JPWO2017213137A1 - Novel compound and agricultural and horticultural agent containing the same as an active ingredient - Google Patents

Abstract

The present invention provides novel agricultural and horticultural agents for controlling harmful organisms in crop production such as agriculture and horticulture.
formula

(Wherein, R ⁴ and R ⁵ are each independently 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 Anilide compounds or thioamide compounds having a specific structure, which have a substituent as shown in (a) are used as an active ingredient.

Description

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

  In the agricultural and horticultural field, various agricultural and horticultural agents for controlling various pests have been developed and put to practical use.

  However, pesticides that have been widely used in the past are not necessarily satisfied with their effects, spectra, residual effects, etc., and also with the requirements such as the number of applications and reduction of the applied dose. In addition, the emergence of pests that have developed resistance to conventional pesticides has also become a problem. For example, in cultivation of vegetables, fruits, flowers, flowers, tea, wheat and rice, for example, triazoles, imidazoles, pyrimidines, benzimidazoles, dicarboximides, phenylamides, Various pathogens that have developed resistance to various strains of fungicides such as strobilurins and SDHI have appeared in various places, and it has become more difficult to control these resistant bacteria year by year. In the field of insecticides and acaricides, we have developed and marketed organophosphorus insecticides, pyrethroid insecticides, benzoylurea insecticides, diamide insecticides, organotin acaricides, etc. However, resistance pests and mites have appeared shortly after launch, and the reduction in effectiveness has become a problem. Therefore, the emergence of novel pesticides that always show sufficient control effects at low doses against various pests that have developed resistance to conventional general-purpose agricultural and horticultural agents, and that have less adverse effects on the environment, is always desirable. It is rare.

  Various new agricultural and horticultural agents have been proposed to meet these demands, but they do not necessarily meet the above demands.

  Patent Documents 1 to 20 and Non-patent Document 1 disclose carboxamide derivatives having the following structures having herbicidal activity or bactericidal activity (CAS number is a reference).

Patent Document 1: Compound of 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 groups represented by the following formulas as substituents of the aniline part of the compound.
Further, 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.

WO 2015/000392 pamphlet Chinese Patent Publication No. 104876922 Chinese Patent Publication No. 101941917 Chinese Patent Publication No. 101747263 U.S. Pat. No. 4,968,343 Unexamined-Japanese-Patent 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 Application Laid-Open No. 61-280477 Japanese Patent Application Laid-Open No. 61-178904 WO 82/00400 Pumplet Belgian Patent Publication No. 889773 JP 56-43269 German Patent Publication No. 2926049 JP-A-54-119476 Japanese Patent Application Laid-Open No. 54-122728 Japanese Patent Application Laid-Open No. 54-32479 Japanese Patent Application Laid-Open No. 52-125626

Journal of the Japanese Society of Pesticides (1985), 10 (2), P257-62.

  In crop production such as agriculture and horticulture, damage by pests is still large, and development of new agricultural and horticultural agents is desired from factors such as resistance to existing drugs and occurrence of resistant pests.

MEANS TO SOLVE THE PROBLEM The present inventors discovered that the compound represented by following Formula (1) which is a novel compound is useful as an agricultural-and-horticulture drug, as a result of earnestly researching so that the said subject might be solved. It has been completed.
That is, the present invention relates to the following [1] to [14].

[1] lower formula (1)
(1)
[In the formula,
R ¹ represents hydrogen, a C _1-12 alkyl group, a C _1-12 haloalkyl group, a C _3-6 alkenyl group, a C _3-6 haloalkenyl group, a C _3-6 alkynyl group, a 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 haloalkoxy group, C _1-6 Alkoxy C _1-6 alkyl group, C _1-6 alkyl carbonyl group, C _1-6 haloalkyl carbonyl group, C _1-6 alkoxy carbonyl group, C _1-6 halo alkoxy carbonyl group, C _1-6 alkoxy C _1-6 Alkyl carbonyl group, C _1-6 alkoxycarbonyl-carbonyl group, mono (di) C _1-6 alkylaminocarbonyl group, mono (di) C _1-6 alkylamino carbonyl-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 each independently represent hydrogen, halogen, a cyano group, a hydroxyl group, a C _1-12 alkyl group, a C _1-12 haloalkyl group, a C _3-8 cycloalkyl group, a 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 , 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 halo alkyl sulphates Alkenyl group, C _1-6 haloalkylsulfonyl group, which may have 1 to 3 identical or different radicals selected from the group consisting of a nitro group or a cyano group), and
V is
Show,
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 hydrogen, halogen, a hydroxyl group, an amino group, a C _1-12 alkyl group, a C _1-12 haloalkyl group, a C _3-8 cycloalkyl group, a 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 groups, C _1-6 alkoxy C _1-6 alkyl group, C _1-6 alkylcarbonyloxy group, an amino Carbonyl group, hydroxy carbo Group represents a nyl group, a formyl group, a nitro group or a cyano group, or when two W's are substituted on adjacent two carbon atoms on a phenyl ring, the two W's are each bonded Together with the selected carbon atom to form a saturated or unsaturated 5- or 6-membered ring,
X may be the same or different, and is hydrogen, halogen, a C _1-12 alkyl group, a C _1-12 haloalkyl group, a C _3-8 cycloalkyl group, a C _1-6 alkoxy group, a 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 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 haloalkynyl 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 each represent a halogen, a C _1-12 alkyl group, a C _1-12 haloalkyl group, a C _3-8 cycloalkyl group, a 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 (Which may have 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 represents hydrogen, a C _1-12 alkyl group, a C _1-12 haloalkyl group, a C _3-6 alkenyl group, a C _3-6 haloalkenyl group, a C _3-6 alkynyl group, a 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 haloalkoxy group, C _1-6 Alkoxy C _1-6 alkyl group, C _1-6 alkyl carbonyl group, C _1-6 haloalkyl carbonyl group, C _1-6 alkoxy carbonyl group, C _1-6 halo alkoxy carbonyl 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, a sulfur atom, a 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 represent an arbitrary integer of 1 or more. ]
The compound represented by these, its N-oxide, or its salt.

[2] V is a 4-position substitution
The compound according to the above [1], its N-oxide or a salt thereof,

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

[4] A method for producing a compound according to the above [1], an N-oxide thereof or a salt thereof, which comprises the following formula (2)
(2)
[Wherein, R ¹ , V ¹ , W, n ¹ are as defined in the formula (1)]
And a compound represented by the following formula (3)
(3)
[Wherein, R ² R ³ , Z ¹ , Z ² , X ² , Y, n ² are as defined in the formula (1)]
A method of production comprising reacting with a compound represented by

[5] A method for producing a compound according to the above [1], an N-oxide thereof or a salt thereof, which comprises the following formula (2)
(2)
[Wherein, R ¹ , V ¹ , W, n ¹ are as defined in the formula (1)]
And a compound represented by the following formula (4)
(4)
[Wherein, Hal represents a halogen, and R ² R ³ , Z ¹ , Z ² , X ² , Y, n ² are as defined in the formula (1)]
A method of production comprising reacting with a compound represented by

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

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

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

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

[10] Use of the agricultural and horticultural drug according to the above [6] 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 the step of treating pests and / or their habitat and / or seeds and / or plant propagation material with the agricultural and horticultural agent according to the above-mentioned [6] .

[13] A pest of a plant comprising a step of treating a place where a useful crop is to be grown, a place where the useful crop is grown, or a growing crop with the agricultural or horticultural drug according to the above-mentioned [6] How to prevent

[14] A method of preparing a pesticide composition, which comprises the step of mixing the agricultural and horticultural drug according to the above-mentioned [6] with an extender and / or a surfactant.

  The compounds of the present invention exhibit excellent effects as agricultural and horticultural agents.

In the definition of the compound of the present invention represented by the above formula (I), "halogen" represents a chlorine atom, a bromine atom, an iodine atom or a fluorine atom.
The “C _1-12 alkyl group” is, 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 And a linear or branched alkyl group having 1 to 12 carbon atoms such as isodecyl group, n-undecyl group, isoundecyl group, n-dodecyl group, isododecyl and the like.
The “C _1-12 haloalkyl group” represents a linear or branched alkyl group having 1 to 12 carbon atoms substituted by one or more halogen atoms which may be the same or different.
The “C _3-8 cycloalkyl group” is, for example, 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, for example, the same or the same or 1-chlorocyclopropyl, 2,2-difluorocyclopropyl, 2,2-dichloro-1-methylcyclopropyl, 4,4-difluorocyclohexyl, etc. The cyclic C3-C8 cycloalkyl group substituted by one or more halogen atoms which may differ is shown.
The “C _3-8 cycloalkyl-C _1-6 alkyl group” means, for example, cyclic C _3-8 carbon atoms such as cyclopropylmethyl, 1-cyclopropylethyl, cyclobutylmethyl, 2-cyclooctylpropyl and the like Indicates a cycloalkyl-C _1-6 alkyl group.

As the C _1-6 haloalkyl group, for example, fluoromethyl group, chloromethyl group, difluoromethyl group, trifluoromethyl group, chlorodifluoromethyl group, bromodifluoromethyl group, dichlorofluoromethyl group, 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- C1-C6 linear or branched alkyl substituted by 1 to 13, preferably 1 to 9 halogen atoms such as trifluorohexyl group, 6-chlorohexyl group, tridecafluorohexyl group Groups are mentioned.
As a C _1-12 haloalkyl group, in addition to the groups exemplified as the above 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 substituted with 1 to 13, and preferably 1 to 9 halogen atoms.

As C _1-6 alkoxy group, for example, methoxy group, ethoxy group, n-propoxy group, isopropoxy group, cyclopropyloxy group, n-butoxy group, sec-butoxy group, tert-butoxy group, n-pentoxy group And linear or branched alkoxy groups having 1 to 6 carbon atoms such as n-hexyloxy group.
As C _1-6 haloalkoxy group, for example, fluoromethoxy group, dichloromethoxy group, trichloromethoxy group, difluoromethoxy group, trifluoromethoxy group, chlorodifluoromethoxy group, bromodifluoromethoxy group, 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 Preferably 1 to 9 such as fluoroethoxy group, 1-fluoroisopropoxy group, 3-fluoropropoxy group, 3-chloropropoxy group, 3-bromopropoxy group, 4-fluorobutoxy group, 4-chlorobutoxy group, etc. C1-C6 linear or branched substituted by a halogen atom A chain alkoxy group is mentioned.

As a C _2-6 alkenyl group, for example, 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 group, 3-hexenyl group, 4-hexenyl group, 5-hexenyl group, 1,1-dimethyl-2-butenyl group, 1,1-dimethyl-3-butenyl group, etc. A C3-C6 linear or branched alkenyl group which has a bond is mentioned.
As a C _3-6 haloalkenyl group, for example, 3-chloro-2-propenyl group, 3, 3-difluoro-2-allyl group, 3, 3-dichloro-2-allyl group, 4, 4, 4- tri 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 the like And a linear or branched alkenyl group having 3 to 6 carbon atoms and substituted by 1 to 13, and preferably 1 to 7 halogen atoms.

As a C _2-6 alkynyl group, for example, ethynyl group, 2-propynyl group, 1-methyl-2-propynyl group, 1,1-dimethyl-2-propynyl group, 1-butynyl group, 2-butynyl group, 3 -Butynyl group, 1-pentynyl group, 2-pentynyl group, 3-pentynyl group, 4-pentynyl group, 1-methyl-2-butynyl group, 1-methyl-3-butynyl group, 1,1-dimethyl-2- C3-C6 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 and the like A linear or branched alkynyloxy group is mentioned.
As a C _3-6 haloalkynyl group, a 4,4,4-trifluoro-2-butynyl group, 5,5,5-trifluoro-3-pentynyl group, 1-methyl-3,3,3-trifluoro C3-C6 linear or branched alkynyl having at least one triple bond at any position such as -2-butynyl group, 1-methyl-5,5,5-trifluoro-2-pentynyl group and the like And groups including 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.

As C _1-6 alkylthio group, for example, methylthio group, ethylthio group, n-propylthio group, isopropylthio group, cyclopropylthio group, n-butylthio group, sec-butylthio group, tert-butylthio group, n-pentylthio group And linear or branched alkylthio groups having 1 to 6 carbon atoms such as n-hexylthio group.

As the C _1-6 alkylsulfinyl group, for example, methylsulfinyl group, ethylsulfinyl group, n-propylsulfinyl group, isosulfinyl group, cyclopropylsulfinyl group, n-butylsulfinyl group, sec-butylsulfinyl group, tert-butyl C1-C6 linear or branched alkyl sulfinyl groups, such as a sulfinyl group, n-pentyl sulfinyl group, n-hexyl sulfinyl group, etc. are mentioned.

As a C _1-6 alkylsulfonyl group, for example, methylsulfonyl group, ethylsulfonyl group, n-propylsulfonyl group, isosulfonyl group, cyclopropylsulfonyl group, n-butylsulfonyl group, sec-butylsulfonyl group, tert-butyl group C1-C6 linear or branched alkylsulfonyl groups, such as a sulfonyl group, n-pentyl sulfonyl group, n-hexyl sulfonyl group, etc. are mentioned.

As C _1-6 haloalkylthio group, for example, difluoromethylthio group, trifluoromethylthio group, monochloromethylthio group, dichloromethylthio group, trichloromethylthio group, monobromomethylthio group, dibromomethylthio group, tribromomethylthio group, 1-fluoro Ethylthio, 2-fluoroethylthio, 2,2-difluoroethylthio, 2,2,2-trifluoroethylthio, 2-chloro-2,2-difluoroethylthio, 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 , 3,3,3-trifluoropropylthio, 1,3-dichloro-2-propylthio, 1,1,1-trifluoro-2-propylthio, 1-chloro-3-fluoro-2-propylthio 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 C1-C6 linear or branched alkylthio groups substituted with 1 to 13, preferably 1 to 9 halogen atoms such as nonafluoro-2-butylthio group.

As C _1-6 haloalkylsulfinyl group, 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 3,3-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, which is substituted with 1 to 13, preferably 1 to 9 halogen atoms, such as nonafluoro-2-butylsulfinyl group.

As a C _1-6 haloalkylsulfonyl group, a difluoromethylsulfonyl group, a trifluoromethylsulfonyl group, a dichloromethylsulfonyl group, a trichloromethylsulfonyl group, a monobromomethylsulfonyl group, a dibromomethylsulfonyl group, 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-dichloromethane -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 Isopropylsulfonyl group, heptafluoro-n-propylsulfonyl group, 4-fluorobutylsulfonyl group, 4,4,4-trifluorobutylsulfonyl group, nonafluoro-n-butylsulfonyl group, nonafluoro-2-butylsulfonyl group, etc. 1 ~ 13 pieces, preferably 1 to A C1-C6 linear or branched alkylsulfonyl group substituted by 9 halogen atoms is mentioned.

The C _1-6 alkoxy C _1-6 alkyl group has, for example, 1 to 6 carbon atoms, such as methoxymethyl group, methoxy-2-ethyl group, ethoxymethyl group, isopropoxymethyl group, tert-butoxy-1-ethyl group, etc. Or a linear or branched alkoxy-C1-C6 linear or branched alkyl group.

As a C1-6 alkyl carbonyl group, a _C1- C6 linear or branched alkyl carbonyl group, such as a methyl carbonyl group, an ethyl carbonyl group, isopropyl carbonyl group, a tert- butyl carbonyl group, is mentioned, for example.
The C _1-6 haloalkylcarbonyl group is, for example, a trifluoromethylcarbonyl group, a chloromethylcarbonyl group, a 3-bromopropylcarbonyl group or the like, preferably substituted by 1 to 9 halogen atoms, and preferably has 1 to 6 carbon atoms A linear or branched alkoxy group is mentioned.

As the C _1-6 alkoxycarbonyl group, for example, a linear or branched alkoxycarbonyl group having 1 to 6 carbon atoms such as methoxycarbonyl group, ethoxycarbonyl group, 1-fluoroisopropoxycarbonyl group, tert-butoxycarbonyl group and the like Can be mentioned.
The C _1-6 haloalkoxycarbonyl group is, for example, preferably 1 to 13 of trifluoromethoxycarbonyl group, 2-chloroethoxycarbonyl group, isopropoxycarbonyl group, 2,2,2-trifluoroethoxycarbonyl group, etc. And C 1 -C 6 linear or branched alkyl groups substituted by 1 to 9 halogen atoms.

As the C _1-6 alkoxy C _1-6 alkylcarbonyl group, for example, methoxymethylcarbonyl group, methoxy-2-ethylcarbonyl group, ethoxymethylcarbonyl group, isopropoxymethylcarbonyl group, tert-butoxy-1-ethyl group and the like C1-C6 linear or branched alkoxy-C1-C6 linear or branched alkyl group is mentioned.

Mono (di) C _1-6 alkylamino group denotes mono C _1-6 alkylamino group or a di C _1-6 alkylamino group,
The mono C _1-6 alkylamino group, for example methylamino group, ethylamino group, and linear or branched alkylamino group having 1 to 6 carbon atoms such as 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, N-methyl-N-ethylamino and diethylamino. .
Examples of the mono C _1-6 alkylaminocarbonyl group include a linear or branched alkylaminocarbonyl group having 1 to 6 carbon atoms such as methylaminocarbonyl group, ethylaminocarbonyl group, tert-butylaminocarbonyl group, etc. Be
Examples of the di-C _1-6 alkylaminocarbonyl group include linear or branched dialkylaminocarbonyl having 1 to 6 carbon atoms such as dimethylaminocarbonyl group, N-methyl-N-ethylaminocarbonyl group, diethylaminocarbonyl group and the like Groups are mentioned.

As C _1-6 hydroxyalkyl group, for example, hydroxymethyl group, dihydroxymethyl group, 1-hydroxyethyl group, 2-hydroxyethyl group, 1,2-dihydroxyethyl group, 1-hydroxyisopropyl group, 3-hydroxypropyl group, And 4-hydroxybutyl group, 6-hydroxyhexyl group, and preferably 1 to 2 hydroxy-substituted linear or branched alkyl groups having 1 to 6 carbon atoms.

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

  In the present invention, "heteroaryl" may be monocyclic or polycyclic, and a heterocyclic group containing one or more identical or different ring-constituting heteroatoms can be used. The type of hetero atom is not particularly limited, and examples thereof include nitrogen atom, oxygen atom and sulfur atom. Examples of the heterocyclic group include furyl group, thienyl group, pyrrolyl group, oxazolyl group, isoxazolyl group, dihydroisoxazolyl group, thiazolyl group, isothiazolyl group, imidazolyl group, pyrazolyl group, oxadiazolyl group, thiadiazolyl group, triazolyl group And 5- to 7-membered monocyclic heterocyclic groups such as tetrazolyl group, pyrrolidinyl group, pyridyl group, pyridazinyl group, pyrimidinyl group, pyrazinyl group, azepinyl group, oxazepinyl group, piperidinyl group, morpholinyl group and the like. As the polycyclic heterocyclic group, benzofuranyl group, isobenzofuranyl group, benzothienyl group, indolyl group, isoindolyl group, indazolyl group, benzoxazolyl group, benzoisoxazolyl group, benzothiazolyl group, benzoisothiazo 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 carborinyl group, acridinyl group, 2-acridinyl, 3-acridinyl, 4-acridinyl, 9-acridinyl, phenoxazinyl group, phenothiazinyl group, phenazinyl group and the like.

Y represents a (Y ¹ ) n ³ -heteroaryl-A- group or a (Y ¹ ) n ⁴ -aryl-A- group, and preferred examples of the substituent include a (Y ¹ ) n ³ -pyridyloxy group or Y ¹ ) n ⁴ -phenoxy group is mentioned. n ³ and n ⁴ are each independently, 1 or more represents any integer, preferably an integer of 1 to 10, more preferably an integer of 1 to 5.
As (Y ¹ ) n ³ -pyridyloxy group, for example, 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 is 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 compounds of the present invention represented by the above formula (I), two W's are substituted on adjacent two carbon atoms on the phenyl ring, these W's are bonded to each other, and each W is bonded Together with the carbon atom to form a saturated or unsaturated 5- or 6-membered ring, for example, a condensed ring 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 W's substituted on adjacent two 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 - to form a.

  Examples of the salt of the compound of the present invention represented by the above formula (1) include mineral acid salts such as hydrochlorides, sulfates, nitrates and phosphates, acetates, fumarates, maleates and oxalates, The organic acid salts such as methanesulfonic acid salt, benzenesulfonic acid salt, p-toluenesulfonic acid salt and the like can be exemplified.

  The compound of the present invention represented by the above formula (1) may contain one or more asymmetric centers in its structural formula, and when two or more optical isomers and diastereomers exist. The present invention also encompasses all of the respective optical isomers and the mixtures in which they are contained in any proportion. Moreover, the compound represented by the said Formula (1) of this invention may contain a geometric isomer and a rotational isomer. Although two geometrical isomers derived from a carbon-carbon double bond may exist in the formula in the structure, the present invention provides each geometrical isomer, rotational isomer and a mixture containing them in any ratio. Are all included.

Among the compounds of the present invention, R ¹ and R ³ are a hydrogen atom, R ² is a hydrogen atom, a halogen atom, a C _1-3 alkyl group, a C _1-3 alkoxy, a C _1-3 haloalkoxy, a C _1-3 alkoxy The compound which shows a C _1-3 alkyl group is preferable, and also the compound which R ² shows a methyl group, an ethyl group, and a propyl group is especially preferable.
Among the compounds of the present invention, compounds in which Y represents a hydrogen atom are preferred.

  Hereinafter, the novel compound represented by the above formula (1) of the present invention and a representative production method thereof are shown, but the present invention is not limited thereto.

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 scheme 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.

  As the solvent, 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 aforementioned solvents.

  Examples of the base include organic bases such as triethylamine, pyridine, 1,8-diazabicyclo [5.4.0] undec-7-ene (DBU), 4-dimethylaminopyridine and the like; sodium hydroxide, potassium hydroxide and the like 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 hydrogencarbonate 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), trifluoroacetic anhydride and the like. .

  The reaction temperature is, for example, -30 ° C to 150 ° C, preferably -5 ° C to 80 ° C. After completion of the reaction, the desired product may be isolated from the reaction system by a conventional method, and if necessary, it can be purified by washing with a solvent, recrystallization, column chromatography or the like to produce the desired product.

Reaction formula 2
[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 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 the reaction, and examples thereof include aromatic hydrocarbons such as benzene, toluene and xylene; ketones such as acetone, methyl ethyl ketone and methyl isobutyl ketone; Halogenated hydrocarbons such as methylene chloride; esters such as methyl acetate and ethyl acetate; or ethers such as tetrahydrofuran, dioxane, diethyl ether, 1,2-dimethoxyethane; water; acetonitrile, N, N Polar solvents such as dimethylformamide, N-methyl-2-pyrrolidone, dimethylsulfoxide etc. or mixed solvents of the aforementioned solvents.

  Examples of the base include organic bases such as triethylamine, pyridine, 1,8-diazabicyclo [5.4.0] undec-7-ene (DBU), 4-dimethylaminopyridine and the like; sodium hydroxide, potassium hydroxide and the like 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 hydrogencarbonate Hydrogen carbonates; metal alkoxides such as sodium methoxide and potassium ethoxide; metal hydrides such as sodium hydride and potassium hydride.

  The reaction temperature is, for example, -30 ° C to 150 ° C, preferably -5 ° C to 80 ° C. After completion of the reaction, the desired product may be isolated from the reaction system by a conventional method, and if necessary, it can be purified by washing with a solvent, recrystallization, column chromatography or the like to produce the desired product.

  The compound represented by the said Formula (4) or the compound represented by the said Formula (3) can be manufactured according to the method of 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 haloalkyl carbonyl group, C _1-6 alkoxycarbonyl group, C _1-6 haloalkoxycarbonyl group, C _1-6 alkoxy C _1-6 alkylcarbonyl group, C _{1- The} reaction for obtaining (1 ′ ′) from ₆ alkylsulfonyl group, C _1-6 haloalkylsulfonyl group or cyano group can be carried out in the presence of a solvent and a base.

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

  Examples of the base include organic bases such as triethylamine, pyridine, 1,8-diazabicyclo [5.4.0] undec-7-ene (DBU), 4-dimethylaminopyridine and the like; sodium hydroxide, potassium hydroxide and the like 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 hydrogencarbonate Hydrogen carbonates; metal alkoxides such as sodium methoxide and potassium ethoxide; metal hydrides such as sodium hydride and potassium hydride.

  The reaction temperature is, for example, -30 ° C to 150 ° C, preferably -5 ° C to 80 ° C. After completion of the reaction, the desired product may be isolated from the reaction system by a conventional method, and if necessary, it can be purified by washing with a solvent, recrystallization, column chromatography or the like to produce the desired product.

Reaction formula 4
[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)]

  From (6) and (2), the reaction for obtaining (7) 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 the reaction, and examples thereof include aromatic hydrocarbons such as benzene, toluene and xylene; ketones such as acetone, methyl ethyl ketone and methyl isobutyl ketone; Halogenated hydrocarbons such as methylene chloride; esters such as methyl acetate and ethyl acetate; or ethers such as tetrahydrofuran, dioxane, diethyl ether, 1,2-dimethoxyethane; water; acetonitrile, N, N Polar solvents such as dimethylformamide, N-methyl-2-pyrrolidone, dimethylsulfoxide etc. or mixed solvents of the aforementioned solvents.

  Examples of the base include organic bases such as triethylamine, pyridine, 1,8-diazabicyclo [5.4.0] undec-7-ene (DBU), 4-dimethylaminopyridine and the like; sodium hydroxide, potassium hydroxide and the like 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 hydrogencarbonate Hydrogen carbonates; metal alkoxides such as sodium methoxide and potassium ethoxide; metal hydrides such as sodium hydride and potassium hydride.

  The reaction temperature is, for example, -30 ° C to 150 ° C, preferably -5 ° C to 80 ° C. After completion of the reaction, the desired product may be isolated from the reaction system by a conventional method, and if necessary, it can be purified by washing with a solvent, recrystallization, column chromatography or the like to produce the desired product.

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

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

  Examples of the base include organic bases such as triethylamine, pyridine, 1,8-diazabicyclo [5.4.0] undec-7-ene (DBU), 4-dimethylaminopyridine and the like; sodium hydroxide, potassium hydroxide and the like 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 hydrogencarbonate Hydrogen carbonates; metal alkoxides such as sodium methoxide and potassium ethoxide; metal hydrides such as sodium hydride and potassium hydride.

  The reaction temperature is, for example, -30 ° C to 150 ° C, preferably -5 ° C to 80 ° C. After completion of the reaction, the desired product may be isolated from the reaction system by a conventional method, and if necessary, it can be purified by washing with a solvent, recrystallization, column chromatography or the like to produce the desired product.

Representative compounds represented by the formula (1) are illustrated in Tables 1 to 6, but the present invention is not limited thereto.
Physical properties in the table indicate properties or melting point (° C), "n-" is normal, "s-" is secondary, "t-" is tertiary, and "i-" is "C-" is cyclo, "Me" is methyl, "Et" is ethyl, "Pr" is propyl, "Bu" is butyl, "Hex" is hexyl "Ph" represents a phenyl group. In addition, “H” in the column of “(W) n ¹ ” or “(Y 1) n ³ ” indicates that W or Y ¹ is a hydrogen atom, and “(Y 1) n ³ ” What is shown as "5-CF3" in the column indicates that the 5-position of the pyridyl group is substituted with CF3, and so forth.

In the general formula (A) (in the formula (1), X is H, Y is a 4-position (Y ¹ ) n ³ -pyridyloxy group, Z ¹ is O, Z ² is O).
(A)
R ³ = H, provided that Compound No. 12 represents R ³ = Me.

General formula (B) (In formula (1), X is H, Y is (Y ¹ ) n ³ -pyridyloxy group at 2-position, Z ¹ is O, Z ² is O.)
(B)
It shows R ³ = H.

Table 2

General formula (C) (In formula (1), X is H, Y is (Y ¹ ) n ³ -pyridyloxy group at ³ -position, Z ¹ is O, Z ² is O.)
(C)
It shows R ³ = H.

Table 3

General formula (D) (In formula (1), X is H, Y is a 4-position (Y ¹ ) n ⁴ -phenoxy group, Z ¹ is O, Z ² is O)
(D)
It shows R ³ = H.

Table 4

General formula (E) (In formula (1), X is H, Y is 5-trifluoromethylpyridyloxy group at 4-position, Z ¹ is O, Z ² is N-R ⁶ )
(E)
It shows R ³ = H.

Table 5

In the general formula (F) (in the 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 Indicates O.)
(F)

Table 6

The agricultural and horticultural drug according to the present invention contains, as an active ingredient, at least one selected from the group consisting of a compound of the formula (1) or an N-oxide thereof or a salt thereof.
The amount of the active ingredient contained in the agricultural and horticultural drug of the present invention is preferably 0.01 to 90% by mass, more preferably 0.05 to 85% by mass, still more preferably 0. It is about 05 to 80% by mass.

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

  Examples of bactericidal agents (common name) which can be mixed or used together with a preparation containing the compound of the formula (1) of the present invention or its N-oxide or a salt thereof as an active ingredient are shown below. It is not limited to this.

  As a bactericidal agent that inhibits nucleic acid synthesis, for example, benalaxyl (benalaxyl), benalaxyl M (benalaxyl M), furalaxyl (furalaxyl), metalaxyl (metalaxyl), metalaxyl M (metalaxyl M), oxadixyl, oxrace (ofurace), (Bupirimate), dimethirimol (dimethirimol), ethylimol (ethirimol), hydroxyisoxazole (hydroxyioxazole), hymexazole (hymexazol), octilinone (octhilinone), oxolinic acid and the like.

  Examples of bactericidal agents that inhibit mitosis and cell division include benomyl, carbendazim (carbendazim), fuberidazole, thiabendazole, thiabendazole, thiophanate, thiophanate methyl (thiophanate-methyl), dietophencarb (diethofenb) And zoramide), zarylamide (zariamido), ethaboxam, pencycuron, fluopicolide and the like.

  As a bactericidal agent that inhibits respiration, for example, diflumetrim, tolfenpyrad, tebufenpyrad, fenazaquin, pyridaben, pyridaben, fenpyroximate, pyrimidiphene, rotenone (rotenilone) benodanil), flutolanil (flutolanil), mepronil (mepronil), isofetamide (isofetamid), fluopyram (fluopyram), fenfuram (fenfuram), carboxin (carboxin), oxycarboxin (oxycarboxin), thifluzami (Thifluzamide), benzobindiflupyr (benzovdiflupyr), bixafen (bixafen), fluxapyroxad (fluxapyroxad), furametopyr (furametpyr), isopyrazam, penflufen (penflufen), penthiopyrad (penthiopyrad), sedaxane, Boscalid (boscalid), pyraziflumid (pyraziflumid), pydiflumetofen (pydiflumetofen), isoflucypram (Isoflucypram), azoxystrobin (azoxystrobin), spiderxistrobin (coumoxystrobin), enoxastrobin (enoxastorobin (enoxasrobin) robin), fluphenoxystrobin, picoxystrobin, pyraoxystrobin, pyraclostrobin, pyramethostrobin, triclopyricarb, cresoximmethyl (pyroxystrobin) kresoxim-methyl), trifloxystrobin, dimoxystrobin, phenaminstrobin, metominostrobin, oryzastrobin, famoxadone, fluoxastrobin, fenamidone ), Pyribencarb (cyribofn), cyazofamid (cyazofamid), amisulbrom (amisulbrom), binapakryl (binapacryl), meptyldinocap (meptyldinocap), dinocap (dinocap), fluzinam (fluazinam), silthiofam (silthioptam), There may be mentioned teffloquin and the like.

  Examples of bactericidal agents that inhibit amino acid and protein synthesis include andoprim (andoprim), cyprodinil, mepanipyrim, pyrimethanil, pyrasithanil, blasticidin S, kasugamycin (kasugamycin), streptomycin (strepomycin) And oxytetracycline), mildiomycin and the like.

  Examples of bactericidal agents that inhibit signal transduction include quinoxyfen (quinoxyfen), proquinazid (proquinazid), fenpiclonil (fenpiclonil), fludioxonil (fludioxonil), clozolinate (chlozolinate), iprodione (iprodione), procymidone (procymidone), vinclozolin (vinclozolin) Can be mentioned.

  Examples of bactericidal agents that inhibit lipid and cell membrane synthesis include edifenphos, iprobenphos, pyrazophos, isoprothiolane, biphenyl, chlorophenyl, chloroneb, quintozene, technazen, tolclophos. Methyl (tolclofos-methyl), ecromezole (echlomezole), iodocarb (iodocarb), propamocarb (propamocarb), prothiocarb (prothiocarb) and the like can be mentioned.

  Examples of bactericidal agents that inhibit sterol biosynthesis in cell membranes include, for example, triforine, pyrifenox, pilisoxazole, fenarimol, nuarimol, imazalil, oxiposaconazole, Peflazoate (pefurazoate), prochloraz (prochloraz), triflumizole (triflumizole), azaconazole (azaconazole), bitertanol (bitertanol), bromuconazole (bromuconazole), cyproconazole (cyproconazole), difenoconazole (difenoconazole) iniconazole), epoxiconazole (epoxiconazole), etaconazole (etaconazole), fenbuconazole (fenbuconazole), fluquinconazole (fluquinconazole), flusilazole (flusilazole), fluotrimazole (fluotrimazole), fluconazole (furconazole), fur triahol flutriafol), hexaconazole (hexaconazole), imibenconazole (imibenconazole), ipconazole (ipconazole), metconazole (metaconazole), microbutanil (myclobutanil), penconazole (penconazole) Propiconazole (propiconazole), Simeconazole (simeconazole), Tebuconazole (tebuconazole), Tetraconazole (tetraconazole), Triadimefon (triadimefon), Triadimenol (triadimenol), Triticonazole (triticonazole), Prothioconazole (prothioconazole) Uniconazole P (uniconazole-P), buthiobate (buthiobate), diclobutrazol (diclobutrazol), aldimorph (aldimorph), dodemorph (dodemorph), fenpropimorph (fenpropimorph), tridemorph (tridemorph), Fenpropidin (fenpropidin), piperaline (piperalin), spiroxamine (spiroxamine), fenhexamid (fenhexamid), fenpyrazamine (fenpyrazamine), florpirauxifen (florpyrauxifen), ipfentrifluconazole (ipfentrifluconazole), naftifine (naftifine) Terbinafine (terbinafine) etc. are mentioned.

  As bactericidal agents that inhibit cell wall biosynthesis, for example, validamycin (validamycin), polyoxin (polyoxin), dimethomorph (dimetomorph), flumorph (flumorph), pyrimorph (pyrimorph), beniba avalikab (benthiavalicarb), iprobaricarb (iprovalicarb), valeraterate (Valifenalate), mandipropamide (mandipropamid) and the like.

  Examples of bactericidal agents that inhibit cell wall melanin synthesis include fushalides (phthalides), pyroxilons (pyroquilons), tricyclazoles (tricyclazoles), carpropamides (carpropamids), diclocymets, phenoxanyls, and the like.

  As fungicides for inducing the resistance of host plants, for example, probenazole (probenazole), thiazinil (thiadinil), isotianil (isotianil), laminarin (laminarin), extract from giant knotweed, acibenzolar-S methyl (acibenzolar-S) -Methyl) and the like.

  For example, copper (copper), DBEDC (complex of bis (ethylenediamine) copper-bis- (dodecylbenzenesulfonic acid)), copper hydroxide (copper hydroxide), copper nonylphenol sulfonate nonylphenol sulfonate, copper oxychloride, basic copper sulfate, organic copper (oxine-copper), sulfur (sulfur), lime sulfur compound (calcium polysulfide), silver (silver), DD (1,3-dichloropropene), dazomet (dazo) et. al., methyl bromide, methylisothiocyanate, carbam (metam-ammonium), manzeb (mancozeb), maneb (maneb), methiram (metilam), propineb (propineb), thiuram (thiram), etc. Zinc sulfate (zinc sulfate), zineb (zineb), ziram (ziram), captan (captan), captafol, capretol (folpet), chlorothalonil, dichlofluanid, tolylfluanid (tolylfluanid) , Guazatine, iminoctadine Salt (iminoctadine acetate), iminoctadine carbonochloridate tagine Alves Sil salt (iminoctadine-DBS), triazine (anilazine), dithianon (dithianon), Kinomechioneto (chinomethionat), Furuoruimido (fluoroimide), Daisen stainless (dithane-stainless), and the like.

  Other fungicides include, for example, cymoxanil, fosetyl, phosphoric acid, phosphite, tecloftalam, triazoxide, flusulfamide, diclomedin diclomezine), methasulfocarb, cyflufenamide, metrafenone, pyriofenone, dodine, flutianil, flumiii, ferimzone, oxathiapiproline , Tolprocarb, picalbutrazox, machine oil (petroleum oil), organic oil (organic oil), potassium hydrogen carbonate (potassium hydrogen carbonate), sodium hydrogen carbonate (sodium hydrogen carbonate), hypochlorous acid Sodium (sodium hypochlorite), calcium carbonate (calcium carbonate), benthiazole (dithiobutrazole), flumetober (flumetover), thiadiazine (thiadiazin), diklone (dichlone), organotin (organo-tino) ) Shiitake mycelium extract (extract from mushroom), quinofumerin (Quinofumelin), quinoline compound described in WO 2011/018174 pamphlet, Pyridazine compound described in WO 2005/121104 pamphlet, WO 2011/162397 The pyrazole compound as described in the pamphlet, the tetrazolinone compound as described in the pamphlet of WO2013 / 162072, etc. are mentioned.

  An example of a compound (common name) having insecticidal activity, acaricidal activity or centripetal activity which can be mixed or used together with a preparation comprising the compound of the formula (1) of the present invention or its N-oxide or salt thereof as an active ingredient Although shown, insecticides, acaricides or nematocides which can be mixed or used together are not necessarily limited thereto.

  Examples of organophosphorus agents include acephate, azinphos-methyl, chlorpyrifos, diazinon, dichlorvos, dimethon-S-methyl, dimethoate, and the like. Dimethylvinphos, disulfon (disulfoton), ethion (ethion), fenitrothion (fentrothion), fenthion (fenthion), isoxathion (isoxathion), malathion (malathion), methamidophos (methamidophos), methidathion (methidathon) on, monocrotophos, naled, oxidoprofos (oxideprofos), parathion, parathion, phenthoate, phosalone (phosalone), pyrimiphos-methyl, pyridaphenthion, profenofos ( profenofos), prothiophos (propaphos), pyraclofos (pyraclofos), salithion (salithion), sulprofos (sulprofos), thiometon (thiometon), tetrachlorvin phos (tetrachlorvinfos), trichlorfon (t ichlorphon), mention may be made of Bamidochin (vamidothion) and the like.

  As a carbamate agent, for example, alaniccarb (alanycarb), bendiocarb (benfurocarb), carbaryl (carbaryl), carbofuran (carbofuran), carbosulfan (carbosulfan), ethiophene carb (ethiofencarb), fenobucarb (fenobucarb), frathiocarb (Furathiocarb), isoprocarb (isoprocarb), methomil (methomyl), metolcarb (metolcarb), pirimicarb (pirimicarb), propoxur, thiodicarb and the like.

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

  As pyrethroid agents, for example, acrolinathrin (acrinathrin), allethrin (allethrin), bifenthrin (bifenthrin), cycloprothrin (cycloprothrin), cyfluthrin (cyfluthrin), cyhalothrin (cyhalothrin), cypenothrin (cyphenothrin), cypermethrin (cypermethrin), deltamethamtine deltamethrin), etofenprox (ethofenprox), fenpropathrin (fenpropathrin), fenvalerate (fenvalerate), flucythrinate (flucythrinate), flufenprox (flufenprox), fluvalinate (fluvali) ate, framethrin (furamethrin), halophenprox (halfenprox), imiprothrin (imiprothrin) permethrin (permethrin), phenothrin (phenothrin), prarethrin (prallethrin), pyrethrin (pyrethrins), resmethrin (resmethrin), silafluofen (silafluofen), (Tefluthrin), tralomethrin (tralomethrin), transfluthrin etc. can be mentioned.

  Examples of neonicotinoid agents include acetamiprid (acetamiprid), clothianidin, dinotefran, dinotefran, imidacloprid, nitenpyram, thiacloprid, thiamethoxam and the like.

  Examples of the diamide agent include chlorantraniliprole (cyanoraniliprore), cyantraniliriprole (cyantraniliprore), cyclaniliprol (cyclaniliprore), tetraniriprole (tetraniliprole), flubenziamide and the like.

  Examples of insect growth regulators such as benzoylurea agents include bistrifluron (chlorofluazuron), diflubenzuron (diflubenzuron), flucycloxuron (flucycloxuron), flufenoxuron, flufenoxuron, hexaflumuron (hexaflumuron) And lufenuron, novaluron, noviflumuron, teflubenzuron, triflumuron, buprofezin, cyromazine and the like.

  Examples of phenylpyrazole agents include ethiprole (etiprole), fipronil (fipronil), acetoprole (acetoprole), pyrafluprole (pyrafluprole), pyriprole (pyriplore) and the like.

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

  Examples of diacylhydrazone agents include chromafenozide halofenozide, methoxyfenozide, tebufenozide and the like.

  Examples of juvenile hormone agents include diofenolan, fenoxycarb, hydroprene, methoprene, pyriproxyfen and the like.

  Examples of insecticidal substances produced by microorganisms include abamectin (abamectin), emamectin benzoate (emamectin-benzoate), ivermectin (ivermectin), lepimectin (lepimectin), milbemectin (milbemectin), nemadectin (nemadectin), and nikkomycin (Nikkomycin) Polyoxin complex (polioxin), spinetoram (spinetram), spinosad (spinosad), BT agent (Bacillus thuringiensis and insecticidal protein product), etc. can be mentioned.

  As insecticidal substances derived from natural products, for example, anabasine (azabasa), azadiractin (azadiractin), deguelin (deguelin), fatty acid glyceride (decanolyoctanoylglycerol), hydroxypropyl starch (hydroxy propyl starch), soybean lecithin (lecithin), nicotine (nicotine) ), Nornicotine (nornicotine), sodium oleate (oreic acid sodium salt), machine oil (petroleum oil), propylene glycol monofatty acid ester (propylene glycol monolaurate), rapeseed oil (rape oil), rotenone (rotenone), sorbita Fatty acid esters (Sorbitan fattyacid ester), starch (starch) and the like.

  Other insecticides include, for example, afidpyropene, brofranilide, chlorfenapyr, diafenthiuron, dichloromezotiaz, DBEDC (Dodecylbenzenesulfonylic acid bis ethylenediamine hydrochloride) (Flonicamido), flomethoquin (flometoquin), fluphenerim (flufenerim), fluhexafon (fluhexafon), flupyradifurone (flupyradifurone), hydramethylnon (hydramethylnon) Indoxacarb (indoxacarb), metaflumizone (metaflumizone), meta aldehyde (metaldehyde), nicotine sulfate (nicotin sulfate), pimetrozine (pymetrozine), pyridalyl (pyridalyl), pyrifluquina zon (pyrifluquinq zon), spirotetramat (spirotetramat), sulphuramide (sulfuramide) And sulfoxaflor (sulfoxaflor), triflumezopyrim, tolfenpyrad (tolfenpyrad), triazamate etc.).

  As acaricides, for example, acequinocyl, acynonapyr, amidoflumet (amidoflumet), amitraz, azocyclotin, azocyclotin, benzoxiate, bifenazate, binapacryl, binisocryl Rate (bromopropylate), quinomethionate (chnomethionate), clofenthezine (clofantezine), sienopyraphen (cyenopyrafen), ciflumethofen (cyflumetofen), tricyclohexyl tin hydroxide (cyhexatin), dicofol (dicofol), dienoclo (Dienochlor), diflovidazine (diflovidazin), etoxazole (ethoxazole), fenazaflor (fenazaflor), fenazaquin (fenazaquin), fenbutatin oxide, phenothiocarb (fenothiocarb), fenpyroximate, , Pirimidifen, polynactin complex (polynactins), propargite (propargite), pyflubumide (pyflubumide), pyridaben (pyridaben), spirodiclofen (spirodino) clofen), spiromesifen, tebufenpyrad, tetradifon and the like.

  As a nematocide, for example, aluminum phosphide (aluminum phosphide), benclothiaz (benclothiaz), kazusaphos (cadusafos), ethoprofhos (ethoprophos), fluensulfone (fluensulfone), fluopyram (fluopyram), foschiazate (fosthiazate), furfural (furfural) , Imicyafos (imicyafos), levamisol hydrochloride (levamisol hydrochloride), mesulfenphos (mesulfenfos), carb (metam-ammonium), methyl isocyanate (methyl isothiocyanate), morantartarterate , Oxamyl (oxamyl), thifluzamide (thifluzamide), can be exemplified Chiokisazafen (thioxazafen) or the like.

  As bait bait, for example, chlorofacinone (chlorphacinone), coumatetralyl (coumatetralyl), difacine (diphacinone), monofluoroacetic acid salt (sodium fluoride), warfarin (warfarin) and the like can be mentioned.

  The composition provided by the present invention can be used for the prevention or control of harmful pests in situations such as agriculture, indoors, forests, livestock, and sanitation. Specific usage situations, target pests, and usage methods are shown below, but the contents of the present invention are not limited thereto.

  The agricultural and horticultural drug compositions of the present invention are agricultural products such as food crops (rice, barley, wheat, rye, oats, etc., potatoes, potato, sweet potato, taro, yams, soybeans, soybeans, red beans, etc. Sora beans, peas, beans, peanuts and other beans, corn, salmon, buckwheat, etc., vegetables (cabbage, Chinese cabbage, daikon radish, salmon, broccoli, cauliflower, crucifers, etc. cruciferous crops, pumpkin, cucumber, watermelon, Cucurbitaceous crops such as melon, zucchini, cucumber, garlic, eggplants, solanaceous crops such as eggplants, tomatoes, peppers, peppers, peppers, mussels such as okra etc. Amoyaceous crops such as spinach and common bean, Seriaceae crops such as carrots, honeybees, parsley, celery and wheat, Chrysanthemum crops such as lettuce and burdocks, garlic, onions, green onions, leeks, etc Green onions, asparagus, shiso, lotus root etc., mushrooms (shiitake mushrooms, mushrooms etc), fruit trees and fruits (citrus fruits, apples, pears, peaches, plums, cherry blossoms, li, persimmon, persimmon, persimmon, persimmon, persimmon, no flowers, Akebono, blueberries, raspberries, pineapples, mangoes, kiwifruits, bananas, strawberries, olives, walnuts, chestnuts, almonds, etc., perfumes, etc. ornamental products (lavender, rosemary, thyme, sage, pepper, ginger, etc.), special purpose Crops (tobacco, tea, sugar beet, sugar cane, bitter gourd, sesame, konnyaku, hop, cotton, hemp, olive, gum, coffee, seeds, sunflower, persimmon etc.), grass and feed crops (timothy, clover, alfalfa etc.) Bean grass, corn, sorghum, grass such as orchardgrass, etc., turf (Korai grass, bentgrass etc.), forest trees Abies (Abies sp.), Pines, pines, hija, cedar, mulberry etc. and ornamental plants (Kiku, roses, carnations, lilies, Eustoma grandiflorum, persimmon root sprouts, starches, herbs such as orchids, ginseng, cherry blossoms, It is used in the cultivation scene of garden trees, etc.).

  Pests targeted by the pharmaceutical composition for agricultural and horticultural purposes of the present invention include fungi and bacteria such as Eumycota, Myxomycota, Bacteriomycota, Actinomycota, etc. It can be used to control the diseases that they cause.

Specific examples of the disease include rice blast (Pyricularia oryzae), sesame leaf blight (Cochliobolus miyabeanus), sheath blight (Rhizoctonia solani), inner blanching disease (Pantoea ananatis), fool disease (Gibberella fujikuroi), Seedling blight (Pythium graminicolum), brown stripe disease (Acidovorax avene subsp. Avenae), leaf sheath browning disease (Pseudomonas fuscovaginae), leaf blight disease (Xanthomonas oryzae pv. Oryzae), blight disease (Burkholderia plantarii etc.) Powdery mildew (Erysiphe graminis), Fusarium head blight (Gi berella zeae), rust (Puccinia striiformis, P. graminis, P. recondita, P. hordei), snow blight (Typhula sp., Micronectriella nivalis), naked panicle disease (Ustilago tritici, U. nuda), brown scab (Tilletia caries), eye diseases (Pseudocercosporella herpotrichoides), scab (Rhynchosporium secalis), leaf blight (Septoria tritici), blight (Leptosphaeria nodorum), web blight (Pyrenophora teres), scab (Helminthosporium sp.) tum Ikata), black node disease (Pseudomonas syringae pv. japonica), etc .; citrus black spot (Diaporthe citri), scab (Elsinoe fawcetti), fruit rot (Penicillium digitatum, P. italicum), brown rot (Phytophthora) citrophthora ,, P. nicotianae, black scab (Phyllostictina citricarpa), etc .; apple monilia disease (Monilinia mali), brown spot disease (Diplocarpon mali), decay disease (Valsa mali), powdery mildew (Podosphaera leucotricha), spotted leaf litter Disease (Alternaria mali), black star Disease (Venturia inaequalis), melanose disease (Mycospherella pomi), anthracnose (Colletotrichum acutatum, Glomerella cingulata), ringworm disease (Botyosphaeria berengeriana), red star disease (Gymnosporangium yamadae), soot blight disease (Zygophiala jamaicensis) (Gloeodes pomigena) et al .; no scab (Venturia nashicola, V.). pirina), powdery mildew (Phyllactinia mali), black spot (Alternaria kikuchiana), red star disease (Gymnosporangium haraeanum), marsh disease (Monilinia fructigena), ring disease (Botyosphaeria berengeriana), etc .; Monilinia fructicola), Anthrax disease (Glomerella cingulata), Phytophthora blight (Monilinia kusanoi), etc .; peach scab (Monilinia fructicola), scab (Cladosporium carpophilum), phomopsis putrefaction (Phomopsis sp.), Borehole bacteria Disease (Xanthomonas camp estris pv. pruni), etc .; grape rot (Elsinoe ampelina), late rot (Colletotrichum acutatum, Glomerella cingulata), powdery mildew (Uncinula necator), rust (Phakopsora ampelopsidis), blacklot disease (Gignardia bidwellii) Downy mildew (Plasmopara viticola),
Blight scab (Cladosporium viticolum), root-head cancerous bacterial disease (Agrobacterium vitis), etc .; persimmon anthracnose (Gloeosporium kaki), powdery mildew (Phyllactinia kakicola), deciduous disease (Cercospora kaki, Mycoshaerella nawae), kiwi fruit Scleroderma (Phomopsis sp.), Anthracnose (Colletotrichum gloeosporioides, Colletotrichum acutatum), white scab (Rosellinia necatrix), scarlet brown spot (Phyllosticta eriobotryae), horny mildew (Pseudocercospora eriobotryae), etc. of Anthracnose (Colletotrichum lagenarium), powdery mildew (Sphaerotheca fuliginea, Oidiopsis taurica), vine blight (Didymella bryoniae), vine scab (Fusarium oxysporum), downy mildew (Pseudoperonospora cubensis), epidemic (Phytophthora sp.) Seedling blight (Pythium sp., Rhizoctonia solani), etc .; Spotted blight of cucumber (Pseudomonas syringae pv. Lochrymans), margin blight (Pseudomonas viridiflava), brown spot blight (Xanthomonas campestris pv. Cucurbitae) Etc .; Melon brown spot blight (Xanthomonas campestris pv. Cucurbitae), hairy root disease (Agrobacterium rhizogens), oncosis (Streptomyces sp.) Etc .; Pancreatic fruit blight disease (Acidovorax avenae pv. Citrulli) etc; Blight of the eggplant vegetables (Ralstonia solanacearum), etc .; tomato blight (Alternaria solani), leaf blight (Cladosporium fulvum), plague (Phytophthora infestans), mildew (Pseudocercospora fuligena), powdery mildew (Erysiphe) cichoracearum), caustic agent (Clavibac) er michiganense subsp. michiganense), stem rot (Pseudomonas corrugata), soft rot (Pectobacterium carotovorum subsp. carotovorum), etc .; Blight (Corynespora melongenae), brown scab (Paracercospora egenula), brown rot (Phytophthora capsici), half-body wilt (Verticillium dahliae) etc .; dwarf diseases of cruciferous vegetables (Peronospora parasitica), black spot (Alt) rnaria japonica), white rot (Cercosporella brassicae), soft rot (Pectobacterium carotovorum subsp. carotovorum), yellow rot (Verticillium dahliae), etc .; black rot (Pseudomonas syringae pv. Etc. Lettuce downy mildew (Bremia lactucae) bottom blight (Rhizoctonia solani), rot (Pseudomonas cichorii, Pseudomonas viridiflava), blight disease (Xanthomonas campestris pv. vitians), downy mildew of green onion (Peronospora destructor), black spot (Alternaria porri), rust (Puccinia allii), white scab (Sclerotium rolfsii), etc .; purpura of cereus (Cercospora kikuchii), anthracnose (Cercospora kikuchii) Colletotrichum truncatum, Colletotrichum trifolii, Glomerella glycines, Gloeosporium sp.),
Downy mildew (Peronospora manshurica), stem blight (Phytophthora sojae), mildew (Elsinoe glycines), black spot (Diaporthe phaseolorum var. Sojae), blight disease (Pseudomonas savastanoi pv. Glycinea), leaf blight (Xanthomonas campestris) pv. glycines), etc .; Anthracnose (Colletotrichum lindemthianum), blight (Pseudomonas savastanoi pv. phaseolicola), leaf blight (Xanthomonas campestris pv. phaseoli), leaf blight (Rhizoctonia sola) i) et al .; black spot disease (Cercospora personata), brown spot (Cercospora arachidicola) etc .; Erysiphe pisi etc .; Phytophthial disease (Alternaria solani), plague (Phytophthora infestans) ), Leaf rot (Rhizoctonia solani), soft rot (Pectobacterium carotovorum subsp. Carotovorum), etc .; strawberry powdery mildew (Sphaerotheca humuli), anthracnose (Colletotrichum gloeosporioides, Colletotrichum actatum, Glomerellaculatingulata) Phytophthora nicotianae), cotton rot (Dendrophoma obscurans), bacterial blight (Pseudomonas marginalis pv. Marginalis), etc .; Tea brown rot (Pseudocercospora theae), anthracnose (Discula theae-sinensis), rot blotch (Pestalotiopsis) theae, Pestalotiopsis longiseta), net blight (Exobasidium reticulatum), blast (Exobasidium vexans), scab (Elsinoe leucospila), scab (Pseudomonas syringae pv. Theae), scab (Xanthomonas campestris pv. theicola), etc .; Tobacco scab (Alternaria longipes), powdery mildew (Erysiphe cichoracearum), anthracnose (Colletotrichum tabacum), downy mildew (Peronospora tabacina), plague (Phytophthora) nicotianae), blight disease (Ralstonia solanacearum), cavity disease (Pectobacterium carotovorum subsp. carotovorum), etc .; brown spot disease of cervix (Cercospora beticola), root rot (Rhizoctonia solani, Thanatephorus cucu) eris), seedling blight (Aphanomyces cochliodes), etc .; rose blight (Diplocarpon rosae), powdery mildew (Sphaerotheca pannosa), etc .; brown leaf blight (Septoria chrysanthemi-indici), white rust (Puccinia horiana) Botrytis cinerea etc .; Botrytis cinerea of various crops such as eggplant, cucumber and lettuce; sclerotia sclerotiorum; snow blight of grasses (Pythium iwayamai, Tyohula) incarnate, Fusarium nivale, Sclerotinia boreali ), Powdery mildew (Erysiphe graminis), farying disease (Lycoperdon perlatum (Lycoperdon perlatum, Lepista subnudo, Marasmius oreades), pseudo leaf disease (Ceratobasidium spp.), Blight disease (Gaemannomyces graminis), cavalaria leaf blight (Curvularia geniculata) Leaf rot (Rhizoctonia solani), Pythium disease (Pythium periplocum, Pythium vanterpoolii), rust (Puccinia spp.), Dollar spot disease (Sclerotinia homoeocarpa), etc .; Bentgrass (Pythium aphanidermatum), charcoal Disease (Colletotrichum sp. ), Berry rot of Botrytis (Botryosphaeria sp.), Anthracnose (Glomerella cingulata), Ring disease of Pheasant (Phoma exigua), Spotted disease (Phyllosticta hydrangeae), Leaf blotch (Corynespora cassiicola), Leaf Rot (Rhizoctonia solani), powdery mildew (Oidium sp.), Anthracnose (Glomerella cingulata), Botrytis (Cercospora hydrangae), Ginkgo moth (Gonatobotryum apiculatum), red blight (Erythricium salmonicolor), Red blight (Gymnosporangium yamadae), white scab Rosellinia necatrix), maple such chromone disease (Rhytisma acerinum), ring Sheath blight (Cristulariella moricola),
Blight mildew (Diaporthe sp.), Soub spot disease (Cercospora sp.), Anthracnose (Colletotrichum gloeosporioides), red blight (Erythricium salmonicolor), powdery mildew (Uncinula sp., Sawadaea sp., Oidium sp.) White leaf spot (Phomatospora albomaculans), powdery mildew (Uncinula sp., Microsphaera alphitoides, Erysiphe gracilis), mildew (Armillaria mellea), brown heart disease (Phaeolus schweinitzii), brown leaves Plaque (Septoria chinensis), blight (D aporthe melanocarpa, Diaporthe alleghaniensis, anthrax anthrax (Glomerella cingulata), tinea scabies (Passalora okinawaensis), spotted disease (Phaeosphaerella gardeniae), brown spot disease of burns (Pseudocercospora zelkove) , Back ulcerative powdery mildew (Phyllactinia magnoliae), Spotted disease (Phyllosticta concentrica), Oncosis of nematode (Nectria galligana), Root-head oncosis (Agrobacterium tumefaciens), Powdery mildew (P) odosphaera longiseta, podosphaera tridactyla), spiny nest disease (Taphrina wiesneri), juvenile mildew (Monilinia kasanoi), blight disease (Armillaria mellea), blight disease (Valsa ambiens), prickly scab (Sphaceloma punicae) , Powdery mildew of the slipper (Uncinuliella australiana), brown spot (Pseudocercospora lythracearum), ring leaf blight (Cristulariella moricola), scab mildew (Pseudocercospora crataegi), white spot of mildew (Bagcheea albo) -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. Blight disease (Cercospora sequoiae), fine powder blight disease (Macrophoma phaseolina), red blight disease (Ascochyta sp.), Apricot powdery mildew (Microsphaera izuensis), brown spot disease (Septoria azaleae) White scab (Rosellinia necatrix), seedling blight (Rhizoctonia solani), leaf blight (Pseudocercospora handelii), spotted disease (Phyllosticta maxima), flower rot fungus (Ovulinia azaleae), bulbous disease (Exobasidium pentasporium) ), Tsubaki (Phytophthora cinnamomi), anthrax (Glome) ella cingulata), Blight disease (Armillariella mellea), Powdery mildew of roses (Sphaerotheca pannosa, Oidium sp.), Downy mildew (Peronospora sparsa), Spot disease (Cercospora rosicola, Mycosphaerella rosicola), Epidemic megasperma), scab (Marssonina rosae, Diplocarpon rosae), rot (Cryptosporella umbrina), scab (Rosellinia necatrix), Hinoki plague (Armillariella mellea), Pestalotias (Pestalotips) s sp., Fusarium head blight (Erwinia herbicola pv. millettiae), poinsettia root rot (Rythium sp.), swine plague (Phytophthora cactorum), powdery mildew (Erysiphe paeoniae), bud blight (Alternaria sp.) ), Anthrax disease (Gloeosporium sp.), Brown spot disease (Pseudocercospora variicolor), Sclerotinia sclerotiorum, Botrytis disease (Botrytis paeoniae), White Coat Blight (Rosellinia necatrix), Mako disease (Oidium) euonymi-japonici), brown spot (Pseudocercospora destr) ctiva), pine of kelp disease (Cronartium quercuum), seedling blight (Rhizoctonia solani, Fusarium sp. , Pythium sp,,), Leaf blight (Pseudocercospora pini-densiflorae), Dazzling back-spot disease (Coccoidea querricola), Mycorrhizal mildew (Microsphaera pulchra), Spot disease (Pseudocercospora cornicola), Panacea Of Marzonina leaf blight disease (Marssonina brunnea) of Eucalyptus (Cercospora epicoccoides) of Eucalyptus, Pseudococcospora spiraeicola of snow bream (Pseudocercospora spiraeicola), powdery mildew (Sphaerotheca spiraeae), powdery mildew of lilac (Microphageae)枯Nuclear disease (Sclerotinia sclerotiorum), morning glory vulgaris (Fusarium oxysporum f. Sp. Batatas), carnation powdery mildew (Oidium dianthi), Gerbera powdery mildew (Sphaerotheca fuliginea), anthracnose (Colletotrichum sp.) Sclerotinia sclerotiorum, Fusarium wilt (Fusarium oxysporum), powdery mildew (Erysiphe cichoracearum), sclerotia sclerotiorum, Verticillium dahliae, Fusarium talisophila (Fusarium) Anthrax of goldfish ( Colletotrichum gloeosporioides), powdery mildew (Oidium subgenus Reticuloidium), sclerotis disease (Sclerotinia sclerotium), cosmos anthracnose (Colletotrichum acutatum, Gloeosporium sp.), Powdery mildew (Sphaerotheca fucica) Powdery mildew (Oidium sp.), Damping-off disease (Fusarium moniliforme), sclerotis disease (Sclerotinia sclerotiorum), powdery mildew of sweetype (Oidium sp.), Wilt disease (Fusarium sp.) ), Half body wilt (Verticillium dahliae), anthrax (Glomerella cingulata, Colletotrichum gloeosporioides), anthracnose of Statis (Glomerella cingulata), powdery mildew (Oidium sp.), Stock wilt (Fusarium oxysporum Schlecht. sp. conglutinans), sclerotis disease (Sclerotinia sclerotiorum), anthracnose (Colletotrichum gloeosporioides, Colletotrichum higginsianum), damping-off disease (Fusarium avenaceum), half-body wilt (Verticilliu) m dahliae), Anthracnose (Colletotrichum acutatum),
Stem rot (Fusarium avenaceum), powdery mildew (Oidium sp.), Sclerotis disease (Sclerotinia sclerotiorum), sunflower powdery mildew (Sphaerotheca fusca, Erysiphe cichoracearum), sclerotis disease (Sclerotinia sclerotiorum), brown spot disease (Sclerotinia sclerotiorum) Septoria helianthi), half body wilt (Verticillium dahliae), powdery mildew of petunia (Sphaerotheca fuliginea, Oidium sp.), Sclerotia sclerotiorum, marigold half body wilt (Verticillium dahliae), etc. can be mentioned. .

  Pests such as, for example, Arthropoda, Lepidoptera, Coleoptera, Hymenoptera (Hemiptera), Heteroptera and Homoptera (Homoptera), Thymicidae (Thysanoptera), Hymenodiae (Hymenoptera), Fly (Diptera), Grasshopper (Orthoptera), Termite (Isoptera), Earwig (Dermaptera), Arthropoda: Collembola (Collembola), Arthropoda: Crustacean, etc. Lepidoptera (Isopada), Arachnid Arachnid Acrid (Acari), Mollusca Hypertripoda Primate (Arcitaenioglossa), Linear Anthropoda Phylens Tylenx (Ty) enchida), mention may be made of the Doriraimusu eyes, etc. of the tail gland rope. Specific examples of these pests are shown below, but the pests are not limited thereto.

  For example, Helicoverpa armigera, Heliothis spp., Hegrothis spp., Agrotis segetum, Autographa nigrisigna, Trichoplusia nigros, for example, Lepidoptera of Arthropoda. ), Spodoptera (Mamestra brassicae), Spodoptera exigua, Spodoptera litura, etc., Psylidae, such as Plutella xylostella, etc., and Ancholycidae (Adoxophys orana fasciata), Maki (Adoxophyes honmai), Midarekacmonhamaki (Archips fuscocupreanus), Chahamaki (Homona magnanima), Chanohoshiga (Caloptilia theivora), Nashihimeshini (Grapholita molesta), etc., Minogaceae Chaminoga (Eumeta minuscula), etc. (Lyonetia prunifoliella malinella), Momohamoguriga (Lyonetia clerkella), etc., a Phyllocnistis citrella, such as the family Phyllocnistis citrella, Phyllonorycter ringoniella, etc. Sprigidae (Acrolepiopsis sapporensis), etc., Scrayfish (Synanthedon quercus), etc., Pseudomorpha spp. Iraga (Monema flavecens), Hirohairairaaga (Parasa lepida), Himeuroiraga (Scopelodes contracus), and the like, Tsutoga Nematoda (Chilo suppressalis), Sankameiga (Scirpophaga incertulas) , Cnaphalocrocis medinalis, H. pallidata (Hellulla undalis), C. pterocarpus (Conogethes punctiferlis), cotton helicoid moth (Diaphania indica), Shibata Toga (Parapediasia teterrella), etc., Trichoderma spp. Family Papilio xuthus, etc., White-billed Butterfly (Pieris rapae crucivora), etc., Lymicidae (Lampides boeticus), etc., Phyllididae (Ascotis selenaria), etc. Megashrimp Shrimp (Agrius convolvuli), etc., Pteris (Phalera flavescens), etc., Pteris (Eprocorcis pseudoconspersa), Scutellariata (Euporcis pseudomons), Orygia recens approximans, etc., etc. Adults such as Spilosoma imparilis), Hyphantria cunea, etc., grape berry (Endopiza viteana), codling moth (Laspeyresia pomonella), larvae, eggs and the like can be mentioned.

  As an order of the order Coleoptera (Coleoptera), for example, Anomala cuprea, Anophia cuprea, Anopheles moth (Popillia japonica), Anemone spinach (Oxycetonia jucunda), etc., Anomala geniculata etc. , Click beetles (Melanotus fortnumi), etc., ladybirds (Epilachna vigintioctopunctata), etc., longhorn beetles (Anoplophora malasiaca), grape tiger beetle (Xylotrechus pyrrh) (Derus) et al., Green leaf beetles (Aulacophora femoralis), Rootworm species (Diabrotica spp.), Chrysomelidae (Phyllotreta striolata), Ground beetles (Cassida nebulosa), Radish beetles (Phaedon brassicae), Pterocarpus (Oulema carrageus) Epilachna varivestis), Colorado potato beetle (Leptinotarsa decemlineata), etc., Othossidae (Rhynchites heros), etc., Apiidae Weevil (Cylas formicarius), etc., etc. (Curculio sikkimensis), rice water weevil (Lissorhoptrus oryzophilus), cotton weevil (Anthonomus gradis grandis), weeping weevil (Sphenophrus venatus vestitus), etc. Can.

  As heteroptera of the order Hemiptera (Hemiptera), for example, the sea bug (Eurydema rugosum) of the family Hemiptera, Eysarcoris lewisi, Eysarcoris parvus, Erysarcoris parvus, southern white stink bug (Nezara viridula), Bugs (Plautia stali), Halymorpha mista, etc., Scutellariaeidae (Urochela luteovoria), etc., Longhorn Bugs (Togo hemipterus), etc., Heliphagidae Hoso Harimushi ( letus punctiger) and the like, spider spider bug (Leptocorisa chinensis) and the like of the gospel bug family, Dysdeercus cingulatus and the like of the gospel bug family, stephanitis nashi of the gossip family, stephanitis pyrioides etc., and the like Adults, larvae, and eggs of the beetles (Apolygus spinolai), red-tailed snail (Stenotus rubrovittalus), red-tailed snail (Trigonotylus coelestialium), etc. It can be mentioned.

  As homopterus (Homoptera) of the order Hemiptera, for example, Platypleura kaempferi of the semifamily, such as the flathead beetle (Arboridia apicalis) of the leafhopper family, the green leafhopper (Empoasca onukii), the black leafhopper , White-winged Tuna Leafhopper (Nephotettix virescens), etc., Ground planthopper (Laodelphax striatellus), Tobiirounka (Nilaparvata lugens), Sejironka (Sogatella furcifera), etc., Aobahagoromomo (Geishadistinct) ssima) et al., Psylla pyrisuga of the family Phyllidae, Diaphorina citri, etc., Aleurocanthus spiniferus of the family of the family Bemisia (Aleurocanthus spiniferus), Silverleaf whitefly (Bemisia argentifolii), various species of the whitefly (Bemisia tabaci) Citrus whitefly (Dialeurodes citri), Monascus sinensis (Trialeurodes vaporariorum), etc., Phylloxera grapevine nematodes (Viteus vitifolii) etc., Aphisidae aphids (Aphis citricola), Aphid aphids (Aphis citricola) vora), cotton aphid (Aphis gossypii), potato longhorn aphid (Aulacorthum solani), radish aphid (Brevicoryne brassicae), comican aphid (Toxoptera aurantii), red-handed aphid (Toxoptera citricidus), aphid Aphids (Schizaphis piricola), Nasimidrio aphids (Nippolachnus piri), Pseudonymous aphids (Lipaphis erysimi), Pectinous aphids (Hyalopterus pruni), Aescariella (Pleotr) Chophorus chrysanthemi), Aphids aphid (Macrosiphoniella sanborni), Aquidella aphid (Megoura crassicauda), Aquilegia aphid (Sitobion ibarae), Alyptophus aphid (Macosiphum euphagium), as described in U.S. Pat. ), Red-winged aphid (Rhopalosiphum rufiabdominalis), Green-winged Aphid (Rhopalosiphum padi), Green-winged Aphid (Sitobion akebiae), Red-winged Aphid (Er) osma lanigerum) and the like, Icerya purchasi such as Ivya scale beetle (Icerya purchasi) and the like, Pseudococcus comstocki of the meal scale family (Pseudococcus comstocki), Mycorrhiza (Phenacoccus viburnae), and (Ceroplastes ceriferus), ruby (Ceroplastes rubens), etc., Red-backed scale insect (Aonidiella aurantii) of the red-tailed worm family (Aonidiella aurantii), Nashi-maru scale insect (Comstockaspis perniciosa), the red-billed scale insect (Pseu) aulacaspis pentagoa), Yano yanonensis (Unaspis yanonensis) adults such as, mention may be made of the larvae and eggs and the like.

  As thrips (Thysanoptera), for example, thrips thrips (Scirtothrips dorsalis), thrips thrips (Thrips palmi), Scutellariae thrips (Thrips tabaci), thrips settles (Thrips setosus), thrips thrips (Franklini intima) Yellow thrips (Frankliniella occidentalis), Croton thrips (Heliothrips haemorrhoidalis), etc., Buprestidae (Ponticulothrips diospyrosi), Oryza thrips (Haplothrips acul) atus) adult, etc., it can be mentioned the larvae and eggs and the like.

  As Hymenoptera (Hymenoptera), for example, the cuttlefish (Athalia rosae ruficornis), Chulepen sawfly (Arge pagana), etc .; Examples include adults, larvae, eggs and the like such as the black-billed bee (Megachile nipponica nipponica) and the like, and the black-and-white ant (Formica japonica) and the like.

  As the order Diptera (Diptera), for example, soybean fly (Asphondylia yushimai), etc. of the family Tatidae (Ashphilidae), and the fruit fly (Rhacochlaena japonica) of the family of fruit fly (Bactrocera cucurbitae), etc. Drosophila melanogaster (Drosophila suzukii) et al., The leafminer family Lamimyza trifolii, Lyamatolya (Chromatomyia horticola), a rice leafminer fly (Agromyza oryzae), a leaf lice fly (Liriomyza bryoniae), etc. The seedcorn maggot (Delia platura), onion maggot (Delia antiqua) adult like, can be cited larvae and eggs, and the like.

  As the grasshopper (Orthoptera), for example, adults of the grasshopper (Rspolia lineosa), etc., the shrew of the crickets (Truljalia hibinonis), etc., the cricket (Gryllotalpa orientalis), etc., and the locust scum (Oxya yezoensis) etc. Examples include larvae and eggs.

  As the termite (Isoptera), for example, adults such as termite Odontotermes formosanus, larvae, eggs and the like can be mentioned.

  For example, adults, larvae, eggs and the like of the leafhopper (Labidura riparia) of the family Anemoneidae can be mentioned as Dermaptera (Dermaptera).

  Examples of Collembola of the Arthropod lateral insect class include adults, larvae, eggs and the like of the beetles (Sminthurus viridis) of the Martobidae family, such as the Onychiurus matsumotoi of the family of the beetles of the family White Beetle family.

  Examples of an isopod of the Arthropoda crustacean (Isopada) include adults, larvae, eggs and the like, such as Armadillidium vulgare, of the family Gummoth.

  For example, as acarids (Artari) of Arthropodid Arachnida, Polyphagotarsonemus latus, Phytonemus pallidus, etc., Phythaleus major (Penthaleus major), etc., and a spider spider mites of the spider spider mites (Phytonemus majorus) Brevipalpus lewisi), Red-handed spider mite (Brevipalpus phoenicis), etc., Citrus red-eared spider mite (Panonychus citri), Apple red mite (Panonychus ulmi), Nami spider mite (Tetranychus urticae), Kanzawa spider mite (Tetranychus kanzawai), nnensis), red-handed spider mite (Oligonychus ununguis), red-eared spider mite (Eotetranychus kankitus), clover spider mite (Bryobia praetiosa), etc., Eriophysalis mites (Aculops pelekassi), Western rust mite (Eriophyes chibaensis), Grape leafminus tick (Colomerus vitis), leafminus tick (Aculus fockeui), or the like, snail (Calacarus carinatus), etc., Acaridae (Tyrophagus putrescentiae), Robin mites (Rhizoglyphus robin) i) and the like, such as adults, larvae and eggs.

  For example, Archaenioglossata of the molluscid archiopoda, Promeona caniculata (Pumacea canaliculata), etc., Plumonata such as the African mirid (Achatina fulica), slug family slugs (Meghimatium bilineatum), elderfish (Milax gagates), elderfish (Lehmannina valentiana), and staphylinidae (Acusta de specta sieboldiana) etc. can be mentioned.

  For example, as an order of the Thylenxidea (Tylenchida) of the Linear Animal Paraphyllia, such as the Anguinaceae, Ditylenchus destructor, et al. ), Minty nematode (Pratylenchus coffeae), etc., and the Hoplaromycidae (Helicotylenchus dihystera), etc., and the heteroderiaceous potato cyst nematode (Globodera rostochiensis), etc., and the sweet potato family Neisseria (Meloidogy) e 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, as the order of Dorilimes of the Uropodids, there can be mentioned Longidurus's family Oxiphinema sp., And Trichodolicum family Trichodorus sp.

  The pharmaceutical composition for agricultural and horticultural use of the present invention is a drug which 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 agriculture and horticulture of the present invention is resistant to existing agents such as benzimidazole agents, dicarboximide agents, anilinopyrimidine agents, strobilurin agents, SDHI agents, fluazinam agents, etc. It also has excellent bactericidal activity against resistant bacteria.

  The pharmaceutical composition for agricultural and horticultural purposes of the present invention can also be used for the prevention and treatment of diseases of the skin of human and domestic animals / pets and organs such as digestive system and respiratory system.

  Specific examples of pathogens that cause disease include, for example, Trichophyton rubrum, Trichophyton mentagrophytes, etc., Trichophyton mentagrophytes, etc., fungi such as Candida albicans, etc., Candida fungi, Aspergillus fumigatus, etc., Aspergillus coli, Escherichia coli, Pseudomonas aeruginosa Gram-negative bacteria such as Pseudomonas aeruginosa, Gram-positive bacteria such as Staphylococcus aureus, etc. may be mentioned.

  The compound represented by the formula (1) of the agricultural and horticultural drug of the present invention is a compound having an insecticidal activity, an acaricidal activity or a nematode activity other than the compound having a bactericidal activity, and further an active compound other than them. Can also be present as a mixture of In order to control diseases and / or weeds that occur simultaneously at the time of use, use in combination with a compound having bactericidal activity, herbicidal activity or plant growth regulating activity reduces the control effort as well as the dose reduction, etc. Synergistic effects can also be expected. Moreover, more effective control effects such as synergetic effects can be expected by using it in combination with repellents, synergists and the like.

  The agricultural and horticultural agents of the present invention may be in the form which can be taken as they are or generally in the form of agricultural chemicals, such as wettable powders, water dispersible granules, dry flowables, aqueous solvents, emulsions, solutions, oils, suspensions, aqueous suspensions and emulsions. It can be used in the form of flowable agents such as agents, capsules, powders, granules, fine granules, baits, tablets, sprays, aerosols, and the like. The agricultural and horticultural drug of the present invention contains the active ingredient in a total amount of 0.1 to 99.9% by mass, preferably 0.2 to 80% by mass.

  In order to set it as the said dosage form, the various agrochemical adjuvant conventionally used can be suitably used in the technical field of the chemical | medical agent for agriculture and horticulture. Such agrochemical adjuvant can be used, for example, for the purpose of improvement of the effect of an agricultural and horticultural drug, stabilization, and improvement of dispersibility. Examples of pesticide adjuvants include carriers (diluents), spreading agents, emulsifiers, wetting agents, dispersants, disintegrants 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, and the like Naphthalene, cyclohexane, animal and vegetable oils, fatty acids and the like can be mentioned. Further, as the solid carrier, clay, kaolin, talc, diatomaceous earth, silica, calcium carbonate, montmorillonite, bentonite, feldspar, quartz, alumina, saw dust, nitrocellulose, starch, gum arabic etc. can be used.

  As the emulsifying agent and the dispersing agent, usual surfactants can be used. For example, anionic surfactants such as higher alcohol sodium sulfate, stearyltrimethyl ammonium chloride, polyoxyethylene alkyl phenyl ether, lauryl betaine and the like Cationic surfactants, nonionic surfactants, amphoteric surfactants and the like can be used. Further, spreading agents; wetting agents such as dialkyl sulfosuccinates; 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 fungi and other pests, soil is usually applied to the foliage of the plant in places where damage by these pests is occurring or where there is a possibility that damage may occur. All layer mix, line application, side line application, floor soil mix, cell seedling treatment, planting hole treatment, stock source treatment, top dress, rice box treatment, water surface application, etc. Can also be used. In addition, it can be used by immersing seeds in a drug, seed treatment such as seed dressing, carp treatment, application to a nutrient solution in hydroponic culture, smoking or trunk injection.

  When used, it varies depending on the type and amount of harmful organisms and the type of crop or tree to be treated, cultivation form and growth condition, but generally 0.01 to 1000 g in total amount of active ingredients per 10 ares, preferably 0 Apply 1 to 100 g. To treat this, dilute with water in the case of water dispersible granules, water dispersible granules, dry flowables, aqueous solvents, emulsions, solutions, flowables such as aqueous suspensions / aqueous emulsions, capsules etc. Although it varies depending on the type of the target plant, cultivation form and growth condition, it may generally be applied to crops etc. at an application rate of 10 to 1000 liters per 10 ares. Moreover, if it is a powder, a spray, or an aerosol agent, it may be processed to a crop etc. in the state of the formulation.

  For example, when the target pest harms plants in the soil, or when the drug is absorbed from the root to control the target pest, the preparation may be diluted or diluted with water, for example. Method of applying to plant stock origin or nursery bed for raising seedlings, method of spraying granules on plant origin for plant origin or seedling for raising seedlings, powder, wettable powder, granules before sowing or transplanting Method of spraying wettable powders, granules etc. and mixing with the whole soil, before planting or planting plants, planting holes, forming powders etc. powders, wettable powders, water dispersible granules, granules, fine granules And the like. In wettable powders, water dispersible granules, water solvents, emulsions, solutions, flowable agents such as aqueous suspensions and aqueous emulsions, and capsules etc. diluted with water, generally an application rate of 5 to 500 liters per 10 ares Then, it may be sprayed on the soil surface or irrigated in the soil so as to be even throughout the treated area. In the case of powders, granules, fine granules or baits, etc., they may be dispersed on the soil surface evenly in the whole area to be treated in the state of the preparation. Spraying or irrigation may be around the seeds, crops or trees that you want to protect against harm. It is also possible to cultivate during or after spraying to disperse the active ingredient mechanically. When treated on soil, the total amount of active ingredients per 10 are generally 0.01, although it varies depending on the type and amount of harmful organisms, the type of crops and trees to be treated, the type of cultivation, growth state or soil type. 1000 to 1000 g, preferably 0.1 to 500 g are applied.

  The method of applying rice to the nursery box may differ depending on the application time of sowing application, planting period application, transplantation application, etc. For example, powder, water dispersible granules, granules, fine granules, etc. As it is, it may be applied by diluting it with water in the case of water dispersible granules, water dispersible granules, water solvents, emulsions, solutions, flowable agents such as aqueous suspensions / emulsions, capsules and the like. It can be applied by mixing with the soil, and mixing with the soil and the powder or granules, for example, mixing with the bed soil, mixing with the soil, mixing into the whole soil, etc. Alternatively, the culture soil and the various preparations may be alternately layered and applied.

  As a method of application to paddy fields, solid preparations such as jumbo agents, pack agents, granules, and water dispersible granules, and liquid preparations such as flowables and emulsions are usually sprayed on flooded paddy fields. In addition, at the time of rice planting, it is also possible to spray or inject a suitable preparation as it is or mixed with fertilizer etc. into the soil. In addition, by using a chemical solution such as a wettable powder, an emulsion, or a flowable as a water inlet to a paddy field such as a water port or an irrigation device, it can be applied labor-saving along with the supply of water.

  As a method of seed treatment, for example, a method of immersing seeds in a liquid state by diluting or not diluting a liquid or solid preparation, allowing a drug to adhere and permeate, mixing a solid preparation or a liquid preparation with the seeds, The method of making it coat | covering and making it adhere to the surface of a seed, the method of mixing with adhesive carriers, such as resin and a polymer, the method of coating on a seed, the method of spraying on seed vicinity simultaneously with planting etc. are mentioned. The “seed” that performs the seed treatment means a plant at an early stage of cultivation used for propagation of the plant, and for example, in addition to the seed, bulbs, tubers, seeds, shoots, shoots, straws, bulbs or cuttings The plant body for reproduction can be mentioned. In addition, the "soil" or "cultivation carrier" of a plant when applied is a support for cultivating a crop, in particular a support for growing a root, and the material is not particularly limited, but the plant is It may be any material that can grow, so-called soil, nursery mat, water, etc., and specific materials include, for example, sand, pumice, vermiculite, diatomaceous earth, agar, gel-like substance, polymer substance, rock Wool, glass wool, wood chips, bark and the like can be mentioned. When used, the total amount of the active ingredient per kilogram of seed is 0.001 to 50 g, preferably 0.01 to 10 g.

  As treatment of seeding of the cultivation plant to be transplanted and treatment of the seedling raising period, in addition to direct treatment to seeds, irrigation treatment of liquid medicine or dispersion treatment of granules to a seedling for raising seedlings is preferable. In addition, it is also a preferable treatment to treat granules into planting holes at the time of planting, or to mix it with a cultivation carrier near the transplanting site.

  The pharmaceutical composition for agricultural and horticultural purposes of the present invention can be used to prevent or treat the onset or spread of diseases of organs such as skin, digestive system and respiratory system by infesting the body surface or body of humans and domestic animals and pets. It can be used. In such a situation, mixing the compound of the present invention into a small amount of a meal or feed, etc., a suitable orally ingestible pharmaceutical composition, etc., eg tablets, pills containing a pharmaceutically acceptable carrier or coating substance, Capsules, pastes, gels, beverages, medicated feed, medicated drinking water, medicated supplements, sustained release large pills, and other sustained release devices that are intended to be retained in the gastrointestinal tract, etc. Oral administration or spray, powder, etc. It can be administered transdermally as a grease, cream, ointment, emulsion, lotion, spot-on, pour-on, shampoo and the like. In order to achieve the effect by such a method, generally, the total amount of the active ingredient compounds is contained in a weight ratio of 0.0001 to 0.1%, preferably 0.001 to 0.01%.

  EXAMPLES 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 at all 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 of (4-heptafluoroisopropyl) aniline and 327 mg of (R) -2- [4-[[5- (trifluoromethyl) -2-pyridyl] oxy] phenoxy] propionic acid and 0.42 ml of triethylamine in 10 ml of tetrahydrofuran Then, 260 mg of 2-chloro-1-methylpyridinium iodide was added little by little and stirred at room temperature overnight. The reaction solution 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 a compound (number 5) listed in Table 1.
1 H-NMR (CDCl 3), δ ppm: 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 (1 H, dd), 8.36 (1 H, bs), 8.42 (1 H, 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) (Scheme 2)
A solution of 481 mg of (2-chloro-4-heptafluoroisopropyl-6-methyl) aniline in 2 ml of N-methyl-2-pyrrolidone was prepared as (R) -2- [4-[[5- (trifluoromethyl)- 430 mg of 2-pyridyl] oxy] phenoxy] propionyl chloride was added little by little and stirred at room temperature for 2 hours. Water was added to the reaction solution and extracted with ethyl acetate. The obtained organic layer was washed with water and dried over anhydrous magnesium sulfate, and the solvent was evaporated 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 (number 43) described in Table 1. The melting point of the obtained compound was 90-100 ° C.
1 H-NMR (CDCl 3), 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 (1 H, s), 7.52 (1 H, s), 7. 91 (1 H, dd), 8.03 (1 H, bs), 8.42 (1 H, s)
From the analysis of HPLC, one peak with a retention time of 16.3 minutes (R isomer) was confirmed.

-HPLC analysis conditions-
Column: CHIRALPAK AD 10 μm 4.6 mm × 250 mm (manufactured by Daicel Chemical Industries, Ltd.)
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 amount: 5 μL

Example 3
2- [4-[[5- (trifluoromethyl) -2-pyridyl] oxy] phenoxy] -N-methoxymethylcarbonyl-N-[(2-chloro-4-heptafluoroisopropyl-6-methyl) phenyl Synthesis of Propanamide (Compound No. 54) (Scheme 3)
(R) -2- [4-[[5- (trifluoromethyl) -2-pyridyl] oxy] phenoxy] -N-[(2-chloro-4-heptafluoroisopropyl-6-methyl) phenyl] propane To a solution of 200 mg of amide in 5 ml of DMF, 20 mg of 60% NaH in Oil was added and stirred at room temperature. After 10 minutes, 0.058 ml of methoxymethyl carbonyl chloride was added and the mixture was stirred at room temperature for 6 hours. Water was added to the reaction solution and extracted with ethyl acetate. The obtained organic layer was washed with water and then with saturated aqueous sodium hydrogen carbonate solution. The extract was dried over anhydrous magnesium sulfate and the solvent was evaporated 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 object compound (number 54) described 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 (1.3 H, s), 3.86 (1.2 H, q), 4.23 (0.8 H, q), 5.30 (0.5 H, b), 5.83 (0.6 H, b), 6.70 (1 H, d), 6.89-7.05 (4H, m), 7.38 (0.5 H, s), 7.46 (0.6 H, s), 7.61 (1 H, s), 7.87 (1 H, dd), 8.42 (1 H, 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 (synthesis of intermediate)
0.22 ml of methoxymethyl carbonyl chloride was added little by little to a solution of 481 mg of (2-chloro-4-heptafluoroisopropyl-6-methyl) aniline in 2 ml of N-methyl-2-pyrrolidone and stirred at room temperature for 1 hour. Water was added to the reaction solution and extracted with ethyl acetate. The obtained organic layer was washed with water and then with saturated aqueous sodium hydrogen carbonate solution. The extract was dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure. There was obtained 720 mg (solid) of the desired compound N-methoxymethylcarbonyl- (2-chloro-4-heptafluoroisopropyl-6-methyl) aniline. Used for the next reaction without further purification.
¹ H-NMR (CDCl 3), δ ppm: 2.36 (3 H, s), 3.57 (3 H, s), 4.12 (2 H, s), 7. 40 (1 H, s), 7.54 (1 H, s), 8. 15 (1 H, bs )

4-2) N-Methoxymethylcarbonyl- (2-chloro-4-heptafluoroisopropyl-6-methyl) aniline 50 mg of 60% NaH in Oil was added to a solution of 382 mg of DMF in 3 ml of DMF and stirred at room temperature. After cooling to 0 to 10 ° C., 420 mg of (R) -2- [4-[[5- (trifluoromethyl) -2-pyridyl] oxy] phenoxy] propionyl chloride was added little by little. 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 evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane: ethyl acetate = 3: 1 Rf = 0.3) to give 310 mg (oil) of the target compound (number 54) described in Table 1. The Rf value and ¹ H-NMR were identical to the compound of Example 3.

Example 5
2- [4-[[5- (trifluoromethyl) -2-pyridyl] oxy] phenoxy] -N-[(2-chloro-4-heptafluoroisopropyl-6-methyl) phenyl] propanamide (compound number 45, Synthesis of 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) aniline To a solution of 929 mg of 3 ml of N-methyl-2-pyrrolidone was added 0.38 ml of 2-bromopropionyl bromide little by little and stirred at room temperature for 1 hour. Water was added to the reaction solution and extracted with ethyl acetate. The obtained organic layer was washed with water and then with saturated aqueous sodium hydrogen carbonate solution. The extract was dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane: ethyl acetate = 3: 1 Rf = 0.3) to obtain 1280 mg of the target intermediate (oil).
¹ H-NMR (CDCl 3), δ ppm: 2.20 (3 H, d), 2.36 (3 H, s), 4.62 (1 H, q), 7.41 (1 H, s), 7.55 (1 H, s), 7.92 (1 H, bs )

5-2) 0.90 g of anhydrous potassium carbonate is added to a solution of 10.28 g of 4-[[5- (trifluoromethyl) -2-pyridyl] oxy] phenol in 10 ml of N-methyl-2-pyrrolidone and stirred, 0.44 g of bromo-N-[(2-chloro-4-heptafluoroisopropyl-6-methyl) phenyl] propanamide was added in small portions. The mixture was stirred at room temperature for 5 hours and then heated and stirred at 105 ° C. for 2 hours. After cooling to room temperature, water was added to the reaction solution and extracted with ethyl acetate. The obtained organic layer was washed with water and then with saturated aqueous sodium hydrogen carbonate solution. The extract was dried over anhydrous magnesium sulfate and the solvent was evaporated 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 objective compound (number 45) described in Table 1. The melting point of the obtained compound was 112-114 ° C.
¹ H-NMR (CDCl 3), 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 (1 H, s), 7.52 (1 H, s), 7. 91 (1 H, dd), 8.03 (1 H, bs), 8.42 (1 H, s)
From the analysis of HPLC, the racemate was confirmed at a peak area ratio of 1: 1 at a retention time of 13.7 minutes (S form) and 16.3 minutes (R form).

-HPLC analysis conditions-
Column: CHIRALPAK AD 10 μm 4.6 mm × 250 mm (manufactured by Daicel Chemical Industries, Ltd.)
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 amount: 5 μL

The ¹ H-NMR data of the compounds produced in the same manner as in the above Examples is shown in Table 7 below.

  Hereinafter, although the preparation containing the compound of the present invention will be specifically described with reference to some preparation examples, the compound of the present invention, auxiliary components and the addition amount thereof are of course limited to only the following preparation examples is not. In the preparation examples, all parts are by weight.

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

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

Formulation Example 3 Hydratable powder-2
Compound of the present invention (20 parts), Nip seal NS-K (White carbon, Tosoh Silica Corporation, trade name) (20 parts), Kaolin clay (Kaolinite, Takehara Chemical Industry Co., trade name) (50 parts) , Lunox 1000 C (naphthalene sulfonate condensate, Toho Chemical Industry Co., Ltd., trade name) (5 parts) and Solpol 5276 (nonionic surfactant, Toho Chemical Industry Co., Ltd., trade name) (5 parts), air mill The mixture was uniformly mixed and ground to obtain a wettable powder.

Production Example 4 Granulating water-dispersible powder Compound (20 parts) of the present invention, demol N (naphthalene sulfonate formalin condensate, Kao Corporation, trade name) (5 parts), Airol CT-1 L (dioctyl sulfosuccinate, Toho Chemical Industry Co., Ltd. (trade name) (1 part), Serogen 701A (Carboxymethylcellulose, Daiichi Kogyo Seiyaku Co., Ltd.) (1 part) and Kaolin clay (Kaolinite, Takehara Chemical Co., Ltd. trade name) (73 parts) The mixture was uniformly mixed and ground in an air mill. Water was added to the mixture and the mixture was thoroughly mixed, and then extruded and granulated, and dried and sized to obtain a water dispersible powder.

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

Formulation Example 6 Water solvent-2
The compound of the present invention (50 parts), Neucargen BX-C (Na alkylnaphthalene sulfonate, manufactured by Takemoto Yushi Co., Ltd., trade name) (5 parts), water-soluble carrier potassium chloride (45 parts) are uniformly mixed and crushed Water solvent was obtained.

Formulation Example 7 Flowable Agent-1
Propylene glycol (5 parts) mixed in advance, Sorpol 7933 (anionic surfactant, Toho Chemical Industries, Ltd., trade name) (5 parts), water (50 parts) The compound of the present invention (20 parts) Are dispersed into a slurry-like mixture, and then this slurry-like mixture is wet-milled, and then xanthan gum (Kelzan, tricrystal corporation, trade name) (0.2 parts) in water (19.8 parts) A well-mixed dispersion was added to obtain a flowable agent.

Formulation Example 8 Flowable Agent-2
Compound of the present invention (20 parts), Neucargen 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 premixed and the slurry-like mixture was wet milled. Next, xanthan gum (0.2 parts) was thoroughly mixed and dispersed in water (16.8 parts) to prepare a gel-like product, which was thoroughly mixed with the crushed slurry to obtain a flowable agent.

Formulation Example 9 EW-1
Compound of the present invention (20 parts) and Solpol CA-42 (non-ionic activator, Toho Chemical Industry Co., Ltd., trade name) (15 parts) and preservative Proxel GX-L (Lonza Japan Co., Ltd., trade name) (0 parts) .1 part) was mixed and homogenized, then water (59.6 parts) was gradually added while stirring to obtain a dispersion. Xanthan gum dispersed in propylene glycol (5.0 parts) by adding antifoam anti-home E-20 (emulsion-type modified silicone, Kao Corporation, trade name) (0.1 parts) to the obtained dispersion and dispersing it in propylene glycol (5.0 parts) An emulsion preparation was obtained by adding (Kelzan, Sanyo Co., Ltd., trade name) (0.2 parts) (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 surfactant Leodol 430V (polyoxyethylene sorbit tetraoleate, trade name of Kao Corporation) (24 parts). Liquid obtained in water (50.6 parts), antifoam anti-home E-20 (emulsion-type modified silicone, Kao Corporation, trade name) (0.1 part), preservative Proxel GX-L (Lonza) Japan Co., Ltd. (brand name) (0.1 part) was added, then dispersed using a homogenizer, and dispersed in propylene glycol (5.0 parts) xanthan gum (Kelzan, tricrystal Co., Ltd., trade name) ( 0.2 parts were added to obtain an emulsion preparation (mechanical emulsification method).

Formulation Example 11 ME Agent-1
The compound of the present invention (0.01 part) and Solpol CA-42 (non-ionic activator, Toho Chemical Industry Co., Ltd., trade name) (0.1 part) are mixed and homogenized, then water is gradually added while stirring. (99.79 parts) was added. Preservative Proxel GX-L (Lonza Japan KK, 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 Neucargen D-945 (polyoxyethylene (20 moles) sorbitan monooleate, Takemoto Oil & Fat Co., Ltd., trade name) (20 parts) are mixed and homogenized while stirring Water (69.9 parts) was slowly added. Preservative Proxel GX-L (Lonza Japan KK, trade name) (0.1 parts) was added to the dispersion to obtain a microemulsion.

Formulation Example 13 ME Agent-3
Compounds of the present invention (0.01 part), solvent Solvesso 200 (Exxon Mobil, trade name) (0.08 parts) and Neucargen ST-30 (polyoxyethylene aryl phenyl ether formaldehyde condensate and polyoxyalkylene aryl phenyl ether) And a mixture of alkylbenzene sulfonate and xylene, Takemoto Oil & Fat Co., Ltd. (trade name) (0.12 parts), mixed with a surfactant, homogenized, and water (99.69 parts) while stirring I added it gradually. Preservative Proxel GX-L (Lonza Japan KK, trade name) (0.1 parts) 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 (lignin sulfonate sodium, Nippon Paper Industries Co., Ltd., trade name) (5 parts), Lanox P-65 L (alkyl allyl sulfonate, Toho Chemical Industry Co., Ltd., Brand name) (2 parts), Sado bentonite (Kanto Bentonite Industrial Co., Ltd.) (20 parts) and kaolin clay (Kaolinite, Takehara Chemical Industry Co., Ltd., trade name) (58 parts) were uniformly mixed and crushed in an air mill. . Water was added to the mixture and the mixture was thoroughly mixed, and then extruded and granulated, and dried and sized to obtain granules.

Formulation Example 15 Granule-2
Compound (5 parts) of the present invention which has been mixed with silicon sand (90 parts) in a rolling granulator and allowed to hydrate, and then ground and mixed beforehand, Sun Extract P-252 (sodium lignin sulfonate, Nippon Paper Industries Co., Ltd. , 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) (trade name) After adding 0.5 part) and coating, it was dried and sized to obtain granules.

Formulation Example 16 Granule-3
Ishikawa Light (Ishikawa Light Industry Co., Ltd., trade name) (89 parts) is added to a rolling granulator and allowed to hydrate, and then the compound of the present invention (5 parts) which has been pulverized and mixed in advance, sun extract P- 252 (Lignin sulfonate sodium, Nippon Paper Industries Co., Ltd., trade name) (3 parts), Airrol CT-1 L (dioctyl sulfosuccinate, Toho Chemical Industry Co., Ltd., trade name) (0.5 parts), Solpol 5276 (non- 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 added, coated and dried. The granules were obtained.

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

Formulation example 18 fine particle agent-2
The compound of the present invention (5 parts) is optionally air milled or mechanochemically ground. Binder Toxanone GR-31A (polycarboxylic acid type anionic surfactant) diluted with solvent after uniformly mixing powdered base material and extender No. 6 silica sand (Ube Sand Industry Co., Ltd., trade name) (85 parts) An aqueous solution of the agent, Sanyo Chemical Industries, Ltd. (trade name) (10 parts) was sprayed and mixed, and the obtained granular composition was dried and sieved to obtain a fine particle agent.

Formulation Example 19 Powder Agent Compound of the present invention (2 parts), Nip Seal NS-K (White Carbon, Tosoh Silica Corporation, trade name) (10 parts) and Kaolin clay (Kaolinite, Takehara Chemical Co., Ltd., trade name) (88 parts) was mixed and pulverized uniformly in an air mill to obtain a powder.

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

Formulation Example 21 Seed Coating Powder Compound of the present invention (10 parts), Sun Extract P-252 (sodium lignin sulfonate, trade name of Nippon Paper Industries Co., Ltd., 6 parts), Gosenol GL05 (polyvinyl alcohol, Nippon Synthetic Chemical Industry Co., Ltd. A powder prepared by uniformly mixing and grinding a company and a trade name (1 part) and clay (Nippon Talc Co., Ltd. trade name) (83 parts) and a pre-wetted seed are mixed, air-dried and coated seeds I got

Formulation Example 22 Oily Suspension Formulation Compound of the present invention (20 parts), Neucargen C-120 (POE tristyryl phenyl ether, Takemoto Oil & Fats, trade name) (5 parts), Leodol TW-O 120 V (POE sorbitan monoole Eate, Kao Co., Ltd. (brand name) (10 parts), oleic acid methyl ester (Kanto Chemical Co., Ltd., reagent) (62 parts), Esben NZ (organic bentonite, Hojun Co., product name) (3 parts) The slurry-like dispersion was wet-milled 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 as comparative controls are indicated by the following compound symbols.
Comparative compound A (compound described in Patent Document 17)

Comparative compound B (analogous compounds 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)

The ¹ H-NMR data of the comparative compounds A to E are shown in Table 8 below.

Table 8

Test Example Test for Cucumber Powdery Mildew A water-diluted solution of the emulsion prepared according to Preparation Example 1 was sprayed over the whole cucumber seedlings (seedlings of about 1.5 leaf stage) at a rate of 5 ml / pot using a spray gun. The day after spraying, a spore suspension (1.0 × 10 ⁵ spores / ml) of a predetermined concentration was spray-inoculated on the surface of the first true leaves. After inoculation, it moved to a glasshouse, and after 12 days, the incidence was examined based on the following lesion area rate. Based on the following formula, the control value was calculated from the incidence of the untreated area and the incidence of the treated area.
Disease severity 0 (paque area ratio: 0%), disease severity 6.25 (paque area ratio: 0 to less than 6.3%), disease severity 12.5 (paque area ratio: 6.3 to 12). Less than 5%), disease severity 25 (paque area ratio: less than 12.5 to 25%), disease severity 50 (paque area ratio: less than 25 to 50%), disease severity 100 (paque area ratio: 50%) that's all)

Control value (%) = [1-(treatment disease incidence / untreated disease incidence)] × 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 control 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-diluted solution of the emulsion prepared according to Formulation Example 1 was sprayed on a whole of a wheat seedling (seedling at about 1.5 leaf stage) at a rate of 5 ml / pot using a spray gun. On the next day of spraying, inoculation was carried out by transferring the seedlings after spraying to a glass greenhouse and placing diseased seedlings of wheat powdery mildew around. The incidence was examined 12 days after inoculation based on the following lesion area rate. Based on the following formula, the control value was calculated from the incidence of the untreated area and the incidence of the treated area.
Disease severity 0 (paque area ratio: 0%), disease severity 6.25 (paque area ratio: 0 to less than 6.3%), disease severity 12.5 (paque area ratio: 6.3 to 12). Less than 5%), disease severity 25 (paque area ratio: less than 12.5 to 25%), disease severity 50 (paque area ratio: less than 25 to 50%), disease severity 100 (paque area ratio: 50%) that's all)

Control value (%) = [1-(treatment disease incidence / untreated disease incidence)] × 100

As a result, the 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 price was over 70. On the other hand, the comparative agents A, B, C, D and E were the control values 0, 22, 20, 25 and 25 respectively at the concentration of 400 ppm.

Test Example: Test of Insecticidal Effect against Psyllid Mosquitoes A water dilution of the emulsion prepared according to Formulation Example 1 was dispersed in a sufficient amount using an air brush on the leaf of the pot planted icy seedling grown for two weeks after sowing. . After the drug solution was air-dried, five 3rd instar larvae of Conagaya were inoculated, placed in a PET cup made of a 430 ml container, covered with a mesh lid, and kept in a thermostatic chamber at 23 ° C. Five days after the treatment, the condition of the larva was divided into three, survival, abnormal and death, and observed, and the larval mortality (%) was determined by the following equation based on the observation result. In addition, the test was implemented by testing 1 seedling in each section.

Larva mortality (%) = (number of dead insects + number of abnormal insects) / number of insects tested × 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% kill rate at a concentration of 500 ppm. The
On the other hand, the comparative agents A, B, C, D, and E had a 0% kill rate at a concentration of 500 ppm.

Test Example: Insecticidal effect test on tomato rust mite A PET cup made of 430 ml capacity was filled with water and a lid with a hole (approximately 5 mm in diameter) opened at the center. About 1 cm wide and about 14 cm long cotton wool was inserted through the hole in the lid so as to be immersed in the water in the cup, and about 8 cm square cotton wool was placed thereon to ensure that the water in the cup was constantly replenished. Place three leaf disks (1 cm x 1 cm) made of small leaves in the early stage of tomato true leaf development on absorbent cotton so that the back of the leaf is on top, and on this leaf disk, small pieces of leaf infected with tomato rust mite I inoculated it. Twenty-four hours after inoculation, this cup was placed in an acrylic cylinder 45 cm high and 12 cm in diameter, and an aqueous brush of water diluted with an emulsion prepared according to Formulation Example 1 was sprayed using an air brush. (1 concentration, 1 repeat). After spraying, it was kept in a temperature-controlled room at 25 ° C. After 7 days of treatment, the number of viable larvae is 100 (density suppression rate: 100%), 80 (same as 99-80%), 50 (same: 79-50%), 0 (same as 50%). It evaluated and the control value was computed with the following Formula based on the result.

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

A: 100 disks, B: 80 disks, C: 50 disks, D: 0 disks.
As a result, Compound Nos. 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 showed a control value of 100% at a concentration of 500 ppm.
On the other hand, the control 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 drugs.

Claims (14)

Formula (1)
(1)
[In the formula,
R ¹ represents hydrogen, a C _1-12 alkyl group, a C _1-12 haloalkyl group, a C _3-6 alkenyl group, a C _3-6 haloalkenyl group, a C _3-6 alkynyl group, a 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 haloalkoxy group, C _1-6 Alkoxy C _1-6 alkyl group, C _1-6 alkyl carbonyl group, C _1-6 haloalkyl carbonyl group, C _1-6 alkoxy carbonyl group, C _1-6 halo alkoxy carbonyl group, C _1-6 alkoxy C _1-6 Alkyl carbonyl group, C _1-6 alkoxycarbonyl-carbonyl group, mono (di) C _1-6 alkylaminocarbonyl group, mono (di) C _1-6 alkylamino carbonyl-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 each independently represent hydrogen, halogen, a cyano group, a hydroxyl group, a C _1-12 alkyl group, a C _1-12 haloalkyl group, a C _3-8 cycloalkyl group, a 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 , 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 halo alkyl sulphates Alkenyl group, C _1-6 haloalkylsulfonyl group, which may have 1 to 3 identical or different radicals selected from the group consisting of a nitro group or a cyano group), and
V is
Show,
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 hydrogen, halogen, a hydroxyl group, an amino group, a C _1-12 alkyl group, a C _1-12 haloalkyl group, a C _3-8 cycloalkyl group, a 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 groups, C _1-6 alkoxy C _1-6 alkyl group, C _1-6 alkylcarbonyloxy group, an amino Carbonyl group, hydroxy carbo Group represents a nyl group, a formyl group, a nitro group or a cyano group, or when two W's are substituted on adjacent two carbon atoms on a phenyl ring, the two W's are each bonded Together with the selected carbon atom to form a saturated or unsaturated 5- or 6-membered ring,
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 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 haloalkynyl 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 each represent a halogen, a C _1-12 alkyl group, a C _1-12 haloalkyl group, a C _3-8 cycloalkyl group, a 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 (Which may have 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 represents hydrogen, a C _1-12 alkyl group, a C _1-12 haloalkyl group, a C _3-6 alkenyl group, a C _3-6 haloalkenyl group, a C _3-6 alkynyl group, a 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 haloalkoxy group, C _1-6 Alkoxy C _1-6 alkyl group, C _1-6 alkyl carbonyl group, C _1-6 haloalkyl carbonyl group, C _1-6 alkoxy carbonyl group, C _1-6 halo alkoxy carbonyl 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, a sulfur atom, a 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 represent an arbitrary integer of 1 or more. ]
The compound represented by these, its N-oxide, or its salt. V is 4-position substitution
And the N-oxide or a salt thereof. R ³ represents a hydrogen atom, Y is (Y ¹⁾ n ³ - pyridyloxy a group A compound according to claim 1 or 2, their N- oxides or salts thereof. A method for producing a compound according to claim 1, its N-oxide or a salt thereof, which comprises the following formula (2)
(2)
[Wherein, R ¹ , V ¹ , W, n ¹ are as defined in the formula (1)]
And a compound represented by the following formula (3)
(3)
[Wherein, R ² R ³ , Z ¹ , Z ² , X ² , Y, n ² are as defined in the formula (1)]
A method of production comprising reacting with a compound represented by A method for producing a compound according to claim 1, its N-oxide or a salt thereof, which comprises the following formula (2)
(2)
[Wherein, R ¹ , V ¹ , W, n ¹ are as defined in the formula (1)]
And a compound represented by the following formula (4)
(4)
[Wherein, Hal represents a halogen, and R ² R ³ , Z ¹ , Z ² , X ² , Y, n ² are as defined in the formula (1)]
A method of production comprising reacting with a compound represented by   An agricultural and horticultural drug containing the compound according to any one of claims 1 to 3, its N-oxide or a salt thereof.   The fungicide for agriculture and horticulture containing the compound of any one of Claims 1-3, its N-oxide, or its salt.   The agricultural and horticultural insecticide containing the compound of any one of Claims 1-3, its N-oxide, or its salt.   An agricultural and horticultural acaricide comprising the compound according to any one of claims 1 to 3, its N-oxide or a salt thereof.   Use of the agricultural and horticultural agent 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 the step of treating pests and / or their habitat and / or seeds and / or plant propagation material with the agricultural and horticultural agent 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 according to claim 6 with an agricultural or horticultural drug according to claim 6 .   A method of preparing a pesticide composition, comprising the step of mixing the agricultural and horticultural agent according to claim 6 with a bulking agent and / or a surfactant.