Method for controlling harmful arthropods or harmful nematodes using zoanthamine analog

Abstract

The present invention provides a method for controlling harmful arthropods or harmful nematodes. Compounds represented by formula (I) [in the formula, R1 represents a hydrogen atom, etc., R2 represents ORA2, R3, R7, R14, R17, R19, and R25 represent hydrogen atoms, R4 represents a methyl group, etc., R5 represents a methyl group, etc., R6 represents a hydrogen atom, etc., R8 represents a hydrogen atom, etc., R9 represents a methyl group, etc., R10 represents a hydrogen atom, etc., R11 represents ORA9, R12 represents a hydrogen atom, etc., R13 represents a hydrogen atom, etc., R15 represents a hydrogen atom, etc., R16 represents a hydrogen atom, etc., R18 represents a methyl group, etc., R20 represents a hydrogen atom, etc., R21 represents a methyl group, etc., R22 represents a hydrogen atom, etc., R23 represents a hydrogen atom, etc., R24 represents a hydrogen atom, etc., R26 represents a hydrogen atom, etc., R27 represents a C1-C3 alkoxy group, etc., and RA2 and RA9 represent hydrogen atoms, etc.], N-oxides thereof, and salts of the same can be used for controlling harmful arthropods or harmful nematodes.

Description

Method for controlling harmful arthropods or harmful nematodes using zoanthamine analogues

[0001] This patent application claims priority and the benefit of Japanese Patent Application No. 2022-032312 (filed March 3, 2022) and Japanese Patent Application No. 2022-133984 (filed August 25, 2022) under the Paris Convention, the entire contents of which are incorporated herein by reference.

[0002] The present invention relates to a method for controlling harmful arthropods or harmful nematodes using a zoanthamine analogue.

[0003] Various compounds have been investigated so far for the purpose of controlling harmful arthropods or harmful nematodes (see, for example, Non-Patent Document 1). Meanwhile, Non-Patent Document 2 describes that zoanthamines and their salts inhibit IL-6 production by osteoblasts and also inhibit the loss of bone mass and bone strength due to osteoporosis.

[0004] "The Pesticide Manual 18th Edition", British Crop Protection Council, 2018, ISBN 978-1999896614 "Bulletin of the Chemical Society of Japan", 1998, Vol. 71, pp. 771-779

[0005] An object of the present invention is to provide a method for controlling harmful arthropods or harmful nematodes.

[0006] The present invention includes, but is not limited to, the following embodiments: [1] Formula (I) [In the formula, R 1 is a hydrogen atom, a C1-C3 alkyl group, or CHOR A1 represents R 2 is OR A2 represents R 3 represents a hydrogen atom, R 4 is a methyl group or CH2OR A3 represents R 5 is a methyl group or CH2OR A4 represents R6 is a hydrogen atom or OR A5 represents R 7 represents a hydrogen atom, R 8 represents a hydrogen atom, a halogen atom, a methoxy group, or OR A6 represents R 9 is a methyl group or CH2OR A7 represents R 10 is a hydrogen atom or OR A8 represents R 11 is OR A9 represents R 12 is a hydrogen atom or OR A10 represents R 13 represents a hydrogen atom, a dichloromethyl group, a hydroxy(methoxy)methyl group, a hydroxy(ethoxy)methyl group, or OR A11 represents R 14 represents a hydrogen atom, R 15 is a hydrogen atom or OR A12 represents R 16 represents a hydrogen atom, a halogen atom, or OR A13 represents R 17 represents a hydrogen atom, R 18 is a methyl group, or CH2OR A14 represents R 19 represents a hydrogen atom, R 20 is a hydrogen atom or OR A15 represents R 21 is a methyl group, CH2OR A16 or CH2NHCH2C(O)OCH3, R 22 is a hydrogen atom or OR A17 represents R 23 is a hydrogen atom or OR A18 represents R 24 is a hydrogen atom, a C1-C3 alkoxy group, or OR A19 represents R 25 represents a hydrogen atom, R 26 is a hydrogen atom or OR A20 represents R 27 represents a C1-C3 alkoxy group or a hydroxy group, R A1 , R A2 , R A3 , RA4 , R A5 , R A6 , R A7 , R A8 , R A9 , R A10 , R A11 , R A12 , R A13 , R A14 , R A15 , R A16 , R A17 , R A18 , R A19 , and R A20 are the same or different and represent a hydrogen atom, a (C1-C6 alkyl)carbonyl group, or a (C3-C6 cycloalkyl)carbonyl group; R 1 and R 27 Together # 1 -CH2-O- may be formed, 1 is R 1 represents the bonding position with the carbon atom to which R is bonded; 2 and R 3 may be taken together to form an oxo group, and R 3 and R 18 Together # 3 -O-CHR B1 - may be formed, 3 is R 3 represents the bonding position with the carbon atom to which R is bonded; 4 and R 27 Together # 4 -CH2-O- may be formed, 4 is R 4 represents the bonding position with the carbon atom to which R is bonded; 6 and R 27 may be taken together to form a bond, and R 7 and R 11 may be taken together to form —O—, R 13 and R 14 may be taken together to form an oxo group, and R 15 and R 16 and may form a double bond together with the carbon atom to which they are attached, R 15 and R 18Together # 15 -O-CHR B2 - may be formed, 15 is R 15 represents the bonding position with the carbon atom to which R is bonded; 15 and R 27 may be taken together to form —O—, R 16 and R 17 may be taken together to form an oxo group, and R 18 and R 22 Together # 18 -CH2-O- may be formed, 18 is R 18 represents the bonding position with the carbon atom to which R is bonded; 18 and R 23 may be taken together to form —CH—, R 19 , R 20 , R 22 , R 23 , R 25 , and R 26 may form a benzene ring together with the carbon atom to which they are attached, R 21 and R 22 may be taken together to form =CH2, R 22 and R 23 and may form a double bond together with the carbon atom to which they are attached, R 24 and R 25 may be taken together to form an oxo group, and R B1 and R B2 and R are the same or different and represent a hydrogen atom, a C1-C3 alkoxy group, or a hydroxy group, excluding zoanthamin, norzoanthamin, zoanthaminone, and norzoanthaminone.], or an N-oxide thereof, or a salt thereof (hereinafter, the compound represented by formula (I), or the N-oxide thereof, or a salt thereof will be referred to as the present compound) to a harmful arthropod or a harmful nematode, or to a habitat of the harmful arthropod or the harmful nematode. [2] In formula (I), R 1 , R 2 , R3 , R 4 , R 6 , R 7 , R 11 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , R 21 , R 22 , R 23 , R 24 , R 25 , R 26 , and R 27 The method according to [1], wherein the combination of a:R is any one of the combinations a to g: 1 is a hydrogen atom, a C1-C3 alkyl group, or CH2OR A1 and R 2 is OR A2 and R 3 is a hydrogen atom, and R 2 and R 3 may be taken together to form an oxo group, and R 4 is a methyl group or CH2OR A3 and R 6 is a hydrogen atom or OR A5 and R 7 and R 11 and together form -O-, and R 13 is a hydrogen atom, a dichloromethyl group, a hydroxy(methoxy)methyl group, a hydroxy(ethoxy)methyl group, or OR A11 and R 14 is a hydrogen atom, and R 13 and R 14 may be taken together to form an oxo group, and R 15 and R 27 and together form -O-, and R 16 is a hydrogen atom, a halogen atom, or OR A13 and R 17 is a hydrogen atom, and R 16 and R 17 may be taken together to form an oxo group, and R 18 is a methyl group, or CH2OR A14 and R19 is a hydrogen atom, and R 20 is a hydrogen atom or OR A15 and R 21 is a methyl group, CH2OR A16 or CHNHCHC(O)OCH, and R 22 is a hydrogen atom or OR A17 and R 21 and R 22 may be taken together to form =CH2, and R 23 is a hydrogen atom, or OR A18 and R 18 and R 23 may be taken together to form —CH—, and R 22 and R 23 and may form a double bond together with the carbon atom to which they are attached, and R 24 is a hydrogen atom, a C1-C3 alkoxy group, or OR A19 and R 25 is a hydrogen atom, and R 24 and R 25 may be taken together to form an oxo group, and R 26 is a hydrogen atom or OR A20 a combination of: b: R 1 is a hydrogen atom, a C1-C3 alkyl group, or CH2OR A1 and R 2 and R 3 and together form an oxo group, and R 4 is a methyl group or CH2OR A3 and R 6 is a hydrogen atom or OR A5 and R 7 and R 11 and together form -O-, and R 13 is a hydrogen atom, a dichloromethyl group, a hydroxy(methoxy)methyl group, a hydroxy(ethoxy)methyl group, or OR A11 and R 14 is a hydrogen atom, and R 15 and R 27 and together form -O-, and R 16 is a hydrogen atom, a halogen atom, or OR A13 and R 17 is a hydrogen atom, and R18 is a methyl group, or CH2OR A14 and R 19 , R 20 , R 22 , R 23 , R 25 , and R 26 form a benzene ring together with the carbon atoms to which they are attached, and R 21 is a methyl group, CH2OR A16 or CHNHCHC(O)OCH, and R 24 is a C1-C3 alkoxy group, or OR A19 a combination of: c: R 1 is a hydrogen atom, a C1-C3 alkyl group, or CH2OR A1 and R 2 is OR A2 and R 3 is a hydrogen atom, and R 2 and R 3 may be taken together to form an oxo group, and R 3 and R 18 Together # 3 -O-CHR B1 - may be formed, and R 4 and R 27 Together # 4 -CH2-O- is formed, and R 6 is a hydrogen atom or OR A5 and R 7 and R 11 and together form -O-, and R 13 is a hydrogen atom, a dichloromethyl group, a hydroxy(methoxy)methyl group, a hydroxy(ethoxy)methyl group, or OR A11 and R 14 is a hydrogen atom, and R 15 is a hydrogen atom or OR A12 and R 16 is a hydrogen atom, a halogen atom, or OR A13 and R 15 and R 16 and may form a double bond together with the carbon atom to which they are attached, and R 17 is a hydrogen atom, and R 16 and R 17may be taken together to form an oxo group, and R 18 is a methyl group, or CH2OR A14 and R 15 and R 18 Together # 15 —O—CHR B2 - may be formed, and R 19 is a hydrogen atom, and R 20 is a hydrogen atom or OR A15 and R 21 is a methyl group, CH2OR A16 or CHNHCHC(O)OCH, and R 22 is a hydrogen atom or OR A17 and R 18 and R 22 Together # 18 may form —CH—O—, and R 23 is a hydrogen atom, or OR A18 and R 22 and R 23 and may form a double bond together with the carbon atom to which they are attached, and R 24 and R 25 and together form an oxo group, and R 26 is a hydrogen atom or OR A20 a combination of: d: R 1 and R 27 Together # 1 -CH2-O- is formed, and R 2 and R 3 and together form an oxo group, and R 4 is a methyl group or CH2OR A3 and R 6 is a hydrogen atom or OR A5 and R 7 and R 11 and together form -O-, and R 13 is a hydrogen atom, a dichloromethyl group, a hydroxy(methoxy)methyl group, a hydroxy(ethoxy)methyl group, or OR A11 and R 14 is a hydrogen atom, and R 15 is a hydrogen atom or OR A12 and R 16 is a hydrogen atom, a halogen atom, or ORA13 and R 17 is a hydrogen atom, and R 16 and R 17 may be taken together to form an oxo group, and R 18 is a methyl group, or CH2OR A14 and R 19 is a hydrogen atom, and R 20 is a hydrogen atom or OR A15 and R 21 is a methyl group, CH2OR A16 or CHNHCHC(O)OCH, and R 22 and R 23 and form a double bond together with the carbon atom to which they are attached, and R 24 and R 25 and together form an oxo group, and R 26 is a hydrogen atom or OR A20 a combination in which e:R 1 is a hydrogen atom, a C1-C3 alkyl group, or CH2OR A1 and R 2 and R 3 and together form an oxo group, and R 4 is a methyl group or CH2OR A3 and R 6 is a hydrogen atom or OR A5 and R 7 and R 11 and together form -O-, and R 13 is a hydrogen atom, a dichloromethyl group, a hydroxy(methoxy)methyl group, a hydroxy(ethoxy)methyl group, or OR A11 and R 14 is a hydrogen atom, and R 15 is a hydrogen atom or OR A12 and R 16 is a hydrogen atom, a halogen atom, or OR A13 and R 15 and R 16 and may form a double bond together with the carbon atom to which they are attached, and R 17 is a hydrogen atom, and R 18 is a methyl group, or CH2OR A14 and R 19 is a hydrogen atom, and R20 is a hydrogen atom or OR A15 and R 21 is a methyl group, CH2OR A16 or CHNHCHC(O)OCH, and R 22 is a hydrogen atom or OR A17 and R 23 is a hydrogen atom, or OR A18 and R 22 and R 23 and may form a double bond together with the carbon atom to which they are attached, and R 24 is a hydrogen atom, a C1-C3 alkoxy group, or OR A19 and R 25 is a hydrogen atom, and R 24 and R 25 may be taken together to form an oxo group, and R 26 is a hydrogen atom or OR A20 and R 27 is a C1-C3 alkoxy group or a hydroxy group. 1 is a hydrogen atom, a C1-C3 alkyl group, or CH2OR A1 and R 2 and R 3 and together form an oxo group, and R 4 is a methyl group or CH2OR A3 and R 6 and R 27 and together form a bond, and R 7 and R 11 and together form -O-, and R 13 is a hydrogen atom, a dichloromethyl group, a hydroxy(methoxy)methyl group, a hydroxy(ethoxy)methyl group, or OR A11 and R 14 is a hydrogen atom, and R 15 is a hydrogen atom or OR A12 and R 16 is a hydrogen atom, a halogen atom, or OR A13 and R 17 is a hydrogen atom, and R 18 is a methyl group, or CH2OR A14 and R 19 is a hydrogen atom, and R 20 is a hydrogen atom or ORA15 and R 21 is a methyl group, CH2OR A16 or CHNHCHC(O)OCH, and R 22 is a hydrogen atom or OR A17 and R 23 is a hydrogen atom, or OR A18 and R 22 and R 23 and may form a double bond together with the carbon atom to which they are attached, and R 24 is a hydrogen atom, a C1-C3 alkoxy group, or OR A19 and R 25 is a hydrogen atom, and R 24 and R 25 may be taken together to form an oxo group, and R 26 is a hydrogen atom or OR A20 and g: R 1 is a hydrogen atom, a C1-C3 alkyl group, or CH2OR A1 and R 2 and R 3 and together form an oxo group, and R 4 is a methyl group or CH2OR A3 and R 6 is a hydrogen atom or OR A5 and R 7 is a hydrogen atom, and R 11 is OR A9 and R 13 is a hydrogen atom, a dichloromethyl group, a hydroxy(methoxy)methyl group, a hydroxy(ethoxy)methyl group, or OR A11 and R 14 is a hydrogen atom, and R 15 is a hydrogen atom or OR A12 and R 16 is a hydrogen atom, a halogen atom, or OR A13 and R 17 is a hydrogen atom, and R 18 is a methyl group, or CH2OR A14 and R 19 is a hydrogen atom, and R 20 is a hydrogen atom or OR A15 and R 21 is a methyl group, CH2ORA16 or CHNHCHC(O)OCH, and R 22 is a hydrogen atom or OR A17 and R 23 is a hydrogen atom, or OR A18 and R 22 and R 23 and may form a double bond together with the carbon atom to which they are attached, and R 24 and R 25 and together form an oxo group, and R 26 is a hydrogen atom or OR A20 and R 27 is a C1-C3 alkoxy group or a hydroxy group. [3] In formula (I), R 5 is a methyl group, and R 1 , R 2 , R 3 , R 4 , R 6 , R 7 , R 11 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , R 21 , R 22 , R 23 , R 24 , R 25 , R 26 , and R 27 The combination of a 1 ~g 1 The method according to [1] or [2], wherein the combination is any one of: 1 :R 1 is a hydrogen atom, a C1-C3 alkyl group, or CH2OR A1 and R 2 is OR A2 and R 3 is a hydrogen atom, and R 2 and R 3 may be taken together to form an oxo group, and R 4 is a methyl group, and R 6 is a hydrogen atom, and R 7 and R 11and together form -O-, and R 13 is a hydrogen atom, and R 14 is a hydrogen atom, and R 13 and R 14 may be taken together to form an oxo group, and R 15 and R 27 and together form -O-, and R 16 is a hydrogen atom, a halogen atom, or OR A13 and R 17 is a hydrogen atom, and R 16 and R 17 may be taken together to form an oxo group, and R 18 is a methyl group, and R 19 is a hydrogen atom, and R 20 is a hydrogen atom, and R 21 is a methyl group or CH2OR A16 and R 22 is a hydrogen atom or OR A17 and R 21 and R 22 may be taken together to form =CH2, and R 23 is a hydrogen atom, or OR A18 and R 18 and R 23 may be taken together to form —CH—, and R 22 and R 23 and may form a double bond together with the carbon atom to which they are attached, and R 24 is a hydrogen atom or OR A19 and R 25 is a hydrogen atom, and R 24 and R 25 may be taken together to form an oxo group, and R 26 is a hydrogen atom; b 1 :R 1 is a hydrogen atom or a methyl group, and R 2 and R 3 and together form an oxo group, and R 4 is a methyl group, and R 6 is a hydrogen atom, and R 7 and R 11 and together form -O-, and R 13 is a hydrogen atom, and R14 is a hydrogen atom, and R 15 and R 27 and together form -O-, and R 16 is a hydrogen atom or a halogen atom, and R 17 is a hydrogen atom, and R 18 is a methyl group, and R 19 , R 20 , R 22 , R 23 , R 25 , and R 26 form a benzene ring together with the carbon atoms to which they are attached, and R 21 is a methyl group, and R 24 is a C1-C3 alkoxy group or OR A19 a combination in which 1 :R 1 is a methyl group, and R 2 is OR A2 and R 3 is a hydrogen atom, and R 2 and R 3 may be taken together to form an oxo group, and R 3 and R 18 Together # 3 -O-CHR B1 - may be formed, and R 4 and R 27 Together # 4 -CH2-O- is formed, and R 6 is a hydrogen atom or OR A5 and R 7 and R 11 and together form -O-, and R 13 is a hydrogen atom or OR A11 and R 14 is a hydrogen atom, and R 15 is a hydrogen atom, and R 16 is a hydrogen atom, a halogen atom, or OR A13 and R 15 and R 16 and may form a double bond together with the carbon atom to which they are attached, and R 17 is a hydrogen atom, and R 16 and R 17 may be taken together to form an oxo group, and R18 is a methyl group, and R 15 and R 18 Together # 15 -O-CHR B2 - may be formed, and R 19 is a hydrogen atom, and R 20 is a hydrogen atom or OR A15 and R 21 is a methyl group, CH2OR A16 or CHNHCHC(O)OCH, and R 22 is a hydrogen atom, and R 18 and R 22 Together # 18 may form —CH—O—, and R 23 is a hydrogen atom, and R 22 and R 23 and may form a double bond together with the carbon atom to which they are attached, and R 24 and R 25 and together form an oxo group, and R 26 is a hydrogen atom or OR A20 a combination in which 1 :R 1 and R 27 Together # 1 -CH2-O- is formed, and R 2 and R 3 and together form an oxo group, and R 4 is a methyl group, and R 6 is a hydrogen atom, and R 7 and R 11 and together form -O-, and R 13 is a hydrogen atom, and R 14 is a hydrogen atom, and R 15 is a hydrogen atom or OR A12 and R 16 is a hydrogen atom, a halogen atom, or OR A13 and R 17 is a hydrogen atom, and R 16 and R 17 may be taken together to form an oxo group, and R 18 is a methyl group, and R 19 is a hydrogen atom, and R 20 is a hydrogen atom, and R21 is a methyl group, and R 22 and R 23 and form a double bond together with the carbon atom to which they are attached, and R 24 and R 25 and together form an oxo group, and R 26 is a hydrogen atom; 1 :R 1 is a hydrogen atom or a C1-C3 alkyl group, and R 2 and R 3 and together form an oxo group, and R 4 is a methyl group, and R 6 is a hydrogen atom, and R 7 and R 11 and together form -O-, and R 13 is a hydrogen atom, a dichloromethyl group, a hydroxy(methoxy)methyl group, or a hydroxy(ethoxy)methyl group, and R 14 is a hydrogen atom, and R 15 is a hydrogen atom, and R 16 is a hydrogen atom, a halogen atom, or OR A13 and R 15 and R 16 and may form a double bond together with the carbon atom to which they are attached, and R 17 is a hydrogen atom, and R 18 is a methyl group, and R 19 is a hydrogen atom, and R 20 is a hydrogen atom, and R 21 is a methyl group, and R 22 is a hydrogen atom, and R 23 is a hydrogen atom, and R 22 and R 23 and may form a double bond together with the carbon atom to which they are attached, and R 24 is OR A19 and R 25 is a hydrogen atom, and R 24 and R 25 may be taken together to form an oxo group, and R 26 is a hydrogen atom, and R 27 is a C1-C3 alkoxy group or a hydroxy group; f 1 :R1 is a hydrogen atom or a C1-C3 alkyl group, and R 2 and R 3 and together form an oxo group, and R 4 is a methyl group, and R 6 and R 27 and together form a bond, and R 7 and R 11 and together form -O-, and R 13 is a hydrogen atom, and R 14 is a hydrogen atom, and R 15 is a hydrogen atom, and R 16 is a hydrogen atom, a halogen atom, or OR A13 and R 17 is a hydrogen atom, and R 18 is a methyl group, and R 19 is a hydrogen atom, and R 20 is a hydrogen atom, and R 21 is a methyl group, and R 22 is a hydrogen atom, and R 23 is a hydrogen atom, and R 22 and R 23 and may form a double bond together with the carbon atom to which they are attached, and R 24 is OR A19 and R 25 is a hydrogen atom, and R 24 and R 25 may be taken together to form an oxo group, and R 26 is a hydrogen atom; and g 1 :R 1 is a hydrogen atom or a C1-C3 alkyl group, and R 2 and R 3 and together form an oxo group, and R 4 is a methyl group, and R 6 is a hydrogen atom, and R 7 is a hydrogen atom, and R 11 is OR A9 and R 13 is a hydrogen atom, and R 14 is a hydrogen atom, and R 15 is a hydrogen atom, and R 16 is a hydrogen atom, a halogen atom, or OR A13 and R17 is a hydrogen atom, and R 18 is a methyl group, and R 19 is a hydrogen atom, and R 20 is a hydrogen atom, and R 21 is a methyl group, and R 22 is a hydrogen atom, and R 23 is a hydrogen atom, and R 22 and R 23 and may form a double bond together with the carbon atom to which they are attached, and R 24 and R 25 and together form an oxo group, and R 26 is a hydrogen atom, and R 27 is a C1-C3 alkoxy group or a hydroxy group. [4] In formula (I), R 5 is a methyl group, and R 8 is a hydrogen atom, a halogen atom, a methoxy group, or a hydroxy group, and R 9 is a methyl group or CHOH, and R 10 is a hydrogen atom, an acetyloxy group, or a hydroxy group, and R 12 [5] The method according to any one of [1] to [3], wherein in formula (I), R A2 is a hydrogen atom, and R A5 is a hydrogen atom, and R A8 is a hydrogen atom or an acetyl group, and R A9 is a hydrogen atom, and R A11 is a hydrogen atom, and R A12 is a hydrogen atom, and R A13 is a hydrogen atom, and R A15 is a hydrogen atom, and R A16 is a hydrogen atom, and R A17 is a hydrogen atom, and R A18 is a hydrogen atom, and R A19 is a hydrogen atom or an acetyl group, and R A20 is a hydrogen atom, and R B1 is a hydrogen atom or a methoxy group, and R B2 is a hydrogen atom or a methoxy group, R 1 , R 2 , R 3 , R 4 , R 5, R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , R 21 , R 22 , R 23 , R 24 , R 25 , R 26 , and R 27 The combination of a 2 ~g 2 The method according to [1] or [2], wherein the combination is any one of: 2 :R 1 is a hydrogen atom, a C1-C3 alkyl group, or CHOH, and R 2 is OR A2 and R 3 is a hydrogen atom, and R 2 and R 3 may be taken together to form an oxo group, and R 4 is a methyl group, and R 5 is a methyl group, and R 6 is a hydrogen atom, and R 7 and R 11 and together form -O-, and R 8 is a hydrogen atom, and R 9 is a methyl group or CHOH, and R 10 is a hydrogen atom or OR A8 and R 12 is a hydrogen atom or a hydroxy group, and R 13 is a hydrogen atom, and R 14 is a hydrogen atom, and R 13 and R 14 may be taken together to form an oxo group, and R 15 and R 27 and together form -O-, and R 16 is a hydrogen atom, a halogen atom, or OR A13 and R17 is a hydrogen atom, and R 16 and R 17 may be taken together to form an oxo group, and R 18 is a methyl group, and R 19 is a hydrogen atom, and R 20 is a hydrogen atom, and R 21 is a methyl group or CH2OR A16 and R 22 is a hydrogen atom or OR A17 and R 21 and R 22 may be taken together to form =CH2, and R 23 is a hydrogen atom, or OR A18 and R 18 and R 23 may be taken together to form —CH—, and R 22 and R 23 and may form a double bond together with the carbon atom to which they are attached, and R 24 is a hydrogen atom or a hydroxy group, and R 25 is a hydrogen atom, and R 24 and R 25 may be taken together to form an oxo group, and R 26 is a hydrogen atom; b 2 :R 1 is a hydrogen atom or a methyl group, and R 2 and R 3 and together form an oxo group, and R 4 is a methyl group, and R 5 is a methyl group, and R 6 is a hydrogen atom, and R 7 and R 11 and together form -O-, and R 8 is a hydrogen atom, and R 9 is a methyl group, and R 10 is a hydrogen atom, and R 12 is a hydrogen atom, and R 13 is a hydrogen atom, and R 14 is a hydrogen atom, and R 15 and R 27 and together form -O-, and R 16 is a hydrogen atom or a halogen atom, and R17 is a hydrogen atom, and R 18 is a methyl group, and R 19 , R 20 , R 22 , R 23 , R 25 , and R 26 form a benzene ring together with the carbon atoms to which they are attached, and R 21 is a methyl group, and R 24 is a C1-C3 alkoxy group or OR A19 a combination in which 2 :R 1 is a methyl group, and R 2 is OR A2 and R 3 is a hydrogen atom, and R 2 and R 3 may be taken together to form an oxo group, and R 3 and R 18 Together # 3 —O—CHR B1 - may be formed, and R 4 and R 27 Together # 4 -CH2-O- is formed, and R 5 is a methyl group, and R 6 is a hydrogen atom or OR A5 and R 7 and R 11 and together form -O-, and R 8 is a hydrogen atom, a halogen atom, a methoxy group, or a hydroxy group, and R 9 is a methyl group or CHOH, and R 10 is a hydrogen atom or a hydroxy group, and R 12 is a hydrogen atom, and R 13 is a hydrogen atom or OR A11 and R 14 is a hydrogen atom, and R 15 is a hydrogen atom, and R 16 is a hydrogen atom, a halogen atom, or OR A13 and R 15 and R 16 and may form a double bond together with the carbon atom to which they are attached, and R 17 is a hydrogen atom, and R16 and R 17 may be taken together to form an oxo group, and R 18 is a methyl group, and R 15 and R 18 Together # 15 -O-CHR B2 - may be formed, and R 19 is a hydrogen atom, and R 20 is a hydrogen atom or OR A15 and R 21 is a methyl group, CH2OR A16 or CHNHCHC(O)OCH, and R 22 is a hydrogen atom, and R 18 and R 22 Together # 18 may form —CH—O—, and R 23 is a hydrogen atom, and R 22 and R 23 and may form a double bond together with the carbon atom to which they are attached, and R 24 and R 25 and together form an oxo group, and R 26 is a hydrogen atom or OR A20 a combination in which 2 :R 1 and R 27 Together # 1 -CH2-O- is formed, and R 2 and R 3 and together form an oxo group, and R 4 is a methyl group, and R 5 is a methyl group, and R 6 is a hydrogen atom, and R 7 and R 11 and together form -O-, and R 8 is a hydrogen atom, and R 9 is a methyl group, and R 10 is a hydrogen atom or a hydroxy group, and R 12 is a hydrogen atom, and R 13 is a hydrogen atom, and R 14 is a hydrogen atom, and R 15 is a hydrogen atom or OR A12 and R 16is a hydrogen atom, a halogen atom, or OR A13 and R 17 is a hydrogen atom, and R 16 and R 17 may be taken together to form an oxo group, and R 18 is a methyl group, and R 19 is a hydrogen atom, and R 20 is a hydrogen atom, and R 21 is a methyl group, and R 22 and R 23 and form a double bond together with the carbon atom to which they are attached, and R 24 and R 25 and together form an oxo group, and R 26 is a hydrogen atom; 2 :R 1 is a hydrogen atom or a C1-C3 alkyl group, and R 2 and R 3 and together form an oxo group, and R 4 is a methyl group, and R 5 is a methyl group, and R 6 is a hydrogen atom, and R 7 and R 11 and together form -O-, and R 8 is a hydrogen atom, and R 9 is a methyl group, and R 10 is a hydrogen atom, and R 12 is a hydrogen atom, and R 13 is a hydrogen atom, a dichloromethyl group, a hydroxy(methoxy)methyl group, or a hydroxy(ethoxy)methyl group, and R 14 is a hydrogen atom, and R 15 is a hydrogen atom, and R 16 is a hydrogen atom or a halogen atom, and R 15 and R 16 and may form a double bond together with the carbon atom to which they are attached, and R 17 is a hydrogen atom, and R 18 is a methyl group, and R 19 is a hydrogen atom, and R 20 is a hydrogen atom, and R 21 is a methyl group, and R 22 is a hydrogen atom, and R 23is a hydrogen atom, and R 22 and R 23 and may form a double bond together with the carbon atom to which they are attached, and R 24 is a hydroxy group, and R 25 is a hydrogen atom, and R 24 and R 25 may be taken together to form an oxo group, and R 26 is a hydrogen atom, and R 27 is a C1-C3 alkoxy group or a hydroxy group; f 2 :R 1 is a hydrogen atom or a C1-C3 alkyl group, and R 2 and R 3 and together form an oxo group, and R 4 is a methyl group, and R 5 is a methyl group, and R 6 and R 27 and together form a bond, and R 7 and R 11 and together form -O-, and R 8 is a hydrogen atom, and R 9 is a methyl group, and R 10 is a hydrogen atom, and R 12 is a hydrogen atom, and R 13 is a hydrogen atom, and R 14 is a hydrogen atom, and R 15 is a hydrogen atom, and R 16 is a hydrogen atom or a halogen atom, and R 17 is a hydrogen atom, and R 18 is a methyl group, and R 19 is a hydrogen atom, and R 20 is a hydrogen atom, and R 21 is a methyl group, and R 22 is a hydrogen atom, and R 23 is a hydrogen atom, and R 22 and R 23 and may form a double bond together with the carbon atom to which they are attached, and R 24 is OR A19 and R 25 is a hydrogen atom, and R 24 and R 25may be taken together to form an oxo group, and R 26 is a hydrogen atom; and g 2 :R 1 is a hydrogen atom or a C1-C3 alkyl group, and R 2 and R 3 and together form an oxo group, and R 4 is a methyl group, and R 5 is a methyl group, and R 6 is a hydrogen atom, and R 7 is a hydrogen atom, and R 8 is a hydrogen atom, and R 9 is a methyl group, and R 10 is a hydrogen atom, and R 11 is OR A9 and R 12 is a hydrogen atom, and R 13 is a hydrogen atom, and R 14 is a hydrogen atom, and R 15 is a hydrogen atom, and R 16 is a hydrogen atom, a halogen atom, or OR A13 and R 17 is a hydrogen atom, and R 18 is a methyl group, and R 19 is a hydrogen atom, and R 20 is a hydrogen atom, and R 21 is a methyl group, and R 22 is a hydrogen atom, and R 23 is a hydrogen atom, and R 22 and R 23 and may form a double bond together with the carbon atom to which they are attached, and R 24 and R 25 and together form an oxo group, and R 26 is a hydrogen atom, and R 27is a C1-C3 alkoxy group or a hydroxy group. [6] A composition for controlling harmful arthropods or harmful nematodes, containing the compound represented by formula (I) according to any one of [1] to [5], or an N-oxide thereof, or a salt thereof. [7] The composition according to [6], further containing one or more components selected from the group consisting of group (a), group (b), group (c), group (d), and group (e): Group (a): the group consisting of insecticidal active ingredients, acaricidal active ingredients, and nematocidal active ingredients; Group (b): fungicidal active ingredients; Group (c): plant growth regulator ingredients; Group (d): repellent ingredients; Group (e): biological control material. [8] A method for controlling harmful arthropods or harmful nematodes, comprising applying an effective amount of the composition according to [7] to harmful arthropods or harmful nematodes, or to a habitat of harmful arthropods or harmful nematodes. [9] A seed or a vegetative reproductive organ carrying an effective amount of the compound represented by formula (I) according to any one of [1] to [5], or an N-oxide thereof, or a salt thereof, or an effective amount of the composition according to [7].

[10] A composition for controlling arthropod pests or nematodes pests, comprising the compound represented by formula (I) according to any one of [1] to [5], or an N-oxide thereof, or a salt thereof, and an inert carrier.

[11] A composition for controlling arthropod pests or nematodes pests, comprising the compound represented by formula (II) according to any one of [1] to [5], or an N-oxide thereof, or a salt thereof, and an inert carrier. [In the formula, R 1 is a hydrogen atom, a C1-C3 alkyl group, or CHOR A1 represents R 2 is OR A2 represents R 3 represents a hydrogen atom, R 4 is a methyl group or CH2OR A3 represents R 5 is a methyl group or CH2OR A4 represents R 6 is a hydrogen atom or OR A5 represents R 8 represents a hydrogen atom, a halogen atom, a methoxy group, or OR A6 represents R 9 is a methyl group or CH2OR A7 represents R 10 is a hydrogen atom or OR A8 represents R 12 is a hydrogen atom or OR A10represents R 13 represents a hydrogen atom, R 14 represents a hydrogen atom, X represents a halogen atom, R 18 is a methyl group, or CH2OR A14 represents R 19 represents a hydrogen atom, R 20 is a hydrogen atom or OR A15 represents R 21 is a methyl group, CH2OR A16 or CH2NHCH2C(O)OCH3, R 22 is a hydrogen atom or OR A17 represents R 23 is a hydrogen atom or OR A18 represents R 24 is a hydrogen atom, a C1-C3 alkoxy group, or OR A19 represents R 25 represents a hydrogen atom, R 26 is a hydrogen atom or OR A20 represents R A1 , R A2 , R A3 , R A4 , R A5 , R A6 , R A7 , R A8 , R A10 , R A14 , R A15 , R A16 , R A17 , R A18 , R A19 , and R A20 are the same or different and represent a hydrogen atom, a (C1-C6 alkyl)carbonyl group, or a (C3-C6 cycloalkyl)carbonyl group; R 2 and R 3 may be taken together to form an oxo group, and R 3 and R 18 Together # 3 -O-CHR B1 - may be formed, 3 is R 3 represents the bonding position with the carbon atom to which R is bonded; 13 and R 14may be taken together to form an oxo group, and R 18 and R 22 Together # 18 -CH2-O- may be formed, 18 is R 18 represents the bonding position with the carbon atom to which R is bonded; 18 and R 23 may be taken together to form —CH—, R 19 , R 20 , R 22 , R 23 , R 25 , and R 26 may form a benzene ring together with the carbon atom to which they are attached, R 21 and R 22 may be taken together to form =CH2, R 22 and R 23 and may form a double bond together with the carbon atom to which they are attached, R 24 and R 25 may be taken together to form an oxo group, and R B1 represents a hydrogen atom or a C1-C3 alkoxy group.] or an N-oxide thereof or a salt thereof (hereinafter, the compound represented by formula (II), or an N-oxide thereof or a salt thereof will be referred to as Compound A of the present invention).

[12] In formula (II), R 2 and R 3 and together form an oxo group, and R 4 is a methyl group, and R 5 is a methyl group, and R 6 is a hydrogen atom, and R 8 is a hydrogen atom, and R 9 is a methyl group, and R 10 is a hydrogen atom, and R 12 is a hydrogen atom, and R 18 is a methyl group, and R 20 is a hydrogen atom, and R 21 is a methyl group, and R 22 is a hydrogen atom or OR A17 and R 21 and R 22may be taken together to form =CH2, and R 23 is a hydrogen atom or OR A18 and R 18 and R 23 may be taken together to form —CH—, and R 22 and R 23 and may form a double bond together with the carbon atom to which they are attached, and R 24 is a hydrogen atom or OR A19 and R 25 is a hydrogen atom, and R 24 and R 25 may be taken together to form an oxo group, and R 26 is a hydrogen atom.

[13] A compound represented by formula (AA1), formula (AA2), formula (AA3), formula (BB1), formula (EE1), formula (EE3), formula (EE4), formula (EE5), formula (EE6), formula (EE7), formula (GG1), formula (GG2), or formula (GG3), or an N-oxide thereof or a salt thereof, or a compound represented by formula (EE2) (hereinafter, the compound represented by

[13] , or an N-oxide thereof, or a salt thereof will be referred to as compound B of the present invention).

[14] A compound represented by formula (AA1), formula (AA2), formula (AA3), formula (BB1), formula (EE1), formula (EE3), formula (EE4), formula (EE5), formula (EE6), formula (GG1), or formula (GG3) according to

[13] , or an N-oxide thereof or a salt thereof, or a compound represented by formula (EE2).

[15] A composition for controlling arthropod pests or nematodes pests, containing the compound according to any one of

[11] to

[14] , or an N-oxide thereof, or a salt thereof.

[16] The composition according to

[15] , further containing one or more components selected from the group consisting of group (a), group (b), group (c), group (d), and group (e): Group (a): the group consisting of insecticidal active ingredients, acaricidal active ingredients, and nematocidal active ingredients; Group (b): fungicidal active ingredients; Group (c): plant growth regulators; Group (d): repellent ingredients; Group (e): biological control materials.

[17] A method for controlling harmful arthropods or harmful nematodes, comprising applying an effective amount of the composition according to

[16] to harmful arthropods or harmful nematodes, or to a habitat of harmful arthropods or harmful nematodes.

[18] A seed or a vegetative reproductive organ carrying an effective amount of the compound according to any of

[11] to

[14] , or its N-oxide, or a salt thereof, or an effective amount of the composition according to

[16] .

[19] A composition for controlling arthropod pests or nematodes pests, comprising the compound according to any one of

[11] to

[14] , its N-oxide, or a salt thereof, and an inert carrier.

[0007] According to the present invention, harmful arthropods or harmful nematodes can be controlled.

[0008] The substituents in the present invention will be explained below: A halogen atom means a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.

[0009] In this specification, Me represents a methyl group, Et represents an ethyl group, and Ac represents an acetyl group. A hydroxy(methoxy)methyl group is a CH(OH)(OCH3) group.

[0010] Compound A of the present invention and compound B of the present invention will be referred to as the compounds of the present invention.

[0011] Zoanthamin, norzoanthamin, zoanthaminone, and norzoanthaminone are compounds disclosed in Heterocyclic Communications, 1995, 1(2-3), 207-214, and are the following compounds, respectively. Zoanthamin is a compound represented by the formula (X): In the compound represented by the formula 1 is a methyl group, and R 16 and R 17 and R are each a hydrogen atom. Norzoanthamine is a compound represented by formula (X) 1 , R 16 and R 17 is a hydrogen atom. Zoantaminon is a compound represented by formula (X) in which R 1 is a methyl group, and R 16 and R 17 together form an oxo group. Norzoantaminone is a compound represented by formula (X) in which R 1 is a hydrogen atom, and R 16 and R 17 The compound represented by formula (X) is a compound represented by formula (I) in which R 2 and R 3 and together form an oxo group, and R 4 and R 5 is a methyl group, and R 6 is a hydrogen atom, and R 7 and R 11 and together form -O-, and R 8 is a hydrogen atom, and R 9 is a methyl group, and R 10 , R 12 , R 13 , R 14 is a hydrogen atom, and R 15 and R 27 and together form -O-, and R 18 is a methyl group, and R 19 and R 20 is a hydrogen atom, and R 21 is a methyl group, and R 22 and R 23and form a double bond together with the carbon atom to which they are attached, and R 24 and R 25 and together form an oxo group, and R 26 is a hydrogen atom.

[0012] The present compound and the compound of the present invention may exist as one or more stereoisomers. Examples of stereoisomers include enantiomers, diastereomers, geometric isomers, etc. The present compound and the compound of the present invention include each stereoisomer and a mixture of stereoisomers in any ratio.

[0013] The salt of the compound represented by formula (I) or its N-oxide refers to an acid addition salt. Examples of acids that form acid addition salts include inorganic acids such as hydrogen chloride, phosphoric acid, and sulfuric acid; and organic acids such as acetic acid, trifluoroacetic acid, benzoic acid, and p-toluenesulfonic acid. For example, an example of a salt of the compound represented by formula (I) is a compound represented by the following formula: [In the formula, X - represents an anion formed by the loss of a proton from an acid, and the other symbols have the same meanings as above.

[0014] The following compounds are examples of the present compound.

[0015] [Embodiment 1] In the present compound, R 1 , R 2 , R 3 , R 4 , R 6 , R 7 , R 11 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , R 21 , R 22 , R 23 , R 24 , R 25 , R 26 , and R 27 A compound in which the combination of a:R is any one of a to g: 1is a hydrogen atom, a C1-C3 alkyl group, or CH2OR A1 and R 2 is OR A2 and R 3 is a hydrogen atom, and R 2 and R 3 may be taken together to form an oxo group, and R 4 is a methyl group or CH2OR A3 and R 6 is a hydrogen atom or OR A5 and R 7 and R 11 and together form -O-, and R 13 is a hydrogen atom, a dichloromethyl group, a hydroxy(methoxy)methyl group, a hydroxy(ethoxy)methyl group, or OR A11 and R 14 is a hydrogen atom, and R 13 and R 14 may be taken together to form an oxo group, and R 15 and R 27 and together form -O-, and R 16 is a hydrogen atom, a halogen atom, or OR A13 and R 17 is a hydrogen atom, and R 16 and R 17 may be taken together to form an oxo group, and R 18 is a methyl group, or CH2OR A14 and R 19 is a hydrogen atom, and R 20 is a hydrogen atom or OR A15 and R 21 is a methyl group, CH2OR A16 or CHNHCHC(O)OCH, and R 22 is a hydrogen atom or OR A17 and R 21 and R 22 may be taken together to form =CH2, and R 23 is a hydrogen atom, or OR A18 and R 18 and R 23 may be taken together to form —CH—, and R 22 and R 23and may form a double bond together with the carbon atom to which they are attached, and R 24 is a hydrogen atom, a C1-C3 alkoxy group, or OR A19 and R 25 is a hydrogen atom, and R 24 and R 25 may be taken together to form an oxo group, and R 26 is a hydrogen atom or OR A20 a combination of: b: R 1 is a hydrogen atom, a C1-C3 alkyl group, or CH2OR A1 and R 2 and R 3 and together form an oxo group, and R 4 is a methyl group or CH2OR A3 and R 6 is a hydrogen atom or OR A5 and R 7 and R 11 and together form -O-, and R 13 is a hydrogen atom, a dichloromethyl group, a hydroxy(methoxy)methyl group, a hydroxy(ethoxy)methyl group, or OR A11 and R 14 is a hydrogen atom, and R 15 and R 27 and together form -O-, and R 16 is a hydrogen atom, a halogen atom, or OR A13 and R 17 is a hydrogen atom, and R 18 is a methyl group, or CH2OR A14 and R 19 , R 20 , R 22 , R 23 , R 25 , and R 26 form a benzene ring together with the carbon atoms to which they are attached, and R 21 is a methyl group, CH2OR A16 or CHNHCHC(O)OCH, and R 24 is a C1-C3 alkoxy group, or OR A19 a combination of: c: R 1 is a hydrogen atom, a C1-C3 alkyl group, or CH2OR A1and R 2 is OR A2 and R 3 is a hydrogen atom, and R 2 and R 3 may be taken together to form an oxo group, and R 3 and R 18 Together # 3 -O-CHR B1 - may be formed, and R 4 and R 27 Together # 4 -CH2-O- is formed, and R 6 is a hydrogen atom or OR A5 and R 7 and R 11 and together form -O-, and R 13 is a hydrogen atom, a dichloromethyl group, a hydroxy(methoxy)methyl group, a hydroxy(ethoxy)methyl group, or OR A11 and R 14 is a hydrogen atom, and R 15 is a hydrogen atom or OR A12 and R 16 is a hydrogen atom, a halogen atom, or OR A13 and R 15 and R 16 and may form a double bond together with the carbon atom to which they are attached, and R 17 is a hydrogen atom, and R 16 and R 17 may be taken together to form an oxo group, and R 18 is a methyl group, or CH2OR A14 and R 15 and R 18 Together # 15 -O-CHR B2 - may be formed, and R 19 is a hydrogen atom, and R 20 is a hydrogen atom or OR A15 and R 21 is a methyl group, CH2OR A16 or CHNHCHC(O)OCH, and R 22 is a hydrogen atom or OR A17 and R 18 and R 22Together # 18 may form —CH—O—, and R 23 is a hydrogen atom, or OR A18 and R 22 and R 23 and may form a double bond together with the carbon atom to which they are attached, and R 24 and R 25 and together form an oxo group, and R 26 is a hydrogen atom or OR A20 a combination of: d: R 1 and R 27 Together # 1 -CH2-O- is formed, and R 2 and R 3 and together form an oxo group, and R 4 is a methyl group or CH2OR A3 and R 6 is a hydrogen atom or OR A5 and R 7 and R 11 and together form -O-, and R 13 is a hydrogen atom, a dichloromethyl group, a hydroxy(methoxy)methyl group, a hydroxy(ethoxy)methyl group, or OR A11 and R 14 is a hydrogen atom, and R 15 is a hydrogen atom or OR A12 and R 16 is a hydrogen atom, a halogen atom, or OR A13 and R 17 is a hydrogen atom, and R 16 and R 17 may be taken together to form an oxo group, and R 18 is a methyl group, or CH2OR A14 and R 19 is a hydrogen atom, and R 20 is a hydrogen atom or OR A15 and R 21 is a methyl group, CH2OR A16 or CHNHCHC(O)OCH, and R 22 and R 23 and form a double bond together with the carbon atom to which they are attached, and R 24 and R25 and together form an oxo group, and R 26 is a hydrogen atom or OR A20 a combination in which e:R 1 is a hydrogen atom, a C1-C3 alkyl group, or CH2OR A1 and R 2 and R 3 and together form an oxo group, and R 4 is a methyl group or CH2OR A3 and R 6 is a hydrogen atom or OR A5 and R 7 and R 11 and together form -O-, and R 13 is a hydrogen atom, a dichloromethyl group, a hydroxy(methoxy)methyl group, a hydroxy(ethoxy)methyl group, or OR A11 and R 14 is a hydrogen atom, and R 15 is a hydrogen atom or OR A12 and R 16 is a hydrogen atom, a halogen atom, or OR A13 and R 15 and R 16 and may form a double bond together with the carbon atom to which they are attached, and R 17 is a hydrogen atom, and R 18 is a methyl group, or CH2OR A14 and R 19 is a hydrogen atom, and R 20 is a hydrogen atom or OR A15 and R 21 is a methyl group, CH2OR A16 or CHNHCHC(O)OCH, and R 22 is a hydrogen atom or OR A17 and R 23 is a hydrogen atom, or OR A18 and R 22 and R 23 and may form a double bond together with the carbon atom to which they are attached, and R 24 is a hydrogen atom, a C1-C3 alkoxy group, or OR A19 and R 25 is a hydrogen atom, and R 24 and R25 may be taken together to form an oxo group, and R 26 is a hydrogen atom or OR A20 and R 27 is a C1-C3 alkoxy group or a hydroxy group. 1 is a hydrogen atom, a C1-C3 alkyl group, or CH2OR A1 and R 2 and R 3 and together form an oxo group, and R 4 is a methyl group or CH2OR A3 and R 6 and R 27 and together form a bond, and R 7 and R 11 and together form -O-, and R 13 is a hydrogen atom, a dichloromethyl group, a hydroxy(methoxy)methyl group, a hydroxy(ethoxy)methyl group, or OR A11 and R 14 is a hydrogen atom, and R 15 is a hydrogen atom or OR A12 and R 16 is a hydrogen atom, a halogen atom, or OR A13 and R 17 is a hydrogen atom, and R 18 is a methyl group, or CH2OR A14 and R 19 is a hydrogen atom, and R 20 is a hydrogen atom or OR A15 and R 21 is a methyl group, CH2OR A16 or CHNHCHC(O)OCH, and R 22 is a hydrogen atom or OR A17 and R 23 is a hydrogen atom, or OR A18 and R 22 and R 23 and may form a double bond together with the carbon atom to which they are attached, and R 24 is a hydrogen atom, a C1-C3 alkoxy group, or OR A19 and R 25 is a hydrogen atom, and R 24 and R 25may be taken together to form an oxo group, and R 26 is a hydrogen atom or OR A20 and g: R 1 is a hydrogen atom, a C1-C3 alkyl group, or CH2OR A1 and R 2 and R 3 and together form an oxo group, and R 4 is a methyl group or CH2OR A3 and R 6 is a hydrogen atom or OR A5 and R 7 is a hydrogen atom, and R 11 is OR A9 and R 13 is a hydrogen atom, a dichloromethyl group, a hydroxy(methoxy)methyl group, a hydroxy(ethoxy)methyl group, or OR A11 and R 14 is a hydrogen atom, and R 15 is a hydrogen atom or OR A12 and R 16 is a hydrogen atom, a halogen atom, or OR A13 and R 17 is a hydrogen atom, and R 18 is a methyl group, or CH2OR A14 and R 19 is a hydrogen atom, and R 20 is a hydrogen atom or OR A15 and R 21 is a methyl group, CH2OR A16 or CHNHCHC(O)OCH, and R 22 is a hydrogen atom or OR A17 and R 23 is a hydrogen atom, or OR A18 and R 22 and R 23 and may form a double bond together with the carbon atom to which they are attached, and R 24 and R 25 and together form an oxo group, and R 26 is a hydrogen atom or OR A20 and R 27 is a C1-C3 alkoxy group or a hydroxy group. 1, R 2 , R 3 , R 4 , R 6 , R 7 , R 11 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , R 21 , R 22 , R 23 , R 24 , R 25 , R 26 , and R 27 The compound in which the combination of R is a, b, c, d, e or g. 1 , R 2 , R 3 , R 4 , R 6 , R 7 , R 11 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , R 21 , R 22 , R 23 , R 24 , R 25 , R 26 , and R 27 The compound in which the combination of R is a, b, e, or g. 1 , R 2 , R 3 , R 4 , R 6 , R 7 , R 11 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , R 21 , R 22 , R 23 , R24 , R 25 , R 26 , and R 27 The compound in which the combination of R is combination a, b, or e. 1 , R 2 , R 3 , R 4 , R 6 , R 7 , R 11 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , R 21 , R 22 , R 23 , R 24 , R 25 , R 26 , and R 27 A compound in which the combination of R is combination a. 1 , R 2 , R 3 , R 4 , R 6 , R 7 , R 11 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , R 21 , R 22 , R 23 , R 24 , R 25 , R 26 , and R 27 The combination of a 1 ~g 1 A compound that is any combination of: 1 :R 1 is a hydrogen atom, a C1-C3 alkyl group, or CH2OR A1 and R 2 is OR A2 and R 3 is a hydrogen atom, and R 2 and R 3may be taken together to form an oxo group, and R 4 is a methyl group, and R 6 is a hydrogen atom, and R 7 and R 11 and together form -O-, and R 13 is a hydrogen atom, and R 14 is a hydrogen atom, and R 13 and R 14 may be taken together to form an oxo group, and R 15 and R 27 and together form -O-, and R 16 is a hydrogen atom, a halogen atom, or OR A13 and R 17 is a hydrogen atom, and R 16 and R 17 may be taken together to form an oxo group, and R 18 is a methyl group, and R 19 is a hydrogen atom, and R 20 is a hydrogen atom, and R 21 is a methyl group or CH2OR A16 and R 22 is a hydrogen atom or OR A17 and R 21 and R 22 may be taken together to form =CH2, and R 23 is a hydrogen atom, or OR A18 and R 18 and R 23 may be taken together to form —CH—, and R 22 and R 23 and may form a double bond together with the carbon atom to which they are attached, and R 24 is a hydrogen atom or OR A19 and R 25 is a hydrogen atom, and R 24 and R 25 may be taken together to form an oxo group, and R 26 is a hydrogen atom; b 1 :R 1 is a hydrogen atom or a methyl group, and R 2 and R 3 and together form an oxo group, and R 4is a methyl group, and R 6 is a hydrogen atom, and R 7 and R 11 and together form -O-, and R 13 is a hydrogen atom, and R 14 is a hydrogen atom, and R 15 and R 27 and together form -O-, and R 16 is a hydrogen atom or a halogen atom, and R 17 is a hydrogen atom, and R 18 is a methyl group, and R 19 , R 20 , R 22 , R 23 , R 25 , and R 26 form a benzene ring together with the carbon atoms to which they are attached, and R 21 is a methyl group, and R 24 is a C1-C3 alkoxy group or OR A19 a combination in which 1 :R 1 is a methyl group, and R 2 is OR A2 and R 3 is a hydrogen atom, and R 2 and R 3 may be taken together to form an oxo group, and R 3 and R 18 Together # 3 -O-CHR B1 - may be formed, and R 4 and R 27 Together # 4 -CH2-O- is formed, and R 6 is a hydrogen atom or OR A5 and R 7 and R 11 and together form -O-, and R 13 is a hydrogen atom or OR A11 and R 14 is a hydrogen atom, and R 15 is a hydrogen atom, and R 16 is a hydrogen atom, a halogen atom, or OR A13 and R 15 and R 16and may form a double bond together with the carbon atom to which they are attached, and R 17 is a hydrogen atom, and R 16 and R 17 may be taken together to form an oxo group, and R 18 is a methyl group, and R 15 and R 18 Together # 15 -O-CHR B2 - may be formed, and R 19 is a hydrogen atom, and R 20 is a hydrogen atom or OR A15 and R 21 is a methyl group, CH2OR A16 or CHNHCHC(O)OCH, and R 22 is a hydrogen atom, and R 18 and R 22 Together # 18 may form —CH—O—, and R 23 is a hydrogen atom, and R 22 and R 23 and may form a double bond together with the carbon atom to which they are attached, and R 24 and R 25 and together form an oxo group, and R 26 is a hydrogen atom or OR A20 a combination in which 1 :R 1 and R 27 Together # 1 -CH2-O- is formed, and R 2 and R 3 and together form an oxo group, and R 4 is a methyl group, and R 6 is a hydrogen atom, and R 7 and R 11 and together form -O-, and R 13 is a hydrogen atom, and R 14 is a hydrogen atom, and R 15 is a hydrogen atom or OR A12 and R 16 is a hydrogen atom, a halogen atom, or OR A13 and R 17 is a hydrogen atom, and R 16and R 17 may be taken together to form an oxo group, and R 18 is a methyl group, and R 19 is a hydrogen atom, and R 20 is a hydrogen atom, and R 21 is a methyl group, and R 22 and R 23 and form a double bond together with the carbon atom to which they are attached, and R 24 and R 25 and together form an oxo group, and R 26 is a hydrogen atom; 1 :R 1 is a hydrogen atom or a C1-C3 alkyl group, and R 2 and R 3 and together form an oxo group, and R 4 is a methyl group, and R 6 is a hydrogen atom, and R 7 and R 11 and together form -O-, and R 13 is a hydrogen atom, a dichloromethyl group, a hydroxy(methoxy)methyl group, or a hydroxy(ethoxy)methyl group, and R 14 is a hydrogen atom, and R 15 is a hydrogen atom, and R 16 is a hydrogen atom, a halogen atom, or OR A13 and R 15 and R 16 and may form a double bond together with the carbon atom to which they are attached, and R 17 is a hydrogen atom, and R 18 is a methyl group, and R 19 is a hydrogen atom, and R 20 is a hydrogen atom, and R 21 is a methyl group, and R 22 is a hydrogen atom, and R 23 is a hydrogen atom, and R 22 and R 23 and may form a double bond together with the carbon atom to which they are attached, and R 24 is OR A19 and R 25 is a hydrogen atom, and R 24 and R 25may be taken together to form an oxo group, and R 26 is a hydrogen atom, and R 27 is a C1-C3 alkoxy group or a hydroxy group; f 1 :R 1 is a hydrogen atom or a C1-C3 alkyl group, and R 2 and R 3 and together form an oxo group, and R 4 is a methyl group, and R 6 and R 27 and together form a bond, and R 7 and R 11 and together form -O-, and R 13 is a hydrogen atom, and R 14 is a hydrogen atom, and R 15 is a hydrogen atom, and R 16 is a hydrogen atom, a halogen atom, or OR A13 and R 17 is a hydrogen atom, and R 18 is a methyl group, and R 19 is a hydrogen atom, and R 20 is a hydrogen atom, and R 21 is a methyl group, and R 22 is a hydrogen atom, and R 23 is a hydrogen atom, and R 22 and R 23 and may form a double bond together with the carbon atom to which they are attached, and R 24 is OR A19 and R 25 is a hydrogen atom, and R 24 and R 25 may be taken together to form an oxo group, and R 26 is a hydrogen atom; and g 1 :R 1 is a hydrogen atom or a C1-C3 alkyl group, and R 2 and R 3 and together form an oxo group, and R 4 is a methyl group, and R 6 is a hydrogen atom, and R 7 is a hydrogen atom, and R 11 is OR A9 and R 13is a hydrogen atom, and R 14 is a hydrogen atom, and R 15 is a hydrogen atom, and R 16 is a hydrogen atom, a halogen atom, or OR A13 and R 17 is a hydrogen atom, and R 18 is a methyl group, and R 19 is a hydrogen atom, and R 20 is a hydrogen atom, and R 21 is a methyl group, and R 22 is a hydrogen atom, and R 23 is a hydrogen atom, and R 22 and R 23 and may form a double bond together with the carbon atom to which they are attached, and R 24 and R 25 and together form an oxo group, and R 26 is a hydrogen atom, and R 27 is a C1-C3 alkoxy group or a hydroxy group. 1 , R 2 , R 3 , R 4 , R 6 , R 7 , R 11 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , R 21 , R 22 , R 23 , R 24 , R 25 , R 26 , and R 27 The combination of 1 , b 1 , c 1 , d 1 , e 1 or g 1 [Aspect 8] In aspect 6, the compound 1 , R 2 , R 3 , R 4 , R 6 , R 7 , R11 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , R 21 , R 22 , R 23 , R 24 , R 25 , R 26 , and R 27 The combination of 1 , b 1 , e 1 or g 1 [Aspect 9] In aspect 6, the compound 1 , R 2 , R 3 , R 4 , R 6 , R 7 , R 11 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , R 21 , R 22 , R 23 , R 24 , R 25 , R 26 , and R 27 The combination of 1 , b 1 or e 1 [Aspect 10] In aspect 6, the compound 1 , R 2 , R 3 , R 4 , R 6 , R 7 , R 11 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , R 21 , R 22 , R23 , R 24 , R 25 , R 26 , and R 27 The combination of 1 [Aspect 11] In aspect 6, the compound 1 , R 2 , R 3 , R 4 , R 6 , R 7 , R 11 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , R 21 , R 22 , R 23 , R 24 , R 25 , R 26 , and R 27 The combination of 1 [Aspect 12] In aspect 6, the compound 1 , R 2 , R 3 , R 4 , R 6 , R 7 , R 11 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , R 21 , R 22 , R 23 , R 24 , R 25 , R 26 , and R 27 The combination of 1 [Aspect 13] In aspect 6, the compound 1 , R 2 , R 3 , R 4 , R 6 , R 7 , R 11 , R 13 , R14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , R 21 , R 22 , R 23 , R 24 , R 25 , R 26 , and R 27 The combination of 1 [Embodiment 14] In any of embodiments 1 to 13 or the present compound, R 5 is a methyl group. [Embodiment 15] In any of embodiments 1 to 13 or the present compound, R 5 is a methyl group, and R 8 is a hydrogen atom, a halogen atom, a methoxy group, or a hydroxy group, and R 9 is a methyl group or CHOH, and R 10 is a hydrogen atom, an acetyloxy group, or a hydroxy group, and R 12 is a hydrogen atom or a hydroxy group.

[0016] [Embodiment 16] In the present compound, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , R 21 , R 22 , R 23 , R 24 , R 25 , R 26 , and R 27 The combination of a 2 ~g 2 A compound that is any combination of:2 :R 1 is a hydrogen atom, a C1-C3 alkyl group, or CHOH, and R 2 is OR A2 and R 3 is a hydrogen atom, and R 2 and R 3 may be taken together to form an oxo group, and R 4 is a methyl group, and R 5 is a methyl group, and R 6 is a hydrogen atom, and R 7 and R 11 and together form -O-, and R 8 is a hydrogen atom, and R 9 is a methyl group or CHOH, and R 10 is a hydrogen atom or OR A8 and R 12 is a hydrogen atom or a hydroxy group, and R 13 is a hydrogen atom, and R 14 is a hydrogen atom, and R 13 and R 14 may be taken together to form an oxo group, and R 15 and R 27 and together form -O-, and R 16 is a hydrogen atom, a halogen atom, or OR A13 and R 17 is a hydrogen atom, and R 16 and R 17 may be taken together to form an oxo group, and R 18 is a methyl group, and R 19 is a hydrogen atom, and R 20 is a hydrogen atom, and R 21 is a methyl group or CH2OR A16 and R 22 is a hydrogen atom or OR A17 and R 21 and R 22 may be taken together to form =CH2, and R 23 is a hydrogen atom, or OR A18 and R 18 and R 23 may be taken together to form —CH—, and R 22 and R 23and may form a double bond together with the carbon atom to which they are attached, and R 24 is a hydrogen atom or a hydroxy group, and R 25 is a hydrogen atom, and R 24 and R 25 may be taken together to form an oxo group, and R 26 is a hydrogen atom; b 2 :R 1 is a hydrogen atom or a methyl group, and R 2 and R 3 and together form an oxo group, and R 4 is a methyl group, and R 5 is a methyl group, and R 6 is a hydrogen atom, and R 7 and R 11 and together form -O-, and R 8 is a hydrogen atom, and R 9 is a methyl group, and R 10 is a hydrogen atom, and R 12 is a hydrogen atom, and R 13 is a hydrogen atom, and R 14 is a hydrogen atom, and R 15 and R 27 and together form -O-, and R 16 is a hydrogen atom or a halogen atom, and R 17 is a hydrogen atom, and R 18 is a methyl group, and R 19 , R 20 , R 22 , R 23 , R 25 , and R 26 form a benzene ring together with the carbon atoms to which they are attached, and R 21 is a methyl group, and R 24 is a C1-C3 alkoxy group or OR A19 a combination in which 2 :R 1 is a methyl group, and R 2 is OR A2 and R 3 is a hydrogen atom, and R 2 and R 3 may be taken together to form an oxo group, and R 3 and R18 Together # 3 —O—CHR B1 - may be formed, and R 4 and R 27 Together # 4 -CH2-O- is formed, and R 5 is a methyl group, and R 6 is a hydrogen atom or OR A5 and R 7 and R 11 and together form -O-, and R 8 is a hydrogen atom, a halogen atom, a methoxy group, or a hydroxy group, and R 9 is a methyl group or CHOH, and R 10 is a hydrogen atom or a hydroxy group, and R 12 is a hydrogen atom, and R 13 is a hydrogen atom or OR A11 and R 14 is a hydrogen atom, and R 15 is a hydrogen atom, and R 16 is a hydrogen atom, a halogen atom, or OR A13 and R 15 and R 16 and may form a double bond together with the carbon atom to which they are attached, and R 17 is a hydrogen atom, and R 16 and R 17 may be taken together to form an oxo group, and R 18 is a methyl group, and R 15 and R 18 Together # 15 —O—CHR B2 - may be formed, and R 19 is a hydrogen atom, and R 20 is a hydrogen atom or OR A15 and R 21 is a methyl group, CH2OR A16 or CHNHCHC(O)OCH, and R 22 is a hydrogen atom, and R 18 and R 22 Together # 18 may form —CH—O—, and R 23 is a hydrogen atom, and R 22 and R23 and may form a double bond together with the carbon atom to which they are attached, and R 24 and R 25 and together form an oxo group, and R 26 is a hydrogen atom or OR A20 a combination in which 2 :R 1 and R 27 Together # 1 -CH2-O- is formed, and R 2 and R 3 and together form an oxo group, and R 4 is a methyl group, and R 5 is a methyl group, and R 6 is a hydrogen atom, and R 7 and R 11 and together form -O-, and R 8 is a hydrogen atom, and R 9 is a methyl group, and R 10 is a hydrogen atom or a hydroxy group, and R 12 is a hydrogen atom, and R 13 is a hydrogen atom, and R 14 is a hydrogen atom, and R 15 is a hydrogen atom or OR A12 and R 16 is a hydrogen atom, a halogen atom, or OR A13 and R 17 is a hydrogen atom, and R 16 and R 17 may be taken together to form an oxo group, and R 18 is a methyl group, and R 19 is a hydrogen atom, and R 20 is a hydrogen atom, and R 21 is a methyl group, and R 22 and R 23 and form a double bond together with the carbon atom to which they are attached, and R 24 and R 25 and together form an oxo group, and R 26 is a hydrogen atom; 2 :R 1 is a hydrogen atom or a C1-C3 alkyl group, and R 2 and R 3and together form an oxo group, and R 4 is a methyl group, and R 5 is a methyl group, and R 6 is a hydrogen atom, and R 7 and R 11 and together form -O-, and R 8 is a hydrogen atom, and R 9 is a methyl group, and R 10 is a hydrogen atom, and R 12 is a hydrogen atom, and R 13 is a hydrogen atom, a dichloromethyl group, a hydroxy(methoxy)methyl group, or a hydroxy(ethoxy)methyl group, and R 14 is a hydrogen atom, and R 15 is a hydrogen atom, and R 16 is a hydrogen atom or a halogen atom, and R 15 and R 16 and may form a double bond together with the carbon atom to which they are attached, and R 17 is a hydrogen atom, and R 18 is a methyl group, and R 19 is a hydrogen atom, and R 20 is a hydrogen atom, and R 21 is a methyl group, and R 22 is a hydrogen atom, and R 23 is a hydrogen atom, and R 22 and R 23 and may form a double bond together with the carbon atom to which they are attached, and R 24 is a hydroxy group, and R 25 is a hydrogen atom, and R 24 and R 25 may be taken together to form an oxo group, and R 26 is a hydrogen atom, and R 27 is a C1-C3 alkoxy group or a hydroxy group; f 2 :R 1 is a hydrogen atom or a C1-C3 alkyl group, and R 2 and R 3 and together form an oxo group, and R 4 is a methyl group, and R 5 is a methyl group, and R 6 and R 27and together form a bond, and R 7 and R 11 and together form -O-, and R 8 is a hydrogen atom, and R 9 is a methyl group, and R 10 is a hydrogen atom, and R 12 is a hydrogen atom, and R 13 is a hydrogen atom, and R 14 is a hydrogen atom, and R 15 is a hydrogen atom, and R 16 is a hydrogen atom or a halogen atom, and R 17 is a hydrogen atom, and R 18 is a methyl group, and R 19 is a hydrogen atom, and R 20 is a hydrogen atom, and R 21 is a methyl group, and R 22 is a hydrogen atom, and R 23 is a hydrogen atom, and R 22 and R 23 and may form a double bond together with the carbon atom to which they are attached, and R 24 is OR A19 and R 25 is a hydrogen atom, and R 24 and R 25 may be taken together to form an oxo group, and R 26 is a hydrogen atom; and g 2 :R 1 is a hydrogen atom or a C1-C3 alkyl group, and R 2 and R 3 and together form an oxo group, and R 4 is a methyl group, and R 5 is a methyl group, and R 6 is a hydrogen atom, and R 7 is a hydrogen atom, and R 8 is a hydrogen atom, and R 9 is a methyl group, and R 10 is a hydrogen atom, and R 11 is OR A9 and R 12 is a hydrogen atom, and R 13 is a hydrogen atom, and R 14 is a hydrogen atom, and R 15is a hydrogen atom, and R 16 is a hydrogen atom, a halogen atom, or OR A13 and R 17 is a hydrogen atom, and R 18 is a methyl group, and R 19 is a hydrogen atom, and R 20 is a hydrogen atom, and R 21 is a methyl group, and R 22 is a hydrogen atom, and R 23 is a hydrogen atom, and R 22 and R 23 and may form a double bond together with the carbon atom to which they are attached, and R 24 and R 25 and together form an oxo group, and R 26 is a hydrogen atom, and R 27 is a C1-C3 alkoxy group or a hydroxy group. A2 is a hydrogen atom, and R A5 is a hydrogen atom, and R A8 is a hydrogen atom or an acetyl group, and R A9 is a hydrogen atom, and R A11 is a hydrogen atom, and R A12 is a hydrogen atom, and R A13 is a hydrogen atom, and R A15 is a hydrogen atom, and R A16 is a hydrogen atom, and R A17 is a hydrogen atom, and R A18 is a hydrogen atom, and R A19 is a hydrogen atom or an acetyl group, and R A20 is a hydrogen atom, and R B1 is a hydrogen atom or a methoxy group, and R B2 is a hydrogen atom or a methoxy group. 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13, R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , R 21 , R 22 , R 23 , R 24 , R 25 , R 26 , and R 27 The combination of 2 , b 2 , c 2 , d 2 , e 2 or g 2 [Aspect 19] In aspect 16 or 17, the compound is 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , R 21 , R 22 , R 23 , R 24 , R 25 , R 26 , and R 27 The combination of 2 , b 2 , e 2 or g 2 [Aspect 20] In aspect 16 or 17, the compound 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , R 21 , R 22 , R 23 , R 24 , R 25 , R 26 , and R 27 The combination of 2 , b 2 or e 2 [Aspect 21] In aspect 16 or 17, the compound 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , R 21 , R 22 , R 23 , R 24 , R 25 , R 26 , and R 27 The combination of 2 [Aspect 22] In aspect 16 or 17, the compound 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R15 , R 16 , R 17 , R 18 , R 19 , R 20 , R 21 , R 22 , R 23 , R 24 , R 25 , R 26 , and R 27 The combination of 2 [Aspect 23] In aspect 16 or 17, the compound 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , R 21 , R 22 , R 23 , R 24 , R 25 , R 26 , and R 27 The combination of 2 [Aspect 24] In aspect 16 or 17, the compound is 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , R21 , R 22 , R 23 , R 24 , R 25 , R 26 , and R 27 The combination of 2 A compound which is

[0017] [Embodiment 25] In the present compound, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , R 21 , R 22 , R 23 , R 24 , R 25 , R 26 , and R 27 The combination of a 3 ~g 3 A compound that is any combination of: 3 :R 1 is a hydrogen atom, a methyl group, an ethyl group, or CHOH, and R 2 and R 3 and together form an oxo group, and R 4 is a methyl group, and R 5 is a methyl group, and R 6 is a hydrogen atom, and R 7 and R 11 and together form -O-, and R 8 is a hydrogen atom, and R 9 is a methyl group or CHOH, and R 10 is a hydrogen atom, a hydroxy group, or an acetyloxy group, and R 12 is a hydrogen atom or a hydroxy group, and R 13 is a hydrogen atom, and R14 is a hydrogen atom, and R 13 and R 14 may be taken together to form an oxo group, and R 15 and R 27 and together form -O-, and R 16 is a hydrogen atom, a halogen atom, or a hydroxy group, and R 17 is a hydrogen atom, and R 16 and R 17 may be taken together to form an oxo group, and R 18 is a methyl group, and R 19 is a hydrogen atom, and R 20 is a hydrogen atom, and R 21 is a methyl group or CHOH, and R 22 is a hydrogen atom or a hydroxy group, and R 21 and R 22 may be taken together to form =CH2, and R 23 is a hydrogen atom or a hydroxy group, and R 18 and R 23 may be taken together to form —CH—, and R 22 and R 23 and may form a double bond together with the carbon atom to which they are attached, and R 24 is a hydrogen atom or a hydroxy group, and R 25 is a hydrogen atom, and R 24 and R 25 may be taken together to form an oxo group, and R 26 is a hydrogen atom; b 3 :R 1 is a hydrogen atom or a methyl group, and R 2 and R 3 and together form an oxo group, and R 4 is a methyl group, and R 5 is a methyl group, and R 6 is a hydrogen atom, and R 7 and R 11 and together form -O-, and R 8 is a hydrogen atom, and R 9 is a methyl group, and R 10 is a hydrogen atom, and R 12 is a hydrogen atom, and R13 is a hydrogen atom, and R 14 is a hydrogen atom, and R 15 and R 27 and together form -O-, and R 16 is a hydrogen atom, and R 17 is a hydrogen atom, and R 18 is a methyl group, and R 19 , R 20 , R 22 , R 23 , R 25 , and R 26 form a benzene ring together with the carbon atoms to which they are attached, and R 21 is a methyl group, and R 24 is a hydroxy group or an acetyloxy group; 3 :R 1 is a methyl group, and R 2 is a hydroxy group, and R 3 is a hydrogen atom, and R 2 and R 3 may be taken together to form an oxo group, and R 3 and R 18 Together # 3 -O-CH2- or # 3 -O-CH(OCH3)- may be formed, and R 4 and R 27 Together # 4 -CH2-O- is formed, and R 5 is a methyl group, and R 6 is a hydrogen atom or a hydroxy group, and R 7 and R 11 and together form -O-, and R 8 is a hydrogen atom, a halogen atom, a methoxy group, or a hydroxy group, and R 9 is a methyl group or CHOH, and R 10 is a hydrogen atom or a hydroxy group, and R 12 is a hydrogen atom, and R 13 is a hydrogen atom or a hydroxy group, and R 14 is a hydrogen atom, and R 15 is a hydrogen atom, and R 16 is a hydrogen atom, a halogen atom, or a hydroxy group, and R 15 and R16 and may form a double bond together with the carbon atom to which they are attached, and R 17 is a hydrogen atom, and R 16 and R 17 may be taken together to form an oxo group, and R 18 is a methyl group, and R 15 and R 18 Together # 15 -O-CH2- or # 15 -O-CH(OCH3)- may be formed, and R 19 is a hydrogen atom, and R 20 is a hydrogen atom or a hydroxy group, and R 21 is a methyl group, CHOH, or CHNHCHC(O)OCH, and R 22 is a hydrogen atom, and R 18 and R 22 Together # 18 may form —CH—O—, and R 23 is a hydrogen atom, and R 22 and R 23 and may form a double bond together with the carbon atom to which they are attached, and R 24 and R 25 and together form an oxo group, and R 26 is a hydrogen atom; d 3 :R 1 and R 27 Together # 1 -CH2-O- is formed, and R 2 and R 3 and together form an oxo group, and R 4 is a methyl group, and R 5 is a methyl group, and R 6 is a hydrogen atom, and R 7 and R 11 and together form -O-, and R 8 is a hydrogen atom, and R 9 is a methyl group, and R 10 is a hydrogen atom or a hydroxy group, and R 12 is a hydrogen atom, and R 13 is a hydrogen atom, and R 14 is a hydrogen atom, and R 15is a hydroxy group, and R 16 is a hydrogen atom, and R 17 is a hydrogen atom, and R 16 and R 17 may be taken together to form an oxo group, and R 18 is a methyl group, and R 19 is a hydrogen atom, and R 20 is a hydrogen atom, and R 21 is a methyl group, and R 22 and R 23 and form a double bond together with the carbon atom to which they are attached, and R 24 and R 25 and together form an oxo group, and R 26 is a hydrogen atom; 3 :R 1 is a hydrogen atom or a methyl group, and R 2 and R 3 and together form an oxo group, and R 4 is a methyl group, and R 5 is a methyl group, and R 6 is a hydrogen atom, and R 7 and R 11 and together form -O-, and R 8 is a hydrogen atom, and R 9 is a methyl group, and R 10 is a hydrogen atom, and R 12 is a hydrogen atom, and R 13 is a hydrogen atom, a dichloromethyl group, or a hydroxy(methoxy)methyl group, and R 14 is a hydrogen atom, and R 15 is a hydrogen atom, and R 16 is a hydrogen atom, and R 15 and R 16 and may form a double bond together with the carbon atom to which they are attached, and R 17 is a hydrogen atom, and R 18 is a methyl group, and R 19 is a hydrogen atom, and R 20 is a hydrogen atom, and R 21 is a methyl group, and R 22 is a hydrogen atom, and R 23 is a hydrogen atom, and R 22 and R23 and may form a double bond together with the carbon atom to which they are attached, and R 24 is a hydroxy group, and R 25 is a hydrogen atom, and R 24 and R 25 may be taken together to form an oxo group, and R 26 is a hydrogen atom, and R 27 is a methoxy group or a hydroxy group; f 3 :R 1 is a hydrogen atom or a methyl group, and R 2 and R 3 and together form an oxo group, and R 4 is a methyl group, and R 5 is a methyl group, and R 6 and R 27 and together form a bond, and R 7 and R 11 and together form -O-, and R 8 is a hydrogen atom, and R 9 is a methyl group, and R 10 is a hydrogen atom, and R 12 is a hydrogen atom, and R 13 is a hydrogen atom, and R 14 is a hydrogen atom, and R 15 is a hydrogen atom, and R 16 is a hydrogen atom, and R 17 is a hydrogen atom, and R 18 is a methyl group, and R 19 is a hydrogen atom, and R 20 is a hydrogen atom, and R 21 is a methyl group, and R 22 is a hydrogen atom, and R 23 is a hydrogen atom, and R 22 and R 23 and may form a double bond together with the carbon atom to which they are attached, and R 24 is a hydroxy group or an acetyloxy group, and R 25 is a hydrogen atom, and R 24 and R 25 may be taken together to form an oxo group, and R 26 is a hydrogen atom; and g 3:R 1 is a hydrogen atom or a methyl group, and R 2 and R 3 and together form an oxo group, and R 4 is a methyl group, and R 5 is a methyl group, and R 6 is a hydrogen atom, and R 7 is a hydrogen atom, and R 8 is a hydrogen atom, and R 9 is a methyl group, and R 10 is a hydrogen atom, and R 11 is a hydroxy group, and R 12 is a hydrogen atom, and R 13 is a hydrogen atom, and R 14 is a hydrogen atom, and R 15 is a hydrogen atom, and R 16 is a hydrogen atom, and R 17 is a hydrogen atom, and R 18 is a methyl group, and R 19 is a hydrogen atom, and R 20 is a hydrogen atom, and R 21 is a methyl group, and R 22 is a hydrogen atom, and R 23 is a hydrogen atom, and R 22 and R 23 and may form a double bond together with the carbon atom to which they are attached, and R 24 and R 25 and together form an oxo group, and R 26 is a hydrogen atom, and R 27 is a methoxy group or a hydroxy group. 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R19 , R 20 , R 21 , R 22 , R 23 , R 24 , R 25 , R 26 , and R 27 The combination of 3 , b 3 , c 3 , d 3 , e 3 or g 3 [Aspect 27] In aspect 25, the compound 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , R 21 , R 22 , R 23 , R 24 , R 25 , R 26 , and R 27 The combination of 3 , b 3 , e 3 or g 3 [Aspect 28] In aspect 25, the compound 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R17 , R 18 , R 19 , R 20 , R 21 , R 22 , R 23 , R 24 , R 25 , R 26 , and R 27 The combination of 3 , b 3 or e 3 [Aspect 29] In aspect 25, the compound 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , R 21 , R 22 , R 23 , R 24 , R 25 , R 26 , and R 27 The combination of 3 [Aspect 30] In aspect 25, the compound 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , R21 , R 22 , R 23 , R 24 , R 25 , R 26 , and R 27 The combination of 3 [Aspect 31] In aspect 25, the compound 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , R 21 , R 22 , R 23 , R 24 , R 25 , R 26 , and R 27 The combination of 3 [Aspect 32] In aspect 25, the compound 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , R 21 , R 22 , R 23 , R 24 , R 25 , R 26 , and R27 The combination of 3 A compound which is

[0018] [Embodiment 33] In the present compound, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , R 21 , R 22 , R 23 , R 24 , R 25 , R 26 , and R 27 The combination of a 4 , b 4 , e 4 and g 4 A compound that is any combination of: 4 :R 1 is a hydrogen atom, a methyl group, an ethyl group, or CHOH, and R 2 and R 3 and together form an oxo group, and R 4 is a methyl group, and R 5 is a methyl group, and R 6 is a hydrogen atom, and R 7 and R 11 and together form -O-, and R 8 is a hydrogen atom, and R 9 is a methyl group, and R 10 is a hydrogen atom, and R 12 is a hydrogen atom, and R 13 is a hydrogen atom, and R 14 is a hydrogen atom, and R 15 and R 27 and together form -O-, and R 16is a hydrogen atom or a halogen atom, and R 17 is a hydrogen atom, and R 18 is a methyl group, and R 19 is a hydrogen atom, and R 20 is a hydrogen atom, and R 21 is a methyl group, and R 22 is a hydrogen atom, and R 23 is a hydrogen atom, and R 22 and R 23 and may form a double bond together with the carbon atom to which they are attached, and R 24 and R 25 and together form an oxo group, and R 26 is a hydrogen atom; b 4 :R 1 is a hydrogen atom or a methyl group, and R 2 and R 3 and together form an oxo group, and R 4 is a methyl group, and R 5 is a methyl group, and R 6 is a hydrogen atom, and R 7 and R 11 and together form -O-, and R 8 is a hydrogen atom, and R 9 is a methyl group, and R 10 is a hydrogen atom, and R 12 is a hydrogen atom, and R 13 is a hydrogen atom, and R 14 is a hydrogen atom, and R 15 and R 27 and together form -O-, and R 16 is a hydrogen atom, and R 17 is a hydrogen atom, and R 18 is a methyl group, and R 19 , R 20 , R 22 , R 23 , R 25 , and R 26 form a benzene ring together with the carbon atoms to which they are attached, and R 21 is a methyl group, and R 24 is a hydroxy group or an acetyloxy group; e 4 :R 1is a hydrogen atom or a methyl group, and R 2 and R 3 and together form an oxo group, and R 4 is a methyl group, and R 5 is a methyl group, and R 6 is a hydrogen atom, and R 7 and R 11 and together form -O-, and R 8 is a hydrogen atom, and R 9 is a methyl group, and R 10 is a hydrogen atom, and R 12 is a hydrogen atom, and R 13 is a hydrogen atom, and R 14 is a hydrogen atom, and R 15 is a hydrogen atom, and R 16 is a hydrogen atom, and R 15 and R 16 and may form a double bond together with the carbon atom to which they are attached, and R 17 is a hydrogen atom, and R 18 is a methyl group, and R 19 is a hydrogen atom, and R 20 is a hydrogen atom, and R 21 is a methyl group, and R 22 is a hydrogen atom, and R 23 is a hydrogen atom, and R 22 and R 23 and may form a double bond together with the carbon atom to which they are attached, and R 24 is a hydroxy group, and R 25 is a hydrogen atom, and R 24 and R 25 may be taken together to form an oxo group, and R 26 is a hydrogen atom, and R 27 is a methoxy group or a hydroxy group; and g 4 :R 1 is a hydrogen atom or a methyl group, and R 2 and R 3 and together form an oxo group, and R 4 is a methyl group, and R 5 is a methyl group, and R 6 is a hydrogen atom, and R 7 is a hydrogen atom, and R8 is a hydrogen atom, and R 9 is a methyl group, and R 10 is a hydrogen atom, and R 11 is a hydroxy group, and R 12 is a hydrogen atom, and R 13 is a hydrogen atom, and R 14 is a hydrogen atom, and R 15 is a hydrogen atom, and R 16 is a hydrogen atom, and R 17 is a hydrogen atom, and R 18 is a methyl group, and R 19 is a hydrogen atom, and R 20 is a hydrogen atom, and R 21 is a methyl group, and R 22 is a hydrogen atom, and R 23 is a hydrogen atom, and R 22 and R 23 and may form a double bond together with the carbon atom to which they are attached, and R 24 and R 25 and together form an oxo group, and R 26 is a hydrogen atom, and R 27 is a methoxy group or a hydroxy group. 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , R 21 , R 22 , R 23 , R 24 , R 25 , R 26 , and R 27 The combination of 4[Aspect 35] In aspect 33, the compound 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , R 21 , R 22 , R 23 , R 24 , R 25 , R 26 , and R 27 The combination of 4 [Aspect 36] In aspect 33, the compound 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , R 21 , R 22 , R 23 , R 24 , R 25 , R 26 , and R 27 The combination of 4 [Aspect 37] In aspect 33, the compound 1 , R 2 , R 3 , R 4 , R 5, R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , R 21 , R 22 , R 23 , R 24 , R 25 , R 26 , and R 27 The combination of 4 A compound which is

[0019] The following compounds are examples of the compound of the present invention.

[0020] [Aspect A1] In the compound A of the present invention, R 1 is a hydrogen atom, a methyl group, an ethyl group, or CHOH, and R 2 and R 3 and together form an oxo group, and R 4 is a methyl group, and R 5 is a methyl group, and R 6 is a hydrogen atom, and R 8 is a hydrogen atom, and R 9 is a methyl group, and R 10 is a hydrogen atom, and R 12 is a hydrogen atom, and R 13 is a hydrogen atom, and R 14 is a hydrogen atom, X is a halogen atom, and R 18 is a methyl group, and R 19 is a hydrogen atom, and R 20 is a hydrogen atom, and R 21 is a methyl group, and R 22 is a hydrogen atom, and R 23 is a hydrogen atom, and R 22 and R 23 and may form a double bond together with the carbon atom to which they are attached, and R 24 and R 25and together form an oxo group, and R 26 is a hydrogen atom. [Aspect A2] In the compound A of the present invention, R 1 is a hydrogen atom, a methyl group, an ethyl group, or CHOH, and R 2 and R 3 and together form an oxo group, and R 4 is a methyl group, and R 5 is a methyl group, and R 6 is a hydrogen atom, and R 8 is a hydrogen atom, and R 9 is a methyl group, and R 10 is a hydrogen atom, and R 12 is a hydrogen atom, and R 13 is a hydrogen atom, and R 14 is a hydrogen atom, X is a chlorine atom, and R 18 is a methyl group, and R 19 is a hydrogen atom, and R 20 is a hydrogen atom, and R 21 is a methyl group, and R 22 is a hydrogen atom, and R 23 is a hydrogen atom, and R 22 and R 23 and may form a double bond together with the carbon atom to which they are attached, and R 24 and R 25 and together form an oxo group, and R 26 is a hydrogen atom. [Aspect A3] In the compound A of the present invention, R 1 is a hydrogen atom or a methyl group, and R 2 and R 3 and together form an oxo group, and R 4 is a methyl group, and R 5 is a methyl group, and R 6 is a hydrogen atom, and R 8 is a hydrogen atom, and R 9 is a methyl group, and R 10 is a hydrogen atom, and R 12 is a hydrogen atom, and R 13 is a hydrogen atom, and R 14 is a hydrogen atom, X is a halogen atom, and R 18 is a methyl group, and R 19is a hydrogen atom, and R 20 is a hydrogen atom, and R 21 is a methyl group, and R 22 and R 23 and form a double bond together with the carbon atom to which they are attached, and R 24 and R 25 and together form an oxo group, and R 26 is a hydrogen atom. [Aspect A4] In the compound A of the present invention, R 1 is a hydrogen atom or a methyl group, and R 2 and R 3 and together form an oxo group, and R 4 is a methyl group, and R 5 is a methyl group, and R 6 is a hydrogen atom, and R 8 is a hydrogen atom, and R 9 is a methyl group, and R 10 is a hydrogen atom, and R 12 is a hydrogen atom, and R 13 is a hydrogen atom, and R 14 is a hydrogen atom, X is a chlorine atom, and R 18 is a methyl group, and R 19 is a hydrogen atom, and R 20 is a hydrogen atom, and R 21 is a methyl group, and R 22 and R 23 and form a double bond together with the carbon atom to which they are attached, and R 24 and R 25 and together form an oxo group, and R 26 A compound in which X is a hydrogen atom. [Aspect A5] A compound in which X is a chlorine atom in Compound A of the present invention.

[0021] [Aspect B1] A compound represented by formula (AA1), formula (AA2), formula (AA3), formula (BB1), formula (EE1), formula (EE3), formula (EE4), formula (EE5), formula (EE6), formula (EE7), formula (GG1), formula (GG2), or formula (GG3), or an N-oxide thereof, or a salt thereof. [Aspect B2] A compound represented by formula (AA1), formula (AA2), formula (AA3), formula (BB1), formula (EE1), formula (EE3), formula (EE4), formula (EE5), formula (EE6), formula (GG1), or formula (GG3), or an N-oxide thereof, or a salt thereof. [Aspect B3] A compound represented by formula (AA1) or formula (AA2), or an N-oxide thereof, or a salt thereof. [Aspect B4] A compound represented by formula (EE2).

[0022] Next, the present compound and a method for producing the compound of the present invention will be described.

[0023] This compound is described in Heterocyclic Communications (1995), 1(2-3), 207; Journal of Organic Chemistry (1985), 50(20), 3757; Heterocycles (1989), 28(1), 103; Tetrahedron (1998), 54(27), 7891; Tetrahedron (1999), 55(17), 5539; Marine Drugs (2014), 12(10), 5188; Tetrahedron Letters (2014), 55(39), 5369; Tetrahedron (2015), 71(45), 8601; Journal of Natural Products (2019), 82(10), 2790; Journal of Natural Products (2016), 79(10), 2674; Marine Drugs (2018), 16(7), 242; Tetrahedron Letters (2008), 49(14), 2189; J. Org. Chem. 2020, 85, 12553; Bioorganic Chemistry 109 (2021) 104700; Bulletin of the Chemical Society of Japan (1998), 71(4), 771; Heterocyclic Communications (1998), 4(6), 575; Angewandte Chemie (International ed.(in English) (2009), 48(47), 8905; Chemistry - An Asian Journal (2011), 6(3), 922; Heterocyclic Communications (1995), 1(2-3), 207; Tetrahedron Letters (1997), 38(32), 5683; JP-A-10-101678; U.S. Patent Application Publication No. 2016 / 0036094; Tetrahedron Letters (2008), 49(14), 2189; Abstracts of the 62nd Symposium on Natural Organic Compounds (2020), pp. 2-8, etc. It can also be produced by the following production method.

[0024] Production Method 1 The compound represented by formula (II) (hereinafter referred to as compound (II)) can be produced by reacting a compound represented by formula (II-a) (hereinafter referred to as compound (II-a)) with a halogenating agent. [In the formula, the symbols have the same meanings as defined above.] The reaction is usually carried out in a solvent. Examples of the solvent include halogenated hydrocarbons such as dichloromethane and chloroform; nitriles such as acetonitrile; carbon disulfide; acetic acid; and mixtures of two or more of these. Examples of the halogenating agent include succinimides such as N-chlorosuccinimide, N-bromosuccinimide, and N-iodosuccinimide; and halogens such as fluorine, chlorine, bromine, and iodine. The reaction may be carried out in the presence of an additive. Examples of the additive include p-toluenesulfonic acid monohydrate. In the reaction, the halogenating agent is usually used in a ratio of 1 to 2 moles per mole of compound (II-a). The reaction temperature is usually in the range of −10 to 50°C. The reaction time is usually in the range of 0.1 to 36 hours. After completion of the reaction, water is added to the reaction mixture, which is then extracted with an organic solvent. The resulting organic layer is dried and concentrated to obtain compound (II). Compound (II-a) is known, or can be produced or obtained by the above-mentioned method for obtaining this compound or a method similar to the known method.

[0025] Production Method 2 The present compound and salts of the compound of the present invention can be produced, for example, according to the methods described in JP-A-10-53589, Bulletin of the Chemical Society of Japan (1998), 71(4), 771; Chemistry - An Asian Journal (2011), 6(3), 922; and Pure and Applied Chemistry (2007), 79, 651.

[0026] The present compound can be mixed or used in combination with one or more components selected from the group consisting of Group (a), Group (b), Group (c), Group (d), and Group (e) below (hereinafter referred to as the present component). The term "mixed or used in combination" means that the present compound and the present component are used simultaneously, separately, or with a time interval. When the present compound and the present component are used simultaneously, the present compound and the present component may be contained in separate preparations or in a single preparation. One aspect of the present invention is a composition (hereinafter referred to as Composition A) containing one or more components selected from the group consisting of Group (a), Group (b), Group (c), Group (d), and Group (e), and the present compound.

[0027] The compound of the present invention can be mixed or used in combination with one or more components selected from the group consisting of Group (a), Group (b), Group (c), Group (d), and Group (e) below (i.e., the present component). The term "mixed or used in combination" means that the compound of the present invention and the present component are used simultaneously, separately, or with a time interval. When the compound of the present invention and the present component are used simultaneously, the compound of the present invention and the present component may be contained in separate preparations or in a single preparation. One aspect of the present invention is a composition (hereinafter referred to as Composition B) containing one or more components selected from the group consisting of Group (a), Group (b), Group (c), Group (d), and Group (e), and the compound of the present invention.

[0028] Group (a) includes acetylcholinesterase inhibitors (e.g., carbamate insecticides, organophosphate insecticides), GABAergic chloride channel blockers (e.g., phenylpyrazole insecticides), sodium channel modulators (e.g., pyrethroid insecticides), nicotinic acetylcholine receptor competitive modulators (e.g., neonicotinoid insecticides), nicotinic acetylcholine receptor allosteric modulators, glutamate-gated chloride channel allosteric modulators (e.g., macrolide insecticides), juvenile hormone mimics, multisite inhibitors, chordotonal organ TRPV channel modulators, mite growth inhibitors, microbial insect midgut membrane disruptors, mitochondrial ATP synthase inhibitors, oxidative phosphorylation uncouplers, nicotinic acetylcholine receptor channel blockers (e.g., nereistoxin insecticides), chitin biosynthesis inhibitors, molting inhibitors, ecdysone receptor agonists, octopamine receptor agonists, mitochondrial electron transport chain complexes I and II, The group consisting of inhibitors of classes III and IV, voltage-dependent sodium channel blockers, acetyl-CoA carboxylase inhibitors, ryanodine receptor modulators (e.g., diamide insecticides), chordotonal organ modulators, and other insecticidal, acaricidal, and nematocidal active ingredients, which are described in the IRAC mechanism-based classification.

[0029] Group (b) consists of nucleic acid synthesis inhibitors (e.g., phenylamide fungicides, acylamino acid fungicides), cell division and cytoskeleton inhibitors (e.g., MBC fungicides), respiratory inhibitors (e.g., QoI fungicides, QiI fungicides), amino acid synthesis and protein synthesis inhibitors (e.g., anilinopyridine fungicides), signal transduction inhibitors, lipid synthesis and membrane synthesis inhibitors, sterol biosynthesis inhibitors (e.g., DMI fungicides such as triazoles), cell wall biosynthesis inhibitors, melanin synthesis inhibitors, plant defense inducers, multisite contact-active fungicides, and other fungicidal active ingredients. These are listed in the FRAC classification based on the mechanism of action.

[0030] Group (c) is a group of plant growth regulators.

[0031] Group (d) is a group of repellent ingredients.

[0032] Group (e) is a group of biological control agents consisting of bacteria, fungi, yeasts, protists, viruses, products produced by organisms, plants, and plant extracts.

[0033] Examples of combinations of the present component and the present compound or the compound of the present invention are described below. For example, alanycarb + SX refers to a combination of alanycarb and SX. The abbreviation SX refers to any one of the present compounds or compounds of the present invention selected from the present compounds A-1 to A-23, B-1, B-2, C-1 to C-44, D-1, D-2, E-1 to E-5, F-1 to F-5, G-1, and G-2, and the present compounds AA-1 to AA-3, BB-1, EE-1 to EE-7, and GG-1 to GG-3. The present components described below are all known and can be obtained from commercially available formulations or produced by known methods. When the present component is a microorganism, it can also be obtained from a bacterial depository. The number in parentheses indicates the CAS RN (registered trademark).

[0034] Combinations of the present ingredient of group (a) above with the present compound or the compound of the present invention: abamectin + SX, acephate + SX, acequinocyl + SX, acetamiprid + SX, acetoprole + SX, acrinathrin + SX, acinonapyr + SX, afidopyropen + SX, afoxolaner + SX, alanycarb + SX, aldicarb + SX, allethrin + SX, alpha-cypermethrin + SX, alpha-endosulfan + SX, aluminum phosphide + SX, Amitraz + SX, azadirachtin + SX, azamethiphos + SX, azinphos-ethyl + SX, azinphos-methyl + SX, azocyclotin + SX, bendiocarb + SX, benfluthrin + SX, benfuracarb + SX, bensultap + SX, benzoximate + SX, benzpyrimoxan + SX, beta-cyfluthrin + SX, beta-cypermethrin + SX, bifenazate + SX, Bifenthrin + SX, bioallethrin + SX, bioresmethrin + SX, bistrifluron + SX,Borax + SX, boric acid + SX, broflanilide + SX, bromopropylate + SX, buprofezin + SX, butocarboxim + SX, butoxycarboxim + SX, cadusafos + SX, calcium phosphide + SX, carbaryl + SX, carbofuran + SX, carbosulfan + SX, cartap hydrochloride + SX, cartap + SX, chinomethionate + SX, chlorantraniliprole + SX, Chlordane + SX, chlorethoxyfos + SX, chlorfenapyr + SX, chlorfenvinphos + SX, chlorfluazuron + SX, chlormephos + SX, chloropicrin + SX, chlorpyrifos + SX, chlorpyrifos-methyl + SX, chromafenozide + SX, clofentezine + SX, clothianidin + SX, coumaphos + SX, cryolite + SX, cyanophos + SX, Cyantraniliprole + SX, cyclaniliprole + SX, cyclobutrifluram + SX,Cycloprothrin + SX, cycloxaprid + SX, cyenopyrafen + SX, cyetpyrafen + SX, cyflumetofen + SX, cyfluthrin + SX, cyhalodiamide + SX, cyhalothrin + SX, cyhexatin + SX, cypermethrin + SX, cyphenothrin + SX, cyproflanilide + SX, cyromazine + SX, dazomet + SX, deltamethrin + SX Demeton-S-methyl + SX, diafenthiuron + SX, diazinon + SX, dichlorvos + SX, dichloromezotiaz + SX, dicofol + SX, dicrotophos + SX, diflovidazin + SX, diflubenzuron + SX, dimefluthrin + SX, dimethoate + SX, dimethylvinphos + SX, dimpropyridaz + SX, dinotefuran + SX, disodium octaborate octaborate + SX, disulfoton + SX, DNOC (2-methyl-4,6-dinitrophenol) + SX, doramectin + SX, emamectin benzoate + SX, empenthrin + SX,Endosulfan + SX, EPN (O-ethyl O-(4-nitrophenyl) phenylphosphonothioate) + SX, epsilon-metofluthrin + SX, epsilon-momfluorothrin + SX, esfenvalerate + SX, ethifencarb + SX, ethion + SX, ethiprole + SX, ethoprophos + SX, etofenprox + SX, etoxazole + SX, famphur + SX, fenamiphos + SX, fenazaquin + SX, fenbutatin oxide oxide + SX, fenitrothion + SX, fenmezoditiaz + SX, fenobucarb + SX, fenoxycarb + SX, fenpropathrin + SX, fenpyroximate + SX, fenthion + SX, fenvalerate + SX, fipronil + SX, flometoquin + SX, flonicamid + SX, fluacrypyrim + SX, fluazaindolizine + SX, fluazuron + SX, flubendiamide + SX, fluchlordiniliprole + SX, flucycloxuron + SX, flucythrinate + SX,Fluensulfone + SX, Flufenoprox + SX, Flufenoxuron + SX, Flufiprole + SX, Flumethrin + SX, Flupentiofenox + SX, Flupyradifurone + SX, Flupyrimin + SX, Flupyroxystrobin + SX, Fluralaner + SX, Fluvalinate + SX, Fluxametamide + SX, Formetanate + SX, Fosthiazate + SX, Furamethrin + SX Furathiocarb + SX, gamma-cyhalothrin + SX, GS-omega / kappa HXTX-Hv1a peptide + SX, halfenprox + SX, halofenozide + SX, heptafluthrin + SX, heptenophos + SX, hexaflumuron + SX, hexythiazox + SX, potassium salt of hop beta acid + SX, hydramethylnon + SX, hydroprene + SX, imicyafos + SX, Imidacloprid + SX, imidaclothiz + SX, imiprothrin + SX, indazapyroxamet + SX,Indoxacarb + SX, isocycloseram + SX, isofenphos + SX, isoprocarb + SX, isopropyl-O-(methoxyaminothiophosphoryl) salicylate + SX, isoxathion + SX, ivermectin + SX, kadethrin + SX, kappa-tefluthrin + SX, kappa-bifenthrin + SX, kinoprene + SX, lambda-cyhalothrin + SX, ledprona + SX, Lenoremycin + SX, lepimectin + SX, lime sulfur + SX, lotilaner + SX, lufenuron + SX, machine oil + SX, malathion + SX, mecarbam + SX, meperfluthrin + SX, metaflumizone + SX, metam + SX, metham + SX, methamidophos + SX, methidathion + SX, methiocarb + SX, methomyl + SX, methoprene + SX, methoxychlor + SX, Methoxyfenozide + SX, methyl bromide + SX, metofluthrin + SX, metolcarb + SX, metoxadiazone + SX,Mevinphos + SX, milbemectin + SX, milbemycin oxime + SX, mivorilaner + SX, modoflaner + SX, momfluorothrin + SX, monocrotophos + SX, moxidectin + SX, naled + SX, nicofluprole + SX, nicotine + SX, nicotine sulfate + SX, nitenpyram + SX, novaluron + SX, noviflumuron + SX, omethoate + SX, Oxamyl + SX, oxazosulfyl + SX, oxydemeton-methyl + SX, parathion + SX, parathion-methyl + SX, permethrin + SX, phenothrin + SX, phenthoate + SX, phorate + SX, phosalone + SX, phosmet + SX, phosphamidon + SX, phosphine + SX, phoxim + SX, pirimicarb + SX, pirimiphos-methyl + SX, prallethrin + SX, Profenofos + SX, profluthrin + SX, propargite + SX, propetamphos + SX, propoxur + SX,Propylene glycol alginate + SX, prothiofos + SX, pyflubumide + SX, pymetrozine + SX, pyraclofos + SX, pyrethrins + SX, pyridaben + SX, pyridalyl + SX, pyridaphenthion + SX, pyrifluquinazone + SX, pyrimidifen + SX, pyriminostrobin + SX, pyriprole + SX, pyriproxyfen + SX, quinalphos + SX, resmethrin + SX, rotenone + SX, sarolaner + SX, selamectin + SX, sigma-cypermethrin + SX, silafluofen + SX, sodium borate + SX, sodium metaborate + SX, spidoxamat + SX, spinetoram + SX, spinosad + SX, spirobudifen + SX, spirodiclofen + SX, spiromesifen + SX, spiropidione + SX, spirotetramat + SX, sulfluramid + SX, sulfotep + SX, sulfoxaflor + SX, sulfur + SX, sulfuryl fluoride + SX,Tartar emetic + SX, tau-fluvalinate + SX, tebufenozide + SX, tebufenpyrad + SX, tebupirimfos + SX, teflubenzuron + SX, tefluthrin + SX, temephos + SX, terbufos + SX, tetrachlorantraniliprole + SX, tetrachlorvinphos + SX, tetradifon + SX, tetramethrin + SX, tetramethylfluthrin + SX, Tetraniliprole + SX, theta-cypermethrin + SX, thiacloprid + SX, thiamethoxam + SX, thiocyclam + SX, thiodicarb + SX, thiofanox + SX, thiometon + SX, thiosultap disodium + SX, thiosultap monosodium + SX, tigolaner + SX, thioantraniliprole + SX, tioxazafen + SX, tolfenpyrad + SX, Tralomethrin + SX, transfluthrin + SX, triazamate + SX, triazophos + SX, trichlorfon + SX,Trifluenfuronate + SX, triflumezopyrim + SX, triflumuron + SX, trimethacarb + SX, tyclopyrazoflor + SX, umifoxolaner + SX, vamidothion + SX, 3,5-dimethylphenyl N-methylcarbamate (XMC) + SX, xylylcarb + SX, zeta-cypermethrin + SX, zinc phosphide + SX, 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-methyl-N-(1-oxothietan-3-yl)benzamide (1241050-20-3) + SX, 3-methoxy-N-(5-{5-(trifluoromethyl)-5-[3-(trifluoromethyl)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}indan-1-yl)propanamide (1118626-57-5) + SX, 2-({2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl}imino)-3-(2,2,2-trifluoroethyl)-1,3-thiazolidin-4-one (1445683-71-5) + SX, (2Z)-2-({2-fluoro-4-methyl-5-[(R)-(2,2,2-trifluoroethyl)sulfinyl]phenyl}imino)-3-(2,2,2-trifluoroethyl)-1,3-thiazolidin-4-one (2377084-09-6) + SX, N-{4-chloro-3-[(1-cyanocyclopropyl)carbamoyl]phenyl}-1-methyl-4-(methanesulfonyl)-3-(1,1,2,2,2-pentafluoroethyl)-1H-pyrazole-3-carboxamide (1400768-21-9) + SX, N-[3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl]-2-(methanesulfonyl)propanamide (2396747-83-2) + SX, 1,4-dimethyl-2-[2-(3-pyridinyl)-2H-indazol-5-yl]-1,2,4-triazolidine-3,5-dione (2171099-09-3) + SX, 2-isopropyl-5-[(3,4,4-trifluoro-3-buten-1-yl)sulfonyl]-1,3,4-thiadiazole (2058052-95-0) + SX, N-({2-fluoro-4-[(2S,3S)-2-hydroxy-3-(3,4,5-trichlorophenyl)-3-(trifluoromethyl)pyrrolidin-1-yl]phenyl}methyl)cyclopropanecarboxamide + SX, 7-fluoro-N-[1-(methylsulfanyl)-2-methylpropan-2-yl]-2-(pyridin-3-yl)-2H-indazole-4-carboxamide + SX, 7-fluoro-N-[1-(methanesulfinyl)-2-methylpropan-2-yl]-2-(pyridin-3-yl)-2H-indazole-4-carboxamide + SX, 7-fluoro-N-[1-(methanesulfonyl)-2-methylpropan-2-yl]-2-(pyridin-3-yl)-2H-indazole-4-carboxamide + SX, N-[1-(difluoromethyl)cyclopropyl]-2-(pyridin-3-yl)-2H-indazole-4-carboxamide + SX, 2,9-dihydro-9-(methoxymethyl)-2-(pyridin-3-yl)-10H-pyrazolo[3,4-f]pyrido[2,3-b][1,4]oxazepin-10-one (2607927-97-7) + SX。,

[0035] Combinations of the present ingredient of the above group (b) with the present compound or the compound of the present invention: acibenzolar-S-methyl + SX, aldimorph + SX, ametoctradin + SX, aminopyrifen + SX, amisulbrom + SX, anilazine + SX, azaconazole + SX, azoxystrobin + SX, basic copper sulfate + SX, benalaxyl + SX, benalaxyl-M + SX, benodanil + SX, benomyl + SX, benthiavalicarb + SX, Benthiavalicarb-isopropyl + SX, benzovindiflupyr + SX, binapacryl + SX, biphenyl + SX, bitertanol + SX, bixafen + SX, blasticidin S + SX, Bordeaux mixture + SX, boscalid + SX, bromothalonil + SX, bromuconazole + SX, bupirimate + SX, captafol + SX, captan + SX, carbendazim + SX, carboxin + SX, carpropamid + SX, chinomethionate + SX, chloroinconazide + SX, chloroneb + ​​SX,Chlorothalonil + SX, chlozolinate + SX, copper(II) acetate + SX, copper(II) hydroxide + SX, copper oxychloride + SX, copper(II) sulfate + SX, coumoxystrobin + SX, cyazofamid + SX, cyflufenamid + SX, cymoxanil + SX, cyproconazole + SX, cyprodinil + SX, dichlobentiazox + SX, dichlofluanid + SX Diclocymet + SX, diclomezine + SX, dicloran + SX, diethofencarb + SX, difenoconazole + SX, diflumetorim + SX, dimethachlone + SX, dimethirimol + SX, dimethomorph + SX, dimoxystrobin + SX, diniconazole + SX, diniconazole-M + SX, dinocap + SX, dipotassium hydrogenphosphite + SX, dipymetitrone + SX, dithianon + SX, dodecylbenzenesulphonic acid bisethylenediamine copper(II) salt + SX,Dodemorph + SX, dodine + SX, edifenphos + SX, enoxastrobin + SX, epoxiconazole + SX, etaconazole + SX, ethaboxam + SX, ethirimol + SX, etridiazole + SX, famoxadone + SX, fenamidone + SX, fenaminstrobin + SX, fenarimol + SX, fenbuconazole + SX, fenfuram + SX, fenhexamid + SX, Fenoxanil + SX, fenpiclonil + SX, fenpicoxamid + SX, fenpropidin + SX, fenpropimorph + SX, fenpyrazamine + SX, triphenyltin acetate + SX, triphenyltin chloride + SX, fentin hydroxide + SX, ferbam + SX, ferimzone + SX, florylpicoxamid + SX, fluazinam + SX, flubeneteram + SX, fludioxonil + SX, Flufenoxadiazam + SX, Flufenoxystrobin + SX, Fluindapyr + SX, Flumetylsulforim + SX,Flumorph + SX, fluopicolide + SX, fluopyram + SX, fluopimomide + SX, fluoroimide + SX, fluoxapiprolin + SX, fluoxastrobin + SX, fluoxytioconazole + SX, fluquinconazole + SX, flusilazole + SX, flusulfamide + SX, flutianil + SX, flutolanil + SX, flutriafol + SX, fluxapyroxad + SX, folpet + SX, Fosetyl + SX, fosetyl-aluminium + SX, fuberidazole + SX, furalaxyl + SX, furametpyr + SX, guazatine + SX, hexaconazole + SX, hymexazole + SX, imazalil + SX, imibenconazole + SX, iminoctadine + SX, iminoctadine triacetate + SX, inpyrfluxam + SX, iodocarb + SX, ipconazole + SX Ipfentrifluconazole + SX, Ipflufenoquin + SX, Iprobenfos + SX, Iprodione + SX,Iprovalicarb + SX, isofetamide + SX, isoflucipram + SX, isoprothiolane + SX, isopyrazam + SX, isotianil + SX, kasugamycin + SX, kresoxim-methyl + SX, laminarin + SX, mancozeb + SX, mandestrobin + SX, mandipropamid + SX, maneb + ​​SX, mefentrifluconazole + SX, mepanipyrim + SX, Mepronil + SX, meptyldinocap + SX, metalaxyl + SX, metalaxyl-M + SX, metarylpicoxamid + SX, metconazole + SX, methasulfocarb + SX, metiram + SX, metominostrobin + SX, metrafenone + SX, metyltetraprole + SX, myclobutanil + SX, naftifine + SX, nuarimol + SX, octhilinone + SX Ofurace + SX, orysastrobin + SX, oxadixyl + SX, oxathiapiprolin + SX, oxine-copper + SX, oxolinic acid + SX,Oxpoconazole + SX, oxpoconazole fumarate + SX, oxycarboxin + SX, oxytetracycline + SX, pefurazoate + SX, penconazole + SX, pencycuron + SX, penflufen + SX, penthiopyrad + SX, phenamacril + SX, phosphorous acid + SX, phthalide + SX, picarbutrazox + SX, picoxystrobin + SX, piperalin + SX, polyoxins + SX, Potassium hydrogencarbonate + SX, potassium dihydrogenphosphite + SX, probenazole + SX, prochloraz + SX, procymidone + SX, propamidine + SX, propamocarb + SX, propiconazole + SX, propineb + ​​SX, proquinazid + SX, prothiocarb + SX, prothioconazole + SX, pydiflumetofen + SX, pyraclostrobin + SX, pyrametostrobin + SX, pyraoxystrobin + SX, pyrapropoyne + SX,Pyraziflumid + SX, pyrazophos + SX, pyribencarb + SX, pyributicarb + SX, pyridaclomethyl + SX, pyrifenox + SX, pyrimethanil + SX, pyrimorph + SX, pyriophenone + SX, pyrisoxazole + SX, pyroquilon + SX, quinconazole + SX, quinofumelin + SX, quinoxyfen + SX, quintozene + SX, quinoa saponins Chenopodium quinoa + SX, seboctylamine + SX, sedaxane + SX, silthiofam + SX, simeconazole + SX, sodium hydrogencarbonate + SX, spiroxamine + SX, streptomycin + SX, sulfur + SX, tebuconazole + SX, tebufloquin + SX, teclofthalam + SX, tecnazene + SX, terbinafine + SX, tetraconazole + SX, thiabendazole + SX Thifluzamide + SX, thiophanate + SX, thiophanate-methyl + SX, thiram + SX, thymol + SX,Tiadinil + SX, tolclofos-methyl + SX, tolfenpyrad + SX, tolprocarb + SX, tolylfluanid + SX, triadimefon + SX, triadimenol + SX, triazoxide + SX, triclopyricarb + SX, tricyclazole + SX, tridemorph + SX, trifloxystrobin + SX, triflumizole + SX, triforine + SX, triticonazole + SX, validamycin + SX, valifenalate + SX, vinclozolin + SX, zinc thiazole + SX, zineb + ​​SX, ziram + SX, zoxamide + SX, N'-[4-({3-[(4-chlorophenyl)methyl]-1,2,4-thiadiazol-5-yl}oxy)-2,5-dimethylphenyl]-N-ethyl-N-methylmethanimidamide (1202781-91-6) + SX, N'-{4-[(4,5-dichlorothiazol-2-yl)oxy]-2,5-dimethylphenyl}-N-ethyl-N-methylmethanimidamide (929908-57-6) + SX, N'-(2,5-dimethyl-4-phenoxyphenyl)-N-ethyl-N-methylmethanimidamide (1052688-31-9) + SX,N'-[5-chloro-4-(2-fluorophenoxy)-2-methylphenyl]-N-ethyl-N-methylmethanimidamide (2055589-28-9) + SX, N'-[2-chloro-4-(2-fluorophenoxy)-5-methylphenyl]-N-ethyl-N-methylmethanimidamide (2055756-21-1) + SX, N'-(2-chloro-4-phenoxy-5-methylphenyl)-N-ethyl-N-methylmethanimidamide (2062599-39-5) + SX, N'-[4-(1-hydroxy-1-phenyl-2,2,2-trifluoroethyl)-2-methyl-5-methoxyphenyl]-N-isopropyl-N-methylmethanimidamide (2101814-55-3) + SX, N'-[5-bromo-6-(1-methyl-2-propoxyethoxy)-2-methylpyridin-3-yl]-N-ethyl-N-methylmethanimidamide (1817828-69-5) + SX, 4-(2-bromo-4-fluorophenyl)-N-(2-chloro- 6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine (1362477-26-6) + SX, 2-[6-(3-fluoro-4-methoxyphenyl)-5-methylpyridin-2-yl]quinazoline (1257056-97-5) + SX, ethyl (2Z)-3-amino-2-cyano-3-phenylacrylate (39491-78-6) + SX, N-[(2-chlorothiazol-5-yl)methyl]-N-ethyl-6-methoxy-3-nitropyridin-2-amine (1446247-98-8) + SX, 5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1394057-11-4) + SX, (1R, 2S, 5S)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1801930-06-2) + SX, (1S, 2R, 5R)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1801930-07-3) + SX, 2-(chloromethyl)-5-(4-fluorobenzyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1394057-13-6) + SX, (1R, 2S, 5S)-2-(chloromethyl)-5-(4-fluorobenzyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1801930-08-4) + SX, (1S, 2R, 5R)-2-(chloromethyl)-5-(4-fluorobenzyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1801930-09-5) + SX, methyl 3-[(4-chlorophenyl)methyl]-2-hydroxy-1-methyl-2-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-carboxylate (1791398-02-1) + SX, 1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)-1-[1-(4-bromo-2,6-difluorophenoxy)cyclopropyl]ethanol (2019215-86-0) + SX, 1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)-1-[1-(4-chloro-2,6-difluorophenoxy)cyclopropyl]ethanol (2019215-84-8) + SX, 1-[2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxypropyl]-1H-imidazole-5-carbonitrile (2018316-13-5) + SX, 1-[2-(1-chlorocyclopropyl)-3-(2,3-difluorophenyl)-2-hydroxypropyl]-1H-imidazole-5-carbonitrile (2018317-25-2) + SX, 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)pyridin-3-yl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol (2082661-43-4) + SX, 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)pyridin-3-yl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol (2082660-27-1) + SX, methyl ({2-methyl-5-[1-(4-methoxy-2-methylphenyl)-1H-pyrazol-3-yl]phenyl}methyl)carbamate (1605879-98-8) + SX, 2-(difluoromethyl)-N-[1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]pyridine-3-carboxamide (1616239-21-4) + SX, 2-(difluoromethyl)-N-[3-ethyl-1,1-dimethyl-2,3-dihydro-1H-inden-4-yl]pyridine-3-carboxamide (1847460-02-9) + SX, 2-(difluoromethyl)-N-[3-propyl-1,1-dimethyl-2,3-dihydro-1H-inden-4-yl]pyridine-3-carboxamide (1847460-05-2) + SX, (2E,3Z)-5-{[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide (1445331-27-0) + SX, (2E,3Z)-5-{[1-(2,4-dichlorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide (1445331-54-3) + SX, 5-chloro-4-({2-[6-(4-chlorophenoxy)pyridin-3-yl]ethyl}amino)-6-methylpyrimidine (1605340-92-8) + SX, N-(1-benzyl-1,3-dimethylbutyl)-8-fluoroquinoline-3-carboxamide (2132414-04-9) + SX, N-(1-benzyl-3,3,3-trifluoro-1-methylpropyl)-8-fluoroquinoline-3-carboxamide (2132414-00-5) + SX, 4,4-dimethyl-2-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)isoxazolidin-3-one (2098918-25-1) + SX, 5,5-dimethyl-2-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)isoxazolidin-3-one (2098918-26-2) + SX, N-ethyl-2-methyl-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide + SX, N,2-dimethoxy-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide + SX, N-methoxy-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)cyclopropanecarboxamide + SX, N-methoxy-N'-methyl-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea + SX, N'-ethyl-N-methoxy-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea + SX, N,N'-dimethoxy-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea + SX, N-acetyl-2-(ethanesulfonyl)-N-[2-(methoxycarbonyl)-4-(trifluoromethoxy)phenyl]-4-(trifluoromethyl)benzamide (2043675-28-9) + SX, 3-(4-bromo-7-fluoroindol-1-yl)butan-2-yl N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate + SX, 3-(7-bromoindol-1-yl)butan-2-yl N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate + SX, 3-(7-bromo-4-fluoroindol-1-yl)butan-2-yl N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate + SX, 3-(3,5-dichloropyridin-2-yl)butan-2-yl N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate + SX, 3-(3,5-dichloropyridin-2-yl)butan-2-yl N-{[3-(acetoxymethoxy)-4-methoxypyridin-2-yl]carbonyl}-L-alaninate + SX,(1S)-1-[1-(naphthalen-1-yl)cyclopropyl]ethyl N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate + SX, (1S)-1-[1-(naphthalen-1-yl)cyclopropyl]ethyl N-[(3-acetoxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate + SX, (1S)-1-[1-(naphthalen-1-yl)cyclopropyl]ethyl N-{[3-(acetoxymethoxy)-4-methoxypyridin-2-yl]carbonyl}-L-alaninate + SX, N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)cyclopropanecarboxamide + SX, N-allyl-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)acetamide + SX, N-allyl-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide + SX, N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide + SX, 3,3,3-trifluoro-N-({2-fluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide + SX, 3,3,3-trifluoro-N-({3-fluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide + SX, 3,3,3-trifluoro-N-({2,3-difluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide + SX,N-({2,3-difluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)butanamide + SX, N-methoxy-N-methyl-N'-({ 4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea + SX, N,N-diethyl-N'-({ 4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea + SX, N-methyl-N'-({ 4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea + SX, 1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)pyrrolidin-2-one + SX, 1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)piperidin-2-one + SX, 4-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)morpholin-3-one + SX, 2-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)isoxazolidin-3-one + SX, 3,3-dimethyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)piperidin-2-one + SX, 2-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1,2-oxazinan-3-one + SX, 1-({3-fluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)azepan-2-one + SX, 4,4-dimethyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)pyrrolidin-2-one + SX, 5-methyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)pyrrolidin-2-one + SX, ethyl 1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carboxylate + SX, N-methyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carboxamide + SX, N-propyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carboxamide + SX, N-methoxy-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carboxamide + SX, N-methoxy-N-methyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carboxamide + SX, N,N-dimethyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-1,2,4-triazol-3-amine + SX, N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide + SX, methyl 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propanoate + SX,ethyl 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propanoate + SX, methyl 2-[2-(trifluoromethyl)-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propanoate + SX, 1-(2,3-dimethylpyridin-5-yl)-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline + SX, 1-[2-(difluoromethyl)-3-methylpyridin-5-yl]-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline + SX, 2,2-difluoro-N-[6-({[1-(1-methyl-1H-tetrazol-5-yl)benzimidazol-2-yl]oxy}methyl)pyridin-2-yl]-2-phenoxyacetamide + SX, 1-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluorophenyl)-2-hydroxypropyl]-1H-imidazole-5-carbonitrile + SX, ethyl 1-[(4-{[2-(trifluoromethyl)-1,3-dioxolan-2-yl]methoxy}phenyl)methyl]-1H-pyrazole-4-carboxylate + SX, ethyl 1-[(4-{[(1Z)-2-ethoxy-3,3,3-trifluoro-1-propen-1-yl]oxy}phenyl)methyl]-1H-pyrazole-4-carboxylate + SX, 6-chloro-3-(3-cyclopropyl-2-fluorophenoxy)-N-[2-(2,4-dimethylphenyl)-2,2-difluoroethyl]-5-methylpyridazine-4-carboxamide + SX,6-chloro-3-(3-cyclopropyl-2-fluorophenoxy)-N-[2-(3,4-dimethylphenyl)-2,2-difluoroethyl]-5-methylpyridazine-4-carboxamide + SX, 6-chloro-N-[2-(2-chloro-4-methylphenyl)-2,2-difluoroethyl]-3-(3-cyclopropyl-2-fluorophenoxy)-5-methylpyridazine-4-carboxamide + SX, 2-[cyano(2,6-difluoropyridin-4-yl)amino]-N-(2,2-dimethylcyclobutyl)-5-methylthiazole-4-carboxamide + SX, 2-[cyano(2,6-difluoropyridin-4-yl)amino]-N-(spiro[3.4]octan-1-yl)-5-methylthiazole-4-carboxamide + SX, 2-[cyano(2,6-difluoropyridin-4-yl)amino]-N-hexyl-5-methylthiazole-4-carboxamide + SX, 2-[acetyl(2,6-difluoropyridin-4-yl)amino]-N-(2,2-dimethylcyclobutyl)-5-methylthiazole-4-carboxamide + SX, 2-[(2-methoxyacetyl)(2,6-difluoropyridin-4-yl)amino]-N-(2,2-dimethylcyclobutyl)-5-methylthiazole-4-carboxamide + SX, 2-[(2-methylpropanoyl)(2,6-difluoropyridin-4-yl)amino]-N-(2,2-dimethylcyclobutyl)-5-methylthiazole-4-carboxamide + SX, 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2-fluorophenyl)ethyl]pyrimidin-2-amine + SX,5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2,6-difluorophenyl)ethyl]pyrimidin-2-amine + SX, 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(3,5-difluorophenyl)ethyl]pyrimidin-2-amine + SX, 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(6-chloropyridin-3-yl)ethyl]pyrimidin-2-amine + SX, 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2-fluorophenyl)cyclopropyl]pyrimidin-2-amine + SX, 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2,6-difluorophenyl)cyclopropyl]pyrimidin-2-amine + SX, 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2-fluoro-3-methoxyphenyl)cyclopropyl]pyrimidin-2-amine + SX, 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-2-{[1-(2,6-difluorophenyl)cyclopropyl]oxy}pyrimidine + SX, 3-[3-(3-cyclopropyl-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-[(2,4-dimethylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine + SX, (5S)-3-[3-(3-cyclopropyl-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-[(2,4-dimethylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine + SX,3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyrida zin-4-yl]-5-[(4-bromo-2-methylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine + SX, 3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-[(2-chloro-4-methylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine + SX, (5S)-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-[(2-chloro-4-methylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine + SX, (5R)-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-[(2-chloro-4-methylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine + SX, N-((2S)-1-{3-[2-(5-fluoro-2-methoxyphenyl)-2-hydroxyethyl]-5-[(E)-1-(isopropoxyimino)ethyl]-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl}-3-methylbutan-2-yl)-2-methylpropanamide + SX, N-((2S)-1-{3-[2-(5-fluoro-2-methoxyphenyl)-2-hydroxyethyl]-5-[(E)-1-(isopropoxyimino)ethyl]-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl}-3-methylbutan-2-yl)-2,2-dimethylpropanamide + SX, N-((2S)-1-{3-[2-(5-fluoro-2-methoxyphenyl)-2-hydroxyethyl]-5-[(E)-1-(isopropoxyimino)ethyl]-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl}propan-2-yl)-2-methylpropanamide + SX, N-((2S)-1-{3-[2-(2-methoxyphenyl)-2-hydroxyethyl]-5-[(E)-1-(isopropoxyimino)ethyl]-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl}propan-2-yl)-2-methylpropanamide + SX, N-((2S)-1-{3-[2-(5-fluoro-2-methoxyphenyl)-2-(2-cyanoethoxy)ethyl]-5-[1-(isopropoxyimino)ethyl]-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl}propan-2-yl)-2-methylpropanamide + SX。,

[0036] Combinations of the present component of group (c) above with the present compound or the compound of the present invention: 1-methylcyclopropene + SX, 1,3,5-triazinane-2,4,6-trithione + SX, 1,3-diphenylurea + SX, 2,3,5-triiodobenzoic acid + SX, IAA ((1H-indol-3-yl)acetic acid) + SX, IBA (4-(1H-indol-3-yl)butyric acid) + SX, MCPA (2-(4-chloro-2-methylphenoxy)acetic acid) + SX, MCPB (4-(4-chloro-2-methylphenoxy)butyric acid) + SX, 4-CPA (4-chlorophenoxyacetic acid) + SX, 5-aminolevulinic acid hydrochloride + SX, 6-benzylaminopurine + SX, abscisic acid + SX, AVG (aminoethoxyvinylglycine) + SX, anisiflupurin + SX, ancymidol + SX, butralin + SX, calcium carbonate + SX, calcium chloride + SX, calcium formate + SX, calcium peroxide + SX, calcium polysulfide + SX, calcium sulfate + SX, chlormequat chloride + SX, chlorpropham + SX, choline chloride + SX, cloprop + SX,Cyanamide + SX, cyclanilide + SX, daminozide + SX, decan-1-ol + SX, dichlorprop + SX, dikegulac + SX, dimethipin + SX, diquat + SX, ethephon + SX, ethychlozate + SX, flumetralin + SX, flurprimidol + SX, forchlorfenuron + SX, formononetin + SX, gibberellin A + SX, gibberellin A3 A3) + SX, inabenfide + SX, kinetin + SX, lipochitooligosaccharide SP104 + SX, maleic hydrazide + SX, mefluidide + SX, mepiquat chloride + SX, oxidized glutathione + SX, paclobutrazol + SX, pendimethalin + SX, prohexadione calcium + SX, prohydrojasmon + SX, pyraflufen-ethyl + SX, pyroglutamic acid + SX, sintophen + SX, sodium 1-naphthaleneacetate + SX, sodium cyanate + SX, thidiazuron + SX,Titanium apatite + SX, triapenthenol + SX, tribufos + SX, trinexapac-ethyl + SX, uniconazole-P + SX, 2-(naphthalen-1-yl)acetamide + SX, [4-oxo-4-(2-phenylethyl)amino]butyric acid + SX, methyl 5-(trifluoromethyl)benzo[b]thiophene-2-carboxylate + SX, 3-[(6-chloro-4-phenylquinazolin-2-yl)amino]propan-1-ol + SX.

[0037] Combinations of the present component of the above group (d) with the present compound or the compound of the present invention: anthraquinone + SX, deet + SX, icaridin + SX.

[0038] Note: Abbreviata caucasica + SX, Acuaria spp. + SX, Agamermys decaudata + SX, Agrobacterium radiobacter strain K1026 + SX, Agrobacterium radiobacter strain K84 + SX, Agrobacterium vitis strain VAR03-1 + SX, Allantonema spp. + SX, Alternaria destroys strain 59 + SX, Alternaria detruens + SX, Ampelomyces quisqualis strain AQ10 + SX, Amphimermis spp. + SX, Arthrobotrys dactyloides + SX, Arthrobotrys superba + SX, Aschersonia aleyrodis + SX, Aspergillus flavus strain AF36 + SX, Aspergillus flavus strain NRRL21882 + SX, Aureobasidium pullulans strain DSM14940 + SX, Aureobasidium pullulans strain DSM14941 + SX, Azorhizobium caulinodans strain ZB-SK-5 + SX, Azotobacter chroococcum strain H23 + SX, Azotobacter chroocuccum + SX, Azotobacter vinelandii strain ATCC12837 + SX, Azotobacter + SX, Bacillus acidocaldarius + SX, Bacillus acidoearth + SX, Bacillus albolactis + SX, Bacillus alkalophilus + SX, Bacillus alvei + SX, Bacillus aminoglucosidicus + SX,Bacillus aminovorans + SX, Bacillus amyloliquefaciens strain PTA-4838 (Aveo (trademark) EZ Nematicide) + SX, Bacillus amyloliquefaciens strain AT332 + SX, Bacillus amyloliquefaciens strain B3 + SX, Bacillus amyloliquefaciens strain D747 + SX, Bacillus amyloliquefaciens strain DB101 + SX, Bacillus amyloliquefaciens strain DB102 + SX, Bacillus amyloliquefaciens strain FZB24 + SX, Bacillus amyloliquefaciens strain FZB42 + SX, Bacillus amyloliquefaciens strain GB03 + SX, Bacillus amyloliquefaciens strain IN937a + SX, Bacillus amyloliquefaciens strain MBI600 + SX, Bacillus amyloliquefaciens strain QST713 + SX, Bacillus amyloliquefaciens isolate strain B246 + SX, Bacillus amyloliquefaciens strain F727 + SX, Bacillus amyloliquefaciens subsp. Plantarum strain D747 +SX, Bacillus amylolyticus + SX, Bacillus aneurinolyticus + SX, Bacillus agri + SX, Bacillus atrophaeus + SX, Bacillus atrophaeus strain Abi05 + SX, Bacillus azotoformans + SX, Bacillus badius + SX, Bacillus cereus strain BP01 + SX,Bacillus cereus CNCM strain I-1562 + SX, Bacillus chitinosporus strain AQ746 + SX, Bacillus chitinosporus strain CM-1 + SX, Bacillus circulans + SX, Bacillus coagulans strain TQ33 + SX, Bacillus fastidiosus + SX, Bacillus firmus strain GB-126 + SX, Bacillus firmus strain I-1582 + SX, Bacillus firmus strain NCIM2637 + SX, Bacillus lacticola + SX, Bacillus lactimorbus + SX, Bacillus lactis + SX, Bacillus lautus + SX, Bacillus Lentimorbus + SX, Bacillus lentus + SX, Bacillus licheniformis strain FMCH001 + SX, Bacillus licheniformis strain HB-2 + SX, Bacillus licheniformis strain SB3086 + SX, Bacillus maroccanus + SX, Bacillus medusa + SX, Bacillus megaterium strain YFM3.25 + SX, Bacillus methylotrophicus strain BAC-9912 + SX, Bacillus metiens + SX, Bacillus mojavensis strain SR11 + SX, Bacillus mycoides strain AQ726 + SX, Bacillus mycoides isolate J + SX, Bacillus nematocida + SX, Bacillus nigrificans + SX, Bacillus nigrum + SX, Bacillus popilliae + SX,Bacillus psychrosaccharolyticus + SX, Bacillus pumilus strain AQ717 + SX, Bacillus pumilus strain BUF-33 + SX, Bacillus pumilus strain GB34 + SX, Bacillus pumilus strain QST2808 + SX, Bacillus siamensis + SX, Bacillus simplex strain CGF2856 + SX, Bacillus smithii + SX, Bacillus sp. strain AQ175 + SX, Bacillus sp. strain AQ177 + SX, Bacillus sp. strain AQ178 + SX, Bacillus sphaericus strain 2362 serotype H5a5b + SX, Bacillus sphaericus strain ABTS1743 + SX, Bacillus subtilis strain AFS032321 + SX, Bacillus subtilis strain AQ153 + SX, Bacillus subtilis strain AQ743 + SX, Bacillus subtilis strain B246 + SX, Bacillus subtilis strain C-3102 + SX, Bacillus subtilis strain D747 + SX, Bacillus subtilis strain DB101 + SX, Bacillus subtilis strain DB102 + SX, Bacillus subtilis strain FMCH002 + SX, Bacillus subtilis strain FZB24 + SX, Bacillus subtilis strain GB03 + SX, Bacillus subtilis strain HAI0404 + SX, Bacillus subtilis strain IAB / BS03 + SX, Bacillus subtilis strain MBI600 + SX,Bacillus subtilis strain QST30002 / AQ30002 + SX, Bacillus subtilis strain QST30004 / AQ30004 + SX, Bacillus subtilis strain QST713 + SX, Bacillus subtilis strain QST714 + SX, Bacillus subtilis var. Amyloliquefaciens strain FZB24 + SX, Bacillus subtilis strain Y1336 + SX, Bacillus subtillis subsp.natto + SX, Bacillus subtilis strain RTI477 + SX, Bacillus subtilis strain N5 NRRL B-50391 + SX, Bacillus subtilis strain DSM17231 + SX, Bacillus tequilensis strain NII-0943 + SX, Bacillus thuringiensis strain AQ52 + SX, Bacillus thuringiensis strain BD#32 + SX, Bacillus thuringiensis strain CR-371 + SX, Bacillus thuringiensis strain EX297512 + SX, Bacillus thuringiensis subsp. Aizawai strain ABTS-1857 + SX, Bacillus thuringiensis subsp. Aizawai strain GC-91 + SX, Bacillus thuringiensis subsp. Aizawai strain NB200 + SX, Bacillus thuringiensis subsp. Aizawai Serotype H-7 + SX, Bacillus thuringiensis subsp. Kurstaki strain ABTS351 + SX, Bacillus thuringiensis subsp. Kurstaki strain BMP123 + SX,Bacillus thuringiensis subsp. Kurstaki strain CCT1306 + SX, Bacillus thuringiensis subsp. Kurstaki strain EG2348 + SX, Bacillus thuringiensis subsp. Kurstaki strain EG2371 + SX, Bacillus thuringiensis subsp. Kurstaki strain EG7673 + SX, Bacillus thuringiensis subsp. Kurstaki strain EG7841 + SX, Bacillus thuringiensis subsp. Kurstaki strain EVB113-19 + SX, Bacillus thuringiensis subsp. Kurstaki strain F810 + SX, Bacillus thuringiensis subsp. Kurstaki strain HD-1 + SX, Bacillus thuringiensis subsp. Kurstaki strain M-200 + SX, Bacillus thuringiensis subsp. Kurstaki strain NCIM2514 + SX, Bacillus thuringiensis subsp. Kurstaki strain PB54 + SX, Bacillus thuringiensis subsp. Kurstaki strain SA-11 + SX, Bacillus thuringiensis subsp. Kurstaki strain SA-12 + SX, Bacillus thuringiensis subsp. Kurstaki strain VBTS-2546 + SX, Bacillus thuringiensis subsp. Kurstaki strain Z-52, serotype H-3a,3b + SX, Bacillus thuringiensis subsp. morrisoni + SX,Bacillus thuringiensis subsp. Tenebriosis strain NB 176 + SX, Bacillus thuringiensis subsp. tenebriosis strain SA-10 + SX, Bacillus thuringiensis subsp. Thuringiensis strain MPPL002 + SX, Bacillus thuringiensis subsp. var. colmeri + SX, Bacillus thuringiensis subsp. var. darmstadiensis strain 24-91 + SX, Bacillus thuringiensis subsp. var. dendrolimus + SX, Bacillus thuringiensis subsp. var. galleriae + SX, Bacillus thuringiensis subsp. israelensis strain BMP144 + SX, Bacillus thuringiensis subsp. israelensis strain AM65-52 + SX, Bacillus thuringiensis subsp. israelensis (serotype H-14) strain AM65-52 + SX, Bacillus thuringiensis subsp. israelensis strain EG2215 + SX, Bacillus thuringiensis subsp. israelensis strain SA3A + SX, Bacillus thuringiensis subsp. israelensis strain SUM-6218 + SX, Bacillus thuringiensis subsp. israelensis strain VCRC B17 serotype 11-14 + SX, Bacillus thuringiensis subsp. var. japonensis strain buibui + SX, Bacillus thuringiensis subsp. var. aegypti + SX,Bacillus thuringiensis var. 7216 + SX, Bacillus thuringiensis var. Sandiego strain M-7 + SX, Bacillus thuringiensis var. T36 + SX, Bacillus velezensis + SX, Bacillus velezensis strain RTI301 + SX, Bacillus velezensis strain FZB42 + SX, bacteriophage of Clavibacter michiganesis + SX, Beauveria bassiana strain ANT-03 + SX, Beauveria bassiana strain ATCC74040 + SX, Beauveria bassiana strain GHA + SX, Beauveria bassiana strain PPRI 5339 + SX, Beauveria bassiana strain IMI389521 + SX, Beauveria brongniartii + SX, Deladenus siridicola + SX, Bovienema spp. + SX, Brevibacillus brevis strain 2904 + SX, Brevibacillus brevis strain SS86-3 + SX, Brevibacillus brevis strain SS86-4 + SX, Brevibacillus brevis strain SS86-5 + SX, Brevibacillus laterosporus strain ATCC64 + SX, Brevibacillus laterosporus strain BPM3 + SX, Brevibacillus laterosporus strain G4 + SX, Brevibacillus laterosporus strain NCIMB 41419 + SX, Brevibacillus laterosporus strain NRS1111 + SX,Brevibacillus laterosporus strain NRS1645 + SX, Brevibacillus laterosporus strain NRS1647 + SX, Burkholderia cepacia type Wisconsin strain J82 + SX, Burkholderia cepacia type Wisconsin strain M54 + SX, Burkholderia cepacia type BA-7 + SX, Burkholderia rhinogensis strain A396 + SX, Cameronia spp. + SX, Candida oleophila strain O + SX, Candida saitoana + SX, Candida spp. + SX, Chaetomium cupreum + SX, Chitwoodiella ovofilamenta + SX, Chromobacterium subtsugae strain PRAA4-1T + SX, Cladosporium cladosporioides strain H39 + SX, Conidiobolus obscurus + SX, Coniothyrium minitans strain CGMCC8325 + SX, Coniothyrium minitans strain CGMCC8325 + SX, Coniothyrium minitans strain CON / M / 91-08 + SX, Contortylenchus spp. + SX, Cryptococcus albidus + SX, Culicimermis spp. + SX, Dactyllela ellipsospora + SX, Dactylaria thaumasia + SX, Delftia acidovorans strain RAY209 + SX, Dilophosphora alopecuri + SX, Diplotriaena spp. + SX, Empidomermis spp. + SX, Entomophthora virulenta + SX,Erwinia carotovora subsp. carotovora strain CGE234M403 + SX, Filipjevimermis leipsandra + SX, Fusarium oxysporum strain Fo47 + SX, Fusarium oxysporum strain RS-21 + SX, Fusarium oxysporum strain RS-25 + SX, Fusariumproliferatum + SX, Gastromermis spp. + SX, Gliocladium catenulatum strain J1446 + SX, gluconacetobacter diazotrophicus + SX, Gongylonema spp. + SX, Gynopoecilia pseudovipara + SX, Harpin protein + SX, Heterorhabditis bacteriophora + SX, Heterorhabditis baujardi + SX, Heterorhabditis heliothidis + SX, Heterorhabditis indica + SX, Heterorhabditis marelatus + SX, Heterorhabditis megidis + SX, Heterorhabditis zealandica + SX, Hexamermis spp. + SX, Hirsutella minnesotensis + SX, Hirsutella rhossiliensis + SX, Hirsutella thompsonii + SX, Hydromermis spp. + SX, Isaria fumosorosea + SX, Isomermis spp. + SX, Lactobacillus acidophilus + SX, Lactobacillus brevis + SX, Lactobacillus plantarum + SX, Lactobacillus spp. + SX, Lagenidium giganteum + SX, Lecanicillium lecanii KV01 + SX,Conidia of Lecanicillium lecanii strain DAOM198499 + SX, Lecanicillium lecanii conidia of strain DAOM216596 + SX, Lecanicillium muscarium strain Ve6 + SX, Limnomermis spp. + SX, Lysobacter antibioticus strain 13-1 + SX, Lysobacter enzymogenes strain C3 + SX, Maupasina weissi + SX, Mermis nigrescens + SX, Mesomermis spp. + SX, Metarhizium anisopliae strain F52 + SX, Metarhizium anisopliae var. acridum + SX, Metarhizium anisopliae var. anisopliae BIPESCO 5 / F52 + SX, Metarhiziu m flavoviride + SX, Metschnikowia fructicola strain NRRLY-30752 + SX, Microsphaeropsis ochracea + SX, Monacrosporium phymatopagum + SX, Mucor hiemalis + SX, Muscodor albus strain 620 + SX, Muscodor albus strain QST 20799 + SX, Muscodor albus strain SA13 + SX, Muscodor roseus strain A3-5 + SX, Myrothecium verrucaria strain AARC-0255 + SX, Neomesomermis spp. + SX, Neoparasitylenchus rugulosi + SX, Nomuraea strain CG128 + SX, Nomuraea strain GU87401 + SX, Nomuraea strain SA86101 + SX,Nomuraea strain SR86151 + SX, Nomuraea strain VA9101 + SX, Nosema locustae + SX, Octomyomermis spp. + SX, Ophiostoma piliferum strain D97 + SX, Isaria fumosorosea Apopka strain 97 + SX, Paecilomyces lilacinus strain 251 + SX, Paecilomyces tenuipes strain T1 + SX, Paecilomyces variotii strain Q-09 + SX, Paenibacillus alvei strain 2771 + SX, Paenibacillus alvei strain 46C3 + SX, Paenibacillus alvei strain III2E + SX, Paenibacillus alvei strain III3DT-1A + SX, Paenibacillus alvei strain T36 + SX, Paenibacillus macerans + SX, Paenibacillus polymyxa strain AC-1 + SX, Paenibacillus polymyxa strain BS-0105 + SX, Paenibacillus popilliae + SX, Pandora delphacis + SX, Pantoea agglomerans strain E325 + SX, Pantoea vagans strain C9-1 + SX, Parasitaphelenchus spp. + SX, Parasitorhabditis spp. + SX, Parasitelenchus spp. + SX, Pasteuria nishizawae strain Pn1 + SX, Pasteuria penetrans + SX, Pasteuria ramose + SX, Pasteuria usgae + SX, Pectobacterium carotovorum + SX,Penicillium bilaiae strain ATCC22348 + SX, Penicillium citrinum strain VFI-51 + SX, Penicillium vermiculatum + SX, Perutilimermis culicis + SX, Pasteuria thornei + SX, Phasmarhabditis hermaphrodita + SX, phlebiopsis gigantea strain VRA1992 + SX, Physaloptera spp. + SX, phytophthora palmivora + SX, Pichia anomala strain WRL-076 + SX, pichia guilliermondii strain Z1 + SX, pichia guilliermondii strain Z8 + SX, Pochonia chlamydosporia isolate strain PC10 + SX, Pochonia chlamydosporia + SX, Protrellatus spp. + SX, Pseudomonas aeruginosa strain PN1 + SX, Pseudomonas aeruginosa strain WS-1 + SX, Pseudomonas aureofaciens strain TX-1 + SX, Pseudomonas cepacia type Wisconsin strain J82 + SX, Pseudomonas cepacia type Wisconsin strain M54 + SX, Pseudomonas chlororaphis strain 63-28 + SX, Pseudomonas chlororaphis strain AFS009 + SX, Pseudomonas chlororaphis strain MA342 + SX, pseudomonas fluorescens strain 1629RS + SX, pseudomonas fluorescens strain A506 + SX,pseudomonas fluorescens strain CL145A + SX, Pseudomonas fluorescens strain G7090 + SX, Pseudomonas fluorescens biover B strain XJ3 + SX, Pseudomonas fluorescens biover B strain XS18 + SX, Pseudomonas fluorescens biover A strain LRS12 + SX, Pseudomonas proradix + SX, Pseudomonas putida + SX, Pseudomonas reactans + SX, Pseudomonas resinovorans + SX, Pseudomonas rhodesiae strain HAI-0804 + SX, Pseudomonas sp. strain CAB-02 + SX, Pseudomonas syringae strain 742RS + SX, Pseudomonas syringae strain MA-4 + SX, Pseudozyma flocculosa strain PF-A22UL + SX, Pterygodermatites spp. + SX, puccinia thlaspeos strain woad + SX, Purpureocillium lilacinum + SX, Pythium oligandrum strain DV74 + SX, Pythium oligandrum strain M1 + SX, Rhodococcus globerulus strain AQ719 + SX, Romanomermis spp. + SX, saccharomyces cerevisiae strain LAS02 + SX, saccharomyces cerevisiae strain DDSF623 + SX, sclerotinia minor strain IMI34414 + SX, Serratia entomophila + SX, Serratia marcescens strain 35 + SX,Serratia marcescens strain SRM + SX, Seuratum cadarachense + SX, Sphaerulariopsis spp. + SX, Spirura guianensis + SX, Sporothrix insectorum + SX, Steinernema bibionis + SX, Steinernema carpocapsae + SX, Steinernema feltiae + SX, Steinernema glaseri + SX, Steinernema kraussei + SX, Steinernema riobrave + SX, Steinernema scapterisci + SX, Steinernema scarabaei + SX, Steinernema siamkayai + SX, Steinernema thailandse + SX, Steinernema spp. + SX, Strelkovimermis peterseni + SX, Streptomyces acidiscabies strain RL-110T + SX, Streptomyces candidus strain Y21007-2 + SX, Streptomyces colombiensis + SX, Streptomyces galbus strain QST6047 + SX, Streptomyces goshikiensis + SX, Streptomyces griseoviridis strain K61 + SX, Streptomyces lavendulae + SX, Streptomyces lydicus strain WYCD108US + SX, Streptomyces lydicus strain WYEC108 + SX, Streptomyces microflavus strain AQ6121 + SX, Streptomyces prasinus + SX, Streptomyces rimosus + SX, Streptomyces saraceticus + SX,Streptomyces sp. strain NRRL No.B-30145 + SX, Streptomyces sp. strain WYE20 + SX, Streptomyces sp. strain WYE 324 + SX, Streptomyces venezuelae + SX, Subulura spp. + SX, Sulphuretylenchus elongatus + SX, Talaromyces flavus strain SAY-Y-94-01 + SX, Talaromyces flavus strain V117b + SX, Tetrameres spp. + SX, Thelohania solenopsis + SX, Thiobacillus spp. + SX, Trichoderma album + SX, Trichoderma asperelloides strain JM41R + SX, Trichoderma asperellum strain ICC012 + SX, Trichoderma asperellum T25 + SX, Trichoderma asperellum strain T34 + SX, Trichoderma asperellum strain SKT-1 + SX, Trichoderma asperellum strain TV1 + SX, Trichoderma atroviride strain CNCM 1-1237 + SX, Trichoderma atroviride strain LC52 + SX, Trichoderma atroviride strain IMI 206040 + SX, Trichoderma atroviride strain SC1 + SX, Trichoderma atroviride strain SKT-1 + SX, Trichoderma atroviride strain T11 + SX, Trichoderma gamsii strain ICC080 + SX, Trichoderma harzianum strain 21 + SX,Trichoderma harzianum strain DB 104 + SX, Trichoderma harzianum strain DSM 14944 + SX, Trichoderma harzianum strain ESALQ-1303 + SX, Trichoderma harzianum strain ESALQ-1306 + SX, Trichoderma harzianum strain IIHR-Th-2 + SX, Trichoderma harzianum strain ITEM908 + SX, Trichoderma harzianum strain kd + SX, Trichoderma harzianum strain MO1 + SX, Trichoderma harzianum strain SF + SX, Trichoderma harzianum strain T22 + SX, Trichoderma harzianum strain T39 + SX, Trichoderma harzianum strain T78 + SX, Trichoderma harzianum strain TH35 + SX, Trichoderma harzianum rifai + SX, Trichoderma harzianum strain K2 + SX, Trichoderma harzianum strain F11Bab + SX, Trichoderma harzianum strain RR17Bc + SX, Trichoderma koningii + SX, Trichoderma lignorum + SX, Trichoderma polysporum strain IMI206039 + SX, Trichoderma spp. + SX, trichoderma stromaticum + SX, Trichoderma virens strain G-41 + SX, Trichoderma virens strain GL-21, formaly Gliocladium virens GL-21 + SX, Trichoderma viride + SX,Trichoderma viride strain K5 + SX, Trichoderma viride strain NRRL B-S0S20 + SX, Tsukamurella paurometabola + SX, Typhula phacorrhiza strain 94671 + SX, Ulocladium oudemansii strain HRU3 + SX, Vairimorpha spp. strain Q-09 + SX, Variovorax paradoxus strain GF4526 + SX, Verticillium alboatrum strain WCS850 + SX, Verticillium chlamydosporium + SX, Verticillium dahliae + SX, Verticillium lecani strain NCIM1312 + SX, Virgibacillus pantothenticus strain ATCC14576 + SX, Virgibacillus pantothenticus strain DSM491 + SX, Wolbachia pipientis + SX, Xanthomonas campestris pv poae + SX, Xanthomonas campestris + SX, Xenorhabdus luminescens + SX, Xenorhabdus nematophila + SX, Zoophtora radicans + SX, Acaulospora spp. + SX, Ambispora spp. + SX, Archaeospora spp. + SX, Claroideoglomus spp. + SX, Claroideoglomus etunicatum + SX, Claroideoglomus claroideum + SX, Diversispora spp. + SX, Entrophospora spp. + SX, Funneliformis spp. + SX, Funneliformis mosseae + SX, Geosiphon spp. + SX, Gigaspora spp. + SX,Gigaspora margarita + SX, Gigaspora rosea + SX, Glomus spp. + SX, Glomus aggregatum + SX, Glomus deserticola + SX, Glomus monosporum + SX, Pacispora spp. + SX, Paraglomus spp. + SX, Paraglomus brasilianum + SX, Racocetra spp. + SX, Rhizophagus spp. + SX, Rhizophagus clarus + SX, Rhizophagus intraradices + SX, Rhizophagus irregularis + SX, Rhizophagus irregularis strain DAOM 197198 + SX, Scutellospora spp. + SX, Azorhizobium spp. + SX, Azorhizobium caulinodans + SX, Azospirillum amazonense + SX, Azospirillum brasilense + SX, Azospirillum brasilense strain XOH + SX, Azospirillum brasilense strain Ab-V5 + SX, Azospirillum brasilense strain Ab-V6 + SX, Azospirillum caulinodans + SX, Azospirillum halopraeferens + SX, Azospirillum irakense + SX, Azospirillum lipoferum + SX, Bradyrhizobium spp. + SX, Bradyrhizobium elkanii + SX, Bradyrhizobium elkanii strain SEMIA 587 + SX, Bradyrhizobium elkanii strain SEMIA 5019 + SX, Bradyrhizobium japonicum + SX,Bradyrhizobium japonicum strain TA-11 + SX, Bradyrhizobium japonicum strain USDA 110 + SX, Bradyrhizobium liaoningense + SX, Bradyrhizobium lupini + SX, Bradyrhizobium spp. (Arachis) + SX, Bradyrhizobium spp. (Vigna) + SX, Delftia acidovorans + SX, Delftia acidovorans strain RAY209 + SX, Metylobacterium spp. + SX, Mesorhizobium ciceri + SX, Mesorhizobium huakii + SX, Mesorhizobium loti + SX, Mesorhizobium spp. + SX, Rhizobium etli + SX, Rhizobium galegae + SX, Rhizobium leguminosarum bv. Phaseoli + SX, Rhizobium leguminosarum bv. Trifolii + SX, Rhizobium leguminosarum bv. Viciae + SX, Rhizobium trifolii + SX, Rhizobium tropici + SX, Sinorhizobium fredii + SX, Sinorhizobium meliloti + SX, Arkansas Fungus 18 + SX, Beauveria bassiana strain ATP02 + SX, Beauveria bassiana strain CG716 + SX, Candida oleophila isolate I-182 + SX, Colletotrichum gloeosporioides + SX, Cryptococcus flavescens + SX, Gliocladium roseum + SX, Glomus etunicatum + SX, Glomus iranicum + SX, Laccaria bicolor + SX,Laccaria laccata + SX, Lecanicillium muscarium strain 1 / 1 + SX, Metarhizium anisopliae var. acridum isolate IMI 330189 + SX, Isaria fumosorosea strain FE9901 + SX, Phlebiopsis + SX, Phoma macrostroma strain94-44B + SX, Acaulospora longula + SX, Ambispora leptoticha + SX, cell walls of Saccharomyces cerevisiae strain LAS117 + SX, Claroideoglomus claroideum + SX, Claroideoglomus luteum + SX, Pisolithus tinctorius + SX, Rhizopogon amylopogon + SX, Rhizopogon fulvigleba + SX, Rhizopogon luteolus + SX, Rhizopogon villosullus + SX, Scleroderma cepa + SX, Scleroderma citrinum + SX, Suillus granulatus + SX, Suillus punctatapies + SX, Trichoderma asperellum strain kd + SX, Trichoderma atroviride strain LU132 + SX, Trichoderma atroviride strain 77B + SX, Trichoderma atroviride strain K4 + SX, Trichoderma atroviride strain WW10TC4 + SX, Trichoderma harmatum strain TH382 + SX, Trichoderma lignorum strain TL-0601 + SX, Trichoderma saturnisporium strain PBP-TH-001 + SX,Tsukamurella paurometabola strain C-924 + SX, Gluconactobacter diazotrophicus strain IMI504853 + SX, Clonostachys rosea strain IDAC 040913-01 + SX, Bacillus cereus Bromelia strain NRRL B-50766 + SX, Bacillus cereus Peumo strain NRRL B-50767 + SX, Bacillus thuringiensis Anemophyla strain NRRL B-50765 + SX, Trichoderma harzianuna strain Gomorteka NRRL 67322 + SX, Bacillus licheniformis strain DSM17236 + SX, Bacillus licheniformis strain copihue NRRL B-67023 + SX, Trichoderma reesei + SX, Corynebacterium flavescens strain B2575 + SX, Chlorella + SX, Methylobacterium isolate ISO01 + SX, Methylobacterium isolate ISO02 (NRRL B-50930) + SX, Methylobacterium isolate ISO03 (NRRL B-50931) + SX, Methylobacterium isolate ISO04 (NRRL B-50932) + SX, Methylobacterium isolate ISO07 + SX, Methylobacterium isolate ISO09 (NRRL B-50937) + SX, Methylobacterium isolate ISO10 (NRRL B-50938) + SX, Methylobacterium isolate ISO11 (NRRL B- 50939) + SX, Klebsiella variicola 137 + SX,Adoxophyes orana granulovirus BV-0001 (GV strain BV-0001) + SX, Anticarsia gemmatalis multiple nucleocapsid nucleopolyhedrovirus (MNPV) + SX, Autographa californica MNPV + SX, Cydia pomonella granulosis virus V15 (GV strain V15) + SX, Cydia pomonella granulosis virus V22 (GV strain V22) + SX, Cryptophlebia leucotreta granulosis virus (GV) + SX, Cydia pomonella granulosis virus CP4 strain (Cydia pomonella GV strain CP4) + SX, Cydia pomonella granulosis virus R5 strain (Cydia pomonella GV strain R5) + SX, Dendrolimus punctatus cypovirus + SX, Helicoverpa armigera nucleopolyhedrovirus BV-0003 (Helicoverpa armigera NPV (nucleopolyhedrovirus) strain BV-0003) + SX, Helicoverpa zea nucleopolyhedrovirus (Helicoverpa zea NPV) + SX, Lymantria dispar nucleopolyhedrovirus (Lymantria dispar NPV) + SX, Mamestra brassicae nucleopolyhedrovirus (Mamestra brassicae NPV) + SX, Mamestra configurata nuclear polyhedrosis virus (Mamestra configurata NPV) + SX, Neodiprion abietis nuclear polyhedrosis virus (Neodiprion abietis NPV) + SX,Neodiprion lecontei nucleopolyhedrosis virus (NPV) + SX, Neodiprion sertifer nucleopolyhedrosis virus (NPV) + SX, Nosema locustae + SX, Orgyia pseudotsugata nucleopolyhedrosis virus (NPV) + SX, Pieris rapae granulosis virus (GV) + SX, Plodia interpunctella granulosis virus (GV) + SX, Spodoptera exigua nucleopolyhedrosis virus (MNPV) + SX, Spodoptera littoralis nucleopolyhedrosis virus (MNPV) + SX, Spodoptera litura nuclear polyhedrosis virus (NPV) + SX, BT crop protein Cry1Ab (BT crop protein Cry1Ab) + SX, BT crop protein Cry1Ac (BT crop protein Cry1Ac) + SX, BT crop protein Cry1Fa (BT crop protein Cry1Fa) + SX, BT crop protein Cry1A.105 (BT crop protein Cry1A.105) + SX, BT crop protein Cry2Ab (BT crop protein Cry2Ab) + SX, BT crop protein Vip3A (BT crop protein Vip3A) + SX, BT crop protein mCry3A (BT crop protein mCry3A) + SX, BT crop protein Cry3Ab (BT crop protein Cry3Ab) + SX, BT crop protein Cry3Bb (BT crop protein Cry3Bb) + SX, BT crop protein Cry34Ab1 / Cry35Ab1 (BT crop protein Cry34Ab1 / Cry35Ab1) + SX, chitin + SX,Colletochlorin B + SX, concanamycin A + SX, ryanodine + SX, cevadine + SX, veratridine + SX, pyrethrin I + SX, pyrethrin II + SX, cinerin I + SX, cinerin II + SX, jasmolin I + SX, jasmolin II + SX, oak leaves and bark of Quercus + SX, dried leaves of Dryopteris filix-mas + SX, extract of Artemisia absinthium + SX, Cassia nigricans extract (extract of Cassia nigricans) + SX, Clitoria ternatea extract (extract of clitoria ternatea) + SX, Comfrey extract (extract of Symphytum officinale) + SX, Chenopodium ambrosioides extract (extract of Chenopodium ambrosioides) + SX, Tansy extract (extract of Tanacetum vulgare) + SX, Urtica dioica extract (extract of Urtica dioica) + SX, Viscum album extract (extract of Viscum album) + SX, Chenopodium anthelminticum seed oil (oil of the seeds of Chenopodium anthelminticum) + SX, Quassia amara wood extract (wood extract of Quassia amara) + SX, Melaleuca alternifolia tea tree extract (extract of Melaleuca alternifolia) + SX, Reynoutria knotweed extract (extract of Reynoutria sachalinensis) + SX,Extract of the cotyledons of lupine plantlets (BLAD) + SX, garlic extract (Allium sativum extract) + SX, horsetail extract (Equisetum arvense extract) + SX, nasturtium extract (Tropaeol majus extract) + SX, neem extract (Azadirachta indica extract) + SX, Quillaja extract + SX, yellow mustard powder + SX, Schoenocaulon spp. seed extract + SX, Pyrethrum extract + SX, Gougerotin + SX, matrine + SX, ascaridole + SX, capsaicin + SX Deguelin + SX, nootkatone + SX, pellitorine + SX, piperine + SX, tabog extract (extract from Swinglea glutinosa) + SX, cytokinin + SX, N,N'-diformylurea + SX, salicylic acid + SX.

[0039] The ratio of this compound or the compound of the present invention to this component is not particularly limited, and examples thereof include a weight ratio (this compound or the compound of the present invention:this component) of 1000:1 to 1:1000, 500:1 to 1:500, 100:1 to 1:100, 50:1, 20:1, 10:1, 9:1, 8:1, 7:1, 6:1, 5:1, 4:1, 3:1, 2:1, 1:1, 1:2, 1:3, 1:4, 1:5, 1:6, 1:7, 1:8, 1:9, 1:10, 1:20, 1:50, and the like.

[0040] The present compound and the compound of the present invention are effective against harmful arthropods such as harmful insects and harmful mites, and harmful nematodes. Examples of harmful arthropods and harmful nematodes include the following.

[0041] Hemiptera: Small brown planthopper (Laodelphax striatellus), Brown planthopper (Nilaparvata lugens), White-backed planthopper (Sogatella furcifera), Corn planthopper (Peregrinus maidis), Yellow leafhopper (Javesella pellucida), Black horned planthopper (Perkinsiella saccharicida), Tagosodes orizicolus, Stenocranus pacificus and other Delphacidae; Green rice leafhopper (Nephotettix cincticeps), Taiwan green rice leafhopper (Nephotettix virescens), Black-striped green rice leafhopper (Nephotettix nigropictus), Lightning leafhopper (Recilia dorsalis), Tea green leafhopper (Empoasca Cicadellidae, such as the potato leafhopper (Empoasca fabae), the corn leafhopper (Dalbulus maidis), the white giant leafhopper (Cofana spectra), and Amrasca biguttula biguttula; Aphrophoridae, such as the European spittlebug (Philaenus spumarius); Cercopidae, such as Mahanarva posticata and Mahanarva fimbriolata;Black bean aphid (Aphis fabae), soybean aphid (Aphis glycines), cotton aphid (Aphis gossypii), European apple aphid (Aphis pomi), willow aphid (Aphis spiraecola), green peach aphid (Myzus persicae), strawberry aphid (Brachycaudus helichrysi), radish aphid (Brevicoryne brassicae), rosy apple aphid (Dysaphis plantaginea), false radish aphid (Lipaphis erysimi), tulip aphid (Macrosiphum euphorbiae), potato aphid (Aulacorthum solani), lettuce aphid (Nasonovia ribisnigri), wheat collar aphid (Rhopalosiphum padi), corn aphid (Rhopalosiphum maidis), citrus black aphid (Toxoptera citricida), peach butterbur aphid (Hyalopterus pruni), barnyard millet aphid (Melanaphis sacchari), Japanese black aphid (Tetraneura nigriabdominalis), cotton aphid (Ceratovacuna lanigera), apple aphid (Eriosoma lanigerum), English grain aphid (Sitobion avenae), etc. Aphididae; grape aphid (Daktulosphaira vitifoliae), pecan phylloxera (Phylloxera devastatrix), pecan leaf phylloxera (Phylloxera notabilis), southern pecan leaf phylloxera (Phylloxera Phylloxeridae, such as (Russelae);Adelgidae, such as the Japanese hemlock aphid (Adelges tsugae), the balsam woolly aphid (Adelges piceae), and the small brown aphid (Aphrastasia pectinatae); Scotinophara lurida, Scotinophara coarctata, Nezara antennata, Eysarcoris aeneus, Eysarcoris lewisi, Eysarcoris ventralis, Eysarcoris annamita, Halyomorpha halys, and Nezara Pentatomidae, such as the brown stink bug (Euschistus heros), the red-banded stink bug (Piezodorus guildinii), Oebalus pugnax, Dichelops melacanthus, and the spotted stink bug (Piezodorus hybneri); Cydnidae, such as the narrow-banded stink bug (Riptortus clavatus), the spider stink bug (Leptocorisa chinensis), and the narrow-banded stink bug (Leptocorisa acuta); Cletus punctiger, Leptoglossus Coreidae, such as Cavelerius saccharivorus, Togo hemipterus, and Blissus leucopterus; Lygaeidae, such as Cavelerius saccharivorus, Togo hemipterus, and Blissus leucopterus;Miridae (Miridae) such as the red-bearded green rice bug (Trigonotylus caelestialium), the red-striped rice bug (Stenotus rubrovittatus), the long-spined wheat rice bug (Stenodema calcarata), and the rusty rice bug (Lygus lineolaris); Aleyrodidae (Aleyrodidae) such as the greenhouse whitefly (Trialeurodes vaporariorum), the tobacco whitefly (Bemisia tabaci), the citrus whitefly (Dialeurodes citri), the citrus spine whitefly (Aleurocanthus spiniferus), the tea spine whitefly (Aleurocanthus camelliae), and the Japanese oak leaf butterflies (Pealius euryae); cyanophylli), red scale (Aonidiella aurantii), pear scale (Diaspidiotus perniciosus), mulberry scale (Pseudaulacaspis pentagona), Yanon scale (Unaspis yanonensis), false Yanon scale (Unaspis citri) and other scale insects (Diaspididae); Coccidae such as ruby ​​scale (Ceroplastes rubens); Margarodidae such as Icerya purchasi and yellow cotton scale (Icerya seychellarum);Pseudococcidae, such as the eggplant mealybug (Phenacoccus solani), the sable mealybug (Phenacoccus solenopsis), the wisteria mealybug (Planococcus kraunhiae), the mulberry mealybug (Pseudococcus comstocki), the citrus mealybug (Planococcus citri), the moth mealybug (Pseudococcus calceolariae), the long-legged mealybug (Pseudococcus longispinus), and the tuttlemey bug (Brevennia rehi); the citrus psyllid (Diaphorina citri), the citrus psyllid (Trioza erytreae), the pear psyllid (Cacopsylla pyrisuga), and the Chinese pear psyllid (Cacopsylla Psyllidae, such as the Japanese chinensis, the potato psyllid (Bactericera cockerelli), and the cacopsylla (Cacopsylla pyricola); Tingidae, such as the plane tree earworm (Corythucha ciliata), the goldenrod earworm (Corythucha marmorata), the Japanese pear earworm (Stephanitis nashi), and the azalea earworm (Stephanitis pyrioides); Cimicidae, such as the bedbug (Cimex lectularius) and the netted whitefly (Cimex hemipterus); Cicadidae, such as the Quesada gigas; Triatoma infestans, Triatoma rubrofasciata, and Triatoma Reduviidae, such as the Venezuelan assassin bug (Rhodonius prolixus);

[0042] Lepidoptera: Chilo suppressalis, Dark-headed stem borer, Chilo polychrysus, White stem borer, Scirpophaga innotata, Scirpophaga incertulas, Rupela albina, Rice leaf borer, Cnaphalocrocis medinalis, Marasmia patnalis, Rice casino borer, Marasmia exigua, Cotton borer, Notarcha derogata, European corn borer, Ostrinia furnacalis, European corn borer, Hellula undalis, Black-spotted corn borer, Herpetogramma luctuosale, Rice stalk moth, Nymphula Crambidae, such as the Japanese corn moth (Elasmopalpus lignosellus), the Indian meal moth (Plodia interpunctella), the Japanese two-spotted moth (Euzophera batangensis), and the Japanese striped moth (Cadra cautella);Common cutworm (Spodoptera litura), beet armyworm (Spodoptera exigua), armyworm (Mythimna separata), armyworm (Mamestra brassicae), rice armyworm (Sesamia inferens), white armyworm (Spodoptera mauritia), two-banded cutworm (Naranga aenescens), leaf fall armyworm (Spodoptera frugiperda), African armyworm (Spodoptera exempta), Spodoptera cosmioides, semi-tropical armyworm (Spodoptera eridania), red cutworm (Agrotis ipsilon), turnip cutworm (Agrotis segetum), red rice looper (Autographa nigrisigna), rice yellow looper (Plusia festucae), soybean Heliothis spp. such as the cotton bollworm (Chrysodeixis includens), Trichoplusia spp., and Heliothis spp. such as the false tobacco budworm (Heliothis virescens), Helicoverpa spp. such as the cotton bollworm (Helicoverpa armigera) and the corn earworm (Helicoverpa zea), Noctuidae such as the velvet bean caterpillar (Anticarsia gemmatalis), the cotton leafworm (Alabama argillacea), and the hop wine borer (Hydraecia immanis); Pieridae such as the cabbage white butterfly (Pieris rapae);Pear fruit moth (Grapholita molesta), plum fruit moth (Grapholita dimorpha), bean fruit moth (Leguminivora glycinivorella), adzuki bean pea moth (Matsumuraeses azukivora), apple smaller tortrix (Adoxophyes orana fasciata), tea smaller tortrix (Adoxophyes honmai), tea tortrix (Homona magnanima), green tea tortrix (Archips fuscocupreanus), codling moth (Cydia pomonella), citrus fruit borer (Tetramoera schistaceana), bean shoot borer (Epinotia aporema), citrus fruit borer (Citripestis sagittiferella), European grape wine moth (Lobesia Tortricidae such as Caloptilia theivora and Phyllonorycter ringoniella; Gracilariae such as Carposinidae; Leucoptera coffeella, Lyonetiidae such as Lyonetia clerkella, Lyonetia prunifoliella; Lymantria spp. such as Lymantria dispar, Euproctis spp. such as Euproctis pseudoconspersa; Plutella xylostella Plutellidae, such as Plutellidae (Plutella xylostella);Gelechiidae (Gelechiidae) such as the peach leaf moth (Anarsia lineatella), the potato leaf moth (Helcystogramma triannulella), the red bollworm moth (Pectinophora gossypiella), the potato tuber moth (Pthorimaea operculella), and the tomato leaf moth (Tuta absoluta); Arctiidae (Arctiidae) such as the American fall webworm (Hyphantria cunea); Castniidae (Castniidae) such as the giant sugarcane borer (Telchin licus); Cossidae (Cossidae) such as the small box moth (Cossus insularis); Geometridae (Geometridae) such as the mugwort geometrid (Ascotis selenaria); Parasa Limacodidae such as Stathmopodidae (Stathmopoda masinissa) and the like; Sphingidae such as Acherontia lachesis (Sphingidae); Sesiidae such as Nokona feralis (Nokona feralis), Synanthedon hector (Synanthedon tenuis) and the like; Hesperiidae such as Parnara guttata (Parnara guttata); Tineidae such as Tinea translucens (Tineola bisselliella) and the like.

[0043] Thysanoptera: Thripidae such as Frankliniella occidentalis, Thrips palmi, Scirtothrips dorsalis, Thrips tabaci, Frankliniella intonsa, Stenchaetothrips biformis, Echinothrips americanus, and Scirtothrips perseae; Phlaeothripidae such as Haplothrips aculeatus.

[0044] Diptera: Anthomyiidae such as Delia platura, Delia antiqua, and Pegomya cunicularia; Ulidiidae such as Tetanops myopaeformis; Agromyzidae such as Agromyza oryzae, Liriomyza sativae, Liriomyza trifolii, and Chromatomyia horticola; Chloropidae such as Chlorops oryzae; Bactrocera Tephritidae, such as the Oriental fruit fly (Bactrocera dorsalis), the eggplant fly (Bactrocera latifrons), the olive fruit fly (Bactrocera oleae), the Queensland fruit fly (Bactrocera tryoni), the Mediterranean fruit fly (Ceratitis capitata), the apple maggot (Rhagoletis pomonella), and the cherry fruit fly (Rhacochlaena japonica); Ephydridae, such as the rice leafminer (Hydrellia griseola), the Asian rice leafminer (Hydrellia philippina), and the rice leafminer (Hydrellia sasakii); Drosophila suzukii Drosophilidae, such as Drosophila melanogaster (Drosophila suzukii) and Drosophila melanogaster; Phoridae, such as Megaselia spiracularis; Psychodidae, such as Clogmia albipunctata;Sciaridae (Sciaridae) such as Bradysia difformis and Bradysia odoriphaga; Cecidomyiidae (Cecidomyiidae) such as Mayetiola destructor and Orseolia oryzae; Diopsidae (Diopsis macrophthalma); Glossinidae (Tsetse flies) such as Glossina palpalis and Glossina morsitans; Simuliidae (Simuliidae) such as Simulium japonicum and Simulium damnosum; Phlebotominae (Phlebotominae); Tipula aino (Craned fly), Tipula oleracea (Common crane fly), and Tipula Tipulidae such as Culex pipiens pallens, Culex tritaeniorhynchus, Culex pipiens f. molestus, Culex quinquefasciatus, Culex pipiens pipiens, Culex vishnui, Aedes albopictus, Aedes aegypti, Anopheles sinensis, Anopheles gambiae, Anopheles stephensi, Anopheles coluzzii, Anopheles albimanus, Anopheles sundaicus, Anopheles mosquito family (Culicidae) such as arabiensis, Anopheles funestus, Anopheles darlingi, Anopheles farauti, Anopheles minimus;Simulidae (Family Simuliidae) such as Prosimulium yezoensis and Simulium ornatum; Tabanidae (Family Tabanus trigonus) and other such flies; Muscidae (Family Musca domestica), Muscina stabulans, Stomoxys calcitrans, Haematobia irritans and other such flies; Calliphoridae (Family Sarcophagidae); Chironomidae (Family Chironomidae) such as Chironomus plumosus, Chironomus yoshimatsui, Glyptotendipes tokunagai and other such flies; Fannidae (Family Fannidae);

[0045] Coleoptera: Diabrotica spp. (e.g., Western corn rootworm (Diabrotica virgifera virgifera), Southern corn rootworm (Diabrotica undecimpunctata howardi), Northern corn rootworm (Diabrotica barberi), Mexican corn rootworm (Diabrotica virgifera zeae), Banded cucumber beetle (Diabrotica balteata), Cucumber beetle (Diabrotica speciosa), etc.), Bean leaf beetle (Cerotoma trifurcata), Red-necked leaf beetle (Oulema melanopus), Cucumber beetle (Aulacophora femoralis), Striped flea beetle (Phyllotreta striolata), Cabbage leaf beetle (Phyllotreta cruciferae), Western black leaf beetle (Phyllotreta pusilla, cabbage stem beetle (Psylliodes chrysocephala), hop beetle (Psylliodes punctulata), Colorado potato beetle (Leptinotarsa ​​decemlineata), rice leaf beetle (Oulema oryzae), grape colaspis (Colaspis brunnea), corn beetle (Chaetocnema pulicaria), sweet potato leaf beetle (Chaetocnema confinis), potato beetle (Epitrix cucumeris), rice spur beetle (Dicladispa armigera), southern corn leaf beetle (Myochrous denticollis), four-spotted tortoise beetle (Laccoptera quadrimaculata), tobacco flea beetle (Epitrix hirtipennis), radish leaf beetle (Phaedon Chrysomelidae, such as the two-striped leaf beetle (Medythia nigrobilineata);Carabidae beetles such as the seed corn beetle (Stenolophus lecontei) and the slender seed corn beetle (Clivina impressifrons); Phyllophaga spp. such as the cuprea beetle (Anomala cuprea), the rufocuprea beetle (Anomala rufocuprea), the green beetle (Anomala albopilosa), the Japanese beetle (Popillia japonica), the long-legged beetle (Heptophylla picea), the European chafer (Rhizotrogus majalis), the black marsh beetle (Tomarus gibbosus), the black beetle (Holotrichia spp.), and the June beetle (Phyllophaga crinita); Diloboderus spp. such as Diloboderus abderus. Scarabaeidae (Scarabaeidae) such as Araecerus coffeae (Boll weevil); Anthriibidae (Anthriibidae) such as Cylas formicarius (Sweet potato weevil); Bruchidae (Brachiidae) such as Zabrotes subfasciatus (Brazilian bean weevil); Scolytidae (Scolytidae) such as Tomicus piniperda (Pine bark beetle), Hypothenemus hampei (Coffee berry borer);Potato weevil (Euscepes postfasciatus), alfalfa weevil (Hypera postica), maize weevil (Sitophilus zeamais), rice weevil (Sitophilus oryzae), granaria weevil (Sitophilus granarius), rice weevil (Echinocnemus squameus), rice water weevil (Lissorhoptrus oryzophilus), white grain weevil (Rhabdoscelus lineaticollis), boll weevil (Anthonomus grandis), grass band weevil (Sphenophorus venatus), southern cornbill bug (Sphenophorus callosus), soybean stalk weevil (Sternechus subsignatus), sugarcane weevil (Sphenophorus levis), rust gourd weevil (Scepticus The Aracanthus spp. (Aracanthus spp.) such as Aracanthus griseus, Scepticus uniformis, Aracanthus mourei, and the cotton root borer (Eutinobothrus brasiliensis) are also included in the Curculionidae family; the Tenebrionidae (Tenebrionidae) such as Tribolium castaneum, Tribolium confusum, and Alphitobius diaperinus are also included in the Coccinellidae family; the Flat-headed Ladybird (Lyctus brunneus), the Rhizopertha dominica); Ptinidae; Cerambycidae, such as Anoplophora malasiaca, Migdolus fryanus, and Aromia bungii;Elateridae beetles such as the Okinawan wireworm beetle (Melanotus okinawensis), the brown-headed wireworm beetle (Agriotes fuscicollis), the comb beetle (Melanotus legatus), the foot-striped wireworm beetle (Anchastus spp.), the Conoderus spp., the Ctenicera spp., the Limonius spp., and the Aeolus spp.; Staphylinidae beetles such as the blue-leaf rove beetle (Paederus fuscipes); the small-leaved weevils (Anthrenus verbasci) and the white-striped weevils (Dermestes Dermestidae such as Trogoderma granarium (Trogoderma maculates) and the like; Anobiidae such as Lasioderma serricorne (tobacco beetle) and Stegobium paniceum (Anobiidae); Laemophloeidae such as Cryptolestes ferrugineus (Laemophloeidae); Silvanidae such as Oryzaephilus surinamensis (Silvanidae); Nitidulidae such as Brassicogethes aeneus (Blossom beetle).

[0046] Orthoptera: Migratory locust (Locusta migratoria), Moroccan locust (Dociostaurus maroccanus), Australian locust (Chortoicetes terminifera), Red locust (Nomadacris septemfasciata), Brown locust (Locustana pardalina), Tree locust (Anacridium melanorhodon), Italian locust (Calliptamus italicus), Differential grasshopper (Melanoplus differentialis), Two-striped grasshopper (Melanoplus bivittatus), Migratory grasshopper (Melanoplus sanguinipes), Red-legged grasshopper (Melanoplus femurrubrum), Clear-winged grasshopper (Camnula pellucida), Desert grasshopper (Schistocerca The grasshoppers (Acrididae) include the common locust (Oxya gregaria), yellow-winged locust (Gastrimargus musicus), sparse-throated locust (Austracris guttulosa), oriental grasshopper (Oxya yezoensis), long-winged locust (Oxya japonica), and Taiwan grasshopper (Patanga succincta); the grasshoppers (Gryllotalpidae) include the common house cricket (Gryllotalpa orientalis); the crickets (Gryllidae) include the European house cricket (Acheta domestica) and the field cricket (Teleogryllus emma); and the katydids (Tettigoniidae) include the Mormon cricket (Anabrus simplex).

[0047] Hymenoptera: Tenthredinidae such as Athalia rosae and Athalia japonica; Solenopsis spp. such as Solenopsis invicta and Solenopsis geminata, Atta spp. such as Atta capiguara, Acromyrmex spp., Paraponera clavata, Ochetellus glaber, Monomorium pharaonis, Linepithema humile, Formica japonica, Pristomyrmex punctutus, Pheidole Camponotus spp. such as Camponotus noda, Pheidole megacephala, Camponotus japonicus, Camponotus obscuripes, Pogonomyrmex spp. such as Pogonomyrmex occidentalis, Wasmania spp. such as Wasmania auropunctata, Formicidae such as Anoplolepis gracilipes; Vespa mandarinia, Vespa simillima, Vespa analis, Vespa Vespidae, such as Polistes velutina and Polistes jokahamae; Siricidae, such as Urocerus gigas; and Bethylidae.

[0048] Blattodea: Ectobiidae, such as the German cockroach (Blattella germanica); Blattidae, such as the American cockroach (Periplaneta fuliginosa), the American cockroach (Periplaneta americana), the American cockroach (Periplaneta australasiae), the brown cockroach (Periplaneta brunnea), and the Asian cockroach (Blatta orientalis); Reticulitermes speratus, Coptotermes formosanus, Incisitermes minor, Cryptotermes domesticus, Odontotermes formosanus, and Neotermes Termites of the family Termitidae, such as the Satsuma termite (Glyptotermes satsumensis), Nakajima termite (Glyptotermes nakajimai), Katan termite (Glyptotermes fuscus), Hodotermopsis sjostedti, Koshu termite (Coptotermes guangzhouensis), Amami termite (Reticulitermes amamianus), Miyatake termite (Reticulitermes miyatakei), Formosan termite (Reticulitermes kanmonensis), Takasago termite (Nasutitermes takasagoensis), Snocapritermes nitobei, Sinocapritermes mushae, and Cornitermes cumulans.

[0049] Order Siphonaptera: Family Pulicidae such as human flea (Pulex irritans), cat flea (Ctenocephalides felis), dog flea (Ctenocephalides canis), rat flea (Xenopsylla cheopis), chicken flea (Echidnophaga gallinacea), etc.; Family Hectopsyllidae such as sand flea (Tunga penetrans); Family Ceratophyllidae such as European rat flea (Nosopsyllus fasciatus).

[0050] Psocodae: Pediculidae, such as head louse (Pediculus humanus capitis); Pthiridae, such as pubic louse (Pthirus pubis); Haematopinidae, such as cow louse (Haematopinus eurysternus) and pig louse (Haematopinus suis); Linognathidae, such as cow louse (Linognathus vituli), sheep trunk louse (Linognathus ovillus), and woolly cow louse (Solenopotes capillatus); Bovicola bovis, sheep louse (Bovicola ovis), Bovicola breviceps, Damalinia Bovicoliidae, such as Trichodectes canis and Felicola subrostratus; Menoponidae, such as Menopon gallinae, Menacanthus stramineus, and Trinoton spp.; Trimenoponidae, such as Cummingsia spp.; Trogiidae, such as Trogium pulsatorium; Liposcelis corrodens and Liposcelis Liposcelidae or Liposcelididae, such as Liposcelis bostrychophila, Liposcelis pearmani, and Liposcelis entomophila.

[0051] Thysanura: Family Lepismatidae, including the Japanese silverfish (Ctenolepisma villosa) and the European silverfish (Lepisma saccharina).

[0052] Acari: Tetranychidae such as Tetranychus urticae, Tetranychus kanzawai, Tetranychus evansi, Panonychus citri, Panonychus ulmi, Oligonychus spp.; Aculops pelekassi, Aculops citri, Aculops lycopersici, Calacarus carinatus, Acaphylla theavagrans, Eriophyes chibaensis, Aculops spp. Eriophyidae such as Aceria diospyri, Aceria tosichella, and Shevtchenkella sp.; Tarsonemidae such as Polyphagotarsonemus latus; Tenuipalpidae such as Brevipalpus phoenicis; Tuckerellidae;Haemaphysalis longicornis, Haemaphysalis flava, Haemaphysalis japonica, Haemaphysalis campanulata, Dermacentor variabilis, Dermacentor taiwanensis, Rocky Mountain wood tick (Dermacentor andersoni), Dermacentor reticulatus, Ixodes ovatus, Ixodes persulcatus, Black-legged tick (Ixodes scapularis), Western black-legged tick (Ixodes pacificus), Ixodes holocyclus, Ixodes ricinus, Lone star tick (Amblyomma Ixodidae ticks such as Amblyomma americanum, Amblyomma maculatum, Rhipicephalus microplus, Rhipicephalus annulatus, Rhipicephalus sanguineus, Rhipicephalus appendiculatus, and Rhipicephalus decoloratus; Argasidae ticks such as Argas persicus, Ornithodoros hermsi, and Ornithodoros turicata; Acaridae ticks such as Tyrophagus putrescentiae and Tyrophagus similis; Dermatophagoides farinae and Dermatophagoides pteronyssinus. Pyroglyphidae, such as Pteronyssinus;Cheyletidae such as Cheyletus eruditus, Cheyletus malaccensis, Chelacaropsis moorei, and Cheyletiella yasguri; Psoroptidae such as Psoroptes ovis, Psoroptes equi, Knemidocoptes mutans, Otodectes cynotis, and Chorioptes spp.; Notoedres cati, Notoedres muris, and Sarcoptes Sarcoptidae such as Listrophorus scabiei; Listrophoridae such as Listrophorus gibbus; Dermanyssidae such as Dermanyssus gallinae; Macronyssidae such as Ornithonyssus sylviarum and Ornithonyssus bacoti; Varroa destructor such as Varroa jacobsoni; Demodex canis and Demodex cati; Leptotrombidium akamushi and Leptotrombidium Trombiculidae, such as Leptotrombidium scutellare, Leptotrombidium pallidum, and Leptotrombidium scutellare.

[0053] Araneae: Eutichuridae, such as Cheiracanthium japonicum; Theridiidae, such as Latrodectus hasseltii. Polydesmida: Paradoxosomatidae, such as Oxidus gracilis and Nedyopus tambanus. Isopoda: Armadillidiidae, such as Armadillidium vulgare. Chilopoda: Scutigeridae such as Thereuonema hilgendorfi; Scolopendridae such as Scolopendra subspinipes; Ethopolyidae such as Bothropolys rugosus.

[0054] Nematoda: Aphelenchoididae, such as the rice root-lesion nematode (Aphelenchoides besseyi); Pratylenchidae, such as the southern root-lesion nematode (Pratylenchus coffeae), Pratylenchus brachyurus, the wheat root-lesion nematode (Pratylenchus neglectus), and Radopholus similis; Java root-knot nematode (Meloidogyne javanica), sweet potato root-knot nematode (Meloidogyne incognita), guava root-knot nematodes (Meloidogyne enterolobii), northern root-knot nematode (Meloidogyne hapla), soybean cyst nematode (Heterodera glycines), potato cyst nematode (Globodera Heteroderidae (Heteroderidae) such as Globodera pallida (potato white cyst nematode), Meloidogyne chitwoodi (Colombian root-knot nematode); Hoplolaimidae (Hoplolaimidae) such as Rotylenchulus reniformis; Anguinidae (Anguinidae) such as Nothotylenchus acris (strawberry root nematode) and Ditylenchus dipsaci (sea stalk nematode); Tylenchulidae (Tylenchulus semipenetrans) and other citrus root nematodes; Longidoridae (Longidoridae) such as Xiphinema index (grape nematode); Trichodoridae; Bursaphelenchus Parasitaphelenchidae such as Trichuris suis, Trichuris ovis, and Trichuris discolor;Capillariidae, such as Capillaria suis, Calodium hepaticum, Paracapillaria philippinensis, Pearsonema plica, and Pearsibena spp.; Trichinellidae, such as Trichinella spiralis and Trichinella britovi; Strongyloides papillosus, Strongyloides planiceps, Strongyloides ransomi, and Strongyloides stercoralis; Strongyloides edentatus, Strongylus vulgaris, Triodontophorus spp., Oesophagodontus spp., and Cylicostephanus Strongylidae such as spp.; Chabertiidae such as Oesophagostomum dentatum, Oesophagostomum radiatum, and Chabertia ovina; Stephanuridae such as Stephanurus dentatus; Dioctophymatidae such as Dioctophyme renale; Brazilian hookworm (Ancylostoma braziliense), dog hookworm (Ancylostoma caninum), Duodenale hookworm (Ancylostoma duodenale), Uncinaria stenocephala, cattle hookworm (Bunostomum phlebotomum), sheep hookworm (Bunostomum trigonocephalum), Globocephalus Ancylostomatidae, such as Syngamus skrjabinomorpha, Syngamus trachea, and Cyathostoma bronchialis;Metastrongylidae such as Metastrongylus apri; Dictyocaulidae such as Dictyocaulus filaria and Dictyocaulus viviparus; Crenosomatidae such as Crenosoma aerophila and Crenosoma vulpis; Angiostrongylidae such as Angiostrongylus cantonensis, Angiostrongylus vasorum, and Aelurostrongylus abstrusus; Filaroididae such as Filaroides hirthi and Filaroides osleri; Trichostrongylidae such as Trichostrongylus axei, Trichostrongylus colubriformis, and Obeliscoides cuniculi; Haemonchus Haemonchidae, such as Hyostrongylus rubidus, Mecistocirrus digitatus, and Ostertagia ostertagi; Molineidae, such as Nematodirus filicollis and Nematodirus spathiger; Oxyuridae, such as Enterobius vermicularis, Oxyuris equi, and Passalurus ambiguus; Heterakidae, such as Heterakis gallinarum; Ascarididae, such as Ascaris lumbricoides, Ascaris suum, and Parascaris equorum; Toxocara canis, Toxocara cati, and Toxocara Toxocaridae, such as Anisakis spp.; Anisakidae, such as Anisakis spp.;Ascaridiidae such as chicken roundworm (Ascaridia galli); Gnathostomatidae such as Gnathostoma doloresi; Physalopteridae such as Physaloptera felidis and Physaloptera rara; Thelaziidae such as Thelazia callipaeda and Thelazia gulosa; Gongylonematidae such as Gongylonema pulchrum; Habronematidae such as Habronema majus, Habronema muscae, and Draschia megastoma; Dracunculidae such as Dracunculus medinensis; Spirocercidae such as Ascarops strongylina; Stephanofilaria Filariidae such as Parafilaria okinawaensis, Parafilaria multipapillosa, Parafilaria bovicola, etc.; Setariidae such as Setaria digitata and Setaria equina, etc.; Onchocercidae such as Dirofilaria immitis, Brugia malayi, Onchocerca cervicalis, Onchocerca gibsoni, Dipetalonema reconditum, Wuchereria bancrofti, etc.;

[0055] The harmful insects, harmful arthropods such as harmful mites, and harmful nematodes may be harmful insects, harmful arthropods such as harmful mites, and harmful nematodes that have reduced sensitivity to insecticides, acaricides, or nematocides, or that have developed drug resistance.

[0056] The method for controlling harmful arthropods or harmful nematodes of the present invention is carried out by applying an effective amount of the present compound, the compound of the present invention, Composition A, or Composition B directly to the harmful arthropods or harmful nematodes and / or to the habitat of the harmful arthropods or harmful nematodes (plants, soil, inside a house, animals, etc.). Examples of the method for controlling harmful arthropods or harmful nematodes of the present invention include foliage treatment, soil treatment, root treatment, shower treatment, fumigation treatment, water surface treatment, and seed treatment.

[0057] The present compound, the compound of the present invention, Composition A, and Composition B are typically mixed with an inert carrier such as a solid carrier, liquid carrier, or gaseous carrier, and a surfactant, and formulation adjuvants such as binders, dispersants, and stabilizers are added as needed to formulate them into aqueous suspensions, oil suspensions, oil solutions, emulsifiable concentrates, emulsion formulations, microemulsions, microcapsule formulations, wettable powders, water dispersible granules, dusts, granules, tablets, aerosols, resin formulations, and the like. In addition to these formulations, the present compound, the compound of the present invention, Composition A, and Composition B can also be formulated into dosage forms described in the Manual on development and use of FAO and WHO Specifications for pesticides, FAO Plant Production and Protection Papers-271 to 276, prepared by the FAO / WHO Joint Meeting on Pesticide Specifications, 2016, ISSN:0259-2517. These formulations typically contain 0.0001 to 99% by weight of the present compound, the compound of the present invention, Composition A, or Composition B.

[0058] Examples of solid carriers include clay (pyrophyllite clay, kaolin clay, etc.), talc, calcium carbonate, diatomaceous earth, zeolite, bentonite, acid clay, attapulgite, white carbon, ammonium sulfate, vermiculite, perlite, pumice, silica sand, fine powder and granular chemical fertilizers (ammonium sulfate, ammonium phosphate, ammonium nitrate, urea, ammonium chloride, etc.), and resins (polyethylene, polypropylene, polyester, polyurethane, polyamide, polyvinyl chloride, etc.).

[0059] Examples of liquid carriers include water, alcohols (ethanol, cyclohexanol, benzyl alcohol, propylene glycol, polyethylene glycol, etc.), ketones (acetone, cyclohexanone, etc.), aromatic hydrocarbons (xylene, phenylxylylethane, methylnaphthalene, etc.), aliphatic hydrocarbons (hexane, cyclohexane, etc.), esters (ethyl acetate, methyl oleate, propylene carbonate, etc.), nitriles (acetonitrile, etc.), ethers (ethylene glycol dimethyl ether, etc.), amides (N,N-dimethylformamide, N,N-dimethyloctanamide, etc.), sulfoxides (dimethyl sulfoxide, etc.), lactams (N-methylpyrrolidone, N-octylpyrrolidone, etc.), fatty acids (oleic acid, etc.), and vegetable oils (soybean oil, etc.).

[0060] Examples of gaseous carriers include fluorocarbons, butane gas, LPG (liquefied petroleum gas), dimethyl ether, nitrogen, and carbon dioxide gas.

[0061] Examples of surfactants include nonionic surfactants (polyoxyethylene alkyl ethers, polyoxyethylene alkylaryl ethers, polyethylene glycol fatty acid esters, etc.) and anionic surfactants (alkyl sulfonates, alkylaryl sulfonates, alkyl sulfates, etc.).

[0062] Other formulation adjuvants include binders, dispersants, colorants, stabilizers, etc., and specific examples include polysaccharides (starch, gum arabic, cellulose derivatives, alginic acid, etc.), lignin derivatives, synthetic water-soluble polymers (polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acids, etc.), acid isopropyl phosphate, and dibutylhydroxytoluene.

[0063] In addition, adjuvants can be used as components that enhance or support the efficacy of the present compound and the compound of the present invention. Specific examples include Nimbus (registered trademark), Assist (registered trademark), Aureo (registered trademark), Iharol (registered trademark), Silwet L-77 (registered trademark), BreakThru (registered trademark), Sundance II (registered trademark), Induce (registered trademark), Penetrator (registered trademark), AgriDex (registered trademark), Lutensol A8 (registered trademark), NP-7 (registered trademark), Triton (registered trademark), Nufilm (registered trademark), Emulgator NP7 (registered trademark), Emulad (registered trademark), TRITON X 45 (registered trademark), AGRAL 90 (registered trademark), AGROTIN (registered trademark), ARPON (registered trademark), EnSpray N (registered trademark), and BANOLE (registered trademark).

[0064] In the present invention, the plant includes the whole plant, stems and leaves, flowers, spikes, fruits, trunks, branches, crowns, seeds, vegetative reproductive organs, and seedlings.

[0065] Vegetative reproductive organs refer to plant roots, stems, leaves, and other parts that can grow when separated from the main body and placed in soil. Examples of vegetative reproductive organs include tuberous roots, creeping roots, bulbs, corms (or solid bulbs), tubers, rhizomes, stolons, rhizophores, cane cuttings, propagules, and vine cuttings. Stolons are sometimes called runners, and propagules are also called bulbils and are divided into broad buds and bulbils. Vines refer to shoots (a collective term for leaves and stems) of plants such as sweet potatoes and Japanese yams. Bulbs, corms, tubers, rhizomes, stem fragments, rhizophores, and tuberous roots are collectively called bulbils. Potato cultivation begins by planting tubers in the soil, and the tubers used are generally called seed potatoes.

[0066] Examples of methods for controlling harmful arthropods or harmful nematodes by applying an effective amount of the present compound, the compound of the present invention, Composition A, or Composition B to soil include a method of applying an effective amount of the present compound, the compound of the present invention, Composition A, or Composition B to the soil before or after planting a plant; a method of applying an effective amount of the present compound, the compound of the present invention, Composition A, or Composition B to the rhizosphere of a crop to be protected from damage such as feeding by harmful arthropods or harmful nematodes; and a method of systemically translocating an effective amount of the present compound, the compound of the present invention, Composition A, or Composition B from the roots or the like into the interior of the plant body to control harmful arthropods or harmful nematodes that feed on plants. More specifically, for example, planting hole treatment (spraying in planting holes, mixing in planting hole treatment soil), plant base treatment (spraying in planting holes, mixing in plant base soil, plant base irrigation, plant base treatment in the latter half of the seedling raising period), planting furrow treatment (spraying in planting furrows, mixing in planting furrow soil), row treatment (row spraying, row soil mixing, row spraying in the growing season), row treatment at sowing (row spraying at sowing, mixing in row soil at sowing), overall treatment (overall soil spraying, overall soil mixing), side row treatment, water surface treatment (water surface application, water surface application after flooding), other soil spray treatments (foliar spraying of granules during the growing season, spraying under the crown or around the main trunk, soil surface spraying, soil surface mixing, seeding hole spraying, furrow surface spraying, spraying between plants), and others. Other irrigation treatments include soil irrigation, seedling irrigation, chemical injection treatment, ground level irrigation, chemical drip irrigation, chemigation), seedling tray treatments (seedling tray spraying, seedling tray irrigation, seedling tray flooding), seedling tray treatments (seedling tray spraying, seedling tray irrigation, seedling tray flooding), seedling bed treatments (seedling bed spraying, seedling bed irrigation, water seedling bed spraying, seedling immersion), bed soil mixing treatments (bed soil mixing, bed soil mixing before sowing, spraying before soil covering at sowing, spraying after soil covering at sowing, covering soil mixing), and other treatments (hilling soil mixing, plowing in, topsoil mixing, rain-drop soil mixing, planting position treatment, granular inflorescence spraying, paste fertilizer mixing).

[0067] Seed treatments include, for example, treatment of seeds or vegetative reproductive organs with the present compound, the compound of the present invention, Composition A, or Composition B. More specifically, examples include spray treatments in which a suspension of the present compound, the compound of the present invention, Composition A, or Composition B is sprayed onto the surface of seeds or vegetative reproductive organs in a mist; smear treatments in which the present compound, the compound of the present invention, Composition A, or Composition B is applied to seeds or vegetative reproductive organs; immersion treatments in which seeds or vegetative reproductive organs are immersed in a solution of the present compound, the compound of the present invention, Composition A, or Composition B for a certain period of time; and methods of coating seeds or vegetative reproductive organs with a carrier containing the present compound, the compound of the present invention, Composition A, or Composition B (film coating treatment, pellet coating treatment, etc.). Seed potatoes are particularly examples of such vegetative reproductive organs. When treating seeds or vegetative reproductive organs with Composition A or Composition B, the seeds or vegetative reproductive organs can be treated with a single formulation of Composition A or Composition B, or different formulations of Composition A or Composition B can be applied to the seeds or vegetative reproductive organs in multiple separate applications. Examples of methods for treating seeds or vegetative reproductive organs in multiple separate formulations with Composition A or Composition B include a method of treating seeds or vegetative reproductive organs with a formulation containing only the present compound or the compound of the present invention as an active ingredient, air-drying the seeds or vegetative reproductive organs, and then treating with a formulation containing the present component; and a method of treating seeds or vegetative reproductive organs with a formulation containing the present compound or the compound of the present invention and this component as active ingredients, air-drying the seeds or vegetative reproductive organs, and then treating with a formulation containing a component other than the present component that has already been treated. In the present invention, seeds or vegetative reproductive organs bearing the present compound, the compound of the present invention, Composition A, or Composition B refer to seeds or vegetative reproductive organs in a state in which the present compound, the compound of the present invention, Composition A, or Composition B is attached to the surface of the seeds or vegetative reproductive organs. The seeds or vegetative reproductive organs bearing the present compound, the compound of the present invention, Composition A, or Composition B may have materials other than the present compound, the compound of the present invention, Composition A, or Composition B attached to them before or after the attachment of the present compound, the compound of the present invention, Composition A, or Composition B to the seeds or vegetative reproductive organs. Furthermore, when Composition A or Composition B is attached to the surface of the seeds or vegetative reproductive organs in the form of a layer, the layer may consist of one layer or multiple layers.Furthermore, when it consists of a plurality of layers, each layer contains one or more active ingredients, or it consists of a layer containing one or more active ingredients and a layer containing no active ingredient. Seeds or vegetative reproductive organs carrying the present compound, the compound of the present invention, Composition A, or Composition B can be obtained, for example, by applying a formulation containing the present compound, the compound of the present invention, Composition A, or Composition B to seeds or vegetative reproductive organs by the above-mentioned seed treatment method.

[0068] When the present compound, the compound of the present invention, Composition A, or Composition B is used for controlling harmful arthropods or harmful nematodes in the agricultural field, the application rate is 10,000 m 2 The amount of the present compound or the compound of the present invention applied per kg of seed or vegetative reproductive organ is usually 1 to 10,000 g. When treating seeds or vegetative reproductive organs, the amount of the present compound or the compound of the present invention applied per kg of seed or vegetative reproductive organ is usually in the range of 0.001 to 100 g. When the present compound, the compound of the present invention, Composition A, or Composition B is formulated as an emulsifiable concentrate, wettable powder, flowable concentrate, or the like, it is usually diluted with water to an active ingredient concentration of 0.01 to 10,000 ppm before application, and granules, dusts, and the like are usually applied as is.

[0069] In addition, the present compound, the compound of the present invention, Composition A, or Composition B can also be applied by wrapping a resin preparation processed into a sheet or string shape around crops, stretching it near crops, or spreading it on the soil around the base of the plants.

[0070] When the present compound, the compound of the present invention, Composition A, or Composition B is used to control harmful arthropods or harmful nematodes living in houses, the application rate is 1 / 2 m / day for surface application. 2 The amount of the present compound or the compound of the present invention per 1 m of treatment space is usually 0.01 to 1000 mg. 3 When the present compound, the compound of the present invention, Composition A, or Composition B is formulated as an emulsifiable concentrate, wettable powder, flowable concentrate, or the like, it is usually applied after diluting with water so that the active ingredient concentration is 0.1 to 10,000 ppm, whereas oil solutions, aerosols, fumigants, poison baits, and the like are applied as is.

[0071] When the present compound, the compound of the present invention, Composition A, or Composition B is used to control harmful arthropods or harmful nematodes that parasitize livestock such as cattle, horses, pigs, sheep, goats, and chickens, or small animals such as dogs, cats, rats, and mice, it can be administered to animals by methods known in veterinary medicine. Specific methods of use include oral administration by incorporating the compound into tablets, capsules, chewable tablets, feed, etc.; administration by suppository or injection (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.); spraying, applying, or dripping oil solutions, aqueous solutions, spot-on preparations, pour-on preparations, shampoos, lotions, pastes, etc.; or processing resin preparations into collars, ear tags, bracelets, and clothing and attaching them to the animal. The amount of the present compound when administered to animals is typically in the range of 0.1 to 1,000 mg per kg of the animal's body weight.

[0072] Furthermore, the present compound, the compound of the present invention, Composition A, or Composition B can be used as an agent for controlling harmful arthropods or harmful nematodes in agricultural lands such as fields, paddy fields, lawns, orchards, etc. Examples of plants include the following.

[0073] Corn (horse-tooth, hard grain, soft grain, explosive, glutinous, sweet, field corn), rice (long grain, short grain, medium grain, japonica, tropical japonica, indica, javanica, paddy rice, upland rice, floating rice, direct-seeded rice, transplanted rice, glutinous rice), wheat (bread wheat (hard, soft, medium, red wheat, white wheat), durum wheat, spelt wheat, club wheat, each winter wheat type, spring wheat type), barley (two-row barley (= beer barley), six-row barley, naked barley, waxy barley, each winter barley type, spring barley type), rye (winter rye type, spring rye type), triticale (winter triticale type, spring triticale type), oats (winter oat type, spring oat type), sorghum, cotton (upland type, pima type), soybean (fully harvested seed varieties, edamame varieties, green-harvested varieties, indeterminate, determinate, semi-determinate types), peanuts, buckwheat, sugar beet (sugar production, animal feed, root vegetable, leafy vegetable, fuel), rapeseed (winter rapeseed type, spring rapeseed type), canola (winter canola type, spring canola type), sunflower (oil production, food, ornamental), sugarcane, tobacco, tea plant, mulberry, solanaceous vegetables (eggplant, tomato, bell pepper, chili pepper) , potatoes, etc.), Cucurbitaceae vegetables (cucumber, pumpkin, zucchini, watermelon, melon, etc.), Cruciferous vegetables (radish, turnip, horseradish, kohlrabi, Chinese cabbage, cabbage, mustard greens, broccoli, cauliflower, etc.), Asteraceae vegetables (burdock, garland chrysanthemum, artichoke, lettuce, etc.), Liliaceae vegetables (leeks, onions, garlic, asparagus, etc.), Umbelliferae vegetables (carrots, parsley, celery, parsley, etc.), Chenopodiaceae vegetables (spinach, Swiss chard, etc.), Lamiaceae vegetables (perilla, mint, basil, etc.), strawberries, sweet potatoes, yams, scallions, Sweet potatoes, pome fruits (apples, European pears, Japanese pears, Chinese pears, quince, quince, etc.), stone fruits (peaches, plums, nectarines, plums, cherries, apricots, prunes, etc.), citrus fruits (Satsuma mandarins, oranges, lemons, limes, grapefruits, etc.), nuts (chestnuts, walnuts, hazelnuts, almonds, pistachios, cashew nuts, macadamia nuts, etc.), berries (blueberries, cranberries, blackberries, raspberries, etc.), grapes, persimmons, figs, olives, loquats, bananas, coffee, dates, coconuts, ornamental plants, forest plants,Turfgrass, pasture grass,

[0074] The above-mentioned plants are not particularly limited as long as they are varieties that are commonly cultivated, and include plants that can be produced by natural crossbreeding, plants that can be generated by mutation, F1 hybrid plants, and genetically modified crops. Examples of genetically modified crops include plants that have been conferred resistance to herbicides such as HPPD (4-hydroxyphenylpyruvate dioxygenase enzyme) inhibitors such as isoxaflutole, ALS (acetolactate synthase) inhibitors such as imazethapyr and thifensulfuron methyl, EPSP (5-enolpyruvylshikimate-3-phosphate synthase) inhibitors, glutamine synthetase inhibitors, PPO (protoporphyrinogen oxidase) inhibitors, bromoxynil, or dicamba; plants that are capable of synthesizing selective toxins known to be found in the genus Bacillus, such as Bacillus thuringiensis; and plants that can be conferred specific insecticidal activity by synthesizing gene fragments that partially match endogenous genes derived from harmful insects and inducing gene silencing (RNAi; RNA interference) in the target harmful insect.

[0075] The present invention will be explained in more detail below with reference to production examples, formulation examples and test examples, but the present invention is not limited to these examples.

[0076] When the physical properties of a compound are measured by liquid chromatography / mass spectrometry (hereinafter referred to as LCMS), the measured molecular ion value [M+H] + or [M-H] - and retention time (hereinafter referred to as RT). The conditions for liquid chromatography (hereinafter referred to as LC) and mass spectrometry (hereinafter referred to as MS) are as follows.

[0077] [LC conditions] Column: L-column2 ODS, inner diameter 4.6 mm, length 30 mm, particle size 3 μm (Chemicals Evaluation and Research Institute, Japan) UV measurement wavelength: 254 nm Mobile phase: Solution A: 0.1% formic acid aqueous solution, Solution B: 0.1% formic acid acetonitrile Flow rate: 2.0 mL / min Pump: 2 LC-20AD (Shimadzu Corporation) (high pressure gradient) Gradient conditions: Solution was delivered at the concentration gradient shown in [Table LC1].

[0078]

[0079] [MS conditions] Detector: LCMS-2020 (Shimadzu Corporation) Ionization method: DUIS

[0080] Preparation Example 1 The present compounds A-1 to A-4 can be obtained according to the method described in Heterocyclic Communications (1995), 1(2-3), 207, etc. The identification of the obtained compounds is as follows: 1 Measurement of H-NMR spectrum, 13 This can be done by measuring the C-NMR spectrum, etc.

[0081] Preparation Example 2 The compounds C-1 to C-3 can be obtained according to the methods described in Journal of Organic Chemistry (1985), 50(20), 3757; Heterocycles (1989), 28(1), 103, etc. The compounds obtained can be identified by the following methods: 1 Measurement of H-NMR spectrum, 13 This can be done by measuring the C-NMR spectrum, etc.

[0082] The physical properties of the compound obtained by the above method are shown below. Compound C-1: 1H-NMR (CDCl3) δ: 0.92(3H, d, J=6.4Hz), 1.06 (3H, d, J=6.9Hz), 1.16 (1H, d, J=13Hz), 1.25 (3H, d, J=7.0Hz), 1.47-1.75 (5H, m), 1.87 (1H, dd. (1H, dd, J=13Hz, 5.4Hz), 3.00 (1H, br s), 3.14 (1H, d, J=6.6Hz), 3.15 (1H, br s), 3.52 (1H, d, J=9.0Hz), 3.57 (1H, d, J=18Hz), 3.84 (1H, s), 3.95 (1H, d, J=9.0Hz), 4.22 (1H, d, J=9.3Hz), 4.62 (1H, br s), 4.92 (1H, d, J=9.3Hz), 5.88 (1H, s).

[0083] Preparation Example 3 Compounds A-5 to A-12 and B-1 can be obtained according to the methods described in Tetrahedron (1998), 54(27), 7891; Tetrahedron (1999), 55(17), 5539; Marine Drugs (2014), 12(10), 5188; Angewandte Chemie (International ed. in English) (2009), 48(47), 8905-8, Chemistry - An Asian Journal (2011), 6(3), 922-931, etc. The compounds obtained can be identified by the following methods. 1 Measurement of H-NMR spectrum, 13 This can be done by measuring the C-NMR spectrum, etc.

[0084] The physical properties of the compound obtained by the above method are shown below. Compound B-1: 1H-NMR (CDCl3) δ: 0.93 (3H, d, J=6.5Hz), 1.07 (3H, s), 1.11 (3H, s), 1.12-1.15 (1H, m), 1.17 (3H, s), 1.54 (3H, d, J=7.0Hz), 1.46-1.55 (3H, m), 1.72-1.82 (2H, m), 1.91 (1H, dd, J=14Hz, 4.5Hz), 2.15 (1H, dd, J=13Hz, 5.0Hz), 2.30 (3H, s), 2.31-2.37 (1H, m), 2.44 (1H, dd, J=20Hz, 1.0Hz), 2.50 (1H, d, J=14Hz), 2.65 (1H, d, J=14Hz), 3.37 (1H, t, J=6.4Hz), 3.42 (1H, d, J=6.4Hz), 3.55 (1H, q, J=6.9Hz), 3.56 (1H, s), 3.91 (1H, d, J=20Hz), 4.57-4.61 (1H, m), 4.89 (1H, br s), 6.48 (1H, s), 6.55 (1H, s).

[0085] Preparation Example 4 Compounds C-4 to C-28 and D-1 can be obtained according to the methods described in Tetrahedron Letters (2014), 55(39), 5369; Tetrahedron (2015), 71(45), 8601; Journal of Natural Products (2019), 82(10), 2790; Journal of Natural Products (2016), 79(10), 2674, etc. The compounds obtained can be identified by the following method. 1 Measurement of H-NMR spectrum, 13 This can be done by measuring the C-NMR spectrum, etc.

[0086] The physical properties of the compounds obtained by the method mentioned above are below. This compound C-4: 1 H-NMR (C5D5N) δ: 0.86(3H, d, J=6.4Hz), 1.09-1.19 (2H, m), 1.22 (3H, d, J=7.3Hz), 1.43 (2H, dd, J=8.6Hz, 2.4Hz), 1.47 (3H, s), 1.63 (3H, s), 1.68-1.72 (1H, m), 1.91-1.99 (1H, m), 2.25-2.35 (3H, m), 2.42-2.49 (1H, m), 2.54 (1H, dd, J=14Hz, 4.6Hz), 2.58 (1H, d, J=4.1Hz), 3.05-3.12 (1H, m), 3.30 (1H, d, J=6.6Hz), 3.49 (1H, dq, J=7.3Hz, 4.6Hz), 3.60 (1H, t, J=6.6Hz), 3.64 (2H, s), 3.71 (1H, s), 3.93 (1H, d, J=8.7Hz), 4.14 (1H, d, J=8.7Hz), 4.35 (1H, d, J=9.7Hz), 4.47 (1H, br s), 4.56 (1H, d, J=9.7Hz), 4.62-4.63 (1H, m), 5.99 (1H, s). Compound C-7: 1H-NMR (C5D5N) δ: 0.85(3H, d, J=6.2Hz), 1.06 (3H, s), 1.08-1.15 (1H, m), 1.24 (3H, d, J=7.3Hz), 1.37-1.42 (3H, m), 1.70 (1H, dt, J=12Hz, 3.6Hz), 1.81 (1H, td, J=13Hz, 3.6Hz), 1.87 (3H, s), 2.20-2.23 (2H, m), 2.32 (1H, td, J=13Hz, 3.7Hz), 2.52 (1H, dd, J=17Hz, 12Hz), 2.66 (1H, dd, J=15Hz, 4.8Hz), 2.71 (1H, dd, J=17Hz, 4.2Hz), 2.73 (1H, d, J=6.5Hz), 3.27 (1H, ddd, J=16Hz, 12Hz, 4.2Hz), 3.47 (1H, dq, J=7.3Hz, 4.8Hz), 3.63 (1H, s), 3.73 (1H, t, J=6.5Hz), 3.81 (2H, s), 4.26 (1H, d, J=9.8Hz), 4.42 (1H, d, J=9.8Hz), 4.49 (1H, br s), 4.51 (1H, d, J=9.4Hz), 4.62 (1H, d, J=9.4Hz), 6.01 (1H, s).

[0087] Preparation Example 5: Compounds A-13 and A-14 can be obtained according to the method described in Marine Drugs (2018), 16(7), 242, etc. The compounds obtained can be identified by the following method. 1 Measurement of H-NMR spectrum, 13 This can be done by measuring the C-NMR spectrum, etc.

[0088] Preparation Example 6: Compound A-15 can be obtained according to the method described in Tetrahedron Letters (2008), 49(14), 2189, etc. The compound obtained can be identified by the following method. 1 Measurement of H-NMR spectrum, 13 This can be done by measuring the C-NMR spectrum, etc.

[0089] Production Example 7: Compounds C-29 to C-35 and D-2 can be obtained according to the method described in J. Org. Chem. 2020, 85, 12553, etc. The compounds obtained can be identified by the following method. 1 Measurement of H-NMR spectrum, 13 This can be done by measuring the C-NMR spectrum, etc.

[0090] Production Example 8 Compounds C-36 to C-44, A-16, and A-17 can be obtained according to the method described in Bioorganic Chemistry 109 (2021) 104700, etc. The compounds obtained can be identified by 1 Measurement of H-NMR spectrum, 13 This can be done by measuring the C-NMR spectrum, etc.

[0091] Preparation Example 9 The compounds E-1, A-18, G-1, G-2 and A-20 can be obtained according to the method described in Bulletin of the Chemical Society of Japan (1998), 71(4), 771-779, etc. The compounds obtained can be identified by the following method. 1 Measurement of H-NMR spectrum, 13 This can be done by measuring the C-NMR spectrum, etc.

[0092] The physical properties of the compound obtained by the above method are shown below. Compound E-1: 1H-NMR (CDCl3) δ: 0.92 (3H, d, J=6.5Hz), 1.00 (3H, s), 1.09-1.17 (1H, m), 1.14 (3H, s), 1.23 (3H, s), 1.50 (1H, dd, J=12Hz, 9.0Hz), 1.76-2.01 (6H, m), 2.00 (3H, s), 2.16 (1H, dd, J=11Hz, 4.1Hz), 2.26-2.35 (1H, m), 2.43 (1H, dd, J=18Hz, 4.1Hz), 2.52 (1H, d, J=15Hz), 2.51-2.67 (3H, m), 2.89 (1H, s), 3.13 (1H, dd, J=7.4Hz, 6.6Hz), 3.23 (1H, d, J=15Hz), 3.22-3.29 (1H, m), 3.68 (3H, s), 3.72 (1H, dd, J=7.4Hz, 7.0Hz) 4.10 (1H, s), 4.60-4.62 (1H, m), 5.90 (1H, s). This compound A-18: 1 H-NMR (CDCl3) δ:0.91 (3H, d, J=6.5Hz), 0.99 (3H, s), 0.99 (3H, s), 1.05-1.09 (1H, m), 1.11 (3H, d, J=6.1Hz), 1.15 (3H, s), 1.24-1.30 (2H, m), 1.39-1.50 (2H, m), 1.64-1.81 (3H, m), 1.84-1.9, (3H, m), 1.87 (1H, d, J=14Hz), 2.06 (1H, dd, J=13Hz, 13Hz), 2.09 (1H, dd, J=13Hz, 5.0Hz), 2.18 (1H, d, J=14Hz), 2.24-2.35 (2H, m), 2.35 (1H, d, J=20Hz), 2.48 (1H, dd, J=13Hz, 3.9Hz), 2.66-2.78 (2H, m), 2.81 (1H, s), 3.23 (1H, dd, J=6.8Hz, 6.1Hz), 3.27 (1H, d, J=6.1Hz), 3.62 (1H, d, J=20Hz), 4.54-4.56 (1H, m).

[0093] Preparation Example 10: Compounds A-19, F-4, and F-5 can be obtained according to the method described in Heterocyclic Communications (1998), 4(6), 575-580, etc. The compounds obtained can be identified by the following method. 1 Measurement of H-NMR spectrum, 13 This can be done by measuring C-NMR spectrum, mass spectrum, etc.

[0094] The physical properties of the compound obtained by the above method are shown below. Compound A-19: LCMS: 498 [M+H] + , RT=1.25 minutes

[0095] Preparation Example 11 The present compounds B-2 and A-23 can be obtained according to the methods described in Angewandte Chemie (International ed. in English) (2009), 48(47), 8905-8, Chemistry - An Asian Journal (2011), 6(3), 922-931, etc. The identification of the obtained compounds can be carried out by 1 Measurement of H-NMR spectrum, 13 This can be done by measuring the C-NMR spectrum, etc.

[0096] The physical properties of the compound obtained by the above method are shown below. Compound B-2: 1H-NMR (CDCl3) δ: 0.93 (3H, d, J=6.5Hz), 0.98-1.04 (1H, m), 1.10(3H, s), 1.11 (3H, s), 1.17 (3H, s), 1.48 (1H, dd, J=14Hz, 2.4Hz), 1.59-1.62 (2H, m), 1.74 (1H, dd, J=13Hz, 3.8Hz), 1.79 (1H, dd, J=10Hz, 2.4Hz), 1.89 (1H, dd, J=13Hz, 4.8Hz), 2.14 (1H, dd, J=13Hz, 4.7Hz), 2.32 (3H, s), 2.34-2.40 (1H, m), 2.46 (1H, dd, J=20Hz, 1.1Hz), 2.53 (1H, d, J=14Hz), 2.61 (1H, d, J=14Hz), 3.22 (1H, s), 3.38 (1H, d, J=6.5Hz), 3.38 (1H, d, J=21Hz), 3.42 (1H, d, J=6.5Hz), 3.64 (1H, d, J=21Hz), 3.76 (1H, d, J=20Hz), 4.58-4.61 (1H, m), 4.87 (1H, br s), 6.51 (1H, s), 6.59 (1H, s)

[0097] Preparation Example 12: Compounds F-1 to F-3 can be obtained according to the methods described in Tetrahedron Letters (1997), 38(32), 5683-5686, Bulletin of the Chemical Society of Japan (1998), 71(4), 771-779, etc. The compounds obtained can be identified by the following methods: 1 Measurement of H-NMR spectrum, 13 This can be done by measuring the C-NMR spectrum, etc.

[0098] The physical properties of the compound obtained by the above method are shown below. Compound F-1: 11H-NMR (CDCl3) δ: 0.86 (3H, d, J=6.5Hz), 0.91 (3H, s), 1.01 (3H, s), 1.09 (1H, dd, J=13Hz, 12Hz), 1.32 (1H, ddd, J=14Hz, 11Hz, 2.4Hz), 1.40 (3H, s), 1.43 - 1.50 (2H, m), 1.71 (1H, dd, J=14Hz, 4.4Hz), 1.80 (1H, dd, J=14Hz, 2.3Hz), 1.86 (1H, dd, J=14Hz, 3.3Hz), 1.92 (1H, dd, J=14Hz, 3.4Hz), 1.90 - 1.96 (1H, m), 2.02 (3H, s), 2.09 (1H, ddd, J=15Hz, 8.5Hz, 5.1Hz), 2.27 - 2.34 (2H, m), 2.37 (1H, dd, J=13Hz, 11Hz), 2.54 (1H, s), 2.56 - 2.64 (2H, m), 2.70 - 2.75 (2H, m), 2.79 (1H, dd, J=11Hz, 7.4Hz), 3.18 (1H, dd, J=14Hz, 2.0Hz), 3.25 (1H, dd, J=11Hz, 1.3Hz), 3.48 (1H, d, J=15Hz), 4.49 - 4.53 (1H, m), 5.91 (1H, s). This compound F-2: 11H-NMR (CDCl3) δ: 0.85 (3H, d, J = 6.5 Hz), 0.92 (3H, s), 1.02 (3H, s), 1.08 (1H, dd, J = 13 Hz, 12 Hz), 1.26 - 1.31 (1H, m), 1.33 (3H, s), 1.39 - 1.48 (2H, m), 1.68 (1H, dd, J = 15 Hz, 4.1 Hz), 1.74 (3H, s), 1.73 - 1.80 (3H, m), 1.85 (1H, dd, J = 14 Hz, 3.1 Hz), 1.89 - 1.96 (4H, m), 2.08 (1H, dd, J = 14 Hz, 11 Hz), 2.55 (1H, s), 2.54 - 2.57 (1H, m), 2.72 (1H, dd, J = 5.0 Hz, 3.1 Hz), 2.78 (1H, dd, J = 11 Hz, 7.5 Hz), 2.84 (1H, dd, J = 14 Hz, 4.5 Hz), 3.18 (1H, dd, J = 14 Hz, 2.0 Hz), 3.23 (1H, dd, J = 11 Hz, 1.3 Hz), 3.52 (1H, d, J = 14 Hz), 3.95 (1H, br s), 4.48 - 4.52 (1H, m), 5.38 (1H, s). This compound F-3: 1H-NMR (CDCl3) δ: 0.85 (3H, d, J=6.5Hz), 0.92 (3H, s), 1.01 (3H, s), 1.08 (1H, dd, J=13Hz, 12Hz), 1.25-1.32 (1H, m), 1.34 (3H, s), 1.42 (1H, dd, J=13Hz, 5.0Hz), 1.44-1.49 (1H, m), 1.69 (1H, dd, J=14Hz, 4.1Hz), 1.74 (3H, s), 1.76-1.87 (3H, m), 1.88 (1H, dd, J=11Hz, 3.1Hz), 1.93-2.03 (4H, m), 2.05 (3H, s), 2.07-2.12 (1H, m), 2.53-2.58 (2H, m), 2.61 (1H, s), 2.72 (1H, dd, J=5.0Hz, 3.1Hz), 2.78 (1H, dd, J=11Hz, 7.4Hz), 3.17 (1H, dd, J=14Hz, 2.0Hz), 3.23 (1H, d, J=11Hz), 3.51 (1H, d, J=14Hz), 4.50 (1H, d, J=5.9Hz), 5.22 (1H, d, J=7.6Hz), 5.31 (1H, s).

[0099] Preparation Example 13: Compounds A-21 and A-22 can be obtained according to the method described in JP-A-10-101678. The compounds obtained can be identified by the following method. 1 Measurement of H-NMR spectrum, 13 This can be done by measuring the C-NMR spectrum, etc.

[0100] Preparation Example 14 The present compounds E-2 and E-3 can be obtained in accordance with the method described in the specification of U.S. Patent Application Publication No. 2016 / 0036094, etc. The identification of the obtained compounds is as follows: 1 Measurement of H-NMR spectrum, 13 This can be done by measuring the C-NMR spectrum, etc.

[0101] Preparation Example 15: Compounds E-4 and E-5 can be obtained according to the method described in the Abstracts of the 62nd Symposium on Natural Organic Compounds (2020), pages 2-8, etc. The compounds obtained can be identified by the following method. 1 Measurement of H-NMR spectrum, 13 This can be done by measuring the C-NMR spectrum, etc.

[0102] Production Example 16: 300 mg of norzoanthamine was dissolved in 54 mL of methanol, and 100 mg of 10% palladium carbon (NX type, hydrous, manufactured by N.E. Chemcat Corporation) was added. The atmosphere in the reaction vessel was replaced with hydrogen, and the mixture was stirred at room temperature for 3 hours. After completion of the reaction, the resulting mixture was filtered through Celite (registered trademark), and the resulting solid was washed three times with 20 mL of methanol. The resulting filtrate and washings were combined and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (chloroform:methanol = 1:0 → 9:1) to obtain 110 mg of the present compound GG-1 as a white solid. Compound GG-1 of the present invention: 1 H-NMR (CDCl3) δ: 0.95 (3H, d, J=6.3Hz), 0.96 (3H, s), 1.06 (3H, s), 1.11 (3H, d, J=6.5Hz), 1.12 (3H, s), 1.14-1.42 (4H, m), 1.59-1.73 (4H, m), 1.76-1.89 (2H, m), 1.84 (1H, dd, J=13Hz, 3.8Hz), 1.92-2.03 (3H, m), 2.05 (1H, d, J=13Hz), 2.40-2.49 (4H, m), 2.53 (1H, s), 2.56-2.60 (2H, m), 2.63-2.67 (2H, m), 2.94 (1H, d, J=15Hz), 3.40 (1H, dt, J=13Hz, 4.4Hz), 3.72-3.77 (1H, m), 4.05 (1H, d, J=15Hz).

[0103] Production Example 17: 61 mg of the present invention compound GG-1 was dissolved in 2 mL of chloroform, 0.5 mL of methanol was added, and the mixture was cooled in an ice bath. 313 mg of trimethylsilyldiazomethane was added, and the mixture was stirred in an ice bath for 1 hour. After completion of the reaction, the resulting mixture was concentrated under reduced pressure, and the residue was subjected to silica gel column chromatography (chloroform:methanol = 1:0 → 9:1) to obtain 49.8 mg of the present invention compound GG-2 as a white amorphous substance. Compound GG-2 of the present invention: 1 H-NMR (CDCl3) δ: 0.88 (3H, s), 0.93 (3H, d, J=6.8Hz), 0.99-1.01 (2H, m), 1.09 (3H, d, J=6.5Hz), 1.10-1.13 (1H, m), 1.15 (3H, s), 1.16 (3H, s), 1.25-1.39 (3H, m), 1.43-1.52 (1H, m), 1.64-1.70 (1H, m), 1.65 (1H, dd, J=12Hz), 1.78-1.90 (3H, m), 1.96-2.06 (2H, m), 2.01 (1H, d, J=12Hz), 2.14 (1H, dd, J=13Hz, 10Hz), 2.37-2.44 (5H, m), 2.49 (1H, s), 2.53-2.62 (2H, m), 3.29 (1H, dd, J=14Hz, 3.3Hz), 3.47 (1H, d, J=16Hz), 3.66 (3H, s), 3.82-3.89 (1H, m), 3.99 (1H, d, J=16Hz).

[0104] Preparation Example 18: 30 mg of the present compound A-18 was dissolved in 3 mL of chloroform, 0.3 mL of methyl iodide and 86.6 mg of silver oxide were added, and the mixture was heated under reflux for 50 hours. After completion of the reaction, the mixture was cooled to room temperature, and the resulting mixture was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (chloroform:methanol=1:0→9:1) to obtain 34 mg of the present compound EE-1 as a pale yellow amorphous substance. Compound EE-1 of the present invention: LCMS: 498 [M+H] + , RT=1.28 minutes

[0105] Preparation Example 19: 30 mg of the present compound A-18 was dissolved in 3 mL of methanol, 0.5 mL of 1.2 N hydrochloric acid was added, and the mixture was stirred at room temperature for 1 hour. After completion of the reaction, the resulting mixture was concentrated under reduced pressure to obtain 28.6 mg of the present compound EE-2. Compound EE-2 of the present invention: 1 H-NMR (CD3OD) δ: 1.01 (3H, s), 1.02 (3H, d, J=6.8Hz), 1.13 (3H, d, J=6.3Hz), 1.32 (3H, s), 1.39 (1H, t, J=12Hz), 1.45 (3H, s), 1.45-1.49 (1H, m), 1.61-1.68 (1H, m), 1.79 (1H, dt, J=15Hz, 3.5Hz), 1.86-2.09 (6H, m), 1.97 (1H, d, J=13Hz), 2.19 (1H, t, J=13Hz), 2.22-2.29 (2H, m), 2.36-2.41 (2H, m), 2.46-2.52 (1H, m), 2.52 (1H, dd, J=15Hz, 4.8Hz), 2.73 (1H, d, J=13Hz), 2.80 (1H, dd, J=13Hz, 4.8Hz), 2.84 (1H, d, J=15Hz), 3.24 (1H, s), 3.24 (1H, d, J=15Hz), 4.18 (1H, dd, J=13Hz, 6.5Hz), 4.29 (1H, d, J=13Hz), 4.89-4.90 (1H, m).

[0106] The compound EE-2 of the present invention is the hydrochloride salt of the compound A-18.

[0107] Preparation Example 20: 28 mg of the present compound B-2 was dissolved in 3 mL of tetrahydrofuran, 23.1 mg of pyridine and 14.9 mg of acetic anhydride were added, and the mixture was stirred at room temperature for 4 hours. After completion of the reaction, the resulting mixture was concentrated under reduced pressure, and the resulting residue was subjected to silica gel column chromatography (chloroform:methanol=1:0→9:1) to obtain 35 mg of the present compound BB-1 as a pale yellow amorphous substance. Compound BB-1 of the present invention: 1H-NMR (CDCl3) δ: 0.93 (3H, d, J=6.5Hz), 1.09 (3H, s), 1.10 (3H, s), 1.10-1.15 (1H, m), 1.17 (3H, s), 1.50 (1H, dt, J=17Hz, 6.3Hz), 1.46-1.53 ​​(2H, m), 1.71-1.82 (2H, m), 1.89 (1H, dd, J=14Hz, 4.8Hz), 2.13 (1H, dd, J=13Hz, 4.5Hz), 2.31 (3H, s), 2.33-2.36 (1H, m), 2.38 (3H, s), 2.46 (1H, dd, J=20Hz, 1.2Hz), 2.53 (1H, d, J=14Hz), 2.64 (1H, d, J=14Hz), 3.20 (1H, s), 3.36 (1H, d, J=22Hz), 3.41 (1H, d, J=6.3Hz), 3.43 (1H, d, J=6.3Hz), 3.50 (1H, d, J=22Hz), 3.72 (1H, d, J=20Hz), 4.60 (1H, s), 6.82 (1H, s), 6.89 (1H, s).

[0108] Production Example 21: 30 mg of zoanthamin was dissolved in 1 mL of methanol, and 6.0 mg of sodium borohydride was added in an ice bath. The ice bath was removed and the mixture was stirred at room temperature for 1 hour. After completion of the reaction, 10 mL of water was added to the resulting mixture, and the mixture was extracted three times with 20 mL of chloroform. The resulting organic layers were combined, dried over sodium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (chloroform:methanol = 1:0 → 19:1) to obtain 26.4 mg of the present compound EE-3 as a white solid. Compound EE-3 of the present invention: 1H-NMR (CDCl3) δ: 0.90 (3H, d, J=6.5Hz), 0.99 (1H, t, J=5.6Hz), 1.03 (3H, s), 1.04 (3H, s), 1.16 (3H, s), 1.16 (3H, d, J=7.0Hz), 1.34-1.40 (2H, m), 1.45-1.50 (1H, m), 1.66 (1H, dd, J=15Hz, 5.2Hz), 1.79-1.86 (3H, m), 1.95 (1H, dd, J=15Hz, 1.9Hz), 2.02 (3H, s), 2.26-2.42 (5H, m), 2.59 (1H, dd, J=13Hz, 5.1Hz), 2.69-2.76 (2H, m), 2.80 (1H, d, J=8.7Hz), 2.83 (1H, s), 2.88 (1H, d, J=14Hz), 3.19 (1H, dd, J=7.1Hz, 5.3Hz), 3.54 (1H, d, J=14Hz), 4.38 (1H, br s), 5.94 (1H, s), 10.28 (1H, br s).

[0109] Production Example 22: 110 mg of zoanthamine was dissolved in 100 mL of chloroform, and 3 mL of methanol and 69.7 mg of sodium cyanoborohydride were added, followed by stirring at room temperature for 40 minutes. After completion of the reaction, 20 mL of water was added, and the mixture was extracted twice with 30 mL of chloroform. The resulting organic layer was dried over anhydrous sodium sulfate and then filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was subjected to silica gel column chromatography (chloroform:ethanol = 1:0 → 9:1) to give 47.7 mg of the present compound EE-3 and 26.9 mg of the present compound GG-3. Compound GG-3 of the present invention: 1H-NMR (CDCl3) δ: 0.93 (3H, d, J=6.8Hz), 1.03 (3H, s), 1.16 (3H, d, J=6.8Hz), 1.20 (3H, s), 1.23-1.26 (1H, m), 1.30 (3H, s), 1.33-1.55 (6H, m), 1.78-1.83 (3H, m), 1.90 (1H, d, J=15Hz), 1.93 (1H, dd, J=14Hz, 5.8Hz), 1.99 (3H, s), 2.16 (1H, dd, J=17Hz, 11Hz), 2.34 (1H, dd, J=17Hz, 4.9Hz), 2.42-2.52 (3H, m), 2.60 (1H, dd, J=13Hz, 4.9Hz), 2.66 (1H, dd, J=13Hz, 7.7Hz), 2.74 (1H, s), 2.92 (1H, d, J=13Hz), 2.99 (1H, t, J=6.5Hz), 3.48 (1H, d, J=15Hz), 3.92 (1H, td, J=6.5Hz, 3.1Hz), 4.99 (1H, br s), 5.92 (1H, s).

[0110] Production Example 23: 30 mg of zoanthamine was dissolved in 3 mL of chloroform, 0.3 mL of methyl iodide and 84.1 mg of silver(I) oxide were added, and the mixture was heated under reflux for 34 hours. After completion of the reaction, the mixture was cooled to room temperature. The resulting mixture was subjected to silica gel column chromatography (chloroform:methanol = 1:0 → 19:1) to obtain 28.8 mg of the present compound EE-4 as a white solid. Compound EE-4 of the present invention: 1H-NMR (CDCl3) δ: 0.92 (3H, d, J=6.5Hz), 1.00 (3H, s), 1.09-1.15 (1H, m), 1.18 (3H, d, J=6.9Hz), 1.18 (3H, s), 1.20 (3H, s), 1.22-1.26 (1H, m), 1.44-1.51 (2H, m), 1.77-1.97 (5H, m), 2.00 (3H, s), 2.23-2.44 (3H, m), 2.52 (1H, d, J=15Hz), 2.58 (1H, dd, J=13Hz, 5.7Hz), 3.02 (1H, dd, J=6.9Hz, 5.7Hz), 3.13 (1H, dd, J=8.2Hz, 6.6Hz), 3.24 (1H, t, J=8.2Hz), 3.27 (1H, d, J=15Hz), 3.28 (1H, s), 3.68 (3H, s), 4.18 (1H, s), 4.61 (1H, d, J=6.6Hz), 5.90 (1H, s).

[0111] Production Example 24: 25 mg of the present compound EE-3 was dissolved in 1 mL of chloroform. In an ice bath, 0.25 mL of methanol and 125 mg of trimethylsilyldiazomethane (2 M diethyl ether solution) were added, and the mixture was allowed to return to room temperature and stirred for 1 hour. After completion of the reaction, the mixture was concentrated under reduced pressure, and the residue was subjected to silica gel column chromatography (chloroform:methanol = 1:0 → 9:1) to obtain 23.1 mg of the present compound EE-5 as a white solid. Compound EE-5 of the present invention: 1H-NMR (CDCl3) δ: 0.89 (3H, d, J=6.5Hz), 0.94-1.00 (1H, m), 1.09 (3H, s), 1.11 (3H, d, J=7.0Hz), 1.14 (3H, s), 1.28-1.38 (2H, m), 1.40 (3H, s), 1.43-1.50 (1H, m), 1.64 (1H, dd, J=15Hz, 5.6Hz), 1.73-1.81 (2H, m), 1.90 (1H, dd, J=13Hz, 3.2Hz), 1.94-1.99 (1H, m), 2.00 (3H, s), 2.09 (1H, dd, J=12Hz, 5.0Hz), 2.19-2.34 (3H, m), 2.43 (1H, td, J=15Hz, 5.1Hz), 2.53 (1H, dd, J=13Hz, 5.0Hz), 2.58-2.61 (2H, m), 2.67 (1H, d, J=6.8Hz), 2.73 (1H, s), 2.84 (1H, d, J=16Hz), 3.09 (1H, dd, J=7.0Hz, 5.2Hz), 3.28 (1H, d, J=16Hz), 3.68 (3H, s), 4.38 (1H, br s), 5.92 (1H, s).

[0112] Production Example 25: 21.3 mg of the present compound A-18 was dissolved in 3 mL of ethanol. 5.0 mg of sodium borohydride was added in an ice bath, and the mixture was stirred for 1 hour. After completion of the reaction, 10 mL of water was added to the resulting mixture, which was then extracted three times with 10 mL of chloroform. The resulting organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (chloroform:methanol = 1:0 → 9:1) to obtain 17.8 mg of the present compound EE-6 as a pale yellow solid. The present compound EE-6: LCMS: 488 [M+H] + , RT=1.10 minutes

[0113] Test Example 26: 30 mg of zoanthamin was dissolved in 4.5 mL of ethanol. 10.3 mg of sodium borohydride was added in an ice bath, and the mixture was stirred for 1 hour. After completion of the reaction, 5 mL of acetone was added to the resulting mixture in an ice bath, and the mixture was stirred for 10 minutes, then returned to room temperature and stirred for 30 minutes. 10 mL of water was added to the resulting mixture, and the mixture was extracted three times with 10 mL of chloroform. The resulting organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (chloroform:ethanol = 1:0 → 9:1) to obtain 34.8 mg of the present compound EE-7. The present compound EE-7: LCMS: 502 [M+H] + , RT=1.29 minutes

[0114] Production Example 27: 20 mg of norzoanthamine was dissolved in 5 mL of acetonitrile, 3.84 mg of p-toluenesulfonic acid monohydrate and 5.93 mg of N-chlorosuccinimide were added, and the mixture was stirred at room temperature for 20 hours. After completion of the reaction, 5 mL of water was added to the resulting mixture, and the mixture was extracted three times with 5 mL of chloroform. The resulting organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (chloroform:methanol = 1:0 → 9:1) to obtain 23.8 mg of the present compound AA-1 as a white solid. Compound AA-1 of the present invention: 1H-NMR (CDCl3) δ: 0.92 (3H, d, J=6.7Hz), 1.01 (3H, s), 1.11 (1H, t, J=13Hz), 1.19 (3H, s), 1.49 (3H, s), 1.51-1.61 (3H, m), 1.77 (1H, d, J=13Hz), 1.69-1.79 (1H, m), 1.94 (1H, dd, J=13Hz, 4.3Hz), 2.02 (3H, s), 2.12 (1H, dd, J=13Hz, 4.9Hz), 2.22-2.36 (2H, m), 2.42 (1H, d, J=20Hz), 2.45 (1H, dd, J=6.4Hz, 5.8Hz), 2.54 (1H, dd, J=18Hz, 3.2Hz), 2.62-2.66 (1H, m), 2.72 (1H, dd, J=14Hz, 5.8Hz), 2.92 (1H, ddd, J=14Hz, 10Hz, 3.2Hz), 3.00 (1H, s), 3.24 (1H, d, J=6.8Hz), 3.83 (1H, d, J=20Hz), 3.84 (1H, t, J=6.8Hz), 4.27 (1H, s), 4.62 (1H, d, J=5.9Hz), 5.91 (1H, s).

[0115] Production Example 28 Compound AA-2 of the present invention was quantitatively obtained as a white solid according to Production Example 27, except that zoanthamine was used instead of norzoanthamine. Compound AA-2 of the present invention: 1H-NMR (CDCl3) δ: 0.92 (3H, d, J=6.3Hz), 0.97 (3H, s), 1.11 (1H, t, J=13Hz), 1.18 (3H, s), 1.19 (3H, d, J=6.9Hz), 1.51 (3H, s), 1.52-1.61 (3H, m), 1.77 (1H, d, J=13Hz), 1.69-1.78 (1H, m), 1.95 (1H, dd, J=13Hz, 3.9Hz), 2.01 (3H, s), 2.13 (1H, dd, J=14Hz, 5.1Hz), 2.19 (1H, dd, J=18Hz, 11Hz), 2.27-2.35 (1H, m), 2.42 (1H, d, J=21Hz), 2.49 (1H, dd, J=18Hz, 3.6Hz), 2.60 (1H, dd, J=14Hz, 5.3Hz), 3.06 (1H, dd, J=6.9Hz, 5.3Hz), 3.14 (1H, ddd, J=14Hz, 11Hz, 3.6Hz), 3.24 (1H, d, J=7.2Hz), 3.39 (1H, s), 3.83 (1H, d, J=21Hz), 3.85 (1H, t, J=7.2Hz), 4.28 (1H, s), 4.62 (1H, d, J=6.1Hz), 5.91(1H, s).

[0116] Production Example 29

[0117] 300 mg of norzoanthamine was dissolved in 10 mL of tetrahydrofuran, and 630 mg of triethylamine was added. The mixture was cooled in a dry ice-ethanol bath, and 823 mg of tert-butyldimethylsilyl trifluoromethanesulfonate was added, followed by stirring at -70°C for 3 hours. After completion of the reaction, 5 mL of saturated aqueous sodium bicarbonate solution was added at -70°C, and the mixture was then returned to room temperature and stirred at room temperature for 10 minutes. 10 mL of water was added, and the mixture was extracted three times with chloroform. The resulting organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (hexane:ethyl acetate = 4:1 → 1:2) to obtain 257 mg of compound AA-3a as a white solid.

[0118] 40 mg of compound AA-3a was dissolved in 1.5 mL of tetrahydrofuran and cooled in a salt-ice bath. 305 μL of lithium hexamethyldisilazane (LHMDS) (1.1 M tetrahydrofuran solution) was added, followed by stirring at 20°C for 1 hour. 106 μL of ethyl iodide was added, and the mixture was stirred at 20°C for 3 hours. After completion of the reaction, water was added, and the mixture was extracted three times with ethyl acetate. The resulting organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. 73.9 mg of tris(dimethylamino)sulfonium difluorotrimethylsilicate (TASF) dissolved in 2 mL of acetone was added to the resulting residue, and the mixture was stirred at room temperature for 1 hour. After completion of the reaction, 5 mL of phosphate buffer adjusted to pH 7 was added, and the mixture was extracted three times with ethyl acetate. The resulting organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The resulting residue was subjected to reverse phase column chromatography (water:acetonitrile=4:1→3:1) to obtain 6.0 mg of the present compound AA-3 as a pale yellow solid. Compound AA-3 of the present invention: 1 H-NMR (CDCl3) δ: 0.85 (3H, t, J=7.4Hz), 0.92 (3H, d, J=6.5Hz), 1.00 (6H, s), 1.10 (1H, t, J=13Hz), 1.21 (3H, s), 1.36-1.51 (3H, m), 1.66-1.81 (2H, m), 1.92 (1H, d, J=14Hz), 1.87-2.01 (3H, m), 2.01 (3H, s), 2.11 (1H, dd, J=13Hz, 5.0Hz), 2.16 (1H, d, J=14Hz), 2.19-2.23 (2H, m), 2.24-2.30 (1H, m), 2.37 (1H, d, J=20Hz), 2.41-2.47 (1H, m), 2.65 (1H, dd, J=13Hz, 5.6Hz), 2.80-2.85 (1H, m), 3.24 (1H, t, J=6.4Hz), 3.26 (1H, br s), 3.29 (1H, d, J=6.4Hz), 3.67 (1H, d, J=20Hz), 4.56 (1H, d, J=5.7Hz), 5.92(1H, s).

[0119] Preparation Example 29-1 A compound prepared in accordance with Preparation Example 29 and its physical properties are shown below. Compound A-1: 1 H-NMR (CDCl3) δ: 0.92 (3H, d, J=6.5Hz), 1.00 (6H, s), 1.10 (1H, t, J=13Hz), 1.19 (3H, s), 1.44-1.51 (2H, m), 1.69-1.80 (2H, m), 1.85-2.02 (2H, m), 1.92 (1H, d, J=14Hz), 2.02 (3H, s), 2.10 (1H, dd, J=13Hz, 5.1Hz), 2.18 (1H, d, J=14Hz), 2.23-2.31 (3H, m), 2.38 (1H, d, J=20Hz), 2.52-2.60 (1H, m), 2.79 (1H, dd, J=14Hz, 5.9Hz), 3.06-3.08 (1H, m), 3.23 (1H, s), 3.21-3.26 (1H, m), 3.29 (1H, d, J=6.1Hz), 3.70 (1H, d, J=20Hz), 3.91 (1H, dd, J=11Hz, 4.5Hz), 3.99 (1H, dd, J=11Hz, 6.4Hz), 4.55-4.57 (1H, m), 5.93 (1H, s).

[0120] Next, formulation examples of the present compounds and the compounds of the present invention are shown. Note that "parts" means "parts by weight." Furthermore, "Compound S" represents Compounds A-1 to A-23, B-1, B-2, C-1 to C-44, D-1, D-2, E-1 to E-5, F-1 to F-5, G-1, and G-2 of the present invention, as well as Compounds AA-1 to AA-3, BB-1, EE-1 to EE-7, and GG-1 to GG-3 of the present invention.

[0121] Formulation Example 1 35 parts of a mixture of polyoxyethylene alkyl ether sulfate ammonium salt and silica (weight ratio 1:1), 10 parts of any one of the present compounds S, and 55 parts of water are mixed and finely pulverized by a wet pulverization method to obtain a formulation.

[0122] Formulation Example 2 50 parts of any one of the present compounds S, 3 parts of calcium lignosulfonate, 2 parts of sodium lauryl sulfate, and 45 parts of silica are ground and mixed to obtain a formulation.

[0123] Formulation Example 3: A formulation is obtained by mixing 5 parts of any one of the present compounds S, 9 parts of polyoxyethylene styrylphenyl ether, 5 parts of polyoxyethylene decyl ether (number of ethylene oxide added: 5), 6 parts of calcium dodecylbenzenesulfonate, and 75 parts of xylene.

[0124] Formulation Example 4: 2 parts of any one of the present compounds S, 1 part of silica, 2 parts of calcium lignosulfonate, 30 parts of bentonite, and 65 parts of kaolin clay are pulverized and mixed, and an appropriate amount of water is added and kneaded. The mixture is granulated in a granulator and then dried to obtain a formulation.

[0125] Formulation Example 5 10 parts of any one of the present compounds S is mixed with a mixture of 18 parts of benzyl alcohol and 9 parts of DMSO, and 6.3 parts of GERONOL (registered trademark) TE250, 2.7 parts of Ethylan (registered trademark) NS-500LQ, and 54 parts of solvent naphtha are added thereto and mixed to obtain a formulation.

[0126] Formulation Example 6: 0.1 parts of any one of the present compounds S and 39.9 parts of kerosene are mixed and dissolved, placed in an aerosol container, and filled with 60 parts of liquefied petroleum gas (a mixture of propane, butane, and isobutane; saturated vapor pressure: 0.47 MPa (25°C)) to obtain a formulation.

[0127] Formulation Example 7: 0.2 parts of any one of the present compounds S, 50 parts of pyrethrum extract residue powder, 30 parts of Tabu powder, and 19.8 parts of wood flour are mixed, an appropriate amount of water is added, and the mixture is kneaded. The mixture is then extruded into a plate-shaped sheet, and then wound into a spiral shape using a die-cutting machine to obtain a formulation.

[0128] Next, the efficacy of the present compound and the compounds of the present invention against harmful arthropods and harmful nematodes will be shown by test examples. In the following test examples, the tests were carried out at 25°C. The untreated group refers to a group in which the same procedures as the treated group were carried out except that the test compound was not used.

[0129] Test Method 1: A test compound is formulated according to the method described in Formulation Example 5, and water containing 0.03% by volume of Syndyne (registered trademark) is added to this to prepare a diluted solution containing the test compound at a predetermined concentration. The diluted solution is sprayed at a rate of 20 mL per seedling on cabbage (Brassicae oleracea) seedlings (at the third to fourth true leaf stage) planted in a container. Ten third-instar larvae of the common cutworm are then released. After six days, the number of surviving insects is counted and the mortality rate is calculated using the following formula: Mortality rate (%) = (1 - number of surviving insects / 10) x 100

[0130] Test Example 1-1 A test was carried out according to Test Method 1 using the following compounds of the present invention and compounds of the present invention as test compounds at a predetermined concentration of 200 ppm. As a result, all of the following compounds of the present invention and compounds of the present invention showed insect mortality rates of 80% or more. Compounds of the present invention: A-1, A-18, A-19, B-1, B-2 Compounds of the present invention: AA-1, AA-2, AA-3, BB-1, EE-2, EE-3, EE-5, GG-3

[0131] Test Method 2: A test compound is formulated according to the method described in Formulation Example 5, and water containing 0.03% by volume of Syndyne (registered trademark) is added to prepare a diluted solution containing the test compound at a predetermined concentration. The diluted solution is sprayed at a rate of 20 mL per seedling on cabbage (Brassicae oleracea) seedlings (at the third to fourth true leaf stage) planted in a container. Ten third-instar diamondback moth larvae are then released. After six days, the number of surviving insects is counted and the mortality rate is calculated using the following formula: Mortality rate (%) = (1 - number of surviving insects / 10) x 100

[0132] Test Example 2-1 A test was carried out according to Test Method 2 using the following compounds of the present invention and compounds of the present invention as test compounds at a predetermined concentration of 200 ppm. As a result, all of the following compounds of the present invention and compounds of the present invention showed insect mortality rates of 80% or more. Compounds of the present invention: A-1, A-18, A-19, B-1, B-2, E-1 Compounds of the present invention: AA-1, AA-2, AA-3, BB-1, EE-2, EE-4, EE-5, EE-6

[0133] Test Method 3 A test compound is formulated according to the method described in Formulation Example 5, and water containing 0.03% by volume of Syndyne (registered trademark) is added to prepare a diluted solution containing the test compound at a predetermined concentration. Approximately 30 cotton aphids (all stages) are inoculated onto cucumber (Cucumis sativus) seedlings (at the second true leaf stage) planted in a container. One day later, the diluted solution is sprayed onto the seedlings at a rate of 10 mL per seedling. After a further five days, the number of surviving insects is counted, and the control titer is calculated using the following formula: Control titer (%) = {1 - (Cb x Tai) / (Cai x Tb)} x 100. The letters in the formula have the following meanings: Cb: number of test insects in the untreated area Cai: number of surviving insects at the time of investigation in the untreated area Tb: number of test insects in the treated area Tai: number of surviving insects at the time of investigation in the treated area

[0134] Test Example 3-1 A test was carried out according to Test Method 3 using the following compounds of the present invention and compounds of the present invention as test compounds at a predetermined concentration of 200 ppm. As a result, all of the following compounds of the present invention and compounds of the present invention showed a control value of 90% or more. Compounds of the present invention: A-1, A-18, A-19, B-1, B-2, E-1 Compounds of the present invention: AA-1, AA-2, AA-3, BB-1, EE-1, EE-2, EE-3, EE-5, GG-3

[0135] Test Method 4: A test compound is formulated according to the method described in Formulation Example 5, and water containing 0.03% by volume of Syndyne (registered trademark) is added to prepare a diluted solution containing the test compound at a predetermined concentration. The diluted solution is sprayed at a rate of 10 mL per seedling on rice (Oryza sativa) seedlings (at the second true leaf stage) planted in a container. Then, 20 third-instar larvae of the brown planthopper are released. After 6 days, the number of surviving insects is counted, and the mortality rate is calculated using the following formula: Mortality rate (%) = {1 - number of surviving insects / 20} x 100

[0136] Test Example 4-1 A test was carried out according to Test Method 4 using the following compounds of the present invention and compounds of the present invention as test compounds at a predetermined concentration of 200 ppm. As a result, all of the following compounds of the present invention and compounds of the present invention showed insect mortality rates of 90% or more. Compounds of the present invention: A-1, A-18, A-19, B-2, E-1 Compounds of the present invention: AA-1, AA-2, AA-3, EE-2, EE-3, EE-4, EE-5, GG-1, GG-3

[0137] Test Method 5: A test compound is formulated according to the method described in Formulation Example 5, and water containing 0.03% by volume of Syndyne (registered trademark) is added to prepare a diluted solution containing the test compound at a predetermined concentration. The diluted solution is sprayed at a rate of 10 mL per seedling on cabbage (Brassicae oleracea) seedlings (at the second true leaf stage) planted in a container. The second true leaves are then cut off and placed in a container, into which approximately 20 larvae of western flower thrips are released. After 6 days, the number of surviving insects is counted, and the mortality rate is calculated using the following formula: Mortality rate (%) = {1 - number of surviving insects / 20} x 100

[0138] Test Example 5-1 A test was carried out according to Test Method 5 using the following compounds of the present invention and compounds of the present invention as test compounds at a predetermined concentration of 200 ppm. As a result, all of the following compounds of the present invention and compounds of the present invention showed insect mortality rates of 90% or more. Compounds of the present invention: A-18, A-19, B-1, E-1 Compounds of the present invention: AA-1, AA-2, BB-1, EE-4, EE-1, EE-2, EE-3, EE-5, EE-6, GG-3

[0139] Test Method 6 A test compound is formulated according to the method described in Formulation Example 5, and water containing 0.03% by volume of Syndyne (registered trademark) is added to prepare a diluted solution containing the test compound at a predetermined concentration. Adult Bemisia tabaci are released onto tomato (Lycopersicon esculentum) seedlings planted in a container and allowed to lay eggs for approximately 24 hours. The seedlings are stored for 8 days, and larvae are allowed to hatch from the laid eggs. The diluted solution is sprayed onto the seedlings at a rate of 10 mL per seedling. After 7 days, the number of surviving insects is counted, and the control titer is calculated using the following formula: Control titer (%) = {1 - (Cb x Tai) / (Cai x Tb)} x 100. The letters in the formula have the following meanings: Cb: number of insects in the untreated area immediately before treatment Cai: number of surviving insects at the time of inspection in the untreated area Tb: number of insects in the treated area immediately before treatment Tai: number of surviving insects at the time of inspection in the treated area

[0140] Test Example 6-1 A test was carried out according to Test Method 6 using the following compounds of the present invention and compounds of the present invention as test compounds at a predetermined concentration of 200 ppm. As a result, all of the following compounds of the present invention and compounds of the present invention showed a control value of 90% or more. Compounds of the present invention: A-1, E-1 Compounds of the present invention: AA-1, AA-2, AA-3, EE-1, EE-2

[0141] Test Method 7: 60 mg of a test compound was dissolved in 600 μL of acetone containing 5% Tween® 20, and water was added to prepare a dilution containing the test compound at a predetermined concentration. 20 mL of the dilution was mixed with 400 mL of soil contaminated with nematodes, and the roots of healthy tomato seedlings (at the 3- to 4-leaf stage) were transplanted thereto. Immediately after transplantation, 40 mL of the dilution was irrigated into the soil. After 10 days, the roots were removed from the soil and washed with water. The extent of root damage (degree of root galls) was assessed according to Zeck's root gall index (Zeck, WM (1971): Pflanzenschutz-Nachrichten. Bayer AG, 24, 141-144). [Zeck's root gall index] 0: No root galls were observed. 1: A few small root galls could be observed with careful observation. 2: Several small galls similar to those in 1 are easily visible. 3: There are many small galls, some of which have fused together. Root function is largely intact. 4: There are many small galls, and some large galls. Most of the roots are functioning. 5: 25% of the roots are heavily clubbed and non-functioning. 6: 50% of the roots are heavily clubbed and non-functioning. 7: 75% of the roots are heavily clubbed, and the ability to regenerate has been lost. 8: There are no healthy roots, and the plant's nutrient absorption is inhibited. The stems and leaves are still green. 9: The root system is completely covered with galls and is rotting. The plant is dying. 10: Both the plant and the roots are dead.

[0142] Test Example 7 A test was carried out according to Test Method 7 using Compound AA-1 of the present invention as a test compound at a predetermined concentration of 1000 ppm. As a result, the root club index of the treatment group with Compound AA-1 of the present invention was "1". On the other hand, the root club index of the untreated group was "4". From the above, Compound AA-1 of the present invention reduced root club formation.

[0143] Test Method 8: After dissolving the test compound in acetone containing a surfactant, pour it into a 20 mL container and dissolve the test compound at a concentration of 10 mg / mL. 2 , surfactant 40 mg / m 2 The inner surface of the container is evenly coated with the solution so that the coating becomes 0.01g, and then dried. Five adult female Culex mosquitoes are placed in the container and the lid is closed. After a predetermined time has passed, the condition of the Culex mosquitoes is examined and the mortality rate is calculated using the following formula: Mortality rate (%) = (number of dead insects / number of test insects) x 100

[0144] Test Example 8 The results of a test carried out according to Test Method 8 are shown below. The test was carried out for 1 day, and the following compounds of the present invention were used as test compounds. As a result, the following compounds of the present invention and the compounds of the present invention all showed insect mortality of 80% or more. Compounds of the present invention: A-19, B-1, B-2, E-1 Compounds of the present invention: AA-1, AA-2, AA-3, BB-1, EE-1, EE-2, EE-3, EE-4, EE-5, EE-6, GG-1, GG-2, GG-3

[0145] The present compound and the compound of the present invention exhibit excellent control effects against harmful arthropods or harmful nematodes.

Claims

1. Formula (I) 【Chemistry 1】 [During the ceremony, R 1 is a hydrogen atom, a C1-C3 alkyl group, or CH 2 OR A1 represents R 2 is OR A2 represents R 3 represents a hydrogen atom, R 4 is a methyl group or CH 2 OR A3 represents R 5 is a methyl group or CH 2 OR A4 represents R 6 is a hydrogen atom or OR A5 represents R 7 represents a hydrogen atom, R 8 represents a hydrogen atom, a halogen atom, a methoxy group, or OR A6 represents R 9 is a methyl group or CH 2 OR A7 represents R 10 is a hydrogen atom or OR A8 represents R 11 is OR A9 represents R 12 is a hydrogen atom or OR A10 represents R 13 represents a hydrogen atom, a dichloromethyl group, a hydroxy(methoxy)methyl group, a hydroxy(ethoxy)methyl group, or OR A11 represents R 14 represents a hydrogen atom, R 15 is a hydrogen atom or OR A12 represents R 16 represents a hydrogen atom, a halogen atom, or OR A13 represents R 17 represents a hydrogen atom, R 18 is a methyl group or CH 2 OR A14 represents R 19 represents a hydrogen atom, R 20 is a hydrogen atom or OR A15 represents R 21 is a methyl group, CH 2 OR A16 , or CH 2 NHCH 2 C(O)OCH 3 represents R 22 is a hydrogen atom or OR A17 represents R 23 is a hydrogen atom or OR A18 represents R 24 is a hydrogen atom, a C1-C3 alkoxy group, or OR A19 represents R 25 represents a hydrogen atom, R 26 is a hydrogen atom or OR A20 represents R 27 represents a C1-C3 alkoxy group or a hydroxy group, R A1 , R A2 , R A3 , R A4 , R A5 , R A6 , R A7 , R A8 , R A9 , R A10 , R A11 , R A12 , R A13 , R A14 , R A15 , R A16 , R A17 , R A18 , R A19 , and R A20 are the same or different and represent a hydrogen atom, a (C1-C6 alkyl)carbonyl group, or a (C3-C6 cycloalkyl)carbonyl group; R 1 and R 27 Together # 1 -CH 2 -O- may be formed, 1 is R 1 represents the bonding position with the carbon atom to which it is bonded, R 2 and R 3 and may together form an oxo group, R 3 and R 18 Together # 3 —O—CHR B1 - may be formed, 3 is R 3 represents the bonding position with the carbon atom to which it is bonded, R 4 and R 27 Together # 4 -CH 2 -O- may be formed, 4 is R 4 represents the bonding position with the carbon atom to which it is bonded, R 6 and R 27 and may together form a bond, R 7 and R 11 and may be taken together to form —O—, R 13 and R 14 and may together form an oxo group, R 15 and R 16 and may form a double bond together with the carbon atom to which they are attached, R 15 and R 18 Together # 15 —O—CHR B2 - may be formed, 15 is R 15 represents the bonding position with the carbon atom to which it is bonded, R 15 and R 27 and may be taken together to form —O—, R 16 and R 17 and may together form an oxo group, R 18 and R 22 Together # 18 -CH 2 -O- may be formed, 18 is R 18 represents the bonding position with the carbon atom to which it is bonded, R 18 and R 23 Together with -CH 2 - may be formed, R 19 , R 20 , R 22 , R 23 , R 25 , and R 26 may form a benzene ring together with the carbon atom to which they are attached, R 21 and R 22 Together = CH 2 and R 22 and R 23 and may form a double bond together with the carbon atom to which they are attached, R 24 and R 25 and may together form an oxo group, R B1 and R B2 are the same or different and represent a hydrogen atom, a C1-C3 alkoxy group, or a hydroxy group. However, zoanthamin, norzoanthamin, zoanthaminone, and norzoanthaminone are excluded. A method for controlling harmful arthropods or harmful nematodes, which comprises applying an effective amount of a compound represented by the following formula (I): or an N-oxide or a salt thereof to harmful arthropods or harmful nematodes or to a habitat of harmful arthropods or harmful nematodes.

2. In formula (I), R 1 , R 2 , R 3 , R 4 , R 6 , R 7 , R 11 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , R 21 , R 22 , R 23 , R 24 , R 25 , R 26 , and R 27 The method according to claim 1, wherein the combination of is any combination of a to g: a:R 1 is a hydrogen atom, a C1-C3 alkyl group, or CH 2 OR A1 and R 2 is OR A2 and R 3 is a hydrogen atom, and R 2 and R 3 may be taken together to form an oxo group, and R 4 is a methyl group or CH 2 OR A3 and R 6 is a hydrogen atom or OR A5 and R 7 and R 11 and together form -O-, and R 13 is a hydrogen atom, a dichloromethyl group, a hydroxy(methoxy)methyl group, a hydroxy(ethoxy)methyl group, or OR A11 and R 14 is a hydrogen atom, and R 13 and R 14 may be taken together to form an oxo group, and R 15 and R 27 and together form -O-, and R 16 is a hydrogen atom, a halogen atom, or OR A13 and R 17 is a hydrogen atom, and R 16 and R 17 may be taken together to form an oxo group, and R 18 is a methyl group, or CH 2 OR A14 and R 19 is a hydrogen atom, and R 20 is a hydrogen atom or OR A15 and R 21 is a methyl group, CH 2 OR A16 , or CH 2 NHCH 2 C(O)OCH 3 and R 22 is a hydrogen atom or OR A17 and R 21 and R 22 Together = CH 2 and R 23 is a hydrogen atom, or OR A18 and R 18 and R 23 Together with -CH 2 - may be formed, and R 22 and R 23 and may form a double bond together with the carbon atom to which they are attached, and R 24 is a hydrogen atom, a C1-C3 alkoxy group, or OR A19 and R 25 is a hydrogen atom, and R 24 and R 25 may be taken together to form an oxo group, and R 26 is a hydrogen atom or OR A20 A combination in which: b:R 1 is a hydrogen atom, a C1-C3 alkyl group, or CH 2 OR A1 and R 2 and R 3 and together form an oxo group, and R 4 is a methyl group or CH 2 OR A3 and R 6 is a hydrogen atom or OR A5 and R 7 and R 11 and together form -O-, and R 13 is a hydrogen atom, a dichloromethyl group, a hydroxy(methoxy)methyl group, a hydroxy(ethoxy)methyl group, or OR A11 and R 14 is a hydrogen atom, and R 15 and R 27 and together form -O-, and R 16 is a hydrogen atom, a halogen atom, or OR A13 and R 17 is a hydrogen atom, and R 18 is a methyl group, or CH 2 OR A14 and R 19 , R 20 , R 22 , R 23 , R 25 , and R 26 form a benzene ring together with the carbon atoms to which they are attached, and R 21 is a methyl group, CH 2 OR A16 , or CH 2 NHCH 2 C(O)OCH 3 and R 24 is a C1-C3 alkoxy group, or OR A19 A combination in which: c:R 1 is a hydrogen atom, a C1-C3 alkyl group, or CH 2 OR A1 and R 2 is OR A2 and R 3 is a hydrogen atom, and R 2 and R 3 may be taken together to form an oxo group, and R 3 and R 18 Together # 3 —O—CHR B1 - may be formed, and R 4 and R 27 Together # 4 -CH 2 -O-, and R 6 is a hydrogen atom or OR A5 and R 7 and R 11 and together form -O-, and R 13 is a hydrogen atom, a dichloromethyl group, a hydroxy(methoxy)methyl group, a hydroxy(ethoxy)methyl group, or OR A11 and R 14 is a hydrogen atom, and R 15 is a hydrogen atom or OR A12 and R 16 is a hydrogen atom, a halogen atom, or OR A13 and R 15 and R 16 and may form a double bond together with the carbon atom to which they are attached, and R 17 is a hydrogen atom, and R 16 and R 17 may be taken together to form an oxo group, and R 18 is a methyl group, or CH 2 OR A14 and R 15 and R 18 Together # 15 —O—CHR B2 - may be formed, and R 19 is a hydrogen atom, and R 20 is a hydrogen atom or OR A15 and R 21 is a methyl group, CH 2 OR A16 , or CH 2 NHCH 2 C(O)OCH 3 and R 22 is a hydrogen atom or OR A17 and R 18 and R 22 Together # 18 -CH 2 -O- may be formed, and R 23 is a hydrogen atom, or OR A18 and R 22 and R 23 and may form a double bond together with the carbon atom to which they are attached, and R 24 and R 25 and together form an oxo group, and R 26 is a hydrogen atom or OR A20 A combination in which: d:R 1 and R 27 Together # 1 -CH 2 -O-, and R 2 and R 3 and together form an oxo group, and R 4 is a methyl group or CH 2 OR A3 and R 6 is a hydrogen atom or OR A5 and R 7 and R 11 and together form -O-, and R 13 is a hydrogen atom, a dichloromethyl group, a hydroxy(methoxy)methyl group, a hydroxy(ethoxy)methyl group, or OR A11 and R 14 is a hydrogen atom, and R 15 is a hydrogen atom or OR A12 and R 16 is a hydrogen atom, a halogen atom, or OR A13 and R 17 is a hydrogen atom, and R 16 and R 17 may be taken together to form an oxo group, and R 18 is a methyl group, or CH 2 OR A14 and R 19 is a hydrogen atom, and R 20 is a hydrogen atom or OR A15 and R 21 is a methyl group, CH 2 OR A16 , or CH 2 NHCH 2 C(O)OCH 3 and R 22 and R 23 and form a double bond together with the carbon atom to which they are attached, and R 24 and R 25 and together form an oxo group, and R 26 is a hydrogen atom or OR A20 A combination in which: e:R 1 is a hydrogen atom, a C1-C3 alkyl group, or CH 2 OR A1 and R 2 and R 3 and together form an oxo group, and R 4 is a methyl group or CH 2 OR A3 and R 6 is a hydrogen atom or OR A5 and R 7 and R 11 and together form -O-, and R 13 is a hydrogen atom, a dichloromethyl group, a hydroxy(methoxy)methyl group, a hydroxy(ethoxy)methyl group, or OR A11 and R 14 is a hydrogen atom, and R 15 is a hydrogen atom or OR A12 and R 16 is a hydrogen atom, a halogen atom, or OR A13 and R 15 and R 16 and may form a double bond together with the carbon atom to which they are attached, and R 17 is a hydrogen atom, and R 18 is a methyl group, or CH 2 OR A14 and R 19 is a hydrogen atom, and R 20 is a hydrogen atom or OR A15 and R 21 is a methyl group, CH 2 OR A16 , or CH 2 NHCH 2 C(O)OCH 3 and R 22 is a hydrogen atom or OR A17 and R 23 is a hydrogen atom, or OR A18 and R 22 and R 23 and may form a double bond together with the carbon atom to which they are attached, and R 24 is a hydrogen atom, a C1-C3 alkoxy group, or OR A19 and R 25 is a hydrogen atom, and R 24 and R 25 may be taken together to form an oxo group, and R 26 is a hydrogen atom or OR A20 and R 27 is a C1-C3 alkoxy group or a hydroxy group f:R 1 is a hydrogen atom, a C1-C3 alkyl group, or CH 2 OR A1 and R 2 and R 3 and together form an oxo group, and R 4 is a methyl group or CH 2 OR A3 and R 6 and R 27 and together form a bond, and R 7 and R 11 and together form -O-, and R 13 is a hydrogen atom, a dichloromethyl group, a hydroxy(methoxy)methyl group, a hydroxy(ethoxy)methyl group, or OR A11 and R 14 is a hydrogen atom, and R 15 is a hydrogen atom or OR A12 and R 16 is a hydrogen atom, a halogen atom, or OR A13 and R 17 is a hydrogen atom, and R 18 is a methyl group, or CH 2 OR A14 and R 19 is a hydrogen atom, and R 20 is a hydrogen atom or OR A15 and R 21 is a methyl group, CH 2 OR A16 , or CH 2 NHCH 2 C(O)OCH 3 and R 22 is a hydrogen atom or OR A17 and R 23 is a hydrogen atom, or OR A18 and R 22 and R 23 and may form a double bond together with the carbon atom to which they are attached, and R 24 is a hydrogen atom, a C1-C3 alkoxy group, or OR A19 and R 25 is a hydrogen atom, and R 24 and R 25 may be taken together to form an oxo group, and R 26 is a hydrogen atom or OR A20 and g:R 1 is a hydrogen atom, a C1-C3 alkyl group, or CH 2 OR A1 and R 2 and R 3 and together form an oxo group, and R 4 is a methyl group or CH 2 OR A3 and R 6 is a hydrogen atom or OR A5 and R 7 is a hydrogen atom, and R 11 is OR A9 and R 13 is a hydrogen atom, a dichloromethyl group, a hydroxy(methoxy)methyl group, a hydroxy(ethoxy)methyl group, or OR A11 and R 14 is a hydrogen atom, and R 15 is a hydrogen atom or OR A12 and R 16 is a hydrogen atom, a halogen atom, or OR A13 and R 17 is a hydrogen atom, and R 18 is a methyl group, or CH 2 OR A14 and R 19 is a hydrogen atom, and R 20 is a hydrogen atom or OR A15 and R 21 is a methyl group, CH 2 OR A16 , or CH 2 NHCH 2 C(O)OCH 3 and R 22 is a hydrogen atom or OR A17 and R 23 is a hydrogen atom, or OR A18 and R 22 and R 23 and may form a double bond together with the carbon atom to which they are attached, and R 24 and R 25 and together form an oxo group, and R 26 is a hydrogen atom or OR A20 and R 27 is a C1-C3 alkoxy group or a hydroxy group.

3. In formula (I), R 5 is a methyl group, and R 1 , R 2 , R 3 , R 4 , R 6 , R 7 , R 11 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , R 21 , R 22 , R 23 , R 24 , R 25 , R 26 , and R 27 The combination of a 1 ~g 1 10. The method of claim 1, wherein the combination of: a 1 :R 1 is a hydrogen atom, a C1-C3 alkyl group, or CH 2 OR A1 and R 2 is OR A2 and R 3 is a hydrogen atom, and R 2 and R 3 may be taken together to form an oxo group, and R 4 is a methyl group, and R 6 is a hydrogen atom, and R 7 and R 11 and together form -O-, and R 13 is a hydrogen atom, and R 14 is a hydrogen atom, and R 13 and R 14 may be taken together to form an oxo group, and R 15 and R 27 and together form -O-, and R 16 is a hydrogen atom, a halogen atom, or OR A13 and R 17 is a hydrogen atom, and R 16 and R 17 may be taken together to form an oxo group, and R 18 is a methyl group, and R 19 is a hydrogen atom, and R 20 is a hydrogen atom, and R 21 is a methyl group or CH 2 OR A16 and R 22 is a hydrogen atom or OR A17 and R 21 and R 22 Together = CH 2 and R 23 is a hydrogen atom, or OR A18 and R 18 and R 23 Together with -CH 2 - may be formed, and R 22 and R 23 and may form a double bond together with the carbon atom to which they are attached, and R 24 is a hydrogen atom or OR A19 and R 25 is a hydrogen atom, and R 24 and R 25 may be taken together to form an oxo group, and R 26 is a hydrogen atom; b 1 :R 1 is a hydrogen atom or a methyl group, and R 2 and R 3 and together form an oxo group, and R 4 is a methyl group, and R 6 is a hydrogen atom, and R 7 and R 11 and together form -O-, and R 13 is a hydrogen atom, and R 14 is a hydrogen atom, and R 15 and R 27 and together form -O-, and R 16 is a hydrogen atom or a halogen atom, and R 17 is a hydrogen atom, and R 18 is a methyl group, and R 19 , R 20 , R 22 , R 23 , R 25 , and R 26 form a benzene ring together with the carbon atoms to which they are attached, and R 21 is a methyl group, and R 24 is a C1-C3 alkoxy group or OR A19 A combination in which: c 1 :R 1 is a methyl group, and R 2 is OR A2 and R 3 is a hydrogen atom, and R 2 and R 3 may be taken together to form an oxo group, and R 3 and R 18 Together # 3 —O—CHR B1 - may be formed, and R 4 and R 27 Together # 4 -CH 2 -O-, and R 6 is a hydrogen atom or OR A5 and R 7 and R 11 and together form -O-, and R 13 is a hydrogen atom or OR A11 and R 14 is a hydrogen atom, and R 15 is a hydrogen atom, and R 16 is a hydrogen atom, a halogen atom, or OR A13 and R 15 and R 16 and may form a double bond together with the carbon atom to which they are attached, and R 17 is a hydrogen atom, and R 16 and R 17 may be taken together to form an oxo group, and R 18 is a methyl group, and R 15 and R 18 Together # 15 —O—CHR B2 - may be formed, and R 19 is a hydrogen atom, and R 20 is a hydrogen atom or OR A15 and R 21 is a methyl group, CH 2 OR A16 , or CH 2 NHCH 2 C(O)OCH 3 and R 22 is a hydrogen atom, and R 18 and R 22 Together # 18 -CH 2 -O- may be formed, and R 23 is a hydrogen atom, and R 22 and R 23 and may form a double bond together with the carbon atom to which they are attached, and R 24 and R 25 and together form an oxo group, and R 26 is a hydrogen atom or OR A20 A combination in which: d 1 :R 1 and R 27 Together # 1 -CH 2 -O-, and R 2 and R 3 and together form an oxo group, and R 4 is a methyl group, and R 6 is a hydrogen atom, and R 7 and R 11 and together form -O-, and R 13 is a hydrogen atom, and R 14 is a hydrogen atom, and R 15 is a hydrogen atom or OR A12 and R 16 is a hydrogen atom, a halogen atom, or OR A13 and R 17 is a hydrogen atom, and R 16 and R 17 may be taken together to form an oxo group, and R 18 is a methyl group, and R 19 is a hydrogen atom, and R 20 is a hydrogen atom, and R 21 is a methyl group, and R 22 and R 23 and form a double bond together with the carbon atom to which they are attached, and R 24 and R 25 and together form an oxo group, and R 26 is a hydrogen atom; e 1 :R 1 is a hydrogen atom or a C1-C3 alkyl group, and R 2 and R 3 and together form an oxo group, and R 4 is a methyl group, and R 6 is a hydrogen atom, and R 7 and R 11 and together form -O-, and R 13 is a hydrogen atom, a dichloromethyl group, a hydroxy(methoxy)methyl group, or a hydroxy(ethoxy)methyl group, and R 14 is a hydrogen atom, and R 15 is a hydrogen atom, and R 16 is a hydrogen atom, a halogen atom, or OR A13 and R 15 and R 16 and may form a double bond together with the carbon atom to which they are attached, and R 17 is a hydrogen atom, and R 18 is a methyl group, and R 19 is a hydrogen atom, and R 20 is a hydrogen atom, and R 21 is a methyl group, and R 22 is a hydrogen atom, and R 23 is a hydrogen atom, and R 22 and R 23 and may form a double bond together with the carbon atom to which they are attached, and R 24 is OR A19 and R 25 is a hydrogen atom, and R 24 and R 25 may be taken together to form an oxo group, and R 26 is a hydrogen atom, and R 27 is a C1-C3 alkoxy group or a hydroxy group; f 1 :R 1 is a hydrogen atom or a C1-C3 alkyl group, and R 2 and R 3 and together form an oxo group, and R 4 is a methyl group, and R 6 and R 27 and together form a bond, and R 7 and R 11 and together form -O-, and R 13 is a hydrogen atom, and R 14 is a hydrogen atom, and R 15 is a hydrogen atom, and R 16 is a hydrogen atom, a halogen atom, or OR A13 and R 17 is a hydrogen atom, and R 18 is a methyl group, and R 19 is a hydrogen atom, and R 20 is a hydrogen atom, and R 21 is a methyl group, and R 22 is a hydrogen atom, and R 23 is a hydrogen atom, and R 22 and R 23 and may form a double bond together with the carbon atom to which they are attached, and R 24 is OR A19 and R 25 is a hydrogen atom, and R 24 and R 25 may be taken together to form an oxo group, and R 26 is a hydrogen atom; and g 1 :R 1 is a hydrogen atom or a C1-C3 alkyl group, and R 2 and R 3 and together form an oxo group, and R 4 is a methyl group, and R 6 is a hydrogen atom, and R 7 is a hydrogen atom, and R 11 is OR A9 and R 13 is a hydrogen atom, and R 14 is a hydrogen atom, and R 15 is a hydrogen atom, and R 16 is a hydrogen atom, a halogen atom, or OR A13 and R 17 is a hydrogen atom, and R 18 is a methyl group, and R 19 is a hydrogen atom, and R 20 is a hydrogen atom, and R 21 is a methyl group, and R 22 is a hydrogen atom, and R 23 is a hydrogen atom, and R 22 and R 23 and may form a double bond together with the carbon atom to which they are attached, and R 24 and R 25 and together form an oxo group, and R 26 is a hydrogen atom, and R 27 is a C1-C3 alkoxy group or a hydroxy group.

4. In formula (I), R 5 is a methyl group, and R 8 is a hydrogen atom, a halogen atom, a methoxy group, or a hydroxy group, and R 9 is a methyl group or CH 2 OH and R 10 is a hydrogen atom, an acetyloxy group, or a hydroxy group, and R 12 The method of claim 1 , wherein is a hydrogen atom or a hydroxy group.

5. In formula (I), R A2 is a hydrogen atom, and R A5 is a hydrogen atom, and R A8 is a hydrogen atom or an acetyl group, and R A9 is a hydrogen atom, and R A11 is a hydrogen atom, and R A12 is a hydrogen atom, and R A13 is a hydrogen atom, and R A15 is a hydrogen atom, and R A16 is a hydrogen atom, and R A17 is a hydrogen atom, and R A18 is a hydrogen atom, and R A19 is a hydrogen atom or an acetyl group, and R A20 is a hydrogen atom, and R B1 is a hydrogen atom or a methoxy group, and R B2 is a hydrogen atom or a methoxy group, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , R 21 , R 22 , R 23 , R 24 , R 25 , R 26 , and R 27 The combination of a 2 ~g 2 10. The method of claim 1, wherein the combination of: a 2 :R 1 is a hydrogen atom, a C1-C3 alkyl group, or CH 2 OH and R 2 is OR A2 and R 3 is a hydrogen atom, and R 2 and R 3 may be taken together to form an oxo group, and R 4 is a methyl group, and R 5 is a methyl group, and R 6 is a hydrogen atom, and R 7 and R 11 and together form -O-, and R 8 is a hydrogen atom, and R 9 is a methyl group or CH 2 OH and R 10 is a hydrogen atom or OR A8 and R 12 is a hydrogen atom or a hydroxy group, and R 13 is a hydrogen atom, and R 14 is a hydrogen atom, and R 13 and R 14 may be taken together to form an oxo group, and R 15 and R 27 and together form -O-, and R 16 is a hydrogen atom, a halogen atom, or OR A13 and R 17 is a hydrogen atom, and R 16 and R 17 may be taken together to form an oxo group, and R 18 is a methyl group, and R 19 is a hydrogen atom, and R 20 is a hydrogen atom, and R 21 is a methyl group or CH 2 OR A16 and R 22 is a hydrogen atom or OR A17 and R 21 and R 22 Together = CH 2 and R 23 is a hydrogen atom, or OR A18 and R 18 and R 23 Together with -CH 2 - may be formed, and R 22 and R 23 and may form a double bond together with the carbon atom to which they are attached, and R 24 is a hydrogen atom or a hydroxy group, and R 25 is a hydrogen atom, and R 24 and R 25 may be taken together to form an oxo group, and R 26 is a hydrogen atom; b 2 :R 1 is a hydrogen atom or a methyl group, and R 2 and R 3 and together form an oxo group, and R 4 is a methyl group, and R 5 is a methyl group, and R 6 is a hydrogen atom, and R 7 and R 11 and together form -O-, and R 8 is a hydrogen atom, and R 9 is a methyl group, and R 10 is a hydrogen atom, and R 12 is a hydrogen atom, and R 13 is a hydrogen atom, and R 14 is a hydrogen atom, and R 15 and R 27 and together form -O-, and R 16 is a hydrogen atom or a halogen atom, and R 17 is a hydrogen atom, and R 18 is a methyl group, and R 19 , R 20 , R 22 , R 23 , R 25 , and R 26 form a benzene ring together with the carbon atoms to which they are attached, and R 21 is a methyl group, and R 24 is a C1-C3 alkoxy group or OR A19 A combination in which: c 2 :R 1 is a methyl group, and R 2 is OR A2 and R 3 is a hydrogen atom, and R 2 and R 3 may be taken together to form an oxo group, and R 3 and R 18 Together # 3 —O—CHR B1 - may be formed, and R 4 and R 27 Together # 4 -CH 2 -O-, and R 5 is a methyl group, and R 6 is a hydrogen atom or OR A5 and R 7 and R 11 and together form -O-, and R 8 is a hydrogen atom, a halogen atom, a methoxy group, or a hydroxy group, and R 9 is a methyl group or CH 2 OH and R 10 is a hydrogen atom or a hydroxy group, and R 12 is a hydrogen atom, and R 13 is a hydrogen atom or OR A11 and R 14 is a hydrogen atom, and R 15 is a hydrogen atom, and R 16 is a hydrogen atom, a halogen atom, or OR A13 and R 15 and R 16 and may form a double bond together with the carbon atom to which they are attached, and R 17 is a hydrogen atom, and R 16 and R 17 may be taken together to form an oxo group, and R 18 is a methyl group, and R 15 and R 18 Together # 15 —O—CHR B2 - may be formed, and R 19 is a hydrogen atom, and R 20 is a hydrogen atom or OR A15 and R 21 is a methyl group, CH 2 OR A16 , or CH 2 NHCH 2 C(O)OCH 3 and R 22 is a hydrogen atom, and R 18 and R 22 Together # 18 -CH 2 -O- may be formed, and R 23 is a hydrogen atom, and R 22 and R 23 and may form a double bond together with the carbon atom to which they are attached, and R 24 and R 25 and together form an oxo group, and R 26 is a hydrogen atom or OR A20 A combination in which: d 2 :R 1 and R 27 Together # 1 -CH 2 -O-, and R 2 and R 3 and together form an oxo group, and R 4 is a methyl group, and R 5 is a methyl group, and R 6 is a hydrogen atom, and R 7 and R 11 and together form -O-, and R 8 is a hydrogen atom, and R 9 is a methyl group, and R 10 is a hydrogen atom or a hydroxy group, and R 12 is a hydrogen atom, and R 13 is a hydrogen atom, and R 14 is a hydrogen atom, and R 15 is a hydrogen atom or OR A12 and R 16 is a hydrogen atom, a halogen atom, or OR A13 and R 17 is a hydrogen atom, and R 16 and R 17 may be taken together to form an oxo group, and R 18 is a methyl group, and R 19 is a hydrogen atom, and R 20 is a hydrogen atom, and R 21 is a methyl group, and R 22 and R 23 and form a double bond together with the carbon atom to which they are attached, and R 24 and R 25 and together form an oxo group, and R 26 is a hydrogen atom; e 2 :R 1 is a hydrogen atom or a C1-C3 alkyl group, and R 2 and R 3 and together form an oxo group, and R 4 is a methyl group, and R 5 is a methyl group, and R 6 is a hydrogen atom, and R 7 and R 11 and together form -O-, and R 8 is a hydrogen atom, and R 9 is a methyl group, and R 10 is a hydrogen atom, and R 12 is a hydrogen atom, and R 13 is a hydrogen atom, a dichloromethyl group, a hydroxy(methoxy)methyl group, or a hydroxy(ethoxy)methyl group, and R 14 is a hydrogen atom, and R 15 is a hydrogen atom, and R 16 is a hydrogen atom or a halogen atom, and R 15 and R 16 and may form a double bond together with the carbon atom to which they are attached, and R 17 is a hydrogen atom, and R 18 is a methyl group, and R 19 is a hydrogen atom, and R 20 is a hydrogen atom, and R 21 is a methyl group, and R 22 is a hydrogen atom, and R 23 is a hydrogen atom, and R 22 and R 23 and may form a double bond together with the carbon atom to which they are attached, and R 24 is a hydroxy group, and R 25 is a hydrogen atom, and R 24 and R 25 may be taken together to form an oxo group, and R 26 is a hydrogen atom, and R 27 is a C1-C3 alkoxy group or a hydroxy group; f 2 :R 1 is a hydrogen atom or a C1-C3 alkyl group, and R 2 and R 3 and together form an oxo group, and R 4 is a methyl group, and R 5 is a methyl group, and R 6 and R 27 and together form a bond, and R 7 and R 11 and together form -O-, and R 8 is a hydrogen atom, and R 9 is a methyl group, and R 10 is a hydrogen atom, and R 12 is a hydrogen atom, and R 13 is a hydrogen atom, and R 14 is a hydrogen atom, and R 15 is a hydrogen atom, and R 16 is a hydrogen atom or a halogen atom, and R 17 is a hydrogen atom, and R 18 is a methyl group, and R 19 is a hydrogen atom, and R 20 is a hydrogen atom, and R 21 is a methyl group, and R 22 is a hydrogen atom, and R 23 is a hydrogen atom, and R 22 and R 23 and may form a double bond together with the carbon atom to which they are attached, and R 24 is OR A19 and R 25 is a hydrogen atom, and R 24 and R 25 may be taken together to form an oxo group, and R 26 is a hydrogen atom; and g 2 :R 1 is a hydrogen atom or a C1-C3 alkyl group, and R 2 and R 3 and together form an oxo group, and R 4 is a methyl group, and R 5 is a methyl group, and R 6 is a hydrogen atom, and R 7 is a hydrogen atom, and R 8 is a hydrogen atom, and R 9 is a methyl group, and R 10 is a hydrogen atom, and R 11 is OR A9 and R 12 is a hydrogen atom, and R 13 is a hydrogen atom, and R 14 is a hydrogen atom, and R 15 is a hydrogen atom, and R 16 is a hydrogen atom, a halogen atom, or OR A13 and R 17 is a hydrogen atom, and R 18 is a methyl group, and R 19 is a hydrogen atom, and R 20 is a hydrogen atom, and R 21 is a methyl group, and R 22 is a hydrogen atom, and R 23 is a hydrogen atom, and R 22 and R 23 and may form a double bond together with the carbon atom to which they are attached, and R 24 and R 25 and together form an oxo group, and R 26 is a hydrogen atom, and R 27 is a C1-C3 alkoxy group or a hydroxy group.

6. A composition for controlling harmful arthropods or harmful nematodes, comprising the compound represented by formula (I) according to any one of claims 1 to 5, or an N-oxide thereof, or a salt thereof.

7. The composition according to claim 6, further comprising one or more components selected from the group consisting of group (a), group (b), group (c), group (d), and group (e): Group (a): A group consisting of insecticidal active ingredients, acaricidal active ingredients and nematocidal active ingredients; Group (b): bactericidal active ingredient; Group (c): plant growth regulating ingredients; Group (d): repellent components; Group (e): biological control agents.

8. A method for controlling harmful arthropods or harmful nematodes, which comprises applying an effective amount of the composition according to claim 7 to harmful arthropods or harmful nematodes or to habitats of harmful arthropods or harmful nematodes.

9. A seed or a vegetative reproductive organ carrying an effective amount of a compound represented by formula (I) according to any one of claims 1 to 5, or an N-oxide thereof, or a salt thereof.

10. A seed or vegetative reproductive organ carrying an effective amount of the composition of claim 7.

11. A composition for controlling harmful arthropods or harmful nematodes, comprising a compound represented by formula (I) according to any one of claims 1 to 5, or an N-oxide thereof, or a salt thereof, and an inert carrier.

12. Formula (II) 【Chemistry 2】 [During the ceremony, R 1 is a hydrogen atom, a C1-C3 alkyl group, or CH 2 OR A1 represents R 2 is OR A2 represents R 3 represents a hydrogen atom, R 4 is a methyl group or CH 2 OR A3 represents R 5 is a methyl group or CH 2 OR A4 represents R 6 is a hydrogen atom or OR A5 represents R 8 represents a hydrogen atom, a halogen atom, a methoxy group, or OR A6 represents R 9 is a methyl group or CH 2 OR A7 represents R 10 is a hydrogen atom or OR A8 represents R 12 is a hydrogen atom or OR A10 represents R 13 represents a hydrogen atom, R 14 represents a hydrogen atom, X represents a halogen atom; R 18 is a methyl group or CH 2 OR A14 represents R 19 represents a hydrogen atom, R 20 is a hydrogen atom or OR A15 represents R 21 is a methyl group, CH 2 OR A16 , or CH 2 NHCH 2 C(O)OCH 3 represents R 22 is a hydrogen atom or OR A17 represents R 23 is a hydrogen atom or OR A18 represents R 24 is a hydrogen atom, a C1-C3 alkoxy group, or OR A19 represents R 25 represents a hydrogen atom, R 26 is a hydrogen atom or OR A20 represents R A1 , R A2 , R A3 , R A4 , R A5 , R A6 , R A7 , R A8 , R A10 , R A14 , R A15 , R A16 , R A17 , R A18 , R A19 , and R A20 are the same or different and represent a hydrogen atom, a (C1-C6 alkyl)carbonyl group, or a (C3-C6 cycloalkyl)carbonyl group; R 2 and R 3 and may together form an oxo group, R 3 and R 18 Together # 3 —O—CHR B1 - may be formed, 3 is R 3 represents the bonding position with the carbon atom to which it is bonded, R 13 and R 14 and may together form an oxo group, R 18 and R 22 Together # 18 -CH 2 -O- may be formed, 18 is R 18 represents the bonding position with the carbon atom to which it is bonded, R 18 and R 23 Together with -CH 2 - may be formed, R 19 , R 20 , R 22 , R 23 , R 25 , and R 26 may form a benzene ring together with the carbon atom to which they are attached, R 21 and R 22 Together = CH 2 and R 22 and R 23 and may form a double bond together with the carbon atom to which they are attached, R 24 and R 25 and may together form an oxo group, R B1 represents a hydrogen atom or a C1-C3 alkoxy group. or an N-oxide thereof, or a salt thereof.

13. In formula (II), R 2 and R 3 and together form an oxo group, and R 4 is a methyl group, and R 5 is a methyl group, and R 6 is a hydrogen atom, and R 8 is a hydrogen atom, and R 9 is a methyl group, and R 10 is a hydrogen atom, and R 12 is a hydrogen atom, and R 18 is a methyl group, and R 20 is a hydrogen atom, and R 21 is a methyl group, and R 22 is a hydrogen atom or OR A17 and R 21 and R 22 Together = CH 2 and R 23 is a hydrogen atom or OR A18 and R 18 and R 23 Together with -CH 2 - may be formed, and R 22 and R 23 and may form a double bond together with the carbon atom to which they are attached, and R 24 is a hydrogen atom or OR A19 and R 25 is a hydrogen atom, and R 24 and R 25 may be taken together to form an oxo group, and R 26 The compound according to claim 12, wherein is a hydrogen atom.

14. A compound represented by formula (AA1), formula (AA2), formula (AA3), formula (BB1), formula (EE1), formula (EE3), formula (EE4), formula (EE5), formula (EE6), formula (EE7), formula (GG1), formula (GG2), or formula (GG3), or an N-oxide thereof or a salt thereof, or a compound represented by formula (EE2). 【Transformation 3】 【Chemistry 4】 【Transformation 5】 【Transformation 6】 【Transformation 7】 【Transformation 8】

15. A compound represented by formula (AA1), formula (AA2), formula (AA3), formula (BB1), formula (EE1), formula (EE3), formula (EE4), formula (EE5), formula (EE6), formula (GG1), or formula (GG3), or an N-oxide thereof or a salt thereof, or a compound represented by formula (EE2), according to claim 14.

16. A composition for controlling harmful arthropods or harmful nematodes, comprising the compound according to any one of claims 12 to 15, or an N-oxide thereof, or a salt thereof.

17. The composition of claim 16, further comprising one or more components selected from the group consisting of group (a), group (b), group (c), group (d), and group (e): Group (a): A group consisting of insecticidal active ingredients, acaricidal active ingredients and nematocidal active ingredients; Group (b): bactericidal active ingredient; Group (c): plant growth regulating ingredients; Group (d): repellent components; Group (e): biological control agents.

18. A method for controlling harmful arthropods or harmful nematodes, which comprises applying an effective amount of the composition according to claim 17 to harmful arthropods or harmful nematodes or to a habitat of harmful arthropods or harmful nematodes.

19. A seed or vegetative reproductive organ carrying an effective amount of the compound according to any one of claims 12 to 15, or an N-oxide thereof, or a salt thereof.

20. 18. A seed or vegetative reproductive organ carrying an effective amount of the composition of claim 17.

21. A composition for controlling harmful arthropods or harmful nematodes, comprising the compound according to any one of claims 12 to 15, or an N-oxide thereof, or a salt thereof, and an inert carrier.

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