Development of organic compounds exhibiting insecticidal activity against acarines

Abstract

The present invention relates to an acaricide comprising a compound represented by formula (1) or a salt thereof. # imgabs0 #

Description

Technical Field

[0001] The present invention relates to the preparation of organic compounds showing insecticidal activity against mites and ticks. Background Art

[0002] In recent years, infections mediated by mites and ticks have spread worldwide, and various acaricides for repelling mites and ticks have been studied. For example, Patent Document 1 discloses costic acid as an acaricide for repelling Varroa destructor, a mite that parasitizes honeybees.

[0003] Prior art literature

[0004] Patent Literature

[0005] Patent Document 1: European Patent No. 2346328 Summary of the Invention

[0006] Problems to be solved by the invention

[0007] However, mites and ticks resistant to existing acaricides such as costus acid described in Patent Document 1 have emerged. Therefore, there is a need for new acaricides capable of repelling mites and ticks resistant to existing acaricides.

[0008] The object of the present invention is to provide a new acaricide.

[0009] Solutions for solving problems

[0010] The present inventors have discovered a compound that exhibits a repellent effect on mites and ticks resistant to existing acaricides, thereby completing the present invention.

[0011] The present invention is as follows. [1]

[0013] A miticide comprising a compound represented by the following formula (1) or a salt thereof.

[0014]

[0015] (In formula (1),

[0016] R1 is absent or is a hydrogen atom, and R2 is a hydrogen atom; or, R1 and R2 together with their adjacent carbon atoms form an optionally substituted 6-membered saturated carbocyclic ring,

[0017] R3 is a hydrogen atom or an alkyl group,

[0018] R4 is optionally substituted alkyl, alkenyl, alkynyl, hydroxyalkyl, cycloalkyl, cycloalkylalkyl, aryl, heteroaryl, aralkyl, CHO or CO2R5,

[0019] R5 is a hydrogen atom or an optionally substituted alkyl, alkenyl, alkynyl, hydroxyalkyl, cycloalkyl, cycloalkylalkyl, aryl, heteroaryl, or aralkyl group,

[0020] R6 and R7 together form a double bond or an epoxy ring,

[0021] R8 and R9 are each independently a hydrogen atom or OH,

[0022] The dotted part is a single bond or a double bond.

[0023] However, the case where formula (1) has a structure represented by the following formula (2) is excluded.)

[0024] [2]

[0026] The acaricide according to [1], wherein R3 is an alkyl group having 1 to 5 carbon atoms. [3]

[0028] The acaricide according to [1] or [2], wherein R4 is an optionally substituted alkyl group having 1 to 5 carbon atoms, CHO or CO2R5,

[0029] R5 is an alkyl group having 1 to 5 carbon atoms. [4]

[0031] The acaricide according to any one of [1] to [3], comprising a compound represented by the following formula (3) or a salt thereof.

[0032]

[0033] (In formula (3),

[0034] The meanings of R3 to R9 are the same as above.

[0035] The dotted part is a single bond or a double bond.

[0036] R 10 and R 10 When the dotted line between adjacent carbon atoms is a single bond, R 10 For OH,

[0037] R 10 and R 10 When the dotted line between adjacent carbon atoms is a double bond, R 10 is an oxygen atom, CH2, CHCHO, or CHCO2R 11 ,

[0038] R 11is a hydrogen atom or an optionally substituted alkyl, alkenyl, alkynyl, hydroxyalkyl, cycloalkyl, cycloalkylalkyl, aryl, heteroaryl or aralkyl group,

[0039] R 12 and R 13 are each independently a hydrogen atom or OH.

[0040] However, the case where formula (3) is a structure represented by the following formula (2) is excluded.)

[0041] [5]

[0043] A miticide comprising a compound represented by the following formula (4) to (12) or a salt thereof.

[0044] [6]

[0046] The acaricide according to any one of [1] to [5], which targets Varroa mites or cattle ticks. [7]

[0048] The acaricide according to any one of [1] to [6], which is used in combination with another acaricide. [8]

[0050] The acaricide according to [7], wherein the other acaricide is selected from the group consisting of Tebufenpyrad, Pyridaben, Fenpyroximate, Milbemectin, Abamectin, Chlorfenapyr, Etoxazole, Acequinocyl, Bifenazate, Spiromesifen, Spirotetramat One or more of the group consisting of cyflutetramat, cyflumetofen, cyenopyrafen, pyflubumide, fenpyroximate, acynonapyr, amitraz, fluvalinate, thymol, flumethrin, formic acid, oxalic acid and a compound represented by the following formula (2), and salts of these compounds.

[0051] [9]

[0053] A method for expelling mites and ticks, comprising using the acaricide according to any one of [1] to [8] against mites and ticks.

[10]

[0055] The method for exterminating mites and ticks according to [9], wherein the acaricide is used against mites and ticks by a vapor diffusion method or a contact method.

[11]

[0057] The method for expelling mites and ticks according to [9] or

[10] , wherein the acaricide is allowed to act on honeybees to expel mites and ticks parasitizing the honeybees.

[12]

[0059] The method for exterminating mites and ticks according to any one of [9] to

[11] , wherein the method is used in combination with other acaricides.

[13]

[0061] The method for expelling mites and ticks according to

[12] , wherein the other acaricide is one or more selected from the group consisting of tebufenpyrad, pyraclostrobin, fenpyraclostrobin, imipenem, abamectin, chlorfenapyr, etoxazole, acequinoxaline, bifenazate, spiromesifen, spirotetramat, cyflumetofen, cypermethrin, pyraclostrobin, pyrazoline, fenpyraclostrobin, fluazifop, amitraz, fluvalinate, thymol, flumethrin, formic acid, oxalic acid and the compound represented by the following formula (2), and the salts of these compounds.

[0062]

[0063] Effects of the Invention

[0064] According to the present invention, a novel acaricide can be provided. BRIEF DESCRIPTION OF THE DRAWINGS

[0065] Figure 1 It is a figure which shows the result of Example.

[0066] Figure 2 It is a figure which shows the result of Example.

[0067] Figure 3 It is a figure which shows the result of Example.

[0068] Figure 4 It is a figure which shows the result of Example.

[0069] Figure 5 It is a figure which shows the result of Example. DETAILED DESCRIPTION

[0070] An embodiment of the present invention (hereinafter referred to as “this embodiment”) will be described in detail below. However, the present invention is not limited to this description and various modifications can be made without departing from the spirit and scope of the invention.

[0071] 1. Acaricide

[0072] 1.1. Compound represented by formula (1) or its salt

[0073] The acaricide of this embodiment (hereinafter also referred to as "acaricide") comprises a compound represented by the following formula (1) or a salt thereof. The compound represented by the following formula (1) or a salt thereof may be used alone or in combination of two or more.

[0074]

[0075] (In formula (1),

[0076] R1 is absent or is a hydrogen atom, and R2 is a hydrogen atom; or, R1 and R2 together with their adjacent carbon atoms form an optionally substituted 6-membered saturated carbocyclic ring,

[0077] R3 is a hydrogen atom or an alkyl group,

[0078] R4 is optionally substituted alkyl, alkenyl, alkynyl, hydroxyalkyl, cycloalkyl, cycloalkylalkyl, aryl, heteroaryl, aralkyl, CHO or CO2R5,

[0079] R5 is a hydrogen atom or an optionally substituted alkyl, alkenyl, alkynyl, hydroxyalkyl, cycloalkyl, cycloalkylalkyl, aryl, heteroaryl or aralkyl group,

[0080] R6 and R7 together form a double bond or an epoxy ring,

[0081] R8 and R9 are each independently a hydrogen atom or OH,

[0082] The dotted part is a single bond or a double bond.

[0083] However, the case of the structure represented by the following formula (2) is not included.)

[0084]

[0085] In this embodiment, the alkyl group refers to n H 2n+2 A monovalent group formed by removing one hydrogen atom from any carbon atom of an alkane represented by alkyl. The alkyl group is not particularly limited, and specific examples thereof include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, neopentyl, and 3-pentyl.

[0086] In this embodiment, alkenyl refers to n H 2n The alkylene group is a monovalent group formed by removing one hydrogen atom from any carbon atom of an alkene group shown in the figure. The alkenyl group may be a group having an unsaturated carbon bond formed by removing two hydrogen atoms from an alkyl group, or may have multiple unsaturated carbon bonds within the group. The alkenyl group is not particularly limited, and specific examples thereof include vinyl, n-1-propenyl, n-2-propenyl, 1-methylvinyl, n-1-butenyl, n-2-butenyl, n-3-butenyl, 2-methyl-1-propenyl, 2-methyl-2-propenyl, 1-ethylvinyl, 1-methyl-1-propenyl, 1-methyl-2-propenyl, n-1-pentenyl, n-2-pentenyl, n-3-pentenyl, n-4-pentenyl, 1-n-propylvinyl, 1-n-propenyl, 1-n-butylvin ... -methyl-1-butenyl, 1-methyl-2-butenyl, 1-methyl-3-butenyl, 2-ethyl-2-propenyl, 2-methyl-1-butenyl, 2-methyl-2-butenyl, 2-methyl-3-butenyl, 3-methyl-1-butenyl, 3-methyl-2-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1-isopropylvinyl, 1,2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl, etc.

[0087] In this embodiment, alkynyl refers to n H 2n-2 A monovalent group formed by removing one hydrogen atom from any carbon atom of an alkyne as shown. An alkynyl group may be a group having a carbon-carbon triple bond formed by removing four hydrogen atoms from an alkyl group, or may have a plurality of unsaturated carbon bonds including a carbon-carbon triple bond within the group. The alkynyl group is not particularly limited, and specific examples thereof include ethynyl, n-1-propynyl, n-2-propynyl, n-1-butynyl, n-2-butynyl, n-3-butynyl, 1-methyl-2-propynyl, n-1-pentynyl, n-2-pentynyl, n-3-pentynyl, n-4-pentynyl, 1-methyl-n-butynyl, 2-methyl-n-butynyl, 3-methyl-n-butynyl, and 1,1-dimethyl-n-propynyl.

[0088] In the present embodiment, hydroxyalkyl refers to a group in which one or more hydrogen atoms of an alkyl group are replaced by OH. Hydroxyalkyl is not particularly limited, and specific examples include CH2OH, CH2CH2OH, CH(OH)CH3, CH2CH2CH2OH, CH2CH(OH)CH2, CH(OH)CH2CH3, CH2CH2CH2CH2OH, CH2CH2CH(OH)CH3, CH2CH(OH)CH2CH3, CH2CH2CH2CH2OH, CH2CH2CH(OH)CH3, CH2CH(OH)CH2CH3, CH2CH2CH2CH2OH, CH2CH2CH2CH(OH)CH3, CH2CH2CH(OH)CH2CH3, CH2CH(OH)CH2CH3, CH2CH(OH)CH2CH2CH3, CH(OH)CH2CH2CH3, CH(OH)CH2OH, CH(CH3)OH, and CH(CH2OH)2.

[0089] In the present embodiment, a cycloalkyl group refers to a monovalent group formed by removing one hydrogen atom from any carbon atom of a cycloalkane. The cycloalkyl group is not particularly limited, and specific examples thereof include cyclopropyl, cyclobutyl, and cyclopentyl.

[0090] In the present embodiment, the cycloalkylalkyl group refers to a group in which a hydrogen atom of an alkyl group is substituted with a cycloalkyl group. Examples of the cycloalkylalkyl group include, but are not limited to, cyclopropylmethyl, cyclobutylmethyl, cyclopropylethyl, and cyclopropyldimethyl.

[0091] In the present embodiment, an aryl group refers to a monovalent group formed by removing one hydrogen from an aromatic hydrocarbon. Specific examples of the aryl group include, but are not limited to, phenyl, tolyl, xylyl, naphthyl, phenanthrenyl, and anthracenyl.

[0092] In the present embodiment, heteroaryl refers to a monovalent group formed by removing one hydrogen from an aromatic ring containing a heteroatom. The heteroatom is not particularly limited, and specifically B, O, N, P, Si, Se, S, etc. can be listed. As heteroaryl, it is not particularly limited, and specifically pyrrolyl, furyl, thienyl, pyrazolyl, imidazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, tetrazolyl, pyridyl, furyl, pyridazinyl, pyrimidinyl, pyrazinyl, quinolyl, isoquinolyl, naphthyridinyl, quinoxalinyl, cinnolinyl, quinazolinyl, phthalazinyl, imidazopyridyl, imidazothiazolyl, imidazooxazolyl, benzothiazolyl, benzoxazolyl, benzimidazolyl, indolyl, isoindolyl, indazolyl, pyrrolopyridinyl, thienopyridinyl, furopyridinyl, benzothiadiazolyl, benzoxadiazolyl, pyridopyrimidinyl, benzofuranyl, benzothiophenyl, 1,3-benzodioxole, thienofuranyl, chromenyl, chromanyl, coumarinyl and quinolone, etc.

[0093] In the present embodiment, the aralkyl group refers to a group in which a hydrogen atom of an alkyl group is substituted with an aryl group or a heteroaryl group. The aralkyl group is not particularly limited, and specific examples thereof include benzyl and phenethyl groups.

[0094] The compound represented by formula (1) may have one or more asymmetric carbon atoms in its structural formula. The compound represented by formula (1) may be an optical isomer or a mixture containing each optical isomer in any ratio.

[0095] The salt of the compound represented by formula (1) is not particularly limited as long as it is an acceptable salt as an agricultural and horticultural agent, an animal agent, etc., and examples thereof include salts of inorganic acids such as hydrochlorides, sulfates, nitrates, and phosphates; salts of organic acids such as acetates, fumarates, maleates, oxalates, methanesulfonates, benzenesulfonates, and p-toluenesulfonates; and salts of inorganic or organic bases such as sodium salts, potassium salts, calcium salts, and trimethylammonium salts.

[0096] In this embodiment, the optionally substituted group is not particularly limited, and for example, it may have a halogen, imine, amine, thiol, alcohol, ketone, nitrile, aldehyde, amide, acryloyl halide, ester, carboxyl group, alkoxy group, thioalkoxy group, nitro group, nitroso group, etc. as a substituent. For example, in the optionally substituted alkyl group, the substituent of the alkyl group is not particularly limited, and examples thereof include halogen, imine, amine, thiol, alcohol, ketone, nitrile, aldehyde, amide, acryloyl halide, ester, carboxyl group, alkoxy group, thioalkoxy group, nitro group, nitroso group, etc.

[0097] When R2 in the above formula (1) is a hydrogen atom, the compound represented by formula (1) is represented by the following formula (1A).

[0098]

[0099] (In formula (1A),

[0100] R1 does not exist or is a hydrogen atom,

[0101] The meanings of R3 to R9 are the same as above.

[0102] The dotted part is a single bond or a double bond.)

[0103] In the above formula (1A), it is preferred that R1 does not exist and the dotted line portion is a double bond. In this case, the compound represented by formula (1) is represented by the following formula (1A').

[0104]

[0105] (In formula (1A'),

[0106] R3 to R9 have the same meanings as above.)

[0107] In the above formula (1), when R1 and R2 together with their adjacent carbon atoms form an optionally substituted 6-membered saturated carbocyclic ring, the compound represented by formula (1) is represented by the following formula (1B).

[0108]

[0109] (In formula (1B),

[0110] R3 to R9 have the same meanings as above.

[0111] However, the case of the structure represented by the above formula (2) is not included.)

[0112] In the above formula (1B), ring A may have a substituent, and examples of the substituent include an alkyl group, an alkenyl group, an alkynyl group, a hydroxyalkyl group, a carbonyl group (═O), a ═C n H 2n ,OH,CHO,CH2CHO,CHCHO,CHCO2R 11 、CO2R 14 、CH2CO2R 15 wait.

[0113] R 11 、R 14 and R 15 Each is independently a hydrogen atom or an optionally substituted alkyl group, alkenyl group, alkynyl group, hydroxyalkyl group, cycloalkyl group, cycloalkylalkyl group, aryl group, heteroaryl group or aralkyl group.

[0114] The substituent is CHCO2R 11 When R 11, preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, or an alkynyl group having 2 to 5 carbon atoms. As the alkyl group having 1 to 5 carbon atoms, an alkyl group having 1 to 4 carbon atoms is preferred, an alkyl group having 1 to 3 carbon atoms is more preferred, a methyl group or an ethyl group is further preferred, and a methyl group is further preferred. As the alkenyl group having 2 to 5 carbon atoms, an alkenyl group having 2 to 4 carbon atoms is preferred, a vinyl group, n-1-propenyl group, n-2-propenyl group, or 1-methylvinyl group is more preferred, and a vinyl group is further preferred. As the alkynyl group having 2 to 5 carbon atoms, an alkynyl group having 2 to 4 carbon atoms is preferred, an ethynyl group, n-1-propynyl group, or n-2-propynyl group is more preferred, and an ethynyl group is further preferred.

[0115] Substituent is CO2R 14 When R 14 , preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, or an alkynyl group having 2 to 5 carbon atoms. As the alkyl group having 1 to 5 carbon atoms, an alkyl group having 1 to 4 carbon atoms is preferred, an alkyl group having 1 to 3 carbon atoms is more preferred, a methyl group or an ethyl group is further preferred, and a methyl group is further preferred. As the alkenyl group having 2 to 5 carbon atoms, an alkenyl group having 2 to 4 carbon atoms is preferred, a vinyl group, n-1-propenyl group, n-2-propenyl group, or 1-methylvinyl group is more preferred, and a vinyl group is further preferred. As the alkynyl group having 2 to 5 carbon atoms, an alkynyl group having 2 to 4 carbon atoms is preferred, an ethynyl group, n-1-propynyl group, or n-2-propynyl group is more preferred, and an ethynyl group is further preferred.

[0116] The substituent is CHCO2R 15 When R 15 , preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, or an alkynyl group having 2 to 5 carbon atoms. As the alkyl group having 1 to 5 carbon atoms, an alkyl group having 1 to 4 carbon atoms is preferred, an alkyl group having 1 to 3 carbon atoms is more preferred, a methyl group or an ethyl group is further preferred, and a methyl group is further preferred. As the alkenyl group having 2 to 5 carbon atoms, an alkenyl group having 2 to 4 carbon atoms is preferred, a vinyl group, n-1-propenyl group, n-2-propenyl group, or 1-methylvinyl group is more preferred, and a vinyl group is further preferred. As the alkynyl group having 2 to 5 carbon atoms, an alkynyl group having 2 to 4 carbon atoms is preferred, an ethynyl group, n-1-propynyl group, or n-2-propynyl group is more preferred, and an ethynyl group is further preferred.

[0117] When the substituent is an alkyl group, an alkyl group having 1 to 5 carbon atoms is preferred, an alkyl group having 1 to 4 carbon atoms is more preferred, an alkyl group having 1 to 3 carbon atoms is further preferred, a methyl group or an ethyl group is further preferred, and a methyl group is particularly preferred.

[0118] When the substituent is an alkenyl group, an alkenyl group having 2 to 5 carbon atoms is preferred, an alkenyl group having 2 to 4 carbon atoms is more preferred, vinyl group, n-1-propenyl group, n-2-propenyl group or 1-methylvinyl group is further preferred, and vinyl group is further preferred.

[0119] When the substituent is an alkynyl group, an alkynyl group having 2 to 5 carbon atoms is preferred, an alkynyl group having 2 to 4 carbon atoms is more preferred, an ethynyl group, n-1-propynyl group or n-2-propynyl group is further preferred, and an ethynyl group is further preferred.

[0120] When the substituent is a hydroxyalkyl group, a hydroxyalkyl group having 1 to 5 carbon atoms is preferred, a hydroxyalkyl group having 1 to 4 carbon atoms is more preferred, a hydroxyalkyl group having 1 to 3 carbon atoms is further preferred, and CH2OH, CH2CH2OH or CH(OH)CH3 is further preferred.

[0121] The substituent is =C n H 2n When n is 1 to 5, =C n H 2n , more preferably n is 1 to 4 =C n H 2n , more preferably n is 1 to 3 =C n H 2n , further preferably =CH2 or =C2H4, particularly preferably =CH2.

[0122] As the substituent of ring A, alkyl, carbonyl, ═C n H 2n , OH, more preferably carbonyl, =C n H 2n , OH, more preferably carbonyl, =C n H 2n , further preferably carbonyl, =CH2.

[0123] In the above formula (1), when R3 is an alkyl group, an alkyl group having 1 to 5 carbon atoms is preferred, an alkyl group having 1 to 4 carbon atoms is more preferred, an alkyl group having 1 to 3 carbon atoms is further preferred, a methyl group or an ethyl group is further preferred, and a methyl group is particularly preferred.

[0124] In the above formula (1), R4 is preferably an optionally substituted alkyl group having 1 to 5 carbon atoms, CHO, or CO2R5. When R4 is an optionally substituted alkyl group having 1 to 5 carbon atoms, R4 is more preferably an optionally substituted alkyl group having 1 to 4 carbon atoms, further preferably an optionally substituted alkyl group having 1 to 3 carbon atoms, further preferably a methyl group or an ethyl group, and particularly preferably a methyl group. When R4 is CO2R5, R5 is preferably an alkyl group having 1 to 5 carbon atoms, more preferably an alkyl group having 1 to 4 carbon atoms, further preferably an alkyl group having 1 to 3 carbon atoms, further preferably a methyl group or an ethyl group, and particularly preferably a methyl group.

[0125] In the above formula (1), when R6 and R7 together form a double bond, the compound represented by formula (1) is represented by the following formula (1C).

[0126]

[0127] (In formula (1C),

[0128] The meanings of R1~R5 and R8~R9 are the same as above.

[0129] The dotted part is a single bond or a double bond.

[0130] However, the case of the structure represented by the above formula (2) is not included.)

[0131] In the above formula (1), when R6 and R7 together form an epoxy ring, the compound represented by formula (1) is represented by the following formula (1D).

[0132]

[0133] (In formula (1D),

[0134] The meanings of R1~R5 and R8~R9 are the same as above.

[0135] The dotted part is a single bond or a double bond.)

[0136] In the above formula (1), when the dotted line portion is a double bond, the compound represented by formula (1) is represented by the following formula (1E). In this case, R1 does not exist in formula (1) and R2 is a hydrogen atom.

[0137]

[0138] (In formula (1E),

[0139] R3 to R9 have the same meanings as above.)

[0140] In the above formula (1), when the dotted line portion is a single bond, the compound represented by formula (1) is represented by the following formula (1F). In this case, R1 and R2 in formula (1) are each a hydrogen atom.

[0141]

[0142] (In formula (1F),

[0143] R3 to R9 have the same meanings as above.)

[0144] In the above formula (1), when R1 and R2 together with their adjacent carbon atoms form an optionally substituted 6-membered saturated carbocyclic ring, the dotted portion is a single bond, and R6 and R7 together form a double bond, the compound represented by formula (1) is as shown in the following formula (1G).

[0145]

[0146] (In formula (1G),

[0147] R3 to R5 and R8 to R9 have the same meanings as above.

[0148] However, the case of the structure represented by the above formula (2) is not included.)

[0149] In the above formula (1), when R1 and R2 together with the carbon atoms adjacent to them form an optionally substituted 6-membered saturated carbon ring, the dotted portion is a single bond, and R6 and R7 together form an epoxy ring, the compound represented by formula (1) is as shown in the following formula (1H).

[0150]

[0151] (In formula (1H),

[0152] R3 to R5, R8 to R9 have the same meanings as above.)

[0153] Preferred examples of the compound represented by the above formula (1B) include compounds represented by the following formula (3).

[0154]

[0155] (In formula (3),

[0156] The meanings of R3 to R9 are the same as above.

[0157] The dotted part is a single bond or a double bond.

[0158] R 10 and R 10 When the dotted line between adjacent carbon atoms is a single bond, R 10 For OH,

[0159] R 10 and R 10 When the dotted line between adjacent carbon atoms is a double bond, R 10 is an oxygen atom, CH2, CHCHO, or CHCO2R 11 ,

[0160] R 11 is a hydrogen atom or an optionally substituted alkyl, alkenyl, alkynyl, hydroxyalkyl, cycloalkyl, cycloalkylalkyl, aryl, heteroaryl or aralkyl group,

[0161] R 12 and R 13 are each independently a hydrogen atom or OH.

[0162] However, the case of the structure represented by the following formula (2) is not included.)

[0163]

[0164] As R11 , preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, or an alkynyl group having 2 to 5 carbon atoms. As the alkyl group having 1 to 5 carbon atoms, an alkyl group having 1 to 4 carbon atoms is preferred, an alkyl group having 1 to 3 carbon atoms is more preferred, a methyl group or an ethyl group is further preferred, and a methyl group is further preferred. As the alkenyl group having 2 to 5 carbon atoms, an alkenyl group having 2 to 4 carbon atoms is preferred, a vinyl group, n-1-propenyl group, n-2-propenyl group, or 1-methylvinyl group is more preferred, and a vinyl group is further preferred. As the alkynyl group having 2 to 5 carbon atoms, an alkynyl group having 2 to 4 carbon atoms is preferred, an ethynyl group, n-1-propynyl group, or n-2-propynyl group is more preferred, and an ethynyl group is further preferred.

[0165] When R1 and R2 together with their adjacent carbon atoms form an optionally substituted 6-membered saturated carbocyclic ring, specific examples of the compound represented by the above formula (1) include compounds represented by the following formulas (3A) to (3F).

[0166]

[0167] (In formula (3A) to formula (3F),

[0168] R3 to R9 have the same meanings as above.

[0169] However, the case of the structure represented by the above formula (2) is not included.)

[0170] More specifically, the compound represented by the above formula (1) or a salt thereof is preferably a compound represented by the following formula (1B') or (1E') or a salt thereof.

[0171]

[0172] (In formula (1B'),

[0173] R3 to R9 have the same meanings as above.

[0174] However, the case of the structure represented by the above formula (2) is not included.

[0175] In addition, in formula (1E'),

[0176] R3 to R9 have the same meanings as above.)

[0177] In the compounds represented by the above formulae, each group in the formulae may be any combination of a preferred group, a more preferred group, a further preferred group, a still further preferred group, and a particularly preferred group. That is, when illustrating two groups in the compounds represented by the formulae, the compounds may be compounds represented by the formulae having the following structure: x and R vThe structure is formed by any combination of groups selected from preferred groups, more preferred groups, further preferred groups, further preferred groups, and particularly preferred groups. The compounds represented by each formula can be, for example, selected preferred groups as R x , select a more preferred group as R v The compound represented by the formula can be selected as a particularly preferred group as R x , select a further preferred group as R v The compound represented by the formula .

[0178] More specifically, examples of the acaricide of the present embodiment include compounds represented by the following formulae (13) to (21) or salts thereof.

[0179]

[0180] As the acaricide of the present embodiment, compounds represented by the above formulae (13) to (18) or salts thereof are preferred as the compound represented by the above formula (1) or a salt thereof.

[0181] More specifically, examples of the acaricide of the present embodiment include compounds represented by the following formulae (4) to (12) or salts thereof.

[0182]

[0183] It should be noted that when the acaricide of this embodiment contains the compound represented by formula (5) or its salt and the compound represented by formula (10) or its salt, the molar number of the compound represented by formula (5) or its salt relative to the molar number of the compound represented by formula (10) or its salt is 2 to 10, 3 to 9, or 4 to 8.

[0184] As the acaricide of the present embodiment, the compound represented by the above formula (1) or a salt thereof is preferably a compound represented by the above formula (4) to (9) or a salt thereof.

[0185] 1.2. Synthesis of the compound represented by formula (1) or its salt

[0186] The compound represented by formula (1) or its salt is not particularly limited and can be synthesized, for example, based on the method described in J. Pestic. Sci. 48 (3), 111-115 (2023). In addition, compounds represented by formula (1) that are not described in the above literature can also be prepared based on the method described in the above literature.

[0187] The catalyst used in the method for producing the compound represented by formula (1) or a salt thereof is not limited to the catalysts disclosed in the above-mentioned literature, and examples thereof include inorganic catalysts such as zinc compounds, nickel compounds, platinum compounds, and lithium compounds; and organic catalysts such as proline and MacMillan catalysts.

[0188] The base used in the method for producing the compound represented by formula (1) or a salt thereof is not limited to the bases disclosed in the above-mentioned literature, and examples thereof include inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, etc.; acetates such as sodium acetate and potassium acetate; alkali metal alcoholates such as potassium tert-butoxide, sodium methoxide, sodium ethoxide; tertiary amines such as triethylamine and diisopropylethylamine; and nitrogen-containing aromatic compounds such as pyridine and dimethylaminopyridine.

[0189] The solvent used in the method for producing the compound represented by formula (1) or a salt thereof is not particularly limited to the solvents disclosed in the above-mentioned literature as long as it does not inhibit the reaction. Examples thereof include aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated aliphatic hydrocarbons such as dichloromethane, chloroform, and carbon tetrachloride; halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene; chain or cyclic ethers such as diethyl ether, methyl tert-butyl ether, dioxane, and tetrahydrofuran; esters such as ethyl acetate; amides such as dimethylformamide and dimethylacetamide; ketones such as acetone and methyl ethyl ketone; and polar solvents such as dimethyl sulfoxide, 1,3-dimethyl-2-imidazolidinone, and water.

[0190] Alternatively, as a method of producing the compound represented by formula (1) or a salt thereof, a commercially available product may be used directly, a component extracted from a plant or the like may be used directly, or a compound may be synthesized / derived from a component extracted from a plant or the like.

[0191] 1.3. Other compounds

[0192] The acaricide of this embodiment may contain, in addition to the compound represented by formula (1) or its salt, effective substances contained in existing acaricides; solid carriers, liquid carriers, dispersants, wetting agents, tackifiers, thickeners, antifreeze agents, decomposition inhibitors, preservatives, antioxidants, defoaming agents, light stabilizers and other additives.

[0193] The compounds that are active substances contained in existing acaricides are not particularly limited, and examples thereof include tebufenpyrad, pyridabenz, fenpyroximate, mibemycin, abamectin, chlorfenapyr, etoxazole, acequinoxaline, bifenazate, spiromesifen, spirotetramat, cyflumetofen, cypermethrin, pyrazoanilide, fenpyroximate, fluazifop, amitraz, fluvalinate, thymol, flumethrin, formic acid, oxalic acid, and compounds represented by the following formula (2), as well as salts of these compounds. The compounds that are active substances contained in existing acaricides may be used alone or in combination of two or more.

[0194]

[0195] The content of the compound that is an active substance contained in existing acaricides is preferably 1-30% by mass, 5-25% by mass, or 10-20% by mass relative to the total amount of the acaricide. Alternatively, the acaricide may not contain the compound that is an active substance contained in existing acaricides.

[0196] The solid carrier is not particularly limited, and examples thereof include natural minerals such as quartz, clay, kaolinite, pyrophyllite, sericite, talc, bentonite, acid clay, attapulgite, zeolite, and diatomaceous earth; inorganic salts such as calcium carbonate, ammonium sulfate, sodium sulfate, and potassium chloride; organic solid carriers such as synthetic silicic acid, synthetic silicates, starch, cellulose, and plant powders (such as sawdust, coconut shells, corn cobs, and tobacco stems); plastic carriers such as polyethylene, polypropylene, and polyvinylidene chloride; urea, inorganic hollow bodies, plastic hollow bodies, and fumed silica. The solid carrier may be used alone or in combination of two or more.

[0197] The content of the solid carrier is preferably 1-80% by mass, 5-70% by mass, 10-60% by mass, 15-50% by mass, 20-40% by mass, or 25-35% by mass relative to the total amount of the acaricide. Alternatively, the acaricide may not contain a solid carrier.

[0198] The liquid carrier is not particularly limited, and examples thereof include alcohols, such as monohydric alcohols such as methanol, ethanol, propanol, isopropanol, and butanol; polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, hexylene glycol, polyethylene glycol, polypropylene glycol, and glycerol; polyol compounds such as propylene glycol ether; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, and cyclohexanone; ethers such as diethyl ether, dioxane, ethylene glycol monoethyl ether, dipropyl ether, and tetrahydrofuran; and aliphatic hydrocarbons such as normal paraffins, cycloparaffins, isoparaffins, kerosene, and mineral oil. Aromatic hydrocarbons such as benzene, toluene, xylene, solvent naphtha, and alkylnaphthalene; halogenated aliphatic hydrocarbons such as dichloromethane, chloroform, and carbon tetrachloride; esters such as ethyl acetate, diisopropyl naphthoate, dibutyl phthalate, dioctyl phthalate, and dimethyl adipate; lactones such as γ-butyrolactone; amides such as dimethylformamide, diethylformamide, dimethylacetamide, and N-alkylpyrrolidone; nitriles such as acetonitrile; sulfur compounds such as dimethyl sulfoxide; vegetable oils such as soybean oil, rapeseed oil, cottonseed oil, and castor oil; and water. The liquid carrier may be used alone or in combination of two or more.

[0199] The content of the liquid carrier is preferably 1-80% by mass, 5-70% by mass, 10-60% by mass, 15-50% by mass, 20-40% by mass, or 25-35% by mass relative to the total amount of the acaricide. Alternatively, the acaricide may contain no liquid carrier.

[0200] The surfactant used as the dispersant or wetting agent is not particularly limited, and examples thereof include sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters, sucrose fatty acid esters, polyoxyethylene fatty acid esters, polyoxyethylene resin acid esters, polyoxyethylene fatty acid diesters, polyoxyethylene alkyl ethers, polyoxyethylene alkylaryl ethers, polyoxyethylene alkylphenyl ethers, polyoxyethylene dialkylphenyl ethers, polyoxyethylene alkylphenyl ether formaldehyde condensates, polyoxyethylene polyoxypropylene block copolymers, polystyrene polyoxyethylene block polymers, alkyl polyoxyethylene polypropylene block copolymer ethers, polyoxyethylene alkylamines, polyoxyethylene fatty acid amides, polyoxyethylene fatty acid biphenyl ethers, polyalkylene benzyl phenyl ethers, polyoxyalkylene styryl phenyl ethers, acetylene glycol, acetylene glycol to which polyoxyalkylene is added, polyoxyethylene ether-type silicones, ester-type silicones, fluorine-based surfactants, polyoxyethylene castor oil, polyoxyethylene Nonionic surfactants such as hydrogenated castor oil; anionic surfactants such as alkyl sulfates, polyoxyethylene alkyl ether sulfates, polyoxyethylene alkylphenyl ether sulfates, polyoxyethylene styrylphenyl ether sulfates, alkylbenzene sulfonates, alkylaryl sulfonates, lignin sulfonates, alkyl sulfosuccinates, naphthalene sulfonates, alkylnaphthalene sulfonates, salts of formaldehyde condensates of naphthalenesulfonic acid, salts of formaldehyde condensates of alkylnaphthalenesulfonic acid, fatty acid salts, polycarboxylates, polyacrylic acids, N-methyl-fatty acyl sarcosinates, resinates, polyoxyethylene alkyl ether phosphates, polyoxyethylene alkylphenyl ether phosphates; cationic surfactants such as laurylamine hydrochloride, stearylamine hydrochloride, oleylamine hydrochloride, stearylamine acetate, stearylaminopropylamine acetate, alkyltrimethylammonium chloride, alkyldimethylbenzalkonium chloride, and alkylamine salts; amphoteric surfactants such as amino acid type or betaine type.

[0201] The content of the dispersant and wetting agent is preferably 1 to 10% by mass, 2 to 9% by mass, or 3 to 8% by mass relative to the total amount of the acaricide. Alternatively, the acaricide may not contain a dispersant and a wetting agent.

[0202] The thickener is not particularly limited, and examples thereof include carboxymethyl cellulose, salts thereof, dextrin, water-soluble starch, xanthan gum, guar gum, sucrose, polyvinyl pyrrolidone, gum arabic, polyvinyl alcohol, polyvinyl acetate, sodium polyacrylate, polyethylene glycol having an average molecular weight of 6,000 to 20,000, polyethylene oxide having an average molecular weight of 100,000 to 5,000,000, phospholipids (e.g., cephalin, lecithin, etc.), cellulose powder, dextrin, modified starch, polyaminocarboxylic acid chelate, cross-linked polyvinyl pyrrolidone, copolymers of maleic acid and styrene, (meth)acrylic acid copolymers, half esters of polymers composed of polyols and dicarboxylic anhydrides, water-soluble salts of polystyrene sulfonic acid, paraffin wax, terpenes, polyamide resins, polyacrylates, polyethylene oxide, waxes, polyvinyl alkyl ethers, alkylphenol formaldehyde condensates, and synthetic resin emulsions.

[0203] The content of the thickener is preferably 1 to 10% by mass, 2 to 9% by mass, or 3 to 8% by mass relative to the total amount of the acaricide. Alternatively, the acaricide may not contain a thickener.

[0204] The thickener is not particularly limited, and examples thereof include water-soluble polymers such as xanthan gum, guar gum, diutan gum, carboxymethyl cellulose, polyvinyl pyrrolidone, carboxyvinyl polymers, acrylic polymers, starch compounds, and polysaccharides, and inorganic fine powders such as high-purity bentonite and fumed silica.

[0205] The content of the thickener is preferably 1 to 10% by mass, 2 to 9% by mass, or 3 to 8% by mass relative to the total amount of the acaricide. Alternatively, the acaricide may not contain a thickener.

[0206] The antifreeze agent is not particularly limited, and examples thereof include polyols such as ethylene glycol, diethylene glycol, propylene glycol, and glycerin.

[0207] The content of the antifreeze agent is preferably 1 to 10% by mass, 2 to 9% by mass, or 3 to 8% by mass relative to the total amount of the acaricide. Alternatively, the acaricide may not contain an antifreeze agent.

[0208] The decomposition inhibitor is not particularly limited, and examples thereof include desiccants such as zeolite, quicklime, and magnesium oxide; antioxidants such as phenol compounds, amine compounds, sulfur compounds, and phosphoric acid compounds; and ultraviolet absorbers such as salicylic acid compounds and benzophenone compounds.

[0209] The content of the anti-decomposition agent is preferably 1 to 10% by mass, 2 to 9% by mass, or 3 to 8% by mass relative to the total amount of the acaricide. Alternatively, the acaricide may not contain the anti-decomposition agent.

[0210] The preservative is not particularly limited, and examples thereof include potassium sorbate and 1,2-benzothiazoline-3-one.

[0211] The content of the preservative is preferably 1 to 10% by mass, 2 to 9% by mass, or 3 to 8% by mass relative to the total amount of the acaricide. Alternatively, the acaricide may not contain a preservative.

[0212] The antioxidant is not particularly limited, and examples thereof include phenol compounds, amine compounds, sulfur compounds, and phosphoric acid compounds.

[0213] The content of the antioxidant is preferably 1 to 10% by mass, 2 to 9% by mass, or 3 to 8% by mass relative to the total amount of the acaricide. Alternatively, the acaricide may not contain an antioxidant.

[0214] The light stabilizer is not particularly limited, and examples thereof include salicylic acid compounds and benzophenone compounds.

[0215] The content of the light stabilizer is preferably 1 to 10% by mass, 2 to 9% by mass, or 3 to 8% by mass relative to the total amount of the acaricide. Alternatively, the acaricide may not contain a light stabilizer.

[0216] When the acaricide contains other compounds, the content of the compound represented by formula (1) or a salt thereof is preferably 10 to 95% by mass, 20 to 90% by mass, 30 to 90% by mass, 40 to 90% by mass, 50 to 90% by mass, 60 to 90% by mass, or 70 to 90% by mass relative to the total amount of the acaricide. Furthermore, when the acaricide does not contain other compounds, the acaricide may consist essentially of the compound represented by formula (1) or a salt thereof, or may consist of the compound represented by formula (1) or a salt thereof.

[0217] It should be noted that essential oils and the like containing the compound represented by formula (1) or a salt thereof can be used as the acaricide of this embodiment. These essential oils and the like may contain the other compounds mentioned above.

[0218] 2. Method for manufacturing acaricide

[0219] The compound represented by formula (1) or a salt thereof can be produced by the above-mentioned production method to serve as the acaricide of this embodiment. Alternatively, the compound represented by formula (1) or a salt thereof can be produced by the above-mentioned production method, and the compound represented by formula (1) or a salt thereof can be mixed with other compounds to serve as the acaricide of this embodiment. For example, the acaricide of this embodiment can be a water-dispersible agent, a solvent-dispersible agent such as an alcohol dispersion, a granule, a powder, an emulsion, an aqueous solvent, a suspension, a water-dispersible granule, a floating agent, an aerosol, a mist, a heat-evaporating agent, a fumigant, a poison bait, a microcapsule, or the like.

[0220] 3. How to use acaricide

[0221] The acaricide of this embodiment can be used directly or diluted with a solvent such as water, ethanol, or acetone. Examples of methods for using the acaricide of this embodiment include spreading the acaricide on plants or soil; administering the acaricide to livestock such as cattle, pigs, and bees, and pets such as dogs and cats, using tablets, capsules, impregnation solutions, mixing into feed, suppositories, or injections; administering the acaricide to livestock such as cattle, pigs, and bees, and pets such as dogs and cats, by spraying, pouring, or dripping; and administering the acaricide to livestock such as cattle, pigs, and bees, and pets such as dogs and cats, by vaporizing the acaricide and placing the livestock such as cattle, pigs, and bees, and pets such as dogs and cats in the vaporized space. It should be noted that methods of administering the acaricide to livestock and pets by spraying, pouring, or dripping are also referred to as contact methods. A method of administering the acaricide to livestock and pets by vaporizing the acaricide and placing the livestock and pets in a space where the vapor exists is also called a vapor diffusion method.

[0222] The acaricide of this embodiment can be used for both preventive and actual expulsion of mites and ticks. For example, to expel mites and ticks that are parasitic on livestock and pets, the acaricide can be applied to the mites and ticks, or the acaricide can be applied to the livestock and pets when the livestock and pets are not parasitic on mites and ticks.

[0223] In this embodiment, it is preferred to administer the acaricide to mites and ticks by vapor diffusion or contact. Furthermore, in this embodiment, it is preferred to administer the acaricide to bees or cattle, which are livestock species, and administer the acaricide to mites and ticks that parasitize bees or cattle. Furthermore, in this embodiment, it is more preferred to administer the acaricide to bees, which are livestock species, and administer the acaricide to mites and ticks that parasitize bees. Furthermore, in this embodiment, it is further preferred to administer the acaricide to bees, which are livestock species, and administer the acaricide to mites and ticks that parasitize bees.

[0224] It should be noted that the effects of acaricides include, in addition to killing mites and ticks, inhibiting the growth and reproduction of mites and ticks, preventing parasitism by mites and ticks, promoting deparasitism by mites and ticks, and avoiding parasitism by mites and ticks.

[0225] In addition, in this embodiment, the use of the compound includes allowing the compound to act on the target to be repelled by conventional methods, including spreading the compound.

[0226] 4. Eliminate the object

[0227] The acaricide of the present embodiment is intended to repel mites and ticks. The mites and ticks to be repelled are not particularly limited, and examples thereof include Tetranychus urticae, Tetranychus cinnabarinus, Tetranychus kanzawai, Panonychus citri, Panonychus ulmi, Aculops pelekassi, Acullus schlechtendali, Polyphagotarsonemus latus, Brevipalpus, Eotetranychus, Rhizoglyphus robini, Tyrophagus putrescentiae, Dermatophagoides farinae Hughes, Rhipicephalus microplus, Haemaphysalis longicornis, and the like. longicornis), hard ticks, Varroa mites, cattle ticks, and the larvae and eggs of these ticks. Among them, the acaricide of this embodiment is suitable for use against Varroa mites that parasitize honeybees and cattle ticks that parasitize cattle ticks. Examples of Varroa mites that parasitize honeybees include Varroa destructor. Examples of cattle ticks that parasitize cattle include Rhipicephalus microplus.

[0228] The acaricide of this embodiment also has excellent repellent effects against drug-resistant mites and ticks. Furthermore, the acaricide of this embodiment has low toxicity to the objects infested by mites and ticks, thus preventing adverse effects on these objects. For example, when the acaricide of this embodiment is used on bees infested with drug-resistant Varroa mites or cattle infested with drug-resistant cattle ticks, the Varroa mites and cattle ticks can be repelled without adverse effects on the bees or cattle.

[0229] Example

[0230] The present invention will be described in more detail below using Examples and Comparative Examples. The present invention is not limited in any way by the following Examples. In addition, the experiments in Examples and Comparative Examples were conducted at room temperature (25°C) and 1 atm unless otherwise specified.

[0231] 1. Preparation of acaricide

[0232] The following compounds represented by formulae (4) to (8), (10), (22) to (23) were synthesized according to the method described in J. Pestic. Sci. 48(3), 111-115(2023).

[0233]

[0234] The compound represented by the following formula (9) was synthesized by using (s)-(-)-limonene (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) and formylation thereof.

[0235]

[0236] As the compound represented by the following formula (24), a commercially available product sold as Amitraz was used.

[0237]

[0238] The compounds of formulae (4) to (9) and (32) to (34) thus obtained were each subjected to the acaricidal activity test described below as acaricides. Separately, the compound of formula (5) and the compound of formula (10) were mixed at a molar ratio of compound (5) to compound (10) = 6:1, and the resulting mixture was subjected to the acaricidal activity test described below as acaricide.

[0239] 2. Acaricidal activity test

[0240] Vapor diffusion method

[0241] [Example 1]

[0242] First, a plurality of Varroa destructans mites were placed at the bottom of a 30 mL glass vial. The compound of formula (4) obtained above was then dissolved in acetone at a concentration of 10 mg / mL to obtain an acetone solution of the compound of formula (4). 60 μL of this acetone solution was permeated into filter paper, which was then placed on the cap of the vial. The acetone was then removed from the vial, and 20 μL of water was added to maintain the humidity within the vial. The vial was then sealed and placed in an environment at 20°C. The time of sealing the vial was set to 0 h, and the viability of the Varroa destructans mites was checked every two hours. Specifically, the Varroa destructans were observed under a microscope, and death was determined when no movement of the limbs of the mite was detected. The ratio (%) of the number of dead Varroa destructans to the number of Varroa destructans initially placed was calculated as the Varroa mortality rate (%). It should be noted that the Varroa destructans did not directly contact the filter paper.

[0243] [Comparative Example 1]

[0244] The acaricidal activity test was conducted in the same manner as in Example 1 except that the compound of formula (22) was used instead of the compound of formula (4) in Example 1.

[0245] [Comparative Example 2]

[0246] The acaricidal activity test was conducted in the same manner as in Example 1 except that the compound of formula (23) was used instead of the compound of formula (4) in Example 1.

[0247] [Example 2]

[0248] The acaricidal activity test was conducted in the same manner as in Example 1 except that the compound of formula (5) was used instead of the compound of formula (4) in Example 2.

[0249] [Example 3]

[0250] The acaricidal activity test was conducted in the same manner as in Example 1 except that the compound of formula (6) was used instead of the compound of formula (4) in Example 3.

[0251] [Example 4]

[0252] The acaricidal activity test was conducted in the same manner as in Example 1 except that the compound of formula (7) was used instead of the compound of formula (4) in Example 4.

[0253] [Example 5]

[0254] The acaricidal activity test was conducted in the same manner as in Example 1 except that the compound of formula (8) was used instead of the compound of formula (4) in Example 5.

[0255] [Example 6]

[0256] The acaricidal activity test was conducted in the same manner as in Example 1 except that the compound of formula (9) was used instead of the compound of formula (4) in Example 6.

[0257] [Example 7]

[0258] First, the compound of formula (5) and the compound of formula (10) were mixed at a molar ratio of compound of formula (5):compound of formula (10) = 6:1 to obtain a mixture. Acaricidal activity was then tested in the same manner as in Example 1, except that the above mixture was used instead of the compound of formula (4) in Example 7.

[0259] [Comparative Example 1-1]

[0260] In Control Example 1, the acaricidal activity test was carried out in the same manner as in Example 1 except that the compound of formula (4) was not used.

[0261] [Comparative Example 1-2]

[0262] In Control Example 1-2, the same test as in Control Example 1-1 was performed on a different day from that in Control Example 1-1.

[0263] [Comparative Examples 1-3]

[0264] In Control Example 1-3, the same test as in Control Example 1-1 was performed on a different day from that in Control Example 1-1 and Control Example 1-2.

[0265] The results of Example 1, Comparative Example 1, Comparative Example 2 and Control Example 1-1 are shown in Figure 1 In addition, the results of Examples 2 to 6 and Comparative Examples 1-2 are shown in Figure 2 In addition, the results of Example 7 and Comparative Examples 1-3 are shown in Figure 3 It should be noted that the results are shown in Figure 1 All the tests were conducted on the same day. Figure 2 All the tests were conducted on the same day. Figure 3 All the tests were carried out on the same day. In addition, regarding Example 6, the experiment was terminated after 20 hours.

[0266] 2.2. Contact method

[0267] [Example 8]

[0268] The compound of formula (4) obtained above was dissolved in acetone at a concentration of 100 mg / L to obtain an acetone solution of the compound of formula (4). 0.5 mL of the acetone solution was placed in a 20 mL glass vial. The vial was manually rotated horizontally for 2 hours in a fume hood at room temperature to completely evaporate the acetone. The compound of formula (4) was then uniformly precipitated onto the inner wall of the vial. A plurality of Varroa destructans belonging to the varroa mite were placed in the vial. The vial was then sealed and placed in an environment of 20°C. The time when the vial was sealed was set to 0 hours, and the life and death of the Varroa destructans was confirmed every 2 hours. Specifically, the Varroa destructans were observed under a microscope, and the Varroa destructans were judged to be dead when no movement of the limbs of the Varroa destructans was detected. Then, the ratio (%) of the number of dead Varroa destructans to the number of Varroa destructans initially placed was calculated as the Varroa mortality rate (Varroa mortality: %).

[0269] [Comparative Example 3]

[0270] In Comparative Example 3, the acaricidal activity test was conducted in the same manner as in Example 8, except that the compound of formula (23) was used instead of the compound of formula (4).

[0271] [Comparative Example 4-1]

[0272] In Comparative Example 4-1, the acaricidal activity test was carried out in the same manner as in Example 8, except that the compound of formula (24) was used instead of the compound of formula (4).

[0273] [Comparative Example 4-2]

[0274] In Comparative Example 4-2, the same test as in Comparative Example 4-1 was performed on a different day from that in Comparative Example 4-1.

[0275] [Comparative Example 2-1]

[0276] In Control Example 2-1, the acaricidal activity test was carried out in the same manner as in Example 8, except that the compound of formula (4) was not used.

[0277] [Comparative Example 2-2]

[0278] In Control Example 2-2, the same test as in Control Example 2-1 was performed on a different day from that in Control Example 2-1.

[0279] The results of Control Example 2-1, Comparative Example 3, and Comparative Example 4-1 are shown in Figure 4 In addition, the results of Control Example 2-2, Comparative Example 4-2, and Example 8 are shown in Figure 5 It should be noted that the results are shown in Figure 4 All the tests were conducted on the same day. Figure 5 All tests were performed on the same day.

Claims

1. An acaricide comprising a compound represented by the following formula (1) or a salt thereof, In formula (1), R1 is absent or is a hydrogen atom, R2 is a hydrogen atom; or R1 and R2 together with their adjacent carbon atoms form an optionally substituted 6-membered saturated carbocyclic ring, R3 is a hydrogen atom or an alkyl group, R4 is optionally substituted alkyl, alkenyl, alkynyl, hydroxyalkyl, cycloalkyl, cycloalkylalkyl, aryl, heteroaryl, aralkyl, CHO or CO2R5, R5 is a hydrogen atom or an optionally substituted alkyl, alkenyl, alkynyl, hydroxyalkyl, cycloalkyl, cycloalkylalkyl, aryl, heteroaryl or aralkyl group, R6 and R7 together form a double bond or an epoxy ring, R8 and R9 are each independently a hydrogen atom or OH, The dotted part is a single bond or a double bond. in, Excluding the case where formula (1) is a structure represented by the following formula (2), 2. The acaricide according to claim 1, wherein R3 is an alkyl group having 1 to 5 carbon atoms.

3. The acaricide according to claim 1, wherein R4 is an optionally substituted alkyl group having 1 to 5 carbon atoms, CHO or CO2R5, R5 is an alkyl group having 1 to 5 carbon atoms.

4. The acaricide according to claim 1, wherein Containing a compound represented by the following formula (3) or a salt thereof, In formula (3), The meanings of R3 to R9 are the same as above. The dotted part is a single bond or a double bond. When R 10 and R 10 When the dotted line between adjacent carbon atoms is a single bond, R 10 For OH, When R 10 and R 10 When the dotted line between adjacent carbon atoms is a double bond, R 10 is an oxygen atom, CH2, CHCHO, or CHCO2R 11 , R 11 is a hydrogen atom or an optionally substituted alkyl, alkenyl, alkynyl, hydroxyalkyl, cycloalkyl, cycloalkylalkyl, aryl, heteroaryl or aralkyl group, R 12 and R 13 are each independently a hydrogen atom or OH, However, the case where formula (3) is a structure represented by the following formula (2) is not included.

5. An acaricide comprising a compound represented by the following formula (4) to (12) or a salt thereof, The acaricide according to claim 1 , which is used to repel Varroa mites or cattle ticks.

7. The acaricide according to claim 1, which is used in combination with other acaricides.

8. The acaricide according to claim 7, wherein The other acaricides are selected from one or more of the group consisting of tebufenpyrad, pyridabenz, fenpyroximate, mibemycin, abamectin, chlorfenapyr, etoxazole, acequinoxaline, bifenazate, spiromesifen, spirotetramat, cyflumetofen, cypermethrin, pyraclostrobin, pyrazoanilide, fenpyroximate, fluazifop, amitraz, fluvalinate, thymol, flumethrin, formic acid, oxalic acid and compounds represented by the following formula (2), and salts of these compounds.

9. A method for expelling mites and ticks, comprising using the acaricide according to any one of claims 1 to 8 against mites and ticks.

10. The method for expelling mites and ticks according to claim 9, wherein: The acaricide is applied to mites in a vapor diffusion method or a contact method.

11. The method for expelling mites and ticks according to claim 9, wherein: The acaricide is allowed to act on honeybees to expel mites and ticks parasitic on the honeybees.

12. The method for expelling mites and ticks according to claim 9, wherein: Use in combination with other acaricides.

13. The method for expelling mites and ticks according to claim 12, wherein: The other acaricide is one or more selected from the group consisting of tebufenpyrad, pyridabenz, fenpyroximate, mibemycin, abamectin, chlorfenapyr, etoxazole, acequinoxaline, bifenazate, spiromesifen, spirotetramat, cyflumetofen, cypermethrin, pyrazoanilide, fenpyroximate, fluazifop, amitraz, fluvalinate, thymol, flumethrin, formic acid, oxalic acid and compounds represented by the following formula (2), and salts of these compounds.

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