measurement wavelength: 213 nm, flow rate: 0.5 ml / min, oven temperature: 40 ° C., sample concentration: 0.1 mg / mL, injection volume: 5 μL

Example 3 FIG.
2- [4-[[5- (Trifluoromethyl) -2-pyridyl] oxy] phenoxy] -N-methoxymethylcarbonyl-N-[(2-chloro-4-heptafluoroisopropyl-6-methyl) phenyl ] Synthesis of propanamide (Compound No. 54) (Reaction Scheme 3)
(R) -2- [4-[[5- (Trifluoromethyl) -2-pyridyl] oxy] phenoxy] -N-[(2-chloro-4-heptafluoroisopropyl-6-methyl) phenyl] propane To a solution of amide 200 mg in DMF 5 ml, 60% NaH in Oil 20 mg was added and stirred at room temperature. Ten minutes later, 0.058 ml of methoxymethylcarbonyl chloride was added, and the mixture was stirred at room temperature for 6 hours. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with water and saturated aqueous sodium hydrogen carbonate. The extract was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (hexane: ethyl acetate = 3: 1 Rf = 0.3) to obtain 120 mg (oil) of the target compound (No. 54) shown in Table 1.
¹ H-NMR (CDCl 3), δ ppm: 1.62 (1.3 H, d), 1.72 (1.7 H, d), 2.23 (1.7 H, s), 2.26 (1.3 H, s), 3.41 (1.7 H, s), 3.45 (1.3H, s), 3.86 (1.2H, q), 4.23 (0.8H, q), 5.30 (0.5H, b), 5.83 (0.6H, b), 6.70 (1H, d), 6.89-7.05 (4H, m), 7.38 (0.5H, s), 7.46 (0.6H, s), 7.61 (1H, s), 7.87 (1H, dd), 8.42 (1H, bs)
The rotamer ratio was 55:45.

Example 4
2- [4-[[5- (Trifluoromethyl) -2-pyridyl] oxy] phenoxy] -N-methoxymethylcarbonyl-N-[(2-chloro-4-heptafluoroisopropyl-6-methyl) phenyl ] Alternative route synthesis of propanamide (Compound No. 54) (Scheme 2)

4-1) N-methoxymethylcarbonyl- (2-chloro-4-heptafluoroisopropyl-6-methyl) aniline (intermediate synthesis)
To a solution of 48 ml of (2-chloro-4-heptafluoroisopropyl-6-methyl) aniline in 2 ml of N-methyl-2-pyrrolidone, 0.22 ml of methoxymethylcarbonyl chloride was added little by little and stirred at room temperature for 1 hour. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with water and saturated aqueous sodium hydrogen carbonate. The extract was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The target compound N-methoxymethylcarbonyl- (2-chloro-4-heptafluoroisopropyl-6-methyl) aniline 720 mg (solid) was obtained. Used in the next reaction without further purification.
¹ H-NMR (CDCl3), δ ppm: 2.36 (3H, s), 3.57 (3H, s), 4.12 (2H, s), 7.40 (1H, s), 7.54 (1H, s), 8.15 (1H, bs )

4-2) 60% NaH in Oil (50 mg) was added to a solution of 382 mg of N-methoxymethylcarbonyl- (2-chloro-4-heptafluoroisopropyl-6-methyl) aniline in 3 ml of DMF, and the mixture was stirred at room temperature. After cooling to 0-10 ° C., 420 mg of (R) -2- [4-[[5- (trifluoromethyl) -2-pyridyl] oxy] phenoxy] propionyl chloride was added in small portions. Stir at room temperature for 6 hours. The reaction solution was poured into water and extracted with ethyl acetate. The obtained organic layer was washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (hexane: ethyl acetate = 3: 1 Rf = 0.3) to obtain 310 mg (oil) of the target compound shown in Table 1 (No. 54). The compound of Example 3 was identical in Rf value and ¹ H-NMR.

Example 5
2- [4-[[5- (Trifluoromethyl) -2-pyridyl] oxy] phenoxy] -N-[(2-chloro-4-heptafluoroisopropyl-6-methyl) phenyl] propanamide (Compound No. 45, racemate) (Scheme 4)

5-1) Synthesis of 2-bromo-N-[(2-chloro-4-heptafluoroisopropyl-6-methyl) phenyl] propanamide (intermediate) (2-chloro-4-heptafluoroisopropyl-6 -Methyl) To a solution of aniline 929 mg of N-methyl-2-pyrrolidone 3 ml, 0.38 ml of 2-bromopropionyl bromide was added little by little and stirred at room temperature for 1 hour. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with water and saturated aqueous sodium hydrogen carbonate. The extract was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (hexane: ethyl acetate = 3: 1 Rf = 0.3) to obtain 1280 mg (oil) of the desired intermediate.
¹ H-NMR (CDCl3), δ ppm: 2.20 (3H, d), 2.36 (3H, s), 4.62 (1H, q), 7.41 (1H, s), 7.55 (1H, s), 7.92 (1H, bs )

5-2) After adding 0.90 g of anhydrous potassium carbonate to a solution of 1.28 g of 4-[[5- (trifluoromethyl) -2-pyridyl] oxy] phenol in 10 ml of N-methyl-2-pyrrolidone and stirring, Bromo-N-[(2-chloro-4-heptafluoroisopropyl-6-methyl) phenyl] propanamide 0.44 g was added in small portions. After stirring at room temperature for 5 hours, the mixture was heated and stirred at 105 ° C. for 2 hours. After cooling to room temperature, water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with water and saturated aqueous sodium hydrogen carbonate. The extract was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (hexane: ethyl acetate = 3: 1) to obtain 0.1 g (solid) of the target compound (No. 45) shown in Table 1. The melting point of the obtained compound was 112-114 ° C.
¹ H-NMR (CDCl3), δ ppm: 1.76 (3H, d), 2.30 (3H, s), 4.87 (1H, q), 7.02 (1H, d), 7.07 (2H, d), 7.13 (2H, d ), 7.39 (1H, s), 7.52 (1H, s), 7.91 (1H, dd), 8.03 (1H, bs), 8.42 (1H, s)
From the analysis of HPLC, a racemate was confirmed with a peak area ratio of 1: 1 having a retention time of 13.7 minutes (S form) and 16.3 minutes (R form).

Table ¹ below shows the ¹ H-NMR data of compounds produced in the same manner as in the above Examples.

The formulation containing the compound of the present invention will be specifically described below by giving some formulation examples. Of course, the compound of the present invention, auxiliary components and the amount of addition thereof are limited to the following formulation examples. is not. In the preparation examples, “part” means all parts by weight.

Formulation Example 1 Emulsion Compound of the present invention (10 parts), xylene (60 parts), N-methyl-2-pyrrolidone (20 parts), Solpol 3005X (mixture of nonionic surfactant and anionic surfactant, Toho Chemical Industry Co., Ltd. (trade name) (10 parts) was uniformly mixed and dissolved to obtain an emulsion.

Formulation Example 2 Wetting Agent-1
Compound of the present invention (20 parts), Nipseal NS-K (white carbon, Tosoh Silica Co., Ltd., trade name) (10 parts), Kaolin clay (Kaolinite, Takehara Chemical Co., Ltd., trade name) (60 parts) Sun Extract P-252 (sodium lignin sulfonate, Nippon Paper Industries Co., Ltd., trade name) (5 parts) and Lunox P-65L (alkyl allyl sulfonate, Toho Chemical Industry Co., Ltd., trade name) (5 parts) The mixture was uniformly mixed and ground with an air mill to obtain a wettable powder.

Formulation Example 3 Wetting Agent-2
Compound of the present invention (20 parts), Nipseal NS-K (white carbon, Tosoh Silica Co., Ltd., trade name) (20 parts), Kaolin clay (Kaolinite, Takehara Chemical Co., Ltd., trade name) (50 parts) , Lunox 1000C (Naphthalenesulfonate condensate, Toho Chemical Co., Ltd., trade name) (5 parts) and Solpol 5276 (Nonionic surfactant, Toho Chemical Co., Ltd., trade name) (5 parts) The mixture was pulverized and mixed uniformly to obtain a wettable powder.

Production Example 4 Granule wettable powder Compound of the present invention (20 parts), Demol N (Naphthalenesulfonate formalin condensate, Kao Corporation, trade name) (5 parts), Aerol CT-1L (Dioctylsulfosuccinate, Toho) Chemical Industry Co., Ltd., trade name) (1 part), Cellogen 701A (Carboxymethylcellulose, Daiichi Kogyo Seiyaku Co., Ltd.) (1 part) and Kaolin clay (Kaolinite, Takehara Chemical Industry Co., Ltd., trade name) (73 parts) Was mixed and ground uniformly with an air mill. Water was added to this mixture and kneaded well, followed by extrusion granulation and dry granulation to obtain a granulated wettable powder.

Formulation Example 5 Aqueous solvent-1
The compound of the present invention (20 parts), Lunox P-65L (alkyl allyl sulfonate, Toho Chemical Industry Co., Ltd., trade name) (3 parts), water-soluble carrier potassium chloride (77 parts) were mixed and ground uniformly. A water solvent was obtained.

Formulation Example 6 Aqueous solvent-2
The compound of the present invention (50 parts), Newkalgen BX-C (Na alkylnaphthalene sulfonate, Takemoto Yushi Co., Ltd., trade name) (5 parts), water-soluble carrier potassium chloride (45 parts) are uniformly mixed and pulverized. Thus, an aqueous solvent was obtained.

Formulation Example 7 Flowable Agent-1
Premixed propylene glycol (5 parts), Solpol 7933 (anionic surfactant, Toho Chemical Co., Ltd., trade name) (5 parts), water (50 parts) and compound of the present invention (20 parts) Was dispersed into a slurry mixture, and this slurry mixture was then wet pulverized, and then xanthan gum (Kelzan, Sanki Co., Ltd., trade name) (0.2 parts) was previously added to water (19.8 parts). What was well mixed and dispersed was added to obtain a flowable agent.

Formulation Example 8 Flowable Agent-2
Compound of the present invention (20 parts), Newkalgen FS-26 (mixture of dioctyl sulfosuccinate and polyoxyethylene tristyryl phenyl ether, Takemoto Yushi Co., Ltd., trade name) (5 parts), propylene glycol (8 parts), Water (50 parts) was mixed in advance, and the slurry mixture was wet pulverized. Next, xanthan gum (0.2 parts) was thoroughly mixed and dispersed in water (16.8 parts) to prepare a gel-like material, which was thoroughly mixed with the pulverized slurry to obtain a flowable agent.

Formulation Example 9 EW-1
Compound of the present invention (20 parts) and Solpol CA-42 (nonionic activator, Toho Chemical Co., Ltd., trade name) (15 parts) and preservative Proxel GX-L (Lonza Japan Co., Ltd., trade name) (0 0.1 part) was mixed and homogenized, and then water (59.6 parts) was gradually added with stirring to obtain a dispersion. Antifoaming agent Antihome E-20 (emulsion-type modified silicone, Kao Corporation, trade name) (0.1 part) was added to the obtained dispersion, and xanthan gum dispersed in propylene glycol (5.0 parts) (Kelzan, Sanki Co., Ltd., trade name) (0.2 parts) was added to obtain an emulsion formulation (phase inversion emulsification method).

Formulation Example 10 EW-2
The compound of the present invention (10 parts) was dissolved in xylene (10 parts) and mixed with the surfactant Rheidol 430V (polyoxyethylene sorbite tetraoleate, Kao Corporation, trade name) (24 parts). Liquid obtained in water (50.6 parts), antifoaming agent Antihome E-20 (emulsion-type modified silicone, Kao Corporation, trade name) (0.1 part), preservative Proxel GX-L (Lonza) Japan Co., Ltd. (trade name) (0.1 part) was added, and then dispersed using a homogenizer, and then dispersed in propylene glycol (5.0 parts) (xanthan gum, Sanki Co., Ltd., trade name) ( 0.2 part) was added to obtain an emulsion formulation (mechanical emulsification method).

Formulation Example 11 ME Agent-1
The compound of the present invention (0.01 part) and Solpol CA-42 (nonionic activator, Toho Chemical Co., Ltd., trade name) (0.1 part) were mixed and homogenized, and then gradually mixed with stirring. (99.79 parts) was added. Preservative Proxel GX-L (Lonza Japan Co., Ltd., trade name) (0.1 part) was added to the dispersion to obtain a microemulsion.

Formulation Example 12 ME Agent-2
The compound of the present invention (10 parts) and New Calgen D-945 (polyoxyethylene (20 mol) sorbitan monooleate, Takemoto Yushi Co., Ltd., trade name) (20 parts) were mixed and homogenized, and then stirred. Gradually water (69.9 parts) was added. Preservative Proxel GX-L (Lonza Japan Co., Ltd., trade name) (0.1 part) was added to the dispersion to obtain a microemulsion.

Formulation Example 13 ME Agent-3
The compound of the present invention (0.01 part) was mixed with a solvent Solvesso 200 (Exxon Mobil, trade name) (0.08 part) and New Calgen ST-30 (polyoxyethylene arylphenyl ether formaldehyde condensate and polyoxyalkylene aryl phenyl ether). And a mixture of alkylbenzene sulfonate and xylene, Takemoto Yushi Co., Ltd., trade name) (0.12 parts), mixed with a surfactant and homogenized, and water (99.69 parts) is added while stirring. Gradually added. Preservative Proxel GX-L (Lonza Japan Co., Ltd., trade name) (0.1 part) was added to the dispersion to obtain a microemulsion.

Formulation Example 14 Granule-1
Compound of the present invention (15 parts), Sun extract P-252 (sodium lignin sulfonate, Nippon Paper Industries Co., Ltd., trade name) (5 parts), Lunox P-65L (alkyl allyl sulfonate, Toho Chemical Co., Ltd.) (Product name) (2 parts), Sado bentonite (Kanto bentonite industry Co., Ltd.) (20 parts) and kaolin clay (Kaolinite, Takehara Chemical Co., Ltd., trade name) (58 parts) were uniformly mixed and ground in an air mill. . Water was added to this mixture and kneaded well, followed by extrusion granulation and dry sizing to obtain granules.

Formulation Example 15 Granule-2
Silica sand (90 parts) was placed in a rolling granulator and allowed to contain water, and then the compound of the present invention (5 parts) and sun extract P-252 (sodium lignin sulfonate, Nippon Paper Industries Co., Ltd.) previously pulverized and mixed. , Trade name) (4 parts), GOHSENOL GL05 (polyvinyl alcohol, Nippon Synthetic Chemical Industry Co., Ltd., trade name) (0.5 parts) and nip seal NS-K (white carbon, Tosoh Silica Corporation, trade name) ( 0.5 parts), and after coating, dry sized to obtain granules.

Formulation Example 16 Granule-3
Ishikawa Light (Ishikawa Light Industry Co., Ltd., trade name) (89 parts) was placed in a rolling granulator, and after adding water, the compound of the present invention (5 parts), Sun Extract P- 252 (sodium lignin sulfonate, Nippon Paper Industries Co., Ltd., trade name) (3 parts), Aerol CT-1L (dioctyl sulfosuccinate, Toho Chemical Co., Ltd., trade name) (0.5 parts), Solpol 5276 Ion activator, Toho Chemical Industry Co., Ltd., trade name) (2 parts) and Gohsenol GL05 (polyvinyl alcohol, Nippon Synthetic Chemical Industry Co., Ltd., trade name) (0.5 parts) are coated, dried and sized. To obtain granules.

Formulation Example 17 Fine granules-1
The compound of the present invention (2 parts) was diluted with a solvent, and mixed with Ishikawa Light (Ishikawa Light Industry Co., Ltd., trade name) (98 parts) while spraying the diluted solution. The obtained granular composition was dried and sieved to obtain a fine granule.

Formulation Example 18 Fine granules-2
The compound of the present invention (5 parts) is subjected to air mill grinding or mechanochemical grinding as required. Toxanone GR-31A (polycarboxylic acid type anionic surface active agent) was obtained by uniformly mixing powdery bulk material with No. 6 silica sand (Ube Sand Industry Co., Ltd., trade name) (85 parts) and then diluting with a solvent. An aqueous solution of the agent, Sanyo Kasei Kogyo Co., Ltd., trade name) (10 parts) was mixed while sprayed, and the resulting granular composition was dried and sieved to obtain a fine granule.

Formulation Example 19 Powder A compound of the present invention (2 parts), Nipseal NS-K (white carbon, Tosoh Silica Co., Ltd., trade name) (10 parts) and Kaolin clay (Kaolinite, Takehara Chemical Co., Ltd., trade name) (88 parts) was uniformly mixed and ground with an air mill to obtain a powder.

Formulation Example 20 DL Powder Compound (5 parts) of the present invention, propylene glycol (0.5 part) and DL clay (Showa KDE Co., Ltd., trade name) (94.5 parts) are uniformly mixed and pulverized. Obtained.

Formulation Example 21 Seed coating powder Compound of the present invention (10 parts), Sun extract P-252 (sodium lignin sulfonate, Nippon Paper Industries Co., Ltd., trade name) (6 parts), Gohsenol GL05 (polyvinyl alcohol, Nippon Synthetic Chemical Industry Co., Ltd.) Company, product name) (1 part) and clay (Nippon Talc Co., Ltd. product name) (83 parts) are uniformly mixed and pulverized, and pre-moistened seeds are mixed, air-dried, and coated seeds Got.

Formulation Example 22 Oily Suspension Formulation Compound (20 parts) of the present invention, Newkalgen C-120 (POE tristyryl phenyl ether, Takemoto Yushi Co., Ltd., trade name) (5 parts), Rheodor TW-O120V (POE sorbitan monoole) Eight, Kao Corporation, trade name) (10 parts), oleic acid methyl ester (Kanto Chemical Co., Reagents) (62 parts), Sven NZ (Organic Bentonite, Hojun Co., Ltd., trade name) (3 parts) The slurry dispersion was wet pulverized to obtain an oily suspension formulation.

Next, the action effect and usefulness of the compound of the present invention will be described with reference to specific examples. The compounds used for comparison are indicated by the following compound symbols.
Comparative compound A (compound described in Patent Document 17)

Comparative compound B (analogous compound of comparative drugs A, C, D)

Comparative compound C (compound described in Patent Document 19)

Comparative compound D (compound described in Patent Document 13)

Comparative compound E (compound described in Patent Document 1)

Table ¹ below shows the ¹ H-NMR data of Comparative Compounds A to E.

Table 8

Test Example Test for Cucumber Powdery Mildew A water dilution of the emulsion prepared according to Formulation Example 1 was sprayed over the entire cucumber seedling (approximately 1.5 leaf seedlings) at a rate of 5 ml / pot using a spray gun. On the next day after spraying, the leaf surface of the first true leaf was spray-inoculated with a spore suspension (1.0 × 10 ⁵ spores / ml) having a predetermined concentration. After inoculation, it moved to the glass greenhouse, and after 12 days, the severity was investigated based on the following lesion area ratio. Based on the following formula, the control value was calculated from the severity of the untreated group and the severity of the treated group.
Disease severity 0 (sickness area rate: 0%), disease severity 6.25 (sickness area rate: 0 to less than 6.3%), disease severity 12.5 (sickness area rate: 6.3 to 12. Less than 5%), disease severity 25 (sickness area rate: less than 12.5-25%), disease severity 50 (sickness area rate: less than 25-50%), disease severity 100 (sickness area rate: 50%) more than)

Control value (%) = [1− (Disease level of treated area / Disease level of untreated area)] × 100

As a result, compound numbers 5, 6, 7, 8, 14, 15, 19, 20, 21, 22, 24, 36, 37, 40, 43, 46, 47, 49, 52, 54, 57, 58, 60 61, 62, 63, 65, 68, 77, 78, 80, 87, 94, 99, 102, 103, 105, 110, 111, 116, 117, 119, 122, 123, 124, 126, 130, 135 136, 140, 141, 142, 146, 148, 151, 152, 154, 156, 162, 165, 166, 167, 170, 173, 183, 192, 193, 196, 200, 201, 202, 203, 204 , 207, 208, 209, 210, 214, 215, 216, 217, 219, 220, 221, 222, 223, 226, 227, 228, 229, 2 0,231,232,233,234,239,240,241,261,4-2,4-3,6-5,6-11 was a control value of 100 at a concentration of 400ppm.

On the other hand, the comparative agents A, B, C, D, and E had a control value of 0 at a concentration of 400 ppm.

Test Example Test for Wheat Powdery Mildew A water dilution of the emulsion prepared according to Formulation Example 1 was sprayed over the whole wheat seedling (approximately 1.5 leaf seedlings) at a rate of 5 ml / pot using a spray gun. On the next day after spraying, the seedlings after spraying were moved to a glass greenhouse and inoculated by placing seedlings with wheat powdery mildew around them. 12 days after the inoculation, the disease severity was investigated based on the following lesion area ratio. Based on the following formula, the control value was calculated from the severity of the untreated group and the severity of the treated group.
Disease severity 0 (sickness area rate: 0%), disease severity 6.25 (sickness area rate: 0 to less than 6.3%), disease severity 12.5 (sickness area rate: 6.3 to 12. Less than 5%), disease severity 25 (sickness area rate: less than 12.5-25%), disease severity 50 (sickness area rate: less than 25-50%), disease severity 100 (sickness area rate: 50%) more than)

Control value (%) = [1− (Disease level of treated area / Disease level of untreated area)] × 100

As a result, compound numbers 19, 22, 24, 36, 43, 54, 68, 80, 105, 119, 122, 165, 166, 200, 201, 202, 203, 207, 208, 261 are controlled at a concentration of 400 ppm. The value was 70 or more. On the other hand, the comparative agents A, B, C, D, and E had control values of 0, 22, 20, 25, and 25, respectively, at a concentration of 400 ppm.

Test example: Insecticidal effect test on Japanese horseshoe moth The water-diluted emulsion prepared according to Formulation Example 1 was sprayed onto the leaves of potted rice seedlings grown for two weeks after seeding using an airbrush. . After the chemical solution was air-dried, 5 third instar larvae were inoculated, placed in a 430 ml container in a PET cup, covered with a mesh, and then kept in a thermostatic chamber at 23 ° C. Five days after the treatment, the state of the larvae was observed in three parts: survival, abnormality, and death, and the larval mortality (%) was determined by the following formula based on the observation results. The test was conducted using 1 seedling in each group.

Larval mortality rate (%) = (number of dead insects + number of abnormal insects) / number of test insects x 100

As a result, compound numbers 19, 22, 38, 39, 41, 47, 48, 52, 57, 59, 60, 61, 63, 79, 87, 102, 103, 104, 105, 117, 127, 129, 130 146, 147, 173, 192, 193, 195, 196, 200, 201, 202, 203, 221, 4-3, 6-5, 6-7 show 100% insecticidal rate at a concentration of 500 ppm It was.
On the other hand, the comparative agents A, B, C, D and E had an insecticidal rate of 0% at a concentration of 500 ppm.

Test Example: Insecticidal effect test against tomato rust mites Water was put into a 430 ml capacity PET cup, and a lid with a hole (diameter: about 5 mm) was formed in the center. Absorbent cotton having a width of about 1 cm and a length of about 14 cm was inserted so as to be immersed in the water in the cup through the hole of the lid, and about 8 cm square of absorbent cotton was placed thereon so that the water in the cup was constantly replenished. Place three leaf discs (1cm x 1cm) made from small leaves in the initial stage of tomato leaf development on absorbent cotton so that the back of the leaf is on top. Vaccinated. 24 hours after inoculation, this cup was placed in an acrylic cylinder having a height of 45 cm and a diameter of 12 cm, and an aqueous dilution of an emulsion prepared according to Formulation Example 1 was sprayed with 2.0 ml per cup using an air brush. (1 concentration, 1 repetition). After spraying, it was kept in a constant temperature room at 25 ° C. Seven days after the treatment, the number of surviving larvae was divided into four levels: 100 (density suppression rate: 100%), 80 (same: 99-80%), 50 (same: 79-50%), 0 (same: less than 50%) The control value was calculated by the following formula based on the evaluation.

Control value = (A × 100 + B × 80 + C × 50) / (A + B + C + D)

A: 100 disks, B: 80 disks, C: 50 disks, D: 0 disks.
As a result, compound numbers 20, 36, 37, 43, 47, 52, 53, 54, 61, 65, 66, 68, 71, 77, 78, 79, 85, 87, 94, 95, 147, 168, 169 , 180, 181, 182, 183, 185, 190, 192, 2-1, 3-1 exhibited a control value of 100% at a concentration of 500 ppm.
On the other hand, the comparative agents A, B, C, D and E had a control value of 0 at a concentration of 500 ppm.

The novel compound of the present invention can be preferably used as an active ingredient of agricultural and horticultural agents.

Claims

The following formula (1)

(1)
[Where
R 1 is hydrogen, C 1-12 alkyl group, C 1-12 haloalkyl group, C 3-6 alkenyl group, C 3-6 haloalkenyl group, C 3-6 alkynyl group, C 3-6 haloalkynyl group, C 3-8 cycloalkyl group, C 3-8 halocycloalkyl group, C 3-8 cycloalkyl-C 1-6 alkyl group, C 1-6 alkoxy group, C 1-6 haloalkoxy group, C 1-6 Alkoxy C 1-6 alkyl group, C 1-6 alkylcarbonyl group, C 1-6 haloalkylcarbonyl group, C 1-6 alkoxycarbonyl group, C 1-6 haloalkoxycarbonyl group, C 1-6 alkoxy C 1-6 Alkylcarbonyl group, C 1-6 alkoxycarbonyl-carbonyl group, mono (di) C 1-6 alkylaminocarbonyl group, mono (di) C 1-6 alkylaminocarbonyl-carbonyl group, C 1-6 alkylcarbonyloxy C 1-6 alkylcarbonyl group, C 1-6 alkylsulfonyl group C 1-6 haloalkylsulfonyl group, benzyl group, cyano group, hydroxyl group or formyl group,
R 2 and R 3 are each independently hydrogen, halogen, cyano group, hydroxyl group, C 1-12 alkyl group, C 1-12 haloalkyl group, C 3-8 cycloalkyl group, C 1-6 hydroxyalkyl group, C 1-12 alkoxy group, C 1-6 alkoxy C 1-6 alkyl group, C 1-6 alkylthio group, C 1-6 alkylsulfonyl group, C 1-6 alkylsulfinyl group or phenyl group (wherein the phenyl is , Halogen, C 1-12 alkyl group, C 1-12 haloalkyl group, C 3-8 cycloalkyl group, C 1-6 alkoxy group, C 3-6 alkenyloxy group, C 3-6 alkynyloxy group, C 1-6 haloalkoxy group, C 3-6 haloalkenyloxy group, C 3-6 haloalkynyloxy group, C 1-6 alkylthio group, C 1-6 alkylsulfinyl group, C 1-6 alkylsulfonyl group, C 1 -6 haloalkylthio group, C 1-6 halo alkyl sulphates Alkenyl group, C 1-6 haloalkylsulfonyl group, the same or different groups may have 1 to 3) is selected from the group consisting of a nitro group or a cyano group,
V is

Indicate
R 4 and R 5 each independently represent hydrogen, halogen, C 1-3 alkyl group, C 1-3 haloalkyl group, C 1-3 alkoxy group, C 1-3 haloalkoxy group or hydroxyl group;
W may be the same or different, and may be hydrogen, halogen, hydroxyl group, amino group, C 1-12 alkyl group, C 1-12 haloalkyl group, C 3-8 cycloalkyl group, C 1-6 alkoxy group, mono ( Di) C 1-6 alkylamino group, C 3-6 alkenyloxy group, C 3-6 alkynyloxy group, C 1-6 haloalkoxy group, C 3-6 haloalkenyloxy group, C 3-6 haloalkynyloxy group, C 1-6 alkylthio group, C 1-6 alkylsulfinyl group, C 1-6 alkylsulfonyl group, C 1-6 haloalkylthio group, C 1-6 haloalkylsulfinyl group, C 1-6 haloalkylsulfonyl groups, C 1-6 alkoxycarbonyl group, mono (di) C 1-6 alkylaminocarbonyl group, C 1-6 hydroxyalkyl group, C 1-6 alkoxy C 1-6 alkyl group, C 1-6 alkylcarbonyloxy group, amino Carbonyl group, hydroxycarbo When it represents a nyl group, a formyl group, a nitro group or a cyano group, or when two Ws are substituted with two adjacent carbon atoms on the phenyl ring, the two Ws are bonded to each other. May form a saturated or unsaturated 5- or 6-membered ring together with the carbon atoms
X may be the same or different and is hydrogen, halogen, C 1-12 alkyl group, C 1-12 haloalkyl group, C 3-8 cycloalkyl group, C 1-6 alkoxy group, C 3-6 alkenyloxy group C 3-6 alkynyloxy group, C 1-6 haloalkoxy group, C 3-6 haloalkenyloxy group, C 3-6 haloalkynyloxy group, C 1-6 alkylthio group, C 1-6 alkylsulfinyl group, C 1-6 alkylsulfonyl groups, C 1-6 haloalkylthio group, C 1-6 haloalkylsulfinyl group, C 1-6 haloalkylsulfonyl group, a nitro group or a cyano group,
Y represents a (Y 1 ) n 3 -heteroaryl-A- group or a (Y 1 ) n 4 -aryl-A- group;
Y 1 may be the same or different and is hydrogen, halogen, C 1-12 alkyl group, C 1-12 haloalkyl group, C 3-8 cycloalkyl group, C 1-6 alkoxy group, C 3-6 alkenyloxy. Group, C 3-6 alkynyloxy group, C 1-6 haloalkoxy group, C 3-6 haloalkenyloxy group, C 3-6 haloalkynyloxy group, C 1-6 alkylthio group, C 1-6 alkylsulfinyl group , C 1-6 alkylsulfonyl group, C 1-6 haloalkylthio group, C 1-6 haloalkylsulfinyl group, C 1-6 haloalkylsulfonyl group, a pentafluorosulfanyl group, C 2-6 alkenyl, C 2-6 alkynyl Group, C 1-6 alkoxy C 1-6 alkyl group, C 1-6 alkylcarbonyl group, C 1-6 haloalkylcarbonyl group, C 1-6 alkoxycarbonyl group, C 1-6 haloalkoxycarbonyl group, C 1- 6 alkoxy C 1-6 Arukiruka Boniru group, mono (di) C 1-6 alkylaminocarbonyl group, an amino group, mono (di) C 1-6 alkylamino group, mono (di) C 1-6 alkylcarbonylamino group, a nitro group, a cyano group, An aryl group or a heteroaryl group (wherein the aryl and heteroaryl are, respectively, halogen, C 1-12 alkyl group, C 1-12 haloalkyl group, C 3-8 cycloalkyl group, C 1-6 alkoxy group, C 3-6 alkenyloxy group, C 3-6 alkynyloxy group, C 1-6 haloalkoxy group, C 3-6 haloalkenyloxy group, C 3-6 haloalkynyloxy group, C 1-6 alkylthio group, C 1 -6 alkylsulfinyl group, C 1-6 alkylsulfonyl group, C 1-6 haloalkylthio group, C 1-6 haloalkylsulfinyl group, C 1-6 haloalkylsulfonyl group, is selected from the group consisting of a nitro group or a cyano group Having 1 to 3 identical or different groups)
Z 1 represents an oxygen atom or a sulfur atom,
Z 2 represents an oxygen atom, a sulfur atom or NR 6 ;
R 6 is hydrogen, C 1-12 alkyl group, C 1-12 haloalkyl group, C 3-6 alkenyl group, C 3-6 haloalkenyl group, C 3-6 alkynyl group, C 3-6 haloalkynyl group, C 3-8 cycloalkyl group, C 3-8 halocycloalkyl group, C 3-8 cycloalkyl-C 1-6 alkyl group, C 1-6 alkoxy group, C 1-6 haloalkoxy group, C 1-6 Alkoxy C 1-6 alkyl group, C 1-6 alkylcarbonyl group, C 1-6 haloalkylcarbonyl group, C 1-6 alkoxycarbonyl group, C 1-6 haloalkoxycarbonyl group, C 1-6 alkoxy C 1-6 Alkylcarbonyl group, C 1-6 alkoxycarbonyl-carbonyl group, mono (di) C 1-6 alkylaminocarbonyl group, mono (di) C 1-6 alkylaminocarbonyl-carbonyl group, C 1-6 alkylsulfonyl group, C 1-6 haloalkylsulfonyl group, a benzyl group, a cyano group, Shows the acid group or formyl group,
A represents an oxygen atom, sulfur atom, sulfinyl or sulfonyl group,
n 1 and n 2 each independently represent an integer of 1 to 4,
n 3 and n 4 each independently represents an arbitrary integer of 1 or more. ]
Or an N-oxide or salt thereof.
V is 4-substituted

The compound according to claim 1, which shows: N-oxide or a salt thereof.
The compound, its N-oxide or a salt thereof according to claim 1 or 2, wherein R 3 represents a hydrogen atom and Y represents a (Y 1 ) n 3 -pyridyloxy group.
A method for producing the compound according to claim 1, its N-oxide or a salt thereof, comprising:

(2)
[Wherein R 1 , V 1 , W, and n 1 are as defined in Formula (1)]
And a compound represented by the following formula (3):

(3)
[Wherein R 2 R 3 , Z 1 , Z 2 , X 1 , Y, n 2 are as defined in Formula (1)]
The manufacturing method including making the compound represented by these react.
A method for producing the compound according to claim 1, its N-oxide or a salt thereof, comprising:

(2)
[Wherein R 1 , V 1 , W, and n 1 are as defined in Formula (1)]
And a compound represented by the following formula (4):

(4)
[In the formula, Hal represents halogen, and R 2 R 3 , Z 1 , Z 2 , X 1 , Y, and n 2 are as defined in Formula (1)]
The manufacturing method including making the compound represented by these react.
An agricultural and horticultural agent containing the compound according to any one of claims 1 to 3, its N-oxide or a salt thereof.
An agricultural and horticultural fungicide containing the compound according to any one of claims 1 to 3, its N-oxide or a salt thereof.
An agricultural and horticultural insecticide containing the compound according to any one of claims 1 to 3, its N-oxide or a salt thereof.
An agricultural and horticultural acaricide containing the compound according to any one of claims 1 to 3, its N-oxide or a salt thereof.
Use of the agricultural and horticultural chemical according to claim 6 for controlling plant pests.
The use according to claim 10, wherein the pest is a pathogen.
A method for controlling plant pests, comprising a step of treating pests and / or their habitats and / or seeds and / or plant propagation materials with the agricultural and horticultural chemicals according to claim 6.
A method for preventing plant pests, comprising the step of treating a place where a useful crop is to be grown or a place where the useful crop is grown or a growing crop with the agricultural and horticultural chemical according to claim 6. .
A method for preparing an agrochemical composition, comprising the step of mixing the agricultural and horticultural agent according to claim 6 with a bulking agent and / or a surfactant.